#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:50:43 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178408 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/29/4022922.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_4022922
loop_
_publ_author_name
'Chun Zhang'
'Chuan-Feng Chen'
_publ_section_title
;
 Triptycene-Based Expanded Oxacalixarenes: Synthesis,
 Structure, and Tubular Assemblies in the Solid State
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3880
_journal_page_last               3888
_journal_paper_doi               10.1021/jo0702490
_journal_volume                  72
_journal_year                    2007
_chemical_formula_moiety         'C46 H24 Cl2 N6 O4'
_chemical_formula_sum            'C46 H24 Cl2 N6 O4'
_chemical_formula_weight         795.61
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 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                 119.396(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            12
_cell_length_a                   41.277(15)
_cell_length_b                   19.829(6)
_cell_length_c                   29.101(10)
_cell_measurement_reflns_used    8871
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.0
_cell_measurement_theta_min      1.6
_cell_volume                     20752(12)
_computing_cell_refinement       CrystalClear
_computing_data_collection       CrystalClear
_computing_data_reduction        CrystalClear
_computing_publication_material  'CrystalStructure 3.7.0'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 7.31
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  confocal
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71070
_diffrn_reflns_av_R_equivalents  0.1001
_diffrn_reflns_av_sigmaI/netI    0.0933
_diffrn_reflns_limit_h_max       49
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            72734
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.57
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.9877
_exptl_absorpt_correction_T_min  0.9756
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Jacobson, R. (1998) Private communication'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.764
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             4896
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.207
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.052
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.971
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     785
_refine_ls_number_reflns         18163
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.971
_refine_ls_R_factor_all          0.1716
_refine_ls_R_factor_gt           0.0835
_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)+(0.1140P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2176
_refine_ls_wR_factor_ref         0.2605
_reflns_number_gt                8299
_reflns_number_total             18163
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo0702490si20070206_041838.cif
_cod_data_source_block           shelxl
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               4022922
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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
Cl1 Cl 0.62254(5) 0.34724(7) 0.00989(6) 0.1256(6) Uani 1 1 d .
Cl2 Cl 0.96212(4) 0.76529(10) 0.44300(8) 0.1536(7) Uani 1 1 d .
Cl3 Cl 0.70516(4) 0.25885(9) 0.46185(6) 0.1309(7) Uani 1 1 d .
N1 N 0.65690(9) 0.52453(16) 0.11158(12) 0.0605(8) Uani 1 1 d .
N2 N 0.64260(10) 0.47351(18) 0.02946(13) 0.0739(10) Uani 1 1 d .
N3 N 0.63888(9) 0.40936(17) 0.09705(13) 0.0681(9) Uani 1 1 d .
N4 N 0.84157(10) 0.74607(17) 0.34673(15) 0.0719(9) Uani 1 1 d .
N5 N 0.89787(11) 0.72239(19) 0.42601(17) 0.0903(12) Uani 1 1 d .
N6 N 0.89899(11) 0.7883(2) 0.35800(18) 0.0853(11) Uani 1 1 d .
N7 N 0.61403(8) 0.39462(17) 0.36545(12) 0.0655(9) Uani 1 1 d .
N8 N 0.64542(10) 0.3243(2) 0.44097(13) 0.0818(11) Uani 1 1 d .
N9 N 0.66929(9) 0.33890(19) 0.38127(13) 0.0782(11) Uani 1 1 d .
O1 O 0.66000(9) 0.58012(15) 0.04411(11) 0.0833(9) Uani 1 1 d .
O2 O 0.65095(8) 0.45820(13) 0.17203(10) 0.0732(8) Uani 1 1 d .
O3 O 0.84411(9) 0.68340(16) 0.41562(12) 0.0911(9) Uani 1 1 d .
O4 O 0.84633(9) 0.81031(15) 0.28501(13) 0.0815(8) Uani 1 1 d .
O5 O 0.64035(7) 0.40299(16) 0.31134(10) 0.0818(9) Uani 1 1 d .
O6 O 0.59432(8) 0.37763(16) 0.42646(11) 0.0833(9) Uani 1 1 d .
C1 C 0.65292(11) 0.5243(2) 0.06338(17) 0.0655(11) Uani 1 1 d .
C2 C 0.63666(12) 0.4184(2) 0.05060(18) 0.0773(12) Uani 1 1 d .
C3 C 0.64905(11) 0.4662(2) 0.12485(15) 0.0610(10) Uani 1 1 d .
C4 C 0.66027(12) 0.5126(2) 0.20723(17) 0.0627(10) Uani 1 1 d .
C5 C 0.68954(11) 0.50391(19) 0.25757(17) 0.0617(10) Uani 1 1 d .
H5 H 0.7038 0.4648 0.2666 0.074 Uiso 1 1 calc R
C6 C 0.69737(11) 0.5540(2) 0.29434(15) 0.0598(10) Uani 1 1 d .
C7 C 0.72662(11) 0.5523(2) 0.35170(15) 0.0632(10) Uani 1 1 d .
H7 H 0.7416 0.5111 0.3611 0.076 Uiso 1 1 calc R
C8 C 0.75005(12) 0.6158(2) 0.36273(16) 0.0657(11) Uani 1 1 d .
C9 C 0.78841(12) 0.6201(2) 0.38286(15) 0.0669(11) Uani 1 1 d .
H9 H 0.8029 0.5814 0.3910 0.080 Uiso 1 1 calc R
C10 C 0.80424(13) 0.6831(3) 0.39041(17) 0.0755(12) Uani 1 1 d .
