#------------------------------------------------------------------------------
#$Date: 2021-11-06 22:41:47 +0200 (Sat, 06 Nov 2021) $
#$Revision: 270502 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158300.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7158300
loop_
_publ_author_name
'Wang, Rui-Li'
'Jia, Shi-Kun'
'Guo, Ya-Jun'
'Yi, Yang'
'Hua, Yuan-Zhao'
'Lu, Hui-Jie'
'Wang, Min-Can'
_publ_section_title
;
Dinuclear zinc-catalyzed enantioselective formal [3 + 2] cycloaddition of
N-2,2,2-trifluoroethylisatin ketimines with low reactivity aurone
derivatives.
;
_journal_issue 39
_journal_name_full 'Organic & biomolecular chemistry'
_journal_page_first 8492
_journal_page_last 8496
_journal_paper_doi 10.1039/d1ob01599k
_journal_volume 19
_journal_year 2021
_chemical_formula_sum 'C29 H24 Br F3 N2 O5'
_chemical_formula_weight 617.41
_space_group_crystal_system triclinic
_space_group_IT_number 1
_space_group_name_Hall 'P 1'
_space_group_name_H-M_alt 'P 1'
_atom_sites_solution_hydrogens mixed
_audit_creation_method SHELXL-2014/7
_audit_update_record
;
2020-11-02 deposited with the CCDC. 2021-09-14 downloaded from the CCDC.
;
_cell_angle_alpha 113.621(8)
_cell_angle_beta 101.541(7)
_cell_angle_gamma 100.342(7)
_cell_formula_units_Z 1
_cell_length_a 7.0824(5)
_cell_length_b 9.9984(8)
_cell_length_c 11.3089(9)
_cell_measurement_temperature 293(2)
_cell_volume 688.15(11)
_computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature 293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_radiation_type CuK\a
_diffrn_radiation_wavelength 1.54184
_diffrn_reflns_av_R_equivalents 0.0400
_diffrn_reflns_av_unetI/netI 0.0616
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max 7
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_l_max 13
_diffrn_reflns_limit_l_min -13
_diffrn_reflns_number 7450
_diffrn_reflns_point_group_measured_fraction_full 0.791
_diffrn_reflns_point_group_measured_fraction_max 0.791
_diffrn_reflns_theta_full 67.108
_diffrn_reflns_theta_max 67.108
_diffrn_reflns_theta_min 4.476
_exptl_absorpt_coefficient_mu 2.584
_exptl_crystal_density_diffrn 1.490
_exptl_crystal_F_000 314
_exptl_crystal_size_max 0.160
_exptl_crystal_size_mid 0.140
_exptl_crystal_size_min 0.100
_refine_diff_density_max 0.527
_refine_diff_density_min -0.366
_refine_diff_density_rms 0.053
_refine_ls_abs_structure_details
;
Flack x determined using 995 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack 0.003(16)
_refine_ls_extinction_coef 0.0043(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref 1.028
_refine_ls_hydrogen_treatment mixed
_refine_ls_matrix_type full
_refine_ls_number_parameters 372
_refine_ls_number_reflns 3900
_refine_ls_number_restraints 21
_refine_ls_restrained_S_all 1.051
_refine_ls_R_factor_all 0.0595
_refine_ls_R_factor_gt 0.0487
_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^)+(0.0643P)^2^+0.0394P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme calc
_refine_ls_wR_factor_gt 0.1188
_refine_ls_wR_factor_ref 0.1303
_reflns_Friedel_coverage 0.583
_reflns_Friedel_fraction_full 0.583
_reflns_Friedel_fraction_max 0.583
_reflns_number_gt 3281
_reflns_number_total 3900
_reflns_threshold_expression 'I > 2\s(I)'
_cod_data_source_file d1ob01599k2.cif
_cod_data_source_block 202008157
_cod_depositor_comments 'Adding full bibliography for 7158300.cif.'
