#------------------------------------------------------------------------------
#$Date: 2025-11-29 12:52:59 +0100 (Sat 29 de Nov de 2025) $
#$Revision: 303491 $
#$URL: svn://www.crystallography.net/cod/cif/7/25/13/7251371.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7251371
loop_
_publ_author_name
'Kumar, Satyanand'
'Kumar, Ravi'
'Mishra, Rakesh K.'
'Awasthi, Satish Kumar'
_publ_section_title
;
 Exploring weak noncovalent interactions in a few halo-substituted
 quinolones.
;
_journal_issue                   44
_journal_name_full               'RSC advances'
_journal_page_first              37216
_journal_page_last               37225
_journal_paper_doi               10.1039/d5ra03605d
_journal_volume                  15
_journal_year                    2025
_chemical_formula_moiety         'C15 H11 Cl F N4 O3'
_chemical_formula_sum            'C15 H11 Cl F N4 O3'
_chemical_formula_weight         349.73
_chemical_name_common            QUINOLONE
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-10-19 deposited with the CCDC.	2025-09-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 108.764(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.8502(14)
_cell_length_b                   20.148(3)
_cell_length_c                   9.0629(14)
_cell_measurement_reflns_used    4145
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      29.200
_cell_measurement_theta_min      0.918
_cell_volume                     1530.2(4)
_computing_cell_refinement       'CrysAlis PRO (Oxford diffraction 2009)'
_computing_data_collection       'CrysAlis PRO (Oxford diffraction 2009)'
_computing_data_reduction        'CrysAlis PRO'
_computing_molecular_graphics    'Mercury   (Macrae, et al. 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'OXFORD DIFFRACTION XCALIBUR SAPPHIRE3'
_diffrn_measurement_method       Ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1279
_diffrn_reflns_av_sigmaI/netI    0.2325
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10764
_diffrn_reflns_theta_full        29.20
_diffrn_reflns_theta_max         29.20
_diffrn_reflns_theta_min         2.98
_diffrn_standards_decay_%        numb
_diffrn_standards_interval_count numb
_diffrn_standards_interval_time  numb
_diffrn_standards_number         numb
_exptl_absorpt_coefficient_mu    0.284
_exptl_absorpt_correction_T_max  0.972
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrysAlis PRO; Oxford Diffraction, 2009)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       nidle
_exptl_crystal_F_000             716.0
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.394
_refine_diff_density_min         -0.369
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         3622
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.960
_refine_ls_R_factor_all          0.2713
_refine_ls_R_factor_gt           0.0896
_refine_ls_shift/su_max          0.00
_refine_ls_shift/su_mean         0.00
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1018P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1878
_refine_ls_wR_factor_ref         0.3029
_reflns_number_gt                2136
_reflns_number_total             2895
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d5ra03605d2.cif
_cod_data_source_block           12_CCDC1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7251371
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.1695(2) 0.20206(9) 0.5535(2) 0.0633(7) Uani 1 1 d . . .
N1 N 0.6816(6) 0.0869(2) 0.5480(5) 0.0358(13) Uani 1 1 d . . .
F1 F 0.1673(5) 0.09191(18) 0.7638(5) 0.0647(13) Uani 1 1 d . . .
O1 O 0.6210(6) -0.0627(2) 0.8300(5) 0.0561(14) Uani 1 1 d . . .
C9 C 0.5505(7) 0.0880(3) 0.6004(7) 0.0351(15) Uani 1 1 d . . .
N4 N 0.8060(7) 0.3072(3) 0.6001(7) 0.0516(16) Uani 1 1 d . . .
O2 O 1.0152(6) -0.0588(2) 0.6589(6) 0.0652(15) Uani 1 1 d . . .
O3 O 0.9233(6) -0.1031(2) 0.8382(6) 0.0628(15) Uani 1 1 d . . .
C10 C 0.7087(8) 0.1401(3) 0.4464(7) 0.0385(16) Uani 1 1 d . . .
H10A H 0.6118 0.1469 0.3595 0.046 Uiso 1 1 calc R . .
H10B H 0.7919 0.1262 0.4046 0.046 Uiso 1 1 calc R . .
C8 C 0.4387(7) 0.1396(3) 0.5556(7) 0.0432(17) Uani 1 1 d . . .
H8 H 0.4508 0.1729 0.4894 0.052 Uiso 1 1 calc R . .
C3 C 0.6482(8) -0.0172(3) 0.7501(8) 0.0415(16) Uani 1 1 d . . .
N2 N 0.8475(8) 0.2070(3) 0.6831(7) 0.0585(17) Uani 1 1 d . . .
H2 H 0.8809 0.1733 0.7432 0.070 Uiso 1 1 calc R . .
C1 C 0.7904(7) 0.0379(3) 0.5949(7) 0.0382(16) Uani 1 1 d . . .
H1 H 0.8781 0.0389 0.5597 0.046 Uiso 1 1 calc R . .
C2 C 0.7807(7) -0.0129(3) 0.6903(7) 0.0389(16) Uani 1 1 d . . .
C11 C 0.7561(7) 0.2035(3) 0.5324(7) 0.0355(15) Uani 1 1 d . . .
C6 C 0.2935(8) 0.0897(4) 0.7098(8) 0.0506(19) Uani 1 1 d . . .
