#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:39:23 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178879 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/08/4110869.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_4110869
loop_
_publ_author_name
'Michal Rafilovich'
'Joel Bernstein'
_publ_section_title
;
 Serendipity and Four Polymorphic Structures of Benzidine, C12H12N2
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              12185
_journal_page_last               12191
_journal_paper_doi               10.1021/ja063224b
_journal_volume                  128
_journal_year                    2006
_chemical_formula_sum            'C12 H12 N2'
_chemical_formula_weight         184.24
_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                 99.966(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            18
_cell_length_a                   11.3178(14)
_cell_length_b                   22.552(3)
_cell_length_c                   18.076(2)
_cell_measurement_temperature    295(2)
_cell_volume                     4544.1(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1458
_diffrn_reflns_av_sigmaI/netI    0.2220
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            39535
_diffrn_reflns_theta_full        28.30
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         1.46
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.212
_exptl_crystal_description       prism
_exptl_crystal_F_000             1764
_refine_diff_density_max         0.160
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.704
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     700
_refine_ls_number_reflns         11265
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.704
_refine_ls_R_factor_all          0.2691
_refine_ls_R_factor_gt           0.0489
_refine_ls_shift/su_max          0.013
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0655P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1082
_refine_ls_wR_factor_ref         0.1795
_reflns_number_gt                2308
_reflns_number_total             11265
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja063224bsi20060509_051213.cif
_cod_data_source_block           cobenz
_cod_original_cell_volume        4544.0(10)
_cod_database_code               4110869
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
C4 C 0.8769(4) 0.38754(18) 0.45240(18) 0.0609(10) Uani 1 1 d .
C7 C 0.7470(4) 0.40066(17) 0.43793(18) 0.0612(10) Uani 1 1 d .
N1 N 1.2507(3) 0.35697(14) 0.49597(16) 0.0893(11) Uani 1 1 d .
H2 H 1.2786 0.3236 0.5143 0.107 Uiso 1 1 calc R
H1 H 1.2991 0.3846 0.4876 0.107 Uiso 1 1 calc R
C8 C 0.6598(4) 0.3559(2) 0.4190(2) 0.0690(12) Uani 1 1 d .
C3 C 0.9242(4) 0.33311(18) 0.4794(2) 0.0686(11) Uani 1 1 d .
C12 C 0.7035(5) 0.4580(2) 0.4417(2) 0.0717(12) Uani 1 1 d .
C1 C 1.1273(4) 0.3663(2) 0.4798(2) 0.0691(11) Uani 1 1 d .
C5 C 0.9591(5) 0.4306(2) 0.4400(2) 0.0751(13) Uani 1 1 d .
N2 N 0.3760(3) 0.44008(15) 0.38928(18) 0.0940(11) Uani 1 1 d .
H11 H 0.3233 0.4125 0.3783 0.113 Uiso 1 1 calc R
H12 H 0.3536 0.4765 0.3905 0.113 Uiso 1 1 calc R
C10 C 0.4983(4) 0.4256(2) 0.4052(2) 0.0716(12) Uani 1 1 d .
C2 C 1.0475(4) 0.3225(2) 0.4928(2) 0.0743(12) Uani 1 1 d .
C6 C 1.0813(5) 0.4205(2) 0.4526(2) 0.0753(13) Uani 1 1 d .
C9 C 0.5379(4) 0.3684(2) 0.4040(2) 0.0740(12) Uani 1 1 d .
C11 C 0.5823(5) 0.4708(2) 0.4261(2) 0.0788(14) Uani 1 1 d .
C40 C 0.3717(4) 0.07400(16) 0.2127(2) 0.0663(11) Uani 1 1 d .
C25 C 0.6873(4) 0.2833(2) 0.1948(2) 0.0740(12) Uani 1 1 d .
C28 C 0.4507(4) 0.3109(2) 0.21494(18) 0.0650(11) Uani 1 1 d .
C43 C 0.2409(4) 0.08621(17) 0.1987(2) 0.0685(11) Uani 1 1 d .
