#------------------------------------------------------------------------------
#$Date: 2025-12-02 02:56:58 +0100 (Tue 02 de Dec de 2025) $
#$Revision: 303994 $
#$URL: svn://www.crystallography.net/cod/cif/7/16/09/7160910.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_7160910
loop_
_publ_author_name
'Rakshit, Ankita J.'
'Saikia, Raktim Abha'
'Deka, Snata'
'Thakur, Ashim Jyoti'
_publ_section_title
;
 Copper-catalyzed N-arylation of Isatins Employing Aryl(TMP)iodonium Salts
;
_journal_name_full               'Organic & Biomolecular Chemistry'
_journal_paper_doi               10.1039/D5OB01451D
_journal_year                    2025
_chemical_formula_moiety         'C14 H8 Br N O2'
_chemical_formula_sum            'C14 H8 Br N O2'
_chemical_formula_weight         302.12
_chemical_name_common            1-(4-bromophenyl)isatin
_chemical_name_systematic        1-(4-bromophenyl)indoline-2,3-dione
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2025-06-12
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2025.05.31 svn.r86d253d1 for OlexSys, GUI svn.r7254)
;
_audit_update_record
;
2025-06-12 deposited with the CCDC.	2025-11-28 downloaded from the CCDC.
;
_cell_angle_alpha                98.65(5)
_cell_angle_beta                 88.67(5)
_cell_angle_gamma                89.92(5)
_cell_formula_units_Z            8
_cell_length_a                   3.938(6)
_cell_length_b                   13.90(2)
_cell_length_c                   43.76(6)
_cell_measurement_reflns_used    11731
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      29.108
_cell_measurement_theta_min      1.413
_cell_volume                     2367(6)
_computing_molecular_graphics    'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-alpha (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2016/6 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.968
_diffrn_measured_fraction_theta_max 0.920
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_unetI/netI     0.4577
_diffrn_reflns_Laue_measured_fraction_full 0.968
_diffrn_reflns_Laue_measured_fraction_max 0.920
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            11731
_diffrn_reflns_point_group_measured_fraction_full 0.968
_diffrn_reflns_point_group_measured_fraction_max 0.920
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.108
_diffrn_reflns_theta_min         1.413
_exptl_absorpt_coefficient_mu    3.465
_exptl_crystal_density_diffrn    1.696
_exptl_crystal_description       needle
_exptl_crystal_F_000             1200
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.792
_refine_diff_density_min         -1.488
_refine_diff_density_rms         0.222
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.840
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     650
_refine_ls_number_reflns         11731
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      0.842
_refine_ls_R_factor_all          0.2525
_refine_ls_R_factor_gt           0.0983
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2385
_refine_ls_wR_factor_ref         0.3318
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4339
_reflns_number_total             11731
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ob01451d3.cif
_cod_data_source_block           ajt_164p_181124_0u
_cod_database_code               7160910
_shelx_shelxl_version_number     2016/6
_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.
;
_olex2_refinement_description
;
1. Others
 Fixed Uiso: H5D(0.038) H5C(0.037) H7B(0.03) H14C(0.037) H7A(0.031) H7D(0.033)
 H7C(0.03) H12C(0.04) H6D(0.044) H10C(0.032) H6C(0.036) H5A(0.032) H13C(0.04)
 H14D(0.033) H11D(0.048) H5B(0.032) H14B(0.035) H6B(0.034) H10D(0.034)
 H11A(0.047) H11C(0.044) H13B(0.031) H12A(0.046) H14A(0.045) H12D(0.047)
 H13D(0.045) H10B(0.04) H11B(0.041) H10A(0.043) H12B(0.055) H6A(0.04)
 H13A(0.047)
 Fixed X: H5D(0.506281) H5C(-0.339443) H7B(0.190957) H14C(0.194892)
 H7A(1.133909) H7D(0.635978) H7C(-0.30094) H12C(-0.034338) H6D(0.431486) H10C(-
 0.219293) H6C(-0.479161) H5A(1.02275) H13C(0.185531) H14D(0.761837)
 H11D(1.09212) H5B(0.142452) H14B(0.696594) H6B(0.035751) H10D(1.120833)
 H11A(1.233131) H11C(-0.235488) H13B(0.680134) H12A(1.421565) H14A(1.624992)
 H12D(0.924158) H13D(0.738242) H10B(0.258093) H11B(0.267663) H10A(1.258982)
 H12B(0.466937) H6A(0.924944) H13A(1.597893)
 Fixed Y: H5D(0.312617) H5C(0.773928) H7B(0.592305) H14C(0.934671)
 H7A(1.117518) H7D(0.383599) H7C(0.905651) H12C(0.995173) H6D(0.41791)
 H10C(0.730327) H6C(0.903059) H5A(1.185678) H13C(1.04496) H14D(0.135183)
 H11D(0.458533) H5B(0.730362) H14B(0.567921) H6B(0.597229) H10D(0.386874)
 H11A(1.290821) H11C(0.841384) H13B(0.454169) H12A(1.131073) H14A(1.116601)
 H12D(0.369679) H13D(0.211814) H10B(0.768658) H11B(0.660809) H10A(1.365276)
 H12B(0.497593) H6A(1.082236) H13A(1.041599)
 Fixed Z: H5D(0.017983) H5C(0.041988) H7B(0.368969) H14C(0.164291)
 H7A(0.388475) H7D(0.11099) H7C(0.13122) H12C(0.256888) H6D(0.064259)
 H10C(0.211816) H6C(0.08023) H5A(0.482772) H13C(0.211577) H14D(0.170437)
 H11D(0.197205) H5B(0.457266) H14B(0.334373) H6B(0.421809) H10D(0.143734)
 H11A(0.278796) H11C(0.255751) H13B(0.29002) H12A(0.264678) H14A(0.354937)
 H12D(0.233994) H13D(0.222164) H10B(0.290799) H11B(0.242621) H10A(0.330917)
 H12B(0.244862) H6A(0.437179) H13A(0.304554)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-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
Br1D Br 0.8018(3) 0.12013(10) 0.00091(3) 0.0314(4) Uani 1 1 d . . . . .