_cod_original_cell_volume 688.15(10)
_cod_database_code 7158300
_shelx_shelxl_version_number 2014/7
_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 0.683
_shelx_estimated_absorpt_t_max 0.782
_shelx_res_file
;
202008157.res created by SHELXL-2014/7
TITL 202008157 in P1 #1
REM reset to P1 #1
CELL 1.54184 7.082436 9.998368 11.30887 113.6211 101.5411 100.3417
ZERR 1 0.000546 0.000794 0.000912 0.0077 0.0068 0.0066
LATT -1
SFAC C H Br F N O
UNIT 29 24 1 3 2 5
EQIV $1 -1+X,+Y,+Z
DFIX 0.87 N2 H2
DFIX 1.63 C29 C28
DFIX 0.87 N1 H1
DFIX 1.45 C28 O5
DFIX 1.55 O5 C26
DFIX 1.53 C27 C26
ISOR 0.01 0.02 C27 C26
L.S. 4 0 0
PLAN 20
SIZE 0.16 0.14 0.1
MPLA C1 C2 N1 C3 C4 C5 C6 C7 C8
MPLA C2 C9 C18 N2
MPLA C17 C18 C9
MPLA C9 C10 C11 C12 C13 C14 C15 C16 O3
MPLA C20 C21 C22 C23 C24 C25
HTAB N1 O4
HTAB N2 O4_$1
bond $h
conf
fmap 2
acta
REM
REM
REM
WGHT 0.064300 0.039400
EXTI 0.004299
FVAR 12.23611
BR1 3 -0.078910 -0.209140 0.795190 11.00000 0.11780 0.12549 =
0.12136 0.09625 0.07604 0.04785
C1 1 0.700232 0.187246 0.392594 11.00000 0.04033 0.06922 =
0.04683 0.03305 0.02131 0.02129
C2 1 0.504973 0.232769 0.411506 11.00000 0.03160 0.04180 =
0.04042 0.02100 0.01117 0.00671
C3 1 0.548530 0.386833 0.410803 11.00000 0.04242 0.04057 =
0.04464 0.02250 0.00982 0.00266
C4 1 0.735515 0.419863 0.394901 11.00000 0.05386 0.06119 =
0.05764 0.03133 0.02076 0.00690
C5 1 0.811016 0.548945 0.380265 11.00000 0.07785 0.06469 =
0.09066 0.04214 0.03650 0.00346
AFIX 43
H5 2 0.938927 0.571639 0.371174 11.00000 -1.20000
AFIX 0
C6 1 0.688498 0.642243 0.379754 11.00000 0.12154 0.04508 =
0.07777 0.02979 0.03413 -0.00266
AFIX 43
H6 2 0.733577 0.727945 0.367916 11.00000 -1.20000
AFIX 0
C7 1 0.501924 0.610563 0.396385 11.00000 0.09209 0.04708 =
0.07023 0.03026 0.02376 0.02276
AFIX 43
H7 2 0.422758 0.675408 0.396489 11.00000 -1.20000
AFIX 0
C8 1 0.429957 0.482955 0.413048 11.00000 0.06121 0.04817 =
0.06036 0.02879 0.01986 0.01788
AFIX 43
H8 2 0.304063 0.462401 0.425521 11.00000 -1.20000
AFIX 0
C9 1 0.457205 0.226164 0.537170 11.00000 0.03299 0.04285 =
0.03535 0.01884 0.01222 0.01285
C10 1 0.633862 0.306301 0.670442 11.00000 0.03485 0.04996 =
0.04674 0.02376 0.00779 0.00898
C11 1 0.568895 0.421569 0.764474 11.00000 0.04536 0.04598 =
0.04386 0.02094 0.01187 0.00790
C12 1 0.377498 0.414452 0.697113 11.00000 0.04216 0.03514 =
0.03839 0.01553 0.01680 0.00375
C13 1 0.270141 0.509921 0.759461 11.00000 0.05931 0.05499 =
0.05973 0.02829 0.03058 0.02528
AFIX 43
H13 2 0.141291 0.503608 0.714257 11.00000 -1.20000
AFIX 0
C14 1 0.366085 0.614441 0.892231 11.00000 0.08727 0.06202 =
0.05610 0.01366 0.03392 0.02538
AFIX 43
H14 2 0.299299 0.681076 0.937301 11.00000 -1.20000
AFIX 0
C15 1 0.555856 0.625576 0.961910 11.00000 0.08890 0.06968 =
0.04897 0.00889 0.02130 0.01545
AFIX 43
H15 2 0.613465 0.698438 1.051833 11.00000 -1.20000
AFIX 0
C16 1 0.661980 0.529231 0.899355 11.00000 0.06114 0.07005 =
0.04212 0.01754 0.00305 0.00693
AFIX 43
H16 2 0.790498 0.536070 0.945557 11.00000 -1.20000
AFIX 0
C17 1 0.361299 0.055212 0.483408 11.00000 0.03817 0.04122 =
0.03969 0.01967 0.01390 0.01466
AFIX 13
H17 2 0.467436 0.005116 0.469352 11.00000 -1.20000
AFIX 0
C18 1 0.223451 0.016814 0.341483 11.00000 0.03619 0.04018 =
0.03555 0.01659 0.00790 0.00548
AFIX 13
H18 2 0.096521 0.039743 0.349870 11.00000 -1.20000
AFIX 0
C19 1 0.179618 -0.147900 0.239804 11.00000 0.05946 0.04629 =
0.04079 0.01599 0.01171 0.00337
C20 1 0.260227 0.004991 0.570182 11.00000 0.04168 0.03455 =
0.03659 0.01655 0.01256 0.01147
C21 1 0.340587 -0.083868 0.623243 11.00000 0.05434 0.05478 =
0.05141 0.03155 0.01985 0.02130
AFIX 43
H21 2 0.461125 -0.102777 0.611593 11.00000 -1.20000
AFIX 0
C22 1 0.242805 -0.144304 0.693138 11.00000 0.07638 0.06487 =
