#------------------------------------------------------------------------------
#$Date: 2023-06-05 06:25:30 +0200 (Mon 05 de Jun de 2023) $
#$Revision: 284267 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/65/7246584.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_7246584
loop_
_publ_author_name
'Zhang, Min'
'Wang, Min-Yu'
'Yu, Yue-Ming'
'Meng, Su-Su'
'Yan, Cui-Wei'
'Wu, Zhi-Yong'
'Li, Yan-Tuan'
_publ_section_title
;
 Supramolecular self-assembly with p-coumaric acid offers the first
 cocrystal for perfecting the physicochemical peculiarity and enhancing
 the antifungal effect of drug bifonazole
;
_journal_issue                   18
_journal_name_full               CrystEngComm
_journal_page_first              2789
_journal_page_last               2801
_journal_paper_doi               10.1039/D3CE00082F
_journal_volume                  25
_journal_year                    2023
_chemical_formula_sum            'C31 H26 N2 O3'
_chemical_formula_weight         474.54
_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   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-11-05 deposited with the CCDC.	2023-04-06 downloaded from the CCDC.
;
_cell_angle_alpha                97.669(3)
_cell_angle_beta                 90.451(3)
_cell_angle_gamma                112.261(2)
_cell_formula_units_Z            2
_cell_length_a                   8.7502(3)
_cell_length_b                   9.7243(3)
_cell_length_c                   16.2580(5)
_cell_measurement_reflns_used    12313
_cell_measurement_temperature    303(2)
_cell_measurement_theta_max      68.71
_cell_measurement_theta_min      2.75
_cell_volume                     1266.25(7)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      303(2)
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54186
_diffrn_reflns_av_R_equivalents  0.0345
_diffrn_reflns_av_unetI/netI     0.0322
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -4
_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            10545
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.686
_diffrn_reflns_theta_max         68.712
_diffrn_reflns_theta_min         2.748
_diffrn_source                   'GeniX 3D HF Cu'
_exptl_absorpt_coefficient_mu    0.642
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.1691
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.245
_exptl_crystal_description       block
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_refine_diff_density_max         0.464
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.067
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     429
_refine_ls_number_reflns         4533
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0654
_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)+(0.1114P)²+0.3669P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.1818
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3931
_reflns_number_total             4533
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ce00082f2.cif
_cod_data_source_block           shelx
_cod_depositor_comments          'Adding full bibliography for 7246584.cif.'
_cod_database_code               7246584
_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_min   0.927
_shelx_estimated_absorpt_t_max   0.956
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
N1 N 0.03373(18) 0.40258(19) 0.19590(10) 0.0449(4) Uani 1 1 d . . . . .
N2 N 0.26803(19) 0.53503(19) 0.14636(12) 0.0501(4) Uani 1 1 d . . . . .
C1 C 0.1936(3) 0.4909(3) 0.21380(14) 0.0533(5) Uani 1 1 d . . . . .
C2 C 0.1486(2) 0.4728(2) 0.08293(13) 0.0466(5) Uani 1 1 d . . . . .
C3 C 0.0044(2) 0.3918(2) 0.11215(12) 0.0460(4) Uani 1 1 d . . . . .
C4 C -0.0929(2) 0.3348(2) 0.25410(12) 0.0467(5) Uani 1 1 d . . . . .
C5 C -0.0156(2) 0.2844(2) 0.32281(12) 0.0489(5) Uani 1 1 d . . . . .
C6 C 0.0310(3) 0.3659(3) 0.40150(15) 0.0665(6) Uani 1 1 d . . . . .
C7 C 0.1015(4) 0.3159(4) 0.46131(17) 0.0811(8) Uani 1 1 d . . . . .
C8 C 0.1296(4) 0.1869(4) 0.4435(2) 0.0826(8) Uani 1 1 d . . . . .
C9 C 0.0889(5) 0.1065(4) 0.3652(3) 0.1053(13) Uani 1 1 d . . . . .
C10 C 0.0153(5) 0.1543(3) 0.3046(2) 0.0860(9) Uani 1 1 d . . . . .
C11 C -0.1827(2) 0.4364(2) 0.28533(12) 0.0480(5) Uani 1 1 d . . . . .
C12 C -0.3419(3) 0.3704(3) 0.31125(16) 0.0611(6) Uani 1 1 d . . . . .
C13 C -0.4293(3) 0.4568(3) 0.34010(17) 0.0624(6) Uani 1 1 d . . . . .
