#------------------------------------------------------------------------------
#$Date: 2020-10-23 07:36:19 +0300 (Fri, 23 Oct 2020) $
#$Revision: 258573 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/22/2022269.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_2022269
loop_
_publ_author_name
'Okezue, Mercy'
'Smith, Daniel'
'Zeller, Matthias'
'Byrn, Stephen R.'
'Smith, Pamela'
'Bogandowich-Knipp, Susan'
'Purcell, Dale K.'
'Clase, Kari L.'
_publ_section_title
;
 Crystal structures of salts of bedaquiline
;
_journal_coeditor_code           OV3143
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229620013455
_journal_volume                  76
_journal_year                    2020
_chemical_absolute_configuration ad
_chemical_formula_iupac
'C32 H32 Br N2 O2 +, C7 H5 O2 -, 0.742C2 H3 N, H2 O'
_chemical_formula_moiety
'C32 H32 Br N2 O2 +, C7 H5 O2 -, 0.742(C2 H3 N), H2 O'
_chemical_formula_sum            'C40.48 H41.23 Br N2.74 O5'
_chemical_formula_weight         726.10
_chemical_name_common
;
Bedaqulinium benzoate acetonitrile 0.742-solvate monohydrate
;
_chemical_name_systematic
'[4-(6-Bromo-2-methoxyquinolin-3-yl)-3-hydroxy-3-(naphthalen-1-yl)-4-phenylbutyl]dimethylazanium benzoate acetonitrile 0.742-solvate monohydrate'
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 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                 101.093(3)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   12.8661(8)
_cell_length_b                   8.0386(5)
_cell_length_c                   17.4704(10)
_cell_measurement_reflns_used    9023
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      79.0807
_cell_measurement_theta_min      2.5773
_cell_volume                     1773.12(19)
_computing_cell_refinement
;
SAINT (Bruker, 2019)
;
_computing_data_collection
;
APEX3 (Bruker, 2019)
;
_computing_data_reduction
;
SAINT (Bruker, 2019)
;
_computing_molecular_graphics
;
Mercury (Macrae et al.,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015) and
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 1.000
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type
;
Bruker D8 Quest diffractometer with PhotonIII_C14 charge-integrating and
photon counting pixel array detector
;
_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  0.0603
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            39739
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         80.060
_diffrn_reflns_theta_min         2.577
_diffrn_source                   'I-mu-S microsource X-ray tube'
_diffrn_source_current           '1.0 mA'
_diffrn_source_voltage           '50 kV'
_exptl_absorpt_coefficient_mu    1.970
_exptl_absorpt_correction_T_max  0.7543
_exptl_absorpt_correction_T_min  0.5987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS2016; Krause et al.,  2015)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_description       needle
_exptl_crystal_F_000             757
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_refine_diff_density_max         0.399
_refine_diff_density_min         -0.499
_refine_ls_abs_structure_details
;
Flack x determined using 2778 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al.,  2013)
;
_refine_ls_abs_structure_Flack   0.004(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     515
_refine_ls_number_reflns         7360
_refine_ls_number_restraints     195
_refine_ls_restrained_S_all      1.052
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0347
_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)+(0.0233P)²+1.0420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0847
_reflns_number_gt                6750
_reflns_number_total             7360
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ov3143sup1.cif
_cod_data_source_block           4b
_cod_original_cell_volume        1773.13(19)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2022269
_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   0.580
_shelx_estimated_absorpt_t_max   0.908
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, 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 1.09186(3) 0.23149(6) -0.10436(2) 0.04184(12) Uani d 1 . .
O O1 0.7542(2) 0.3259(3) 0.20992(15) 0.0271(5) Uani d 1 . .
H H1B 0.734(4) 0.292(2) 0.168(3) 0.041 Uiso calc 1 . .
O O2 1.08646(19) 0.0320(3) 0.35039(14) 0.0297(5) Uani d 1 . .
O O3 0.4583(2) 0.2868(4) 0.05847(18) 0.0497(8) Uani d 1 . .
O O4 0.3385(2) 0.4448(4) -0.01724(15) 0.0373(6) Uani d 1 . .
