#------------------------------------------------------------------------------
#$Date: 2018-02-23 09:33:53 +0200 (Fri, 23 Feb 2018) $
#$Revision: 206613 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/89/1548987.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_1548987
loop_
_publ_author_name
'Sikine, Meriem'
'Kandri Rodi, Youssef'
'Ouzidan, Younes'
'Jasinski, Jerry P.'
'Kaur, Manpreet'
'Essassi, El Mokhtar'
_publ_section_title
;
7-Bromo-1,4-bis(prop-2-ynyl)pyrido[2,3-b]pyrazine-2,3(1H,4H)-dione
;
_journal_coeditor_code HB4210
_journal_issue 2
_journal_name_full IUCrData
_journal_page_first x180266
_journal_paper_doi 10.1107/S2414314618002663
_journal_volume 3
_journal_year 2018
_chemical_formula_iupac 'C13 H8 Br N3 O2'
_chemical_formula_moiety 'C13 H8 Br N3 O2'
_chemical_formula_sum 'C13 H8 Br N3 O2'
_chemical_formula_weight 318.13
_chemical_name_systematic
7-Bromo-1,4-bis(prop-2-ynyl)pyrido[2,3-b]pyrazine-2,3(1H,4H)-dione
_space_group_crystal_system monoclinic
_space_group_IT_number 14
_space_group_name_Hall '-P 2ybc'
_space_group_name_H-M_alt 'P 1 21/c 1'
_symmetry_space_group_name_Hall '-P 2ybc'
_symmetry_space_group_name_H-M 'P 1 21/c 1'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary dual
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha 90
_cell_angle_beta 92.382(5)
_cell_angle_gamma 90
_cell_formula_units_Z 4
_cell_length_a 10.1922(5)
_cell_length_b 17.3470(10)
_cell_length_c 7.0216(4)
_cell_measurement_reflns_used 1740
_cell_measurement_temperature 293(2)
_cell_measurement_theta_max 71.3600
_cell_measurement_theta_min 4.3380
_cell_volume 1240.37(12)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2015)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al., 2009)
;
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature 293(2)
_diffrn_detector_area_resol_mean 16.0416
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measurement_device 'four-circle diffractometer'
_diffrn_measurement_device_type 'Rigaku Oxford Diffraction model name?'
_diffrn_measurement_method '\w scans'
_diffrn_radiation_monochromator graphite
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0253
_diffrn_reflns_limit_h_max 9
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_k_max 18
_diffrn_reflns_limit_k_min -20
_diffrn_reflns_limit_l_max 7
_diffrn_reflns_limit_l_min -8
_diffrn_reflns_number 4477
_diffrn_reflns_theta_full 67.684
_diffrn_reflns_theta_max 71.272
_diffrn_reflns_theta_min 4.342
_exptl_absorpt_coefficient_mu 4.547
_exptl_absorpt_correction_T_max 1.00000
_exptl_absorpt_correction_T_min 0.42804
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2015)
;
_exptl_crystal_colour red
_exptl_crystal_density_diffrn 1.704
_exptl_crystal_description prism
_exptl_crystal_F_000 632
_exptl_crystal_size_max 0.22
_exptl_crystal_size_mid 0.16
_exptl_crystal_size_min 0.1
_refine_diff_density_max 0.501
_refine_diff_density_min -0.434
_refine_ls_extinction_method none
_refine_ls_goodness_of_fit_ref 1.056
_refine_ls_hydrogen_treatment constr
_refine_ls_matrix_type full
_refine_ls_number_parameters 172
_refine_ls_number_reflns 2361
_refine_ls_number_restraints 0
_refine_ls_restrained_S_all 1.056
_refine_ls_R_factor_all 0.0441
_refine_ls_R_factor_gt 0.0359
_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^)+(0.0557P)^2^+0.1537P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.0935
_refine_ls_wR_factor_ref 0.1009
