#------------------------------------------------------------------------------
#$Date: 2023-10-06 03:04:55 +0300 (Fri, 06 Oct 2023) $
#$Revision: 286734 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/72/7247204.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7247204
loop_
_publ_author_name
'Meng, Lingshan'
'Li, Duanxiu'
'Zhu, Yujing'
'Wang, Jianming'
'Deng, Zongwu'
'Zhang, Hailu'
_publ_section_title
;
 Pirfenidone--flavonoid cocrystals with reduced solubility and dissolution
 rate
;
_journal_issue                   36
_journal_name_full               CrystEngComm
_journal_page_first              5133
_journal_page_last               5140
_journal_paper_doi               10.1039/D3CE00402C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C15 H10 O5, 2(C12 H11 N O)'
_chemical_formula_sum            'C39 H32 N2 O7'
_chemical_formula_weight         640.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_block_doi                 10.5517/ccdc.csd.cc2dfmn4
_audit_creation_date             2023-02-25
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-03-09 deposited with the CCDC.	2023-08-15 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 98.594(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.9053(6)
_cell_length_b                   8.2831(2)
_cell_length_c                   20.9395(5)
_cell_measurement_reflns_used    9855
_cell_measurement_temperature    273(2)
_cell_measurement_theta_max      72.098
_cell_measurement_theta_min      4.271
_cell_volume                     3242.19(15)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'XS  (Sheldrick, 2008)'
_diffrn_ambient_temperature      273(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.0652
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            21466
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.806
_diffrn_reflns_theta_min         4.271
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.3766
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1575 before and 0.0909 after correction.
The Ratio of minimum to maximum transmission is 0.4997.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.313
_exptl_crystal_description       block
_exptl_crystal_F_000             1344
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.187
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.2(3)
_refine_ls_extinction_coef       0.0031(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.127
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     443
_refine_ls_number_reflns         6267
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.126
_refine_ls_R_factor_all          0.0604
_refine_ls_R_factor_gt           0.0566
_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)+(0.1275P)²+0.0028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1742
_refine_ls_wR_factor_ref         0.1822
_reflns_Friedel_coverage         0.943
_reflns_Friedel_fraction_full    0.968
_reflns_Friedel_fraction_max     0.940
_reflns_number_gt                5684
_reflns_number_total             6267
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00402c2.cif
_cod_data_source_block           t
_cod_depositor_comments
'Adding full bibliography for 7247203--7247204.cif.'
_cod_database_code               7247204
_shelx_shelxl_version_number     2018/3
_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_max   0.930
_shelx_estimated_absorpt_t_min   0.866
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.8(3)
 0.2(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3.a Riding coordinates:
 O5(H5)
3.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C23(H23), C24(H24), C26(H26), C17(H17), C27(H27), C19(H19),
 C5A(H5A), C3A(H3A), C2A(H2A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 C12A(H12A), C5B(H5B), C3B(H3B), C2B(H2B), C12B(H12B), C11B(H11B), C10B(H10B),
 C9B(H9B), C8B(H8B)
3.c Idealised Me refined as rotating group:
 C6A(H6AA,H6AB,H6AC), C6B(H6BA,H6BB,H6BC)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O2 O 0.25670(16) 1.4190(3) 0.33899(14) 0.0603(7) Uani 1 1 d . . . . .
O3 O 0.20912(17) 0.9665(3) 0.39716(14) 0.0635(7) Uani 1 1 d . . . . .
O4 O 0.15377(19) 1.0948(4) 0.49174(16) 0.0688(8) Uani 1 1 d . . . . .
H4 H 0.171(4) 1.026(10) 0.458(3) 0.103 Uiso 1 1 d . U . . .
O5 O 0.14578(19) 1.6690(4) 0.49716(18) 0.0742(8) Uani 1 1 d . . . . .
H5 H 0.133899 1.650772 0.532564 0.111 Uiso 1 1 d R U . . .
O6 O 0.25959(19) 0.6350(4) 0.13622(15) 0.0700(8) Uani 1 1 d . . . . .
H6 H 0.284(4) 0.538(11) 0.154(3) 0.105 Uiso 1 1 d . U . . .