C14 C -0.3650(3) 0.6117(3) 0.34252(12) 0.0508(5) Uani 1 1 d . . . . .
C15 C -0.2074(3) 0.6762(3) 0.31573(14) 0.0565(5) Uani 1 1 d . . . . .
C16 C -0.1177(3) 0.5899(3) 0.28803(14) 0.0559(5) Uani 1 1 d . . . . .
C17 C -0.4629(3) 0.7026(3) 0.37197(14) 0.0550(5) Uani 1 1 d . . . . .
C18 C -0.5581(4) 0.6713(4) 0.44017(18) 0.0740(7) Uani 1 1 d . . . . .
C19 C -0.6524(4) 0.7522(4) 0.4667(2) 0.0910(9) Uani 1 1 d . . . . .
C20 C -0.6569(5) 0.8641(4) 0.4268(3) 0.0975(10) Uani 1 1 d . . . . .
C21 C -0.5647(5) 0.8971(4) 0.3585(3) 0.0977(11) Uani 1 1 d . . . . .
C22 C -0.4664(4) 0.8190(3) 0.33260(19) 0.0747(7) Uani 1 1 d . . . . .
O1 O 0.56364(19) 0.72859(18) 0.12637(12) 0.0647(5) Uani 1 1 d . . . . .
O2 O 0.67675(18) 0.55989(16) 0.10006(11) 0.0592(4) Uani 1 1 d . . . . .
O3 O 1.61466(17) 1.26483(18) 0.09986(13) 0.0668(5) Uani 1 1 d . . . . .
C23 C 0.6873(2) 0.6882(2) 0.11041(12) 0.0432(4) Uani 1 1 d . . . . .
C24 C 0.8423(2) 0.8204(2) 0.10739(13) 0.0468(5) Uani 1 1 d . . . . .
C25 C 0.9886(2) 0.8106(2) 0.10660(13) 0.0455(4) Uani 1 1 d . . . . .
C26 C 1.1482(2) 0.9329(2) 0.10425(12) 0.0445(4) Uani 1 1 d . . . . .
C27 C 1.1664(2) 1.0781(2) 0.09379(14) 0.0489(5) Uani 1 1 d . . . . .
C28 C 1.3205(2) 1.1906(2) 0.09305(14) 0.0488(5) Uani 1 1 d . . . . .
C29 C 1.4604(2) 1.1593(2) 0.10129(14) 0.0475(5) Uani 1 1 d . . . . .
C30 C 1.4445(3) 1.0154(3) 0.1092(2) 0.0735(8) Uani 1 1 d . . . . .
C31 C 1.2913(3) 0.9051(2) 0.1109(2) 0.0675(7) Uani 1 1 d . . . . .
H1 H 0.245(3) 0.514(3) 0.2684(18) 0.069(7) Uiso 1 1 d . . . . .
H1A H 0.472(4) 0.644(4) 0.132(2) 0.085(9) Uiso 1 1 d . . . . .
H2 H 0.168(3) 0.485(3) 0.0272(16) 0.058(6) Uiso 1 1 d . . . . .
H3 H -0.101(3) 0.334(3) 0.0873(16) 0.061(7) Uiso 1 1 d . . . . .
H3A H 1.609(4) 1.365(4) 0.102(2) 0.086(9) Uiso 1 1 d . . . . .
H4 H -0.169(3) 0.240(3) 0.2212(14) 0.048(6) Uiso 1 1 d . . . . .
H6 H 0.012(3) 0.462(3) 0.4155(17) 0.069(7) Uiso 1 1 d . . . . .
H7 H 0.131(4) 0.384(4) 0.522(2) 0.096(10) Uiso 1 1 d . . . . .
H8 H 0.186(5) 0.152(4) 0.488(2) 0.106(11) Uiso 1 1 d . . . . .
H9 H 0.108(6) 0.019(6) 0.350(3) 0.140(16) Uiso 1 1 d . . . . .
H10 H -0.014(5) 0.093(5) 0.250(3) 0.117(13) Uiso 1 1 d . . . . .
H12 H -0.388(3) 0.260(3) 0.3078(17) 0.070(7) Uiso 1 1 d . . . . .
H13 H -0.538(4) 0.407(4) 0.3577(19) 0.085(9) Uiso 1 1 d . . . . .
H15 H -0.162(3) 0.778(3) 0.3201(15) 0.056(6) Uiso 1 1 d . . . . .
H16 H -0.006(4) 0.642(3) 0.2709(17) 0.069(7) Uiso 1 1 d . . . . .
