#------------------------------------------------------------------------------ #$Date: 2021-10-01 02:48:56 +0300 (Fri, 01 Oct 2021) $ #$Revision: 269414 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/36/7243648.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_7243648 loop_ _publ_author_name 'Orecchia, Patrizio' 'Petkova, Desislava Slavcheva' 'Goetz, Roland' 'Rominger, Frank' 'Hashmi, A. Stephen K.' 'Schaub, Thomas' _publ_section_title ; Pd-Catalysed Suzuki--Miyaura cross-coupling of aryl chlorides at low catalyst loadings in water for the synthesis of industrially important fungicides ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D1GC02602J _journal_year 2021 _chemical_formula_sum 'C18 H12 Cl2 N2 O' _chemical_formula_weight 343.20 _chemical_name_common Boscalid _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-05-27 deposited with the CCDC. 2021-08-27 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.746(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 14.8126(13) _cell_length_b 11.5893(9) _cell_length_c 18.7010(15) _cell_measurement_reflns_used 3484 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 21.05 _cell_measurement_theta_min 2.18 _cell_volume 3208.9(5) _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-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT-2018/2 (Sheldrick 2015)' _diffrn_ambient_temperature 200(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker APEX-II Quazar area detector' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0851 _diffrn_reflns_av_unetI/netI 0.0691 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 28243 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.406 _diffrn_reflns_theta_max 24.406 _diffrn_reflns_theta_min 2.068 _diffrn_source 'ImuS microsource' _exptl_absorpt_coefficient_mu 0.409 _exptl_absorpt_correction_T_max 0.9582 _exptl_absorpt_correction_T_min 0.9114 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Sheldrick, G. M. (2008). SADABS. University of G\"ottingen, Germany. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.421 _exptl_crystal_description plate _exptl_crystal_F_000 1408 _exptl_crystal_size_max 0.180 _exptl_crystal_size_mid 0.078 _exptl_crystal_size_min 0.032 _refine_diff_density_max 0.277 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.058 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 423 _refine_ls_number_reflns 5283 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.1146 _refine_ls_R_factor_gt 0.0537 _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/[\s^2^(Fo^2^)+(0.0621P)^2^+1.7281P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1205 _refine_ls_wR_factor_ref 0.1473 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3100 _reflns_number_total 5283 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1gc02602j2.cif _cod_data_source_block po1 _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 7243648 _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 0.930 _shelx_estimated_absorpt_t_max 0.987 _shelx_res_file ; TITL po1 in P2(1)/c po1.res created by SHELXL-2018/3 at 10:41:55 on 05-Jan-2021 REM REM schoene Messung, 0.86 A, problemlose Loesung und exakt die REM erwartete Struktur, zwei unabh\"angige Molek\"ule, Wasserstoffatome REM gesehen, H11 an N11 frei verfeinert, sonst alle an konstruierten REM Positionen ber\"ucksichtigt, leider literaturbekannt REM (https://doi.org/10.1039/C9CE00306A) REM REM REM REM CELL 0.71073 14.81260 11.58930 