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#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/76/4027686.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_4027686
loop_
_publ_author_name
'Yi-Xin Fang'
'Liang Zhao'
'De-Xian Wang'
'Mei-Xiang Wang'
_publ_section_title
;
 Synthesis, Structure and Metal Binding Property of Internally
 1,3-Arylene-Bridged Azacalix[6]aromatics
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              10073
_journal_page_last               10082
_journal_paper_doi               10.1021/jo301528f
_journal_volume                  77
_journal_year                    2012
_chemical_formula_sum            'C40.25 H34.5 Cl0.5 N12'
_chemical_formula_weight         704.02
_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                109.330(8)
_cell_angle_beta                 101.227(7)
_cell_angle_gamma                98.434(7)
_cell_formula_units_Z            2
_cell_length_a                   10.6023(9)
_cell_length_b                   13.3109(12)
_cell_length_c                   13.4391(12)
_cell_measurement_temperature    100
_cell_volume                     1709.2(3)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_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  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0562
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            8335
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9697
_exptl_absorpt_correction_T_min  0.9407
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             737
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.689
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.077
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.007
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     486
_refine_ls_number_reflns         8336
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.007
_refine_ls_R_factor_all          0.0783
_refine_ls_R_factor_gt           0.0602
_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)+(0.0500P)²+2.8500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1396
_refine_ls_wR_factor_ref         0.1458
_reflns_number_gt                6515
_reflns_number_total             8335
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo301528f_si_002_2.cif
_cod_data_source_block           Compound2
_cod_original_formula_sum        'C40.25 H34.50 Cl0.50 N12'
_cod_database_code               4027686
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
N4 N 0.3216(3) 0.2669(2) 0.2578(2) 0.0167(6) Uani 1 1 d .
N6 N 0.5673(2) 0.5128(2) 0.3014(2) 0.0156(6) Uani 1 1 d .
N7 N 0.5587(2) 0.6597(2) 0.2493(2) 0.0162(6) Uani 1 1 d .
N2 N 0.0938(2) 0.3756(2) 0.2383(2) 0.0164(6) Uani 1 1 d .
N5 N 0.5434(3) 0.3564(2) 0.3406(2) 0.0170(6) Uani 1 1 d .
N8 N 0.5355(3) 0.8066(2) 0.2002(2) 0.0153(6) Uani 1 1 d .
N1 N 0.1089(3) 0.5587(2) 0.2756(2) 0.0162(6) Uani 1 1 d .
N10 N 0.3119(3) 0.9346(2) 0.2218(2) 0.0200(6) Uani 1 1 d .
C24 C 0.6188(3) 0.7541(2) 0.2366(3) 0.0161(7) Uani 1 1 d .
C23 C 0.6174(3) 0.6192(2) 0.3273(3) 0.0160(7) Uani 1 1 d .
C19 C 0.6036(3) 0.4664(3) 0.3736(3) 0.0159(7) Uani 1 1 d .
N12 N 0.1184(3) 0.7396(2) 0.3014(2) 0.0174(6) Uani 1 1 d .
N11 N 0.1491(3) 0.9195(2) 0.3145(2) 0.0222(7) Uani 1 1 d .
C16 C 0.4556(3) 0.3030(2) 0.1436(3) 0.0168(7) Uani 1 1 d .
H16 H 0.5373 0.3329 0.1373 0.020 Uiso 1 1 calc R
C8 C -0.0879(3) 0.4480(3) 0.2897(3) 0.0198(7) Uani 1 1 d .
H8 H -0.1262 0.5076 0.3110 0.024 Uiso 1 1 calc R
C37 C 0.0940(3) 0.8717(3) 0.4639(3) 0.0221(8) Uani 1 1 d .
H37 H 0.0950 0.9436 0.5047 0.026 Uiso 1 1 calc R
N3 N 0.0950(3) 0.1927(2) 0.1905(2) 0.0193(6) Uani 1 1 d .
C13 C 0.2201(3) 0.2225(2) 0.1697(3) 0.0181(7) Uani 1 1 d .
C17 C 0.4375(3) 0.3077(2) 0.2450(3) 0.0161(7) Uani 1 1 d .
