Improving aqueous solubility of ciprofloxacin: three different stoichiometric hydrated salt forms with oxalic acid
Rapeenun, Peerapon; Nalaoh, Phattananawee; Promarak, Vinich; Flood, Adrian E.; CrystEngComm 25 (2023) 4461–4469; doi:10.1039/D3CE00514C

data_7247057
_publ_section_title
;
 Improving aqueous solubility of ciprofloxacin: three different
 stoichiometric hydrated salt forms with oxalic acid
;
_journal_issue                   31
_journal_name_full               CrystEngComm
_journal_page_first              4461
_journal_page_last               4469
_journal_paper_doi               10.1039/D3CE00514C
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         '6(C17 H19 F N3 O3), 3(C2 O4), 2(H2 O)'
_chemical_formula_sum            'C108 H118 F6 N18 O32'
_chemical_formula_weight         2294.20
_chemical_name_common            'Hexa-Ciprofloxacin tri-oxalate dihydrate'
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_audit_creation_date             2021-12-23
_audit_creation_method
;
Olex2 1.5
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_audit_update_record
;
2021-12-23 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                90.753(5)
_cell_angle_beta                 93.648(4)
_cell_angle_gamma                94.741(5)
_cell_formula_units_Z            2
_cell_length_a                   13.7549(18)
_cell_length_b                   13.9237(19)
_cell_length_c                   30.361(4)
_cell_measurement_reflns_used    9850
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      28.74
_cell_measurement_theta_min      2.31
_cell_volume                     5782.1(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.5 (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEX2 area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            180592
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.484
_diffrn_reflns_theta_min         1.940
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_correction_T_min  0.7025
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1538 before and 0.0796 after correction.
The Ratio of minimum to maximum transmission is 0.9419.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.318
_exptl_crystal_description       prism
_exptl_crystal_F_000             2404
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_size_max          0.68
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.383
_refine_diff_density_min         -0.375
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1537
_refine_ls_number_reflns         26489
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0405
_refine_ls_shift/su_max          0.002
_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^+1.8298P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1092
_reflns_Friedel_coverage         0.000
_reflns_number_gt                20468
_reflns_number_total             26489
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00514c2.cif
_cod_data_source_block           mo_adf_c32_moka100k_0m
_cod_depositor_comments
'Adding full bibliography for 7247055--7247057.cif.'
_cod_database_code               7247057
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.986
_shelx_estimated_absorpt_t_min   0.932
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(O6) = Uanis(O16)
3. Others
 Fixed Sof: C2(0.6667) H2A(0.6667) H2B(0.6667) C8(0.6667) H8A(0.6667)
 H8B(0.6667) C69(0.6667) H69(0.6667) C83(0.66667) H83(0.66667) C84(0.66667)
 H84A(0.66667) H84B(0.66667) C85(0.66667) H85A(0.66667) H85B(0.66667)
 C110(0.33333) H11G(0.33333) H11H(0.33333) C109(0.33333) H109(0.33333)
 C111(0.33333) H11I(0.33333) H11J(0.33333) C112(0.33333) H112(0.33333)
 C113(0.33333) H11A(0.33333) H11B(0.33333) C114(0.33333) H11C(0.33333)
 H11D(0.33333)
4.a Free rotating group:
 O30(H30A,H30B), O31(H31A,H31B)
4.b Ternary CH refined with riding coordinates:
 C18(H18), C36(H36), C52(H52), C69(H69), C83(H83), C100(H100), C109(H109),
 C112(H112)
4.c Secondary CH2 refined with riding coordinates:
 N2(H2C,H2D), C2(H2A,H2B), C4(H4A,H4B), N5(H5A,H5B), C5(H5C,H5D), C6(H6A,H6B),
 C7(H7A,H7B), N8(H8C,H8D), C8(H8A,H8B), N11(H11E,H11F), N14(H14A,H14B),
 N17(H17A,H17B), C19(H19A,H19B), C20(H20A,H20B), C22(H22A,H22B), C23(H23A,H23B),
  C24(H24A,H24B), C25(H25A,H25B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,
 H39B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B), C53(H53A,H53B),
 C54(H54A,H54B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B),
  C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B), C73(H73A,H73B), C84(H84A,
 H84B), C85(H85A,H85B), C86(H86A,H86B), C87(H87A,H87B), C88(H88A,H88B),
 C89(H89A,H89B), C101(H10A,H10B), C102(H10C,H10D), C110(H11G,H11H), C111(H11I,
 H11J), C113(H11A,H11B), C114(H11C,H11D)
4.d Aromatic/amide H refined with riding coordinates:
 C10(H10), C13(H13), C15(H15), C28(H28), C31(H31), C34(H34), C44(H44),
 C47(H47), C49(H49), C62(H62), C65(H65), C67(H67), C75(H75), C78(H78), C80(H80),
  C92(H92), C95(H95), C98(H98)
4.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O8(H8), O11(H11), O14(H14), O17(H17)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              39340
_shelx_fab_checksum              22353
_olex2_submission_special_instructions 'No special instructions were received'