#------------------------------------------------------------------------------
#$Date: 2023-03-06 10:36:50 +0200 (Mon, 06 Mar 2023) $
#$Revision: 281656 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/68/8106836.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_8106836
loop_
_publ_author_name
'Van Tonder, Johannes'
'Visser, Hendrik G.'
'Koen, Renier'
_publ_section_title
;
 The crystal structure of 6-chloro-2,4-diphenylquinoline
;
_journal_issue                   1
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              233
_journal_page_last               235
_journal_paper_doi               10.1515/ncrs-2015-0102
_journal_volume                  231
_journal_year                    2016
_chemical_formula_moiety         'C21 H14 Cl N'
_chemical_formula_sum            'C21 H14 Cl N'
_chemical_formula_weight         315.78
_chemical_name_systematic        6-Chloro-2,4-diphenylquinoline
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/6
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 90.000(5)
_cell_angle_gamma                90.000(5)
_cell_formula_units_Z            4
_cell_length_a                   7.686(5)
_cell_length_b                   10.161(5)
_cell_length_c                   19.899(5)
_cell_measurement_reflns_used    9452
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.14
_cell_measurement_theta_min      2.86
_cell_volume                     1554.1(13)
_computing_cell_refinement       'Saint-Plus (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2012)'
_computing_data_reduction        'SAINT-Plus and XPREP (Bruker, 2008)'
_computing_molecular_graphics    'DIAMOND 3.0c (Brandenburg & Putz, 2004)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            26440
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.997
_diffrn_reflns_theta_min         2.865
_exptl_absorpt_coefficient_mu    0.244
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.350
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       cuboid
_exptl_crystal_F_000             656.0
_exptl_crystal_size_max          0.651
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.389
_exptl_transmission_factor_max   0.908
_exptl_transmission_factor_min   0.870
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.054
_refine_ls_abs_structure_details
;
 Flack x determined using 1656 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.00(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3753
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.066
_refine_ls_R_factor_all          0.0340
_refine_ls_R_factor_gt           0.0318
_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)+(0.0441P)²+0.1791P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0765
_refine_ls_wR_factor_ref         0.0783
_reflns_Friedel_coverage         0.942
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                3585
_reflns_number_total             3754
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2015-0102_suppl.cif
_cod_data_source_block           shelx
_cod_database_code               8106836
_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.
;
_shelxl_version_number           2014/6
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'-x+1/2, y, z+1/2'
'x+1/2, -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 0.4676(2) 0.1223(2) 0.46425(9) 0.0172(4) Uani 1 1 d . . . . .
C3 C 0.5642(2) 0.06912(18) 0.57738(10) 0.0162(4) Uani 1 1 d . . . . .
C5 C 0.6280(2) -0.1710(2) 0.59797(10) 0.0189(4) Uani 1 1 d . . . . .
H5 H 0.6766 -0.1534 0.6398 0.023 Uiso 1 1 calc R U . . .
N N 0.4495(2) -0.00261(17) 0.44632(8) 0.0192(3) Uani 1 1 d . . . . .
C26 C 0.7223(2) 0.2223(2) 0.65356(10) 0.0187(4) Uani 1 1 d . . . . .
H26 H 0.7630 0.2657 0.6155 0.022 Uiso 1 1 calc R U . . .
C9 C 0.4961(3) -0.09624(19) 0.49227(10) 0.0181(4) Uani 1 1 d . . . . .
C2 C 0.5187(2) 0.16069(19) 0.53010(10) 0.0172(4) Uani 1 1 d . . . . .
H2 H 0.5213 0.2496 0.5412 0.021 Uiso 1 1 calc R U . . .
C11 C 0.4301(3) 0.2240(2) 0.41211(9) 0.0178(4) Uani 1 1 d . . . . .
C6 C 0.6191(3) -0.2973(2) 0.57484(11) 0.0216(4) Uani 1 1 d . . . . .
C4 C 0.5627(2) -0.06669(18) 0.55779(9) 0.0160(4) Uani 1 1 d . . . . .
C7 C 0.5424(3) -0.3293(2) 0.51262(11) 0.0246(4) Uani 1 1 d . . . . .
H7 H 0.5322 -0.4166 0.4992 0.030 Uiso 1 1 calc R U . . .
C21 C 0.6127(2) 0.11313(19) 0.64642(9) 0.0164(4) Uani 1 1 d . . . . .
C24 C 0.7085(3) 0.2034(2) 0.77420(10) 0.0250(5) Uani 1 1 d . . . . .
H24 H 0.7423 0.2323 0.8166 0.030 Uiso 1 1 calc R U . . .
