Ciprofloxacin salts of benzene mono/di-carboxylate: crystal structures and the improvement of solubility
Zhu, Yujun; Liu, Ruoxi; Wang, Leyao; Chen, Chen; Zhao, Yupei; Guo, Wei; Zhang, Zhihui; CrystEngComm 26 (2024) 2662–2672; doi:10.1039/D4CE00213J

data_7248566
_publ_section_title
;
 Ciprofloxacin salts of benzene mono/di-carboxylate: crystal structures
 and the improvement of solubility
;
_journal_issue                   20
_journal_name_full               CrystEngComm
_journal_page_first              2662
_journal_page_last               2672
_journal_paper_doi               10.1039/D4CE00213J
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C17 H19 F N3 O3, 0.5(C8 H4 O4), 3(H2 O)'
_chemical_formula_sum            'C21 H27 F N3 O8'
_chemical_formula_weight         468.45
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2024-04-01
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-04-04 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                95.552(8)
_cell_angle_beta                 98.490(8)
_cell_angle_gamma                92.972(8)
_cell_formula_units_Z            2
_cell_length_a                   7.311(2)
_cell_length_b                   11.567(4)
_cell_length_c                   13.026(4)
_cell_measurement_reflns_used    1224
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.01
_cell_measurement_theta_min      2.25
_cell_volume                     1081.9(6)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0351
_diffrn_reflns_av_unetI/netI     0.0702
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6128
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.590
_exptl_absorpt_coefficient_mu    0.116
_exptl_absorpt_correction_T_max  0.8915
_exptl_absorpt_correction_T_min  0.7426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             494
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.411
_refine_diff_density_min         -0.450
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         3786
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.1039
_refine_ls_R_factor_gt           0.0588
_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^)+(0.1638P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1749
_refine_ls_wR_factor_ref         0.2561
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2347
_reflns_number_total             3786
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00213j2.cif
_cod_data_source_block           3
_cod_depositor_comments
'Adding full bibliography for 7248565--7248569.cif.'
_cod_original_cell_volume        1082.0(6)
_cod_database_code               7248566
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.975
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O7-O8_$1
 2.771 with sigma of 0.005
3.a Free rotating group:
 O6(H6A,H6B), O7(H7A,H7B), O8(H8A,H8B)
3.b Ternary CH refined with riding coordinates:
 C15(H15)
3.c Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,H16B), C17(H17A,
 H17B), N1(H1C,H1D)
3.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C18(H18), C20(H20)
3.e Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_checksum              42251
_olex2_submission_special_instructions 'No special instructions were received'