O O5 0.6707(3) 0.2738(4) 0.05844(16) 0.0387(7) Uani d 1 . .
H H5D 0.674(5) 0.174(4) 0.041(3) 0.058 Uiso d 1 . .
H H5E 0.607(2) 0.288(7) 0.058(3) 0.058 Uiso d 1 . .
N N1 0.5911(2) -0.1342(4) 0.14353(17) 0.0272(6) Uani d 1 . .
H H1 0.618783 -0.106871 0.095314 0.033 Uiso calc 1 . .
N N2 1.1414(2) 0.0196(4) 0.23270(18) 0.0292(6) Uani d 1 . .
C C1 0.9000(2) 0.1962(4) 0.29767(17) 0.0228(7) Uani d 1 . .
H H1A 0.913127 0.113403 0.341185 0.027 Uiso calc 1 . .
C C2 0.7781(3) 0.1907(4) 0.26263(18) 0.0228(7) Uani d 1 . .
C C3 0.7471(3) 0.0265(4) 0.21840(19) 0.0234(7) Uani d 1 . .
H H3A 0.772164 0.028938 0.168253 0.028 Uiso calc 1 . .
H H3B 0.782695 -0.067448 0.249584 0.028 Uiso calc 1 . .
C C4 0.6277(3) -0.0017(5) 0.20251(19) 0.0249(7) Uani d 1 . .
H H4A 0.605984 -0.032128 0.252035 0.030 Uiso calc 1 . .
H H4B 0.591887 0.103914 0.184090 0.030 Uiso calc 1 . .
C C5 0.6308(3) -0.3018(5) 0.1703(2) 0.0391(9) Uani d 1 . .
H H5A 0.605300 -0.383658 0.129406 0.059 Uiso calc 1 . .
H H5B 0.604938 -0.331264 0.217728 0.059 Uiso calc 1 . .
H H5C 0.708438 -0.301159 0.181360 0.059 Uiso calc 1 . .
C C6 0.4732(3) -0.1344(6) 0.1230(2) 0.0366(9) Uani d 1 . .
H H6A 0.448325 -0.025168 0.102189 0.055 Uiso calc 1 . .
H H6B 0.444151 -0.158068 0.169733 0.055 Uiso calc 1 . .
H H6C 0.449601 -0.219985 0.083535 0.055 Uiso calc 1 . .
C C7 0.7184(2) 0.2225(5) 0.33036(16) 0.0237(6) Uani d 1 . .
C C8 0.6696(3) 0.3737(5) 0.3321(2) 0.0322(8) Uani d 1 . .
H H8 0.670541 0.448836 0.290297 0.039 Uiso calc 1 . .
C C9 0.6182(3) 0.4236(6) 0.3928(2) 0.0391(9) Uani d 1 . .
H H9 0.586471 0.530466 0.391630 0.047 Uiso calc 1 . .
C C10 0.6143(3) 0.3178(6) 0.4529(2) 0.0371(9) Uani d 1 . .
H H10 0.578544 0.350206 0.493248 0.045 Uiso calc 1 . .
C C11 0.6629(3) 0.1604(5) 0.4556(2) 0.0328(8) Uani d 1 . .
C C12 0.6601(4) 0.0520(6) 0.5190(2) 0.0464(11) Uani d 1 . .
H H12 0.624115 0.086173 0.559045 0.056 Uiso calc 1 . .
C C13 0.7070(5) -0.0985(7) 0.5241(3) 0.0578(14) Uani d 1 . .
H H13 0.704267 -0.168798 0.567337 0.069 Uiso calc 1 . .
C C14 0.7601(4) -0.1511(6) 0.4650(3) 0.0477(11) Uani d 1 . .
H H14 0.793019 -0.257285 0.468543 0.057 Uiso calc 1 . .
C C15 0.7646(3) -0.0505(5) 0.4024(2) 0.0329(8) Uani d 1 . .
H H15 0.800873 -0.088643 0.363250 0.040 Uiso calc 1 . .
C C16 0.7167(3) 0.1088(5) 0.3945(2) 0.0261(7) Uani d 1 . .
C C17 0.9317(3) 0.3644(4) 0.33358(19) 0.0243(7) Uani d 1 . .