C6 C 0.3321(3) 0.6086(2) 0.2576(3) 0.0141(7) Uani 1 1 d .
H6 H 0.3607 0.6417 0.3333 0.017 Uiso 1 1 calc R
C21 C 0.7493(3) 0.6339(3) 0.4967(3) 0.0210(8) Uani 1 1 d .
H21 H 0.8120 0.6751 0.5623 0.025 Uiso 1 1 calc R
C25 C 0.7557(3) 0.7893(3) 0.2603(3) 0.0202(8) Uani 1 1 d .
H25 H 0.8123 0.7493 0.2828 0.024 Uiso 1 1 calc R
C18 C 0.5483(3) 0.3075(3) 0.4237(3) 0.0222(8) Uani 1 1 d .
H18A H 0.6373 0.3030 0.4504 0.033 Uiso 1 1 calc R
H18B H 0.4918 0.2354 0.3922 0.033 Uiso 1 1 calc R
H18C H 0.5189 0.3519 0.4831 0.033 Uiso 1 1 calc R
C38 C 0.0673(3) 0.7892(3) 0.5015(3) 0.0187(7) Uani 1 1 d .
H38 H 0.0471 0.8056 0.5686 0.022 Uiso 1 1 calc R
N9 N 0.4893(3) 0.9450(2) 0.1421(2) 0.0202(6) Uani 1 1 d .
C2 C 0.1570(3) 0.5072(3) 0.0951(3) 0.0191(7) Uani 1 1 d .
H2 H 0.0691 0.4712 0.0612 0.023 Uiso 1 1 calc R
C1 C 0.1987(3) 0.5565(2) 0.2074(3) 0.0137(7) Uani 1 1 d .
C22 C 0.7115(3) 0.6826(3) 0.4242(3) 0.0191(8) Uani 1 1 d .
H22 H 0.7477 0.7558 0.4394 0.023 Uiso 1 1 calc R
C7 C 0.0356(3) 0.4583(3) 0.2690(3) 0.0164(7) Uani 1 1 d .
C27 C 0.7189(3) 0.9439(3) 0.2130(3) 0.0197(8) Uani 1 1 d .
H27 H 0.7506 1.0099 0.2068 0.024 Uiso 1 1 calc R
C5 C 0.4205(3) 0.6109(2) 0.1958(3) 0.0146(7) Uani 1 1 d .
C3 C 0.2460(4) 0.5115(3) 0.0333(3) 0.0215(8) Uani 1 1 d .
H3 H 0.2170 0.4791 -0.0424 0.026 Uiso 1 1 calc R
C26 C 0.8033(3) 0.8862(3) 0.2487(3) 0.0218(8) Uani 1 1 d .
H26 H 0.8940 0.9129 0.2654 0.026 Uiso 1 1 calc R
C14 C 0.2276(3) 0.2112(3) 0.0652(3) 0.0192(8) Uani 1 1 d .
H14 H 0.1544 0.1771 0.0056 0.023 Uiso 1 1 calc R
C28 C 0.5839(3) 0.8988(3) 0.1865(3) 0.0179(7) Uani 1 1 d .
C34 C 0.1907(3) 0.8849(3) 0.2164(3) 0.0197(8) Uani 1 1 d .
C9 C -0.1511(3) 0.3440(3) 0.2769(3) 0.0205(8) Uani 1 1 d .
H9 H -0.2337 0.3334 0.2905 0.025 Uiso 1 1 calc R
C30 C 0.3548(3) 0.8990(3) 0.1315(3) 0.0186(7) Uani 1 1 d .
C12 C 0.0254(4) 0.0802(3) 0.1484(3) 0.0283(9) Uani 1 1 d .
H12A H -0.0509 0.0686 0.0906 0.042 Uiso 1 1 calc R
H12B H -0.0018 0.0624 0.2058 0.042 Uiso 1 1 calc R
H12C H 0.0824 0.0344 0.1206 0.042 Uiso 1 1 calc R
C20 C 0.6963(3) 0.5242(3) 0.4748(3) 0.0187(7) Uani 1 1 d .
