#------------------------------------------------------------------------------
#$Date: 2021-03-27 08:13:50 +0200 (Sat, 27 Mar 2021) $
#$Revision: 263391 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243789.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_2243789
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          'C32 H32 Br N2 O2 +, C4 H3 O4 -, 0.476H2 O'
_chemical_formula_moiety         'C32 H32 Br N2 O2 +, C4 H3 O4 -, 0.476(H2 O)'
_chemical_formula_sum            'C36 H35.96 Br N2 O6.48'
_chemical_formula_weight         680.17
_chemical_name_common
;
Bedaquilinium maleate 0.476-hydrate
;
_chemical_name_systematic
'[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate 0.476-hydrate'
_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     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.3762(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7469(5)
_cell_length_b                   13.2627(4)
_cell_length_c                   17.8602(6)
_cell_measurement_reflns_used    9805
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.0660
_cell_measurement_theta_min      2.5786
_cell_volume                     3578.7(2)
_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 0.992
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type
;
Bruker AXS D8 Quest with PhotonIII_C14 CPAD
;
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_monochromator  'laterally graded multilayer (Goebel) mirror'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0400
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15060
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.762
_diffrn_reflns_theta_min         2.578
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.942
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.6457
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.262
_exptl_crystal_description       block
_exptl_crystal_F_000             1411
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.351
_refine_diff_density_min         -0.461
_refine_ls_abs_structure_details
;
Flack x determined using 2633 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.019(8)
_refine_ls_extinction_coef       0.00103(15)
_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   1.084
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     430
_refine_ls_number_reflns         7003
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0413
_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)+(0.0255P)²+3.0883P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1065
_reflns_number_gt                6474
_reflns_number_total             7003
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2038sup1.cif
_cod_data_source_block           hemihydrate
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2243789
_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   0.686
_shelx_estimated_absorpt_t_max   0.786
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 0.30375(5) 0.01666(6) 0.48115(4) 0.0839(3) Uani d 1 . .
O O1 0.48764(16) 0.27255(18) 0.16376(15) 0.0333(5) Uani d 1 . .
H H1O 0.440678 0.288534 0.174294 0.040 Uiso calc 1 . .
O O2 0.56686(17) 0.48680(18) 0.36191(15) 0.0366(6) Uani d 1 . .
O O3 0.48874(18) 0.6977(2) 0.21055(18) 0.0454(7) Uani d 1 . .
O O4 0.5661(2) 0.7107(3) 0.12579(16) 0.0555(9) Uani d 1 . .
O O5 0.7100(2) 0.7702(3) 0.12234(17) 0.0541(8) Uani d 1 . .
H H5 0.642(4) 0.739(4) 0.118(3) 0.065 Uiso d 1 . .
O O6 0.83376(18) 0.8188(2) 0.20818(18) 0.0459(7) Uani d 1 . .
N N1 0.39765(18) 0.5691(2) 0.09891(17) 0.0289(6) Uani d 1 . .
H H1 0.430917 0.620889 0.136586 0.035 Uiso calc 1 . .
N N2 0.46061(19) 0.4070(3) 0.40605(17) 0.0343(7) Uani d 1 . .
C C1 0.6050(2) 0.3244(3) 0.27938(19) 0.0298(7) Uani d 1 . .
H H1A 0.643444 0.384240 0.299018 0.036 Uiso calc 1 . .
C C2 0.5524(2) 0.3481(3) 0.1918(2) 0.0289(7) Uani d 1 . .
C C3 0.5040(2) 0.4505(3) 0.18735(18) 0.0278(7) Uani d 1 . .
H H3A 0.459479 0.445909 0.216773 0.033 Uiso calc 1 . .
H H3B 0.547308 0.503311 0.212095 0.033 Uiso calc 1 . .
C C4 0.4581(2) 0.4805(3) 0.10285(19) 0.0296(7) Uani d 1 . .
H H4A 0.503360 0.497710 0.076116 0.036 Uiso calc 1 . .
H H4B 0.423422 0.422623 0.075196 0.036 Uiso calc 1 . .
C C5 0.3164(2) 0.5436(3) 0.1216(2) 0.0381(8) Uani d 1 . .
