#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025762.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_4025762
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_moiety         'C27 H14 N6'
_chemical_formula_sum            'C27 H14 N6'
_chemical_formula_weight         422.44
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 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                 100.12(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.556(3)
_cell_length_b                   8.2956(17)
_cell_length_c                   19.778(4)
_cell_measurement_reflns_used    456
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     2189.5(8)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_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  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0349
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            14855
_diffrn_reflns_theta_full        25.50
_diffrn_reflns_theta_max         25.50
_diffrn_reflns_theta_min         2.89
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.9921
_exptl_absorpt_correction_T_min  0.9695
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            blue-black
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       strip
_exptl_crystal_F_000             872
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.154
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.188
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         4065
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.188
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0534
_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)+(0.0383P)²+0.5961P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1150
_reflns_number_gt                3663
_reflns_number_total             4065
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101456v_si_003.cif
_cod_data_source_block           sa51
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Multi-scan' changed to
'multi-scan' according to the built-in table from CIF Core dictionary
named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_database_code               4025762
loop_
_symmetry_equiv_pos_as_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_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 0.70539(11) 0.70190(17) 0.12432(7) 0.0360(4) Uani 1 1 d . . .
N2 N 1.09026(13) 0.7153(2) -0.04433(8) 0.0470(4) Uani 1 1 d . . .
N3 N 1.31754(13) 1.0472(2) 0.05264(9) 0.0543(5) Uani 1 1 d . . .
N4 N 1.17030(15) 1.3647(2) 0.11239(10) 0.0620(5) Uani 1 1 d . . .
N5 N 1.21308(14) 1.2670(2) 0.31242(9) 0.0590(5) Uani 1 1 d . . .
N6 N 1.09450(16) 0.7879(3) 0.27667(10) 0.0664(6) Uani 1 1 d . . .
C1 C 0.66406(14) 0.5268(2) 0.02306(9) 0.0432(5) Uani 1 1 d . . .
H1A H 0.6920 0.6035 -0.0039 0.052 Uiso 1 1 calc R . .
C2 C 0.62451(16) 0.3829(3) -0.00595(10) 0.0504(5) Uani 1 1 d . . .
H2A H 0.6276 0.3597 -0.0526 0.060 Uiso 1 1 calc R . .
C3 C 0.58085(16) 0.2735(3) 0.03217(11) 0.0516(5) Uani 1 1 d . . .
H3A H 0.5548 0.1750 0.0120 0.062 Uiso 1 1 calc R . .
C4 C 0.57505(16) 0.3075(2) 0.09953(11) 0.0499(5) Uani 1 1 d . . .
H4A H 0.5429 0.2339 0.1254 0.060 Uiso 1 1 calc R . .
C5 C 0.61604(14) 0.4487(2) 0.12977(10) 0.0410(4) Uani 1 1 d . . .
H5A H 0.6125 0.4713 0.1764 0.049 Uiso 1 1 calc R . .
C6 C 0.66224(13) 0.5572(2) 0.09183(9) 0.0350(4) Uani 1 1 d . . .
C7 C 0.65204(13) 0.7782(2) 0.17263(9) 0.0344(4) Uani 1 1 d . . .
C8 C 0.56154(14) 0.8543(2) 0.14926(10) 0.0415(4) Uani 1 1 d . . .
H8A H 0.5345 0.8557 0.1016 0.050 Uiso 1 1 calc R . .
C9 C 0.51049(15) 0.9284(2) 0.19555(11) 0.0486(5) Uani 1 1 d . . .
H9A H 0.4487 0.9815 0.1796 0.058 Uiso 1 1 calc R . .
C10 C 0.54949(15) 0.9248(2) 0.26482(11) 0.0488(5) Uani 1 1 d . . .
H10A H 0.5140 0.9743 0.2967 0.059 Uiso 1 1 calc R . .
C11 C 0.63995(15) 0.8494(2) 0.28805(10) 0.0447(5) Uani 1 1 d . . .
H11A H 0.6669 0.8485 0.3357 0.054 Uiso 1 1 calc R . .
C12 C 0.69148(14) 0.7750(2) 0.24205(9) 0.0382(4) Uani 1 1 d . . .
H12A H 0.7534 0.7223 0.2580 0.046 Uiso 1 1 calc R . .
C13 C 0.79814(13) 0.7604(2) 0.11749(8) 0.0331(4) Uani 1 1 d . . .
C14 C 0.82763(13) 0.9165(2) 0.14188(9) 0.0352(4) Uani 1 1 d . . .
H14A H 0.7820 0.9817 0.1611 0.042 Uiso 1 1 calc R . .
C15 C 0.92068(13) 0.9746(2) 0.13809(9) 0.0339(4) Uani 1 1 d . . .
H15A H 0.9389 1.0788 0.1560 0.041 Uiso 1 1 calc R . .
C16 C 0.99074(13) 0.8848(2) 0.10847(8) 0.0318(4) Uani 1 1 d . . .
