#------------------------------------------------------------------------------
#$Date: 2022-06-22 09:23:47 +0300 (Wed, 22 Jun 2022) $
#$Revision: 276143 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/92/1559239.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_1559239
loop_
_publ_author_name
'Liu, Zhong'
'Tu, Xian-Shuang'
'Guo, Le-Tao'
'Wang, Xiao-Chen'
_publ_section_title
;
 Aluminum--Catalyzed Tunable Halodefluorination of Trifluoromethyl- and
 Difluoroalkyl-Substituted Olefins
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D0SC03883K
_journal_year                    2020
_chemical_formula_sum            'C15 H11 Cl3'
_chemical_formula_weight         297.58
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-05-13 deposited with the CCDC.	2020-10-01 downloaded from the CCDC.
;
_cell_angle_alpha                105.723(5)
_cell_angle_beta                 108.005(5)
_cell_angle_gamma                100.048(4)
_cell_formula_units_Z            8
_cell_length_a                   13.0257(7)
_cell_length_b                   13.3355(7)
_cell_length_c                   18.0392(9)
_cell_measurement_reflns_used    12015
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      31.0430
_cell_measurement_theta_min      2.3330
_cell_volume                     2752.0(3)
_computing_cell_refinement       crystalclear
_computing_data_collection       crystalclear
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      113(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'rigaku saturn'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0462
_diffrn_reflns_av_unetI/netI     0.0585
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            21382
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.020
_diffrn_reflns_theta_max         25.020
_diffrn_reflns_theta_min         1.654
_diffrn_source                   'rotating anode'
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_correction_T_min  0.69505
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.436
_exptl_crystal_description       blocks
_exptl_crystal_F_000             1216
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.120
_refine_diff_density_max         1.298
_refine_diff_density_min         -0.698
_refine_diff_density_rms         0.144
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         9633
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.081
_refine_ls_R_factor_all          0.1175
_refine_ls_R_factor_gt           0.0986
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1770P)²+9.2942P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2926
_refine_ls_wR_factor_ref         0.3124
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7399
_reflns_number_total             9633
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d0sc03883k2.cif
_cod_data_source_block           r20191017b
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'MULTI-SCAN' was
changed to 'multi-scan' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

2022-06-10
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum            'C30 H22 Cl6'
_cod_original_formula_weight         595.17
_cod_original_formula_units_Z            4
_cod_database_code               1559239
_shelx_shelxl_version_number     2018/3
_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_min   0.882
_shelx_estimated_absorpt_t_max   0.927
loop_
_space_group_symop_operation_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_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 1.02887(13) 1.07745(15) 0.13947(11) 0.0495(5) Uani 1 1 d . . . . .
Cl2 Cl 0.96141(16) 1.20156(16) -0.02980(15) 0.0624(6) Uani 1 1 d . . . . .
Cl3 Cl 0.74975(17) 1.04603(16) -0.13977(12) 0.0563(5) Uani 1 1 d . . . . .
Cl4 Cl 0.1341(2) 0.28381(15) 0.87671(14) 0.0619(6) Uani 1 1 d . . . . .
Cl5 Cl 0.00863(17) -0.01493(16) 0.68494(14) 0.0647(6) Uani 1 1 d . . . . .
Cl6 Cl 0.12043(17) 0.06591(16) 0.59034(11) 0.0560(5) Uani 1 1 d . . . . .
Cl7 Cl 0.45699(16) 0.89798(15) 0.36535(11) 0.0505(5) Uani 1 1 d . . . . .
Cl8 Cl 0.74425(16) 1.00931(15) 0.54972(14) 0.0580(5) Uani 1 1 d . . . . .
Cl9 Cl 0.68841(16) 0.89681(15) 0.65150(11) 0.0539(5) Uani 1 1 d . . . . .
Cl10 Cl -0.09178(18) 0.25171(15) 0.60474(15) 0.0679(7) Uani 1 1 d . . . . .
Cl11 Cl -0.20718(18) 0.2923(2) 0.80398(14) 0.0670(6) Uani 1 1 d . . . . .
Cl12 Cl -0.03428(17) 0.49288(19) 0.90000(11) 0.0616(6) Uani 1 1 d . . . . .
C1 C 0.4592(5) 0.6213(5) -0.0431(4) 0.0341(13) Uani 1 1 d . . . . .
H1 H 0.517766 0.602218 -0.059604 0.041 Uiso 1 1 calc R U . . .
C2 C 0.3712(5) 0.5400(5) -0.0483(4) 0.0371(14) Uani 1 1 d . . . . .
H2 H 0.369324 0.465935 -0.069385 0.045 Uiso 1 1 calc R U . . .
