#------------------------------------------------------------------------------
#$Date: 2023-09-20 04:48:29 +0300 (Wed, 20 Sep 2023) $
#$Revision: 286428 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022863.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_2022863
loop_
_publ_author_name
'Sakamoto, Nasa'
'Gato, Katsuhiko'
_publ_section_title
;
 Crystal structure of a 1:1 co-crystal of quabodepistat (OPC-167832) with
 2,5-dihydroxybenzoic acid using microcrystal electron diffraction
;
_journal_coeditor_code           DJ2052
_journal_issue                   10
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_paper_doi               10.1107/S2056989023006047
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C21 H20 Cl F3 N2 O4, C7 H6 O4'
_chemical_formula_moiety         'C21 H20 Cl F3 N2 O4, C7 H6 O4'
_chemical_formula_sum            'C28 H26 Cl F3 N2 O8'
_chemical_formula_weight         610.96
_chemical_name_common            quabodepistat-2,5-dihydroxybenzoicacid
_chemical_name_systematic
'5-{[(3R,4R)-1-(4-Chloro-2,6-difluorophenyl)-3,4-dihydroxypiperidin-4-yl]methoxy}-8-fluoro-3,4-dihydroquinolin-2(1H)-one--2,5-dihydroxybenzoic acid (1/1)'
_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   geom
_audit_creation_method
;
Olex2 1.5
(compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.30(9)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   5.6(3)
_cell_length_b                   9.6(3)
_cell_length_c                   28.2(3)
_cell_measurement_reflns_used    411
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      0.8340
_cell_measurement_theta_min      0.1030
_cell_volume                     1516(10)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2022)
;
_computing_molecular_graphics
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
Olex2 1.5 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
SHELXL2018/3 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXD  (Sheldrick, 2008)
;
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'HPC area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_measured_fraction_theta_full 0.931
_diffrn_measured_fraction_theta_max 0.931
_diffrn_measurement_device_type  'Rigaku XtaLAB Synergy-ED'
_diffrn_measurement_method       rotation
_diffrn_radiation_type           electron
_diffrn_radiation_wavelength     0.0251
_diffrn_reflns_av_R_equivalents  0.1491
_diffrn_reflns_av_unetI/netI     0.1595
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            8548
_diffrn_reflns_theta_full        0.799
_diffrn_reflns_theta_max         0.799
_diffrn_reflns_theta_min         0.107
_diffrn_source                   'thermionic-emission electron gun'
_exptl_absorpt_coefficient_mu    0.000
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_description       'thin platelets'
_exptl_crystal_F_000             224
_exptl_crystal_size_max          1
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.149
_refine_diff_density_min         -0.146
_refine_ls_abs_structure_details
;
 All f" are zero, so absolute structure could not be determined
;
_refine_ls_extinction_coef       37E1(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
'SHELXL2018/3 (Sheldrick, 2015)'
;
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     348
_refine_ls_number_reflns         4096
_refine_ls_number_restraints     537
_refine_ls_restrained_S_all      1.034
_refine_ls_R_factor_all          0.2455
_refine_ls_R_factor_gt           0.1602
_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)+(0.2805P)²+0.1700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4121
_refine_ls_wR_factor_ref         0.4803
_reflns_number_gt                2030
_reflns_number_total             4096
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            dj2052sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        152E1(11)
_cod_database_code               2022863
_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.
;
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
C C2 0.960(3) 0.5589(17) 0.7945(6) 0.070(5) Uani d 1 . .
C C11 0.804(4) 0.6700(17) 0.7886(5) 0.068(4) Uani d 1 . .
C C6 0.660(3) 0.7121(17) 0.8261(6) 0.063(4) Uani d 1 . .
C C5 0.673(3) 0.6431(19) 0.8694(6) 0.072(5) Uani d 1 . .
C C4 0.829(3) 0.5320(19) 0.8752(5) 0.075(5) Uani d 1 . .
H H4 0.837583 0.485853 0.904220 0.090 Uiso calc 1 . .
C C3 0.973(3) 0.4899(16) 0.8378(6) 0.073(5) Uani d 1 . .
