#------------------------------------------------------------------------------
#$Date: 2016-03-22 10:39:23 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178879 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/08/4110872.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_4110872
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                 99.153(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            18
_cell_length_a                   11.6310(13)
_cell_length_b                   16.1892(19)
_cell_length_c                   24.173(3)
_cell_measurement_temperature    298(2)
_cell_volume                     4493.7(9)
_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      298(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  0.0694
_diffrn_reflns_av_sigmaI/netI    0.0766
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            39061
_diffrn_reflns_theta_full        28.33
_diffrn_reflns_theta_max         28.33
_diffrn_reflns_theta_min         1.52
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.225
_exptl_crystal_description       needle
_exptl_crystal_F_000             1764
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.843
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     764
_refine_ls_number_reflns         11194
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.843
_refine_ls_R_factor_all          0.1611
_refine_ls_R_factor_gt           0.0478
_refine_ls_shift/su_max          0.116
_refine_ls_shift/su_mean         0.005
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0710P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1137
_refine_ls_wR_factor_ref         0.1625
_reflns_number_gt                3875
_reflns_number_total             11194
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja063224bsi20060509_051310.cif
_cod_data_source_block           cobenz3
_cod_database_code               4110872
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
C1 C 0.2655(2) 0.49338(13) 0.16437(8) 0.0591(6) Uani 1 1 d .
C2 C 0.3892(2) 0.47264(13) 0.16471(8) 0.0583(6) Uani 1 1 d .
C3 C 0.4605(2) 0.51830(15) 0.13481(9) 0.0616(6) Uani 1 1 d .
N4 N -0.0878(2) 0.55707(16) 0.16452(10) 0.0785(6) Uani 1 1 d .
C5 C 0.5745(2) 0.49763(15) 0.13349(9) 0.0624(6) Uani 1 1 d .
C6 C 0.6246(2) 0.42908(15) 0.16206(9) 0.0636(6) Uani 1 1 d .
N3 N 0.7418(2) 0.40821(16) 0.16107(10) 0.0797(6) Uani 1 1 d .
C8 C 0.0856(3) 0.48081(16) 0.20237(11) 0.0781(8) Uani 1 1 d .
C9 C 0.0278(2) 0.53398(14) 0.16295(9) 0.0643(6) Uani 1 1 d .
C10 C 0.2055(2) 0.54676(16) 0.12507(10) 0.0739(7) Uani 1 1 d .
C11 C 0.5568(2) 0.38378(17) 0.19301(10) 0.0737(7) Uani 1 1 d .
C12 C 0.4424(3) 0.40518(16) 0.19433(10) 0.0711(7) Uani 1 1 d .
C13 C 0.2013(3) 0.46137(17) 0.20311(11) 0.0784(8) Uani 1 1 d .
C14 C 0.0903(3) 0.56658(18) 0.12386(11) 0.0788(8) Uani 1 1 d .
C15 C 0.3345(2) 0.66150(14) 0.00412(8) 0.0589(6) Uani 1 1 d .
C16 C 0.2868(2) 0.58646(16) -0.01607(9) 0.0646(6) Uani 1 1 d .
C17 C 0.6343(2) 0.71881(15) 0.07899(11) 0.0681(7) Uani 1 1 d .
C18 C 0.7072(2) 0.68063(14) 0.04649(9) 0.0637(6) Uani 1 1 d .
C19 C 0.4619(2) 0.67203(13) 0.01736(9) 0.0569(6) Uani 1 1 d .
C20 C 0.0915(2) 0.63716(19) -0.02296(9) 0.0719(7) Uani 1 1 d .
C21 C 0.1677(2) 0.57457(19) -0.02910(10) 0.0701(7) Uani 1 1 d .
N7 N 0.8277(2) 0.67922(17) 0.06292(11) 0.0827(7) Uani 1 1 d .
C23 C 0.5149(2) 0.71445(14) 0.06492(10) 0.0645(6) Uani 1 1 d .
C24 C 0.6559(2) 0.64051(15) -0.00181(10) 0.0675(6) Uani 1 1 d .
C25 C 0.2562(2) 0.72346(17) 0.01214(11) 0.0733(7) Uani 1 1 d .
C26 C 0.5363(2) 0.63615(16) -0.01559(10) 0.0674(7) Uani 1 1 d .
C27 C 0.1375(3) 0.7119(2) -0.00072(12) 0.0829(8) Uani 1 1 d .
