#------------------------------------------------------------------------------
#$Date: 2025-10-31 00:41:27 +0100 (Fri 31 de Oct de 2025) $
#$Revision: 303112 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/11/7251179.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_7251179
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                 104.354(16)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.630(7)
_cell_length_b                   6.5439(6)
_cell_length_c                   16.5404(16)
_cell_measurement_pressure       0.76
_cell_measurement_reflns_used    5492
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.285
_cell_measurement_theta_min      2.542
_cell_volume                     3107.0(9)
_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 0.352
_diffrn_measured_fraction_theta_max 0.352
_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  0.0732
_diffrn_reflns_av_unetI/netI     0.0500
_diffrn_reflns_Laue_measured_fraction_full 0.352
_diffrn_reflns_Laue_measured_fraction_max 0.352
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5492
_diffrn_reflns_point_group_measured_fraction_full 0.352
_diffrn_reflns_point_group_measured_fraction_max 0.352
_diffrn_reflns_theta_full        23.285
_diffrn_reflns_theta_max         23.285
_diffrn_reflns_theta_min         2.542
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6705
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.545
_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         0.102
_refine_diff_density_min         -0.101
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.151
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         792
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      0.975
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0418
_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)+(0.0594P)²+0.4936P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0967
_refine_ls_wR_factor_ref         0.1154
_reflns_Friedel_coverage         0.000
_reflns_number_gt                493
_reflns_number_total             792
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00855g2.cif
_cod_data_source_block           OFLO_0p76
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7251179
_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   0.977
_shelx_estimated_absorpt_t_max   0.994
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 0.5698(3) 0.7053(5) 0.7813(2) 0.055(5) Uani 1 1 d D . . . .
O1 O 0.6463(4) 0.6114(6) 0.5657(3) 0.039(5) Uani 1 1 d D . . . .
O4 O 0.4377(4) 0.8010(6) 0.2708(3) 0.042(6) Uani 1 1 d D . . . .
C11 C 0.5243(5) 0.7320(9) 0.5581(4) 0.028(5) Uani 1 1 d D . . . .
O2 O 0.4442(4) 0.8159(6) 0.5210(3) 0.034(5) Uani 1 1 d D . . . .
N3 N 0.5625(5) 0.6932(8) 0.4464(4) 0.029(5) Uani 1 1 d D . . . .
N1 N 0.6505(5) 0.6222(8) 0.7395(4) 0.028(5) Uani 1 1 d D . . . .
C7 C 0.5682(6) 0.6976(11) 0.6979(5) 0.027(5) Uani 1 1 d D . . . .
C10 C 0.5644(5) 0.6870(9) 0.5319(4) 0.024(4) Uani 1 1 d D . . . .
C3 C 0.5222(6) 0.7330(10) 0.3911(5) 0.028(5) Uani 1 1 d D . . . .
H3 H 0.522101 0.734872 0.334856 0.033 Uiso 1 1 calc R U . . .
C8 C 0.6094(6) 0.6535(10) 0.6758(5) 0.027(4) Uani 1 1 d D . . . .
O3 O 0.4009(4) 0.8606(7) 0.3700(3) 0.044(5) Uani 1 1 d D . . . .
H3A H 0.406819 0.858495 0.421106 0.066 Uiso 1 1 calc R U . . .
C4 C 0.4814(6) 0.7707(10) 0.4118(5) 0.029(5) Uani 1 1 d D . . . .
C6 C 0.5256(5) 0.7352(9) 0.6439(4) 0.027(5) Uani 1 1 d D . . . .
H6 H 0.499156 0.761270 0.662893 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6058(5) 0.6472(10) 0.5892(4) 0.027(5) Uani 1 1 d D . . . .
N2 N 0.7428(4) 0.6125(8) 0.8383(3) 0.042(5) Uani 1 1 d D . . . .
C13 C 0.4387(6) 0.8112(10) 0.3452(5) 0.034(5) Uani 1 1 d D . . . .
C16 C 0.7114(5) 0.7787(10) 0.8472(4) 0.042(6) Uani 1 1 d D . . . .
H16A H 0.729214 0.903203 0.862497 0.050 Uiso 1 1 calc R U . . .
H16B H 0.696470 0.745941 0.891600 0.050 Uiso 1 1 calc R U . . .
C5 C 0.4797(5) 0.7727(9) 0.4972(4) 0.026(5) Uani 1 1 d D . . . .
C1 C 0.6378(5) 0.5361(9) 0.4806(3) 0.041(6) Uani 1 1 d D . . . .
H1A H 0.623045 0.403030 0.476661 0.049 Uiso 1 1 calc R U . . .
H1B H 0.667275 0.520902 0.465461 0.049 Uiso 1 1 calc R U . . .
C12 C 0.6276(6) 0.8919(9) 0.4201(4) 0.049(8) Uani 1 1 d D . . . .
H12A H 0.605299 0.978978 0.384174 0.074 Uiso 1 1 calc R U . . .
H12B H 0.655244 0.883493 0.399778 0.074 Uiso 1 1 calc R U . . .
