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#$Date: 2025-10-31 01:41:27 +0200 (Fri, 31 Oct 2025) $
#$Revision: 303112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/11/7251171.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7251171
loop_
_publ_author_name
'Gasol-Cardona, Julia'
'Ward, Martin R.'
'Comboni, Davide'
'Michael, Hanfland'
'Scatena, Rebecca'
'Warren, Mark R.'
'Maloney, Andrew G. P.'
'Oswald, Iain D. H.'
_publ_section_title
;
 Pressure-Induced Phase Behaviour and Compressibility of the Racemic and
 Chiral Solid Forms, Ofloxacin and Levofloxacin
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/D5CE00855G
_journal_year                    2025
_chemical_formula_moiety         'C18 H20 F N3 O4'
_chemical_formula_sum            'C18 H20 F N3 O4'
_chemical_formula_weight         361.37
_chemical_name_systematic        Ofloxacin
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2019/3
_audit_update_record
;
2025-08-19 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.15(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   30.251(10)
_cell_length_b                   6.8318(8)
_cell_length_c                   16.845(2)
_cell_measurement_pressure       0.0
_cell_measurement_reflns_used    5571
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.320
_cell_measurement_theta_min      2.505
_cell_volume                     3360.3(13)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-ac7-013 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.338
_diffrn_measured_fraction_theta_max 0.338
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0793
_diffrn_reflns_av_unetI/netI     0.0591
_diffrn_reflns_Laue_measured_fraction_full 0.338
_diffrn_reflns_Laue_measured_fraction_max 0.338
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5571
_diffrn_reflns_point_group_measured_fraction_full 0.338
_diffrn_reflns_point_group_measured_fraction_max 0.338
_diffrn_reflns_theta_full        23.320
_diffrn_reflns_theta_max         23.320
_diffrn_reflns_theta_min         2.505
_exptl_absorpt_coefficient_mu    0.109
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6250
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_description       needle
_exptl_crystal_F_000             1520
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: Nitrobenzene'
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.083
_refine_diff_density_min         -0.089
_refine_diff_density_rms         0.023
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         826
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      0.899
_refine_ls_R_factor_all          0.1127
_refine_ls_R_factor_gt           0.0415
_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/[σ²(Fo²)+(0.0428P)²+2.7240P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0814
_refine_ls_wR_factor_ref         0.1057
_reflns_Friedel_coverage         0.000
_reflns_number_gt                450
_reflns_number_total             826
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00855g2.cif
_cod_data_source_block           OFLO_AMBIENT
_cod_original_cell_volume        3360.3(12)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7251171
_shelx_shelxl_version_number     2019/3
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.978
_shelx_estimated_absorpt_t_max   0.995
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.5692(3) 0.7039(5) 0.7763(2) 0.074(7) Uani 1 1 d D . . . .
O1 O 0.6440(4) 0.6193(7) 0.5651(3) 0.059(5) Uani 1 1 d D . . . .
O4 O 0.4393(4) 0.7992(6) 0.2722(3) 0.062(7) Uani 1 1 d D . . . .
C11 C 0.5229(5) 0.7323(10) 0.5551(4) 0.042(5) Uani 1 1 d D . . . .
O2 O 0.4444(4) 0.8125(7) 0.5178(3) 0.058(6) Uani 1 1 d D . . . .
N3 N 0.5612(5) 0.6967(9) 0.4471(4) 0.044(5) Uani 1 1 d D . . . .
N1 N 0.6474(5) 0.6309(10) 0.7343(4) 0.047(5) Uani 1 1 d D . . . .
C7 C 0.5663(6) 0.6995(12) 0.6928(5) 0.039(5) Uani 1 1 d D . . . .
C10 C 0.5624(6) 0.6919(10) 0.5306(5) 0.042(5) Uani 1 1 d D . . . .
C3 C 0.5214(7) 0.7357(13) 0.3918(6) 0.046(6) Uani 1 1 d D . . . .
H3 H 0.521153 0.738781 0.336500 0.056 Uiso 1 1 calc R U . . .
C8 C 0.6077(6) 0.6587(11) 0.6725(5) 0.041(5) Uani 1 1 d D . . . .
