#------------------------------------------------------------------------------
#$Date: 2025-10-31 01:41:27 +0200 (Fri, 31 Oct 2025) $
#$Revision: 303112 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/25/11/7251172.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_7251172
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                 102.951(18)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   28.443(9)
_cell_length_b                   6.0167(7)
_cell_length_c                   15.7781(17)
_cell_measurement_pressure       5.2
_cell_measurement_reflns_used    3791
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.285
_cell_measurement_theta_min      2.649
_cell_volume                     2631.5(10)
_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 0.350
_diffrn_measured_fraction_theta_max 0.350
_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  0.0567
_diffrn_reflns_av_unetI/netI     0.0417
_diffrn_reflns_Laue_measured_fraction_full 0.350
_diffrn_reflns_Laue_measured_fraction_max 0.350
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3791
_diffrn_reflns_point_group_measured_fraction_full 0.350
_diffrn_reflns_point_group_measured_fraction_max 0.350
_diffrn_reflns_theta_full        23.285
_diffrn_reflns_theta_max         23.285
_diffrn_reflns_theta_min         2.649
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6691
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_diffrn    1.824
_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         0.099
_refine_diff_density_min         -0.133
_refine_diff_density_rms         0.028
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         666
_refine_ls_number_restraints     248
_refine_ls_restrained_S_all      0.866
_refine_ls_R_factor_all          0.0605
_refine_ls_R_factor_gt           0.0307
_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)+(0.0534P)²+0.3586P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0703
_refine_ls_wR_factor_ref         0.0836
_reflns_Friedel_coverage         0.000
_reflns_number_gt                469
_reflns_number_total             666
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d5ce00855g2.cif
_cod_data_source_block           OFLO_5p2
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               7251172
_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   0.973
_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 0.5705(2) 0.7006(4) 0.79277(16) 0.028(5) Uani 1 1 d D . . . .
O1 O 0.6501(4) 0.5807(5) 0.5668(2) 0.033(4) Uani 1 1 d D . . . .
O4 O 0.4341(3) 0.8178(4) 0.2664(2) 0.022(5) Uani 1 1 d D . . . .
C11 C 0.5247(4) 0.7259(8) 0.5617(3) 0.024(4) Uani 1 1 d D . . . .
O2 O 0.4420(3) 0.8249(5) 0.5270(2) 0.025(4) Uani 1 1 d D . . . .
N3 N 0.5632(4) 0.6827(7) 0.4436(3) 0.024(4) Uani 1 1 d D . . . .
N1 N 0.6520(4) 0.5984(6) 0.7472(3) 0.024(4) Uani 1 1 d D . . . .
C7 C 0.5681(5) 0.6871(9) 0.7058(4) 0.021(4) Uani 1 1 d D . . . .
C10 C 0.5659(5) 0.6756(8) 0.5327(3) 0.021(4) Uani 1 1 d D . . . .
C3 C 0.5222(6) 0.7308(9) 0.3866(4) 0.022(4) Uani 1 1 d D . . . .
H3 H 0.522368 0.734881 0.327760 0.026 Uiso 1 1 calc R U . . .
C8 C 0.6101(5) 0.6305(8) 0.6811(4) 0.019(4) Uani 1 1 d D . . . .
O3 O 0.3980(4) 0.8782(5) 0.3748(2) 0.032(5) Uani 1 1 d D . . . .
H3A H 0.403712 0.857604 0.427480 0.048 Uiso 1 1 calc R U . . .
C4 C 0.4806(5) 0.7736(8) 0.4110(3) 0.021(4) Uani 1 1 d D . . . .
C6 C 0.5256(5) 0.7342(8) 0.6517(3) 0.020(4) Uani 1 1 d D . . . .
H6 H 0.498354 0.770282 0.672280 0.024 Uiso 1 1 calc R U . . .
C9 C 0.6077(5) 0.6249(8) 0.5913(4) 0.024(4) Uani 1 1 d D . . . .
N2 N 0.7477(3) 0.5911(6) 0.8424(2) 0.026(5) Uani 1 1 d D . . . .
C13 C 0.4360(5) 0.8239(8) 0.3450(4) 0.027(5) Uani 1 1 d D . . . .
C16 C 0.7168(4) 0.7747(8) 0.8518(3) 0.028(5) Uani 1 1 d D . . . .
H16A H 0.736054 0.908894 0.864264 0.034 Uiso 1 1 calc R U . . .
H16B H 0.702006 0.746829 0.900466 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4789(4) 0.7771(8) 0.5008(3) 0.020(4) Uani 1 1 d D . . . .
C1 C 0.6437(4) 0.5184(7) 0.4769(3) 0.029(5) Uani 1 1 d D . . . .
H1A H 0.630720 0.368895 0.468824 0.034 Uiso 1 1 calc R U . . .
H1B H 0.674808 0.518274 0.461246 0.034 Uiso 1 1 calc R U . . .
C12 C 0.6314(5) 0.9047(7) 0.4203(3) 0.027(6) Uani 1 1 d D . . . .
H12A H 0.610132 0.999123 0.380007 0.040 Uiso 1 1 calc R U . . .