0.06203 0.04541 0.03380 0.03487
AFIX 43
H22 2 0.296047 -0.204549 0.727371 11.00000 -1.20000
AFIX 0
C23 1 0.066207 -0.113996 0.711149 11.00000 0.07057 0.05774 =
0.05282 0.03552 0.02775 0.01561
C24 1 -0.013927 -0.022882 0.664881 11.00000 0.04676 0.07006 =
0.05703 0.03595 0.02598 0.02166
AFIX 43
H24 2 -0.131646 -0.001255 0.680289 11.00000 -1.20000
AFIX 0
C25 1 0.084449 0.036327 0.594587 11.00000 0.04394 0.05656 =
0.04645 0.03165 0.01967 0.01931
AFIX 43
H25 2 0.031582 0.098606 0.562924 11.00000 -1.20000
AFIX 0
F1 4 0.340925 -0.192672 0.221772 11.00000 0.09452 0.05826 =
0.07068 0.01967 0.03634 0.03238
F2 4 0.075323 -0.243842 0.273792 11.00000 0.11948 0.05166 =
0.07418 0.02751 0.03985 -0.00475
F3 4 0.069790 -0.172831 0.117682 11.00000 0.09563 0.06749 =
0.04447 0.01499 -0.00393 0.00010
N1 5 0.825629 0.305779 0.392343 11.00000 0.04275 0.06973 =
0.08754 0.04052 0.03212 0.01687
H1 2 0.924198 0.287044 0.360793 11.00000 0.04195
N2 5 0.333092 0.118212 0.298389 11.00000 0.03658 0.04015 =
0.03819 0.02056 0.00740 0.00739
H2 2 0.262403 0.161676 0.264314 11.00000 0.03573
O1 6 0.730289 0.066218 0.373188 11.00000 0.05442 0.06989 =
0.07184 0.03972 0.02823 0.03209
O2 6 0.788207 0.270076 0.683146 11.00000 0.04412 0.07916 =
0.05694 0.02983 0.00551 0.02333
O3 6 0.305379 0.305259 0.565216 11.00000 0.03448 0.04318 =
0.04222 0.01898 0.01101 0.01447
C26 1 0.893698 0.184209 0.074073 11.00000 0.13889 0.13866 =
0.11301 0.04077 0.02600 0.07359
C27 1 0.676629 0.073333 0.016428 11.00000 0.10800 0.19865 =
0.13392 0.03503 0.03790 0.01307
AFIX 137
H27A 2 0.580901 0.130849 0.023481 11.00000 -1.50000
H27B 2 0.662873 0.016728 0.067152 11.00000 -1.50000
H27C 2 0.652307 0.004075 -0.076885 11.00000 -1.50000
AFIX 0
C28 1 1.097068 0.344260 0.016112 11.00000 0.17959 0.22712 =
0.14614 0.13019 0.02446 0.02314
AFIX 23
H28A 2 1.122061 0.421121 0.108099 11.00000 -1.20000
H28B 2 1.082016 0.393476 -0.042294 11.00000 -1.20000
AFIX 0
C29 1 1.281005 0.283328 0.008076 11.00000 0.23599 0.18453 =
0.14473 0.04589 0.03040 -0.02663
AFIX 137
H29A 2 1.395633 0.354973 0.083209 11.00000 -1.50000
H29B 2 1.308697 0.269623 -0.075071 11.00000 -1.50000
H29C 2 1.253518 0.187347 0.011072 11.00000 -1.50000
AFIX 0
O4 6 1.016798 0.238072 0.177883 11.00000 0.06235 0.14721 =
0.06057 0.04876 0.01138 0.03575
O5 6 0.902432 0.223632 -0.024055 11.00000 0.21723 0.20524 =
0.09253 0.09160 0.03484 0.08538
HKLF 4
REM 202008157 in P1 #1
REM R1 = 0.0487 for 3281 Fo > 4sig(Fo) and 0.0595 for all 3900 data
REM 372 parameters refined using 21 restraints
END
WGHT 0.0643 0.0394
REM Highest difference peak 0.527, deepest hole -0.366, 1-sigma level 0.053
Q1 1 0.0549 -0.1198 0.8729 11.00000 0.05 0.53
Q2 1 1.0264 0.2645 0.0716 11.00000 0.05 0.42
Q3 1 0.6652 0.1946 0.0198 11.00000 0.05 0.27
Q4 1 -0.0073 -0.1935 0.7401 11.00000 0.05 0.26
Q5 1 0.7590 0.2182 0.0226 11.00000 0.05 0.23
Q6 1 0.3829 0.5042 0.6938 11.00000 0.05 0.19
Q7 1 0.4906 0.0902 -0.0161 11.00000 0.05 0.19
Q8 1 0.5470 0.0657 0.0408 11.00000 0.05 0.18
Q9 1 1.1122 0.2827 0.4122 11.00000 0.05 0.18
Q10 1 1.4679 0.5149 0.1062 11.00000 0.05 0.17
Q11 1 0.6254 -0.0163 0.3017 11.00000 0.05 0.17
Q12 1 0.8396 0.3428 0.5399 11.00000 0.05 0.17
Q13 1 -0.1775 -0.0936 0.5774 11.00000 0.05 0.17
Q14 1 0.8973 0.2158 0.7447 11.00000 0.05 0.17
Q15 1 0.2067 0.7817 0.8878 11.00000 0.05 0.17
Q16 1 0.1146 0.4408 0.6766 11.00000 0.05 0.16
Q17 1 0.2638 -0.0238 0.3992 11.00000 0.05 0.16
Q18 1 0.7860 0.1313 -0.0371 11.00000 0.05 0.16
Q19 1 0.7289 0.6594 1.1064 11.00000 0.05 0.16
Q20 1 0.1424 0.3173 0.7240 11.00000 0.05 0.16
;
_shelx_res_checksum 8266
loop_
_space_group_symop_operation_xyz
'x, y, z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.07891(12) -0.20914(10) 0.79519(10) 0.0991(5) Uani 1 1 d . . . . .