18.70100 90.0000 91.7462 90.0000 ZERR 8.00 0.00130 0.00090 0.00150 0.0000 0.0022 0.0000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O CL UNIT 144 96 16 8 16 TEMP -73.160 SIZE 0.032 0.078 0.18 L.S. 4 ACTA BOND $H CONF FMAP 2 PLAN 9 WGHT 0.062100 1.728100 FVAR 0.07044 RESI 1 CL1 5 0.630471 0.095780 0.696546 11.00000 0.05543 0.03869 = 0.06785 -0.01628 0.02415 -0.00630 CL2 5 0.881567 -0.128407 0.780413 11.00000 0.08545 0.03456 = 0.06459 -0.00136 0.01928 0.00661 C10 1 0.637741 0.330902 0.772625 11.00000 0.02694 0.02270 = 0.02641 -0.00169 0.00025 0.00389 O10 4 0.672132 0.364110 0.717403 11.00000 0.04003 0.03773 = 0.01850 0.00030 0.00489 -0.00741 N11 3 0.673880 0.356087 0.837499 11.00000 0.02623 0.03171 = 0.02387 0.00404 0.00498 -0.00563 H11 2 0.650080 0.326443 0.866069 11.00000 0.01897 C11 1 0.551172 0.264330 0.772836 11.00000 0.02659 0.03158 = 0.02551 0.00392 0.00038 0.00295 C12 1 0.538501 0.159640 0.737403 11.00000 0.03718 0.03090 = 0.03052 0.00056 0.00216 0.00019 N13 3 0.463161 0.100253 0.734188 11.00000 0.04040 0.04244 = 0.04535 -0.00456 0.00245 -0.01344 C14 1 0.393329 0.144214 0.768179 11.00000 0.03398 0.04793 = 0.05732 0.00522 -0.00459 -0.01308 AFIX 43 H14 2 0.337932 0.102854 0.766587 11.00000 -1.20000 AFIX 0 C15 1 0.397343 0.246083 0.805331 11.00000 0.02911 0.05313 = 0.05698 0.00255 0.00947 -0.00213 AFIX 43 H15 2 0.345791 0.274496 0.828678 11.00000 -1.20000 AFIX 0 C16 1 0.477753 0.306838 0.808255 11.00000 0.03734 0.03031 = 0.05030 -0.00377 0.00548 -0.00224 AFIX 43 H16 2 0.482432 0.377034 0.834338 11.00000 -1.20000 AFIX 0 C21 1 0.753368 0.425859 0.844912 11.00000 0.03516 0.03158 = 0.01898 0.00066 -0.00238 -0.00011 C22 1 0.836395 0.380834 0.826287 11.00000 0.02857 0.03287 = 0.02116 -0.00050 -0.00007 0.00034 C23 1 0.910142 0.455255 0.827017 11.00000 0.03027 0.04329 = 0.04471 -0.00581 0.00370 -0.00404 AFIX 43 H23 2 0.967295 0.427581 0.812935 11.00000 -1.20000 AFIX 0 C24 1 0.901257 0.568826 0.847960 11.00000 0.04644 0.03759 = 0.05480 -0.00426 -0.00065 -0.01319 AFIX 43 H24 2 0.951813 0.619181 0.847015 11.00000 -1.20000 AFIX 0 C25 1 0.819165 0.609449 0.870267 11.00000 0.05355 0.03006 = 0.04699 -0.00816 -0.00010 -0.00406 AFIX 43 H25 2 0.813986 0.686393 0.887173 11.00000 -1.20000 AFIX 0 C26 1 0.745026 0.538316 0.867945 11.00000 0.03407 0.03615 = 0.03409 -0.00022 0.00104 0.00486 AFIX 43 H26 2 0.688085 0.566489 0.882176 11.00000 -1.20000 AFIX 0 C31 1 0.846754 0.255727 0.811192 11.00000 0.02198 0.03447 = 0.02924 -0.00194 0.00031 -0.00231 C32 1 0.871740 0.212646 0.745143 11.00000 0.03983 0.03359 = 0.03137 0.00203 0.00783 0.00517 AFIX 43 H32 2 0.882676 0.264186 0.706866 11.00000 -1.20000 AFIX 0 C33 1 0.880668 0.094965 0.735151 11.00000 0.04603 0.04289 = 0.03395 -0.00996 0.00897 0.01008 AFIX 43 H33 2 0.896096 0.066043 0.689587 11.00000 -1.20000 AFIX 0 C34 1 0.867486 0.019921 0.790270 11.00000 0.03855 0.02919 = 0.04644 0.00006 0.00596 0.00361 C35 1 0.843757 0.060451 0.855387 11.00000 0.04391 0.04164 = 0.03399 0.00456 0.00548 0.00028 AFIX 43 H35 2 0.835119 0.008488 0.893867 11.00000 -1.20000 AFIX 0 C36 1 0.832388 0.176965 0.865087 11.00000 0.04827 0.03833 = 0.02853 -0.00429 0.00704 0.00067 AFIX 43 H36 2 0.814062 0.204239 0.910300 11.00000 -1.20000 AFIX 0 RESI 2 CL1 5 0.467987 0.125358 0.527646 11.00000 0.07555 0.05729 = 0.11788 -0.03116 0.02738 -0.01935 CL2 5 0.818971 0.866658 0.594951 11.00000 0.08832 0.04132 = 0.07658 -0.00400 0.00347 -0.00948 O10 4 0.629191 0.268096 0.465080 11.00000 0.05509 0.08032 = 0.02251 -0.01590 0.00227 0.00936 C10 1 0.625488 0.298368 0.527814 11.00000 0.04190 0.03052 = 0.03169 -0.00276 0.00453 -0.00222 N11 3 0.697422 0.306961 0.572907 11.00000 0.03474 0.03888 = 0.01947 -0.00303 0.00427 -0.00452 H11 2 0.687241 0.330027 0.619155 11.00000 0.04864 C11 1 0.538023 0.334285 0.559670 11.00000 0.04232 0.03789 = 0.01832 -0.00388 0.00073 0.00590 C12 1 0.463888 0.263447 0.562680 11.00000 0.04161 0.04735 = 0.04586 -0.00628 0.00367 0.00192 N13 3 0.386511 0.289797 0.591801 11.00000 0.03676 0.08035 = 0.06454 -0.00832 0.00223 0.00218 C14 1 0.380084 0.396240 0.618471 11.00000 0.05021 0.08850 = 0.04618 -0.01004 0.00120 0.02966 AFIX 43 H14 2 0.325648 0.417108 0.640736 11.00000 -1.20000 AFIX 0 C15 1 0.446533 0.476253 0.615683 11.00000 0.06696 0.05847 = 0.04309 -0.01779 -0.00594 0.02376 AFIX 43 H15 2 0.437335 0.552380 0.632836 11.00000 -1.20000 AFIX 0 C16 1 0.528216 0.444644 0.587266 11.00000 0.05979 0.04834 = 0.03225 -0.00702 0.00116 0.00299 AFIX 43 H16 2 0.576958 0.497876 0.586670 11.00000 -1.20000 AFIX 0 C21 1 0.786449 0.273595 0.554010 11.00000 0.04213 0.03679 = 0.01684 0.00295 0.00253 0.00495 C22 1 0.856030 0.355651 0.556916 11.00000 0.03911 0.03905 = 0.02379 0.00479 -0.00110 0.00323 C23 1 0.942591 0.317358 0.540303 11.00000 0.03798 0.05083 = 0.03854 0.00422 -0.00142 0.00280 AFIX 43 H23 2 0.991690 0.370075 0.542987 11.00000 -1.20000 AFIX 0 C24 1 0.957972 0.205774 0.520308 11.00000 0.04497 0.05282 = 0.05131 0.01237 0.00840 0.01991 AFIX 43 H24 2 1.017178 0.182386 0.508571 11.00000 -1.20000 AFIX 0 C25 1 0.888156 0.126754 0.517028 11.00000 0.06109 0.04031 = 0.04128 0.00522 0.01038 0.01566 AFIX 43 H25 2 0.898983 0.049548 0.502530 11.00000 -1.20000 AFIX 0 C26 1 0.802868 0.160829 0.534929 11.00000 0.05142 0.03677 = 0.02723 0.00546 0.00656 0.00101 AFIX 43 H26 2 0.754951 0.106316 0.534143 11.00000 -1.20000 AFIX 0 C31 1 0.841688 0.480405 0.571999 11.00000 0.03262 0.04046 = 0.02927 0.00120 0.00379 -0.00365 C32 1 0.775663 0.542546 0.534482 11.00000 0.04264 0.03956 = 0.03111 0.00080 -0.00119 -0.00479 AFIX 43 H32 2 0.734900 0.503099 0.502815 11.00000 -1.20000 AFIX 0 C33 1 0.767996 0.661462 0.542335 11.00000 0.04883 0.03752 = 0.03834 0.00398 -0.00132 0.00335 AFIX 43 H33 2 0.722914 0.703310 0.516065 11.00000 -1.20000 AFIX 0 C34 1 0.826313 0.716707 0.588369 11.00000 0.04850 0.03818 = 0.04331 -0.00357 0.00640 -0.00228 C35 1 0.891213 0.658040 0.627715 11.00000 0.05140 0.04862 = 0.05129 -0.00739 -0.01299 -0.01179 AFIX 43 H35 2 0.930412 0.698019 0.660341 11.00000 -1.20000 AFIX 0 C36 1 0.898684 0.540641 0.619240 11.00000 0.04442 0.04942 = 0.04635 -0.00043 -0.00465 -0.00292 AFIX 43 H36 2 0.943702 0.499798 0.646204 11.00000 -1.20000 RESI 0 AFIX 0 HKLF 4 REM po1 in P2(1)/c REM wR2 = 0.147345, GooF = S = 1.03217, Restrained GooF = 1.03217 for all data REM R1 = 0.053719 for 3100 Fo > 4sig(Fo) and 0.114582 for all 5283 data REM 423 parameters refined using 0 restraints END WGHT 0.0621 1.7216 REM Highest difference peak 0.277, deepest hole -0.376, 1-sigma level 0.058 Q1 1 0.3978 0.4716 0.5880 11.00000 0.05 0.28 Q2 1 0.5261 0.1117 0.5695 11.00000 0.05 0.22 Q3 1 0.5837 0.2988 0.7648 11.00000 0.05 0.22 Q4 1 0.6476 0.0574 0.7461 11.00000 0.05 0.21 Q5 1 0.5240 0.2787 0.8031 11.00000 0.05 0.21 Q6 1 0.8239 0.3101 0.5379 11.00000 0.05 0.20 Q7 1 0.5753 0.1406 0.6894 11.00000 0.05 0.20 Q8 1 0.8595 -0.1614 0.7095 11.00000 0.05 0.20 Q9 1 0.8061 0.3935 0.8559 11.00000 0.05 0.20 ; _shelx_res_checksum 93747 