H20 H 0.7210 0.4911 0.5243 0.022 Uiso 1 1 calc R
C10 C -0.0945(3) 0.2561(3) 0.2445(3) 0.0180(7) Uani 1 1 d .
H10 H -0.1374 0.1864 0.2357 0.022 Uiso 1 1 calc R
C4 C 0.3782(3) 0.5636(3) 0.0824(3) 0.0173(7) Uani 1 1 d .
H4 H 0.4374 0.5668 0.0401 0.021 Uiso 1 1 calc R
C36 C 0.1198(3) 0.8425(3) 0.3612(3) 0.0193(8) Uani 1 1 d .
C31 C 0.2801(3) 0.8186(3) 0.0355(3) 0.0229(8) Uani 1 1 d .
H31 H 0.3139 0.7970 -0.0252 0.028 Uiso 1 1 calc R
C40 C 0.0961(3) 0.6617(2) 0.3421(3) 0.0156(7) Uani 1 1 d .
C32 C 0.1543(4) 0.7705(3) 0.0307(3) 0.0252(8) Uani 1 1 d .
H32 H 0.1010 0.7163 -0.0337 0.030 Uiso 1 1 calc R
C39 C 0.0693(3) 0.6820(3) 0.4431(3) 0.0213(8) Uani 1 1 d .
H39 H 0.0534 0.6267 0.4702 0.026 Uiso 1 1 calc R
C11 C 0.0300(3) 0.2757(3) 0.2252(3) 0.0162(7) Uani 1 1 d .
C29 C 0.5240(4) 1.0582(3) 0.1512(4) 0.0380(10) Uani 1 1 d .
H29A H 0.5632 1.1044 0.2264 0.057 Uiso 1 1 calc R
H29B H 0.4459 1.0798 0.1242 0.057 Uiso 1 1 calc R
H29C H 0.5859 1.0652 0.1090 0.057 Uiso 1 1 calc R
C33 C 0.1076(3) 0.8036(3) 0.1226(3) 0.0215(8) Uani 1 1 d .
H33 H 0.0227 0.7723 0.1216 0.026 Uiso 1 1 calc R
C15 C 0.3499(3) 0.2531(3) 0.0532(3) 0.0202(8) Uani 1 1 d .
H15 H 0.3599 0.2473 -0.0156 0.024 Uiso 1 1 calc R
C35 C 0.1926(4) 1.0350(3) 0.3876(3) 0.0332(10) Uani 1 1 d .
H35A H 0.2696 1.0445 0.4438 0.050 Uiso 1 1 calc R
H35B H 0.1232 1.0570 0.4201 0.050 Uiso 1 1 calc R
H35C H 0.2133 1.0791 0.3465 0.050 Uiso 1 1 calc R
Cl1 Cl 0.54373(15) 1.11744(12) 0.55171(13) 0.0150(3) Uani 0.50 1 d P
C41 C 0.4696(12) 0.9880(9) 0.5594(10) 0.0150(3) Uani 0.25 1 d P
H41A H 0.3833 0.9915 0.5704 0.018 Uiso 0.25 1 d PR
H41B H 0.5221 0.9801 0.6219 0.018 Uiso 0.25 1 d PR
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
_geom_angle_site_symmetry_3
C13 N4 C17 117.6(3) . .
C23 N6 C19 119.2(3) . .
C24 N7 C23 123.8(3) . .
C24 N7 C5 119.4(2) . .
C23 N7 C5 115.8(2) . .
C7 N2 C11 118.6(3) . .
C19 N5 C17 119.2(3) . .
C19 N5 C18 118.3(3) . .
C17 N5 C18 117.4(3) . .
C24 N8 C28 118.9(3) . .
C7 N1 C40 123.9(3) . .
C7 N1 C1 118.3(2) . .
C40 N1 C1 117.7(2) . .
C34 N10 C30 116.6(3) . .
N8 C24 C25 122.9(3) . .
N8 C24 N7 114.6(3) . .
C25 C24 N7 122.5(3) . .
N6 C23 C22 122.5(3) . .
N6 C23 N7 112.9(3) . .
C22 C23 N7 124.5(3) . .
