#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/31/2223181.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2223181
loop_
_publ_author_name
'Wang, Shu-Liang'
'Li, Qing'
'Wang, Xiang-Shan'
'Tu, Shu-Jiang'
_publ_section_title
;
 3-(4-Chlorophenyl)-1-(4-nitrophenyl)benzo[f]quinoline
;
_journal_coeditor_code           PV2192
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2137
_journal_paper_doi               10.1107/S1600536809031122
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C25 H15 Cl N2 O2'
_chemical_formula_moiety         'C25 H15 Cl N2 O2'
_chemical_formula_sum            'C25 H15 Cl N2 O2'
_chemical_formula_weight         410.84
_chemical_melting_point_gt       559
_chemical_melting_point_lt       561
_chemical_name_systematic
;
3-(4-Chlorophenyl)-1-(4-nitrophenyl)benzo[f]quinoline
;
_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
_cell_angle_alpha                108.182(4)
_cell_angle_beta                 105.366(4)
_cell_angle_gamma                92.739(3)
_cell_formula_units_Z            2
_cell_length_a                   9.1390(12)
_cell_length_b                   9.5350(11)
_cell_length_c                   11.9668(17)
_cell_measurement_reflns_used    3276
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      27.9
_cell_measurement_theta_min      1.9
_cell_volume                     945.6(2)
_computing_cell_refinement       'CrystalClear (Rigaku, 1999)'
_computing_data_collection       'CrystalClear (Rigaku, 1999)'
_computing_data_reduction        'CrystalClear (Rigaku, 1999)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure/MSC (Rigaku/MSC (2003)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      113(2)
_diffrn_detector_area_resol_mean 14.63
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_sigmaI/netI    0.0468
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11798
_diffrn_reflns_theta_full        27.87
_diffrn_reflns_theta_max         27.87
_diffrn_reflns_theta_min         2.27
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.9515
_exptl_absorpt_correction_T_min  0.9264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 1999)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.443
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.363
_refine_diff_density_min         -0.470
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4467
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0599
_refine_ls_R_factor_gt           0.0493
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0619P)²+0.2446P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1209
_refine_ls_wR_factor_ref         0.1285
_reflns_number_gt                3779
_reflns_number_total             4467
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pv2192.cif
_cod_data_source_block           I
_cod_database_code               2223181
_cod_database_fobs_code          2223181
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 -0.44740(5) 1.45046(5) 0.65255(4) 0.03265(15) Uani d . 1 . .
O O1 0.11873(18) 0.19922(14) 0.55020(13) 0.0390(4) Uani d . 1 . .
O O2 0.20781(16) 0.29045(15) 0.43402(12) 0.0373(3) Uani d . 1 . .
N N1 0.09795(15) 1.16854(15) 0.97919(12) 0.0190(3) Uani d . 1 . .
N N2 0.16218(16) 0.30287(16) 0.52288(13) 0.0237(3) Uani d . 1 . .
C C1 0.03104(17) 1.11236(17) 0.85802(15) 0.0180(3) Uani d . 1 . .
C C2 0.05962(18) 0.97511(17) 0.78672(15) 0.0197(3) Uani d . 1 . .
H H2 0.0085 0.9370 0.7008 0.024 Uiso calc R 1 . .
C C3 0.16056(18) 0.89462(17) 0.83916(14) 0.0178(3) Uani d . 1 . .
C C4 0.24330(17) 0.95634(17) 0.96652(15) 0.0181(3) Uani d . 1 . .
C C5 0.20143(17) 1.09302(17) 1.03223(15) 0.0184(3) Uani d . 1 . .
C C6 0.26619(18) 1.15733(18) 1.16297(15) 0.0212(3) Uani d . 1 . .
H H6 0.2361 1.2475 1.2062 0.025 Uiso calc R 1 . .
C C7 0.36952(19) 1.09148(19) 1.22567(15) 0.0228(4) Uani d . 1 . .
H H7 0.4074 1.1337 1.3128 0.027 Uiso calc R 1 . .
C C8 0.42320(18) 0.95928(18) 1.16351(15) 0.0208(3) Uani d . 1 . .
C C9 0.36459(18) 0.89220(17) 1.03335(15) 0.0193(3) Uani d . 1 . .
C C10 0.43260(18) 0.77063(18) 0.97623(16) 0.0221(4) Uani d . 1 . .
H H10 0.4000 0.7273 0.8890 0.027 Uiso calc R 1 . .
