#------------------------------------------------------------------------------
#$Date: 2022-10-01 05:04:56 +0300 (Sat, 01 Oct 2022) $
#$Revision: 278297 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/41/2244190.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_2244190
loop_
_publ_author_name
'Stapf, Manuel'
'Leibiger, Betty'
'Schwarzer, Anke'
'Mazik, Monika'
_publ_section_title
;
 Crystal structures of
 2-[3,5-bis(bromomethyl)-2,4,6-triethylbenzyl]isoindoline-1,3-dione and
 2-{5-(bromomethyl)-3-[(1,3-dioxoisoindolin-2-yl)methyl]-2,4,6-triethylbenzyl}isoindoline-1,3-dione
;
_journal_coeditor_code           ZQ2264
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              919
_journal_page_last               923
_journal_paper_doi               10.1107/S205698902100788X
_journal_volume                  77
_journal_year                    2021
_chemical_formula_iupac          'C23 H25 Br2 N O2'
_chemical_formula_moiety         'C23 H25 Br2 N O2'
_chemical_formula_sum            'C23 H25 Br2 N O2'
_chemical_formula_weight         507.26
_chemical_name_systematic
;
2-[3,5-Bis(bromomethyl)-2,4,6-triethylbenzyl]isoindoline-1,3-dione
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.099(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.367(2)
_cell_length_b                   19.966(3)
_cell_length_c                   16.919(4)
_cell_measurement_reflns_used    2236
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      2.57
_cell_volume                     4338.4(14)
_computing_cell_refinement
;
X-AREA (Stoe, 2009)
;
_computing_data_collection
;
X-AREA (Stoe, 2009)
;
_computing_data_reduction
;
X-RED (Stoe, 2009)
;
_computing_molecular_graphics
;
XP (Sheldrick, 2008)
;
_computing_publication_material
;
WinGX (Farrugia, 2012), publCIF (Westrip, 2010)
and shelXle
(Hübschle et al.,  2011)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT2018/2 (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      153(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0672
_diffrn_reflns_av_unetI/netI     0.0398
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            48044
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         2.584
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_source_voltage           50
_exptl_absorpt_coefficient_mu    3.755
_exptl_absorpt_correction_T_max  0.4722
_exptl_absorpt_correction_T_min  0.3236
_exptl_absorpt_correction_type   integration
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_description       piece
_exptl_crystal_F_000             2048
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.170
_refine_diff_density_max         0.776
_refine_diff_density_min         -0.846
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     516
_refine_ls_number_reflns         8523
_refine_ls_number_restraints     5
_refine_ls_restrained_S_all      1.021
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0355
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0287P)²+3.7348P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0686
_refine_ls_wR_factor_ref         0.0798
_reflns_number_gt                5961
_reflns_number_total             8523
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            zq2264sup1.cif
_cod_data_source_block           1
_cod_original_cell_volume        4338.5(14)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2244190
_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   0.315
_shelx_estimated_absorpt_t_max   0.568
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
_atom_site_disorder_assembly
_atom_site_disorder_group
Br Br1A 0.16416(3) 0.64628(2) 0.09609(2) 0.04094(10) Uani d 1 . .
Br Br2A 0.55611(3) 0.52669(2) 0.36556(3) 0.05486(13) Uani d 1 . .
O O1A 0.1498(2) 0.36605(13) 0.49979(14) 0.0395(6) Uani d 1 . .
O O2A 0.1109(2) 0.57148(12) 0.37508(16) 0.0469(7) Uani d 1 . .
N N1A 0.1343(2) 0.46167(13) 0.41932(16) 0.0279(6) Uani d 1 . .
C C1A 0.2142(2) 0.51420(15) 0.16832(19) 0.0235(7) Uani d 1 . .
C C2A 0.3218(2) 0.50277(15) 0.19315(19) 0.0246(7) Uani d 1 . .
C C3A 0.3659(2) 0.46791(15) 0.26682(19) 0.0241(7) Uani d 1 . .
C C4A 0.3024(2) 0.44455(15) 0.31516(18) 0.0229(7) Uani d 1 . .
C C5A 0.1951(2) 0.45732(15) 0.29062(18) 0.0225(7) Uani d 1 . .
C C6A 0.1501(2) 0.49312(15) 0.21738(18) 0.0230(7) Uani d 1 . .
C C7A 0.1661(3) 0.54733(15) 0.0867(2) 0.0287(7) Uani d 1 . .
H H7A 0.093934 0.530854 0.064312 0.034 Uiso calc 1 . .
H H7B 0.205959 0.534699 0.047632 0.034 Uiso calc 1 . .
C C8A 0.3894(3) 0.52472(18) 0.1391(2) 0.0340(8) Uani d 1 . .
H H8A 0.459884 0.535976 0.174052 0.041 Uiso calc 1 . .
H H8B 0.359230 0.565484 0.108240 0.041 Uiso calc 1 . .
C C9A 0.3974(3) 0.4693(2) 0.0781(2) 0.0448(10) Uani d 1 . .
H H9A 0.441493 0.484750 0.044129 0.067 Uiso calc 1 . .