C17 C 0.96119(13) 0.7287(2) 0.08481(8) 0.0339(4) Uani 1 1 d . . .
H17A H 1.0069 0.6636 0.0656 0.041 Uiso 1 1 calc R . .
C18 C 0.86839(13) 0.6686(2) 0.08886(9) 0.0348(4) Uani 1 1 d . . .
H18A H 0.8509 0.5633 0.0721 0.042 Uiso 1 1 calc R . .
C19 C 1.08632(13) 0.9561(2) 0.10232(8) 0.0325(4) Uani 1 1 d . . .
C20 C 1.14391(13) 0.9198(2) 0.05391(9) 0.0337(4) Uani 1 1 d . . .
C21 C 1.11340(14) 0.8051(2) -0.00031(9) 0.0356(4) Uani 1 1 d . . .
C22 C 1.24065(14) 0.9904(2) 0.05378(9) 0.0392(4) Uani 1 1 d . . .
C23 C 1.12629(12) 1.0824(2) 0.15401(9) 0.0356(4) Uani 1 1 d . . .
C24 C 1.15254(14) 1.2409(2) 0.13056(9) 0.0400(4) Uani 1 1 d . . .
C25 C 1.13780(13) 1.0550(2) 0.22222(9) 0.0384(4) Uani 1 1 d . . .
C26 C 1.17943(14) 1.1748(3) 0.27203(10) 0.0439(5) Uani 1 1 d . . .
C27 C 1.11247(14) 0.9047(2) 0.25052(9) 0.0428(5) 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 C6 123.90(14) . . ?
C13 N1 C7 118.92(14) . . ?
C6 N1 C7 116.81(14) . . ?
C6 C1 C2 119.22(18) . . ?
C6 C1 H1A 120.4 . . ?
C2 C1 H1A 120.4 . . ?
C3 C2 C1 120.73(18) . . ?
C3 C2 H2A 119.6 . . ?
C1 C2 H2A 119.6 . . ?
C4 C3 C2 119.86(18) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.21(19) . . ?
C3 C4 H4A 119.9 . . ?
C5 C4 H4A 119.9 . . ?
C4 C5 C6 119.93(18) . . ?
C4 C5 H5A 120.0 . . ?
C6 C5 H5A 120.0 . . ?
C1 C6 C5 119.94(16) . . ?
C1 C6 N1 120.95(16) . . ?
C5 C6 N1 119.10(15) . . ?
C12 C7 C8 120.34(16) . . ?
C12 C7 N1 119.84(16) . . ?
C8 C7 N1 119.81(16) . . ?
C9 C8 C7 119.87(18) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C10 C9 C8 119.88(19) . . ?
C10 C9 H9A 120.1 . . ?
C8 C9 H9A 120.1 . . ?
C9 C10 C11 120.20(18) . . ?
C9 C10 H10A 119.9 . . ?
C11 C10 H10A 119.9 . . ?
C10 C11 C12 120.25(18) . . ?
C10 C11 H11A 119.9 . . ?
C12 C11 H11A 119.9 . . ?
C7 C12 C11 119.45(18) . . ?
C7 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
N1 C13 C18 122.78(15) . . ?
N1 C13 C14 119.82(15) . . ?
C18 C13 C14 117.37(16) . . ?
C15 C14 C13 120.87(16) . . ?
C15 C14 H14A 119.6 . . ?
C13 C14 H14A 119.6 . . ?
C14 C15 C16 122.12(16) . . ?
C14 C15 H15A 118.9 . . ?
C16 C15 H15A 118.9 . . ?
C17 C16 C15 116.70(15) . . ?
C17 C16 C19 123.56(15) . . ?
C15 C16 C19 119.72(15) . . ?
C18 C17 C16 121.66(16) . . ?
C18 C17 H17A 119.2 . . ?
C16 C17 H17A 119.2 . . ?
C17 C18 C13 121.25(16) . . ?
C17 C18 H18A 119.4 . . ?
C13 C18 H18A 119.4 . . ?
C20 C19 C16 126.61(16) . . ?
C20 C19 C23 116.64(15) . . ?
C16 C19 C23 116.75(14) . . ?
C19 C20 C22 122.93(16) . . ?
C19 C20 C21 122.78(16) . . ?
C22 C20 C21 114.28(15) . . ?
N2 C21 C20 178.62(19) . . ?
N3 C22 C20 179.0(2) . . ?
C25 C23 C24 118.52(17) . . ?
C25 C23 C19 121.95(16) . . ?
C24 C23 C19 119.52(15) . . ?
N4 C24 C23 178.2(2) . . ?
C23 C25 C27 122.90(17) . . ?
C23 C25 C26 121.96(17) . . ?
C27 C25 C26 115.11(16) . . ?
N5 C26 C25 178.5(2) . . ?
N6 C27 C25 176.2(2) . . ?
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 1.376(2) . ?
N1 C6 1.437(2) . ?
N1 C7 1.442(2) . ?
N2 C21 1.147(2) . ?
N3 C22 1.148(2) . ?
