#------------------------------------------------------------------------------
#$Date: 2016-03-22 12:32:36 +0200 (Tue, 22 Mar 2016) $
#$Revision: 178953 $
#$URL: svn://www.crystallography.net/cod/cif/4/11/82/4118267.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_4118267
loop_
_publ_author_name
'Ming Li'
'A. Dieter Schlüter'
'Junji Sakamoto'
_publ_contact_author_email       schweizer@org.chem.ethz.ch
_publ_contact_author_name        'B. Schweizer'
_publ_section_title
;
 Solid-State Photopolymerization of a Shape-Persistent Macrocycle with Two
 1,8-Diazaanthracene Units in a Single Crystal
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              11721
_journal_page_last               11725
_journal_paper_doi               10.1021/ja3038905
_journal_volume                  134
_journal_year                    2012
_chemical_formula_moiety         'C62 H44 N4, C H Cl3'
_chemical_formula_sum            'C63 H45 Cl3 N4'
_chemical_formula_weight         964.38
_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                109.431(5)
_cell_angle_beta                 95.060(4)
_cell_angle_gamma                94.026(5)
_cell_formula_units_Z            2
_cell_length_a                   8.8876(10)
_cell_length_b                   16.169(2)
_cell_length_c                   17.719(2)
_cell_measurement_reflns_used    1694
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      26.06
_cell_measurement_theta_min      2.45
_cell_volume                     2378.4(5)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Platon, Ortep'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement
'OLEX2 (Dolomanov, 2009), SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω 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  0.0647
_diffrn_reflns_av_sigmaI/netI    0.1508
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            20852
_diffrn_reflns_theta_full        27.56
_diffrn_reflns_theta_max         27.56
_diffrn_reflns_theta_min         2.54
_exptl_absorpt_coefficient_mu    0.241
_exptl_absorpt_correction_T_max  0.9952
_exptl_absorpt_correction_T_min  0.9534
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_description       rod
_exptl_crystal_F_000             1004
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_refine_diff_density_max         1.177
_refine_diff_density_min         -0.491
_refine_diff_density_rms         0.086
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     655
_refine_ls_number_reflns         10805
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.1877
_refine_ls_R_factor_gt           0.0798
_refine_ls_shift/su_max          0.006
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1846
_refine_ls_wR_factor_ref         0.2371
_reflns_number_gt                4883
_reflns_number_total             10805
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ja3038905_si_003.cif
_cod_data_source_block           sc262811_0m
_cod_database_code               4118267
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
Cl1 Cl 1.67379(18) 0.24016(12) 0.24949(9) 0.0429(5) Uani 0.816(2) 1 d P A 1
Cl2 Cl 1.51648(16) 0.27584(11) 0.11637(8) 0.0360(4) Uani 0.816(2) 1 d P A 1
Cl3 Cl 1.41783(18) 0.34487(10) 0.27449(9) 0.0407(4) Uani 0.816(2) 1 d P A 1
C65 C 1.5781(7) 0.3200(5) 0.2207(4) 0.0419(16) Uani 0.816(2) 1 d P A 1
H65A H 1.6545 0.3793 0.2336 0.050 Uiso 0.816(2) 1 calc PR A 1
Cl1A Cl 0.9931(13) 0.2367(9) 0.3865(6) 0.112(5) Uani 0.184(2) 1 d PD . 2
Cl2A Cl 0.8366(17) 0.2630(9) 0.2509(8) 0.143(6) Uani 0.184(2) 1 d PD . 2
Cl3A Cl 1.0917(16) 0.1596(9) 0.2279(8) 0.127(5) Uani 0.184(2) 1 d PD . 2
C65A C 0.937(2) 0.1858(15) 0.2812(10) 0.0419(16) Uani 0.184(2) 1 d PD . 2
H65 H 0.8615 0.1266 0.2705 0.050 Uiso 0.184(2) 1 calc PR A 2
N1 N 0.8603(3) 0.9144(2) 0.41471(19) 0.0147(7) Uani 1 1 d . . .
N11 N 0.6159(3) 0.6453(2) 0.35986(19) 0.0150(7) Uani 1 1 d . . .
N33 N 0.8824(3) 0.8593(2) 0.13915(19) 0.0156(8) Uani 1 1 d . . .
N43 N 0.6370(3) 0.5892(2) 0.08198(19) 0.0147(7) Uani 1 1 d . . .
C2 C 0.8382(4) 0.9977(3) 0.4214(2) 0.0168(9) Uani 1 1 d . . .
H2 H 0.9001 1.0495 0.4703 0.020 Uiso 1 1 calc R . .
C3 C 0.7399(4) 1.0201(3) 0.3684(2) 0.0170(9) Uani 1 1 d . . .
H3 H 0.7269 1.0871 0.3767 0.020 Uiso 1 1 calc R . .
C4 C 0.6573(4) 0.9520(3) 0.3033(2) 0.0141(9) Uani 1 1 d . . .
C5 C 0.6780(4) 0.8653(3) 0.2961(2) 0.0122(8) Uani 1 1 d . . .
C6 C 0.5952(4) 0.7855(2) 0.2286(2) 0.0122(8) Uani 1 1 d . . .
H6 H 0.4935 0.8063 0.2055 0.015 Uiso 1 1 calc R . .
C7 C 0.5466(4) 0.7168(3) 0.2640(2) 0.0123(8) Uani 1 1 d . . .
C8 C 0.4070(4) 0.6654(3) 0.2407(2) 0.0150(9) Uani 1 1 d . . .
C9 C 0.3718(4) 0.6057(3) 0.2799(2) 0.0164(9) Uani 1 1 d . . .
