#------------------------------------------------------------------------------
#$Date: 2019-05-17 13:38:46 +0300 (Fri, 17 May 2019) $
#$Revision: 215244 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/16/2021624.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021624
loop_
_publ_author_name
'Piontek, Mateusz'
'Morgenstern, Bernd'
'Steinbr\"uck, Nils'
'Oberhausen, Bastian'
'Kickelbick, Guido'
'Hegetschweiler, Kaspar'
_publ_section_title
;
HBr or not HBr? That is the question: crystal structure of
6-hydroxy-1,4-diazepane-1,4-diium dibromide redetermined
;
_journal_coeditor_code KU3242
_journal_issue 6
_journal_name_full 'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi 10.1107/S2053229619005321
_journal_volume 75
_journal_year 2019
_chemical_formula_iupac 'C5 H14 N2 O 2+, 2Br -'
_chemical_formula_moiety 'C5 H14 N2 O 2+, 2(Br -)'
_chemical_formula_sum 'C5 H14 Br2 N2 O'
_chemical_formula_weight 278.00
_chemical_name_systematic
;
6-Hydroxy-1,4-diazepane-1,4-diium dibromide
;
_space_group_crystal_system orthorhombic
_space_group_IT_number 19
_space_group_name_Hall 'P 2ac 2ab'
_space_group_name_H-M_alt 'P 21 21 21'
_symmetry_space_group_name_Hall 'P 2ac 2ab'
_symmetry_space_group_name_H-M 'P 21 21 21'
_atom_sites_solution_hydrogens mixed
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_audit_creation_method SHELXL-2014/6
_cell_angle_alpha 90
_cell_angle_beta 90
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 7.7005(4)
_cell_length_b 9.2774(5)
_cell_length_c 12.6853(6)
_cell_measurement_reflns_used 1133
_cell_measurement_temperature 142(2)
_cell_measurement_theta_max 25.69
_cell_measurement_theta_min 3.80
_cell_volume 906.25(8)
_computing_cell_refinement
;
SAINT (Bruker, 2010)
;
_computing_data_collection
;
APEX2 (Bruker, 2010)
;
_computing_data_reduction
;
SAINT (Bruker, 2010)
;
_computing_molecular_graphics
;
DIAMOND (Brandenburg, 2007)
;
_computing_publication_material
;
PLATON (Spek, 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2014 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 142(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type 'Bruker APEXII CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_reflns_av_R_equivalents 0.0502
_diffrn_reflns_av_unetI/netI 0.0815
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_k_min -10
_diffrn_reflns_limit_l_max 15
_diffrn_reflns_limit_l_min -16
_diffrn_reflns_number 4858
_diffrn_reflns_theta_full 25.242
_diffrn_reflns_theta_max 27.585
_diffrn_reflns_theta_min 2.720
_diffrn_source 'sealed tube'
_exptl_absorpt_coefficient_mu 8.889
_exptl_absorpt_correction_T_max 0.7456
_exptl_absorpt_correction_T_min 0.5761
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour colourless
_exptl_crystal_density_diffrn 2.038
_exptl_crystal_description needle
_exptl_crystal_F_000 544
_exptl_crystal_size_max 0.228
_exptl_crystal_size_mid 0.070
_exptl_crystal_size_min 0.019
_refine_diff_density_max 0.614
_refine_diff_density_min -0.512
_refine_ls_abs_structure_details
;
Flack x determined using 646 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack 0.05(2)
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 0.932
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 106
_refine_ls_number_reflns 2089
_refine_ls_number_restraints 5
_refine_ls_restrained_S_all 0.931
_refine_ls_R_factor_all 0.0483
_refine_ls_R_factor_gt 0.0372
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0594
_refine_ls_wR_factor_ref 0.0632
_reflns_number_gt 1789
_reflns_number_total 2089
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file ku3242sup1.cif
_cod_data_source_block I
_cod_database_code 2021624
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min 0.236
_shelx_estimated_absorpt_t_max 0.849
_shelx_hkl_file
;
1 0 0 7.00 4.50
-1 0 0 5.30 4.30
2 0 0 9487.25 473.25
-2 0 0 9510.35 472.85
-3 0 0 -2.30 8.10
3 0 0 0.70 8.80
4 0 0 277.57 30.80
-4 0 0 216.88 25.50
4 0 0 222.18 26.80
-5 0 0 3.20 11.40
