#------------------------------------------------------------------------------
#$Date: 2016-03-26 14:51:57 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180279 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/65/7116584.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_7116584
loop_
_publ_author_name
'Takashi Kubo'
'Shogo Miyazaki'
'Takuya Kodama'
'Mitsuya Aoba'
'Yasukazu Hirao'
'Hiroyuki Kurata'
_publ_section_title
;
 A facile synthesis of trinaphtho[3.3.3]propellane and its pi-extension
 and the formation of a two-dimensional honeycomb molecular assembly
;
_journal_name_full               Chem.Commun.
_journal_page_first              3801
_journal_paper_doi               10.1039/C4cc09883H
_journal_volume                  51
_journal_year                    2015
_chemical_formula_moiety         'C50 H24, 1.5(C12 H4 N4), C6 H5 Cl'
_chemical_formula_sum            'C74 H35 Cl N6'
_chemical_formula_weight         1043.53
_chemical_name_systematic        FAP-TCNQ
_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
_audit_update_record
;
2014-12-04 deposited with the CCDC.
2015-01-26 downloaded from the CCDC.
;
_cell_angle_alpha                109.2553(9)
_cell_angle_beta                 90.5719(11)
_cell_angle_gamma                109.4063(8)
_cell_formula_units_Z            2
_cell_length_a                   10.6327(3)
_cell_length_b                   14.0819(4)
_cell_length_c                   19.8579(8)
_cell_measurement_reflns_used    15975
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      54.96
_cell_measurement_theta_min      6.09
_cell_volume                     2623.52(15)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        'teXsan Ver. 2.0'
_computing_publication_material  'teXsan Ver. 2.0'
_computing_structure_refinement  SHELXL97
_computing_structure_solution    SHELXS97
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID Imaging Plate'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_av_sigmaI/netI    0.0697
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            26103
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         3.05
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.321
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1076
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: chlorobenzene'
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.336
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     730
_refine_ls_number_reflns         11925
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.041
_refine_ls_R_factor_all          0.0965
_refine_ls_R_factor_gt           0.0520
_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)+(0.0838P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1319
_refine_ls_wR_factor_ref         0.1668
_reflns_number_gt                6932
_reflns_number_total             11925
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c4cc09883h2.cif
_cod_data_source_block           xsm3x28
_cod_database_code               7116584
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
C1 C 0.58005(19) 0.17340(15) 0.29182(9) 0.0310(4) Uani 1 1 d .
C2 C 0.68409(19) 0.10191(14) 0.27193(9) 0.0304(4) Uani 1 1 d .
C3 C 0.70611(18) 0.08131(14) 0.34097(9) 0.0305(4) Uani 1 1 d .
C4 C 0.77972(19) 0.02959(15) 0.36284(10) 0.0349(4) Uani 1 1 d .
H1 H 0.8305 -0.0034 0.3302 0.042 Uiso 1 1 calc R
C5 C 0.7808(2) 0.02496(15) 0.43335(10) 0.0372(4) Uani 1 1 d .
H2 H 0.8316 -0.0115 0.4470 0.045 Uiso 1 1 calc R
C6 C 0.7086(2) 0.07296(15) 0.48224(10) 0.0353(4) Uani 1 1 d .
C7 C 0.6838(2) 0.08958(15) 0.55741(10) 0.0392(5) Uani 1 1 d .
C8 C 0.7320(2) 0.05901(16) 0.60926(11) 0.0443(5) Uani 1 1 d .
H3 H 0.7916 0.0202 0.5987 0.053 Uiso 1 1 calc R
C9 C 0.6907(2) 0.08669(18) 0.67671(11) 0.0525(6) Uani 1 1 d .
H4 H 0.7227 0.0663 0.7126 0.063 Uiso 1 1 calc R
C10 C 0.6039(2) 0.14346(18) 0.69303(11) 0.0514(6) Uani 1 1 d .
H5 H 0.5776 0.1612 0.7398 0.062 Uiso 1 1 calc R
C11 C 0.5547(2) 0.17490(17) 0.64201(11) 0.0450(5) Uani 1 1 d .
H6 H 0.4951 0.2137 0.6534 0.054 Uiso 1 1 calc R
C12 C 0.5948(2) 0.14839(15) 0.57425(10) 0.0376(5) Uani 1 1 d .
C13 C 0.5614(2) 0.17120(15) 0.50963(10) 0.0348(4) Uani 1 1 d .
C14 C 0.4883(2) 0.22394(16) 0.48941(10) 0.0374(4) Uani 1 1 d .
H7 H 0.4381 0.2568 0.5226 0.045 Uiso 1 1 calc R
C15 C 0.48720(19) 0.22979(15) 0.41862(10) 0.0354(4) Uani 1 1 d .
H8 H 0.4363 0.2666 0.4055 0.042 Uiso 1 1 calc R
C16 C 0.55911(19) 0.18260(14) 0.36932(9) 0.0317(4) Uani 1 1 d .
C17 C 0.63214(18) 0.12857(14) 0.39047(9) 0.0310(4) Uani 1 1 d .