Br1A Br 1.3021(3) 1.38006(10) 0.49914(3) 0.0313(4) Uani 1 1 d . . . . .
Br1C Br -0.0123(3) 0.58475(11) 0.04110(3) 0.0368(4) Uani 1 1 d . . . . .
Br1B Br 0.4877(3) 0.91517(11) 0.45889(3) 0.0364(4) Uani 1 1 d . . . . .
O1A O 1.767(2) 1.4311(7) 0.3725(2) 0.037(2) Uani 1 1 d . . . . .
O1B O 0.791(2) 0.8734(7) 0.3230(2) 0.036(2) Uani 1 1 d . . . . .
O2A O 1.645(2) 1.4758(7) 0.4401(2) 0.034(2) Uani 1 1 d . . . . .
O2C O 0.252(2) 0.5362(6) 0.1109(2) 0.032(2) Uani 1 1 d . . . . .
O1C O 0.286(2) 0.6273(8) 0.1760(2) 0.041(2) Uani 1 1 d . . . . .
N1A N 1.468(3) 1.2883(8) 0.3797(2) 0.029(3) Uani 1 1 d . . . . .
N1D N 0.964(3) 0.2082(8) 0.1206(2) 0.029(2) Uani 1 1 d . . . . .
O2D O 1.149(2) 0.0244(7) 0.0600(2) 0.033(2) Uani 1 1 d . . . . .
C4B C 0.383(3) 0.8107(9) 0.4280(3) 0.023(3) Uani 1 1 d . . . . .
O1D O 1.265(2) 0.0677(7) 0.1275(2) 0.039(2) Uani 1 1 d . . . . .
O2B O 0.743(2) 0.9668(7) 0.3881(2) 0.039(2) Uani 1 1 d . . . . .
C4C C -0.117(3) 0.6888(10) 0.0718(3) 0.030(3) Uani 1 1 d . . . . .
C1D C 1.107(3) 0.1213(9) 0.1101(3) 0.025(3) Uani 1 1 d D . . . .
N1C N 0.009(3) 0.7538(8) 0.1560(2) 0.029(2) Uani 1 1 d . . . . .
C5D C 0.583(3) 0.2962(9) 0.0365(4) 0.032(3) Uani 1 1 d . . . . .
H5D H 0.506281 0.312617 0.017983 0.038 Uiso 1 1 calc R U . . .
C4A C 1.247(3) 1.2927(9) 0.4628(3) 0.026(3) Uani 1 1 d . . . . .
N1B N 0.510(2) 0.7465(7) 0.3437(2) 0.024(2) Uani 1 1 d . . . . .
C3B C 0.474(3) 0.8123(10) 0.3966(3) 0.030(3) Uani 1 1 d . . . . .
C5C C -0.285(3) 0.7726(10) 0.0625(3) 0.030(3) Uani 1 1 d . . . . .
H5C H -0.339443 0.773928 0.041988 0.037 Uiso 1 1 calc R U . . .
C2D C 1.049(3) 0.0982(9) 0.0754(3) 0.027(3) Uani 1 1 d D . . . .
C7B C 0.235(3) 0.6467(9) 0.3834(3) 0.025(3) Uani 1 1 d . . . . .
H7B H 0.190957 0.592305 0.368969 0.030 Uiso 1 1 calc R U . . .
C14C C 0.109(3) 0.9163(10) 0.1825(3) 0.031(3) Uani 1 1 d . . . . .
H14C H 0.194892 0.934671 0.164291 0.037 Uiso 1 1 calc R U . . .
C3A C 1.376(3) 1.3158(9) 0.4340(3) 0.025(3) Uani 1 1 d . . . . .
C8D C 0.825(3) 0.2499(9) 0.0931(3) 0.027(3) Uani 1 1 d . . . . .
C3D C 0.867(3) 0.1832(10) 0.0662(3) 0.031(3) Uani 1 1 d . . . . .
C2B C 0.636(3) 0.8838(9) 0.3787(3) 0.027(3) Uani 1 1 d D . . . .
C8C C -0.103(3) 0.7699(9) 0.1253(3) 0.022(3) Uani 1 1 d . . . . .
C4D C 0.746(3) 0.2067(9) 0.0378(3) 0.025(3) Uani 1 1 d . . . . .
C3C C -0.026(3) 0.6880(8) 0.1035(3) 0.025(3) Uani 1 1 d . . . . .
C7A C 1.162(3) 1.1618(9) 0.4064(3) 0.026(3) Uani 1 1 d . . . . .