_reflns_number_gt 1994
_reflns_number_total 2361
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file hb4210sup1.cif
_cod_data_source_block I
_cod_original_cell_volume 1240.38(12)
_cod_database_code 1548987
_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 0.434
_shelx_estimated_absorpt_t_max 0.659
_shelx_hkl_file
;
-1 0 0 435.25 6.62
-2 0 0 31.78 2.54
-3 0 0 436.42 11.11
-4 0 0 1189.12 21.25
-5 0 0 383.84 15.83
-6 0 0 151.60 11.94
-7 0 0 27.98 5.93
-8 0 0 105.82 4.76
-9 0 0 829.48 13.44
-9 0 0 826.67 13.92
-10 0 0 4.25 1.21
-10 0 0 2.71 0.83
-11 0 0 4.56 1.11
-11 0 0 2.87 1.14
-1 1 0 1631.88 11.03
-1 1 0 1648.50 17.33
-2 1 0 746.24 14.51
-2 -1 0 736.67 11.10
-2 -1 0 744.25 9.93
-3 1 0 790.71 17.00
-4 1 0 151.59 8.60
-4 1 0 149.50 8.40
-5 1 0 44.15 5.47
-5 -1 0 43.31 5.44
-5 1 0 50.38 5.40
-6 1 0 331.31 17.28
-6 -1 0 321.60 17.36
-7 1 0 397.16 21.97
-7 -1 0 396.04 22.27
-8 1 0 177.43 6.24
-8 -1 0 178.31 6.12
-9 1 0 43.75 3.15
-9 1 0 43.39 3.27
-9 -1 0 41.00 3.15
-10 -1 0 13.28 1.77
-10 1 0 11.92 1.84
-10 -1 0 13.44 1.95
-10 1 0 14.34 1.84
-11 1 0 65.48 3.60
-11 1 0 68.13 4.00
-11 -1 0 70.56 3.63
-11 -1 0 62.96 3.77
-12 -1 0 12.58 1.63
0 2 0 69.59 2.44
0 2 0 77.14 2.42
-1 2 0 335.17 6.59
-1 2 0 341.00 5.59
-1 2 0 322.76 8.82
-2 -2 0 290.19 6.60
-2 2 0 300.18 10.24
-2 2 0 300.53 6.74
-3 2 0 788.49 18.75
-4 2 0 10.91 2.56
-4 2 0 9.78 2.61
-5 -2 0 477.81 17.91
-5 2 0 493.46 18.00
-5 2 0 455.63 17.63
-6 2 0 19.90 4.47
-6 -2 0 22.94 4.80
-7 2 0 1.84 2.08
-8 2 0 140.78 5.65
-8 -2 0 145.53 5.52
-8 2 0 154.10 5.51
-9 -2 0 -0.01 0.81
-9 2 0 -1.09 1.12
-9 2 0 0.40 0.57
-10 -2 0 -0.49 0.81
-10 -2 0 0.61 0.82
-10 2 0 -0.22 0.73
-11 -2 0 0.13 1.02
-11 2 0 1.75 0.74
-11 2 0 2.07 1.28
-12 -2 0 6.70 1.22
-12 2 0 2.69 0.69
0 3 0 3.51 0.70
0 3 0 2.72 0.74
-1 3 0 32.23 2.26
-1 3 0 32.76 3.23
-1 3 0 35.27 2.75
-1 3 0 32.34 2.52
-2 3 0 381.92 10.56
-2 -3 0 366.91 6.88
-2 3 0 377.53 8.83
-3 3 0 231.25 10.83
-3 3 0 244.77 7.68
-3 -3 0 228.15 7.96
-3 3 0 248.85 10.08
-4 3 0 414.77 15.02
-4 3 0 442.25 16.40
-5 3 0 611.01 21.15
-5 3 0 611.84 20.82
-6 3 0 59.50 7.55
-7 3 0 -0.49 1.79
-8 3 0 -0.38 0.66
-8 3 0 0.51 0.64
-8 -3 0 -0.90 1.00
-9 3 0 9.87 1.69
-9 3 0 10.87 1.65
-9 -3 0 8.85 1.55
-10 -3 0 6.27 1.44
-10 -3 0 6.98 1.25
-10 3 0 5.46 1.43
-10 3 0 7.93 1.50
-11 -3 0 -0.08 0.79
-11 3 0 -0.34 0.80
-12 -3 0 1.20 0.73
-12 3 0 -0.24 0.56
0 4 0 157.48 5.28
0 4 0 167.47 3.78
-1 4 0 199.27 6.64
-1 4 0 195.50 6.54
-1 4 0 215.97 8.12
-2 4 0 35.72 3.17
-2 4 0 31.23 3.99
-2 4 0 35.21 3.48
-2 -4 0 28.72 1.81
-3 4 0 102.10 7.46
-3 -4 0 103.18 5.10
-3 4 0 97.14 6.69
-3 4 0 96.78 5.31
-4 4 0 408.36 16.22
-4 4 0 389.20 15.09
-5 4 0 326.97 15.86
-5 4 0 320.60 15.58
-6 4 0 -0.23 1.76
-6 4 0 -0.18 1.08
-7 4 0 77.42 9.64
-8 4 0 -0.50 0.80
-8 4 0 -0.01 0.57
-8 -4 0 0.41 0.56
-9 4 0 38.21 3.20
-9 4 0 43.20 3.20
-9 -4 0 37.70 3.06
-10 -4 0 1.14 0.85
-10 4 0 1.00 1.13
-10 4 0 1.54 0.84
-11 4 0 12.87 1.70
-11 -4 0 11.51 1.69
-12 -4 0 3.41 0.94
0 5 0 0.15 0.42
0 5 0 9.90 1.63
-1 5 0 48.27 4.19
-1 5 0 46.68 3.61
1 5 0 45.88 2.27
-1 5 0 43.58 3.32
-2 5 0 806.42 18.85
-2 5 0 768.65 16.72
-2 5 0 774.96 16.29
-3 5 0 1565.71 23.51
-3 5 0 1554.41 27.65
-3 5 0 1614.81 29.66
-4 5 0 0.90 1.35
-4 5 0 4.83 2.27
-4 5 0 1.37 1.15
-5 5 0 89.16 8.59
-5 5 0 83.73 8.17
-6 5 0 335.38 18.06
-6 5 0 353.18 18.77
-7 5 0 255.90 17.74
-8 5 0 4.32 1.27
-8 5 0 3.63 1.00
-8 -5 0 3.69 1.16
-9 5 0 3.80 1.30