C18 C 0.63378(19) 0.12366(15) 0.45810(10) 0.0332(4) Uani 1 1 d .
C19 C 0.60153(19) 0.00106(14) 0.20961(9) 0.0308(4) Uani 1 1 d .
C20 C 0.6219(2) -0.09195(15) 0.16907(10) 0.0346(4) Uani 1 1 d .
H9 H 0.7059 -0.0992 0.1769 0.041 Uiso 1 1 calc R
C21 C 0.5182(2) -0.17761(15) 0.11535(10) 0.0368(5) Uani 1 1 d .
H10 H 0.5340 -0.2413 0.0886 0.044 Uiso 1 1 calc R
C22 C 0.3954(2) -0.16873(15) 0.10196(9) 0.0340(4) Uani 1 1 d .
C23 C 0.2670(2) -0.23141(16) 0.05306(10) 0.0394(5) Uani 1 1 d .
C24 C 0.2230(3) -0.33186(18) -0.00063(11) 0.0535(6) Uani 1 1 d .
H11 H 0.2782 -0.3745 -0.0106 0.064 Uiso 1 1 calc R
C25 C 0.0959(3) -0.3694(2) -0.03982(13) 0.0645(7) Uani 1 1 d .
H12 H 0.0638 -0.4390 -0.0760 0.077 Uiso 1 1 calc R
C26 C 0.0163(3) -0.3075(2) -0.02702(13) 0.0632(7) Uani 1 1 d .
H13 H -0.0686 -0.3341 -0.0556 0.076 Uiso 1 1 calc R
C27 C 0.0576(2) -0.20708(19) 0.02680(11) 0.0499(6) Uani 1 1 d .
H14 H 0.0014 -0.1653 0.0356 0.060 Uiso 1 1 calc R
C28 C 0.1826(2) -0.16859(16) 0.06760(10) 0.0381(5) Uani 1 1 d .
C29 C 0.25414(19) -0.06573(16) 0.12703(9) 0.0346(4) Uani 1 1 d .
C30 C 0.2321(2) 0.02719(16) 0.16713(10) 0.0369(5) Uani 1 1 d .
H15 H 0.1489 0.0348 0.1577 0.044 Uiso 1 1 calc R
C31 C 0.33264(19) 0.11149(16) 0.22233(10) 0.0355(4) Uani 1 1 d .
H16 H 0.3152 0.1742 0.2496 0.043 Uiso 1 1 calc R
C32 C 0.45548(19) 0.10326(15) 0.23679(9) 0.0310(4) Uani 1 1 d .
C33 C 0.47666(19) 0.00923(14) 0.19531(9) 0.0301(4) Uani 1 1 d .
C34 C 0.80843(19) 0.17790(14) 0.25482(9) 0.0305(4) Uani 1 1 d .
C35 C 0.92989(19) 0.17166(15) 0.23441(10) 0.0346(4) Uani 1 1 d .
H17 H 0.9485 0.1083 0.2292 0.042 Uiso 1 1 calc R
C36 C 1.0289(2) 0.25960(15) 0.22091(10) 0.0360(4) Uani 1 1 d .
H18 H 1.1119 0.2536 0.2068 0.043 Uiso 1 1 calc R
C37 C 1.00424(19) 0.35238(15) 0.22824(9) 0.0330(4) Uani 1 1 d .
C38 C 1.06910(19) 0.45567(15) 0.21654(10) 0.0346(4) Uani 1 1 d .
C39 C 1.1896(2) 0.49579(16) 0.19101(10) 0.0412(5) Uani 1 1 d .
H19 H 1.2501 0.4576 0.1815 0.049 Uiso 1 1 calc R
C40 C 1.2196(2) 0.59275(17) 0.17981(12) 0.0470(5) Uani 1 1 d .
H20 H 1.3004 0.6200 0.1613 0.056 Uiso 1 1 calc R
C41 C 1.1340(2) 0.65063(17) 0.19511(12) 0.0487(5) Uani 1 1 d .
H21 H 1.1566 0.7165 0.1867 0.058 Uiso 1 1 calc R
C42 C 1.0151(2) 0.61320(16) 0.22273(11) 0.0421(5) Uani 1 1 d .
H22 H 0.9581 0.6542 0.2346 0.051 Uiso 1 1 calc R
C43 C 0.9812(2) 0.51541(15) 0.23259(10) 0.0354(4) Uani 1 1 d .
C44 C 0.8584(2) 0.45188(15) 0.25507(10) 0.0355(4) Uani 1 1 d .
C45 C 0.7371(2) 0.45924(16) 0.27481(11) 0.0390(5) Uani 1 1 d .
H23 H 0.7192 0.5227 0.2796 0.047 Uiso 1 1 calc R
C46 C 0.6377(2) 0.37214(15) 0.28826(10) 0.0374(5) Uani 1 1 d .
H24 H 0.5545 0.3785 0.3015 0.045 Uiso 1 1 calc R
C47 C 0.66111(19) 0.27927(14) 0.28226(9) 0.0317(4) Uani 1 1 d .
C48 C 0.78570(19) 0.27333(14) 0.26265(9) 0.0304(4) Uani 1 1 d .
