Molecular salts of quinine: a crystal engineering route to enhance the aqueous solubility
Divya, Indira S.; Amrutha, Surendran; SeethaLekshmi, Sunil; Varughese, Sunil; CrystEngComm 23 (2021) 6942–6951; doi:10.1039/D1CE00791B

data_7243428
_publ_section_title
;
 Molecular salts of quinine: a crystal engineering route to enhance the
 aqueous solubility
;
_journal_issue                   39
_journal_name_full               CrystEngComm
_journal_page_first              6942
_journal_page_last               6951
_journal_paper_doi               10.1039/D1CE00791B
_journal_volume                  23
_journal_year                    2021
_chemical_formula_moiety         'C20 H25 N2 O2, C7 H5 O3, C H4 O'
_chemical_formula_sum            'C28 H34 N2 O6'
_chemical_formula_weight         494.57
_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_Hall           'P 2ac 2ab'
_space_group_name_H-M_alt        'P 21 21 21'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2020-10-12
_audit_creation_method
;
Olex2 1.3
(compiled 2020.07.16 svn.r6f6c53a7 for OlexSys, GUI svn.r6139)
;
_audit_update_record
;
2020-10-13 deposited with the CCDC.	2021-08-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   6.5291(19)
_cell_length_b                   19.368(6)
_cell_length_c                   20.431(6)
_cell_measurement_reflns_used    778
_cell_measurement_temperature    298
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.1
_cell_volume                     2583.6(13)
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1172
_diffrn_reflns_av_unetI/netI     0.1294
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18359
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.245
_diffrn_reflns_theta_min         3.171
_diffrn_source_current           40.0
_diffrn_source_power             2.0
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.892
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Jacobson Unpublished Results'
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.17
_refine_diff_density_max         0.131
_refine_diff_density_min         -0.168
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details
;
 Flack x determined using 727 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -1.1(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.825
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     350
_refine_ls_number_reflns         4623
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      0.825
_refine_ls_R_factor_all          0.1069
_refine_ls_R_factor_gt           0.0510
_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^)+(0.0138P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0819
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.982
_reflns_number_gt                2582
_reflns_number_total             4623
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00791b2.cif
_cod_data_source_block           datam_CCDC7
_cod_depositor_comments
'Adding full bibliography for 7243420--7243429.cif.'
_cod_database_code               7243428
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.985
_shelx_estimated_absorpt_t_min   0.980
_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
2. Restrained distances
 O35-H35
 0.83 with sigma of 0.02
3.a Ternary CH refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C11(H11)
3.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C5(H5A,H5B), C7(H7A,H7B), C8(H8A,H8B)
3.c Me refined with riding coordinates:
 C24(H24A,H24B,H24C)
3.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C15(H15), C19(H19), C21(H21), C22(H22), C29(H29), C30(H30),
 C32(H32), C33(H33)
3.e Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C)
;
_shelx_res_checksum              21099
_shelx_hkl_checksum              67469
_olex2_submission_special_instructions 'No special instructions were received'