H7A H 1.133909 1.117518 0.388475 0.031 Uiso 1 1 calc R U . . .
C7D C 0.664(3) 0.3390(10) 0.0930(3) 0.027(3) Uani 1 1 d . . . . .
H7D H 0.635978 0.383599 0.110990 0.033 Uiso 1 1 calc R U . . .
C7C C -0.260(3) 0.8507(10) 0.1166(3) 0.025(3) Uani 1 1 d . . . . .
H7C H -0.300940 0.905651 0.131220 0.030 Uiso 1 1 calc R U . . .
C1C C 0.160(3) 0.6602(10) 0.1551(3) 0.032(3) Uani 1 1 d D . . . .
C9A C 1.449(3) 1.2460(9) 0.3471(3) 0.029(3) Uani 1 1 d . . . . .
C12C C -0.029(3) 0.9521(10) 0.2384(3) 0.033(3) Uani 1 1 d . . . . .
H12C H -0.034338 0.995173 0.256888 0.040 Uiso 1 1 calc R U . . .
C6D C 0.544(3) 0.3591(10) 0.0645(4) 0.037(3) Uani 1 1 d . . . . .
H6D H 0.431486 0.417910 0.064259 0.044 Uiso 1 1 calc R U . . .
C10C C -0.144(3) 0.7936(10) 0.2115(3) 0.027(3) Uani 1 1 d . . . . .
H10C H -0.219293 0.730327 0.211816 0.032 Uiso 1 1 calc R U . . .
C2C C 0.136(3) 0.6187(12) 0.1207(3) 0.037(3) Uani 1 1 d D . . . .
C6C C -0.360(3) 0.8500(10) 0.0853(3) 0.030(3) Uani 1 1 d . . . . .
H6C H -0.479161 0.903059 0.080230 0.036 Uiso 1 1 calc R U . . .
C5A C 1.092(3) 1.2033(9) 0.4639(3) 0.027(3) Uani 1 1 d . . . . .
H5A H 1.022750 1.185678 0.482772 0.032 Uiso 1 1 calc R U . . .
C13C C 0.103(3) 0.9821(10) 0.2111(3) 0.033(3) Uani 1 1 d . . . . .
H13C H 0.185531 1.044960 0.211577 0.040 Uiso 1 1 calc R U . . .
C14D C 0.829(3) 0.1996(9) 0.1757(3) 0.028(3) Uani 1 1 d . . . . .
H14D H 0.761837 0.135183 0.170437 0.033 Uiso 1 1 calc R U . . .
C1A C 1.614(3) 1.3803(9) 0.3891(3) 0.027(3) Uani 1 1 d D . . . .
C11D C 1.030(3) 0.3939(12) 0.1914(3) 0.040(4) Uani 1 1 d . . . . .
H11D H 1.092120 0.458533 0.197205 0.048 Uiso 1 1 calc R U . . .
C1B C 0.658(4) 0.8374(9) 0.3460(3) 0.033(3) Uani 1 1 d D . . . .
C5B C 0.211(3) 0.7297(9) 0.4367(3) 0.027(3) Uani 1 1 d . . . . .
H5B H 0.142452 0.730362 0.457266 0.032 Uiso 1 1 calc R U . . .
C14B C 0.610(3) 0.5851(9) 0.3163(3) 0.029(3) Uani 1 1 d . . . . .
H14B H 0.696594 0.567921 0.334373 0.035 Uiso 1 1 calc R U . . .
C8B C 0.396(3) 0.7301(8) 0.3750(3) 0.021(3) Uani 1 1 d . . . . .
C9B C 0.492(3) 0.6780(9) 0.3161(3) 0.027(3) Uani 1 1 d . . . . .
C6B C 0.144(3) 0.6504(9) 0.4154(3) 0.028(3) Uani 1 1 d . . . . .
H6B H 0.035751 0.597229 0.421809 0.034 Uiso 1 1 calc R U . . .
C10D C 1.047(3) 0.3513(10) 0.1590(3) 0.028(3) Uani 1 1 d . . . . .
H10D H 1.120833 0.386874 0.143734 0.034 Uiso 1 1 calc R U . . .
C9C C -0.020(3) 0.8237(9) 0.1833(3) 0.026(3) Uani 1 1 d . . . . .
C11A C 1.314(4) 1.2560(12) 0.2937(4) 0.040(4) Uani 1 1 d . . . . .
H11A H 1.233131 1.290821 0.278796 0.047 Uiso 1 1 calc R U . . .
C11C C -0.148(3) 0.8598(11) 0.2376(3) 0.036(3) Uani 1 1 d . . . . .
H11C H -0.235488 0.841384 0.255751 0.044 Uiso 1 1 calc R U . . .
C13B C 0.601(3) 0.5172(8) 0.2898(3) 0.026(3) Uani 1 1 d . . . . .
H13B H 0.680134 0.454169 0.290020 0.031 Uiso 1 1 calc R U . . .
C12A C 1.421(4) 1.1604(11) 0.2852(3) 0.039(4) Uani 1 1 d . . . . .
H12A H 1.421565 1.131073 0.264678 0.046 Uiso 1 1 calc R U . . .
C8A C 1.323(3) 1.2515(8) 0.4054(3) 0.024(3) Uani 1 1 d . . . . .
C14A C 1.549(3) 1.1509(11) 0.3397(4) 0.037(3) Uani 1 1 d . . . . .