-9 5 0 1.75 0.74
-9 -5 0 2.15 0.84
-10 5 0 47.54 3.37
-10 -5 0 48.08 3.44
-11 5 0 32.28 2.53
-11 -5 0 33.04 2.68
0 6 0 5366.00 37.66
0 6 0 5338.15 23.08
1 6 0 1456.79 15.02
-1 6 0 1445.84 19.60
-1 6 0 1454.64 23.33
-1 6 0 1433.65 21.75
-2 6 0 26.59 3.59
-2 6 0 25.97 3.35
-2 6 0 24.49 3.66
-3 6 0 160.35 8.45
-3 6 0 158.51 9.49
-3 6 0 155.66 9.20
-4 6 0 1196.49 28.45
-4 6 0 1214.50 28.74
-5 6 0 258.79 14.79
-5 6 0 262.75 14.60
-6 6 0 57.55 7.72
-6 6 0 61.43 8.01
-7 6 0 1.33 0.79
-7 6 0 0.64 0.72
-7 -6 0 1.31 0.66
-8 -6 0 167.25 6.42
-8 6 0 156.38 6.05
-8 6 0 162.11 6.53
-9 6 0 291.42 8.69
-9 6 0 274.26 8.21
-9 -6 0 276.17 8.35
-10 6 0 23.22 2.41
-10 -6 0 20.80 2.37
-11 -6 0 -0.77 0.69
-11 6 0 -0.74 0.76
0 7 0 15.15 2.11
-1 7 0 366.94 12.08
-1 7 0 378.78 10.49
-1 7 0 363.08 11.76
-2 7 0 970.77 21.76
-2 7 0 988.95 22.74
-2 7 0 997.46 20.61
-3 7 0 724.35 20.60
-3 7 0 766.11 19.96
-3 7 0 736.07 20.54
-4 7 0 66.52 6.10
-4 7 0 53.60 6.32
-4 7 0 56.96 6.31
-5 7 0 52.66 6.95
-5 7 0 56.78 6.98
-6 7 0 187.98 14.15
-6 7 0 197.85 14.01
-7 7 0 281.81 8.01
-7 7 0 281.99 8.39
-7 -7 0 272.12 8.03
-8 7 0 87.35 4.61
-8 -7 0 87.63 4.77
-9 7 0 10.17 1.75
-9 -7 0 10.37 1.71
-10 -7 0 36.30 2.93
-10 7 0 35.81 2.87
-11 7 0 44.93 2.79
-11 -7 0 45.70 2.88
0 8 0 250.91 8.83
-1 8 0 339.25 12.15
-1 8 0 321.85 11.55
-2 8 0 45.88 4.52
-2 8 0 40.45 4.27
-2 8 0 35.43 4.33
-2 8 0 35.52 4.64
-3 8 0 112.95 8.32
-3 8 0 103.40 7.98
-3 8 0 111.12 8.16
-4 8 0 175.37 10.56
-4 8 0 188.17 12.08
-4 8 0 168.82 11.14
-5 8 0 52.25 7.11
-5 8 0 59.78 7.31
-6 8 0 54.36 3.48
-6 8 0 58.20 8.11
-7 -8 0 2.44 1.01
-7 8 0 1.84 0.70
-8 -8 0 7.29 1.50
-8 8 0 4.47 1.27
-9 -8 0 28.30 2.68
-9 8 0 24.81 2.55
-10 -8 0 12.28 1.71
-10 8 0 8.57 1.45
-11 8 0 2.83 0.78
-11 -8 0 1.84 0.67
0 9 0 0.66 1.35
-1 9 0 85.11 6.10
-1 9 0 100.87 7.03
-2 9 0 35.00 4.90
-2 9 0 36.63 4.30
-2 9 0 31.52 3.95
-2 9 0 34.14 4.39
-3 9 0 1.19 1.20
-3 9 0 4.31 1.85
-3 9 0 1.48 0.94
-4 9 0 20.03 4.09
-4 9 0 15.71 3.39
-4 9 0 17.75 3.72
-5 9 0 7.64 3.16
-5 9 0 3.85 1.79
-5 9 0 4.28 2.04
-6 -9 0 4.35 1.22
-6 9 0 2.82 0.81
-6 -9 0 3.09 0.94
-6 -9 0 4.06 1.05
-7 -9 0 3.62 1.07
-7 9 0 -1.09 1.12
-8 -9 0 1.21 0.66
-8 9 0 -0.21 0.92
-9 9 0 0.60 0.86
-9 -9 0 1.57 0.73
-10 9 0 -0.11 0.71
-10 -9 0 0.30 0.58
-11 9 0 0.71 0.51
0 10 0 534.78 17.51
-1 10 0 0.83 1.25
-1 10 0 1.09 1.22
-2 10 0 18.91 3.79
-2 10 0 12.91 2.69
-2 10 0 17.17 3.04
-3 10 0 72.73 6.99
-3 10 0 84.34 7.42
-3 10 0 84.30 7.80
-4 10 0 25.23 4.46
-4 10 0 25.50 4.75
-4 10 0 29.05 4.76
-5 10 0 262.89 14.95
-5 10 0 254.60 15.09
-5 10 0 242.41 7.55
-5 -10 0 256.01 7.50
-5 10 0 235.18 15.00
-6 -10 0 0.11 0.78
-6 -10 0 0.57 1.01
-7 10 0 42.31 3.39
-8 -10 0 1.63 0.88
-8 10 0 2.30 1.04
-9 -10 0 53.75 3.55
-9 10 0 59.43 3.69
-10 10 0 0.67 0.67
0 11 0 3.02 1.57
-1 11 0 142.93 10.28
-1 11 0 140.42 9.15
-2 11 0 427.66 17.69
-3 11 0 233.18 13.41
-4 11 0 9.98 2.94
-4 11 0 9.09 2.77
-5 -11 0 37.18 2.92
-5 11 0 37.88 3.14
-5 -11 0 40.28 3.05
-6 -11 0 373.54 9.52
-6 11 0 354.10 9.65
-6 -11 0 375.66 9.20
-7 11 0 14.64 2.10
-8 11 0 14.56 2.05
-9 -11 0 41.40 3.02
-9 11 0 42.42 2.98
-10 11 0 10.91 1.34
0 12 0 798.83 23.53
-1 12 0 278.62 15.13
1 12 0 298.29 15.03
-2 12 0 0.04 1.03
-3 12 0 199.17 12.78
-4 -12 0 201.39 6.64
-4 12 0 200.36 6.78
-4 -12 0 210.90 6.43
-5 12 0 234.17 7.61
-5 -12 0 250.19 7.37
-5 -12 0 231.95 7.44
-6 12 0 51.31 3.76
-6 -12 0 48.84 3.45
-6 -12 0 51.33 3.59
-7 12 0 8.60 1.74
