#------------------------------------------------------------------------------
#$Date: 2021-03-27 08:13:50 +0200 (Sat, 27 Mar 2021) $
#$Revision: 263391 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243792.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_2243792
loop_
_publ_author_name
'Zeller, Matthias'
'Bogdanowich-Knipp, Susan'
'Smith, Pamela'
'Purcell, Dale K.'
'Okezue, Mercy'
'Smith, Daniel T.'
'Byrn, Stephen R.'
'Clase, Kari L.'
_publ_section_title
;
 Maleate salts of bedaquiline
;
_journal_coeditor_code           TX2038
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              433
_journal_page_last               445
_journal_paper_doi               10.1107/S2056989021002991
_journal_volume                  77
_journal_year                    2021
_chemical_absolute_configuration ad
_chemical_formula_iupac
'2C32 H32 Br N2 O2 +, 2C4 H3 O4 -, 0.495C6 H14, 2.01C3 H6 O'
_chemical_formula_moiety
'2(C32 H32 Br N2 O2 +), 2(C4 H3 O4 -), 0.495(C6 H14), 2.01(C3 H6 O)'
_chemical_formula_sum            'C81 H89 Br2 N4 O14'
_chemical_formula_weight         1502.51
_chemical_name_common
;
Bedaquilinium maleate--hexane--acetone (1/0.248/1)
;
_chemical_name_systematic
;[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate--hexane--acetone
(1/0.248/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     isomor
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 107.6347(18)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   16.0678(9)
_cell_length_b                   13.6440(8)
_cell_length_c                   17.8720(8)
_cell_measurement_reflns_used    9698
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.6786
_cell_measurement_theta_min      2.5268
_cell_volume                     3733.9(3)
_computing_cell_refinement
;
SAINT (Bruker, 2020)
;
_computing_data_collection
;
APEX3 (Bruker, 2020)
;
_computing_data_reduction
;
SAINT (Bruker, 2020)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015b),
shelXle  (Hübschle et al.,  2011)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 7.4074
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest with PhotonII CPAD
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'Triumph curved graphite crystal'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0586
_diffrn_reflns_av_unetI/netI     0.0738
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            73087
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.141
_diffrn_reflns_theta_min         2.392
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.153
_exptl_absorpt_correction_T_max  0.4978
_exptl_absorpt_correction_T_min  0.4388
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             1570.1
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.605
_refine_diff_density_min         -0.622
_refine_ls_abs_structure_details
;
Flack x determined using 3753 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.006(3)
_refine_ls_extinction_coef       0.0034(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018/3 (Sheldrick, 2015b)
;
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     558
_refine_ls_number_reflns         14074
_refine_ls_number_restraints     407
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0815
_refine_ls_R_factor_gt           0.0466
_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/[σ²(Fo²)+(0.0357P)²+1.6623P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1096
_refine_ls_wR_factor_ref         0.1261
_reflns_number_gt                9700
_reflns_number_total             14074
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2038sup1.cif
_cod_data_source_block           acetone_hexane
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2243792
_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   0.608
_shelx_estimated_absorpt_t_max   0.794
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
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 Br1 0.28108(4) 0.03150(4) 0.45830(4) 0.1050(2) Uani d 1 . .
O O1 0.48565(12) 0.26573(13) 0.16549(10) 0.0360(4) Uani d 1 . .
H H1O 0.440644 0.279937 0.177824 0.043 Uiso calc 1 . .
O O2 0.56438(12) 0.47869(14) 0.36251(10) 0.0366(4) Uani d 1 . .
O O3 0.50234(13) 0.68019(15) 0.21207(12) 0.0437(4) Uani d 1 . .
O O4 0.57291(17) 0.6900(3) 0.12449(13) 0.0702(8) Uani d 1 . .
O O5 0.70949(16) 0.7561(2) 0.11557(13) 0.0668(8) Uani d 1 . .
H H5 0.642(3) 0.727(4) 0.122(3) 0.080 Uiso d 1 . .
O O6 0.82960(13) 0.81698(18) 0.19657(14) 0.0513(5) Uani d 1 . .
N N1 0.40093(12) 0.55897(14) 0.10162(11) 0.0292(4) Uani d 1 . .
H H1 0.437687 0.607063 0.139756 0.035 Uiso calc 1 . .
N N2 0.45948(13) 0.40362(16) 0.40492(11) 0.0328(4) Uani d 1 . .
C C1 0.60196(15) 0.31733(18) 0.28231(13) 0.0309(4) Uani d 1 . .