H14A H 1.624992 1.116601 0.354937 0.045 Uiso 1 1 calc R U . . .
C12D C 0.924(4) 0.3407(11) 0.2134(4) 0.039(3) Uani 1 1 d . . . . .
H12D H 0.924158 0.369679 0.233994 0.047 Uiso 1 1 calc R U . . .
C13D C 0.817(3) 0.2452(12) 0.2065(3) 0.037(3) Uani 1 1 d . . . . .
H13D H 0.738242 0.211814 0.222164 0.045 Uiso 1 1 calc R U . . .
C10B C 0.350(3) 0.7065(10) 0.2896(3) 0.033(3) Uani 1 1 d . . . . .
H10B H 0.258093 0.768658 0.290799 0.040 Uiso 1 1 calc R U . . .
C11B C 0.345(3) 0.6421(10) 0.2608(4) 0.034(3) Uani 1 1 d . . . . .
H11B H 0.267663 0.660809 0.242621 0.041 Uiso 1 1 calc R U . . .
C10A C 1.328(3) 1.3010(11) 0.3251(3) 0.036(3) Uani 1 1 d . . . . .
H10A H 1.258982 1.365276 0.330917 0.043 Uiso 1 1 calc R U . . .
C9D C 0.949(3) 0.2553(10) 0.1521(3) 0.028(3) Uani 1 1 d . . . . .
C2A C 1.556(3) 1.4019(10) 0.4239(3) 0.035(3) Uani 1 1 d D . . . .
C12B C 0.472(4) 0.5441(12) 0.2625(4) 0.046(4) Uani 1 1 d . . . . .
H12B H 0.466937 0.497593 0.244862 0.055 Uiso 1 1 calc R U . . .
C6A C 1.041(3) 1.1401(9) 0.4364(3) 0.034(3) Uani 1 1 d . . . . .
H6A H 0.924944 1.082236 0.437179 0.040 Uiso 1 1 calc R U . . .
C13A C 1.535(4) 1.1067(11) 0.3096(3) 0.039(4) Uani 1 1 d . . . . .
H13A H 1.597893 1.041599 0.304554 0.047 Uiso 1 1 calc R U . . .
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'
Br Br -0.2901 2.4595 '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'
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
C1A N1A C9A 122.0(10) . . ?
C1A N1A C8A 110.4(10) . . ?
C8A N1A C9A 127.3(10) . . ?
C1D N1D C8D 108.3(10) . . ?
C1D N1D C9D 126.5(11) . . ?
C9D N1D C8D 125.3(10) . . ?
C3B C4B Br1B 121.3(9) . . ?
C3B C4B C5B 120.2(12) . . ?
C5B C4B Br1B 118.5(9) . . ?
C5C C4C Br1C 117.4(10) . . ?
C3C C4C Br1C 121.5(10) . . ?
C3C C4C C5C 121.1(12) . . ?
N1D C1D C2D 108.4(10) . . ?
O1D C1D N1D 124.1(11) . . ?
O1D C1D C2D 127.6(11) . . ?
C1C N1C C8C 111.7(10) . . ?
C1C N1C C9C 123.6(11) . . ?
C9C N1C C8C 124.6(11) . . ?
C4D C5D H5D 121.8 . . ?
C6D C5D H5D 121.8 . . ?
C6D C5D C4D 116.4(14) . . ?
C3A C4A Br1A 120.0(9) . . ?
C5A C4A Br1A 120.1(10) . . ?
C5A C4A C3A 119.8(12) . . ?
C1B N1B C8B 108.5(10) . . ?
C1B N1B C9B 125.4(10) . . ?
C9B N1B C8B 126.0(10) . . ?
C4B C3B C2B 135.7(12) . . ?
C8B C3B C4B 117.9(12) . . ?
C8B C3B C2B 106.4(10) . . ?
C4C C5C H5C 121.4 . . ?
C6C C5C C4C 117.3(12) . . ?
C6C C5C H5C 121.4 . . ?
O2D C2D C1D 122.6(12) . . ?
O2D C2D C3D 130.4(12) . . ?
C3D C2D C1D 107.0(10) . . ?
C8B C7B H7B 121.7 . . ?
C8B C7B C6B 116.5(12) . . ?
C6B C7B H7B 121.7 . . ?
C13C C14C H14C 121.6 . . ?
C9C C14C H14C 121.6 . . ?
C9C C14C C13C 116.9(12) . . ?
C4A C3A C8A 121.1(12) . . ?
C4A C3A C2A 135.0(12) . . ?
C8A C3A C2A 103.7(10) . . ?
C3D C8D N1D 110.2(11) . . ?
C3D C8D C7D 121.4(13) . . ?
C7D C8D N1D 128.3(11) . . ?
C8D C3D C2D 106.0(12) . . ?
C8D C3D C4D 119.5(12) . . ?
C4D C3D C2D 134.4(12) . . ?
O2B C2B C3B 129.0(11) . . ?
O2B C2B C1B 123.7(12) . . ?
C1B C2B C3B 107.2(10) . . ?
C3C C8C N1C 109.8(11) . . ?
C7C C8C N1C 129.5(11) . . ?
C7C C8C C3C 120.7(12) . . ?
C5D C4D Br1D 117.8(11) . . ?
C5D C4D C3D 121.1(12) . . ?
C3D C4D Br1D 121.1(10) . . ?
