#------------------------------------------------------------------------------
#$Date: 2021-03-27 08:13:50 +0200 (Sat, 27 Mar 2021) $
#$Revision: 263391 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243794.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_2243794
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 -'
_chemical_formula_moiety         'C32 H32 Br N2 O2, C4 H3 O4'
_chemical_formula_sum            'C36 H35 Br N2 O6'
_chemical_formula_weight         671.56
_chemical_name_common
;
Bedaquilinium maleate
;
_chemical_name_systematic
'[4-(6-bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium 3-carboxyprop-2-enoate'
_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
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 106.500(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.7494(12)
_cell_length_b                   13.3568(11)
_cell_length_c                   17.8634(14)
_cell_measurement_reflns_used    9787
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      31.5885
_cell_measurement_theta_min      2.5436
_cell_volume                     3603.0(5)
_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  0.0486
_diffrn_reflns_av_unetI/netI     0.0610
_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       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            78970
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.142
_diffrn_reflns_theta_min         2.544
_diffrn_source                   'fine focus sealed tube X-ray source'
_diffrn_source_current           '30 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.185
_exptl_absorpt_correction_T_max  0.7401
_exptl_absorpt_correction_T_min  0.6783
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al.,  2015)
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_description       block
_exptl_crystal_F_000             1392
_exptl_crystal_size_max          0.480
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.210
_refine_diff_density_max         0.764
_refine_diff_density_min         -0.626
_refine_ls_abs_structure_details
;
Flack x determined using 4139 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.044(3)
_refine_ls_extinction_coef       0.0076(12)
_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   1.063
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         13639
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.063
_refine_ls_R_factor_all          0.0615
_refine_ls_R_factor_gt           0.0415
_refine_ls_shift/su_max          0.011
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0554P)²+0.5224P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1103
_refine_ls_wR_factor_ref         0.1193
_reflns_number_gt                10346
_reflns_number_total             13639
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2038sup1.cif
_cod_data_source_block           desolvated_sq
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2243794
_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   0.600
_shelx_estimated_absorpt_t_max   0.789
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 0.30118(3) 0.01862(4) 0.48056(3) 0.08775(18) Uani d 1 . .
O O1 0.48679(9) 0.26938(11) 0.16351(8) 0.0299(3) Uani d 1 . .
H H1O 0.440910 0.283392 0.176451 0.036 Uiso calc 1 . .
O O2 0.56679(11) 0.48352(12) 0.36136(9) 0.0353(3) Uani d 1 . .
O O3 0.49001(11) 0.69078(14) 0.21060(10) 0.0412(4) Uani d 1 . .
O O4 0.56582(13) 0.7067(2) 0.12477(10) 0.0561(6) Uani d 1 . .
O O5 0.70934(14) 0.76777(19) 0.12131(10) 0.0527(5) Uani d 1 . .
H H5 0.647(3) 0.747(3) 0.117(2) 0.063 Uiso d 1 . .
O O6 0.83287(11) 0.81603(15) 0.20731(11) 0.0433(4) Uani d 1 . .
N N1 0.39737(10) 0.56465(13) 0.09851(9) 0.0253(3) Uani d 1 . .
H H1 0.430837 0.615719 0.136472 0.030 Uiso calc 1 . .
N N2 0.46071(12) 0.40514(16) 0.40537(10) 0.0341(4) Uani d 1 . .
C C1 0.60427(12) 0.32105(15) 0.27931(10) 0.0273(3) Uani d 1 . .
H H1A 0.643206 0.380148 0.298957 0.033 Uiso calc 1 . .
C C2 0.55192(12) 0.34523(14) 0.19163(10) 0.0246(3) Uani d 1 . .
C C3 0.50350(12) 0.44640(15) 0.18668(10) 0.0260(3) Uani d 1 . .
H H3A 0.459011 0.441802 0.216096 0.031 Uiso calc 1 . .
H H3B 0.546765 0.498851 0.211502 0.031 Uiso calc 1 . .
C C4 0.45728(13) 0.47672(15) 0.10240(10) 0.0274(3) Uani d 1 . .