C1 C 0.7002(10) 0.1872(9) 0.3926(7) 0.0476(15) Uani 1 1 d . . . . .
C2 C 0.5050(8) 0.2328(7) 0.4115(6) 0.0376(12) Uani 1 1 d . . . . .
C3 C 0.5485(10) 0.3868(7) 0.4108(7) 0.0433(14) Uani 1 1 d . . . . .
C4 C 0.7355(11) 0.4199(9) 0.3949(8) 0.0568(18) Uani 1 1 d . . . . .
C5 C 0.8110(15) 0.5489(10) 0.3803(10) 0.076(2) Uani 1 1 d . . . . .
H5 H 0.9389 0.5716 0.3712 0.091 Uiso 1 1 calc R U . . .
C6 C 0.6885(17) 0.6422(9) 0.3798(10) 0.084(3) Uani 1 1 d . . . . .
H6 H 0.7336 0.7279 0.3679 0.101 Uiso 1 1 calc R U . . .
C7 C 0.5019(14) 0.6106(9) 0.3964(9) 0.068(2) Uani 1 1 d . . . . .
H7 H 0.4228 0.6754 0.3965 0.082 Uiso 1 1 calc R U . . .
C8 C 0.4300(12) 0.4830(8) 0.4130(8) 0.0546(17) Uani 1 1 d . . . . .
H8 H 0.3041 0.4624 0.4255 0.065 Uiso 1 1 calc R U . . .
C9 C 0.4572(8) 0.2262(7) 0.5372(6) 0.0361(12) Uani 1 1 d . . . . .
C10 C 0.6339(9) 0.3063(7) 0.6704(7) 0.0444(14) Uani 1 1 d . . . . .
C11 C 0.5689(10) 0.4216(7) 0.7645(7) 0.0459(14) Uani 1 1 d . . . . .
C12 C 0.3775(9) 0.4145(7) 0.6971(6) 0.0393(13) Uani 1 1 d . . . . .
C13 C 0.2701(11) 0.5099(8) 0.7595(8) 0.0539(17) Uani 1 1 d . . . . .
H13 H 0.1413 0.5036 0.7143 0.065 Uiso 1 1 calc R U . . .
C14 C 0.3661(15) 0.6144(10) 0.8922(9) 0.070(2) Uani 1 1 d . . . . .
H14 H 0.2993 0.6811 0.9373 0.085 Uiso 1 1 calc R U . . .
C15 C 0.5559(16) 0.6256(11) 0.9619(9) 0.076(3) Uani 1 1 d . . . . .
H15 H 0.6135 0.6984 1.0518 0.092 Uiso 1 1 calc R U . . .
C16 C 0.6620(13) 0.5292(10) 0.8994(8) 0.064(2) Uani 1 1 d . . . . .
H16 H 0.7905 0.5361 0.9456 0.077 Uiso 1 1 calc R U . . .
C17 C 0.3613(9) 0.0552(7) 0.4834(6) 0.0384(13) Uani 1 1 d . . . . .
H17 H 0.4674 0.0051 0.4694 0.046 Uiso 1 1 calc R U . . .
C18 C 0.2235(9) 0.0168(7) 0.3415(6) 0.0388(13) Uani 1 1 d . . . . .
H18 H 0.0965 0.0397 0.3499 0.047 Uiso 1 1 calc R U . . .
C19 C 0.1796(11) -0.1479(8) 0.2398(7) 0.0524(16) Uani 1 1 d . . . . .
C20 C 0.2602(9) 0.0050(7) 0.5702(6) 0.0373(12) Uani 1 1 d . . . . .
C21 C 0.3406(11) -0.0839(8) 0.6232(7) 0.0495(16) Uani 1 1 d . . . . .
H21 H 0.4611 -0.1028 0.6116 0.059 Uiso 1 1 calc R U . . .
C22 C 0.2428(12) -0.1443(9) 0.6931(8) 0.0577(18) Uani 1 1 d . . . . .
H22 H 0.2960 -0.2045 0.7274 0.069 Uiso 1 1 calc R U . . .
C23 C 0.0662(12) -0.1140(8) 0.7111(7) 0.0557(18) Uani 1 1 d . . . . .
C24 C -0.0139(11) -0.0229(9) 0.6649(8) 0.0531(17) Uani 1 1 d . . . . .
H24 H -0.1316 -0.0013 0.6803 0.064 Uiso 1 1 calc R U . . .
C25 C 0.0844(9) 0.0363(8) 0.5946(7) 0.0444(14) Uani 1 1 d . . . . .
H25 H 0.0316 0.0986 0.5629 0.053 Uiso 1 1 calc R U . . .
F1 F 0.3409(8) -0.1927(5) 0.2218(5) 0.0745(13) Uani 1 1 d . . . . .
F2 F 0.0753(9) -0.2438(5) 0.2738(5) 0.0847(16) Uani 1 1 d . . . . .
