#------------------------------------------------------------------------------
#$Date: 2025-10-31 00:41:27 +0100 (Fri 31 de Oct de 2025) $
#$Revision: 303112 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/11/7251175.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_7251175
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                 103.278(15)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.697(7)
_cell_length_b                   6.1346(5)
_cell_length_c                   15.9813(14)
_cell_measurement_pressure       3.62
_cell_measurement_reflns_used    4764
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.266
_cell_measurement_theta_min      2.619
_cell_volume                     2738.2(8)
_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 0.348
_diffrn_measured_fraction_theta_max 0.348
_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  0.0598
_diffrn_reflns_av_unetI/netI     0.0428
_diffrn_reflns_Laue_measured_fraction_full 0.348
_diffrn_reflns_Laue_measured_fraction_max 0.348
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            4764
_diffrn_reflns_point_group_measured_fraction_full 0.348
_diffrn_reflns_point_group_measured_fraction_max 0.348
_diffrn_reflns_theta_full        23.266
_diffrn_reflns_theta_max         23.266
_diffrn_reflns_theta_min         2.619
_exptl_absorpt_coefficient_mu    0.134
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6464
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.753
_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         0.154
_refine_diff_density_min         -0.143
_refine_diff_density_rms         0.032
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         686
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      0.912
_refine_ls_R_factor_all          0.0687
_refine_ls_R_factor_gt           0.0375
_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)+(0.0446P)²+4.3269P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0803
_refine_ls_wR_factor_ref         0.0965
_reflns_Friedel_coverage         0.000
_reflns_number_gt                483
_reflns_number_total             686
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00855g2.cif
_cod_data_source_block           OFLO_3p62
_cod_original_cell_volume        2738.2(7)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7251175
_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   0.974
_shelx_estimated_absorpt_t_max   0.993
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 0.5703(3) 0.7019(5) 0.78986(19) 0.028(5) Uani 1 1 d D . . . .
O1 O 0.6490(4) 0.5899(6) 0.5663(3) 0.034(5) Uani 1 1 d D . . . .
O4 O 0.4348(4) 0.8118(5) 0.2676(2) 0.021(6) Uani 1 1 d D . . . .
C11 C 0.5237(5) 0.7283(9) 0.5606(4) 0.026(4) Uani 1 1 d D . . . .
O2 O 0.4419(4) 0.8239(6) 0.5255(3) 0.030(5) Uani 1 1 d D . . . .
N3 N 0.5635(5) 0.6850(8) 0.4449(3) 0.026(4) Uani 1 1 d D . . . .
N1 N 0.6509(5) 0.6056(7) 0.7445(3) 0.030(4) Uani 1 1 d D . . . .
C7 C 0.5673(6) 0.6914(9) 0.7025(4) 0.023(4) Uani 1 1 d D . . . .
C10 C 0.5653(5) 0.6792(9) 0.5327(4) 0.026(4) Uani 1 1 d D . . . .
C3 C 0.5227(6) 0.7305(10) 0.3891(5) 0.023(5) Uani 1 1 d D . . . .
H3 H 0.522819 0.733305 0.330945 0.028 Uiso 1 1 calc R U . . .
C8 C 0.6098(6) 0.6375(9) 0.6797(4) 0.026(4) Uani 1 1 d D . . . .
O3 O 0.3991(4) 0.8721(6) 0.3737(3) 0.031(5) Uani 1 1 d D . . . .
H3A H 0.406110 0.872503 0.426403 0.047 Uiso 1 1 calc R U . . .
C4 C 0.4807(6) 0.7730(9) 0.4116(4) 0.023(4) Uani 1 1 d D . . . .
C6 C 0.5246(6) 0.7354(9) 0.6488(4) 0.028(5) Uani 1 1 d D . . . .
H6 H 0.497548 0.768361 0.668948 0.033 Uiso 1 1 calc R U . . .
