#------------------------------------------------------------------------------
#$Date: 2023-11-16 04:55:55 +0200 (Thu, 16 Nov 2023) $
#$Revision: 287638 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/31/23/2312353.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_2312353
loop_
_publ_author_name
'Zhang, Yanli'
'Liu, Hui'
'Chen, Zongxin'
'Meng, Jialei'
'Li, Yunfeng'
'Qi, Luyao'
'Zhang, Suiliang'
'Chen, Xiaofeng'
'Lei, Ming'
_publ_section_title
;
 A drug-drug cocrystal and a co-amorphous form, prepared from honokiol and
 ligustrazine, inspired by Chinese patent medicine.
;
_journal_coeditor_code           TQ5012SUP1
_journal_issue                   6
_journal_name_full
'Acta crystallographica Section B, Structural science, crystal engineering and materials'
_journal_paper_doi               10.1107/S2052520623008648
_journal_volume                  79
_journal_year                    2023
_chemical_formula_moiety         'C18 H18 O2, 2(C4 H6 N)'
_chemical_formula_sum            'C26 H30 N2 O2'
_chemical_formula_weight         402.52
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2022-12-01
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90.211(2)
_cell_angle_beta                 102.112(2)
_cell_angle_gamma                93.805(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0045(5)
_cell_length_b                   9.2035(6)
_cell_length_c                   15.8210(10)
_cell_measurement_reflns_used    1966
_cell_measurement_temperature    170
_cell_measurement_theta_max      25.468
_cell_measurement_theta_min      2.599
_cell_volume                     1136.88(13)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      170
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_av_unetI/netI     0.1019
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            13033
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.400
_diffrn_reflns_theta_min         2.218
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6779
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0910 before and 0.0614 after correction. The Ratio of minimum to maximum transmission is 0.9094. The λ/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_description       block
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     277
_refine_ls_number_reflns         4620
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1490
_refine_ls_R_factor_gt           0.0692
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0507P)²+0.6051P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1332
_refine_ls_wR_factor_ref         0.1748
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2504
_reflns_number_total             4620
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tq5012sup1.cif
_cod_data_source_block           I
_cod_database_code               2312353
_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   0.996
_shelx_estimated_absorpt_t_min   0.991
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C16(H16A,H16B)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C11(H11), C3(H3), C13(H13), C2(H2A), C14(H14), C8(H8), C17(H17)
2.c X=CH2 refined with riding coordinates:
 C18(H18A,H18B), C9(H9A,H9B)
2.d Idealised Me refined as rotating group:
 C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C26(H26A,H26B,
 H26C)
2.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O1(H1)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.7872(3) 0.7071(2) 0.30418(12) 0.0443(6) Uani 1 1 d . . . . .
H2 H 0.849753 0.778956 0.328024 0.066 Uiso 1 1 calc GR . . . .
O1 O 0.1798(3) 0.2572(2) 0.32208(14) 0.0461(6) Uani 1 1 d . . . . .
H1 H 0.239946 0.205196 0.358250 0.069 Uiso 1 1 calc GR . . . .
N2 N 0.9480(3) 0.9087(2) 0.42915(15) 0.0318(6) Uani 1 1 d . . . . .
N1 N 0.3864(3) 0.0782(3) 0.44324(15) 0.0350(6) Uani 1 1 d . . . . .
C20 C 0.9122(4) 1.0494(3) 0.42433(18) 0.0298(7) Uani 1 1 d . . . . .
C10 C 0.6020(4) 0.6474(3) 0.16905(18) 0.0284(7) Uani 1 1 d . . . . .
C5 C 0.3147(4) 0.5449(3) 0.18896(18) 0.0315(7) Uani 1 1 d . . . . .
H5 H 0.263994 0.611822 0.147290 0.038 Uiso 1 1 calc R . . . .
C21 C 1.0341(4) 0.8584(3) 0.50411(19) 0.0319(7) Uani 1 1 d . . . . .
C6 C 0.2077(4) 0.4489(3) 0.22482(19) 0.0333(7) Uani 1 1 d . . . . .
C25 C 0.5872(4) 0.0593(3) 0.57552(18) 0.0343(7) Uani 1 1 d . . . . .
C24 C 0.4726(4) 0.1387(3) 0.51810(19) 0.0335(7) Uani 1 1 d . . . . .
C4 C 0.4926(4) 0.5471(3) 0.21150(18) 0.0288(7) Uani 1 1 d . . . . .
C11 C 0.5646(4) 0.6655(3) 0.07937(18) 0.0334(7) Uani 1 1 d . . . . .
H11 H 0.466584 0.612748 0.046065 0.040 Uiso 1 1 calc R . . . .
C3 C 0.5635(4) 0.4490(3) 0.27314(18) 0.0324(7) Uani 1 1 d . . . . .
H3 H 0.684449 0.448158 0.290369 0.039 Uiso 1 1 calc R . . . .
