#------------------------------------------------------------------------------
#$Date: 2025-10-16 02:18:34 +0300 (Thu, 16 Oct 2025) $
#$Revision: 302879 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/10/7251007.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_7251007
loop_
_publ_author_name
'Naumkina, Yelizaveta'
'Kratochvil, B.'
'Korotkova, Elena'
'Cejka, Jan'
_publ_section_title
;
 New forms of apremilast with halogen derivates of benzoic acid
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00770D
_journal_year                    2025
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C22 H24 N2 O7 S, 1/2(C7 H5 Br O2)'
_chemical_formula_sum            'C25.5 H26.5 Br0.5 N2 O8 S'
_chemical_formula_weight         561.02
_chemical_melting_point          ?
_chemical_name_common            'bis(apremilast) 4-bromobenzoic acid'
_chemical_name_systematic
'bis(N-{2-[1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl]-1,3-dioxo-2,3-dihydro-1H-isoindol-4-yl}acetamide) 4-bromobenzoic acid'
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_audit_update_record
;
2025-07-30 deposited with the CCDC.	2025-10-13 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   13.2266(3)
_cell_length_b                   13.4694(3)
_cell_length_c                   28.8772(6)
_cell_measurement_reflns_used    9838
_cell_measurement_temperature    180
_cell_measurement_theta_max      42.39
_cell_measurement_theta_min      3.06
_cell_volume                     5144.6(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.15'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Bruker Venture D8'
_diffrn_measurement_method       'φ & ω scans'
_diffrn_radiation_monochromator  polycapillary
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_av_unetI/netI     0.023
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            10186
_diffrn_reflns_theta_full        72.382
_diffrn_reflns_theta_max         72.382
_diffrn_reflns_theta_min         3.061
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    2.481
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_correction_T_min  0.58
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Siemens, 1996)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       bipyramidal
_exptl_crystal_F_000             2327.987
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Methyl Ethyl Ketone'
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.67
_refine_diff_density_min         -0.86
_refine_ls_abs_structure_details
; 
 Parsons, Flack & Wagner (2013), 
 4003 Friedel Pairs 
;
_refine_ls_abs_structure_Flack   0.001(2)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0000
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     680
_refine_ls_number_reflns         10180
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0423
_refine_ls_R_factor_gt           0.0414
_refine_ls_shift/su_max          0.0004565
_refine_ls_shift/su_mean         0.0000579
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method= Modified Sheldrick 
 w=1/[σ²(F²) + ( 0.08P)² + 4.03P] 
 ,where P=(max(Fo²,0) + 2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1185
_refine_ls_wR_factor_gt          0.1181
_refine_ls_wR_factor_ref         0.1185
_reflns_limit_h_max              16
_reflns_limit_h_min              -16
_reflns_limit_k_max              16
_reflns_limit_k_min              0
_reflns_limit_l_max              35
_reflns_limit_l_min              0
_reflns_number_gt                9877
_reflns_number_total             10186
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.88
_oxford_diffrn_Wilson_scale      13.30
_oxford_refine_ls_scale          0.2873(2)
_cod_data_source_file            d5ce00770d3.cif
_cod_data_source_block           APR_4BrBA
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '-' was changed to '?' --
the value is undefined or not given.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C25.50 H26.50 Br0.50 N2 O8 S'
_cod_database_code               7251007
_oxford_refine_reflns_threshold_expression I>-3.0\s(I)
_refine_ls_r_factor_ref          0.0423
_reflns_number_all               10180
_oxford_hooft_y                  -0.002(5)
_oxford_bijvoet_difference       0.001(2)
_oxford_refined_flack_x          -0.003(13)
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x+1/2,-y,z+1/2
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_attached_hydrogens
H22 H 0.898(2) -0.255(2) 0.6049(8) 0.036(2) 1.0000 Uiso D . . . . .
H320 H -0.009(2) 0.895(2) 0.1483(8) 0.031(2) 1.0000 Uiso D . . . . .
O69 O 0.3848(2) 0.2317(2) 0.39641(10) 0.0528 1.0000 Uani D . . . . .
O68 O 0.3433(3) 0.2761(2) 0.46864(10) 0.0583 1.0000 Uani . . . . . .
C61 C 0.3159(2) 0.3901(2) 0.40639(11) 0.0351 1.0000 Uani . . . . . .
C62 C 0.3515(3) 0.4192(3) 0.36294(13) 0.0425 1.0000 Uani . . . . . .