N6 C19 N5 115.0(3) . .
N6 C19 C20 122.6(3) . .
N5 C19 C20 122.4(3) . .
C40 N12 C36 119.2(3) . .
C36 N11 C34 117.9(3) . .
C36 N11 C35 117.5(3) . .
C34 N11 C35 119.0(3) . .
C15 C16 C17 118.4(3) . .
C15 C16 H16 120.8 . .
C17 C16 H16 120.8 . .
C9 C8 C7 116.2(3) . .
C9 C8 H8 121.9 . .
C7 C8 H8 121.9 . .
C38 C37 C36 116.7(3) . .
C38 C37 H37 121.7 . .
C36 C37 H37 121.7 . .
C11 N3 C13 116.9(3) . .
C11 N3 C12 120.6(3) . .
C13 N3 C12 120.3(3) . .
N4 C13 C14 124.6(3) . .
N4 C13 N3 115.0(3) . .
C14 C13 N3 120.3(3) . .
N4 C17 C16 122.7(3) . .
N4 C17 N5 116.4(3) . .
C16 C17 N5 120.9(3) . .
C5 C6 C1 120.5(3) . .
C5 C6 H6 119.8 . .
C1 C6 H6 119.8 . .
C22 C21 C20 121.8(3) . .
C22 C21 H21 119.1 . .
C20 C21 H21 119.1 . .
C26 C25 C24 117.1(3) . .
C26 C25 H25 121.5 . .
C24 C25 H25 121.5 . .
N5 C18 H18A 109.5 . .
N5 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N5 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
C37 C38 C39 122.4(3) . .
C37 C38 H38 118.8 . .
C39 C38 H38 118.8 . .
C28 N9 C30 116.7(3) . .
C28 N9 C29 120.0(3) . .
C30 N9 C29 118.1(3) . .
C1 C2 C3 119.9(3) . .
C1 C2 H2 120.1 . .
C3 C2 H2 120.1 . .
C2 C1 C6 119.4(3) . .
C2 C1 N1 122.2(3) . .
C6 C1 N1 118.4(3) . .
C21 C22 C23 117.7(3) . .
C21 C22 H22 121.1 . .
C23 C22 H22 121.1 . .
N2 C7 C8 123.9(3) . .
N2 C7 N1 113.9(3) . .
C8 C7 N1 122.2(3) . .
C26 C27 C28 117.0(3) . .
C26 C27 H27 121.5 . .
C28 C27 H27 121.5 . .
C6 C5 C4 120.3(3) . .
C6 C5 N7 119.6(3) . .
C4 C5 N7 120.1(3) . .
C2 C3 C4 121.1(3) . .
C2 C3 H3 119.5 . .
C4 C3 H3 119.5 . .
C25 C26 C27 121.3(3) . .
C25 C26 H26 119.4 . .
C27 C26 H26 119.4 . .
C13 C14 C15 117.0(3) . .
C13 C14 H14 121.5 . .
C15 C14 H14 121.5 . .
N8 C28 N9 114.9(3) . .
N8 C28 C27 122.7(3) . .
N9 C28 C27 122.4(3) . .
N10 C34 C33 123.6(3) . .
N10 C34 N11 116.0(3) . .
C33 C34 N11 120.4(3) . .
C10 C9 C8 121.6(3) . .
C10 C9 H9 119.2 . .
C8 C9 H9 119.2 . .
N10 C30 C31 123.8(3) . .
N10 C30 N9 115.9(3) . .
C31 C30 N9 120.1(3) . .
N3 C12 H12A 109.5 . .
N3 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
N3 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
C21 C20 C19 116.1(3) . .
C21 C20 H20 121.9 . .
C19 C20 H20 121.9 . .
C9 C10 C11 117.3(3) . .
C9 C10 H10 121.3 . .
C11 C10 H10 121.3 . .
C5 C4 C3 118.9(3) . .
C5 C4 H4 120.6 . .
C3 C4 H4 120.6 . .
N12 C36 N11 115.5(3) . .
N12 C36 C37 122.5(3) . .
N11 C36 C37 122.0(3) . .
C32 C31 C30 118.6(3) . .