H H4A 0.502469 0.493565 0.075593 0.033 Uiso calc 1 . .
H H4B 0.422292 0.419415 0.074655 0.033 Uiso calc 1 . .
C C5 0.31575(13) 0.53959(18) 0.12091(14) 0.0361(4) Uani d 1 . .
H H5A 0.280149 0.491610 0.083411 0.054 Uiso calc 1 . .
H H5B 0.281213 0.600655 0.120786 0.054 Uiso calc 1 . .
H H5C 0.332157 0.510016 0.173268 0.054 Uiso calc 1 . .
C C6 0.37409(14) 0.61089(17) 0.01966(12) 0.0337(4) Uani d 1 . .
H H6A 0.350953 0.559350 -0.019928 0.051 Uiso calc 1 . .
H H6B 0.427036 0.641283 0.010792 0.051 Uiso calc 1 . .
H H6C 0.328913 0.662530 0.016106 0.051 Uiso calc 1 . .
C C7 0.61572(13) 0.34273(15) 0.14022(10) 0.0266(3) Uani d 1 . .
C C8 0.59959(15) 0.27345(17) 0.08056(11) 0.0333(4) Uani d 1 . .
H H8 0.550296 0.229713 0.072955 0.040 Uiso calc 1 . .
C C9 0.65464(18) 0.26575(19) 0.03025(12) 0.0399(5) Uani d 1 . .
H H9 0.640823 0.218576 -0.011255 0.048 Uiso calc 1 . .
C C10 0.72683(17) 0.3253(2) 0.04103(13) 0.0406(5) Uani d 1 . .
H H10 0.763934 0.318524 0.007670 0.049 Uiso calc 1 . .
C C11 0.74731(15) 0.39708(19) 0.10124(13) 0.0374(5) Uani d 1 . .
C C12 0.82271(18) 0.4602(2) 0.11175(18) 0.0514(6) Uani d 1 . .
H H12 0.860130 0.451201 0.078903 0.062 Uiso calc 1 . .
C C13 0.84281(18) 0.5327(3) 0.16696(19) 0.0530(6) Uani d 1 . .
H H13 0.892498 0.575123 0.171845 0.064 Uiso calc 1 . .
C C14 0.78832(17) 0.5440(2) 0.21732(17) 0.0447(5) Uani d 1 . .
H H14 0.802454 0.593757 0.256962 0.054 Uiso calc 1 . .
C C15 0.71539(14) 0.48429(17) 0.20974(13) 0.0345(4) Uani d 1 . .
H H15 0.679896 0.494250 0.244118 0.041 Uiso calc 1 . .
C C16 0.69124(13) 0.40771(16) 0.15184(11) 0.0294(4) Uani d 1 . .
C C17 0.66524(14) 0.23088(18) 0.28874(11) 0.0320(4) Uani d 1 . .
C C18 0.64028(17) 0.13930(19) 0.25149(14) 0.0404(5) Uani d 1 . .
H H18 0.583392 0.132137 0.215185 0.048 Uiso calc 1 . .
C C19 0.6984(2) 0.0582(2) 0.26725(19) 0.0524(7) Uani d 1 . .
H H19 0.680885 -0.003562 0.241076 0.063 Uiso calc 1 . .
C C20 0.7809(2) 0.0665(3) 0.3203(2) 0.0636(9) Uani d 1 . .
H H20 0.819505 0.010366 0.331850 0.076 Uiso calc 1 . .
C C21 0.8066(2) 0.1569(3) 0.35611(19) 0.0645(10) Uani d 1 . .
H H21 0.863956 0.163296 0.391798 0.077 Uiso calc 1 . .
C C22 0.74975(16) 0.2403(2) 0.34109(14) 0.0453(6) Uani d 1 . .
H H22 0.768577 0.302392 0.366257 0.054 Uiso calc 1 . .
C C23 0.54206(12) 0.31305(16) 0.33015(10) 0.0278(4) Uani d 1 . .