C63 C 0.3143(3) 0.5052(3) 0.34288(13) 0.0441 1.0000 Uani . . . . . .
C64 C 0.2418(3) 0.5593(2) 0.36631(13) 0.0398 1.0000 Uani . . . . . .
C65 C 0.2068(3) 0.5323(3) 0.40898(13) 0.0413 1.0000 Uani . . . . . .
C66 C 0.2459(3) 0.4469(3) 0.42958(12) 0.0396 1.0000 Uani . . . . . .
C67 C 0.3499(3) 0.2941(3) 0.42755(13) 0.0427 1.0000 Uani . . . . . .
H621 H 0.4017 0.3817 0.3473 0.0501 1.0000 Uiso R . . . . .
H631 H 0.3392 0.5278 0.3139 0.0525 1.0000 Uiso R . . . . .
H651 H 0.1571 0.5709 0.4234 0.0497 1.0000 Uiso R . . . . .
H661 H 0.2217 0.4281 0.4605 0.0480 1.0000 Uiso R . . . . .
Br70 Br 0.18516(3) 0.67344(3) 0.338294(19) 0.0617 1.0000 Uani . . . . . .
S1 S 0.86402(5) -0.31091(5) 0.40524(2) 0.0278 1.0000 Uani . . . . . .
O1 O 0.85725(17) -0.02023(16) 0.43600(7) 0.0319 1.0000 Uani . . . . . .
O2 O 0.79218(15) -0.26382(15) 0.54276(6) 0.0282 1.0000 Uani . . . . . .
O3 O 1.0675(2) -0.2049(2) 0.66866(9) 0.0500 1.0000 Uani . . . . . .
O4 O 0.95254(16) -0.26942(18) 0.42685(8) 0.0357 1.0000 Uani . . . . . .
O5 O 0.82378(19) -0.40148(17) 0.42436(9) 0.0423 1.0000 Uani . . . . . .
O6 O 0.50696(17) 0.05694(18) 0.37447(8) 0.0379 1.0000 Uani . . . . . .
O7 O 0.37529(17) 0.04647(18) 0.43976(8) 0.0382 1.0000 Uani . . . . . .
N1 N 0.80465(17) -0.15101(17) 0.48215(7) 0.0226 1.0000 Uani . . . . . .
N2 N 0.94922(19) -0.2202(2) 0.61238(8) 0.0304 1.0000 Uani D . . . . .
C1 C 0.9771(2) -0.1465(2) 0.58123(10) 0.0280 1.0000 Uani D . . . . .
C2 C 1.0566(2) -0.0779(2) 0.58780(11) 0.0335 1.0000 Uani . . . . . .
C3 C 1.0752(2) -0.0033(3) 0.55567(12) 0.0371 1.0000 Uani . . . . . .
C4 C 1.0176(2) 0.0075(2) 0.51537(11) 0.0324 1.0000 Uani . . . . . .
C5 C 0.9411(2) -0.0615(2) 0.50912(9) 0.0253 1.0000 Uani . . . . . .
C6 C 0.8659(2) -0.0706(2) 0.47066(9) 0.0255 1.0000 Uani . . . . . .
C7 C 0.83328(19) -0.1936(2) 0.52445(9) 0.0223 1.0000 Uani . . . . . .
C8 C 0.9212(2) -0.1354(2) 0.54097(9) 0.0242 1.0000 Uani . . . . . .
C9 C 0.9912(2) -0.2446(3) 0.65405(10) 0.0338 1.0000 Uani D . . . . .
C10 C 0.9345(3) -0.3228(3) 0.68092(12) 0.0458 1.0000 Uani . . . . . .
C11 C 0.7256(2) -0.1949(2) 0.45252(9) 0.0230 1.0000 Uani . . . . . .
C12 C 0.7667(2) -0.2204(2) 0.40424(9) 0.0238 1.0000 Uani . . . . . .
C13 C 0.8892(3) -0.3276(3) 0.34635(11) 0.0434 1.0000 Uani . . . . . .
C14 C 0.6329(2) -0.1293(2) 0.44913(9) 0.0236 1.0000 Uani . . . . . .
C15 C 0.6169(2) -0.0645(2) 0.41151(9) 0.0273 1.0000 Uani . . . . . .
C16 C 0.5299(2) -0.0079(2) 0.40938(10) 0.0280 1.0000 Uani . . . . . .
C17 C 0.4585(2) -0.0133(2) 0.44511(11) 0.0281 1.0000 Uani . . . . . .
