#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025761.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_4025761
loop_
_publ_author_name
'Xianglin Tang'
'Weimin Liu'
'Jiasheng Wu'
'Chun-Sing Lee'
'Juanjuan You'
'Pengfei Wang'
_publ_section_title
;
 Synthesis, Crystal Structures, and Photophysical Properties of
 Triphenylamine-Based Multicyano Derivatives
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7273
_journal_page_last               7278
_journal_paper_doi               10.1021/jo101456v
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C26 H15 N5'
_chemical_formula_weight         397.43
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/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                 113.5500(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.5051(4)
_cell_length_b                   13.3289(4)
_cell_length_c                   13.1464(4)
_cell_measurement_reflns_used    7307
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.00
_cell_measurement_theta_min      2.25
_cell_volume                     2169.36(11)
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0334
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            7307
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.25
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.9903
_exptl_absorpt_correction_T_min  0.9550
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR by T.Higashi    8 March, 1995'
_exptl_crystal_colour            'dark blue'
_exptl_crystal_density_diffrn    1.217
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.53
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.232
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     280
_refine_ls_number_reflns         3817
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0944
_refine_ls_R_factor_gt           0.0680
_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)+(0.0558P)²+0.4458P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1422
_reflns_number_gt                3082
_reflns_number_total             3817
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101456v_si_002.cif
_cod_data_source_block           a
_cod_database_code               4025761
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.68690(15) 0.06378(15) 0.85376(15) 0.0315(5) Uani 1 1 d . . .
N2 N 1.3303(2) 0.21549(19) 0.8297(2) 0.0589(7) Uani 1 1 d . . .
N3 N 1.14275(18) 0.3179(2) 1.0061(2) 0.0540(7) Uani 1 1 d . . .
N4 N 1.13220(19) -0.1083(2) 0.54139(18) 0.0503(6) Uani 1 1 d . . .
N5 N 1.0105(2) -0.15382(19) 0.79668(18) 0.0557(7) Uani 1 1 d . . .
C1 C 0.67624(17) 0.08917(18) 0.95521(18) 0.0299(5) Uani 1 1 d . . .
C2 C 0.6960(2) 0.1853(2) 0.9971(2) 0.0464(7) Uani 1 1 d . . .
H2 H 0.7196 0.2357 0.9607 0.056 Uiso 1 1 calc R . .
C3 C 0.6813(3) 0.2078(2) 1.0927(3) 0.0591(8) Uani 1 1 d . . .
H3 H 0.6944 0.2741 1.1215 0.071 Uiso 1 1 calc R . .
C4 C 0.6479(2) 0.1355(3) 1.1468(2) 0.0516(8) Uani 1 1 d . . .
H4 H 0.6382 0.1518 1.2126 0.062 Uiso 1 1 calc R . .
C5 C 0.6288(2) 0.0402(2) 1.1054(2) 0.0455(7) Uani 1 1 d . . .
H5 H 0.6057 -0.0099 1.1424 0.055 Uiso 1 1 calc R . .
C6 C 0.64312(19) 0.0166(2) 1.00935(19) 0.0353(6) Uani 1 1 d . . .
H6 H 0.6300 -0.0498 0.9809 0.042 Uiso 1 1 calc R . .
C7 C 0.58990(18) 0.03137(19) 0.76352(18) 0.0312(5) Uani 1 1 d . . .
C8 C 0.5020(2) 0.0942(2) 0.7232(2) 0.0432(7) Uani 1 1 d . . .
H8 H 0.5056 0.1596 0.7533 0.052 Uiso 1 1 calc R . .
C9 C 0.4073(2) 0.0610(3) 0.6377(2) 0.0558(9) Uani 1 1 d . . .
H9 H 0.3456 0.1033 0.6103 0.067 Uiso 1 1 calc R . .
C10 C 0.4032(2) -0.0329(3) 0.5930(2) 0.0562(9) Uani 1 1 d . . .
H10 H 0.3389 -0.0548 0.5340 0.067 Uiso 1 1 calc R . .
C11 C 0.4907(2) -0.0948(3) 0.6326(2) 0.0531(8) Uani 1 1 d . . .
H11 H 0.4875 -0.1595 0.6011 0.064 Uiso 1 1 calc R . .
C12 C 0.5845(2) -0.0632(2) 0.7189(2) 0.0426(6) Uani 1 1 d . . .
H12 H 0.6451 -0.1068 0.7475 0.051 Uiso 1 1 calc R . .