N8 N -0.0305(2) 0.6260(3) -0.03521(12) 0.0951(9) Uani 1 1 d .
C29 C 0.4064(2) 0.87697(16) 0.16040(10) 0.0702(7) Uani 1 1 d .
C30 C 0.2827(2) 0.85374(15) 0.15724(9) 0.0681(7) Uani 1 1 d .
N6 N -0.0729(3) 0.79660(18) 0.15927(11) 0.0866(7) Uani 1 1 d .
C32 C 0.0449(3) 0.81548(17) 0.15942(10) 0.0738(7) Uani 1 1 d .
C33 C 0.1918(3) 0.90230(18) 0.13052(12) 0.0824(8) Uani 1 1 d .
C34 C 0.1335(3) 0.76479(18) 0.18540(12) 0.0848(8) Uani 1 1 d .
C35 C 0.4953(3) 0.83579(19) 0.19442(11) 0.0789(8) Uani 1 1 d .
C36 C 0.4409(3) 0.94381(19) 0.13133(14) 0.0895(9) Uani 1 1 d .
C37 C 0.2485(3) 0.78362(18) 0.18437(12) 0.0846(8) Uani 1 1 d .
C38 C 0.0759(3) 0.88371(19) 0.13128(12) 0.0841(8) Uani 1 1 d .
C39 C 0.6102(3) 0.8607(2) 0.19984(13) 0.0899(9) Uani 1 1 d .
C40 C 0.6421(3) 0.9289(2) 0.17239(14) 0.0900(8) Uani 1 1 d .
N5 N 0.7593(2) 0.95384(16) 0.17823(12) 0.1202(9) Uani 1 1 d .
H5A H 0.8122 0.9261 0.1993 0.144 Uiso 1 1 calc R
H5B H 0.7780 0.9968 0.1607 0.144 Uiso 1 1 calc R
C42 C 0.5557(3) 0.9705(2) 0.13749(16) 0.1005(10) Uani 1 1 d .
C43 C 1.0580(2) 0.17672(15) 0.17716(9) 0.0649(6) Uani 1 1 d .
C44 C 0.9173(2) 0.13823(15) 0.24128(10) 0.0681(6) Uani 1 1 d .
N2 N 0.6021(2) 0.17025(15) 0.23460(11) 0.0822(7) Uani 1 1 d .
C46 C 0.8074(2) 0.13710(15) 0.25517(11) 0.0711(7) Uani 1 1 d .
C47 C 1.0972(2) 0.24833(16) 0.15486(10) 0.0684(7) Uani 1 1 d .
C48 C 0.7114(2) 0.16665(14) 0.21860(10) 0.0652(6) Uani 1 1 d .
C49 C 0.9389(2) 0.17015(14) 0.19043(9) 0.0624(6) Uani 1 1 d .
C50 C 0.7309(2) 0.19577(16) 0.16663(10) 0.0716(7) Uani 1 1 d .
C51 C 0.8420(2) 0.19814(16) 0.15353(10) 0.0692(7) Uani 1 1 d .
C52 C 1.2078(2) 0.25463(18) 0.14128(11) 0.0728(7) Uani 1 1 d .
N1 N 1.3972(2) 0.1933(2) 0.13471(13) 0.0950(8) Uani 1 1 d .
C54 C 1.2839(2) 0.18888(18) 0.14937(11) 0.0744(7) Uani 1 1 d .
C55 C 1.1386(3) 0.11246(17) 0.18738(12) 0.0785(8) Uani 1 1 d .
C56 C 1.2492(3) 0.11851(19) 0.17435(13) 0.0850(8) Uani 1 1 d .
C57 C 0.7066(6) 0.9345(3) 0.00381(16) 0.1504(19) Uani 1 1 d .
N9 N 0.5934(4) 0.9095(2) 0.00357(18) 0.199(2) Uani 1 1 d .
H9A H 0.5441 0.9428 0.0147 0.239 Uiso 1 1 calc R
H9B H 0.5719 0.8607 -0.0077 0.239 Uiso 1 1 calc R
C60 C 0.9405(4) 0.9871(2) 0.00127(14) 0.1258(18) Uani 1 1 d .
C58 C 0.7893(7) 0.8851(3) -0.01471(18) 0.148(2) Uani 1 1 d .
C59 C 0.9003(6) 0.9108(3) -0.0162(2) 0.156(2) Uani 1 1 d .
C61 C 0.8599(7) 1.0367(3) 0.0207(2) 0.194(3) Uani 1 1 d .