H H9B 0.327785 0.458744 0.042768 0.067 Uiso calc 1 . .
H H9C 0.428167 0.429159 0.108595 0.067 Uiso calc 1 . .
C C10A 0.4810(3) 0.45441(16) 0.2934(2) 0.0308(8) Uani d 1 . .
H H10A 0.507217 0.450900 0.244241 0.037 Uiso calc 1 . .
H H10B 0.494319 0.411194 0.323135 0.037 Uiso calc 1 . .
C C11A 0.3497(3) 0.40134(16) 0.39013(19) 0.0269(7) Uani d 1 . .
H H11A 0.308225 0.406023 0.430053 0.032 Uiso calc 1 . .
H H11B 0.421453 0.416754 0.417113 0.032 Uiso calc 1 . .
C C12A 0.3520(3) 0.32768(17) 0.3655(2) 0.0347(8) Uani d 1 . .
H H12A 0.392091 0.301699 0.412842 0.052 Uiso calc 1 . .
H H12B 0.384727 0.323864 0.320503 0.052 Uiso calc 1 . .
H H12C 0.280706 0.310351 0.347287 0.052 Uiso calc 1 . .
C C13A 0.1249(3) 0.42863(16) 0.33988(19) 0.0270(7) Uani d 1 . .
H H13A 0.051651 0.431931 0.306061 0.032 Uiso calc 1 . .
H H13B 0.141356 0.380507 0.350038 0.032 Uiso calc 1 . .
C C14A 0.1440(3) 0.42633(18) 0.4930(2) 0.0301(8) Uani d 1 . .
C C15A 0.1469(3) 0.47882(19) 0.5564(2) 0.0329(8) Uani d 1 . .
C C16A 0.1600(3) 0.4726(2) 0.6405(2) 0.0425(9) Uani d 1 . .
H H16A 0.165391 0.430161 0.666754 0.051 Uiso calc 1 . .
C C17A 0.1650(3) 0.5332(2) 0.6847(2) 0.0499(11) Uani d 1 . .
H H17A 0.174875 0.531280 0.742489 0.060 Uiso calc 1 . .
C C18A 0.1561(3) 0.5948(2) 0.6471(3) 0.0508(10) Uani d 1 . .
H H18A 0.160339 0.634344 0.679134 0.061 Uiso calc 1 . .
C C19A 0.1409(3) 0.5999(2) 0.5630(2) 0.0464(10) Uani d 1 . .
H H19A 0.133774 0.642245 0.536402 0.056 Uiso calc 1 . .
C C20A 0.1366(3) 0.54083(18) 0.5190(2) 0.0345(8) Uani d 1 . .
C C21A 0.1250(3) 0.53045(18) 0.4296(2) 0.0328(8) Uani d 1 . .
C C22A 0.0342(2) 0.50790(17) 0.1894(2) 0.0286(7) Uani d 1 . .
H H22A 0.022597 0.549713 0.156644 0.034 Uiso calc 1 . .
H H22B 0.008679 0.515234 0.238308 0.034 Uiso calc 1 . .
C C23A -0.0282(3) 0.45160(19) 0.1379(2) 0.0377(9) Uani d 1 . .
H H23A -0.101033 0.465459 0.116564 0.057 Uiso calc 1 . .
H H23B -0.024207 0.411552 0.172112 0.057 Uiso calc 1 . .
H H23C 0.000531 0.441538 0.091847 0.057 Uiso calc 1 . .
Br Br1B 0.67396(3) 0.39932(2) 0.09585(2) 0.04119(10) Uani d 1 . .
Br Br2B 1.04422(3) 0.25251(2) 0.36780(2) 0.03582(9) Uani d 1 . .
O O1B 0.6272(2) 0.11607(13) 0.48916(16) 0.0435(7) Uani d 1 . .
O O2B 0.61521(19) 0.32716(12) 0.38071(14) 0.0350(6) Uani d 1 . .
N N1B 0.6197(2) 0.21507(14) 0.41532(16) 0.0300(6) Uani d 1 . .
C C1B 0.7055(2) 0.26581(14) 0.16601(18) 0.0225(7) Uani d 1 . .
C C2B 0.8113(2) 0.24748(15) 0.19156(18) 0.0234(6) Uani d 1 . .
C C3B 0.8472(2) 0.20833(15) 0.26292(18) 0.0236(7) Uani d 1 . .
C C4B 0.7787(3) 0.18849(15) 0.30865(19) 0.0252(7) Uani d 1 . .
C C5B 0.6737(2) 0.20943(15) 0.28466(19) 0.0245(7) Uani d 1 . .
C C6B 0.6371(2) 0.24923(16) 0.21354(18) 0.0249(7) Uani d 1 . .
C C7B 0.6642(3) 0.30068(16) 0.0850(2) 0.0295(7) Uani d 1 . .
H H7C 0.590476 0.287854 0.060999 0.035 Uiso calc 1 . .
H H7D 0.703943 0.285679 0.046832 0.035 Uiso calc 1 . .
C C8B 0.8845(3) 0.26902(16) 0.14208(19) 0.0279(7) Uani d 1 . .
H H8C 0.954519 0.277115 0.179979 0.033 Uiso calc 1 . .