C C24 0.50506(13) 0.22578(18) 0.34412(11) 0.0313(4) Uani d 1 . .
H H24 0.519625 0.165058 0.322953 0.038 Uiso calc 1 . .
C C25 0.44448(13) 0.2244(2) 0.39030(11) 0.0341(4) Uani d 1 . .
C C26 0.40745(17) 0.1344(2) 0.40884(14) 0.0434(5) Uani d 1 . .
H H26 0.423475 0.071736 0.391709 0.052 Uiso calc 1 . .
C C27 0.34766(18) 0.1393(3) 0.45222(15) 0.0509(7) Uani d 1 . .
C C28 0.32165(16) 0.2313(3) 0.47676(13) 0.0517(7) Uani d 1 . .
H H28 0.279078 0.233155 0.505230 0.062 Uiso calc 1 . .
C C29 0.35782(15) 0.3182(2) 0.45953(12) 0.0433(6) Uani d 1 . .
H H29 0.339912 0.380171 0.476248 0.052 Uiso calc 1 . .
C C30 0.42172(13) 0.3177(2) 0.41708(11) 0.0350(4) Uani d 1 . .
C C31 0.51959(13) 0.40074(16) 0.36695(10) 0.0297(4) Uani d 1 . .
C C32 0.5520(2) 0.5719(2) 0.40070(17) 0.0498(6) Uani d 1 . .
H H32A 0.492849 0.598347 0.374896 0.075 Uiso calc 1 . .
H H32B 0.596679 0.622211 0.399067 0.075 Uiso calc 1 . .
H H32C 0.556169 0.555802 0.455161 0.075 Uiso calc 1 . .
C C33 0.55723(15) 0.71778(17) 0.19319(12) 0.0339(4) Uani d 1 . .
C C34 0.63133(15) 0.76090(18) 0.25665(12) 0.0359(4) Uani d 1 . .
H H34 0.619022 0.768985 0.305370 0.043 Uiso calc 1 . .
C C35 0.71187(15) 0.78980(18) 0.25582(12) 0.0351(4) Uani d 1 . .
H H35 0.748219 0.813825 0.304432 0.042 Uiso calc 1 . .
C C36 0.75467(15) 0.79076(17) 0.19113(13) 0.0343(4) Uani d 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'
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 . . 118.04(19) ?
C33 O4 H5 . . 112.6(16) ?
C36 O5 H5 . . 113(2) ?
C6 N1 C5 . . 110.41(15) ?
C6 N1 C4 . . 110.68(15) ?
C5 N1 C4 . . 113.10(16) ?
C6 N1 H1 . . 107.5 ?
C5 N1 H1 . . 107.5 ?
C4 N1 H1 . . 107.5 ?
C31 N2 C30 . . 117.48(19) ?
C23 C1 C17 . . 111.90(16) ?
C23 C1 C2 . . 111.31(15) ?
C17 C1 C2 . . 113.99(15) ?
C23 C1 H1A . . 106.3 ?
C17 C1 H1A . . 106.3 ?
C2 C1 H1A . . 106.3 ?
O1 C2 C3 . . 107.91(15) ?
O1 C2 C7 . . 107.43(15) ?
C3 C2 C7 . . 112.34(15) ?
O1 C2 C1 . . 108.89(15) ?
C3 C2 C1 . . 110.23(14) ?
C7 C2 C1 . . 109.92(14) ?
C4 C3 C2 . . 112.22(15) ?
C4 C3 H3A . . 109.2 ?
C2 C3 H3A . . 109.2 ?
C4 C3 H3B . . 109.2 ?
C2 C3 H3B . . 109.2 ?
H3A C3 H3B . . 107.9 ?
N1 C4 C3 . . 111.81(14) ?
N1 C4 H4A . . 109.3 ?
C3 C4 H4A . . 109.3 ?
N1 C4 H4B . . 109.3 ?
C3 C4 H4B . . 109.3 ?
H4A C4 H4B . . 107.9 ?
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 . . 118.65(18) ?
C8 C7 C2 . . 117.80(18) ?
C16 C7 C2 . . 123.55(16) ?
