#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:39:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178436 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/57/4025763.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_4025763
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         'C32 H19 N5'
_chemical_formula_sum            'C32 H19 N5'
_chemical_formula_weight         473.52
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                99.24(3)
_cell_angle_beta                 91.06(3)
_cell_angle_gamma                116.77(3)
_cell_formula_units_Z            4
_cell_length_a                   10.190(2)
_cell_length_b                   10.426(2)
_cell_length_c                   27.174(5)
_cell_measurement_reflns_used    826
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.17
_cell_volume                     2530.6(11)
_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 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0417
_diffrn_reflns_av_sigmaI/netI    0.0455
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            26084
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.45
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9888
_exptl_absorpt_correction_T_min  0.9777
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'
_exptl_crystal_colour            plate
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       black
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.595
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.171
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     684
_refine_ls_number_reflns         8882
_refine_ls_number_restraints     277
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0884
_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)+(0.0572P)²+2.1036P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1826
_refine_ls_wR_factor_ref         0.1911
_reflns_number_gt                7571
_reflns_number_total             8882
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101456v_si_004.cif
_cod_data_source_block           sa327
_cod_original_cell_volume        2530.6(9)
_cod_database_code               4025763
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 1.1919(3) -0.0211(3) 0.19793(9) 0.0448(6) Uani 1 1 d U . .
N2 N 0.2375(4) -0.5834(3) -0.05419(12) 0.0680(9) Uani 1 1 d U . .
N3 N 0.2914(4) -0.2673(4) -0.15205(13) 0.0737(10) Uani 1 1 d U . .
N4 N 1.1569(3) 0.6265(3) 0.04888(11) 0.0583(8) Uani 1 1 d U . .
N5 N 1.3110(3) 0.3442(3) 0.09642(12) 0.0607(8) Uani 1 1 d U . .
N6 N 0.6898(3) 0.9947(3) 0.30105(11) 0.0541(7) Uani 1 1 d DU . .
N7 N 0.3254(4) 1.5934(4) 0.55660(13) 0.0714(9) Uani 1 1 d U . .
N8 N 0.0421(4) 1.2656(4) 0.64595(13) 0.0714(9) Uani 1 1 d U . .
N9 N 0.0272(4) 0.3634(3) 0.45158(13) 0.0710(10) Uani 1 1 d U A .
N10 N 0.4469(3) 0.6085(3) 0.40306(13) 0.0655(9) Uani 1 1 d U A .
C1 C 1.3242(4) -0.1667(4) 0.18792(13) 0.0509(8) Uani 1 1 d U . .
H1A H 1.4131 -0.0803 0.1872 0.061 Uiso 1 1 calc R . .
C2 C 1.3263(4) -0.2999(4) 0.18512(13) 0.0568(9) Uani 1 1 d U . .
H2A H 1.4169 -0.3046 0.1823 0.068 Uiso 1 1 calc R . .
C3 C 1.1983(4) -0.4249(4) 0.18635(12) 0.0538(9) Uani 1 1 d U . .
H3A H 1.2008 -0.5152 0.1856 0.065 Uiso 1 1 calc R . .
C4 C 1.0675(4) -0.4191(4) 0.18861(13) 0.0559(9) Uani 1 1 d U . .
H4A H 0.9783 -0.5061 0.1882 0.067 Uiso 1 1 calc R . .
C5 C 1.0639(4) -0.2870(4) 0.19149(13) 0.0517(8) Uani 1 1 d U . .
H5A H 0.9726 -0.2834 0.1933 0.062 Uiso 1 1 calc R . .
C6 C 1.1927(3) -0.1607(3) 0.19170(11) 0.0404(7) Uani 1 1 d U . .
C7 C 1.2517(4) 0.0721(4) 0.24555(13) 0.0549(9) Uani 1 1 d U . .
C8 C 1.3523(5) 0.2144(5) 0.24982(18) 0.0779(12) Uani 1 1 d U . .
H8A H 1.3851 0.2554 0.2209 0.093 Uiso 1 1 calc R . .
C9 C 1.4087(6) 0.3028(5) 0.29965(18) 0.0876(14) Uani 1 1 d U . .
H9A H 1.4810 0.4023 0.3039 0.105 Uiso 1 1 calc R . .
C10 C 1.3565(6) 0.2410(5) 0.34029(18) 0.0989(18) Uani 1 1 d U . .
H10A H 1.3947 0.2989 0.3728 0.119 Uiso 1 1 calc R . .
C11 C 1.2507(6) 0.0981(5) 0.33593(16) 0.0858(14) Uani 1 1 d U . .
H11A H 1.2126 0.0590 0.3648 0.103 Uiso 1 1 calc R . .
C12 C 1.2012(6) 0.0129(5) 0.28874(14) 0.0773(13) Uani 1 1 d U . .
H12A H 1.1319 -0.0874 0.2852 0.093 Uiso 1 1 calc R . .
C13 C 1.1104(3) 0.0070(3) 0.16319(11) 0.0363(7) Uani 1 1 d U . .
C14 C 1.0676(3) -0.0766(3) 0.11453(11) 0.0377(7) Uani 1 1 d U . .