H9 H 0.2655 0.5666 0.2648 0.020 Uiso 1 1 calc R . .
C10 C 0.4777(4) 0.5987(3) 0.3385(2) 0.0168(9) Uani 1 1 d . . .
H10 H 0.4489 0.5541 0.3685 0.020 Uiso 1 1 calc R . .
C12 C 0.6476(4) 0.7024(3) 0.3230(2) 0.0131(9) Uani 1 1 d . . .
C13 C 0.8044(4) 0.7548(3) 0.3437(2) 0.0119(8) Uani 1 1 d . . .
C14 C 0.7801(4) 0.8501(3) 0.3529(2) 0.0120(8) Uani 1 1 d . . .
C15 C 0.5579(4) 0.9743(3) 0.2464(2) 0.0140(9) Uani 1 1 d . . .
C16 C 0.4790(4) 0.9973(3) 0.2000(2) 0.0168(9) Uani 1 1 d . . .
C17 C 0.3794(5) 1.0263(3) 0.1474(3) 0.0224(10) Uani 1 1 d . . .
C18 C 0.3598(4) 0.9831(3) 0.0644(2) 0.0186(9) Uani 1 1 d . . .
H18 H 0.4179 0.9270 0.0393 0.022 Uiso 1 1 calc R . .
C19 C 0.2652(4) 1.0122(3) 0.0137(3) 0.0209(10) Uani 1 1 d . . .
C20 C 0.1838(5) 1.0822(3) 0.0470(3) 0.0314(12) Uani 1 1 d . . .
H20 H 0.1092 1.1039 0.0092 0.038 Uiso 1 1 calc R . .
C21 C 0.1990(5) 1.1246(3) 0.1303(3) 0.0304(11) Uani 1 1 d . . .
H21 H 0.1361 1.1785 0.1554 0.036 Uiso 1 1 calc R . .
C22 C 0.2967(5) 1.0965(3) 0.1809(3) 0.0269(11) Uani 1 1 d . . .
H22 H 0.3076 1.1284 0.2442 0.032 Uiso 1 1 calc R . .
C23 C 0.2450(5) 0.9670(3) -0.0758(3) 0.0266(11) Uani 1 1 d . . .
H23A H 0.3213 0.9164 -0.0917 0.040 Uiso 1 1 calc R . .
H23B H 0.2699 1.0145 -0.1049 0.040 Uiso 1 1 calc R . .
H23C H 0.1292 0.9374 -0.0953 0.040 Uiso 1 1 calc R . .
C24 C 0.3027(4) 0.6725(3) 0.1768(2) 0.0150(9) Uani 1 1 d . . .
C25 C 0.2215(4) 0.6774(3) 0.1218(2) 0.0151(9) Uani 1 1 d . . .
C26 C 0.1308(4) 0.6832(3) 0.0533(2) 0.0157(9) Uani 1 1 d . . .
C27 C 0.0008(4) 0.6248(3) 0.0172(2) 0.0152(9) Uani 1 1 d . . .
H27 H -0.0348 0.5769 0.0426 0.018 Uiso 1 1 calc R . .
C28 C -0.0823(4) 0.6286(3) -0.0513(2) 0.0170(9) Uani 1 1 d . . .
C29 C -0.0353(4) 0.6927(3) -0.0831(2) 0.0216(10) Uani 1 1 d . . .
H29 H -0.0982 0.6966 -0.1353 0.026 Uiso 1 1 calc R . .
C30 C 0.0933(5) 0.7515(3) -0.0473(3) 0.0230(10) Uani 1 1 d . . .
H30 H 0.1280 0.8000 -0.0722 0.028 Uiso 1 1 calc R . .
C31 C 0.1757(5) 0.7470(3) 0.0204(2) 0.0207(10) Uani 1 1 d . . .
H31 H 0.2735 0.7921 0.0477 0.025 Uiso 1 1 calc R . .
C32 C 0.8887(4) 0.7471(3) 0.4189(2) 0.0159(9) Uani 1 1 d . . .
H32A H 0.8226 0.7704 0.4687 0.024 Uiso 1 1 calc R . .
H32B H 0.9973 0.7866 0.4328 0.024 Uiso 1 1 calc R . .
H32C H 0.9061 0.6790 0.4087 0.024 Uiso 1 1 calc R . .
C34 C 1.0190(4) 0.9071(3) 0.1617(2) 0.0162(9) Uani 1 1 d . . .
H34 H 1.0475 0.9526 0.1325 0.019 Uiso 1 1 calc R . .
C35 C 1.1247(4) 0.8999(3) 0.2211(2) 0.0166(9) Uani 1 1 d . . .
H35 H 1.2297 0.9404 0.2380 0.020 Uiso 1 1 calc R . .
C36 C 1.0903(4) 0.8384(3) 0.2582(2) 0.0132(9) Uani 1 1 d . . .
C37 C 0.9513(4) 0.7860(2) 0.2335(2) 0.0108(8) Uani 1 1 d . . .
C38 C 0.9027(4) 0.7170(2) 0.2685(2) 0.0119(8) Uani 1 1 d . . .
H38 H 1.0045 0.6961 0.2913 0.014 Uiso 1 1 calc R . .
C39 C 0.8200(4) 0.6375(2) 0.2009(2) 0.0120(8) Uani 1 1 d . . .
C40 C 0.8377(4) 0.5505(3) 0.1940(2) 0.0142(9) Uani 1 1 d . A .
C41 C 0.7565(4) 0.4830(3) 0.1272(2) 0.0174(9) Uani 1 1 d . . .