C22 C 0.25781(19) 1.0025(4) 0.27180(17) 0.0517(7) Uani 1 1 d . . . . .
C13 C 0.2679(2) 1.2856(5) 0.3045(2) 0.0578(8) Uani 1 1 d . . . . .
H13 H 0.289296 1.300717 0.267694 0.069 Uiso 1 1 calc R U . . .
C23 C 0.2312(2) 1.0256(5) 0.20615(19) 0.0587(9) Uani 1 1 d . . . . .
H23 H 0.211706 1.125053 0.192374 0.070 Uiso 1 1 calc R U . . .
C14 C 0.2509(2) 1.1331(5) 0.31842(18) 0.0518(8) Uani 1 1 d . . . . .
C24 C 0.2334(2) 0.9030(5) 0.16164(19) 0.0629(9) Uani 1 1 d . . . . .
H24 H 0.216236 0.921265 0.118270 0.076 Uiso 1 1 calc R U . . .
C15 C 0.22162(19) 1.1035(4) 0.37799(17) 0.0498(8) Uani 1 1 d . . . . .
C25 C 0.2610(2) 0.7534(5) 0.18126(19) 0.0546(8) Uani 1 1 d . . . . .
C16 C 0.1699(2) 1.2391(5) 0.46743(18) 0.0530(8) Uani 1 1 d . . . . .
C26 C 0.2896(2) 0.7291(5) 0.24607(19) 0.0561(8) Uani 1 1 d . . . . .
H26 H 0.310296 0.630639 0.259427 0.067 Uiso 1 1 calc R U . . .
C17 C 0.1503(2) 1.3786(6) 0.4963(2) 0.0605(9) Uani 1 1 d . . . . .
H17 H 0.126744 1.372294 0.532204 0.073 Uiso 1 1 calc R U . . .
C27 C 0.2868(2) 0.8530(5) 0.29049(18) 0.0548(8) Uani 1 1 d . . . . .
H27 H 0.304828 0.835170 0.333711 0.066 Uiso 1 1 calc R U . . .
C18 C 0.16576(19) 1.5299(5) 0.47156(19) 0.0572(8) Uani 1 1 d . . . . .
C19 C 0.2026(2) 1.5425(5) 0.41928(19) 0.0567(8) Uani 1 1 d . . . . .
H19 H 0.214334 1.642548 0.403686 0.068 Uiso 1 1 calc R U . . .
C20 C 0.22104(18) 1.4015(4) 0.39136(18) 0.0509(8) Uani 1 1 d . . . . .
C21 C 0.20550(19) 1.2468(5) 0.41279(18) 0.0490(7) Uani 1 1 d . . . . .
O1A O 0.34030(17) 0.3807(4) 0.17950(15) 0.0654(7) Uani 1 1 d . . . . .
N1A N 0.42249(17) 0.2160(4) 0.14301(15) 0.0535(7) Uani 1 1 d . . . . .
C5A C 0.4467(3) 0.1335(5) 0.0934(2) 0.0624(9) Uani 1 1 d . . . . .
H5A H 0.492595 0.089967 0.100085 0.075 Uiso 1 1 calc R U . . .
C4A C 0.4058(3) 0.1139(5) 0.0351(2) 0.0724(12) Uani 1 1 d . . . . .
C3A C 0.3356(3) 0.1763(7) 0.0282(2) 0.0794(13) Uani 1 1 d . . . . .
H3A H 0.304839 0.158073 -0.010130 0.095 Uiso 1 1 calc R U . . .
C2A C 0.3118(3) 0.2624(7) 0.0760(2) 0.0725(11) Uani 1 1 d . . . . .
H2A H 0.265368 0.302658 0.069779 0.087 Uiso 1 1 calc R U . . .
C1A C 0.3571(2) 0.2916(5) 0.13545(19) 0.0554(8) Uani 1 1 d . . . . .
C6A C 0.4348(5) 0.0285(8) -0.0189(3) 0.101(2) Uani 1 1 d . . . . .
H6AA H 0.447681 0.106625 -0.048970 0.151 Uiso 1 1 calc R U . . .