C3 C 0.2874(5) 0.5664(5) -0.0232(4) 0.0408(15) Uani 1 1 d . . . . .
H3 H 0.228753 0.511021 -0.025196 0.049 Uiso 1 1 calc R U . . .
C4 C 0.2885(5) 0.6752(5) 0.0053(4) 0.0413(15) Uani 1 1 d . . . . .
H4 H 0.229723 0.693797 0.021708 0.050 Uiso 1 1 calc R U . . .
C5 C 0.3752(5) 0.7560(5) 0.0096(4) 0.0370(14) Uani 1 1 d . . . . .
H5 H 0.375184 0.829692 0.028824 0.044 Uiso 1 1 calc R U . . .
C6 C 0.4624(5) 0.7307(5) -0.0138(3) 0.0306(13) Uani 1 1 d . . . . .
C7 C 0.5588(5) 0.8189(5) -0.0049(3) 0.0301(12) Uani 1 1 d . . . . .
C8 C 0.5838(5) 0.9243(5) 0.0502(4) 0.0336(13) Uani 1 1 d . . . . .
H8 H 0.538971 0.939757 0.082159 0.040 Uiso 1 1 calc R U . . .
C9 C 0.6727(5) 1.0070(5) 0.0592(4) 0.0353(14) Uani 1 1 d . . . . .
H9 H 0.687856 1.077823 0.097225 0.042 Uiso 1 1 calc R U . . .
C10 C 0.7401(5) 0.9876(5) 0.0132(4) 0.0338(13) Uani 1 1 d . . . . .
C11 C 0.7167(5) 0.8817(5) -0.0407(4) 0.0330(13) Uani 1 1 d . . . . .
H11 H 0.762348 0.865900 -0.071953 0.040 Uiso 1 1 calc R U . . .
C12 C 0.6284(5) 0.7997(5) -0.0491(4) 0.0320(13) Uani 1 1 d . . . . .
H12 H 0.614701 0.728424 -0.086013 0.038 Uiso 1 1 calc R U . . .
C13 C 0.8350(5) 1.0775(5) 0.0245(4) 0.0357(14) Uani 1 1 d . . . . .
C14 C 0.9189(6) 1.1416(6) 0.1108(5) 0.0507(18) Uani 1 1 d . . . . .
H14A H 0.880228 1.147574 0.150498 0.061 Uiso 1 1 calc R U . . .
H14B H 0.952439 1.215823 0.113722 0.061 Uiso 1 1 calc R U . . .
C15 C 0.8473(6) 1.1047(5) -0.0394(5) 0.0442(16) Uani 1 1 d . . . . .
C16 C 0.5083(6) 0.5846(5) 0.7263(4) 0.0402(15) Uani 1 1 d . . . . .
H16 H 0.431253 0.577784 0.698088 0.048 Uiso 1 1 calc R U . . .
C17 C 0.5901(6) 0.6679(5) 0.7277(4) 0.0431(15) Uani 1 1 d . . . . .
H17 H 0.568081 0.716147 0.699652 0.052 Uiso 1 1 calc R U . . .
C18 C 0.7035(6) 0.6818(5) 0.7693(4) 0.0428(15) Uani 1 1 d . . . . .
H18 H 0.759553 0.739280 0.770764 0.051 Uiso 1 1 calc R U . . .
C19 C 0.7325(6) 0.6089(6) 0.8087(5) 0.0544(19) Uani 1 1 d . . . . .
H19 H 0.809597 0.616745 0.837680 0.065 Uiso 1 1 calc R U . . .
C20 C 0.6510(6) 0.5252(6) 0.8064(5) 0.0524(18) Uani 1 1 d . . . . .
H20 H 0.673796 0.476254 0.833489 0.063 Uiso 1 1 calc R U . . .
C21 C 0.5364(5) 0.5102(5) 0.7656(4) 0.0334(13) Uani 1 1 d . . . . .
C22 C 0.4490(5) 0.4202(5) 0.7620(4) 0.0306(12) Uani 1 1 d . . . . .
C23 C 0.4748(5) 0.3513(5) 0.8076(4) 0.0387(14) Uani 1 1 d . . . . .
H23 H 0.550831 0.362473 0.841567 0.046 Uiso 1 1 calc R U . . .
C24 C 0.3915(5) 0.2673(5) 0.8041(4) 0.0371(14) Uani 1 1 d . . . . .
H24 H 0.411997 0.222270 0.835579 0.044 Uiso 1 1 calc R U . . .
C25 C 0.2800(5) 0.2476(5) 0.7561(4) 0.0327(13) Uani 1 1 d . . . . .
C26 C 0.2528(5) 0.3148(5) 0.7101(4) 0.0416(15) Uani 1 1 d . . . . .