H H8D 0.859366 0.311679 0.113665 0.033 Uiso calc 1 . .
C C9B 0.8929(3) 0.21651(19) 0.0782(2) 0.0359(8) Uani d 1 . .
H H9D 0.939746 0.232899 0.047079 0.054 Uiso calc 1 . .
H H9E 0.823776 0.208315 0.040526 0.054 Uiso calc 1 . .
H H9F 0.920501 0.174702 0.106241 0.054 Uiso calc 1 . .
C C10B 0.9591(3) 0.18730(17) 0.2891(2) 0.0300(7) Uani d 1 . .
H H10C 0.985816 0.183927 0.240246 0.036 Uiso calc 1 . .
H H10D 0.964949 0.142577 0.315289 0.036 Uiso calc 1 . .
C C11B 0.8180(3) 0.14231(16) 0.3819(2) 0.0311(8) Uani d 0.820(6) A 1
H H11C 0.891146 0.153595 0.410628 0.037 Uiso calc 0.820(6) A 1
H H11D 0.775821 0.148948 0.421073 0.037 Uiso calc 0.820(6) A 1
C C12B 0.8113(4) 0.0699(2) 0.3550(3) 0.0406(12) Uani d 0.820(6) A 1
H H12D 0.848945 0.041825 0.401198 0.061 Uiso calc 0.820(6) A 1
H H12E 0.842563 0.064919 0.309354 0.061 Uiso calc 0.820(6) A 1
H H12F 0.738156 0.056104 0.337049 0.061 Uiso calc 0.820(6) A 1
C C11C 0.8180(3) 0.14231(16) 0.3819(2) 0.0311(8) Uani d 0.180(6) A 2
H H11E 0.758897 0.115163 0.388690 0.037 Uiso calc 0.180(6) A 2
H H11F 0.869688 0.111156 0.370233 0.037 Uiso calc 0.180(6) A 2
C C12C 0.8641(17) 0.1758(10) 0.4567(12) 0.0406(12) Uani d 0.180(6) A 2
H H12G 0.932253 0.193439 0.455771 0.061 Uiso calc 0.180(6) A 2
H H12H 0.872996 0.144431 0.502612 0.061 Uiso calc 0.180(6) A 2
H H12I 0.819208 0.212918 0.463481 0.061 Uiso calc 0.180(6) A 2
C C13B 0.5994(3) 0.18597(17) 0.3324(2) 0.0330(8) Uani d 1 . .
H H13C 0.527408 0.197432 0.300662 0.040 Uiso calc 1 . .
H H13D 0.603806 0.136584 0.337432 0.040 Uiso calc 1 . .
C C14B 0.6311(3) 0.17670(19) 0.4873(2) 0.0333(8) Uani d 1 . .
C C15B 0.6500(3) 0.22625(19) 0.5562(2) 0.0335(8) Uani d 1 . .
C C16B 0.6689(3) 0.2166(2) 0.6403(2) 0.0412(9) Uani d 1 . .
H H16B 0.671296 0.173089 0.663423 0.049 Uiso calc 1 . .
C C17B 0.6840(3) 0.2739(2) 0.6891(2) 0.0480(10) Uani d 1 . .
H H17B 0.696999 0.269143 0.746899 0.058 Uiso calc 1 . .
C C18B 0.6808(3) 0.3374(2) 0.6561(2) 0.0464(10) Uani d 1 . .
H H18B 0.691568 0.375124 0.691637 0.056 Uiso calc 1 . .
C C19B 0.6621(3) 0.3470(2) 0.5715(2) 0.0398(9) Uani d 1 . .
H H19B 0.659735 0.390576 0.548338 0.048 Uiso calc 1 . .
C C20B 0.6471(2) 0.29004(18) 0.5229(2) 0.0305(8) Uani d 1 . .
C C21B 0.6258(3) 0.28343(18) 0.4321(2) 0.0300(7) Uani d 1 . .
C C22B 0.5264(2) 0.27532(17) 0.1873(2) 0.0303(7) Uani d 1 . .
H H22C 0.525540 0.319108 0.159625 0.036 Uiso calc 1 . .
H H22D 0.502198 0.282707 0.236834 0.036 Uiso calc 1 . .
C C23B 0.4509(3) 0.2279(2) 0.1292(3) 0.0509(10) Uani d 1 . .
H H23D 0.382770 0.249568 0.109135 0.076 Uiso calc 1 . .
H H23E 0.443652 0.186717 0.158665 0.076 Uiso calc 1 . .
H H23F 0.477779 0.216890 0.082429 0.076 Uiso calc 1 . .
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_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 0 -1 0.1036
17 30 8 0.1303
8 -15 4 0.1283
8 -15 -4 0.0886
19 -30 -21 0.0953
27 -5 -30 0.1193
16 30 -19 0.1295
0 1 0 0.0825
1 30 14 0.0933
-2 -7 30 0.1346
-1 -30 20 0.1273
-17 -30 -14 0.1239
-25 30 9 0.1099
-29 -2 30 0.1067
-30 -26 29 0.1055
0 -1 0 0.0975
-1 -30 -13 0.0961
-3 7 -30 0.1368
1 30 -17 0.1159
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C21A N1A C14A . . 111.9(3) ?
