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_7247055
_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
'C17 H19 F N3 O3, 0.5(C2 H2 O4), 0.5(C2 O4), H2 O'
_chemical_formula_sum            'C19 H22 F N3 O8'
_chemical_formula_weight         439.39
_chemical_name_common
'Bis(Ciprofloxacin) oxalic acid 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                70.605(2)
_cell_angle_beta                 84.799(2)
_cell_angle_gamma                76.466(2)
_cell_formula_units_Z            2
_cell_length_a                   7.2373(5)
_cell_length_b                   11.5245(8)
_cell_length_c                   12.2725(8)
_cell_measurement_reflns_used    9756
_cell_measurement_temperature    140.0
_cell_measurement_theta_max      28.29
_cell_measurement_theta_min      2.99
_cell_volume                     938.61(11)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 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      140.00
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 0.998
_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  0.0270
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            29847
_diffrn_reflns_point_group_measured_fraction_full 0.998
_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         1.919
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.128
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.7085
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1056 before and 0.0481 after correction.
The Ratio of minimum to maximum transmission is 0.9501.
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    1.555
_exptl_crystal_description       block
_exptl_crystal_F_000             460
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_size_max          0.48
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.477
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.051
_refine_ls_extinction_coef       0.046(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     302
_refine_ls_number_reflns         4303
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0334
_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^)+(0.0479P)^2^+0.4312P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0906
_refine_ls_wR_factor_ref         0.0929
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3926
_reflns_number_total             4303
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00514c2.cif
_cod_data_source_block           mo_adf_1per1ciox_moka100k_0m
_cod_depositor_comments
'Adding full bibliography for 7247055--7247057.cif.'
_cod_database_code               7247055
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.972
_shelx_estimated_absorpt_t_min   0.941
_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 O(H) groups
2.a Ternary CH refined with riding coordinates:
 C15(H15)
2.b Secondary CH2 refined with riding coordinates:
 C1(H1C,H1D), C2(H2A,H2B), C9(H9A,H9B), C10(H10A,H10B), C16(H16A,H16B),
 C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C4(H4), C6(H6), C12(H12)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              87738
_olex2_submission_special_instructions 'No special instructions were received'