#------------------------------------------------------------------------------
#$Date: 2020-04-16 03:55:08 +0300 (Thu, 16 Apr 2020) $
#$Revision: 250817 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/03/82/4038265.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_4038265
loop_
_publ_author_name
'Yang, Xiao'
'Zhang, Di'
'Liao, Yinhui'
'Zhao, Dahui'
_publ_section_title
;
 Toward an Air-Stable Triradical with Strong Spin Coupling: Synthesis of
 Substituted Truxene-5,10,15-triyl.
;
_journal_name_full               'The Journal of organic chemistry'
_journal_paper_doi               10.1021/acs.joc.9b03077
_journal_year                    2020
_chemical_formula_moiety         'C52 H35 Cl9 O3'
_chemical_formula_sum            'C52 H35 Cl9 O3'
_chemical_formula_weight         1026.85
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
????
;
_cell_angle_alpha                90
_cell_angle_beta                 111.906(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   15.913(4)
_cell_length_b                   15.005(3)
_cell_length_c                   20.527(5)
_cell_measurement_reflns_used    13205
_cell_measurement_temperature    103(2)
_cell_measurement_theta_max      27.4852
_cell_measurement_theta_min      1.3571
_cell_volume                     4547.4(18)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'CIFTAB (Sheldrick, 2013)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      103(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'MM007-HF CCD(Saturn 724+)'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0636
_diffrn_reflns_av_unetI/netI     0.0609
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            35686
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.507
_diffrn_reflns_theta_min         1.728
_diffrn_source                   'Rotating Anode'
_exptl_absorpt_coefficient_mu    0.600
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7766
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'
_exptl_crystal_colour            brown
_exptl_crystal_density_diffrn    1.500
_exptl_crystal_description       block
_exptl_crystal_F_000             2096
_exptl_crystal_size_max          0.265
_exptl_crystal_size_mid          0.172
_exptl_crystal_size_min          0.145
_refine_diff_density_max         0.876
_refine_diff_density_min         -0.562
_refine_diff_density_rms         0.079
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.210
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     582
_refine_ls_number_reflns         10393
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.210
_refine_ls_R_factor_all          0.1006
_refine_ls_R_factor_gt           0.0855
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0423P)²+9.5026P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1619
_refine_ls_wR_factor_ref         0.1697
_reflns_Friedel_coverage         0.000
_reflns_number_gt                8928
_reflns_number_total             10393
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            jo9b03077_si_002.cif
_cod_data_source_block           mx6700
_cod_original_cell_volume        4547.5(18)
_cod_database_code               4038265
_shelx_shelxl_version_number     2016/6
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.918
_shelx_estimated_absorpt_t_min   0.857
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C8(H8), C9(H9), C10(H10), C11(H11), C21(H21), C23(H23), C26(H26), C27(H27),
 C28(H28), C29(H29), C35(H35), C37(H37), C41(H41), C42(H42), C43(H43), C44(H44),
  C49(H49), C51(H51)
2.c Idealised Me refined as rotating group:
 C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C32(H32A,H32B,
 H32C), C39(H39A,H39B,H39C)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.19879(7) 0.51308(7) 0.62911(6) 0.0360(2) Uani 1 1 d . . . . .
C1 C 0.4261(2) 0.6504(2) 0.8020(2) 0.0241(8) Uani 1 1 d . . . . .
O1 O 0.3612(2) 0.68374(19) 0.88764(15) 0.0358(7) Uani 1 1 d . . . . .
Cl2 Cl 0.26374(8) 0.43328(8) 0.39812(6) 0.0452(3) Uani 1 1 d . . . . .
O2 O 0.56001(18) 0.53965(18) 0.93139(14) 0.0298(6) Uani 1 1 d . . . . .
C2 C 0.4265(3) 0.5799(2) 0.7470(2) 0.0251(8) Uani 1 1 d . . . . .
O3 O 0.43191(18) 0.44404(17) 0.80616(15) 0.0295(6) Uani 1 1 d . . . . .
Cl3 Cl 0.51106(7) 0.61959(7) 0.60551(5) 0.0333(2) Uani 1 1 d . . . . .
C3 C 0.4809(3) 0.4955(2) 0.7728(2) 0.0255(8) Uani 1 1 d . . . . .
C4 C 0.5775(3) 0.5252(2) 0.8220(2) 0.0246(8) Uani 1 1 d . . . . .
Cl4 Cl 0.75606(8) 0.34855(7) 0.88366(6) 0.0414(3) Uani 1 1 d . . . . .
C5 C 0.5862(3) 0.5882(2) 0.8812(2) 0.0246(8) Uani 1 1 d . . . . .
Cl5 Cl 1.04214(8) 0.55739(9) 0.91366(7) 0.0519(3) Uani 1 1 d . . . . .
