Pressure-induced phase behaviour and compressibility of the racemic and chiral solid forms, ofloxacin and levofloxacin
Gasol-Cardona, Julia; Ward, Martin R.; Comboni, Davide; Hanfland, Micheal; Scatena, Rebecca; Warren, Mark R.; Maloney, Andrew G. P.; Oswald, Iain D. H.; CrystEngComm 27 (2025) 7662–7676; doi:10.1039/D5CE00855G

data_7251173
_publ_section_title
;
 Pressure-induced phase behaviour and compressibility of the racemic and
 chiral solid forms, ofloxacin and levofloxacin
;
_journal_issue                   47
_journal_name_full               CrystEngComm
_journal_page_first              7662
_journal_page_last               7676
_journal_paper_doi               10.1039/D5CE00855G
_journal_volume                  27
_journal_year                    2025
_chemical_formula_moiety         'C18 H20 F N3 O4, 0.5(H2 O)'
_chemical_formula_sum            'C18 H21 F N3 O4.5'
_chemical_formula_weight         370.38
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2025-09-25
_audit_creation_method
;
Olex2 1.5-ac7-013
(compiled 2025.01.02 svn.rf662f148 for Rigaku Oxford Diffraction, GUI svn.r7109)
;
_audit_update_record
;
2025-10-08 deposited with the CCDC.	2025-10-29 downloaded from the CCDC.
;
_cell_angle_alpha                81.661(9)
_cell_angle_beta                 109.861(12)
_cell_angle_gamma                79.082(7)
_cell_formula_units_Z            4
_cell_length_a                   13.985(2)
_cell_length_b                   6.0616(6)
_cell_length_c                   17.534(3)
_cell_measurement_reflns_used    1597
_cell_measurement_temperature    297.00
_cell_measurement_theta_max      22.06
_cell_measurement_theta_min      3.25
_cell_volume                     1336.9(4)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_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      297.00
_diffrn_measured_fraction_theta_full 0.345
_diffrn_measured_fraction_theta_max 0.345
_diffrn_measurement_device_type  'Bruker Photon III'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0570
_diffrn_reflns_av_unetI/netI     0.0876
_diffrn_reflns_Laue_measured_fraction_full 0.345
_diffrn_reflns_Laue_measured_fraction_max 0.345
_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       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7462
_diffrn_reflns_point_group_measured_fraction_full 0.338
_diffrn_reflns_point_group_measured_fraction_max 0.338
_diffrn_reflns_theta_full        23.277
_diffrn_reflns_theta_max         23.277
_diffrn_reflns_theta_min         2.435
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.143
_exptl_absorpt_correction_T_max  0.7449
_exptl_absorpt_correction_T_min  0.6557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0683 before and 0.0586 after correction.
The Ratio of minimum to maximum transmission is 0.8803.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            Colourless
_exptl_crystal_density_diffrn    1.840
_exptl_crystal_description       lathe
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.322
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.072
_refine_ls_abs_structure_details
;
 Flack x determined using 606 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.6(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     396
_refine_ls_number_reflns         2614
_refine_ls_number_restraints     114
_refine_ls_restrained_S_all      1.095
_refine_ls_R_factor_all          0.1436
_refine_ls_R_factor_gt           0.0864
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2288
_refine_ls_wR_factor_ref         0.2761
_reflns_Friedel_coverage         0.961
_reflns_Friedel_fraction_full    0.331
_reflns_Friedel_fraction_max     0.331
_reflns_number_gt                1587
_reflns_number_total             2614
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5ce00855g2.cif
_cod_data_source_block           levo_hh_20241120_11_0m
_cod_depositor_comments
'Adding full bibliography for 7251165--7251187.cif.'