N8 N -0.1291(3) 0.12600(14) 0.16659(17) 0.0911(11) Uani 1 1 d .
H47 H -0.1599 0.1492 0.1306 0.109 Uiso 1 1 calc R
H48 H -0.1733 0.1119 0.1967 0.109 Uiso 1 1 calc R
C39 C 0.4379(5) 0.0752(2) 0.1552(3) 0.0811(14) Uani 1 1 d .
C30 C 0.6568(4) 0.3403(2) 0.2106(2) 0.0743(12) Uani 1 1 d .
N5 N 0.8036(3) 0.26939(16) 0.18316(16) 0.0911(11) Uani 1 1 d .
H25 H 0.8571 0.2967 0.1859 0.109 Uiso 1 1 calc R
H26 H 0.8213 0.2335 0.1733 0.109 Uiso 1 1 calc R
C31 C 0.3289(4) 0.3266(2) 0.2276(2) 0.0693(11) Uani 1 1 d .
C27 C 0.4832(5) 0.2539(2) 0.1991(2) 0.0763(13) Uani 1 1 d .
C46 C -0.0084(4) 0.11129(19) 0.1761(2) 0.0746(12) Uani 1 1 d .
C38 C 0.5581(5) 0.0611(2) 0.1654(3) 0.0802(14) Uani 1 1 d .
C29 C 0.5405(5) 0.3534(3) 0.2201(2) 0.0766(13) Uani 1 1 d .
C47 C 0.0439(4) 0.07349(19) 0.2339(2) 0.0787(13) Uani 1 1 d .
C26 C 0.5982(5) 0.2406(3) 0.1891(2) 0.0831(15) Uani 1 1 d .
C48 C 0.1659(4) 0.06292(18) 0.2447(2) 0.0802(13) Uani 1 1 d .
H46 H 0.1995 0.0390 0.2848 0.096 Uiso 1 1 calc R
C45 C 0.0636(5) 0.1338(2) 0.1279(3) 0.0821(14) Uani 1 1 d .
C41 C 0.4338(4) 0.06049(19) 0.2833(2) 0.0801(13) Uani 1 1 d .
C37 C 0.6165(4) 0.04403(18) 0.2349(2) 0.0800(12) Uani 1 1 d .
N7 N 0.7384(3) 0.02651(17) 0.2451(2) 0.1097(13) Uani 1 1 d .
H38 H 0.7760 0.0266 0.2077 0.132 Uiso 1 1 calc R
H37 H 0.7749 0.0158 0.2888 0.132 Uiso 1 1 calc R
C44 C 0.1854(5) 0.1220(2) 0.1399(2) 0.0798(13) Uani 1 1 d .
C36 C 0.2743(4) 0.3797(2) 0.2031(2) 0.0857(13) Uani 1 1 d .
H31 H 0.3149 0.4059 0.1765 0.103 Uiso 1 1 calc R
C42 C 0.5544(4) 0.0459(2) 0.2944(2) 0.0905(14) Uani 1 1 d .
H42 H 0.5943 0.0372 0.3426 0.109 Uiso 1 1 calc R
C34 C 0.1020(5) 0.3579(3) 0.2568(3) 0.1051(19) Uani 1 1 d .
C35 C 0.1622(5) 0.3953(2) 0.2167(3) 0.1027(16) Uani 1 1 d .
H32 H 0.1277 0.4311 0.1986 0.123 Uiso 1 1 calc R
C32 C 0.2646(5) 0.2886(2) 0.2667(2) 0.1001(15) Uani 1 1 d .
H34 H 0.2973 0.2522 0.2835 0.120 Uiso 1 1 calc R
N6 N -0.0157(3) 0.3724(2) 0.2701(2) 0.1444(18) Uani 1 1 d .
H35 H -0.0544 0.3476 0.2931 0.173 Uiso 1 1 calc R
H36 H -0.0478 0.4058 0.2551 0.173 Uiso 1 1 calc R
C33 C 0.1507(6) 0.3048(4) 0.2812(3) 0.1069(19) Uani 1 1 d .
