#------------------------------------------------------------------------------
#$Date: 2021-03-27 08:13:50 +0200 (Sat, 27 Mar 2021) $
#$Revision: 263391 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/37/2243793.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_2243793
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 0.995
_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            78980
_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         0.888
_refine_diff_density_min         -0.738
_refine_ls_abs_structure_details
;
Flack x determined using 4138 quotients
[(I⁺)-(I⁻)]/[(I⁺)+(I⁻)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.044(3)
_refine_ls_extinction_coef       0.0113(14)
_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   1.055
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     418
_refine_ls_number_reflns         13641
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.055
_refine_ls_R_factor_all          0.0691
_refine_ls_R_factor_gt           0.0477
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0725P)²+0.8990P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1424
_reflns_number_gt                10348
_reflns_number_total             13641
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tx2038sup1.cif
_cod_data_source_block           desolvated
_cod_original_sg_symbol_H-M      'C 2'
_cod_database_code               2243793
_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 0.30125(4) 0.01859(5) 0.48058(3) 0.0879(2) Uani d 1 . .
O O1 0.48670(11) 0.26945(13) 0.16346(10) 0.0303(3) Uani d 1 . .
H H1O 0.441024 0.283221 0.176802 0.036 Uiso calc 1 . .
O O2 0.56663(13) 0.48363(14) 0.36126(10) 0.0353(4) Uani d 1 . .
O O3 0.48998(13) 0.69083(16) 0.21057(12) 0.0413(4) Uani d 1 . .
O O4 0.56590(16) 0.7068(2) 0.12480(12) 0.0564(7) Uani d 1 . .
O O5 0.70940(16) 0.7676(2) 0.12134(12) 0.0530(6) Uani d 1 . .
H H5 0.648(3) 0.747(4) 0.119(3) 0.064 Uiso d 1 . .
O O6 0.83299(13) 0.81615(17) 0.20737(13) 0.0435(4) Uani d 1 . .
N N1 0.39732(12) 0.56474(15) 0.09851(10) 0.0256(3) Uani d 1 . .
H H1 0.430746 0.615825 0.136485 0.031 Uiso calc 1 . .
N N2 0.46078(14) 0.40519(19) 0.40536(11) 0.0344(4) Uani d 1 . .
C C1 0.60435(14) 0.32110(18) 0.27931(12) 0.0275(4) Uani d 1 . .
H H1A 0.643297 0.380159 0.299045 0.033 Uiso calc 1 . .
C C2 0.55201(14) 0.34533(16) 0.19164(12) 0.0248(4) Uani d 1 . .
C C3 0.50343(14) 0.44634(17) 0.18665(12) 0.0260(4) Uani d 1 . .
H H3A 0.458870 0.441573 0.215984 0.031 Uiso calc 1 . .
H H3B 0.546585 0.498846 0.211574 0.031 Uiso calc 1 . .
C C4 0.45729(15) 0.47679(17) 0.10240(12) 0.0277(4) Uani d 1 . .
H H4A 0.502527 0.493699 0.075660 0.033 Uiso calc 1 . .
H H4B 0.422337 0.419506 0.074578 0.033 Uiso calc 1 . .
C C5 0.31566(15) 0.5397(2) 0.12082(16) 0.0365(5) Uani d 1 . .
H H5A 0.281758 0.488848 0.085036 0.055 Uiso calc 1 . .
H H5B 0.279469 0.600029 0.117796 0.055 Uiso calc 1 . .
H H5C 0.331985 0.513607 0.174296 0.055 Uiso calc 1 . .
C C6 0.37408(17) 0.6109(2) 0.01963(14) 0.0341(5) Uani d 1 . .
H H6A 0.351408 0.559273 -0.019970 0.051 Uiso calc 1 . .
H H6B 0.426940 0.641772 0.010933 0.051 Uiso calc 1 . .
H H6C 0.328558 0.662211 0.015885 0.051 Uiso calc 1 . .
C C7 0.61578(15) 0.34283(17) 0.14019(12) 0.0270(4) Uani d 1 . .
C C8 0.59948(17) 0.2735(2) 0.08053(13) 0.0332(5) Uani d 1 . .
H H8 0.550112 0.229909 0.072930 0.040 Uiso calc 1 . .
C C9 0.6545(2) 0.2657(2) 0.03022(14) 0.0405(6) Uani d 1 . .
H H9 0.640743 0.218480 -0.011245 0.049 Uiso calc 1 . .
