#------------------------------------------------------------------------------ #$Date: 2019-11-07 23:17:27 +0200 (Thu, 07 Nov 2019) $ #$Revision: 223980 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/70/06/7700627.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_7700627 loop_ _publ_author_name 'Thapa, Rajesh' 'Kilyanek, Stefan M.' _publ_section_title ; Synthesis and structural characterization of 20-membered macrocyclic rings bearing trans-chelating bis(N-heterocyclic carbene) ligands and the catalytic activity of their palladium(ii) complexes. ; _journal_issue 33 _journal_name_full 'Dalton transactions (Cambridge, England : 2003)' _journal_page_first 12577 _journal_page_last 12590 _journal_paper_doi 10.1039/c9dt02147g _journal_volume 48 _journal_year 2019 _chemical_formula_moiety 'C32 H44 N6, 2(C H Cl3), 2(Br)' _chemical_formula_sum 'C34 H46 Br2 Cl6 N6' _chemical_formula_weight 911.29 _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_Hall '-P 2ac 2ab' _space_group_name_H-M_alt 'P b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-07-18 deposited with the CCDC. 2019-07-23 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.350(3) _cell_length_b 16.797(6) _cell_length_c 25.649(8) _cell_measurement_reflns_used 2245 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.32 _cell_measurement_theta_min 2.43 _cell_volume 4028(2) _computing_cell_refinement 'SAINT (Bruker, 2007)' _computing_data_collection 'APEX2 (Bruker, 2007)' _computing_data_reduction 'SAINT (Bruker, 2007)' _computing_molecular_graphics 'Mercury (CCDC, 2016)' _computing_publication_material 'SHELXL-2018/3 (Sheldrick, 2015b)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2015b)' _computing_structure_solution 'SHELXT (Sheldrick, 2015a)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker APEX CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0759 _diffrn_reflns_av_unetI/netI 0.0501 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 149026 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.569 _diffrn_reflns_theta_min 1.588 _exptl_absorpt_coefficient_mu 2.443 _exptl_absorpt_correction_T_max 0.775 _exptl_absorpt_correction_T_min 0.509 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'TWINABS 2012/1 (Sheldrick, 2015c)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.503 _exptl_crystal_description block _exptl_crystal_F_000 1856 _exptl_crystal_size_max 0.320 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_min 0.110 _refine_diff_density_max 3.282 _refine_diff_density_min -0.783 _refine_diff_density_rms 0.202 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 218 _refine_ls_number_reflns 11335 