H H1A 0.640880 0.374982 0.301923 0.037 Uiso calc 1 . .
C C2 0.54990(15) 0.33968(17) 0.19372(12) 0.0293(4) Uani d 1 . .
C C3 0.50225(15) 0.43881(17) 0.18800(12) 0.0282(4) Uani d 1 . .
H H3A 0.459176 0.434483 0.217451 0.034 Uiso calc 1 . .
H H3B 0.545234 0.490092 0.213099 0.034 Uiso calc 1 . .
C C4 0.45543(16) 0.46892(18) 0.10393(13) 0.0312(4) Uani d 1 . .
H H4A 0.498951 0.482057 0.076072 0.037 Uiso calc 1 . .
H H4B 0.417505 0.414569 0.076535 0.037 Uiso calc 1 . .
C C5 0.32133(17) 0.5395(2) 0.12599(18) 0.0437(6) Uani d 1 . .
H H5A 0.284267 0.491520 0.090222 0.066 Uiso calc 1 . .
H H5B 0.288771 0.600620 0.124098 0.066 Uiso calc 1 . .
H H5C 0.338747 0.513454 0.179618 0.066 Uiso calc 1 . .
C C6 0.37641(18) 0.6054(2) 0.02278(15) 0.0388(5) Uani d 1 . .
H H6A 0.345648 0.557539 -0.016892 0.058 Uiso calc 1 . .
H H6B 0.429230 0.627598 0.011272 0.058 Uiso calc 1 . .
H H6C 0.338160 0.661574 0.021921 0.058 Uiso calc 1 . .
C C7 0.61170(16) 0.33633(18) 0.14255(13) 0.0334(5) Uani d 1 . .
C C8 0.5954(2) 0.2673(2) 0.08362(14) 0.0426(6) Uani d 1 . .
H H8 0.546889 0.224460 0.075988 0.051 Uiso calc 1 . .
C C9 0.6497(2) 0.2587(3) 0.03370(15) 0.0533(8) Uani d 1 . .
H H9 0.636836 0.210335 -0.006425 0.064 Uiso calc 1 . .
C C10 0.7186(2) 0.3182(3) 0.04292(17) 0.0529(8) Uani d 1 . .
H H10 0.754151 0.311643 0.009299 0.063 Uiso calc 1 . .
C C11 0.7386(2) 0.3900(3) 0.10180(17) 0.0477(7) Uani d 1 . .
C C12 0.8104(2) 0.4549(3) 0.1104(2) 0.0638(10) Uani d 1 . .
H H12 0.845434 0.447108 0.076433 0.077 Uiso calc 1 . .
C C13 0.8306(2) 0.5266(4) 0.1644(2) 0.0657(9) Uani d 1 . .
H H13 0.878384 0.569256 0.168070 0.079 Uiso calc 1 . .
C C14 0.7799(2) 0.5372(3) 0.2152(2) 0.0537(7) Uani d 1 . .
H H14 0.794272 0.587019 0.254109 0.064 Uiso calc 1 . .
C C15 0.70973(18) 0.4770(2) 0.20992(16) 0.0415(6) Uani d 1 . .
H H15 0.676695 0.486501 0.245324 0.050 Uiso calc 1 . .
C C16 0.68507(16) 0.4007(2) 0.15300(14) 0.0360(5) Uani d 1 . .
C C17 0.66129(17) 0.2277(2) 0.29397(14) 0.0374(5) Uani d 1 . .
C C18 0.6378(2) 0.1398(2) 0.2548(2) 0.0508(7) Uani d 1 . .
H H18 0.581932 0.133510 0.216972 0.061 Uiso calc 1 . .
C C19 0.6951(3) 0.0602(3) 0.2700(2) 0.0641(9) Uani d 1 . .
H H19 0.678486 0.000948 0.241496 0.077 Uiso calc 1 . .
C C20 0.7750(3) 0.0670(3) 0.3256(2) 0.0708(11) Uani d 1 . .
H H20 0.813448 0.012276 0.337027 0.085 Uiso calc 1 . .
C C21 0.7987(3) 0.1538(4) 0.3645(3) 0.0800(13) Uani d 1 . .
H H21 0.854203 0.159268 0.403026 0.096 Uiso calc 1 . .
C C22 0.7429(2) 0.2343(3) 0.34874(19) 0.0566(8) Uani d 1 . .
H H22 0.761007 0.294280 0.375823 0.068 Uiso calc 1 . .
