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#$Date: 2022-06-07 10:49:44 +0300 (Tue, 07 Jun 2022) $
#$Revision: 275862 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/53/8105346.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_8105346
loop_
_publ_author_name
'Shu-Fang, Fang'
'Jia, Gu'
'Yuan-Zhen, Xiong'
'Guo-Ping, Huang'
'Jian-Ping, Huang'
_publ_section_title
;
 Crystal structure of
 7-ethoxy-6,8-difluoro-4-oxo-1-pyridin-2-ylmethyl-1,4-dihydro-quinoline-3-carboxylic
 acid, C18H14F2N2O4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              971
_journal_page_last               973
_journal_paper_doi               10.1515/ncrs-2020-0128
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C18 H14 F2 N2 O4'
_chemical_formula_sum            'C18 H14 F2 N2 O4'
_chemical_formula_weight         360.31
_chemical_name_common
;
7-Ethoxy-6,8-difluoro-4-oxo-1-pyridin-2-ylmethyl-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   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                83.409(6)
_cell_angle_beta                 83.283(6)
_cell_angle_gamma                83.728(6)
_cell_formula_units_Z            2
_cell_length_a                   6.377(3)
_cell_length_b                   9.466(5)
_cell_length_c                   13.367(7)
_cell_measurement_reflns_used    2709
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      27.49
_cell_measurement_theta_min      2.54
_cell_volume                     792.3(7)
_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 0.964
_diffrn_measured_fraction_theta_max 0.961
_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  0.0410
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.964
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5426
_diffrn_reflns_point_group_measured_fraction_full 0.964
_diffrn_reflns_point_group_measured_fraction_max 0.961
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.500
_diffrn_reflns_theta_min         2.795
_exptl_absorpt_coefficient_mu    0.123
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             372
_exptl_crystal_size_max          0.190
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.246
_refine_diff_density_rms         0.051
_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       .
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2843
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0959
_refine_ls_R_factor_gt           0.0587
_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)+(0.0779P)²+0.5244P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1511
_refine_ls_wR_factor_ref         0.1814
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1825
_reflns_number_total             2843
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2020-0128_suppl.cif
_cod_data_source_block           4014_0m
_cod_database_code               8105346
_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   0.977
_shelx_estimated_absorpt_t_max   0.984
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 0.0338(4) 0.6786(3) 0.3201(2) 0.0374(6) Uani 1 1 d . . . . .
C2 C 0.1475(5) 0.7476(3) 0.3806(2) 0.0467(7) Uani 1 1 d . . . . .
C3 C 0.0867(5) 0.7612(4) 0.4815(2) 0.0567(9) Uani 1 1 d . . . . .
C4 C -0.0974(5) 0.7005(4) 0.5253(2) 0.0565(9) Uani 1 1 d . . . . .
C5 C -0.2151(5) 0.6337(3) 0.4698(2) 0.0500(8) Uani 1 1 d . . . . .
H5 H -0.3386 0.5963 0.5003 0.060 Uiso 1 1 calc R U . . .
C6 C -0.1519(4) 0.6211(3) 0.3681(2) 0.0387(7) Uani 1 1 d . . . . .
C7 C -0.2776(5) 0.5457(3) 0.3109(2) 0.0419(7) Uani 1 1 d . . . . .
C8 C -0.2015(4) 0.5319(3) 0.2085(2) 0.0381(6) Uani 1 1 d . . . . .
C9 C -0.0209(4) 0.5922(3) 0.1665(2) 0.0385(7) Uani 1 1 d . . . . .
H9 H 0.0235 0.5834 0.0985 0.046 Uiso 1 1 calc R U . . .
C10 C -0.3117(5) 0.4531(3) 0.1427(2) 0.0460(7) Uani 1 1 d . . . . .
C11 C 0.2754(4) 0.7323(3) 0.1591(2) 0.0431(7) Uani 1 1 d . . . . .
H11A H 0.3068 0.6932 0.0945 0.052 Uiso 1 1 calc R U . . .
H11B H 0.3999 0.7101 0.1954 0.052 Uiso 1 1 calc R U . . .
C12 C 0.2304(5) 0.8931(3) 0.1405(2) 0.0412(7) Uani 1 1 d . . . . .
C13 C -0.0044(6) 1.0889(4) 0.1141(3) 0.0687(10) Uani 1 1 d . . . . .
H13 H -0.1436 1.1284 0.1100 0.082 Uiso 1 1 calc R U . . .
C14 C 0.1522(7) 1.1788(4) 0.0984(3) 0.0645(10) Uani 1 1 d . . . . .
H14 H 0.1202 1.2768 0.0840 0.077 Uiso 1 1 calc R U . . .
C15 C 0.3554(6) 1.1222(4) 0.1044(3) 0.0660(10) Uani 1 1 d . . . . .
H15 H 0.4653 1.1810 0.0941 0.079 Uiso 1 1 calc R U . . .