H H5A 0.281406 0.494176 0.084779 0.057 Uiso calc 1 . .
H H5B 0.281123 0.604731 0.120611 0.057 Uiso calc 1 . .
H H5C 0.332940 0.515003 0.174331 0.057 Uiso calc 1 . .
C C6 0.3746(2) 0.6148(3) 0.0197(2) 0.0356(8) Uani d 1 . .
H H6A 0.348869 0.563192 -0.019349 0.053 Uiso calc 1 . .
H H6B 0.428209 0.642151 0.009674 0.053 Uiso calc 1 . .
H H6C 0.331672 0.669221 0.016597 0.053 Uiso calc 1 . .
C C7 0.6162(2) 0.3460(3) 0.14034(19) 0.0295(7) Uani d 1 . .
C C8 0.5999(3) 0.2769(3) 0.0803(2) 0.0359(8) Uani d 1 . .
H H8 0.550478 0.233013 0.072570 0.043 Uiso calc 1 . .
C C9 0.6545(3) 0.2695(3) 0.0299(2) 0.0423(9) Uani d 1 . .
H H9 0.640299 0.222296 -0.011847 0.051 Uiso calc 1 . .
C C10 0.7265(3) 0.3288(3) 0.0404(2) 0.0430(9) Uani d 1 . .
H H10 0.763079 0.322213 0.006498 0.052 Uiso calc 1 . .
C C11 0.7480(3) 0.4006(3) 0.1014(2) 0.0401(9) Uani d 1 . .
C C12 0.8229(3) 0.4631(4) 0.1120(3) 0.0544(11) Uani d 1 . .
H H12 0.859811 0.454499 0.078529 0.065 Uiso calc 1 . .
C C13 0.8443(3) 0.5352(4) 0.1683(3) 0.0560(12) Uani d 1 . .
H H13 0.894833 0.576837 0.173912 0.067 Uiso calc 1 . .
C C14 0.7905(3) 0.5467(3) 0.2176(3) 0.0471(10) Uani d 1 . .
H H14 0.804887 0.596659 0.257288 0.056 Uiso calc 1 . .
C C15 0.7170(2) 0.4875(3) 0.2103(2) 0.0375(8) Uani d 1 . .
H H15 0.681837 0.497728 0.245051 0.045 Uiso calc 1 . .
C C16 0.6919(2) 0.4111(3) 0.1521(2) 0.0316(7) Uani d 1 . .
C C17 0.6665(2) 0.2338(3) 0.2887(2) 0.0340(7) Uani d 1 . .
C C18 0.6427(3) 0.1422(3) 0.2516(2) 0.0415(9) Uani d 1 . .
H H18 0.586140 0.135021 0.214926 0.050 Uiso calc 1 . .
C C19 0.7002(3) 0.0608(4) 0.2671(3) 0.0558(12) Uani d 1 . .
H H19 0.682897 -0.001380 0.240840 0.067 Uiso calc 1 . .
C C20 0.7823(4) 0.0694(4) 0.3204(3) 0.0641(14) Uani d 1 . .
H H20 0.821473 0.013425 0.331189 0.077 Uiso calc 1 . .
C C21 0.8069(3) 0.1597(5) 0.3579(3) 0.0659(15) Uani d 1 . .
H H21 0.863077 0.165785 0.395277 0.079 Uiso calc 1 . .
C C22 0.7503(3) 0.2422(4) 0.3417(2) 0.0476(10) Uani d 1 . .
H H22 0.768804 0.304756 0.366877 0.057 Uiso calc 1 . .
C C23 0.5424(2) 0.3152(3) 0.33007(19) 0.0301(7) Uani d 1 . .
C C24 0.5058(2) 0.2271(3) 0.34449(19) 0.0321(7) Uani d 1 . .
H H24 0.520783 0.166081 0.323320 0.039 Uiso calc 1 . .
C C25 0.4456(2) 0.2245(3) 0.3907(2) 0.0361(8) Uani d 1 . .
C C26 0.4097(3) 0.1350(4) 0.4095(2) 0.0434(9) Uani d 1 . .
H H26 0.426466 0.071968 0.392785 0.052 Uiso calc 1 . .