H14A H 1.0918 -0.1546 0.1054 0.045 Uiso 1 1 calc R . .
C15 C 0.9908(3) -0.0463(3) 0.08002(11) 0.0360(7) Uani 1 1 d U . .
H15A H 0.9614 -0.1050 0.0474 0.043 Uiso 1 1 calc R . .
C16 C 0.9545(3) 0.0695(3) 0.09179(11) 0.0355(6) Uani 1 1 d U . .
C17 C 0.9945(3) 0.1497(3) 0.14095(11) 0.0363(7) Uani 1 1 d U . .
H17A H 0.9698 0.2273 0.1501 0.044 Uiso 1 1 calc R . .
C18 C 1.0684(3) 0.1187(3) 0.17601(11) 0.0378(7) Uani 1 1 d U . .
H18A H 1.0917 0.1730 0.2093 0.045 Uiso 1 1 calc R . .
C19 C 0.8801(3) 0.1072(3) 0.05387(10) 0.0350(6) Uani 1 1 d U . .
C20 C 0.7519(3) 0.0039(3) 0.02373(11) 0.0361(7) Uani 1 1 d U . .
C21 C 0.6688(3) -0.1410(3) 0.03423(11) 0.0402(7) Uani 1 1 d U . .
H21A H 0.7006 -0.1648 0.0630 0.048 Uiso 1 1 calc R . .
C22 C 0.5475(3) -0.2439(3) 0.00470(12) 0.0418(7) Uani 1 1 d U . .
H22A H 0.4949 -0.3375 0.0134 0.050 Uiso 1 1 calc R . .
C23 C 0.4965(3) -0.2142(3) -0.03977(11) 0.0371(7) Uani 1 1 d U . .
C24 C 0.5764(3) -0.0694(3) -0.04999(11) 0.0380(7) Uani 1 1 d U . .
H24A H 0.5444 -0.0455 -0.0787 0.046 Uiso 1 1 calc R . .
C25 C 0.6960(3) 0.0334(3) -0.01972(11) 0.0380(7) Uani 1 1 d U . .
H25A H 0.7450 0.1286 -0.0274 0.046 Uiso 1 1 calc R . .
C26 C 0.3761(3) -0.3212(3) -0.07150(12) 0.0425(7) Uani 1 1 d U . .
C27 C 0.2983(4) -0.4675(4) -0.06221(12) 0.0482(8) Uani 1 1 d U . .
C28 C 0.3281(4) -0.2932(4) -0.11642(13) 0.0498(8) Uani 1 1 d U . .
C29 C 0.9443(3) 0.2587(3) 0.04809(10) 0.0356(6) Uani 1 1 d U . .
H29A H 0.8797 0.2875 0.0330 0.043 Uiso 1 1 calc R . .
C30 C 1.0854(3) 0.3644(3) 0.06164(11) 0.0370(7) Uani 1 1 d U . .
C31 C 1.1252(4) 0.5108(3) 0.05444(11) 0.0423(7) Uani 1 1 d U . .
C32 C 1.2071(4) 0.3467(3) 0.08153(12) 0.0423(7) Uani 1 1 d U . .
C33 C 0.9556(2) 1.1532(2) 0.31265(6) 0.063(3) Uani 0.333(9) 1 d PU A 1
H33A H 0.9739 1.0747 0.3181 0.075 Uiso 0.333(9) 1 calc PR A 1
C34 C 1.0732(2) 1.2905(2) 0.31321(6) 0.068(4) Uani 0.333(9) 1 d PRU A 1
H34A H 1.1718 1.3058 0.3191 0.082 Uiso 0.333(9) 1 calc PR A 1
C35 C 1.0465(2) 1.4053(2) 0.30518(6) 0.058(4) Uani 0.333(9) 1 d PRU A 1
H35A H 1.1268 1.4992 0.3056 0.070 Uiso 0.333(9) 1 calc PR A 1
C36 C 0.9021(2) 1.3829(2) 0.29658(6) 0.069(4) Uani 0.333(9) 1 d PRU A 1
H36A H 0.8839 1.4614 0.2911 0.082 Uiso 0.333(9) 1 calc PR A 1
C37 C 0.7845(2) 1.2456(2) 0.29602(6) 0.059(3) Uani 0.333(9) 1 d PRU A 1
H37A H 0.6859 1.2303 0.2901 0.071 Uiso 0.333(9) 1 calc PR A 1
C38 C 0.8113(2) 1.1308(2) 0.30406(6) 0.053(3) Uani 0.333(9) 1 d PRDU A 1
C33' C 0.9436(2) 1.1906(2) 0.30657(6) 0.0691(19) Uani 0.667(9) 1 d PRU A 2
H33B H 0.9786 1.1221 0.3107 0.083 Uiso 0.667(9) 1 calc PR A 2
C34' C 1.0435(2) 1.3349(2) 0.30573(6) 0.078(2) Uani 0.667(9) 1 d PRU A 2
H34B H 1.1466 1.3651 0.3093 0.094 Uiso 0.667(9) 1 calc PR A 2
C35' C 0.9923(2) 1.4351(2) 0.29968(6) 0.071(2) Uani 0.667(9) 1 d PRU A 2
H35B H 1.0605 1.5337 0.2991 0.085 Uiso 0.667(9) 1 calc PR A 2
C36' C 0.8413(2) 1.3909(2) 0.29448(6) 0.076(2) Uani 0.667(9) 1 d PRU A 2
H36B H 0.8063 1.4594 0.2903 0.091 Uiso 0.667(9) 1 calc PR A 2
C37' C 0.7415(2) 1.2466(2) 0.29532(6) 0.0645(19) Uani 0.667(9) 1 d PRU A 2
H37B H 0.6383 1.2165 0.2918 0.077 Uiso 0.667(9) 1 calc PR A 2
C38' C 0.7927(2) 1.1465(2) 0.30137(6) 0.0507(16) Uani 0.667(9) 1 d PRDU A 2
C39 C 0.6854(2) 0.8801(2) 0.26345(6) 0.0534(9) Uani 1 1 d RU A .