O3 O 0.4027(5) 0.8547(7) 0.3683(4) 0.063(6) Uani 1 1 d D . . . .
H3A H 0.407853 0.842018 0.418253 0.094 Uiso 1 1 calc R U . . .
C4 C 0.4815(6) 0.7706(11) 0.4117(5) 0.047(5) Uani 1 1 d D . . . .
C6 C 0.5240(6) 0.7356(12) 0.6393(5) 0.047(6) Uani 1 1 d D . . . .
H6 H 0.498105 0.760368 0.657543 0.057 Uiso 1 1 calc R U . . .
C9 C 0.6040(5) 0.6528(11) 0.5879(5) 0.043(5) Uani 1 1 d D . . . .
N2 N 0.7388(5) 0.6185(11) 0.8370(4) 0.081(7) Uani 1 1 d D . . . .
C13 C 0.4397(6) 0.8066(12) 0.3447(5) 0.051(6) Uani 1 1 d D . . . .
C16 C 0.7071(5) 0.7712(12) 0.8445(5) 0.072(7) Uani 1 1 d D . . . .
H16A H 0.724137 0.890508 0.862527 0.086 Uiso 1 1 calc R U . . .
H16B H 0.692015 0.733968 0.886417 0.086 Uiso 1 1 calc R U . . .
C5 C 0.4788(5) 0.7745(10) 0.4954(5) 0.043(5) Uani 1 1 d D . . . .
C1 C 0.6361(5) 0.5448(9) 0.4815(4) 0.060(7) Uani 1 1 d D . . . .
H1A H 0.622258 0.415844 0.477833 0.072 Uiso 1 1 calc R U . . .
H1B H 0.664983 0.533360 0.467049 0.072 Uiso 1 1 calc R U . . .
C12 C 0.6269(6) 0.8836(9) 0.4218(4) 0.060(9) Uani 1 1 d D . . . .
H12A H 0.605697 0.970176 0.386069 0.090 Uiso 1 1 calc R U . . .
H12B H 0.653872 0.870142 0.402253 0.090 Uiso 1 1 calc R U . . .
H12C H 0.635167 0.936368 0.476473 0.090 Uiso 1 1 calc R U . . .
C2 C 0.6046(6) 0.6831(10) 0.4225(5) 0.048(6) Uani 1 1 d D . . . .
H2 H 0.598093 0.627509 0.367035 0.058 Uiso 1 1 calc R U . . .
C17 C 0.6718(5) 0.8112(11) 0.7670(4) 0.069(7) Uani 1 1 d D . . . .
H17A H 0.650219 0.906837 0.777010 0.083 Uiso 1 1 calc R U . . .
H17B H 0.686260 0.865548 0.726792 0.083 Uiso 1 1 calc R U . . .
C15 C 0.7143(5) 0.4429(11) 0.8072(4) 0.066(6) Uani 1 1 d D . . . .
H15A H 0.699280 0.395248 0.847811 0.079 Uiso 1 1 calc R U . . .
H15B H 0.735724 0.343444 0.799795 0.079 Uiso 1 1 calc R U . . .
C18 C 0.7737(6) 0.5827(13) 0.9120(5) 0.112(8) Uani 1 1 d D . . . .
H18A H 0.790472 0.701270 0.929478 0.168 Uiso 1 1 calc R U . . .
H18B H 0.794267 0.483592 0.902556 0.168 Uiso 1 1 calc R U . . .
H18C H 0.759707 0.539403 0.953865 0.168 Uiso 1 1 calc R U . . .
C14 C 0.6795(5) 0.4749(11) 0.7283(4) 0.066(6) Uani 1 1 d D . . . .
H14A H 0.694811 0.508777 0.686211 0.079 Uiso 1 1 calc R U . . .
H14B H 0.662672 0.354425 0.711729 0.079 Uiso 1 1 calc R U . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 O1 C1 113.0(10) . . ?
C10 C11 C6 120.3(11) . . ?
C10 C11 C5 122.1(7) . . ?
C6 C11 C5 117.6(10) . . ?
C3 N3 C10 119.0(12) . . ?
C3 N3 C2 121.2(7) . . ?
