#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/31/2233146.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_2233146
loop_
_publ_author_name
'Yuan, Jianchao'
'Xie, Xiaoli'
'Liu, Yufeng'
'Miao, Chengping'
'Li, Jing'
_publ_section_title
;
 (E)-N-{(E)-2-[(3,5-Dimethylbiphenyl-4-yl)imino]acenaphthen-1-ylidene}-2,6-dimethyl-4-phenylaniline
;
_journal_coeditor_code           FY2034
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o210
_journal_paper_doi               10.1107/S1600536811054092
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C40 H32 N2'
_chemical_formula_moiety         'C40 H32 N2'
_chemical_formula_sum            'C40 H32 N2'
_chemical_formula_weight         540.68
_chemical_name_systematic
;
(E)-N-{(E)-2-[(3,5-Dimethylbiphenyl-4-
yl)imino]acenaphthen-1-ylidene}-2,6-dimethyl-4-phenylaniline
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 124.084(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   22.994(14)
_cell_length_b                   8.676(5)
_cell_length_c                   18.652(18)
_cell_measurement_reflns_used    3073
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      25.72
_cell_measurement_theta_min      2.14
_cell_volume                     3082(4)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008b)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008b)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008b)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008b)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0306
_diffrn_reflns_av_sigmaI/netI    0.0331
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            10667
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.14
_exptl_absorpt_coefficient_mu    0.067
_exptl_absorpt_correction_T_max  0.9873
_exptl_absorpt_correction_T_min  0.9847
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 2008a)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.165
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.19
_refine_diff_density_max         0.227
_refine_diff_density_min         -0.195
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.161
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2857
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.161
_refine_ls_R_factor_all          0.1140
_refine_ls_R_factor_gt           0.0591
_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)+(0.0705P)²+3.4006P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1613
_refine_ls_wR_factor_ref         0.2114
_reflns_number_gt                1596
_reflns_number_total             2857
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            fy2034.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2233146
_cod_database_fobs_code          2233146
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
C C1 0.2760(2) 0.8437(6) 0.7549(2) 0.1024(15) Uani d . 1 1
H H1 0.2411 0.7699 0.7368 0.123 Uiso calc R 1 1
C C2 0.3295(3) 0.8543(8) 0.8419(3) 0.132(2) Uani d . 1 1