C9 C 0.6074(5) 0.6331(10) 0.5911(4) 0.026(4) Uani 1 1 d D . . . .
N2 N 0.7468(4) 0.5962(7) 0.8417(3) 0.031(5) Uani 1 1 d D . . . .
C13 C 0.4369(6) 0.8195(9) 0.3449(4) 0.026(5) Uani 1 1 d D . . . .
C16 C 0.7154(5) 0.7778(9) 0.8508(3) 0.032(6) Uani 1 1 d D . . . .
H16A H 0.734293 0.909766 0.864046 0.038 Uiso 1 1 calc R U . . .
H16B H 0.700419 0.748805 0.898271 0.038 Uiso 1 1 calc R U . . .
C5 C 0.4782(5) 0.7756(9) 0.4998(4) 0.023(4) Uani 1 1 d D . . . .
C1 C 0.6440(5) 0.5203(8) 0.4785(3) 0.034(6) Uani 1 1 d D . . . .
H1A H 0.631063 0.373582 0.471283 0.041 Uiso 1 1 calc R U . . .
H1B H 0.675023 0.519528 0.464101 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6313(6) 0.9007(8) 0.4203(4) 0.029(7) Uani 1 1 d D . . . .
H12A H 0.609811 0.992417 0.380459 0.043 Uiso 1 1 calc R U . . .
H12B H 0.661448 0.892414 0.404055 0.043 Uiso 1 1 calc R U . . .
H12C H 0.636100 0.960676 0.477110 0.043 Uiso 1 1 calc R U . . .
C2 C 0.6103(6) 0.6770(9) 0.4191(4) 0.028(5) Uani 1 1 d D . . . .
H2 H 0.604625 0.620432 0.360268 0.033 Uiso 1 1 calc R U . . .
C17 C 0.6773(5) 0.8116(8) 0.7700(3) 0.029(5) Uani 1 1 d D . . . .
H17A H 0.655225 0.923651 0.779412 0.035 Uiso 1 1 calc R U . . .
H17B H 0.691921 0.860009 0.724163 0.035 Uiso 1 1 calc R U . . .
C15 C 0.7195(5) 0.3962(8) 0.8176(3) 0.030(5) Uani 1 1 d D . . . .
H15A H 0.703310 0.356397 0.862354 0.036 Uiso 1 1 calc R U . . .
H15B H 0.741129 0.278631 0.811619 0.036 Uiso 1 1 calc R U . . .
C18 C 0.7834(5) 0.5641(10) 0.9211(3) 0.039(6) Uani 1 1 d D . . . .
H18A H 0.801919 0.694978 0.934575 0.059 Uiso 1 1 calc R U . . .
H18B H 0.803992 0.446076 0.913505 0.059 Uiso 1 1 calc R U . . .
H18C H 0.768252 0.530203 0.967164 0.059 Uiso 1 1 calc R U . . .
C14 C 0.6833(5) 0.4272(9) 0.7343(3) 0.035(5) Uani 1 1 d D . . . .
H14A H 0.699430 0.462305 0.688839 0.042 Uiso 1 1 calc R U . . .
H14B H 0.665237 0.293931 0.718731 0.042 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 116.2(10) . . ?
C10 C11 C6 120.3(10) . . ?
C10 C11 C5 121.8(6) . . ?
C6 C11 C5 117.8(10) . . ?
C3 N3 C10 120.3(11) . . ?
C3 N3 C2 122.1(6) . . ?
C10 N3 C2 116.7(11) . . ?
C8 N1 C14 118.2(6) . . ?
C8 N1 C17 112.2(6) . . ?
C14 N1 C17 111.6(9) . . ?
C6 C7 F1 118.1(10) . . ?
C6 C7 C8 127.0(7) . . ?
F1 C7 C8 114.9(11) . . ?
C9 C10 N3 120.9(11) . . ?
C9 C10 C11 120.5(6) . . ?
N3 C10 C11 118.5(11) . . ?