H41 H 0.7705 0.4159 0.1178 0.021 Uiso 1 1 calc R . .
C42 C 0.6588(4) 0.5057(3) 0.0744(2) 0.0162(9) Uani 1 1 d . . .
H42 H 0.5973 0.4543 0.0250 0.019 Uiso 1 1 calc R . .
C44 C 0.7176(4) 0.6533(3) 0.1442(2) 0.0123(8) Uani 1 1 d . . .
C45 C 0.6946(4) 0.7491(3) 0.1544(2) 0.0119(8) Uani 1 1 d . . .
C46 C 0.8509(4) 0.8011(3) 0.1756(2) 0.0132(8) Uiso 1 1 d . . .
C47 C 1.1937(4) 0.8315(3) 0.3220(2) 0.0155(9) Uani 1 1 d . . .
C48 C 1.2776(4) 0.8273(3) 0.3774(2) 0.0153(9) Uani 1 1 d . . .
C49 C 1.3670(4) 0.8190(3) 0.4457(2) 0.0143(9) Uani 1 1 d . . .
C50 C 1.4990(4) 0.8747(3) 0.4817(2) 0.0162(9) Uani 1 1 d . . .
H50 H 1.5367 0.9232 0.4575 0.019 Uiso 1 1 calc R . .
C050 C 1.7214(4) 0.9298(3) 0.5904(2) 0.0236(10) Uani 1 1 d . . .
H05A H 1.8135 0.9136 0.5539 0.035 Uiso 1 1 calc R . .
H05B H 1.7532 0.9242 0.6486 0.035 Uiso 1 1 calc R . .
H05C H 1.6976 0.9966 0.5981 0.035 Uiso 1 1 calc R . .
C51 C 1.5830(4) 0.8677(3) 0.5496(2) 0.0173(9) Uani 1 1 d . . .
C051 C -0.2206(4) 0.5645(3) -0.0916(2) 0.0237(10) Uani 1 1 d . . .
H05D H -0.1964 0.4987 -0.0956 0.035 Uiso 1 1 calc R . .
H05E H -0.2500 0.5663 -0.1515 0.035 Uiso 1 1 calc R . .
H05F H -0.3144 0.5824 -0.0568 0.035 Uiso 1 1 calc R . .
C52 C 1.5304(5) 0.8018(3) 0.5784(2) 0.0218(10) Uani 1 1 d . . .
H52 H 1.5929 0.7945 0.6291 0.026 Uiso 1 1 calc R . .
C53 C 1.3993(5) 0.7456(3) 0.5428(3) 0.0227(10) Uani 1 1 d . . .
H53 H 1.3626 0.6964 0.5665 0.027 Uiso 1 1 calc R . .
C54 C 1.3168(5) 0.7538(3) 0.4764(2) 0.0203(10) Uani 1 1 d . . .
H54 H 1.2163 0.7112 0.4489 0.024 Uiso 1 1 calc R . .
C55 C 0.9302(4) 0.5258(3) 0.2511(2) 0.0167(9) Uani 1 1 d . . .
C56 C 0.9929(7) 0.4961(6) 0.2970(5) 0.0207(14) Uiso 0.816(2) 1 d P A 1
C57 C 1.0655(6) 0.4547(4) 0.3487(3) 0.0218(12) Uiso 0.816(2) 1 d P A 1
C57A C 1.1185(19) 0.4752(12) 0.3538(9) 0.0218(12) Uiso 0.184(2) 1 d PGD A 2
C58A C 1.133(2) 0.5133(13) 0.4373(10) 0.0237(11) Uiso 0.184(2) 1 d PG A 2
H58 H 1.0661 0.5645 0.4647 0.028 Uiso 0.184(2) 1 calc PR A 2
C59A C 1.234(2) 0.4842(14) 0.4848(7) 0.028(11) Uiso 0.184(2) 1 d PG A 2
C60A C 1.321(2) 0.4171(13) 0.4489(9) 0.041(7) Uiso 0.184(2) 1 d PG A 2
H60 H 1.3988 0.3949 0.4851 0.049 Uiso 0.184(2) 1 calc PR A 2
C61A C 1.3073(18) 0.3790(11) 0.3654(10) 0.039(7) Uiso 0.184(2) 1 d PG A 2
H61 H 1.3739 0.3278 0.3381 0.046 Uiso 0.184(2) 1 calc PR A 2
C62A C 1.2059(19) 0.4080(11) 0.3179(7) 0.026(6) Uiso 0.184(2) 1 d PG A 2
H62 H 1.1951 0.3790 0.2543 0.031 Uiso 0.184(2) 1 calc PR A 2
C58 C 1.1434(7) 0.5077(4) 0.4236(3) 0.0237(11) Uiso 0.816(2) 1 d P A 1
H58A H 1.1513 0.5774 0.4410 0.028 Uiso 0.816(2) 1 calc PR A 1
C59 C 1.2110(8) 0.4672(5) 0.4754(4) 0.027(2) Uiso 0.816(2) 1 d P A 1
C60 C 1.2035(6) 0.3765(4) 0.4506(3) 0.0246(13) Uani 0.816(2) 1 d P A 1
H60A H 1.2581 0.3460 0.4884 0.029 Uiso 0.816(2) 1 calc PR A 1
C61 C 1.1247(6) 0.3242(4) 0.3760(4) 0.0323(14) Uani 0.816(2) 1 d P A 1
H61A H 1.1168 0.2545 0.3581 0.039 Uiso 0.816(2) 1 calc PR A 1
C62 C 1.0569(6) 0.3644(3) 0.3258(3) 0.0228(12) Uani 0.816(2) 1 d P A 1
H62A H 0.9980 0.3250 0.2691 0.027 Uiso 0.816(2) 1 calc PR A 1
C63 C 1.2846(8) 0.5221(5) 0.5584(4) 0.0379(18) Uiso 0.816(2) 1 d P A 1
H63A H 1.3989 0.5469 0.5549 0.057 Uiso 0.816(2) 1 calc PR A 1
H63B H 1.2879 0.4821 0.5966 0.057 Uiso 0.816(2) 1 calc PR A 1
H63C H 1.2198 0.5769 0.5834 0.057 Uiso 0.816(2) 1 calc PR A 1
C64 C 0.6104(4) 0.7565(3) 0.0778(2) 0.0163(9) Uani 1 1 d . . .