H H2 0.3303 0.7877 0.8815 0.159 Uiso calc R 1 1
C C3 0.3807(3) 0.9614(9) 0.8696(3) 0.135(3) Uani d . 1 1
H H3 0.4158 0.9705 0.9283 0.162 Uiso calc R 1 1
C C4 0.3807(2) 1.0559(8) 0.8112(4) 0.126(2) Uani d . 1 1
H H4 0.4165 1.1278 0.8300 0.151 Uiso calc R 1 1
C C5 0.3271(2) 1.0452(6) 0.7229(3) 0.1089(16) Uani d . 1 1
H H5 0.3277 1.1089 0.6832 0.131 Uiso calc R 1 1
C C6 0.27359(18) 0.9396(5) 0.6951(2) 0.0804(11) Uani d . 1 1
C C7 0.21565(18) 0.9254(4) 0.6012(2) 0.0691(9) Uani d . 1 1
C C8 0.22787(19) 0.9461(4) 0.5373(2) 0.0719(10) Uani d . 1 1
H H8 0.2729 0.9726 0.5534 0.086 Uiso calc R 1 1
C C9 0.1758(2) 0.9289(4) 0.4504(2) 0.0707(10) Uani d . 1 1
C C10 0.10860(19) 0.8859(3) 0.42739(19) 0.0639(9) Uani d . 1 1
C C11 0.09402(17) 0.8687(4) 0.4894(2) 0.0668(9) Uani d . 1 1
C C12 0.14776(18) 0.8885(4) 0.5757(2) 0.0720(10) Uani d . 1 1
H H12 0.1382 0.8768 0.6177 0.086 Uiso calc R 1 1
C C13 0.02861(17) 0.7530(3) 0.29823(18) 0.0617(9) Uani d . 1 1
C C14 0.04351(15) 0.5886(3) 0.32523(18) 0.0526(8) Uani d . 1 1
C C15 0.0000 0.5015(4) 0.2500 0.0497(10) Uani d S 1 2
C C16 0.0000 0.3396(5) 0.2500 0.0642(12) Uani d S 1 2
C C17 0.0457(2) 0.2681(4) 0.3300(2) 0.0833(12) Uani d . 1 1
H H17 0.0476 0.1610 0.3334 0.100 Uiso calc R 1 1
C C18 0.08782(19) 0.3537(4) 0.4034(2) 0.0753(10) Uani d . 1 1
H H18 0.1177 0.3028 0.4555 0.090 Uiso calc R 1 1
C C19 0.08738(16) 0.5154(3) 0.4025(2) 0.0619(9) Uani d . 1 1
H H19 0.1162 0.5712 0.4532 0.074 Uiso calc R 1 1
C C20 0.1907(3) 0.9524(5) 0.3822(2) 0.1042(15) Uani d . 1 1
H H20A 0.2376 0.9908 0.4088 0.156 Uiso calc R 1 1
H H20B 0.1579 1.0253 0.3402 0.156 Uiso calc R 1 1
H H20C 0.1861 0.8559 0.3542 0.156 Uiso calc R 1 1
C C21 0.02117(19) 0.8275(5) 0.4649(3) 0.0984(14) Uani d . 1 1
H H21A -0.0123 0.8974 0.4212 0.148 Uiso calc R 1 1
H H21B 0.0194 0.8350 0.5151 0.148 Uiso calc R 1 1
H H21C 0.0101 0.7240 0.4430 0.148 Uiso calc R 1 1
N N1 0.05454(16) 0.8787(3) 0.33777(16) 0.0755(9) Uani d . 1 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'
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
C6 C1 C2 . . 121.2(5)
C6 C1 H1 . . 119.4
C2 C1 H1 . . 119.4
C3 C2 C1 . . 120.3(6)
C3 C2 H2 . . 119.9
C1 C2 H2 . . 119.9
C2 C3 C4 . . 119.8(5)
C2 C3 H3 . . 120.1
C4 C3 H3 . . 120.1
C3 C4 C5 . . 120.4(5)
C3 C4 H4 . . 119.8
C5 C4 H4 . . 119.8
C6 C5 C4 . . 119.8(5)
C6 C5 H5 . . 120.1
C4 C5 H5 . . 120.1
C1 C6 C5 . . 118.5(4)
C1 C6 C7 . . 120.4(4)
C5 C6 C7 . . 121.1(4)
C8 C7 C12 . . 117.9(3)
C8 C7 C6 . . 121.4(3)
C12 C7 C6 . . 120.8(3)
C9 C8 C7 . . 122.5(3)
C9 C8 H8 . . 118.7
C7 C8 H8 . . 118.7
C8 C9 C10 . . 117.9(3)
C8 C9 C20 . . 121.3(4)
C10 C9 C20 . . 120.8(3)
C11 C10 C9 . . 121.0(3)
C11 C10 N1 . . 121.2(3)
C9 C10 N1 . . 117.3(3)
C10 C11 C12 . . 118.9(3)
C10 C11 C21 . . 121.4(3)
C12 C11 C21 . . 119.7(4)
C11 C12 C7 . . 121.7(3)
C11 C12 H12 . . 119.2
C7 C12 H12 . . 119.2
N1 C13 C14 . . 133.3(3)
N1 C13 C13 . 2 120.18(17)
C14 C13 C13 . 2 106.44(15)
C19 C14 C15 . . 119.7(3)