H H3 1.077324 0.415597 0.841680 0.087 Uiso calc 1 . .
C C10 0.796(5) 0.753(2) 0.7416(8) 0.069(5) Uani d 1 . .
H H10A 0.957975 0.785032 0.735893 0.083 Uiso calc 1 . .
H H10B 0.759602 0.686397 0.716684 0.083 Uiso calc 1 . .
C C9 0.631(5) 0.878(3) 0.7338(10) 0.075(5) Uani d 1 . .
H H9A 0.528342 0.859999 0.706630 0.090 Uiso calc 1 . .
H H9B 0.726751 0.959210 0.726908 0.090 Uiso calc 1 . .
C C8 0.476(5) 0.906(3) 0.7778(9) 0.068(5) Uani d 1 . .
N N7 0.479(5) 0.824(2) 0.8206(10) 0.067(5) Uani d 1 . .
H H7 0.359249 0.842859 0.846624 0.080 Uiso calc 1 . .
C C32 0.785(2) 0.0552(14) 0.9171(6) 0.053(4) Uani d 1 . .
C C37 0.611(3) 0.1500(15) 0.9033(5) 0.054(4) Uani d 1 . .
H H37 0.608891 0.184541 0.872468 0.065 Uiso calc 1 . .
C C36 0.440(2) 0.1933(15) 0.9357(6) 0.057(5) Uani d 1 . .
C C35 0.443(2) 0.1417(17) 0.9818(6) 0.059(5) Uani d 1 . .
H H35 0.327933 0.170661 1.003412 0.071 Uiso calc 1 . .
C C34 0.617(3) 0.0469(18) 0.9955(5) 0.064(5) Uani d 1 . .
H H34 0.619200 0.012343 1.026363 0.076 Uiso calc 1 . .
C C33 0.789(2) 0.0036(15) 0.9632(6) 0.059(4) Uani d 1 . .
O O40 1.128(4) -0.085(2) 0.8909(11) 0.069(6) Uani d 1 . .
C C15 1.307(4) 0.340(2) 0.7081(11) 0.081(5) Uani d 1 . .
C C38 0.975(3) 0.005(2) 0.8818(8) 0.053(4) Uani d 1 . .
O O42 0.251(4) 0.291(2) 0.9211(10) 0.061(6) Uani d 1 . .
H H42 0.156468 0.302044 0.943037 0.092 Uiso calc 1 . .
C C14 1.241(6) 0.397(3) 0.7565(12) 0.082(5) Uani d 1 . .
H H14A 1.151605 0.326933 0.773690 0.099 Uiso calc 1 . .
H H14B 1.386475 0.415660 0.774296 0.099 Uiso calc 1 . .
O O12 0.319(5) 1.000(2) 0.7774(9) 0.075(7) Uani d 1 . .
O O41 0.958(4) -0.099(2) 0.9792(11) 0.076(7) Uani d 1 . .
H H41 1.043887 -0.121798 0.956939 0.114 Uiso calc 1 . .
F F13 0.511(6) 0.688(2) 0.9048(10) 0.079(7) Uani d 1 . .
O O1 1.104(4) 0.520(2) 0.7540(12) 0.077(5) Uani d 1 . .
O O39 0.968(4) 0.071(2) 0.8400(11) 0.066(5) Uani d 1 . .
H H39 1.072100 0.039139 0.822607 0.099 Uiso calc 1 . .
C C17 1.138(5) 0.243(2) 0.6290(10) 0.090(6) Uani d 1 . .
H H17A 1.232176 0.158593 0.628400 0.108 Uiso calc 1 . .
H H17B 0.988301 0.225125 0.612765 0.108 Uiso calc 1 . .
O O21 0.972(5) 0.185(3) 0.7110(12) 0.098(8) Uani d 1 . .
H H21 0.828359 0.200591 0.711408 0.148 Uiso calc 1 . .
C C20 1.438(5) 0.447(2) 0.6775(10) 0.089(6) Uani d 1 . .
H H20A 1.346328 0.532911 0.678027 0.106 Uiso calc 1 . .
H H20B 1.591213 0.466927 0.692442 0.106 Uiso calc 1 . .