C C18 0.9390(3) 0.3895(5) 0.41323(19) 0.0287(7) Uani d 1 . .
H H18 0.925588 0.299474 0.445188 0.034 Uiso calc 1 . .
C C19 0.9654(3) 0.5436(5) 0.4466(2) 0.0319(8) Uani d 1 . .
H H19 0.970429 0.558180 0.501130 0.038 Uiso calc 1 . .
C C20 0.9846(3) 0.6768(5) 0.4009(2) 0.0340(8) Uani d 1 . .
H H20 1.002007 0.782928 0.423684 0.041 Uiso calc 1 . .
C C21 0.9780(3) 0.6530(5) 0.3214(2) 0.0341(8) Uani d 1 . .
H H21 0.991414 0.743347 0.289646 0.041 Uiso calc 1 . .
C C22 0.9520(3) 0.4987(5) 0.2883(2) 0.0301(8) Uani d 1 . .
H H22 0.947839 0.484164 0.233828 0.036 Uiso calc 1 . .
C C23 0.9726(3) 0.1487(4) 0.2416(2) 0.0241(7) Uani d 1 . .
C C24 0.9580(3) 0.1938(4) 0.16468(18) 0.0242(7) Uani d 1 . .
H H24 0.896018 0.253246 0.141633 0.029 Uiso calc 1 . .
C C25 1.0347(3) 0.1528(5) 0.1189(2) 0.0263(7) Uani d 1 . .
C C26 1.0240(3) 0.2018(5) 0.04000(19) 0.0289(8) Uani d 1 . .
H H26 0.964322 0.264196 0.015139 0.035 Uiso calc 1 . .
C C27 1.1014(3) 0.1574(5) 0.0004(2) 0.0312(8) Uani d 1 . .
C C28 1.1884(3) 0.0584(5) 0.0338(2) 0.0361(9) Uani d 1 . .
H H28 1.238547 0.023743 0.003564 0.043 Uiso calc 1 . .
C C29 1.2000(3) 0.0124(6) 0.1104(3) 0.0378(9) Uani d 1 . .
H H29 1.259208 -0.052812 0.133734 0.045 Uiso calc 1 . .
C C30 1.1246(3) 0.0612(5) 0.1550(2) 0.0285(7) Uani d 1 . .
C C31 1.0703(3) 0.0644(4) 0.2727(2) 0.0251(7) Uani d 1 . .
C C32 1.1850(3) -0.0452(6) 0.3846(3) 0.0427(10) Uani d 1 . .
H H32A 1.191281 -0.152129 0.358991 0.064 Uiso calc 1 . .
H H32B 1.187118 -0.063515 0.440374 0.064 Uiso calc 1 . .
H H32C 1.243771 0.027348 0.377926 0.064 Uiso calc 1 . .
C C33 0.3819(3) 0.3840(5) 0.0484(2) 0.0310(8) Uani d 1 . .