C32 C31 H31 120.7 . .
C30 C31 H31 120.7 . .
N12 C40 C39 122.9(3) . .
N12 C40 N1 113.8(3) . .
C39 C40 N1 123.3(3) . .
C31 C32 C33 119.2(3) . .
C31 C32 H32 120.4 . .
C33 C32 H32 120.4 . .
C38 C39 C40 116.3(3) . .
C38 C39 H39 121.8 . .
C40 C39 H39 121.8 . .
N2 C11 N3 115.6(3) . .
N2 C11 C10 122.2(3) . .
N3 C11 C10 122.2(3) . .
N9 C29 H29A 109.5 . .
N9 C29 H29B 109.5 . .
H29A C29 H29B 109.5 . .
N9 C29 H29C 109.5 . .
H29A C29 H29C 109.5 . .
H29B C29 H29C 109.5 . .
C32 C33 C34 118.1(3) . .
C32 C33 H33 120.9 . .
C34 C33 H33 120.9 . .
C16 C15 C14 119.6(3) . .
C16 C15 H15 120.2 . .
C14 C15 H15 120.2 . .
N11 C35 H35A 109.5 . .
N11 C35 H35B 109.5 . .
H35A C35 H35B 109.5 . .
N11 C35 H35C 109.5 . .
H35A C35 H35C 109.5 . .
H35B C35 H35C 109.5 . .
C41 Cl1 C41 67.5(7) 2_676 .
Cl1 C41 Cl1 112.5(7) 2_676 .
Cl1 C41 C41 60.9(6) 2_676 2_676
Cl1 C41 C41 51.6(5) . 2_676
Cl1 C41 H41A 109.1 2_676 .
Cl1 C41 H41A 108.3 . .
C41 C41 H41A 125.0 2_676 .
Cl1 C41 H41B 110.5 2_676 .
Cl1 C41 H41B 108.6 . .
C41 C41 H41B 126.7 2_676 .
H41A C41 H41B 107.8 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N4 C13 1.328(4) .
N4 C17 1.336(4) .
N6 C23 1.338(4) .
N6 C19 1.339(4) .
N7 C24 1.401(4) .
N7 C23 1.412(4) .
N7 C5 1.445(4) .
N2 C7 1.328(4) .
N2 C11 1.338(4) .
N5 C19 1.391(4) .
N5 C17 1.416(4) .
N5 C18 1.465(4) .
N8 C24 1.322(4) .
N8 C28 1.343(4) .
N1 C7 1.410(4) .
N1 C40 1.410(4) .
N1 C1 1.442(4) .
N10 C34 1.332(4) .
N10 C30 1.343(4) .
C24 C25 1.396(4) .
C23 C22 1.387(5) .
C19 C20 1.404(5) .
N12 C40 1.335(4) .
N12 C36 1.335(4) .
N11 C36 1.397(4) .
N11 C34 1.425(4) .
N11 C35 1.469(4) .
C16 C15 1.375(5) .
C16 C17 1.395(4) .
C16 H16 0.9300 .
C8 C9 1.386(5) .
C8 C7 1.387(4) .
C8 H8 0.9300 .
C37 C38 1.368(5) .
C37 C36 1.398(5) .
C37 H37 0.9300 .
N3 C11 1.385(4) .
N3 C13 1.435(4) .
N3 C12 1.435(4) .
C13 C14 1.381(5) .
C6 C5 1.372(4) .
C6 C1 1.402(4) .
C6 H6 0.9300 .
C21 C22 1.368(5) .
C21 C20 1.395(5) .
C21 H21 0.9300 .
C25 C26 1.384(5) .
C25 H25 0.9300 .
C18 H18A 0.9600 .
C18 H18B 0.9600 .
C18 H18C 0.9600 .
C38 C39 1.388(5) .
C38 H38 0.9300 .
N9 C28 1.389(4) .
N9 C30 1.426(4) .
N9 C29 1.456(4) .
C2 C1 1.379(4) .
C2 C3 1.380(5) .
C2 H2 0.9300 .
C22 H22 0.9300 .
C27 C26 1.379(5) .
C27 C28 1.394(4) .