C21A N1A C13A . . 124.6(3) ?
C14A N1A C13A . . 123.2(3) ?
C2A C1A C6A . . 121.0(3) ?
C2A C1A C7A . . 119.3(3) ?
C6A C1A C7A . . 119.7(3) ?
C1A C2A C3A . . 119.3(3) ?
C1A C2A C8A . . 120.3(3) ?
C3A C2A C8A . . 120.3(3) ?
C2A C3A C4A . . 120.4(3) ?
C2A C3A C10A . . 119.7(3) ?
C4A C3A C10A . . 119.9(3) ?
C5A C4A C3A . . 119.9(3) ?
C5A C4A C11A . . 120.3(3) ?
C3A C4A C11A . . 119.6(3) ?
C4A C5A C6A . . 120.2(3) ?
C4A C5A C13A . . 120.2(3) ?
C6A C5A C13A . . 119.5(3) ?
C1A C6A C5A . . 119.1(3) ?
C1A C6A C22A . . 119.5(3) ?
C5A C6A C22A . . 121.4(3) ?
C1A C7A Br1A . . 112.1(2) ?
C1A C7A H7A . . 109.2 ?
Br1A C7A H7A . . 109.2 ?
C1A C7A H7B . . 109.2 ?
Br1A C7A H7B . . 109.2 ?
H7A C7A H7B . . 107.9 ?
C2A C8A C9A . . 111.2(3) ?
C2A C8A H8A . . 109.4 ?
C9A C8A H8A . . 109.4 ?
C2A C8A H8B . . 109.4 ?
C9A C8A H8B . . 109.4 ?
H8A C8A H8B . . 108.0 ?
C8A C9A H9A . . 109.5 ?
C8A C9A H9B . . 109.5 ?
H9A C9A H9B . . 109.5 ?
C8A C9A H9C . . 109.5 ?
H9A C9A H9C . . 109.5 ?
H9B C9A H9C . . 109.5 ?
C3A C10A Br2A . . 110.9(2) ?
C3A C10A H10A . . 109.5 ?
Br2A C10A H10A . . 109.5 ?
C3A C10A H10B . . 109.5 ?
Br2A C10A H10B . . 109.5 ?
H10A C10A H10B . . 108.1 ?
C4A C11A C12A . . 110.7(3) ?
C4A C11A H11A . . 109.5 ?
C12A C11A H11A . . 109.5 ?
C4A C11A H11B . . 109.5 ?
C12A C11A H11B . . 109.5 ?
H11A C11A H11B . . 108.1 ?
C11A C12A H12A . . 109.5 ?
C11A C12A H12B . . 109.5 ?
H12A C12A H12B . . 109.5 ?
C11A C12A H12C . . 109.5 ?
H12A C12A H12C . . 109.5 ?
H12B C12A H12C . . 109.5 ?
N1A C13A C5A . . 114.9(3) ?
N1A C13A H13A . . 108.5 ?
C5A C13A H13A . . 108.5 ?
N1A C13A H13B . . 108.5 ?
C5A C13A H13B . . 108.5 ?
H13A C13A H13B . . 107.5 ?
O1A C14A N1A . . 124.9(3) ?
O1A C14A C15A . . 129.9(3) ?
N1A C14A C15A . . 105.2(3) ?
C20A C15A C16A . . 121.2(3) ?
C20A C15A C14A . . 108.7(3) ?
C16A C15A C14A . . 130.1(4) ?
C15A C16A C17A . . 116.0(4) ?
C15A C16A H16A . . 122.0 ?
C17A C16A H16A . . 122.0 ?
C18A C17A C16A . . 122.4(4) ?
C18A C17A H17A . . 118.8 ?
C16A C17A H17A . . 118.8 ?
C17A C18A C19A . . 120.7(4) ?
C17A C18A H18A . . 119.7 ?
C19A C18A H18A . . 119.7 ?
C18A C19A C20A . . 117.5(4) ?
C18A C19A H19A . . 121.2 ?
C20A C19A H19A . . 121.2 ?
C15A C20A C19A . . 122.1(3) ?
C15A C20A C21A . . 108.1(3) ?
C19A C20A C21A . . 129.8(4) ?
O2A C21A N1A . . 125.0(3) ?
O2A C21A C20A . . 129.1(3) ?
N1A C21A C20A . . 106.0(3) ?
C6A C22A C23A . . 112.6(3) ?
C6A C22A H22A . . 109.1 ?
C23A C22A H22A . . 109.1 ?
C6A C22A H22B . . 109.1 ?
C23A C22A H22B . . 109.1 ?
H22A C22A H22B . . 107.8 ?
C22A C23A H23A . . 109.5 ?
C22A C23A H23B . . 109.5 ?
H23A C23A H23B . . 109.5 ?
C22A C23A H23C . . 109.5 ?
H23A C23A H23C . . 109.5 ?
H23B C23A H23C . . 109.5 ?
C21B N1B C14B . . 111.7(3) ?
C21B N1B C13B . . 124.5(3) ?