C49 C 0.87997(19) 0.35652(15) 0.25003(10) 0.0335(4) Uani 1 1 d .
N1 N 0.3166(3) 0.2730(2) 0.08920(16) 0.0970(9) Uani 1 1 d .
C50 C 0.3082(3) 0.1883(2) 0.05345(15) 0.0655(7) Uani 1 1 d .
C51 C 0.2931(3) 0.0821(2) 0.00634(12) 0.0538(6) Uani 1 1 d .
C52 C 0.1668(3) 0.0226(2) -0.03904(13) 0.0574(7) Uani 1 1 d .
N2 N 0.0661(3) -0.0217(2) -0.07492(12) 0.0773(7) Uani 1 1 d .
C53 C 0.3955(2) 0.04148(18) 0.00351(11) 0.0472(6) Uani 1 1 d .
C54 C 0.5207(2) 0.10304(19) 0.04985(12) 0.0504(6) Uani 1 1 d .
H25 H 0.5330 0.1724 0.0837 0.060 Uiso 1 1 calc R
C55 C 0.3789(2) -0.06400(19) -0.04611(11) 0.0500(6) Uani 1 1 d .
H26 H 0.2960 -0.1067 -0.0766 0.060 Uiso 1 1 calc R
N3 N 0.3648(2) 0.44080(18) 0.54257(12) 0.0649(6) Uani 1 1 d .
C56 C 0.3294(2) 0.46964(19) 0.50094(13) 0.0501(6) Uani 1 1 d .
C57 C 0.2814(2) 0.50282(18) 0.44827(11) 0.0477(5) Uani 1 1 d .
C58 C 0.3221(2) 0.4689(2) 0.37834(13) 0.0642(7) Uani 1 1 d .
N4 N 0.3527(3) 0.4416(3) 0.32213(13) 0.0954(9) Uani 1 1 d .
C59 C 0.2011(2) 0.56446(16) 0.46379(11) 0.0418(5) Uani 1 1 d .
C60 C 0.1608(2) 0.59863(16) 0.53429(11) 0.0401(5) Uani 1 1 d .
H27 H 0.1915 0.5797 0.5714 0.048 Uiso 1 1 calc R
C61 C 0.0802(2) 0.65691(16) 0.54821(11) 0.0403(5) Uani 1 1 d .
H28 H 0.0550 0.6787 0.5950 0.048 Uiso 1 1 calc R
C62 C 0.0315(2) 0.68685(16) 0.49324(11) 0.0407(5) Uani 1 1 d .
C63 C 0.0742(2) 0.65418(17) 0.42327(11) 0.0464(5) Uani 1 1 d .
H29 H 0.0453 0.6745 0.3865 0.056 Uiso 1 1 calc R
C64 C 0.1542(2) 0.59549(18) 0.40915(11) 0.0458(5) Uani 1 1 d .
H30 H 0.1800 0.5742 0.3624 0.055 Uiso 1 1 calc R
N5 N -0.1421(2) 0.8019(2) 0.62782(13) 0.0823(8) Uani 1 1 d .
C65 C -0.1006(2) 0.7774(2) 0.57424(14) 0.0576(6) Uani 1 1 d .
C66 C -0.0524(2) 0.74475(18) 0.50643(12) 0.0492(5) Uani 1 1 d .
C67 C -0.1003(3) 0.7751(2) 0.45194(15) 0.0657(7) Uani 1 1 d .
N6 N -0.1384(3) 0.7982(2) 0.40815(14) 0.0991(9) Uani 1 1 d .
Cl1 Cl 0.06733(7) 0.15477(6) 0.78989(4) 0.0734(2) Uani 1 1 d .
C68 C 0.2137(2) 0.2678(2) 0.81960(15) 0.0587(6) Uani 1 1 d .
C69 C 0.2375(3) 0.3330(3) 0.89017(17) 0.0756(8) Uani 1 1 d .
H31 H 0.1761 0.3168 0.9227 0.091 Uiso 1 1 calc R
C70 C 0.3557(4) 0.4251(3) 0.9134(2) 0.0954(11) Uani 1 1 d .
H32 H 0.3746 0.4721 0.9623 0.114 Uiso 1 1 calc R
C71 C 0.4429(3) 0.4471(3) 0.8662(2) 0.0907(11) Uani 1 1 d .
H33 H 0.5224 0.5093 0.8822 0.109 Uiso 1 1 calc R
C72 C 0.4162(3) 0.3792(3) 0.7952(2) 0.0788(9) Uani 1 1 d .
H34 H 0.4777 0.3948 0.7626 0.095 Uiso 1 1 calc R
C73 C 0.3004(3) 0.2886(2) 0.77128(16) 0.0663(7) Uani 1 1 d .
H35 H 0.2814 0.2418 0.7224 0.080 Uiso 1 1 calc R
C74 C 0.37855(19) -0.07213(15) 0.14332(9) 0.0320(4) 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'
Cl Cl 0.1484 0.1585 '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
C32 C1 C16 114.56(15) .
C32 C1 C47 115.07(15) .
C16 C1 C47 114.83(15) .