C6 C 0.5240(3) 0.6692(3) 0.84855(19) 0.0251(8) Uani 1 1 d . . . . .
Cl6 Cl 0.70881(7) 0.66831(6) 0.75277(5) 0.0328(2) Uani 1 1 d . . . . .
Cl7 Cl 0.55119(8) 0.84649(7) 0.98153(6) 0.0402(3) Uani 1 1 d . . . . .
C7 C 0.3718(3) 0.7256(3) 0.7560(2) 0.0271(8) Uani 1 1 d . . . . .
Cl8 Cl 0.49257(11) 1.13571(8) 0.81983(9) 0.0709(5) Uani 1 1 d . . . . .
C8 C 0.3429(3) 0.8060(3) 0.7734(2) 0.0295(9) Uani 1 1 d . . . . .
H8 H 0.360556 0.823468 0.821186 0.035 Uiso 1 1 calc R . . . .
C9 C 0.2877(3) 0.8609(3) 0.7200(2) 0.0353(10) Uani 1 1 d . . . . .
H9 H 0.268853 0.916896 0.731330 0.042 Uiso 1 1 calc R . . . .
Cl9 Cl 0.54283(8) 0.82038(7) 0.71583(6) 0.0414(3) Uani 1 1 d . . . . .
C10 C 0.2601(3) 0.8349(3) 0.6507(2) 0.0378(10) Uani 1 1 d . . . . .
H10 H 0.223454 0.873810 0.614868 0.045 Uiso 1 1 calc R . . . .
C11 C 0.2850(3) 0.7523(3) 0.6326(2) 0.0323(9) Uani 1 1 d . . . . .
H11 H 0.263967 0.733410 0.585020 0.039 Uiso 1 1 calc R . . . .
C12 C 0.3415(3) 0.6985(2) 0.6860(2) 0.0264(8) Uani 1 1 d . . . . .
C13 C 0.3777(3) 0.6094(2) 0.6821(2) 0.0254(8) Uani 1 1 d . . . . .
C14 C 0.3699(3) 0.6137(2) 0.8440(2) 0.0266(8) Uani 1 1 d . . . . .
H14A H 0.309414 0.594171 0.811389 0.032 Uiso 1 1 calc R . . . .
H14B H 0.401140 0.562073 0.872926 0.032 Uiso 1 1 calc R . . . .
C15 C 0.2822(3) 0.6804(3) 0.9066(3) 0.0402(11) Uani 1 1 d . . . . .
C16 C 0.2804(3) 0.5959(3) 0.9447(3) 0.0459(12) Uani 1 1 d . . . . .
H16A H 0.270755 0.545257 0.912564 0.069 Uiso 1 1 calc GR . . . .
H16B H 0.231077 0.598514 0.962310 0.069 Uiso 1 1 calc GR . . . .
H16C H 0.338258 0.588524 0.984246 0.069 Uiso 1 1 calc GR . . . .
C17 C 0.2965(4) 0.7587(4) 0.9556(3) 0.0582(15) Uani 1 1 d . . . . .
H17A H 0.352493 0.750027 0.996685 0.087 Uiso 1 1 calc GR . . . .
H17B H 0.245200 0.763460 0.970814 0.087 Uiso 1 1 calc GR . . . .
H17C H 0.301231 0.813468 0.931183 0.087 Uiso 1 1 calc GR . . . .
C18 C 0.1953(3) 0.6913(4) 0.8414(3) 0.0581(15) Uani 1 1 d . . . . .
H18A H 0.200281 0.744347 0.815240 0.087 Uiso 1 1 calc GR . . . .
H18B H 0.143492 0.697945 0.855905 0.087 Uiso 1 1 calc GR . . . .
H18C H 0.186424 0.638571 0.811393 0.087 Uiso 1 1 calc GR . . . .
C19 C 0.3526(3) 0.5639(3) 0.6127(2) 0.0262(8) Uani 1 1 d . . . . .
C20 C 0.2701(3) 0.5207(3) 0.5825(2) 0.0284(8) Uani 1 1 d . . . . .
C21 C 0.2416(3) 0.4800(3) 0.5174(2) 0.0324(9) Uani 1 1 d . . . . .
H21 H 0.184746 0.450473 0.498831 0.039 Uiso 1 1 calc R . . . .
C22 C 0.2981(3) 0.4834(3) 0.4797(2) 0.0320(9) Uani 1 1 d . . . . .
C23 C 0.3805(3) 0.5259(3) 0.5069(2) 0.0301(9) Uani 1 1 d . . . . .
H23 H 0.419221 0.527608 0.481151 0.036 Uiso 1 1 calc R . . . .
C24 C 0.4068(3) 0.5663(3) 0.5724(2) 0.0276(8) Uani 1 1 d . . . . .