C13 C 0.78335(17) 0.07478(18) 0.84240(18) 0.0279(5) Uani 1 1 d . . .
C14 C 0.78993(18) 0.0632(2) 0.73939(19) 0.0340(6) Uani 1 1 d . . .
H14 H 0.7272 0.0454 0.6761 0.041 Uiso 1 1 calc R . .
C15 C 0.88618(18) 0.0773(2) 0.72902(18) 0.0328(6) Uani 1 1 d . . .
H15 H 0.8886 0.0689 0.6583 0.039 Uiso 1 1 calc R . .
C16 C 0.98084(17) 0.10389(18) 0.81951(17) 0.0275(5) Uani 1 1 d . . .
C17 C 0.97410(18) 0.11288(18) 0.92293(17) 0.0295(5) Uani 1 1 d . . .
H17 H 1.0371 0.1297 0.9864 0.035 Uiso 1 1 calc R . .
C18 C 0.87906(18) 0.09807(19) 0.93448(18) 0.0300(5) Uani 1 1 d . . .
H18 H 0.8775 0.1036 1.0059 0.036 Uiso 1 1 calc R . .
C19 C 1.08001(18) 0.12323(17) 0.80433(17) 0.0275(5) Uani 1 1 d . . .
C20 C 1.15688(18) 0.19207(18) 0.86364(19) 0.0298(5) Uani 1 1 d . . .
C21 C 1.2538(2) 0.20490(19) 0.8454(2) 0.0369(6) Uani 1 1 d . . .
C22 C 1.14688(18) 0.2598(2) 0.9435(2) 0.0359(6) Uani 1 1 d . . .
C23 C 1.10058(18) 0.06906(18) 0.71746(18) 0.0302(5) Uani 1 1 d . . .
H23 H 1.1291 0.1069 0.6741 0.036 Uiso 1 1 calc R . .
C24 C 1.08291(17) -0.02837(18) 0.69381(17) 0.0285(5) Uani 1 1 d . . .
C25 C 1.11001(19) -0.0731(2) 0.6082(2) 0.0354(6) Uani 1 1 d . . .
C26 C 1.0419(2) -0.0968(2) 0.75219(19) 0.0363(6) 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'
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
C13 N1 C1 121.68(18) . . ?
C13 N1 C7 122.13(18) . . ?
C1 N1 C7 116.11(17) . . ?
C6 C1 C2 119.8(2) . . ?
C6 C1 N1 119.2(2) . . ?
C2 C1 N1 121.0(2) . . ?
C1 C2 C3 119.3(3) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 121.0(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 119.6(2) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.1(3) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.2(3) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C8 C7 C12 120.1(2) . . ?
C8 C7 N1 119.8(2) . . ?
C12 C7 N1 120.1(2) . . ?
C7 C8 C9 119.3(3) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
C10 C9 C8 120.1(3) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C10 C11 C12 119.9(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C7 C12 C11 120.1(3) . . ?
C7 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
N1 C13 C14 121.4(2) . . ?
N1 C13 C18 120.9(2) . . ?
C14 C13 C18 117.7(2) . . ?
C15 C14 C13 120.6(2) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 122.0(2) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C15 C16 C17 117.0(2) . . ?
C15 C16 C19 120.44(19) . . ?
C17 C16 C19 122.5(2) . . ?
C18 C17 C16 121.5(2) . . ?
C18 C17 H17 119.2 . . ?
C16 C17 H17 119.2 . . ?
C17 C18 C13 121.1(2) . . ?
C17 C18 H18 119.4 . . ?
C13 C18 H18 119.4 . . ?
C20 C19 C16 124.8(2) . . ?
C20 C19 C23 115.8(2) . . ?
C16 C19 C23 119.4(2) . . ?
C19 C20 C22 124.6(2) . . ?
C19 C20 C21 121.3(2) . . ?
C22 C20 C21 114.1(2) . . ?
N2 C21 C20 179.3(3) . . ?
N3 C22 C20 176.0(3) . . ?
C24 C23 C19 126.0(2) . . ?
C24 C23 H23 117.0 . . ?
C19 C23 H23 117.0 . . ?
C23 C24 C26 124.3(2) . . ?
C23 C24 C25 120.4(2) . . ?
C26 C24 C25 115.2(2) . . ?
N4 C25 C24 179.5(3) . . ?
N5 C26 C24 177.5(3) . . ?
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
N1 C13 1.377(3) . ?
N1 C1 1.438(3) . ?
N1 C7 1.438(3) . ?
N2 C21 1.140(3) . ?