C C34 0.3376(12) 0.439(3) 0.1162(6) 0.030(2) Uani d 0.742(7) A 1
C C35 0.2342(10) 0.5018(15) 0.1055(5) 0.0338(19) Uani d 0.742(7) A 1
H H35 0.193862 0.513732 0.054183 0.041 Uiso calc 0.742(7) A 1
C C36 0.1905(9) 0.5461(17) 0.1683(5) 0.047(2) Uani d 0.742(7) A 1
H H36 0.118077 0.577683 0.160811 0.057 Uiso calc 0.742(7) A 1
C C37 0.2530(7) 0.5447(12) 0.2437(5) 0.0531(19) Uani d 0.742(7) A 1
H H37 0.225227 0.586384 0.286502 0.064 Uiso calc 0.742(7) A 1
C C38 0.3550(6) 0.4828(10) 0.2555(4) 0.0467(16) Uani d 0.742(7) A 1
H H38 0.396204 0.475671 0.306703 0.056 Uiso calc 0.742(7) A 1
C C39 0.3966(5) 0.4313(9) 0.1920(4) 0.0371(14) Uani d 0.742(7) A 1
H H39 0.466935 0.389697 0.200206 0.044 Uiso calc 0.742(7) A 1
C C34B 0.331(4) 0.429(8) 0.1208(16) 0.0242(7) Uani d 0.258(7) A 2
C C35B 0.239(3) 0.526(5) 0.1165(17) 0.035(4) Uani d 0.258(7) A 2
H H35B 0.202750 0.564683 0.067136 0.042 Uiso calc 0.258(7) A 2
C C36B 0.202(3) 0.567(5) 0.1825(16) 0.044(4) Uani d 0.258(7) A 2
H H36B 0.150076 0.651410 0.181779 0.053 Uiso calc 0.258(7) A 2
C C37B 0.2432(18) 0.479(3) 0.2514(14) 0.047(3) Uani d 0.258(7) A 2
H H37B 0.205535 0.477535 0.293157 0.056 Uiso calc 0.258(7) A 2
C C38B 0.3375(16) 0.396(3) 0.2586(11) 0.047(3) Uani d 0.258(7) A 2
H H38B 0.373369 0.359002 0.308434 0.057 Uiso calc 0.258(7) A 2
C C39B 0.3805(17) 0.365(3) 0.1932(11) 0.039(3) Uani d 0.258(7) A 2
H H39B 0.443068 0.299799 0.197365 0.047 Uiso calc 0.258(7) A 2
N N3 0.4791(5) -0.2008(8) 0.3556(4) 0.0620(18) Uani d 0.742(7) A 1
C C40 0.4502(5) -0.0703(9) 0.3379(4) 0.0477(16) Uani d 0.742(7) A 1
C C41 0.4178(6) 0.0985(10) 0.3164(5) 0.063(2) Uani d 0.742(7) A 1
H H41A 0.473979 0.155009 0.295727 0.12(4) Uiso calc 0.742(7) A 1
H H41B 0.404449 0.158210 0.362451 0.14(5) Uiso calc 0.742(7) A 1
H H41C 0.352857 0.096518 0.276432 0.06(2) Uiso calc 0.742(7) A 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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 H1B . . 109.5 ?
C31 O2 C32 . . 116.9(3) ?
H5D O5 H5E . . 104(5) ?
C5 N1 C6 . . 110.4(3) ?
C5 N1 C4 . . 112.7(3) ?
C6 N1 C4 . . 109.8(3) ?
C5 N1 H1 . . 107.9 ?
C6 N1 H1 . . 107.9 ?
C4 N1 H1 . . 107.9 ?
C31 N2 C30 . . 117.9(3) ?
C17 C1 C23 . . 109.9(3) ?
C17 C1 C2 . . 110.9(3) ?
C23 C1 C2 . . 115.5(3) ?
C17 C1 H1A . . 106.7 ?
C23 C1 H1A . . 106.7 ?
C2 C1 H1A . . 106.7 ?
O1 C2 C3 . . 109.1(3) ?
O1 C2 C7 . . 107.0(3) ?
C3 C2 C7 . . 113.9(3) ?
O1 C2 C1 . . 107.8(3) ?
C3 C2 C1 . . 111.2(3) ?
C7 C2 C1 . . 107.6(2) ?
C4 C3 C2 . . 111.8(3) ?
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 . . 113.9(3) ?
N1 C4 H4A . . 108.8 ?
C3 C4 H4A . . 108.8 ?
N1 C4 H4B . . 108.8 ?
C3 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
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 . . 117.8(3) ?
C8 C7 C2 . . 117.3(3) ?
C16 C7 C2 . . 124.7(3) ?
C7 C8 C9 . . 123.5(4) ?
C7 C8 H8 . . 118.3 ?
C9 C8 H8 . . 118.3 ?
C10 C9 C8 . . 119.6(4) ?
C10 C9 H9 . . 120.2 ?
C8 C9 H9 . . 120.2 ?
C9 C10 C11 . . 120.4(4) ?
C9 C10 H10 . . 119.8 ?
C11 C10 H10 . . 119.8 ?
C10 C11 C12 . . 120.1(4) ?
C10 C11 C16 . . 120.5(4) ?
C12 C11 C16 . . 119.5(4) ?
C13 C12 C11 . . 121.7(4) ?
C13 C12 H12 . . 119.2 ?