-8 12 0 124.63 5.36
-9 -12 0 61.52 3.49
-9 12 0 67.06 3.51
-10 12 0 13.24 1.32
0 13 0 3.55 1.99
1 13 0 143.05 10.77
-2 -13 0 362.12 8.54
-2 13 0 371.99 8.60
-3 13 0 455.05 9.86
-3 -13 0 472.20 9.94
-3 -13 0 456.48 8.97
-4 -13 0 62.54 3.54
-4 -13 0 61.00 3.76
-4 13 0 61.47 3.77
-5 -13 0 79.72 4.11
-5 -13 0 85.29 4.57
-5 13 0 79.72 4.44
-6 13 0 284.09 8.42
-7 13 0 118.28 5.30
-8 13 0 41.66 2.96
-9 -13 0 0.39 0.52
-9 13 0 2.05 0.82
0 14 0 143.91 5.42
-1 14 0 137.70 5.34
-1 -14 0 125.36 5.08
-2 14 0 8.56 1.39
-2 -14 0 4.89 1.13
-3 14 0 174.50 6.18
-3 -14 0 179.65 6.20
-4 14 0 13.72 1.91
-4 -14 0 11.73 1.61
-4 -14 0 12.67 1.82
-5 14 0 78.83 4.35
-5 -14 0 77.27 3.90
-5 -14 0 78.07 4.26
-6 14 0 56.31 3.70
-7 14 0 -0.20 0.84
-8 14 0 7.50 1.28
-9 14 0 31.34 1.98
-9 -14 0 26.72 1.83
0 15 0 -0.32 0.59
-1 15 0 4.73 1.15
-1 -15 0 6.83 1.41
-2 15 0 0.17 0.60
-2 -15 0 -0.63 0.74
-3 15 0 22.15 2.28
-3 -15 0 18.95 2.06
-4 15 0 73.25 4.11
-4 -15 0 68.65 3.52
-4 -15 0 69.47 3.87
-5 15 0 0.73 1.00
-5 -15 0 -0.47 0.68
-6 15 0 1.08 0.89
-7 15 0 1.73 0.90
-8 -15 0 8.03 1.24
-8 15 0 11.34 1.40
0 -16 0 0.15 0.72
-1 -16 0 161.54 5.61
-1 16 0 165.59 5.87
-2 16 0 1.72 0.90
-2 -16 0 1.51 0.87
-3 16 0 15.22 1.86
-3 -16 0 15.44 1.87
-4 -16 0 42.59 2.90
-4 16 0 41.44 3.03
-5 16 0 29.06 2.59
-6 16 0 0.54 0.72
-7 16 0 5.26 1.09
-8 16 0 28.02 1.77
-8 -16 0 22.83 1.64
0 -17 0 -0.34 0.81
-1 -17 0 16.91 1.87
1 -17 0 19.88 2.10
-2 -17 0 134.46 4.95
-2 17 0 141.52 5.29
-3 -17 0 75.98 3.71
-3 17 0 83.25 4.10
-4 17 0 2.61 0.95
-5 17 0 50.08 3.06
-6 17 0 50.01 2.83
-7 17 0 39.05 2.17
0 -18 0 171.58 5.32
1 -18 0 10.56 1.49
-1 -18 0 9.19 1.34
-2 -18 0 6.21 1.10
2 -18 0 4.95 1.16
-3 18 0 18.79 1.88
-3 -18 0 19.18 1.76
-4 18 0 141.06 4.82
-5 18 0 54.82 2.87
-6 18 0 18.06 1.52
0 -19 0 -1.11 0.75
-1 -19 0 27.01 1.94
1 -19 0 26.04 1.97
2 -19 0 103.73 3.77
-2 -19 0 100.25 3.61
3 -19 0 55.05 2.75
4 -19 0 8.27 1.17
5 -19 0 2.19 0.69
0 -20 0 24.64 1.65
1 -20 0 47.03 2.28
-1 -20 0 51.41 2.32
2 -20 0 0.52 0.52
3 -20 0 11.65 1.12
-12 0 1 -0.23 0.58
-11 0 1 0.63 0.62
-11 0 1 1.85 1.02
-10 0 1 0.12 1.04
-10 0 1 -0.15 0.72
-9 0 1 -0.04 0.80
-8 0 1 0.65 0.74
-7 0 1 -3.24 2.36
-6 0 1 1.15 0.97
-5 0 1 0.29 1.22
-5 0 1 0.65 1.08
-4 0 1 2.39 1.30
-4 0 1 2.79 1.59
-3 0 1 0.67 0.71
-3 0 1 0.66 1.31
-2 0 1 0.25 0.95
-1 0 1 1.26 0.83
0 0 1 6.06 1.12
0 0 -1 4.31 0.61
1 0 1 0.44 0.69
-3 0 -1 1.14 1.34
-4 0 -1 1.26 1.67
-5 0 -1 1.70 2.39
-6 0 -1 1.52 2.12
-7 0 -1 6.22 3.27
-8 0 -1 -0.60 0.70
-8 0 -1 -0.31 0.76
-9 0 -1 1.18 0.89
-10 0 -1 0.63 1.02
-11 0 -1 0.30 0.96
-12 0 -1 1.63 0.87
-12 1 1 18.64 1.66
-12 -1 1 15.63 1.51
-11 1 1 7.62 1.88
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1 0 -7 0.00 1.10
0 0 -7 0.90 1.20
-1 0 -7 -1.14 1.21
-2 0 -7 0.05 1.28
-2 0 -7 -0.97 0.77
-3 0 -7 -1.99 1.55
-3 0 -7 0.94 0.91
-4 0 -7 0.54 0.95
-5 0 -7 -0.88 0.86
-6 0 -7 -0.51 0.70
-7 -1 7 1.88 0.70
7 -1 -7 3.72 0.73
7 1 -7 3.10 0.77
-6 1 7 3.63 1.00
-6 -1 7 2.10 0.87
6 -1 -7 2.30 0.84
6 1 -7 3.02 0.98
5 -1 -7 29.01 2.47
5 1 -7 23.22 2.40
-5 1 7 30.41 2.60
-5 -1 7 26.81 2.41
4 -1 -7 2.44 1.13
4 1 -7 2.05 1.23
3 -1 -7 4.53 1.41
3 1 -7 2.46 1.19
2 -1 -7 0.31 1.14
2 1 -7 1.61 1.42
1 -1 -7 23.57 2.72
1 1 -7 22.03 2.69
0 -1 -7 32.10 3.20
0 1 -7 33.20 3.22
-1 -1 -7 0.21 1.14
-1 1 -7 -1.99 1.45
-2 -1 -7 6.06 1.87
-2 1 -7 4.80 1.62
-2 -1 -7 5.46 1.30
-3 -1 -7 3.10 1.07
-3 -1 -7 4.57 1.84
-3 1 -7 3.25 1.39
-3 1 -7 2.37 1.09
