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#$Date: 2022-05-13 12:05:33 +0300 (Fri, 13 May 2022) $
#$Revision: 275403 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/52/8105248.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_8105248
loop_
_publ_author_name
'Huang, Jian-Xiong'
'Huang, Cui-Xin'
'Huang, Guo-Ping'
'Xiong, Yuan-Zhen'
'Huang, Jian-Ping'
_publ_section_title
;
 Crystal structure of
 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-quinoline-3-carboxylic
 acid, C18H13F2N1O4
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              655
_journal_page_last               657
_journal_paper_doi               10.1515/ncrs-2019-0885
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C18 H13 F2 N O4'
_chemical_formula_sum            'C18 H13 F2 N O4'
_chemical_formula_weight         345.29
_chemical_name_systematic
;
Crystal structure of 7-ethoxyl-6,8-difluoro-4-oxo-1-phenyl-1,4-dihydro-
quinoline-3-carboxylic acid
;
_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
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                101.390(2)
_cell_angle_beta                 93.169(2)
_cell_angle_gamma                104.901(2)
_cell_formula_units_Z            2
_cell_length_a                   7.9002(13)
_cell_length_b                   9.9371(16)
_cell_length_c                   10.6852(17)
_cell_measurement_reflns_used    3362
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.55
_cell_measurement_theta_min      2.59
_cell_volume                     789.7(2)
_computing_cell_refinement       'APEX2, SAINT and SADABS [1]'
_computing_data_collection       'APEX2, SAINT and SADABS [1]'
_computing_data_reduction        'APEX2, SAINT and SADABS [1]'
_computing_molecular_graphics    'Diamond 4.0 [3]'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014) [2]'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_Laue_measured_fraction_full 0.991
_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       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7108
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.582
_diffrn_reflns_theta_min         2.586
_exptl_absorpt_coefficient_mu    0.118
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.452
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             356
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.376
_refine_diff_density_min         -0.288
_refine_diff_density_rms         0.040
_refine_ls_abs_structure_details
;
 Flack x determined using 1462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Crystallogr. B69 (2013) 249-259).
;
_refine_ls_extinction_coef       0.050(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         3570
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0762
_refine_ls_R_factor_gt           0.0567
_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/[σ²(Fo²)+(0.0200P)²+0.4500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1223
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2540
_reflns_number_total             3570
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0885_suppl.cif
_cod_data_source_block           3943_0m
_cod_database_code               8105248
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.980
_shelx_estimated_absorpt_t_max   0.985
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.4506(2) 0.9283(2) 0.22163(18) 0.0471(4) Uani 1 1 d . . . . .
C2 C 0.3893(3) 0.9929(2) 0.3322(2) 0.0549(5) Uani 1 1 d . . . . .
C3 C 0.4781(3) 1.1266(2) 0.4043(2) 0.0576(5) Uani 1 1 d . . . . .
C4 C 0.6346(3) 1.1962(2) 0.3637(2) 0.0602(5) Uani 1 1 d . . . . .
C5 C 0.7006(3) 1.1387(2) 0.2587(2) 0.0591(5) Uani 1 1 d . . . . .
H5 H 0.8062 1.1886 0.2352 0.071 Uiso 1 1 calc R U . . .
C6 C 0.6092(2) 1.0036(2) 0.18536(19) 0.0486(4) Uani 1 1 d . . . . .
C7 C 0.6816(3) 0.9439(2) 0.0716(2) 0.0527(5) Uani 1 1 d . . . . .
C8 C 0.5830(3) 0.8058(2) 0.00262(19) 0.0521(5) Uani 1 1 d . . . . .
C9 C 0.4304(3) 0.7387(2) 0.0438(2) 0.0551(5) Uani 1 1 d . . . . .
H9 H 0.3691 0.6485 -0.0036 0.066 Uiso 1 1 calc R U . . .
C10 C 0.6395(3) 0.7308(3) -0.1160(2) 0.0659(6) Uani 1 1 d . . . . .
C11 C 0.1959(2) 0.7050(2) 0.17521(19) 0.0496(5) Uani 1 1 d . . . . .
C12 C 0.0408(3) 0.7171(3) 0.1228(3) 0.0711(7) Uani 1 1 d . . . . .
H12 H 0.0394 0.7837 0.0729 0.085 Uiso 1 1 calc R U . . .
C13 C -0.1147(3) 0.6279(3) 0.1457(3) 0.0766(7) Uani 1 1 d . . . . .
H13 H -0.2218 0.6349 0.1109 0.092 Uiso 1 1 calc R U . . .
C14 C -0.1135(3) 0.5302(2) 0.2182(2) 0.0649(6) Uani 1 1 d . . . . .
H14 H -0.2190 0.4722 0.2343 0.078 Uiso 1 1 calc R U . . .
C15 C 0.0434(3) 0.5179(3) 0.2671(3) 0.0752(7) Uani 1 1 d . . . . .
H15 H 0.0445 0.4496 0.3153 0.090 Uiso 1 1 calc R U . . .
C16 C 0.2005(3) 0.6056(2) 0.2460(2) 0.0660(6) Uani 1 1 d . . . . .