F3 F 0.0698(8) -0.1728(5) 0.1177(5) 0.0803(14) Uani 1 1 d . . . . .
N1 N 0.8256(10) 0.3058(8) 0.3923(8) 0.0628(17) Uani 1 1 d D . . . .
H1 H 0.924(7) 0.287(7) 0.361(6) 0.042(18) Uiso 1 1 d D . . . .
N2 N 0.3331(7) 0.1182(6) 0.2984(5) 0.0385(11) Uani 1 1 d D . . . .
H2 H 0.262(8) 0.162(7) 0.264(6) 0.036(16) Uiso 1 1 d D . . . .
O1 O 0.7303(7) 0.0662(6) 0.3732(5) 0.0592(13) Uani 1 1 d . . . . .
O2 O 0.7882(7) 0.2701(6) 0.6831(5) 0.0612(13) Uani 1 1 d . . . . .
O3 O 0.3054(6) 0.3053(5) 0.5652(4) 0.0397(9) Uani 1 1 d . . . . .
C26 C 0.894(2) 0.1842(18) 0.0741(16) 0.133(5) Uani 1 1 d D U . . .
C27 C 0.677(2) 0.073(2) 0.0164(18) 0.165(7) Uani 1 1 d D U . . .
H27A H 0.5809 0.1308 0.0235 0.248 Uiso 1 1 calc R U . . .
H27B H 0.6629 0.0167 0.0672 0.248 Uiso 1 1 calc R U . . .
H27C H 0.6523 0.0041 -0.0769 0.248 Uiso 1 1 calc R U . . .
C28 C 1.097(3) 0.344(3) 0.016(2) 0.178(9) Uani 1 1 d D . . . .
H28A H 1.1221 0.4211 0.1081 0.213 Uiso 1 1 calc R U . . .
H28B H 1.0820 0.3935 -0.0423 0.213 Uiso 1 1 calc R U . . .
C29 C 1.281(4) 0.283(3) 0.008(2) 0.216(11) Uani 1 1 d D . . . .
H29A H 1.3956 0.3550 0.0832 0.323 Uiso 1 1 calc R U . . .
H29B H 1.3087 0.2696 -0.0751 0.323 Uiso 1 1 calc R U . . .
H29C H 1.2535 0.1873 0.0111 0.323 Uiso 1 1 calc R U . . .
O4 O 1.0168(10) 0.2381(10) 0.1779(7) 0.090(2) Uani 1 1 d . . . . .
O5 O 0.902(2) 0.2236(16) -0.0241(10) 0.162(5) Uani 1 1 d D . . . .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Br1 0.1178(9) 0.1255(9) 0.1214(9) 0.0962(8) 0.0760(7) 0.0479(7)
C1 0.040(3) 0.069(4) 0.047(4) 0.033(3) 0.021(3) 0.021(3)
C2 0.032(3) 0.042(3) 0.040(3) 0.021(3) 0.011(2) 0.007(2)
C3 0.042(3) 0.041(3) 0.045(3) 0.022(3) 0.010(3) 0.003(3)
C4 0.054(4) 0.061(4) 0.058(4) 0.031(4) 0.021(3) 0.007(3)
C5 0.078(6) 0.065(5) 0.091(7) 0.042(5) 0.036(5) 0.003(4)
C6 0.122(8) 0.045(4) 0.078(6) 0.030(4) 0.034(6) -0.003(5)
C7 0.092(6) 0.047(4) 0.070(5) 0.030(4) 0.024(5) 0.023(4)
C8 0.061(4) 0.048(4) 0.060(4) 0.029(3) 0.020(4) 0.018(3)
C9 0.033(3) 0.043(3) 0.035(3) 0.019(3) 0.012(2) 0.013(2)
C10 0.035(3) 0.050(4) 0.047(4) 0.024(3) 0.008(3) 0.009(3)
C11 0.045(4) 0.046(3) 0.044(4) 0.021(3) 0.012(3) 0.008(3)
C12 0.042(3) 0.035(3) 0.038(3) 0.016(3) 0.017(3) 0.004(3)
C13 0.059(4) 0.055(4) 0.060(4) 0.028(4) 0.031(3) 0.025(3)
C14 0.087(6) 0.062(5) 0.056(5) 0.014(4) 0.034(5) 0.025(4)
C15 0.089(7) 0.070(5) 0.049(5) 0.009(4) 0.021(5) 0.015(5)
C16 0.061(5) 0.070(5) 0.042(4) 0.018(4) 0.003(4) 0.007(4)
C17 0.038(3) 0.041(3) 0.040(3) 0.020(3) 0.014(3) 0.015(3)
C18 0.036(3) 0.040(3) 0.036(3) 0.017(3) 0.008(2) 0.005(2)
C19 0.059(4) 0.046(4) 0.041(4) 0.016(3) 0.012(3) 0.003(3)
C20 0.042(3) 0.035(3) 0.037(3) 0.017(3) 0.013(2) 0.011(2)
C21 0.054(4) 0.055(4) 0.051(4) 0.032(3) 0.020(3) 0.021(3)
C22 0.076(5) 0.065(4) 0.062(5) 0.045(4) 0.034(4) 0.035(4)
C23 0.071(5) 0.058(4) 0.053(4) 0.036(4) 0.028(4) 0.016(4)