C11 C12 H12 . . 119.2 ?
C12 C13 C14 . . 119.8(4) ?
C12 C13 H13 . . 120.1 ?
C14 C13 H13 . . 120.1 ?
C15 C14 C13 . . 120.6(4) ?
C15 C14 H14 . . 119.7 ?
C13 C14 H14 . . 119.7 ?
C14 C15 C16 . . 121.8(4) ?
C14 C15 H15 . . 119.1 ?
C16 C15 H15 . . 119.1 ?
C15 C16 C11 . . 116.7(3) ?
C15 C16 C7 . . 125.1(3) ?
C11 C16 C7 . . 118.2(3) ?
C18 C17 C22 . . 118.1(3) ?
C18 C17 C1 . . 120.3(3) ?
C22 C17 C1 . . 121.5(3) ?
C19 C18 C17 . . 121.0(3) ?
C19 C18 H18 . . 119.5 ?
C17 C18 H18 . . 119.5 ?
C18 C19 C20 . . 120.4(3) ?
C18 C19 H19 . . 119.8 ?
C20 C19 H19 . . 119.8 ?
C19 C20 C21 . . 119.1(4) ?
C19 C20 H20 . . 120.4 ?
C21 C20 H20 . . 120.4 ?
C22 C21 C20 . . 120.4(3) ?
C22 C21 H21 . . 119.8 ?
C20 C21 H21 . . 119.8 ?
C21 C22 C17 . . 121.0(3) ?
C21 C22 H22 . . 119.5 ?
C17 C22 H22 . . 119.5 ?
C24 C23 C31 . . 116.1(3) ?
C24 C23 C1 . . 125.3(3) ?
C31 C23 C1 . . 118.2(3) ?
C23 C24 C25 . . 120.7(3) ?
C23 C24 H24 . . 119.6 ?
C25 C24 H24 . . 119.6 ?
C30 C25 C26 . . 119.9(3) ?
C30 C25 C24 . . 117.8(3) ?
C26 C25 C24 . . 122.4(3) ?
C27 C26 C25 . . 118.6(3) ?
C27 C26 H26 . . 120.7 ?
C25 C26 H26 . . 120.7 ?
C26 C27 C28 . . 122.5(4) ?
C26 C27 Br1 . . 119.2(3) ?
C28 C27 Br1 . . 118.3(3) ?
C29 C28 C27 . . 119.1(3) ?
C29 C28 H28 . . 120.4 ?
C27 C28 H28 . . 120.4 ?
C28 C29 C30 . . 120.6(4) ?
C28 C29 H29 . . 119.7 ?
C30 C29 H29 . . 119.7 ?
N2 C30 C29 . . 118.9(3) ?
N2 C30 C25 . . 121.9(3) ?
C29 C30 C25 . . 119.2(3) ?
N2 C31 O2 . . 119.6(3) ?
N2 C31 C23 . . 125.4(3) ?
O2 C31 C23 . . 115.0(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 . . 124.6(4) ?
O3 C33 C34 . . 119.5(5) ?
O4 C33 C34 . . 115.9(5) ?
O3 C33 C34B . . 118.1(11) ?
O4 C33 C34B . . 117.2(11) ?
C39 C34 C35 . . 118.2(9) ?
C39 C34 C33 . . 121.6(9) ?
C35 C34 C33 . . 120.2(9) ?
C36 C35 C34 . . 120.7(8) ?
C36 C35 H35 . . 119.6 ?
C34 C35 H35 . . 119.6 ?
C35 C36 C37 . . 119.9(8) ?
C35 C36 H36 . . 120.1 ?
C37 C36 H36 . . 120.1 ?
C38 C37 C36 . . 119.9(7) ?
C38 C37 H37 . . 120.0 ?
C36 C37 H37 . . 120.0 ?
C37 C38 C39 . . 119.4(6) ?
C37 C38 H38 . . 120.3 ?
C39 C38 H38 . . 120.3 ?
C38 C39 C34 . . 121.6(7) ?
C38 C39 H39 . . 119.2 ?
C34 C39 H39 . . 119.2 ?
C39B C34B C35B . . 119(2) ?