H64A H 0.5928 0.8246 0.0877 0.024 Uiso 1 1 calc R . .
H64B H 0.5019 0.7169 0.0635 0.024 Uiso 1 1 calc R . .
H64C H 0.6773 0.7333 0.0284 0.024 Uiso 1 1 calc R . .
C63A C 1.251(4) 0.535(2) 0.5811(18) 0.0379(18) Uiso 0.184(2) 1 d P A 2
H63D H 1.3690 0.5571 0.6033 0.057 Uiso 0.184(2) 1 calc PR A 2
H63E H 1.2080 0.4911 0.6104 0.057 Uiso 0.184(2) 1 calc PR A 2
H63F H 1.1865 0.5916 0.5940 0.057 Uiso 0.184(2) 1 calc PR A 2
C56A C 1.021(4) 0.498(3) 0.295(2) 0.0207(14) Uiso 0.184(2) 1 d PD A 2
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'
Cl Cl 0.1484 0.1585 '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
Cl2 C65 Cl3 109.3(3) . .
Cl2 C65 Cl1 108.6(4) . .
Cl3 C65 Cl1 109.6(3) . .
Cl2 C65 H65A 109.8 . .
Cl3 C65 H65A 109.8 . .
Cl1 C65 H65A 109.8 . .
C65A Cl3A C21 155.7(10) . 1_645
C65A Cl3A C22 161.9(11) . 1_645
C21 Cl3A C22 38.1(3) 1_645 1_645
Cl3A C65A Cl2A 110.7(13) . .
Cl3A C65A Cl1A 111.9(12) . .
Cl2A C65A Cl1A 106.0(12) . .
Cl3A C65A H65 109.4 . .
Cl2A C65A H65 109.4 . .
Cl1A C65A H65 109.4 . .
C14 N1 C2 117.1(3) . .
C12 N11 C10 116.9(3) . .
C46 N33 C34 117.0(3) . .
C42 N43 C44 117.3(3) . .
N1 C2 C3 124.0(4) . .
N1 C2 H2 118.0 . .
C3 C2 H2 118.0 . .
C2 C3 C4 118.5(4) . .
C2 C3 H3 120.8 . .
C4 C3 H3 120.8 . .
C5 C4 C3 118.2(3) . .
C5 C4 C15 122.7(4) . .
C3 C4 C15 119.1(4) . .
C14 C5 C4 118.7(4) . .
C14 C5 C6 117.9(3) . .
C4 C5 C6 123.5(3) . .
C7 C6 C5 108.5(3) . .
C7 C6 C45 113.3(3) . .
C5 C6 C45 112.4(3) . .
C7 C6 H6 107.4 . .
C5 C6 H6 107.4 . .
C45 C6 H6 107.4 . .
C8 C7 C12 117.8(4) . .
C8 C7 C6 123.5(3) . .
C12 C7 C6 118.7(3) . .
C7 C8 C9 118.4(4) . .
C7 C8 C24 120.7(4) . .
C9 C8 C24 120.8(4) . .
C10 C9 C8 118.8(4) . .
C10 C9 H9 120.6 . .
C8 C9 H9 120.6 . .
N11 C10 C9 123.9(4) . .
N11 C10 H10 118.1 . .
C9 C10 H10 118.1 . .
N11 C12 C7 124.1(3) . .
N11 C12 C13 118.7(3) . .
C7 C12 C13 117.2(3) . .
C32 C13 C12 111.4(3) . .
C32 C13 C14 112.3(3) . .
C12 C13 C14 106.9(3) . .
C32 C13 C38 109.1(3) . .
C12 C13 C38 108.9(3) . .
C14 C13 C38 108.1(3) . .
N1 C14 C5 123.6(4) . .
N1 C14 C13 118.0(3) . .
C5 C14 C13 118.4(3) . .
C16 C15 C4 176.5(4) . .
C15 C16 C17 177.1(4) . .
C22 C17 C18 119.6(4) . .
C22 C17 C16 119.0(4) . .
C18 C17 C16 121.3(4) . .
C17 C18 C19 121.1(4) . .
C17 C18 H18 119.5 . .
C19 C18 H18 119.5 . .
C20 C19 C18 119.1(4) . .
C20 C19 C23 119.3(4) . .
C18 C19 C23 121.5(4) . .
C19 C20 C21 120.4(4) . .
C19 C20 H20 119.8 . .
C21 C20 H20 119.8 . .
C20 C21 C22 120.4(4) . .
C20 C21 Cl3A 145.6(6) . 1_465
C22 C21 Cl3A 81.0(5) . 1_465
C20 C21 H21 119.8 . .
C22 C21 H21 119.8 . .
Cl3A C21 H21 47.8 1_465 .
C17 C22 C21 119.4(4) . .
C17 C22 Cl3A 155.2(5) . 1_465
C21 C22 Cl3A 61.0(4) . 1_465
C17 C22 H22 120.3 . .