C11 C 0.78408(14) 0.7415(2) 0.37921(18) 0.0807(13) Uani 1 1 d .
H11 H 0.7958 0.7832 0.3855 0.097 Uiso 1 1 calc R
C12 C 0.74624(13) 0.7372(2) 0.35843(18) 0.0769(12) Uani 1 1 d .
H12 H 0.7319 0.7762 0.3498 0.092 Uiso 1 1 calc R
C13 C 0.72944(12) 0.6745(2) 0.35039(16) 0.0681(11) Uani 1 1 d .
C14 C 0.68760(12) 0.6610(2) 0.32698(17) 0.0703(11) Uani 1 1 d .
H14 H 0.6727 0.7024 0.3177 0.084 Uiso 1 1 calc R
C15 C 0.67579(12) 0.6131(2) 0.28019(17) 0.0662(11) Uani 1 1 d .
C16 C 0.64697(12) 0.6212(2) 0.22953(18) 0.0749(12) Uani 1 1 d .
H16 H 0.6329 0.6605 0.2202 0.090 Uiso 1 1 calc R
C17 C 0.63877(11) 0.5700(2) 0.19187(17) 0.0685(11) Uani 1 1 d .
H17 H 0.6193 0.5749 0.1575 0.082 Uiso 1 1 calc R
C18 C 0.68469(12) 0.6192(2) 0.36870(16) 0.0717(12) Uani 1 1 d .
C19 C 0.66322(14) 0.6332(3) 0.3915(2) 0.0987(16) Uani 1 1 d .
H19 H 0.6492 0.6726 0.3833 0.118 Uiso 1 1 calc R
C20 C 0.66286(18) 0.5861(4) 0.4278(2) 0.114(2) Uani 1 1 d .
H20 H 0.6484 0.5949 0.4436 0.136 Uiso 1 1 calc R
C21 C 0.68261(18) 0.5299(4) 0.4399(2) 0.1097(19) Uani 1 1 d .
H21 H 0.6818 0.4999 0.4639 0.132 Uiso 1 1 calc R
C22 C 0.70441(13) 0.5150(3) 0.41719(17) 0.0885(14) Uani 1 1 d .
H22 H 0.7180 0.4752 0.4256 0.106 Uiso 1 1 calc R
C23 C 0.70579(12) 0.5597(2) 0.38205(17) 0.0732(12) Uani 1 1 d .
C24 C 0.86137(13) 0.7199(2) 0.3940(2) 0.0754(12) Uani 1 1 d .
C25 C 0.91366(12) 0.7582(3) 0.4038(2) 0.0892(15) Uani 1 1 d .
C26 C 0.86250(14) 0.7804(2) 0.3320(2) 0.0750(12) Uani 1 1 d .
C27 C 0.80753(13) 0.8143(2) 0.25344(19) 0.0711(11) Uani 1 1 d .
C28 C 0.79296(14) 0.7991(2) 0.20035(19) 0.0766(12) Uani 1 1 d .
H28 H 0.8082 0.7838 0.1874 0.092 Uiso 1 1 calc R
C29 C 0.75539(14) 0.8072(2) 0.16743(18) 0.0705(11) Uani 1 1 d .
C30 C 0.73399(14) 0.7922(2) 0.10779(19) 0.0883(14) Uani 1 1 d .
H30 H 0.7500 0.7752 0.0942 0.106 Uiso 1 1 calc R
C31 C 0.70398(12) 0.7428(2) 0.10093(17) 0.0724(12) Uani 1 1 d .
C32 C 0.69696(13) 0.6793(2) 0.07710(16) 0.0782(13) Uani 1 1 d .
H32 H 0.7123 0.6622 0.0649 0.094 Uiso 1 1 calc R
C33 C 0.66711(13) 0.6423(2) 0.07186(16) 0.0754(12) Uani 1 1 d .
C34 C 0.64307(13) 0.6662(2) 0.08852(18) 0.0793(13) Uani 1 1 d .
H34 H 0.6227 0.6408 0.0836 0.095 Uiso 1 1 calc R
C35 C 0.65021(13) 0.7296(2) 0.11296(18) 0.0817(13) Uani 1 1 d .
H35 H 0.6347 0.7466 0.1249 0.098 Uiso 1 1 calc R
C36 C 0.68078(13) 0.7670(2) 0.11930(17) 0.0752(12) Uani 1 1 d .
C37 C 0.69149(13) 0.8373(2) 0.14319(19) 0.0856(13) Uani 1 1 d .
H37 H 0.6755 0.8544 0.1566 0.103 Uiso 1 1 calc R
C38 C 0.73212(13) 0.8311(2) 0.18551(17) 0.0742(12) Uani 1 1 d .
C39 C 0.74753(13) 0.8458(2) 0.23885(19) 0.0752(12) Uani 1 1 d .
H39 H 0.7323 0.8611 0.2518 0.090 Uiso 1 1 calc R
C40 C 0.78559(13) 0.8380(2) 0.27331(18) 0.0744(12) Uani 1 1 d .
H40 H 0.7959 0.8486 0.3089 0.089 Uiso 1 1 calc R
C41 C 0.71415(16) 0.8564(2) 0.0815(2) 0.0925(15) Uani 1 1 d .
C42 C 0.71683(19) 0.8864(3) 0.0419(2) 0.117(2) Uani 1 1 d .