C22 C 0.4565(4) 0.21294(17) 0.4966(2) 0.0708(11) Uani 1 1 d .
C19 C 0.6902(4) 0.19473(15) 0.4649(2) 0.0635(11) Uani 1 1 d .
C24 C 0.6704(5) 0.21037(17) 0.5364(2) 0.0716(12) Uani 1 1 d .
C52 C 0.5599(3) 0.99552(19) 0.4897(2) 0.0693(12) Uani 1 1 d .
N4 N 0.3419(3) 0.22395(14) 0.51104(18) 0.0946(11) Uani 1 1 d .
H24 H 0.3322 0.2350 0.5551 0.114 Uiso 1 1 calc R
H23 H 0.2807 0.2197 0.4759 0.114 Uiso 1 1 calc R
C16 C 0.8114(4) 0.18431(15) 0.4490(2) 0.0643(11) Uani 1 1 d .
C17 C 0.9085(5) 0.17159(18) 0.5049(2) 0.0743(13) Uani 1 1 d .
C13 C 1.0419(4) 0.15789(19) 0.4175(3) 0.0851(13) Uani 1 1 d .
C20 C 0.5871(5) 0.18834(18) 0.4111(2) 0.0747(13) Uani 1 1 d .
N3 N 1.1559(3) 0.14476(17) 0.40179(19) 0.1144(14) Uani 1 1 d .
H13 H 1.2140 0.1370 0.4379 0.137 Uiso 1 1 calc R
H14 H 1.1679 0.1445 0.3561 0.137 Uiso 1 1 calc R
C14 C 0.9481(5) 0.1732(2) 0.3615(3) 0.0966(17) Uani 1 1 d .
C23 C 0.5566(5) 0.21941(18) 0.5517(3) 0.0768(13) Uani 1 1 d .
C15 C 0.8371(5) 0.1855(2) 0.3768(3) 0.0836(16) Uani 1 1 d .
C54 C 0.7591(5) 1.0309(3) 0.4805(3) 0.0980(16) Uani 1 1 d .
C18 C 1.0216(5) 0.15850(19) 0.4901(3) 0.0788(13) Uani 1 1 d .
C49 C 0.7857(5) 0.9807(2) 0.4439(3) 0.0845(13) Uani 1 1 d .
C51 C 0.5902(5) 0.9442(2) 0.4549(3) 0.0843(15) Uani 1 1 d .
C53 C 0.6503(6) 1.0375(2) 0.5023(3) 0.0905(16) Uani 1 1 d .
C50 C 0.7003(6) 0.9369(2) 0.4337(3) 0.0950(17) Uani 1 1 d .
C21 C 0.4743(5) 0.1968(2) 0.4256(2) 0.0803(13) Uani 1 1 d .
N9 N 0.8918(6) 0.9769(3) 0.4130(4) 0.1221(19) Uani 1 1 d .
H53 H 0.637(3) 1.0685(16) 0.5276(19) 0.078(15) Uiso 1 1 d .
H49 H 0.938(5) 1.004(3) 0.441(3) 0.17(3) Uiso 1 1 d .
H19 H 0.601(2) 0.1757(12) 0.3634(15) 0.042(9) Uiso 1 1 d .
H7 H 0.690(3) 0.3124(16) 0.4116(18) 0.094(13) Uiso 1 1 d .
H41 H 0.390(3) 0.0606(13) 0.3341(17) 0.081(11) Uiso 1 1 d .
H18 H 0.897(2) 0.1673(12) 0.5528(16) 0.046(10) Uiso 1 1 d .
H40 H 0.400(3) 0.0848(13) 0.1116(16) 0.051(11) Uiso 1 1 d .
H5 H 0.928(3) 0.4654(16) 0.4205(19) 0.082(14) Uiso 1 1 d .
H30 H 0.717(3) 0.3723(14) 0.2145(17) 0.071(12) Uiso 1 1 d .
H16 H 0.967(3) 0.1753(15) 0.3174(18) 0.073(13) Uiso 1 1 d .
