Zwitterionic <i>versus</i> neutral molecules of fluoroquinolones: crystal structure of danofloxacin dihydrate
Felczak, Aleksandra; Kalinowska-Lis, Urszula; Kusz, Joachim; Checińska, Lilianna; Acta Crystallographica Section C 78 (2022) –; doi:10.1107/S2053229622010300

data_2022694
_publ_section_title
;
 Zwitterionic <i>versus</i> neutral molecules of fluoroquinolones: crystal
 structure of danofloxacin dihydrate
;
_journal_coeditor_code           VP3026
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2053229622010300
_journal_volume                  78
_journal_year                    2022
_chemical_absolute_configuration rmad
_chemical_formula_iupac          'C19 H20 F N3 O3, 2H2 O'
_chemical_formula_moiety         'C19 H20 F N3 O3, 2(H2 O)'
_chemical_formula_sum            'C19 H24 F N3 O5'
_chemical_formula_weight         393.41
_chemical_name_common
;
Danofloxacin dihydrate
;
_chemical_name_systematic
'(1<i>S</i>,4<i>S</i>)-5-(3-Carboxylato-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydroquinolin-7-yl)-2-methyl-2,5-diazabicyclo[2.2.1]heptan-2-ium dihydrate'
_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
_atom_sites_solution_primary     difmap
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.1815(2)
_cell_length_b                   10.6840(3)
_cell_length_c                   23.5104(7)
_cell_measurement_reflns_used    5102
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      74.9670
_cell_measurement_theta_min      3.6660
_cell_volume                     1803.89(9)
_computing_cell_refinement
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_collection
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_data_reduction
;
CrysAlis PRO (Rigaku OD, 2017)
;
_computing_molecular_graphics
;
Mercury (Macrae <i>et al.</i>,  2020)
;
_computing_publication_material
;
publCIF (Westrip, 2010)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_av_unetI/netI     0.0423
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10288
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         77.330
_diffrn_reflns_theta_min         3.760
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.945
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.50341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(CrysAlis PRO; Rigaku OD, 2017)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.449
_exptl_crystal_description       needle
_exptl_crystal_F_000             832
_exptl_crystal_size_max          0.262
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.055
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.340
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1277 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   0.05(14)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.097
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     274
_refine_ls_number_reflns         3612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.097
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0464
_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^)+(0.0787P)^2^+0.4590P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1251
_refine_ls_wR_factor_ref         0.1308
_reflns_number_gt                3329
_reflns_number_total             3612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            vp3026sup1.cif
_cod_data_source_block           DFX-Cu
_cod_database_code               2022694
_shelx_hkl_checksum              3668
_shelx_res_checksum              44619
_cod_database_fobs_code 2022694