C C27 0.3499(3) 0.1392(4) 0.4524(2) 0.0511(11) Uani d 1 . .
C C28 0.3230(3) 0.2303(4) 0.4767(2) 0.0511(11) Uani d 1 . .
H H28 0.280267 0.231305 0.505079 0.061 Uiso calc 1 . .
C C29 0.3584(3) 0.3182(4) 0.4597(2) 0.0441(10) Uani d 1 . .
H H29 0.339894 0.380429 0.476275 0.053 Uiso calc 1 . .
C C30 0.4221(2) 0.3183(3) 0.4178(2) 0.0359(8) Uani d 1 . .
C C31 0.5198(2) 0.4035(3) 0.36758(19) 0.0309(7) Uani d 1 . .
C C32 0.5519(3) 0.5748(3) 0.4034(3) 0.0503(10) Uani d 1 . .
H H32A 0.493257 0.602628 0.377597 0.075 Uiso calc 1 . .
H H32B 0.597264 0.625486 0.403543 0.075 Uiso calc 1 . .
H H32C 0.554939 0.556447 0.457197 0.075 Uiso calc 1 . .
C C33 0.5569(2) 0.7229(3) 0.1938(2) 0.0363(8) Uani d 1 . .
C C34 0.6313(3) 0.7650(3) 0.2571(2) 0.0377(8) Uani d 1 . .
H H34 0.618840 0.773706 0.305769 0.045 Uiso calc 1 . .
C C35 0.7131(2) 0.7926(3) 0.2566(2) 0.0369(8) Uani d 1 . .
H H35 0.749826 0.815444 0.305430 0.044 Uiso calc 1 . .
C C36 0.7555(3) 0.7933(3) 0.1923(2) 0.0372(8) Uani d 1 . .
O O7 0.4482(13) 0.8469(14) 0.3326(10) 0.106(9) Uani d 0.276(17) . .
H H7A 0.461417 0.803439 0.303738 0.159 Uiso d 0.276(17) . .
H H7B 0.477841 0.899199 0.331524 0.159 Uiso d 0.276(17) . .
O O8 0.500000 0.777(3) 0.500000 0.30(4) Uani d 0.40(4) . .
H H8A 0.488152 0.815245 0.454344 0.443 Uiso d 0.40(4) . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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 . . 117.0(3) ?
C33 O4 H5 . . 115(3) ?
C36 O5 H5 . . 114(3) ?
C5 N1 C6 . . 110.8(3) ?
C5 N1 C4 . . 113.1(3) ?
C6 N1 C4 . . 110.2(3) ?
C5 N1 H1 . . 107.5 ?
C6 N1 H1 . . 107.5 ?
C4 N1 H1 . . 107.5 ?
C31 N2 C30 . . 117.7(3) ?
C23 C1 C17 . . 111.8(3) ?
C23 C1 C2 . . 111.0(3) ?
C17 C1 C2 . . 113.9(3) ?
C23 C1 H1A . . 106.6 ?
C17 C1 H1A . . 106.6 ?
C2 C1 H1A . . 106.6 ?
O1 C2 C7 . . 107.5(3) ?
O1 C2 C3 . . 107.9(3) ?
C7 C2 C3 . . 112.3(3) ?
O1 C2 C1 . . 109.5(3) ?
C7 C2 C1 . . 109.8(3) ?
C3 C2 C1 . . 109.8(3) ?
C4 C3 C2 . . 111.6(3) ?
C4 C3 H3A . . 109.3 ?
C2 C3 H3A . . 109.3 ?
C4 C3 H3B . . 109.3 ?
C2 C3 H3B . . 109.3 ?
H3A C3 H3B . . 108.0 ?
N1 C4 C3 . . 111.5(3) ?
N1 C4 H4A . . 109.3 ?
C3 C4 H4A . . 109.3 ?
N1 C4 H4B . . 109.3 ?
C3 C4 H4B . . 109.3 ?
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(3) ?
C8 C7 C2 . . 117.9(3) ?
C16 C7 C2 . . 123.7(3) ?
C7 C8 C9 . . 122.0(4) ?
C7 C8 H8 . . 119.0 ?
C9 C8 H8 . . 119.0 ?
C10 C9 C8 . . 120.6(4) ?