C32 C1 C2 103.53(13) .
C16 C1 C2 103.32(13) .
C47 C1 C2 103.27(13) .
C19 C2 C34 116.51(14) .
C19 C2 C3 113.58(15) .
C34 C2 C3 114.36(15) .
C19 C2 C1 103.22(14) .
C34 C2 C1 103.52(13) .
C3 C2 C1 103.37(13) .
C4 C3 C17 117.72(16) .
C4 C3 C2 134.69(16) .
C17 C3 C2 107.59(14) .
C3 C4 C5 121.17(16) .
C3 C4 H1 119.4 .
C5 C4 H1 119.4 .
C6 C5 C4 120.75(17) .
C6 C5 H2 119.6 .
C4 C5 H2 119.6 .
C5 C6 C18 116.65(17) .
C5 C6 C7 138.80(18) .
C18 C6 C7 104.55(16) .
C8 C7 C12 120.18(17) .
C8 C7 C6 131.26(19) .
C12 C7 C6 108.56(16) .
C9 C8 C7 118.3(2) .
C9 C8 H3 120.9 .
C7 C8 H3 120.9 .
C8 C9 C10 121.6(2) .
C8 C9 H4 119.2 .
C10 C9 H4 119.2 .
C9 C10 C11 121.06(19) .
C9 C10 H5 119.5 .
C11 C10 H5 119.5 .
C12 C11 C10 118.4(2) .
C12 C11 H6 120.8 .
C10 C11 H6 120.8 .
C11 C12 C7 120.47(18) .
C11 C12 C13 131.01(19) .
C7 C12 C13 108.52(15) .
C14 C13 C18 117.29(17) .
C14 C13 C12 139.03(17) .
C18 C13 C12 103.65(16) .
C13 C14 C15 120.54(16) .
C13 C14 H7 119.7 .
C15 C14 H7 119.7 .
C16 C15 C14 120.90(17) .
C16 C15 H8 119.5 .
C14 C15 H8 119.5 .
C15 C16 C17 117.89(16) .
C15 C16 C1 134.59(16) .
C17 C16 C1 107.52(14) .
C18 C17 C16 121.13(16) .
C18 C17 C3 120.67(16) .
C16 C17 C3 118.19(16) .
C17 C18 C6 123.04(16) .
C17 C18 C13 122.24(17) .
C6 C18 C13 114.71(16) .
C20 C19 C33 117.57(17) .
C20 C19 C2 134.48(17) .
C33 C19 C2 107.89(15) .
C19 C20 C21 121.03(18) .
C19 C20 H9 119.5 .
C21 C20 H9 119.5 .
C22 C21 C20 120.83(16) .
C22 C21 H10 119.6 .
C20 C21 H10 119.6 .
C21 C22 C74 116.81(18) .
C21 C22 C23 139.20(17) .
C74 C22 C23 103.96(16) .
C24 C23 C28 120.0(2) .
C24 C23 C22 131.6(2) .
C28 C23 C22 108.36(16) .
C23 C24 C25 118.7(2) .
C23 C24 H11 120.7 .
C25 C24 H11 120.7 .
C26 C25 C24 121.2(2) .
C26 C25 H12 119.4 .
C24 C25 H12 119.4 .
C25 C26 C27 121.2(2) .
C25 C26 H13 119.4 .
C27 C26 H13 119.4 .
C26 C27 C28 118.8(2) .
C26 C27 H14 120.6 .
C28 C27 H14 120.6 .
C27 C28 C23 120.08(19) .
C27 C28 C29 131.31(19) .
C23 C28 C29 108.59(18) .
C30 C29 C74 116.96(18) .
C30 C29 C28 138.86(19) .
C74 C29 C28 104.18(16) .
C29 C30 C31 120.86(17) .
C29 C30 H15 119.6 .
C31 C30 H15 119.6 .
C32 C31 C30 120.86(16) .
C32 C31 H16 119.6 .
C30 C31 H16 119.6 .
C31 C32 C33 117.57(17) .
C31 C32 C1 134.72(16) .
C33 C32 C1 107.66(15) .
C74 C33 C32 121.12(17) .
C74 C33 C19 121.24(16) .
C32 C33 C19 117.64(17) .
C35 C34 C48 117.59(17) .
C35 C34 C2 134.57(15) .
C48 C34 C2 107.84(15) .
C34 C35 C36 121.06(16) .
C34 C35 H17 119.5 .
C36 C35 H17 119.5 .
C37 C36 C35 120.51(17) .
C37 C36 H18 119.7 .
C35 C36 H18 119.7 .
C36 C37 C49 116.91(17) .
C36 C37 C38 138.87(17) .
C49 C37 C38 104.15(15) .
C39 C38 C43 120.05(18) .
C39 C38 C37 131.40(18) .
C43 C38 C37 108.47(16) .
C40 C39 C38 118.58(19) .
C40 C39 H19 120.7 .
C38 C39 H19 120.7 .
C41 C40 C39 121.39(19) .
C41 C40 H20 119.3 .
C39 C40 H20 119.3 .
C40 C41 C42 120.69(19) .