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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_1 Cl 0.63047(8) 0.09578(9) 0.69655(6) 0.0535(4) Uani 1 1 d . . . . . Cl2_1 Cl 0.88157(9) -0.12841(10) 0.78041(7) 0.0612(4) Uani 1 1 d . . . . . C10_1 C 0.6377(2) 0.3309(3) 0.77262(19) 0.0254(9) Uani 1 1 d . . . . . O10_1 O 0.67213(17) 0.3641(2) 0.71740(12) 0.0320(6) Uani 1 1 d . . . . . N11_1 N 0.6739(2) 0.3561(3) 0.83750(18) 0.0272(8) Uani 1 1 d . . . . . H11_1 H 0.650(2) 0.326(3) 0.8661(19) 0.019(12) Uiso 1 1 d . . . . . C11_1 C 0.5512(2) 0.2643(3) 0.77284(19) 0.0279(9) Uani 1 1 d . . . . . C12_1 C 0.5385(3) 0.1596(3) 0.7374(2) 0.0328(10) Uani 1 1 d . . . . . N13_1 N 0.4632(2) 0.1003(3) 0.73419(18) 0.0427(9) Uani 1 1 d . . . . . C14_1 C 0.3933(3) 0.1442(4) 0.7682(2) 0.0465(12) Uani 1 1 d . . . . . H14_1 H 0.337932 0.102854 0.766587 0.056 Uiso 1 1 calc R U . . . C15_1 C 0.3973(3) 0.2461(4) 0.8053(2) 0.0462(12) Uani 1 1 d . . . . . H15_1 H 0.345791 0.274496 0.828678 0.055 Uiso 1 1 calc R U . . . C16_1 C 0.4778(3) 0.3068(3) 0.8083(2) 0.0392(10) Uani 1 1 d . . . . . H16_1 H 0.482432 0.377034 0.834338 0.047 Uiso 1 1 calc R U . . . C21_1 C 0.7534(3) 0.4259(3) 0.84491(18) 0.0286(9) Uani 1 1 d . . . . . C22_1 C 0.8364(2) 0.3808(3) 0.82629(18) 0.0275(9) Uani 1 1 d . . . . . C23_1 C 0.9101(3) 0.4553(4) 0.8270(2) 0.0394(11) Uani 1 1 d . . . . . H23_1 H 0.967295 0.427581 0.812935 0.047 Uiso 1 1 calc R U . . . C24_1 C 0.9013(3) 0.5688(4) 0.8480(2) 0.0463(12) Uani 1 1 d . . . . . H24_1 H 0.951813 0.619181 0.847015 0.056 Uiso 1 1 calc R U . . . C25_1 C 0.8192(3) 0.6094(4) 0.8703(2) 0.0436(11) Uani 1 1 d . . . . . H25_1 H 0.813986 0.686393 0.887173 0.052 Uiso 1 1 calc R U . . . C26_1 C 0.7450(3) 0.5383(3) 0.8679(2) 0.0348(10) Uani 1 1 d . . . . . H26_1 H 0.688085 0.566489 0.882176 0.042 Uiso 1 1 calc R U . . . C31_1 C 0.8468(2) 0.2557(3) 0.81119(19) 0.0286(9) Uani 1 1 d . . . . . C32_1 C 0.8717(3) 0.2126(3) 0.7451(2) 0.0348(10) Uani 1 1 d . . . . . H32_1 H 0.882676 0.264186 0.706866 0.042 Uiso 1 1 calc R U . . . C33_1 C 0.8807(3) 0.0950(4) 0.7352(2) 0.0408(11) Uani 1 1 d . . . . . H33_1 H 0.896096 0.066043 0.689587 0.049 Uiso 1 1 calc R U . . . C34_1 C 0.8675(3) 0.0199(3) 0.7903(2) 0.0380(10) Uani 1 1 d . . . . . C35_1 C 0.8438(3) 0.0605(4) 0.8554(2) 0.0398(11) Uani 1 1 d . . . . . H35_1 H 0.835119 0.008488 0.893867 0.048 Uiso 1 1 calc R U . . . C36_1 C 0.8324(3) 0.1770(3) 0.8651(2) 0.0383(10) Uani 1 1 d . . . . . H36_1 H 0.814062 0.204239 0.910300 0.046 Uiso 1 1 calc R U . . . Cl1_2 Cl 0.46799(10) 0.12536(11) 0.52765(9) 0.0831(5) Uani 1 1 d . . . . . Cl2_2 Cl 0.81897(10) 0.86666(10) 0.59495(7) 0.0687(4) Uani 1 1 d . . . . . O10_2 O 0.6292(2) 0.2681(3) 0.46508(14) 0.0526(8) Uani 1 1 d . . . . . C10_2 C 0.6255(3) 0.2984(3) 0.5278(2) 0.0346(10) Uani 1 1 d . . . . . N11_2 N 0.6974(2) 0.3070(3) 0.57291(17) 0.0310(8) Uani 1 1 d . . . . . H11_2 H 0.687(3) 0.330(3) 0.619(2) 0.049(13) Uiso 1 1 d . . . . . C11_2 C 0.5380(3) 0.3343(3) 0.55967(19) 0.0328(10) Uani 1 1 d . . . . . C12_2 C 0.4639(3) 0.2634(4) 0.5627(2) 0.0449(11) Uani 1 1 d . . . . . N13_2 N 0.3865(3) 0.2898(4) 0.5918(2) 0.0605(11) Uani 1 1 d . . . . . C14_2 C 0.3801(4) 0.3962(5) 0.6185(3) 0.0616(14) Uani 1 1 d . . . . . H14_2 H 0.325648 0.417108 0.640736 0.074 Uiso 1 1 calc R U . . . C15_2 C 0.4465(4) 0.4763(4) 0.6157(2) 0.0563(13) Uani 1 1 d . . . . . H15_2 H 0.437335 0.552380 0.632836 0.068 Uiso 1 1 calc R U . . . C16_2 C 0.5282(3) 0.4446(4) 0.5873(2) 0.0468(12) Uani 