C25 C 0.5014(3) 0.4400(2) 0.7182(2) 0.0274(8) Uani 1 1 d . . . . .
C26 C 0.4445(3) 0.3851(3) 0.6663(2) 0.0319(9) Uani 1 1 d . . . . .
H26 H 0.382084 0.379964 0.658991 0.038 Uiso 1 1 calc R . . . .
C27 C 0.4815(3) 0.3376(3) 0.6249(2) 0.0368(10) Uani 1 1 d . . . . .
H27 H 0.443345 0.301046 0.587912 0.044 Uiso 1 1 calc R . . . .
C28 C 0.5726(3) 0.3429(3) 0.6370(2) 0.0374(10) Uani 1 1 d . . . . .
H28 H 0.596258 0.310692 0.607784 0.045 Uiso 1 1 calc R . . . .
C29 C 0.6302(3) 0.3948(3) 0.6914(2) 0.0334(9) Uani 1 1 d . . . . .
H29 H 0.693184 0.397487 0.700414 0.040 Uiso 1 1 calc R . . . .
C30 C 0.5937(3) 0.4426(2) 0.7322(2) 0.0280(8) Uani 1 1 d . . . . .
C31 C 0.6387(3) 0.4968(2) 0.7958(2) 0.0269(8) Uani 1 1 d . . . . .
C32 C 0.4789(3) 0.3663(3) 0.8420(2) 0.0350(10) Uani 1 1 d . . . . .
H32A H 0.496853 0.329931 0.809715 0.052 Uiso 1 1 calc GR . . . .
H32B H 0.438985 0.331426 0.858892 0.052 Uiso 1 1 calc GR . . . .
H32C H 0.532993 0.384233 0.882028 0.052 Uiso 1 1 calc GR . . . .
C33 C 0.7389(3) 0.5107(3) 0.8224(2) 0.0277(8) Uani 1 1 d . . . . .
C34 C 0.7989(3) 0.4472(3) 0.8636(2) 0.0316(9) Uani 1 1 d . . . . .
C35 C 0.8919(3) 0.4599(3) 0.8923(2) 0.0371(10) Uani 1 1 d . . . . .
H35 H 0.930881 0.415861 0.921357 0.044 Uiso 1 1 calc R . . . .
C36 C 0.9259(3) 0.5383(3) 0.8773(2) 0.0362(10) Uani 1 1 d . . . . .
C37 C 0.8710(3) 0.6022(3) 0.8329(2) 0.0327(9) Uani 1 1 d . . . . .
H37 H 0.895982 0.654431 0.821154 0.039 Uiso 1 1 calc R . . . .
C38 C 0.7777(3) 0.5871(3) 0.8060(2) 0.0283(8) Uani 1 1 d . . . . .
C39 C 0.5569(3) 0.5939(3) 0.9882(2) 0.0341(9) Uani 1 1 d . . . . .
H39A H 0.503190 0.632173 0.971314 0.051 Uiso 1 1 calc GR . . . .
H39B H 0.611468 0.631038 1.006176 0.051 Uiso 1 1 calc GR . . . .
H39C H 0.554090 0.555462 1.025953 0.051 Uiso 1 1 calc GR . . . .
C40 C 0.6777(3) 0.6315(3) 0.91753(19) 0.0250(8) Uani 1 1 d . . . . .
C41 C 0.7582(3) 0.5947(3) 0.9619(2) 0.0285(8) Uani 1 1 d . . . . .
H41 H 0.762167 0.532886 0.972577 0.034 Uiso 1 1 calc R . . . .
C42 C 0.8335(3) 0.6495(3) 0.9909(2) 0.0321(9) Uani 1 1 d . . . . .
H42 H 0.889544 0.625055 1.021135 0.039 Uiso 1 1 calc R . . . .
C43 C 0.8268(3) 0.7401(3) 0.9755(2) 0.0328(9) Uani 1 1 d . . . . .
H43 H 0.879114 0.776664 0.994265 0.039 Uiso 1 1 calc R . . . .
C44 C 0.7447(3) 0.7782(3) 0.9332(2) 0.0315(9) Uani 1 1 d . . . . .
H44 H 0.740011 0.840386 0.923756 0.038 Uiso 1 1 calc R . . . .
C45 C 0.6696(3) 0.7225(2) 0.9051(2) 0.0257(8) Uani 1 1 d . . . . .
C46 C 0.5737(3) 0.7441(3) 0.8631(2) 0.0262(8) Uani 1 1 d . . . . .
C47 C 0.5477(3) 0.8395(3) 0.8484(2) 0.0291(8) Uani 1 1 d . . . . .
C48 C 0.5398(3) 0.8929(3) 0.9017(2) 0.0339(9) Uani 1 1 d . . . . .
C49 C 0.5213(3) 0.9836(3) 0.8927(3) 0.0396(11) Uani 1 1 d . . . . .