C18 C 0.4747(2) -0.0758(2) 0.48218(9) 0.0283 1.0000 Uani . . . . . .
C19 C 0.5607(2) -0.1347(2) 0.48387(9) 0.0272 1.0000 Uani . . . . . .
C20 C 0.5769(2) 0.0638(3) 0.33618(11) 0.0361 1.0000 Uani . . . . . .
C21 C 0.5367(4) 0.1404(5) 0.30355(19) 0.0838 1.0000 Uani . . . . . .
C22 C 0.2992(2) 0.0407(3) 0.47502(11) 0.0363 1.0000 Uani . . . . . .
H21 H 1.0953 -0.0836 0.6130 0.0403 1.0000 Uiso R . . . . .
H662 H 1.1275 0.0413 0.5614 0.0440 1.0000 Uiso R . . . . .
H41 H 1.0294 0.0582 0.4945 0.0404 1.0000 Uiso R . . . . .
H101 H 0.9748 -0.3436 0.7061 0.0690 1.0000 Uiso R . . . . .
H102 H 0.8732 -0.2952 0.6924 0.0698 1.0000 Uiso R . . . . .
H103 H 0.9207 -0.3796 0.6628 0.0693 1.0000 Uiso R . . . . .
H111 H 0.7053 -0.2553 0.4668 0.0266 1.0000 Uiso R . . . . .
H121 H 0.7135 -0.2436 0.3854 0.0288 1.0000 Uiso R . . . . .
H122 H 0.7933 -0.1634 0.3893 0.0289 1.0000 Uiso R . . . . .
H131 H 0.9391 -0.3795 0.3442 0.0650 1.0000 Uiso R . . . . .
H132 H 0.8280 -0.3470 0.3317 0.0649 1.0000 Uiso R . . . . .
H133 H 0.9149 -0.2642 0.3342 0.0638 1.0000 Uiso R . . . . .
H151 H 0.6636 -0.0598 0.3888 0.0330 1.0000 Uiso R . . . . .
H181 H 0.4277 -0.0783 0.5047 0.0344 1.0000 Uiso R . . . . .
H191 H 0.5703 -0.1786 0.5085 0.0327 1.0000 Uiso R . . . . .
H201 H 0.6430 0.0820 0.3467 0.0421 1.0000 Uiso R . . . . .
H202 H 0.5797 -0.0019 0.3219 0.0435 1.0000 Uiso R . . . . .
H211 H 0.5269 0.2003 0.3208 0.1252 1.0000 Uiso R . . . . .
H212 H 0.5839 0.1514 0.2789 0.1251 1.0000 Uiso R . . . . .
H213 H 0.4733 0.1176 0.2918 0.1253 1.0000 Uiso R . . . . .
H221 H 0.3295 0.0577 0.5030 0.0534 1.0000 Uiso R . . . . .
H222 H 0.2464 0.0863 0.4679 0.0531 1.0000 Uiso R . . . . .
H223 H 0.2734 -0.0253 0.4761 0.0534 1.0000 Uiso R . . . . .
S31 S 0.09552(5) 0.94246(5) 0.33989(2) 0.0290 1.0000 Uani . . . . . .
O31 O -0.21168(15) 0.94752(17) 0.32686(7) 0.0314 1.0000 Uani . . . . . .
O32 O 0.01512(15) 1.00289(16) 0.20986(7) 0.0289 1.0000 Uani . . . . . .
O33 O -0.0830(2) 0.72915(18) 0.08843(7) 0.0406 1.0000 Uani . . . . . .
O34 O 0.04997(19) 0.85651(17) 0.31846(8) 0.0379 1.0000 Uani . . . . . .
O35 O 0.18159(19) 0.9855(2) 0.31680(9) 0.0477 1.0000 Uani . . . . . .
O36 O -0.29910(19) 1.40725(17) 0.32929(7) 0.0388 1.0000 Uani . . . . . .
O37 O -0.28777(17) 1.27407(17) 0.39419(7) 0.0346 1.0000 Uani . . . . . .
N33 N -0.09017(16) 0.99805(17) 0.27439(7) 0.0233 1.0000 Uani . . . . . .
N32 N -0.04720(18) 0.84610(18) 0.14327(8) 0.0270 1.0000 Uani D . . . . .
C31 C -0.1153(2) 0.8215(2) 0.17822(9) 0.0249 1.0000 Uani D . . . . .
C32 C -0.1841(2) 0.7419(2) 0.17688(10) 0.0311 1.0000 Uani . . . . . .