N3 C3 C4 124.1(7) . . ?
N3 C3 H3 118.0 . . ?
C4 C3 H3 118.0 . . ?
C7 C8 N1 118.9(6) . . ?
C7 C8 C9 115.2(12) . . ?
N1 C8 C9 125.8(12) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.9(12) . . ?
C3 C4 C13 120.3(7) . . ?
C5 C4 C13 118.8(12) . . ?
C7 C6 C11 116.0(11) . . ?
C7 C6 H6 122.0 . . ?
C11 C6 H6 122.0 . . ?
O1 C9 C10 122.1(6) . . ?
O1 C9 C8 116.9(11) . . ?
C10 C9 C8 120.9(11) . . ?
C15 N2 C16 111.3(9) . . ?
C15 N2 C18 110.6(5) . . ?
C16 N2 C18 110.7(5) . . ?
O4 C13 O3 120.6(12) . . ?
O4 C13 C4 123.9(11) . . ?
O3 C13 C4 115.4(7) . . ?
N2 C16 C17 111.3(5) . . ?
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 124.5(12) . . ?
O2 C5 C11 121.1(6) . . ?
C4 C5 C11 114.3(11) . . ?
O1 C1 C2 109.0(6) . . ?
O1 C1 H1A 109.9 . . ?
C2 C1 H1A 109.9 . . ?
O1 C1 H1B 109.9 . . ?
C2 C1 H1B 109.9 . . ?
H1A C1 H1B 108.3 . . ?
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 C12 110.6(8) . . ?
N3 C2 C1 109.3(7) . . ?
C12 C2 C1 111.9(11) . . ?
N3 C2 H2 108.3 . . ?
C12 C2 H2 108.3 . . ?
C1 C2 H2 108.3 . . ?
N1 C17 C16 110.1(5) . . ?
N1 C17 H17A 109.6 . . ?
C16 C17 H17A 109.6 . . ?
N1 C17 H17B 109.6 . . ?
C16 C17 H17B 109.6 . . ?
H17A C17 H17B 108.2 . . ?
N2 C15 C14 110.4(5) . . ?
N2 C15 H15A 109.6 . . ?
C14 C15 H15A 109.6 . . ?
N2 C15 H15B 109.6 . . ?
C14 C15 H15B 109.6 . . ?
H15A C15 H15B 108.1 . . ?
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 108.8(5) . . ?
N1 C14 H14A 109.9 . . ?
C15 C14 H14A 109.9 . . ?
N1 C14 H14B 109.9 . . ?
C15 C14 H14B 109.9 . . ?
H14A C14 H14B 108.3 . . ?
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 1.380(6) . ?
O1 C9 1.369(14) . ?
O1 C1 1.442(6) . ?
O4 C13 1.223(7) . ?
C11 C10 1.399(13) . ?
C11 C6 1.405(7) . ?
C11 C5 1.467(11) . ?
O2 C5 1.241(13) . ?
N3 C3 1.328(15) . ?
N3 C10 1.393(7) . ?
N3 C2 1.493(16) . ?
N1 C8 1.393(15) . ?
N1 C14 1.469(11) . ?
N1 C17 1.482(10) . ?
C7 C6 1.350(16) . ?
C7 C8 1.391(18) . ?
C10 C9 1.374(15) . ?
C3 C4 1.358(17) . ?
C3 H3 0.9300 . ?
C8 C9 1.402(8) . ?
O3 C13 1.314(15) . ?
O3 H3A 0.8200 . ?
C4 C5 1.428(9) . ?
C4 C13 1.477(14) . ?
C6 H6 0.9300 . ?
N2 C15 1.459(10) . ?
N2 C16 1.461(11) . ?
N2 C18 1.462(9) . ?
C16 C17 1.503(10) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.529(14) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.497(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 1.501(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
C3 N3 C10 C9 -179.8(7) . . . . ?
C2 N3 C10 C9 -10.1(9) . . . . ?