-4 -1 -7 70.98 3.75
-4 1 -7 76.03 4.15
-5 -1 -7 -1.50 0.87
-5 1 -7 0.20 0.83
-6 -1 -7 4.84 1.02
-6 1 -7 4.74 1.06
-7 -2 7 2.63 0.73
7 2 -7 1.99 0.68
6 -2 -7 24.39 1.87
6 2 -7 21.17 2.10
-6 -2 7 25.29 2.22
-5 -2 7 0.93 0.63
5 -2 -7 1.14 0.87
5 2 -7 1.09 1.08
4 -2 -7 11.16 1.74
4 2 -7 11.24 1.98
3 -2 -7 29.13 2.71
3 2 -7 32.20 3.05
2 -2 -7 38.68 3.25
2 2 -7 40.98 3.41
1 -2 -7 13.01 2.09
1 2 -7 10.42 1.97
0 -2 -7 8.28 1.83
0 2 -7 7.76 1.71
-1 -2 -7 14.85 2.39
-1 2 -7 12.45 2.02
-2 -2 -7 36.00 3.78
-2 2 -7 39.80 3.48
-3 2 -7 40.17 3.22
-3 -2 -7 40.72 2.79
-4 -2 -7 0.51 0.78
-4 2 -7 0.10 0.92
-5 -2 -7 8.05 1.23
-5 2 -7 9.63 1.61
-6 -2 -7 19.82 1.72
-6 2 -7 25.37 2.14
-7 -3 7 2.43 0.69
7 3 -7 2.60 0.79
-6 -3 7 7.45 1.24
6 -3 -7 8.47 1.12
6 3 -7 8.44 1.48
5 -3 -7 77.83 3.52
5 3 -7 82.71 4.41
-5 -3 7 86.16 4.05
4 -3 -7 8.59 1.46
4 3 -7 12.82 1.99
3 -3 -7 9.85 1.71
3 3 -7 11.62 2.10
2 -3 -7 5.16 1.42
2 3 -7 3.82 1.32
1 -3 -7 92.07 4.99
1 3 -7 96.94 5.02
0 -3 -7 29.90 3.05
0 3 -7 32.71 2.99
-1 -3 -7 23.12 2.92
-1 3 -7 23.81 2.61
-2 -3 -7 1.86 1.64
-3 -3 -7 2.88 1.80
-3 3 -7 1.83 1.09
-4 3 -7 49.08 3.46
-5 -3 -7 10.93 1.36
-5 3 -7 10.53 1.60
-6 -3 -7 1.68 0.74
-6 3 -7 1.04 0.77
7 4 -7 4.51 0.87
-6 -4 7 9.42 1.26
6 4 -7 9.97 1.50
5 -4 -7 26.01 2.00
5 4 -7 27.80 2.64
4 -4 -7 16.91 1.87
4 4 -7 17.61 2.23
3 -4 -7 27.61 2.52
3 4 -7 29.99 2.83
2 -4 -7 31.96 2.76
2 4 -7 38.26 3.04
1 -4 -7 2.23 1.35
1 4 -7 0.63 0.94
0 -4 -7 0.60 1.28
0 4 -7 1.88 0.94
-1 -4 -7 11.71 2.22
-1 4 -7 14.16 1.92
-2 -4 -7 33.04 3.60
-3 4 -7 18.27 2.26
-3 -4 -7 15.17 2.62
-4 4 -7 6.17 1.48
-5 4 -7 7.37 1.37
-6 4 -7 34.14 2.30
7 5 -7 -0.28 0.56
6 5 -7 6.19 1.17
5 5 -7 7.02 1.34
4 -5 -7 10.44 1.44
4 5 -7 13.91 1.88
3 -5 -7 2.38 1.05
3 5 -7 4.19 1.26
2 -5 -7 2.24 1.02
2 5 -7 4.53 1.12
1 -5 -7 6.65 1.46
1 5 -7 10.06 1.53
0 5 -7 21.69 2.18
0 -5 -7 15.71 2.28
-1 -5 -7 3.17 1.37
-2 -5 -7 1.81 1.43
-3 -5 -7 15.80 1.66
-3 5 -7 14.84 2.06
-4 5 -7 12.96 1.76
-5 5 -7 5.09 1.20
-6 5 -7 1.80 0.67
6 6 -7 -0.23 0.66
5 6 -7 11.14 1.52
4 -6 -7 0.79 0.68
4 6 -7 -0.37 0.78
3 -6 -7 1.40 0.73
3 6 -7 0.36 0.82
2 -6 -7 2.49 0.87
2 6 -7 3.15 0.96
1 -6 -7 4.28 1.32
1 6 -7 6.07 1.19
0 -6 -7 -0.81 1.13
-1 -6 -7 1.42 0.81
-1 -6 -7 1.01 1.35
-2 -6 -7 0.58 0.75
-2 -6 -7 2.22 1.51
-3 -6 -7 0.34 0.65
-3 6 -7 2.43 1.07
-4 6 -7 3.69 1.03
-5 6 -7 0.98 0.63
6 7 -7 -0.22 0.50
5 7 -7 7.94 1.15
4 7 -7 7.23 1.21
3 -7 -7 2.74 1.03
3 7 -7 2.79 0.86
2 -7 -7 0.37 0.80
2 7 -7 0.92 0.63
1 -7 -7 1.35 0.79
1 -7 -7 1.66 1.13
0 -7 -7 52.97 3.15
0 -7 -7 57.95 3.87
-1 -7 -7 0.36 0.75
-1 -7 -7 -1.04 1.11
-2 -7 -7 4.63 1.21
-3 -7 -7 -3.38 0.99
-3 7 -7 0.14 0.72
-4 7 -7 42.41 2.71
-5 7 -7 2.30 0.81
5 -8 -7 0.54 0.52
5 8 -7 0.17 0.44
4 8 -7 1.73 0.68
3 8 -7 36.70 2.18
2 -8 -7 27.78 2.29
2 -8 -7 28.78 2.45
1 -8 -7 11.29 1.63
1 -8 -7 13.78 1.95
0 -8 -7 1.32 0.82
0 -8 -7 1.21 0.94
-1 -8 -7 40.37 2.89
-2 -8 -7 11.49 1.63
-3 8 -7 27.96 2.20
-3 -8 -7 25.76 2.17
-4 8 -7 1.24 0.72
4 -9 -7 9.76 1.26
3 -9 -7 12.00 1.49
2 -9 -7 -0.09 0.71
1 -9 -7 68.28 3.63
1 -9 -7 70.88 3.74
0 -9 -7 19.31 2.02
-1 -9 -7 4.44 1.13
-2 -9 -7 0.19 0.68
-3 -9 -7 3.48 1.04
-3 9 -7 4.38 0.93
-4 9 -7 40.09 2.17
3 -10 -7 13.37 1.44
2 -10 -7 47.21 2.76
1 -10 -7 9.82 1.47
0 -10 -7 -1.19 0.92
-1 -10 -7 7.03 1.26
-2 -10 -7 4.74 1.07
-3 10 -7 14.63 1.34
-3 -10 -7 15.05 1.57
3 -11 -7 4.92 0.82
2 -11 -7 21.17 1.76
1 -11 -7 2.04 0.79
0 -11 -7 14.98 1.60
-1 -11 -7 -0.83 0.73