C62 C 0.7465(6) 1.0123(3) 0.0214(2) 0.226(3) Uani 1 1 d .
H62 H 0.6952 1.0492 0.0342 0.272 Uiso 1 1 calc R
H12 H 0.4639(18) 0.7419(13) 0.0880(9) 0.070(7) Uiso 1 1 d .
H8 H 0.4304(18) 0.5665(14) 0.1155(9) 0.073(7) Uiso 1 1 d .
H2 H 1.2306(19) 0.3054(15) 0.1244(9) 0.074(7) Uiso 1 1 d .
H9 H 0.6193(19) 0.5319(14) 0.1119(9) 0.076(7) Uiso 1 1 d .
H3 H 1.0433(19) 0.2964(14) 0.1494(9) 0.077(7) Uiso 1 1 d .
H14 H 0.3396(19) 0.5391(14) -0.0200(9) 0.074(7) Uiso 1 1 d .
H4 H 0.8543(18) 0.2176(13) 0.1172(9) 0.069(6) Uiso 1 1 d .
H11 H 0.7051(19) 0.6104(14) -0.0257(9) 0.082(7) Uiso 1 1 d .
H10 H 0.6674(19) 0.7487(15) 0.1120(10) 0.086(8) Uiso 1 1 d .
H5 H 0.7939(19) 0.1143(14) 0.2920(10) 0.081(7) Uiso 1 1 d .
H13 H 0.288(2) 0.7760(17) 0.0279(10) 0.088(8) Uiso 1 1 d .
H1 H 1.113(2) 0.0643(15) 0.2033(9) 0.077(7) Uiso 1 1 d .
H7 H 0.3945(19) 0.3714(14) 0.2143(9) 0.080(7) Uiso 1 1 d .
H6 H 0.236(2) 0.4280(15) 0.2308(10) 0.088(8) Uiso 1 1 d .
H15 H 0.139(2) 0.5185(17) -0.0408(11) 0.102(9) Uiso 1 1 d .
H20 H 0.592(2) 0.3345(15) 0.2162(10) 0.085(7) Uiso 1 1 d .
H24 H 0.476(2) 0.7863(18) 0.2181(11) 0.108(10) Uiso 1 1 d .
H26 H 0.110(2) 0.7145(16) 0.2046(10) 0.092(8) Uiso 1 1 d .
H29 H 0.855(3) 0.721(2) 0.0878(13) 0.134(13) Uiso 1 1 d .
H25 H 0.307(2) 0.7439(17) 0.2033(11) 0.101(9) Uiso 1 1 d .
H30 H 0.5012(19) 0.6042(14) -0.0489(10) 0.083(7) Uiso 1 1 d .
H21 H 0.250(2) 0.5709(16) 0.0976(11) 0.103(9) Uiso 1 1 d .
H19 H 0.761(2) 0.3537(18) 0.1757(11) 0.102(10) Uiso 1 1 d .
H18 H 0.590(2) 0.1325(18) 0.2620(12) 0.108(10) Uiso 1 1 d .
H23 H 0.385(2) 0.9728(18) 0.1096(11) 0.106(11) Uiso 1 1 d .
H17 H 0.660(2) 0.2164(14) 0.1385(10) 0.082(7) Uiso 1 1 d .
H22 H 0.578(3) 1.019(2) 0.1161(14) 0.144(13) Uiso 1 1 d .
H16 H 0.983(2) 0.1157(15) 0.2679(10) 0.087(8) Uiso 1 1 d .
H28 H -0.086(2) 0.7619(19) 0.1872(12) 0.109(11) Uiso 1 1 d .
H27 H 0.018(2) 0.9219(18) 0.1157(12) 0.113(11) Uiso 1 1 d .
H43 H 1.303(2) 0.0703(16) 0.1822(10) 0.093(8) Uiso 1 1 d .
H35 H 0.051(2) 0.6050(16) 0.0958(11) 0.097(9) Uiso 1 1 d .
H44 H 0.086(2) 0.7538(16) 0.0060(10) 0.095(9) Uiso 1 1 d .
H34 H 0.040(2) 0.4552(16) 0.2275(11) 0.102(9) Uiso 1 1 d .
H36 H 0.212(2) 0.9509(18) 0.1097(11) 0.107(10) Uiso 1 1 d .
H32 H -0.118(2) 0.5890(18) 0.1349(12) 0.111(12) Uiso 1 1 d .