C21 C22 H22 120.3 . .
Cl3A C22 H22 65.3 1_465 .
C19 C23 H23A 109.5 . .
C19 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C19 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C25 C24 C8 177.1(4) . .
C24 C25 C26 176.9(4) . .
C31 C26 C27 119.3(4) . .
C31 C26 C25 119.2(4) . .
C27 C26 C25 121.4(4) . .
C28 C27 C26 120.9(4) . .
C28 C27 H27 119.6 . .
C26 C27 H27 119.6 . .
C27 C28 C29 118.8(4) . .
C27 C28 C051 121.2(4) . .
C29 C28 C051 120.0(4) . .
C30 C29 C28 120.7(4) . .
C30 C29 H29 119.7 . .
C28 C29 H29 119.7 . .
C31 C30 C29 120.1(4) . .
C31 C30 H30 119.9 . .
C29 C30 H30 119.9 . .
C30 C31 C26 120.1(4) . .
C30 C31 H31 119.9 . .
C26 C31 H31 119.9 . .
C13 C32 H32A 109.5 . .
C13 C32 H32B 109.5 . .
H32A C32 H32B 109.5 . .
C13 C32 H32C 109.5 . .
H32A C32 H32C 109.5 . .
H32B C32 H32C 109.5 . .
N33 C34 C35 123.5(4) . .
N33 C34 H34 118.3 . .
C35 C34 H34 118.3 . .
C34 C35 C36 118.7(4) . .
C34 C35 H35 120.6 . .
C36 C35 H35 120.6 . .
C35 C36 C37 118.6(3) . .
C35 C36 C47 120.4(3) . .
C37 C36 C47 121.0(4) . .
C46 C37 C36 118.0(3) . .
C46 C37 C38 118.7(3) . .
C36 C37 C38 123.3(3) . .
C37 C38 C39 108.6(3) . .
C37 C38 C13 112.6(3) . .
C39 C38 C13 113.3(3) . .
C37 C38 H38 107.3 . .
C39 C38 H38 107.3 . .
C13 C38 H38 107.3 . .
C40 C39 C44 118.5(4) . .
C40 C39 C38 123.8(3) . .
C44 C39 C38 117.6(3) . .
C39 C40 C41 117.8(4) . .
C39 C40 C55 123.9(4) . .
C41 C40 C55 118.3(4) . .
C42 C41 C40 119.0(4) . .
C42 C41 H41 120.5 . .
C40 C41 H41 120.5 . .
N43 C42 C41 123.6(4) . .
N43 C42 H42 118.2 . .
C41 C42 H42 118.2 . .
N43 C44 C39 123.6(4) . .
N43 C44 C45 118.3(3) . .
C39 C44 C45 118.0(3) . .
C46 C45 C44 107.3(3) . .
C46 C45 C64 111.6(3) . .
C44 C45 C64 111.4(3) . .
C46 C45 C6 109.4(3) . .
C44 C45 C6 107.9(3) . .
C64 C45 C6 109.2(3) . .
N33 C46 C37 124.1(3) . .
N33 C46 C45 118.4(3) . .
C37 C46 C45 117.5(3) . .
C48 C47 C36 177.9(4) . .
C47 C48 C49 175.1(4) . .
C50 C49 C54 120.2(4) . .
C50 C49 C48 121.4(4) . .
C54 C49 C48 118.4(4) . .
C49 C50 C51 120.9(4) . .
C49 C50 H50 119.5 . .
C51 C50 H50 119.5 . .
C51 C050 H05A 109.5 . .
C51 C050 H05B 109.5 . .
H05A C050 H05B 109.5 . .
C51 C050 H05C 109.5 . .
H05A C050 H05C 109.5 . .
H05B C050 H05C 109.5 . .
C52 C51 C50 117.4(4) . .
C52 C51 C050 121.5(4) . .
C50 C51 C050 121.0(4) . .
C28 C051 H05D 109.5 . .
C28 C051 H05E 109.5 . .
H05D C051 H05E 109.5 . .
C28 C051 H05F 109.5 . .
H05D C051 H05F 109.5 . .
H05E C051 H05F 109.5 . .
C53 C52 C51 122.2(4) . .
C53 C52 H52 118.9 . .
C51 C52 H52 118.9 . .
C54 C53 C52 119.8(4) . .
C54 C53 H53 120.1 . .
C52 C53 H53 120.1 . .
C53 C54 C49 119.5(4) . .
C53 C54 H54 120.3 . .
C49 C54 H54 120.3 . .
C56 C55 C56A 11(2) . .
C56 C55 C40 171.3(6) . .
C56A C55 C40 173.1(18) . .
C55 C56 C57 176.3(9) . .
C62 C57 C58 120.4(5) . .
C62 C57 C56 120.5(6) . .
C58 C57 C56 119.1(6) . .
C58A C57A C62A 120.0 . .
C58A C57A C56A 127.5(19) . .
C62A C57A C56A 112.5(19) . .
C59A C58A C57A 120.0 . .
C59A C58A H58 120.0 . .
C57A C58A H58 120.0 . .
C58A C59A C60A 120.0 . .
C58A C59A C63A 117.1(15) . .
C60A C59A C63A 122.8(16) . .
C61A C60A C59A 120.0 . .
C61A C60A H60 120.0 . .
C59A C60A H60 120.0 . .
C60A C61A C62A 120.0 . .
C60A C61A H61 120.0 . .
C62A C61A H61 120.0 . .
C61A C62A C57A 120.0 . .
C61A C62A H62 120.0 . .
C57A C62A H62 120.0 . .