H12C H 0.635431 0.947371 0.475608 0.074 Uiso 1 1 calc R U . . .
C2 C 0.6072(5) 0.6814(9) 0.4215(4) 0.031(5) Uani 1 1 d D . . . .
H2 H 0.601062 0.623995 0.365106 0.037 Uiso 1 1 calc R U . . .
C17 C 0.6749(4) 0.8128(9) 0.7678(4) 0.038(6) Uani 1 1 d D . . . .
H17A H 0.652799 0.914376 0.776753 0.046 Uiso 1 1 calc R U . . .
H17B H 0.689355 0.863877 0.725204 0.046 Uiso 1 1 calc R U . . .
C15 C 0.7166(4) 0.4264(9) 0.8116(3) 0.035(5) Uani 1 1 d D . . . .
H15A H 0.700475 0.385659 0.853419 0.042 Uiso 1 1 calc R U . . .
H15B H 0.737838 0.317552 0.806147 0.042 Uiso 1 1 calc R U . . .
C18 C 0.7785(5) 0.5815(11) 0.9154(4) 0.063(6) Uani 1 1 d D . . . .
H18A H 0.795698 0.705854 0.930490 0.095 Uiso 1 1 calc R U . . .
H18B H 0.799272 0.475012 0.907507 0.095 Uiso 1 1 calc R U . . .
H18C H 0.764063 0.543094 0.959130 0.095 Uiso 1 1 calc R U . . .
C14 C 0.6819(4) 0.4575(9) 0.7299(3) 0.036(5) Uani 1 1 d D . . . .
H14A H 0.697800 0.492875 0.687142 0.043 Uiso 1 1 calc R U . . .
H14B H 0.664380 0.332790 0.713179 0.043 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 112.4(9) . . ?
C10 C11 C6 120.2(10) . . ?
C10 C11 C5 120.9(6) . . ?
C6 C11 C5 118.9(10) . . ?
C3 N3 C10 120.1(11) . . ?
C3 N3 C2 121.8(6) . . ?
C10 N3 C2 117.6(11) . . ?
C8 N1 C14 118.7(6) . . ?
C8 N1 C17 112.4(7) . . ?
C14 N1 C17 112.8(10) . . ?
F1 C7 C6 116.4(10) . . ?
F1 C7 C8 117.4(11) . . ?
C6 C7 C8 126.2(7) . . ?
C9 C10 C11 120.6(6) . . ?
C9 C10 N3 120.4(11) . . ?
C11 C10 N3 118.9(11) . . ?
N3 C3 C4 124.2(7) . . ?
N3 C3 H3 117.9 . . ?
C4 C3 H3 117.9 . . ?
C7 C8 C9 115.1(12) . . ?
C7 C8 N1 118.9(7) . . ?
C9 C8 N1 126.0(12) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.3(12) . . ?
C3 C4 C13 119.7(7) . . ?
C5 C4 C13 120.1(12) . . ?
C7 C6 C11 116.4(11) . . ?
C7 C6 H6 121.8 . . ?
C11 C6 H6 121.8 . . ?
O1 C9 C10 122.0(6) . . ?
O1 C9 C8 116.3(11) . . ?
C10 C9 C8 121.6(11) . . ?
C15 N2 C18 111.6(6) . . ?
C15 N2 C16 110.4(9) . . ?
C18 N2 C16 111.0(6) . . ?
O4 C13 O3 120.8(13) . . ?
O4 C13 C4 122.7(11) . . ?
O3 C13 C4 116.5(7) . . ?
N2 C16 C17 111.2(6) . . ?
N2 C16 H16A 109.4 . . ?
C17 C16 H16A 109.4 . . ?
N2 C16 H16B 109.4 . . ?
C17 C16 H16B 109.4 . . ?
H16A C16 H16B 108.0 . . ?
O2 C5 C4 123.8(12) . . ?
O2 C5 C11 120.6(7) . . ?
C4 C5 C11 115.5(10) . . ?
O1 C1 C2 110.3(6) . . ?
O1 C1 H1A 109.6 . . ?
C2 C1 H1A 109.6 . . ?
O1 C1 H1B 109.6 . . ?
C2 C1 H1B 109.6 . . ?
H1A C1 H1B 108.1 . . ?
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 106.9(6) . . ?
N3 C2 C12 110.3(8) . . ?
C1 C2 C12 114.1(11) . . ?
N3 C2 H2 108.5 . . ?
C1 C2 H2 108.5 . . ?
C12 C2 H2 108.5 . . ?
N1 C17 C16 110.3(6) . . ?
N1 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
N2 C15 C14 110.9(5) . . ?
N2 C15 H15A 109.5 . . ?
C14 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 108.0 . . ?
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 108.4(6) . . ?
N1 C14 H14A 110.0 . . ?
C15 C14 H14A 110.0 . . ?
N1 C14 H14B 110.0 . . ?
C15 C14 H14B 110.0 . . ?
H14A C14 H14B 108.4 . . ?
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 1.369(6) . ?
O1 C9 1.368(13) . ?
O1 C1 1.454(6) . ?
O4 C13 1.225(7) . ?