C4C C3C C2C 135.8(11) . . ?
C8C C3C C4C 118.6(11) . . ?
C8C C3C C2C 105.6(11) . . ?
C8A C7A H7A 121.0 . . ?
C8A C7A C6A 118.0(12) . . ?
C6A C7A H7A 121.0 . . ?
C8D C7D H7D 121.3 . . ?
C8D C7D C6D 117.4(12) . . ?
C6D C7D H7D 121.3 . . ?
C8C C7C H7C 119.8 . . ?
C8C C7C C6C 120.5(12) . . ?
C6C C7C H7C 119.8 . . ?
O1C C1C N1C 127.4(12) . . ?
O1C C1C C2C 131.0(13) . . ?
N1C C1C C2C 101.5(12) . . ?
C14A C9A N1A 116.3(13) . . ?
C14A C9A C10A 122.8(14) . . ?
C10A C9A N1A 120.9(11) . . ?
C13C C12C H12C 120.2 . . ?
C11C C12C H12C 120.2 . . ?
C11C C12C C13C 119.6(13) . . ?
C5D C6D C7D 124.2(13) . . ?
C5D C6D H6D 117.9 . . ?
C7D C6D H6D 117.9 . . ?
C9C C10C H10C 120.9 . . ?
C11C C10C H10C 120.9 . . ?
C11C C10C C9C 118.1(13) . . ?
O2C C2C C3C 128.8(12) . . ?
O2C C2C C1C 119.9(13) . . ?
C3C C2C C1C 111.3(12) . . ?
C5C C6C C7C 121.7(13) . . ?
C5C C6C H6C 119.2 . . ?
C7C C6C H6C 119.2 . . ?
C4A C5A H5A 120.3 . . ?
C4A C5A C6A 119.4(12) . . ?
C6A C5A H5A 120.3 . . ?
C14C C13C H13C 119.8 . . ?
C12C C13C C14C 120.4(12) . . ?
C12C C13C H13C 119.8 . . ?
C13D C14D H14D 120.8 . . ?
C13D C14D C9D 118.4(12) . . ?
C9D C14D H14D 120.8 . . ?
O1A C1A N1A 126.9(11) . . ?
O1A C1A C2A 127.2(12) . . ?
N1A C1A C2A 105.9(10) . . ?
C10D C11D H11D 119.6 . . ?
C12D C11D H11D 119.6 . . ?
C12D C11D C10D 120.9(14) . . ?
O1B C1B N1B 124.3(11) . . ?
O1B C1B C2B 127.2(12) . . ?
N1B C1B C2B 108.5(10) . . ?
C4B C5B H5B 119.7 . . ?
C6B C5B C4B 120.6(12) . . ?
C6B C5B H5B 119.7 . . ?
C9B C14B H14B 119.9 . . ?
C9B C14B C13B 120.1(13) . . ?
C13B C14B H14B 119.9 . . ?
C3B C8B N1B 109.4(10) . . ?
C3B C8B C7B 122.8(12) . . ?
C7B C8B N1B 127.8(11) . . ?
C14B C9B N1B 118.6(13) . . ?
C14B C9B C10B 121.9(13) . . ?
C10B C9B N1B 119.5(12) . . ?
C7B C6B H6B 119.0 . . ?
C5B C6B C7B 121.9(12) . . ?
C5B C6B H6B 119.0 . . ?
C11D C10D H10D 121.7 . . ?
C9D C10D C11D 116.5(13) . . ?
C9D C10D H10D 121.7 . . ?
N1C C9C C10C 119.2(11) . . ?
C14C C9C N1C 118.4(11) . . ?
C14C C9C C10C 122.1(12) . . ?
C12A C11A H11A 119.9 . . ?
C12A C11A C10A 120.2(15) . . ?
C10A C11A H11A 119.9 . . ?
C12C C11C H11C 118.5 . . ?
C10C C11C C12C 122.9(14) . . ?
C10C C11C H11C 118.5 . . ?
C14B C13B H13B 120.2 . . ?
C14B C13B C12B 119.6(12) . . ?
C12B C13B H13B 120.2 . . ?
C11A C12A H12A 120.9 . . ?
C11A C12A C13A 118.2(13) . . ?
C13A C12A H12A 120.9 . . ?
N1A C8A C3A 112.0(10) . . ?
C7A C8A N1A 128.8(12) . . ?
C7A C8A C3A 119.0(12) . . ?
C9A C14A H14A 120.4 . . ?
C9A C14A C13A 119.2(15) . . ?
C13A C14A H14A 120.4 . . ?
C11D C12D H12D 118.5 . . ?
C11D C12D C13D 123.0(15) . . ?
C13D C12D H12D 118.5 . . ?
C14D C13D H13D 120.5 . . ?
C12D C13D C14D 119.0(14) . . ?
C12D C13D H13D 120.5 . . ?
C9B C10B H10B 119.2 . . ?
C9B C10B C11B 121.5(13) . . ?
C11B C10B H10B 119.2 . . ?
C10B C11B H11B 123.0 . . ?
C10B C11B C12B 113.9(14) . . ?
C12B C11B H11B 123.0 . . ?
C9A C10A C11A 118.5(13) . . ?
C9A C10A H10A 120.7 . . ?
C11A C10A H10A 120.7 . . ?
N1D C9D C14D 118.3(12) . . ?
