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_7247056
_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), C2 H O4 -, H2 O'
_chemical_formula_sum            'C20 H23 F N3 O10'
_chemical_formula_weight         484.41
_chemical_melting_point          505.47
_chemical_name_common
'Bis(Ciprofloxacin) oxalic acid dioxalate 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             2021-04-10
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2021-07-01 deposited with the CCDC.	2023-07-14 downloaded from the CCDC.
;
_cell_angle_alpha                77.766(4)
_cell_angle_beta                 89.132(4)
_cell_angle_gamma                82.126(4)
_cell_formula_units_Z            2
_cell_length_a                   7.1349(8)
_cell_length_b                   11.9568(14)
_cell_length_c                   12.3200(13)
_cell_measurement_reflns_used    9916
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      27.17
_cell_measurement_theta_min      2.88
_cell_volume                     1017.4(2)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_temperature      100.0
_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  0.0602
_diffrn_reflns_av_unetI/netI     0.0267
_diffrn_reflns_Laue_measured_fraction_full 0.999
_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       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            43420
_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         26.733
_diffrn_reflns_theta_min         2.167
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1736 before and 0.0551 after correction.
The Ratio of minimum to maximum transmission is 0.9388.
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    1.581
_exptl_crystal_description       prism
_exptl_crystal_F_000             506
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
_exptl_crystal_size_max          0.49
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     332
_refine_ls_number_reflns         4315
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0353
_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^)+(0.0460P)^2^+0.4257P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0864
_refine_ls_wR_factor_ref         0.0916
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3548
_reflns_number_total             4315
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3ce00514c2.cif
_cod_data_source_block           mo_adf_20210409_c18run1_moka10
_cod_depositor_comments
'Adding full bibliography for 7247055--7247057.cif.'
_cod_database_code               7247056
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.937
_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:
 C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B), C13(H13A,H13B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,
 H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C5(H5), C8(H8)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              11692
_olex2_submission_special_instructions 'No special instructions were received'