C57 C58 C59 119.2(6) . .
C57 C58 H58A 120.4 . .
C59 C58 H58A 120.4 . .
C60 C59 C58 119.4(7) . .
C60 C59 C63 120.1(6) . .
C58 C59 C63 120.4(7) . .
C59 C60 C61 120.8(5) . .
C59 C60 H60A 119.6 . .
C61 C60 H60A 119.6 . .
C62 C61 C60 119.5(5) . .
C62 C61 H61A 120.3 . .
C60 C61 H61A 120.3 . .
C57 C62 C61 120.6(5) . .
C57 C62 H62A 119.7 . .
C61 C62 H62A 119.7 . .
C45 C64 H64A 109.5 . .
C45 C64 H64B 109.5 . .
H64A C64 H64B 109.5 . .
C45 C64 H64C 109.5 . .
H64A C64 H64C 109.5 . .
H64B C64 H64C 109.5 . .
C59A C63A H63D 109.5 . .
C59A C63A H63E 109.5 . .
H63D C63A H63E 109.5 . .
C59A C63A H63F 109.5 . .
H63D C63A H63F 109.5 . .
H63E C63A H63F 109.5 . .
C55 C56A C57A 173(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C65 1.780(7) .
Cl2 C65 1.765(6) .
Cl3 C65 1.779(6) .
C65 H65A 1.0800 .
Cl1A C65A 1.779(16) .
Cl2A C65A 1.776(17) .
Cl3A C65A 1.736(16) .
Cl3A C21 1.983(13) 1_645
Cl3A C22 2.240(13) 1_645
C65A H65 1.0800 .
N1 C14 1.338(5) .
N1 C2 1.343(5) .
N11 C12 1.325(5) .
N11 C10 1.348(5) .
N33 C46 1.335(5) .
N33 C34 1.344(5) .
N43 C42 1.341(5) .
N43 C44 1.341(5) .
C2 C3 1.378(5) .
C2 H2 1.0600 .
C3 C4 1.405(5) .
C3 H3 1.0600 .
C4 C5 1.393(5) .
C4 C15 1.434(5) .
C5 C14 1.390(5) .
C5 C6 1.523(5) .
C6 C7 1.502(5) .
C6 C45 1.619(5) .
C6 H6 1.0800 .
C7 C8 1.392(5) .
C7 C12 1.407(5) .
C8 C9 1.398(5) .
C8 C24 1.439(5) .
C9 C10 1.377(5) .
C9 H9 1.0600 .
C10 H10 1.0600 .
C12 C13 1.527(5) .
C13 C32 1.516(5) .
C13 C14 1.527(5) .
C13 C38 1.627(5) .
C15 C16 1.202(5) .
C16 C17 1.441(5) .
C17 C22 1.388(6) .
C17 C18 1.391(6) .
C18 C19 1.393(5) .
C18 H18 1.0600 .
C19 C20 1.377(6) .
C19 C23 1.498(6) .
C20 C21 1.395(6) .
C20 H20 1.0600 .
C21 C22 1.398(6) .
C21 Cl3A 1.983(13) 1_465
C21 H21 1.0600 .
C22 Cl3A 2.240(13) 1_465
C22 H22 1.0600 .
C23 H23A 1.0800 .
C23 H23B 1.0800 .
C23 H23C 1.0800 .
C24 C25 1.188(5) .
C25 C26 1.431(5) .
C26 C31 1.395(6) .
C26 C27 1.396(5) .
C27 C28 1.386(5) .
C27 H27 1.0600 .
C28 C29 1.391(6) .
C28 C051 1.507(5) .
C29 C30 1.391(6) .
C29 H29 1.0600 .
C30 C31 1.375(6) .
C30 H30 1.0600 .
C31 H31 1.0600 .
C32 H32A 1.0800 .
C32 H32B 1.0800 .
C32 H32C 1.0800 .
C34 C35 1.389(5) .
C34 H34 1.0600 .
C35 C36 1.392(5) .
C35 H35 1.0600 .
C36 C37 1.395(5) .
C36 C47 1.433(5) .
C37 C46 1.395(5) .
C37 C38 1.502(5) .
C38 C39 1.521(5) .
C38 H38 1.0800 .
C39 C40 1.392(5) .
C39 C44 1.395(5) .
C40 C41 1.411(5) .
C40 C55 1.423(5) .
C41 C42 1.376(5) .
C41 H41 1.0600 .
C42 H42 1.0600 .
C44 C45 1.528(5) .
C45 C46 1.520(5) .
C45 C64 1.536(5) .
C47 C48 1.202(5) .
C48 C49 1.438(5) .
C49 C50 1.390(5) .
C49 C54 1.403(6) .
C50 C51 1.400(5) .
C50 H50 1.0600 .
C050 C51 1.494(5) .
C050 H05A 1.0800 .
C050 H05B 1.0800 .
C050 H05C 1.0800 .
C51 C52 1.395(6) .
C051 H05D 1.0800 .
C051 H05E 1.0800 .
C051 H05F 1.0800 .
C52 C53 1.386(6) .
C52 H52 1.0600 .
C53 C54 1.380(5) .
C53 H53 1.0600 .
C54 H54 1.0600 .
C55 C56 1.192(7) .
C55 C56A 1.28(2) .
C56 C57 1.440(8) .
C57 C62 1.373(7) .
C57 C58 1.404(8) .
C57A C58A 1.3900 .
C57A C62A 1.3900 .
C57A C56A 1.455(19) .
C58A C59A 1.3900 .
C58A H58 1.0600 .
C59A C60A 1.3900 .
C59A C63A 1.62(3) .