C7 C8 C9 . . 121.8(2) ?
C7 C8 H8 . . 119.1 ?
C9 C8 H8 . . 119.1 ?
C10 C9 C8 . . 120.4(2) ?
C10 C9 H9 . . 119.8 ?
C8 C9 H9 . . 119.8 ?
C9 C10 C11 . . 120.58(19) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.4(2) ?
C10 C11 C16 . . 119.9(2) ?
C12 C11 C16 . . 119.7(2) ?
C13 C12 C11 . . 122.2(2) ?
C13 C12 H12 . . 118.9 ?
C11 C12 H12 . . 118.9 ?
C12 C13 C14 . . 118.7(3) ?
C12 C13 H13 . . 120.6 ?
C14 C13 H13 . . 120.6 ?
C15 C14 C13 . . 121.0(3) ?
C15 C14 H14 . . 119.5 ?
C13 C14 H14 . . 119.5 ?
C14 C15 C16 . . 122.1(2) ?
C14 C15 H15 . . 119.0 ?
C16 C15 H15 . . 119.0 ?
C15 C16 C7 . . 125.18(17) ?
C15 C16 C11 . . 116.2(2) ?
C7 C16 C11 . . 118.64(19) ?
C18 C17 C22 . . 118.9(2) ?
C18 C17 C1 . . 123.96(19) ?
C22 C17 C1 . . 117.0(2) ?
C19 C18 C17 . . 120.3(3) ?
C19 C18 H18 . . 119.8 ?
C17 C18 H18 . . 119.8 ?
C20 C19 C18 . . 120.9(3) ?
C20 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C21 C20 C19 . . 119.1(2) ?
C21 C20 H20 . . 120.5 ?
C19 C20 H20 . . 120.5 ?
C20 C21 C22 . . 121.4(3) ?
C20 C21 H21 . . 119.3 ?
C22 C21 H21 . . 119.3 ?
C17 C22 C21 . . 119.4(3) ?
C17 C22 H22 . . 120.3 ?
C21 C22 H22 . . 120.3 ?
C24 C23 C31 . . 116.22(18) ?
C24 C23 C1 . . 123.66(18) ?
C31 C23 C1 . . 120.11(19) ?
C23 C24 C25 . . 120.6(2) ?
C23 C24 H24 . . 119.7 ?
C25 C24 H24 . . 119.7 ?
C26 C25 C30 . . 120.5(2) ?
C26 C25 C24 . . 122.3(2) ?
C30 C25 C24 . . 117.3(2) ?
C27 C26 C25 . . 118.9(3) ?
C27 C26 H26 . . 120.5 ?
C25 C26 H26 . . 120.5 ?
C26 C27 C28 . . 121.5(3) ?
C26 C27 Br1 . . 119.1(3) ?
C28 C27 Br1 . . 119.43(19) ?
C29 C28 C27 . . 119.7(2) ?
C29 C28 H28 . . 120.1 ?
C27 C28 H28 . . 120.1 ?
C28 C29 C30 . . 121.4(3) ?
C28 C29 H29 . . 119.3 ?
C30 C29 H29 . . 119.3 ?
N2 C30 C25 . . 122.26(18) ?
N2 C30 C29 . . 119.8(2) ?
C25 C30 C29 . . 117.9(2) ?
N2 C31 O2 . . 119.39(19) ?
N2 C31 C23 . . 125.7(2) ?
O2 C31 C23 . . 114.91(17) ?
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 . . 122.5(2) ?
O3 C33 C34 . . 117.47(19) ?
O4 C33 C34 . . 120.0(2) ?
C35 C34 C33 . . 130.2(2) ?
C35 C34 H34 . . 114.9 ?
C33 C34 H34 . . 114.9 ?
C34 C35 C36 . . 130.7(2) ?
C34 C35 H35 . . 114.6 ?
C36 C35 H35 . . 114.6 ?
O6 C36 O5 . . 122.4(2) ?
O6 C36 C35 . . 117.5(2) ?
O5 C36 C35 . . 119.99(19) ?