C40 C 0.6474(2) 0.7417(2) 0.27357(6) 0.0745(12) Uani 1 1 d RU . .
H40A H 0.6242 0.7225 0.3062 0.089 Uiso 1 1 calc R . .
C41 C 0.6430(6) 0.6313(5) 0.23637(17) 0.0847(14) Uani 1 1 d U A .
H41A H 0.6142 0.5364 0.2434 0.102 Uiso 1 1 calc R . .
C42 C 0.6796(5) 0.6582(5) 0.18993(16) 0.0747(12) Uani 1 1 d U . .
H42A H 0.6765 0.5823 0.1646 0.090 Uiso 1 1 calc R A .
C43 C 0.7207(4) 0.7934(5) 0.17972(14) 0.0678(11) Uani 1 1 d U A .
H43A H 0.7488 0.8121 0.1475 0.081 Uiso 1 1 calc R . .
C44 C 0.7223(4) 0.9067(4) 0.21628(13) 0.0596(10) Uani 1 1 d U . .
H44A H 0.7485 1.0003 0.2085 0.072 Uiso 1 1 calc R A .
C45 C 0.5864(4) 0.9691(4) 0.33642(12) 0.0439(7) Uani 1 1 d U A .
C46 C 0.6255(3) 1.0586(4) 0.38384(12) 0.0445(7) Uani 1 1 d U . .
H46A H 0.7216 1.1389 0.3918 0.053 Uiso 1 1 calc R A .
C47 C 0.5263(3) 1.0316(3) 0.41892(11) 0.0405(7) Uani 1 1 d U A .
H47A H 0.5554 1.0931 0.4511 0.049 Uiso 1 1 calc R . .
C48 C 0.3828(3) 0.9155(3) 0.40845(11) 0.0376(7) Uani 1 1 d U . .
C49 C 0.3437(3) 0.8300(3) 0.36008(11) 0.0401(7) Uani 1 1 d U A .
H49A H 0.2463 0.7522 0.3516 0.048 Uiso 1 1 calc R . .
C50 C 0.4423(4) 0.8557(3) 0.32482(12) 0.0449(8) Uani 1 1 d U . .
H50A H 0.4126 0.7961 0.2923 0.054 Uiso 1 1 calc R A .
C51 C 0.2767(3) 0.8843(3) 0.44592(10) 0.0363(6) Uani 1 1 d U A .
C52 C 0.2549(3) 0.9937(3) 0.47667(11) 0.0368(7) Uani 1 1 d U . .
C53 C 0.3193(3) 1.1424(3) 0.46847(11) 0.0395(7) Uani 1 1 d U A .
H53A H 0.3767 1.1664 0.4411 0.047 Uiso 1 1 calc R . .
C54 C 0.3010(3) 1.2480(3) 0.49830(11) 0.0413(7) Uani 1 1 d U . .
H54A H 0.3448 1.3442 0.4913 0.050 Uiso 1 1 calc R A .
C55 C 0.2167(3) 1.2184(3) 0.54038(11) 0.0403(7) Uani 1 1 d U A .
C56 C 0.1507(3) 1.0712(3) 0.54869(11) 0.0427(7) Uani 1 1 d U . .
H56A H 0.0932 1.0474 0.5761 0.051 Uiso 1 1 calc R A .
C57 C 0.1685(3) 0.9654(3) 0.51844(11) 0.0391(7) Uani 1 1 d U A .
H57A H 0.1222 0.8687 0.5250 0.047 Uiso 1 1 calc R . .
C58 C 0.1996(3) 1.3276(4) 0.57189(12) 0.0455(8) Uani 1 1 d U . .
C59 C 0.2684(4) 1.4756(4) 0.56401(13) 0.0514(8) Uani 1 1 d U A .
C60 C 0.1136(4) 1.2957(4) 0.61348(13) 0.0523(8) Uani 1 1 d U A .
C61 C 0.1893(3) 0.7334(3) 0.45107(11) 0.0395(7) Uani 1 1 d U . .
H61A H 0.1003 0.7128 0.4661 0.047 Uiso 1 1 calc R A .