H26 H 0.176544 0.303352 0.676439 0.050 Uiso 1 1 calc R U . . .
C27 C 0.3361(6) 0.3983(5) 0.7129(4) 0.0417(15) Uani 1 1 d . . . . .
H27 H 0.315223 0.441929 0.680127 0.050 Uiso 1 1 calc R U . . .
C28 C 0.1909(5) 0.1620(5) 0.7571(4) 0.0373(14) Uani 1 1 d . . . . .
C29 C 0.1831(6) 0.1686(6) 0.8389(4) 0.0452(16) Uani 1 1 d . . . . .
H29A H 0.258006 0.176242 0.879380 0.054 Uiso 1 1 calc R U . . .
H29B H 0.130459 0.101029 0.832833 0.054 Uiso 1 1 calc R U . . .
C30 C 0.1163(6) 0.0834(5) 0.6874(4) 0.0425(15) Uani 1 1 d . . . . .
C31 C 0.2537(5) 0.3698(5) 0.4732(4) 0.0393(15) Uani 1 1 d . . . . .
H31 H 0.308127 0.353355 0.450544 0.047 Uiso 1 1 calc R U . . .
C32 C 0.1767(6) 0.2868(5) 0.4752(4) 0.0441(16) Uani 1 1 d . . . . .
H32 H 0.179217 0.214122 0.454454 0.053 Uiso 1 1 calc R U . . .
C33 C 0.0953(6) 0.3079(5) 0.5072(4) 0.0415(15) Uani 1 1 d . . . . .
H33 H 0.041792 0.250330 0.508130 0.050 Uiso 1 1 calc R U . . .
C34 C 0.0936(5) 0.4158(5) 0.5382(4) 0.0377(14) Uani 1 1 d . . . . .
H34 H 0.038878 0.431885 0.560660 0.045 Uiso 1 1 calc R U . . .
C35 C 0.1711(5) 0.4986(5) 0.5361(4) 0.0354(14) Uani 1 1 d . . . . .
H35 H 0.168726 0.571224 0.557149 0.042 Uiso 1 1 calc R U . . .
C36 C 0.2536(5) 0.4784(5) 0.5039(4) 0.0327(13) Uani 1 1 d . . . . .
C37 C 0.3356(5) 0.5680(5) 0.5000(3) 0.0310(13) Uani 1 1 d . . . . .
C38 C 0.3579(5) 0.6764(5) 0.5494(4) 0.0336(13) Uani 1 1 d . . . . .
H38 H 0.320669 0.693343 0.586968 0.040 Uiso 1 1 calc R U . . .
C39 C 0.4333(5) 0.7594(5) 0.5446(4) 0.0357(14) Uani 1 1 d . . . . .
H39 H 0.446902 0.832247 0.578811 0.043 Uiso 1 1 calc R U . . .
C40 C 0.4892(5) 0.7376(5) 0.4904(4) 0.0351(13) Uani 1 1 d . . . . .
C41 C 0.4668(6) 0.6311(5) 0.4401(4) 0.0395(15) Uani 1 1 d . . . . .
H41 H 0.503648 0.614857 0.402220 0.047 Uiso 1 1 calc R U . . .
C42 C 0.3906(5) 0.5475(5) 0.4445(4) 0.0389(15) Uani 1 1 d . . . . .
H42 H 0.375750 0.475109 0.409021 0.047 Uiso 1 1 calc R U . . .
C43 C 0.5708(5) 0.8256(5) 0.4852(4) 0.0372(14) Uani 1 1 d . . . . .
C44 C 0.5596(6) 0.8289(6) 0.4003(4) 0.0469(17) Uani 1 1 d . . . . .
H44A H 0.536395 0.753887 0.360398 0.056 Uiso 1 1 calc R U . . .
H44B H 0.633365 0.866969 0.402359 0.056 Uiso 1 1 calc R U . . .
C45 C 0.6549(6) 0.8999(5) 0.5525(5) 0.0434(16) Uani 1 1 d . . . . .
C46 C 0.3512(5) 0.7787(5) 0.7819(4) 0.0376(14) Uani 1 1 d . . . . .
H46 H 0.373178 0.738217 0.817053 0.045 Uiso 1 1 calc R U . . .
C47 C 0.4326(6) 0.8612(5) 0.7818(4) 0.0413(15) Uani 1 1 d . . . . .
H47 H 0.509152 0.876240 0.816384 0.050 Uiso 1 1 calc R U . . .
C48 C 0.4027(6) 0.9212(5) 0.7319(4) 0.0441(16) Uani 1 1 d . . . . .
H48 H 0.457999 0.978424 0.732360 0.053 Uiso 1 1 calc R U . . .