H16 H 0.3076 0.5972 0.2795 0.079 Uiso 1 1 calc R U . . .
C17 C 0.3312(7) 1.2929(8) 0.5078(5) 0.116(2) Uani 0.778(8) 1 d . . P A 1
H17A H 0.3557 1.3628 0.5886 0.139 Uiso 0.778(8) 1 calc R U P A 1
H17B H 0.3738 1.3419 0.4409 0.139 Uiso 0.778(8) 1 calc R U P A 1
C17B C 0.2551(17) 1.1689(19) 0.5515(14) 0.084(6) Uani 0.222(8) 1 d . . P A 2
H17C H 0.2633 1.2121 0.6421 0.101 Uiso 0.222(8) 1 calc R U P A 2
H17D H 0.1958 1.0681 0.5397 0.101 Uiso 0.222(8) 1 calc R U P A 2
C18 C 0.1513(7) 1.2320(7) 0.4809(5) 0.176(2) Uani 1 1 d . . . . .
H18A H 0.1255 1.1736 0.3954 0.265 Uiso 1 1 calc R U . A 1
H18B H 0.0923 1.3059 0.4873 0.265 Uiso 1 1 calc R U . A 1
H18C H 0.1113 1.1742 0.5413 0.265 Uiso 1 1 calc R U . A 1
F1 F 0.24205(18) 0.92385(14) 0.37377(14) 0.0829(5) Uani 1 1 d . . . . .
F2 F 0.7215(2) 1.32612(14) 0.43496(14) 0.0861(5) Uani 1 1 d . . . . .
N1 N 0.3622(2) 0.79323(17) 0.14763(16) 0.0513(4) Uani 1 1 d . . . . .
O1 O 0.7907(2) 0.7983(2) -0.15055(17) 0.0796(5) Uani 1 1 d . . . . .
H1 H 0.834(4) 0.889(4) -0.090(3) 0.119 Uiso 1 1 d . U . . .
O2 O 0.5548(2) 0.6152(2) -0.17739(18) 0.0904(6) Uani 1 1 d . . . . .
O3 O 0.8214(2) 1.01177(18) 0.03759(16) 0.0755(5) Uani 1 1 d . . . . .
O4 O 0.4248(2) 1.18338(19) 0.51602(16) 0.0793(5) Uani 1 1 d . . . . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 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'
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
N1 C1 C2 123.14(17) . .
N1 C1 C6 119.09(17) . .
C2 C1 C6 117.76(18) . .
F1 C2 C3 117.17(19) . .
F1 C2 C1 120.32(18) . .
C3 C2 C1 122.49(18) . .
O4 C3 C2 121.9(2) . .
O4 C3 C4 120.6(2) . .
C2 C3 C4 117.19(19) . .
F2 C4 C5 120.2(2) . .
F2 C4 C3 117.0(2) . .
C5 C4 C3 122.87(19) . .
C4 C5 C6 119.69(19) . .
C5 C6 C1 120.00(19) . .
C5 C6 C7 118.89(18) . .
C1 C6 C7 121.11(18) . .
O3 C7 C8 122.8(2) . .
O3 C7 C6 121.34(19) . .
C8 C7 C6 115.83(17) . .
C9 C8 C7 119.86(19) . .
C9 C8 C10 118.0(2) . .
C7 C8 C10 122.19(19) . .
N1 C9 C8 124.71(19) . .
O2 C10 O1 121.2(2) . .
O2 C10 C8 122.9(2) . .
O1 C10 C8 115.9(2) . .
C12 C11 C16 121.60(19) . .
C12 C11 N1 119.49(18) . .
C16 C11 N1 118.77(18) . .
C11 C12 C13 118.3(2) . .
C14 C13 C12 121.1(2) . .
C13 C14 C15 119.5(2) . .
C14 C15 C16 120.6(2) . .
C11 C16 C15 118.8(2) . .
C18 C17 O4 111.0(6) . .
O4 C17B C18 113.9(13) . .
C9 N1 C1 119.40(16) . .
C9 N1 C11 116.46(16) . .
C1 N1 C11 124.15(16) . .
C3 O4 C17B 129.7(6) . .
C3 O4 C17 115.0(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.397(2) .
C1 C2 1.402(3) .
C1 C6 1.402(2) .
C2 F1 1.337(2) .
C2 C3 1.381(3) .
C3 O4 1.354(3) .
C3 C4 1.391(3) .
C4 F2 1.348(2) .
C4 C5 1.349(3) .
C5 C6 1.401(3) .
C6 C7 1.457(3) .
C7 O3 1.251(2) .
C7 C8 1.422(3) .
C8 C9 1.361(3) .
C8 C10 1.491(3) .
C9 N1 1.340(3) .
C10 O2 1.207(3) .
C10 O1 1.321(3) .
C11 C12 1.363(3) .
C11 C16 1.364(3) .
C11 N1 1.460(2) .
C12 C13 1.383(3) .
C13 C14 1.357(3) .
C14 C15 1.363(3) .
C15 C16 1.380(3) .
C17 C18 1.383(7) .
C17 O4 1.478(6) .
C17B O4 1.393(13) .
C17B C18 1.420(16) .