-2 -11 -7 -0.65 0.72
-2 11 -7 0.58 0.49
1 -12 -7 0.23 0.51
0 -12 -7 0.48 0.53
-1 -12 -7 -0.15 0.50
5 0 -8 3.13 0.78
4 0 -8 13.98 1.63
3 0 -8 5.00 1.38
2 0 -8 2.61 1.34
1 0 -8 -1.90 1.20
0 0 -8 0.87 1.11
-1 0 -8 45.56 3.58
-2 0 -8 35.61 3.09
-3 0 -8 7.72 1.08
5 1 -8 1.97 0.73
4 -1 -8 5.50 1.14
4 1 -8 5.42 1.17
3 -1 -8 8.67 1.56
3 1 -8 7.52 1.57
2 -1 -8 12.27 1.93
2 1 -8 10.57 1.77
1 -1 -8 3.91 1.40
1 1 -8 5.94 1.54
0 -1 -8 17.43 2.40
0 1 -8 18.28 2.20
-1 -1 -8 0.08 1.16
-1 1 -8 -1.34 1.00
-1 1 -8 2.02 0.86
-2 1 -8 8.65 1.32
-2 -1 -8 8.74 1.87
-2 1 -8 8.15 1.51
-3 1 -8 52.10 2.76
5 2 -8 24.69 1.86
4 -2 -8 0.25 0.60
4 2 -8 0.94 0.88
3 -2 -8 6.34 1.35
3 2 -8 6.22 1.41
2 -2 -8 2.32 1.12
2 2 -8 -0.10 1.00
1 -2 -8 5.71 1.62
1 2 -8 7.42 1.50
0 2 -8 25.31 2.07
0 -2 -8 30.89 3.04
0 2 -8 28.05 2.54
-1 -2 -8 5.01 1.63
-1 2 -8 6.27 1.34
-1 2 -8 5.34 1.08
-2 2 -8 24.29 2.09
-2 -2 -8 30.39 3.09
-3 2 -8 3.83 0.98
4 -3 -8 9.36 1.22
4 3 -8 12.95 1.53
3 -3 -8 0.55 0.74
3 3 -8 2.18 1.00
2 -3 -8 0.51 0.85
2 3 -8 1.00 0.74
1 -3 -8 -0.57 1.11
1 3 -8 0.22 0.83
0 -3 -8 1.46 1.19
0 3 -8 0.09 0.75
-1 3 -8 -0.53 0.66
-1 3 -8 -0.48 0.78
-2 3 -8 0.15 0.67
-3 3 -8 1.68 0.71
4 4 -8 0.34 0.56
3 -4 -8 8.93 1.31
3 4 -8 11.39 1.43
2 -4 -8 11.84 1.61
2 4 -8 9.94 1.36
1 -4 -8 4.16 1.37
1 4 -8 3.71 0.94
0 -4 -8 2.54 1.21
0 4 -8 5.61 1.10
-1 4 -8 16.60 1.70
-1 -4 -8 16.65 2.37
-2 4 -8 1.90 0.82
-3 4 -8 0.42 0.57
3 -5 -8 0.69 0.65
3 5 -8 0.75 0.58
2 5 -8 16.40 1.50
2 -5 -8 14.06 1.63
1 -5 -8 28.66 2.46
1 5 -8 28.31 1.93
0 -5 -8 1.25 1.09
-1 -5 -8 0.96 1.04
-1 5 -8 1.41 0.81
-2 5 -8 19.19 1.75
-3 5 -8 13.47 1.36
2 -6 -8 9.26 1.28
1 -6 -8 -0.52 0.78
0 -6 -8 16.18 1.96
-1 6 -8 9.43 1.24
-2 6 -8 10.23 1.21
-1 7 -8 0.35 0.47
0 0 0 0.00 0.00
TITL Ozidan-SM-4 in P2(1)/c
REM P2(1)/c (#14 in standard setting)
CELL 1.54184 10.192203 17.347021 7.021556 90.0000 92.3825 90.0000
ZERR 4.00 0.000490 0.000983 0.000427 0.0000 0.0047 0.0000
LATT 1
SYMM -x, y+1/2,-z+1/2
SFAC C H N S Br
UNIT 52.00 32.00 12.00 8.00 4.00
TREF
HKLF 4
END
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)'
;
_shelx_hkl_checksum 65774
_shelx_res_file
;
TITL ozidan-sm-4_a.res in P2(1)/c
REM Old TITL Ozidan-SM-4 in P21/c #14
REM SHELXT solution in P2(1)/c
REM R1 0.134, Rweak 0.008, Alpha 0.042, Orientation as input
REM Formula found by SHELXT: C11 N7 Br
CELL 1.54184 10.1922 17.347 7.0216 90 92.382 90
ZERR 4 0.0005 0.001 0.0004 0 0.005 0
LATT 1
SYMM -X,0.5+Y,0.5-Z
SFAC C H Br N O
UNIT 52 32 4 12 8
EQIV $1 1-X,-0.5+Y,0.5-Z
L.S. 50
PLAN 15
SIZE 0.22 0.16 0.1
TEMP 20(2)
HTAB C6 O2_$1
BOND $H
list 4
fmap 2
acta
OMIT 4 2 0
OMIT -1 7 1
OMIT 2 6 1
OMIT 0 8 1
REM
REM
REM
WGHT 0.055700 0.153700
FVAR 0.39698
BR1 3 0.114013 0.166644 0.361634 11.00000 0.05471 0.03934 =
0.06449 0.00276 0.00117 -0.01276
O1 5 0.639700 0.497481 0.153061 11.00000 0.04801 0.05208 =
0.06807 0.00305 0.00802 -0.01377
O2 5 0.426682 0.560844 0.309697 11.00000 0.06392 0.03216 =
0.09093 -0.00502 0.01523 -0.00606
N1 4 0.555100 0.377407 0.187517 11.00000 0.03492 0.04035 =
0.04382 -0.00073 0.00386 0.00027
N2 4 0.329298 0.443524 0.328446 11.00000 0.03863 0.02930 =
0.04097 -0.00276 0.00293 0.00247
N3 4 0.471835 0.254641 0.233803 11.00000 0.04093 0.03613 =
0.04325 -0.00358 -0.00148 0.00660
C1 1 0.550755 0.455772 0.200237 11.00000 0.04027 0.04327 =
0.04113 0.00121 -0.00136 -0.00395
C2 1 0.429175 0.491691 0.283096 11.00000 0.04223 0.03435 =
0.04911 -0.00143 0.00063 -0.00396