H49 H 0.515248 1.018284 0.929371 0.048 Uiso 1 1 calc R . . . .
C50 C 0.5121(3) 1.0216(3) 0.8303(3) 0.0440(12) Uani 1 1 d . . . . .
C51 C 0.5179(3) 0.9728(3) 0.7751(3) 0.0432(11) Uani 1 1 d . . . . .
H51 H 0.509298 1.000220 0.731355 0.052 Uiso 1 1 calc R . . . .
C52 C 0.5368(3) 0.8820(3) 0.7857(2) 0.0335(9) 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C2 C1 C14 108.7(3) . . ?
C6 C1 C2 107.7(3) . . ?
C6 C1 C14 112.6(3) . . ?
C7 C1 C2 102.2(3) . . ?
C7 C1 C6 117.7(3) . . ?
C7 C1 C14 107.2(3) . . ?
C14 O1 C15 116.3(3) . . ?
C39 O2 C5 113.5(3) . . ?
C3 C2 C1 118.3(3) . . ?
C13 C2 C1 109.9(3) . . ?
C13 C2 C3 131.8(3) . . ?
C32 O3 C3 114.2(3) . . ?
C2 C3 C4 106.5(3) . . ?
C2 C3 C25 116.8(3) . . ?
O3 C3 C2 105.9(3) . . ?
O3 C3 C4 115.1(3) . . ?
O3 C3 C25 111.1(3) . . ?
C25 C3 C4 101.7(3) . . ?
C5 C4 C3 118.4(3) . . ?
C31 C4 C3 109.7(3) . . ?
C31 C4 C5 131.2(4) . . ?
O2 C5 C4 107.2(3) . . ?
O2 C5 C6 113.3(3) . . ?
O2 C5 C40 110.3(3) . . ?
C4 C5 C6 106.9(3) . . ?
C4 C5 C40 116.7(3) . . ?
C40 C5 C6 102.6(3) . . ?
C1 C6 C5 117.7(3) . . ?
C46 C6 C1 132.5(4) . . ?
C46 C6 C5 109.3(3) . . ?
C8 C7 C1 130.9(4) . . ?
C8 C7 C12 119.9(4) . . ?
C12 C7 C1 108.8(3) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(4) . . ?
C9 C8 H8 120.5 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.7(4) . . ?
C10 C9 H9 119.6 . . ?
C9 C10 H10 119.5 . . ?
C9 C10 C11 120.9(4) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 H11 120.9 . . ?
C12 C11 C10 118.1(4) . . ?
C12 C11 H11 120.9 . . ?
C7 C12 C13 109.2(3) . . ?
C11 C12 C7 121.1(4) . . ?
C11 C12 C13 129.7(4) . . ?
C2 C13 C12 109.9(3) . . ?
C2 C13 C19 130.2(3) . . ?
C12 C13 C19 119.8(3) . . ?
C1 C14 H14A 110.2 . . ?
C1 C14 H14B 110.2 . . ?
O1 C14 C1 107.4(3) . . ?
O1 C14 H14A 110.2 . . ?
O1 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
O1 C15 C16 111.0(4) . . ?
O1 C15 C17 102.8(4) . . ?
O1 C15 C18 110.7(4) . . ?
C16 C15 C17 109.8(4) . . ?
C16 C15 C18 111.1(4) . . ?
C17 C15 C18 111.2(4) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C13 120.8(3) . . ?
C20 C19 C24 115.9(4) . . ?
C24 C19 C13 123.2(3) . . ?
C19 C20 Cl1 119.2(3) . . ?
C21 C20 Cl1 117.2(3) . . ?
C21 C20 C19 123.6(4) . . ?
C20 C21 H21 120.8 . . ?
C20 C21 C22 118.4(4) . . ?
C22 C21 H21 120.8 . . ?
C21 C22 Cl2 119.2(3) . . ?
C23 C22 Cl2 120.3(3) . . ?
C23 C22 C21 120.5(4) . . ?
C22 C23 H23 120.3 . . ?
C22 C23 C24 119.5(4) . . ?
C24 C23 H23 120.3 . . ?
C19 C24 Cl3 119.3(3) . . ?
C23 C24 Cl3 118.6(3) . . ?
C23 C24 C19 122.1(4) . . ?
C26 C25 C3 129.2(4) . . ?
C26 C25 C30 120.9(4) . . ?
C30 C25 C3 109.5(3) . . ?
C25 C26 H26 121.0 . . ?
C25 C26 C27 117.9(4) . . ?
C27 C26 H26 121.0 . . ?
C26 C27 H27 119.5 . . ?
C28 C27 C26 121.0(4) . . ?
C28 C27 H27 119.5 . . ?
C27 C28 H28 119.7 . . ?
