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_7230504
_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         'C5 H11 N O2, C15 H12 O5'
_chemical_formula_sum            'C20 H23 N O7'
_chemical_formula_weight         389.39
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_Hall           'C 2y'
_space_group_name_H-M_alt        'C 1 2 1'
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   mixed
_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
;
2018-04-02 deposited with the CCDC.
2018-04-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.0997(19)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.6006(7)
_cell_length_b                   6.6844(3)
_cell_length_c                   13.5560(5)
_cell_measurement_reflns_used    3847
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      68.55
_cell_measurement_theta_min      4.10
_cell_volume                     1956.00(13)
_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    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_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  0.0279
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            7511
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.567
_diffrn_reflns_theta_min         4.096
_exptl_absorpt_coefficient_mu    0.841
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         3430
_refine_ls_number_restraints     147
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0578
_refine_ls_R_factor_gt           0.0524
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0670P)^2^+1.6902P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1438
_refine_ls_wR_factor_ref         0.1489
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                3067
_reflns_number_total             3430
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8ce00341f2.cif
_cod_data_source_block           xl_sq
_cod_depositor_comments
'Adding full bibliography for 7230503--7230504.cif.'
_cod_database_code               7230504
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.837
_shelx_estimated_absorpt_t_min   0.811
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(6)
 0.3(6)
2. 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
3. Restrained distances
 C1'A-C2A
 1.5 with sigma of 0.02
 C6'A-C2A \\sim C2A-C2'A
 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uanis(C2) \\sim Ueq, Uanis(C3) \\sim Ueq, Uanis(C3A) \\sim Ueq, Uanis(C2A)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Rigid body (RIGU) restrains
 C1', C1'A, C2, C2', C2'A, C2A, C3, C3', C3'A, C3A, C4', C4'A, C5', C5'A, C6',
 C6'A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1, C1', C1'A, C2, C2A, C3, C3A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 Sof(O3A)=Sof(H3A)=Sof(C2A)=Sof(H2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C6'A)=
 Sof(H6'A)=Sof(C5'A)=Sof(H5'A)=Sof(C4'A)=Sof(C3'A)=Sof(H3'A)=Sof(C2'A)=
 Sof(H2'A)=Sof(C1'A)=1-FVAR(1)
 Sof(O3)=Sof(H3)=Sof(C2)=Sof(H2)=Sof(C2')=Sof(H2')=Sof(C3')=Sof(H3')=Sof(C4')=
 Sof(C5')=Sof(H5')=Sof(C6')=Sof(H6')=Sof(C1')=Sof(C3)=Sof(H3B)=Sof(H3C)=FVAR(1)
7.a Riding coordinates:
 O3(H3), O3A(H3A)
7.b Ternary CH refined with riding coordinates:
 C2(H2), C2A(H2A)
7.c Secondary CH2 refined with riding coordinates:
 C3(H3B,H3C), C3A(H3AA,H3AB), C11(H11A,H11B)
7.d Aromatic/amide H refined with riding coordinates:
 C2'(H2'), C3'(H3'), C5'(H5'), C6'(H6'), C6(H6), C6'A(H6'A), C5'A(H5'A),
 C3'A(H3'A), C2'A(H2'A), C8(H8)
7.e Fitted hexagon refined as free rotating group:
 C2'(C3',C4',C5',C6',C1'), C6'A(C5'A,C4'A,C3'A,C2'A,C1'A)
7.f Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
7.g Idealised tetrahedral OH refined as rotating group:
 O4(H4), O5(H5)
;
_shelx_res_checksum              9689
_shelx_fab_checksum              96356
_olex2_submission_special_instructions 'No special instructions were received'