#------------------------------------------------------------------------------ #$Date: 2021-01-04 20:16:21 +0200 (Mon, 04 Jan 2021) $ #$Revision: 260470 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/77/7127753.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_7127753 loop_ _publ_author_name 'Xue, Ze-Jian' 'Li, Meng-Yao' 'Zhu, Bin-Bin' 'He, Zhi-Tao' 'Feng, Chen-Guo' 'Lin, Guo-Qiang' _publ_section_title ; Stereoselective synthesis of conjugated trienes via 1,4-palladium migration/Heck sequence. ; _journal_issue 92 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 14420 _journal_page_last 14422 _journal_paper_doi 10.1039/d0cc06452a _journal_volume 56 _journal_year 2020 _chemical_absolute_configuration ad _chemical_formula_sum 'C24 H19 Cl' _chemical_formula_weight 342.84 _space_group_crystal_system orthorhombic _space_group_IT_number 29 _space_group_name_Hall 'P 2c -2ac' _space_group_name_H-M_alt 'P c a 21' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2020-09-08 deposited with the CCDC. 2020-10-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.8825(10) _cell_length_b 21.5798(16) _cell_length_c 8.2395(7) _cell_measurement_reflns_used 2736 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 44.078 _cell_measurement_theta_min 5.317 _cell_volume 1935.0(3) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXS-97 (Sheldrick 2008)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0323 _diffrn_reflns_av_unetI/netI 0.0472 _diffrn_reflns_Laue_measured_fraction_full 0.994 _diffrn_reflns_Laue_measured_fraction_max 0.994 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 9118 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.983 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.987 _diffrn_reflns_theta_min 2.658 _exptl_absorpt_coefficient_mu 0.200 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6345 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.177 _exptl_crystal_description prismatic _exptl_crystal_F_000 720 _exptl_crystal_size_max 0.170 _exptl_crystal_size_mid 0.140 _exptl_crystal_size_min 0.110 _refine_diff_density_max 0.142 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.024 _refine_ls_abs_structure_details ; Flack x determined using 900 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons and Flack (2004), Acta Cryst. A60, s61). ; _refine_ls_abs_structure_Flack 0.02(4) _refine_ls_extinction_coef 0.029(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 3743 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0781 _refine_ls_R_factor_gt 0.0449 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0420P)^2^+0.0540P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0894 _refine_ls_wR_factor_ref 0.1086 _reflns_Friedel_coverage 0.837 _reflns_Friedel_fraction_full 0.974 _reflns_Friedel_fraction_max 0.970 _reflns_number_gt 2557 _reflns_number_total 