H6AB H 0.398903 -0.042619 -0.040598 0.151 Uiso 1 1 calc R U . . .
H6AC H 0.476254 -0.033009 -0.001486 0.151 Uiso 1 1 calc R U . . .
C7A C 0.4685(2) 0.2275(5) 0.20453(19) 0.0542(8) Uani 1 1 d . . . . .
C8A C 0.5357(2) 0.2945(6) 0.2091(3) 0.0684(10) Uani 1 1 d . . . . .
H8A H 0.552702 0.330448 0.172171 0.082 Uiso 1 1 calc R U . . .
C9A C 0.5777(3) 0.3081(7) 0.2688(3) 0.0843(15) Uani 1 1 d . . . . .
H9A H 0.623372 0.351964 0.272014 0.101 Uiso 1 1 calc R U . . .
C10A C 0.5523(3) 0.2572(7) 0.3232(3) 0.0873(16) Uani 1 1 d . . . . .
H10A H 0.580270 0.270008 0.363391 0.105 Uiso 1 1 calc R U . . .
C11A C 0.4856(3) 0.1872(8) 0.3192(3) 0.0824(14) Uani 1 1 d . . . . .
H11A H 0.469155 0.150731 0.356324 0.099 Uiso 1 1 calc R U . . .
C12A C 0.4431(2) 0.1713(6) 0.2595(2) 0.0642(10) Uani 1 1 d . . . . .
H12A H 0.398186 0.123553 0.256197 0.077 Uiso 1 1 calc R U . . .
O1B O 0.0912(2) 0.3840(5) 0.10356(18) 0.0822(10) Uani 1 1 d . . . . .
N1B N 0.01651(17) 0.2287(4) 0.15477(15) 0.0528(7) Uani 1 1 d . . . . .
C5B C -0.0090(2) 0.1824(5) 0.2101(2) 0.0591(8) Uani 1 1 d . . . . .
H5B H -0.046283 0.108300 0.207177 0.071 Uiso 1 1 calc R U . . .
C4B C 0.0189(3) 0.2422(6) 0.2691(2) 0.0684(11) Uani 1 1 d . . . . .
C3B C 0.0755(3) 0.3522(7) 0.2708(3) 0.0768(13) Uani 1 1 d . . . . .
H3B H 0.095797 0.394559 0.310470 0.092 Uiso 1 1 calc R U . . .
C2B C 0.1015(2) 0.3989(6) 0.2172(2) 0.0696(11) Uani 1 1 d . . . . .
H2B H 0.139326 0.471797 0.220751 0.084 Uiso 1 1 calc R U . . .
C1B C 0.0722(2) 0.3383(5) 0.1553(2) 0.0597(9) Uani 1 1 d . . . . .
C6B C -0.0094(4) 0.1874(11) 0.3293(3) 0.104(2) Uani 1 1 d . . . . .
H6BA H -0.033338 0.275788 0.346722 0.155 Uiso 1 1 calc R U . . .
H6BB H 0.029606 0.151511 0.360768 0.155 Uiso 1 1 calc R U . . .
H6BC H -0.042571 0.100227 0.318753 0.155 Uiso 1 1 calc R U . . .
C7B C -0.0192(2) 0.1660(5) 0.09413(18) 0.0544(8) Uani 1 1 d . . . . .
C12B C 0.0194(3) 0.0812(6) 0.0536(2) 0.0670(10) Uani 1 1 d . . . . .
H12B H 0.068405 0.065400 0.064765 0.080 Uiso 1 1 calc R U . . .
C11B C -0.0166(3) 0.0209(8) -0.0039(2) 0.0844(14) Uani 1 1 d . . . . .
H11B H 0.008231 -0.036375 -0.031603 0.101 Uiso 1 1 calc R U . . .
C10B C -0.0886(3) 0.0450(9) -0.0200(3) 0.0882(16) Uani 1 1 d . . . . .
H10B H -0.112057 0.006083 -0.059189 0.106 Uiso 1 1 calc R U . . .
C9B C -0.1265(3) 0.1258(8) 0.0207(3) 0.0814(14) Uani 1 1 d . . . . .
H9B H -0.175690 0.138249 0.009918 0.098 Uiso 1 1 calc R U . . .