C33 C -0.2510(2) 0.7248(2) 0.21266(11) 0.0339 1.0000 Uani . . . . . .
C34 C -0.2553(2) 0.7858(2) 0.25187(10) 0.0305 1.0000 Uani . . . . . .
C35 C -0.1871(2) 0.8627(2) 0.25334(9) 0.0250 1.0000 Uani . . . . . .
C36 C -0.1684(2) 0.9383(2) 0.28957(9) 0.0257 1.0000 Uani . . . . . .
C37 C -0.0547(2) 0.9661(2) 0.23091(9) 0.0226 1.0000 Uani . . . . . .
C38 C -0.11800(19) 0.8804(2) 0.21787(9) 0.0225 1.0000 Uani . . . . . .
C39 C -0.0360(2) 0.8025(2) 0.10021(10) 0.0301 1.0000 Uani D . . . . .
C40 C 0.0377(3) 0.8545(3) 0.06916(11) 0.0392 1.0000 Uani . . . . . .
C41 C -0.0395(2) 1.0760(2) 0.30200(9) 0.0238 1.0000 Uani . . . . . .
C42 C 0.0009(2) 1.0339(2) 0.34783(9) 0.0253 1.0000 Uani . . . . . .
C43 C 0.1275(3) 0.9121(3) 0.39750(12) 0.0447 1.0000 Uani . . . . . .
C44 C -0.1084(2) 1.1645(2) 0.30999(9) 0.0238 1.0000 Uani . . . . . .
C45 C -0.1659(2) 1.1759(2) 0.35052(9) 0.0258 1.0000 Uani . . . . . .
C46 C -0.2289(2) 1.2574(2) 0.35629(9) 0.0269 1.0000 Uani . . . . . .
C47 C -0.2355(2) 1.3299(2) 0.32085(10) 0.0278 1.0000 Uani . . . . . .
C48 C -0.1777(2) 1.3186(2) 0.28113(9) 0.0285 1.0000 Uani . . . . . .
C49 C -0.1140(2) 1.2370(2) 0.27607(9) 0.0285 1.0000 Uani . . . . . .
C50 C -0.2859(2) 1.2007(2) 0.43046(10) 0.0320 1.0000 Uani . . . . . .
C51 C -0.3669(3) 1.2294(3) 0.46500(11) 0.0436 1.0000 Uani . . . . . .
C52 C -0.3090(3) 1.4783(3) 0.29298(12) 0.0479 1.0000 Uani . . . . . .
H321 H -0.1830 0.6987 0.1519 0.0383 1.0000 Uiso R . . . . .
H331 H -0.2911 0.6706 0.2105 0.0412 1.0000 Uiso R . . . . .
H341 H -0.2998 0.7736 0.2754 0.0365 1.0000 Uiso R . . . . .
H401 H 0.0970 0.8699 0.0859 0.0599 1.0000 Uiso R . . . . .
H402 H 0.0062 0.9144 0.0578 0.0594 1.0000 Uiso R . . . . .
H403 H 0.0542 0.8138 0.0428 0.0594 1.0000 Uiso R . . . . .
H411 H 0.0194 1.0977 0.2848 0.0295 1.0000 Uiso R . . . . .
H421 H -0.0532 1.0050 0.3663 0.0307 1.0000 Uiso R . . . . .
H422 H 0.0319 1.0888 0.3648 0.0302 1.0000 Uiso R . . . . .
H431 H 0.0705 0.8841 0.4131 0.0670 1.0000 Uiso R . . . . .
H432 H 0.1487 0.9713 0.4122 0.0664 1.0000 Uiso R . . . . .
H433 H 0.1822 0.8654 0.3960 0.0668 1.0000 Uiso R . . . . .
H451 H -0.1612 1.1284 0.3735 0.0315 1.0000 Uiso R . . . . .
H481 H -0.1815 1.3642 0.2578 0.0338 1.0000 Uiso R . . . . .
H491 H -0.0750 1.2319 0.2498 0.0344 1.0000 Uiso R . . . . .
H501 H -0.2209 1.1976 0.4440 0.0383 1.0000 Uiso R . . . . .
H502 H -0.3024 1.1365 0.4188 0.0382 1.0000 Uiso R . . . . .
H511 H -0.3510 1.2941 0.4775 0.0653 1.0000 Uiso R . . . . .
H512 H -0.3667 1.1842 0.4907 0.0658 1.0000 Uiso R . . . . .