H37 H 0.664(3) 0.8257(19) 0.2228(12) 0.122(12) Uiso 1 1 d .
H42 H 1.404(3) 0.238(2) 0.1133(13) 0.121(14) Uiso 1 1 d .
H39 H 0.761(3) 0.835(2) -0.0246(14) 0.134(14) Uiso 1 1 d .
H31 H 0.768(3) 0.418(2) 0.1287(14) 0.133(13) Uiso 1 1 d .
H45 H -0.056(3) 0.582(2) -0.0546(14) 0.137(18) Uiso 1 1 d .
H33 H -0.133(3) 0.5091(19) 0.1773(12) 0.128(11) Uiso 1 1 d .
H41 H 1.426(3) 0.141(3) 0.1260(16) 0.177(18) Uiso 1 1 d .
H48 H 0.873(3) 0.6629(18) 0.0365(13) 0.117(11) Uiso 1 1 d .
H46 H 0.535(3) 0.1797(18) 0.2063(13) 0.119(12) Uiso 1 1 d .
H49 H -0.130(3) 0.841(2) 0.1505(15) 0.165(17) Uiso 1 1 d .
H47 H -0.060(3) 0.674(2) -0.0463(16) 0.156(19) Uiso 1 1 d .
H53 H 0.958(4) 0.870(3) -0.0282(17) 0.188(18) Uiso 1 1 d .
H60 H 0.883(4) 1.091(3) 0.034(2) 0.22(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
C10 C1 C13 115.4(2) .
C10 C1 C2 122.0(2) .
C13 C1 C2 122.7(2) .
C3 C2 C12 115.4(2) .
C3 C2 C1 122.4(2) .
C12 C2 C1 122.2(2) .
C5 C3 C2 122.6(2) .
C3 C5 C6 121.0(2) .
C11 C6 C5 117.7(3) .
C11 C6 N3 121.3(3) .
C5 C6 N3 121.0(2) .
C13 C8 C9 121.3(3) .
C8 C9 C14 117.3(3) .
C8 C9 N4 120.9(2) .
C14 C9 N4 121.8(3) .
C14 C10 C1 122.9(2) .
C12 C11 C6 121.0(3) .
C11 C12 C2 122.4(2) .
C8 C13 C1 122.3(3) .
C10 C14 C9 120.8(3) .
C25 C15 C16 116.5(2) .
C25 C15 C19 123.0(2) .
C16 C15 C19 120.5(2) .
C21 C16 C15 122.0(3) .
C23 C17 C18 121.3(3) .
C24 C18 C17 117.7(2) .
C24 C18 N7 120.7(2) .
C17 C18 N7 121.5(2) .
C26 C19 C23 116.3(2) .
C26 C19 C15 121.4(2) .
C23 C19 C15 122.2(2) .
C21 C20 C27 117.9(3) .
C21 C20 N8 121.8(3) .
C27 C20 N8 120.1(3) .
C20 C21 C16 120.9(3) .
C17 C23 C19 121.7(2) .
C26 C24 C18 120.7(2) .
C27 C25 C15 121.7(3) .
C24 C26 C19 122.3(2) .
C25 C27 C20 120.9(3) .
C36 C29 C35 115.4(3) .
C36 C29 C30 122.1(3) .
C35 C29 C30 122.5(3) .
C33 C30 C37 115.0(3) .
C33 C30 C29 122.8(3) .
C37 C30 C29 122.0(3) .
C38 C32 C34 117.7(3) .
C38 C32 N6 120.4(3) .
C34 C32 N6 121.8(3) .
C38 C33 C30 122.8(3) .
C37 C34 C32 121.0(3) .
C39 C35 C29 122.4(3) .
C29 C36 C42 122.7(3) .
C34 C37 C30 122.5(3) .
C32 C38 C33 120.9(3) .
C40 C39 C35 121.4(3) .
C39 C40 C42 117.6(3) .
C39 C40 N5 121.0(3) .
C42 C40 N5 121.4(3) .
C40 C42 C36 120.5(3) .
C47 C43 C55 116.1(2) .
C47 C43 C49 121.6(2) .
C55 C43 C49 122.4(2) .
C46 C44 C49 121.8(2) .
C44 C46 C48 121.6(2) .
C52 C47 C43 122.0(2) .
N2 C48 C50 121.7(2) .
N2 C48 C46 121.0(2) .
C50 C48 C46 117.3(2) .
C44 C49 C51 116.3(2) .
C44 C49 C43 121.8(2) .
C51 C49 C43 121.9(2) .