C8B C -0.0914(2) 0.1889(6) 0.0779(2) 0.0661(10) Uani 1 1 d . . . . .
H8B H -0.116699 0.246524 0.105209 0.079 Uiso 1 1 calc R U . . .
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C13 O2 C20 118.2(3) . . ?
C16 O4 H4 97(4) . . ?
C18 O5 H5 109.5 . . ?
C25 O6 H6 112(4) . . ?
C23 C22 C14 119.6(3) . . ?
C27 C22 C23 117.8(3) . . ?
C27 C22 C14 122.6(3) . . ?
O2 C13 H13 117.0 . . ?
C14 C13 O2 126.0(4) . . ?
C14 C13 H13 117.0 . . ?
C22 C23 H23 119.4 . . ?
C24 C23 C22 121.1(3) . . ?
C24 C23 H23 119.4 . . ?
C13 C14 C22 119.8(3) . . ?
C13 C14 C15 118.5(3) . . ?
C15 C14 C22 121.7(3) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
O3 C15 C14 123.1(3) . . ?
O3 C15 C21 121.5(3) . . ?
C21 C15 C14 115.3(3) . . ?
O6 C25 C24 118.3(4) . . ?
O6 C25 C26 122.3(3) . . ?
C24 C25 C26 119.4(3) . . ?
O4 C16 C17 119.0(4) . . ?
O4 C16 C21 120.4(3) . . ?
C17 C16 C21 120.6(4) . . ?
C25 C26 H26 120.2 . . ?
C27 C26 C25 119.7(3) . . ?
C27 C26 H26 120.2 . . ?
C16 C17 H17 120.0 . . ?
C16 C17 C18 120.0(4) . . ?
C18 C17 H17 120.0 . . ?
C22 C27 C26 121.5(3) . . ?
C22 C27 H27 119.2 . . ?
C26 C27 H27 119.2 . . ?
O5 C18 C17 122.0(4) . . ?
O5 C18 C19 117.0(4) . . ?
C19 C18 C17 121.0(4) . . ?
C18 C19 H19 121.2 . . ?
C20 C19 C18 117.5(4) . . ?
C20 C19 H19 121.2 . . ?
O2 C20 C21 120.1(3) . . ?
C19 C20 O2 115.8(3) . . ?
C19 C20 C21 124.1(3) . . ?
C16 C21 C15 122.1(3) . . ?
C20 C21 C15 121.2(3) . . ?
C20 C21 C16 116.6(3) . . ?
C5A N1A C7A 118.7(3) . . ?
C1A N1A C5A 122.3(3) . . ?
C1A N1A C7A 119.0(3) . . ?
N1A C5A H5A 119.0 . . ?
C4A C5A N1A 121.9(4) . . ?
C4A C5A H5A 119.0 . . ?
C5A C4A C3A 116.9(4) . . ?
C5A C4A C6A 120.6(5) . . ?
C3A C4A C6A 122.5(5) . . ?
C4A C3A H3A 119.1 . . ?
C2A C3A C4A 121.7(4) . . ?
C2A C3A H3A 119.1 . . ?
C3A C2A H2A 119.6 . . ?
C3A C2A C1A 120.8(5) . . ?
C1A C2A H2A 119.6 . . ?
O1A C1A N1A 120.3(3) . . ?
O1A C1A C2A 123.8(4) . . ?
N1A C1A C2A 115.9(4) . . ?
C4A C6A H6AA 109.5 . . ?
C4A C6A H6AB 109.5 . . ?
C4A C6A H6AC 109.5 . . ?
H6AA C6A H6AB 109.5 . . ?
H6AA C6A H6AC 109.5 . . ?
H6AB C6A H6AC 109.5 . . ?
C8A C7A N1A 121.0(4) . . ?
C8A C7A C12A 120.4(4) . . ?
C12A C7A N1A 118.6(4) . . ?
C7A C8A H8A 120.1 . . ?
C7A C8A C9A 119.7(5) . . ?
C9A C8A H8A 120.1 . . ?
C8A C9A H9A 119.9 . . ?
C10A C9A C8A 120.2(5) . . ?