H42 H 0.7317 0.8678 0.0294 0.140 Uiso 1 1 calc R
C43 C 0.6979(3) 0.9430(5) 0.0209(3) 0.159(3) Uani 1 1 d .
H43 H 0.7010 0.9649 -0.0049 0.191 Uiso 1 1 calc R
C44 C 0.6736(2) 0.9706(3) 0.0363(3) 0.149(3) Uani 1 1 d .
H44 H 0.6600 1.0092 0.0200 0.178 Uiso 1 1 calc R
C45 C 0.66981(16) 0.9376(3) 0.0784(2) 0.117(2) Uani 1 1 d .
H45 H 0.6539 0.9543 0.0899 0.141 Uiso 1 1 calc R
C46 C 0.69100(16) 0.8806(2) 0.1002(2) 0.0940(15) Uani 1 1 d .
C47 C 0.61834(11) 0.3660(2) 0.40938(16) 0.0724(12) Uani 1 1 d .
C48 C 0.66914(12) 0.3147(2) 0.42336(17) 0.0813(13) Uani 1 1 d .
C49 C 0.64076(11) 0.3791(2) 0.35420(15) 0.0634(10) Uani 1 1 d .
C50 C 0.61057(11) 0.4435(2) 0.27469(16) 0.0628(10) Uani 1 1 d .
C51 C 0.58973(11) 0.4179(2) 0.22460(16) 0.0641(11) Uani 1 1 d .
H51 H 0.5938 0.3746 0.2164 0.077 Uiso 1 1 calc R
C52 C 0.56231(10) 0.4590(2) 0.18654(14) 0.0568(10) Uani 1 1 d .
C53 C 0.53627(10) 0.4387(2) 0.12879(15) 0.0612(10) Uani 1 1 d .
H53 H 0.5401 0.3923 0.1210 0.073 Uiso 1 1 calc R
C54 C 0.49716(10) 0.4511(2) 0.12099(14) 0.0593(10) Uani 1 1 d .
C55 C 0.46822(11) 0.4049(2) 0.10320(14) 0.0640(11) Uani 1 1 d .
H55 H 0.4717 0.3606 0.0960 0.077 Uiso 1 1 calc R
C56 C 0.43418(12) 0.4258(2) 0.09644(15) 0.0669(11) Uani 1 1 d .
C57 C 0.42806(12) 0.4901(2) 0.10548(17) 0.0737(12) Uani 1 1 d .
H57 H 0.4047 0.5031 0.0995 0.088 Uiso 1 1 calc R
C58 C 0.45682(12) 0.5367(2) 0.12367(16) 0.0712(11) Uani 1 1 d .
H58 H 0.4529 0.5808 0.1307 0.085 Uiso 1 1 calc R
C59 C 0.49161(11) 0.5170(2) 0.13141(15) 0.0632(11) Uani 1 1 d .
C60 C 0.52609(10) 0.5612(2) 0.15015(16) 0.0670(11) Uani 1 1 d .
H60 H 0.5224 0.6079 0.1576 0.080 Uiso 1 1 calc R
C61 C 0.55668(10) 0.5238(2) 0.19801(15) 0.0574(10) Uani 1 1 d .
C62 C 0.57785(11) 0.5481(2) 0.24851(17) 0.0701(11) Uani 1 1 d .
H62 H 0.5740 0.5916 0.2567 0.084 Uiso 1 1 calc R
C63 C 0.60540(11) 0.5071(3) 0.28775(16) 0.0731(12) Uani 1 1 d .
H63 H 0.6198 0.5232 0.3220 0.088 Uiso 1 1 calc R
C64 C 0.54129(11) 0.4901(2) 0.09478(15) 0.0669(11) Uani 1 1 d .
C65 C 0.55022(11) 0.4768(3) 0.05596(17) 0.0900(15) Uani 1 1 d .
H65 H 0.5547 0.4329 0.0492 0.108 Uiso 1 1 calc R
C66 C 0.55239(14) 0.5315(5) 0.0266(2) 0.117(2) Uani 1 1 d .
H66 H 0.5576 0.5232 -0.0006 0.141 Uiso 1 1 calc R
C67 C 0.54698(15) 0.5972(4) 0.0373(2) 0.113(2) Uani 1 1 d .
H67 H 0.5491 0.6326 0.0179 0.135 Uiso 1 1 calc R
C68 C 0.53849(12) 0.6101(3) 0.0768(2) 0.1006(17) Uani 1 1 d .
H68 H 0.5343 0.6539 0.0841 0.121 Uiso 1 1 calc R
C69 C 0.53628(10) 0.5543(3) 0.10624(16) 0.0703(12) 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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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_3
C3 N1 C1 112.9(3) .
C1 N2 C2 110.1(3) .
C2 N3 C3 110.5(3) .
C24 N4 C26 111.9(4) .
C25 N5 C24 109.8(4) .
C25 N6 C26 111.0(4) .
C47 N7 C49 113.7(3) .
C48 N8 C47 110.6(4) .
C49 N9 C48 111.5(3) .
C1 O1 C33 120.4(3) .
C3 O2 C4 120.8(3) .
C24 O3 C10 119.5(3) .
C26 O4 C27 122.3(3) .
C49 O5 C50 121.1(3) .
C47 O6 C56 123.1(3) 2_655
N2 C1 N1 128.0(4) .
N2 C1 O1 111.9(4) .