C60A C61A 1.3900 .
C60A H60 1.0600 .
C61A C62A 1.3900 .
C61A H61 1.0600 .
C62A H62 1.0600 .
C58 C59 1.411(7) .
C58 H58A 1.0600 .
C59 C60 1.378(9) .
C59 C63 1.504(10) .
C60 C61 1.401(8) .
C60 H60A 1.0600 .
C61 C62 1.386(7) .
C61 H61A 1.0600 .
C62 H62A 1.0600 .
C63 H63A 1.0800 .
C63 H63B 1.0800 .
C63 H63C 1.0800 .
C64 H64A 1.0800 .
C64 H64B 1.0800 .
C64 H64C 1.0800 .
C63A H63D 1.0800 .
C63A H63E 1.0800 .
C63A H63F 1.0800 .
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
C21 Cl3A C65A Cl2A -48(3) 1_645 .
C22 Cl3A C65A Cl2A -176(3) 1_645 .
C21 Cl3A C65A Cl1A -166(2) 1_645 .
C22 Cl3A C65A Cl1A 66(4) 1_645 .
C14 N1 C2 C3 -0.5(5) . .
N1 C2 C3 C4 0.0(6) . .
C2 C3 C4 C5 0.6(5) . .
C2 C3 C4 C15 -178.1(3) . .
C3 C4 C5 C14 -0.6(5) . .
C15 C4 C5 C14 178.1(3) . .
C3 C4 C5 C6 179.8(3) . .
C15 C4 C5 C6 -1.5(5) . .
C14 C5 C6 C7 42.2(4) . .
C4 C5 C6 C7 -138.2(4) . .
C14 C5 C6 C45 -84.0(4) . .
C4 C5 C6 C45 95.7(4) . .
C5 C6 C7 C8 140.1(3) . .
C45 C6 C7 C8 -94.2(4) . .
C5 C6 C7 C12 -40.8(4) . .
C45 C6 C7 C12 84.8(4) . .
C12 C7 C8 C9 3.2(5) . .
C6 C7 C8 C9 -177.7(3) . .
C12 C7 C8 C24 -175.8(3) . .
C6 C7 C8 C24 3.3(5) . .
C7 C8 C9 C10 -1.5(5) . .
C24 C8 C9 C10 177.4(3) . .
C12 N11 C10 C9 1.8(6) . .
C8 C9 C10 N11 -1.1(6) . .
C10 N11 C12 C7 0.1(5) . .
C10 N11 C12 C13 -178.3(3) . .
C8 C7 C12 N11 -2.6(5) . .
C6 C7 C12 N11 178.3(3) . .
C8 C7 C12 C13 175.8(3) . .
C6 C7 C12 C13 -3.3(5) . .
N11 C12 C13 C32 -13.1(5) . .
C7 C12 C13 C32 168.4(3) . .
N11 C12 C13 C14 -136.1(3) . .
C7 C12 C13 C14 45.4(4) . .
N11 C12 C13 C38 107.3(4) . .
C7 C12 C13 C38 -71.2(4) . .
C2 N1 C14 C5 0.6(5) . .
C2 N1 C14 C13 179.4(3) . .
C4 C5 C14 N1 0.0(5) . .
C6 C5 C14 N1 179.7(3) . .
C4 C5 C14 C13 -178.9(3) . .
C6 C5 C14 C13 0.8(5) . .
C32 C13 C14 N1 14.4(5) . .
C12 C13 C14 N1 136.9(3) . .
C38 C13 C14 N1 -106.0(3) . .
C32 C13 C14 C5 -166.7(3) . .
C12 C13 C14 C5 -44.2(4) . .
C38 C13 C14 C5 72.9(4) . .
C5 C4 C15 C16 -158(6) . .
C3 C4 C15 C16 21(7) . .
C4 C15 C16 C17 -92(11) . .
C15 C16 C17 C22 30(9) . .
C15 C16 C17 C18 -147(9) . .
C22 C17 C18 C19 3.8(6) . .
C16 C17 C18 C19 -179.0(4) . .
C17 C18 C19 C20 -3.4(6) . .
C17 C18 C19 C23 179.1(4) . .
C18 C19 C20 C21 1.6(7) . .
C23 C19 C20 C21 179.1(4) . .
C19 C20 C21 C22 -0.1(7) . .
C19 C20 C21 Cl3A -122.4(10) . 1_465
C18 C17 C22 C21 -2.2(6) . .
C16 C17 C22 C21 -179.6(4) . .
C18 C17 C22 Cl3A 81.4(12) . 1_465
C16 C17 C22 Cl3A -95.9(12) . 1_465
C20 C21 C22 C17 0.5(7) . .
Cl3A C21 C22 C17 151.5(6) 1_465 .
C20 C21 C22 Cl3A -151.1(7) . 1_465
C7 C8 C24 C25 58(9) . .
C9 C8 C24 C25 -120(8) . .
C8 C24 C25 C26 -14(15) . .
C24 C25 C26 C31 -50(8) . .
C24 C25 C26 C27 128(8) . .
C31 C26 C27 C28 1.0(6) . .
C25 C26 C27 C28 -177.1(3) . .
C26 C27 C28 C29 -0.9(6) . .
C26 C27 C28 C051 178.5(4) . .
C27 C28 C29 C30 0.4(6) . .
C051 C28 C29 C30 -179.0(4) . .
C28 C29 C30 C31 0.0(6) . .
C29 C30 C31 C26 0.2(6) . .
C27 C26 C31 C30 -0.6(6) . .
C25 C26 C31 C30 177.5(3) . .
C46 N33 C34 C35 -1.5(5) . .