O O22 1.469(3) 0.224(2) 0.7149(14) 0.083(7) Uani d 1 . .
H H22 1.401436 0.161832 0.729667 0.125 Uiso calc 1 . .
C C16 1.087(4) 0.283(2) 0.6810(9) 0.083(5) Uani d 1 . .
H H16 0.976517 0.361826 0.679004 0.100 Uiso calc 1 . .
C C23 1.265(6) 0.344(3) 0.5511(9) 0.131(7) Uani d 1 . .
C C28 1.434(5) 0.264(3) 0.5280(10) 0.150(8) Uani d 1 . .
C C27 1.440(5) 0.261(3) 0.4787(10) 0.164(9) Uani d 1 . .
H H27 1.553704 0.206657 0.463185 0.197 Uiso calc 1 . .
C C26 1.277(6) 0.339(4) 0.4525(9) 0.170(9) Uani d 1 . .
C C25 1.108(5) 0.419(3) 0.4756(10) 0.162(9) Uani d 1 . .
H H25 0.998639 0.471406 0.458099 0.194 Uiso calc 1 . .
C C24 1.102(5) 0.422(3) 0.5249(10) 0.148(8) Uani d 1 . .
Cl Cl31 1.268(6) 0.322(4) 0.3905(9) 0.215(12) Uani d 1 . .
F F29 0.929(10) 0.501(5) 0.548(2) 0.172(14) Uani d 1 . .
F F30 1.615(9) 0.176(5) 0.551(2) 0.158(13) Uani d 1 . .
C C19 1.485(4) 0.410(3) 0.6254(10) 0.092(6) Uani d 1 . .
H H19A 1.534890 0.492210 0.608241 0.111 Uiso calc 1 . .
H H19B 1.612402 0.341921 0.623696 0.111 Uiso calc 1 . .
N N18 1.268(5) 0.353(3) 0.6034(11) 0.101(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 0.0000 0.0000 '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'
Cl Cl 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0000 0.0000 '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
C11 C2 C3 . . 120.0 ?
C11 C2 O1 . . 117(2) ?
C3 C2 O1 . . 123(2) ?
C2 C11 C10 . . 120.8(16) ?
C6 C11 C2 . . 120.0 ?
C6 C11 C10 . . 119.2(19) ?
C11 C6 N7 . . 122(2) ?
C5 C6 C11 . . 120.0 ?
C5 C6 N7 . . 117.9(18) ?
C6 C5 C4 . . 120.0 ?
C6 C5 F13 . . 116(2) ?
C4 C5 F13 . . 124(2) ?
C5 C4 H4 . . 120.0 ?
C3 C4 C5 . . 120.0 ?
C3 C4 H4 . . 120.0 ?
C2 C3 H3 . . 120.0 ?
C4 C3 C2 . . 120.0 ?
C4 C3 H3 . . 120.0 ?
C11 C10 H10A . . 106.6 ?
C11 C10 H10B . . 106.6 ?
H10A C10 H10B . . 106.6 ?
C9 C10 C11 . . 123(2) ?
C9 C10 H10A . . 106.6 ?
C9 C10 H10B . . 106.6 ?
C10 C9 H9A . . 109.3 ?
C10 C9 H9B . . 109.3 ?
C10 C9 C8 . . 111(3) ?
H9A C9 H9B . . 108.0 ?
C8 C9 H9A . . 109.3 ?
C8 C9 H9B . . 109.3 ?
N7 C8 C9 . . 125(2) ?
O12 C8 C9 . . 121(3) ?
O12 C8 N7 . . 114(3) ?
C6 N7 H7 . . 120.4 ?
C8 N7 C6 . . 119(3) ?
C8 N7 H7 . . 120.4 ?
C37 C32 C33 . . 120.0 ?
C37 C32 C38 . . 121(2) ?
C33 C32 C38 . . 119.1(19) ?
C32 C37 H37 . . 120.0 ?
C36 C37 C32 . . 120.0 ?
C36 C37 H37 . . 120.0 ?
C37 C36 C35 . . 120.0 ?
