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_7248569
_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         '4(C17 H19 F N3 O3), 2(C8 H4 O4), 5(H2 O)'
_chemical_formula_sum            'C84 H94 F4 N12 O25'
_chemical_formula_weight         1747.71
_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                84.737(2)
_cell_angle_beta                 86.232(2)
_cell_angle_gamma                69.254(2)
_cell_formula_units_Z            1
_cell_length_a                   10.5368(12)
_cell_length_b                   13.7042(16)
_cell_length_c                   15.0079(17)
_cell_measurement_reflns_used    5753
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.10
_cell_measurement_theta_min      2.42
_cell_volume                     2016.8(4)
_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      295.15
_diffrn_measured_fraction_theta_full 0.980
_diffrn_measured_fraction_theta_max 0.784
_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  0.0219
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.784
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            14122
_diffrn_reflns_point_group_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.784
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.575
_diffrn_reflns_theta_min         1.593
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.983
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.439
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             918
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.488
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     580
_refine_ls_number_reflns         9715
_refine_ls_number_restraints     12
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0869
_refine_ls_R_factor_gt           0.0610
_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^)+(0.1651P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1872
_refine_ls_wR_factor_ref         0.2345
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6935
_reflns_number_total             9715
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00213j2.cif
_cod_data_source_block           2
_cod_depositor_comments
'Adding full bibliography for 7248565--7248569.cif.'
_cod_database_code               7248569
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.978
_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. Uiso/Uaniso restraints and constraints
Uanis(O11) \\sim Ueq, Uanis(O11A) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
3. Others
 Sof(O11A)=Sof(H11C)=Sof(H11D)=1-FVAR(1)
 Sof(O11)=Sof(H11A)=Sof(H11B)=FVAR(1)
 Fixed Sof: O13(0.5) H13A(0.5) H13B(0.5)
4.a Riding coordinates:
 O11(H11A,H11B), O11A(H11C,H11D), O12(H12A,H12B), O13(H13A,H13B)
4.b Ternary CH refined with riding coordinates:
 C14(H14), C31(H31)
4.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C15(H15A,
 H15B), C16(H16A,H16B), N4(H4C,H4D), C18(H18A,H18B), C19(H19A,H19B), C20(H20A,
 H20B), C21(H21A,H21B), C32(H32A,H32B), C33(H33A,H33B)
4.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C9(H9), C13(H13), C24(H24), C27(H27), C30(H30), C37(H37), C39(H39),
 C40(H40), C41(H41)
4.e Idealised tetrahedral OH refined as rotating group:
 O2(H2), O6(H6A)
;
_shelx_res_checksum              21637
_olex2_submission_special_instructions 'No special instructions were received'