C39B C34B C33 . . 117(2) ?
C35B C34B C33 . . 124(2) ?
C36B C35B C34B . . 121(2) ?
C36B C35B H35B . . 119.6 ?
C34B C35B H35B . . 119.6 ?
C35B C36B C37B . . 118(2) ?
C35B C36B H36B . . 121.2 ?
C37B C36B H36B . . 121.2 ?
C38B C37B C36B . . 120(2) ?
C38B C37B H37B . . 119.8 ?
C36B C37B H37B . . 119.8 ?
C37B C38B C39B . . 120.0(17) ?
C37B C38B H38B . . 120.0 ?
C39B C38B H38B . . 120.0 ?
C38B C39B C34B . . 119.7(19) ?
C38B C39B H39B . . 120.2 ?
C34B C39B H39B . . 120.2 ?
N3 C40 C41 . . 177.7(8) ?
C40 C41 H41A . . 109.5 ?
C40 C41 H41B . . 109.5 ?
H41A C41 H41B . . 109.5 ?
C40 C41 H41C . . 109.5 ?
H41A C41 H41C . . 109.5 ?
H41B C41 H41C . . 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 . 1.905(4) ?
O1 C2 . 1.419(4) ?
O1 H1B . 0.77(5) ?
O2 C31 . 1.358(4) ?
O2 C32 . 1.434(4) ?
O3 C33 . 1.241(5) ?
O4 C33 . 1.273(5) ?
O5 H5D . 0.86(3) ?
O5 H5E . 0.82(3) ?
N1 C5 . 1.484(5) ?
N1 C6 . 1.490(5) ?
N1 C4 . 1.494(4) ?
N1 H1 . 1.0000 ?
N2 C31 . 1.305(5) ?
N2 C30 . 1.374(5) ?
C1 C17 . 1.513(5) ?
C1 C23 . 1.526(4) ?
C1 C2 . 1.572(4) ?
C1 H1A . 1.0000 ?
C2 C3 . 1.543(5) ?
C2 C7 . 1.551(4) ?
C3 C4 . 1.525(5) ?
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 . 1.370(6) ?
C7 C16 . 1.449(5) ?
C8 C9 . 1.411(5) ?
C8 H8 . 0.9500 ?
C9 C10 . 1.359(6) ?
C9 H9 . 0.9500 ?
C10 C11 . 1.408(6) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.416(6) ?
C11 C16 . 1.440(5) ?
C12 C13 . 1.347(7) ?
C12 H12 . 0.9500 ?
C13 C14 . 1.408(6) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.370(5) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.417(5) ?
C15 H15 . 0.9500 ?
C17 C18 . 1.391(5) ?
C17 C22 . 1.393(5) ?
C18 C19 . 1.383(5) ?
C18 H18 . 0.9500 ?
C19 C20 . 1.386(5) ?
C19 H19 . 0.9500 ?
C20 C21 . 1.387(5) ?
C20 H20 . 0.9500 ?
C21 C22 . 1.383(5) ?
C21 H21 . 0.9500 ?
C22 H22 . 0.9500 ?
C23 C24 . 1.370(5) ?
C23 C31 . 1.440(5) ?
C24 C25 . 1.423(5) ?
C24 H24 . 0.9500 ?
C25 C30 . 1.413(5) ?
C25 C26 . 1.415(5) ?
C26 C27 . 1.365(5) ?
C26 H26 . 0.9500 ?
C27 C28 . 1.406(6) ?
C28 C29 . 1.369(6) ?
C28 H28 . 0.9500 ?
C29 C30 . 1.412(5) ?
C29 H29 . 0.9500 ?
C32 H32A . 0.9800 ?
C32 H32B . 0.9800 ?
C32 H32C . 0.9800 ?
C33 C34 . 1.478(12) ?
C33 C34B . 1.57(3) ?
C34 C39 . 1.395(11) ?
C34 C35 . 1.401(10) ?
C35 C36 . 1.373(9) ?
C35 H35 . 0.9500 ?
C36 C37 . 1.405(10) ?
C36 H36 . 0.9500 ?
C37 C38 . 1.381(10) ?
C37 H37 . 0.9500 ?