C27 C28 C29 120.7(4) . . ?
C29 C28 H28 119.7 . . ?
C28 C29 H29 120.8 . . ?
C30 C29 C28 118.5(4) . . ?
C30 C29 H29 120.8 . . ?
C25 C30 C31 108.9(3) . . ?
C29 C30 C25 120.8(4) . . ?
C29 C30 C31 130.2(4) . . ?
C4 C31 C30 110.0(3) . . ?
C4 C31 C33 129.9(4) . . ?
C30 C31 C33 120.0(3) . . ?
O3 C32 H32A 109.5 . . ?
O3 C32 H32B 109.5 . . ?
O3 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C34 C33 C31 121.6(4) . . ?
C34 C33 C38 116.2(4) . . ?
C38 C33 C31 122.2(4) . . ?
C33 C34 Cl4 119.0(3) . . ?
C35 C34 Cl4 117.8(3) . . ?
C35 C34 C33 123.1(4) . . ?
C34 C35 H35 121.0 . . ?
C36 C35 C34 118.0(4) . . ?
C36 C35 H35 121.0 . . ?
C35 C36 Cl5 119.3(3) . . ?
C35 C36 C37 122.3(4) . . ?
C37 C36 Cl5 118.4(3) . . ?
C36 C37 H37 121.2 . . ?
C36 C37 C38 117.7(4) . . ?
C38 C37 H37 121.2 . . ?
C33 C38 Cl6 119.7(3) . . ?
C37 C38 Cl6 117.8(3) . . ?
C37 C38 C33 122.5(4) . . ?
O2 C39 H39A 109.5 . . ?
O2 C39 H39B 109.5 . . ?
O2 C39 H39C 109.5 . . ?
H39A C39 H39B 109.5 . . ?
H39A C39 H39C 109.5 . . ?
H39B C39 H39C 109.5 . . ?
C41 C40 C5 129.8(4) . . ?
C41 C40 C45 121.0(4) . . ?
C45 C40 C5 109.0(3) . . ?
C40 C41 H41 120.5 . . ?
C40 C41 C42 119.0(4) . . ?
C42 C41 H41 120.5 . . ?
C41 C42 H42 120.0 . . ?
C41 C42 C43 120.0(4) . . ?
C43 C42 H42 120.0 . . ?
C42 C43 H43 119.4 . . ?
C42 C43 C44 121.1(4) . . ?
C44 C43 H43 119.4 . . ?
C43 C44 H44 120.9 . . ?
C43 C44 C45 118.1(4) . . ?
C45 C44 H44 120.9 . . ?
C40 C45 C44 120.5(4) . . ?
C40 C45 C46 109.1(3) . . ?
C44 C45 C46 130.4(4) . . ?
C6 C46 C45 109.9(3) . . ?
C6 C46 C47 131.6(4) . . ?
C45 C46 C47 118.3(3) . . ?
C48 C47 C46 119.4(4) . . ?
C52 C47 C46 124.0(4) . . ?
C52 C47 C48 116.5(4) . . ?
C47 C48 Cl7 120.2(3) . . ?
C49 C48 Cl7 117.6(4) . . ?
C49 C48 C47 122.2(4) . . ?
C48 C49 H49 120.7 . . ?
C50 C49 C48 118.7(4) . . ?
C50 C49 H49 120.7 . . ?
C49 C50 Cl8 118.8(4) . . ?
C49 C50 C51 122.3(4) . . ?
C51 C50 Cl8 118.9(4) . . ?
C50 C51 H51 121.1 . . ?
C50 C51 C52 117.8(4) . . ?
C52 C51 H51 121.1 . . ?
C47 C52 Cl9 119.6(3) . . ?
C47 C52 C51 122.6(4) . . ?
C51 C52 Cl9 117.8(4) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C20 1.739(4) . ?
C1 C2 1.548(5) . ?
C1 C6 1.519(5) . ?
C1 C7 1.518(5) . ?
C1 C14 1.555(5) . ?
O1 C14 1.421(5) . ?
O1 C15 1.447(5) . ?
Cl2 C22 1.728(4) . ?
O2 C5 1.444(4) . ?
O2 C39 1.438(5) . ?
C2 C3 1.514(5) . ?
C2 C13 1.342(5) . ?
O3 C3 1.438(5) . ?
O3 C32 1.433(5) . ?
Cl3 C24 1.736(4) . ?
C3 C4 1.556(5) . ?
C3 C25 1.526(5) . ?
C4 C5 1.505(5) . ?
C4 C31 1.347(5) . ?
Cl4 C34 1.743(4) . ?
C5 C6 1.553(5) . ?
C5 C40 1.513(5) . ?
Cl5 C36 1.741(4) . ?
C6 C46 1.342(5) . ?
Cl6 C38 1.728(4) . ?