C14B N1B C13B . . 123.8(3) ?
C2B C1B C6B . . 121.2(3) ?
C2B C1B C7B . . 119.1(3) ?
C6B C1B C7B . . 119.7(3) ?
C3B C2B C1B . . 118.9(3) ?
C3B C2B C8B . . 120.9(3) ?
C1B C2B C8B . . 120.3(3) ?
C2B C3B C4B . . 120.6(3) ?
C2B C3B C10B . . 119.0(3) ?
C4B C3B C10B . . 120.4(3) ?
C3B C4B C5B . . 120.3(3) ?
C3B C4B C11C . . 119.3(3) ?
C5B C4B C11C . . 120.4(3) ?
C3B C4B C11B . . 119.3(3) ?
C5B C4B C11B . . 120.4(3) ?
C6B C5B C4B . . 119.6(3) ?
C6B C5B C13B . . 120.3(3) ?
C4B C5B C13B . . 120.0(3) ?
C5B C6B C1B . . 119.4(3) ?
C5B C6B C22B . . 121.6(3) ?
C1B C6B C22B . . 119.1(3) ?
C1B C7B Br1B . . 112.3(2) ?
C1B C7B H7C . . 109.1 ?
Br1B C7B H7C . . 109.1 ?
C1B C7B H7D . . 109.1 ?
Br1B C7B H7D . . 109.1 ?
H7C C7B H7D . . 107.9 ?
C2B C8B C9B . . 112.3(3) ?
C2B C8B H8C . . 109.1 ?
C9B C8B H8C . . 109.1 ?
C2B C8B H8D . . 109.1 ?
C9B C8B H8D . . 109.1 ?
H8C C8B H8D . . 107.9 ?
C8B C9B H9D . . 109.5 ?
C8B C9B H9E . . 109.5 ?
H9D C9B H9E . . 109.5 ?
C8B C9B H9F . . 109.5 ?
H9D C9B H9F . . 109.5 ?
H9E C9B H9F . . 109.5 ?
C3B C10B Br2B . . 110.8(2) ?
C3B C10B H10C . . 109.5 ?
Br2B C10B H10C . . 109.5 ?
C3B C10B H10D . . 109.5 ?
Br2B C10B H10D . . 109.5 ?
H10C C10B H10D . . 108.1 ?
C12B C11B C4B . . 110.9(3) ?
C12B C11B H11C . . 109.5 ?
C4B C11B H11C . . 109.5 ?
C12B C11B H11D . . 109.5 ?
C4B C11B H11D . . 109.5 ?
H11C C11B H11D . . 108.0 ?
C11B C12B H12D . . 109.5 ?
C11B C12B H12E . . 109.5 ?
H12D C12B H12E . . 109.5 ?
C11B C12B H12F . . 109.5 ?
H12D C12B H12F . . 109.5 ?
H12E C12B H12F . . 109.5 ?
C12C C11C C4B . . 114.2(8) ?
C12C C11C H11E . . 108.7 ?
C4B C11C H11E . . 108.7 ?
C12C C11C H11F . . 108.7 ?
C4B C11C H11F . . 108.7 ?
H11E C11C H11F . . 107.6 ?
C11C C12C H12G . . 109.5 ?
C11C C12C H12H . . 109.5 ?
H12G C12C H12H . . 109.5 ?
C11C C12C H12I . . 109.5 ?
H12G C12C H12I . . 109.5 ?
H12H C12C H12I . . 109.5 ?
N1B C13B C5B . . 114.2(3) ?
N1B C13B H13C . . 108.7 ?
C5B C13B H13C . . 108.7 ?
N1B C13B H13D . . 108.7 ?
C5B C13B H13D . . 108.7 ?
H13C C13B H13D . . 107.6 ?
O1B C14B N1B . . 124.7(3) ?
O1B C14B C15B . . 129.8(3) ?
N1B C14B C15B . . 105.5(3) ?
C16B C15B C20B . . 121.3(4) ?
C16B C15B C14B . . 130.6(3) ?
C20B C15B C14B . . 108.1(3) ?
C15B C16B C17B . . 116.7(4) ?
C15B C16B H16B . . 121.7 ?
C17B C16B H16B . . 121.7 ?
C18B C17B C16B . . 122.1(4) ?
C18B C17B H17B . . 118.9 ?
C16B C17B H17B . . 118.9 ?
C17B C18B C19B . . 121.2(4) ?
C17B C18B H18B . . 119.4 ?
C19B C18B H18B . . 119.4 ?
C20B C19B C18B . . 116.7(4) ?
C20B C19B H19B . . 121.6 ?
C18B C19B H19B . . 121.6 ?
C19B C20B C15B . . 122.0(3) ?
C19B C20B C21B . . 129.8(3) ?
C15B C20B C21B . . 108.2(3) ?
O2B C21B N1B . . 124.8(3) ?
O2B C21B C20B . . 128.8(3) ?
N1B C21B C20B . . 106.3(3) ?
C6B C22B C23B . . 113.1(3) ?
C6B C22B H22C . . 108.9 ?
C23B C22B H22C . . 108.9 ?
C6B C22B H22D . . 108.9 ?