C3 N3 C10 C11 -1.8(10) . . . . ?
C2 N3 C10 C11 167.8(5) . . . . ?
C6 C11 C10 C9 1.3(10) . . . . ?
C5 C11 C10 C9 -179.3(7) . . . . ?
C6 C11 C10 N3 -176.7(6) . . . . ?
C5 C11 C10 N3 2.8(9) . . . . ?
C10 N3 C3 C4 -0.2(12) . . . . ?
C2 N3 C3 C4 -169.3(6) . . . . ?
C6 C7 C8 N1 177.5(7) . . . . ?
F1 C7 C8 N1 -1.8(9) . . . . ?
C6 C7 C8 C9 1.2(11) . . . . ?
F1 C7 C8 C9 -178.1(5) . . . . ?
C14 N1 C8 C7 140.3(7) . . . . ?
C17 N1 C8 C7 -87.7(8) . . . . ?
C14 N1 C8 C9 -43.8(10) . . . . ?
C17 N1 C8 C9 88.2(8) . . . . ?
N3 C3 C4 C5 1.2(12) . . . . ?
N3 C3 C4 C13 -179.3(7) . . . . ?
F1 C7 C6 C11 178.4(5) . . . . ?
C8 C7 C6 C11 -0.9(11) . . . . ?
C10 C11 C6 C7 -0.4(10) . . . . ?
C5 C11 C6 C7 -179.8(6) . . . . ?
C1 O1 C9 C10 -20.9(9) . . . . ?
C1 O1 C9 C8 161.6(5) . . . . ?
N3 C10 C9 O1 -0.4(11) . . . . ?
C11 C10 C9 O1 -178.3(6) . . . . ?
N3 C10 C9 C8 176.9(6) . . . . ?
C11 C10 C9 C8 -1.0(10) . . . . ?
C7 C8 C9 O1 177.3(6) . . . . ?
N1 C8 C9 O1 1.2(10) . . . . ?
C7 C8 C9 C10 -0.2(10) . . . . ?
N1 C8 C9 C10 -176.2(6) . . . . ?
C3 C4 C13 O4 3.9(10) . . . . ?
C5 C4 C13 O4 -176.6(6) . . . . ?
C3 C4 C13 O3 -175.8(7) . . . . ?
C5 C4 C13 O3 3.6(9) . . . . ?
C15 N2 C16 C17 -56.2(7) . . . . ?
C18 N2 C16 C17 -179.5(6) . . . . ?
C3 C4 C5 O2 176.2(7) . . . . ?
C13 C4 C5 O2 -3.3(11) . . . . ?
C3 C4 C5 C11 -0.3(10) . . . . ?
C13 C4 C5 C11 -179.7(5) . . . . ?
C10 C11 C5 O2 -178.3(7) . . . . ?
C6 C11 C5 O2 1.2(9) . . . . ?
C10 C11 C5 C4 -1.7(9) . . . . ?
C6 C11 C5 C4 177.8(6) . . . . ?
C9 O1 C1 C2 49.2(10) . . . . ?
C3 N3 C2 C12 84.2(9) . . . . ?
C10 N3 C2 C12 -85.3(8) . . . . ?
C3 N3 C2 C1 -152.2(6) . . . . ?
C10 N3 C2 C1 38.3(7) . . . . ?
O1 C1 C2 N3 -56.7(10) . . . . ?
O1 C1 C2 C12 66.1(12) . . . . ?
C8 N1 C17 C16 168.8(7) . . . . ?
C14 N1 C17 C16 -56.0(7) . . . . ?
N2 C16 C17 N1 54.0(9) . . . . ?
C16 N2 C15 C14 58.9(7) . . . . ?
C18 N2 C15 C14 -177.7(6) . . . . ?
C8 N1 C14 C15 -169.3(8) . . . . ?
C17 N1 C14 C15 58.4(7) . . . . ?
N2 C15 C14 N1 -59.3(9) . . . . ?