H21 H 0.544(3) 0.2230(14) 0.6019(19) 0.076(12) Uiso 1 1 d .
H43 H 0.233(3) 0.1406(15) 0.1065(19) 0.082(14) Uiso 1 1 d .
H6 H 1.136(3) 0.4495(16) 0.4351(18) 0.087(14) Uiso 1 1 d .
H8 H 0.472(3) 0.3290(17) 0.381(2) 0.120(14) Uiso 1 1 d .
H4 H 0.860(3) 0.2942(16) 0.4854(18) 0.104(13) Uiso 1 1 d .
H15 H 1.088(3) 0.1435(15) 0.532(2) 0.098(13) Uiso 1 1 d .
H20 H 0.400(3) 0.1862(15) 0.3900(19) 0.084(12) Uiso 1 1 d .
H45 H -0.005(3) 0.0553(16) 0.2762(19) 0.100(13) Uiso 1 1 d .
H17 H 0.788(3) 0.1953(15) 0.3449(17) 0.054(13) Uiso 1 1 d .
H28 H 0.427(3) 0.2222(14) 0.1966(17) 0.067(12) Uiso 1 1 d .
H3 H 1.072(3) 0.2784(18) 0.510(2) 0.112(15) Uiso 1 1 d .
H22 H 0.741(3) 0.2127(14) 0.5756(18) 0.077(12) Uiso 1 1 d .
H51 H 0.711(3) 0.9093(15) 0.4076(19) 0.064(14) Uiso 1 1 d .
H39 H 0.598(3) 0.0620(16) 0.1282(19) 0.082(15) Uiso 1 1 d .
H27 H 0.618(3) 0.2076(14) 0.1786(18) 0.058(14) Uiso 1 1 d .
H10 H 0.764(3) 0.4904(17) 0.4551(19) 0.107(15) Uiso 1 1 d .
H52 H 0.532(3) 0.9173(15) 0.4505(17) 0.064(13) Uiso 1 1 d .
H29 H 0.526(4) 0.3913(18) 0.225(2) 0.102(18) Uiso 1 1 d .
H33 H 0.111(4) 0.273(2) 0.305(2) 0.14(2) Uiso 1 1 d .
H44 H 0.038(4) 0.1630(18) 0.088(2) 0.118(17) Uiso 1 1 d .
H9 H 0.558(3) 0.5060(15) 0.4259(19) 0.075(14) Uiso 1 1 d .
H54 H 0.823(4) 1.0596(17) 0.491(2) 0.100(16) Uiso 1 1 d .
H50 H 0.915(4) 0.9442(19) 0.410(3) 0.11(2) Uiso 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_3
C5 C4 C3 116.4(4) .
C5 C4 C7 120.3(4) .
C3 C4 C7 123.3(4) .
C12 C7 C8 116.0(4) .
C12 C7 C4 121.8(4) .
C8 C7 C4 122.2(4) .
C1 N1 H2 120.0 .
C1 N1 H1 120.0 .
H2 N1 H1 120.0 .
C9 C8 C7 122.1(4) .
C9 C8 H7 120(2) .
C7 C8 H7 118(2) .
C4 C3 C2 121.6(4) .
C4 C3 H4 119.6(18) .
C2 C3 H4 118.5(18) .
C11 C12 C7 122.1(5) .
C11 C12 H10 121(2) .
C7 C12 H10 117(2) .
C2 C1 C6 118.3(4) .
C2 C1 N1 121.1(4) .
C6 C1 N1 120.6(4) .
C6 C5 C4 122.5(5) .
C6 C5 H5 121(2) .
C4 C5 H5 116(2) .
C10 N2 H11 120.0 .
C10 N2 H12 120.0 .
H11 N2 H12 120.0 .
C9 C10 C11 118.9(5) .
C9 C10 N2 122.0(4) .
C11 C10 N2 119.1(5) .
C1 C2 C3 120.6(4) .
C1 C2 H3 125(2) .
C3 C2 H3 115(2) .