C23B C22B H22D . . 108.9 ?
H22C C22B H22D . . 107.8 ?
C22B C23B H23D . . 109.5 ?
C22B C23B H23E . . 109.5 ?
H23D C23B H23E . . 109.5 ?
C22B C23B H23F . . 109.5 ?
H23D C23B H23F . . 109.5 ?
H23E C23B H23F . . 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Br1A C7A . 1.983(3) ?
Br2A C10A . 1.975(3) ?
O1A C14A . 1.210(4) ?
O2A C21A . 1.208(4) ?
N1A C21A . 1.394(4) ?
N1A C14A . 1.406(4) ?
N1A C13A . 1.471(4) ?
C1A C2A . 1.401(4) ?
C1A C6A . 1.412(4) ?
C1A C7A . 1.505(4) ?
C2A C3A . 1.406(4) ?
C2A C8A . 1.517(4) ?
C3A C4A . 1.411(4) ?
C3A C10A . 1.503(4) ?
C4A C5A . 1.402(4) ?
C4A C11A . 1.519(4) ?
C5A C6A . 1.412(4) ?
C5A C13A . 1.528(4) ?
C6A C22A . 1.518(4) ?
C7A H7A . 0.9900 ?
C7A H7B . 0.9900 ?
C8A C9A . 1.536(5) ?
C8A H8A . 0.9900 ?
C8A H8B . 0.9900 ?
C9A H9A . 0.9800 ?
C9A H9B . 0.9800 ?
C9A H9C . 0.9800 ?
C10A H10A . 0.9900 ?
C10A H10B . 0.9900 ?
C11A C12A . 1.531(5) ?
C11A H11A . 0.9900 ?
C11A H11B . 0.9900 ?
C12A H12A . 0.9800 ?
C12A H12B . 0.9800 ?
C12A H12C . 0.9800 ?
C13A H13A . 0.9900 ?
C13A H13B . 0.9900 ?
C14A C15A . 1.493(5) ?
C15A C20A . 1.380(5) ?
C15A C16A . 1.390(5) ?
C16A C17A . 1.414(6) ?
C16A H16A . 0.9500 ?
C17A C18A . 1.375(6) ?
C17A H17A . 0.9500 ?
C18A C19A . 1.384(6) ?
C18A H18A . 0.9500 ?
C19A C20A . 1.387(5) ?
C19A H19A . 0.9500 ?
C20A C21A . 1.491(5) ?
C22A C23A . 1.521(5) ?
C22A H22A . 0.9900 ?
C22A H22B . 0.9900 ?
C23A H23A . 0.9800 ?
C23A H23B . 0.9800 ?
C23A H23C . 0.9800 ?
Br1B C7B . 1.979(3) ?
Br2B C10B . 1.980(3) ?
O1B C14B . 1.212(4) ?
O2B C21B . 1.213(4) ?
N1B C21B . 1.392(4) ?
N1B C14B . 1.411(4) ?
N1B C13B . 1.472(4) ?
C1B C2B . 1.407(4) ?
C1B C6B . 1.415(4) ?
C1B C7B . 1.499(4) ?
C2B C3B . 1.406(4) ?
C2B C8B . 1.516(4) ?
C3B C4B . 1.409(4) ?
C3B C10B . 1.498(4) ?
C4B C5B . 1.412(4) ?
C4B C11C . 1.517(4) ?
C4B C11B . 1.517(4) ?
C5B C6B . 1.411(4) ?
C5B C13B . 1.518(4) ?
C6B C22B . 1.514(4) ?
C7B H7C . 0.9900 ?
C7B H7D . 0.9900 ?
C8B C9B . 1.532(4) ?
C8B H8C . 0.9900 ?
C8B H8D . 0.9900 ?
C9B H9D . 0.9800 ?
C9B H9E . 0.9800 ?
C9B H9F . 0.9800 ?
C10B H10C . 0.9900 ?
C10B H10D . 0.9900 ?
C11B C12B . 1.510(5) ?
C11B H11C . 0.9900 ?
C11B H11D . 0.9900 ?
C12B H12D . 0.9800 ?
C12B H12E . 0.9800 ?
C12B H12F . 0.9800 ?
C11C C12C . 1.41(2) ?
C11C H11E . 0.9900 ?
C11C H11F . 0.9900 ?
C12C H12G . 0.9800 ?
C12C H12H . 0.9800 ?
C12C H12I . 0.9800 ?
C13B H13C . 0.9900 ?
C13B H13D . 0.9900 ?
C14B C15B . 1.496(5) ?
C15B C16B . 1.388(5) ?
C15B C20B . 1.389(5) ?
C16B C17B . 1.392(6) ?
C16B H16B . 0.9500 ?
C17B C18B . 1.380(6) ?
C17B H17B . 0.9500 ?
C18B C19B . 1.398(5) ?
C18B H18B . 0.9500 ?
C19B C20B . 1.385(5) ?
C19B H19B . 0.9500 ?
C20B C21B . 1.488(5) ?
C22B C23B . 1.527(5) ?
C22B H22C . 0.9900 ?
C22B H22D . 0.9900 ?
C23B H23D . 0.9800 ?