N1 C1 O1 120.1(4) .
N3 C2 N2 130.3(4) .
N3 C2 Cl1 114.6(4) .
N2 C2 Cl1 115.1(3) .
N1 C3 N3 128.2(4) .
N1 C3 O2 120.4(4) .
N3 C3 O2 111.3(4) .
C17 C4 C5 122.5(4) .
C17 C4 O2 119.8(4) .
C5 C4 O2 117.6(4) .
C6 C5 C4 119.0(4) .
C6 C5 H5 120.5 .
C4 C5 H5 120.5 .
C5 C6 C15 120.0(4) .
C5 C6 C7 127.0(4) .
C15 C6 C7 113.0(3) .
C6 C7 C23 105.6(3) .
C6 C7 C8 107.3(3) .
C23 C7 C8 106.4(3) .
C6 C7 H7 112.4 .
C23 C7 H7 112.4 .
C8 C7 H7 112.4 .
C13 C8 C9 119.0(4) .
C13 C8 C7 113.3(4) .
C9 C8 C7 127.7(4) .
C10 C9 C8 118.3(4) .
C10 C9 H9 120.8 .
C8 C9 H9 120.8 .
C11 C10 C9 123.0(4) .
C11 C10 O3 121.9(4) .
C9 C10 O3 114.9(4) .
C10 C11 C12 118.7(4) .
C10 C11 H11 120.7 .
C12 C11 H11 120.7 .
C11 C12 C13 119.8(4) .
C11 C12 H12 120.1 .
C13 C12 H12 120.1 .
C8 C13 C12 121.2(4) .
C8 C13 C14 112.5(4) .
C12 C13 C14 126.3(4) .
C18 C14 C15 104.8(3) .
C18 C14 C13 104.6(4) .
C15 C14 C13 107.5(3) .
C18 C14 H14 113.1 .
C15 C14 H14 113.1 .
C13 C14 H14 113.1 .
C16 C15 C6 120.1(4) .
C16 C15 C14 127.7(4) .
C6 C15 C14 112.2(4) .
C15 C16 C17 120.1(4) .
C15 C16 H16 120.0 .
C17 C16 H16 120.0 .
C4 C17 C16 118.3(4) .
C4 C17 H17 120.9 .
C16 C17 H17 120.9 .
C19 C18 C23 119.8(5) .
C19 C18 C14 126.8(5) .
C23 C18 C14 113.4(3) .
C18 C19 C20 118.3(5) .
C18 C19 H19 120.8 .
C20 C19 H19 120.8 .
C21 C20 C19 121.5(5) .
C21 C20 H20 119.3 .
C19 C20 H20 119.3 .
C20 C21 C22 120.9(6) .
C20 C21 H21 119.5 .
C22 C21 H21 119.5 .
C23 C22 C21 119.4(5) .
C23 C22 H22 120.3 .
C21 C22 H22 120.3 .
C22 C23 C18 120.1(4) .
C22 C23 C7 127.9(5) .
C18 C23 C7 111.9(4) .
N4 C24 N5 128.9(4) .
N4 C24 O3 119.6(4) .
N5 C24 O3 111.5(4) .
N6 C25 N5 130.5(4) .
N6 C25 Cl2 115.9(4) .
N5 C25 Cl2 113.7(4) .
N6 C26 N4 128.0(5) .
N6 C26 O4 113.1(4) .
N4 C26 O4 118.9(4) .
C40 C27 C28 121.8(5) .
C40 C27 O4 121.3(4) .
C28 C27 O4 116.6(4) .
C29 C28 C27 118.3(4) .
C29 C28 H28 120.8 .
C27 C28 H28 120.8 .
C28 C29 C38 122.0(4) .
C28 C29 C30 126.1(4) .
C38 C29 C30 111.9(4) .
C41 C30 C31 105.9(4) .
C41 C30 C29 106.1(4) .
C31 C30 C29 104.6(3) .
C41 C30 H30 113.1 .
C31 C30 H30 113.1 .
C29 C30 H30 113.1 .
C36 C31 C32 119.1(4) .
C36 C31 C30 113.6(4) .
C32 C31 C30 127.3(4) .
C33 C32 C31 119.4(4) .
C33 C32 H32 120.3 .
C31 C32 H32 120.3 .
C32 C33 C34 122.4(4) .
C32 C33 O1 116.7(4) .
C34 C33 O1 120.7(4) .
C33 C34 C35 118.4(4) .
C33 C34 H34 120.8 .
C35 C34 H34 120.8 .
C36 C35 C34 119.6(4) .
C36 C35 H35 120.2 .
C34 C35 H35 120.2 .
C31 C36 C35 121.0(4) .
C31 C36 C37 113.0(4) .
C35 C36 C37 126.0(5) .
C46 C37 C38 106.2(4) .
C46 C37 C36 105.1(4) .
C38 C37 C36 104.6(4) .
C46 C37 H37 113.4 .
C38 C37 H37 113.4 .
C36 C37 H37 113.4 .
C29 C38 C39 118.3(4) .
C29 C38 C37 114.5(4) .
C39 C38 C37 127.2(4) .
C38 C39 C40 121.1(4) .
C38 C39 H39 119.5 .
C40 C39 H39 119.5 .
C27 C40 C39 118.5(4) .
C27 C40 H40 120.8 .
C39 C40 H40 120.8 .
C42 C41 C46 122.7(6) .
C42 C41 C30 123.7(6) .