C38 C39 . 1.385(8) ?
C38 H38 . 0.9500 ?
C39 H39 . 0.9500 ?
C34B C39B . 1.40(2) ?
C34B C35B . 1.41(2) ?
C35B C36B . 1.37(2) ?
C35B H35B . 0.9500 ?
C36B C37B . 1.41(2) ?
C36B H36B . 0.9500 ?
C37B C38B . 1.37(2) ?
C37B H37B . 0.9500 ?
C38B C39B . 1.384(19) ?
C38B H38B . 0.9500 ?
C39B H39B . 0.9500 ?
N3 C40 . 1.136(9) ?
C40 C41 . 1.448(10) ?
C41 H41A . 0.9800 ?
C41 H41B . 0.9800 ?
C41 H41C . 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 H1B O5 . 0.77 1.94 2.691(4) 163.3 yes
O5 H5D O4 2_645 0.86(3) 1.89(3) 2.738(4) 168(6) yes
O5 H5E O3 . 0.82(3) 1.92(3) 2.734(4) 172(6) yes
N1 H1 O4 2_645 1.00 1.62 2.619(4) 177.7 yes
C5 H5C Br1 2_745 0.98 3.13 3.964(4) 143.6 yes
C6 H6A O3 . 0.98 2.63 3.562(6) 158.5 yes
C28 H28 O5 2_745 0.95 2.66 3.498(5) 147.8 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
C17 C1 C2 O1 . . . . 54.5(3) ?
C23 C1 C2 O1 . . . . -71.4(3) ?
C17 C1 C2 C3 . . . . 174.1(3) ?
C23 C1 C2 C3 . . . . 48.2(4) ?
C17 C1 C2 C7 . . . . -60.6(3) ?
C23 C1 C2 C7 . . . . 173.6(3) ?
O1 C2 C3 C4 . . . . -76.1(3) ?
C7 C2 C3 C4 . . . . 43.4(4) ?
C1 C2 C3 C4 . . . . 165.1(3) ?
C5 N1 C4 C3 . . . . 65.3(4) ?
C6 N1 C4 C3 . . . . -171.3(3) ?
C2 C3 C4 N1 . . . . 165.5(3) ?
O1 C2 C7 C8 . . . . -8.1(4) ?
C3 C2 C7 C8 . . . . -128.8(3) ?
C1 C2 C7 C8 . . . . 107.5(3) ?
O1 C2 C7 C16 . . . . 176.3(3) ?
C3 C2 C7 C16 . . . . 55.6(4) ?
C1 C2 C7 C16 . . . . -68.1(4) ?
C16 C7 C8 C9 . . . . -0.1(6) ?
C2 C7 C8 C9 . . . . -175.9(3) ?
C7 C8 C9 C10 . . . . -0.9(6) ?
C8 C9 C10 C11 . . . . 1.2(6) ?
C9 C10 C11 C12 . . . . 178.9(4) ?
C9 C10 C11 C16 . . . . -0.5(6) ?
C10 C11 C12 C13 . . . . -179.1(5) ?
C16 C11 C12 C13 . . . . 0.4(7) ?
C11 C12 C13 C14 . . . . -0.3(8) ?
C12 C13 C14 C15 . . . . 0.1(8) ?
C13 C14 C15 C16 . . . . 0.0(7) ?
C14 C15 C16 C11 . . . . 0.1(6) ?
C14 C15 C16 C7 . . . . 179.7(4) ?
C10 C11 C16 C15 . . . . 179.2(4) ?
C12 C11 C16 C15 . . . . -0.3(6) ?
C10 C11 C16 C7 . . . . -0.5(5) ?
C12 C11 C16 C7 . . . . -179.9(4) ?
C8 C7 C16 C15 . . . . -178.9(4) ?
C2 C7 C16 C15 . . . . -3.3(5) ?
C8 C7 C16 C11 . . . . 0.7(5) ?
C2 C7 C16 C11 . . . . 176.3(3) ?
C23 C1 C17 C18 . . . . -135.1(3) ?
C2 C1 C17 C18 . . . . 95.9(4) ?
C23 C1 C17 C22 . . . . 46.4(4) ?