H12B H 0.662118 0.896996 0.404735 0.040 Uiso 1 1 calc R U . . .
H12C H 0.635633 0.964272 0.477992 0.040 Uiso 1 1 calc R U . . .
C2 C 0.6101(5) 0.6757(8) 0.4176(3) 0.025(5) Uani 1 1 d D . . . .
H2 H 0.604690 0.619445 0.357935 0.030 Uiso 1 1 calc R U . . .
C17 C 0.6781(4) 0.8088(7) 0.7706(3) 0.026(5) Uani 1 1 d D . . . .
H17A H 0.655801 0.922856 0.780552 0.031 Uiso 1 1 calc R U . . .
H17B H 0.692412 0.857138 0.723483 0.031 Uiso 1 1 calc R U . . .
C15 C 0.7203(4) 0.3868(7) 0.8186(3) 0.024(5) Uani 1 1 d D . . . .
H15A H 0.704164 0.346047 0.864429 0.028 Uiso 1 1 calc R U . . .
H15B H 0.742082 0.267206 0.812146 0.028 Uiso 1 1 calc R U . . .
C18 C 0.7845(4) 0.5575(9) 0.9223(3) 0.035(6) Uani 1 1 d D . . . .
H18A H 0.802757 0.691790 0.936689 0.052 Uiso 1 1 calc R U . . .
H18B H 0.805621 0.439258 0.913905 0.052 Uiso 1 1 calc R U . . .
H18C H 0.769233 0.519517 0.968834 0.052 Uiso 1 1 calc R U . . .
C14 C 0.6838(4) 0.4181(7) 0.7355(3) 0.028(5) Uani 1 1 d D . . . .
H14A H 0.699788 0.453556 0.688908 0.033 Uiso 1 1 calc R U . . .
H14B H 0.665393 0.282584 0.720208 0.033 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 113.9(8) . . ?
C10 C11 C6 120.8(9) . . ?
C10 C11 C5 121.6(5) . . ?
C6 C11 C5 117.6(8) . . ?
C3 N3 C10 121.9(10) . . ?
C3 N3 C2 121.7(5) . . ?
C10 N3 C2 115.5(10) . . ?
C8 N1 C14 117.1(5) . . ?
C8 N1 C17 111.3(5) . . ?
C14 N1 C17 112.5(8) . . ?
C6 C7 F1 117.6(9) . . ?
C6 C7 C8 125.8(6) . . ?
F1 C7 C8 116.6(10) . . ?
C9 C10 C11 119.9(5) . . ?
C9 C10 N3 122.1(10) . . ?
C11 C10 N3 117.9(10) . . ?
N3 C3 C4 122.7(6) . . ?
N3 C3 H3 118.7 . . ?
C4 C3 H3 118.7 . . ?
C7 C8 C9 116.2(11) . . ?
C7 C8 N1 117.9(6) . . ?
C9 C8 N1 125.8(11) . . ?
C13 O3 H3A 109.5 . . ?
C3 C4 C5 120.9(10) . . ?
C3 C4 C13 120.5(6) . . ?
C5 C4 C13 118.6(10) . . ?
C7 C6 C11 116.2(9) . . ?
C7 C6 H6 121.9 . . ?
C11 C6 H6 121.9 . . ?
C10 C9 O1 122.6(5) . . ?
C10 C9 C8 121.0(10) . . ?
O1 C9 C8 116.3(10) . . ?
C16 N2 C15 111.8(8) . . ?
C16 N2 C18 110.7(4) . . ?
C15 N2 C18 110.1(4) . . ?
O4 C13 O3 121.0(10) . . ?
O4 C13 C4 122.7(9) . . ?
O3 C13 C4 116.4(6) . . ?
N2 C16 C17 111.4(4) . . ?
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 123.6(10) . . ?
O2 C5 C11 121.4(5) . . ?
C4 C5 C11 115.0(9) . . ?
O1 C1 C2 111.6(5) . . ?
O1 C1 H1A 109.3 . . ?
C2 C1 H1A 109.3 . . ?
O1 C1 H1B 109.3 . . ?
C2 C1 H1B 109.3 . . ?
H1A C1 H1B 108.0 . . ?
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 110.4(7) . . ?
N3 C2 C1 109.3(5) . . ?
C12 C2 C1 111.2(10) . . ?
N3 C2 H2 108.6 . . ?
C12 C2 H2 108.6 . . ?
C1 C2 H2 108.6 . . ?
N1 C17 C16 109.2(5) . . ?
N1 C17 H17A 109.8 . . ?
C16 C17 H17A 109.8 . . ?
N1 C17 H17B 109.8 . . ?
C16 C17 H17B 109.8 . . ?
H17A C17 H17B 108.3 . . ?
N2 C15 C14 110.2(4) . . ?
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 108.2(5) . . ?
N1 C14 H14A 110.1 . . ?
C15 C14 H14A 110.1 . . ?
N1 C14 H14B 110.1 . . ?
C15 C14 H14B 110.1 . . ?
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 1.361(5) . ?
O1 C9 1.372(13) . ?
O1 C1 1.439(5) . ?