C46 C41 C30 113.4(5) .
C43 C42 C41 119.2(7) .
C43 C42 H42 120.4 .
C41 C42 H42 120.4 .
C42 C43 C44 122.3(8) .
C42 C43 H43 118.8 .
C44 C43 H43 118.8 .
C43 C44 C45 118.9(7) .
C43 C44 H44 120.6 .
C45 C44 H44 120.6 .
C46 C45 C44 116.6(7) .
C46 C45 H45 121.7 .
C44 C45 H45 121.7 .
C45 C46 C41 120.2(6) .
C45 C46 C37 126.6(6) .
C41 C46 C37 113.2(5) .
N7 C47 O6 120.9(3) .
N7 C47 N8 126.9(4) .
O6 C47 N8 112.2(4) .
N9 C48 N8 130.5(4) .
N9 C48 Cl3 115.8(3) .
N8 C48 Cl3 113.7(3) .
N9 C49 O5 112.0(3) .
N9 C49 N7 126.8(4) .
O5 C49 N7 121.2(3) .
C63 C50 C51 122.3(4) .
C63 C50 O5 120.7(4) .
C51 C50 O5 116.7(4) .
C50 C51 C52 118.0(4) .
C50 C51 H51 121.0 .
C52 C51 H51 121.0 .
C61 C52 C51 121.4(4) .
C61 C52 C53 113.5(3) .
C51 C52 C53 125.1(4) .
C64 C53 C54 105.6(3) .
C64 C53 C52 107.1(3) .
C54 C53 C52 103.9(3) .
C64 C53 H53 113.2 .
C54 C53 H53 113.2 .
C52 C53 H53 113.2 .
C59 C54 C55 120.0(4) .
C59 C54 C53 113.1(3) .
C55 C54 C53 126.8(4) .
C56 C55 C54 118.9(4) .
C56 C55 H55 120.6 .
C54 C55 H55 120.6 .
C57 C56 C55 122.0(4) .
C57 C56 O6 122.8(4) 2_655
C55 C56 O6 114.8(4) 2_655
C56 C57 C58 119.7(4) .
C56 C57 H57 120.1 .
C58 C57 H57 120.1 .
C57 C58 C59 119.7(4) .
C57 C58 H58 120.1 .
C59 C58 H58 120.1 .
C54 C59 C58 119.7(4) .
C54 C59 C60 113.2(3) .
C58 C59 C60 127.1(4) .
C59 C60 C61 104.8(3) .
C59 C60 C69 103.9(3) .
C61 C60 C69 105.9(3) .
C59 C60 H60 113.8 .
C61 C60 H60 113.8 .
C69 C60 H60 113.8 .
C62 C61 C52 119.4(4) .
C62 C61 C60 127.5(4) .
C52 C61 C60 113.1(4) .
C61 C62 C63 120.1(4) .
C61 C62 H62 119.9 .
C63 C62 H62 119.9 .
C50 C63 C62 118.8(4) .
C50 C63 H63 120.6 .
C62 C63 H63 120.6 .
C69 C64 C65 121.1(4) .
C69 C64 C53 112.8(4) .
C65 C64 C53 126.1(5) .
C64 C65 C66 118.1(6) .
C64 C65 H65 120.9 .
C66 C65 H65 120.9 .
C67 C66 C65 121.6(6) .
C67 C66 H66 119.2 .
C65 C66 H66 119.2 .
C68 C67 C66 119.7(6) .
C68 C67 H67 120.1 .
C66 C67 H67 120.1 .
C67 C68 C69 118.3(6) .
C67 C68 H68 120.9 .
C69 C68 H68 120.9 .
C64 C69 C68 121.1(4) .
C64 C69 C60 115.1(4) .
C68 C69 C60 123.7(5) .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C2 1.748(4) .
Cl2 C25 1.756(5) .
Cl3 C48 1.748(4) .
N1 C3 1.309(5) .
N1 C1 1.330(5) .
N2 C1 1.326(5) .
N2 C2 1.335(5) .
N3 C2 1.321(5) .
N3 C3 1.330(5) .
N4 C24 1.315(5) .
N4 C26 1.326(5) .
N5 C25 1.327(6) .
N5 C24 1.327(5) .
N6 C25 1.306(6) .
N6 C26 1.322(5) .
N7 C47 1.329(5) .
N7 C49 1.332(4) .
N8 C48 1.323(5) .
N8 C47 1.331(5) .
N9 C49 1.316(5) .
N9 C48 1.319(5) .
O1 C1 1.336(4) .
O1 C33 1.424(5) .
O2 C3 1.346(4) .
O2 C4 1.404(4) .
O3 C24 1.366(5) .
O3 C10 1.436(5) .
O4 C26 1.330(5) .
O4 C27 1.404(5) .
O5 C49 1.327(4) .
O5 C50 1.417(4) .
O6 C47 1.329(4) .
O6 C56 1.404(5) 2_655
C4 C17 1.377(5) .
C4 C5 1.378(5) .
C5 C6 1.377(5) .
C5 H5 0.9300 .
C6 C15 1.406(5) .
C6 C7 1.505(5) .
C7 C23 1.512(5) .
C7 C8 1.521(5) .
C7 H7 0.9800 .
C8 C13 1.382(5) .
C8 C9 1.395(5) .
C9 C10 1.377(6) .
C9 H9 0.9300 .
C10 C11 1.369(6) .
C11 C12 1.373(6) .
C11 H11 0.9300 .
