#------------------------------------------------------------------------------
#$Date: 2021-10-14 05:46:49 +0300 (Thu, 14 Oct 2021) $
#$Revision: 269945 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/56/49/1564917.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_1564917
loop_
_publ_author_name
'Patel, Dinesh G.'
'Cox, Jordan M.'
'Bender, Branden M.'
'Benedict, Jason B.'
_publ_section_title
;
 3',5'-Dichloro-N,N-diphenyl-[1,1'-biphenyl]-4-amine
;
_journal_coeditor_code           HB4393
_journal_issue                   10
_journal_name_full               IUCrData
_journal_page_first              x211016
_journal_paper_doi               10.1107/S2414314621010166
_journal_volume                  6
_journal_year                    2021
_chemical_formula_iupac          'C24 H17 Cl2 N'
_chemical_formula_moiety         'C24 H17 Cl2 N'
_chemical_formula_sum            'C24 H17 Cl2 N'
_chemical_formula_weight         390.28
_chemical_name_common
;
4-(3,5-Dichlorophenyl)-N,N-diphenylaniline
;
_chemical_name_systematic
;
3',5'-Dichloro-N,N-diphenyl-[1,1'-biphenyl]-4-amine
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 110.4472(18)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   14.5188(11)
_cell_length_b                   7.7744(7)
_cell_length_c                   18.0700(16)
_cell_measurement_reflns_used    6404
_cell_measurement_temperature    90
_cell_measurement_theta_max      32.09
_cell_measurement_theta_min      2.88
_cell_volume                     1911.1(3)
_computing_cell_refinement
;
SAINT (Bruker, 2018)
;
_computing_data_collection
;
APEX3  (Bruker, 2018)
;
_computing_data_reduction
;
SAINT (Bruker, 2018)
;
_computing_molecular_graphics
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_publication_material
;
OLEX2 (Dolomanov et al.,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015)
;
_computing_structure_solution
;
olex2.solve (Dolomanov et al.,  2009)
;
_diffrn_ambient_temperature      90
_diffrn_detector                 'Bruker APEX2 area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.944
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker SMART APEXII area detector'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            18024
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         32.093
_diffrn_reflns_theta_min         1.559
_diffrn_source                   'microfocus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    0.348
_exptl_absorpt_correction_T_max  0.7463
_exptl_absorpt_correction_T_min  0.6773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2018)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             808
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.451
_refine_diff_density_min         -0.298
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         6318
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.018
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0584P)²+0.2620P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1053
_refine_ls_wR_factor_ref         0.1163
_reflns_number_gt                4600
_reflns_number_total             6318
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            hb4393sup1.cif
_cod_data_source_block           I
_cod_database_code               1564917
_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   0.897
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.58639(3) 0.75629(5) 0.37567(2) 0.02440(10) Uani d 1 . .
Cl Cl2 0.50900(3) 0.69374(6) 0.06326(2) 0.03003(11) Uani d 1 . .
C C4 0.22713(10) 0.73656(17) 0.17719(8) 0.0137(3) Uani d 1 . .
C C13 -0.10562(10) 0.75089(17) 0.21142(7) 0.0125(2) Uani d 1 . .
N N1 -0.07602(9) 0.73451(16) 0.14480(6) 0.0144(2) Uani d 1 . .
C C19 -0.14718(10) 0.75157(18) 0.06761(7) 0.0141(3) Uani d 1 . .
C C10 0.53724(11) 0.72175(18) 0.21805(9) 0.0190(3) Uani d 1 . .
H H10 0.605687 0.714403 0.227325 0.023 Uiso calc 1 . .
C C7 0.33384(11) 0.73663(17) 0.19079(8) 0.0147(3) Uani d 1 . .
C C1 0.02498(10) 0.73489(17) 0.15553(7) 0.0130(3) Uani d 1 . .
C C20 -0.23743(11) 0.6683(2) 0.04815(8) 0.0187(3) Uani d 1 . .
H H20 -0.250201 0.594839 0.085468 0.022 Uiso calc 1 . .
C C21 -0.30879(12) 0.6926(2) -0.02586(9) 0.0253(3) Uani d 1 . .