Cl7 C48 1.727(5) . ?
C7 C8 1.385(5) . ?
C7 C12 1.396(5) . ?
Cl8 C50 1.740(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.391(6) . ?
C9 H9 0.9500 . ?
C9 C10 1.378(6) . ?
Cl9 C52 1.738(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.393(6) . ?
C11 H11 0.9500 . ?
C11 C12 1.388(5) . ?
C12 C13 1.469(5) . ?
C13 C19 1.494(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C16 1.496(6) . ?
C15 C17 1.508(7) . ?
C15 C18 1.533(7) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.386(5) . ?
C19 C24 1.401(5) . ?
C20 C21 1.383(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.388(6) . ?
C22 C23 1.376(6) . ?
C23 H23 0.9500 . ?
C23 C24 1.389(5) . ?
C25 C26 1.384(6) . ?
C25 C30 1.388(6) . ?
C26 H26 0.9500 . ?
C26 C27 1.397(6) . ?
C27 H27 0.9500 . ?
C27 C28 1.379(6) . ?
C28 H28 0.9500 . ?
C28 C29 1.390(6) . ?
C29 H29 0.9500 . ?
C29 C30 1.383(5) . ?
C30 C31 1.478(5) . ?
C31 C33 1.494(5) . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 C34 1.390(6) . ?
C33 C38 1.402(5) . ?
C34 C35 1.386(6) . ?
C35 H35 0.9500 . ?
C35 C36 1.376(6) . ?
C36 C37 1.386(6) . ?
C37 H37 0.9500 . ?
C37 C38 1.395(6) . ?
C39 H39A 0.9800 . ?
C39 H39B 0.9800 . ?
C39 H39C 0.9800 . ?
C40 C41 1.380(5) . ?
C40 C45 1.387(5) . ?
C41 H41 0.9500 . ?
C41 C42 1.390(6) . ?
C42 H42 0.9500 . ?
C42 C43 1.390(6) . ?
C43 H43 0.9500 . ?
C43 C44 1.394(6) . ?
C44 H44 0.9500 . ?
C44 C45 1.394(5) . ?
C45 C46 1.482(5) . ?
C46 C47 1.490(5) . ?
C47 C48 1.399(6) . ?
C47 C52 1.387(6) . ?
C48 C49 1.390(6) . ?
C49 H49 0.9500 . ?
C49 C50 1.358(7) . ?
C50 C51 1.381(7) . ?
C51 H51 0.9500 . ?
C51 C52 1.395(6) . ?
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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C20 C21 C22 -178.6(3) . . . . ?
C1 C2 C3 O3 72.1(4) . . . . ?
C1 C2 C3 C4 -50.9(4) . . . . ?
C1 C2 C3 C25 -163.7(3) . . . . ?
C1 C2 C13 C12 0.4(4) . . . . ?
C1 C2 C13 C19 -175.2(4) . . . . ?
C1 C6 C46 C45 -172.7(4) . . . . ?
C1 C6 C46 C47 11.6(7) . . . . ?
C1 C7 C8 C9 -175.3(4) . . . . ?
C1 C7 C12 C11 175.8(4) . . . . ?
C1 C7 C12 C13 -3.3(4) . . . . ?
Cl2 C22 C23 C24 179.6(3) . . . . ?
O2 C5 C6 C1 -66.0(4) . . . . ?
O2 C5 C6 C46 120.2(3) . . . . ?
O2 C5 C40 C41 51.3(5) . . . . ?
O2 C5 C40 C45 -123.0(3) . . . . ?
C2 C1 C6 C5 -50.6(4) . . . . ?
C2 C1 C6 C46 121.5(4) . . . . ?
C2 C1 C7 C8 175.9(4) . . . . ?
C2 C1 C7 C12 3.3(4) . . . . ?
C2 C1 C14 O1 -172.8(3) . . . . ?
C2 C3 C4 C5 52.9(4) . . . . ?
C2 C3 C4 C31 -118.8(3) . . . . ?
C2 C3 C25 C26 -74.8(5) . . . . ?
C2 C3 C25 C30 112.5(4) . . . . ?
C2 C13 C19 C20 95.2(5) . . . . ?
C2 C13 C19 C24 -88.7(5) . . . . ?
O3 C3 C4 C5 -64.2(4) . . . . ?
O3 C3 C4 C31 124.2(3) . . . . ?
O3 C3 C25 C26 46.7(5) . . . . ?
O3 C3 C25 C30 -125.9(3) . . . . ?
C3 C2 C13 C12 -177.2(4) . . . . ?
C3 C2 C13 C19 7.2(7) . . . . ?
C3 C4 C5 O2 69.0(4) . . . . ?
C3 C4 C5 C6 -52.7(4) . . . . ?
C3 C4 C5 C40 -166.8(3) . . . . ?