C C11 0.54513(19) 0.71333(19) 1.04391(17) 0.0253(4) Uani d . 1 . .
H H11 0.5879 0.6308 1.0029 0.030 Uiso calc R 1 . .
C C12 0.59711(19) 0.7757(2) 1.17264(17) 0.0265(4) Uani d . 1 . .
H H12 0.6725 0.7342 1.2192 0.032 Uiso calc R 1 . .
C C13 0.53780(19) 0.89731(19) 1.23024(16) 0.0244(4) Uani d . 1 . .
H H13 0.5746 0.9411 1.3173 0.029 Uiso calc R 1 . .
C C14 -0.08359(18) 1.19683(17) 0.80328(15) 0.0187(3) Uani d . 1 . .
C C15 -0.17082(19) 1.14279(18) 0.67950(15) 0.0224(4) Uani d . 1 . .
H H15 -0.1543 1.0514 0.6265 0.027 Uiso calc R 1 . .
C C16 -0.28137(19) 1.22157(19) 0.63335(16) 0.0237(4) Uani d . 1 . .
H H16 -0.3407 1.1840 0.5492 0.028 Uiso calc R 1 . .
C C17 -0.30481(18) 1.35505(19) 0.71036(16) 0.0222(4) Uani d . 1 . .
C C18 -0.21770(19) 1.41347(19) 0.83272(16) 0.0236(4) Uani d . 1 . .
H H18 -0.2323 1.5067 0.8845 0.028 Uiso calc R 1 . .
C C19 -0.10882(19) 1.33288(18) 0.87788(15) 0.0209(3) Uani d . 1 . .
H H19 -0.0497 1.3713 0.9620 0.025 Uiso calc R 1 . .
C C20 0.16339(17) 0.74070(17) 0.75715(15) 0.0184(3) Uani d . 1 . .
C C21 0.21663(19) 0.71865(18) 0.65500(15) 0.0216(3) Uani d . 1 . .
H H21 0.2540 0.8023 0.6383 0.026 Uiso calc R 1 . .
C C22 0.21556(18) 0.57585(18) 0.57745(15) 0.0214(3) Uani d . 1 . .
H H22 0.2528 0.5604 0.5082 0.026 Uiso calc R 1 . .
C C23 0.15882(18) 0.45621(17) 0.60359(14) 0.0193(3) Uani d . 1 . .
C C24 0.09988(19) 0.47391(18) 0.70168(15) 0.0221(4) Uani d . 1 . .
H H24 0.0590 0.3899 0.7161 0.027 Uiso calc R 1 . .
C C25 0.10213(19) 0.61767(18) 0.77824(15) 0.0215(3) Uani d . 1 . .
H H25 0.0616 0.6326 0.8458 0.026 Uiso calc R 1 . .
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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C1 N1 C5 . . 118.45(14) ?
O1 N2 O2 . . 124.78(15) ?
O1 N2 C23 . . 117.66(14) ?
O2 N2 C23 . . 117.56(14) ?
N1 C1 C2 . . 121.44(14) ?
N1 C1 C14 . . 117.00(14) ?
C2 C1 C14 . . 121.43(14) ?
C3 C2 C1 . . 121.03(15) ?
C3 C2 H2 . . 119.5 ?
C1 C2 H2 . . 119.5 ?
C2 C3 C4 . . 119.17(14) ?
C2 C3 C20 . . 115.55(14) ?
C4 C3 C20 . . 125.06(14) ?
C3 C4 C5 . . 115.47(14) ?
C3 C4 C9 . . 125.96(14) ?
C5 C4 C9 . . 118.57(14) ?
N1 C5 C4 . . 124.14(15) ?
N1 C5 C6 . . 115.65(14) ?
C4 C5 C6 . . 120.19(14) ?
C7 C6 C5 . . 120.86(15) ?
C7 C6 H6 . . 119.6 ?
C5 C6 H6 . . 119.6 ?
C6 C7 C8 . . 121.35(15) ?
C6 C7 H7 . . 119.3 ?
C8 C7 H7 . . 119.3 ?
C13 C8 C9 . . 119.58(15) ?
C13 C8 C7 . . 120.33(15) ?
C9 C8 C7 . . 120.06(15) ?
C10 C9 C8 . . 117.29(15) ?
C10 C9 C4 . . 124.07(15) ?
C8 C9 C4 . . 118.58(14) ?