O4 C13 1.230(6) . ?
C11 C10 1.384(12) . ?
C11 C6 1.416(6) . ?
C11 C5 1.468(10) . ?
O2 C5 1.245(11) . ?
N3 C3 1.335(15) . ?
N3 C10 1.392(6) . ?
N3 C2 1.480(15) . ?
N1 C8 1.411(14) . ?
N1 C14 1.450(10) . ?
N1 C17 1.471(8) . ?
C7 C6 1.344(14) . ?
C7 C8 1.380(16) . ?
C10 C9 1.366(14) . ?
C3 C4 1.348(16) . ?
C3 H3 0.9300 . ?
C8 C9 1.403(7) . ?
O3 C13 1.313(13) . ?
O3 H3A 0.8200 . ?
C4 C5 1.430(7) . ?
C4 C13 1.482(14) . ?
C6 H6 0.9300 . ?
N2 C16 1.439(9) . ?
N2 C15 1.458(9) . ?
N2 C18 1.461(8) . ?
C16 C17 1.505(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C1 C2 1.511(12) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C12 C2 1.502(9) . ?
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 1.491(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 2.5(8) . . . . ?
C5 C11 C10 C9 -178.8(6) . . . . ?
C6 C11 C10 N3 -176.4(5) . . . . ?
C5 C11 C10 N3 2.3(8) . . . . ?
C3 N3 C10 C9 179.5(6) . . . . ?
C2 N3 C10 C9 -11.5(8) . . . . ?
C3 N3 C10 C11 -1.6(9) . . . . ?
C2 N3 C10 C11 167.4(5) . . . . ?
C10 N3 C3 C4 -0.6(10) . . . . ?
C2 N3 C3 C4 -169.0(6) . . . . ?
C6 C7 C8 C9 0.7(10) . . . . ?
F1 C7 C8 C9 -177.7(4) . . . . ?
C6 C7 C8 N1 176.6(6) . . . . ?
F1 C7 C8 N1 -1.9(8) . . . . ?
C14 N1 C8 C7 141.0(7) . . . . ?
C17 N1 C8 C7 -87.6(7) . . . . ?
C14 N1 C8 C9 -43.7(8) . . . . ?
C17 N1 C8 C9 87.7(7) . . . . ?
N3 C3 C4 C5 2.2(10) . . . . ?
N3 C3 C4 C13 -179.4(6) . . . . ?
F1 C7 C6 C11 177.9(4) . . . . ?
C8 C7 C6 C11 -0.5(10) . . . . ?
C10 C11 C6 C7 -1.1(9) . . . . ?
C5 C11 C6 C7 -179.8(5) . . . . ?
C11 C10 C9 O1 -177.9(5) . . . . ?
N3 C10 C9 O1 1.0(9) . . . . ?
C11 C10 C9 C8 -2.3(9) . . . . ?
N3 C10 C9 C8 176.6(5) . . . . ?
C1 O1 C9 C10 -20.0(7) . . . . ?
C1 O1 C9 C8 164.3(4) . . . . ?
C7 C8 C9 C10 0.7(9) . . . . ?
N1 C8 C9 C10 -174.7(6) . . . . ?
C7 C8 C9 O1 176.5(6) . . . . ?
N1 C8 C9 O1 1.1(8) . . . . ?
C3 C4 C13 O4 3.9(9) . . . . ?
C5 C4 C13 O4 -177.7(5) . . . . ?
C3 C4 C13 O3 -175.6(6) . . . . ?
C5 C4 C13 O3 2.8(8) . . . . ?
C15 N2 C16 C17 -55.7(6) . . . . ?
C18 N2 C16 C17 -178.9(5) . . . . ?
C3 C4 C5 O2 176.8(6) . . . . ?
C13 C4 C5 O2 -1.6(9) . . . . ?
C3 C4 C5 C11 -1.5(8) . . . . ?
C13 C4 C5 C11 -179.9(5) . . . . ?
C10 C11 C5 O2 -179.1(6) . . . . ?
C6 C11 C5 O2 -0.4(8) . . . . ?
C10 C11 C5 C4 -0.8(8) . . . . ?
C6 C11 C5 C4 177.9(5) . . . . ?
C9 O1 C1 C2 47.9(8) . . . . ?
C3 N3 C2 C12 84.5(8) . . . . ?
C10 N3 C2 C12 -84.5(7) . . . . ?
C3 N3 C2 C1 -152.9(5) . . . . ?
C10 N3 C2 C1 38.1(6) . . . . ?
O1 C1 C2 N3 -56.8(8) . . . . ?
O1 C1 C2 C12 65.4(10) . . . . ?
C8 N1 C17 C16 169.5(6) . . . . ?
C14 N1 C17 C16 -56.8(6) . . . . ?
N2 C16 C17 N1 53.5(8) . . . . ?
C16 N2 C15 C14 58.5(6) . . . . ?
C18 N2 C15 C14 -178.0(5) . . . . ?
C8 N1 C14 C15 -169.6(6) . . . . ?
C17 N1 C14 C15 59.6(6) . . . . ?
N2 C15 C14 N1 -59.0(8) . . . . ?