C51 C50 C48 120.6(2) .
C50 C51 C49 122.3(2) .
C54 C52 C47 120.7(3) .
C56 C54 C52 118.3(3) .
C56 C54 N1 119.9(3) .
C52 C54 N1 121.8(3) .
C56 C55 C43 122.2(3) .
C55 C56 C54 120.5(3) .
N9 C57 C62 122.7(5) .
N9 C57 C58 123.0(5) .
C62 C57 C58 114.2(6) .
C59 C60 C61 114.6(5) .
C59 C60 C60 122.0(5) 3_775
C61 C60 C60 123.4(5) 3_775
C59 C58 C57 123.0(6) .
H53 C59 C58 119(3) .
H53 C59 C60 118(3) .
C58 C59 C60 123.3(5) .
C60 C61 C62 122.9(5) .
C57 C62 C61 122.0(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C10 1.388(3) .
C1 C13 1.388(3) .
C1 C2 1.476(3) .
C2 C3 1.396(3) .
C2 C12 1.395(3) .
C3 C5 1.372(3) .
N4 C9 1.401(3) .
C5 C6 1.385(3) .
C6 C11 1.381(3) .
C6 N3 1.408(3) .
C8 C13 1.378(4) .
C8 C9 1.378(3) .
C9 C14 1.385(3) .
C10 C14 1.374(4) .
C11 C12 1.380(3) .
C15 C25 1.389(3) .
C15 C16 1.391(3) .
C15 C19 1.475(3) .
C16 C21 1.385(3) .
C17 C23 1.377(3) .
C17 C18 1.390(3) .
C18 C24 1.385(3) .
C18 N7 1.395(3) .
C19 C26 1.393(3) .
C19 C23 1.396(3) .
C20 C21 1.369(4) .
C20 C27 1.395(4) .
C20 N8 1.415(3) .
C24 C26 1.380(3) .
C25 C27 1.380(4) .
C29 C36 1.384(4) .
C29 C35 1.385(3) .
C29 C30 1.477(3) .
C30 C33 1.392(3) .
C30 C37 1.400(4) .
N6 C32 1.403(3) .
C32 C38 1.375(4) .
C32 C34 1.387(4) .
C33 C38 1.384(4) .
C34 C37 1.375(4) .
C35 C39 1.382(4) .
C36 C42 1.388(4) .
C39 C40 1.369(4) .
C40 C42 1.380(4) .
C40 N5 1.407(3) .
C43 C47 1.386(3) .
C43 C55 1.395(3) .
C43 C49 1.475(3) .
C44 C46 1.372(3) .
C44 C49 1.393(3) .
N2 C48 1.387(3) .
C46 C48 1.395(3) .
C47 C52 1.380(3) .
C48 C50 1.394(3) .
C49 C51 1.397(3) .
C50 C51 1.380(3) .
C52 C54 1.378(3) .
N1 C54 1.421(3) .
C54 C56 1.379(4) .
C55 C56 1.375(4) .
C57 N9 1.377(6) .
C57 C62 1.387(6) .
C57 C58 1.379(7) .
C60 C59 1.364(6) .
C60 C61 1.374(6) .
C60 C60 1.456(8) 3_775
C58 C59 1.361(7) .
C59 H53 1.01(4) .
C61 C62 1.379(8) .
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
C10 C1 C2 C3 15.0(3) .
C13 C1 C2 C3 -164.9(2) .
C10 C1 C2 C12 -164.1(2) .
C13 C1 C2 C12 16.1(3) .
C12 C2 C3 C5 1.3(3) .
C1 C2 C3 C5 -177.8(2) .
C2 C3 C5 C6 0.3(3) .
C3 C5 C6 C11 -1.7(3) .
C3 C5 C6 N3 -179.5(2) .
C13 C8 C9 C14 0.5(4) .
C13 C8 C9 N4 -176.3(2) .
C13 C1 C10 C14 -0.5(4) .
C2 C1 C10 C14 179.7(2) .
C5 C6 C11 C12 1.4(3) .
N3 C6 C11 C12 179.2(2) .
C6 C11 C12 C2 0.3(4) .
C3 C2 C12 C11 -1.6(3) .
C1 C2 C12 C11 177.5(2) .
C9 C8 C13 C1 -0.5(4) .
C10 C1 C13 C8 0.4(4) .
C2 C1 C13 C8 -179.8(2) .
C1 C10 C14 C9 0.5(4) .
C8 C9 C14 C10 -0.5(4) .