C24 0.047(4) 0.070(5) 0.057(4) 0.036(4) 0.026(3) 0.022(3)
C25 0.044(4) 0.057(4) 0.046(4) 0.032(3) 0.020(3) 0.019(3)
F1 0.095(4) 0.058(2) 0.071(3) 0.020(2) 0.036(3) 0.032(2)
F2 0.119(4) 0.052(2) 0.074(3) 0.028(2) 0.040(3) -0.005(3)
F3 0.096(4) 0.067(3) 0.044(2) 0.015(2) -0.004(2) 0.000(3)
N1 0.043(3) 0.070(4) 0.088(5) 0.041(4) 0.032(3) 0.017(3)
N2 0.037(3) 0.040(3) 0.038(3) 0.021(2) 0.007(2) 0.007(2)
O1 0.054(3) 0.070(3) 0.072(4) 0.040(3) 0.028(3) 0.032(3)
O2 0.044(3) 0.079(3) 0.057(3) 0.030(3) 0.006(2) 0.023(2)
O3 0.034(2) 0.043(2) 0.042(2) 0.019(2) 0.0110(18) 0.0145(17)
C26 0.139(10) 0.139(9) 0.113(9) 0.041(7) 0.026(7) 0.074(8)
C27 0.108(11) 0.199(16) 0.134(12) 0.035(11) 0.038(9) 0.013(10)
C28 0.18(2) 0.23(3) 0.146(17) 0.130(19) 0.024(16) 0.023(19)
C29 0.24(3) 0.18(2) 0.145(19) 0.046(16) 0.030(19) -0.027(19)
O4 0.062(4) 0.147(7) 0.061(4) 0.049(4) 0.011(3) 0.036(4)
O5 0.217(13) 0.205(12) 0.093(7) 0.092(8) 0.035(8) 0.085(11)
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'
F F 0.0727 0.0534 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 N1 125.9(6) . . ?
O1 C1 C2 127.1(6) . . ?
N1 C1 C2 106.8(6) . . ?
N2 C2 C3 113.0(5) . . ?
N2 C2 C9 103.7(4) . . ?
C3 C2 C9 117.5(5) . . ?
N2 C2 C1 108.8(5) . . ?
C3 C2 C1 101.8(5) . . ?
C9 C2 C1 112.1(5) . . ?
C4 C3 C8 120.1(6) . . ?
C4 C3 C2 108.4(6) . . ?
C8 C3 C2 131.3(6) . . ?
C3 C4 C5 121.7(8) . . ?
C3 C4 N1 110.1(6) . . ?
C5 C4 N1 128.1(7) . . ?
C6 C5 C4 117.5(8) . . ?
C6 C5 H5 121.3 . . ?
C4 C5 H5 121.3 . . ?
C7 C6 C5 121.2(7) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.7(8) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C3 C8 C7 118.8(7) . . ?
C3 C8 H8 120.6 . . ?
C7 C8 H8 120.6 . . ?
O3 C9 C17 109.0(4) . . ?
O3 C9 C10 105.2(5) . . ?
C17 C9 C10 116.9(5) . . ?
O3 C9 C2 107.6(4) . . ?
C17 C9 C2 101.6(5) . . ?
C10 C9 C2 116.2(5) . . ?
O2 C10 C11 131.4(6) . . ?
O2 C10 C9 123.1(6) . . ?
C11 C10 C9 105.4(5) . . ?
C12 C11 C16 120.2(7) . . ?
C12 C11 C10 107.6(6) . . ?
C16 C11 C10 132.2(7) . . ?
O3 C12 C13 123.4(6) . . ?
O3 C12 C11 114.1(5) . . ?
C13 C12 C11 122.5(6) . . ?
C14 C13 C12 115.8(7) . . ?
C14 C13 H13 122.1 . . ?
C12 C13 H13 122.1 . . ?
C13 C14 C15 123.4(8) . . ?
C13 C14 H14 118.3 . . ?
C15 C14 H14 118.3 . . ?
C14 C15 C16 120.6(8) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 117.5(8) . . ?
C15 C16 H16 121.2 . . ?
C11 C16 H16 121.2 . . ?
C20 C17 C9 117.5(5) . . ?
C20 C17 C18 116.1(5) . . ?
C9 C17 C18 100.1(4) . . ?
C20 C17 H17 107.5 . . ?
C9 C17 H17 107.5 . . ?
C18 C17 H17 107.5 . . ?
N2 C18 C19 110.4(5) . . ?
N2 C18 C17 105.2(4) . . ?
C19 C18 C17 112.8(5) . . ?
N2 C18 H18 109.4 . . ?
C19 C18 H18 109.4 . . ?
C17 C18 H18 109.4 . . ?
F1 C19 F2 105.9(6) . . ?
F1 C19 F3 106.1(6) . . ?
F2 C19 F3 107.0(6) . . ?
F1 C19 C18 114.8(6) . . ?
F2 C19 C18 112.2(6) . . ?
F3 C19 C18 110.3(6) . . ?
C25 C20 C21 118.0(6) . . ?