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.0872 _refine_ls_R_factor_gt 0.0597 _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^)+(0.1150P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1605 _refine_ls_wR_factor_ref 0.1750 _reflns_Friedel_coverage 0.000 _reflns_number_gt 7787 _reflns_number_total 11335 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9dt02147g2.cif _cod_data_source_block 16062b _cod_depositor_comments 'Adding full bibliography for 7700623--7700627.cif.' _cod_database_code 7700627 _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 0.509 _shelx_estimated_absorpt_t_max 0.775 _shelx_res_file ; TITL 16062b.res in Pbca 16062b.res created by SHELXL-2018/3 at 13:51:57 on 15-Jul-2019 REM Old TITL 16062 in Pbca REM SHELXT solution in Pbca REM R1 0.227, Rweak 0.010, Alpha 0.027, Orientation as input REM Formula found by SHELXT: C17 N6 Br CELL 0.71073 9.350 16.797 25.649 90.000 90.000 90.000 ZERR 4.000 0.003 0.006 0.008 0.000 0.000 0.000 LATT 1 SYMM 1/2-X, -Y, 1/2+Z SYMM -X, 1/2+Y, 1/2-Z SYMM 1/2+X, 1/2-Y, -Z SFAC C H N Cl Br UNIT 136 184 24 24 8 TEMP -173.16 SIZE 0.11 0.12 0.32 ACTA CONF WPDB -2 EQIV $1 -x+3/2, y-1/2, z EQIV $2 -x+1, -y+1, -z+1 EQIV $3 -x+2, -y+1, -z+1 HTAB C3 Br1_$1 HTAB C4 Br1_$2 HTAB C6 Br1_$3 HTAB C7 Br1 HTAB C8 Br1_$2 HTAB C10 Cl1S_$1 HTAB C1S Br1 HTAB L.S. 10 2 BOND $H FMAP 2 PLAN 20 WGHT 0.115000 BASF 0.15785 FVAR 0.25240 N1 3 0.442196 0.368681 0.357282 11.00000 0.02167 0.01966 = 0.03117 -0.00295 -0.00184 -0.00111 N2 3 0.695737 0.358596 0.483442 11.00000 0.02363 0.02023 = 0.03120 -0.00064 -0.00209 0.00397 N3 3 0.746834 0.447161 0.541432 11.00000 0.02318 0.01961 = 0.02812 0.00072 0.00106 0.00070 C1 1 0.598973 0.372631 0.363104 11.00000 0.02467 0.02618 = 0.02817 -0.00324 -0.00108 -0.00245 AFIX 23 H1A 2 0.624811 0.423156 0.380605 11.00000 -1.20000 H1B 2 0.643578 0.372780 0.328098 11.00000 -1.20000 AFIX 0 C2 1 0.658678 0.303253 0.394485 11.00000 0.02760 0.02643 = 0.03606 -0.00680 -0.00290 0.00192 AFIX 23 H2A 2 0.627773 0.252929 0.377850 11.00000 -1.20000 H2B 2 0.764410 0.305203 0.392867 11.00000 -1.20000 AFIX 0 C3 1 0.613451 0.301771 0.451381 11.00000 0.03015 0.02071 = 0.03615 -0.00314 -0.00215 -0.00172 AFIX 23 H3A 2 0.510439 0.314877 0.453827 11.00000 -1.20000 H3B 2 0.627007 0.247369 0.465386 11.00000 -1.20000 AFIX 0 C4 1 0.641256 0.412084 0.516052 11.00000 0.02319 0.01851 = 0.02812 0.00169 -0.00063 0.00170 AFIX 43 H4 2 0.542383 0.423283 0.520408 11.00000 -1.20000 AFIX 0 C5 1 0.842613 0.359877 0.488585 11.00000 0.02344 0.03743 = 0.03841 -0.00473 -0.00091 0.00839 AFIX 43 H5 2 0.909007 0.327455 0.470275 11.00000 -1.20000 AFIX 0 C6 1 0.874222 0.415924 0.524565 11.00000 0.02024 0.03562 = 