C40 C41 H21 119.7 .
C42 C41 H21 119.7 .
C43 C42 C41 119.04(19) .
C43 C42 H22 120.5 .
C41 C42 H22 120.5 .
C42 C43 C38 120.19(18) .
C42 C43 C44 131.12(18) .
C38 C43 C44 108.61(16) .
C45 C44 C49 117.06(17) .
C45 C44 C43 138.78(17) .
C49 C44 C43 104.08(16) .
C44 C45 C46 120.70(17) .
C44 C45 H23 119.6 .
C46 C45 H23 119.6 .
C47 C46 C45 120.98(17) .
C47 C46 H24 119.5 .
C45 C46 H24 119.5 .
C46 C47 C48 117.65(17) .
C46 C47 C1 134.73(17) .
C48 C47 C1 107.63(14) .
C49 C48 C34 121.13(16) .
C49 C48 C47 121.12(16) .
C34 C48 C47 117.73(17) .
C48 C49 C37 122.80(16) .
C48 C49 C44 122.48(17) .
C37 C49 C44 114.68(17) .
N1 C50 C51 177.4(3) .
C53 C51 C52 122.4(2) .
C53 C51 C50 122.0(2) .
C52 C51 C50 115.5(2) .
N2 C52 C51 177.8(3) .
C51 C53 C54 121.0(2) .
C51 C53 C55 120.7(2) .
C54 C53 C55 118.26(19) .
C55 C54 C53 120.9(2) 2_655
C55 C54 H25 119.5 2_655
C53 C54 H25 119.5 .
C54 C55 C53 120.8(2) 2_655
C54 C55 H26 119.6 2_655
C53 C55 H26 119.6 .
N3 C56 C57 178.3(3) .
C59 C57 C56 121.98(19) .
C59 C57 C58 121.8(2) .
C56 C57 C58 116.26(19) .
N4 C58 C57 179.0(2) .
C57 C59 C64 120.24(19) .
C57 C59 C60 121.5(2) .
C64 C59 C60 118.23(18) .
C61 C60 C59 120.83(19) .
C61 C60 H27 119.6 .
C59 C60 H27 119.6 .
C60 C61 C62 121.05(18) .
C60 C61 H28 119.5 .
C62 C61 H28 119.5 .
C66 C62 C61 121.60(18) .
C66 C62 C63 120.56(19) .
C61 C62 C63 117.84(18) .
C64 C63 C62 121.2(2) .
C64 C63 H29 119.4 .
C62 C63 H29 119.4 .
C63 C64 C59 120.84(19) .
C63 C64 H30 119.6 .
C59 C64 H30 119.6 .
N5 C65 C66 178.5(3) .
C62 C66 C65 123.1(2) .
C62 C66 C67 121.7(2) .
C65 C66 C67 115.2(2) .
N6 C67 C66 179.3(3) .
C69 C68 C73 122.5(3) .
C69 C68 Cl1 118.6(2) .
C73 C68 Cl1 118.9(2) .
C68 C69 C70 118.1(3) .
C68 C69 H31 120.9 .
C70 C69 H31 120.9 .
C71 C70 C69 120.2(3) .
C71 C70 H32 119.9 .
C69 C70 H32 119.9 .
C70 C71 C72 120.2(3) .
C70 C71 H33 119.9 .
C72 C71 H33 119.9 .
C71 C72 C73 120.4(3) .
C71 C72 H34 119.8 .
C73 C72 H34 119.8 .
C68 C73 C72 118.6(3) .
C68 C73 H35 120.7 .
C72 C73 H35 120.7 .
C33 C74 C29 122.60(16) .
C33 C74 C22 122.50(17) .
C29 C74 C22 114.90(18) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C32 1.521(3) .
C1 C16 1.526(2) .
C1 C47 1.529(3) .
C1 C2 1.697(2) .
C2 C19 1.520(3) .
C2 C34 1.522(3) .
C2 C3 1.523(2) .
C3 C4 1.383(2) .
C3 C17 1.400(2) .
C4 C5 1.423(3) .
C4 H1 0.9500 .
C5 C6 1.384(3) .
C5 H2 0.9500 .
C6 C18 1.402(3) .
C6 C7 1.473(3) .
C7 C8 1.391(3) .
C7 C12 1.428(3) .
C8 C9 1.385(3) .
C8 H3 0.9500 .
C9 C10 1.386(3) .
C9 H4 0.9500 .
C10 C11 1.391(3) .
C10 H5 0.9500 .
C11 C12 1.384(3) .
C11 H6 0.9500 .
C12 C13 1.488(3) .
C13 C14 1.375(3) .
C13 C18 1.412(2) .
C14 C15 1.435(3) .
C14 H7 0.9500 .
C15 C16 1.381(2) .
C15 H8 0.9500 .
C16 C17 1.398(2) .
C17 C18 1.368(2) .
C19 C20 1.381(2) .
C19 C33 1.404(2) .
C20 C21 1.433(3) .
C20 H9 0.9500 .
C21 C22 1.383(3) .
C21 H10 0.9500 .
C22 C74 1.409(2) .
C22 C23 1.482(3) .