C23B H23E . 0.9800 ?
C23B H23F . 0.9800 ?
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
_geom_hbond_publ_flag
C10A H10B O2B . 0.99 2.35 3.223(4) 147.2 yes
C11A H11A N1A . 0.99 2.54 3.283(4) 131.9 yes
C13A H13B Br2B 1_455 0.99 2.92 3.746(3) 141.6 yes
C13A H13B O1A . 0.99 2.52 2.914(4) 103.4 yes
C9B H9F Br2A 2_645 0.98 3.00 3.921(4) 157.8 yes
C11B H11D N1B . 0.99 2.45 3.207(4) 133.0 yes
C12B H12D Br1B 2_645 0.98 2.86 3.499(4) 123.3 yes
C13B H13D O1B . 0.99 2.53 2.928(4) 103.6 yes
C22B H22D O2B . 0.99 2.64 3.322(4) 126.4 yes
C23B H23E O2A 2_545 0.98 2.43 3.226(5) 137.6 yes
C22A H22B O2A . 0.99 2.59 3.278(4) 126.3 yes
C9B H9D <i>Cg</i>4 4_565 0.98 2.96 3.731(5) 137 yes
C23B H23D <i>Cg</i>4 4_665 0.98 2.92 3.542(5) 122 yes
C12C H12I N1B . 0.98 2.56 3.24(2) 126.3 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C6A C1A C2A C3A . . . . 2.0(5) ?
C7A C1A C2A C3A . . . . -175.9(3) ?
C6A C1A C2A C8A . . . . 179.0(3) ?
C7A C1A C2A C8A . . . . 1.1(4) ?
C1A C2A C3A C4A . . . . 0.1(5) ?
C8A C2A C3A C4A . . . . -176.9(3) ?
C1A C2A C3A C10A . . . . 179.0(3) ?
C8A C2A C3A C10A . . . . 2.0(5) ?
C2A C3A C4A C5A . . . . -1.3(4) ?
C10A C3A C4A C5A . . . . 179.8(3) ?
C2A C3A C4A C11A . . . . 174.2(3) ?
C10A C3A C4A C11A . . . . -4.7(4) ?
C3A C4A C5A C6A . . . . 0.4(4) ?
C11A C4A C5A C6A . . . . -175.1(3) ?
C3A C4A C5A C13A . . . . 176.4(3) ?
C11A C4A C5A C13A . . . . 0.9(4) ?
C2A C1A C6A C5A . . . . -2.9(4) ?
C7A C1A C6A C5A . . . . 175.0(3) ?
C2A C1A C6A C22A . . . . 178.5(3) ?
C7A C1A C6A C22A . . . . -3.6(4) ?
C4A C5A C6A C1A . . . . 1.7(4) ?
C13A C5A C6A C1A . . . . -174.3(3) ?
C4A C5A C6A C22A . . . . -179.8(3) ?
C13A C5A C6A C22A . . . . 4.2(4) ?
C2A C1A C7A Br1A . . . . -89.3(3) ?
C6A C1A C7A Br1A . . . . 92.8(3) ?
C1A C2A C8A C9A . . . . -89.4(4) ?
C3A C2A C8A C9A . . . . 87.6(4) ?
C2A C3A C10A Br2A . . . . 91.8(3) ?
C4A C3A C10A Br2A . . . . -89.3(3) ?
C5A C4A C11A C12A . . . . 90.8(3) ?
C3A C4A C11A C12A . . . . -84.7(4) ?
C21A N1A C13A C5A . . . . 52.9(4) ?
C14A N1A C13A C5A . . . . -133.3(3) ?
C4A C5A C13A N1A . . . . 73.6(4) ?
C6A C5A C13A N1A . . . . -110.4(3) ?
C21A N1A C14A O1A . . . . 177.5(3) ?
C13A N1A C14A O1A . . . . 3.0(5) ?
C21A N1A C14A C15A . . . . -3.3(4) ?
C13A N1A C14A C15A . . . . -177.8(3) ?
O1A C14A C15A C20A . . . . -179.5(4) ?
N1A C14A C15A C20A . . . . 1.3(4) ?
O1A C14A C15A C16A . . . . 2.2(6) ?
N1A C14A C15A C16A . . . . -176.9(3) ?
C20A C15A C16A C17A . . . . -1.6(5) ?
C14A C15A C16A C17A . . . . 176.5(3) ?
C15A C16A C17A C18A . . . . 0.8(6) ?
C16A C17A C18A C19A . . . . 0.4(6) ?
C17A C18A C19A C20A . . . . -0.8(6) ?
C16A C15A C20A C19A . . . . 1.3(5) ?
C14A C15A C20A C19A . . . . -177.2(3) ?
C16A C15A C20A C21A . . . . 179.4(3) ?
C14A C15A C20A C21A . . . . 0.9(4) ?
C18A C19A C20A C15A . . . . 0.0(6) ?
C18A C19A C20A C21A . . . . -177.7(4) ?
C14A N1A C21A O2A . . . . -176.4(3) ?
C13A N1A C21A O2A . . . . -2.0(6) ?
C14A N1A C21A C20A . . . . 3.9(4) ?