C5 C6 C1 120.6(5) .
C5 C6 H6 120(2) .
C1 C6 H6 119(2) .
C10 C9 C8 120.3(4) .
C10 C9 H8 121.6(18) .
C8 C9 H8 117.5(18) .
C12 C11 C10 120.4(5) .
C12 C11 H9 121(3) .
C10 C11 H9 119(3) .
C41 C40 C39 116.3(4) .
C41 C40 C43 122.2(4) .
C39 C40 C43 121.5(4) .
C30 C25 C26 117.3(5) .
C30 C25 N5 121.1(5) .
C26 C25 N5 121.6(5) .
C27 C28 C29 116.0(5) .
C27 C28 C31 123.0(5) .
C29 C28 C31 121.0(4) .
C48 C43 C44 115.7(5) .
C48 C43 C40 121.5(4) .
C44 C43 C40 122.8(4) .
C46 N8 H47 120.0 .
C46 N8 H48 120.0 .
H47 N8 H48 120.0 .
C38 C39 C40 123.1(5) .
C38 C39 H40 120(2) .
C40 C39 H40 117(2) .
C25 C30 C29 120.1(5) .
C25 C30 H30 120.4(19) .
C29 C30 H30 119(2) .
C25 N5 H25 120.0 .
C25 N5 H26 120.0 .
H25 N5 H26 120.0 .
C36 C31 C32 116.8(4) .
C36 C31 C28 122.3(4) .
C32 C31 C28 120.9(5) .
C26 C27 C28 121.4(5) .
C26 C27 H28 118(2) .
C28 C27 H28 120(2) .
N8 C46 C45 120.5(4) .
N8 C46 C47 121.3(5) .
C45 C46 C47 118.3(5) .
C37 C38 C39 119.7(5) .
C37 C38 H39 119(3) .
C39 C38 H39 121(3) .
C28 C29 C30 123.0(5) .
C28 C29 H29 122(3) .
C30 C29 H29 114(3) .
C48 C47 C46 119.6(5) .
C48 C47 H45 116.5(19) .
C46 C47 H45 123.5(19) .
C27 C26 C25 122.1(5) .
C27 C26 H27 123(3) .
C25 C26 H27 115(3) .
C47 C48 C43 123.3(4) .
C47 C48 H46 118.3 .
C43 C48 H46 118.3 .
C44 C45 C46 120.6(5) .
C44 C45 H44 114(3) .
C46 C45 H44 125(3) .
C40 C41 C42 121.2(4) .
C40 C41 H41 122.2(16) .
C42 C41 H41 116.6(16) .
C38 C37 C42 118.4(5) .
C38 C37 N7 120.2(5) .
C42 C37 N7 121.4(4) .
C37 N7 H38 120.0 .
C37 N7 H37 120.0 .
H38 N7 H37 120.0 .
C45 C44 C43 122.3(5) .
C45 C44 H43 118(2) .
C43 C44 H43 120(2) .
C35 C36 C31 122.5(5) .
C35 C36 H31 118.7 .
C31 C36 H31 118.7 .
C37 C42 C41 121.0(4) .
C37 C42 H42 119.5 .
C41 C42 H42 119.5 .
C33 C34 C35 120.3(6) .
C33 C34 N6 118.9(7) .
C35 C34 N6 120.8(7) .
C34 C35 C36 119.6(5) .
C34 C35 H32 120.2 .
C36 C35 H32 120.2 .
C31 C32 C33 120.7(5) .
C31 C32 H34 119.7 .
C33 C32 H34 119.7 .
C34 N6 H35 120.0 .
C34 N6 H36 120.0 .
H35 N6 H36 120.0 .
C34 C33 C32 120.1(6) .
C34 C33 H33 126(3) .
C32 C33 H33 113(3) .
C23 C22 C21 117.7(5) .
C23 C22 N4 121.4(4) .
C21 C22 N4 120.9(4) .
C20 C19 C24 115.1(4) .
C20 C19 C16 123.0(4) .
C24 C19 C16 121.8(4) .
