Pharmaceutical cocrystals of naringenin with improved dissolution performance
Luo, Chun; Liang, Wendong; Chen, Xin; Wang, Jianming; Deng, Zongwu; Zhang, Hailu; CrystEngComm 20 (2018) 3025–; doi:10.1039/C8CE00341F

data_7230503
_publ_section_title
;
 Pharmaceutical cocrystals of naringenin with improved dissolution
 performance
;
_journal_issue                   22
_journal_name_full               CrystEngComm
_journal_page_first              3025
_journal_paper_doi               10.1039/C8CE00341F
_journal_volume                  20
_journal_year                    2018
_chemical_formula_moiety         '2(C6 H6 N2 O), C15 H12 O5'
_chemical_formula_sum            'C27 H24 N4 O7'
_chemical_formula_weight         516.50
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-11
_audit_creation_method
;
Olex2 1.2-alpha
(compiled 2017.12.08 svn.r3473 for OlexSys, GUI svn.r5433)
;
_audit_update_record
;
2018-01-29 deposited with the CCDC.
2018-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.632(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.2424(8)
_cell_length_b                   5.0793(3)
_cell_length_c                   33.737(2)
_cell_measurement_reflns_used    3714
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      68.49
_cell_measurement_theta_min      4.79
_cell_volume                     2428.8(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_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      123.15
_diffrn_measured_fraction_theta_full 0.956
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_unetI/netI     0.0326
_diffrn_reflns_Laue_measured_fraction_full 0.956
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_number            8332
_diffrn_reflns_point_group_measured_fraction_full 0.956
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.479
_diffrn_reflns_theta_min         4.788
_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_description       block
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         4204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.050
_refine_ls_R_factor_all          0.0623
_refine_ls_R_factor_gt           0.0473
_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^)+(0.1065P)^2^+0.1295P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1374
_refine_ls_wR_factor_ref         0.1485
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3325
_reflns_number_total             4204
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00341f2.cif
_cod_data_source_block           NAR-INM
_cod_depositor_comments
'Adding full bibliography for 7230503--7230504.cif.'
_cod_database_code               7230503
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.950
_shelx_estimated_absorpt_t_min   0.793
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Sof(C15)=Sof(H15)=Sof(C14)=Sof(H14)=Sof(C12)=Sof(H12)=Sof(C13)=Sof(H13)=1-
 FVAR(1)
 Sof(C15A)=Sof(H15A)=Sof(C14A)=Sof(H14A)=Sof(C12A)=Sof(H12A)=Sof(C13A)=
 Sof(H13A)=FVAR(1)
 Sof(H3BC)=Sof(H3BD)=Sof(C2)=Sof(H2)=Sof(C5')=Sof(H5')=Sof(C6')=Sof(H6')=
 Sof(C1')=Sof(C3')=Sof(H3')=Sof(C2')=Sof(H2')=1-FVAR(2)
 Sof(H3AA)=Sof(H3AB)=Sof(C2A)=Sof(H2A)=Sof(C6'A)=Sof(H6'A)=Sof(C1'A)=Sof(C5'A)=
 Sof(H5'A)=Sof(C3'A)=Sof(H3'A)=Sof(C2'A)=Sof(H2'A)=FVAR(2)
3.a Ternary CH refined with riding coordinates:
 C2A(H2A), C2(H2)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3BC,H3BD), C3(H3AA,H3AB)
3.c Aromatic/amide H refined with riding coordinates:
 C12'(H12'), C13'(H13'), C14'(H14'), C15'(H15'), C15A(H15A), C14A(H14A),
 C12A(H12A), C13A(H13A), C15(H15), C14(H14), C12(H12), C13(H13), C6(H6), C8(H8),
  C6'A(H6'A), C5'A(H5'A), C3'A(H3'A), C2'A(H2'A), C5'(H5'), C6'(H6'), C3'(H3'),
 C2'(H2')
3.d X=CH2 refined with riding coordinates:
 N2'(H2'B,H2'C), N2(H2B,H2C)
3.e Idealised tetrahedral OH refined as rotating group:
 O5(H5), O4(H4), O3(H3)
;
_shelx_res_checksum              42799
_olex2_submission_special_instructions 'No special instructions were received'