N4 C24 1.128(2) . ?
N5 C26 1.142(2) . ?
N6 C27 1.144(3) . ?
C1 C6 1.388(3) . ?
C1 C2 1.391(3) . ?
C1 H1A 0.9500 . ?
C2 C3 1.378(3) . ?
C2 H2A 0.9500 . ?
C3 C4 1.377(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.386(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(2) . ?
C5 H5A 0.9500 . ?
C7 C12 1.383(2) . ?
C7 C8 1.385(3) . ?
C8 C9 1.385(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.379(3) . ?
C9 H9A 0.9500 . ?
C10 C11 1.381(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.385(3) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C18 1.413(2) . ?
C13 C14 1.415(2) . ?
C14 C15 1.365(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.413(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.411(2) . ?
C16 C19 1.449(2) . ?
C17 C18 1.368(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.371(2) . ?
C19 C23 1.497(2) . ?
C20 C22 1.437(3) . ?
C20 C21 1.439(3) . ?
C23 C25 1.350(2) . ?
C23 C24 1.459(3) . ?
C25 C27 1.433(3) . ?
C25 C26 1.443(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
C6 C1 C2 C3 2.2(3) . . . . ?
C1 C2 C3 C4 0.8(3) . . . . ?
C2 C3 C4 C5 -2.2(3) . . . . ?
C3 C4 C5 C6 0.7(3) . . . . ?
C2 C1 C6 C5 -3.7(3) . . . . ?
C2 C1 C6 N1 177.84(17) . . . . ?
C4 C5 C6 C1 2.3(3) . . . . ?
C4 C5 C6 N1 -179.21(17) . . . . ?
C13 N1 C6 C1 -46.2(3) . . . . ?
C7 N1 C6 C1 140.95(18) . . . . ?
C13 N1 C6 C5 135.39(18) . . . . ?
C7 N1 C6 C5 -37.5(2) . . . . ?
C13 N1 C7 C12 -63.7(2) . . . . ?
C6 N1 C7 C12 109.58(18) . . . . ?
C13 N1 C7 C8 116.36(19) . . . . ?
C6 N1 C7 C8 -70.4(2) . . . . ?
C12 C7 C8 C9 0.4(3) . . . . ?
N1 C7 C8 C9 -179.67(16) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C8 C9 C10 C11 0.9(3) . . . . ?
C9 C10 C11 C12 -0.9(3) . . . . ?
C8 C7 C12 C11 -0.4(3) . . . . ?
N1 C7 C12 C11 179.67(16) . . . . ?
C10 C11 C12 C7 0.6(3) . . . . ?
C6 N1 C13 C18 -12.6(3) . . . . ?
C7 N1 C13 C18 160.12(16) . . . . ?
C6 N1 C13 C14 169.63(16) . . . . ?
C7 N1 C13 C14 -17.6(2) . . . . ?
N1 C13 C14 C15 177.43(16) . . . . ?
C18 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C16 1.6(3) . . . . ?
C14 C15 C16 C17 -2.1(2) . . . . ?
C14 C15 C16 C19 176.51(16) . . . . ?
C15 C16 C17 C18 1.5(2) . . . . ?
C19 C16 C17 C18 -177.01(16) . . . . ?
C16 C17 C18 C13 -0.5(3) . . . . ?
N1 C13 C18 C17 -177.91(16) . . . . ?
C14 C13 C18 C17 -0.1(2) . . . . ?
C17 C16 C19 C20 26.3(3) . . . . ?
C15 C16 C19 C20 -152.19(17) . . . . ?
C17 C16 C19 C23 -153.77(16) . . . . ?
C15 C16 C19 C23 27.8(2) . . . . ?
C16 C19 C20 C22 -176.54(16) . . . . ?
C23 C19 C20 C22 3.5(3) . . . . ?
C16 C19 C20 C21 2.1(3) . . . . ?
C23 C19 C20 C21 -177.80(16) . . . . ?
C19 C20 C21 N2 154(9) . . . . ?
C22 C20 C21 N2 -27(9) . . . . ?
C19 C20 C22 N3 -135(12) . . . . ?
C21 C20 C22 N3 47(12) . . . . ?
C20 C19 C23 C25 -125.82(19) . . . . ?
C16 C19 C23 C25 54.2(2) . . . . ?
C20 C19 C23 C24 55.1(2) . . . . ?
C16 C19 C23 C24 -124.90(17) . . . . ?
C25 C23 C24 N4 -92(7) . . . . ?
C19 C23 C24 N4 87(7) . . . . ?
C24 C23 C25 C27 178.80(17) . . . . ?
C19 C23 C25 C27 -0.3(3) . . . . ?
C24 C23 C25 C26 -3.0(3) . . . . ?
C19 C23 C25 C26 177.89(16) . . . . ?
C23 C25 C26 N5 -153(8) . . . . ?
C27 C25 C26 N5 25(9) . . . . ?
C23 C25 C27 N6 174(3) . . . . ?
C26 C25 C27 N6 -4(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659295