C37 C36 O42 . . 120(3) ?
C35 C36 O42 . . 119.6(18) ?
C36 C35 H35 . . 120.0 ?
C34 C35 C36 . . 120.0 ?
C34 C35 H35 . . 120.0 ?
C35 C34 H34 . . 120.0 ?
C35 C34 C33 . . 120.0 ?
C33 C34 H34 . . 120.0 ?
C32 C33 O41 . . 122.8(19) ?
C34 C33 C32 . . 120.0 ?
C34 C33 O41 . . 117(3) ?
C14 C15 C20 . . 112(3) ?
C14 C15 C16 . . 112(3) ?
C20 C15 C16 . . 110(3) ?
O22 C15 C14 . . 109(3) ?
O22 C15 C20 . . 107(4) ?
O22 C15 C16 . . 107(4) ?
O40 C38 C32 . . 124(3) ?
O40 C38 O39 . . 122(2) ?
O39 C38 C32 . . 114(2) ?
C36 O42 H42 . . 109.5 ?
C15 C14 H14A . . 108.9 ?
C15 C14 H14B . . 108.9 ?
H14A C14 H14B . . 107.7 ?
O1 C14 C15 . . 113(3) ?
O1 C14 H14A . . 108.9 ?
O1 C14 H14B . . 108.9 ?
C33 O41 H41 . . 109.5 ?
C14 O1 C2 . . 119(3) ?
C38 O39 H39 . . 109.5 ?
H17A C17 H17B . . 107.9 ?
C16 C17 H17A . . 109.1 ?
C16 C17 H17B . . 109.1 ?
N18 C17 H17A . . 109.1 ?
N18 C17 H17B . . 109.1 ?
N18 C17 C16 . . 112(2) ?
C16 O21 H21 . . 109.5 ?
C15 C20 H20A . . 107.9 ?
C15 C20 H20B . . 107.9 ?
H20A C20 H20B . . 107.2 ?
C19 C20 C15 . . 117(2) ?
C19 C20 H20A . . 107.9 ?
C19 C20 H20B . . 107.9 ?
C15 O22 H22 . . 109.5 ?
C15 C16 H16 . . 105.0 ?
C17 C16 C15 . . 114(3) ?
C17 C16 H16 . . 105.0 ?
O21 C16 C15 . . 107(3) ?
O21 C16 C17 . . 119(3) ?
O21 C16 H16 . . 105.0 ?
C28 C23 C24 . . 120.0 ?
C28 C23 N18 . . 120(2) ?
C24 C23 N18 . . 120(2) ?
C23 C28 C27 . . 120.0 ?
C23 C28 F30 . . 126(3) ?
C27 C28 F30 . . 114(3) ?
C28 C27 H27 . . 120.0 ?
C26 C27 C28 . . 120.0 ?
C26 C27 H27 . . 120.0 ?
C27 C26 Cl31 . . 119.7(11) ?
C25 C26 C27 . . 120.0 ?
C25 C26 Cl31 . . 120.1(13) ?
C26 C25 H25 . . 120.0 ?
C26 C25 C24 . . 120.0 ?
C24 C25 H25 . . 120.0 ?
C23 C24 F29 . . 120(4) ?
C25 C24 C23 . . 120.0 ?
C25 C24 F29 . . 120(3) ?
C20 C19 H19A . . 109.6 ?
C20 C19 H19B . . 109.6 ?
H19A C19 H19B . . 108.1 ?
N18 C19 C20 . . 110(3) ?
N18 C19 H19A . . 109.6 ?
N18 C19 H19B . . 109.6 ?
C17 N18 C23 . . 116(3) ?
C19 N18 C17 . . 118(3) ?
C19 N18 C23 . . 117(3) ?
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
C2 C11 . 1.3900 ?
C2 C3 . 1.3900 ?
C2 O1 . 1.45(4) ?
C11 C6 . 1.3900 ?
C11 C10 . 1.55(2) ?
C6 C5 . 1.3900 ?
C6 N7 . 1.49(6) ?
C5 C4 . 1.3900 ?
C5 F13 . 1.42(5) ?
C4 H4 . 0.9300 ?