C11 C10 C9 . . 121.62(16) ?
C11 C10 H10 . . 119.2 ?
C9 C10 H10 . . 119.2 ?
C10 C11 C12 . . 120.63(16) ?
C10 C11 H11 . . 119.7 ?
C12 C11 H11 . . 119.7 ?
C13 C12 C11 . . 119.08(15) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C12 C13 C8 . . 121.65(16) ?
C12 C13 H13 . . 119.2 ?
C8 C13 H13 . . 119.2 ?
C19 C14 C15 . . 118.20(15) ?
C19 C14 C1 . . 119.49(14) ?
C15 C14 C1 . . 122.29(14) ?
C16 C15 C14 . . 120.53(15) ?
C16 C15 H15 . . 119.7 ?
C14 C15 H15 . . 119.7 ?
C17 C16 C15 . . 119.71(15) ?
C17 C16 H16 . . 120.1 ?
C15 C16 H16 . . 120.1 ?
C16 C17 C18 . . 121.18(15) ?
C16 C17 Cl1 . . 119.34(13) ?
C18 C17 Cl1 . . 119.48(13) ?
C17 C18 C19 . . 118.48(15) ?
C17 C18 H18 . . 120.8 ?
C19 C18 H18 . . 120.8 ?
C18 C19 C14 . . 121.87(15) ?
C18 C19 H19 . . 119.1 ?
C14 C19 H19 . . 119.1 ?
C21 C20 C25 . . 119.49(15) ?
C21 C20 C3 . . 120.79(14) ?
C25 C20 C3 . . 119.58(14) ?
C22 C21 C20 . . 120.64(15) ?
C22 C21 H21 . . 119.7 ?
C20 C21 H21 . . 119.7 ?
C23 C22 C21 . . 118.27(15) ?
C23 C22 H22 . . 120.9 ?
C21 C22 H22 . . 120.9 ?
C24 C23 C22 . . 122.69(15) ?
C24 C23 N2 . . 118.94(15) ?
C22 C23 N2 . . 118.37(14) ?
C23 C24 C25 . . 118.12(15) ?
C23 C24 H24 . . 120.9 ?
C25 C24 H24 . . 120.9 ?
C24 C25 C20 . . 120.71(15) ?
C24 C25 H25 . . 119.6 ?
C20 C25 H25 . . 119.6 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C17 . 1.7414(17) ?
O1 N2 . 1.2142(19) ?
O2 N2 . 1.2165(19) ?
N1 C1 . 1.333(2) ?
N1 C5 . 1.359(2) ?
N2 C23 . 1.487(2) ?
C1 C2 . 1.401(2) ?
C1 C14 . 1.490(2) ?
C2 C3 . 1.377(2) ?
C2 H2 . 0.9500 ?
C3 C4 . 1.424(2) ?
C3 C20 . 1.495(2) ?
C4 C5 . 1.425(2) ?
C4 C9 . 1.464(2) ?
C5 C6 . 1.432(2) ?
C6 C7 . 1.351(2) ?
C6 H6 . 0.9500 ?
C7 C8 . 1.432(2) ?
C7 H7 . 0.9500 ?
C8 C13 . 1.412(2) ?
C8 C9 . 1.423(2) ?
C9 C10 . 1.413(2) ?
C10 C11 . 1.379(2) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.402(3) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.368(2) ?
C12 H12 . 0.9500 ?
C13 H13 . 0.9500 ?
C14 C19 . 1.396(2) ?
C14 C15 . 1.398(2) ?
C15 C16 . 1.388(2) ?
C15 H15 . 0.9500 ?
C16 C17 . 1.383(2) ?
C16 H16 . 0.9500 ?
C17 C18 . 1.385(2) ?
C18 C19 . 1.386(2) ?
C18 H18 . 0.9500 ?
C19 H19 . 0.9500 ?
C20 C21 . 1.393(2) ?
C20 C25 . 1.396(2) ?
C21 C22 . 1.386(2) ?
C21 H21 . 0.9500 ?
C22 C23 . 1.386(2) ?
C22 H22 . 0.9500 ?
C23 C24 . 1.384(2) ?
C24 C25 . 1.386(2) ?
C24 H24 . 0.9500 ?
C25 H25 . 0.9500 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C24 H24 Cg 1_545 0.95 2.72 3.510(12) 142
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C5 N1 C1 C2 . . . . 3.2(2) ?