C4 C 0.5333(7) 0.0378(3) 0.6999(7) 0.0360(15) Uani 1 1 d . . .
C13 C 0.9162(8) -0.0604(3) 0.7255(8) 0.0471(18) Uani 1 1 d . . .
C5 C 0.4027(7) 0.0396(3) 0.7554(8) 0.0449(17) Uani 1 1 d . . .
H5 H 0.3904 0.0068 0.8229 0.054 Uiso 1 1 calc R . .
N3 N 0.8782(7) 0.2694(3) 0.7251(8) 0.0592(17) Uani 1 1 d . . .
C12 C 0.7274(8) 0.2683(3) 0.4747(8) 0.0459(18) Uani 1 1 d . . .
C7 C 0.3104(8) 0.1403(3) 0.6107(7) 0.0414(16) Uani 1 1 d . . .
C14 C 1.0574(9) -0.1503(4) 0.8796(9) 0.063(2) Uani 1 1 d . . .
H14A H 1.0768 -0.1657 0.7858 0.075 Uiso 1 1 calc R . .
H14B H 1.0314 -0.1885 0.9320 0.075 Uiso 1 1 calc R . .
C15 C 1.2013(11) -0.1176(5) 0.9826(9) 0.093(3) Uani 1 1 d . . .
H15A H 1.2266 -0.0799 0.9302 0.139 Uiso 1 1 calc R . .
H15B H 1.2890 -0.1483 1.0086 0.139 Uiso 1 1 calc R . .
H15C H 1.1824 -0.1033 1.0761 0.139 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C9 119.6(5) . . ?
C1 N1 C10 118.9(5) . . ?
C9 N1 C10 121.4(5) . . ?
N1 C9 C4 119.1(5) . . ?
N1 C9 C8 120.2(5) . . ?
C4 C9 C8 120.7(5) . . ?
N3 N4 C12 110.6(6) . . ?
C13 O3 C14 116.9(5) . . ?
N1 C10 C11 111.7(5) . . ?
N1 C10 H10A 109.3 . . ?
C11 C10 H10A 109.3 . . ?
N1 C10 H10B 109.3 . . ?
C11 C10 H10B 109.3 . . ?
H10A C10 H10B 107.9 . . ?
C7 C8 C9 119.4(6) . . ?
C7 C8 H8 120.3 . . ?
C9 C8 H8 120.3 . . ?
O1 C3 C2 126.7(6) . . ?
O1 C3 C4 119.5(6) . . ?
C2 C3 C4 113.8(5) . . ?
N3 N2 C11 110.1(6) . . ?
N3 N2 H2 125.0 . . ?
C11 N2 H2 125.0 . . ?
N1 C1 C2 124.6(5) . . ?
N1 C1 H1 117.7 . . ?
C2 C1 H1 117.7 . . ?
C1 C2 C3 120.5(6) . . ?
C1 C2 C13 114.2(5) . . ?
C3 C2 C13 125.3(6) . . ?
N2 C11 C12 107.9(5) . . ?
N2 C11 C10 123.6(6) . . ?
C12 C11 C10 128.3(6) . . ?
F1 C6 C5 119.9(6) . . ?
F1 C6 C7 118.6(6) . . ?
C5 C6 C7 121.5(6) . . ?
C9 C4 C5 119.1(6) . . ?
C9 C4 C3 122.4(5) . . ?
C5 C4 C3 118.4(6) . . ?
O2 C13 O3 122.6(6) . . ?
O2 C13 C2 122.6(6) . . ?
O3 C13 C2 114.8(6) . . ?
C6 C5 C4 119.7(6) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 H5 120.2 . . ?
N2 N3 N4 107.5(6) . . ?
N4 C12 C11 104.0(6) . . ?
C8 C7 C6 119.6(6) . . ?
C8 C7 Cl1 120.1(5) . . ?
C6 C7 Cl1 120.3(5) . . ?
O3 C14 C15 109.6(7) . . ?
O3 C14 H14A 109.8 . . ?
C15 C14 H14A 109.8 . . ?
O3 C14 H14B 109.8 . . ?
C15 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C7 1.719(7) . ?
N1 C1 1.349(7) . ?
N1 C9 1.388(7) . ?
N1 C10 1.481(7) . ?
F1 C6 1.357(7) . ?
O1 C3 1.239(7) . ?
C9 C4 1.397(8) . ?
C9 C8 1.401(8) . ?
N4 N3 1.344(8) . ?
N4 C12 1.371(8) . ?
O2 C13 1.214(7) . ?
O3 C13 1.322(7) . ?
O3 C14 1.472(8) . ?
C10 C11 1.486(8) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C8 C7 1.380(8) . ?
C8 H8 0.9300 . ?
C3 C2 1.444(8) . ?
C3 C4 1.473(8) . ?
N2 N3 1.317(7) . ?
N2 C11 1.347(8) . ?
N2 H2 0.8600 . ?
C1 C2 1.361(8) . ?
C1 H1 0.9300 . ?
C2 C13 1.486(8) . ?
C11 C12 1.399(8) . ?
C6 C5 1.367(9) . ?
C6 C7 1.398(9) . ?
C4 C5 1.401(7) . ?
C5 H5 0.9300 . ?
C14 C15 1.471(10) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