C62 C 0.2166(3) 0.6180(3) 0.43749(11) 0.0403(7) Uani 1 1 d U A .
C63 C 0.1104(4) 0.4763(4) 0.44525(12) 0.0503(8) Uani 1 1 d U . .
C64 C 0.3478(4) 0.6199(3) 0.41784(13) 0.0453(8) Uani 1 1 d U . .
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 C7 121.7(3) . . ?
C13 N1 C6 120.9(2) . . ?
C7 N1 C6 116.1(2) . . ?
C38 N6 C45 121.5(3) . . ?
C38 N6 C39 116.0(2) . . ?
C45 N6 C39 122.2(2) . . ?
C38 N6 C38' 12.5 . . ?
C45 N6 C38' 116.3(2) . . ?
C39 N6 C38' 121.1(2) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 H1A 120.2 . . ?
C2 C1 H1A 120.2 . . ?
C3 C2 C1 120.4(3) . . ?
C3 C2 H2A 119.8 . . ?
C1 C2 H2A 119.8 . . ?
C4 C3 C2 119.8(3) . . ?
C4 C3 H3A 120.1 . . ?
C2 C3 H3A 120.1 . . ?
C3 C4 C5 120.3(3) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 120.1(3) . . ?
C6 C5 H5A 120.0 . . ?
C4 C5 H5A 120.0 . . ?
C1 C6 C5 119.8(3) . . ?
C1 C6 N1 119.5(3) . . ?
C5 C6 N1 120.6(3) . . ?
C8 C7 C12 120.4(4) . . ?
C8 C7 N1 121.5(4) . . ?
C12 C7 N1 118.1(3) . . ?
C7 C8 C9 118.5(4) . . ?
C7 C8 H8A 120.8 . . ?
C9 C8 H8A 120.8 . . ?
C10 C9 C8 119.1(4) . . ?
C10 C9 H9A 120.5 . . ?
C8 C9 H9A 120.5 . . ?
C9 C10 C11 122.5(4) . . ?
C9 C10 H10A 118.8 . . ?
C11 C10 H10A 118.8 . . ?
C10 C11 C12 118.4(5) . . ?
C10 C11 H11A 120.8 . . ?
C12 C11 H11A 120.8 . . ?
C11 C12 C7 121.2(4) . . ?
C11 C12 H12A 119.4 . . ?
C7 C12 H12A 119.4 . . ?
N1 C13 C14 120.4(3) . . ?
N1 C13 C18 121.2(3) . . ?
C14 C13 C18 118.4(3) . . ?
C15 C14 C13 120.3(3) . . ?
C15 C14 H14A 119.8 . . ?
C13 C14 H14A 119.8 . . ?
C14 C15 C16 121.6(3) . . ?
C14 C15 H15A 119.2 . . ?
C16 C15 H15A 119.2 . . ?
C17 C16 C15 117.4(3) . . ?
C17 C16 C19 121.1(3) . . ?
C15 C16 C19 121.5(3) . . ?
C18 C17 C16 121.5(3) . . ?
C18 C17 H17A 119.2 . . ?
C16 C17 H17A 119.2 . . ?
C17 C18 C13 120.6(3) . . ?
C17 C18 H18A 119.7 . . ?
C13 C18 H18A 119.7 . . ?
C20 C19 C29 119.4(3) . . ?
C20 C19 C16 122.8(2) . . ?
C29 C19 C16 117.8(3) . . ?
C19 C20 C25 122.8(3) . . ?
C19 C20 C21 121.3(3) . . ?
C25 C20 C21 115.9(3) . . ?
C22 C21 C20 122.3(3) . . ?
C22 C21 H21A 118.9 . . ?
C20 C21 H21A 118.9 . . ?
C21 C22 C23 121.0(3) . . ?
C21 C22 H22A 119.5 . . ?
C23 C22 H22A 119.5 . . ?
C26 C23 C24 121.4(3) . . ?
C26 C23 C22 121.4(3) . . ?
C24 C23 C22 117.2(3) . . ?
C25 C24 C23 121.3(3) . . ?
C25 C24 H24A 119.4 . . ?
C23 C24 H24A 119.4 . . ?
C24 C25 C20 122.3(3) . . ?
C24 C25 H25A 118.9 . . ?
C20 C25 H25A 118.9 . . ?
C23 C26 C28 121.4(3) . . ?
C23 C26 C27 121.7(3) . . ?
C28 C26 C27 116.8(3) . . ?
N2 C27 C26 179.0(4) . . ?
N3 C28 C26 178.4(4) . . ?
C30 C29 C19 128.0(3) . . ?
C30 C29 H29A 116.0 . . ?
C19 C29 H29A 116.0 . . ?
C29 C30 C31 119.1(3) . . ?
C29 C30 C32 126.9(3) . . ?
C31 C30 C32 113.9(3) . . ?
N4 C31 C30 179.8(4) . . ?
N5 C32 C30 174.1(3) . . ?
C34 C33 C38 120.0 . . ?
C34 C33 H33A 120.0 . . ?
C38 C33 H33A 120.0 . . ?