C5 N1 C1 C14 . . . . 179.07(13) ?
N1 C1 C2 C3 . . . . -1.3(2) ?
C14 C1 C2 C3 . . . . -177.01(14) ?
C1 C2 C3 C4 . . . . -3.6(2) ?
C1 C2 C3 C20 . . . . 171.36(14) ?
C2 C3 C4 C5 . . . . 6.1(2) ?
C20 C3 C4 C5 . . . . -168.31(14) ?
C2 C3 C4 C9 . . . . -173.89(14) ?
C20 C3 C4 C9 . . . . 11.7(3) ?
C1 N1 C5 C4 . . . . -0.2(2) ?
C1 N1 C5 C6 . . . . -178.50(14) ?
C3 C4 C5 N1 . . . . -4.4(2) ?
C9 C4 C5 N1 . . . . 175.56(14) ?
C3 C4 C5 C6 . . . . 173.80(14) ?
C9 C4 C5 C6 . . . . -6.2(2) ?
N1 C5 C6 C7 . . . . 179.58(15) ?
C4 C5 C6 C7 . . . . 1.2(2) ?
C5 C6 C7 C8 . . . . 2.9(3) ?
C6 C7 C8 C13 . . . . 176.32(15) ?
C6 C7 C8 C9 . . . . -1.7(2) ?
C13 C8 C9 C10 . . . . -4.0(2) ?
C7 C8 C9 C10 . . . . 174.05(14) ?
C13 C8 C9 C4 . . . . 178.58(14) ?
C7 C8 C9 C4 . . . . -3.4(2) ?
C3 C4 C9 C10 . . . . 10.0(3) ?
C5 C4 C9 C10 . . . . -170.04(15) ?
C3 C4 C9 C8 . . . . -172.80(14) ?
C5 C4 C9 C8 . . . . 7.2(2) ?
C8 C9 C10 C11 . . . . 3.6(2) ?
C4 C9 C10 C11 . . . . -179.09(15) ?
C9 C10 C11 C12 . . . . -0.7(3) ?
C10 C11 C12 C13 . . . . -1.9(3) ?
C11 C12 C13 C8 . . . . 1.5(3) ?
C9 C8 C13 C12 . . . . 1.5(2) ?
C7 C8 C13 C12 . . . . -176.50(15) ?
N1 C1 C14 C19 . . . . 3.9(2) ?
C2 C1 C14 C19 . . . . 179.74(15) ?
N1 C1 C14 C15 . . . . -174.37(15) ?
C2 C1 C14 C15 . . . . 1.5(2) ?
C19 C14 C15 C16 . . . . -1.2(2) ?
C1 C14 C15 C16 . . . . 177.03(15) ?
C14 C15 C16 C17 . . . . 0.3(3) ?
C15 C16 C17 C18 . . . . 1.3(3) ?
C15 C16 C17 Cl1 . . . . -178.25(13) ?
C16 C17 C18 C19 . . . . -1.9(3) ?
Cl1 C17 C18 C19 . . . . 177.61(12) ?
C17 C18 C19 C14 . . . . 1.0(3) ?
C15 C14 C19 C18 . . . . 0.6(2) ?
C1 C14 C19 C18 . . . . -177.75(15) ?
C2 C3 C20 C21 . . . . 66.7(2) ?
C4 C3 C20 C21 . . . . -118.66(18) ?
C2 C3 C20 C25 . . . . -108.78(17) ?
C4 C3 C20 C25 . . . . 65.8(2) ?
C25 C20 C21 C22 . . . . -2.9(2) ?
C3 C20 C21 C22 . . . . -178.39(15) ?
C20 C21 C22 C23 . . . . 0.7(2) ?
C21 C22 C23 C24 . . . . 1.7(2) ?
C21 C22 C23 N2 . . . . -178.06(14) ?
O1 N2 C23 C24 . . . . -3.1(2) ?
O2 N2 C23 C24 . . . . 176.60(14) ?
O1 N2 C23 C22 . . . . 176.65(15) ?
O2 N2 C23 C22 . . . . -3.6(2) ?
C22 C23 C24 C25 . . . . -1.8(2) ?
N2 C23 C24 C25 . . . . 177.99(14) ?
C23 C24 C25 C20 . . . . -0.5(2) ?
C21 C20 C25 C24 . . . . 2.8(2) ?
C3 C20 C25 C24 . . . . 178.38(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24743039