5 0 0 -6.30 13.50
6 0 0 -4.40 15.70
7 0 0 -6.90 18.50
8 0 0 1396.06 100.09
9 0 0 -10.80 23.10
10 0 0 894.91 92.79
0 1 0 1.40 5.20
0 -1 0 4.30 5.10
1 -1 0 9.90 6.40
1 1 0 2.90 7.30
-1 1 0 1.90 6.00
1 1 0 -1.20 7.40
-1 -1 0 0.60 6.40
-1 -1 0 -0.40 7.20
2 1 0 3276.87 167.18
2 -1 0 3263.67 166.38
-2 1 0 3185.68 165.58
2 1 0 3183.08 166.88
-3 1 0 486.45 35.20
3 -1 0 524.05 35.90
3 1 0 481.95 36.20
3 1 0 486.35 36.70
-4 1 0 11.10 11.50
4 1 0 6.70 13.50
4 -1 0 9.20 11.10
-5 1 0 640.34 46.80
5 1 0 636.84 51.89
6 1 0 1900.91 112.29
-6 1 0 1689.93 102.89
7 1 0 1268.67 92.69
7 -1 0 1362.16 93.29
8 -1 0 471.45 59.49
8 1 0 551.24 63.29
9 1 0 445.26 64.09
9 -1 0 362.26 55.99
10 -1 0 21.90 31.60
0 2 0 1213.68 71.29
0 -2 0 1214.68 70.49
1 2 0 9575.44 488.95
1 2 0 9643.44 489.15
-1 2 0 9999.00 488.55
-1 -2 0 9751.02 489.15
2 -2 0 1072.39 64.59
2 2 0 1086.89 66.39
2 2 0 1109.79 68.29
-2 2 0 1123.49 64.89
-3 2 0 235.68 26.10
3 -2 0 196.68 25.20
3 2 0 210.18 26.90
3 2 0 282.27 33.70
-4 2 0 3214.68 173.58
4 2 0 3150.98 182.58
4 2 0 3414.26 178.88
5 2 0 414.26 45.70
5 2 0 339.47 45.10
-5 2 0 391.96 37.80
6 2 0 1122.99 86.39
-6 2 0 1303.57 80.19
6 2 0 1384.76 97.69
7 2 0 88.99 29.70
8 2 0 116.59 35.60
8 -2 0 127.39 34.20
9 2 0 962.50 96.89
9 -2 0 997.80 86.59
0 3 0 7.70 14.10
-1 3 0 1144.99 73.39
-1 -3 0 1231.08 74.49
1 3 0 1210.38 74.79
1 3 0 1155.48 74.89
2 3 0 389.66 38.70
-2 -3 0 327.17 35.50
2 3 0 343.87 37.70
-2 3 0 387.06 34.20
3 3 0 1086.69 74.49
3 3 0 1004.90 71.99
-3 3 0 1215.98 71.49
-4 3 0 71.39 19.00
4 3 0 105.59 24.80
4 3 0 55.59 21.90
5 3 0 76.99 25.60
5 3 0 87.89 26.70
-5 3 0 89.59 21.50
-6 3 0 528.45 46.50
6 3 0 588.54 65.19
6 3 0 610.94 62.29
7 3 0 365.36 52.59
8 3 0 245.48 48.30
9 3 0 203.38 48.20
0 4 0 2715.33 155.78
-1 4 0 62.09 22.10
-1 -4 0 64.59 21.70
1 4 0 60.19 22.00
2 4 0 63.89 23.30
-2 4 0 55.59 18.80
2 4 0 46.00 18.20
-2 -4 0 72.89 22.30
3 4 0 2880.41 164.88
3 4 0 2817.22 163.98
-3 4 0 2903.81 160.88
4 4 0 3397.36 188.98
4 4 0 3237.08 190.58
-4 4 0 3334.07 183.58
5 4 0 3956.40 220.58
-5 4 0 3949.00 212.78
5 4 0 3775.52 223.18
6 4 0 1023.80 80.99
-6 4 0 938.31 72.19
7 4 0 448.56 59.99
8 4 0 49.20 30.30
9 4 0 112.59 38.90
0 5 0 24.30 19.80
0 -5 0 26.60 19.20
-1 -5 0 66.09 22.90
1 5 0 33.00 21.10
-1 5 0 64.29 26.20
-2 5 0 3092.69 176.98
2 5 0 3070.09 178.48
-2 -5 0 3030.60 176.18
2 5 0 3067.79 177.58
-3 -5 0 6.40 18.60
-3 5 0 18.90 18.60
3 5 0 -14.00 18.70
3 5 0 0.80 14.40
4 5 0 558.84 61.09
-4 5 0 615.84 54.69
4 5 0 570.44 63.69
5 5 0 243.88 44.00
-5 5 0 174.18 33.50
5 5 0 179.18 37.30
6 5 0 118.69 35.80
7 5 0 81.99 35.00
8 5 0 19.00 30.50
9 5 0 -41.00 28.80
0 6 0 1271.27 96.09
0 -6 0 1235.88 89.39
-1 6 0 900.81 77.89
1 6 0 1044.60 81.69
-1 -6 0 899.21 72.09
2 6 0 156.98 37.30
-2 -6 0 141.99 32.70
-2 6 0 105.79 29.10
-3 6 0 1913.31 123.99
3 6 0 1796.52 124.29
-3 -6 0 1912.21 125.99
3 6 0 1909.41 127.49
-4 6 0 1185.48 85.49
4 6 0 944.41 84.59
4 6 0 1060.59 85.29
-5 6 0 1980.70 126.19
5 6 0 1893.41 133.59
6 6 0 301.47 52.09
7 6 0 373.86 63.49
8 6 0 102.29 43.40
0 7 0 -0.10 24.50
0 -7 0 -10.50 20.00
-1 -7 0 462.25 55.29
1 7 0 667.33 76.79
-1 7 0 399.06 56.69
2 7 0 3.50 23.80
-2 -7 0 14.30 23.40
-2 7 0 18.50 23.20
3 7 0 350.96 55.29
-3 -7 0 312.77 49.90
-3 7 0 278.37 47.30
4 7 0 156.08 43.00
-4 7 0 136.89 36.40
-5 7 0 48.00 27.40
5 7 0 -5.50 27.10
6 7 0 663.23 84.09
7 7 0 109.59 45.20
8 7 0 309.67 66.89
0 -8 0 725.53 74.79
0 8 0 611.84 76.09
1 8 0 3532.95 224.38
-1 8 0 3815.32 225.08
-1 -8 0 3590.54 215.68
-2 8 0 517.75 71.19
-2 -8 0 514.35 65.49
2 8 0 439.36 65.89
-3 8 0 33.00 30.50
-3 -8 0 16.50 28.60
3 8 0 68.39 37.60
4 8 0 680.83 84.29
-4 8 0 504.25 70.49
5 8 0 18.90 33.10
6 8 0 136.39 51.39
7 8 0 301.27 69.49
0 -9 0 26.30 25.80
0 9 0 -10.60 29.30
1 9 0 81.49 42.60
-1 -9 0 104.09 36.00
-1 9 0 224.48 52.89
1 -9 0 144.99 36.40
-2 9 0 202.18 48.40
2 9 0 130.49 48.90
-2 -9 0 165.98 45.30
3 9 0 208.48 54.19
-3 9 0 163.68 48.50
4 9 0 27.00 38.10
-4 9 0 -16.70 29.40