C10D C9D N1D 119.5(12) . . ?
C10D C9D C14D 122.2(12) . . ?
O2A C2A C3A 127.4(12) . . ?
O2A C2A C1A 124.7(12) . . ?
C3A C2A C1A 107.9(11) . . ?
C13B C12B C11B 122.8(14) . . ?
C13B C12B H12B 118.6 . . ?
C11B C12B H12B 118.6 . . ?
C7A C6A H6A 118.8 . . ?
C5A C6A C7A 122.4(12) . . ?
C5A C6A H6A 118.8 . . ?
C12A C13A H13A 119.5 . . ?
C14A C13A C12A 121.0(13) . . ?
C14A C13A H13A 119.5 . . ?
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
Br1D C4D 1.870(13) . ?
Br1A C4A 1.866(13) . ?
Br1C C4C 1.859(13) . ?
Br1B C4B 1.882(13) . ?
O1A C1A 1.232(15) . ?
O1B C1B 1.290(15) . ?
O2A C2A 1.215(16) . ?
O2C C2C 1.245(17) . ?
O1C C1C 1.202(17) . ?
N1A C9A 1.460(17) . ?
N1A C1A 1.410(16) . ?
N1A C8A 1.416(16) . ?
N1D C1D 1.342(16) . ?
N1D C8D 1.523(17) . ?
N1D C9D 1.433(15) . ?
O2D C2D 1.199(15) . ?
C4B C3B 1.413(18) . ?
C4B C5B 1.413(17) . ?
O1D C1D 1.313(15) . ?
O2B C2B 1.243(15) . ?
C4C C5C 1.45(2) . ?
C4C C3C 1.44(2) . ?
C1D C2D 1.526(14) . ?
N1C C8C 1.471(18) . ?
N1C C1C 1.425(18) . ?
N1C C9C 1.424(15) . ?
C5D H5D 0.9300 . ?
C5D C4D 1.408(18) . ?
C5D C6D 1.40(2) . ?
C4A C3A 1.431(17) . ?
C4A C5A 1.391(18) . ?
N1B C1B 1.383(16) . ?
N1B C8B 1.482(16) . ?
N1B C9B 1.424(16) . ?
C3B C2B 1.490(18) . ?
C3B C8B 1.410(19) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.380(19) . ?
C2D C3D 1.491(19) . ?
C7B H7B 0.9300 . ?
C7B C8B 1.414(17) . ?
C7B C6B 1.428(18) . ?
C14C H14C 0.9300 . ?
C14C C13C 1.433(18) . ?
C14C C9C 1.388(19) . ?
C3A C8A 1.444(18) . ?
C3A C2A 1.509(19) . ?
C8D C3D 1.391(18) . ?
C8D C7D 1.392(18) . ?
C3D C4D 1.43(2) . ?
C2B C1B 1.479(14) . ?
C8C C3C 1.401(16) . ?
C8C C7C 1.388(18) . ?
C3C C2C 1.46(2) . ?
C7A H7A 0.9300 . ?
C7A C8A 1.406(17) . ?
C7A C6A 1.459(19) . ?
C7D H7D 0.9300 . ?
C7D C6D 1.41(2) . ?
C7C H7C 0.9300 . ?
C7C C6C 1.434(19) . ?
C1C C2C 1.534(15) . ?
C9A C14A 1.368(19) . ?
C9A C10A 1.41(2) . ?
C12C H12C 0.9300 . ?
C12C C13C 1.41(2) . ?
C12C C11C 1.36(2) . ?
C6D H6D 0.9300 . ?
C10C H10C 0.9300 . ?
C10C C9C 1.436(17) . ?
C10C C11C 1.354(19) . ?
C6C H6C 0.9300 . ?
C5A H5A 0.9300 . ?
C5A C6A 1.399(18) . ?
C13C H13C 0.9300 . ?
C14D H14D 0.9300 . ?
C14D C13D 1.404(19) . ?
C14D C9D 1.452(18) . ?
C1A C2A 1.521(14) . ?
C11D H11D 0.9300 . ?
C11D C10D 1.453(19) . ?
C11D C12D 1.36(2) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.363(18) . ?
C14B H14B 0.9300 . ?
C14B C9B 1.374(18) . ?
C14B C13B 1.381(18) . ?
C9B C10B 1.41(2) . ?
C6B H6B 0.9300 . ?
C10D H10D 0.9300 . ?
C10D C9D 1.382(18) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.39(2) . ?
C11A C10A 1.42(2) . ?
C11C H11C 0.9300 . ?
C13B H13B 0.9300 . ?
C13B C12B 1.41(2) . ?
C12A H12A 0.9300 . ?
C12A C13A 1.47(2) . ?
C14A H14A 0.9300 . ?
C14A C13A 1.37(2) . ?
C12D H12D 0.9300 . ?
C12D C13D 1.39(2) . ?
C13D H13D 0.9300 . ?
C10B H10B 0.9300 . ?
C10B C11B 1.433(19) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.46(2) . ?
C10A H10A 0.9300 . ?
C12B H12B 0.9300 . ?
C6A H6A 0.9300 . ?
C13A H13A 0.9300 . ?
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
Br1A C4A C3A C8A -177.2(9) . . . . ?
Br1A C4A C3A C2A -2(2) . . . . ?
Br1A C4A C5A C6A 177.6(10) . . . . ?