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 . 1.897(3) ?
O1 C2 . 1.428(2) ?
O1 H1O . 0.8400 ?
O2 C31 . 1.352(3) ?
O2 C32 . 1.426(3) ?
O3 C33 . 1.239(3) ?
O4 C33 . 1.276(3) ?
O4 H5 . 1.42(4) ?
O5 C36 . 1.286(3) ?
O5 H5 . 1.01(4) ?
O6 C36 . 1.230(3) ?
N1 C6 . 1.485(2) ?
N1 C5 . 1.489(2) ?
N1 C4 . 1.496(2) ?
N1 H1 . 1.0000 ?
N2 C31 . 1.302(3) ?
N2 C30 . 1.363(3) ?
C1 C23 . 1.517(3) ?
C1 C17 . 1.520(3) ?
C1 C2 . 1.582(2) ?
C1 H1A . 1.0000 ?
C2 C3 . 1.542(3) ?
C2 C7 . 1.542(3) ?
C3 C4 . 1.529(2) ?
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 . 1.380(3) ?
C7 C16 . 1.439(3) ?
C8 C9 . 1.418(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.356(4) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.408(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.425(4) ?
C11 C16 . 1.439(3) ?
C12 C13 . 1.353(5) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.417(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.373(3) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.427(3) ?
C15 H15 . 0.9500 ?
C17 C18 . 1.395(4) ?
C17 C22 . 1.398(3) ?
C18 C19 . 1.394(3) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.378(5) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.373(6) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.406(4) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 C24 . 1.358(3) ?
C23 C31 . 1.436(3) ?
C24 C25 . 1.428(3) ?
C24 H24 . 0.9500 ?
C25 C26 . 1.415(4) ?
C25 C30 . 1.418(4) ?
C26 C27 . 1.381(4) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.405(5) ?
C28 C29 . 1.365(5) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.422(3) ?
C29 H29 . 0.9500 ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C33 C34 . 1.492(3) ?
C34 C35 . 1.330(3) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.494(3) ?
C35 H35 . 0.9500 ?
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 2.820(2) 179.8 yes
O5 H5 O4 . 1.01(4) 1.42(4) 2.420(3) 169(4) yes
N1 H1 O3 . 1.00 1.71 2.705(2) 172.4 yes
N1 H1 O4 . 1.00 2.51 3.186(2) 124.7 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 . . . . -57.1(2) ?
C17 C1 C2 O1 . . . . 70.6(2) ?
C23 C1 C2 C3 . . . . 61.1(2) ?
C17 C1 C2 C3 . . . . -171.18(17) ?
C23 C1 C2 C7 . . . . -174.55(16) ?
C17 C1 C2 C7 . . . . -46.8(2) ?
O1 C2 C3 C4 . . . . -65.28(19) ?
C7 C2 C3 C4 . . . . 53.0(2) ?
C1 C2 C3 C4 . . . . 175.92(16) ?
C6 N1 C4 C3 . . . . 163.50(17) ?
C5 N1 C4 C3 . . . . -72.0(2) ?
C2 C3 C4 N1 . . . . 169.68(16) ?
O1 C2 C7 C8 . . . . 0.3(2) ?
C3 C2 C7 C8 . . . . -118.21(19) ?
C1 C2 C7 C8 . . . . 118.66(18) ?
O1 C2 C7 C16 . . . . -178.92(16) ?
C3 C2 C7 C16 . . . . 62.6(2) ?
C1 C2 C7 C16 . . . . -60.6(2) ?
C16 C7 C8 C9 . . . . -0.8(3) ?
C2 C7 C8 C9 . . . . 179.92(18) ?
C7 C8 C9 C10 . . . . 1.8(3) ?
C8 C9 C10 C11 . . . . -1.3(3) ?
C9 C10 C11 C12 . . . . -179.3(2) ?
C9 C10 C11 C16 . . . . -0.1(3) ?
C10 C11 C12 C13 . . . . 177.4(3) ?
C16 C11 C12 C13 . . . . -1.8(4) ?