5 9 0 340.67 69.79
6 9 0 240.58 57.69
0 -10 0 2848.31 180.78
0 10 0 2697.23 193.08
1 -10 0 -13.90 24.20
1 10 0 -5.00 37.50
-1 10 0 9.50 35.30
-1 -10 0 17.10 29.70
2 10 0 971.30 112.59
2 -10 0 678.73 83.79
-2 10 0 658.13 89.39
3 10 0 81.39 44.30
-3 10 0 59.19 40.70
4 10 0 -19.90 33.00
5 10 0 294.97 68.69
0 11 0 -4.10 35.40
-1 11 0 26.10 42.40
1 11 0 -25.40 35.50
2 11 0 157.58 58.49
-2 11 0 111.99 49.50
-3 11 0 -27.60 35.50
3 11 0 38.60 44.90
4 11 0 -6.00 38.20
0 12 0 13.60 44.70
1 12 0 135.89 58.79
-1 12 0 258.57 65.49
0 0 -1 0.90 2.40
0 0 1 0.20 2.30
0 0 -1 4.70 2.70
1 0 1 89.19 12.00
-1 0 -1 87.79 12.50
2 0 -1 254.47 18.00
2 0 1 285.77 26.10
-2 0 -1 237.48 23.80
3 0 1 2422.56 138.29
3 0 -1 2614.64 131.29
-3 0 -1 2461.85 135.69
4 0 -1 149.88 20.40
4 0 1 123.59 23.10
-4 0 -1 151.88 23.20
4 0 -1 106.39 17.50
5 0 -1 3446.56 177.58
5 0 1 3210.78 183.08
5 0 -1 3348.26 178.48
-5 0 -1 3190.78 179.08
6 0 -1 503.35 44.50
-6 0 -1 454.45 46.50
6 0 1 396.96 48.40
7 0 -1 54.59 23.50
7 0 1 54.99 26.80
8 0 -1 195.98 37.20
8 0 1 211.58 41.30
9 0 -1 81.69 32.10
9 0 1 94.79 36.50
10 0 1 19.90 33.50
10 0 -1 41.90 31.70
0 -1 1 164.38 15.40
0 -1 -1 195.48 15.70
0 1 -1 194.18 16.50
0 1 1 184.58 15.70
0 -1 -1 184.98 12.00
0 1 1 185.78 12.40
-1 1 1 1370.46 77.79
1 1 -1 1296.77 81.79
1 1 -1 1281.37 78.99
-1 -1 -1 1370.46 81.59
-1 -1 -1 1274.27 80.59
-1 1 -1 1755.52 82.29
1 1 1 1740.43 82.39
-1 -1 1 1832.52 84.49
1 -1 -1 1784.82 79.19
2 -1 1 2466.45 123.59
2 1 -1 2338.37 120.09
-2 -1 -1 2269.67 123.99
-2 1 1 2342.47 117.69
2 1 -1 2355.46 125.39
2 1 1 2132.89 122.99
2 1 1 2333.27 123.99
2 -1 -1 2264.77 118.69
-2 1 -1 2253.57 122.69
-2 -1 1 2287.87 118.89
-3 1 1 3795.12 184.68
3 1 -1 3597.24 194.98
3 1 -1 3748.32 188.08
-3 -1 -1 3596.64 191.78
3 1 -1 3551.44 187.58
3 -1 -1 3586.14 186.68
3 1 1 3581.64 191.68
-3 1 -1 3521.55 190.38
-4 1 1 331.07 25.70
-4 -1 -1 323.77 35.20
4 1 -1 347.27 29.70
4 1 -1 333.27 32.00
-4 1 -1 285.07 32.60
4 1 1 376.96 39.00
4 -1 -1 250.27 28.50
5 1 -1 1231.78 77.79
-5 1 1 1090.19 71.29
5 1 -1 1309.67 80.19
5 -1 -1 1327.97 78.19
5 1 1 1328.47 85.09
-5 1 -1 1476.15 82.89
6 1 -1 128.49 26.30
6 1 1 109.29 29.20
-6 1 -1 123.49 26.40
7 -1 1 1568.74 109.59
7 1 -1 1684.93 106.89
7 1 1 1641.74 111.29
7 -1 -1 1605.64 104.39
8 1 -1 186.48 37.30
8 -1 1 104.19 34.40
8 -1 -1 150.08 34.50
8 1 1 187.58 42.80
9 1 -1 405.96 56.09
9 -1 1 393.26 60.89
9 1 1 312.97 56.09
9 -1 -1 291.67 48.40
0 2 1 735.13 48.00
0 -2 -1 738.03 44.20
0 -2 -1 743.03 47.40
0 2 -1 719.43 48.30
-1 2 1 2627.84 133.29
-1 -2 -1 2501.65 132.09
1 2 -1 2571.84 134.49
1 2 -1 2597.44 136.59
1 2 1 2407.56 131.69
-1 2 -1 2520.25 134.49
-1 -2 1 2505.45 136.39
1 -2 -1 2480.65 132.89
1 2 1 2330.97 133.69
2 2 -1 628.14 43.30
2 2 -1 641.44 47.10
-2 2 1 608.54 40.30
2 2 1 689.53 46.00
2 2 1 675.73 46.10
-2 -2 1 622.84 46.90
-2 2 -1 659.03 44.30
2 -2 -1 628.34 41.30
3 2 -1 272.27 29.30
-3 2 1 301.07 25.00
3 2 -1 326.87 36.00
-3 2 -1 298.87 32.30
3 2 1 222.18 30.40
3 -2 -1 265.57 27.30
4 2 -1 3250.37 191.08
-4 2 1 3234.38 178.48
4 2 -1 3452.55 184.98
4 2 1 3556.54 189.08
4 -2 -1 3456.15 182.28
-4 2 -1 3662.93 185.68
5 2 -1 130.49 25.10
5 2 -1 122.79 30.50
-5 2 1 85.49 17.00
5 2 1 146.99 29.50
-5 2 -1 167.58 27.80
6 2 -1 475.25 58.49
6 2 -1 433.66 50.29
-6 2 -1 532.55 51.59
6 2 1 566.44 59.09
7 2 -1 354.26 48.90
7 2 1 384.16 53.49
8 2 -1 374.26 51.69
8 -2 1 218.98 45.20
8 -2 -1 236.98 40.70
8 2 1 313.37 50.29
9 -2 1 315.47 56.09
9 2 -1 416.06 59.29
9 -2 -1 323.17 51.99
9 2 1 304.47 56.49
0 3 1 2511.75 138.89
0 3 -1 2402.06 138.79
0 -3 -1 2547.05 134.79
-1 -3 -1 2571.64 136.19
1 3 -1 2552.04 139.69
-1 3 1 2505.65 138.69
1 3 1 2340.47 138.79
-1 3 -1 2536.35 139.29
1 3 1 2515.05 136.59
-1 -3 1 2524.55 141.79
-2 3 1 4231.78 218.18
2 3 -1 4144.09 220.28
2 3 -1 4322.27 223.78
2 3 1 3993.40 220.78
2 3 1 4115.29 219.78
-2 3 -1 4014.40 219.78
-2 -3 1 4257.17 224.08
3 3 -1 1209.18 75.89
3 3 -1 1139.29 77.89
-3 3 1 1260.47 71.49