C15 C 0.7472(4) 0.7264(3) 0.21658(18) 0.0335(7) Uani 1 1 d . . . . .
C13 C 0.8053(4) 0.8330(3) 0.08633(19) 0.0379(8) Uani 1 1 d . . . . .
H13 H 0.874881 0.896600 0.058792 0.045 Uiso 1 1 calc R . . . .
C2 C 0.4609(4) 0.3532(3) 0.30952(19) 0.0354(7) Uani 1 1 d . . . . .
H2A H 0.512007 0.286657 0.351328 0.043 Uiso 1 1 calc R . . . .
C1 C 0.2851(4) 0.3523(3) 0.28618(19) 0.0336(7) Uani 1 1 d . . . . .
C12 C 0.6633(4) 0.7564(3) 0.03679(18) 0.0351(7) Uani 1 1 d . . . . .
C14 C 0.8478(4) 0.8187(3) 0.17508(19) 0.0368(7) Uani 1 1 d . . . . .
H14 H 0.945973 0.872006 0.207830 0.044 Uiso 1 1 calc R . . . .
C19 C 0.8116(4) 1.0984(3) 0.33986(19) 0.0390(8) Uani 1 1 d . . . . .
H19A H 0.816193 1.027247 0.294304 0.058 Uiso 1 1 calc GR . . . .
H19B H 0.860492 1.193423 0.325777 0.058 Uiso 1 1 calc GR . . . .
H19C H 0.692227 1.106585 0.344183 0.058 Uiso 1 1 calc GR . . . .
C7 C 0.0157(4) 0.4447(3) 0.1960(2) 0.0431(8) Uani 1 1 d . . . . .
H7A H -0.036205 0.439627 0.247565 0.052 Uiso 1 1 calc R . . . .
H7B H -0.016214 0.536140 0.165924 0.052 Uiso 1 1 calc R . . . .
C22 C 1.0677(4) 0.6992(3) 0.5067(2) 0.0452(9) Uani 1 1 d . . . . .
H22A H 1.022568 0.654451 0.449434 0.068 Uiso 1 1 calc GR . . . .
H22B H 1.011017 0.650785 0.549177 0.068 Uiso 1 1 calc GR . . . .
H22C H 1.191296 0.688939 0.523032 0.068 Uiso 1 1 calc GR . . . .
C23 C 0.4427(4) 0.2941(3) 0.5377(2) 0.0460(9) Uani 1 1 d . . . . .
H23A H 0.356420 0.330286 0.490615 0.069 Uiso 1 1 calc GR . . . .
H23B H 0.550115 0.354521 0.543444 0.069 Uiso 1 1 calc GR . . . .
H23C H 0.402151 0.298394 0.591933 0.069 Uiso 1 1 calc GR . . . .
C16 C 0.6186(5) 0.7704(3) -0.06066(19) 0.0447(8) Uani 1 1 d . . . . .
H16A H 0.711661 0.732971 -0.085256 0.054 Uiso 1 1 calc R . . . .
H16B H 0.512648 0.708705 -0.083832 0.054 Uiso 1 1 calc R . . . .
C26 C 0.6846(5) 0.1228(4) 0.6605(2) 0.0525(9) Uani 1 1 d . . . . .
H26A H 0.751603 0.048088 0.693044 0.079 Uiso 1 1 calc GR . . . .
H26B H 0.603995 0.156861 0.693789 0.079 Uiso 1 1 calc GR . . . .
H26C H 0.761895 0.204809 0.650223 0.079 Uiso 1 1 calc GR . . . .
C8 C -0.0554(5) 0.3195(4) 0.1376(3) 0.0605(11) Uani 1 1 d . . . . .
H8 H -0.044127 0.225586 0.161951 0.073 Uiso 1 1 calc R . . . .
C17 C 0.5928(6) 0.9210(4) -0.0895(2) 0.0672(12) Uani 1 1 d . . . . .
H17 H 0.494063 0.962818 -0.078378 0.081 Uiso 1 1 calc R . . . .
C18 C 0.6904(7) 1.0020(4) -0.1282(2) 0.0909(16) Uani 1 1 d . . . . .
H18A H 0.790894 0.965425 -0.140823 0.109 Uiso 1 1 calc R . . . .
H18B H 0.661771 1.098086 -0.144023 0.109 Uiso 1 1 calc R . . . .
C9 C -0.1286(6) 0.3235(6) 0.0596(3) 0.0953(16) Uani 1 1 d . . . . .
H9A H -0.143456 0.414494 0.031825 0.114 Uiso 1 1 calc R . . . .
H9B H -0.169420 0.235556 0.028203 0.114 Uiso 1 1 calc R . . . .
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'
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
C15 O2 H2 109.5 . . ?
C1 O1 H1 109.5 . . ?
C21 N2 C20 119.2(2) . . ?
C24 N1 C25 118.8(3) . 2_656 ?
N2 C20 C21 120.2(3) . 2_776 ?