Br1C C4C C5C C6C -179.5(9) . . . . ?
Br1C C4C C3C C8C 178.0(8) . . . . ?
Br1C C4C C3C C2C -2.8(19) . . . . ?
Br1B C4B C3B C2B -4(2) . . . . ?
Br1B C4B C3B C8B 178.2(8) . . . . ?
Br1B C4B C5B C6B -176.9(9) . . . . ?
O1A C1A C2A O2A 3(2) . . . . ?
O1A C1A C2A C3A -176.4(13) . . . . ?
O1C C1C C2C O2C 2(2) . . . . ?
O1C C1C C2C C3C -176.7(14) . . . . ?
N1A C9A C14A C13A 179.5(11) . . . . ?
N1A C9A C10A C11A -179.8(11) . . . . ?
N1A C1A C2A O2A -179.4(13) . . . . ?
N1A C1A C2A C3A 1.4(14) . . . . ?
N1D C1D C2D O2D -179.8(12) . . . . ?
N1D C1D C2D C3D 2.0(13) . . . . ?
N1D C8D C3D C2D -2.5(13) . . . . ?
N1D C8D C3D C4D 178.6(10) . . . . ?
N1D C8D C7D C6D -177.3(11) . . . . ?
O2D C2D C3D C8D -177.6(13) . . . . ?
O2D C2D C3D C4D 1(2) . . . . ?
C4B C3B C2B O2B 1(2) . . . . ?
C4B C3B C2B C1B 179.8(14) . . . . ?
C4B C3B C8B N1B 179.7(10) . . . . ?
C4B C3B C8B C7B -0.8(17) . . . . ?
C4B C5B C6B C7B -1.8(19) . . . . ?
O1D C1D C2D O2D 0(2) . . . . ?
O1D C1D C2D C3D -178.1(11) . . . . ?
O2B C2B C1B O1B 1(2) . . . . ?
O2B C2B C1B N1B -179.0(12) . . . . ?
C4C C5C C6C C7C 3.6(18) . . . . ?
C4C C3C C2C O2C 2(2) . . . . ?
C4C C3C C2C C1C -179.2(13) . . . . ?
C1D N1D C8D C3D 4.0(13) . . . . ?
C1D N1D C8D C7D -178.5(12) . . . . ?
C1D N1D C9D C14D -49.4(17) . . . . ?
C1D N1D C9D C10D 130.6(14) . . . . ?
C1D C2D C3D C8D 0.5(13) . . . . ?
C1D C2D C3D C4D 179.1(12) . . . . ?
N1C C8C C3C C4C 179.6(10) . . . . ?
N1C C8C C3C C2C 0.2(12) . . . . ?
N1C C8C C7C C6C -177.6(11) . . . . ?
N1C C1C C2C O2C 178.8(11) . . . . ?
N1C C1C C2C C3C -0.3(13) . . . . ?
C4A C3A C8A N1A 179.3(11) . . . . ?
C4A C3A C8A C7A -4.4(18) . . . . ?
C4A C3A C2A O2A 3(3) . . . . ?
C4A C3A C2A C1A -178.2(13) . . . . ?
C4A C5A C6A C7A 4(2) . . . . ?
N1B C9B C10B C11B 176.3(10) . . . . ?
C3B C4B C5B C6B 2.9(18) . . . . ?
C3B C2B C1B O1B -177.8(13) . . . . ?
C3B C2B C1B N1B 2.4(15) . . . . ?
C5C C4C C3C C8C 0.1(16) . . . . ?
C5C C4C C3C C2C 179.3(12) . . . . ?
C2D C3D C4D Br1D 0.7(19) . . . . ?
C2D C3D C4D C5D -178.9(12) . . . . ?
C3A C4A C5A C6A -5.0(18) . . . . ?
C8D N1D C1D O1D 176.7(11) . . . . ?
C8D N1D C1D C2D -3.5(13) . . . . ?
C8D N1D C9D C14D 131.5(13) . . . . ?
C8D N1D C9D C10D -48.4(17) . . . . ?
C8D C3D C4D Br1D 179.1(9) . . . . ?
C8D C3D C4D C5D -0.5(17) . . . . ?
C8D C7D C6D C5D -1.4(19) . . . . ?
C3D C8D C7D C6D 0.0(18) . . . . ?
C2B C3B C8B N1B 1.2(13) . . . . ?
C2B C3B C8B C7B -179.3(11) . . . . ?
C8C N1C C1C O1C 177.0(13) . . . . ?
C8C N1C C1C C2C 0.4(13) . . . . ?
C8C N1C C9C C14C -51.9(17) . . . . ?
C8C N1C C9C C10C 135.0(12) . . . . ?
C8C C3C C2C O2C -178.9(12) . . . . ?
C8C C3C C2C C1C 0.1(13) . . . . ?
C8C C7C C6C C5C -4.3(18) . . . . ?
C4D C5D C6D C7D 1.7(18) . . . . ?
C3C C4C C5C C6C -1.5(17) . . . . ?
C3C C8C C7C C6C 2.8(16) . . . . ?
C7D C8D C3D C2D 179.7(11) . . . . ?
C7D C8D C3D C4D 0.9(18) . . . . ?
C7C C8C C3C C4C -0.7(16) . . . . ?
C7C C8C C3C C2C 179.9(10) . . . . ?