-3 3 -1 1103.59 74.39
3 3 1 1152.28 77.29
3 3 1 1096.09 76.39
4 3 -1 392.96 46.20
4 3 -1 371.86 41.20
-4 3 1 373.86 34.60
4 3 1 377.06 43.90
-4 3 -1 403.56 42.10
4 3 1 517.65 53.09
-5 3 1 433.26 38.90
5 3 -1 486.15 50.39
5 3 -1 531.45 57.79
5 3 1 516.55 54.79
5 3 1 509.35 56.29
-5 3 -1 543.55 46.70
6 3 -1 1979.10 130.59
6 3 -1 1871.61 121.09
6 3 1 1996.30 132.09
-6 3 -1 1874.31 116.99
6 3 1 1923.81 126.09
7 3 -1 117.29 32.80
7 3 1 80.19 32.60
8 3 -1 723.23 76.19
8 3 1 583.84 75.89
9 3 -1 62.99 34.80
9 -3 1 100.69 37.70
9 3 1 82.59 37.90
0 4 -1 4689.23 246.68
0 -4 -1 4600.94 239.98
0 4 1 4349.16 244.28
-1 -4 -1 1273.07 77.49
-1 4 1 1278.37 81.89
1 4 -1 1179.68 81.79
-1 -4 1 1284.57 82.79
-1 4 -1 1090.69 79.89
1 4 1 1169.78 81.49
-2 -4 -1 1049.20 71.99
2 4 -1 1035.40 74.19
2 4 -1 896.41 72.59
-2 4 1 1189.38 73.29
2 4 1 1082.69 71.19
-2 4 -1 1125.09 74.99
2 4 1 1065.99 74.09
-2 -4 1 1017.90 74.19
-3 4 1 594.54 48.40
3 4 -1 543.15 55.29
3 4 -1 581.24 59.09
3 4 1 575.54 50.89
-3 -4 1 587.34 59.19
-3 4 -1 676.13 52.69
3 4 1 629.14 54.49
4 4 -1 82.89 28.20
-4 4 1 67.69 19.60
4 4 -1 97.29 25.70
-4 4 -1 60.39 21.70
4 4 1 75.79 24.20
4 4 1 47.80 22.50
-5 4 1 163.98 27.30
5 4 -1 180.58 33.20
5 4 -1 177.78 35.50
5 4 1 158.98 35.60
-5 4 -1 155.38 29.80
5 4 1 173.38 37.60
6 4 -1 41.90 26.10
6 4 1 26.00 27.80
-6 4 -1 22.10 18.60
7 4 -1 299.97 49.00
7 4 1 317.27 54.39
8 4 -1 643.74 73.99
8 4 1 654.03 80.29
9 4 -1 497.85 70.09
9 4 1 582.24 81.09
0 5 1 1300.37 93.59
0 5 -1 1309.67 93.99
0 -5 -1 1448.16 88.79
-1 5 1 736.93 63.89
1 5 -1 754.12 65.39
-1 -5 -1 695.83 57.89
-1 -5 1 818.32 65.89
1 5 1 860.21 66.59
-1 5 -1 880.11 67.29
-2 -5 -1 2275.67 129.39
-2 5 1 2062.49 129.19
2 5 -1 1980.40 130.09
-2 5 -1 2123.19 131.39
2 5 1 2143.49 128.69
2 5 1 2087.69 131.39
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3 -1 -12 359.16 43.50
3 1 12 320.27 54.29
-3 -1 12 394.86 52.19
-3 1 -12 393.36 64.19
-4 -1 -12 752.92 90.59
4 1 -12 758.42 58.39
4 -1 12 782.92 88.69
-4 1 -12 718.33 88.69
4 -1 -12 772.22 55.99
4 1 12 898.91 96.89
5 -1 12 69.19 36.00
-5 -1 -12 85.39 43.20
5 1 12 61.39 40.30
-5 1 -12 60.09 37.60
6 -1 12 528.75 77.19
-6 -1 -12 406.96 74.49
-6 1 -12 788.02 101.99
6 1 12 720.83 91.29
0 -2 -12 160.38 38.20
0 2 -12 204.98 40.30
1 -2 12 349.57 53.69
1 2 -12 312.77 48.00
-1 -2 -12 364.56 57.69
1 -2 -12 375.36 50.59
1 2 12 424.66 53.69
-1 -2 12 344.57 55.59
-1 2 -12 348.77 52.29
-2 -2 -12 111.49 39.10
2 2 -12 129.99 31.80
2 -2 12 105.99 37.50
2 -2 -12 158.28 31.60
2 2 12 211.18 42.90
-2 -2 12 179.78 41.40
-2 2 -12 152.48 43.00
3 2 -12 254.67 39.00
3 -2 12 257.97 52.29
-3 -2 -12 197.18 52.09
3 -2 -12 261.57 37.80
-3 -2 12 261.67 47.10
-3 2 -12 266.27 55.49
3 2 12 349.07 58.49
4 2 -12 117.49 26.40
4 -2 12 153.28 43.70
-4 -2 -12 123.59 41.40
-4 -2 12 65.79 33.30
4 2 12 128.89 42.60
-4 2 -12 88.59 40.90
5 2 -12 607.84 48.90
-5 -2 -12 599.64 86.19
5 -2 12 482.65 76.79
5 2 12 508.45 74.99
-5 2 -12 709.73 93.59
6 -2 12 43.90 40.00
-6 -2 -12 66.29 42.60
6 2 12 16.60 33.20
-6 2 -12 45.30 40.90
0 3 -12 910.61 88.69
0 -3 -12 743.43 80.39
1 -3 12 1105.89 87.99
-1 -3 -12 755.42 84.79
1 3 -12 888.01 80.39
1 3 12 850.61 77.79
-1 -3 12 1128.39 95.19
1 -3 -12 1006.90 82.49
-1 3 -12 1149.78 91.59
2 -3 12 610.74 73.59
2 3 -12 600.84 67.39
-2 -3 -12 507.75 72.19
-2 -3 12 555.34 73.99
-2 3 -12 510.55 71.49
2 -3 -12 517.85 60.89
2 3 12 554.54 69.69
-3 -3 -12 999.10 105.69
3 -3 12 936.01 101.09
3 3 -12 1052.29 81.09
-3 3 -12 894.51 104.29
-3 -3 12 1269.27 100.29
3 3 12 1116.69 107.49
4 3 -12 196.18 35.00
4 -3 12 226.98 52.79
-4 -3 -12 194.88 51.29
4 3 12 99.89 41.00
-4 3 -12 224.98 54.99
5 3 -12 433.46 48.50
5 -3 12 539.55 79.79
-5 -3 -12 347.37 70.89
-5 3 -12 563.44 86.09
5 3 12 453.35 75.09
6 -3 12 118.69 44.40
-6 -3 -12 134.99 51.19
6 3 12 92.79 46.40
-6 3 -12 165.98 51.59
0 4 -12 254.27 49.20
0 -4 -12 396.76 59.89
1 4 -12 523.05 66.09
-1 -4 -12 414.56 63.49
1 4 12 490.85 96.19
-1 -4 12 525.45 110.99
