A 1:2 cocrystal of genistein with isonicotinamide: crystal structure and Hirshfeld surface analysis
Sowa, Michał; Ślepokura, Katarzyna; Matczak-Jon, Ewa; Acta Crystallographica Section C 69 (2013) 1267–1272; doi:10.1107/S0108270113029545

data_2019219
_publ_section_title
;
 A 1:2 cocrystal of genistein with isonicotinamide: crystal structure and
 Hirshfeld surface analysis
;
_journal_coeditor_code           FM3012
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1267
_journal_page_last               1272
_journal_paper_doi               10.1107/S0108270113029545
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C15 H10 O5 , 2C6 H6 N2 O'
_chemical_formula_moiety         'C15 H10 O5, 2(C6 H6 N2 O)'
_chemical_formula_sum            'C27 H22 N4 O7'
_chemical_formula_weight         514.48
_chemical_name_systematic
;
5,7-Dihydroxy-3-(4-hydroxyphenyl)chromen-4-one--pyridine-4-carboxamide (1/2)
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL2013
_cell_angle_alpha                109.61(3)
_cell_angle_beta                 95.34(3)
_cell_angle_gamma                109.75(3)
_cell_formula_units_Z            2
_cell_length_a                   8.233(3)
_cell_length_b                   11.872(4)
_cell_length_c                   13.773(4)
_cell_measurement_reflns_used    6644
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      36.69
_cell_measurement_theta_min      3.00
_cell_volume                     1160.7(8)
_computing_cell_refinement       'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_data_collection       'CrysAlis CCD (Oxford Diffraction, 2010)'
_computing_data_reduction        'CrysAlis RED (Oxford Diffraction, 2010)'
_computing_molecular_graphics
;
OLEX2 (Dolomanov <i>et al.</i>, 2009) and (DIAMOND (Brandenburg,
2005)
;
_computing_publication_material  'SHELXL2013 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      120(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.573
_diffrn_measurement_device_type
'Kuma KM4-CCD kappa-geometry diffractometer with a Sapphire 2 CCD camera'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0330
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            12982
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         36.772
_diffrn_reflns_theta_min         3.006
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis RED; Oxford Diffraction, 2010)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.472
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.366
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     371
_refine_ls_number_reflns         6651
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0755
_refine_ls_R_factor_gt           0.0550
_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/[\s^2^(Fo^2^)+(0.0950P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1409
_refine_ls_wR_factor_ref         0.1504
_reflns_number_gt                4659
_reflns_number_total             6651
_reflns_threshold_expression     I>2\s(I)
_cod_data_source_file            fm3012.cif
_cod_data_source_block           I
_cod_original_cell_volume        1160.7(7)
_cod_database_code               2019219
_shelx_estimated_absorpt_t_min   0.970
_shelx_estimated_absorpt_t_max   0.986
_shelx_hkl_checksum              34052
_shelx_res_checksum              2599
_shelxl_version_number           20.13