3743 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc06452a2.cif _cod_data_source_block d8v20300 _cod_database_code 7127753 _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 0.967 _shelx_estimated_absorpt_t_max 0.978 _shelxl_version_number 2013-4 _shelx_res_file ; TITL d8v20300_a.res in Pca2(1) CELL 0.71073 10.8825 21.5798 8.2395 90 90 90 ZERR 4 0.001 0.0016 0.0007 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5+X,-Y,+Z SYMM 0.5-X,+Y,0.5+Z SFAC C H Cl UNIT 96 76 4 OMIT 0 2 0 OMIT -3.00 52.00 L.S. 7 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 conf htab mpla c19 > c24 mpla c1 > c6 mpla c13 > c18 wpdb -1 size 0.17 0.14 0.11 TEMP 20.23 WGHT 0.042000 0.054000 EXTI 0.029209 FVAR 1.16612 CL1 3 0.797395 0.204489 0.467619 11.00000 0.04610 0.18853 = 0.14557 -0.03443 0.00226 -0.01095 C1 1 0.445618 0.227404 0.354195 11.00000 0.05797 0.06490 = 0.07228 0.00957 -0.00016 -0.00179 AFIX 43 H1 2 0.400284 0.252936 0.285763 11.00000 -1.20000 AFIX 0 C2 1 0.572286 0.234093 0.360607 11.00000 0.06090 0.08173 = 0.08641 -0.00264 0.01310 -0.01558 AFIX 43 H2 2 0.611754 0.263596 0.296952 11.00000 -1.20000 AFIX 0 C3 1 0.637754 0.196755 0.461602 11.00000 0.04398 0.09598 = 0.08321 -0.02039 0.00087 -0.00394 C4 1 0.582058 0.153044 0.557069 11.00000 0.05867 0.09101 = 0.07234 -0.00326 -0.00956 0.01433 AFIX 43 H4 2 0.628182 0.128479 0.626995 11.00000 -1.20000 AFIX 0 C5 1 0.455727 0.146120 0.547486 11.00000 0.04946 0.07116 = 0.06251 0.00463 -0.00131 0.00113 AFIX 43 H5 2 0.417412 0.115725 0.609468 11.00000 -1.20000 AFIX 0 C6 1 0.385173 0.183606 0.447303 11.00000 0.04744 0.05603 = 0.05581 -0.00245 0.00076 0.00158 C7 1 0.249598 0.175555 0.435726 11.00000 0.04410 0.06181 = 0.05808 0.00344 0.00037 0.00094 C8 1 0.173523 0.224980 0.443489 11.00000 0.04782 0.06938 = 0.07778 -0.00253 -0.00518 0.00345 AFIX 43 H8 2 0.091838 0.217466 0.416793 11.00000 -1.20000 AFIX 0 C9 1 0.202758 0.287413 0.487587 11.00000 0.05624 0.06417 = 0.08972 -0.00349 0.00249 0.00433 AFIX 43 H9 2 0.282195 0.295141 0.523947 11.00000 -1.20000 AFIX 0 C10 1 0.125852 0.335437 0.481001 11.00000 0.06606 0.07011 = 0.09638 -0.00198 0.00009 0.00612 AFIX 43 H10 2 0.047758 0.328298 0.439153 11.00000 -1.20000 AFIX 0 C11 1 0.153834 0.397046 0.533132 11.00000 0.07080 0.06776 = 0.09314 0.00106 0.00009 0.00822 AFIX 43 H11 2 0.230321 0.404039 0.580025 11.00000 -1.20000 AFIX 0 C12 1 0.077516 0.445235 0.519018 11.00000 0.07471 0.07118 = 0.09902 -0.00026 -0.00296 0.00815 AFIX 43 H12 2 0.001428 0.437351 0.471960 11.00000 -1.20000 AFIX 0 C13 1 0.101125 0.509322 0.569977 11.00000 0.06553 0.06407 = 0.08965 0.00406 0.00506 0.00907 C14 1 0.019696 0.555281 0.519927 11.00000 0.07518 0.07273 = 0.12690 0.00291 0.00223 0.01510 AFIX 43 H14 2 -0.048123 0.544784 0.456992 11.00000 -1.20000 AFIX 0 C15 1 0.038902 0.616105 0.562955 11.00000 0.08446 0.07223 = 0.15366 