-1 4 -12 513.95 70.89
-2 -4 -12 62.99 38.20
2 4 -12 14.50 25.60
2 4 12 21.50 27.30
-2 4 -12 25.40 30.40
-3 -4 -12 32.70 36.50
3 4 -12 38.50 26.60
3 -4 12 55.69 35.00
3 4 12 47.30 34.70
-3 4 -12 53.69 36.30
4 -4 12 224.08 52.09
-4 -4 -12 184.48 53.29
4 4 -12 272.07 42.10
4 4 12 241.58 54.69
-4 4 -12 193.28 52.99
5 -4 12 95.19 41.90
5 4 -12 149.19 34.30
-5 -4 -12 90.49 45.20
-5 4 -12 133.79 51.49
5 4 12 145.99 48.50
-6 -4 -12 258.77 64.49
6 -4 12 94.09 44.30
6 4 12 153.08 52.59
-6 4 -12 215.38 60.79
0 5 -12 6.10 31.20
1 5 -12 595.24 73.79
-1 5 -12 743.93 86.59
2 5 -12 775.32 85.59
2 5 12 832.72 92.19
-2 5 -12 901.41 102.99
3 5 -12 655.03 74.69
3 5 12 727.13 88.09
-3 5 -12 530.15 78.89
4 5 -12 52.69 29.80
4 5 12 61.69 36.20
-4 5 -12 112.69 46.60
5 5 -12 415.56 57.39
5 5 12 504.15 77.89
-5 5 -12 470.15 80.89
0 6 -12 416.56 66.09
1 6 -12 111.39 40.00
-1 6 -12 118.39 44.00
2 6 -12 52.29 34.50
2 6 12 89.29 66.59
-2 6 -12 28.10 34.10
3 6 -12 10.40 26.70
-3 6 -12 45.00 37.50
3 6 12 -16.60 30.10
4 6 -12 355.76 57.59
-4 6 -12 302.47 68.19
4 6 12 334.67 68.59
0 7 -12 215.58 51.29
1 7 -12 434.76 73.49
-1 7 -12 514.75 76.39
2 7 -12 294.57 57.89
-2 7 -12 319.07 64.39
3 7 -12 519.55 75.09
-3 7 -12 576.84 91.69
3 7 12 719.63 93.39
0 8 -12 -4.70 34.10
1 8 -12 138.59 51.59
-1 8 -12 222.08 58.79
0 0 -13 -1.50 24.50
-1 0 -13 2617.94 174.28
1 0 -13 2768.42 167.58
-2 0 -13 19.80 30.20
2 0 13 8.60 24.90
2 0 -13 19.00 23.20
-3 0 -13 99.59 42.00
3 0 -13 177.58 32.80
3 0 13 174.28 46.80
4 0 13 35.40 33.00
4 0 -13 81.39 22.80
-4 0 -13 57.49 40.20
5 0 13 34.70 36.60
-5 0 -13 149.09 49.60
6 0 13 -27.90 31.50
-6 0 -13 129.79 54.79
0 1 -13 176.88 40.60
0 -1 -13 52.29 34.10
-1 -1 -13 479.45 68.69
1 1 -13 582.44 66.19
-1 -1 13 591.14 66.49
-1 1 -13 601.04 72.89
1 -1 -13 558.14 64.69
-2 -1 -13 49.80 36.50
2 1 -13 65.49 27.80
2 -1 13 111.79 37.60
2 -1 -13 92.39 30.20
2 1 13 74.99 33.10
-2 1 -13 155.38 42.90
3 -1 13 351.96 59.59
3 1 -13 425.26 50.59
-3 -1 -13 375.66 68.59
-3 1 -13 327.27 60.79
3 -1 -13 394.66 47.90
3 1 13 384.86 61.29
4 -1 13 90.39 37.90
-4 -1 -13 158.18 52.19
4 1 -13 92.59 25.50
4 -1 -13 73.09 21.80
4 1 13 104.59 42.90
-4 1 -13 67.79 40.00
5 -1 13 78.29 41.00
-5 -1 -13 81.99 45.00
5 1 13 87.69 43.90
-5 1 -13 121.79 48.40
6 -1 13 406.66 73.79
-6 -1 -13 381.96 73.89
-6 1 -13 369.86 75.39
6 1 13 366.46 70.09
0 2 -13 1924.61 132.29
0 -2 -13 1817.52 131.29
-1 -2 -13 75.59 36.00
1 2 -13 76.39 31.20
-1 -2 13 1.20 24.50
1 -2 -13 38.10 28.30
-1 2 -13 94.09 35.90
2 2 -13 550.44 63.39
-2 -2 -13 494.75 72.69
2 -2 13 370.66 58.99
2 2 13 471.85 63.59
2 -2 -13 515.85 57.89
-2 -2 13 539.65 67.29
-2 2 -13 526.45 75.39
-3 -2 -13 497.25 74.79
3 -2 13 604.24 78.19
3 2 -13 661.53 65.29
-3 2 -13 504.25 77.39
3 2 13 583.24 76.49
3 -2 -13 540.75 57.79
-3 -2 13 577.24 90.19
4 -2 13 201.68 51.29
4 2 -13 98.99 27.80
-4 -2 -13 148.79 49.40
-4 2 -13 79.99 39.70
4 2 13 92.39 40.90
-5 -2 -13 758.02 95.39
5 2 13 699.83 91.39
-5 2 -13 518.15 87.39
0 -3 -13 166.08 43.60
0 3 -13 189.48 45.60
-1 -3 -13 15.00 31.50
1 3 -13 35.30 27.10
-1 3 -13 33.00 31.50
1 -3 -13 51.09 29.40
-1 -3 13 27.90 30.60
-2 -3 -13 698.73 86.29
2 -3 13 652.13 79.29
2 3 -13 575.34 68.49
-2 -3 13 533.45 73.89
2 -3 -13 643.14 71.19
2 3 13 727.73 80.79
-2 3 -13 596.34 78.09
-3 -3 -13 210.68 54.39
3 -3 13 73.49 37.10
3 3 -13 143.79 36.30
3 3 13 194.68 50.09
-3 3 -13 168.18 48.60
4 -3 13 81.49 39.30
-4 -3 -13 150.78 49.90
4 3 -13 133.59 32.80
4 3 13 120.39 45.20
-4 3 -13 116.69 47.20
5 -3 13 117.59 43.00
-5 -3 -13 197.08 55.69
5 3 -13 207.98 39.30
-5 3 -13 224.08 57.49
5 3 13 279.37 61.29
0 -4 -13 -4.20 28.20
0 4 -13 10.20 28.00
1 4 -13 22.20 30.20
-1 -4 -13 47.90 37.30
-1 4 -13 32.70 31.40
2 -4 13 393.26 62.39
2 4 -13 328.87 53.19
-2 -4 -13 259.67 59.59
-2 4 -13 257.27 55.29
3 4 -13 244.08 46.70
-3 -4 -13 289.37 62.39
3 -4 13 370.26 66.39
3 4 13 296.27 58.49
-3 4 -13 372.76 69.69
4 -4 13 721.53 94.19
-4 -4 -13 812.02 105.19
4 4 -13 859.51 74.89