C33 C34 C35 120.0 . . ?
C33 C34 H34A 120.0 . . ?
C35 C34 H34A 120.0 . . ?
C36 C35 C34 120.0 . . ?
C36 C35 H35A 120.0 . . ?
C34 C35 H35A 120.0 . . ?
C35 C36 C37 120.0 . . ?
C35 C36 H36A 120.0 . . ?
C37 C36 H36A 120.0 . . ?
C38 C37 C36 120.0 . . ?
C38 C37 H37A 120.0 . . ?
C36 C37 H37A 120.0 . . ?
N6 C38 C37 117.43(16) . . ?
N6 C38 C33 122.52(16) . . ?
C37 C38 C33 120.0 . . ?
C34' C33' C38' 120.0 . . ?
C34' C33' H33B 120.0 . . ?
C38' C33' H33B 120.0 . . ?
C33' C34' C35' 120.0 . . ?
C33' C34' H34B 120.0 . . ?
C35' C34' H34B 120.0 . . ?
C34' C35' C36' 120.0 . . ?
C34' C35' H35B 120.0 . . ?
C36' C35' H35B 120.0 . . ?
C37' C36' C35' 120.0 . . ?
C37' C36' H36B 120.0 . . ?
C35' C36' H36B 120.0 . . ?
C36' C37' C38' 120.0 . . ?
C36' C37' H37B 120.0 . . ?
C38' C37' H37B 120.0 . . ?
C37' C38' C33' 120.0 . . ?
C37' C38' N6 120.60(15) . . ?
C33' C38' N6 119.38(15) . . ?
C44 C39 C40 118.9(2) . . ?
C44 C39 N6 119.7(3) . . ?
C40 C39 N6 121.37(13) . . ?
C41 C40 C39 120.5(2) . . ?
C41 C40 H40A 119.8 . . ?
C39 C40 H40A 119.8 . . ?
C42 C41 C40 120.3(4) . . ?
C42 C41 H41A 119.8 . . ?
C40 C41 H41A 119.8 . . ?
C43 C42 C41 120.1(4) . . ?
C43 C42 H42A 120.0 . . ?
C41 C42 H42A 120.0 . . ?
C42 C43 C44 121.0(4) . . ?
C42 C43 H43A 119.5 . . ?
C44 C43 H43A 119.5 . . ?
C39 C44 C43 119.2(4) . . ?
C39 C44 H44A 120.4 . . ?
C43 C44 H44A 120.4 . . ?
C46 C45 C50 118.7(3) . . ?
C46 C45 N6 120.3(3) . . ?
C50 C45 N6 121.0(3) . . ?
C47 C46 C45 120.5(3) . . ?
C47 C46 H46A 119.7 . . ?
C45 C46 H46A 119.7 . . ?
C46 C47 C48 121.5(3) . . ?
C46 C47 H47A 119.2 . . ?
C48 C47 H47A 119.2 . . ?
C47 C48 C49 117.2(3) . . ?
C47 C48 C51 122.0(3) . . ?
C49 C48 C51 120.9(3) . . ?
C50 C49 C48 121.7(3) . . ?
C50 C49 H49A 119.2 . . ?
C48 C49 H49A 119.2 . . ?
C49 C50 C45 120.3(3) . . ?
C49 C50 H50A 119.8 . . ?
C45 C50 H50A 119.8 . . ?
C52 C51 C61 118.7(3) . . ?
C52 C51 C48 123.0(3) . . ?
C61 C51 C48 118.2(3) . . ?
C51 C52 C57 122.3(3) . . ?
C51 C52 C53 122.0(3) . . ?
C57 C52 C53 115.7(3) . . ?
C54 C53 C52 122.2(3) . . ?
C54 C53 H53A 118.9 . . ?
C52 C53 H53A 118.9 . . ?
C53 C54 C55 121.4(3) . . ?
C53 C54 H54A 119.3 . . ?
C55 C54 H54A 119.3 . . ?
C58 C55 C56 121.3(3) . . ?
C58 C55 C54 121.7(3) . . ?
C56 C55 C54 117.1(3) . . ?
C57 C56 C55 121.3(3) . . ?
C57 C56 H56A 119.3 . . ?
C55 C56 H56A 119.3 . . ?
C56 C57 C52 122.3(3) . . ?
C56 C57 H57A 118.8 . . ?
C52 C57 H57A 118.8 . . ?
C55 C58 C60 120.9(3) . . ?
C55 C58 C59 121.1(3) . . ?
C60 C58 C59 118.1(3) . . ?
N7 C59 C58 178.1(4) . . ?
N8 C60 C58 177.8(4) . . ?
C62 C61 C51 129.1(3) . . ?
C62 C61 H61A 115.4 . . ?
C51 C61 H61A 115.4 . . ?
C61 C62 C63 119.0(3) . . ?
C61 C62 C64 127.2(3) . . ?
C63 C62 C64 113.7(3) . . ?
N9 C63 C62 179.3(4) . . ?
N10 C64 C62 173.6(4) . . ?
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 1.395(4) . ?
N1 C7 1.422(4) . ?