H H21 -0.370919 0.637873 -0.038583 0.030 Uiso calc 1 . .
C C14 -0.05678(10) 0.65661(18) 0.28000(7) 0.0140(3) Uani d 1 . .
H H14 -0.005075 0.580467 0.281248 0.017 Uiso calc 1 . .
C C8 0.40304(11) 0.75138(17) 0.26757(8) 0.0160(3) Uani d 1 . .
H H8 0.381605 0.767131 0.311129 0.019 Uiso calc 1 . .
C C16 -0.16027(11) 0.7831(2) 0.34467(8) 0.0189(3) Uani d 1 . .
H H16 -0.179045 0.793924 0.389821 0.023 Uiso calc 1 . .
C C6 0.06067(11) 0.64239(19) 0.10468(8) 0.0167(3) Uani d 1 . .
H H6 0.016417 0.577499 0.062682 0.020 Uiso calc 1 . .
C C3 0.19096(10) 0.82689(17) 0.22789(8) 0.0136(3) Uani d 1 . .
H H3 0.235370 0.889506 0.270698 0.016 Uiso calc 1 . .
C C2 0.09205(10) 0.82738(17) 0.21728(8) 0.0140(3) Uani d 1 . .
H H2 0.069372 0.891289 0.252341 0.017 Uiso calc 1 . .
C C9 0.50190(11) 0.74299(18) 0.27962(9) 0.0174(3) Uani d 1 . .
C C24 -0.12794(12) 0.8547(2) 0.01149(8) 0.0195(3) Uani d 1 . .
H H24 -0.066167 0.910609 0.024041 0.023 Uiso calc 1 . .
C C15 -0.08374(11) 0.67414(19) 0.34618(8) 0.0178(3) Uani d 1 . .
H H15 -0.049628 0.611252 0.392795 0.021 Uiso calc 1 . .
C C12 0.36787(11) 0.71894(19) 0.12771(9) 0.0181(3) Uani d 1 . .
H H12 0.322600 0.711890 0.075086 0.022 Uiso calc 1 . .
C C17 -0.20905(11) 0.87587(19) 0.27654(8) 0.0175(3) Uani d 1 . .
H H17 -0.261409 0.950418 0.275312 0.021 Uiso calc 1 . .
C C11 0.46825(12) 0.71177(19) 0.14253(9) 0.0197(3) Uani d 1 . .
C C23 -0.19930(13) 0.8754(2) -0.06270(9) 0.0266(4) Uani d 1 . .
H H23 -0.185790 0.944557 -0.101048 0.032 Uiso calc 1 . .
C C18 -0.18223(10) 0.86104(18) 0.21019(8) 0.0152(3) Uani d 1 . .
H H18 -0.215906 0.925670 0.164021 0.018 Uiso calc 1 . .
C C22 -0.28971(13) 0.7965(2) -0.08128(9) 0.0295(4) Uani d 1 . .
H H22 -0.338688 0.813149 -0.131806 0.035 Uiso calc 1 . .
C C5 0.15979(11) 0.64454(19) 0.11497(8) 0.0168(3) Uani d 1 . .
H H5 0.182456 0.582695 0.079321 0.020 Uiso calc 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'
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
C3 C4 C7 . . 120.19(12) ?
C3 C4 C5 . . 117.83(13) ?
C5 C4 C7 . . 121.97(12) ?
C14 C13 N1 . . 119.61(12) ?
C18 C13 N1 . . 121.12(12) ?
C18 C13 C14 . . 119.26(12) ?
C13 N1 C19 . . 119.49(11) ?
C1 N1 C13 . . 119.47(11) ?
C1 N1 C19 . . 119.91(11) ?
C20 C19 N1 . . 120.09(12) ?
C20 C19 C24 . . 119.57(13) ?
C24 C19 N1 . . 120.33(13) ?
C9 C10 H10 . . 121.5 ?
C11 C10 H10 . . 121.5 ?
C11 C10 C9 . . 117.00(14) ?
C8 C7 C4 . . 120.64(12) ?
C12 C7 C4 . . 120.76(13) ?
C12 C7 C8 . . 118.59(13) ?
C6 C1 N1 . . 120.92(12) ?
C2 C1 N1 . . 120.80(12) ?