4 4 13 902.71 103.39
-4 4 -13 704.93 96.39
-5 -4 -13 415.36 78.29
5 4 -13 593.84 63.19
-5 4 -13 454.95 81.69
5 4 13 611.84 88.89
0 5 -13 47.60 33.90
1 5 -13 165.78 45.00
-1 5 -13 144.59 44.40
2 5 -13 144.49 41.80
-2 5 -13 138.39 47.30
3 5 -13 572.54 71.69
3 5 13 497.05 77.89
-3 5 -13 552.14 81.39
4 5 -13 265.37 46.80
4 -5 13 125.19 50.19
-4 5 -13 148.29 50.49
4 5 13 197.58 52.59
0 6 -13 158.38 51.29
1 6 -13 387.86 64.09
-1 6 -13 288.37 64.19
2 6 -13 423.66 65.99
-2 6 -13 319.37 65.79
3 6 -13 175.48 45.20
-3 6 -13 93.79 46.00
0 7 -13 179.98 53.69
1 7 -13 91.89 42.00
-1 7 -13 43.40 41.50
2 7 -13 360.46 63.09
-2 7 -13 298.57 66.99
0 0 -14 -9.30 25.70
1 0 -14 103.99 34.90
-1 0 -14 94.79 38.40
2 0 -14 441.46 57.19
-2 0 -14 456.65 70.89
3 0 14 432.76 66.69
-3 0 -14 375.36 68.19
3 0 -14 448.16 53.19
4 0 -14 1388.56 94.79
-4 0 -14 1581.34 132.29
4 0 14 1436.36 123.09
5 0 14 -12.00 31.90
-5 0 -14 9.20 38.40
0 1 -14 424.36 63.09
0 -1 -14 419.46 61.69
1 1 -14 98.79 37.70
-1 -1 -14 218.48 50.39
-1 1 -14 155.28 43.80
1 -1 -14 117.89 37.50
-2 -1 -14 501.75 70.09
2 1 -14 473.95 60.29
2 -1 -14 468.15 59.19
-2 1 -14 256.47 56.79
3 -1 14 290.47 56.79
3 1 -14 312.67 46.60
-3 -1 -14 344.87 63.89
-3 1 -14 243.68 56.29
3 1 14 286.87 57.89
3 -1 -14 228.68 40.80
4 -1 14 53.79 37.80
4 1 -14 119.29 29.20
-4 -1 -14 40.90 39.50
4 -1 -14 92.89 25.70
-4 1 -14 101.89 48.10
4 1 14 43.50 38.70
5 -1 14 15.10 37.20
-5 -1 -14 88.09 49.60
5 1 14 -1.80 33.10
-5 1 -14 26.70 39.00
0 2 -14 749.53 83.69
0 -2 -14 732.63 83.99
1 2 -14 53.19 31.40
-1 -2 -14 54.79 36.70
-1 2 -14 50.99 35.70
1 -2 -14 75.09 33.70
-2 -2 -14 680.73 91.09
2 2 -14 632.54 73.79
2 -2 -14 772.12 77.09
-2 2 -14 765.32 91.49
3 2 -14 459.25 59.79
3 -2 14 481.75 71.69
-3 -2 -14 450.55 76.99
3 -2 -14 597.54 61.79
-3 2 -14 498.05 77.59
3 2 14 544.25 77.49
4 2 -14 108.69 29.70
4 -2 14 24.70 34.10
-4 -2 -14 100.49 43.90
-4 2 -14 114.39 49.50
4 2 14 150.48 47.90
-5 -2 -14 497.55 83.79
5 -2 14 454.15 74.49
5 2 14 477.15 80.49
-5 2 -14 518.55 85.69
0 3 -14 38.10 30.80
0 -3 -14 -12.00 27.00
1 3 -14 343.97 58.39
-1 -3 -14 255.37 53.29
-1 3 -14 317.07 59.49
1 -3 -14 245.58 48.30
2 3 -14 101.39 38.70
-2 -3 -14 174.48 51.69
2 -3 -14 120.59 37.70
-2 3 -14 201.48 51.29
3 3 -14 251.27 45.60
-3 -3 -14 186.08 53.79
3 -3 14 99.59 46.00
-3 3 -14 251.87 57.19
4 3 -14 336.47 48.90
-4 -3 -14 280.97 64.99
4 -3 14 246.58 56.29
4 3 14 245.88 56.69
-4 3 -14 317.67 66.09
0 4 -14 651.53 83.89
0 -4 -14 660.73 83.59
-1 -4 -14 941.91 105.09
1 4 -14 973.90 101.39
-1 4 -14 919.41 105.89
-2 -4 -14 327.47 66.29
2 4 -14 448.96 64.19
-2 4 -14 357.36 67.39
3 -4 14 249.38 57.59
-3 -4 -14 298.07 69.49
3 4 -14 214.88 48.90
-3 4 -14 279.87 62.59
4 -4 14 119.29 46.00
4 4 -14 146.39 39.40
-4 -4 -14 82.69 49.60
4 4 14 61.99 43.20
-4 4 -14 141.29 55.59
0 5 -14 -49.40 27.80
1 5 -14 29.70 34.30
-1 5 -14 -53.89 26.50
2 5 -14 79.19 40.90
-2 5 -14 283.17 61.39
3 5 -14 238.98 51.59
-3 5 -14 251.07 59.69
0 6 -14 164.78 50.59
1 6 -14 597.24 84.69
-1 6 -14 577.24 86.29
0 0 -15 6.90 27.90
-1 0 -15 408.16 67.59
1 0 -15 394.86 60.39
2 0 -15 571.34 68.59
-2 0 -15 538.95 81.89
-3 0 -15 58.09 41.40
3 0 -15 23.30 25.80
-4 0 -15 59.69 42.00
4 0 15 70.79 60.49
0 1 -15 107.19 41.80
0 -1 -15 56.99 36.50
-1 -1 -15 445.56 72.99
1 1 -15 429.36 65.89
-1 1 -15 469.85 74.09
1 -1 -15 481.05 67.09
2 1 -15 141.79 38.60
-2 -1 -15 205.78 53.19
2 -1 -15 195.38 43.20
-2 1 -15 144.99 50.29
3 1 -15 831.02 75.59
-3 -1 -15 1011.00 115.99
3 -1 -15 772.92 76.69
-3 1 -15 864.31 108.99
4 1 -15 413.66 57.79
-4 -1 -15 343.47 73.09
4 -1 15 455.95 99.99
-4 1 -15 526.45 83.79
0 -2 -15 275.97 56.99
0 2 -15 330.77 60.39
1 2 -15 130.39 40.30
-1 -2 -15 78.39 41.30
1 -2 -15 119.19 39.80
-1 2 -15 120.99 46.90
-2 -2 -15 27.30 37.10
2 2 -15 -25.80 25.70
-2 2 -15 21.30 34.30
2 -2 -15 27.80 26.60
3 2 -15 180.68 40.90
-3 -2 -15 29.40 40.50
-3 2 -15 117.99 48.50
3 -2 -15 159.38 37.80
0 -3 -15 304.37 57.89
0 3 -15 274.77 57.79
-1 -3 -15 811.42 96.89