C12 C13 1.385(5) .
C12 H12 0.9300 .
C13 C14 1.537(6) .
C14 C18 1.523(6) .
C14 C15 1.531(5) .
C14 H14 0.9800 .
C15 C16 1.376(6) .
C16 C17 1.407(6) .
C16 H16 0.9300 .
C17 H17 0.9300 .
C18 C19 1.370(6) .
C18 C23 1.403(6) .
C19 C20 1.417(8) .
C19 H19 0.9300 .
C20 C21 1.323(8) .
C20 H20 0.9300 .
C21 C22 1.384(7) .
C21 H21 0.9300 .
C22 C23 1.375(6) .
C22 H22 0.9300 .
C27 C40 1.374(6) .
C27 C28 1.388(6) .
C28 C29 1.375(6) .
C28 H28 0.9300 .
C29 C38 1.385(6) .
C29 C30 1.541(6) .
C30 C41 1.504(7) .
C30 C31 1.514(6) .
C30 H30 0.9800 .
C31 C36 1.391(6) .
C31 C32 1.397(6) .
C32 C33 1.376(6) .
C32 H32 0.9300 .
C33 C34 1.385(6) .
C34 C35 1.402(6) .
C34 H34 0.9300 .
C35 C36 1.396(6) .
C35 H35 0.9300 .
C36 C37 1.524(6) .
C37 C46 1.508(7) .
C37 C38 1.522(6) .
C37 H37 0.9800 .
C38 C39 1.389(6) .
C39 C40 1.397(6) .
C39 H39 0.9300 .
C40 H40 0.9300 .
C41 C42 1.349(7) .
C41 C46 1.398(7) .
C42 C43 1.331(10) .
C42 H42 0.9300 .
C43 C44 1.397(10) .
C43 H43 0.9300 .
C44 C45 1.463(9) .
C44 H44 0.9300 .
C45 C46 1.379(7) .
C45 H45 0.9300 .
C50 C63 1.364(6) .
C50 C51 1.375(5) .
C51 C52 1.393(5) .
C51 H51 0.9300 .
C52 C61 1.376(5) .
C52 C53 1.539(5) .
C53 C64 1.504(5) .
C53 C54 1.536(5) .
C53 H53 0.9800 .
C54 C59 1.385(5) .
C54 C55 1.389(5) .
C55 C56 1.383(5) .
C55 H55 0.9300 .
C56 C57 1.349(6) .
C56 O6 1.404(5) 2_655
C57 C58 1.388(6) .
C57 H57 0.9300 .
C58 C59 1.396(5) .
C58 H58 0.9300 .
C59 C60 1.525(5) .
C60 C61 1.535(5) .
C60 C69 1.535(6) .
C60 H60 0.9800 .
C61 C62 1.376(5) .
C62 C63 1.407(6) .
C62 H62 0.9300 .
C63 H63 0.9300 .
C64 C69 1.357(6) .
C64 C65 1.375(6) .
C65 C66 1.410(7) .
C65 H65 0.9300 .
C66 C67 1.383(8) .
C66 H66 0.9300 .
C67 C68 1.381(8) .
C67 H67 0.9300 .
C68 C69 1.428(6) .
C68 H68 0.9300 .
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
C2 N2 C1 N1 -0.8(6) . .
C2 N2 C1 O1 178.5(3) . .
C3 N1 C1 N2 -0.5(6) . .
C3 N1 C1 O1 -179.8(3) . .
C33 O1 C1 N2 172.4(4) . .
C33 O1 C1 N1 -8.2(6) . .
C3 N3 C2 N2 -0.6(7) . .
C3 N3 C2 Cl1 -178.7(3) . .
C1 N2 C2 N3 1.5(7) . .
C1 N2 C2 Cl1 179.6(3) . .
C1 N1 C3 N3 1.7(6) . .
C1 N1 C3 O2 -178.7(3) . .
C2 N3 C3 N1 -1.2(6) . .
C2 N3 C3 O2 179.1(3) . .
C4 O2 C3 N1 1.9(5) . .
C4 O2 C3 N3 -178.3(3) . .
C3 O2 C4 C17 58.7(5) . .
C3 O2 C4 C5 -125.7(4) . .
C17 C4 C5 C6 1.0(6) . .
O2 C4 C5 C6 -174.5(3) . .
C4 C5 C6 C15 -0.5(5) . .
C4 C5 C6 C7 176.4(3) . .
C5 C6 C7 C23 -119.4(4) . .
C15 C6 C7 C23 57.7(4) . .
C5 C6 C7 C8 127.4(4) . .
C15 C6 C7 C8 -55.5(4) . .
C6 C7 C8 C13 56.8(4) . .
C23 C7 C8 C13 -55.8(4) . .
C6 C7 C8 C9 -122.8(4) . .
C23 C7 C8 C9 124.5(4) . .
C13 C8 C9 C10 1.1(5) . .
C7 C8 C9 C10 -179.3(4) . .
C8 C9 C10 C11 0.2(6) . .
C8 C9 C10 O3 174.6(3) . .
C24 O3 C10 C11 -54.9(6) . .
C24 O3 C10 C9 130.6(4) . .
C9 C10 C11 C12 -1.4(7) . .
O3 C10 C11 C12 -175.5(4) . .
C10 C11 C12 C13 1.4(7) . .
C9 C8 C13 C12 -1.0(6) . .
C7 C8 C13 C12 179.3(4) . .