C C23 0.54033(15) 0.31153(18) 0.33221(12) 0.0298(4) Uani d 1 . .
C C24 0.50170(16) 0.22692(18) 0.34487(13) 0.0321(4) Uani d 1 . .
H H24 0.515631 0.166907 0.324504 0.039 Uiso calc 1 . .
C C25 0.44064(16) 0.2275(2) 0.38831(13) 0.0341(5) Uani d 1 . .
C C26 0.39966(19) 0.1409(2) 0.40278(17) 0.0440(6) Uani d 1 . .
H H26 0.414743 0.079158 0.385947 0.053 Uiso calc 1 . .
C C27 0.3380(2) 0.1469(3) 0.4413(2) 0.0521(7) Uani d 1 . .
C C28 0.31484(19) 0.2374(3) 0.46714(17) 0.0495(7) Uani d 1 . .
H H28 0.271320 0.240153 0.493110 0.059 Uiso calc 1 . .
C C29 0.35541(16) 0.3215(2) 0.45464(14) 0.0404(6) Uani d 1 . .
H H29 0.340300 0.382411 0.472727 0.048 Uiso calc 1 . .
C C30 0.41953(15) 0.3185(2) 0.41512(12) 0.0326(5) Uani d 1 . .
C C31 0.51833(15) 0.39829(18) 0.36816(12) 0.0302(4) Uani d 1 . .
C C32 0.5439(2) 0.5672(2) 0.39697(19) 0.0495(7) Uani d 1 . .
H H32A 0.484998 0.589046 0.367337 0.074 Uiso calc 1 . .
H H32B 0.586226 0.618203 0.395465 0.074 Uiso calc 1 . .
H H32C 0.546336 0.554523 0.451582 0.074 Uiso calc 1 . .
C C33 0.56682(18) 0.7043(2) 0.19291(15) 0.0391(5) Uani d 1 . .
C C34 0.64121(18) 0.7502(2) 0.25429(14) 0.0388(5) Uani d 1 . .
H H34 0.632657 0.756615 0.304375 0.047 Uiso calc 1 . .
C C35 0.71764(18) 0.7835(2) 0.25022(15) 0.0392(5) Uani d 1 . .
H H35 0.754338 0.810422 0.297846 0.047 Uiso calc 1 . .
C C36 0.75529(18) 0.7859(2) 0.18370(16) 0.0398(5) Uani d 1 . .
O O7 0.5989(5) 0.8015(5) 0.4370(5) 0.097(3) Uani d 0.505(9) A 1
C C37 0.5409(12) 0.8497(16) 0.3963(12) 0.119(4) Uani d 0.505(9) A 1
C C38 0.4480(8) 0.8322(11) 0.3707(11) 0.128(4) Uani d 0.505(9) A 1
H H38A 0.429939 0.809616 0.316077 0.193 Uiso calc 0.505(9) A 1
H H38B 0.417134 0.893012 0.374591 0.193 Uiso calc 0.505(9) A 1
H H38C 0.433707 0.781911 0.404054 0.193 Uiso calc 0.505(9) A 1
C C39 0.5660(10) 0.9345(9) 0.3579(11) 0.125(5) Uani d 0.505(9) A 1
H H39A 0.626967 0.927640 0.358730 0.187 Uiso calc 0.505(9) A 1
H H39B 0.559451 0.994471 0.385823 0.187 Uiso calc 0.505(9) A 1
H H39C 0.528346 0.938335 0.303383 0.187 Uiso calc 0.505(9) A 1
C C43 0.4921(13) 0.9070(14) 0.3204(10) 0.147(6) Uani d 0.495(9) A 2
H H43A 0.532067 0.903050 0.288555 0.220 Uiso calc 0.495(9) A 2
H H43B 0.482284 0.975965 0.330675 0.220 Uiso calc 0.495(9) A 2
H H43C 0.436329 0.876333 0.292035 0.220 Uiso calc 0.495(9) A 2
C C44 0.5325(15) 0.853(2) 0.3990(11) 0.131(4) Uani d 0.495(9) A 2
H H44A 0.536158 0.782358 0.388301 0.157 Uiso calc 0.495(9) A 2
H H44B 0.592752 0.877463 0.423074 0.157 Uiso calc 0.495(9) A 2
C C45 0.4823(10) 0.8658(17) 0.4569(4) 0.151(5) Uani d 0.495(9) A 2
H H45A 0.450816 0.928805 0.443022 0.181 Uiso calc 0.495(9) A 2