C27 H27 0.9300 .
C5 C4 1.392(5) .
C3 C4 1.390(5) .
C3 H3 0.9300 .
C26 H26 0.9300 .
C14 C15 1.396(5) .
C14 H14 0.9300 .
C34 C33 1.386(5) .
C9 C10 1.374(4) .
C9 H9 0.9300 .
C30 C31 1.370(5) .
C12 H12A 0.9600 .
C12 H12B 0.9600 .
C12 H12C 0.9600 .
C20 H20 0.9300 .
C10 C11 1.398(4) .
C10 H10 0.9300 .
C4 H4 0.9300 .
C31 C32 1.372(5) .
C31 H31 0.9300 .
C40 C39 1.388(5) .
C32 C33 1.380(5) .
C32 H32 0.9300 .
C39 H39 0.9300 .
C29 H29A 0.9600 .
C29 H29B 0.9600 .
C29 H29C 0.9600 .
C33 H33 0.9300 .
C15 H15 0.9300 .
C35 H35A 0.9600 .
C35 H35B 0.9600 .
C35 H35C 0.9600 .
Cl1 C41 1.640(12) 2_676
Cl1 C41 1.830(11) .
C41 Cl1 1.640(12) 2_676
C41 C41 1.93(3) 2_676
C41 H41A 0.9600 .
C41 H41B 0.9600 .
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_4
C28 N8 C24 C25 -1.0(5) . .
C28 N8 C24 N7 179.3(3) . .
C23 N7 C24 N8 -150.8(3) . .
C5 N7 C24 N8 17.1(4) . .
C23 N7 C24 C25 29.4(5) . .
C5 N7 C24 C25 -162.7(3) . .
C19 N6 C23 C22 3.6(4) . .
C19 N6 C23 N7 -172.9(3) . .
C24 N7 C23 N6 -158.1(3) . .
C5 N7 C23 N6 33.6(4) . .
C24 N7 C23 C22 25.5(5) . .
C5 N7 C23 C22 -142.8(3) . .
C23 N6 C19 N5 178.2(3) . .
C23 N6 C19 C20 -2.3(4) . .
C17 N5 C19 N6 -9.5(4) . .
C18 N5 C19 N6 -163.4(3) . .
C17 N5 C19 C20 171.0(3) . .
C18 N5 C19 C20 17.1(4) . .
C17 N4 C13 C14 3.2(4) . .
C17 N4 C13 N3 -172.4(3) . .
C11 N3 C13 N4 80.9(4) . .
C12 N3 C13 N4 -116.1(3) . .
C11 N3 C13 C14 -94.9(4) . .
C12 N3 C13 C14 68.2(4) . .
C13 N4 C17 C16 -1.6(4) . .
C13 N4 C17 N5 178.8(3) . .
C15 C16 C17 N4 -0.7(4) . .
C15 C16 C17 N5 178.9(3) . .
C19 N5 C17 N4 -119.1(3) . .
C18 N5 C17 N4 35.0(4) . .
C19 N5 C17 C16 61.3(4) . .
C18 N5 C17 C16 -144.6(3) . .
N8 C24 C25 C26 2.8(5) . .
N7 C24 C25 C26 -177.4(3) . .
C36 C37 C38 C39 1.9(5) . .
C3 C2 C1 C6 -1.3(5) . .
C3 C2 C1 N1 177.2(3) . .
C5 C6 C1 C2 0.1(5) . .
C5 C6 C1 N1 -178.4(3) . .
C7 N1 C1 C2 58.3(4) . .
C40 N1 C1 C2 -119.3(3) . .
C7 N1 C1 C6 -123.2(3) . .
C40 N1 C1 C6 59.2(4) . .
C20 C21 C22 C23 0.3(5) . .
N6 C23 C22 C21 -2.6(5) . .
N7 C23 C22 C21 173.5(3) . .
C11 N2 C7 C8 0.8(5) . .
C11 N2 C7 N1 -177.3(3) . .
C9 C8 C7 N2 0.1(5) . .
C9 C8 C7 N1 178.0(3) . .
C40 N1 C7 N2 -155.4(3) . .