C4 C3 . 1.3900 ?
C3 H3 . 0.9300 ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C10 C9 . 1.53(5) ?
C9 H9A . 0.9700 ?
C9 H9B . 0.9700 ?
C9 C8 . 1.54(4) ?
C8 N7 . 1.44(4) ?
C8 O12 . 1.26(5) ?
N7 H7 . 1.0100 ?
C32 C37 . 1.3900 ?
C32 C33 . 1.3900 ?
C32 C38 . 1.53(5) ?
C37 H37 . 0.9300 ?
C37 C36 . 1.3900 ?
C36 C35 . 1.3900 ?
C36 O42 . 1.47(6) ?
C35 H35 . 0.9300 ?
C35 C34 . 1.3900 ?
C34 H34 . 0.9300 ?
C34 C33 . 1.3900 ?
C33 O41 . 1.44(5) ?
O40 C38 . 1.24(5) ?
C15 C14 . 1.52(4) ?
C15 C20 . 1.54(4) ?
C15 O22 . 1.45(5) ?
C15 C16 . 1.54(6) ?
C38 O39 . 1.34(4) ?
O42 H42 . 0.8200 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
C14 O1 . 1.41(5) ?
O41 H41 . 0.8200 ?
O39 H39 . 0.8200 ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C17 C16 . 1.54(2) ?
C17 N18 . 1.47(4) ?
O21 H21 . 0.8200 ?
O21 C16 . 1.42(3) ?
C20 H20A . 0.9700 ?
C20 H20B . 0.9700 ?
C20 C19 . 1.53(2) ?
O22 H22 . 0.8200 ?
C16 H16 . 0.9800 ?
C23 C28 . 1.3900 ?
C23 C24 . 1.3900 ?
C23 N18 . 1.47(4) ?
C28 C27 . 1.3900 ?
C28 F30 . 1.46(7) ?
C27 H27 . 0.9300 ?
C27 C26 . 1.3900 ?
C26 C25 . 1.3900 ?
C26 Cl31 . 1.75(3) ?
C25 H25 . 0.9300 ?
C25 C24 . 1.3900 ?
C24 F29 . 1.40(7) ?
C19 H19A . 0.9700 ?
C19 H19B . 0.9700 ?
C19 N18 . 1.46(6) ?
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
C3 H3 O42 1_655 0.93 2.71 3.40(7) 131.2 yes
C9 H9B O22 1_465 0.97 2.94 3.49(11) 116.9 yes
N7 H7 O40 1_465 1.01 1.93 2.93(9) 168.7 yes
C34 H34 O42 2_647 0.93 2.69 3.48(7) 143.0 yes
O42 H42 O41 2_657 0.82 2.48 3.23(6) 152.2 yes
O39 H39 O12 1_645 0.82 1.92 2.73(10) 169.2 yes
O21 H21 O22 1_455 0.82 2.02 2.84(18) 175.3 yes
O22 H22 O12 1_645 0.82 2.11 2.90(7) 164.1 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
C2 C11 C6 C5 . . . . 0.0 ?
C2 C11 C6 N7 . . . . -176(2) ?
C2 C11 C10 C9 . . . . -179(2) ?
C11 C2 C3 C4 . . . . 0.0 ?
C11 C2 O1 C14 . . . . -172(2) ?
C11 C6 C5 C4 . . . . 0.0 ?
C11 C6 C5 F13 . . . . -177(2) ?
C11 C6 N7 C8 . . . . -10(3) ?
C11 C10 C9 C8 . . . . -1(4) ?
C6 C11 C10 C9 . . . . -2(4) ?
C6 C5 C4 C3 . . . . 0.0 ?
C5 C6 N7 C8 . . . . 174(2) ?
C5 C4 C3 C2 . . . . 0.0 ?
C3 C2 C11 C6 . . . . 0.0 ?
C3 C2 C11 C10 . . . . 177(2) ?
C3 C2 O1 C14 . . . . 8(3) ?
C10 C11 C6 C5 . . . . -177(2) ?
C10 C11 C6 N7 . . . . 7(2) ?
C10 C9 C8 N7 . . . . -2(4) ?