C10A C9A H9A 119.9 . . ?
C9A C10A H10A 119.7 . . ?
C9A C10A C11A 120.7(5) . . ?
C11A C10A H10A 119.7 . . ?
C10A C11A H11A 120.1 . . ?
C10A C11A C12A 119.8(5) . . ?
C12A C11A H11A 120.1 . . ?
C7A C12A H12A 120.4 . . ?
C11A C12A C7A 119.2(5) . . ?
C11A C12A H12A 120.4 . . ?
C5B N1B C1B 122.4(3) . . ?
C5B N1B C7B 117.7(3) . . ?
C1B N1B C7B 119.8(3) . . ?
N1B C5B H5B 119.1 . . ?
C4B C5B N1B 121.8(4) . . ?
C4B C5B H5B 119.1 . . ?
C5B C4B C3B 116.8(4) . . ?
C5B C4B C6B 120.7(5) . . ?
C3B C4B C6B 122.5(5) . . ?
C4B C3B H3B 118.8 . . ?
C2B C3B C4B 122.5(4) . . ?
C2B C3B H3B 118.8 . . ?
C3B C2B H2B 119.5 . . ?
C3B C2B C1B 121.1(4) . . ?
C1B C2B H2B 119.5 . . ?
O1B C1B N1B 120.5(4) . . ?
O1B C1B C2B 124.0(4) . . ?
N1B C1B C2B 115.4(4) . . ?
C4B C6B H6BA 109.5 . . ?
C4B C6B H6BB 109.5 . . ?
C4B C6B H6BC 109.5 . . ?
H6BA C6B H6BB 109.5 . . ?
H6BA C6B H6BC 109.5 . . ?
H6BB C6B H6BC 109.5 . . ?
C12B C7B N1B 120.1(3) . . ?
C8B C7B N1B 119.1(4) . . ?
C8B C7B C12B 120.9(4) . . ?
C7B C12B H12B 120.7 . . ?
C11B C12B C7B 118.6(4) . . ?
C11B C12B H12B 120.7 . . ?
C12B C11B H11B 119.8 . . ?
C10B C11B C12B 120.3(5) . . ?
C10B C11B H11B 119.8 . . ?
C11B C10B H10B 119.6 . . ?
C11B C10B C9B 120.8(5) . . ?
C9B C10B H10B 119.6 . . ?
C10B C9B H9B 120.1 . . ?
C10B C9B C8B 119.8(5) . . ?
C8B C9B H9B 120.1 . . ?
C7B C8B C9B 119.6(5) . . ?
C7B C8B H8B 120.2 . . ?
C9B C8B H8B 120.2 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C13 1.355(5) . ?
O2 C20 1.378(5) . ?
O3 C15 1.238(5) . ?
O4 H4 1.00(8) . ?
O4 C16 1.352(5) . ?
O5 H5 0.8200 . ?
O5 C18 1.348(5) . ?
O6 H6 0.98(8) . ?
O6 C25 1.358(5) . ?
C22 C23 1.405(5) . ?
C22 C14 1.476(5) . ?
C22 C27 1.387(5) . ?
C13 H13 0.9300 . ?
C13 C14 1.346(6) . ?
C23 H23 0.9300 . ?
C23 C24 1.384(6) . ?
C14 C15 1.459(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.383(6) . ?
C15 C21 1.449(5) . ?
C25 C26 1.398(5) . ?
C16 C17 1.380(6) . ?
C16 C21 1.413(5) . ?
C26 H26 0.9300 . ?
C26 C27 1.391(6) . ?
C17 H17 0.9300 . ?
C17 C18 1.404(6) . ?
C27 H27 0.9300 . ?
C18 C19 1.386(6) . ?
C19 H19 0.9300 . ?
C19 C20 1.374(5) . ?
C20 C21 1.403(5) . ?
O1A C1A 1.259(5) . ?
N1A C5A 1.379(5) . ?
N1A C1A 1.373(5) . ?
N1A C7A 1.446(5) . ?
C5A H5A 0.9300 . ?
C5A C4A 1.353(7) . ?
C4A C3A 1.410(8) . ?
C4A C6A 1.505(7) . ?