C23 C24 1.383(3) .
C23 C28 1.427(3) .
C24 C25 1.394(3) .
C24 H11 0.9500 .
C25 C26 1.374(3) .
C25 H12 0.9500 .
C26 C27 1.384(3) .
C26 H13 0.9500 .
C27 C28 1.388(3) .
C27 H14 0.9500 .
C28 C29 1.481(3) .
C29 C30 1.386(3) .
C29 C74 1.397(3) .
C30 C31 1.424(3) .
C30 H15 0.9500 .
C31 C32 1.385(3) .
C31 H16 0.9500 .
C32 C33 1.402(2) .
C33 C74 1.368(3) .
C34 C35 1.379(2) .
C34 C48 1.403(2) .
C35 C36 1.440(3) .
C35 H17 0.9500 .
C36 C37 1.379(3) .
C36 H18 0.9500 .
C37 C49 1.408(2) .
C37 C38 1.485(3) .
C38 C39 1.393(3) .
C38 C43 1.427(3) .
C39 C40 1.389(3) .
C39 H19 0.9500 .
C40 C41 1.386(3) .
C40 H20 0.9500 .
C41 C42 1.392(3) .
C41 H21 0.9500 .
C42 C43 1.383(3) .
C42 H22 0.9500 .
C43 C44 1.484(3) .
C44 C45 1.378(3) .
C44 C49 1.408(2) .
C45 C46 1.433(3) .
C45 H23 0.9500 .
C46 C47 1.379(2) .
C46 H24 0.9500 .
C47 C48 1.406(2) .
C48 C49 1.363(3) .
N1 C50 1.142(3) .
C50 C51 1.432(4) .
C51 C53 1.383(3) .
C51 C52 1.431(4) .
C52 N2 1.136(3) .
C53 C54 1.432(3) .
C53 C55 1.437(3) .
C54 C55 1.346(3) 2_655
C54 H25 0.9500 .
C55 C54 1.346(3) 2_655
C55 H26 0.9500 .
N3 C56 1.143(3) .
C56 C57 1.429(3) .
C57 C59 1.378(3) .
C57 C58 1.434(3) .
C58 N4 1.143(3) .
C59 C64 1.437(3) .
C59 C60 1.442(3) .
C60 C61 1.344(3) .
C60 H27 0.9500 .
C61 C62 1.440(3) .
C61 H28 0.9500 .
C62 C66 1.370(3) .
C62 C63 1.442(3) .
C63 C64 1.342(3) .
C63 H29 0.9500 .
C64 H30 0.9500 .
N5 C65 1.146(3) .
C65 C66 1.432(3) .
C66 C67 1.433(3) .
C67 N6 1.137(3) .
Cl1 C68 1.738(3) .
C68 C69 1.364(4) .
C68 C73 1.371(3) .
C69 C70 1.409(4) .
C69 H31 0.9500 .
C70 C71 1.361(4) .
C70 H32 0.9500 .
C71 C72 1.381(4) .
C71 H33 0.9500 .
C72 C73 1.383(4) .
C72 H34 0.9500 .
C73 H35 0.9500 .
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_4
C32 C1 C2 C19 -1.09(16) .
C16 C1 C2 C19 118.66(15) .
C47 C1 C2 C19 -121.39(15) .
C32 C1 C2 C34 120.79(15) .
C16 C1 C2 C34 -119.46(15) .
C47 C1 C2 C34 0.49(17) .
C32 C1 C2 C3 -119.66(15) .
C16 C1 C2 C3 0.09(18) .
C47 C1 C2 C3 120.04(15) .
C19 C2 C3 C4 69.6(3) .
C34 C2 C3 C4 -67.5(3) .
C1 C2 C3 C4 -179.3(2) .
C19 C2 C3 C17 -110.80(17) .
C34 C2 C3 C17 112.12(17) .
C1 C2 C3 C17 0.32(19) .
C17 C3 C4 C5 -0.3(3) .
C2 C3 C4 C5 179.3(2) .
C3 C4 C5 C6 -0.5(3) .
C4 C5 C6 C18 1.1(3) .
C4 C5 C6 C7 -178.4(2) .
C5 C6 C7 C8 0.5(4) .
C18 C6 C7 C8 -179.0(2) .
C5 C6 C7 C12 -179.9(2) .
C18 C6 C7 C12 0.5(2) .
C12 C7 C8 C9 0.3(3) .
C6 C7 C8 C9 179.8(2) .
C7 C8 C9 C10 -0.1(3) .
C8 C9 C10 C11 0.0(4) .
C9 C10 C11 C12 -0.2(3) .
C10 C11 C12 C7 0.4(3) .
C10 C11 C12 C13 -179.3(2) .
C8 C7 C12 C11 -0.5(3) .
C6 C7 C12 C11 179.93(18) .
C8 C7 C12 C13 179.25(18) .
C6 C7 C12 C13 -0.4(2) .
C11 C12 C13 C14 1.8(4) .
C7 C12 C13 C14 -177.9(2) .
C11 C12 C13 C18 179.7(2) .
C7 C12 C13 C18 0.1(2) .