C2 C1 C17 C22 . . . . -82.5(4) ?
C22 C17 C18 C19 . . . . 0.1(5) ?
C1 C17 C18 C19 . . . . -178.4(3) ?
C17 C18 C19 C20 . . . . 0.4(6) ?
C18 C19 C20 C21 . . . . -0.7(6) ?
C19 C20 C21 C22 . . . . 0.4(6) ?
C20 C21 C22 C17 . . . . 0.1(6) ?
C18 C17 C22 C21 . . . . -0.3(6) ?
C1 C17 C22 C21 . . . . 178.2(3) ?
C17 C1 C23 C24 . . . . -86.1(4) ?
C2 C1 C23 C24 . . . . 40.2(5) ?
C17 C1 C23 C31 . . . . 87.0(4) ?
C2 C1 C23 C31 . . . . -146.7(3) ?
C31 C23 C24 C25 . . . . 2.2(5) ?
C1 C23 C24 C25 . . . . 175.4(3) ?
C23 C24 C25 C30 . . . . 1.3(5) ?
C23 C24 C25 C26 . . . . -178.0(3) ?
C30 C25 C26 C27 . . . . 0.6(5) ?
C24 C25 C26 C27 . . . . 179.9(3) ?
C25 C26 C27 C28 . . . . 3.2(6) ?
C25 C26 C27 Br1 . . . . -177.0(3) ?
C26 C27 C28 C29 . . . . -4.1(6) ?
Br1 C27 C28 C29 . . . . 176.1(3) ?
C27 C28 C29 C30 . . . . 1.1(6) ?
C31 N2 C30 C29 . . . . -179.3(4) ?
C31 N2 C30 C25 . . . . 1.4(5) ?
C28 C29 C30 N2 . . . . -176.9(4) ?
C28 C29 C30 C25 . . . . 2.4(6) ?
C26 C25 C30 N2 . . . . 176.0(3) ?
C24 C25 C30 N2 . . . . -3.3(5) ?
C26 C25 C30 C29 . . . . -3.3(6) ?
C24 C25 C30 C29 . . . . 177.4(3) ?
C30 N2 C31 O2 . . . . -177.1(3) ?
C30 N2 C31 C23 . . . . 2.6(5) ?
C32 O2 C31 N2 . . . . 2.4(5) ?
C32 O2 C31 C23 . . . . -177.3(3) ?
C24 C23 C31 N2 . . . . -4.4(5) ?
C1 C23 C31 N2 . . . . -178.2(3) ?
C24 C23 C31 O2 . . . . 175.3(3) ?
C1 C23 C31 O2 . . . . 1.5(5) ?
O3 C33 C34 C39 . . . . 21(2) ?
O4 C33 C34 C39 . . . . -157.5(13) ?
O3 C33 C34 C35 . . . . -159.2(14) ?
O4 C33 C34 C35 . . . . 22(2) ?
C39 C34 C35 C36 . . . . -3(3) ?
C33 C34 C35 C36 . . . . 177.0(13) ?
C34 C35 C36 C37 . . . . 6(2) ?
C35 C36 C37 C38 . . . . -6.6(17) ?
C36 C37 C38 C39 . . . . 3.6(14) ?
C37 C38 C39 C34 . . . . -0.6(16) ?
C35 C34 C39 C38 . . . . 0(2) ?
C33 C34 C39 C38 . . . . 180.0(12) ?
O3 C33 C34B C39B . . . . 4(6) ?
O4 C33 C34B C39B . . . . -179(3) ?
O3 C33 C34B C35B . . . . -175(5) ?
O4 C33 C34B C35B . . . . 2(7) ?
C39B C34B C35B C36B . . . . 4(8) ?
C33 C34B C35B C36B . . . . -177(4) ?
C34B C35B C36B C37B . . . . -14(6) ?
C35B C36B C37B C38B . . . . 19(5) ?
C36B C37B C38B C39B . . . . -15(4) ?
C37B C38B C39B C34B . . . . 5(5) ?
C35B C34B C39B C38B . . . . 1(8) ?
C33 C34B C39B C38B . . . . -178(3) ?

_cod_database_fobs_code 2022269