1 3 -15 622.24 81.59
-1 3 -15 720.63 93.89
1 -3 -15 865.41 91.19
-2 -3 -15 602.64 86.79
2 3 -15 657.83 79.49
-2 3 -15 771.02 97.89
2 -3 -15 548.75 69.09
-3 -3 -15 14.30 36.70
3 3 -15 -3.80 26.20
-3 3 -15 11.00 35.90
0 -4 -15 85.09 44.50
0 4 -15 75.49 40.90
-1 -4 -15 40.40 44.20
1 4 -15 45.40 35.20
-1 4 -15 60.69 41.00
-2 -4 -15 122.39 51.29
2 4 -15 37.60 34.60
-2 4 -15 37.00 41.00
0 0 -16 382.76 67.39
-1 0 -16 50.99 38.50
1 0 -16 71.49 34.30
-2 0 -16 260.97 61.59
2 0 -16 261.57 50.49
0 1 -16 538.55 78.49
0 -1 -16 515.55 77.59
1 1 -16 306.07 57.59
-1 -1 -16 241.98 56.39
1 -1 -16 234.08 53.59
-1 1 -16 295.07 63.39
-2 -1 -16 261.97 62.39
2 1 -16 335.87 55.99
-2 1 -16 246.78 59.59
2 -1 -16 135.69 43.10
0 2 -16 71.89 41.10
0 -2 -16 37.70 35.90
-1 -2 -16 294.87 62.19
1 2 -16 317.37 58.69
-1 2 -16 272.07 60.49
1 -2 -16 221.78 49.60
_computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)'
;
_shelx_hkl_checksum 36163
_shelx_res_file
;
TITL sh4074_a.res in P2(1)2(1)2(1)
REM Old TITL sh4074 in P2(1)2(1)2(1)
REM SHELXT solution in P2(1)2(1)2(1)
REM R1 0.053, Rweak 0.022, Alpha 0.003, Orientation as input
REM Flack x = 0.024 ( 0.021 ) from Parsons' quotients
REM Formula found by SHELXT: C5 N2 O Br2
CELL 0.71073 7.7005 9.2774 12.6853 90.000 90.000 90.000
ZERR 4.000 0.0004 0.0005 0.0006 0.000 0.000 0.000
LATT -1
SYMM 1/2-X, -Y, 1/2+Z
SYMM -X, 1/2+Y, 1/2-Z
SYMM 1/2+X, 1/2-Y, -Z
SFAC C H N O BR
UNIT 20 56 8 4 8
TEMP -130.500
SIZE 0.019 0.07 0.228
DFIX 0.84 0.01 O1 H1O
DFIX 0.88 0.01 N1 H1N N1 H2N N2 H3N N2 H4N
L.S. 10
BOND $H
EQIV $1 -0.5+x, 1.5-y, 1-z
EQIV $2 1-x, -0.5+y, 0.5-z
EQIV $3 0.5-x, 1-y, 0.5+z
HTAB O1 Br2
HTAB N1 Br1
HTAB N1 Br2_$1
HTAB N2 Br1_$2
HTAB N2 Br1_$3
LIST 6
FMAP 2
CONF
ACTA
PLAN 10
WGHT 0.000000
FVAR 0.54944
C1 1 0.584388 0.599471 0.502825 11.00000 0.01015 0.01229 =
0.01445 -0.00206 -0.00174 -0.00342
AFIX 13
H1 2 0.696627 0.629868 0.535658 11.00000 -1.20000
AFIX 0
C2 1 0.590526 0.649313 0.388952 11.00000 0.00861 0.01414 =
0.01704 0.00172 -0.00033 -0.00320
AFIX 23
H2A 2 0.649323 0.744125 0.386013 11.00000 -1.20000
H2B 2 0.661460 0.580258 0.347891 11.00000 -1.20000
AFIX 0
C3 1 0.276054 0.557369 0.366447 11.00000 0.01748 0.01841 =
0.00963 0.00272 0.00124 0.00217
AFIX 23
H3A 2 0.186350 0.558972 0.310554 11.00000 -1.20000
H3B 2 0.220483 0.589232 0.432853 11.00000 -1.20000
AFIX 0
C4 1 0.338979 0.405190 0.380115 11.00000 0.00998 0.01711 =
0.01608 -0.00116 -0.00573 -0.00143
AFIX 23
H4A 2 0.244251 0.337593 0.361676 11.00000 -1.20000
H4B 2 0.436968 0.387393 0.331299 11.00000 -1.20000
AFIX 0
C5 1 0.568779 0.438483 0.520841 11.00000 0.01008 0.01739 =
0.01434 0.00466 -0.00287 -0.00090
AFIX 23
H5A 2 0.660396 0.389036 0.479733 11.00000 -1.20000
H5B 2 0.590151 0.418126 0.596344 11.00000 -1.20000
AFIX 0
N1 3 0.416730 0.662581 0.338056 11.00000 0.01615 0.01279 =
0.01091 0.00202 0.00110 0.00285
H1N 2 0.432901 0.645343 0.270286 11.00000 -1.20000
H2N 2 0.381699 0.753079 0.339546 11.00000 -1.20000
N2 3 0.397009 0.376856 0.490934 11.00000 0.01428 0.01407 =
0.01338 0.00517 -0.00270 0.00597
H3N 2 0.403306 0.282777 0.497870 11.00000 -1.20000
H4N 2 0.321192 0.410245 0.537162 11.00000 -1.20000
O1 4 0.450794 0.677688 0.555782 11.00000 0.01940 0.02108 =
0.01340 -0.00494 -0.00446 0.00733
H1O 2 0.490510 0.660802 0.616112 11.00000 -1.50000
BR1 5 0.486598 0.544477 0.102348 11.00000 0.01361 0.01721 =
0.01335 -0.00176 -0.00083 0.00026
BR2 5 0.611645 0.656659 0.791660 11.00000 0.01656 0.01950 =
0.01201 0.00085 0.00067 -0.00244
HKLF 4
REM sh4074_a.res in P2(1)2(1)2(1)
REM R1 = 0.0372 for 1789 Fo > 4sig(Fo) and 0.0483 for all 2089 data
REM 106 parameters refined using 5 restraints
END
WGHT 0.0000 0.0000
REM Highest difference peak 0.614, deepest hole -0.512, 1-sigma level 0.142
Q1 1 0.3703 0.5379 0.1599 11.00000 0.05 0.61
Q2 1 0.5361 0.6628 0.0804 11.00000 0.05 0.56
Q3 1 0.6045 0.6156 0.7123 11.00000 0.05 0.56
Q4 1 -0.0029 0.6027 0.4801 11.00000 0.05 0.56
Q5 1 0.3707 0.5328 0.0563 11.00000 0.05 0.54