0.01172 0.01222 0.02123 AFIX 43 H15 2 -0.016804 0.646380 0.530715 11.00000 -1.20000 AFIX 0 C16 1 0.139177 0.632208 0.652609 11.00000 0.10874 0.06977 = 0.14220 -0.01013 0.02121 0.00186 AFIX 43 H16 2 0.152457 0.673481 0.679939 11.00000 -1.20000 AFIX 0 C17 1 0.219657 0.588030 0.702014 11.00000 0.10889 0.08075 = 0.12595 -0.01199 -0.01798 0.00140 AFIX 43 H17 2 0.287982 0.599221 0.763147 11.00000 -1.20000 AFIX 0 C18 1 0.201074 0.527149 0.662596 11.00000 0.08995 0.07460 = 0.10608 0.00341 -0.01280 0.01423 AFIX 43 H18 2 0.256432 0.497331 0.698588 11.00000 -1.20000 AFIX 0 C19 1 0.200698 0.112612 0.407361 11.00000 0.04581 0.06446 = 0.05446 0.00802 -0.00475 0.00012 C20 1 0.268776 0.068673 0.323306 11.00000 0.05307 0.06436 = 0.06344 0.00426 -0.00626 -0.00053 AFIX 43 H20 2 0.347856 0.078439 0.289005 11.00000 -1.20000 AFIX 0 C21 1 0.221380 0.010873 0.289754 11.00000 0.08387 0.06320 = 0.08211 -0.00467 -0.01550 -0.00152 AFIX 43 H21 2 0.268087 -0.017625 0.231758 11.00000 -1.20000 AFIX 0 C22 1 0.106439 -0.004779 0.341070 11.00000 0.09983 0.07169 = 0.08491 0.01145 -0.02412 -0.02542 AFIX 43 H22 2 0.074877 -0.043866 0.318227 11.00000 -1.20000 AFIX 0 C23 1 0.037520 0.037157 0.426323 11.00000 0.06369 0.10429 = 0.07681 0.01322 -0.00644 -0.03100 AFIX 43 H23 2 -0.040854 0.026502 0.461619 11.00000 -1.20000 AFIX 0 C24 1 0.084361 0.095401 0.460045 11.00000 0.04759 0.08778 = 0.06373 0.00476 -0.00077 -0.00789 AFIX 43 H24 2 0.037188 0.123442 0.518900 11.00000 -1.20000 AFIX 0 HKLF 4 REM d8v20300_a.res in Pca2(1) REM R1 = 0.0449 for 2557 Fo > 4sig(Fo) and 0.0781 for all 3743 data REM 227 parameters refined using 1 restraints END WGHT 0.0389 0.0738 REM No hydrogen bonds found for HTAB generation REM Highest difference peak 0.142, deepest hole -0.206, 1-sigma level 0.024 Q1 1 0.7853 0.1507 0.4727 11.00000 0.05 0.14 Q2 1 0.7948 0.1603 0.5157 11.00000 0.05 0.12 Q3 1 0.7894 0.1695 0.5543 11.00000 0.05 0.11 Q4 1 0.1485 -0.1024 0.1757 11.00000 0.05 0.10 Q5 1 -0.0797 0.0492 0.4650 11.00000 0.05 0.09 Q6 1 0.1206 -0.0695 0.2531 11.00000 0.05 0.09 Q7 1 0.4068 0.1807 0.5369 11.00000 0.05 0.09 Q8 1 0.3990 0.2644 0.3491 11.00000 0.05 0.09 Q9 1 0.5733 0.1923 0.3317 11.00000 0.05 0.08 Q10 1 0.0712 0.3237 0.6726 11.00000 0.05 0.08 Q11 1 0.8077 0.2904 0.4676 11.00000 0.05 0.08 Q12 1 0.7035 0.2021 0.4674 11.00000 0.05 0.08 Q13 1 0.0918 0.3897 0.6467 11.00000 0.05 0.08 Q14 1 0.0242 0.2386 0.5483 11.00000 0.05 0.08 Q15 1 0.8757 0.2486 0.3944 11.00000 0.05 0.08 Q16 1 -0.0578 0.5608 0.3287 11.00000 0.05 0.08 Q17 1 0.0311 0.1354 0.4954 11.00000 0.05 0.08 Q18 1 -0.0629 0.6413 0.5946 11.00000 0.05 0.08 Q19 1 0.8006 0.2729 0.3430 11.00000 0.05 0.08 Q20 1 0.0432 0.3265 0.3664 11.00000 0.05 0.08 ; _shelx_res_checksum 9103 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, 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 0.79740(9) 0.20449(7) 0.4676(2) 