C1 N1 C7 N2 27.2(4) . .
C40 N1 C7 C8 26.5(5) . .
C1 N1 C7 C8 -151.0(3) . .
C1 C6 C5 C4 1.4(5) . .
C1 C6 C5 N7 -176.6(3) . .
C24 N7 C5 C6 -115.2(3) . .
C23 N7 C5 C6 53.7(4) . .
C24 N7 C5 C4 66.9(4) . .
C23 N7 C5 C4 -124.3(3) . .
C1 C2 C3 C4 0.9(5) . .
C24 C25 C26 C27 -1.5(5) . .
C28 C27 C26 C25 -1.5(5) . .
N4 C13 C14 C15 -2.4(5) . .
N3 C13 C14 C15 173.0(3) . .
C24 N8 C28 N9 176.5(3) . .
C24 N8 C28 C27 -2.4(5) . .
C30 N9 C28 N8 8.8(4) . .
C29 N9 C28 N8 162.8(3) . .
C30 N9 C28 C27 -172.4(3) . .
C29 N9 C28 C27 -18.3(5) . .
C26 C27 C28 N8 3.6(5) . .
C26 C27 C28 N9 -175.2(3) . .
C30 N10 C34 C33 -2.9(5) . .
C30 N10 C34 N11 176.8(3) . .
C36 N11 C34 N10 -117.9(3) . .
C35 N11 C34 N10 35.1(4) . .
C36 N11 C34 C33 61.8(4) . .
C35 N11 C34 C33 -145.2(3) . .
C7 C8 C9 C10 -0.6(5) . .
C34 N10 C30 C31 2.2(5) . .
C34 N10 C30 N9 -173.7(3) . .
C28 N9 C30 N10 82.2(4) . .
C29 N9 C30 N10 -72.3(4) . .
C28 N9 C30 C31 -93.9(4) . .
C29 N9 C30 C31 111.6(4) . .
C22 C21 C20 C19 0.9(5) . .
N6 C19 C20 C21 0.1(4) . .
N5 C19 C20 C21 179.6(3) . .
C8 C9 C10 C11 0.2(5) . .
C6 C5 C4 C3 -1.8(4) . .
N7 C5 C4 C3 176.2(3) . .
C2 C3 C4 C5 0.6(5) . .
C40 N12 C36 N11 177.5(3) . .
C40 N12 C36 C37 -2.4(5) . .
C34 N11 C36 N12 -7.9(4) . .
C35 N11 C36 N12 -161.3(3) . .
C34 N11 C36 C37 172.0(3) . .
C35 N11 C36 C37 18.6(5) . .
C38 C37 C36 N12 0.2(5) . .
C38 C37 C36 N11 -179.6(3) . .
N10 C30 C31 C32 -0.5(5) . .
N9 C30 C31 C32 175.3(3) . .
C36 N12 C40 C39 2.5(5) . .
C36 N12 C40 N1 -174.6(3) . .
C7 N1 C40 N12 -148.7(3) . .
C1 N1 C40 N12 28.8(4) . .
C7 N1 C40 C39 34.3(5) . .
C1 N1 C40 C39 -148.2(3) . .
C30 C31 C32 C33 -0.7(5) . .
C37 C38 C39 C40 -1.8(5) . .
N12 C40 C39 C38 -0.4(5) . .
N1 C40 C39 C38 176.4(3) . .
C7 N2 C11 N3 178.5(3) . .
C7 N2 C11 C10 -1.2(5) . .
C13 N3 C11 N2 -1.8(4) . .
C12 N3 C11 N2 -164.8(3) . .
C13 N3 C11 C10 177.8(3) . .
C12 N3 C11 C10 14.8(5) . .
C9 C10 C11 N2 0.7(5) . .
C9 C10 C11 N3 -178.9(3) . .
C31 C32 C33 C34 0.1(5) . .
N10 C34 C33 C32 1.8(5) . .
N11 C34 C33 C32 -177.9(3) . .
C17 C16 C15 C14 1.5(4) . .
C13 C14 C15 C16 -0.1(5) . .
C41 Cl1 C41 Cl1 0.0 2_676 2_676