C25 C20 C17 123.2(5) . . ?
C21 C20 C17 118.7(6) . . ?
C22 C21 C20 120.7(7) . . ?
C22 C21 H21 119.6 . . ?
C20 C21 H21 119.6 . . ?
C23 C22 C21 119.1(6) . . ?
C23 C22 H22 120.5 . . ?
C21 C22 H22 120.5 . . ?
C24 C23 C22 122.0(6) . . ?
C24 C23 Br1 118.8(6) . . ?
C22 C23 Br1 119.2(5) . . ?
C23 C24 C25 118.4(6) . . ?
C23 C24 H24 120.8 . . ?
C25 C24 H24 120.8 . . ?
C24 C25 C20 121.7(6) . . ?
C24 C25 H25 119.2 . . ?
C20 C25 H25 119.2 . . ?
C1 N1 C4 112.5(6) . . ?
C1 N1 H1 116(5) . . ?
C4 N1 H1 127(5) . . ?
C2 N2 C18 109.9(4) . . ?
C2 N2 H2 110(4) . . ?
C18 N2 H2 115(4) . . ?
C12 O3 C9 107.6(4) . . ?
O4 C26 O5 124.5(16) . . ?
O4 C26 C27 133.5(16) . . ?
O5 C26 C27 101.5(15) . . ?
C26 C27 H27A 109.5 . . ?
C26 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C26 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O5 C28 C29 114.2(18) . . ?
O5 C28 H28A 108.7 . . ?
C29 C28 H28A 108.7 . . ?
O5 C28 H28B 108.7 . . ?
C29 C28 H28B 108.7 . . ?
H28A C28 H28B 107.6 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C26 O5 C28 110.8(13) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C23 1.905(7) . ?
C1 O1 1.207(8) . ?
C1 N1 1.349(9) . ?
C1 C2 1.559(8) . ?
C2 N2 1.460(8) . ?
C2 C3 1.519(8) . ?
C2 C9 1.549(8) . ?
C3 C4 1.372(10) . ?
C3 C8 1.381(10) . ?
C4 C5 1.392(11) . ?
C4 N1 1.397(11) . ?
C5 C6 1.384(14) . ?
C5 H5 0.9300 . ?
C6 C7 1.371(13) . ?
C6 H6 0.9300 . ?
C7 C8 1.386(10) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 O3 1.457(7) . ?
C9 C17 1.529(8) . ?
C9 C10 1.548(8) . ?
C10 O2 1.212(8) . ?
C10 C11 1.440(10) . ?
C11 C12 1.390(9) . ?
C11 C16 1.395(10) . ?
C12 O3 1.367(7) . ?
C12 C13 1.386(9) . ?
C13 C14 1.374(11) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(14) . ?
C14 H14 0.9300 . ?
C15 C16 1.386(13) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 C20 1.508(8) . ?
C17 C18 1.556(8) . ?
C17 H17 0.9800 . ?
C18 N2 1.460(7) . ?
C18 C19 1.512(9) . ?
C18 H18 0.9800 . ?
C19 F1 1.323(9) . ?
C19 F2 1.330(8) . ?
C19 F3 1.341(8) . ?
C20 C25 1.390(9) . ?
C20 C21 1.395(9) . ?
C21 C22 1.386(10) . ?
C21 H21 0.9300 . ?
C22 C23 1.373(11) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(10) . ?
C24 C25 1.385(9) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
N1 H1 0.86(3) . ?
N2 H2 0.85(3) . ?
C26 O4 1.159(16) . ?
C26 O5 1.327(16) . ?
C26 C27 1.557(18) . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 0.9600 . ?
C28 O5 1.508(17) . ?
C28 C29 1.54(2) . ?
C28 H28A 0.9700 . ?
C28 H28B 0.9700 . ?
C29 H29A 0.9600 . ?
C29 H29B 0.9600 . ?
C29 H29C 0.9600 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O4 0.86(3) 2.19(5) 2.916(9) 142(6) .
N2 H2 O4 0.85(3) 2.23(3) 3.060(8) 166(6) 1_455
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 N2 -52.5(8) . . . . ?
N1 C1 C2 N2 123.2(6) . . . . ?
O1 C1 C2 C3 -172.0(7) . . . . ?
N1 C1 C2 C3 3.7(7) . . . . ?
O1 C1 C2 C9 61.6(9) . . . . ?
N1 C1 C2 C9 -122.7(6) . . . . ?
N2 C2 C3 C4 -116.7(6) . . . . ?
C9 C2 C3 C4 122.5(6) . . . . ?
C1 C2 C3 C4 -0.2(7) . . . . ?
N2 C2 C3 C8 57.9(10) . . . . ?
C9 C2 C3 C8 -62.9(9) . . . . ?
C1 C2 C3 C8 174.4(7) . . . . ?
C8 C3 C4 C5 -0.2(12) . . . . ?
C2 C3 C4 C5 175.1(8) . . . . ?
C8 C3 C4 N1 -178.6(7) . . . . ?
C2 C3 C4 N1 -3.2(9) . . . . ?
C3 C4 C5 C6 -1.2(14) . . . . ?
N1 C4 C5 C6 176.8(9) . . . . ?
C4 C5 C6 C7 1.6(15) . . . . ?