N2 C20 C19 116.8(3) . . ?
C21 C20 C19 123.0(3) 2_776 . ?
C11 C10 C4 121.1(3) . . ?
C11 C10 C15 117.2(2) . . ?
C15 C10 C4 121.7(2) . . ?
C6 C5 H5 118.5 . . ?
C4 C5 H5 118.5 . . ?
C4 C5 C6 122.9(3) . . ?
N2 C21 C20 120.6(3) . 2_776 ?
N2 C21 C22 117.1(3) . . ?
C20 C21 C22 122.3(3) 2_776 . ?
C5 C6 C7 121.5(3) . . ?
C1 C6 C5 117.5(3) . . ?
C1 C6 C7 120.9(3) . . ?
N1 C25 C24 120.8(3) 2_656 . ?
N1 C25 C26 117.3(3) 2_656 . ?
C24 C25 C26 121.9(3) . . ?
N1 C24 C25 120.4(3) . . ?
N1 C24 C23 118.1(3) . . ?
C25 C24 C23 121.5(3) . . ?
C5 C4 C10 121.2(2) . . ?
C3 C4 C10 121.5(3) . . ?
C3 C4 C5 117.3(2) . . ?
C10 C11 H11 118.4 . . ?
C12 C11 C10 123.3(3) . . ?
C12 C11 H11 118.4 . . ?
C4 C3 H3 119.5 . . ?
C2 C3 C4 120.9(3) . . ?
C2 C3 H3 119.5 . . ?
O2 C15 C10 117.7(2) . . ?
O2 C15 C14 121.8(3) . . ?
C14 C15 C10 120.5(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 H13 119.4 . . ?
C14 C13 C12 121.3(3) . . ?
C3 C2 H2A 119.5 . . ?
C3 C2 C1 120.9(3) . . ?
C1 C2 H2A 119.5 . . ?
O1 C1 C6 117.8(3) . . ?
C2 C1 O1 121.8(2) . . ?
C2 C1 C6 120.4(2) . . ?
C11 C12 C13 117.7(3) . . ?
C11 C12 C16 121.2(3) . . ?
C13 C12 C16 121.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 C15 120.2(3) . . ?
C13 C14 H14 119.9 . . ?
C20 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C20 C19 H19C 109.5 . . ?
H19A C19 H19B 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C6 C7 H7A 109.0 . . ?
C6 C7 H7B 109.0 . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 C6 112.9(3) . . ?
C8 C7 H7A 109.0 . . ?
C8 C7 H7B 109.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C24 C23 H23A 109.5 . . ?
C24 C23 H23B 109.5 . . ?
C24 C23 H23C 109.5 . . ?
H23A C23 H23B 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C12 C16 H16A 108.8 . . ?
C12 C16 H16B 108.8 . . ?
H16A C16 H16B 107.7 . . ?
C17 C16 C12 113.7(3) . . ?
C17 C16 H16A 108.8 . . ?
C17 C16 H16B 108.8 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C7 C8 H8 116.4 . . ?
C9 C8 C7 127.3(4) . . ?
C9 C8 H8 116.4 . . ?
C16 C17 H17 116.6 . . ?
C18 C17 C16 126.9(4) . . ?
C18 C17 H17 116.6 . . ?
C17 C18 H18A 120.0 . . ?
C17 C18 H18B 120.0 . . ?
H18A C18 H18B 120.0 . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
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 H2 0.8400 . ?
O2 C15 1.370(3) . ?
O1 H1 0.8400 . ?
O1 C1 1.380(3) . ?
N2 C20 1.344(3) . ?
N2 C21 1.341(3) . ?
N1 C25 1.339(4) 2_656 ?
N1 C24 1.338(4) . ?
C20 C21 1.388(4) 2_776 ?
C20 C19 1.496(4) . ?
C10 C4 1.487(4) . ?
C10 C11 1.400(4) . ?
C10 C15 1.400(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.394(4) . ?
C5 C4 1.392(4) . ?
C21 C22 1.506(4) . ?
C6 C1 1.394(4) . ?
C6 C7 1.507(4) . ?
C25 C24 1.395(4) . ?
C25 C26 1.500(4) . ?
C24 C23 1.507(4) . ?
C4 C3 1.389(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.385(4) . ?
C3 H3 0.9500 . ?
C3 C2 1.374(4) . ?
C15 C14 1.392(4) . ?
C13 H13 0.9500 . ?
C13 C12 1.386(4) . ?
C13 C14 1.383(4) . ?
C2 H2A 0.9500 . ?
C2 C1 1.378(4) . ?
C12 C16 1.516(4) . ?
C14 H14 0.9500 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.480(5) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.474(5) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C8 H8 0.9500 . ?
C8 C9 1.251(5) . ?
C17 H17 0.9500 . ?
C17 C18 1.292(5) . ?
C18 H18A 0.9500 . ?
C18 H18B 0.9500 . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?

_cod_database_fobs_code 2312353