C49 C 0.2926(7) 0.8976(6) 0.6816(5) 0.0535(19) Uani 1 1 d . . . . .
H49 H 0.272064 0.938973 0.646892 0.064 Uiso 1 1 calc R U . . .
C50 C 0.2099(6) 0.8148(6) 0.6797(5) 0.0447(16) Uani 1 1 d . . . . .
H50 H 0.134137 0.799270 0.643239 0.054 Uiso 1 1 calc R U . . .
C51 C 0.2378(5) 0.7537(5) 0.7316(4) 0.0352(14) Uani 1 1 d . . . . .
C52 C 0.1510(5) 0.6667(5) 0.7329(3) 0.0328(13) Uani 1 1 d . . . . .
C53 C 0.0357(5) 0.6572(5) 0.6992(4) 0.0359(14) Uani 1 1 d . . . . .
H53 H 0.012163 0.708578 0.675193 0.043 Uiso 1 1 calc R U . . .
C54 C -0.0451(5) 0.5749(5) 0.7001(4) 0.0373(14) Uani 1 1 d . . . . .
H54 H -0.122450 0.570207 0.675779 0.045 Uiso 1 1 calc R U . . .
C55 C -0.0146(5) 0.4995(5) 0.7358(4) 0.0358(14) Uani 1 1 d . . . . .
C56 C 0.1005(6) 0.5080(6) 0.7691(4) 0.0451(16) Uani 1 1 d . . . . .
H56 H 0.123531 0.456215 0.792849 0.054 Uiso 1 1 calc R U . . .
C57 C 0.1808(6) 0.5892(5) 0.7683(4) 0.0413(15) Uani 1 1 d . . . . .
H57 H 0.258019 0.592985 0.792285 0.050 Uiso 1 1 calc R U . . .
C58 C -0.1006(5) 0.4081(5) 0.7339(4) 0.0384(14) Uani 1 1 d . . . . .
C59 C -0.1750(6) 0.3260(6) 0.6504(5) 0.0490(17) Uani 1 1 d . . . . .
H59A H -0.212005 0.362980 0.613557 0.059 Uiso 1 1 calc R U . . .
H59B H -0.234322 0.274754 0.656257 0.059 Uiso 1 1 calc R U . . .
C60 C -0.1111(6) 0.3987(6) 0.8026(4) 0.0477(17) 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'
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 C6 120.8(6) . . ?
C2 C1 H1 119.6 . . ?
C6 C1 H1 119.6 . . ?
C3 C2 C1 120.2(6) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 119.7(6) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C5 C4 C3 120.1(6) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 121.0(6) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.2(6) . . ?
C5 C6 C7 120.6(5) . . ?
C1 C6 C7 121.2(5) . . ?
C12 C7 C8 117.2(6) . . ?
C12 C7 C6 122.1(5) . . ?
C8 C7 C6 120.7(5) . . ?
C9 C8 C7 121.5(6) . . ?
C9 C8 H8 119.3 . . ?
C7 C8 H8 119.3 . . ?
C8 C9 C10 120.9(5) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C9 C10 C11 117.7(6) . . ?
C9 C10 C13 119.7(5) . . ?
C11 C10 C13 122.5(5) . . ?
C12 C11 C10 121.1(6) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C7 121.6(5) . . ?
C11 C12 H12 119.2 . . ?
C7 C12 H12 119.2 . . ?
C15 C13 C10 122.5(6) . . ?
C15 C13 C14 119.0(6) . . ?
C10 C13 C14 118.5(6) . . ?
C13 C14 Cl1 110.9(5) . . ?
C13 C14 H14A 109.5 . . ?
Cl1 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
Cl1 C14 H14B 109.5 . . ?
H14A C14 H14B 108.0 . . ?
C13 C15 Cl2 123.8(6) . . ?
C13 C15 Cl3 123.4(5) . . ?
Cl2 C15 Cl3 112.9(4) . . ?
C17 C16 C21 121.8(6) . . ?
C17 C16 H16 119.1 . . ?
C21 C16 H16 119.1 . . ?
C18 C17 C16 121.0(7) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 117.8(6) . . ?
C17 C18 H18 121.1 . . ?
C19 C18 H18 121.1 . . ?
C20 C19 C18 121.1(6) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 122.1(7) . . ?
C19 C20 H20 119.0 . . ?
C21 C20 H20 119.0 . . ?
C20 C21 C16 116.2(6) . . ?
C20 C21 C22 122.4(6) . . ?
C16 C21 C22 121.4(5) . . ?
C27 C22 C23 116.1(6) . . ?
C27 C22 C21 121.8(5) . . ?
C23 C22 C21 122.0(5) . . ?
