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_7243429
_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 H4 N O3 S, 0.5(C4 O), 2(H2 O)'
_chemical_formula_sum            'C29 H33 N3 O7.5 S'
_chemical_formula_weight         575.64
_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
_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                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.5984(5)
_cell_length_b                   15.7897(5)
_cell_length_c                   23.5416(7)
_cell_measurement_reflns_used    3674
_cell_measurement_temperature    100
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      3.2
_cell_volume                     5798.2(3)
_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      100
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn 724+ HG'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0396
_diffrn_reflns_av_unetI/netI     0.0343
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            69164
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.514
_diffrn_reflns_theta_min         2.580
_exptl_absorpt_coefficient_mu    0.164
_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    1.319
_exptl_crystal_description       block
_exptl_crystal_F_000             2432
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_refine_diff_density_max         1.407
_refine_diff_density_min         -0.531
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.02(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     737
_refine_ls_number_reflns         17621
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0447
_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^)+(0.0665P)^2^+2.4572P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1184
_refine_ls_wR_factor_ref         0.1203
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.993
_reflns_Friedel_fraction_max     0.995
_reflns_number_gt                16878
_reflns_number_total             17621
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d1ce00791b2.cif
_cod_data_source_block           datam_CCDC8
_cod_depositor_comments
;
Adding full bibliography for 7243420--7243429.cif.

2024-10-18
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C58 H66 N6 O15 S2'
_cod_original_formula_weight         1151.28
_cod_original_formula_moiety
'2(C20 H25 N2 O2), 2(C7 H4 N O3 S), C4 O, 4(H2 O)'
_cod_original_formula_units_Z            4
_cod_database_code               7243429
_shelx_shelxl_version_number     2018/3
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 1.02(5)
 -0.02(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
3. Restrained distances
 O90-H90B
 0.95 with sigma of 0.02
4.a Riding coordinates:
 O12(H12), N1(H1), O36(H36), N25(H25), O90(H90A), O93(H93A,H93B), O92(H92A,
 H92B), O91(H91A,H91B)
4.b Ternary CH refined with riding coordinates:
 C2(H2), C4(H4), C8(H8), C11(H11), C27(H27), C28(H28), C30(H30), C35(H35)
4.c Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C5(H5A,H5B), C6(H6A,H6B), C7(H7A,H7B), C26(H26A,H26B), C29(H29A,
 H29B), C31(H31A,H31B), C32(H32A,H32B)
4.d Aromatic/amide H refined with riding coordinates:
 C9(H9), C14(H14), C15(H15), C19(H19), C21(H21), C22(H22), C33(H33), C38(H38),
 C39(H39), C43(H43), C47(H47), C48(H48), C55(H55), C56(H56), C57(H57), C58(H58),
  C66(H66), C67(H67), C68(H68), C69(H69)
4.e X=CH2 refined with riding coordinates:
 C10(H10A,H10B), C34(H34A,H34B)
4.f Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C), C46(H46A,H46B,H46C)
;
_shelx_res_checksum              614
_shelx_hkl_checksum              91463
_olex2_submission_special_instructions 'No special instructions were received'