C11 C12 C13 C14 . . . . 1.8(4) ?
C12 C13 C14 C15 . . . . -1.2(4) ?
C13 C14 C15 C16 . . . . 0.6(4) ?
C14 C15 C16 C7 . . . . -179.7(2) ?
C14 C15 C16 C11 . . . . -0.5(3) ?
C8 C7 C16 C15 . . . . 178.55(19) ?
C2 C7 C16 C15 . . . . -2.2(3) ?
C8 C7 C16 C11 . . . . -0.6(3) ?
C2 C7 C16 C11 . . . . 178.63(17) ?
C10 C11 C16 C15 . . . . -178.2(2) ?
C12 C11 C16 C15 . . . . 1.0(3) ?
C10 C11 C16 C7 . . . . 1.1(3) ?
C12 C11 C16 C7 . . . . -179.7(2) ?
C23 C1 C17 C18 . . . . 80.5(2) ?
C2 C1 C17 C18 . . . . -46.9(3) ?
C23 C1 C17 C22 . . . . -96.3(2) ?
C2 C1 C17 C22 . . . . 136.30(19) ?
C22 C17 C18 C19 . . . . 0.9(3) ?
C1 C17 C18 C19 . . . . -175.8(2) ?
C17 C18 C19 C20 . . . . 0.7(4) ?
C18 C19 C20 C21 . . . . -1.9(5) ?
C19 C20 C21 C22 . . . . 1.4(5) ?
C18 C17 C22 C21 . . . . -1.4(4) ?
C1 C17 C22 C21 . . . . 175.6(2) ?
C20 C21 C22 C17 . . . . 0.2(4) ?
C17 C1 C23 C24 . . . . -37.0(2) ?
C2 C1 C23 C24 . . . . 91.9(2) ?
C17 C1 C23 C31 . . . . 142.75(18) ?
C2 C1 C23 C31 . . . . -88.4(2) ?
C31 C23 C24 C25 . . . . 2.6(3) ?
C1 C23 C24 C25 . . . . -177.69(17) ?
C23 C24 C25 C26 . . . . -177.30(19) ?
C23 C24 C25 C30 . . . . 3.1(3) ?
C30 C25 C26 C27 . . . . 1.1(3) ?
C24 C25 C26 C27 . . . . -178.4(2) ?
C25 C26 C27 C28 . . . . 1.3(4) ?
C25 C26 C27 Br1 . . . . -177.66(17) ?
C26 C27 C28 C29 . . . . -1.9(4) ?
Br1 C27 C28 C29 . . . . 177.10(18) ?
C27 C28 C29 C30 . . . . -0.1(3) ?
C31 N2 C30 C25 . . . . 1.2(3) ?
C31 N2 C30 C29 . . . . 179.20(18) ?
C26 C25 C30 N2 . . . . 175.10(19) ?
C24 C25 C30 N2 . . . . -5.3(3) ?
C26 C25 C30 C29 . . . . -3.0(3) ?
C24 C25 C30 C29 . . . . 176.64(18) ?
C28 C29 C30 N2 . . . . -175.7(2) ?
C28 C29 C30 C25 . . . . 2.4(3) ?
C30 N2 C31 O2 . . . . -172.83(16) ?
C30 N2 C31 C23 . . . . 5.4(3) ?
C32 O2 C31 N2 . . . . 2.3(3) ?
C32 O2 C31 C23 . . . . -176.2(2) ?
C24 C23 C31 N2 . . . . -7.4(3) ?
C1 C23 C31 N2 . . . . 172.90(17) ?
C24 C23 C31 O2 . . . . 170.95(16) ?
C1 C23 C31 O2 . . . . -8.8(2) ?
O3 C33 C34 C35 . . . . 175.4(3) ?
O4 C33 C34 C35 . . . . -2.2(4) ?
C33 C34 C35 C36 . . . . 1.3(5) ?
C34 C35 C36 O6 . . . . -175.7(3) ?
C34 C35 C36 O5 . . . . 5.8(4) ?

_cod_database_fobs_code 2243794