H18 H -0.556(4) 0.583(4) 0.467(2) 0.097(10) Uiso 1 1 d . . . . .
H19 H -0.721(6) 0.728(5) 0.513(3) 0.125(14) Uiso 1 1 d . . . . .
H20 H -0.728(5) 0.931(5) 0.453(3) 0.126(13) Uiso 1 1 d . . . . .
H21 H -0.574(5) 0.973(5) 0.328(3) 0.118(13) Uiso 1 1 d . . . . .
H22 H -0.401(4) 0.842(4) 0.287(2) 0.085(9) Uiso 1 1 d . . . . .
H24 H 0.829(3) 0.913(3) 0.1063(16) 0.060(7) Uiso 1 1 d . . . . .
H25 H 0.993(3) 0.707(3) 0.1088(15) 0.056(6) Uiso 1 1 d . . . . .
H27 H 1.068(3) 1.104(3) 0.0862(17) 0.066(7) Uiso 1 1 d . . . . .
H28 H 1.331(3) 1.288(3) 0.0829(15) 0.059(6) Uiso 1 1 d . . . . .
H30 H 1.541(4) 0.989(4) 0.108(2) 0.090(9) Uiso 1 1 d . . . . .
H31 H 1.291(3) 0.811(3) 0.1136(17) 0.068(7) Uiso 1 1 d . . . . .
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'
O O 0.0492 0.0322 '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'
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
C1 N1 C3 106.83(16) . . ?
C1 N1 C4 128.06(17) . . ?
C3 N1 C4 125.03(16) . . ?
C1 N2 C2 105.39(16) . . ?
N2 C1 N1 111.27(19) . . ?
N2 C1 H1 125.9(16) . . ?
N1 C1 H1 122.8(16) . . ?
C3 C2 N2 110.10(18) . . ?
C3 C2 H2 126.1(15) . . ?
N2 C2 H2 123.8(15) . . ?
C2 C3 N1 106.40(18) . . ?
C2 C3 H3 133.8(15) . . ?
N1 C3 H3 119.8(15) . . ?
N1 C4 C11 112.15(16) . . ?
N1 C4 C5 109.62(15) . . ?
C11 C4 C5 114.36(17) . . ?
N1 C4 H4 104.0(13) . . ?
C11 C4 H4 111.5(13) . . ?
C5 C4 H4 104.4(13) . . ?
C6 C5 C10 118.4(2) . . ?
C6 C5 C4 122.8(2) . . ?
C10 C5 C4 118.7(2) . . ?
C7 C6 C5 120.6(3) . . ?
C7 C6 H6 119.8(16) . . ?
C5 C6 H6 119.6(16) . . ?
C8 C7 C6 120.7(3) . . ?
C8 C7 H7 122.8(19) . . ?
C6 C7 H7 116.4(19) . . ?
C7 C8 C9 119.7(3) . . ?
C7 C8 H8 120(2) . . ?
C9 C8 H8 120(2) . . ?
C8 C9 C10 120.2(3) . . ?
C8 C9 H9 123(3) . . ?
C10 C9 H9 117(3) . . ?
C5 C10 C9 120.3(3) . . ?
C5 C10 H10 122(2) . . ?
C9 C10 H10 118(2) . . ?
C16 C11 C12 117.6(2) . . ?
C16 C11 C4 124.12(18) . . ?
C12 C11 C4 118.26(19) . . ?
C13 C12 C11 120.9(2) . . ?
C13 C12 H12 122.3(17) . . ?
C11 C12 H12 116.8(17) . . ?
C12 C13 C14 121.9(2) . . ?
C12 C13 H13 118.5(19) . . ?
C14 C13 H13 119.6(19) . . ?
C15 C14 C13 116.9(2) . . ?
C15 C14 C17 122.0(2) . . ?
C13 C14 C17 121.1(2) . . ?
C14 C15 C16 121.4(2) . . ?
C14 C15 H15 117.3(16) . . ?
C16 C15 H15 121.2(16) . . ?
C11 C16 C15 121.3(2) . . ?
C11 C16 H16 120.7(16) . . ?
C15 C16 H16 117.9(16) . . ?
C22 C17 C18 117.1(2) . . ?
C22 C17 C14 122.3(2) . . ?
C18 C17 C14 120.7(2) . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18 123(2) . . ?
C17 C18 H18 116(2) . . ?
C20 C19 C18 121.1(3) . . ?
C20 C19 H19 118(3) . . ?
C18 C19 H19 121(3) . . ?