C C10 0.7269(2) 0.3254(2) 0.04101(15) 0.0410(6) Uani d 1 . .
H H10 0.764008 0.318635 0.007665 0.049 Uiso calc 1 . .
C C11 0.74727(17) 0.3971(2) 0.10125(15) 0.0372(5) Uani d 1 . .
C C12 0.8226(2) 0.4605(3) 0.1115(2) 0.0514(7) Uani d 1 . .
H H12 0.859768 0.451730 0.078446 0.062 Uiso calc 1 . .
C C13 0.8427(2) 0.5325(3) 0.1668(2) 0.0540(8) Uani d 1 . .
H H13 0.892496 0.574758 0.171714 0.065 Uiso calc 1 . .
C C14 0.7884(2) 0.5441(2) 0.21744(19) 0.0449(6) Uani d 1 . .
H H14 0.802662 0.593800 0.257128 0.054 Uiso calc 1 . .
C C15 0.71535(16) 0.4843(2) 0.20964(15) 0.0344(5) Uani d 1 . .
H H15 0.679762 0.494282 0.243939 0.041 Uiso calc 1 . .
C C16 0.69118(15) 0.40772(18) 0.15192(13) 0.0298(4) Uani d 1 . .
C C17 0.66522(16) 0.2308(2) 0.28868(13) 0.0323(5) Uani d 1 . .
C C18 0.6404(2) 0.1395(2) 0.25147(17) 0.0405(6) Uani d 1 . .
H H18 0.583556 0.132423 0.215075 0.049 Uiso calc 1 . .
C C19 0.6984(3) 0.0582(3) 0.2672(2) 0.0528(8) Uani d 1 . .
H H19 0.680733 -0.003545 0.241114 0.063 Uiso calc 1 . .
C C20 0.7808(3) 0.0663(3) 0.3199(2) 0.0640(11) Uani d 1 . .
H H20 0.819334 0.010108 0.331427 0.077 Uiso calc 1 . .
C C21 0.8068(2) 0.1574(4) 0.3561(2) 0.0649(11) Uani d 1 . .
H H21 0.864178 0.163800 0.391693 0.078 Uiso calc 1 . .
C C22 0.74995(18) 0.2406(3) 0.34113(16) 0.0457(7) Uani d 1 . .
H H22 0.768692 0.302737 0.366253 0.055 Uiso calc 1 . .
C C23 0.54190(14) 0.31290(19) 0.33007(12) 0.0283(4) Uani d 1 . .
C C24 0.50509(16) 0.2257(2) 0.34414(13) 0.0318(4) Uani d 1 . .
H H24 0.519769 0.164956 0.323111 0.038 Uiso calc 1 . .
C C25 0.44446(15) 0.2244(2) 0.39028(12) 0.0347(5) Uani d 1 . .
C C26 0.40766(19) 0.1342(3) 0.40905(16) 0.0439(6) Uani d 1 . .
H H26 0.423811 0.071423 0.392136 0.053 Uiso calc 1 . .
C C27 0.3479(2) 0.1395(3) 0.45243(17) 0.0510(8) Uani d 1 . .
C C28 0.32176(19) 0.2313(3) 0.47678(15) 0.0518(8) Uani d 1 . .
H H28 0.279070 0.233132 0.505128 0.062 Uiso calc 1 . .
C C29 0.35797(17) 0.3182(3) 0.45956(14) 0.0437(7) Uani d 1 . .
H H29 0.340071 0.380224 0.476292 0.052 Uiso calc 1 . .
C C30 0.42187(15) 0.3178(2) 0.41712(12) 0.0352(5) Uani d 1 . .
C C31 0.51945(15) 0.40092(19) 0.36697(12) 0.0299(4) Uani d 1 . .
C C32 0.5516(3) 0.5718(3) 0.4008(2) 0.0502(7) Uani d 1 . .
H H32A 0.491738 0.596937 0.376121 0.075 Uiso calc 1 . .
H H32B 0.595047 0.623067 0.397856 0.075 Uiso calc 1 . .
H H32C 0.557740 0.555914 0.455671 0.075 Uiso calc 1 . .
C C33 0.55716(17) 0.71776(19) 0.19320(14) 0.0340(5) Uani d 1 . .
C C34 0.63126(18) 0.7609(2) 0.25666(14) 0.0361(5) Uani d 1 . .