C10 N3 C2 119.3(12) . . ?
C8 N1 C14 120.7(8) . . ?
C8 N1 C17 114.9(8) . . ?
C14 N1 C17 111.0(12) . . ?
C6 C7 F1 117.4(11) . . ?
C6 C7 C8 127.4(8) . . ?
F1 C7 C8 115.2(12) . . ?
C11 C10 C9 121.5(7) . . ?
C11 C10 N3 119.7(11) . . ?
C9 C10 N3 118.8(11) . . ?
N3 C3 C4 123.9(8) . . ?
N3 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
N1 C8 C9 125.9(14) . . ?
N1 C8 C7 119.8(7) . . ?
C9 C8 C7 114.4(13) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 122.0(13) . . ?
C3 C4 C13 118.7(8) . . ?
C5 C4 C13 119.3(12) . . ?
C7 C6 C11 115.4(12) . . ?
C7 C6 H6 122.3 . . ?
C11 C6 H6 122.3 . . ?
O1 C9 C10 122.5(7) . . ?
O1 C9 C8 116.4(12) . . ?
C10 C9 C8 121.0(12) . . ?
C15 N2 C18 111.1(8) . . ?
C15 N2 C16 109.9(11) . . ?
C18 N2 C16 113.5(7) . . ?
O4 C13 O3 121.6(14) . . ?
O4 C13 C4 122.6(12) . . ?
O3 C13 C4 115.8(8) . . ?
N2 C16 C17 113.5(7) . . ?
N2 C16 H16A 108.9 . . ?
C17 C16 H16A 108.9 . . ?
N2 C16 H16B 108.9 . . ?
C17 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
O2 C5 C4 125.3(13) . . ?
O2 C5 C11 121.5(8) . . ?
C4 C5 C11 113.2(11) . . ?
O1 C1 C2 109.4(6) . . ?
O1 C1 H1A 109.8 . . ?
C2 C1 H1A 109.8 . . ?
O1 C1 H1B 109.8 . . ?
C2 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C2 C12 H12A 109.5 . . ?
C2 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C2 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N3 C2 C1 107.9(7) . . ?
N3 C2 C12 111.8(9) . . ?
C1 C2 C12 111.2(12) . . ?
N3 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
C12 C2 H2 108.6 . . ?
N1 C17 C16 110.7(8) . . ?
N1 C17 H17A 109.5 . . ?
C16 C17 H17A 109.5 . . ?
N1 C17 H17B 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 108.1 . . ?
N2 C15 C14 111.9(7) . . ?
N2 C15 H15A 109.2 . . ?
C14 C15 H15A 109.2 . . ?
N2 C15 H15B 109.2 . . ?
C14 C15 H15B 109.2 . . ?
H15A C15 H15B 107.9 . . ?
N2 C18 H18A 109.5 . . ?
N2 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N2 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N1 C14 C15 112.0(7) . . ?
N1 C14 H14A 109.2 . . ?
C15 C14 H14A 109.2 . . ?
N1 C14 H14B 109.2 . . ?
C15 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C7 1.386(7) . ?
O1 C9 1.381(14) . ?
O1 C1 1.456(7) . ?
O4 C13 1.220(7) . ?
C11 C10 1.391(13) . ?
C11 C6 1.411(8) . ?
C11 C5 1.473(11) . ?
O2 C5 1.225(13) . ?
N3 C3 1.344(16) . ?
N3 C10 1.397(8) . ?
N3 C2 1.479(16) . ?
N1 C8 1.380(18) . ?
N1 C14 1.464(12) . ?
N1 C17 1.468(11) . ?
C7 C6 1.380(17) . ?
C7 C8 1.410(19) . ?
C10 C9 1.396(16) . ?
C3 C4 1.355(18) . ?
C3 H3 0.9300 . ?
C8 C9 1.402(9) . ?
O3 C13 1.322(16) . ?
O3 H3A 0.8200 . ?
C4 C5 1.434(10) . ?
C4 C13 1.480(15) . ?
C6 H6 0.9300 . ?
N2 C15 1.431(12) . ?
N2 C18 1.440(10) . ?
N2 C16 1.444(13) . ?