0.03689 -0.00168 -0.00255 0.00410 AFIX 43 H6 2 0.967054 0.430862 0.536010 11.00000 -1.20000 AFIX 0 C7 1 0.728906 0.512856 0.579233 11.00000 0.02946 0.02032 = 0.02823 -0.00238 -0.00095 -0.00314 AFIX 23 H7A 2 0.693057 0.560682 0.560846 11.00000 -1.20000 H7B 2 0.822853 0.526156 0.594760 11.00000 -1.20000 AFIX 0 C8 1 0.624541 0.490253 0.622444 11.00000 0.02656 0.02104 = 0.03197 0.00013 -0.00128 -0.00059 AFIX 23 H8A 2 0.528738 0.480670 0.607253 11.00000 -1.20000 H8B 2 0.656794 0.440375 0.639314 11.00000 -1.20000 AFIX 0 C9 1 0.614874 0.555617 0.662806 11.00000 0.02365 0.02425 = 0.02967 -0.00102 0.00124 0.00003 AFIX 23 H9A 2 0.553072 0.537181 0.691728 11.00000 -1.20000 H9B 2 0.711497 0.565248 0.677277 11.00000 -1.20000 AFIX 0 C10 1 0.402704 0.304627 0.321035 11.00000 0.02447 0.02475 = 0.03160 -0.00804 0.00229 -0.00038 AFIX 23 H10A 2 0.472772 0.260726 0.324325 11.00000 -1.20000 H10B 2 0.408053 0.325115 0.284897 11.00000 -1.20000 AFIX 0 C11 1 0.253402 0.272009 0.330757 11.00000 0.02563 0.01695 = 0.02899 -0.00117 -0.00083 0.00197 C12 1 0.200416 0.264647 0.381010 11.00000 0.02994 0.02161 = 0.02798 -0.00249 -0.00266 0.00297 AFIX 43 H12 2 0.254903 0.283303 0.409786 11.00000 -1.20000 AFIX 0 C13 1 0.066943 0.229791 0.389209 11.00000 0.03028 0.01990 = 0.03041 0.00125 0.00556 0.00356 AFIX 43 H13 2 0.030876 0.224878 0.423686 11.00000 -1.20000 AFIX 0 C14 1 -0.013409 0.202325 0.347746 11.00000 0.02352 0.01819 = 0.04427 0.00035 -0.00070 0.00057 AFIX 43 H14 2 -0.104051 0.178438 0.353692 11.00000 -1.20000 AFIX 0 C15 1 0.038497 0.209741 0.297819 11.00000 0.02845 0.02487 = 0.03664 0.00024 -0.00499 -0.00177 AFIX 43 H15 2 -0.016259 0.190695 0.269221 11.00000 -1.20000 AFIX 0 C16 1 0.171103 0.245089 0.289035 11.00000 0.02925 0.02305 = 0.02786 -0.00100 0.00039 0.00135 AFIX 43 H16 2 0.205622 0.250875 0.254406 11.00000 -1.20000 AFIX 0 BR1 5 0.732745 0.595826 0.449621 11.00000 0.02194 0.02736 = 0.03059 0.00455 -0.00005 -0.00012 CL1S 4 1.035327 0.591938 0.329428 11.00000 0.03512 0.02686 = 0.04549 0.00539 -0.00216 -0.00316 CL2S 4 0.764032 0.546603 0.282934 11.00000 0.03250 0.03597 = 0.03879 0.00183 -0.00401 0.00722 CL3S 4 0.952869 0.426059 0.326330 11.00000 0.03006 0.02436 = 0.05977 0.00225 -0.00381 0.00268 C1S 1 0.889062 0.524955 0.332263 11.00000 0.02798 0.02467 = 0.03437 0.00309 -0.00075 0.00269 AFIX 13 H1S 2 0.841072 0.530833 0.366893 11.00000 -1.20000 AFIX 0 HKLF 5 REM 16062b.res in Pbca REM wR2 = 0.1750, GooF = S = 1.006, Restrained GooF = 1.006 for all data REM R1 = 0.0597 for 7787 Fo > 4sig(Fo) and 0.0872 for all 11335 data REM 218 parameters refined using 0 restraints END WGHT 0.1222 0.0000 REM Instructions for potential hydrogen bonds HTAB C3 Br1_$1 