C16 C 0.3980(5) 0.9772(4) 0.1258(3) 0.0569(9) Uani 1 1 d . . . . .
H16 H 0.5364 0.9364 0.1304 0.068 Uiso 1 1 calc R U . . .
C17 C 0.1701(7) 0.8753(4) 0.6228(3) 0.0792(12) Uani 1 1 d . . . . .
H17A H 0.1606 0.7938 0.6737 0.095 Uiso 1 1 calc R U . . .
H17B H 0.0350 0.9334 0.6269 0.095 Uiso 1 1 calc R U . . .
C18 C 0.3431(7) 0.9613(5) 0.6412(3) 0.0824(13) Uani 1 1 d . . . . .
H18A H 0.4733 0.9004 0.6445 0.124 Uiso 1 1 calc R U . . .
H18B H 0.3060 1.0024 0.7041 0.124 Uiso 1 1 calc R U . . .
H18C H 0.3608 1.0361 0.5869 0.124 Uiso 1 1 calc R U . . .
F1 F 0.3271(3) 0.8062(2) 0.34132(13) 0.0661(6) Uani 1 1 d . . . . .
F2 F -0.1595(4) 0.7071(3) 0.62488(14) 0.0873(8) Uani 1 1 d . . . . .
N1 N 0.0956(3) 0.6631(2) 0.21797(17) 0.0384(6) Uani 1 1 d . . . . .
N2 N 0.0306(4) 0.9465(3) 0.1350(2) 0.0574(7) Uani 1 1 d . . . . .
O1 O -0.4862(4) 0.3988(2) 0.18767(18) 0.0618(7) Uani 1 1 d . . . . .
H1 H -0.5087 0.4202 0.2460 0.093 Uiso 1 1 calc R U . . .
O2 O -0.2505(4) 0.4374(3) 0.05602(18) 0.0623(7) Uani 1 1 d . . . . .
O3 O -0.4459(4) 0.4949(2) 0.35270(16) 0.0609(7) Uani 1 1 d . . . . .
O4 O 0.2165(5) 0.8296(4) 0.5283(2) 0.0989(11) 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 123.9(2) . .
N1 C1 C6 119.6(2) . .
C2 C1 C6 116.5(2) . .
F1 C2 C3 115.7(2) . .
F1 C2 C1 120.8(3) . .
C3 C2 C1 123.5(3) . .
O4 C3 C2 115.5(3) . .
O4 C3 C4 127.1(3) . .
C2 C3 C4 117.4(3) . .
F2 C4 C5 119.0(3) . .
F2 C4 C3 119.5(3) . .
C5 C4 C3 121.5(3) . .
C4 C5 C6 120.4(3) . .
C5 C6 C1 120.6(2) . .
C5 C6 C7 119.4(2) . .
C1 C6 C7 120.0(2) . .
O3 C7 C8 122.4(2) . .
O3 C7 C6 120.7(3) . .
C8 C7 C6 116.9(2) . .
C9 C8 C7 120.0(2) . .
C9 C8 C10 117.9(3) . .
C7 C8 C10 122.2(2) . .
N1 C9 C8 123.8(3) . .
O2 C10 O1 121.1(3) . .
O2 C10 C8 124.1(3) . .
O1 C10 C8 114.8(3) . .
N1 C11 C12 112.8(2) . .
N2 C12 C16 122.8(3) . .
N2 C12 C11 117.8(2) . .
C16 C12 C11 119.3(3) . .
N2 C13 C14 123.9(4) . .
C15 C14 C13 118.5(3) . .
C14 C15 C16 119.5(3) . .
C15 C16 C12 118.6(3) . .
O4 C17 C18 108.3(3) . .
C9 N1 C1 119.7(2) . .
C9 N1 C11 116.9(2) . .
C1 N1 C11 123.2(2) . .
C12 N2 C13 116.8(3) . .
C3 O4 C17 125.2(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N1 1.396(3) .
C1 C2 1.403(4) .
C1 C6 1.412(4) .
C2 F1 1.351(3) .
C2 C3 1.376(4) .
C3 O4 1.352(4) .
C3 C4 1.401(4) .
C4 F2 1.350(4) .
C4 C5 1.361(4) .
C5 C6 1.387(4) .
C6 C7 1.459(4) .
C7 O3 1.267(3) .
C7 C8 1.414(4) .
C8 C9 1.374(4) .
C8 C10 1.494(4) .
C9 N1 1.346(3) .
C10 O2 1.200(4) .
C10 O1 1.328(3) .
C11 N1 1.482(3) .
C11 C12 1.515(4) .
C12 N2 1.325(4) .
C12 C16 1.384(4) .
C13 N2 1.344(4) .
C13 C14 1.365(5) .
C14 C15 1.355(5) .
C15 C16 1.373(5) .
C17 O4 1.372(4) .
C17 C18 1.498(5) .