H H45B 0.436974 0.814058 0.443951 0.181 Uiso calc 0.495(9) A 2
O O8A 0.4373(18) 1.0370(17) -0.0198(16) 0.134(7) Uani d 0.230(11) B -1
C C40A 0.489(2) 0.9735(18) -0.0008(19) 0.087(5) Uani d 0.230(11) B -1
C C41A 0.482(3) 0.8753(17) -0.038(2) 0.089(6) Uani d 0.230(11) B -1
H H41A 0.451893 0.881229 -0.094492 0.133 Uiso calc 0.230(11) B -1
H H41B 0.449048 0.831225 -0.014304 0.133 Uiso calc 0.230(11) B -1
H H41C 0.540733 0.848755 -0.030175 0.133 Uiso calc 0.230(11) B -1
C C42A 0.563(2) 0.979(3) 0.071(2) 0.103(8) Uani d 0.230(11) B -1
H H42A 0.615091 0.952339 0.060829 0.155 Uiso calc 0.230(11) B -1
H H42B 0.550070 0.941609 0.112743 0.155 Uiso calc 0.230(11) B -1
H H42C 0.573559 1.047975 0.087216 0.155 Uiso calc 0.230(11) B -1
O O8B 0.4818(16) 1.0511(9) 0.0406(11) 0.120(6) Uani d 0.270(11) B -2
C C40B 0.4889(18) 0.9844(15) 0.0016(16) 0.085(5) Uani d 0.270(11) B -2
C C41B 0.532(3) 0.896(2) 0.044(2) 0.107(7) Uani d 0.270(11) B -2
H H41D 0.592218 0.893131 0.043466 0.160 Uiso calc 0.270(11) B -2
H H41E 0.500248 0.837423 0.018815 0.160 Uiso calc 0.270(11) B -2
H H41F 0.530423 0.899033 0.098710 0.160 Uiso calc 0.270(11) B -2
C C42B 0.454(2) 0.973(3) -0.0838(13) 0.092(7) Uani d 0.270(11) B -2
H H42D 0.496337 0.937141 -0.103146 0.138 Uiso calc 0.270(11) B -2
H H42E 0.442785 1.037169 -0.108707 0.138 Uiso calc 0.270(11) B -2
H H42F 0.399223 0.935305 -0.096539 0.138 Uiso calc 0.270(11) B -2
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'
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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 H1O . . 109.5 ?
C31 O2 C32 . . 116.7(2) ?
C33 O4 H5 . . 108(2) ?
C36 O5 H5 . . 107(2) ?
C6 N1 C5 . . 110.35(19) ?
C6 N1 C4 . . 111.08(18) ?
C5 N1 C4 . . 112.93(19) ?
C6 N1 H1 . . 107.4 ?
C5 N1 H1 . . 107.4 ?
C4 N1 H1 . . 107.4 ?
C31 N2 C30 . . 117.4(2) ?
C23 C1 C17 . . 111.64(19) ?
C23 C1 C2 . . 110.87(18) ?
C17 C1 C2 . . 114.25(19) ?
C23 C1 H1A . . 106.5 ?
C17 C1 H1A . . 106.5 ?
C2 C1 H1A . . 106.5 ?
O1 C2 C7 . . 107.30(18) ?
O1 C2 C3 . . 107.82(18) ?
C7 C2 C3 . . 112.52(19) ?
O1 C2 C1 . . 108.99(19) ?
C7 C2 C1 . . 110.39(18) ?
C3 C2 C1 . . 109.70(17) ?
C4 C3 C2 . . 112.94(18) ?
C4 C3 H3A . . 109.0 ?
C2 C3 H3A . . 109.0 ?
C4 C3 H3B . . 109.0 ?
C2 C3 H3B . . 109.0 ?
H3A C3 H3B . . 107.8 ?
N1 C4 C3 . . 110.99(18) ?
N1 C4 H4A . . 109.4 ?
C3 C4 H4A . . 109.4 ?
N1 C4 H4B . . 109.4 ?
C3 C4 H4B . . 109.4 ?
H4A C4 H4B . . 108.0 ?
N1 C5 H5A . . 109.5 ?
N1 C5 H5B . . 109.5 ?
H5A C5 H5B . . 109.5 ?
N1 C5 H5C . . 109.5 ?
H5A C5 H5C . . 109.5 ?
H5B C5 H5C . . 109.5 ?
N1 C6 H6A . . 109.5 ?