C3A H3A 0.9300 . ?
C3A C2A 1.360(8) . ?
C2A H2A 0.9300 . ?
C2A C1A 1.422(6) . ?
C6A H6AA 0.9600 . ?
C6A H6AB 0.9600 . ?
C6A H6AC 0.9600 . ?
C7A C8A 1.375(6) . ?
C7A C12A 1.391(6) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.383(8) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.367(9) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.379(9) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.388(7) . ?
C12A H12A 0.9300 . ?
O1B C1B 1.250(6) . ?
N1B C5B 1.374(5) . ?
N1B C1B 1.389(5) . ?
N1B C7B 1.442(5) . ?
C5B H5B 0.9300 . ?
C5B C4B 1.361(6) . ?
C4B C3B 1.401(8) . ?
C4B C6B 1.512(8) . ?
C3B H3B 0.9300 . ?
C3B C2B 1.349(8) . ?
C2B H2B 0.9300 . ?
C2B C1B 1.423(6) . ?
C6B H6BA 0.9600 . ?
C6B H6BB 0.9600 . ?
C6B H6BC 0.9600 . ?
C7B C12B 1.390(6) . ?
C7B C8B 1.371(6) . ?
C12B H12B 0.9300 . ?
C12B C11B 1.384(7) . ?
C11B H11B 0.9300 . ?
C11B C10B 1.366(9) . ?
C10B H10B 0.9300 . ?
C10B C9B 1.368(9) . ?
C9B H9B 0.9300 . ?
C9B C8B 1.382(7) . ?
C8B H8B 0.9300 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O4 H4 O3 1.00(8) 1.63(8) 2.601(4) 162(7) . yes
O5 H5 O1B 0.82 1.82 2.628(5) 169.6 2_575 yes
O6 H6 O1A 0.98(8) 1.71(8) 2.678(4) 170(7) . yes
C13 H13 O1A 0.93 2.30 3.227(5) 171.0 1_565 yes
C17 H17 O1B 0.93 2.66 3.302(5) 127.1 2_575 yes
C5A H5A O1B 0.93 2.52 3.406(6) 159.3 3_545 yes
C2A H2A O5 0.93 2.54 3.369(6) 148.7 2_574 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O2 C13 C14 C22 172.1(4) . . . . ?
O2 C13 C14 C15 -4.0(6) . . . . ?
O2 C20 C21 C15 -4.6(5) . . . . ?
O2 C20 C21 C16 179.0(3) . . . . ?
O3 C15 C21 C16 -4.9(5) . . . . ?
O3 C15 C21 C20 178.8(3) . . . . ?
O4 C16 C17 C18 -179.4(3) . . . . ?
O4 C16 C21 C15 4.4(5) . . . . ?
O4 C16 C21 C20 -179.1(3) . . . . ?
O5 C18 C19 C20 -177.8(3) . . . . ?
O6 C25 C26 C27 -177.3(4) . . . . ?
C22 C23 C24 C25 1.1(7) . . . . ?
C22 C14 C15 O3 9.2(5) . . . . ?
C22 C14 C15 C21 -168.8(3) . . . . ?
C13 O2 C20 C19 -171.5(3) . . . . ?
C13 O2 C20 C21 8.2(5) . . . . ?
C13 C14 C15 O3 -174.8(4) . . . . ?
C13 C14 C15 C21 7.3(5) . . . . ?
C23 C22 C14 C13 -46.2(5) . . . . ?
C23 C22 C14 C15 129.8(4) . . . . ?
C23 C22 C27 C26 -0.1(6) . . . . ?
C23 C24 C25 O6 177.5(4) . . . . ?
C23 C24 C25 C26 -2.8(7) . . . . ?
C14 C22 C23 C24 -176.6(4) . . . . ?
C14 C22 C27 C26 176.8(4) . . . . ?
C14 C15 C21 C16 173.1(3) . . . . ?
C14 C15 C21 C20 -3.2(5) . . . . ?
C24 C25 C26 C27 3.0(6) . . . . ?
C25 C26 C27 C22 -1.6(6) . . . . ?
C16 C17 C18 O5 178.1(4) . . . . ?