HTAB C4 Br1_$2 HTAB C6 Br1_$3 HTAB C7 Br1 HTAB C8 Br1_$2 HTAB C10 Cl1S_$1 HTAB C1S Br1 REM Highest difference peak 3.282, deepest hole -0.783, 1-sigma level 0.202 Q1 1 0.9486 0.4287 0.3496 11.00000 0.05 1.02 Q2 1 0.6897 0.5505 0.2886 11.00000 0.05 0.95 Q3 1 0.6762 0.4176 0.5393 11.00000 0.05 0.82 Q4 1 0.7350 0.5943 0.6514 11.00000 0.05 0.78 Q5 1 0.7734 0.3585 0.4826 11.00000 0.05 0.78 Q6 1 0.7486 0.4589 0.5571 11.00000 0.05 0.70 Q7 1 0.2025 0.2666 0.3116 11.00000 0.05 0.68 Q8 1 0.8127 0.4226 0.5411 11.00000 0.05 0.67 Q9 1 0.5703 0.4076 0.6703 11.00000 0.05 0.63 Q10 1 0.0202 0.2163 0.3247 11.00000 0.05 0.61 Q11 1 0.2234 0.2756 0.3526 11.00000 0.05 0.61 Q12 1 0.5005 0.3698 0.3630 11.00000 0.05 0.59 Q13 1 0.7340 0.2146 0.4492 11.00000 0.05 0.58 Q14 1 0.7301 0.5723 0.5513 11.00000 0.05 0.57 Q15 1 0.6787 0.5009 0.5982 11.00000 0.05 0.57 Q16 1 0.9752 0.4076 0.4295 11.00000 0.05 0.57 Q17 1 0.8415 0.3904 0.5112 11.00000 0.05 0.56 Q18 1 0.7316 0.5410 0.6132 11.00000 0.05 0.56 Q19 1 0.3017 0.2776 0.3297 11.00000 0.05 0.55 Q20 1 0.2466 0.2473 0.3881 11.00000 0.05 0.54 ; _shelx_res_checksum 85881 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, 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 N1 N 0.4422(3) 0.36868(19) 0.35728(13) 0.0242(7) Uani 1 1 d . . N2 N 0.6957(4) 0.35860(19) 0.48344(14) 0.0250(7) Uani 1 1 d . . N3 N 0.7468(3) 0.4472(2) 0.54143(14) 0.0236(7) Uani 1 1 d . . C1 C 0.5990(4) 0.3726(2) 0.36310(16) 0.0263(9) Uani 1 1 d . . H1A H 0.624811 0.423156 0.380605 0.032 Uiso 1 1 calc R U H1B H 0.643578 0.372780 0.328098 0.032 Uiso 1 1 calc R U C2 C 0.6587(5) 0.3033(2) 0.39449(16) 0.0300(9) Uani 1 1 d . . H2A H 0.627773 0.252929 0.377850 0.036 Uiso 1 1 calc R U H2B H 0.764410 0.305203 0.392867 0.036 Uiso 1 1 calc R U C3 C 0.6135(5) 0.3018(2) 0.45138(16) 0.0290(9) Uani 1 1 d . . H3A H 0.510439 0.314877 0.453827 0.035 Uiso 1 1 calc R U H3B H 0.627007 0.247369 0.465386 0.035 Uiso 1 1 calc R U C4 C 0.6413(5) 0.4121(2) 0.51605(16) 0.0233(8) Uani 1 1 d . . H4 H 0.542383 0.423283 0.520408 0.028 Uiso 1 1 calc R U C5 C 0.8426(5) 0.3599(3) 0.48859(18) 0.0331(10) Uani 1 1 d . . H5 H 0.909007 0.327455 0.470275 0.040 Uiso 1 1 calc R U C6 C 0.8742(5) 0.4159(3) 0.52457(18) 0.0309(10) Uani 1 1 d . . H6 H 0.967054 0.430862 0.536010 0.037 Uiso 1 1 calc R U C7 C 0.7289(4) 0.5129(3) 0.57923(16) 0.0260(9) Uani 1 1 d . . H7A H 0.693057 0.560682 0.560846 0.031 Uiso 1 1 calc R U H7B H 0.822853 0.526156 0.594760 0.031 Uiso 1 1 calc R U C8 C 0.6245(4) 0.4903(2) 0.62244(16) 0.0265(9) Uani 1 1 d . . H8A H 0.528738 0.480670 0.607253 0.032 Uiso 1 1 calc R U H8B H 0.656794 0.440375 0.639314 0.032 Uiso 1 1 calc R U C9 C 0.6149(4) 0.5556(2) 