C3 C4 C31 C30 -3.6(4) . . . . ?
C3 C4 C31 C33 178.0(4) . . . . ?
C3 C25 C26 C27 -176.7(4) . . . . ?
C3 C25 C30 C29 177.8(4) . . . . ?
C3 C25 C30 C31 1.0(4) . . . . ?
C4 C3 C25 C26 169.7(4) . . . . ?
C4 C3 C25 C30 -2.9(4) . . . . ?
C4 C5 C6 C1 51.8(4) . . . . ?
C4 C5 C6 C46 -122.0(3) . . . . ?
C4 C5 C40 C41 -71.2(5) . . . . ?
C4 C5 C40 C45 114.4(4) . . . . ?
C4 C31 C33 C34 96.5(5) . . . . ?
C4 C31 C33 C38 -85.2(5) . . . . ?
Cl4 C34 C35 C36 -179.1(3) . . . . ?
C5 C4 C31 C30 -173.8(4) . . . . ?
C5 C4 C31 C33 7.8(7) . . . . ?
C5 C6 C46 C45 -0.1(4) . . . . ?
C5 C6 C46 C47 -175.8(4) . . . . ?
C5 C40 C41 C42 -177.9(4) . . . . ?
C5 C40 C45 C44 179.7(3) . . . . ?
C5 C40 C45 C46 2.1(4) . . . . ?
Cl5 C36 C37 C38 -178.0(3) . . . . ?
C6 C1 C2 C3 51.1(4) . . . . ?
C6 C1 C2 C13 -126.8(3) . . . . ?
C6 C1 C7 C8 -66.5(5) . . . . ?
C6 C1 C7 C12 120.9(4) . . . . ?
C6 C1 C14 O1 68.0(4) . . . . ?
C6 C5 C40 C41 172.3(4) . . . . ?
C6 C5 C40 C45 -2.0(4) . . . . ?
C6 C46 C47 C48 99.7(5) . . . . ?
C6 C46 C47 C52 -85.1(6) . . . . ?
Cl7 C48 C49 C50 180.0(3) . . . . ?
C7 C1 C2 C3 175.7(3) . . . . ?
C7 C1 C2 C13 -2.2(4) . . . . ?
C7 C1 C6 C5 -165.2(3) . . . . ?
C7 C1 C6 C46 6.9(6) . . . . ?
C7 C1 C14 O1 -63.0(4) . . . . ?
C7 C8 C9 C10 1.7(6) . . . . ?
C7 C12 C13 C2 1.9(5) . . . . ?
C7 C12 C13 C19 178.0(3) . . . . ?
Cl8 C50 C51 C52 177.8(4) . . . . ?
C8 C7 C12 C11 2.3(6) . . . . ?
C8 C7 C12 C13 -176.8(3) . . . . ?
C8 C9 C10 C11 1.4(7) . . . . ?
C9 C10 C11 C12 -2.6(7) . . . . ?
C10 C11 C12 C7 0.7(6) . . . . ?
C10 C11 C12 C13 179.6(4) . . . . ?
C11 C12 C13 C2 -177.1(4) . . . . ?
C11 C12 C13 C19 -1.0(6) . . . . ?
C12 C7 C8 C9 -3.4(6) . . . . ?
C12 C13 C19 C20 -80.1(5) . . . . ?
C12 C13 C19 C24 96.0(5) . . . . ?
C13 C2 C3 O3 -110.5(5) . . . . ?
C13 C2 C3 C4 126.5(4) . . . . ?
C13 C2 C3 C25 13.7(6) . . . . ?
C13 C19 C20 Cl1 -4.5(5) . . . . ?
C13 C19 C20 C21 177.7(4) . . . . ?
C13 C19 C24 Cl3 3.4(5) . . . . ?
C13 C19 C24 C23 -177.8(4) . . . . ?
C14 C1 C2 C3 -71.2(4) . . . . ?
C14 C1 C2 C13 110.9(4) . . . . ?
C14 C1 C6 C5 69.3(4) . . . . ?
C14 C1 C6 C46 -118.6(4) . . . . ?
C14 C1 C7 C8 61.6(5) . . . . ?
C14 C1 C7 C12 -111.0(3) . . . . ?
C14 O1 C15 C16 59.1(5) . . . . ?
C14 O1 C15 C17 176.5(4) . . . . ?
C14 O1 C15 C18 -64.7(5) . . . . ?
C15 O1 C14 C1 153.3(3) . . . . ?
C19 C20 C21 C22 -0.7(6) . . . . ?
C20 C19 C24 Cl3 179.6(3) . . . . ?
C20 C19 C24 C23 -1.6(6) . . . . ?
C20 C21 C22 Cl2 -179.8(3) . . . . ?
C20 C21 C22 C23 0.3(6) . . . . ?