C9 C8 C13 C14 178.1(3) . .
C7 C8 C13 C14 -1.6(5) . .
C11 C12 C13 C8 -0.2(6) . .
C11 C12 C13 C14 -179.2(4) . .
C8 C13 C14 C18 57.3(4) . .
C12 C13 C14 C18 -123.7(4) . .
C8 C13 C14 C15 -53.8(4) . .
C12 C13 C14 C15 125.2(4) . .
C5 C6 C15 C16 -0.3(6) . .
C7 C6 C15 C16 -177.7(3) . .
C5 C6 C15 C14 177.3(3) . .
C7 C6 C15 C14 0.0(4) . .
C18 C14 C15 C16 121.2(4) . .
C13 C14 C15 C16 -127.9(4) . .
C18 C14 C15 C6 -56.2(4) . .
C13 C14 C15 C6 54.7(4) . .
C6 C15 C16 C17 0.6(6) . .
C14 C15 C16 C17 -176.6(4) . .
C5 C4 C17 C16 -0.8(6) . .
O2 C4 C17 C16 174.6(3) . .
C15 C16 C17 C4 -0.1(6) . .
C15 C14 C18 C19 -121.4(4) . .
C13 C14 C18 C19 125.6(4) . .
C15 C14 C18 C23 56.2(5) . .
C13 C14 C18 C23 -56.8(4) . .
C23 C18 C19 C20 -0.5(7) . .
C14 C18 C19 C20 176.9(4) . .
C18 C19 C20 C21 0.0(8) . .
C19 C20 C21 C22 0.0(9) . .
C20 C21 C22 C23 0.6(8) . .
C21 C22 C23 C18 -1.1(7) . .
C21 C22 C23 C7 -177.8(4) . .
C19 C18 C23 C22 1.1(6) . .
C14 C18 C23 C22 -176.6(4) . .
C19 C18 C23 C7 178.3(4) . .
C14 C18 C23 C7 0.6(5) . .
C6 C7 C23 C22 119.1(5) . .
C8 C7 C23 C22 -127.1(5) . .
C6 C7 C23 C18 -57.8(4) . .
C8 C7 C23 C18 56.0(4) . .
C26 N4 C24 N5 -1.9(7) . .
C26 N4 C24 O3 179.3(4) . .
C25 N5 C24 N4 1.2(7) . .
C25 N5 C24 O3 -179.9(4) . .
C10 O3 C24 N4 -10.0(6) . .
C10 O3 C24 N5 171.0(4) . .
C26 N6 C25 N5 0.8(8) . .
C26 N6 C25 Cl2 -179.4(3) . .
C24 N5 C25 N6 -0.6(8) . .
C24 N5 C25 Cl2 179.6(3) . .
C25 N6 C26 N4 -1.7(7) . .
C25 N6 C26 O4 180.0(4) . .
C24 N4 C26 N6 2.2(6) . .
C24 N4 C26 O4 -179.6(4) . .
C27 O4 C26 N6 -173.0(4) . .
C27 O4 C26 N4 8.5(6) . .
C26 O4 C27 C40 50.9(6) . .
C26 O4 C27 C28 -134.7(4) . .
C40 C27 C28 C29 -1.1(6) . .
O4 C27 C28 C29 -175.4(3) . .
C27 C28 C29 C38 1.2(6) . .
C27 C28 C29 C30 -179.2(4) . .
C28 C29 C30 C41 -124.1(5) . .
C38 C29 C30 C41 55.5(5) . .
C28 C29 C30 C31 124.1(4) . .
C38 C29 C30 C31 -56.3(5) . .
C41 C30 C31 C36 -54.5(5) . .
C29 C30 C31 C36 57.4(5) . .
C41 C30 C31 C32 122.9(5) . .
C29 C30 C31 C32 -125.2(5) . .
C36 C31 C32 C33 0.6(6) . .
C30 C31 C32 C33 -176.7(4) . .
C31 C32 C33 C34 1.2(7) . .
C31 C32 C33 O1 175.9(4) . .
C1 O1 C33 C32 134.1(4) . .
C1 O1 C33 C34 -51.2(6) . .
C32 C33 C34 C35 -1.9(7) . .
O1 C33 C34 C35 -176.4(4) . .
C33 C34 C35 C36 0.7(7) . .
C32 C31 C36 C35 -1.7(6) . .
C30 C31 C36 C35 175.9(4) . .
C32 C31 C36 C37 -178.8(4) . .
C30 C31 C36 C37 -1.2(5) . .
C34 C35 C36 C31 1.1(7) . .
C34 C35 C36 C37 177.7(4) . .
C31 C36 C37 C46 56.4(5) . .
C35 C36 C37 C46 -120.5(5) . .
C31 C36 C37 C38 -55.2(5) . .
C35 C36 C37 C38 127.9(5) . .
C28 C29 C38 C39 -1.3(6) . .
C30 C29 C38 C39 179.1(4) . .
C28 C29 C38 C37 179.3(4) . .
C30 C29 C38 C37 -0.3(5) . .
C46 C37 C38 C29 -54.6(5) . .
C36 C37 C38 C29 56.2(5) . .
C46 C37 C38 C39 126.1(5) . .
C36 C37 C38 C39 -123.1(5) . .
C29 C38 C39 C40 1.2(6) . .
C37 C38 C39 C40 -179.5(4) . .
C28 C27 C40 C39 1.0(6) . .