H H34 0.618957 0.769093 0.305373 0.043 Uiso calc 1 . .
C C35 0.71202(17) 0.7897(2) 0.25575(14) 0.0351(5) Uani d 1 . .
H H35 0.748533 0.813471 0.304385 0.042 Uiso calc 1 . .
C C36 0.75461(17) 0.79078(19) 0.19096(15) 0.0343(5) 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 . . 117.7(2) ?
C33 O4 H5 . . 111.7(19) ?
C36 O5 H5 . . 112(3) ?
C6 N1 C5 . . 110.39(18) ?
C6 N1 C4 . . 110.62(17) ?
C5 N1 C4 . . 113.13(18) ?
C6 N1 H1 . . 107.5 ?
C5 N1 H1 . . 107.5 ?
C4 N1 H1 . . 107.5 ?
C31 N2 C30 . . 117.5(2) ?
C23 C1 C17 . . 111.85(18) ?
C23 C1 C2 . . 111.21(17) ?
C17 C1 C2 . . 113.98(17) ?
C23 C1 H1A . . 106.4 ?
C17 C1 H1A . . 106.4 ?
C2 C1 H1A . . 106.4 ?
O1 C2 C3 . . 107.73(17) ?
O1 C2 C7 . . 107.45(17) ?
C3 C2 C7 . . 112.40(17) ?
O1 C2 C1 . . 108.90(17) ?
C3 C2 C1 . . 110.30(16) ?
C7 C2 C1 . . 109.94(16) ?
C4 C3 C2 . . 112.29(17) ?
C4 C3 H3A . . 109.1 ?
C2 C3 H3A . . 109.1 ?
C4 C3 H3B . . 109.1 ?
C2 C3 H3B . . 109.1 ?
H3A C3 H3B . . 107.9 ?
N1 C4 C3 . . 111.83(17) ?
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 . . 118.8(2) ?
C8 C7 C2 . . 117.7(2) ?
C16 C7 C2 . . 123.44(19) ?
C7 C8 C9 . . 121.7(3) ?
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 . . 120.5(2) ?
C9 C10 H10 . . 119.7 ?
C11 C10 H10 . . 119.7 ?
C10 C11 C12 . . 120.2(3) ?
C10 C11 C16 . . 120.0(3) ?
C12 C11 C16 . . 119.8(3) ?
C13 C12 C11 . . 122.1(3) ?
C13 C12 H12 . . 119.0 ?
C11 C12 H12 . . 119.0 ?
C12 C13 C14 . . 119.1(3) ?
C12 C13 H13 . . 120.5 ?
C14 C13 H13 . . 120.5 ?
C15 C14 C13 . . 120.7(3) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C14 C15 C16 . . 122.3(2) ?
C14 C15 H15 . . 118.8 ?
C16 C15 H15 . . 118.8 ?
C15 C16 C7 . . 125.3(2) ?
C15 C16 C11 . . 116.1(2) ?
C7 C16 C11 . . 118.6(2) ?
C18 C17 C22 . . 119.1(2) ?
C18 C17 C1 . . 124.1(2) ?
C22 C17 C1 . . 116.8(3) ?
C17 C18 C19 . . 120.4(3) ?
C17 C18 H18 . . 119.8 ?
C19 C18 H18 . . 119.8 ?
C20 C19 C18 . . 121.0(4) ?
C20 C19 H19 . . 119.5 ?
C18 C19 H19 . . 119.5 ?
C19 C20 C21 . . 119.0(3) ?
C19 C20 H20 . . 120.5 ?
C21 C20 H20 . . 120.5 ?
C20 C21 C22 . . 121.3(3) ?
C20 C21 H21 . . 119.4 ?
C22 C21 H21 . . 119.4 ?
C17 C22 C21 . . 119.2(4) ?
C17 C22 H22 . . 120.4 ?
C21 C22 H22 . . 120.4 ?
C24 C23 C31 . . 116.3(2) ?
C24 C23 C1 . . 123.8(2) ?
C31 C23 C1 . . 119.9(2) ?
C23 C24 C25 . . 120.6(2) ?
C23 C24 H24 . . 119.7 ?
C25 C24 H24 . . 119.7 ?
C30 C25 C26 . . 120.6(2) ?
C30 C25 C24 . . 117.2(2) ?
C26 C25 C24 . . 122.2(3) ?
C27 C26 C25 . . 118.6(3) ?
C27 C26 H26 . . 120.7 ?