1 1 d . . . . . H16_2 H 0.576958 0.497876 0.586670 0.056 Uiso 1 1 calc R U . . . C21_2 C 0.7864(3) 0.2736(3) 0.55401(18) 0.0319(10) Uani 1 1 d . . . . . C22_2 C 0.8560(3) 0.3557(3) 0.55692(19) 0.0340(10) Uani 1 1 d . . . . . C23_2 C 0.9426(3) 0.3174(4) 0.5403(2) 0.0425(11) Uani 1 1 d . . . . . H23_2 H 0.991690 0.370075 0.542987 0.051 Uiso 1 1 calc R U . . . C24_2 C 0.9580(3) 0.2058(4) 0.5203(2) 0.0496(12) Uani 1 1 d . . . . . H24_2 H 1.017178 0.182386 0.508571 0.059 Uiso 1 1 calc R U . . . C25_2 C 0.8882(3) 0.1268(4) 0.5170(2) 0.0474(12) Uani 1 1 d . . . . . H25_2 H 0.898983 0.049548 0.502530 0.057 Uiso 1 1 calc R U . . . C26_2 C 0.8029(3) 0.1608(4) 0.53493(19) 0.0384(10) Uani 1 1 d . . . . . H26_2 H 0.754951 0.106316 0.534143 0.046 Uiso 1 1 calc R U . . . C31_2 C 0.8417(3) 0.4804(3) 0.5720(2) 0.0341(10) Uani 1 1 d . . . . . C32_2 C 0.7757(3) 0.5425(4) 0.5345(2) 0.0378(10) Uani 1 1 d . . . . . H32_2 H 0.734900 0.503099 0.502815 0.045 Uiso 1 1 calc R U . . . C33_2 C 0.7680(3) 0.6615(4) 0.5423(2) 0.0416(11) Uani 1 1 d . . . . . H33_2 H 0.722914 0.703310 0.516065 0.050 Uiso 1 1 calc R U . . . C34_2 C 0.8263(3) 0.7167(4) 0.5884(2) 0.0432(11) Uani 1 1 d . . . . . C35_2 C 0.8912(3) 0.6580(4) 0.6277(2) 0.0507(12) Uani 1 1 d . . . . . H35_2 H 0.930412 0.698019 0.660341 0.061 Uiso 1 1 calc R U . . . C36_2 C 0.8987(3) 0.5406(4) 0.6192(2) 0.0469(12) Uani 1 1 d . . . . . H36_2 H 0.943702 0.499798 0.646204 0.056 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_1 0.0554(7) 0.0387(7) 0.0679(8) -0.0163(6) 0.0241(6) -0.0063(5) Cl2_1 0.0854(10) 0.0346(7) 0.0646(8) -0.0014(6) 0.0193(7) 0.0066(6) C10_1 0.027(2) 0.023(2) 0.026(2) -0.0017(17) 0.0002(18) 0.0039(17) O10_1 0.0400(16) 0.0377(16) 0.0185(14) 0.0003(12) 0.0049(12) -0.0074(13) N11_1 0.0262(19) 0.032(2) 0.0239(19) 0.0040(16) 0.0050(16) -0.0056(15) C11_1 0.027(2) 0.032(2) 0.026(2) 0.0039(17) 0.0004(17) 0.0029(17) C12_1 0.037(3) 0.031(2) 0.031(2) 0.0006(18) 0.0022(19) 0.0002(19) N13_1 0.040(2) 0.042(2) 0.045(2) -0.0046(17) 0.0025(18) -0.0134(18) C14_1 0.034(3) 0.048(3) 0.057(3) 0.005(2) -0.005(2) -0.013(2) C15_1 0.029(3) 0.053(3) 0.057(3) 0.003(2) 0.009(2) -0.002(2) C16_1 0.037(3) 0.030(2) 0.050(3) -0.004(2) 0.005(2) -0.002(2) C21_1 0.035(2) 0.032(2) 0.019(2) 0.0007(17) -0.0024(17) -0.0001(18) C22_1 0.029(2) 0.033(2) 0.021(2) -0.0005(17) -0.0001(17) 0.0003(18) C23_1 0.030(2) 0.043(3) 0.045(3) -0.006(2) 0.004(2) -0.004(2) C24_1 0.046(3) 0.038(3) 0.055(3) -0.004(2) -0.001(2) -0.013(2) C25_1 0.054(3) 0.030(3) 0.047(3) -0.008(2) 0.000(2) -0.004(2) C26_1 0.034(2) 0.036(3) 0.034(2) -0.0002(19) 0.0010(19) 0.005(2) C31_1 0.022(2) 0.034(2) 0.029(2) -0.0019(18) 0.0003(17) -0.0023(17) C32_1 0.040(2) 0.034(3) 0.031(2) 0.0020(19) 0.0078(19) 0.0052(19) C33_1 0.046(3) 0.043(3) 0.034(2) -0.010(2) 0.009(2) 0.010(2) C34_1 0.039(2) 0.029(2) 0.046(3) 0.000(2) 0.006(2) 0.0036(19) C35_1 0.044(3) 0.042(3) 0.034(2) 0.005(2) 0.005(2) 0.000(2) C36_1 0.048(3) 0.038(3) 0.029(2) -0.0043(19) 0.007(2) 0.001(2) Cl1_2 0.0756(10) 0.0573(9) 0.1179(13) -0.0312(8) 0.0274(9) -0.0194(7) Cl2_2 0.0883(10) 0.0413(8) 0.0766(9) -0.0040(6) 0.0035(8) -0.0095(7) O10_2 0.055(2) 0.080(2) 0.0225(17) -0.0159(15) 0.0023(14) 0.0094(17) C10_2 0.042(3) 0.031(2) 0.032(2) -0.0028(18) 0.005(2) -0.0022(19) N11_2 0.035(2) 0.039(2) 0.0195(18) -0.0030(15) 0.0043(16) -0.0045(16) C11_2 0.042(3) 0.038(3) 0.018(2) -0.0039(18) 0.0007(18) 0.006(2) C12_2 0.042(3) 0.047(3) 0.046(3) -0.006(2) 0.004(2) 0.002(2) N13_2 