N1 C6 1.441(4) . ?
N2 C27 1.143(4) . ?
N3 C28 1.145(4) . ?
N4 C31 1.136(4) . ?
N5 C32 1.139(4) . ?
N6 C38 1.389(3) . ?
N6 C45 1.404(4) . ?
N6 C39 1.426(3) . ?
N6 C38' 1.450(3) . ?
N7 C59 1.152(4) . ?
N8 C60 1.147(4) . ?
N9 C63 1.142(4) . ?
N10 C64 1.142(4) . ?
C1 C6 1.375(4) . ?
C1 C2 1.389(5) . ?
C1 H1A 0.9500 . ?
C2 C3 1.373(5) . ?
C2 H2A 0.9500 . ?
C3 C4 1.363(5) . ?
C3 H3A 0.9500 . ?
C4 C5 1.384(5) . ?
C4 H4A 0.9500 . ?
C5 C6 1.377(5) . ?
C5 H5A 0.9500 . ?
C7 C8 1.355(5) . ?
C7 C12 1.411(5) . ?
C8 C9 1.451(6) . ?
C8 H8A 0.9500 . ?
C9 C10 1.364(6) . ?
C9 H9A 0.9500 . ?
C10 C11 1.374(6) . ?
C10 H10A 0.9500 . ?
C11 C12 1.376(5) . ?
C11 H11A 0.9500 . ?
C12 H12A 0.9500 . ?
C13 C14 1.402(4) . ?
C13 C18 1.409(4) . ?
C14 C15 1.372(4) . ?
C14 H14A 0.9500 . ?
C15 C16 1.407(4) . ?
C15 H15A 0.9500 . ?
C16 C17 1.401(4) . ?
C16 C19 1.470(4) . ?
C17 C18 1.368(4) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.395(4) . ?
C19 C29 1.449(4) . ?
C20 C25 1.436(4) . ?
C20 C21 1.441(4) . ?
C21 C22 1.347(4) . ?
C21 H21A 0.9500 . ?
C22 C23 1.438(4) . ?
C22 H22A 0.9500 . ?
C23 C26 1.382(4) . ?
C23 C24 1.434(4) . ?
C24 C25 1.346(4) . ?
C24 H24A 0.9500 . ?
C25 H25A 0.9500 . ?
C26 C28 1.427(5) . ?
C26 C27 1.436(5) . ?
C29 C30 1.356(4) . ?
C29 H29A 0.9500 . ?
C30 C31 1.441(4) . ?
C30 C32 1.442(5) . ?
C33 C34 1.3900 . ?
C33 C38 1.3900 . ?
C33 H33A 0.9500 . ?
C34 C35 1.3900 . ?
C34 H34A 0.9500 . ?
C35 C36 1.3900 . ?
C35 H35A 0.9500 . ?
C36 C37 1.3900 . ?
C36 H36A 0.9500 . ?
C37 C38 1.3900 . ?
C37 H37A 0.9500 . ?
C33' C34' 1.3900 . ?
C33' C38' 1.3900 . ?
C33' H33B 0.9500 . ?
C34' C35' 1.3900 . ?
C34' H34B 0.9500 . ?
C35' C36' 1.3900 . ?
C35' H35B 0.9500 . ?
C36' C37' 1.3900 . ?
C36' H36B 0.9500 . ?
C37' C38' 1.3900 . ?
C37' H37B 0.9500 . ?
C39 C44 1.378(4) . ?
C39 C40 1.3916 . ?
C40 C41 1.388(5) . ?
C40 H40A 0.9500 . ?
C41 C42 1.359(6) . ?
C41 H41A 0.9500 . ?
C42 C43 1.355(6) . ?
C42 H42A 0.9500 . ?
C43 C44 1.410(5) . ?
C43 H43A 0.9500 . ?
C44 H44A 0.9500 . ?
C45 C46 1.396(4) . ?
C45 C50 1.398(5) . ?
C46 C47 1.369(4) . ?
C46 H46A 0.9500 . ?
C47 C48 1.402(4) . ?
C47 H47A 0.9500 . ?
C48 C49 1.402(4) . ?
C48 C51 1.463(4) . ?
C49 C50 1.370(4) . ?
C49 H49A 0.9500 . ?
C50 H50A 0.9500 . ?
C51 C52 1.406(4) . ?
C51 C61 1.449(4) . ?
C52 C57 1.436(4) . ?
C52 C53 1.443(4) . ?
C53 C54 1.345(4) . ?
C53 H53A 0.9500 . ?
C54 C55 1.432(4) . ?
C54 H54A 0.9500 . ?
C55 C58 1.390(4) . ?
C55 C56 1.431(4) . ?
C56 C57 1.348(4) . ?
C56 H56A 0.9500 . ?
C57 H57A 0.9500 . ?
C58 C60 1.432(5) . ?
C58 C59 1.434(5) . ?
C61 C62 1.351(4) . ?
C61 H61A 0.9500 . ?
C62 C63 1.438(4) . ?
C62 C64 1.442(5) . ?
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 -0.3(5) . . . . ?