C24 C23 C22 121.4(5) . . ?
C24 C23 H23 119.3 . . ?
C22 C23 H23 119.3 . . ?
C25 C24 C23 121.7(6) . . ?
C25 C24 H24 119.1 . . ?
C23 C24 H24 119.1 . . ?
C24 C25 C26 117.7(6) . . ?
C24 C25 C28 121.1(5) . . ?
C26 C25 C28 121.1(5) . . ?
C27 C26 C25 120.8(6) . . ?
C27 C26 H26 119.6 . . ?
C25 C26 H26 119.6 . . ?
C26 C27 C22 122.2(6) . . ?
C26 C27 H27 118.9 . . ?
C22 C27 H27 118.9 . . ?
C30 C28 C29 120.1(6) . . ?
C30 C28 C25 122.3(6) . . ?
C29 C28 C25 117.6(5) . . ?
C28 C29 Cl4 110.1(5) . . ?
C28 C29 H29A 109.6 . . ?
Cl4 C29 H29A 109.6 . . ?
C28 C29 H29B 109.6 . . ?
Cl4 C29 H29B 109.6 . . ?
H29A C29 H29B 108.2 . . ?
C28 C30 Cl6 123.7(6) . . ?
C28 C30 Cl5 124.1(6) . . ?
Cl6 C30 Cl5 112.1(4) . . ?
C32 C31 C36 121.4(6) . . ?
C32 C31 H31 119.3 . . ?
C36 C31 H31 119.3 . . ?
C31 C32 C33 120.8(6) . . ?
C31 C32 H32 119.6 . . ?
C33 C32 H32 119.6 . . ?
C32 C33 C34 118.7(6) . . ?
C32 C33 H33 120.6 . . ?
C34 C33 H33 120.6 . . ?
C35 C34 C33 120.1(6) . . ?
C35 C34 H34 120.0 . . ?
C33 C34 H34 120.0 . . ?
C34 C35 C36 121.7(6) . . ?
C34 C35 H35 119.1 . . ?
C36 C35 H35 119.1 . . ?
C35 C36 C31 117.2(6) . . ?
C35 C36 C37 121.5(5) . . ?
C31 C36 C37 121.3(5) . . ?
C42 C37 C38 117.2(6) . . ?
C42 C37 C36 121.1(5) . . ?
C38 C37 C36 121.7(5) . . ?
C39 C38 C37 121.2(6) . . ?
C39 C38 H38 119.4 . . ?
C37 C38 H38 119.4 . . ?
C38 C39 C40 120.9(6) . . ?
C38 C39 H39 119.5 . . ?
C40 C39 H39 119.5 . . ?
C41 C40 C39 118.6(6) . . ?
C41 C40 C43 119.9(6) . . ?
C39 C40 C43 121.5(6) . . ?
C40 C41 C42 120.6(6) . . ?
C40 C41 H41 119.7 . . ?
C42 C41 H41 119.7 . . ?
C41 C42 C37 121.4(6) . . ?
C41 C42 H42 119.3 . . ?
C37 C42 H42 119.3 . . ?
C45 C43 C40 122.7(6) . . ?
C45 C43 C44 119.3(6) . . ?
C40 C43 C44 118.0(6) . . ?
C43 C44 Cl7 110.8(5) . . ?
C43 C44 H44A 109.5 . . ?
Cl7 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
Cl7 C44 H44B 109.5 . . ?
H44A C44 H44B 108.1 . . ?
C43 C45 Cl9 124.4(5) . . ?
C43 C45 Cl8 124.0(6) . . ?
Cl9 C45 Cl8 111.6(4) . . ?
C47 C46 C51 121.6(6) . . ?
C47 C46 H46 119.2 . . ?
C51 C46 H46 119.2 . . ?
C48 C47 C46 120.2(6) . . ?
C48 C47 H47 119.9 . . ?
C46 C47 H47 119.9 . . ?
C49 C48 C47 119.2(7) . . ?
C49 C48 H48 120.4 . . ?
C47 C48 H48 120.4 . . ?
C48 C49 C50 121.8(7) . . ?
C48 C49 H49 119.1 . . ?
C50 C49 H49 119.1 . . ?
C49 C50 C51 120.2(7) . . ?
C49 C50 H50 119.9 . . ?
C51 C50 H50 119.9 . . ?
C46 C51 C50 117.0(6) . . ?
C46 C51 C52 121.4(6) . . ?
C50 C51 C52 121.6(6) . . ?
C53 C52 C57 116.6(6) . . ?
C53 C52 C51 122.2(5) . . ?
C57 C52 C51 121.2(6) . . ?
C54 C53 C52 121.8(6) . . ?
C54 C53 H53 119.1 . . ?