C10 C9 H9 . . 119.7 ?
C8 C9 H9 . . 119.7 ?
C9 C10 C11 . . 120.6(4) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C12 C11 C10 . . 120.5(4) ?
C12 C11 C16 . . 119.9(4) ?
C10 C11 C16 . . 119.6(4) ?
C13 C12 C11 . . 122.4(4) ?
C13 C12 H12 . . 118.8 ?
C11 C12 H12 . . 118.8 ?
C12 C13 C14 . . 118.5(4) ?
C12 C13 H13 . . 120.8 ?
C14 C13 H13 . . 120.8 ?
C15 C14 C13 . . 121.7(4) ?
C15 C14 H14 . . 119.2 ?
C13 C14 H14 . . 119.2 ?
C14 C15 C16 . . 121.9(4) ?
C14 C15 H15 . . 119.1 ?
C16 C15 H15 . . 119.1 ?
C15 C16 C11 . . 115.8(3) ?
C15 C16 C7 . . 125.5(3) ?
C11 C16 C7 . . 118.7(3) ?
C18 C17 C22 . . 118.2(4) ?
C18 C17 C1 . . 124.2(3) ?
C22 C17 C1 . . 117.5(4) ?
C17 C18 C19 . . 121.0(4) ?
C17 C18 H18 . . 119.5 ?
C19 C18 H18 . . 119.5 ?
C20 C19 C18 . . 120.4(5) ?
C20 C19 H19 . . 119.8 ?
C18 C19 H19 . . 119.8 ?
C21 C20 C19 . . 119.4(4) ?
C21 C20 H20 . . 120.3 ?
C19 C20 H20 . . 120.3 ?
C20 C21 C22 . . 120.6(5) ?
C20 C21 H21 . . 119.7 ?
C22 C21 H21 . . 119.7 ?
C21 C22 C17 . . 120.5(5) ?
C21 C22 H22 . . 119.8 ?
C17 C22 H22 . . 119.8 ?
C24 C23 C31 . . 115.9(3) ?
C24 C23 C1 . . 124.2(3) ?
C31 C23 C1 . . 119.8(3) ?
C23 C24 C25 . . 121.2(3) ?
C23 C24 H24 . . 119.4 ?
C25 C24 H24 . . 119.4 ?
C26 C25 C30 . . 120.1(3) ?
C26 C25 C24 . . 122.8(4) ?
C30 C25 C24 . . 117.2(4) ?
C27 C26 C25 . . 119.2(4) ?
C27 C26 H26 . . 120.4 ?
C25 C26 H26 . . 120.4 ?
C26 C27 C28 . . 121.8(4) ?
C26 C27 Br1 . . 119.3(4) ?
C28 C27 Br1 . . 118.9(3) ?
C29 C28 C27 . . 119.6(4) ?
C29 C28 H28 . . 120.2 ?
C27 C28 H28 . . 120.2 ?
C28 C29 C30 . . 121.0(4) ?
C28 C29 H29 . . 119.5 ?
C30 C29 H29 . . 119.5 ?
N2 C30 C29 . . 119.6(4) ?
N2 C30 C25 . . 122.2(3) ?
C29 C30 C25 . . 118.2(4) ?
N2 C31 O2 . . 120.0(3) ?
N2 C31 C23 . . 125.3(4) ?
O2 C31 C23 . . 114.7(3) ?
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 . . 122.4(3) ?
O3 C33 C34 . . 117.9(3) ?
O4 C33 C34 . . 119.6(3) ?
C35 C34 C33 . . 130.5(3) ?
C35 C34 H34 . . 114.8 ?
C33 C34 H34 . . 114.8 ?
C34 C35 C36 . . 130.6(3) ?
C34 C35 H35 . . 114.7 ?
C36 C35 H35 . . 114.7 ?
O6 C36 O5 . . 122.3(4) ?
O6 C36 C35 . . 117.6(4) ?
O5 C36 C35 . . 120.0(3) ?
H7A O7 H7B . . 108.6 ?
H8A O8 H8A . 2_656 113.8 ?
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 . 1.909(5) ?
O1 C2 . 1.417(4) ?
O1 H1O . 0.8400 ?