C25 C26 H26 . . 120.7 ?
C26 C27 C28 . . 121.7(3) ?
C26 C27 Br1 . . 118.8(3) ?
C28 C27 Br1 . . 119.5(2) ?
C29 C28 C27 . . 119.7(3) ?
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 . . 122.3(2) ?
N2 C30 C29 . . 119.7(3) ?
C25 C30 C29 . . 117.9(3) ?
N2 C31 O2 . . 119.5(2) ?
N2 C31 C23 . . 125.5(2) ?
O2 C31 C23 . . 114.9(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 . . 122.6(2) ?
O3 C33 C34 . . 117.5(2) ?
O4 C33 C34 . . 119.9(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 . . 122.6(2) ?
O6 C36 C35 . . 117.3(2) ?
O5 C36 C35 . . 120.1(2) ?
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 . 1.900(4) ?
O1 C2 . 1.430(3) ?
O1 H1O . 0.8400 ?
O2 C31 . 1.351(3) ?
O2 C32 . 1.427(3) ?
O3 C33 . 1.238(3) ?
O4 C33 . 1.276(3) ?
O4 H5 . 1.43(5) ?
O5 C36 . 1.283(3) ?
O5 H5 . 0.99(5) ?
O6 C36 . 1.233(3) ?
N1 C6 . 1.486(3) ?
N1 C5 . 1.489(3) ?
N1 C4 . 1.497(3) ?
N1 H1 . 1.0000 ?
N2 C31 . 1.299(3) ?
N2 C30 . 1.363(4) ?
C1 C23 . 1.519(3) ?
C1 C17 . 1.520(3) ?
C1 C2 . 1.582(3) ?
C1 H1A . 1.0000 ?
C2 C3 . 1.541(3) ?
C2 C7 . 1.542(3) ?
C3 C4 . 1.529(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 . 1.380(3) ?
C7 C16 . 1.437(3) ?
C8 C9 . 1.419(3) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.358(5) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.408(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.426(5) ?
C11 C16 . 1.440(3) ?
C12 C13 . 1.350(6) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.419(5) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.376(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.425(4) ?
C15 H15 . 0.9500 ?
C17 C18 . 1.391(4) ?
C17 C22 . 1.402(4) ?
C18 C19 . 1.395(4) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.374(6) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.384(7) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.404(5) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 C24 . 1.356(4) ?
C23 C31 . 1.440(3) ?
C24 C25 . 1.428(3) ?
C24 H24 . 0.9500 ?
C25 C30 . 1.417(4) ?
C25 C26 . 1.418(4) ?
C26 C27 . 1.381(4) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.402(6) ?
C28 C29 . 1.366(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 . 1.493(3) ?
C34 C35 . 1.333(4) ?
C34 H34 . 0.9500 ?
C35 C36 . 1.493(4) ?
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 2.818(3) 179.5 yes
O5 H5 O4 . 0.99(5) 1.43(5) 2.419(3) 172(5) yes
N1 H1 O3 . 1.00 1.71 2.704(3) 172.4 yes
N1 H1 O4 . 1.00 2.51 3.188(3) 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 . . . . -56.9(2) ?
C17 C1 C2 O1 . . . . 70.6(2) ?
C23 C1 C2 C3 . . . . 61.1(2) ?
C17 C1 C2 C3 . . . . -171.37(19) ?
C23 C1 C2 C7 . . . . -174.42(19) ?
C17 C1 C2 C7 . . . . -46.9(3) ?
O1 C2 C3 C4 . . . . -65.4(2) ?
C7 C2 C3 C4 . . . . 52.8(2) ?
C1 C2 C3 C4 . . . . 175.85(18) ?
C6 N1 C4 C3 . . . . 163.58(19) ?
C5 N1 C4 C3 . . . . -72.0(2) ?
C2 C3 C4 N1 . . . . 169.78(18) ?
O1 C2 C7 C8 . . . . 0.3(3) ?
C3 C2 C7 C8 . . . . -118.1(2) ?
C1 C2 C7 C8 . . . . 118.7(2) ?
O1 C2 C7 C16 . . . . -178.93(19) ?
C3 C2 C7 C16 . . . . 62.7(2) ?
C1 C2 C7 C16 . . . . -60.5(3) ?
C16 C7 C8 C9 . . . . -0.8(3) ?
C2 C7 C8 C9 . . . . -180.0(2) ?
