Characterization of drug–drug salt forms of metformin and aspirin with improved physicochemical properties
Zhou, Wen-Xiu; Zhao, Hong-Wei; Chen, Huan-Huan; Zhang, Zai-Yong; Chen, Dong-Ying; CrystEngComm 21 (2019) 3770–; doi:10.1039/C9CE00377K

data_7232771
_publ_section_title
;
 Characterization of drug--drug salt forms of metformin and aspirin with
 improved physicochemical properties
;
_journal_issue                   25
_journal_name_full               CrystEngComm
_journal_page_first              3770
_journal_paper_doi               10.1039/C9CE00377K
_journal_volume                  21
_journal_year                    2019
_chemical_formula_moiety         '2(C9 H7 O4), 2(C4 H12 N5), H2 O'
_chemical_formula_sum            'C26 H40 N10 O9'
_chemical_formula_weight         636.68
_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   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-02-20 deposited with the CCDC.    2019-05-09 downloaded from the CCDC.
;
_cell_angle_alpha                69.9000(10)
_cell_angle_beta                 75.107(2)
_cell_angle_gamma                67.877(3)
_cell_formula_units_Z            2
_cell_length_a                   9.0858(9)
_cell_length_b                   11.9718(12)
_cell_length_c                   16.5784(17)
_cell_measurement_reflns_used    3751
_cell_measurement_temperature    205(2)
_cell_measurement_theta_max      26.21
_cell_measurement_theta_min      4.28
_cell_volume                     1551.8(3)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      205.0
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0846
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            14201
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.478
_diffrn_reflns_theta_min         1.322
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.634
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   Bruker;SADABS;2014
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_description       block
_exptl_crystal_F_000             676
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.219
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.962
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6965
_refine_ls_number_restraints     6
_refine_ls_restrained_S_all      0.962
_refine_ls_R_factor_all          0.1049
_refine_ls_R_factor_gt           0.0535
_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^)+(0.0540P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1125
_refine_ls_wR_factor_ref         0.1369
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4046
_reflns_number_total             6965
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9ce00377k2.cif
_cod_data_source_block           20180326_a
_cod_depositor_comments
'Adding full bibliography for 7232770--7232771.cif.'
_cod_database_code               7232771
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.990
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All N(H) groups, All O(H,H) groups
2. Restrained distances
 N4'-H4'A \\sim N4'-H4'B \\sim N1'-H1'A
 with sigma of 0.02
 N4-H4A \\sim N4-H4B \\sim N1-H1B
 with sigma of 0.02
3.a Free rotating group:
 O5(H5A,H5B)
3.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C5'(H5'), C2(H2), C4(H4), C4'(H4'), C2'(H2'), C3(H3), C3'(H3')
3.c X=CH2 refined with riding coordinates:
 N1'(H1'A,H1'B), N2'(H2'A,H2'B), N2(H2A,H2B)
3.d Idealised Me refined as rotating group:
 C13'(H13D,H13E,H13F), C12(H12A,H12B,H12C), C12'(H12D,H12E,H12F), C8(H8A,H8B,
 H8C), C13(H13A,H13B,H13C), C8'(H8'A,H8'B,H8'C)
;
_olex2_submission_special_instructions 'No special instructions were received'