C21 C22 C23 C24 -0.5(6) . . . . ?
C22 C23 C24 Cl3 -180.0(3) . . . . ?
C22 C23 C24 C19 1.2(6) . . . . ?
C24 C19 C20 Cl1 179.2(3) . . . . ?
C24 C19 C20 C21 1.4(6) . . . . ?
C25 C3 C4 C5 175.6(3) . . . . ?
C25 C3 C4 C31 4.0(4) . . . . ?
C25 C26 C27 C28 2.1(6) . . . . ?
C25 C30 C31 C4 1.7(4) . . . . ?
C25 C30 C31 C33 -179.7(3) . . . . ?
C26 C25 C30 C29 4.4(6) . . . . ?
C26 C25 C30 C31 -172.3(3) . . . . ?
C26 C27 C28 C29 0.9(7) . . . . ?
C27 C28 C29 C30 -1.4(6) . . . . ?
C28 C29 C30 C25 -1.2(6) . . . . ?
C28 C29 C30 C31 174.7(4) . . . . ?
C29 C30 C31 C4 -174.6(4) . . . . ?
C29 C30 C31 C33 4.0(6) . . . . ?
C30 C25 C26 C27 -4.7(6) . . . . ?
C30 C31 C33 C34 -81.8(5) . . . . ?
C30 C31 C33 C38 96.5(5) . . . . ?
C31 C4 C5 O2 -121.5(4) . . . . ?
C31 C4 C5 C6 116.8(4) . . . . ?
C31 C4 C5 C40 2.7(6) . . . . ?
C31 C33 C34 Cl4 0.8(5) . . . . ?
C31 C33 C34 C35 -176.4(4) . . . . ?
C31 C33 C38 Cl6 -0.4(5) . . . . ?
C31 C33 C38 C37 177.4(4) . . . . ?
C32 O3 C3 C2 -172.4(3) . . . . ?
C32 O3 C3 C4 -55.0(4) . . . . ?
C32 O3 C3 C25 59.9(4) . . . . ?
C33 C34 C35 C36 -1.9(6) . . . . ?
C34 C33 C38 Cl6 178.0(3) . . . . ?
C34 C33 C38 C37 -4.2(6) . . . . ?
C34 C35 C36 Cl5 178.9(3) . . . . ?
C34 C35 C36 C37 -2.6(7) . . . . ?
C35 C36 C37 C38 3.4(6) . . . . ?
C36 C37 C38 Cl6 178.0(3) . . . . ?
C36 C37 C38 C33 0.1(6) . . . . ?
C38 C33 C34 Cl4 -177.7(3) . . . . ?
C38 C33 C34 C35 5.1(6) . . . . ?
C39 O2 C5 C4 -174.6(3) . . . . ?
C39 O2 C5 C6 -57.0(4) . . . . ?
C39 O2 C5 C40 57.4(4) . . . . ?
C40 C5 C6 C1 175.1(3) . . . . ?
C40 C5 C6 C46 1.3(4) . . . . ?
C40 C41 C42 C43 0.7(6) . . . . ?
C40 C45 C46 C6 -1.2(4) . . . . ?
C40 C45 C46 C47 175.1(3) . . . . ?
C41 C40 C45 C44 4.8(6) . . . . ?
C41 C40 C45 C46 -172.9(3) . . . . ?
C41 C42 C43 C44 2.2(6) . . . . ?
C42 C43 C44 C45 -1.5(6) . . . . ?
C43 C44 C45 C40 -1.9(6) . . . . ?
C43 C44 C45 C46 175.2(4) . . . . ?
C44 C45 C46 C6 -178.6(4) . . . . ?
C44 C45 C46 C47 -2.2(6) . . . . ?
C45 C40 C41 C42 -4.1(6) . . . . ?
C45 C46 C47 C48 -75.7(5) . . . . ?
C45 C46 C47 C52 99.5(5) . . . . ?
C46 C47 C48 Cl7 -5.1(5) . . . . ?
C46 C47 C48 C49 176.0(4) . . . . ?
C46 C47 C52 Cl9 6.2(6) . . . . ?
C46 C47 C52 C51 -176.0(4) . . . . ?
C47 C48 C49 C50 -1.1(6) . . . . ?
C48 C47 C52 Cl9 -178.5(3) . . . . ?
C48 C47 C52 C51 -0.7(6) . . . . ?
C48 C49 C50 Cl8 -178.0(3) . . . . ?
C48 C49 C50 C51 1.9(7) . . . . ?
C49 C50 C51 C52 -2.1(7) . . . . ?
C50 C51 C52 Cl9 179.3(4) . . . . ?
C50 C51 C52 C47 1.5(7) . . . . ?
C52 C47 C48 Cl7 179.4(3) . . . . ?
C52 C47 C48 C49 0.4(6) . . . . ?