N4 C9 C14 C10 176.2(2) .
C25 C15 C16 C21 1.8(3) .
C19 C15 C16 C21 -179.8(2) .
C23 C17 C18 C24 2.3(3) .
C23 C17 C18 N7 -174.8(2) .
C25 C15 C19 C26 -143.8(2) .
C16 C15 C19 C26 37.8(3) .
C25 C15 C19 C23 39.7(3) .
C16 C15 C19 C23 -138.7(2) .
C27 C20 C21 C16 -3.0(3) .
N8 C20 C21 C16 -179.0(2) .
C15 C16 C21 C20 0.5(3) .
C18 C17 C23 C19 -0.4(4) .
C26 C19 C23 C17 -1.4(3) .
C15 C19 C23 C17 175.3(2) .
C17 C18 C24 C26 -2.5(4) .
N7 C18 C24 C26 174.6(2) .
C16 C15 C25 C27 -1.7(3) .
C19 C15 C25 C27 179.9(2) .
C18 C24 C26 C19 0.7(4) .
C23 C19 C26 C24 1.2(3) .
C15 C19 C26 C24 -175.5(2) .
C15 C25 C27 C20 -0.7(4) .
C21 C20 C27 C25 3.0(4) .
N8 C20 C27 C25 179.2(2) .
C36 C29 C30 C33 -7.8(4) .
C35 C29 C30 C33 169.3(2) .
C36 C29 C30 C37 176.6(2) .
C35 C29 C30 C37 -6.2(3) .
C37 C30 C33 C38 0.9(4) .
C29 C30 C33 C38 -174.9(2) .
C38 C32 C34 C37 1.9(4) .
N6 C32 C34 C37 179.0(2) .
C36 C29 C35 C39 1.2(4) .
C30 C29 C35 C39 -176.1(2) .
C35 C29 C36 C42 -2.8(4) .
C30 C29 C36 C42 174.5(3) .
C32 C34 C37 C30 -0.4(4) .
C33 C30 C37 C34 -1.1(4) .
C29 C30 C37 C34 174.8(2) .
C34 C32 C38 C33 -2.0(4) .
N6 C32 C38 C33 -179.1(2) .
C30 C33 C38 C32 0.6(4) .
C29 C35 C39 C40 1.2(4) .
C35 C39 C40 C42 -2.1(4) .
C35 C39 C40 N5 179.9(2) .
C39 C40 C42 C36 0.6(4) .
N5 C40 C42 C36 178.6(3) .
C29 C36 C42 C40 2.0(5) .
C49 C44 C46 C48 1.1(4) .
C55 C43 C47 C52 2.7(4) .
C49 C43 C47 C52 -178.7(2) .
C44 C46 C48 N2 -175.7(2) .
C44 C46 C48 C50 1.4(4) .
C46 C44 C49 C51 -2.3(4) .
C46 C44 C49 C43 175.6(2) .
C47 C43 C49 C44 -133.1(3) .
C55 C43 C49 C44 45.4(3) .
C47 C43 C49 C51 44.7(3) .
C55 C43 C49 C51 -136.8(3) .
N2 C48 C50 C51 174.4(2) .
C46 C48 C50 C51 -2.7(4) .
C48 C50 C51 C49 1.5(4) .
C44 C49 C51 C50 1.0(4) .
C43 C49 C51 C50 -176.9(2) .
C43 C47 C52 C54 0.2(4) .
C47 C52 C54 C56 -3.7(4) .
C47 C52 C54 N1 178.7(2) .
C47 C43 C55 C56 -2.2(4) .
C49 C43 C55 C56 179.3(2) .
C43 C55 C56 C54 -1.2(4) .
C52 C54 C56 C55 4.2(4) .
N1 C54 C56 C55 -178.2(3) .
N9 C57 C58 C59 177.8(5) .
C62 C57 C58 C59 -0.6(7) .
C57 C58 C59 H53 176(3) .
C57 C58 C59 C60 1.0(8) .
C61 C60 C59 H53 -175(3) .
C60 C60 C59 H53 5(3) 3_775
C61 C60 C59 C58 0.1(7) .
C60 C60 C59 C58 -179.4(5) 3_775
C59 C60 C61 C62 -1.4(7) .
C60 C60 C61 C62 178.2(5) 3_775
N9 C57 C62 C61 -179.1(5) .
C58 C57 C62 C61 -0.6(8) .
C60 C61 C62 C57 1.7(9) .