C23 C24 C19 121.9(4) .
C23 C24 H22 122(2) .
C19 C24 H22 116(2) .
C53 C52 C51 114.3(4) .
C53 C52 C52 123.3(5) 3_676
C51 C52 C52 122.4(5) 3_676
C22 N4 H24 120.0 .
C22 N4 H23 120.0 .
H24 N4 H23 120.0 .
C15 C16 C17 114.9(5) .
C15 C16 C19 122.5(4) .
C17 C16 C19 122.6(4) .
C18 C17 C16 123.1(4) .
C18 C17 H18 117.1(19) .
C16 C17 H18 119.4(19) .
C18 C13 C14 117.7(5) .
C18 C13 N3 120.6(4) .
C14 C13 N3 121.6(5) .
C21 C20 C19 123.5(4) .
C21 C20 H19 122.1(17) .
C19 C20 H19 114.3(17) .
C13 N3 H13 120.0 .
C13 N3 H14 120.0 .
H13 N3 H14 120.0 .
C15 C14 C13 121.5(5) .
C15 C14 H16 124(2) .
C13 C14 H16 114(2) .
C24 C23 C22 121.2(5) .
C24 C23 H21 120(2) .
C22 C23 H21 117(2) .
C14 C15 C16 122.6(5) .
C14 C15 H17 119(3) .
C16 C15 H17 118(3) .
C53 C54 C49 120.9(6) .
C53 C54 H54 124(2) .
C49 C54 H54 115(2) .
C13 C18 C17 120.0(5) .
C13 C18 H15 119(2) .
C17 C18 H15 121(2) .
C54 C49 C50 116.8(6) .
C54 C49 N9 121.0(6) .
C50 C49 N9 122.0(6) .
C50 C51 C52 122.2(5) .
C50 C51 H52 126(2) .
C52 C51 H52 112(2) .
C54 C53 C52 123.9(5) .
C54 C53 H53 119(3) .
C52 C53 H53 117(3) .
C49 C50 C51 121.7(6) .
C49 C50 H51 118(3) .
C51 C50 H51 119(3) .
C20 C21 C22 120.6(4) .
C20 C21 H20 124(2) .
C22 C21 H20 115(2) .
C49 N9 H49 101(4) .
C49 N9 H50 114(4) .
H49 N9 H50 121(6) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C4 C5 1.390(5) .
C4 C3 1.393(5) .
C4 C7 1.478(5) .
C7 C12 1.390(5) .
C7 C8 1.411(5) .
N1 C1 1.393(5) .
N1 H2 0.8600 .
N1 H1 0.8600 .
C8 C9 1.389(5) .
C8 H7 1.06(4) .
C3 C2 1.395(5) .
C3 H4 1.16(4) .
C12 C11 1.382(6) .
C12 H10 1.00(4) .
C1 C2 1.385(5) .
C1 C6 1.386(5) .
C5 C6 1.381(6) .
C5 H5 0.91(3) .
N2 C10 1.403(5) .
N2 H11 0.8600 .
N2 H12 0.8600 .
C10 C9 1.368(5) .
C10 C11 1.399(6) .
C2 H3 1.07(4) .
C6 H6 0.99(4) .
C9 H8 1.19(4) .
C11 H9 0.84(3) .
C40 C41 1.380(5) .
C40 C39 1.382(5) .
C40 C43 1.483(5) .
C25 C30 1.375(5) .
C25 C26 1.385(6) .
C25 N5 1.403(5) .
C28 C27 1.380(5) .
C28 C29 1.388(6) .
C28 C31 1.479(5) .
C43 C48 1.390(5) .
C43 C44 1.395(5) .
N8 C46 1.387(4) .
N8 H47 0.8600 .
N8 H48 0.8600 .
C39 C38 1.379(6) .
C39 H40 0.86(3) .
C30 C29 1.388(6) .
C30 H30 0.98(3) .
N5 H25 0.8600 .
N5 H26 0.8600 .
C31 C36 1.384(5) .
C31 C32 1.394(5) .