N1 C6 H6B . . 109.5 ?
H6A C6 H6B . . 109.5 ?
N1 C6 H6C . . 109.5 ?
H6A C6 H6C . . 109.5 ?
H6B C6 H6C . . 109.5 ?
C8 C7 C16 . . 118.5(2) ?
C8 C7 C2 . . 117.8(2) ?
C16 C7 C2 . . 123.8(2) ?
C7 C8 C9 . . 121.5(3) ?
C7 C8 H8 . . 119.3 ?
C9 C8 H8 . . 119.3 ?
C10 C9 C8 . . 120.7(3) ?
C10 C9 H9 . . 119.6 ?
C8 C9 H9 . . 119.6 ?
C9 C10 C11 . . 120.5(3) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C12 . . 120.5(3) ?
C10 C11 C16 . . 120.2(3) ?
C12 C11 C16 . . 119.2(3) ?
C13 C12 C11 . . 122.7(3) ?
C13 C12 H12 . . 118.6 ?
C11 C12 H12 . . 118.6 ?
C12 C13 C14 . . 118.7(4) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C15 C14 C13 . . 121.4(4) ?
C15 C14 H14 . . 119.3 ?
C13 C14 H14 . . 119.3 ?
C14 C15 C16 . . 122.0(3) ?
C14 C15 H15 . . 119.0 ?
C16 C15 H15 . . 119.0 ?
C15 C16 C7 . . 125.4(2) ?
C15 C16 C11 . . 115.9(3) ?
C7 C16 C11 . . 118.7(3) ?
C22 C17 C18 . . 118.1(3) ?
C22 C17 C1 . . 117.6(3) ?
C18 C17 C1 . . 124.3(2) ?
C17 C18 C19 . . 120.9(3) ?
C17 C18 H18 . . 119.6 ?
C19 C18 H18 . . 119.6 ?
C20 C19 C18 . . 120.5(4) ?
C20 C19 H19 . . 119.7 ?
C18 C19 H19 . . 119.7 ?
C21 C20 C19 . . 118.8(3) ?
C21 C20 H20 . . 120.6 ?
C19 C20 H20 . . 120.6 ?
C20 C21 C22 . . 121.2(4) ?
C20 C21 H21 . . 119.4 ?
C22 C21 H21 . . 119.4 ?
C17 C22 C21 . . 120.4(4) ?
C17 C22 H22 . . 119.8 ?
C21 C22 H22 . . 119.8 ?
C24 C23 C31 . . 115.9(2) ?
C24 C23 C1 . . 123.5(2) ?
C31 C23 C1 . . 120.6(2) ?
C23 C24 C25 . . 120.7(2) ?
C23 C24 H24 . . 119.7 ?
C25 C24 H24 . . 119.7 ?
C30 C25 C26 . . 120.1(2) ?
C30 C25 C24 . . 117.8(2) ?
C26 C25 C24 . . 122.1(2) ?
C27 C26 C25 . . 119.3(3) ?
C27 C26 H26 . . 120.3 ?
C25 C26 H26 . . 120.3 ?
C26 C27 C28 . . 121.4(3) ?
C26 C27 Br1 . . 119.3(3) ?
C28 C27 Br1 . . 119.3(2) ?
C29 C28 C27 . . 119.7(3) ?
C29 C28 H28 . . 120.2 ?
C27 C28 H28 . . 120.2 ?
C28 C29 C30 . . 120.8(3) ?
C28 C29 H29 . . 119.6 ?
C30 C29 H29 . . 119.6 ?
N2 C30 C25 . . 122.2(2) ?
N2 C30 C29 . . 119.0(2) ?
C25 C30 C29 . . 118.8(3) ?
N2 C31 O2 . . 119.4(2) ?
N2 C31 C23 . . 125.6(2) ?
O2 C31 C23 . . 115.0(2) ?
O2 C32 H32A . . 109.5 ?
O2 C32 H32B . . 109.5 ?
H32A C32 H32B . . 109.5 ?
O2 C32 H32C . . 109.5 ?
H32A C32 H32C . . 109.5 ?
H32B C32 H32C . . 109.5 ?
O3 C33 O4 . . 122.9(3) ?
O3 C33 C34 . . 117.5(2) ?
O4 C33 C34 . . 119.6(2) ?
C35 C34 C33 . . 130.5(2) ?
C35 C34 H34 . . 114.8 ?
C33 C34 H34 . . 114.8 ?
C34 C35 C36 . . 130.9(2) ?