C18 C13 C14 C15 -0.2(3) .
C12 C13 C14 C15 177.6(2) .
C13 C14 C15 C16 0.1(3) .
C14 C15 C16 C17 0.4(3) .
C14 C15 C16 C1 -180.0(2) .
C32 C1 C16 C15 -68.3(3) .
C47 C1 C16 C15 68.2(3) .
C2 C1 C16 C15 179.9(2) .
C32 C1 C16 C17 111.41(17) .
C47 C1 C16 C17 -112.15(18) .
C2 C1 C16 C17 -0.47(19) .
C15 C16 C17 C18 -0.8(3) .
C1 C16 C17 C18 179.47(17) .
C15 C16 C17 C3 -179.49(17) .
C1 C16 C17 C3 0.8(2) .
C4 C3 C17 C18 0.3(3) .
C2 C3 C17 C18 -179.41(17) .
C4 C3 C17 C16 178.97(17) .
C2 C3 C17 C16 -0.7(2) .
C16 C17 C18 C6 -178.18(19) .
C3 C17 C18 C6 0.5(3) .
C16 C17 C18 C13 0.8(3) .
C3 C17 C18 C13 179.42(18) .
C5 C6 C18 C17 -1.2(3) .
C7 C6 C18 C17 178.50(18) .
C5 C6 C18 C13 179.81(17) .
C7 C6 C18 C13 -0.5(2) .
C14 C13 C18 C17 -0.3(3) .
C12 C13 C18 C17 -178.73(18) .
C14 C13 C18 C6 178.77(18) .
C12 C13 C18 C6 0.3(2) .
C34 C2 C19 C20 69.8(3) .
C3 C2 C19 C20 -66.3(3) .
C1 C2 C19 C20 -177.48(18) .
C34 C2 C19 C33 -112.91(16) .
C3 C2 C19 C33 110.98(16) .
C1 C2 C19 C33 -0.24(17) .
C33 C19 C20 C21 -1.1(3) .
C2 C19 C20 C21 175.93(17) .
C19 C20 C21 C22 0.9(3) .
C20 C21 C22 C74 0.2(3) .
C20 C21 C22 C23 177.8(2) .
C21 C22 C23 C24 1.3(4) .
C74 C22 C23 C24 179.1(2) .
C21 C22 C23 C28 -177.2(2) .
C74 C22 C23 C28 0.54(19) .
C28 C23 C24 C25 0.2(3) .
C22 C23 C24 C25 -178.2(2) .
C23 C24 C25 C26 1.5(4) .
C24 C25 C26 C27 -2.1(4) .
C25 C26 C27 C28 0.8(4) .
C26 C27 C28 C23 1.0(3) .
C26 C27 C28 C29 179.0(2) .
C24 C23 C28 C27 -1.5(3) .
C22 C23 C28 C27 177.23(18) .
C24 C23 C28 C29 -179.95(18) .
C22 C23 C28 C29 -1.2(2) .
C27 C28 C29 C30 3.0(4) .
C23 C28 C29 C30 -178.8(2) .
C27 C28 C29 C74 -176.8(2) .
C23 C28 C29 C74 1.4(2) .
C74 C29 C30 C31 -0.1(3) .
C28 C29 C30 C31 -179.9(2) .
C29 C30 C31 C32 0.7(3) .
C30 C31 C32 C33 -0.1(3) .
C30 C31 C32 C1 -177.27(18) .
C16 C1 C32 C31 67.6(3) .
C47 C1 C32 C31 -68.7(3) .
C2 C1 C32 C31 179.39(19) .
C16 C1 C32 C33 -109.71(16) .
C47 C1 C32 C33 113.95(16) .
C2 C1 C32 C33 2.03(17) .
C31 C32 C33 C74 -1.1(3) .
C1 C32 C33 C74 176.77(15) .
C31 C32 C33 C19 179.60(15) .
C1 C32 C33 C19 -2.5(2) .
C20 C19 C33 C74 0.2(3) .
C2 C19 C33 C74 -177.55(15) .
C20 C19 C33 C32 179.52(15) .
C2 C19 C33 C32 1.7(2) .
C19 C2 C34 C35 -67.1(3) .
C3 C2 C34 C35 68.7(3) .
C1 C2 C34 C35 -179.6(2) .
C19 C2 C34 C48 112.66(17) .
C3 C2 C34 C48 -111.56(16) .
C1 C2 C34 C48 0.15(18) .
C48 C34 C35 C36 -0.7(3) .
C2 C34 C35 C36 179.08(19) .
C34 C35 C36 C37 0.1(3) .
C35 C36 C37 C49 0.7(3) .
C35 C36 C37 C38 -175.5(2) .
C36 C37 C38 C39 0.4(4) .
C49 C37 C38 C39 -176.0(2) .
C36 C37 C38 C43 177.1(2) .
C49 C37 C38 C43 0.6(2) .
C43 C38 C39 C40 -1.8(3) .
C37 C38 C39 C40 174.49(19) .
C38 C39 C40 C41 1.6(3) .
C39 C40 C41 C42 0.4(3) .