0.1267(6) Uani 1 1 d . . . . . C1 C 0.4456(3) 0.22740(14) 0.3542(5) 0.0650(9) Uani 1 1 d . . . . . H1 H 0.4003 0.2529 0.2858 0.078 Uiso 1 1 calc R U . . . C2 C 0.5723(4) 0.23409(17) 0.3606(5) 0.0763(11) Uani 1 1 d . . . . . H2 H 0.6118 0.2636 0.2970 0.092 Uiso 1 1 calc R U . . . C3 C 0.6378(3) 0.19676(19) 0.4616(6) 0.0744(10) Uani 1 1 d . . . . . C4 C 0.5821(3) 0.15304(17) 0.5571(5) 0.0740(10) Uani 1 1 d . . . . . H4 H 0.6282 0.1285 0.6270 0.089 Uiso 1 1 calc R U . . . C5 C 0.4557(3) 0.14612(14) 0.5475(4) 0.0610(9) Uani 1 1 d . . . . . H5 H 0.4174 0.1157 0.6095 0.073 Uiso 1 1 calc R U . . . C6 C 0.3852(3) 0.18361(12) 0.4473(4) 0.0531(7) Uani 1 1 d . . . . . C7 C 0.2496(3) 0.17556(13) 0.4357(4) 0.0547(7) Uani 1 1 d . . . . . C8 C 0.1735(3) 0.22498(13) 0.4435(5) 0.0650(9) Uani 1 1 d . . . . . H8 H 0.0918 0.2175 0.4168 0.078 Uiso 1 1 calc R U . . . C9 C 0.2028(3) 0.28741(13) 0.4876(5) 0.0700(10) Uani 1 1 d . . . . . H9 H 0.2822 0.2951 0.5239 0.084 Uiso 1 1 calc R U . . . C10 C 0.1259(3) 0.33544(15) 0.4810(5) 0.0775(11) Uani 1 1 d . . . . . H10 H 0.0478 0.3283 0.4392 0.093 Uiso 1 1 calc R U . . . C11 C 0.1538(3) 0.39705(15) 0.5331(5) 0.0772(11) Uani 1 1 d . . . . . H11 H 0.2303 0.4040 0.5800 0.093 Uiso 1 1 calc R U . . . C12 C 0.0775(4) 0.44523(15) 0.5190(5) 0.0816(12) Uani 1 1 d . . . . . H12 H 0.0014 0.4374 0.4720 0.098 Uiso 1 1 calc R U . . . C13 C 0.1011(4) 0.50932(15) 0.5700(5) 0.0731(10) Uani 1 1 d . . . . . C14 C 0.0197(4) 0.55528(17) 0.5199(6) 0.0916(14) Uani 1 1 d . . . . . H14 H -0.0481 0.5448 0.4570 0.110 Uiso 1 1 calc R U . . . C15 C 0.0389(5) 0.61611(19) 0.5630(7) 0.1034(15) Uani 1 1 d . . . . . H15 H -0.0168 0.6464 0.5307 0.124 Uiso 1 1 calc R U . . . C16 C 0.1392(5) 0.6322(2) 0.6526(7) 0.1069(16) Uani 1 1 d . . . . . H16 H 0.1525 0.6735 0.6799 0.128 Uiso 1 1 calc R U . . . C17 C 0.2197(5) 0.58803(19) 0.7020(7) 0.1052(17) Uani 1 1 d . . . . . H17 H 0.2880 0.5992 0.7631 0.126 Uiso 1 1 calc R U . . . C18 C 0.2011(4) 0.52715(18) 0.6626(6) 0.0902(13) Uani 1 1 d . . . . . H18 H 0.2564 0.4973 0.6986 0.108 Uiso 1 1 calc R U . . . C19 C 0.2007(3) 0.11261(14) 0.4074(4) 0.0549(8) Uani 1 1 d . . . . . C20 C 0.2688(3) 0.06867(14) 0.3233(4) 0.0603(9) Uani 1 1 d . . . . . H20 H 0.3479 0.0784 0.2890 0.072 Uiso 1 1 calc R U . . . C21 C 0.2214(4) 0.01087(16) 0.2898(5) 0.0764(11) Uani 1 1 d . . . . . H21 H 0.2681 -0.0176 0.2318 0.092 Uiso 1 1 calc R U . . . C22 C 0.1064(5) -0.00478(19) 0.3411(6) 0.0855(12) Uani 1 1 d . . . . . H22 H 0.0749 -0.0439 0.3182 0.103 Uiso 1 1 calc R U . . . C23 C 0.0375(4) 0.03716(19) 0.4263(5) 0.0816(11) Uani 1 1 d . . . . . H23 H -0.0409 0.0265 0.4616 0.098 Uiso 1 1 calc R U . . . C24 C 0.0844(3) 0.09540(16) 0.4600(5) 0.0664(9) Uani 1 1 d . . . . . H24 H 0.0372 0.1234 0.5189 0.080 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0461(6) 0.1885(12) 0.1456(12) -0.0344(11) 