_cod_original_cell_volume        1336.9(3)
_cod_original_formula_sum        'C18 H21 F N3 O4.50'
_cod_database_code               7251173
_shelx_shelxl_version_number     2019/1
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 O4-C11
 1.476 with sigma of 0.02
 C11-C12
 1.483 with sigma of 0.02
 O3-C3
 1.228 with sigma of 0.02
 O2-C10
 1.372 with sigma of 0.02
 C2-C3
 1.516 with sigma of 0.02
 C14-N2
 1.404 with sigma of 0.02
 C6-N2
 1.489 with sigma of 0.02
 C6-C5
 1.228 with sigma of 0.02
 C6-C7
 1.303 with sigma of 0.02
 C4-C5
 1.391 with sigma of 0.02
 C4-C66
 1.462 with sigma of 0.02
 C66-C8
 1.462 with sigma of 0.02
 C8-C7
 1.369 with sigma of 0.02
 C17-C16
 1.352 with sigma of 0.02
 O1-C10
 1.22 with sigma of 0.02
 F1-C5
 1.403 with sigma of 0.02
 O4-C7
 1.395 with sigma of 0.02
 C2-C10
 1.373 with sigma of 0.02
 C1-N1
 1.395 with sigma of 0.02
 C12-N1
 1.402 with sigma of 0.02
 C8-N1
 1.402 with sigma of 0.02
 C1-C2
 1.516 with sigma of 0.02
 C66-C3
 1.443 with sigma of 0.02
 C17-N2
 1.511 with sigma of 0.02
 C13-C12
 1.461 with sigma of 0.02
 C16-N3
 1.464 with sigma of 0.02
 C18-N3
 1.462 with sigma of 0.02
 C15-C14
 1.46 with sigma of 0.02
 C15-N3
 1.435 with sigma of 0.02
 C65-C67
 1.489 with sigma of 0.02
 O16-C65
 1.516 with sigma of 0.02
 O14-C64
 1.334 with sigma of 0.02
 O15-C57
 1.228 with sigma of 0.02
 C71-N12
 1.462 with sigma of 0.02
 C60-C61
 1.462 with sigma of 0.02
 C62-C61
 1.469 with sigma of 0.02
 C60-C59
 1.368 with sigma of 0.02
 C58-C59
 1.303 with sigma of 0.02
 C58-C63
 1.367 with sigma of 0.02
 C70-C71
 1.483 with sigma of 0.02
 C67-N10
 1.443 with sigma of 0.02
 F4-C59
 1.444 with sigma of 0.02
 C74-N12
 1.385 with sigma of 0.02
 O13-C64
 1.228 with sigma of 0.02
 C62-N10
 1.417 with sigma of 0.02
 C55-N10
 1.228 with sigma of 0.02
 C60-N11
 1.22 with sigma of 0.02
 C70-N11
 1.395 with sigma of 0.02
 C73-N11
 1.402 with sigma of 0.02
 C69-C67
 1.402 with sigma of 0.02
 C56-C57
 1.476 with sigma of 0.02
 C55-C56
 1.403 with sigma of 0.02
 C56-C64
 1.373 with sigma of 0.02
 O16-C61
 1.395 with sigma of 0.02
 C63-C62
 1.352 with sigma of 0.02
 C63-C57
 1.525 with sigma of 0.02
 C72-N12
 1.435 with sigma of 0.02
 C72-C73
 1.516 with sigma of 0.02
 O12-C47
 1.382 with sigma of 0.02
 C49-C48
 1.476 with sigma of 0.02
 F3-C41
 1.403 with sigma of 0.02
 C40-C45
 1.374 with sigma of 0.02
 C40-C41
 1.483 with sigma of 0.02
 C45-C44
 1.367 with sigma of 0.02
 C45-C39
 1.443 with sigma of 0.02
 C44-C43
 1.473 with sigma of 0.02
 C42-C43
 1.466 with sigma of 0.02
 C42-C41
 1.464 with sigma of 0.02
 O11-C39
 1.228 with sigma of 0.02
 C44-N7
 1.417 with sigma of 0.02
 C37-N7
 1.22 with sigma of 0.02
 O12-C43
 1.458 with sigma of 0.02
 C42-N8
 1.352 with sigma of 0.02
 C38-C39
 1.489 with sigma of 0.02
 C37-C38
 1.395 with sigma of 0.02
 C53-N8
 1.395 with sigma of 0.02