H513 H -0.4319 1.2335 0.4508 0.0646 1.0000 Uiso R . . . . .
H521 H -0.2415 1.5041 0.2855 0.0704 1.0000 Uiso R . . . . .
H522 H -0.3511 1.5294 0.3039 0.0701 1.0000 Uiso R . . . . .
H523 H -0.3392 1.4475 0.2660 0.0705 1.0000 Uiso R . . . . .
H691 H 0.405(4) 0.177(2) 0.405(2) 0.079(2) 1.0000 Uiso D . . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826
-11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669
'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Br -0.6763 1.2805 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328
2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_site_symmetry_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C67 . O69 . H691 . 119(4) no
C62 . C61 . C66 . 120.5(3) yes
C62 . C61 . C67 . 120.5(3) yes
C66 . C61 . C67 . 118.9(3) yes
C61 . C62 . C63 . 119.4(3) yes
C61 . C62 . H621 . 121.0 no
C63 . C62 . H621 . 119.6 no
C62 . C63 . C64 . 118.9(3) yes
C62 . C63 . H631 . 120.8 no
C64 . C63 . H631 . 120.3 no
C63 . C64 . C65 . 122.5(3) yes
C63 . C64 . Br70 . 119.6(3) yes
C65 . C64 . Br70 . 117.9(3) yes
C64 . C65 . C66 . 118.6(3) yes
C64 . C65 . H651 . 119.4 no
C66 . C65 . H651 . 121.9 no
C65 . C66 . C61 . 120.1(3) yes
C65 . C66 . H661 . 118.7 no
C61 . C66 . H661 . 121.2 no
C61 . C67 . O69 . 112.2(3) yes
C61 . C67 . O68 . 123.3(4) yes
O69 . C67 . O68 . 124.5(3) yes
O4 . S1 . O5 . 117.58(14) yes
O4 . S1 . C12 . 109.31(13) yes
O5 . S1 . C12 . 108.67(14) yes
O4 . S1 . C13 . 108.46(16) yes
O5 . S1 . C13 . 109.52(18) yes
C12 . S1 . C13 . 102.19(15) yes
C16 . O6 . C20 . 117.6(2) yes
C17 . O7 . C22 . 116.8(2) yes
C6 . N1 . C7 . 111.6(2) yes
C6 . N1 . C11 . 125.9(2) yes
C7 . N1 . C11 . 122.2(2) yes
H22 . N2 . C1 . 116.0(13) no
H22 . N2 . C9 . 114.6(13) no
C1 . N2 . C9 . 129.4(3) yes
N2 . C1 . C2 . 125.3(3) yes
N2 . C1 . C8 . 118.5(3) yes
C2 . C1 . C8 . 116.1(3) yes
C1 . C2 . C3 . 121.0(3) yes
C1 . C2 . H21 . 118.6 no
C3 . C2 . H21 . 120.3 no
C2 . C3 . C4 . 122.3(3) yes
C2 . C3 . H662 . 118.7 no
C4 . C3 . H662 . 119.0 no
C3 . C4 . C5 . 115.9(3) yes
C3 . C4 . H41 . 121.8 no
C5 . C4 . H41 . 122.3 no
C4 . C5 . C6 . 129.6(3) yes
C4 . C5 . C8 . 122.4(3) yes
C6 . C5 . C8 . 108.0(2) yes
C5 . C6 . N1 . 105.9(2) yes
C5 . C6 . O1 . 129.0(3) yes
N1 . C6 . O1 . 125.1(3) yes
N1 . C7 . O2 . 125.3(2) yes
N1 . C7 . C8 . 106.0(2) yes
O2 . C7 . C8 . 128.7(2) yes
C7 . C8 . C1 . 129.2(3) yes
C7 . C8 . C5 . 108.5(2) yes
C1 . C8 . C5 . 122.3(3) yes
N2 . C9 . O3 . 122.5(3) yes
N2 . C9 . C10 . 114.8(3) yes
O3 . C9 . C10 . 122.7(3) yes
C9 . C10 . H101 . 108.8 no
C9 . C10 . H102 . 109.3 no
H101 . C10 . H102 . 109.1 no
C9 . C10 . H103 . 112.1 no
H101 . C10 . H103 . 107.2 no
H102 . C10 . H103 . 110.3 no