C3 1 0.336640 0.363621 0.306282 11.00000 0.03626 0.03055 =
0.03059 0.00155 -0.00136 0.00120
C4 1 0.233919 0.314843 0.343316 11.00000 0.03706 0.03593 =
0.03800 -0.00041 0.00204 0.00235
AFIX 43
H4 2 0.153686 0.334151 0.380038 11.00000 -1.20000
AFIX 0
C5 1 0.253681 0.236361 0.324259 11.00000 0.04487 0.03096 =
0.03567 0.00142 -0.00285 -0.00362
C6 1 0.374008 0.207552 0.275398 11.00000 0.04948 0.02903 =
0.04431 -0.00225 -0.00517 0.00325
AFIX 43
H6 2 0.386865 0.154508 0.271503 11.00000 -1.20000
AFIX 0
C7 1 0.452785 0.329834 0.244891 11.00000 0.03557 0.03401 =
0.03413 -0.00204 -0.00204 0.00134
C8 1 0.216127 0.477954 0.421916 11.00000 0.04734 0.03387 =
0.04595 -0.00769 0.00713 0.00521
AFIX 23
H8A 2 0.201002 0.449494 0.537877 11.00000 -1.20000
H8B 2 0.237900 0.530558 0.457830 11.00000 -1.20000
AFIX 0
C9 1 0.095250 0.478452 0.303592 11.00000 0.04501 0.03757 =
0.04910 0.00094 0.01065 0.00849
C10 1 -0.006602 0.478208 0.218419 11.00000 0.04980 0.05388 =
0.05715 -0.00320 0.00452 0.00956
AFIX 163
H10 2 -0.087127 0.478016 0.151081 11.00000 -1.20000
AFIX 0
C11 1 0.674848 0.341537 0.117659 11.00000 0.04102 0.05280 =
0.05904 -0.00326 0.01149 0.00340
AFIX 23
H11A 2 0.652146 0.294353 0.049868 11.00000 -1.20000
H11B 2 0.715955 0.376229 0.029673 11.00000 -1.20000
AFIX 0
C12 1 0.767307 0.324177 0.278524 11.00000 0.03480 0.04519 =
0.07787 0.00228 0.01088 -0.00017
C13 1 0.838946 0.311385 0.409547 11.00000 0.04647 0.07363 =
0.09390 0.01192 -0.00414 0.00250
AFIX 163
H13 2 0.895806 0.301231 0.513542 11.00000 -1.20000
AFIX 0
HKLF 4
REM ozidan-sm-4_a.res in P2(1)/c
REM R1 = 0.0359 for 1994 Fo > 4sig(Fo) and 0.0441 for all 2361 data
REM 172 parameters refined using 0 restraints
END
WGHT 0.0557 0.1537
REM Highest difference peak 0.501, deepest hole -0.434, 1-sigma level 0.071
Q1 1 0.0748 0.1695 0.2452 11.00000 0.05 0.50
Q2 1 0.0827 0.1967 0.4340 11.00000 0.05 0.46
Q3 1 0.3123 0.1258 0.3330 11.00000 0.05 0.46
Q4 1 0.1245 0.1764 0.4946 11.00000 0.05 0.38
Q5 1 0.1690 0.1656 0.4802 11.00000 0.05 0.37
Q6 1 0.8334 0.3375 0.3241 11.00000 0.05 0.27
Q7 1 0.5551 0.3962 0.2354 11.00000 0.05 0.25
Q8 1 0.3226 0.4226 0.2871 11.00000 0.05 0.25
Q9 1 0.5187 0.3604 0.2119 11.00000 0.05 0.25
Q10 1 0.8249 0.3093 0.2866 11.00000 0.05 0.24
Q11 1 0.0623 0.5127 0.2187 11.00000 0.05 0.23
Q12 1 0.3353 0.4090 0.3438 11.00000 0.05 0.23
Q13 1 0.4466 0.5367 0.3327 11.00000 0.05 0.21
Q14 1 0.3267 0.2269 0.3063 11.00000 0.05 0.21
Q15 1 0.2768 0.3388 0.2976 11.00000 0.05 0.21
;
_shelx_res_checksum 32243
_shelxl_version_number 2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Br Br1 0.11401(3) 0.16664(2) 0.36163(5) 0.05288(15) Uani d 1
O O1 0.6397(2) 0.49748(14) 0.1531(4) 0.0559(6) Uani d 1
O O2 0.4267(3) 0.56084(13) 0.3097(4) 0.0620(7) Uani d 1
N N1 0.5551(2) 0.37741(14) 0.1875(3) 0.0396(5) Uani d 1
N N2 0.3293(2) 0.44352(13) 0.3284(3) 0.0363(5) Uani d 1
N N3 0.4718(2) 0.25464(14) 0.2338(3) 0.0402(5) Uani d 1
C C1 0.5508(3) 0.45577(17) 0.2002(4) 0.0416(6) Uani d 1
C C2 0.4292(3) 0.49169(17) 0.2831(4) 0.0419(6) Uani d 1
C C3 0.3366(2) 0.36362(15) 0.3063(4) 0.0325(5) Uani d 1
C C4 0.2339(3) 0.31484(16) 0.3433(4) 0.0370(5) Uani d 1
H H4 0.1537 0.3342 0.3800 0.044 Uiso calc 1
C C5 0.2537(3) 0.23636(15) 0.3243(4) 0.0373(5) Uani d 1
C C6 0.3740(3) 0.20755(16) 0.2754(4) 0.0411(6) Uani d 1
H H6 0.3869 0.1545 0.2715 0.049 Uiso calc 1
C C7 0.4528(3) 0.32983(15) 0.2449(4) 0.0347(5) Uani d 1