C1 C2 C3 C4 2.3(5) . . . . ?
C2 C3 C4 C5 -2.3(5) . . . . ?
C3 C4 C5 C6 0.5(5) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
C2 C1 C6 N1 175.9(3) . . . . ?
C4 C5 C6 C1 1.4(5) . . . . ?
C4 C5 C6 N1 -176.0(3) . . . . ?
C13 N1 C6 C1 120.8(3) . . . . ?
C7 N1 C6 C1 -71.9(4) . . . . ?
C13 N1 C6 C5 -61.8(4) . . . . ?
C7 N1 C6 C5 105.6(4) . . . . ?
C13 N1 C7 C8 -61.6(5) . . . . ?
C6 N1 C7 C8 131.2(4) . . . . ?
C13 N1 C7 C12 117.3(4) . . . . ?
C6 N1 C7 C12 -50.0(4) . . . . ?
C12 C7 C8 C9 1.4(6) . . . . ?
N1 C7 C8 C9 -179.8(4) . . . . ?
C7 C8 C9 C10 -1.5(7) . . . . ?
C8 C9 C10 C11 -0.8(8) . . . . ?
C9 C10 C11 C12 3.2(8) . . . . ?
C10 C11 C12 C7 -3.2(7) . . . . ?
C8 C7 C12 C11 1.0(6) . . . . ?
N1 C7 C12 C11 -177.8(4) . . . . ?
C7 N1 C13 C14 172.6(3) . . . . ?
C6 N1 C13 C14 -20.8(4) . . . . ?
C7 N1 C13 C18 -7.8(5) . . . . ?
C6 N1 C13 C18 158.8(3) . . . . ?
N1 C13 C14 C15 -178.3(3) . . . . ?
C18 C13 C14 C15 2.1(4) . . . . ?
C13 C14 C15 C16 0.9(4) . . . . ?
C14 C15 C16 C17 -2.5(4) . . . . ?
C14 C15 C16 C19 176.3(3) . . . . ?
C15 C16 C17 C18 1.2(4) . . . . ?
C19 C16 C17 C18 -177.6(3) . . . . ?
C16 C17 C18 C13 1.8(4) . . . . ?
N1 C13 C18 C17 176.9(3) . . . . ?
C14 C13 C18 C17 -3.4(4) . . . . ?
C17 C16 C19 C20 -130.3(3) . . . . ?
C15 C16 C19 C20 50.9(4) . . . . ?
C17 C16 C19 C29 49.7(4) . . . . ?
C15 C16 C19 C29 -129.1(3) . . . . ?
C29 C19 C20 C25 12.9(4) . . . . ?
C16 C19 C20 C25 -167.1(3) . . . . ?
C29 C19 C20 C21 -168.2(3) . . . . ?
C16 C19 C20 C21 11.8(4) . . . . ?
C19 C20 C21 C22 -177.8(3) . . . . ?
C25 C20 C21 C22 1.2(4) . . . . ?
C20 C21 C22 C23 1.2(5) . . . . ?
C21 C22 C23 C26 177.0(3) . . . . ?
C21 C22 C23 C24 -2.5(4) . . . . ?
C26 C23 C24 C25 -178.2(3) . . . . ?
C22 C23 C24 C25 1.3(4) . . . . ?
C23 C24 C25 C20 1.1(4) . . . . ?
C19 C20 C25 C24 176.5(3) . . . . ?
C21 C20 C25 C24 -2.4(4) . . . . ?
C24 C23 C26 C28 1.5(5) . . . . ?
C22 C23 C26 C28 -178.1(3) . . . . ?
C24 C23 C26 C27 178.2(3) . . . . ?
C22 C23 C26 C27 -1.3(5) . . . . ?
C23 C26 C27 N2 5(27) . . . . ?
C28 C26 C27 N2 -178(100) . . . . ?
C23 C26 C28 N3 -18(15) . . . . ?
C27 C26 C28 N3 165(14) . . . . ?
C20 C19 C29 C30 -158.5(3) . . . . ?
C16 C19 C29 C30 21.5(4) . . . . ?
C19 C29 C30 C31 -177.3(3) . . . . ?
C19 C29 C30 C32 5.2(5) . . . . ?
C29 C30 C31 N4 163(100) . . . . ?
C32 C30 C31 N4 -19(100) . . . . ?
C29 C30 C32 N5 166(3) . . . . ?
C31 C30 C32 N5 -12(4) . . . . ?
C38 C33 C34 C35 0.0 . . . . ?
C33 C34 C35 C36 0.0 . . . . ?
C34 C35 C36 C37 0.0 . . . . ?
C35 C36 C37 C38 0.0 . . . . ?
C45 N6 C38 C37 -67.4(3) . . . . ?
C39 N6 C38 C37 119.2(2) . . . . ?
C38' N6 C38 C37 1.72(6) . . . . ?
C45 N6 C38 C33 115.3(3) . . . . ?
C39 N6 C38 C33 -58.2(3) . . . . ?
C38' N6 C38 C33 -175.66(9) . . . . ?
C36 C37 C38 N6 -177.44(14) . . . . ?
