Structure, physicochemical properties and pharmacokinetics of resveratrol and piperine cocrystals
He, Hongyan; Zhang, Qi; Wang, Jian-Rong; Mei, Xuefeng; CrystEngComm  (2017) –; doi:10.1039/C7CE01468F

data_7229161
_publ_section_title
;
 Structure, physicochemical properties and pharmacokinetics of resveratrol
 and piperine cocrystals
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01468F
_journal_year                    2017
_chemical_formula_moiety         'C14 H12 O3, H2 O, 3(C17 H19 N O3), C2 H3 N'
_chemical_formula_sum            'C67 H74 N4 O13'
_chemical_formula_weight         1143.30
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-02-19
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2016.02.16 svn.r3264 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-12-15 deposited with the CCDC.
2017-09-14 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.184(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   40.6077(14)
_cell_length_b                   8.7048(3)
_cell_length_c                   17.2621(6)
_cell_measurement_reflns_used    8732
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.81
_cell_measurement_theta_min      2.37
_cell_volume                     6053.9(4)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al., 2007)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0654
_diffrn_reflns_av_unetI/netI     0.0871
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_h_min       -53
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            52344
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.654
_diffrn_reflns_theta_min         1.011
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.087
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6155
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0792 before and 0.0546 after correction.
The Ratio of minimum to maximum transmission is 0.8255.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.798
_refine_diff_density_min         -0.394
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     766
_refine_ls_number_reflns         14030
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1354
_refine_ls_R_factor_gt           0.0665
_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/[\s^2^(Fo^2^)+(0.0652P)^2^+1.8185P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1344
_refine_ls_wR_factor_ref         0.1617
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8359
_reflns_number_total             14030
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01468f2.cif
_cod_data_source_block           mo_2016062_0ma
_cod_database_code               7229161
_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:
 C48(H48A,H48B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B), C36(H36A,
 H36B), C35(H35A,H35B), C51(H51A,H51B), C50(H50A,H50B), C49(H49A,H49B),
 C65(H65A,H65B), C52(H52A,H52B), C53(H53A,H53B), C31(H31A,H31B), C15(H15A,H15B),
  C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,H19B)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C2(H2A), C8(H8), C10(H10), C11(H11), C4(H4), C6(H6), C14(H14),
 C13(H13), C43(H43), C41(H41), C40(H40), C39(H39), C38(H38), C47(H47), C46(H46),
  C55(H55), C56(H56), C57(H57), C58(H58), C60(H60), C63(H63), C64(H64),
 C26(H26), C24(H24), C23(H23), C22(H22), C21(H21), C30(H30), C29(H29)
2.c Tetrahedral OH refined with riding coordinates:
 O1(H1), O3(H3), O2(H2)
2.d Idealised Me refined as rotating group:
 C1S(H1SA,H1SB,H1SC)
;
_shelx_res_checksum              44364
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'