C C8 0.2161(3) 0.47795(16) 0.4219(4) 0.0422(6) Uani d 1
H H8A 0.2010 0.4495 0.5379 0.051 Uiso calc 1
H H8B 0.2379 0.5306 0.4578 0.051 Uiso calc 1
C C9 0.0952(3) 0.47845(17) 0.3036(5) 0.0436(6) Uani d 1
C C10 -0.0066(3) 0.4782(2) 0.2184(5) 0.0535(8) Uani d 1
H H10 -0.0871 0.4780 0.1511 0.064 Uiso calc 1
C C11 0.6748(3) 0.34154(19) 0.1177(5) 0.0507(7) Uani d 1
H H11A 0.6521 0.2944 0.0499 0.061 Uiso calc 1
H H11B 0.7160 0.3762 0.0297 0.061 Uiso calc 1
C C12 0.7673(3) 0.32418(18) 0.2785(6) 0.0524(8) Uani d 1
C C13 0.8389(4) 0.3114(3) 0.4095(7) 0.0715(11) Uani d 1
H H13 0.8958 0.3012 0.5135 0.086 Uiso calc 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
Br1 0.0547(2) 0.0393(2) 0.0645(2) -0.01276(13) 0.00117(15) 0.00276(13)
O1 0.0480(12) 0.0521(13) 0.0681(15) -0.0138(10) 0.0080(10) 0.0030(11)
O2 0.0639(14) 0.0322(11) 0.0909(19) -0.0061(10) 0.0152(13) -0.0050(11)
N1 0.0349(11) 0.0403(12) 0.0438(13) 0.0003(9) 0.0039(9) -0.0007(10)
N2 0.0386(11) 0.0293(10) 0.0410(12) 0.0025(9) 0.0029(9) -0.0028(9)
N3 0.0409(12) 0.0361(11) 0.0433(12) 0.0066(9) -0.0015(9) -0.0036(10)
C1 0.0403(14) 0.0433(15) 0.0411(14) -0.0040(12) -0.0014(11) 0.0012(12)
C2 0.0422(14) 0.0343(14) 0.0491(16) -0.0040(11) 0.0006(11) -0.0014(11)
C3 0.0363(12) 0.0305(12) 0.0306(12) 0.0012(10) -0.0014(9) 0.0015(10)
C4 0.0371(13) 0.0359(13) 0.0380(13) 0.0023(11) 0.0020(10) -0.0004(11)
C5 0.0449(14) 0.0310(13) 0.0357(13) -0.0036(11) -0.0029(10) 0.0014(10)
C6 0.0495(15) 0.0290(13) 0.0443(15) 0.0032(11) -0.0052(12) -0.0022(11)
C7 0.0356(12) 0.0340(13) 0.0341(13) 0.0013(10) -0.0020(9) -0.0020(10)
C8 0.0473(15) 0.0339(13) 0.0460(15) 0.0052(11) 0.0071(12) -0.0077(11)
C9 0.0450(16) 0.0376(14) 0.0491(16) 0.0085(11) 0.0107(12) 0.0009(12)
C10 0.0498(18) 0.0539(18) 0.0571(19) 0.0096(14) 0.0045(14) -0.0032(15)
C11 0.0410(15) 0.0528(18) 0.0590(19) 0.0034(12) 0.0115(13) -0.0033(14)
C12 0.0348(14) 0.0452(16) 0.078(2) -0.0002(12) 0.0109(15) 0.0023(15)
C13 0.0465(19) 0.074(3) 0.094(3) 0.0025(18) -0.004(2) 0.012(2)
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C1 N1 C7 122.8(2)
C1 N1 C11 118.2(2)
C7 N1 C11 118.9(2)
C2 N2 C3 122.5(2)
C2 N2 C8 117.4(2)
C3 N2 C8 119.8(2)
C7 N3 C6 118.7(2)
O1 C1 N1 123.3(3)
O1 C1 C2 119.2(3)
N1 C1 C2 117.5(2)
O2 C2 N2 123.2(3)
O2 C2 C1 119.0(3)
N2 C2 C1 117.7(2)
N2 C3 C7 119.9(2)
C4 C3 N2 122.9(2)
C4 C3 C7 117.3(2)
C3 C4 H4 121.0
C3 C4 C5 118.1(2)
C5 C4 H4 121.0
C4 C5 Br1 120.1(2)
C6 C5 Br1 118.9(2)
C6 C5 C4 121.0(3)
N3 C6 C5 120.9(2)
N3 C6 H6 119.5
C5 C6 H6 119.5
N1 C7 C3 119.3(2)
N3 C7 N1 116.8(2)
N3 C7 C3 123.9(3)
N2 C8 H8A 108.8
N2 C8 H8B 108.8
H8A C8 H8B 107.7
C9 C8 N2 114.0(2)
C9 C8 H8A 108.8
C9 C8 H8B 108.8
C10 C9 C8 175.8(3)
C9 C10 H10 180.0
N1 C11 H11A 109.6
N1 C11 H11B 109.6
H11A C11 H11B 108.1
C12 C11 N1 110.1(3)
C12 C11 H11A 109.6
C12 C11 H11B 109.6
C13 C12 C11 178.3(4)
C12 C13 H13 180.0
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C5 1.894(3)
O1 C1 1.217(4)
O2 C2 1.214(4)
N1 C1 1.363(4)
N1 C7 1.402(4)
N1 C11 1.472(4)
N2 C2 1.365(4)
N2 C3 1.397(3)
N2 C8 1.477(3)
N3 C6 1.331(4)
N3 C7 1.322(4)
C1 C2 1.524(4)
C3 C4 1.379(4)
C3 C7 1.405(4)
C4 H4 0.9300
C4 C5 1.384(4)
C5 C6 1.381(4)
C6 H6 0.9300
C8 H8A 0.9700
C8 H8B 0.9700
C8 C9 1.457(5)
C9 C10 1.176(5)
C10 H10 0.9300
C11 H11A 0.9700
C11 H11B 0.9700
C11 C12 1.472(5)
C12 C13 1.172(6)
C13 H13 0.9300
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
C6 H6 O2 2_645 0.93 2.58 3.326(4) 137
_cod_database_fobs_code 1548987