 C50-N8
 1.402 with sigma of 0.02
 C52-N9
 1.402 with sigma of 0.02
 C51-N9
 1.457 with sigma of 0.02
 C52-C53
 1.303 with sigma of 0.02
 C51-C50
 1.435 with sigma of 0.02
 C48-N7
 1.511 with sigma of 0.02
 O8-C29
 1.464 with sigma of 0.02
 C33-N6
 1.516 with sigma of 0.02
 C36-N6
 1.458 with sigma of 0.02
 C32-N5
 1.457 with sigma of 0.02
 C19-N4
 1.525 with sigma of 0.02
 C29-C30
 1.464 with sigma of 0.02
 C35-C34
 1.367 with sigma of 0.02
 C24-C25
 1.404 with sigma of 0.02
 C26-C25
 1.46 with sigma of 0.02
 C24-C23
 1.347 with sigma of 0.02
 C22-C23
 1.483 with sigma of 0.02
 C22-C27
 1.374 with sigma of 0.02
 C27-C26
 1.352 with sigma of 0.02
 O5-C28
 1.22 with sigma of 0.02
 F2-C23
 1.516 with sigma of 0.02
 O8-C25
 1.402 with sigma of 0.02
 C35-N6
 1.403 with sigma of 0.02
 C34-N5
 1.395 with sigma of 0.02
 C24-N5
 1.373 with sigma of 0.02
 O6-C28
 1.402 with sigma of 0.02
 C30-N4
 1.391 with sigma of 0.02
 C26-N4
 1.466 with sigma of 0.02
 C32-C33
 1.443 with sigma of 0.02
 C31-C30
 1.461 with sigma of 0.02
 C19-C20
 1.228 with sigma of 0.02
 C20-C28
 1.511 with sigma of 0.02
 O16-C61 \\sim O16A-C61
 with sigma of 0.02
 O16-C65 \\sim O16A-C65A
 with sigma of 0.02
 C65-C67 \\sim C65A-C67
 with sigma of 0.02
 O16-C67 \\sim O16A-C67
 with sigma of 0.04
 C61-C65 \\sim C61-C65A
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uiso(O16) = Uiso(O16A)
Uiso(C65) = Uiso(C65A)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Fixed Sof: O16A(0.32436) C65(0.32436) H65A(0.32436) H65B(0.32436)
 H67(0.32436) H67A(0.67564) O16(0.67564) C65A(0.67564) H65C(0.67564)
 H65D(0.67564)
6.a Riding coordinates:
 O17(H17C,H17D), O18(H18D,H18E)
6.b Ternary CH refined with riding coordinates:
 C12(H12), C30(H30), C48(H48), C67(H67), C67(H67A)
6.c Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C14(H14A,H14B), C15(H15A,H15B), C16(H16A,H16B), C17(H17A,
 H17B), C29(H29A,H29B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C47(H47A,H47B), C50(H50A,H50B), C51(H51A,H51B), C52(H52A,H52B),
  C53(H53A,H53B), C65(H65A,H65B), C70(H70A,H70B), C71(H71A,H71B), C72(H72A,
 H72B), C73(H73A,H73B), C65A(H65C,H65D)
6.d Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C19(H19), C22(H22), C37(H37), C40(H40), C55(H55), C58(H58)
6.e Fitted hexagon refined as free rotating group:
 C7(C6,C5,C4,C66,C8), C27(C26,C25,C24,C23,C22), C42(C41,C40,C45,C44,C43),
 C63(C62,C61,C60,C59,C58)
6.f Tetrahedral OH refined with riding coordinates:
 O10(H10)
6.g Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C18(H18A,H18B,H18C), C31(H31A,H31B,H31C), C36(H36A,H36B,
 H36C), C49(H49A,H49B,H49C), C69(H69A,H69B,H69C), C74(H74A,H74B,H74C), C54(H54A,
 H54B,H54C)
6.h Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6), O14(H14)
;
_shelx_res_checksum              86564
_olex2_submission_special_instructions 'No special instructions were received'