C34 C35 H35 . . 114.5 ?
C36 C35 H35 . . 114.5 ?
O6 C36 O5 . . 122.4(3) ?
O6 C36 C35 . . 117.9(3) ?
O5 C36 C35 . . 119.8(2) ?
O7 C37 C38 . . 130.1(18) ?
O7 C37 C39 . . 116.6(15) ?
C38 C37 C39 . . 112.9(17) ?
C37 C38 H38A . . 109.5 ?
C37 C38 H38B . . 109.5 ?
H38A C38 H38B . . 109.5 ?
C37 C38 H38C . . 109.5 ?
H38A C38 H38C . . 109.5 ?
H38B C38 H38C . . 109.5 ?
C37 C39 H39A . . 109.5 ?
C37 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
C37 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
C44 C43 H43A . . 109.5 ?
C44 C43 H43B . . 109.5 ?
H43A C43 H43B . . 109.5 ?
C44 C43 H43C . . 109.5 ?
H43A C43 H43C . . 109.5 ?
H43B C43 H43C . . 109.5 ?
C45 C44 C43 . . 114.0(15) ?
C45 C44 H44A . . 108.8 ?
C43 C44 H44A . . 108.8 ?
C45 C44 H44B . . 108.8 ?
C43 C44 H44B . . 108.8 ?
H44A C44 H44B . . 107.6 ?
C45 C45 C44 2_656 . 127.1(17) ?
C45 C45 H45A 2_656 . 105.5 ?
C44 C45 H45A . . 105.5 ?
C45 C45 H45B 2_656 . 105.5 ?
C44 C45 H45B . . 105.5 ?
H45A C45 H45B . . 106.1 ?
O8A C40A C42A . . 122(3) ?
O8A C40A C41A . . 126(3) ?
C42A C40A C41A . . 112(2) ?
C40A C41A H41A . . 109.5 ?
C40A C41A H41B . . 109.5 ?
H41A C41A H41B . . 109.5 ?
C40A C41A H41C . . 109.5 ?
H41A C41A H41C . . 109.5 ?
H41B C41A H41C . . 109.5 ?
C40A C42A H42A . . 109.5 ?
C40A C42A H42B . . 109.5 ?
H42A C42A H42B . . 109.5 ?
C40A C42A H42C . . 109.5 ?
H42A C42A H42C . . 109.5 ?
H42B C42A H42C . . 109.5 ?
O8B C40B C42B . . 129(2) ?
O8B C40B C41B . . 116(3) ?
C42B C40B C41B . . 115(2) ?
C40B C41B H41D . . 109.5 ?
C40B C41B H41E . . 109.5 ?
H41D C41B H41E . . 109.5 ?
C40B C41B H41F . . 109.5 ?
H41D C41B H41F . . 109.5 ?
H41E C41B H41F . . 109.5 ?
C40B C42B H42D . . 109.5 ?
C40B C42B H42E . . 109.5 ?
H42D C42B H42E . . 109.5 ?
C40B C42B H42F . . 109.5 ?
H42D C42B H42F . . 109.5 ?
H42E C42B H42F . . 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
Br1 C27 . 1.891(3) ?
O1 C2 . 1.422(3) ?
O1 H1O . 0.8400 ?
O2 C31 . 1.344(3) ?
O2 C32 . 1.438(3) ?
O3 C33 . 1.230(3) ?
O4 C33 . 1.271(3) ?
O4 H5 . 1.24(5) ?
O5 C36 . 1.283(3) ?
O5 H5 . 1.18(5) ?
O6 C36 . 1.222(3) ?
N1 C6 . 1.485(3) ?
N1 C5 . 1.495(3) ?
N1 C4 . 1.502(3) ?
N1 H1 . 1.0000 ?
N2 C31 . 1.307(3) ?
N2 C30 . 1.365(3) ?
C1 C23 . 1.522(3) ?
C1 C17 . 1.526(3) ?
C1 C2 . 1.580(3) ?
C1 H1A . 1.0000 ?
C2 C7 . 1.541(3) ?
C2 C3 . 1.542(3) ?
C3 C4 . 1.519(3) ?
C3 H3A . 0.9900 ?
C3 H3B . 0.9900 ?
C4 H4A . 0.9900 ?
C4 H4B . 0.9900 ?
C5 H5A . 0.9800 ?
C5 H5B . 0.9800 ?
C5 H5C . 0.9800 ?
C6 H6A . 0.9800 ?
C6 H6B . 0.9800 ?
