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_7248567
_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
'2(C17 H19 F N3 O3), 2(C7 H5 O3), 3(C7 H6 O3), 2(H2 O)'
_chemical_formula_sum            'C69 H70 F2 N6 O23'
_chemical_formula_weight         1389.31
_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             2024-03-02
_audit_creation_method
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_audit_update_record
;
2024-03-04 deposited with the CCDC.	2024-04-29 downloaded from the CCDC.
;
_cell_angle_alpha                82.783(9)
_cell_angle_beta                 77.177(9)
_cell_angle_gamma                76.989(9)
_cell_formula_units_Z            1
_cell_length_a                   9.194(3)
_cell_length_b                   12.720(4)
_cell_length_c                   14.712(5)
_cell_measurement_reflns_used    1878
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.46
_cell_measurement_theta_min      2.26
_cell_volume                     1629.4(9)
_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    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_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  0.0291
_diffrn_reflns_av_unetI/netI     0.0614
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9181
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         1.424
_diffrn_source                   'Sealed tube'
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  0.9820
_exptl_absorpt_correction_T_min  0.9753
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.414
_refine_diff_density_rms         0.087
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         5695
_refine_ls_number_restraints     75
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.1406
_refine_ls_R_factor_gt           0.0816
_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          0.2455
_refine_ls_wR_factor_ref         0.3041
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3042
_reflns_number_total             5695
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4ce00213j2.cif
_cod_data_source_block           5
_cod_depositor_comments
'Adding full bibliography for 7248565--7248569.cif.'
_cod_original_cell_volume        1629.4(10)
_cod_database_code               7248567
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.982
_shelx_estimated_absorpt_t_min   0.976
_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
O11 \\sim O12 \\sim O13 \\sim C33 \\sim C34 \\sim C36 \\sim C37 \\sim C38 \\sim
C39: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
N3 \\sim C15 \\sim C16 \\sim C17: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
3. Rigid body (RIGU) restrains
 N3, C15
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Fixed Sof: O11(0.5) O12(0.5) H12(0.5) O13(0.5) H13(0.5) C39(0.5) C40(0.5)
 H40(0.5) C36(0.5) H36(0.5) C34(0.5) C33(0.5) C38(0.5) H38(0.5) C37(0.5)
 H37(0.5)
5.a Riding coordinates:
 O9(H9), O10(H10A,H10B)
5.b Ternary CH refined with riding coordinates:
 C15(H15)
5.c Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C16(H16A,
 H16B), C17(H17A,H17B)
5.d Aromatic/amide H refined with riding coordinates:
 C7(H7), C10(H10), C11(H11), C20(H20), C21(H21), C22(H22), C23(H23), C27(H27),
 C28(H28), C29(H29), C30(H30), C40(H40), C36(H36), C38(H38), C37(H37)
5.e Fitted hexagon refined as free rotating group:
 C40(C36,C34,C33,C38,C37)
5.f Tetrahedral OH refined with riding coordinates:
 O6(H6)
5.g Idealised tetrahedral OH refined as rotating group:
 O2(H2), O8(H8), O12(H12), O13(H13)
;
_shelx_res_checksum              62985
_olex2_submission_special_instructions 'No special instructions were received'