Q6 1 0.4014 0.4371 0.1052 11.00000 0.05 0.52
Q7 1 0.1393 0.3672 0.2424 11.00000 0.05 0.51
Q8 1 0.1672 0.4921 0.2030 11.00000 0.05 0.51
Q9 1 0.2321 0.4067 0.1977 11.00000 0.05 0.49
Q10 1 0.6419 0.6402 0.4428 11.00000 0.05 0.49
;
_shelx_res_checksum 40870
_shelxl_version_number 2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
C C1 0.5844(9) 0.5995(7) 0.5028(5) 0.0123(15) Uani d 1
H H1 0.6966 0.6299 0.5357 0.015 Uiso calc 1
C C2 0.5905(8) 0.6493(8) 0.3890(5) 0.0133(15) Uani d 1
H H2A 0.6493 0.7441 0.3860 0.016 Uiso calc 1
H H2B 0.6615 0.5803 0.3479 0.016 Uiso calc 1
C C3 0.2761(9) 0.5574(9) 0.3664(5) 0.0152(16) Uani d 1
H H3A 0.1864 0.5590 0.3106 0.018 Uiso calc 1
H H3B 0.2205 0.5892 0.4329 0.018 Uiso calc 1
C C4 0.3390(9) 0.4052(8) 0.3801(5) 0.0144(17) Uani d 1
H H4A 0.2443 0.3376 0.3617 0.017 Uiso calc 1
H H4B 0.4370 0.3874 0.3313 0.017 Uiso calc 1
C C5 0.5688(8) 0.4385(8) 0.5208(5) 0.0139(16) Uani d 1
H H5A 0.6604 0.3890 0.4797 0.017 Uiso calc 1
H H5B 0.5902 0.4181 0.5963 0.017 Uiso calc 1
N N1 0.4167(7) 0.6626(8) 0.3381(4) 0.0133(13) Uani d 1
H H1N 0.433(8) 0.645(8) 0.2703(17) 0.016 Uiso d 1
H H2N 0.382(9) 0.753(3) 0.340(5) 0.016 Uiso d 1
N N2 0.3970(9) 0.3769(6) 0.4909(5) 0.0139(14) Uani d 1
H H3N 0.403(10) 0.2828(18) 0.498(6) 0.017 Uiso d 1
H H4N 0.321(7) 0.410(7) 0.537(4) 0.017 Uiso d 1
O O1 0.4508(6) 0.6777(6) 0.5558(3) 0.0180(12) Uani d 1
H H1O 0.491(9) 0.661(9) 0.616(3) 0.027 Uiso d 1
Br Br1 0.48660(9) 0.54448(8) 0.10235(5) 0.01472(18) Uani d 1
Br Br2 0.61165(9) 0.65666(9) 0.79166(5) 0.01602(18) Uani d 1
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
C1 0.010(4) 0.012(4) 0.014(3) -0.003(3) -0.002(3) -0.002(3)
C2 0.009(3) 0.014(4) 0.017(3) -0.003(3) 0.000(3) 0.002(4)
C3 0.017(4) 0.018(4) 0.010(3) 0.002(4) 0.001(3) 0.003(4)
C4 0.010(4) 0.017(4) 0.016(4) -0.001(3) -0.006(3) -0.001(3)
C5 0.010(3) 0.017(4) 0.014(3) -0.001(3) -0.003(3) 0.005(3)
N1 0.016(3) 0.013(3) 0.011(3) 0.003(3) 0.001(2) 0.002(3)
N2 0.014(3) 0.014(4) 0.013(3) 0.006(3) -0.003(2) 0.005(3)
O1 0.019(3) 0.021(3) 0.013(2) 0.007(3) -0.004(2) -0.005(2)
Br1 0.0136(3) 0.0172(4) 0.0134(3) 0.0003(3) -0.0008(3) -0.0018(3)
Br2 0.0166(4) 0.0195(4) 0.0120(3) -0.0024(4) 0.0007(3) 0.0008(4)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O1 C1 C5 111.9(6)
O1 C1 C2 108.4(5)
C5 C1 C2 116.5(6)
O1 C1 H1 106.5
C5 C1 H1 106.5
C2 C1 H1 106.5
N1 C2 C1 114.2(5)
N1 C2 H2A 108.7
C1 C2 H2A 108.7
N1 C2 H2B 108.7
C1 C2 H2B 108.7
H2A C2 H2B 107.6
N1 C3 C4 113.9(6)
N1 C3 H3A 108.8
C4 C3 H3A 108.8
N1 C3 H3B 108.8
C4 C3 H3B 108.8
H3A C3 H3B 107.7
N2 C4 C3 111.7(6)
N2 C4 H4A 109.3
C3 C4 H4A 109.3
N2 C4 H4B 109.3
C3 C4 H4B 109.3
H4A C4 H4B 107.9
N2 C5 C1 114.2(6)
N2 C5 H5A 108.7
C1 C5 H5A 108.7
N2 C5 H5B 108.7
C1 C5 H5B 108.7
H5A C5 H5B 107.6
C2 N1 C3 119.3(6)
C2 N1 H1N 106(4)
C3 N1 H1N 103(5)
C2 N1 H2N 110(5)
C3 N1 H2N 113(5)
H1N N1 H2N 104(7)
C5 N2 C4 115.9(6)
C5 N2 H3N 108(5)
C4 N2 H3N 107(5)
C5 N2 H4N 106(5)
C4 N2 H4N 111(4)
H3N N2 H4N 109(7)
C1 O1 H1O 94(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 O1 1.427(8)
C1 C5 1.516(10)
C1 C2 1.517(9)
C1 H1 1.0000
C2 N1 1.491(8)
C2 H2A 0.9900
C2 H2B 0.9900
C3 N1 1.502(9)
C3 C4 1.503(10)
C3 H3A 0.9900
C3 H3B 0.9900
C4 N2 1.498(8)
C4 H4A 0.9900
C4 H4B 0.9900
C5 N2 1.490(9)
C5 H5A 0.9900
C5 H5B 0.9900
N1 H1N 0.883(13)
N1 H2N 0.882(13)
N2 H3N 0.879(13)
N2 H4N 0.884(13)
O1 H1O 0.839(13)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1O Br2 . 0.839(13) 2.41(2) 3.244(4) 170(8)
N1 H1N Br1 . 0.883(13) 2.36(2) 3.230(6) 167(7)
N1 H2N Br2 4_466 0.882(13) 2.79(6) 3.323(6) 120(5)
N2 H3N Br1 3_645 0.879(13) 2.69(5) 3.422(6) 142(6)
N2 H4N Br1 2_565 0.884(13) 2.55(3) 3.355(6) 153(6)
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
O1 C1 C2 N1 -44.8(8)
C5 C1 C2 N1 82.5(8)
N1 C3 C4 N2 88.3(7)
O1 C1 C5 N2 55.6(8)
C2 C1 C5 N2 -69.9(8)
C1 C2 N1 C3 -35.3(9)
C4 C3 N1 C2 -39.4(8)
C1 C5 N2 C4 55.1(8)
C3 C4 N2 C5 -75.7(7)
_cod_database_fobs_code 2021624