C36 C37 C38 C33 0.0 . . . . ?
C34 C33 C38 N6 177.31(15) . . . . ?
C34 C33 C38 C37 0.0 . . . . ?
C38' C33' C34' C35' 0.0 . . . . ?
C33' C34' C35' C36' 0.0 . . . . ?
C34' C35' C36' C37' 0.0 . . . . ?
C35' C36' C37' C38' 0.0 . . . . ?
C36' C37' C38' C33' 0.0 . . . . ?
C36' C37' C38' N6 -178.42(14) . . . . ?
C34' C33' C38' C37' 0.0 . . . . ?
C34' C33' C38' N6 178.44(14) . . . . ?
C38 N6 C38' C37' -174.1 . . . . ?
C45 N6 C38' C37' -56.8(3) . . . . ?
C39 N6 C38' C37' 117.1(2) . . . . ?
C38 N6 C38' C33' 7.50(11) . . . . ?
C45 N6 C38' C33' 124.8(2) . . . . ?
C39 N6 C38' C33' -61.3(3) . . . . ?
C38 N6 C39 C44 -43.0(4) . . . . ?
C45 N6 C39 C44 143.5(3) . . . . ?
C38' N6 C39 C44 -30.1(4) . . . . ?
C38 N6 C39 C40 135.67(18) . . . . ?
C45 N6 C39 C40 -37.8(3) . . . . ?
C38' N6 C39 C40 148.66(19) . . . . ?
C44 C39 C40 C41 -1.6(3) . . . . ?
N6 C39 C40 C41 179.6(3) . . . . ?
C39 C40 C41 C42 1.7(5) . . . . ?
C40 C41 C42 C43 0.0(7) . . . . ?
C41 C42 C43 C44 -1.8(7) . . . . ?
C40 C39 C44 C43 -0.1(4) . . . . ?
N6 C39 C44 C43 178.6(3) . . . . ?
C42 C43 C44 C39 1.8(6) . . . . ?
C38 N6 C45 C46 -22.1(5) . . . . ?
C39 N6 C45 C46 151.0(3) . . . . ?
C38' N6 C45 C46 -35.1(4) . . . . ?
C38 N6 C45 C50 156.9(3) . . . . ?
C39 N6 C45 C50 -30.0(5) . . . . ?
C38' N6 C45 C50 143.9(3) . . . . ?
C50 C45 C46 C47 2.8(5) . . . . ?
N6 C45 C46 C47 -178.2(3) . . . . ?
C45 C46 C47 C48 -0.8(5) . . . . ?
C46 C47 C48 C49 -1.5(4) . . . . ?
C46 C47 C48 C51 179.1(3) . . . . ?
C47 C48 C49 C50 1.8(4) . . . . ?
C51 C48 C49 C50 -178.7(3) . . . . ?
C48 C49 C50 C45 0.2(5) . . . . ?
C46 C45 C50 C49 -2.5(5) . . . . ?
N6 C45 C50 C49 178.5(3) . . . . ?
C47 C48 C51 C52 44.7(4) . . . . ?
C49 C48 C51 C52 -134.7(3) . . . . ?
C47 C48 C51 C61 -135.9(3) . . . . ?
C49 C48 C51 C61 44.6(4) . . . . ?
C61 C51 C52 C57 10.8(4) . . . . ?
C48 C51 C52 C57 -169.9(3) . . . . ?
C61 C51 C52 C53 -169.8(3) . . . . ?
C48 C51 C52 C53 9.5(4) . . . . ?
C51 C52 C53 C54 -178.8(3) . . . . ?
C57 C52 C53 C54 0.6(4) . . . . ?
C52 C53 C54 C55 0.5(5) . . . . ?
C53 C54 C55 C58 178.8(3) . . . . ?
C53 C54 C55 C56 -1.2(4) . . . . ?
C58 C55 C56 C57 -179.3(3) . . . . ?
C54 C55 C56 C57 0.6(4) . . . . ?
C55 C56 C57 C52 0.6(5) . . . . ?
C51 C52 C57 C56 178.3(3) . . . . ?
C53 C52 C57 C56 -1.2(4) . . . . ?
C56 C55 C58 C60 -0.7(5) . . . . ?
C54 C55 C58 C60 179.3(3) . . . . ?
C56 C55 C58 C59 178.7(3) . . . . ?
C54 C55 C58 C59 -1.2(5) . . . . ?
C55 C58 C59 N7 -2(14) . . . . ?
C60 C58 C59 N7 177(100) . . . . ?
C55 C58 C60 N8 -29(11) . . . . ?
C59 C58 C60 N8 152(10) . . . . ?
C52 C51 C61 C62 -159.0(3) . . . . ?
C48 C51 C61 C62 21.6(5) . . . . ?
C51 C61 C62 C63 -178.3(3) . . . . ?
C51 C61 C62 C64 5.5(5) . . . . ?
C61 C62 C63 N9 -139(100) . . . . ?
C64 C62 C63 N9 38(33) . . . . ?
C61 C62 C64 N10 167(3) . . . . ?
C63 C62 C64 N10 -9(4) . . . . ?