N3 C22 1.147(3) . ?
N4 C25 1.137(3) . ?
N5 C26 1.139(3) . ?
C1 C6 1.377(3) . ?
C1 C2 1.379(4) . ?
C2 C3 1.381(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.364(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.388(3) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 C8 1.375(3) . ?
C7 C12 1.380(4) . ?
C8 C9 1.396(4) . ?
C8 H8 0.9500 . ?
C9 C10 1.373(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.363(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.385(4) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C14 1.401(3) . ?
C13 C18 1.408(3) . ?
C14 C15 1.373(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.400(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.403(3) . ?
C16 C19 1.454(3) . ?
C17 C18 1.366(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.371(3) . ?
C19 C23 1.468(3) . ?
C20 C22 1.432(3) . ?
C20 C21 1.432(3) . ?
C23 C24 1.335(3) . ?
C23 H23 0.9500 . ?
C24 C26 1.438(3) . ?
C24 C25 1.444(3) . ?
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
C13 N1 C1 C6 -121.8(2) . . . . ?
C7 N1 C1 C6 61.3(3) . . . . ?
C13 N1 C1 C2 59.8(3) . . . . ?
C7 N1 C1 C2 -117.0(3) . . . . ?
C6 C1 C2 C3 -0.6(4) . . . . ?
N1 C1 C2 C3 177.7(2) . . . . ?
C1 C2 C3 C4 0.4(5) . . . . ?
C2 C3 C4 C5 -0.2(5) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C2 C1 C6 C5 0.5(4) . . . . ?
N1 C1 C6 C5 -177.8(2) . . . . ?
C4 C5 C6 C1 -0.3(4) . . . . ?
C13 N1 C7 C8 -117.4(3) . . . . ?
C1 N1 C7 C8 59.5(3) . . . . ?
C13 N1 C7 C12 63.8(3) . . . . ?
C1 N1 C7 C12 -119.3(2) . . . . ?
C12 C7 C8 C9 0.5(4) . . . . ?
N1 C7 C8 C9 -178.3(2) . . . . ?
C7 C8 C9 C10 -1.3(4) . . . . ?
C8 C9 C10 C11 0.9(4) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C8 C7 C12 C11 0.7(4) . . . . ?
N1 C7 C12 C11 179.5(2) . . . . ?
C10 C11 C12 C7 -1.1(4) . . . . ?
C1 N1 C13 C14 -171.1(2) . . . . ?
C7 N1 C13 C14 5.6(4) . . . . ?
C1 N1 C13 C18 8.9(3) . . . . ?
C7 N1 C13 C18 -174.4(2) . . . . ?
N1 C13 C14 C15 178.1(2) . . . . ?
C18 C13 C14 C15 -2.0(4) . . . . ?
C13 C14 C15 C16 -0.2(4) . . . . ?
C14 C15 C16 C17 1.7(4) . . . . ?
C14 C15 C16 C19 -176.9(2) . . . . ?
C15 C16 C17 C18 -1.1(4) . . . . ?
C19 C16 C17 C18 177.5(2) . . . . ?
C16 C17 C18 C13 -1.1(4) . . . . ?
N1 C13 C18 C17 -177.4(2) . . . . ?
C14 C13 C18 C17 2.6(4) . . . . ?
C15 C16 C19 C20 146.4(2) . . . . ?
C17 C16 C19 C20 -32.1(4) . . . . ?
C15 C16 C19 C23 -31.4(3) . . . . ?
C17 C16 C19 C23 150.1(2) . . . . ?
C16 C19 C20 C22 -4.7(4) . . . . ?
C23 C19 C20 C22 173.2(2) . . . . ?
C16 C19 C20 C21 178.5(2) . . . . ?
C23 C19 C20 C21 -3.6(3) . . . . ?
C19 C20 C21 N2 67(25) . . . . ?
C22 C20 C21 N2 -110(25) . . . . ?
C19 C20 C22 N3 -152(4) . . . . ?
C21 C20 C22 N3 25(4) . . . . ?
C20 C19 C23 C24 139.3(2) . . . . ?
C16 C19 C23 C24 -42.7(3) . . . . ?
C19 C23 C24 C26 -1.1(4) . . . . ?
C19 C23 C24 C25 -178.0(2) . . . . ?
C23 C24 C25 N4 69(30) . . . . ?
C26 C24 C25 N4 -108(30) . . . . ?
C23 C24 C26 N5 -166(7) . . . . ?
C25 C24 C26 N5 11(7) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659294