C1C N1C C8C C3C -0.4(13) . . . . ?
C1C N1C C8C C7C 180.0(11) . . . . ?
C1C N1C C9C C14C 125.9(13) . . . . ?
C1C N1C C9C C10C -47.2(17) . . . . ?
C9A N1A C1A O1A -7(2) . . . . ?
C9A N1A C1A C2A 174.9(11) . . . . ?
C9A N1A C8A C3A -176.4(11) . . . . ?
C9A N1A C8A C7A 8(2) . . . . ?
C9A C14A C13A C12A 1(2) . . . . ?
C6D C5D C4D Br1D 179.6(8) . . . . ?
C6D C5D C4D C3D -0.8(16) . . . . ?
C5A C4A C3A C8A 5.5(18) . . . . ?
C5A C4A C3A C2A -179.6(13) . . . . ?
C13C C14C C9C N1C -174.8(11) . . . . ?
C13C C14C C9C C10C -1.9(19) . . . . ?
C13C C12C C11C C10C 1(2) . . . . ?
C1A N1A C9A C14A 133.2(13) . . . . ?
C1A N1A C9A C10A -48.0(17) . . . . ?
C1A N1A C8A C3A -2.3(14) . . . . ?
C1A N1A C8A C7A -178.1(12) . . . . ?
C11D C10D C9D N1D -179.1(11) . . . . ?
C11D C10D C9D C14D 0.9(18) . . . . ?
C11D C12D C13D C14D 2(2) . . . . ?
C1B N1B C8B C3B 0.3(13) . . . . ?
C1B N1B C8B C7B -179.2(12) . . . . ?
C1B N1B C9B C14B 126.7(14) . . . . ?
C1B N1B C9B C10B -54.2(17) . . . . ?
C5B C4B C3B C2B 176.3(13) . . . . ?
C5B C4B C3B C8B -1.6(17) . . . . ?
C14B C9B C10B C11B -4.7(18) . . . . ?
C14B C13B C12B C11B 0(2) . . . . ?
C8B N1B C1B O1B 178.6(12) . . . . ?
C8B N1B C1B C2B -1.7(14) . . . . ?
C8B N1B C9B C14B -48.7(16) . . . . ?
C8B N1B C9B C10B 130.4(12) . . . . ?
C8B C3B C2B O2B 179.3(13) . . . . ?
C8B C3B C2B C1B -2.2(14) . . . . ?
C8B C7B C6B C5B -0.6(18) . . . . ?
C9B N1B C1B O1B 2(2) . . . . ?
C9B N1B C1B C2B -177.7(11) . . . . ?
C9B N1B C8B C3B 176.3(11) . . . . ?
C9B N1B C8B C7B -3.2(18) . . . . ?
C9B C14B C13B C12B 0.4(18) . . . . ?
C9B C10B C11B C12B 4.8(17) . . . . ?
C6B C7B C8B N1B -178.7(11) . . . . ?
C6B C7B C8B C3B 1.9(17) . . . . ?
C10D C11D C12D C13D -2(2) . . . . ?
C9C N1C C8C C3C 177.6(11) . . . . ?
C9C N1C C8C C7C -2.0(19) . . . . ?
C9C N1C C1C O1C -1(2) . . . . ?
C9C N1C C1C C2C -177.7(11) . . . . ?
C9C C14C C13C C12C 0.2(19) . . . . ?
C9C C10C C11C C12C -2(2) . . . . ?
C11A C12A C13A C14A -3(2) . . . . ?
C11C C12C C13C C14C 1(2) . . . . ?
C11C C10C C9C N1C 175.8(12) . . . . ?
C11C C10C C9C C14C 3.0(19) . . . . ?
C13B C14B C9B N1B -179.1(10) . . . . ?
C13B C14B C9B C10B 1.9(18) . . . . ?
C12A C11A C10A C9A -1(2) . . . . ?
C8A N1A C9A C14A -53.4(17) . . . . ?
C8A N1A C9A C10A 125.4(14) . . . . ?
C8A N1A C1A O1A 178.2(13) . . . . ?
C8A N1A C1A C2A 0.5(13) . . . . ?
C8A C3A C2A O2A 178.1(13) . . . . ?
C8A C3A C2A C1A -2.6(14) . . . . ?
C8A C7A C6A C5A -2.7(19) . . . . ?
C14A C9A C10A C11A -1(2) . . . . ?
C12D C11D C10D C9D 0.5(19) . . . . ?
C13D C14D C9D N1D 179.3(11) . . . . ?
C13D C14D C9D C10D -0.7(19) . . . . ?
C10B C11B C12B C13B -2.6(19) . . . . ?
C10A C9A C14A C13A 1(2) . . . . ?
C10A C11A C12A C13A 2(2) . . . . ?
C9D N1D C1D O1D -2.5(19) . . . . ?
C9D N1D C1D C2D 177.4(11) . . . . ?
C9D N1D C8D C3D -176.9(11) . . . . ?
C9D N1D C8D C7D 0.7(19) . . . . ?
C9D C14D C13D C12D -1.0(19) . . . . ?
C2A C3A C8A N1A 3.0(14) . . . . ?
C2A C3A C8A C7A 179.2(11) . . . . ?
C6A C7A C8A N1A 178.5(12) . . . . ?
C6A C7A C8A C3A 3.0(17) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.9685(12)
2 0.0315(12)