C2 C1 C6 . . 118.28(13) ?
C19 C20 H20 . . 120.0 ?
C21 C20 C19 . . 119.97(14) ?
C21 C20 H20 . . 120.0 ?
C20 C21 H21 . . 119.9 ?
C22 C21 C20 . . 120.27(16) ?
C22 C21 H21 . . 119.9 ?
C13 C14 H14 . . 119.9 ?
C15 C14 C13 . . 120.17(13) ?
C15 C14 H14 . . 119.9 ?
C7 C8 H8 . . 120.0 ?
C9 C8 C7 . . 119.93(13) ?
C9 C8 H8 . . 120.0 ?
C15 C16 H16 . . 120.3 ?
C17 C16 H16 . . 120.3 ?
C17 C16 C15 . . 119.38(12) ?
C1 C6 H6 . . 119.6 ?
C5 C6 C1 . . 120.71(13) ?
C5 C6 H6 . . 119.6 ?
C4 C3 H3 . . 119.3 ?
C2 C3 C4 . . 121.48(13) ?
C2 C3 H3 . . 119.3 ?
C1 C2 H2 . . 119.7 ?
C3 C2 C1 . . 120.70(12) ?
C3 C2 H2 . . 119.7 ?
C10 C9 Cl1 . . 118.44(12) ?
C8 C9 Cl1 . . 119.14(11) ?
C8 C9 C10 . . 122.41(14) ?
C19 C24 H24 . . 120.1 ?
C23 C24 C19 . . 119.81(15) ?
C23 C24 H24 . . 120.1 ?
C14 C15 C16 . . 120.46(13) ?
C14 C15 H15 . . 119.8 ?
C16 C15 H15 . . 119.8 ?
C7 C12 H12 . . 120.2 ?
C11 C12 C7 . . 119.52(14) ?
C11 C12 H12 . . 120.2 ?
C16 C17 H17 . . 119.6 ?
C18 C17 C16 . . 120.81(13) ?
C18 C17 H17 . . 119.6 ?
C10 C11 Cl2 . . 118.69(12) ?
C10 C11 C12 . . 122.51(13) ?
C12 C11 Cl2 . . 118.79(12) ?
C24 C23 H23 . . 119.7 ?
C22 C23 C24 . . 120.60(15) ?
C22 C23 H23 . . 119.7 ?
C13 C18 H18 . . 120.0 ?
C17 C18 C13 . . 119.91(13) ?
C17 C18 H18 . . 120.0 ?
C21 C22 H22 . . 120.1 ?
C23 C22 C21 . . 119.74(14) ?
C23 C22 H22 . . 120.1 ?
C4 C5 H5 . . 119.5 ?
C6 C5 C4 . . 120.99(12) ?
C6 C5 H5 . . 119.5 ?
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 C9 . 1.7435(15) ?
Cl2 C11 . 1.7359(14) ?
C4 C7 . 1.481(2) ?
C4 C3 . 1.3945(18) ?
C4 C5 . 1.401(2) ?
C13 N1 . 1.4182(16) ?
C13 C14 . 1.4007(18) ?
C13 C18 . 1.3977(19) ?
N1 C19 . 1.4226(17) ?
N1 C1 . 1.4105(18) ?
C19 C20 . 1.392(2) ?
C19 C24 . 1.3954(19) ?
C10 H10 . 0.9500 ?
C10 C9 . 1.388(2) ?
C10 C11 . 1.384(2) ?
C7 C8 . 1.405(2) ?
C7 C12 . 1.3985(18) ?
C1 C6 . 1.4010(18) ?
C1 C2 . 1.3968(19) ?
C20 H20 . 0.9500 ?
C20 C21 . 1.389(2) ?
C21 H21 . 0.9500 ?
C21 C22 . 1.388(3) ?
C14 H14 . 0.9500 ?
C14 C15 . 1.3889(18) ?
C8 H8 . 0.9500 ?
C8 C9 . 1.376(2) ?
C16 H16 . 0.9500 ?
C16 C15 . 1.390(2) ?
C16 C17 . 1.389(2) ?
C6 H6 . 0.9500 ?
C6 C5 . 1.385(2) ?
C3 H3 . 0.9500 ?
