Ciprofloxacin salt and salt co-crystal with dihydroxybenzoic acids
Nugraha, Yuda Prasetya; Sugiyama, Haruki; Uekusa, Hidehiro; Acta Crystallographica Section E 78 (2022) –; doi:10.1107/S2056989022001177

data_2244034
_publ_section_title
;
 Ciprofloxacin salt and salt co-crystal with dihydroxybenzoic acids
;
_journal_coeditor_code           DX2042
_journal_issue                   3
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2056989022001177
_journal_volume                  78
_journal_year                    2022
_chemical_formula_iupac          'C17 H19 F N3 O3 +, C7 H6 O4, Cl -, H2 O'
_chemical_formula_moiety         'C17 H19 F N3 O3 +, C7 H6 O4, Cl -, H2 O'
_chemical_formula_sum            'C24 H27 Cl F N3 O8'
_chemical_formula_weight         539.93
_chemical_name_common
;
Ciprofloxacin chloride--3,5-hydroxybenzoic acid--water (1/1/1)
;
_chemical_name_systematic
'4-(3-Carboxy-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)piperazin-1-ium chloride--3,5-hydroxybenzoic acid--water (1/1/1)'
_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
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_cell_angle_alpha                92.997(3)
_cell_angle_beta                 95.219(2)
_cell_angle_gamma                111.557(4)
_cell_formula_units_Z            1
_cell_length_a                   7.2165(2)
_cell_length_b                   8.8298(4)
_cell_length_c                   10.1184(3)
_cell_measurement_reflns_used    10041
_cell_measurement_temperature    93.15
_cell_measurement_theta_max      75.7970
_cell_measurement_theta_min      4.3570
_cell_volume                     594.60(4)
_computing_cell_refinement
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_collection
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_data_reduction
;
CrysAlisPro (Rigaku OD, 2020)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_structure_refinement
;
<i>SHELXL2018/3</i> (Sheldrick, 2015b)
;
_computing_structure_solution
;
<i>SHELXT2018/2</i> (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      93.15
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, DW system, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0273
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            16358
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.461
_diffrn_reflns_theta_min         4.407
_diffrn_source                   'Rotating-anode X-ray tube'
_exptl_absorpt_coefficient_mu    1.995
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83862
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlisPro; Rigaku OD, 2020)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.508
_exptl_crystal_description       block
_exptl_crystal_F_000             282
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.245
_refine_diff_density_min         -0.468
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1889 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.011(7)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.122
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         4420
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.121
_refine_ls_R_factor_all          0.0347
_refine_ls_R_factor_gt           0.0341
_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^)+(0.0589P)^2^+0.0709P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0937
_refine_ls_wR_factor_ref         0.0941
_reflns_number_gt                4323
_reflns_number_total             4420
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            dx2042sup1.cif
_cod_data_source_block           II
_cod_database_code               2244034
_shelx_estimated_absorpt_t_min   0.605
_shelx_estimated_absorpt_t_max   0.907
_shelx_hkl_checksum              14816
_shelx_res_checksum              3217
_cod_database_fobs_code 2244034