C13A N1A C21A C20A . . . . 178.3(3) ?
C15A C20A C21A O2A . . . . 177.4(4) ?
C19A C20A C21A O2A . . . . -4.6(7) ?
C15A C20A C21A N1A . . . . -2.9(4) ?
C19A C20A C21A N1A . . . . 175.0(4) ?
C1A C6A C22A C23A . . . . 91.4(4) ?
C5A C6A C22A C23A . . . . -87.1(4) ?
C6B C1B C2B C3B . . . . 4.1(4) ?
C7B C1B C2B C3B . . . . -173.0(3) ?
C6B C1B C2B C8B . . . . -176.7(3) ?
C7B C1B C2B C8B . . . . 6.2(4) ?
C1B C2B C3B C4B . . . . -0.8(4) ?
C8B C2B C3B C4B . . . . 180.0(3) ?
C1B C2B C3B C10B . . . . 178.5(3) ?
C8B C2B C3B C10B . . . . -0.7(4) ?
C2B C3B C4B C5B . . . . -1.9(5) ?
C10B C3B C4B C5B . . . . 178.8(3) ?
C2B C3B C4B C11C . . . . 175.8(3) ?
C10B C3B C4B C11C . . . . -3.5(4) ?
C2B C3B C4B C11B . . . . 175.8(3) ?
C10B C3B C4B C11B . . . . -3.5(4) ?
C3B C4B C5B C6B . . . . 1.3(5) ?
C11C C4B C5B C6B . . . . -176.4(3) ?
C11B C4B C5B C6B . . . . -176.4(3) ?
C3B C4B C5B C13B . . . . 177.9(3) ?
C11C C4B C5B C13B . . . . 0.2(4) ?
C11B C4B C5B C13B . . . . 0.2(4) ?
C4B C5B C6B C1B . . . . 1.9(4) ?
C13B C5B C6B C1B . . . . -174.7(3) ?
C4B C5B C6B C22B . . . . -177.4(3) ?
C13B C5B C6B C22B . . . . 6.0(4) ?
C2B C1B C6B C5B . . . . -4.7(4) ?
C7B C1B C6B C5B . . . . 172.4(3) ?
C2B C1B C6B C22B . . . . 174.7(3) ?
C7B C1B C6B C22B . . . . -8.2(4) ?
C2B C1B C7B Br1B . . . . -90.8(3) ?
C6B C1B C7B Br1B . . . . 92.0(3) ?
C3B C2B C8B C9B . . . . 86.8(4) ?
C1B C2B C8B C9B . . . . -92.4(4) ?
C2B C3B C10B Br2B . . . . 92.4(3) ?
C4B C3B C10B Br2B . . . . -88.3(3) ?
C3B C4B C11B C12B . . . . -84.5(4) ?
C5B C4B C11B C12B . . . . 93.2(4) ?
C3B C4B C11C C12C . . . . 87.7(10) ?
C5B C4B C11C C12C . . . . -94.6(10) ?
C21B N1B C13B C5B . . . . 54.5(4) ?
C14B N1B C13B C5B . . . . -128.2(3) ?
C6B C5B C13B N1B . . . . -113.3(3) ?
C4B C5B C13B N1B . . . . 70.1(4) ?
C21B N1B C14B O1B . . . . 178.8(3) ?
C13B N1B C14B O1B . . . . 1.2(5) ?
C21B N1B C14B C15B . . . . -2.2(4) ?
C13B N1B C14B C15B . . . . -179.8(3) ?
O1B C14B C15B C16B . . . . 0.6(6) ?
N1B C14B C15B C16B . . . . -178.4(3) ?
O1B C14B C15B C20B . . . . -180.0(4) ?
N1B C14B C15B C20B . . . . 1.1(4) ?
C20B C15B C16B C17B . . . . 0.3(5) ?
C14B C15B C16B C17B . . . . 179.7(3) ?
C15B C16B C17B C18B . . . . -0.1(6) ?
C16B C17B C18B C19B . . . . 0.0(6) ?
C17B C18B C19B C20B . . . . 0.0(6) ?
C18B C19B C20B C15B . . . . 0.2(5) ?
C18B C19B C20B C21B . . . . 180.0(3) ?
C16B C15B C20B C19B . . . . -0.4(5) ?
C14B C15B C20B C19B . . . . -179.9(3) ?
C16B C15B C20B C21B . . . . 179.8(3) ?
C14B C15B C20B C21B . . . . 0.3(4) ?
C14B N1B C21B O2B . . . . -177.6(3) ?
C13B N1B C21B O2B . . . . 0.0(5) ?
C14B N1B C21B C20B . . . . 2.4(4) ?
C13B N1B C21B C20B . . . . 179.9(3) ?
C19B C20B C21B O2B . . . . -1.4(6) ?
C15B C20B C21B O2B . . . . 178.4(3) ?
C19B C20B C21B N1B . . . . 178.7(3) ?
C15B C20B C21B N1B . . . . -1.6(4) ?
C5B C6B C22B C23B . . . . -90.3(4) ?
C1B C6B C22B C23B . . . . 90.3(4) ?

_cod_database_fobs_code 2244190