O4 C27 C40 C39 175.0(3) . .
C38 C39 C40 C27 -1.0(6) . .
C31 C30 C41 C42 -122.1(5) . .
C29 C30 C41 C42 127.0(5) . .
C31 C30 C41 C46 54.9(5) . .
C29 C30 C41 C46 -56.0(5) . .
C46 C41 C42 C43 2.8(9) . .
C30 C41 C42 C43 179.5(5) . .
C41 C42 C43 C44 -3.8(11) . .
C42 C43 C44 C45 2.4(11) . .
C43 C44 C45 C46 0.0(8) . .
C44 C45 C46 C41 -1.0(7) . .
C44 C45 C46 C37 -178.8(5) . .
C42 C41 C46 C45 -0.4(8) . .
C30 C41 C46 C45 -177.4(4) . .
C42 C41 C46 C37 177.8(5) . .
C30 C41 C46 C37 0.7(6) . .
C38 C37 C46 C45 -127.7(5) . .
C36 C37 C46 C45 121.8(5) . .
C38 C37 C46 C41 54.3(5) . .
C36 C37 C46 C41 -56.2(5) . .
C49 N7 C47 O6 178.7(4) . .
C49 N7 C47 N8 -1.2(7) . .
C56 O6 C47 N7 -7.6(7) 2_655 .
C56 O6 C47 N8 172.4(4) 2_655 .
C48 N8 C47 N7 1.0(7) . .
C48 N8 C47 O6 -178.9(4) . .
C49 N9 C48 N8 0.5(7) . .
C49 N9 C48 Cl3 178.5(3) . .
C47 N8 C48 N9 -0.6(7) . .
C47 N8 C48 Cl3 -178.7(3) . .
C48 N9 C49 O5 -179.1(4) . .
C48 N9 C49 N7 -0.7(7) . .
C50 O5 C49 N9 175.6(4) . .
C50 O5 C49 N7 -2.9(6) . .
C47 N7 C49 N9 1.1(6) . .
C47 N7 C49 O5 179.3(4) . .
C49 O5 C50 C63 69.0(5) . .
C49 O5 C50 C51 -116.9(4) . .
C63 C50 C51 C52 -0.6(6) . .
O5 C50 C51 C52 -174.6(3) . .
C50 C51 C52 C61 1.7(5) . .
C50 C51 C52 C53 -179.6(3) . .
C61 C52 C53 C64 55.5(4) . .
C51 C52 C53 C64 -123.3(4) . .
C61 C52 C53 C54 -55.9(4) . .
C51 C52 C53 C54 125.3(4) . .
C64 C53 C54 C59 -54.9(4) . .
C52 C53 C54 C59 57.7(4) . .
C64 C53 C54 C55 122.3(4) . .
C52 C53 C54 C55 -125.2(4) . .
C59 C54 C55 C56 -0.3(5) . .
C53 C54 C55 C56 -177.3(3) . .
C54 C55 C56 C57 1.5(6) . .
C54 C55 C56 O6 174.1(3) . 2_655
C55 C56 C57 C58 -2.0(6) . .
O6 C56 C57 C58 -174.0(4) 2_655 .
C56 C57 C58 C59 1.3(6) . .
C55 C54 C59 C58 -0.3(5) . .
C53 C54 C59 C58 177.0(3) . .
C55 C54 C59 C60 -179.5(3) . .
C53 C54 C59 C60 -2.1(4) . .
C57 C58 C59 C54 -0.2(6) . .
C57 C58 C59 C60 178.9(4) . .
C54 C59 C60 C61 -55.2(4) . .
C58 C59 C60 C61 125.7(4) . .
C54 C59 C60 C69 55.7(4) . .
C58 C59 C60 C69 -123.4(4) . .
C51 C52 C61 C62 -1.9(5) . .
C53 C52 C61 C62 179.2(3) . .
C51 C52 C61 C60 178.0(3) . .
C53 C52 C61 C60 -0.9(4) . .
C59 C60 C61 C62 -123.1(4) . .
C69 C60 C61 C62 127.4(4) . .
C59 C60 C61 C52 57.0(4) . .
C69 C60 C61 C52 -52.4(4) . .
C52 C61 C62 C63 1.0(5) . .
C60 C61 C62 C63 -178.8(3) . .
C51 C50 C63 C62 -0.2(6) . .
O5 C50 C63 C62 173.6(3) . .
C61 C62 C63 C50 0.0(6) . .
C54 C53 C64 C69 56.2(4) . .
C52 C53 C64 C69 -54.0(4) . .
C54 C53 C64 C65 -124.2(4) . .
C52 C53 C64 C65 125.6(4) . .
C69 C64 C65 C66 -2.8(6) . .
C53 C64 C65 C66 177.6(4) . .
C64 C65 C66 C67 2.1(7) . .
C65 C66 C67 C68 -1.3(8) . .
C66 C67 C68 C69 1.2(7) . .
C65 C64 C69 C68 2.8(6) . .
C53 C64 C69 C68 -177.6(3) . .
C65 C64 C69 C60 179.5(4) . .
C53 C64 C69 C60 -0.9(5) . .
C67 C68 C69 C64 -1.9(6) . .
C67 C68 C69 C60 -178.3(4) . .
C59 C60 C69 C64 -55.3(4) . .
C61 C60 C69 C64 54.8(4) . .
C59 C60 C69 C68 121.3(4) . .
C61 C60 C69 C68 -128.6(4) . .