0.037(2) 0.080(3) 0.065(3) -0.008(2) 0.002(2) 0.002(2) C14_2 0.050(3) 0.089(4) 0.046(3) -0.010(3) 0.001(2) 0.030(3) C15_2 0.067(4) 0.058(3) 0.043(3) -0.018(2) -0.006(3) 0.024(3) C16_2 0.060(3) 0.048(3) 0.032(2) -0.007(2) 0.001(2) 0.003(2) C21_2 0.042(3) 0.037(3) 0.017(2) 0.0029(17) 0.0025(18) 0.005(2) C22_2 0.039(3) 0.039(3) 0.024(2) 0.0048(18) -0.0011(18) 0.003(2) C23_2 0.038(3) 0.051(3) 0.039(3) 0.004(2) -0.001(2) 0.003(2) C24_2 0.045(3) 0.053(3) 0.051(3) 0.012(2) 0.008(2) 0.020(3) C25_2 0.061(3) 0.040(3) 0.041(3) 0.005(2) 0.010(2) 0.016(2) C26_2 0.051(3) 0.037(3) 0.027(2) 0.0055(19) 0.007(2) 0.001(2) C31_2 0.033(2) 0.040(3) 0.029(2) 0.0012(19) 0.0038(19) -0.004(2) C32_2 0.043(3) 0.040(3) 0.031(2) 0.0008(19) -0.001(2) -0.005(2) C33_2 0.049(3) 0.038(3) 0.038(3) 0.004(2) -0.001(2) 0.003(2) C34_2 0.049(3) 0.038(3) 0.043(3) -0.004(2) 0.006(2) -0.002(2) C35_2 0.051(3) 0.049(3) 0.051(3) -0.007(2) -0.013(2) -0.012(2) C36_2 0.044(3) 0.049(3) 0.046(3) 0.000(2) -0.005(2) -0.003(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O10_1 C10_1 N11_1 121.8(3) . . ? O10_1 C10_1 C11_1 122.8(3) . . ? N11_1 C10_1 C11_1 115.3(3) . . ? C10_1 N11_1 C21_1 120.9(3) . . ? C10_1 N11_1 H11_1 112(3) . . ? C21_1 N11_1 H11_1 127(3) . . ? C16_1 C11_1 C12_1 116.2(4) . . ? C16_1 C11_1 C10_1 120.3(3) . . ? C12_1 C11_1 C10_1 123.4(3) . . ? N13_1 C12_1 C11_1 125.6(4) . . ? N13_1 C12_1 Cl1_1 115.6(3) . . ? C11_1 C12_1 Cl1_1 118.8(3) . . ? C12_1 N13_1 C14_1 116.7(4) . . ? N13_1 C14_1 C15_1 123.3(4) . . ? N13_1 C14_1 H14_1 118.3 . . ? C15_1 C14_1 H14_1 118.3 . . ? C14_1 C15_1 C16_1 118.9(4) . . ? C14_1 C15_1 H15_1 120.6 . . ? C16_1 C15_1 H15_1 120.6 . . ? C11_1 C16_1 C15_1 119.3(4) . . ? C11_1 C16_1 H16_1 120.4 . . ? C15_1 C16_1 H16_1 120.4 . . ? C26_1 C21_1 C22_1 121.4(4) . . ? C26_1 C21_1 N11_1 118.9(3) . . ? C22_1 C21_1 N11_1 119.7(3) . . ? C21_1 C22_1 C23_1 117.7(4) . . ? C21_1 C22_1 C31_1 120.7(3) . . ? C23_1 C22_1 C31_1 121.4(3) . . ? C24_1 C23_1 C22_1 120.8(4) . . ? C24_1 C23_1 H23_1 119.6 . . ? C22_1 C23_1 H23_1 119.6 . . ? C25_1 C24_1 C23_1 120.2(4) . . ? C25_1 C24_1 H24_1 119.9 . . ? C23_1 C24_1 H24_1 119.9 . . ? C26_1 C25_1 C24_1 119.8(4) . . ? C26_1 C25_1 H25_1 120.1 . . ? C24_1 C25_1 H25_1 120.1 . . ? C25_1 C26_1 C21_1 119.9(4) . . ? C25_1 C26_1 H26_1 120.1 . . ? C21_1 C26_1 H26_1 120.1 . . ? C36_1 C31_1 C32_1 117.5(4) . . ? C36_1 C31_1 C22_1 119.2(3) . . ? C32_1 C31_1 C22_1 123.4(3) . . ? C33_1 C32_1 C31_1 120.2(4) . . ? C33_1 C32_1 H32_1 119.9 . . ? C31_1 C32_1 H32_1 119.9 . . ? C34_1 C33_1 C32_1 120.6(4) . . ? C34_1 C33_1 H33_1 119.7 . . ? C32_1 C33_1 H33_1 119.7 . . ? C35_1 C34_1 C33_1 120.1(4) . . ? C35_1 C34_1 Cl2_1 118.0(3) . . ? C33_1 C34_1 Cl2_1 121.8(3) . . ? C34_1 C35_1 C36_1 119.6(4) . . ? C34_1 C35_1 H35_1 120.2 . . ? C36_1 C35_1 H35_1 120.2 . . ? C35_1 C36_1 C31_1 122.1(4) . . ? C35_1 C36_1 H36_1 119.0 . . ? C31_1 C36_1 H36_1 119.0 . . ? O10_2 C10_2 N11_2 124.3(4) . . ? O10_2 C10_2 C11_2 121.5(4) . . ? N11_2 C10_2 C11_2 114.1(3) . . ? C10_2 N11_2 C21_2 123.1(3) . . ? C10_2 N11_2 H11_2 117(2) . . ? C21_2 N11_2 H11_2 119(2) . . ? C12_2 C11_2 C16_2 116.3(4) . . ? C12_2 C11_2 C10_2 123.5(4) . . ? C16_2 C11_2 C10_2 120.3(4) . . ? N13_2 C12_2 C11_2 125.7(4) . . ? N13_2 C12_2 Cl1_2 114.3(4) . . ? C11_2 C12_2 Cl1_2 120.0(3) . . ? C12_2 N13_2 C14_2 116.1(4) . . ? N13_2 C14_2 C15_2 123.9(4) . . ? N13_2 C14_2 H14_2 118.0 . . ? C15_2 C14_2 H14_2 118.0 . . ? C14_2 C15_2 C16_2 118.5(5) . . ? C14_2 C15_2 H15_2 120.7 . . ? C16_2 C15_2 H15_2 120.7 . . ? C15_2 C16_2 C11_2 119.2(4) . . ? C15_2 C16_2 H16_2 120.4 . . ? C11_2 C16_2 H16_2 120.4 . . ? C26_2 C21_2 C22_2 121.2(4) . . ? C26_2 C21_2 N11_2 119.5(4) . . ? C22_2 C21_2 N11_2 119.3(3) . . ? C23_2 C22_2 C21_2 117.0(4) . . ? C23_2 C22_2 C31_2 119.1(4) . . ? C21_2 C22_2 C31_2 123.8(4) . . ? C24_2 C23_2 C22_2 121.4(4) . . ? C24_2 C23_2 H23_2 119.3 . . ? C22_2 C23_2 H23_2 119.3 . . ? C23_2 C24_2 C25_2 120.6(4) . . ? C23_2 C24_2 H24_2 119.7 . . ? C25_2 C24_2 H24_2 119.7 . . ? C26_2 C25_2 C24_2 119.4(4) . . ? C26_2 C25_2 H25_2 120.3 . . ? C24_2 C25_2 H25_2 120.3 . . ? C25_2 C26_2 C21_2 120.4(4) . . ? C25_2 C26_2 H26_2 119.8 . . ? C21_2 C26_2 H26_2 119.8 . . ? C32_2 C31_2 C36_2 117.7(4) . . ? C32_2 C31_2 C22_2 120.7(4) . . ? C36_2 C31_2 C22_2 121.3(4) . . ? C31_2 C32_2 C33_2 121.3(4) . . ? C31_2 C32_2 H32_2 119.4 . . ? C33_2 C32_2 H32_2 119.4 . . ? C34_2 C33_2 C32_2 118.7(4) . . ? C34_2 C33_2 H33_2 120.6 . . ? C32_2 C33_2 H33_2 120.6 . . ? C33_2 C34_2 C35_2 121.8(4) . . ? C33_2 C34_2 Cl2_2 118.2(4) . . ? C35_2 C34_2 Cl2_2 120.0(4) . . ? C34_2 C35_2 C36_2 119.1(4) . . ? C34_2 C35_2 H35_2 120.5 . . ? C36_2 C35_2 H35_2 120.5 . . ? C35_2 C36_2 C31_2 121.4(4) . . ? C35_2 C36_2 H36_2 119.3 . . ? C31_2 C36_2 H36_2 119.3 . . ? 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_1 C12_1 1.747(4) . ? Cl2_1 C34_1 1.742(4) . ? C10_1 O10_1 1.227(4) . ? C10_1 N11_1 1.343(5) . ? C10_1 C11_1 1.497(5) . ? N11_1 C21_1 1.432(5) . ? N11_1 H11_1 0.73(3) . ? C11_1 C16_1 1.381(5) . ? C11_1 C12_1 1.392(5) . ? C12_1 N13_1 1.311(5) . ? N13_1 C14_1 1.332(5) . ? C14_1 C15_1 1.370(6) . ? C14_1 H14_1 0.9500 . ? C15_1 C16_1 1.383(5) . ? C15_1 H15_1 0.9500 . ? C16_1 H16_1 0.9500 . ? C21_1 C26_1 1.379(5) . ? C21_1 C22_1 1.390(5) . ? C22_1 C23_1 1.392(5) . ? C22_1 C31_1 1.486(5) . ? C23_1 C24_1 1.381(6) . ? C23_1 H23_1 0.9500 . ? C24_1 C25_1 1.380(6) . ? C24_1 H24_1 0.9500 . ? C25_1 C26_1 1.373(5) . ? C25_1 H25_1 0.9500 . ? C26_1 H26_1 0.9500 . ? C31_1 C36_1 1.381(5) . ? C31_1 C32_1 1.393(5) . ? C32_1 C33_1 1.383(5) . ? C32_1 H32_1 0.9500 . ? C33_1 C34_1 1.367(5) . ? C33_1 H33_1 0.9500 . ? C34_1 C35_1 1.361(5) . ? C35_1 C36_1 1.373(5) . ? C35_1 H35_1 0.9500 . ? C36_1 H36_1 0.9500 . ? Cl1_2 C12_2 1.731(4) . ? Cl2_2 C34_2 1.746(4) . ? O10_2 C10_2 1.227(4) . ? C10_2 N11_2 1.342(5) . ? C10_2 C11_2 1.501(5) . ? N11_2 C21_2 1.429(5) . ? N11_2 H11_2 0.92(4) . ? C11_2 C12_2 1.374(6) . ? C11_2 C16_2 1.388(5) . ? C12_2 N13_2 1.320(5) . ? N13_2 C14_2 1.335(6) . ? C14_2 C15_2 1.354(7) . ? C14_2 H14_2 0.9500 . ? C15_2 C16_2 1.386(6) . ? C15_2 H15_2 0.9500 . ? C16_2 H16_2 0.9500 . ? C21_2 C26_2 1.378(5) . ? C21_2 C22_2 1.402(5) . ? C22_2 C23_2 1.401(5) . ? C22_2 C31_2 1.490(5) . ? C23_2 C24_2 1.367(6) . ? C23_2 H23_2 0.9500 . ? C24_2 C25_2 1.381(6) . ? C24_2 H24_2 0.9500 . ? C25_2 C26_2 1.375(6) . ? C25_2 H25_2 0.9500 . ? C26_2 H26_2 0.9500 . ? C31_2 C32_2 1.388(5) . ? C31_2 C36_2 1.391(5) . ? C32_2 C33_2 1.391(5) . ? C32_2 H32_2 0.9500 . ? C33_2 C34_2 1.361(6) . ? C33_2 H33_2 0.9500 . ? C34_2 C35_2 1.373(6) . ? C35_2 C36_2 1.375(6) . ? C35_2 H35_2 0.9500 . ? C36_2 H36_2 0.9500 . ? 