C19 C14 C13 . . 134.2(3)
C15 C14 C13 . . 106.2(2)
C14 C15 C14 2 . 114.8(3)
C14 C15 C16 2 . 122.62(17)
C14 C15 C16 . . 122.62(17)
C17 C16 C17 2 . 127.3(4)
C17 C16 C15 2 . 116.3(2)
C17 C16 C15 . . 116.3(2)
C18 C17 C16 . . 120.8(3)
C18 C17 H17 . . 119.6
C16 C17 H17 . . 119.6
C17 C18 C19 . . 122.3(3)
C17 C18 H18 . . 118.8
C19 C18 H18 . . 118.8
C14 C19 C18 . . 118.2(3)
C14 C19 H19 . . 120.9
C18 C19 H19 . . 120.9
C9 C20 H20A . . 109.5
C9 C20 H20B . . 109.5
H20A C20 H20B . . 109.5
C9 C20 H20C . . 109.5
H20A C20 H20C . . 109.5
H20B C20 H20C . . 109.5
C11 C21 H21A . . 109.5
C11 C21 H21B . . 109.5
H21A C21 H21B . . 109.5
C11 C21 H21C . . 109.5
H21A C21 H21C . . 109.5
H21B C21 H21C . . 109.5
C13 N1 C10 . . 122.7(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
C1 C6 . 1.368(6)
C1 C2 . 1.386(6)
C1 H1 . 0.9300
C2 C3 . 1.355(8)
C2 H2 . 0.9300
C3 C4 . 1.363(8)
C3 H3 . 0.9300
C4 C5 . 1.402(6)
C4 H4 . 0.9300
C5 C6 . 1.381(6)
C5 H5 . 0.9300
C6 C7 . 1.497(5)
C7 C8 . 1.381(5)
C7 C12 . 1.391(5)
C8 C9 . 1.382(4)
C8 H8 . 0.9300
C9 C10 . 1.404(5)
C9 C20 . 1.504(5)
C10 C11 . 1.381(5)
C10 N1 . 1.419(4)
C11 C12 . 1.385(4)
C11 C21 . 1.512(5)
C12 H12 . 0.9300
C13 N1 . 1.263(4)
C13 C14 . 1.487(4)
C13 C13 2 1.522(6)
C14 C19 . 1.368(4)
C14 C15 . 1.403(3)
C15 C14 2 1.403(3)
C15 C16 . 1.404(6)
C16 C17 2 1.400(4)
C16 C17 . 1.400(4)
C17 C18 . 1.370(5)
C17 H17 . 0.9300
C18 C19 . 1.403(4)
C18 H18 . 0.9300
C19 H19 . 0.9300
C20 H20A . 0.9600
C20 H20B . 0.9600
C20 H20C . 0.9600
C21 H21A . 0.9600
C21 H21B . 0.9600
C21 H21C . 0.9600
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_4
_geom_torsion
C6 C1 C2 C3 . . 0.3(8)
C1 C2 C3 C4 . . -2.0(8)
C2 C3 C4 C5 . . 1.5(8)
C3 C4 C5 C6 . . 0.8(7)
C2 C1 C6 C5 . . 2.0(7)
C2 C1 C6 C7 . . 179.5(4)
C4 C5 C6 C1 . . -2.5(6)
C4 C5 C6 C7 . . 180.0(4)
C1 C6 C7 C8 . . -142.6(4)
C5 C6 C7 C8 . . 34.9(5)
C1 C6 C7 C12 . . 36.4(5)
C5 C6 C7 C12 . . -146.1(4)
C12 C7 C8 C9 . . -1.1(5)
C6 C7 C8 C9 . . 177.9(3)
C7 C8 C9 C10 . . -1.3(5)
C7 C8 C9 C20 . . 179.9(3)
C8 C9 C10 C11 . . 3.2(5)
C20 C9 C10 C11 . . -178.0(3)
C8 C9 C10 N1 . . 175.9(3)
C20 C9 C10 N1 . . -5.3(5)
C9 C10 C11 C12 . . -2.7(5)
N1 C10 C11 C12 . . -175.1(3)
C9 C10 C11 C21 . . 177.9(3)
N1 C10 C11 C21 . . 5.5(5)
C10 C11 C12 C7 . . 0.2(5)
C21 C11 C12 C7 . . 179.6(3)
C8 C7 C12 C11 . . 1.7(5)
C6 C7 C12 C11 . . -177.3(3)
N1 C13 C14 C19 . . 4.2(7)
C13 C13 C14 C19 2 . -178.1(4)
N1 C13 C14 C15 . . -176.1(4)
C13 C13 C14 C15 2 . 1.6(4)
C19 C14 C15 C14 . 2 179.1(3)
C13 C14 C15 C14 . 2 -0.65(17)
C19 C14 C15 C16 . . -0.9(3)
C13 C14 C15 C16 . . 179.35(17)
C14 C15 C16 C17 2 2 0.5(2)
C14 C15 C16 C17 . 2 -179.5(2)
C14 C15 C16 C17 2 . -179.5(2)
C14 C15 C16 C17 . . 0.5(2)
C17 C16 C17 C18 2 . 179.8(4)
C15 C16 C17 C18 . . -0.2(4)
C16 C17 C18 C19 . . 0.1(6)
C15 C14 C19 C18 . . 0.8(5)
C13 C14 C19 C18 . . -179.5(4)
C17 C18 C19 C14 . . -0.5(6)
C14 C13 N1 C10 . . -1.7(7)
C13 C13 N1 C10 2 . -179.2(4)
C11 C10 N1 C13 . . -78.7(5)
C9 C10 N1 C13 . . 108.6(4)