C52 C53 H53 119.1 . . ?
C55 C54 C53 121.1(6) . . ?
C55 C54 H54 119.5 . . ?
C53 C54 H54 119.5 . . ?
C54 C55 C56 117.5(6) . . ?
C54 C55 C58 121.5(5) . . ?
C56 C55 C58 120.9(6) . . ?
C57 C56 C55 121.7(6) . . ?
C57 C56 H56 119.1 . . ?
C55 C56 H56 119.1 . . ?
C56 C57 C52 121.3(6) . . ?
C56 C57 H57 119.3 . . ?
C52 C57 H57 119.3 . . ?
C60 C58 C55 122.0(6) . . ?
C60 C58 C59 121.0(7) . . ?
C55 C58 C59 117.0(6) . . ?
C58 C59 Cl10 109.8(5) . . ?
C58 C59 H59A 109.7 . . ?
Cl10 C59 H59A 109.7 . . ?
C58 C59 H59B 109.7 . . ?
Cl10 C59 H59B 109.7 . . ?
H59A C59 H59B 108.2 . . ?
C58 C60 Cl12 123.8(6) . . ?
C58 C60 Cl11 123.8(6) . . ?
Cl12 C60 Cl11 112.4(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 C14 1.806(8) . ?
Cl2 C15 1.720(7) . ?
Cl3 C15 1.723(8) . ?
Cl4 C29 1.810(7) . ?
Cl5 C30 1.725(7) . ?
Cl6 C30 1.722(7) . ?
Cl7 C44 1.804(7) . ?
Cl8 C45 1.723(7) . ?
Cl9 C45 1.717(7) . ?
Cl10 C59 1.822(7) . ?
Cl11 C60 1.732(8) . ?
Cl12 C60 1.716(8) . ?
C1 C2 1.395(9) . ?
C1 C6 1.399(8) . ?
C1 H1 0.9500 . ?
C2 C3 1.368(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.398(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.385(9) . ?
C4 H4 0.9500 . ?
C5 C6 1.391(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.497(9) . ?
C7 C12 1.394(8) . ?
C7 C8 1.398(8) . ?
C8 C9 1.387(9) . ?
C8 H8 0.9500 . ?
C9 C10 1.392(9) . ?
C9 H9 0.9500 . ?
C10 C11 1.398(9) . ?
C10 C13 1.484(9) . ?
C11 C12 1.380(9) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C15 1.343(10) . ?
C13 C14 1.499(9) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C16 C17 1.388(9) . ?
C16 C21 1.403(9) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(10) . ?
C17 H17 0.9500 . ?
C18 C19 1.389(11) . ?
C18 H18 0.9500 . ?
C19 C20 1.382(10) . ?
C19 H19 0.9500 . ?
C20 C21 1.396(9) . ?
C20 H20 0.9500 . ?
C21 C22 1.475(9) . ?
C22 C27 1.392(9) . ?
C22 C23 1.408(9) . ?
C23 C24 1.390(9) . ?
C23 H23 0.9500 . ?
C24 C25 1.375(8) . ?
C24 H24 0.9500 . ?
C25 C26 1.397(9) . ?
C25 C28 1.489(9) . ?
C26 C27 1.390(10) . ?
C26 H26 0.9500 . ?
C27 H27 0.9500 . ?
C28 C30 1.341(9) . ?
C28 C29 1.489(10) . ?
C29 H29A 0.9900 . ?
C29 H29B 0.9900 . ?
C31 C32 1.374(10) . ?
C31 C36 1.404(9) . ?
C31 H31 0.9500 . ?
C32 C33 1.391(10) . ?
C32 H32 0.9500 . ?
C33 C34 1.402(9) . ?
C33 H33 0.9500 . ?
C34 C35 1.376(9) . ?
C34 H34 0.9500 . ?
C35 C36 1.402(9) . ?
C35 H35 0.9500 . ?
C36 C37 1.489(9) . ?
C37 C42 1.398(9) . ?
C37 C38 1.402(8) . ?
C38 C39 1.387(9) . ?
C38 H38 0.9500 . ?
C39 C40 1.389(9) . ?
C39 H39 0.9500 . ?
C40 C41 1.386(9) . ?
C40 C43 1.484(9) . ?
C41 C42 1.395(10) . ?
C41 H41 0.9500 . ?
C42 H42 0.9500 . ?
C43 C45 1.343(10) . ?
C43 C44 1.506(9) . ?
C44 H44A 0.9900 . ?
C44 H44B 0.9900 . ?
C46 C47 1.390(9) . ?
C46 C51 1.397(9) . ?
C46 H46 0.9500 . ?
C47 C48 1.372(10) . ?
C47 H47 0.9500 . ?