C40 C41 C42 C43 -2.1(3) .
C41 C42 C43 C38 1.8(3) .
C41 C42 C43 C44 -174.5(2) .
C39 C38 C43 C42 0.1(3) .
C37 C38 C43 C42 -176.93(18) .
C39 C38 C43 C44 177.21(17) .
C37 C38 C43 C44 0.1(2) .
C42 C43 C44 C45 -0.8(4) .
C38 C43 C44 C45 -177.4(2) .
C42 C43 C44 C49 175.8(2) .
C38 C43 C44 C49 -0.8(2) .
C49 C44 C45 C46 -1.0(3) .
C43 C44 C45 C46 175.3(2) .
C44 C45 C46 C47 0.4(3) .
C45 C46 C47 C48 0.1(3) .
C45 C46 C47 C1 -179.51(19) .
C32 C1 C47 C46 66.6(3) .
C16 C1 C47 C46 -69.6(3) .
C2 C1 C47 C46 178.7(2) .
C32 C1 C47 C48 -113.02(17) .
C16 C1 C47 C48 110.76(17) .
C2 C1 C47 C48 -0.95(18) .
C35 C34 C48 C49 0.5(3) .
C2 C34 C48 C49 -179.36(17) .
C35 C34 C48 C47 178.95(16) .
C2 C34 C48 C47 -0.9(2) .
C46 C47 C48 C49 0.0(3) .
C1 C47 C48 C49 179.71(16) .
C46 C47 C48 C34 -178.49(17) .
C1 C47 C48 C34 1.2(2) .
C34 C48 C49 C37 0.4(3) .
C47 C48 C49 C37 -178.08(17) .
C34 C48 C49 C44 177.82(17) .
C47 C48 C49 C44 -0.6(3) .
C36 C37 C49 C48 -0.9(3) .
C38 C37 C49 C48 176.46(17) .
C36 C37 C49 C44 -178.58(17) .
C38 C37 C49 C44 -1.2(2) .
C45 C44 C49 C48 1.1(3) .
C43 C44 C49 C48 -176.38(17) .
C45 C44 C49 C37 178.75(17) .
C43 C44 C49 C37 1.3(2) .
N1 C50 C51 C53 153(7) .
N1 C50 C51 C52 -25(7) .
C53 C51 C52 N2 -152(7) .
C50 C51 C52 N2 26(7) .
C52 C51 C53 C54 -179.79(19) .
C50 C51 C53 C54 2.3(3) .
C52 C51 C53 C55 0.1(3) .
C50 C51 C53 C55 -177.8(2) .
C51 C53 C54 C55 -178.84(19) 2_655
C55 C53 C54 C55 1.3(3) 2_655
C51 C53 C55 C54 178.84(19) 2_655
C54 C53 C55 C54 -1.3(3) 2_655
N3 C56 C57 C59 89(8) .
N3 C56 C57 C58 -91(8) .
C59 C57 C58 N4 -38(20) .
C56 C57 C58 N4 142(20) .
C56 C57 C59 C64 -179.5(2) .
C58 C57 C59 C64 0.8(3) .
C56 C57 C59 C60 -0.2(3) .
C58 C57 C59 C60 -179.8(2) .
C57 C59 C60 C61 -178.7(2) .
C64 C59 C60 C61 0.7(3) .
C59 C60 C61 C62 0.1(3) .
C60 C61 C62 C66 178.9(2) .
C60 C61 C62 C63 -1.3(3) .
C66 C62 C63 C64 -178.6(2) .
C61 C62 C63 C64 1.6(3) .
C62 C63 C64 C59 -0.8(3) .
C57 C59 C64 C63 179.0(2) .
C60 C59 C64 C63 -0.4(3) .
C61 C62 C66 C65 -1.7(3) .
C63 C62 C66 C65 178.5(2) .
C61 C62 C66 C67 179.6(2) .
C63 C62 C66 C67 -0.2(3) .
N5 C65 C66 C62 -112(11) .
N5 C65 C66 C67 67(11) .
C62 C66 C67 N6 39(28) .
C65 C66 C67 N6 -140(28) .
C73 C68 C69 C70 0.3(4) .
Cl1 C68 C69 C70 -179.3(2) .
C68 C69 C70 C71 -0.2(4) .
C69 C70 C71 C72 -0.1(5) .
C70 C71 C72 C73 0.3(4) .
C69 C68 C73 C72 -0.1(4) .
Cl1 C68 C73 C72 179.50(18) .
C71 C72 C73 C68 -0.3(4) .
C32 C33 C74 C29 1.8(3) .
C19 C33 C74 C29 -178.95(16) .
C32 C33 C74 C22 -178.37(16) .
C19 C33 C74 C22 0.9(3) .
C30 C29 C74 C33 -1.1(3) .
C28 C29 C74 C33 178.75(16) .
C30 C29 C74 C22 179.02(16) .
C28 C29 C74 C22 -1.1(2) .
C21 C22 C74 C33 -1.1(3) .
C23 C22 C74 C33 -179.47(16) .
C21 C22 C74 C29 178.77(15) .
C23 C22 C74 C29 0.4(2) .