C16 C17 C18 C19 -1.9(6) . . . . ?
C17 C16 C21 C15 -174.8(3) . . . . ?
C17 C16 C21 C20 1.7(5) . . . . ?
C17 C18 C19 C20 2.2(5) . . . . ?
C27 C22 C23 C24 0.4(6) . . . . ?
C27 C22 C14 C13 137.0(4) . . . . ?
C27 C22 C14 C15 -47.0(5) . . . . ?
C18 C19 C20 O2 179.1(3) . . . . ?
C18 C19 C20 C21 -0.6(5) . . . . ?
C19 C20 C21 C15 175.1(3) . . . . ?
C19 C20 C21 C16 -1.4(5) . . . . ?
C20 O2 C13 C14 -4.0(6) . . . . ?
C21 C16 C17 C18 -0.2(6) . . . . ?
N1A C5A C4A C3A -2.5(7) . . . . ?
N1A C5A C4A C6A 177.7(5) . . . . ?
N1A C7A C8A C9A 178.1(4) . . . . ?
N1A C7A C12A C11A -177.5(4) . . . . ?
C5A N1A C1A O1A -171.9(4) . . . . ?
C5A N1A C1A C2A 7.8(6) . . . . ?
C5A N1A C7A C8A 57.6(5) . . . . ?
C5A N1A C7A C12A -123.2(4) . . . . ?
C5A C4A C3A C2A 4.7(8) . . . . ?
C4A C3A C2A C1A -0.5(8) . . . . ?
C3A C2A C1A O1A 174.2(5) . . . . ?
C3A C2A C1A N1A -5.6(7) . . . . ?
C1A N1A C5A C4A -3.9(6) . . . . ?
C1A N1A C7A C8A -120.5(4) . . . . ?
C1A N1A C7A C12A 58.7(5) . . . . ?
C6A C4A C3A C2A -175.6(5) . . . . ?
C7A N1A C5A C4A 178.0(4) . . . . ?
C7A N1A C1A O1A 6.1(5) . . . . ?
C7A N1A C1A C2A -174.1(4) . . . . ?
C7A C8A C9A C10A -0.9(8) . . . . ?
C8A C7A C12A C11A 1.6(7) . . . . ?
C8A C9A C10A C11A 2.1(9) . . . . ?
C9A C10A C11A C12A -1.4(9) . . . . ?
C10A C11A C12A C7A -0.4(8) . . . . ?
C12A C7A C8A C9A -1.0(7) . . . . ?
N1B C5B C4B C3B -0.6(6) . . . . ?
N1B C5B C4B C6B -179.1(5) . . . . ?
N1B C7B C12B C11B 179.2(5) . . . . ?
N1B C7B C8B C9B -178.3(4) . . . . ?
C5B N1B C1B O1B -176.1(4) . . . . ?
C5B N1B C1B C2B 0.5(6) . . . . ?
C5B N1B C7B C12B -123.6(4) . . . . ?
C5B N1B C7B C8B 55.3(5) . . . . ?
C5B C4B C3B C2B 0.4(7) . . . . ?
C4B C3B C2B C1B 0.3(7) . . . . ?
C3B C2B C1B O1B 175.7(4) . . . . ?
C3B C2B C1B N1B -0.7(6) . . . . ?
C1B N1B C5B C4B 0.2(6) . . . . ?
C1B N1B C7B C12B 59.7(5) . . . . ?
C1B N1B C7B C8B -121.5(4) . . . . ?
C6B C4B C3B C2B 178.8(5) . . . . ?
C7B N1B C5B C4B -176.5(4) . . . . ?
C7B N1B C1B O1B 0.6(6) . . . . ?
C7B N1B C1B C2B 177.1(3) . . . . ?
C7B C12B C11B C10B 0.2(9) . . . . ?
C12B C7B C8B C9B 0.5(7) . . . . ?
C12B C11B C10B C9B -1.5(10) . . . . ?
C11B C10B C9B C8B 2.3(10) . . . . ?
C10B C9B C8B C7B -1.8(8) . . . . ?
C8B C7B C12B C11B 0.3(7) . . . . ?
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.8(3)
2 0.2(3)