C7 C8 C9 C10 . . . . 1.7(4) ?
C8 C9 C10 C11 . . . . -1.3(4) ?
C9 C10 C11 C12 . . . . -179.1(3) ?
C9 C10 C11 C16 . . . . -0.1(4) ?
C10 C11 C12 C13 . . . . 177.7(3) ?
C16 C11 C12 C13 . . . . -1.4(5) ?
C11 C12 C13 C14 . . . . 1.4(5) ?
C12 C13 C14 C15 . . . . -1.1(5) ?
C13 C14 C15 C16 . . . . 0.8(4) ?
C14 C15 C16 C7 . . . . -179.7(2) ?
C14 C15 C16 C11 . . . . -0.7(4) ?
C8 C7 C16 C15 . . . . 178.4(2) ?
C2 C7 C16 C15 . . . . -2.4(3) ?
C8 C7 C16 C11 . . . . -0.6(3) ?
C2 C7 C16 C11 . . . . 178.6(2) ?
C10 C11 C16 C15 . . . . -178.1(2) ?
C12 C11 C16 C15 . . . . 0.9(3) ?
C10 C11 C16 C7 . . . . 1.0(3) ?
C12 C11 C16 C7 . . . . -180.0(2) ?
C23 C1 C17 C18 . . . . 80.4(3) ?
C2 C1 C17 C18 . . . . -46.8(3) ?
C23 C1 C17 C22 . . . . -96.6(3) ?
C2 C1 C17 C22 . . . . 136.2(2) ?
C22 C17 C18 C19 . . . . 1.2(4) ?
C1 C17 C18 C19 . . . . -175.7(2) ?
C17 C18 C19 C20 . . . . 0.4(5) ?
C18 C19 C20 C21 . . . . -1.7(5) ?
C19 C20 C21 C22 . . . . 1.4(6) ?
C18 C17 C22 C21 . . . . -1.4(4) ?
C1 C17 C22 C21 . . . . 175.7(3) ?
C20 C21 C22 C17 . . . . 0.1(5) ?
C17 C1 C23 C24 . . . . -36.6(3) ?
C2 C1 C23 C24 . . . . 92.1(2) ?
C17 C1 C23 C31 . . . . 142.8(2) ?
C2 C1 C23 C31 . . . . -88.5(2) ?
C31 C23 C24 C25 . . . . 2.8(3) ?
C1 C23 C24 C25 . . . . -177.8(2) ?
C23 C24 C25 C30 . . . . 2.8(3) ?
C23 C24 C25 C26 . . . . -177.2(2) ?
C30 C25 C26 C27 . . . . 1.5(4) ?
C24 C25 C26 C27 . . . . -178.5(2) ?
C25 C26 C27 C28 . . . . 1.2(4) ?
C25 C26 C27 Br1 . . . . -178.0(2) ?
C26 C27 C28 C29 . . . . -2.0(4) ?
Br1 C27 C28 C29 . . . . 177.2(2) ?
C27 C28 C29 C30 . . . . 0.1(4) ?
C31 N2 C30 C25 . . . . 1.1(3) ?
C31 N2 C30 C29 . . . . 179.3(2) ?
C26 C25 C30 N2 . . . . 174.9(2) ?
C24 C25 C30 N2 . . . . -5.1(3) ?
C26 C25 C30 C29 . . . . -3.3(3) ?
C24 C25 C30 C29 . . . . 176.7(2) ?
C28 C29 C30 N2 . . . . -175.8(2) ?
C28 C29 C30 C25 . . . . 2.5(3) ?
C30 N2 C31 O2 . . . . -172.82(19) ?
C30 N2 C31 C23 . . . . 5.4(3) ?
C32 O2 C31 N2 . . . . 2.3(3) ?
C32 O2 C31 C23 . . . . -176.1(2) ?
C24 C23 C31 N2 . . . . -7.4(3) ?
C1 C23 C31 N2 . . . . 173.1(2) ?
C24 C23 C31 O2 . . . . 170.88(19) ?
C1 C23 C31 O2 . . . . -8.6(3) ?
O3 C33 C34 C35 . . . . 175.3(3) ?
O4 C33 C34 C35 . . . . -2.3(5) ?
C33 C34 C35 C36 . . . . 1.6(5) ?
C34 C35 C36 O6 . . . . -175.9(3) ?
C34 C35 C36 O5 . . . . 5.4(5) ?

_cod_database_fobs_code 2243793