C48 C49 1.365(11) . ?
C48 H48 0.9500 . ?
C49 C50 1.387(11) . ?
C49 H49 0.9500 . ?
C50 C51 1.406(9) . ?
C50 H50 0.9500 . ?
C51 C52 1.483(9) . ?
C52 C53 1.404(9) . ?
C52 C57 1.404(9) . ?
C53 C54 1.388(9) . ?
C53 H53 0.9500 . ?
C54 C55 1.383(9) . ?
C54 H54 0.9500 . ?
C55 C56 1.403(9) . ?
C55 C58 1.490(9) . ?
C56 C57 1.374(10) . ?
C56 H56 0.9500 . ?
C57 H57 0.9500 . ?
C58 C60 1.325(10) . ?
C58 C59 1.496(10) . ?
C59 H59A 0.9900 . ?
C59 H59B 0.9900 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C59 H59B Cl11 0.99 2.52 3.063(8) 114.5 . yes
C29 H29B Cl5 0.99 2.51 3.056(7) 114.2 . yes
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
C6 C1 C2 C3 -1.2(9) . . . . ?
C1 C2 C3 C4 2.0(9) . . . . ?
C2 C3 C4 C5 -1.3(10) . . . . ?
C3 C4 C5 C6 -0.3(10) . . . . ?
C4 C5 C6 C1 1.0(9) . . . . ?
C4 C5 C6 C7 -176.9(6) . . . . ?
C2 C1 C6 C5 -0.3(8) . . . . ?
C2 C1 C6 C7 177.7(5) . . . . ?
C5 C6 C7 C12 -160.1(6) . . . . ?
C1 C6 C7 C12 22.1(8) . . . . ?
C5 C6 C7 C8 21.2(8) . . . . ?
C1 C6 C7 C8 -156.6(6) . . . . ?
C12 C7 C8 C9 1.3(8) . . . . ?
C6 C7 C8 C9 -179.9(5) . . . . ?
C7 C8 C9 C10 0.2(9) . . . . ?
C8 C9 C10 C11 -1.5(9) . . . . ?
C8 C9 C10 C13 -179.6(6) . . . . ?
C9 C10 C11 C12 1.3(9) . . . . ?
C13 C10 C11 C12 179.3(6) . . . . ?
C10 C11 C12 C7 0.3(9) . . . . ?
C8 C7 C12 C11 -1.5(8) . . . . ?
C6 C7 C12 C11 179.7(5) . . . . ?
C9 C10 C13 C15 -126.3(7) . . . . ?
C11 C10 C13 C15 55.7(9) . . . . ?
C9 C10 C13 C14 52.5(8) . . . . ?
C11 C10 C13 C14 -125.6(7) . . . . ?
C15 C13 C14 Cl1 -94.6(7) . . . . ?
C10 C13 C14 Cl1 86.6(6) . . . . ?
C10 C13 C15 Cl2 -175.1(5) . . . . ?
C14 C13 C15 Cl2 6.2(9) . . . . ?
C10 C13 C15 Cl3 5.1(9) . . . . ?
C14 C13 C15 Cl3 -173.7(5) . . . . ?
C21 C16 C17 C18 -1.0(10) . . . . ?
C16 C17 C18 C19 0.7(10) . . . . ?
C17 C18 C19 C20 0.1(11) . . . . ?
C18 C19 C20 C21 -0.7(12) . . . . ?
C19 C20 C21 C16 0.5(11) . . . . ?
C19 C20 C21 C22 179.2(7) . . . . ?
C17 C16 C21 C20 0.4(9) . . . . ?
C17 C16 C21 C22 -178.3(6) . . . . ?
C20 C21 C22 C27 -172.1(7) . . . . ?
C16 C21 C22 C27 6.6(9) . . . . ?
C20 C21 C22 C23 7.7(9) . . . . ?
C16 C21 C22 C23 -173.7(6) . . . . ?
C27 C22 C23 C24 -0.7(9) . . . . ?
C21 C22 C23 C24 179.5(6) . . . . ?
C22 C23 C24 C25 -0.2(10) . . . . ?
C23 C24 C25 C26 0.5(10) . . . . ?
C23 C24 C25 C28 -176.0(6) . . . . ?
C24 C25 C26 C27 0.1(10) . . . . ?
C28 C25 C26 C27 176.6(6) . . . . ?
C25 C26 C27 C22 -1.1(11) . . . . ?
C23 C22 C27 C26 1.3(10) . . . . ?
C21 C22 C27 C26 -178.9(6) . . . . ?
C24 C25 C28 C30 -126.5(7) . . . . ?
C26 C25 C28 C30 57.1(9) . . . . ?