N1 . C11 . C12 . 111.5(2) yes
N1 . C11 . C14 . 112.2(2) yes
C12 . C11 . C14 . 111.0(2) yes
N1 . C11 . H111 . 106.9 no
C12 . C11 . H111 . 107.7 no
C14 . C11 . H111 . 107.3 no
C11 . C12 . S1 . 113.33(18) yes
C11 . C12 . H121 . 109.4 no
S1 . C12 . H121 . 108.9 no
C11 . C12 . H122 . 111.2 no
S1 . C12 . H122 . 107.2 no
H121 . C12 . H122 . 106.5 no
S1 . C13 . H131 . 106.7 no
S1 . C13 . H132 . 107.8 no
H131 . C13 . H132 . 110.8 no
S1 . C13 . H133 . 107.5 no
H131 . C13 . H133 . 111.7 no
H132 . C13 . H133 . 112.0 no
C11 . C14 . C15 . 122.2(2) yes
C11 . C14 . C19 . 118.7(2) yes
C15 . C14 . C19 . 119.1(3) yes
C14 . C15 . C16 . 120.1(2) yes
C14 . C15 . H151 . 120.0 no
C16 . C15 . H151 . 119.9 no
C15 . C16 . O6 . 124.7(3) yes
C15 . C16 . C17 . 120.0(3) yes
O6 . C16 . C17 . 115.2(2) yes
C16 . C17 . O7 . 115.3(3) yes
C16 . C17 . C18 . 120.0(3) yes
O7 . C17 . C18 . 124.7(3) yes
C17 . C18 . C19 . 120.2(3) yes
C17 . C18 . H181 . 118.4 no
C19 . C18 . H181 . 121.4 no
C18 . C19 . C14 . 120.6(3) yes
C18 . C19 . H191 . 120.0 no
C14 . C19 . H191 . 119.4 no
O6 . C20 . C21 . 107.4(3) yes
O6 . C20 . H201 . 111.0 no
C21 . C20 . H201 . 110.3 no
O6 . C20 . H202 . 106.8 no
C21 . C20 . H202 . 111.9 no
H201 . C20 . H202 . 109.4 no
C20 . C21 . H211 . 107.6 no
C20 . C21 . H212 . 110.1 no
H211 . C21 . H212 . 110.1 no
C20 . C21 . H213 . 108.4 no
H211 . C21 . H213 . 109.6 no
H212 . C21 . H213 . 110.9 no
O7 . C22 . H221 . 107.5 no
O7 . C22 . H222 . 109.0 no
H221 . C22 . H222 . 110.2 no
O7 . C22 . H223 . 108.9 no
H221 . C22 . H223 . 110.8 no
H222 . C22 . H223 . 110.3 no
O34 . S31 . O35 . 116.98(16) yes
O34 . S31 . C42 . 108.56(13) yes
O35 . S31 . C42 . 109.79(15) yes
O34 . S31 . C43 . 108.52(17) yes
O35 . S31 . C43 . 109.90(18) yes
C42 . S31 . C43 . 102.03(15) yes
C47 . O36 . C52 . 116.0(2) yes
C46 . O37 . C50 . 117.5(2) yes
C36 . N33 . C37 . 110.7(2) yes
C36 . N33 . C41 . 125.5(2) yes
C37 . N33 . C41 . 123.2(2) yes
H320 . N32 . C31 . 116.5(12) no
H320 . N32 . C39 . 115.2(12) no
C31 . N32 . C39 . 128.3(3) yes
N32 . C31 . C32 . 125.4(3) yes
N32 . C31 . C38 . 118.4(3) yes
C32 . C31 . C38 . 116.1(2) yes
C31 . C32 . C33 . 121.4(3) yes
C31 . C32 . H321 . 119.4 no
C33 . C32 . H321 . 119.2 no
C32 . C33 . C34 . 122.2(3) yes
C32 . C33 . H331 . 117.4 no
C34 . C33 . H331 . 120.3 no
C33 . C34 . C35 . 116.1(3) yes
C33 . C34 . H341 . 121.5 no
C35 . C34 . H341 . 122.3 no
C34 . C35 . C36 . 130.5(3) yes
C34 . C35 . C38 . 122.5(3) yes
C36 . C35 . C38 . 107.0(2) yes
C35 . C36 . N33 . 107.5(2) yes
C35 . C36 . O31 . 127.8(3) yes
N33 . C36 . O31 . 124.7(3) yes
N33 . C37 . O32 . 125.1(3) yes
N33 . C37 . C38 . 106.2(2) yes
O32 . C37 . C38 . 128.7(2) yes