0.0023(8) -0.0110(6) C1 0.058(2) 0.065(2) 0.072(2) 0.0096(18) 0.000(2) -0.0018(17) C2 0.061(3) 0.082(3) 0.086(3) -0.003(2) 0.013(2) -0.0156(19) C3 0.0440(19) 0.096(2) 0.083(3) -0.020(2) 0.001(2) -0.0039(19) C4 0.059(2) 0.091(3) 0.072(2) -0.003(2) -0.010(2) 0.014(2) C5 0.049(2) 0.071(2) 0.063(2) 0.0046(17) -0.0013(18) 0.0011(17) C6 0.0474(17) 0.0560(16) 0.0558(17) -0.0024(17) 0.0008(18) 0.0016(14) C7 0.0441(17) 0.0618(17) 0.0581(18) 0.0034(17) 0.0004(17) 0.0009(15) C8 0.0478(19) 0.0694(19) 0.078(2) -0.003(2) -0.005(2) 0.0034(15) C9 0.056(2) 0.0642(19) 0.090(3) -0.003(2) 0.002(2) 0.0043(16) C10 0.066(2) 0.070(2) 0.096(3) -0.002(2) 0.000(2) 0.0061(18) C11 0.071(2) 0.068(2) 0.093(3) 0.001(2) 0.000(2) 0.0082(19) C12 0.075(3) 0.071(2) 0.099(3) 0.000(2) -0.003(2) 0.0081(19) C13 0.066(2) 0.064(2) 0.090(3) 0.004(2) 0.005(2) 0.0091(19) C14 0.075(3) 0.073(2) 0.127(4) 0.003(2) 0.002(3) 0.015(2) C15 0.084(3) 0.072(3) 0.154(5) 0.012(3) 0.012(3) 0.021(2) C16 0.109(4) 0.070(3) 0.142(4) -0.010(3) 0.021(4) 0.002(3) C17 0.109(5) 0.081(3) 0.126(4) -0.012(3) -0.018(3) 0.001(3) C18 0.090(3) 0.075(3) 0.106(3) 0.003(2) -0.013(3) 0.014(2) C19 0.0458(19) 0.0645(18) 0.0545(19) 0.0080(15) -0.0047(16) 0.0001(15) C20 0.053(2) 0.0644(18) 0.063(2) 0.0043(18) -0.0063(18) -0.0005(17) C21 0.084(3) 0.063(2) 0.082(3) -0.0047(19) -0.016(2) -0.002(2) C22 0.100(3) 0.072(2) 0.085(3) 0.011(2) -0.024(3) -0.025(2) C23 0.064(2) 0.104(3) 0.077(3) 0.013(2) -0.006(2) -0.031(2) C24 0.0476(19) 0.088(2) 0.064(2) 0.005(2) -0.0008(19) -0.0079(17) 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 C6 C1 C2 121.5(3) . . ? C6 C1 H1 119.3 . . ? C2 C1 H1 119.3 . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? C2 C3 C4 121.8(3) . . ? C2 C3 Cl1 118.8(3) . . ? C4 C3 Cl1 119.3(3) . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 C6 121.3(3) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? C1 C6 C5 117.7(3) . . ? C1 C6 C7 121.0(3) . . ? C5 C6 C7 121.2(3) . . ? C8 C7 C19 120.8(3) . . ? C8 C7 C6 120.8(3) . . ? C19 C7 C6 118.3(3) . . ? C7 C8 C9 128.2(3) . . ? C7 C8 H8 115.9 . . ? C9 C8 H8 115.9 . . ? C10 C9 C8 125.6(3) . . ? C10 C9 H9 117.2 . . ? C8 C9 H9 117.2 . . ? C9 C10 C11 125.2(4) . . ? C9 C10 H10 117.4 . . ? C11 C10 H10 117.4 . . ? C12 C11 C10 124.4(4) . . ? C12 C11 H11 117.8 . . ? C10 C11 H11 117.8 . . ? C11 C12 C13 126.8(4) . . ? C11 C12 H12 116.6 . . ? C13 C12 H12 116.6 . . ? C18 C13 C14 117.8(3) . . ? C18 C13 C12 123.9(4) . . ? C14 C13 C12 118.4(4) . . ? C15 C14 C13 120.4(4) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 120.3(4) . . ? C16 C15 H15 119.8 . . ? C14 C15 H15 119.8 . . ? C17 C16 C15 120.0(4) . . ? C17 C16 H16 120.0 . . ? C15 C16 H16 120.0 . . ? C16 C17 C18 120.5(5) . . ? C16 C17 H17 119.7 . . ? C18 C17 H17 119.7 . . ? C17 C18 C13 120.9(4) . . ? C17 C18 H18 119.5 . . ? C13 C18 H18 119.5 . . ? C24 C19 