C27 C26 1.378(6) .
C27 H28 0.96(3) .
C46 C45 1.388(6) .
C46 C47 1.398(5) .
C38 C37 1.369(6) .
C38 H39 0.87(3) .
C29 H29 0.88(4) .
C47 C48 1.382(5) .
C47 H45 1.09(4) .
C26 H27 0.81(3) .
C48 H46 0.9300 .
C45 C44 1.385(6) .
C45 H44 0.98(4) .
C41 C42 1.385(5) .
C41 H41 1.12(3) .
C37 C42 1.383(5) .
C37 N7 1.417(5) .
N7 H38 0.8600 .
N7 H37 0.8600 .
C44 H43 0.97(3) .
C36 C35 1.379(6) .
C36 H31 0.9300 .
C42 H42 0.9300 .
C34 C33 1.361(7) .
C34 C35 1.369(6) .
C34 N6 1.432(6) .
C35 H32 0.9300 .
C32 C33 1.407(7) .
C32 H34 0.9300 .
N6 H35 0.8600 .
N6 H36 0.8600 .
C33 H33 0.98(4) .
C22 C23 1.380(5) .
C22 C21 1.381(5) .
C22 N4 1.389(4) .
C19 C20 1.391(5) .
C19 C24 1.395(5) .
C19 C16 1.470(5) .
C24 C23 1.379(6) .
C24 H22 0.97(3) .
C52 C53 1.382(6) .
C52 C51 1.388(6) .
C52 C52 1.481(8) 3_676
N4 H24 0.8600 .
N4 H23 0.8600 .
C16 C15 1.385(5) .
C16 C17 1.387(5) .
C17 C18 1.384(6) .
C17 H18 0.90(3) .
C13 C18 1.372(5) .
C13 C14 1.378(6) .
C13 N3 1.400(5) .
C20 C21 1.360(5) .
C20 H19 0.95(3) .
N3 H13 0.8600 .
N3 H14 0.8600 .
C14 C15 1.361(6) .
C14 H16 0.86(3) .
C23 H21 0.95(3) .
C15 H17 0.76(3) .
C54 C53 1.364(6) .
C54 C49 1.370(6) .
C54 H54 0.97(4) .
C18 H15 1.03(4) .
C49 C50 1.373(7) .
C49 N9 1.412(7) .
C51 C50 1.376(7) .
C51 H52 0.89(3) .
C53 H53 0.86(3) .
C50 H51 0.80(3) .
C21 H20 1.00(3) .
N9 H49 0.90(5) .
N9 H50 0.79(4) .
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
C5 C4 C7 C12 -26.6(5) .
C3 C4 C7 C12 152.7(4) .
C5 C4 C7 C8 153.0(4) .
C3 C4 C7 C8 -27.7(5) .
C12 C7 C8 C9 1.0(5) .
C4 C7 C8 C9 -178.7(3) .
C5 C4 C3 C2 -0.3(5) .
C7 C4 C3 C2 -179.6(4) .
C8 C7 C12 C11 -1.6(6) .
C4 C7 C12 C11 178.1(4) .
C3 C4 C5 C6 0.7(6) .
C7 C4 C5 C6 -180.0(4) .
C6 C1 C2 C3 -0.6(6) .
N1 C1 C2 C3 177.3(3) .
C4 C3 C2 C1 0.3(6) .
C4 C5 C6 C1 -1.1(6) .
C2 C1 C6 C5 1.0(6) .
N1 C1 C6 C5 -176.9(4) .
C11 C10 C9 C8 -3.5(6) .
N2 C10 C9 C8 179.1(3) .
C7 C8 C9 C10 1.6(6) .
C7 C12 C11 C10 -0.4(6) .
C9 C10 C11 C12 3.0(6) .
N2 C10 C11 C12 -179.6(4) .
C41 C40 C43 C48 -26.1(6) .
C39 C40 C43 C48 153.5(4) .
C41 C40 C43 C44 153.1(4) .
C39 C40 C43 C44 -27.4(6) .