C11 C10 1.394(12) . ?
C11 C6 1.409(7) . ?
C11 C5 1.473(11) . ?
O2 C5 1.245(13) . ?
N3 C3 1.337(16) . ?
N3 C10 1.401(7) . ?
N3 C2 1.484(15) . ?
N1 C8 1.413(16) . ?
N1 C14 1.458(11) . ?
N1 C17 1.459(10) . ?
C7 C6 1.376(16) . ?
C7 C8 1.390(18) . ?
C10 C9 1.378(15) . ?
C3 C4 1.356(17) . ?
C3 H3 0.9300 . ?
C8 C9 1.410(8) . ?
O3 C13 1.326(15) . ?
O3 H3A 0.8200 . ?
C4 C5 1.426(9) . ?
C4 C13 1.481(15) . ?
C6 H6 0.9300 . ?
N2 C15 1.453(10) . ?
N2 C18 1.456(9) . ?
N2 C16 1.462(11) . ?
C16 C17 1.497(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.498(13) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.507(10) . ?
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 1.495(9) . ?
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 -0.7(10) . . . . ?
C5 C11 C10 C9 -179.4(7) . . . . ?
C6 C11 C10 N3 -177.4(6) . . . . ?
C5 C11 C10 N3 3.9(10) . . . . ?
C3 N3 C10 C9 -179.6(8) . . . . ?
C2 N3 C10 C9 -7.4(10) . . . . ?
C3 N3 C10 C11 -2.9(11) . . . . ?
C2 N3 C10 C11 169.3(6) . . . . ?
C10 N3 C3 C4 0.5(12) . . . . ?
C2 N3 C3 C4 -171.4(7) . . . . ?
F1 C7 C8 C9 179.9(5) . . . . ?
C6 C7 C8 C9 -0.3(13) . . . . ?
F1 C7 C8 N1 -0.9(11) . . . . ?
C6 C7 C8 N1 178.9(7) . . . . ?
C14 N1 C8 C7 138.6(8) . . . . ?
C17 N1 C8 C7 -86.6(9) . . . . ?
C14 N1 C8 C9 -42.2(11) . . . . ?
C17 N1 C8 C9 92.5(9) . . . . ?
N3 C3 C4 C5 0.9(12) . . . . ?
N3 C3 C4 C13 -179.4(8) . . . . ?
F1 C7 C6 C11 178.5(5) . . . . ?
C8 C7 C6 C11 -1.2(13) . . . . ?
C10 C11 C6 C7 1.7(10) . . . . ?
C5 C11 C6 C7 -179.6(7) . . . . ?
C1 O1 C9 C10 -24.2(9) . . . . ?
C1 O1 C9 C8 159.5(5) . . . . ?
C11 C10 C9 O1 -177.0(6) . . . . ?
N3 C10 C9 O1 -0.4(12) . . . . ?
C11 C10 C9 C8 -0.9(11) . . . . ?
N3 C10 C9 C8 175.7(6) . . . . ?
C7 C8 C9 O1 177.7(7) . . . . ?
N1 C8 C9 O1 -1.4(10) . . . . ?
C7 C8 C9 C10 1.4(11) . . . . ?
N1 C8 C9 C10 -177.7(7) . . . . ?
C3 C4 C13 O4 4.3(11) . . . . ?
C5 C4 C13 O4 -176.1(6) . . . . ?
C3 C4 C13 O3 -175.6(7) . . . . ?
C5 C4 C13 O3 4.1(10) . . . . ?
C15 N2 C16 C17 -56.4(7) . . . . ?
C18 N2 C16 C17 179.4(7) . . . . ?
C3 C4 C5 O2 176.4(7) . . . . ?
C13 C4 C5 O2 -3.3(11) . . . . ?
C3 C4 C5 C11 0.1(10) . . . . ?
C13 C4 C5 C11 -179.6(6) . . . . ?
C10 C11 C5 O2 -178.9(7) . . . . ?
C6 C11 C5 O2 2.4(10) . . . . ?
C10 C11 C5 C4 -2.5(9) . . . . ?
C6 C11 C5 C4 178.8(6) . . . . ?
C9 O1 C1 C2 55.8(9) . . . . ?
C3 N3 C2 C1 -150.9(7) . . . . ?
C10 N3 C2 C1 37.0(8) . . . . ?
C3 N3 C2 C12 84.5(9) . . . . ?
C10 N3 C2 C12 -87.6(8) . . . . ?
O1 C1 C2 N3 -60.9(10) . . . . ?
O1 C1 C2 C12 61.4(11) . . . . ?
C8 N1 C17 C16 167.0(8) . . . . ?
C14 N1 C17 C16 -55.5(7) . . . . ?
N2 C16 C17 N1 53.8(9) . . . . ?
C18 N2 C15 C14 -176.8(7) . . . . ?
C16 N2 C15 C14 59.3(7) . . . . ?
C8 N1 C14 C15 -167.9(8) . . . . ?
C17 N1 C14 C15 57.5(7) . . . . ?
N2 C15 C14 N1 -58.9(9) . . . . ?