C25 C 0.7709(3) 0.2663(2) 0.71691(11) 0.0233(4) Uani 1 1 d . . . . .
H25 H 0.8452 0.3381 0.7211 0.028 Uiso 1 1 calc R U . . .
C16 C 0.5106(3) 0.3473(2) 0.41474(11) 0.0211(4) Uani 1 1 d . . . . .
H16 H 0.5853 0.3669 0.4501 0.025 Uiso 1 1 calc R U . . .
C15 C 0.4806(3) 0.4408(2) 0.36516(11) 0.0240(5) Uani 1 1 d . . . . .
H15 H 0.5339 0.5228 0.3677 0.029 Uiso 1 1 calc R U . . .
C22 C 0.5477(3) 0.0517(2) 0.70432(10) 0.0200(4) Uani 1 1 d . . . . .
H22 H 0.4723 -0.0195 0.7004 0.024 Uiso 1 1 calc R U . . .
C23 C 0.5957(3) 0.0973(2) 0.76781(10) 0.0224(4) Uani 1 1 d . . . . .
H23 H 0.5519 0.0565 0.8061 0.027 Uiso 1 1 calc R U . . .
C13 C 0.2886(3) 0.2893(2) 0.30839(10) 0.0242(5) Uani 1 1 d . . . . .
H13 H 0.2150 0.2696 0.2727 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4828(3) -0.2298(2) 0.47211(10) 0.0218(4) Uani 1 1 d . . . . .
H8 H 0.4329 -0.2502 0.4308 0.026 Uiso 1 1 calc R U . . .
C12 C 0.3171(3) 0.1965(2) 0.35867(10) 0.0210(4) Uani 1 1 d . . . . .
H12 H 0.2606 0.1157 0.3568 0.025 Uiso 1 1 calc R U . . .
C14 C 0.3701(3) 0.4114(2) 0.31148(10) 0.0248(4) Uani 1 1 d . . . . .
H14 H 0.3511 0.4733 0.2779 0.030 Uiso 1 1 calc R U . . .
Cl1 Cl 0.70653(9) -0.42527(5) 0.62263(3) 0.03510(16) 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'
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
N C1 C2 122.62(18) . .
N C1 C11 117.09(17) . .
C2 C1 C11 120.29(17) . .
C2 C3 C4 117.73(18) . .
C2 C3 C21 119.54(17) . .
C4 C3 C21 122.73(17) . .
C6 C5 C4 119.63(18) . .
C1 N C9 117.31(17) . .
C25 C26 C21 120.62(19) . .
N C9 C8 117.23(18) . .
N C9 C4 123.80(17) . .
C8 C9 C4 118.93(18) . .
C3 C2 C1 121.17(18) . .
C16 C11 C12 118.76(19) . .
C16 C11 C1 120.57(18) . .
C12 C11 C1 120.64(18) . .
C5 C6 C7 122.3(2) . .
C5 C6 Cl1 119.83(17) . .
C7 C6 Cl1 117.92(17) . .
C5 C4 C9 118.84(17) . .
C5 C4 C3 124.23(17) . .
C9 C4 C3 116.89(17) . .
C8 C7 C6 119.1(2) . .
C26 C21 C22 118.91(18) . .
C26 C21 C3 118.78(17) . .
C22 C21 C3 122.27(17) . .
C23 C24 C25 119.75(19) . .
C26 C25 C24 120.18(19) . .
C15 C16 C11 120.9(2) . .
C16 C15 C14 119.8(2) . .
C23 C22 C21 120.13(19) . .
C24 C23 C22 120.37(19) . .
C14 C13 C12 120.1(2) . .
C7 C8 C9 120.97(19) . .
C13 C12 C11 120.6(2) . .
C13 C14 C15 119.91(19) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 N 1.326(3) .
C1 C2 1.422(3) .
C1 C11 1.492(3) .
C3 C2 1.369(3) .
C3 C4 1.434(3) .
C3 C21 1.492(3) .
C5 C6 1.365(3) .
C5 C4 1.420(3) .
N C9 1.367(3) .
C26 C25 1.389(3) .
C26 C21 1.400(3) .
C9 C8 1.419(3) .
C9 C4 1.432(3) .
C11 C16 1.398(3) .
C11 C12 1.401(3) .
C6 C7 1.409(3) .
C6 Cl1 1.745(2) .
C7 C8 1.371(3) .
C21 C22 1.402(3) .
C24 C23 1.389(3) .
C24 C25 1.392(3) .
C16 C15 1.389(3) .
C15 C14 1.397(3) .
C22 C23 1.395(3) .
C13 C14 1.391(3) .
C13 C12 1.392(3) .