N33 C34 C35 C36 1.9(6) . .
C34 C35 C36 C37 0.6(5) . .
C34 C35 C36 C47 -177.5(3) . .
C35 C36 C37 C46 -3.1(5) . .
C47 C36 C37 C46 174.9(3) . .
C35 C36 C37 C38 179.4(3) . .
C47 C36 C37 C38 -2.6(5) . .
C46 C37 C38 C39 41.3(4) . .
C36 C37 C38 C39 -141.2(3) . .
C46 C37 C38 C13 -85.0(4) . .
C36 C37 C38 C13 92.5(4) . .
C32 C13 C38 C37 -118.2(3) . .
C12 C13 C38 C37 120.0(3) . .
C14 C13 C38 C37 4.2(4) . .
C32 C13 C38 C39 118.0(3) . .
C12 C13 C38 C39 -3.8(4) . .
C14 C13 C38 C39 -119.6(3) . .
C37 C38 C39 C40 139.7(4) . .
C13 C38 C39 C40 -94.4(4) . .
C37 C38 C39 C44 -42.2(4) . .
C13 C38 C39 C44 83.7(4) . .
C44 C39 C40 C41 3.3(5) . .
C38 C39 C40 C41 -178.6(3) . .
C44 C39 C40 C55 -175.4(3) . .
C38 C39 C40 C55 2.7(6) . .
C39 C40 C41 C42 -3.0(5) . .
C55 C40 C41 C42 175.7(3) . .
C44 N43 C42 C41 1.0(5) . .
C40 C41 C42 N43 0.9(6) . .
C42 N43 C44 C39 -0.7(5) . .
C42 N43 C44 C45 -179.8(3) . .
C40 C39 C44 N43 -1.5(5) . .
C38 C39 C44 N43 -179.7(3) . .
C40 C39 C44 C45 177.6(3) . .
C38 C39 C44 C45 -0.6(5) . .
N43 C44 C45 C46 -137.0(3) . .
C39 C44 C45 C46 43.8(4) . .
N43 C44 C45 C64 -14.6(4) . .
C39 C44 C45 C64 166.2(3) . .
N43 C44 C45 C6 105.3(4) . .
C39 C44 C45 C6 -73.9(4) . .
C7 C6 C45 C46 -119.2(3) . .
C5 C6 C45 C46 4.3(4) . .
C7 C6 C45 C44 -2.8(4) . .
C5 C6 C45 C44 120.7(3) . .
C7 C6 C45 C64 118.4(3) . .
C5 C6 C45 C64 -118.1(3) . .
C34 N33 C46 C37 -1.4(5) . .
C34 N33 C46 C45 177.2(3) . .
C36 C37 C46 N33 3.7(5) . .
C38 C37 C46 N33 -178.7(3) . .
C36 C37 C46 C45 -174.9(3) . .
C38 C37 C46 C45 2.7(5) . .
C44 C45 C46 N33 136.3(3) . .
C64 C45 C46 N33 14.0(5) . .
C6 C45 C46 N33 -107.0(4) . .
C44 C45 C46 C37 -45.0(4) . .
C64 C45 C46 C37 -167.3(3) . .
C6 C45 C46 C37 71.7(4) . .
C35 C36 C47 C48 99(12) . .
C37 C36 C47 C48 -79(12) . .
C36 C47 C48 C49 58(15) . .
C47 C48 C49 C50 -154(5) . .
C47 C48 C49 C54 25(5) . .
C54 C49 C50 C51 -0.8(6) . .
C48 C49 C50 C51 178.2(3) . .
C49 C50 C51 C52 1.2(5) . .
C49 C50 C51 C050 -177.5(4) . .
C50 C51 C52 C53 -0.9(6) . .
C050 C51 C52 C53 177.8(4) . .
C51 C52 C53 C54 0.3(6) . .
C52 C53 C54 C49 0.1(6) . .
C50 C49 C54 C53 0.1(6) . .
C48 C49 C54 C53 -178.9(3) . .
C39 C40 C55 C56 142(4) . .
C41 C40 C55 C56 -36(4) . .
C39 C40 C55 C56A -127(15) . .
C41 C40 C55 C56A 54(15) . .
C56A C55 C56 C57 -102(18) . .
C40 C55 C56 C57 40(13) . .
C55 C56 C57 C62 -1(11) . .
C55 C56 C57 C58 -180(100) . .
C62A C57A C58A C59A 0.0 . .
C56A C57A C58A C59A -179(3) . .
C57A C58A C59A C60A 0.0 . .
C57A C58A C59A C63A 177(2) . .
C58A C59A C60A C61A 0.0 . .
C63A C59A C60A C61A -177(2) . .
C59A C60A C61A C62A 0.0 . .
C60A C61A C62A C57A 0.0 . .
C58A C57A C62A C61A 0.0 . .
C56A C57A C62A C61A 179(2) . .
C62 C57 C58 C59 -0.8(8) . .
C56 C57 C58 C59 178.2(5) . .
C57 C58 C59 C60 2.0(8) . .
C57 C58 C59 C63 -175.3(6) . .
C58 C59 C60 C61 -2.5(9) . .
C63 C59 C60 C61 174.8(5) . .
C59 C60 C61 C62 1.8(8) . .
C58 C57 C62 C61 0.1(8) . .
C56 C57 C62 C61 -179.0(6) . .
C60 C61 C62 C57 -0.5(8) . .
C56 C55 C56A C57A -65(24) . .
C40 C55 C56A C57A 166(14) . .
C58A C57A C56A C55 3(28) . .
C62A C57A C56A C55 -176(26) . .