C6 H6C . 0.9800 ?
C7 C8 . 1.377(4) ?
C7 C16 . 1.436(4) ?
C8 C9 . 1.429(4) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.343(6) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.402(5) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.426(5) ?
C11 C16 . 1.440(3) ?
C12 C13 . 1.344(7) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.398(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.375(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.425(4) ?
C15 H15 . 0.9500 ?
C17 C22 . 1.381(4) ?
C17 C18 . 1.382(5) ?
C18 C19 . 1.396(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.369(6) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.368(7) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.392(5) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 C24 . 1.362(4) ?
C23 C31 . 1.441(3) ?
C24 C25 . 1.424(3) ?
C24 H24 . 0.9500 ?
C25 C30 . 1.410(4) ?
C25 C26 . 1.414(4) ?
C26 C27 . 1.370(4) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.407(5) ?
C28 C29 . 1.371(5) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.415(3) ?
C29 H29 . 0.9500 ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C33 C34 . 1.493(4) ?
C34 C35 . 1.332(4) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.489(4) ?
C35 H35 . 0.9500 ?
O7 C37 . 1.19(2) ?
C37 C38 . 1.443(19) ?
C37 C39 . 1.463(19) ?
C38 H38A . 0.9800 ?
C38 H38B . 0.9800 ?
C38 H38C . 0.9800 ?
C39 H39A . 0.9800 ?
C39 H39B . 0.9800 ?
C39 H39C . 0.9800 ?
C43 C44 . 1.544(13) ?
C43 H43A . 0.9800 ?
C43 H43B . 0.9800 ?
C43 H43C . 0.9800 ?
C44 C45 . 1.501(13) ?
C44 H44A . 0.9900 ?
C44 H44B . 0.9900 ?
C45 C45 2_656 1.473(13) ?
C45 H45A . 0.9900 ?
C45 H45B . 0.9900 ?
O8A C40A . 1.17(2) ?
C40A C42A . 1.47(2) ?
C40A C41A . 1.486(19) ?
C41A H41A . 0.9800 ?
C41A H41B . 0.9800 ?
C41A H41C . 0.9800 ?
C42A H42A . 0.9800 ?
C42A H42B . 0.9800 ?
C42A H42C . 0.9800 ?
O8B C40B . 1.17(2) ?
C40B C42B . 1.47(2) ?
C40B C41B . 1.479(19) ?
C41B H41D . 0.9800 ?
C41B H41E . 0.9800 ?
C41B H41F . 0.9800 ?
C42B H42D . 0.9800 ?
C42B H42E . 0.9800 ?
C42B H42F . 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
O1 H1O O6 3_445 0.84 1.98 2.816(3) 174.7 yes
O5 H5 O4 . 1.18(5) 1.24(5) 2.422(3) 175(5) yes
N1 H1 O3 . 1.00 1.71 2.709(3) 174.2 yes
N1 H1 O4 . 1.00 2.54 3.212(3) 124.6 yes
C32 H32B O7 . 0.98 2.60 3.337(8) 132.1 yes
C34 H34 O7 . 0.95 2.66 3.600(9) 171.2 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
C23 C1 C2 O1 . . . . -57.4(2) ?
C17 C1 C2 O1 . . . . 69.8(3) ?
C23 C1 C2 C7 . . . . -175.0(2) ?
C17 C1 C2 C7 . . . . -47.8(3) ?
C23 C1 C2 C3 . . . . 60.5(3) ?
C17 C1 C2 C3 . . . . -172.3(2) ?
O1 C2 C3 C4 . . . . -65.2(2) ?
C7 C2 C3 C4 . . . . 52.9(3) ?
C1 C2 C3 C4 . . . . 176.2(2) ?
C6 N1 C4 C3 . . . . 163.3(2) ?
C5 N1 C4 C3 . . . . -72.1(3) ?
C2 C3 C4 N1 . . . . 172.86(19) ?
O1 C2 C7 C8 . . . . -0.4(3) ?
C3 C2 C7 C8 . . . . -118.9(2) ?
C1 C2 C7 C8 . . . . 118.2(2) ?
O1 C2 C7 C16 . . . . 179.7(2) ?
C3 C2 C7 C16 . . . . 61.3(3) ?
C1 C2 C7 C16 . . . . -61.6(3) ?
C16 C7 C8 C9 . . . . 0.2(4) ?
C2 C7 C8 C9 . . . . -179.6(2) ?
C7 C8 C9 C10 . . . . -0.1(4) ?