C20 117.4(3) . . ? C24 C19 C7 121.6(3) . . ? C20 C19 C7 121.0(3) . . ? C21 C20 C19 121.2(3) . . ? C21 C20 H20 119.4 . . ? C19 C20 H20 119.4 . . ? C22 C21 C20 120.4(4) . . ? C22 C21 H21 119.8 . . ? C20 C21 H21 119.8 . . ? C21 C22 C23 119.9(4) . . ? C21 C22 H22 120.1 . . ? C23 C22 H22 120.1 . . ? C22 C23 C24 120.1(4) . . ? C22 C23 H23 120.0 . . ? C24 C23 H23 120.0 . . ? C23 C24 C19 121.0(4) . . ? C23 C24 H24 119.5 . . ? C19 C24 H24 119.5 . . ? 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 C3 1.746(3) . ? C1 C6 1.384(4) . ? C1 C2 1.387(5) . ? C1 H1 0.9300 . ? C2 C3 1.360(5) . ? C2 H2 0.9300 . ? C3 C4 1.370(5) . ? C4 C5 1.385(4) . ? C4 H4 0.9300 . ? C5 C6 1.388(4) . ? C5 H5 0.9300 . ? C6 C7 1.489(4) . ? C7 C8 1.352(4) . ? C7 C19 1.477(4) . ? C8 C9 1.431(4) . ? C8 H8 0.9300 . ? C9 C10 1.333(4) . ? C9 H9 0.9300 . ? C10 C11 1.430(5) . ? C10 H10 0.9300 . ? C11 C12 1.336(4) . ? C11 H11 0.9300 . ? C12 C13 1.468(5) . ? C12 H12 0.9300 . ? C13 C18 1.383(5) . ? C13 C14 1.392(5) . ? C14 C15 1.376(5) . ? C14 H14 0.9300 . ? C15 C16 1.363(6) . ? C15 H15 0.9300 . ? C16 C17 1.357(6) . ? C16 H16 0.9300 . ? C17 C18 1.368(5) . ? C17 H17 0.9300 . ? C18 H18 0.9300 . ? C19 C24 1.389(4) . ? C19 C20 1.388(4) . ? C20 C21 1.378(4) . ? C20 H20 0.9300 . ? C21 C22 1.363(6) . ? C21 H21 0.9300 . ? C22 C23 1.369(5) . ? C22 H22 0.9300 . ? C23 C24 1.384(5) . ? C23 H23 0.9300 . ? C24 H24 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_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.3(5) . . . . ? C1 C2 C3 C4 -0.2(6) . . . . ? C1 C2 C3 Cl1 179.2(3) . . . . ? C2 C3 C4 C5 1.3(6) . . . . ? Cl1 C3 C4 C5 -178.1(3) . . . . ? C3 C4 C5 C6 -1.9(5) . . . . ? C2 C1 C6 C5 -0.3(5) . . . . ? C2 C1 C6 C7 -178.1(3) . . . . ? C4 C5 C6 C1 1.4(5) . . . . ? C4 C5 C6 C7 179.2(3) . . . . ? C1 C6 C7 C8 -48.7(5) . . . . ? C5 C6 C7 C8 133.5(3) . . . . ? C1 C6 C7 C19 128.2(3) . . . . ? C5 C6 C7 C19 -49.5(4) . . . . ? C19 C7 C8 C9 172.4(4) . . . . ? C6 C7 C8 C9 -10.7(6) . . . . ? C7 C8 C9 C10 174.4(4) . . . . ? C8 C9 C10 C11 176.6(4) . . . . ? C9 C10 C11 C12 176.9(5) . . . . ? C10 C11 C12 C13 -179.9(4) . . . . ? C11 C12 C13 C18 -9.8(7) . . . . ? C11 C12 C13 C14 168.9(4) . . . . ? C18 C13 C14 C15 -0.4(6) . . . . ? C12 C13 C14 C15 -179.2(4) . . . . ? C13 C14 C15 C16 1.2(8) . . . . ? C14 C15 C16 C17 -1.0(8) . . . . ? C15 C16 C17 C18 0.0(9) . . . . ? C16 C17 C18 C13 0.9(8) . . . . ? C14 C13 C18 C17 -0.7(6) . . . . ? C12 C13 C18 C17 178.1(5) . . . . ? C8 C7 C19 C24 -30.3(5) . . . . ? C6 C7 C19 C24 152.7(3) . . . . ? C8 C7 C19 C20 148.2(3) . . . . ? C6 C7 C19 C20 -28.8(4) . . . . ? C24 C19 C20 C21 1.7(5) . . . . ? C7 C19 C20 C21 -176.9(3) . . . . ? C19 C20 C21 C22 -1.0(5) . . . . ? C20 C21 C22 C23 0.1(6) . . . . ? C21 C22 C23 C24 0.1(6) . . . . ? C22 C23 C24 C19 0.6(6) . . . . ? C20 C19 C24 C23 -1.5(5) . . . . ? C7 C19 C24 C23 177.1(3) . . . . ?