C24 C25 C28 C29 56.2(8) . . . . ?
C26 C25 C28 C29 -120.2(7) . . . . ?
C30 C28 C29 Cl4 -108.1(6) . . . . ?
C25 C28 C29 Cl4 69.3(6) . . . . ?
C29 C28 C30 Cl6 -177.9(5) . . . . ?
C25 C28 C30 Cl6 4.9(9) . . . . ?
C29 C28 C30 Cl5 -0.5(9) . . . . ?
C25 C28 C30 Cl5 -177.7(5) . . . . ?
C36 C31 C32 C33 0.6(10) . . . . ?
C31 C32 C33 C34 -0.5(10) . . . . ?
C32 C33 C34 C35 0.4(9) . . . . ?
C33 C34 C35 C36 -0.3(9) . . . . ?
C34 C35 C36 C31 0.3(9) . . . . ?
C34 C35 C36 C37 178.6(5) . . . . ?
C32 C31 C36 C35 -0.4(9) . . . . ?
C32 C31 C36 C37 -178.7(6) . . . . ?
C35 C36 C37 C42 -158.0(6) . . . . ?
C31 C36 C37 C42 20.3(8) . . . . ?
C35 C36 C37 C38 19.7(8) . . . . ?
C31 C36 C37 C38 -162.1(6) . . . . ?
C42 C37 C38 C39 -1.4(9) . . . . ?
C36 C37 C38 C39 -179.1(5) . . . . ?
C37 C38 C39 C40 0.0(9) . . . . ?
C38 C39 C40 C41 1.0(9) . . . . ?
C38 C39 C40 C43 -179.4(6) . . . . ?
C39 C40 C41 C42 -0.7(9) . . . . ?
C43 C40 C41 C42 179.8(6) . . . . ?
C40 C41 C42 C37 -0.7(10) . . . . ?
C38 C37 C42 C41 1.7(9) . . . . ?
C36 C37 C42 C41 179.4(6) . . . . ?
C41 C40 C43 C45 -130.3(7) . . . . ?
C39 C40 C43 C45 50.1(9) . . . . ?
C41 C40 C43 C44 48.1(8) . . . . ?
C39 C40 C43 C44 -131.5(6) . . . . ?
C45 C43 C44 Cl7 -97.6(7) . . . . ?
C40 C43 C44 Cl7 84.0(6) . . . . ?
C40 C43 C45 Cl9 6.5(9) . . . . ?
C44 C43 C45 Cl9 -171.9(5) . . . . ?
C40 C43 C45 Cl8 -174.6(5) . . . . ?
C44 C43 C45 Cl8 7.0(9) . . . . ?
C51 C46 C47 C48 0.4(10) . . . . ?
C46 C47 C48 C49 -1.0(10) . . . . ?
C47 C48 C49 C50 0.2(11) . . . . ?
C48 C49 C50 C51 1.2(11) . . . . ?
C47 C46 C51 C50 1.0(9) . . . . ?
C47 C46 C51 C52 -179.0(6) . . . . ?
C49 C50 C51 C46 -1.8(9) . . . . ?
C49 C50 C51 C52 178.3(6) . . . . ?
C46 C51 C52 C53 164.2(6) . . . . ?
C50 C51 C52 C53 -15.8(9) . . . . ?
C46 C51 C52 C57 -15.6(9) . . . . ?
C50 C51 C52 C57 164.3(6) . . . . ?
C57 C52 C53 C54 -0.7(9) . . . . ?
C51 C52 C53 C54 179.4(5) . . . . ?
C52 C53 C54 C55 1.2(9) . . . . ?
C53 C54 C55 C56 -1.5(9) . . . . ?
C53 C54 C55 C58 -177.3(6) . . . . ?
C54 C55 C56 C57 1.4(10) . . . . ?
C58 C55 C56 C57 177.3(6) . . . . ?
C55 C56 C57 C52 -1.0(11) . . . . ?
C53 C52 C57 C56 0.6(9) . . . . ?
C51 C52 C57 C56 -179.6(6) . . . . ?
C54 C55 C58 C60 -116.0(7) . . . . ?
C56 C55 C58 C60 68.3(9) . . . . ?
C54 C55 C58 C59 64.3(8) . . . . ?
C56 C55 C58 C59 -111.4(7) . . . . ?
C60 C58 C59 Cl10 -113.4(7) . . . . ?
C55 C58 C59 Cl10 66.3(7) . . . . ?
C55 C58 C60 Cl12 3.9(10) . . . . ?
C59 C58 C60 Cl12 -176.5(5) . . . . ?
C55 C58 C60 Cl11 -178.3(5) . . . . ?
C59 C58 C60 Cl11 1.4(10) . . . . ?