C10 C9 C8 O12 . . . . -176(3) ?
C9 C8 N7 C6 . . . . 7(5) ?
N7 C6 C5 C4 . . . . 176(2) ?
N7 C6 C5 F13 . . . . -1(2) ?
C32 C37 C36 C35 . . . . 0.0 ?
C32 C37 C36 O42 . . . . -178.6(16) ?
C37 C32 C33 C34 . . . . 0.0 ?
C37 C32 C33 O41 . . . . 177.5(17) ?
C37 C32 C38 O40 . . . . -175.6(19) ?
C37 C32 C38 O39 . . . . 6(2) ?
C37 C36 C35 C34 . . . . 0.0 ?
C36 C35 C34 C33 . . . . 0.0 ?
C35 C34 C33 C32 . . . . 0.0 ?
C35 C34 C33 O41 . . . . -177.7(17) ?
C33 C32 C37 C36 . . . . 0.0 ?
C33 C32 C38 O40 . . . . 4(3) ?
C33 C32 C38 O39 . . . . -174.3(16) ?
C15 C14 O1 C2 . . . . 159(2) ?
C15 C20 C19 N18 . . . . 47(3) ?
C38 C32 C37 C36 . . . . 179.5(14) ?
C38 C32 C33 C34 . . . . -179.5(14) ?
C38 C32 C33 O41 . . . . -2(2) ?
O42 C36 C35 C34 . . . . 178.6(16) ?
C14 C15 C20 C19 . . . . -172(2) ?
C14 C15 C16 C17 . . . . 172(2) ?
C14 C15 C16 O21 . . . . -54(3) ?
O12 C8 N7 C6 . . . . -178(2) ?
F13 C5 C4 C3 . . . . 176(2) ?
O1 C2 C11 C6 . . . . 179.7(19) ?
O1 C2 C11 C10 . . . . -3(2) ?
O1 C2 C3 C4 . . . . -180(2) ?
C20 C15 C14 O1 . . . . 56(4) ?
C20 C15 C16 C17 . . . . 46(3) ?
C20 C15 C16 O21 . . . . -180(2) ?
C20 C19 N18 C17 . . . . -48(3) ?
C20 C19 N18 C23 . . . . 165(2) ?
O22 C15 C14 O1 . . . . 174(2) ?
O22 C15 C20 C19 . . . . 69(3) ?
O22 C15 C16 C17 . . . . -70(3) ?
O22 C15 C16 O21 . . . . 65(3) ?
C16 C15 C14 O1 . . . . -69(4) ?
C16 C15 C20 C19 . . . . -46(3) ?
C16 C17 N18 C23 . . . . -163(3) ?
C16 C17 N18 C19 . . . . 51(4) ?
C23 C28 C27 C26 . . . . 0.0 ?
C28 C23 C24 C25 . . . . 0.0 ?
C28 C23 C24 F29 . . . . 178.7(11) ?
C28 C23 N18 C17 . . . . -86(5) ?
C28 C23 N18 C19 . . . . 61(5) ?
C28 C27 C26 C25 . . . . 0.0 ?
C28 C27 C26 Cl31 . . . . -174(3) ?
C27 C26 C25 C24 . . . . 0.0 ?
C26 C25 C24 C23 . . . . 0.0 ?
C26 C25 C24 F29 . . . . -178.7(11) ?
C24 C23 C28 C27 . . . . 0.0 ?
C24 C23 C28 F30 . . . . -179(3) ?
C24 C23 N18 C17 . . . . 97(5) ?
C24 C23 N18 C19 . . . . -116(4) ?
Cl31 C26 C25 C24 . . . . 174(3) ?
F30 C28 C27 C26 . . . . 179(3) ?
N18 C17 C16 C15 . . . . -49(3) ?
N18 C17 C16 O21 . . . . -177(2) ?
N18 C23 C28 C27 . . . . -177(3) ?
N18 C23 C28 F30 . . . . 4(3) ?
N18 C23 C24 C25 . . . . 177(3) ?
N18 C23 C24 F29 . . . . -5(3) ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.747(10)
2 0.253(10)