C41 C40 C39 C38 3.1(6) .
C43 C40 C39 C38 -176.5(4) .
C26 C25 C30 C29 -0.2(6) .
N5 C25 C30 C29 178.4(4) .
C27 C28 C31 C36 -143.3(4) .
C29 C28 C31 C36 38.2(5) .
C27 C28 C31 C32 38.2(5) .
C29 C28 C31 C32 -140.3(4) .
C29 C28 C27 C26 -0.1(6) .
C31 C28 C27 C26 -178.7(4) .
C40 C39 C38 C37 1.1(7) .
C27 C28 C29 C30 -0.3(6) .
C31 C28 C29 C30 178.3(4) .
C25 C30 C29 C28 0.5(6) .
N8 C46 C47 C48 -175.8(4) .
C45 C46 C47 C48 4.4(6) .
C28 C27 C26 C25 0.4(6) .
C30 C25 C26 C27 -0.2(6) .
N5 C25 C26 C27 -178.9(4) .
C46 C47 C48 C43 -2.7(7) .
C44 C43 C48 C47 0.4(6) .
C40 C43 C48 C47 179.6(4) .
N8 C46 C45 C44 176.2(4) .
C47 C46 C45 C44 -4.0(6) .
C39 C40 C41 C42 -3.4(6) .
C43 C40 C41 C42 176.2(4) .
C39 C38 C37 C42 -5.0(7) .
C39 C38 C37 N7 176.7(4) .
C46 C45 C44 C43 1.7(7) .
C48 C43 C44 C45 0.1(6) .
C40 C43 C44 C45 -179.1(4) .
C32 C31 C36 C35 0.5(6) .
C28 C31 C36 C35 -178.1(4) .
C38 C37 C42 C41 4.7(7) .
N7 C37 C42 C41 -177.1(4) .
C40 C41 C42 C37 -0.4(7) .
C33 C34 C35 C36 -2.1(7) .
N6 C34 C35 C36 -178.5(4) .
C31 C36 C35 C34 1.1(7) .
C36 C31 C32 C33 -1.0(6) .
C28 C31 C32 C33 177.5(4) .
C35 C34 C33 C32 1.6(8) .
N6 C34 C33 C32 178.0(4) .
C31 C32 C33 C34 0.1(7) .
C20 C19 C24 C23 -0.7(6) .
C16 C19 C24 C23 -179.1(4) .
C20 C19 C16 C15 20.6(6) .
C24 C19 C16 C15 -161.1(4) .
C20 C19 C16 C17 -158.3(4) .
C24 C19 C16 C17 19.9(6) .
C15 C16 C17 C18 -2.7(6) .
C19 C16 C17 C18 176.3(4) .
C24 C19 C20 C21 0.3(6) .
C16 C19 C20 C21 178.7(4) .
C18 C13 C14 C15 -3.5(8) .
N3 C13 C14 C15 179.5(5) .
C19 C24 C23 C22 0.4(6) .
C21 C22 C23 C24 0.4(6) .
N4 C22 C23 C24 -177.8(4) .
C13 C14 C15 C16 0.9(8) .
C17 C16 C15 C14 2.1(7) .
C19 C16 C15 C14 -176.9(4) .
C14 C13 C18 C17 2.9(7) .
N3 C13 C18 C17 180.0(4) .
C16 C17 C18 C13 0.2(7) .
C53 C54 C49 C50 -2.9(7) .
C53 C54 C49 N9 172.0(5) .
C53 C52 C51 C50 -1.2(6) .
C52 C52 C51 C50 177.8(5) 3_676
C49 C54 C53 C52 -0.2(8) .
C51 C52 C53 C54 2.3(7) .
C52 C52 C53 C54 -176.8(5) 3_676
C54 C49 C50 C51 4.0(7) .
N9 C49 C50 C51 -170.9(5) .
C52 C51 C50 C49 -1.9(8) .
C19 C20 C21 C22 0.5(7) .
C23 C22 C21 C20 -0.8(6) .
N4 C22 C21 C20 177.4(4) .