C37 . C38 . C31 . 129.9(2) yes
C37 . C38 . C35 . 108.6(2) yes
C31 . C38 . C35 . 121.5(3) yes
N32 . C39 . O33 . 122.8(3) yes
N32 . C39 . C40 . 114.1(3) yes
O33 . C39 . C40 . 123.1(3) yes
C39 . C40 . H401 . 109.7 no
C39 . C40 . H402 . 108.3 no
H401 . C40 . H402 . 110.5 no
C39 . C40 . H403 . 110.7 no
H401 . C40 . H403 . 109.8 no
H402 . C40 . H403 . 107.8 no
N33 . C41 . C42 . 111.2(2) yes
N33 . C41 . C44 . 111.6(2) yes
C42 . C41 . C44 . 111.6(2) yes
N33 . C41 . H411 . 107.7 no
C42 . C41 . H411 . 105.8 no
C44 . C41 . H411 . 108.8 no
C41 . C42 . S31 . 113.01(18) yes
C41 . C42 . H421 . 111.3 no
S31 . C42 . H421 . 108.2 no
C41 . C42 . H422 . 107.4 no
S31 . C42 . H422 . 107.2 no
H421 . C42 . H422 . 109.7 no
S31 . C43 . H431 . 110.3 no
S31 . C43 . H432 . 107.3 no
H431 . C43 . H432 . 110.9 no
S31 . C43 . H433 . 106.8 no
H431 . C43 . H433 . 111.1 no
H432 . C43 . H433 . 110.4 no
C41 . C44 . C45 . 122.5(2) yes
C41 . C44 . C49 . 118.6(2) yes
C45 . C44 . C49 . 118.9(3) yes
C44 . C45 . C46 . 120.7(2) yes
C44 . C45 . H451 . 119.2 no
C46 . C45 . H451 . 120.1 no
C45 . C46 . O37 . 124.8(3) yes
C45 . C46 . C47 . 119.7(2) yes
O37 . C46 . C47 . 115.5(3) yes
C46 . C47 . O36 . 115.9(2) yes
C46 . C47 . C48 . 119.1(3) yes
O36 . C47 . C48 . 125.0(3) yes
C47 . C48 . C49 . 120.5(3) yes
C47 . C48 . H481 . 120.4 no
C49 . C48 . H481 . 119.1 no
C48 . C49 . C44 . 121.0(3) yes
C48 . C49 . H491 . 119.0 no
C44 . C49 . H491 . 120.1 no
O37 . C50 . C51 . 107.0(3) yes
O37 . C50 . H501 . 110.3 no
C51 . C50 . H501 . 112.4 no
O37 . C50 . H502 . 111.2 no
C51 . C50 . H502 . 107.7 no
H501 . C50 . H502 . 108.3 no
C50 . C51 . H511 . 108.9 no
C50 . C51 . H512 . 110.2 no
H511 . C51 . H512 . 106.4 no
C50 . C51 . H513 . 111.6 no
H511 . C51 . H513 . 107.8 no
H512 . C51 . H513 . 111.8 no
O36 . C52 . H521 . 108.4 no
O36 . C52 . H522 . 107.4 no
H521 . C52 . H522 . 110.7 no
O36 . C52 . H523 . 110.0 no
H521 . C52 . H523 . 110.4 no
H522 . C52 . H523 . 109.9 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_site_symmetry_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
H22 . N2 . 0.849(18) no
H320 . N32 . 0.842(18) no
O69 . C67 . 1.315(5) yes
O69 . H691 . 0.823(19) no
O68 . C67 . 1.214(5) yes
C61 . C62 . 1.396(5) yes
C61 . C66 . 1.376(5) yes
C61 . C67 . 1.499(4) yes
C62 . C63 . 1.386(5) yes
C62 . H621 . 0.948 no
C63 . C64 . 1.381(5) yes
C63 . H631 . 0.950 no
C64 . C65 . 1.366(5) yes
C64 . Br70 . 1.892(3) yes
C65 . C66 . 1.394(5) yes
C65 . H651 . 0.936 no
C66 . H661 . 0.982 no
S1 . O4 . 1.440(2) yes
S1 . O5 . 1.441(2) yes
S1 . C12 . 1.773(3) yes
S1 . C13 . 1.748(3) yes
O1 . C6 . 1.215(3) yes
O2 . C7 . 1.212(3) yes
O3 . C9 . 1.217(4) yes