C8 C9 C10 C11 . . . . 0.0(4) ?
C9 C10 C11 C12 . . . . -178.4(3) ?
C9 C10 C11 C16 . . . . -0.1(4) ?
C10 C11 C12 C13 . . . . 178.1(4) ?
C16 C11 C12 C13 . . . . -0.2(5) ?
C11 C12 C13 C14 . . . . 1.0(6) ?
C12 C13 C14 C15 . . . . -1.0(6) ?
C13 C14 C15 C16 . . . . 0.2(5) ?
C14 C15 C16 C7 . . . . -178.5(3) ?
C14 C15 C16 C11 . . . . 0.5(4) ?
C8 C7 C16 C15 . . . . 178.7(2) ?
C2 C7 C16 C15 . . . . -1.5(4) ?
C8 C7 C16 C11 . . . . -0.3(3) ?
C2 C7 C16 C11 . . . . 179.5(2) ?
C10 C11 C16 C15 . . . . -178.8(3) ?
C12 C11 C16 C15 . . . . -0.6(4) ?
C10 C11 C16 C7 . . . . 0.3(4) ?
C12 C11 C16 C7 . . . . 178.6(3) ?
C23 C1 C17 C22 . . . . -94.4(3) ?
C2 C1 C17 C22 . . . . 138.8(3) ?
C23 C1 C17 C18 . . . . 83.9(3) ?
C2 C1 C17 C18 . . . . -42.9(4) ?
C22 C17 C18 C19 . . . . -0.2(5) ?
C1 C17 C18 C19 . . . . -178.5(3) ?
C17 C18 C19 C20 . . . . 1.7(5) ?
C18 C19 C20 C21 . . . . -1.7(6) ?
C19 C20 C21 C22 . . . . 0.4(7) ?
C18 C17 C22 C21 . . . . -1.1(5) ?
C1 C17 C22 C21 . . . . 177.3(3) ?
C20 C21 C22 C17 . . . . 1.1(6) ?
C17 C1 C23 C24 . . . . -38.3(3) ?
C2 C1 C23 C24 . . . . 90.3(3) ?
C17 C1 C23 C31 . . . . 142.8(2) ?
C2 C1 C23 C31 . . . . -88.6(2) ?
C31 C23 C24 C25 . . . . 2.7(3) ?
C1 C23 C24 C25 . . . . -176.2(2) ?
C23 C24 C25 C30 . . . . 2.2(3) ?
C23 C24 C25 C26 . . . . -179.7(2) ?
C30 C25 C26 C27 . . . . 1.5(4) ?
C24 C25 C26 C27 . . . . -176.5(3) ?
C25 C26 C27 C28 . . . . -0.3(5) ?
C25 C26 C27 Br1 . . . . 178.4(2) ?
C26 C27 C28 C29 . . . . -0.9(5) ?
Br1 C27 C28 C29 . . . . -179.6(2) ?
C27 C28 C29 C30 . . . . 0.8(4) ?
C31 N2 C30 C25 . . . . 0.7(3) ?
C31 N2 C30 C29 . . . . -180.0(2) ?
C26 C25 C30 N2 . . . . 177.7(2) ?
C24 C25 C30 N2 . . . . -4.1(3) ?
C26 C25 C30 C29 . . . . -1.6(3) ?
C24 C25 C30 C29 . . . . 176.5(2) ?
C28 C29 C30 N2 . . . . -178.9(2) ?
C28 C29 C30 C25 . . . . 0.4(3) ?
C30 N2 C31 O2 . . . . -174.54(19) ?
C30 N2 C31 C23 . . . . 4.9(3) ?
C32 O2 C31 N2 . . . . -1.1(3) ?
C32 O2 C31 C23 . . . . 179.4(2) ?
C24 C23 C31 N2 . . . . -6.6(3) ?
C1 C23 C31 N2 . . . . 172.3(2) ?
C24 C23 C31 O2 . . . . 172.82(19) ?
C1 C23 C31 O2 . . . . -8.2(3) ?
O3 C33 C34 C35 . . . . -179.5(3) ?
O4 C33 C34 C35 . . . . 1.9(5) ?
C33 C34 C35 C36 . . . . -0.6(5) ?
C34 C35 C36 O6 . . . . -176.7(3) ?
C34 C35 C36 O5 . . . . 3.6(5) ?
C43 C44 C45 C45 . . . 2_656 -149.8(15) ?

_cod_database_fobs_code 2243792
