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#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/21/8102143.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_8102143
loop_
_publ_author_name
'Ganszky, Ildikó'
'Kaizer, József'
'Czaun, Miklós'
'Speier, Gábor'
'Párkányi, László'
_publ_section_title
;
Crystal structure of 2-phenylquinolin-3,4-dione, C₁₅H₉NO₂
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              259
_journal_page_last               260
_journal_volume                  222
_journal_year                    2007
_chemical_formula_sum            'C15 H9 N O2'
_chemical_formula_weight         235.23
_chemical_name_systematic
; 
 2-phenylquinolin-3,4-diones  
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                115.26
_cell_angle_beta                 91.28
_cell_angle_gamma                93.45
_cell_formula_units_Z            2
_cell_length_a                   3.822
_cell_length_b                   12.122
_cell_length_c                   13.194
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      39.74
_cell_measurement_theta_min      35.41
_cell_volume                     551.048
_computing_cell_refinement       'CAD4 Express'
_computing_data_collection       'CAD4 Express'
_computing_data_reduction        'XCAD4 (Harms 1996)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.733
_diffrn_measured_fraction_theta_max 0.733
_diffrn_measurement_device_type  'Enraf-Nonius CAD4'
_diffrn_measurement_method       omega/2Theta
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0219
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5225
_diffrn_reflns_theta_full        75.43
_diffrn_reflns_theta_max         75.43
_diffrn_reflns_theta_min         3.71
_diffrn_standards_decay_%        2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.775
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9831
_exptl_absorpt_correction_type   psi-scan
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.200
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.034
_refine_ls_extinction_coef       0.009(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1679
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.054
_refine_ls_R_factor_all          0.0447
_refine_ls_R_factor_gt           0.0373
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0751P)²+0.0445P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1092
_refine_ls_wR_factor_ref         0.1141
_reflns_number_gt                1399
_reflns_number_total             1679
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1267-2033.cff
_cod_data_source_block           gj132
_cod_original_cell_volume        551.0
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               8102143
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_Wyckoff_symbol
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.1682(3) 0.31288(10) 0.42465(9) 0.0477(3) Uani 1 2 i d . . .
O2 O 0.1205(4) 0.15861(11) 0.50219(9) 0.0577(4) Uani 1 2 i d . . .
N1 N 0.3008(3) 0.14129(10) 0.18909(9) 0.0351(3) Uani 1 2 i d . . .
C2 C 0.1649(3) 0.23646(12) 0.26109(11) 0.0331(3) Uani 1 2 i d . . .
C3 C 0.0406(4) 0.24218(12) 0.37037(11) 0.0355(3) Uani 1 2 i d . . .
C4 C 0.1599(4) 0.14536(13) 0.40709(11) 0.0380(3) Uani 1 2 i d . . .
C5 C 0.3073(4) 0.03997(12) 0.31885(11) 0.0347(3) Uani 1 2 i d . . .
C6 C 0.3824(4) -0.06160(13) 0.33695(13) 0.0408(4) Uani 1 2 i d . . .
H6 H 0.3418 -0.0626 0.4058 0.053 Uiso 1 2 i calc R . .
C7 C 0.5171(4) -0.16064(13) 0.25260(14) 0.0448(4) Uani 1 2 i d . . .
H7 H 0.5685 -0.2282 0.2647 0.058 Uiso 1 2 i calc R . .
C8 C 0.5757(4) -0.15935(13) 0.14993(13) 0.0441(4) Uani 1 2 i d . . .
H8 H 0.6645 -0.2266 0.0931 0.057 Uiso 1 2 i calc R . .
C9 C 0.5031(4) -0.05845(13) 0.13100(12) 0.0404(3) Uani 1 2 i d . . .
H9 H 0.5473 -0.0580 0.0621 0.053 Uiso 1 2 i calc R . .
C10 C 0.3647(4) 0.04178(12) 0.21467(11) 0.0335(3) Uani 1 2 i d . . .
C1' C 0.1029(4) 0.33976(12) 0.23306(11) 0.0348(3) Uani 1 2 i d . . .
C2' C 0.1586(4) 0.46018(13) 0.31407(13) 0.0448(4) Uani 1 2 i d . . .
H2' H 0.2332 0.4762 0.3869 0.058 Uiso 1 2 i calc R . .
C3' C 0.1032(5) 0.55591(15) 0.28661(15) 0.0537(4) Uani 1 2 i d . . .
H3' H 0.1430 0.6362 0.3408 0.070 Uiso 1 2 i calc R . .
C4' C -0.0106(5) 0.53268(16) 0.17922(16) 0.0542(4) Uani 1 2 i d . . .
H4' H -0.0474 0.5973 0.1609 0.070 Uiso 1 2 i calc R . .
C5' C -0.0705(5) 0.41330(16) 0.09833(14) 0.0506(4) Uani 1 2 i d . . .
H5' H -0.1505 0.3978 0.0261 0.066 Uiso 1 2 i calc R . .
