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_7243426
_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
'2(C20 H25 N2 O2), C4 H4 O4, C4 H2 O4, 3(H2 O)'
_chemical_formula_sum            'C48 H62 N4 O15'
_chemical_formula_weight         935.01
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2020-10-13
_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                99.531(2)
_cell_angle_beta                 97.444(2)
_cell_angle_gamma                106.711(2)
_cell_formula_units_Z            1
_cell_length_a                   6.5187(3)
_cell_length_b                   10.9299(6)
_cell_length_c                   17.6311(9)
_cell_measurement_reflns_used    3674
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     1165.47(10)
_computing_cell_refinement
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_collection
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_computing_data_reduction
;
CrystalClear-SM Expert 2.1 b29 (Rigaku, 2013)
;
_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    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      99.98
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0569
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            24732
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.249
_diffrn_reflns_theta_min         2.385
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.902
_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    1.332
_exptl_crystal_description       block
_exptl_crystal_F_000             498
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.571
_refine_diff_density_min         -0.411
_refine_diff_density_rms         0.052
_refine_ls_abs_structure_details
;
 Flack x determined using 3172 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     667
_refine_ls_number_reflns         8372
_refine_ls_number_restraints     569
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0444
_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^)+(0.0541P)^2^+0.3699P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1041
_refine_ls_wR_factor_ref         0.1131
_reflns_Friedel_coverage         0.990
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.990
_reflns_number_gt                7393
_reflns_number_total             8372
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00791b2.cif
_cod_data_source_block           datam_CCDC5
_cod_depositor_comments
'Adding full bibliography for 7243420--7243429.cif.'
_cod_database_code               7243426
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.981
_shelx_estimated_absorpt_t_min   0.978
_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, All O(H) groups
2. Restrained distances
 O64-H64
 0.907 with sigma of 0.02
 H91A-O91
 1.004 with sigma of 0.02
3. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms restrained to be isotropic: with sigma of 0.1 and sigma
for terminal atoms of 0.2
5. Others
 Sof(C58A)=Sof(C59A)=1-FVAR(1)
 Sof(C58)=Sof(C59)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C4(H4), C6(H6), C10(H10), C11(H11), C28(H28), C30(H30), C32(H32), C35(H35)
6.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C5(H5A,H5B), C9(H9A,H9B), C26(H26A,H26B), C27(H27A,
 H27B), C29(H29A,H29B), C31(H31A,H31B)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C14(H14), C15(H15), C19(H19), C23(H23), C24(H24), C33(H33), C38(H38),
 C39(H39), C43(H43), C47(H47), C48(H48), C52(H52), C53(H53)
6.d Tetrahedral OH refined with riding coordinates:
 O62(H62)
6.e X=CH2 refined with riding coordinates:
 C8(H8A,H8B), C34(H34A,H34B)
6.f Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              50383
_shelx_hkl_checksum              58340
_olex2_submission_special_instructions 'No special instructions were received'