C3 C2 . 1.3809(19) ?
C2 H2 . 0.9500 ?
C24 H24 . 0.9500 ?
C24 C23 . 1.388(2) ?
C15 H15 . 0.9500 ?
C12 H12 . 0.9500 ?
C12 C11 . 1.388(2) ?
C17 H17 . 0.9500 ?
C17 C18 . 1.3889(18) ?
C23 H23 . 0.9500 ?
C23 C22 . 1.380(3) ?
C18 H18 . 0.9500 ?
C22 H22 . 0.9500 ?
C5 H5 . 0.9500 ?
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
C4 C7 C8 C9 . . . . 176.90(13) ?
C4 C7 C12 C11 . . . . -177.15(13) ?
C4 C3 C2 C1 . . . . 0.8(2) ?
C13 N1 C19 C20 . . . . -45.47(18) ?
C13 N1 C19 C24 . . . . 133.12(14) ?
C13 N1 C1 C6 . . . . 149.15(13) ?
C13 N1 C1 C2 . . . . -30.74(19) ?
C13 C14 C15 C16 . . . . 1.0(2) ?
N1 C13 C14 C15 . . . . 178.69(12) ?
N1 C13 C18 C17 . . . . -179.36(13) ?
N1 C19 C20 C21 . . . . 176.51(13) ?
N1 C19 C24 C23 . . . . -177.65(13) ?
N1 C1 C6 C5 . . . . 179.35(13) ?
N1 C1 C2 C3 . . . . 179.69(12) ?
C19 N1 C1 C6 . . . . -43.08(19) ?
C19 N1 C1 C2 . . . . 137.03(13) ?
C19 C20 C21 C22 . . . . 1.5(2) ?
C19 C24 C23 C22 . . . . 0.8(2) ?
C7 C4 C3 C2 . . . . -179.17(12) ?
C7 C4 C5 C6 . . . . 178.17(13) ?
C7 C8 C9 Cl1 . . . . -178.43(10) ?
C7 C8 C9 C10 . . . . 0.6(2) ?
C7 C12 C11 Cl2 . . . . -178.84(11) ?
C7 C12 C11 C10 . . . . -0.1(2) ?
C1 N1 C19 C20 . . . . 146.77(13) ?
C1 N1 C19 C24 . . . . -34.64(19) ?
C1 C6 C5 C4 . . . . 1.1(2) ?
C20 C19 C24 C23 . . . . 0.9(2) ?
C20 C21 C22 C23 . . . . 0.2(2) ?
C14 C13 N1 C19 . . . . 148.16(13) ?
C14 C13 N1 C1 . . . . -44.03(18) ?
C14 C13 C18 C17 . . . . 0.0(2) ?
C8 C7 C12 C11 . . . . 1.7(2) ?
C16 C17 C18 C13 . . . . 0.3(2) ?
C6 C1 C2 C3 . . . . -0.2(2) ?
C3 C4 C7 C8 . . . . 30.22(19) ?
C3 C4 C7 C12 . . . . -150.93(13) ?
C3 C4 C5 C6 . . . . -0.5(2) ?
C2 C1 C6 C5 . . . . -0.8(2) ?
C9 C10 C11 Cl2 . . . . 177.49(11) ?
C9 C10 C11 C12 . . . . -1.2(2) ?
C24 C19 C20 C21 . . . . -2.1(2) ?
C24 C23 C22 C21 . . . . -1.3(2) ?
C15 C16 C17 C18 . . . . 0.0(2) ?
C12 C7 C8 C9 . . . . -2.0(2) ?
C17 C16 C15 C14 . . . . -0.7(2) ?
C11 C10 C9 Cl1 . . . . -179.96(11) ?
C11 C10 C9 C8 . . . . 1.0(2) ?
C18 C13 N1 C19 . . . . -32.49(19) ?
C18 C13 N1 C1 . . . . 135.33(14) ?
C18 C13 C14 C15 . . . . -0.7(2) ?
C5 C4 C7 C8 . . . . -148.45(14) ?
C5 C4 C7 C12 . . . . 30.4(2) ?
C5 C4 C3 C2 . . . . -0.4(2) ?

_cod_database_fobs_code 1564917