O2 C31 . 1.349(5) ?
O2 C32 . 1.437(5) ?
O3 C33 . 1.237(5) ?
O4 C33 . 1.275(5) ?
O4 H5 . 1.29(6) ?
O5 C36 . 1.290(5) ?
O5 H5 . 1.13(6) ?
O6 C36 . 1.231(5) ?
N1 C5 . 1.487(4) ?
N1 C6 . 1.487(5) ?
N1 C4 . 1.501(4) ?
N1 H1 . 1.0000 ?
N2 C31 . 1.306(5) ?
N2 C30 . 1.366(5) ?
C1 C23 . 1.520(5) ?
C1 C17 . 1.523(5) ?
C1 C2 . 1.581(5) ?
C1 H1A . 1.0000 ?
C2 C7 . 1.541(5) ?
C2 C3 . 1.548(5) ?
C3 C4 . 1.531(4) ?
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 . 1.379(5) ?
C7 C16 . 1.439(5) ?
C8 C9 . 1.413(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.349(7) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.416(6) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.411(7) ?
C11 C16 . 1.438(5) ?
C12 C13 . 1.360(8) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.392(7) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.374(6) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.425(5) ?
C15 H15 . 0.9500 ?
C17 C18 . 1.383(6) ?
C17 C22 . 1.395(6) ?
C18 C19 . 1.386(6) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.376(8) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.373(9) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.388(7) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 C24 . 1.359(5) ?
C23 C31 . 1.443(5) ?
C24 C25 . 1.423(5) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.395(6) ?
C25 C30 . 1.420(6) ?
C26 C27 . 1.372(6) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.390(8) ?
C28 C29 . 1.363(7) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.410(5) ?
C29 H29 . 0.9500 ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C33 C34 . 1.488(5) ?
C34 C35 . 1.342(5) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.482(6) ?
C35 H35 . 0.9500 ?
O7 H7A . 0.8370 ?
O7 H7B . 0.8394 ?
O8 H8A . 0.9355 ?
O8 H8A 2_656 0.9355 ?
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 2.822(4) 174.7 yes
O5 H5 O4 . 1.13(6) 1.29(6) 2.417(4) 169(5) yes
N1 H1 O3 . 1.00 1.71 2.707(4) 172.4 yes
N1 H1 O4 . 1.00 2.49 3.174(4) 124.9 yes
C3 H3A O6 3_445 0.99 2.57 3.308(4) 131.1 yes
C6 H6B O4 2_655 0.98 2.61 3.257(5) 123.7 yes
O7 H7A O3 . 0.84 2.31 3.139(16) 172.3 yes
O8 H8A O7 . 0.94 2.13 3.02(2) 158.0 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 . . . . -56.3(4) ?
C17 C1 C2 O1 . . . . 70.9(4) ?
C23 C1 C2 C7 . . . . -174.1(3) ?
C17 C1 C2 C7 . . . . -46.9(4) ?
C23 C1 C2 C3 . . . . 62.0(4) ?
C17 C1 C2 C3 . . . . -170.8(3) ?
O1 C2 C3 C4 . . . . -65.2(4) ?
C7 C2 C3 C4 . . . . 53.1(4) ?
C1 C2 C3 C4 . . . . 175.6(3) ?
C5 N1 C4 C3 . . . . -71.8(4) ?
C6 N1 C4 C3 . . . . 163.7(3) ?
C2 C3 C4 N1 . . . . 169.4(3) ?
O1 C2 C7 C8 . . . . 0.5(4) ?
C3 C2 C7 C8 . . . . -118.0(3) ?
C1 C2 C7 C8 . . . . 119.5(3) ?
O1 C2 C7 C16 . . . . -178.8(3) ?
C3 C2 C7 C16 . . . . 62.7(4) ?
C1 C2 C7 C16 . . . . -59.8(4) ?
C16 C7 C8 C9 . . . . -0.9(5) ?
C2 C7 C8 C9 . . . . 179.8(3) ?
C7 C8 C9 C10 . . . . 1.8(6) ?
C8 C9 C10 C11 . . . . -1.0(6) ?
C9 C10 C11 C12 . . . . -179.5(4) ?
C9 C10 C11 C16 . . . . -0.6(6) ?
