The crystal structure of 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4- dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate methanol solvate, C27H32FN3O9
Lin, Shu-Ting; Lou, Can; Jiang, Cheng-Jun; Zeitschrift für Kristallographie - New Crystal Structures 238 (2023) 841–843; doi:10.1515/ncrs-2023-0228

data_8107578
_publ_section_title
;
 The crystal structure of
 4-(3-carboxy-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-
 dihydroquinolin-7-yl)-2-methylpiperazin-1-ium 2,5-dihydroxybenzoate
 methanol solvate, C27H32FN3O9
;
_journal_issue                   5
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              841
_journal_page_last               843
_journal_paper_doi               10.1515/ncrs-2023-0228
_journal_volume                  238
_journal_year                    2023
_chemical_formula_moiety         'C19 H23 F N3 O4, C7 H5 O4, C H4 O'
_chemical_formula_sum            'C27 H32 F N3 O9'
_chemical_formula_weight         561.55
_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   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                87.860(3)
_cell_angle_beta                 76.795(2)
_cell_angle_gamma                78.317(2)
_cell_formula_units_Z            2
_cell_length_a                   8.0932(4)
_cell_length_b                   11.8392(7)
_cell_length_c                   14.6782(8)
_cell_measurement_reflns_used    8917
_cell_measurement_temperature    170.00
_cell_measurement_theta_max      60.623
_cell_measurement_theta_min      2.690
_cell_volume                     1340.81(13)
_computing_cell_refinement       'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_data_collection       'Bruker Instrument Service vV6.2.14'
_computing_data_reduction        'SAINT V8.40B (Bruker Nano, Inc., 2019)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      170.00
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'zju Bruker D8 Venture'
_diffrn_measurement_method       '\? and \f scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0488
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            25694
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.623
_diffrn_reflns_theta_min         2.690
_diffrn_source_current           3.57
_diffrn_source_power             0.24954300000000001
_diffrn_source_voltage           69.9
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6597
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1278 before and 0.0812 after correction.
The Ratio of minimum to maximum transmission is 0.9600.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_description       needle
_exptl_crystal_F_000             592
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.339
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     379
_refine_ls_number_reflns         6034
_refine_ls_number_restraints     20
_refine_ls_restrained_S_all      1.144
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0559
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0651P)^2^+0.7242P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1481
_refine_ls_wR_factor_ref         0.1537
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4834
_reflns_number_total             6034
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2023-0228_suppl_001.cif
_cod_data_source_block           0m
_cod_database_code               8107578
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.960
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C2-C5A
 1.53 with sigma of 0.01
 C2-C5 \\sim C2-C5A
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C2 \\sim C5 \\sim C5A: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
4. Others
 Sof(H2B)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(H5AC)=1-FVAR(1)
 Sof(H2A)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(H5C)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C2(H2A), C2(H2B), C17(H17)
5.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), C1(H1C,H1D), C3(H3A,H3B), C4(H4A,H4B), C18(H18A,H18B), C19(H19A,
 H19B)
5.c Aromatic/amide H refined with riding coordinates:
 C8(H8), C14(H14), C20(H20), C22(H22), C23(H23)
5.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C5(H5A,H5B,H5C), C5A(H5AA,H5AB,H5AC), C27(H27A,H27B,H27C)
5.e Idealised tetrahedral OH refined as rotating group:
 O3(H3), O5(H5), O6(H6), O9(H9)
;
_shelx_res_checksum              55540