C6' C -0.0113(4) 0.31691(14) 0.12492(12) 0.0417(3) Uani 1 2 i d . . .
H6' H -0.0482 0.2368 0.0702 0.054 Uiso 1 2 i 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 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C2 N1 C10 120.63(11) . . ?
N1 C2 C1' 119.78(12) . . ?
N1 C2 C3 121.78(12) . . ?
C1' C2 C3 118.28(12) . . ?
O1 C3 C2 122.69(12) . . ?
O1 C3 C4 119.61(12) . . ?
C2 C3 C4 117.43(12) . . ?
O2 C4 C5 125.26(13) . . ?
O2 C4 C3 119.68(13) . . ?
C5 C4 C3 115.04(12) . . ?
C6 C5 C10 120.43(13) . . ?
C6 C5 C4 120.66(13) . . ?
C10 C5 C4 118.90(12) . . ?
C7 C6 C5 119.95(14) . . ?
C6 C7 C8 119.97(13) . . ?
C7 C8 C9 120.62(14) . . ?
C10 C9 C8 120.23(14) . . ?
C9 C10 C5 118.79(12) . . ?
C9 C10 N1 116.76(12) . . ?
C5 C10 N1 124.42(12) . . ?
C6' C1' C2' 119.40(13) . . ?
C6' C1' C2 119.84(12) . . ?
C2' C1' C2 120.76(12) . . ?
C3' C2' C1' 120.23(14) . . ?
C4' C3' C2' 120.11(15) . . ?
C3' C4' C5' 120.14(14) . . ?
C4' C5' C6' 120.05(14) . . ?
C5' C6' C1' 120.05(14) . . ?
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
O1 C3 1.2118(17) . ?
O2 C4 1.2092(18) . ?
N1 C2 1.2893(18) . ?
N1 C10 1.4169(16) . ?
C2 C1' 1.4792(18) . ?
C2 C3 1.5028(19) . ?
C3 C4 1.5362(18) . ?
C4 C5 1.4667(19) . ?
C5 C6 1.3950(18) . ?
C5 C10 1.4059(19) . ?
C6 C7 1.380(2) . ?
C7 C8 1.384(2) . ?
C8 C9 1.391(2) . ?
C9 C10 1.3905(19) . ?
C1' C6' 1.387(2) . ?
C1' C2' 1.393(2) . ?
C2' C3' 1.381(2) . ?
C3' C4' 1.376(3) . ?
C4' C5' 1.384(2) . ?
C5' C6' 1.385(2) . ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C10 N1 C2 C1' 179.53(11) . . . . ?
C10 N1 C2 C3 -5.2(2) . . . . ?
N1 C2 C3 O1 -159.48(14) . . . . ?
C1' C2 C3 O1 15.8(2) . . . . ?
N1 C2 C3 C4 14.6(2) . . . . ?
C1' C2 C3 C4 -170.13(11) . . . . ?
O1 C3 C4 O2 -18.9(2) . . . . ?
C2 C3 C4 O2 166.87(14) . . . . ?
O1 C3 C4 C5 159.40(14) . . . . ?
C2 C3 C4 C5 -14.85(18) . . . . ?
O2 C4 C5 C6 6.7(2) . . . . ?
C3 C4 C5 C6 -171.53(12) . . . . ?
O2 C4 C5 C10 -174.71(15) . . . . ?
C3 C4 C5 C10 7.12(19) . . . . ?
C10 C5 C6 C7 0.6(2) . . . . ?
C4 C5 C6 C7 179.24(13) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
C6 C7 C8 C9 0.6(2) . . . . ?
C7 C8 C9 C10 -1.1(2) . . . . ?
C8 C9 C10 C5 1.3(2) . . . . ?
C8 C9 C10 N1 179.49(12) . . . . ?
C6 C5 C10 C9 -1.1(2) . . . . ?
C4 C5 C10 C9 -179.75(13) . . . . ?
C6 C5 C10 N1 -179.10(12) . . . . ?
C4 C5 C10 N1 2.2(2) . . . . ?
C2 N1 C10 C9 178.32(12) . . . . ?
C2 N1 C10 C5 -3.6(2) . . . . ?
N1 C2 C1' C6' 37.98(19) . . . . ?
C3 C2 C1' C6' -137.42(14) . . . . ?
N1 C2 C1' C2' -141.90(15) . . . . ?
C3 C2 C1' C2' 42.70(19) . . . . ?
C6' C1' C2' C3' -0.5(2) . . . . ?
C2 C1' C2' C3' 179.34(15) . . . . ?
C1' C2' C3' C4' 0.6(3) . . . . ?
C2' C3' C4' C5' 0.1(3) . . . . ?
C3' C4' C5' C6' -0.9(3) . . . . ?
C4' C5' C6' C1' 1.0(3) . . . . ?
C2' C1' C6' C5' -0.3(2) . . . . ?
C2 C1' C6' C5' 179.85(13) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30653915