C19 C20 C21 119.0(3) . . ?
C19 C20 H20 118(2) . . ?
C21 C20 H20 122(2) . . ?
C20 C21 C22 120.3(3) . . ?
C20 C21 H21 119(2) . . ?
C22 C21 H21 121(2) . . ?
C21 C22 C17 121.3(3) . . ?
C21 C22 H22 121(2) . . ?
C17 C22 H22 117(2) . . ?
C23 O1 H1A 108(2) . . ?
C29 O3 H3A 109.8(19) . . ?
O2 C23 O1 124.23(17) . . ?
O2 C23 C24 124.60(18) . . ?
O1 C23 C24 111.17(17) . . ?
C25 C24 C23 122.22(18) . . ?
C25 C24 H24 122.5(16) . . ?
C23 C24 H24 115.3(16) . . ?
C24 C25 C26 126.75(19) . . ?
C24 C25 H25 117.8(14) . . ?
C26 C25 H25 115.4(14) . . ?
C31 C26 C27 117.11(18) . . ?
C31 C26 C25 119.18(18) . . ?
C27 C26 C25 123.70(18) . . ?
C28 C27 C26 121.50(18) . . ?
C28 C27 H27 117.8(16) . . ?
C26 C27 H27 120.8(16) . . ?
C29 C28 C27 119.74(18) . . ?
C29 C28 H28 119.8(15) . . ?
C27 C28 H28 120.3(16) . . ?
O3 C29 C30 118.16(18) . . ?
O3 C29 C28 122.29(18) . . ?
C30 C29 C28 119.52(18) . . ?
C31 C30 C29 120.3(2) . . ?
C31 C30 H30 119.2(19) . . ?
C29 C30 H30 120.2(19) . . ?
C30 C31 C26 121.8(2) . . ?
C30 C31 H31 115.0(17) . . ?
C26 C31 H31 123.2(17) . . ?
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
N1 C1 1.340(3) . ?
N1 C3 1.366(3) . ?
N1 C4 1.479(2) . ?
N2 C1 1.317(3) . ?
N2 C2 1.364(3) . ?
C1 H1 0.95(3) . ?
C2 C3 1.339(3) . ?
C2 H2 0.94(3) . ?
C3 H3 0.93(3) . ?
C4 C11 1.521(3) . ?
C4 C5 1.527(3) . ?
C4 H4 0.99(2) . ?
C5 C6 1.381(3) . ?
C5 C10 1.386(4) . ?
C6 C7 1.381(4) . ?
C6 H6 1.00(3) . ?
C7 C8 1.363(5) . ?
C7 H7 1.09(4) . ?
C8 C9 1.368(5) . ?
C8 H8 1.04(4) . ?
C9 C10 1.393(4) . ?
C9 H9 0.93(5) . ?
C10 H10 0.97(4) . ?
C11 C16 1.376(3) . ?
C11 C12 1.391(3) . ?
C12 C13 1.377(4) . ?
C12 H12 0.98(3) . ?
C13 C14 1.389(3) . ?
C13 H13 0.96(3) . ?
C14 C15 1.383(3) . ?
C14 C17 1.488(3) . ?
C15 C16 1.388(3) . ?
C15 H15 0.91(3) . ?
C16 H16 0.98(3) . ?
C17 C22 1.382(4) . ?
C17 C18 1.388(3) . ?
C18 C19 1.377(4) . ?
C18 H18 1.02(4) . ?
C19 C20 1.352(5) . ?
C19 H19 0.97(4) . ?
C20 C21 1.378(5) . ?
C20 H20 1.11(4) . ?
C21 C22 1.382(5) . ?
C21 H21 0.97(5) . ?
C22 H22 0.93(3) . ?
O1 C23 1.300(2) . ?
O1 H1A 0.92(3) . ?
O2 C23 1.204(2) . ?
O3 C29 1.354(2) . ?
O3 H3A 0.99(3) . ?
C23 C24 1.480(3) . ?
C24 C25 1.319(3) . ?
C24 H24 0.95(3) . ?
C25 C26 1.456(3) . ?
C25 H25 1.03(3) . ?
C26 C31 1.385(3) . ?
C26 C27 1.394(3) . ?
C27 C28 1.379(3) . ?
C27 H27 0.99(3) . ?
C28 C29 1.378(3) . ?
C28 H28 0.95(3) . ?
C29 C30 1.377(3) . ?
C30 C31 1.367(3) . ?
C30 H30 0.97(4) . ?
C31 H31 0.92(3) . ?