C5 C6 C7 C8 -0.6(15) . . . . ?
C4 C3 C8 C7 1.2(11) . . . . ?
C2 C3 C8 C7 -172.9(7) . . . . ?
C6 C7 C8 C3 -0.9(12) . . . . ?
N2 C2 C9 O3 -76.6(5) . . . . ?
C3 C2 C9 O3 48.8(7) . . . . ?
C1 C2 C9 O3 166.2(5) . . . . ?
N2 C2 C9 C17 37.8(5) . . . . ?
C3 C2 C9 C17 163.3(5) . . . . ?
C1 C2 C9 C17 -79.4(6) . . . . ?
N2 C2 C9 C10 165.8(5) . . . . ?
C3 C2 C9 C10 -68.7(7) . . . . ?
C1 C2 C9 C10 48.6(7) . . . . ?
O3 C9 C10 O2 -179.4(6) . . . . ?
C17 C9 C10 O2 59.6(8) . . . . ?
C2 C9 C10 O2 -60.5(8) . . . . ?
O3 C9 C10 C11 1.2(6) . . . . ?
C17 C9 C10 C11 -119.8(6) . . . . ?
C2 C9 C10 C11 120.1(6) . . . . ?
O2 C10 C11 C12 -180.0(7) . . . . ?
C9 C10 C11 C12 -0.6(7) . . . . ?
O2 C10 C11 C16 0.7(13) . . . . ?
C9 C10 C11 C16 -180.0(7) . . . . ?
C16 C11 C12 O3 179.2(6) . . . . ?
C10 C11 C12 O3 -0.3(7) . . . . ?
C16 C11 C12 C13 -1.1(10) . . . . ?
C10 C11 C12 C13 179.5(6) . . . . ?
O3 C12 C13 C14 -179.3(6) . . . . ?
C11 C12 C13 C14 1.0(10) . . . . ?
C12 C13 C14 C15 -0.5(12) . . . . ?
C13 C14 C15 C16 0.1(15) . . . . ?
C14 C15 C16 C11 -0.2(14) . . . . ?
C12 C11 C16 C15 0.6(11) . . . . ?
C10 C11 C16 C15 179.9(8) . . . . ?
O3 C9 C17 C20 -56.1(6) . . . . ?
C10 C9 C17 C20 62.9(7) . . . . ?
C2 C9 C17 C20 -169.5(5) . . . . ?
O3 C9 C17 C18 70.5(5) . . . . ?
C10 C9 C17 C18 -170.5(5) . . . . ?
C2 C9 C17 C18 -43.0(5) . . . . ?
C20 C17 C18 N2 161.2(5) . . . . ?
C9 C17 C18 N2 33.7(6) . . . . ?
C20 C17 C18 C19 -78.4(7) . . . . ?
C9 C17 C18 C19 154.1(5) . . . . ?
N2 C18 C19 F1 60.6(7) . . . . ?
C17 C18 C19 F1 -56.9(7) . . . . ?
N2 C18 C19 F2 -178.4(6) . . . . ?
C17 C18 C19 F2 64.2(8) . . . . ?
N2 C18 C19 F3 -59.2(7) . . . . ?
C17 C18 C19 F3 -176.6(6) . . . . ?
C9 C17 C20 C25 68.2(8) . . . . ?
C18 C17 C20 C25 -50.2(8) . . . . ?
C9 C17 C20 C21 -115.2(6) . . . . ?
C18 C17 C20 C21 126.4(6) . . . . ?
C25 C20 C21 C22 2.7(10) . . . . ?
C17 C20 C21 C22 -174.1(7) . . . . ?
C20 C21 C22 C23 -0.8(12) . . . . ?
C21 C22 C23 C24 -1.6(12) . . . . ?
C21 C22 C23 Br1 175.3(6) . . . . ?
C22 C23 C24 C25 1.9(12) . . . . ?
Br1 C23 C24 C25 -175.1(6) . . . . ?
C23 C24 C25 C20 0.2(11) . . . . ?
C21 C20 C25 C24 -2.4(10) . . . . ?
C17 C20 C25 C24 174.2(6) . . . . ?
O1 C1 N1 C4 169.8(7) . . . . ?
C2 C1 N1 C4 -6.0(9) . . . . ?
C3 C4 N1 C1 6.1(10) . . . . ?
C5 C4 N1 C1 -172.1(8) . . . . ?
C3 C2 N2 C18 -145.1(5) . . . . ?
C9 C2 N2 C18 -16.8(6) . . . . ?
C1 C2 N2 C18 102.7(5) . . . . ?
C19 C18 N2 C2 -132.6(5) . . . . ?
C17 C18 N2 C2 -10.7(6) . . . . ?
C13 C12 O3 C9 -178.6(6) . . . . ?
C11 C12 O3 C9 1.1(6) . . . . ?
C17 C9 O3 C12 124.7(5) . . . . ?
C10 C9 O3 C12 -1.4(6) . . . . ?
C2 C9 O3 C12 -125.9(5) . . . . ?
O4 C26 O5 C28 2(2) . . . . ?
C27 C26 O5 C28 174.8(15) . . . . ?
C29 C28 O5 C26 76(2) . . . . ?