O6 . C16 . 1.368(4) yes
O6 . C20 . 1.445(4) yes
O7 . C17 . 1.373(4) yes
O7 . C22 . 1.434(4) yes
N1 . C6 . 1.393(4) yes
N1 . C7 . 1.402(3) yes
N1 . C11 . 1.474(3) yes
N2 . C1 . 1.390(4) yes
N2 . C9 . 1.365(4) yes
C1 . C2 . 1.412(4) yes
C1 . C8 . 1.386(4) yes
C2 . C3 . 1.390(5) yes
C2 . H21 . 0.894 no
C3 . C4 . 1.398(5) yes
C3 . H662 . 0.931 no
C4 . C5 . 1.386(4) yes
C4 . H41 . 0.925 no
C5 . C6 . 1.495(4) yes
C5 . C8 . 1.381(4) yes
C7 . C8 . 1.481(4) yes
C9 . C10 . 1.508(5) yes
C10 . H101 . 0.944 no
C10 . H102 . 0.951 no
C10 . H103 . 0.946 no
C11 . C12 . 1.535(4) yes
C11 . C14 . 1.514(4) yes
C11 . H111 . 0.951 no
C12 . H121 . 0.942 no
C12 . H122 . 0.948 no
C13 . H131 . 0.963 no
C13 . H132 . 0.950 no
C13 . H133 . 0.985 no
C14 . C15 . 1.409(4) yes
C14 . C19 . 1.387(4) yes
C15 . C16 . 1.382(4) yes
C15 . H151 . 0.902 no
C16 . C17 . 1.400(4) yes
C17 . C18 . 1.379(4) yes
C18 . C19 . 1.389(4) yes
C18 . H181 . 0.899 no
C19 . H191 . 0.933 no
C20 . C21 . 1.495(5) yes
C20 . H201 . 0.957 no
C20 . H202 . 0.977 no
C21 . H211 . 0.957 no
C21 . H212 . 0.960 no
C21 . H213 . 0.955 no
C22 . H221 . 0.930 no
C22 . H222 . 0.952 no
C22 . H223 . 0.954 no
S31 . O34 . 1.444(2) yes
S31 . O35 . 1.441(3) yes
S31 . C42 . 1.771(3) yes
S31 . C43 . 1.765(3) yes
O31 . C36 . 1.225(3) yes
O32 . C37 . 1.212(3) yes
O33 . C39 . 1.216(4) yes
O36 . C47 . 1.361(4) yes
O36 . C52 . 1.426(4) yes
O37 . C46 . 1.362(3) yes
O37 . C50 . 1.440(3) yes
N33 . C36 . 1.382(4) yes
N33 . C37 . 1.408(3) yes
N33 . C41 . 1.478(3) yes
N32 . C31 . 1.393(3) yes
N32 . C39 . 1.383(4) yes
C31 . C32 . 1.407(4) yes
C31 . C38 . 1.394(4) yes
C32 . C33 . 1.380(4) yes
C32 . H321 . 0.926 no
C33 . C34 . 1.400(5) yes
C33 . H331 . 0.903 no
C34 . C35 . 1.375(4) yes
C34 . H341 . 0.914 no
C35 . C36 . 1.481(4) yes
C35 . C38 . 1.393(4) yes
C37 . C38 . 1.474(4) yes
C39 . C40 . 1.499(4) yes
C40 . H401 . 0.945 no
C40 . H402 . 0.965 no
C40 . H403 . 0.963 no
C41 . C42 . 1.536(4) yes
C41 . C44 . 1.518(4) yes
C41 . H411 . 0.968 no
C42 . H421 . 0.974 no
C42 . H422 . 0.977 no
C43 . H431 . 0.956 no
C43 . H432 . 0.947 no
C43 . H433 . 0.960 no
C44 . C45 . 1.404(4) yes
C44 . C49 . 1.385(4) yes
C45 . C46 . 1.388(4) yes
C45 . H451 . 0.923 no
C46 . C47 . 1.418(4) yes
C47 . C48 . 1.387(4) yes
C48 . C49 . 1.393(4) yes
C48 . H481 . 0.914 no
C49 . H491 . 0.919 no
C50 . C51 . 1.514(4) yes
C50 . H501 . 0.946 no
C50 . H502 . 0.953 no
C51 . H511 . 0.967 no
C51 . H512 . 0.959 no
C51 . H513 . 0.955 no
C52 . H521 . 0.982 no
C52 . H522 . 0.939 no
C52 . H523 . 0.968 no
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
_oxford_refln_omitted_details
2 1 0 x .
-6 7 2 x .
5 4 4 x .
0 1 5 x .
-6 12 2 x .
-1 5 25 x .