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 O10_1 C10_1 N11_1 C21_1 1.7(5) . . . . ? C11_1 C10_1 N11_1 C21_1 -175.8(3) . . . . ? O10_1 C10_1 C11_1 C16_1 -120.8(4) . . . . ? N11_1 C10_1 C11_1 C16_1 56.7(5) . . . . ? O10_1 C10_1 C11_1 C12_1 58.0(5) . . . . ? N11_1 C10_1 C11_1 C12_1 -124.6(4) . . . . ? C16_1 C11_1 C12_1 N13_1 1.1(6) . . . . ? C10_1 C11_1 C12_1 N13_1 -177.7(4) . . . . ? C16_1 C11_1 C12_1 Cl1_1 -175.7(3) . . . . ? C10_1 C11_1 C12_1 Cl1_1 5.5(5) . . . . ? C11_1 C12_1 N13_1 C14_1 -0.4(6) . . . . ? Cl1_1 C12_1 N13_1 C14_1 176.6(3) . . . . ? C12_1 N13_1 C14_1 C15_1 -0.1(6) . . . . ? N13_1 C14_1 C15_1 C16_1 -0.2(7) . . . . ? C12_1 C11_1 C16_1 C15_1 -1.4(6) . . . . ? C10_1 C11_1 C16_1 C15_1 177.4(4) . . . . ? C14_1 C15_1 C16_1 C11_1 1.0(6) . . . . ? C10_1 N11_1 C21_1 C26_1 105.6(4) . . . . ? C10_1 N11_1 C21_1 C22_1 -71.9(5) . . . . ? C26_1 C21_1 C22_1 C23_1 -4.2(5) . . . . ? N11_1 C21_1 C22_1 C23_1 173.3(3) . . . . ? C26_1 C21_1 C22_1 C31_1 171.6(3) . . . . ? N11_1 C21_1 C22_1 C31_1 -11.0(5) . . . . ? C21_1 C22_1 C23_1 C24_1 2.2(6) . . . . ? C31_1 C22_1 C23_1 C24_1 -173.6(4) . . . . ? C22_1 C23_1 C24_1 C25_1 1.6(6) . . . . ? C23_1 C24_1 C25_1 C26_1 -3.5(6) . . . . ? C24_1 C25_1 C26_1 C21_1 1.5(6) . . . . ? C22_1 C21_1 C26_1 C25_1 2.4(6) . . . . ? N11_1 C21_1 C26_1 C25_1 -175.1(4) . . . . ? C21_1 C22_1 C31_1 C36_1 -63.0(5) . . . . ? C23_1 C22_1 C31_1 C36_1 112.6(4) . . . . ? C21_1 C22_1 C31_1 C32_1 118.0(4) . . . . ? C23_1 C22_1 C31_1 C32_1 -66.4(5) . . . . ? C36_1 C31_1 C32_1 C33_1 0.5(6) . . . . ? C22_1 C31_1 C32_1 C33_1 179.5(4) . . . . ? C31_1 C32_1 C33_1 C34_1 -1.7(6) . . . . ? C32_1 C33_1 C34_1 C35_1 1.2(6) . . . . ? C32_1 C33_1 C34_1 Cl2_1 -178.0(3) . . . . ? C33_1 C34_1 C35_1 C36_1 0.6(6) . . . . ? Cl2_1 C34_1 C35_1 C36_1 179.8(3) . . . . ? C34_1 C35_1 C36_1 C31_1 -1.9(6) . . . . ? C32_1 C31_1 C36_1 C35_1 1.3(6) . . . . ? C22_1 C31_1 C36_1 C35_1 -177.8(4) . . . . ? O10_2 C10_2 N11_2 C21_2 -4.6(6) . . . . ? C11_2 C10_2 N11_2 C21_2 177.9(3) . . . . ? O10_2 C10_2 C11_2 C12_2 59.5(6) . . . . ? N11_2 C10_2 C11_2 C12_2 -122.9(4) . . . . ? O10_2 C10_2 C11_2 C16_2 -119.6(4) . . . . ? N11_2 C10_2 C11_2 C16_2 58.0(5) . . . . ? C16_2 C11_2 C12_2 N13_2 -2.8(6) . . . . ? C10_2 C11_2 C12_2 N13_2 178.0(4) . . . . ? C16_2 C11_2 C12_2 Cl1_2 178.3(3) . . . . ? C10_2 C11_2 C12_2 Cl1_2 -0.8(6) . . . . ? C11_2 C12_2 N13_2 C14_2 2.1(7) . . . . ? Cl1_2 C12_2 N13_2 C14_2 -179.0(3) . . . . ? C12_2 N13_2 C14_2 C15_2 1.4(7) . . . . ? N13_2 C14_2 C15_2 C16_2 -3.9(7) . . . . ? C14_2 C15_2 C16_2 C11_2 2.9(6) . . . . ? C12_2 C11_2 C16_2 C15_2 0.2(6) . . . . ? C10_2 C11_2 C16_2 C15_2 179.3(4) . . . . ? C10_2 N11_2 C21_2 C26_2 -60.6(5) . . . . ? C10_2 N11_2 C21_2 C22_2 121.0(4) . . . . ? C26_2 C21_2 C22_2 C23_2 -0.6(5) . . . . ? N11_2 C21_2 C22_2 C23_2 177.8(3) . . . . ? C26_2 C21_2 C22_2 C31_2 175.4(4) . . . . ? N11_2 C21_2 C22_2 C31_2 -6.1(5) . . . . ? C21_2 C22_2 C23_2 C24_2 1.7(6) . . . . ? C31_2 C22_2 C23_2 C24_2 -174.6(4) . . . . ? C22_2 C23_2 C24_2 C25_2 -1.0(6) . . . . ? C23_2 C24_2 C25_2 C26_2 -0.8(6) . . . . ? C24_2 C25_2 C26_2 C21_2 1.9(6) . . . . ? C22_2 C21_2 C26_2 C25_2 -1.1(6) . . . . ? N11_2 C21_2 C26_2 C25_2 -179.6(3) . . . . ? C23_2 C22_2 C31_2 C32_2 125.8(4) . . . . ? C21_2 C22_2 C31_2 C32_2 -50.2(5) . . . . ? C23_2 C22_2 C31_2 C36_2 -48.4(5) . . . . ? C21_2 C22_2 C31_2 C36_2 135.6(4) . . . . ? C36_2 C31_2 C32_2 C33_2 1.6(6) . . . . ? C22_2 C31_2 C32_2 C33_2 -172.9(4) . . . . ? C31_2 C32_2 C33_2 C34_2 -0.6(6) . . . . ? C32_2 C33_2 C34_2 C35_2 -0.9(6) . . . . ? C32_2 C33_2 C34_2 Cl2_2 177.4(3) . . . . ? C33_2 C34_2 C35_2 C36_2 1.4(7) . . . . ? Cl2_2 C34_2 C35_2 C36_2 -176.9(3) . . . . ? C34_2 C35_2 C36_2 C31_2 -0.3(7) . . . . ? C32_2 C31_2 C36_2 C35_2 -1.2(6) . . . . ? C22_2 C31_2 C36_2 C35_2 173.3(4) . . . . ?