C16 C17 1.479(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.514(15) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.528(11) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C2 H2 0.9800 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C15 C14 1.480(10) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C11 C10 C9 0.3(12) . . . . ?
C5 C11 C10 C9 179.8(9) . . . . ?
C6 C11 C10 N3 -177.5(7) . . . . ?
C5 C11 C10 N3 2.0(11) . . . . ?
C3 N3 C10 C11 -1.7(13) . . . . ?
C2 N3 C10 C11 170.9(7) . . . . ?
C3 N3 C10 C9 -179.5(9) . . . . ?
C2 N3 C10 C9 -7.0(12) . . . . ?
C10 N3 C3 C4 -0.2(16) . . . . ?
C2 N3 C3 C4 -172.6(8) . . . . ?
C14 N1 C8 C9 -42.8(14) . . . . ?
C17 N1 C8 C9 94.5(10) . . . . ?
C14 N1 C8 C7 138.1(9) . . . . ?
C17 N1 C8 C7 -84.6(11) . . . . ?
C6 C7 C8 N1 178.3(9) . . . . ?
F1 C7 C8 N1 -1.4(13) . . . . ?
C6 C7 C8 C9 -0.9(15) . . . . ?
F1 C7 C8 C9 179.4(6) . . . . ?
N3 C3 C4 C5 1.8(16) . . . . ?
N3 C3 C4 C13 -178.4(9) . . . . ?
F1 C7 C6 C11 179.2(5) . . . . ?
C8 C7 C6 C11 -0.6(16) . . . . ?
C10 C11 C6 C7 0.9(12) . . . . ?
C5 C11 C6 C7 -178.6(8) . . . . ?
C1 O1 C9 C10 -25.3(11) . . . . ?
C1 O1 C9 C8 158.8(6) . . . . ?
C11 C10 C9 O1 -177.6(6) . . . . ?
N3 C10 C9 O1 0.2(13) . . . . ?
C11 C10 C9 C8 -1.9(13) . . . . ?
N3 C10 C9 C8 175.9(6) . . . . ?
N1 C8 C9 O1 -1.1(12) . . . . ?
C7 C8 C9 O1 178.1(7) . . . . ?
N1 C8 C9 C10 -177.1(9) . . . . ?
C7 C8 C9 C10 2.1(13) . . . . ?
C3 C4 C13 O4 2.6(14) . . . . ?
C5 C4 C13 O4 -177.6(7) . . . . ?
C3 C4 C13 O3 -175.0(8) . . . . ?
C5 C4 C13 O3 4.8(12) . . . . ?
C15 N2 C16 C17 -56.3(9) . . . . ?
C18 N2 C16 C17 178.7(9) . . . . ?
C3 C4 C5 O2 177.0(9) . . . . ?
C13 C4 C5 O2 -2.7(14) . . . . ?
C3 C4 C5 C11 -1.4(13) . . . . ?
C13 C4 C5 C11 178.8(7) . . . . ?
C10 C11 C5 O2 -179.0(8) . . . . ?
C6 C11 C5 O2 0.5(12) . . . . ?
C10 C11 C5 C4 -0.5(11) . . . . ?
C6 C11 C5 C4 179.0(7) . . . . ?
C9 O1 C1 C2 55.0(10) . . . . ?
C3 N3 C2 C1 -151.6(9) . . . . ?
C10 N3 C2 C1 36.0(9) . . . . ?
C3 N3 C2 C12 85.8(11) . . . . ?
C10 N3 C2 C12 -86.6(10) . . . . ?
O1 C1 C2 N3 -59.1(10) . . . . ?
O1 C1 C2 C12 63.8(11) . . . . ?
C8 N1 C17 C16 166.8(9) . . . . ?
C14 N1 C17 C16 -51.9(8) . . . . ?
N2 C16 C17 N1 54.5(11) . . . . ?
C18 N2 C15 C14 -177.6(8) . . . . ?
C16 N2 C15 C14 56.0(9) . . . . ?
C8 N1 C14 C15 -167.9(9) . . . . ?
C17 N1 C14 C15 53.3(9) . . . . ?
N2 C15 C14 N1 -56.0(11) . . . . ?