C10 C11 C12 C13 . . . . 177.9(4) ?
C16 C11 C12 C13 . . . . -1.0(7) ?
C11 C12 C13 C14 . . . . 0.7(7) ?
C12 C13 C14 C15 . . . . -0.2(7) ?
C13 C14 C15 C16 . . . . 0.1(6) ?
C14 C15 C16 C11 . . . . -0.5(5) ?
C14 C15 C16 C7 . . . . -179.9(4) ?
C12 C11 C16 C15 . . . . 0.9(5) ?
C10 C11 C16 C15 . . . . -178.0(3) ?
C12 C11 C16 C7 . . . . -179.6(4) ?
C10 C11 C16 C7 . . . . 1.4(5) ?
C8 C7 C16 C15 . . . . 178.7(3) ?
C2 C7 C16 C15 . . . . -2.0(5) ?
C8 C7 C16 C11 . . . . -0.7(5) ?
C2 C7 C16 C11 . . . . 178.6(3) ?
C23 C1 C17 C18 . . . . 80.4(4) ?
C2 C1 C17 C18 . . . . -46.3(5) ?
C23 C1 C17 C22 . . . . -95.5(4) ?
C2 C1 C17 C22 . . . . 137.7(3) ?
C22 C17 C18 C19 . . . . 0.5(6) ?
C1 C17 C18 C19 . . . . -175.4(4) ?
C17 C18 C19 C20 . . . . 0.4(7) ?
C18 C19 C20 C21 . . . . -0.3(8) ?
C19 C20 C21 C22 . . . . -0.9(8) ?
C20 C21 C22 C17 . . . . 1.9(7) ?
C18 C17 C22 C21 . . . . -1.7(6) ?
C1 C17 C22 C21 . . . . 174.5(4) ?
C17 C1 C23 C24 . . . . -36.4(4) ?
C2 C1 C23 C24 . . . . 91.9(4) ?
C17 C1 C23 C31 . . . . 142.4(3) ?
C2 C1 C23 C31 . . . . -89.3(4) ?
C31 C23 C24 C25 . . . . 3.1(5) ?
C1 C23 C24 C25 . . . . -178.1(3) ?
C23 C24 C25 C26 . . . . -177.2(3) ?
C23 C24 C25 C30 . . . . 3.0(5) ?
C30 C25 C26 C27 . . . . 1.8(5) ?
C24 C25 C26 C27 . . . . -178.0(4) ?
C25 C26 C27 C28 . . . . 0.9(6) ?
C25 C26 C27 Br1 . . . . -177.9(3) ?
C26 C27 C28 C29 . . . . -1.8(6) ?
Br1 C27 C28 C29 . . . . 177.0(3) ?
C27 C28 C29 C30 . . . . -0.1(6) ?
C31 N2 C30 C29 . . . . 179.4(3) ?
C31 N2 C30 C25 . . . . 1.0(5) ?
C28 C29 C30 N2 . . . . -175.7(3) ?
C28 C29 C30 C25 . . . . 2.8(5) ?
C26 C25 C30 N2 . . . . 174.9(3) ?
C24 C25 C30 N2 . . . . -5.3(5) ?
C26 C25 C30 C29 . . . . -3.6(5) ?
C24 C25 C30 C29 . . . . 176.2(3) ?
C30 N2 C31 O2 . . . . -172.6(3) ?
C30 N2 C31 C23 . . . . 6.0(5) ?
C32 O2 C31 N2 . . . . 3.5(5) ?
C32 O2 C31 C23 . . . . -175.3(3) ?
C24 C23 C31 N2 . . . . -8.1(5) ?
C1 C23 C31 N2 . . . . 173.0(3) ?
C24 C23 C31 O2 . . . . 170.6(3) ?
C1 C23 C31 O2 . . . . -8.3(4) ?
O3 C33 C34 C35 . . . . 175.8(4) ?
O4 C33 C34 C35 . . . . -1.8(7) ?
C33 C34 C35 C36 . . . . 2.2(8) ?
C34 C35 C36 O6 . . . . -177.1(4) ?
C34 C35 C36 O5 . . . . 4.6(7) ?

_cod_database_fobs_code 2243789