0.66281(16) 0.0259(9) Uani 1 1 d . . H9A H 0.553072 0.537181 0.691728 0.031 Uiso 1 1 calc R U H9B H 0.711497 0.565248 0.677277 0.031 Uiso 1 1 calc R U C10 C 0.4027(4) 0.3046(2) 0.32104(16) 0.0269(9) Uani 1 1 d . . H10A H 0.472772 0.260726 0.324325 0.032 Uiso 1 1 calc R U H10B H 0.408053 0.325115 0.284897 0.032 Uiso 1 1 calc R U C11 C 0.2534(4) 0.2720(2) 0.33076(16) 0.0239(8) Uani 1 1 d . . C12 C 0.2004(5) 0.2646(2) 0.38101(16) 0.0265(9) Uani 1 1 d . . H12 H 0.254903 0.283303 0.409786 0.032 Uiso 1 1 calc R U C13 C 0.0669(4) 0.2298(2) 0.38921(16) 0.0269(9) Uani 1 1 d . . H13 H 0.030876 0.224878 0.423686 0.032 Uiso 1 1 calc R U C14 C -0.0134(5) 0.2023(2) 0.34775(17) 0.0287(9) Uani 1 1 d . . H14 H -0.104051 0.178438 0.353692 0.034 Uiso 1 1 calc R U C15 C 0.0385(5) 0.2097(2) 0.29782(17) 0.0300(9) Uani 1 1 d . . H15 H -0.016259 0.190695 0.269221 0.036 Uiso 1 1 calc R U C16 C 0.1711(4) 0.2451(2) 0.28903(16) 0.0267(9) Uani 1 1 d . . H16 H 0.205622 0.250875 0.254406 0.032 Uiso 1 1 calc R U Br1 Br 0.73274(4) 0.59583(2) 0.44962(2) 0.02663(17) Uani 1 1 d . . Cl1S Cl 1.03533(13) 0.59194(6) 0.32943(5) 0.0358(3) Uani 1 1 d . . Cl2S Cl 0.76403(11) 0.54660(7) 0.28293(5) 0.0358(3) Uani 1 1 d . . Cl3S Cl 0.95287(12) 0.42606(6) 0.32633(5) 0.0381(3) Uani 1 1 d . . C1S C 0.8891(5) 0.5250(2) 0.33226(17) 0.0290(9) Uani 1 1 d . . H1S H 0.841072 0.530833 0.366893 0.035 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 N1 0.0217(17) 0.0197(16) 0.0312(18) -0.0029(14) -0.0018(14) -0.0011(13) N2 0.0236(17) 0.0202(17) 0.0312(18) -0.0006(14) -0.0021(15) 0.0040(14) N3 0.0232(17) 0.0196(17) 0.0281(18) 0.0007(13) 0.0011(13) 0.0007(13) C1 0.025(2) 0.026(2) 0.028(2) -0.0032(17) -0.0011(16) -0.0025(17) C2 0.028(2) 0.026(2) 0.036(2) -0.0068(18) -0.0029(18) 0.0019(17) C3 0.030(2) 0.021(2) 0.036(2) -0.0031(17) -0.0021(18) -0.0017(17) C4 0.023(2) 0.0185(19) 0.028(2) 0.0017(15) -0.0006(16) 0.0017(15) C5 0.023(2) 0.037(2) 0.038(2) -0.005(2) -0.0009(18) 0.0084(18) C6 0.020(2) 0.036(2) 0.037(2) -0.0017(19) -0.0026(18) 0.0041(17) C7 0.029(2) 0.020(2) 0.028(2) -0.0024(16) -0.0010(17) -0.0031(16) C8 0.027(2) 0.021(2) 0.032(2) 0.0001(16) -0.0013(17) -0.0006(16) C9 0.024(2) 0.024(2) 0.030(2) -0.0010(16) 0.0012(16) 0.0000(16) C10 0.024(2) 0.025(2) 0.032(2) -0.0080(17) 0.0023(17) -0.0004(17) C11 0.026(2) 0.0169(19) 0.029(2) -0.0012(16) -0.0008(16) 0.0020(15) C12 0.030(2) 0.022(2) 0.028(2) -0.0025(16) -0.0027(17) 0.0030(17) C13 0.030(2) 0.020(2) 0.030(2) 0.0013(16) 0.0056(17) 0.0036(16) C14 0.024(2) 0.0182(19) 0.044(2) 0.0003(17) -0.0007(18) 0.0006(16) C15 0.028(2) 0.025(2) 0.037(2) 0.0002(17) -0.0050(18) -0.0018(17) C16 0.029(2) 0.023(2) 0.028(2) -0.0010(16) 0.0004(17) 0.0014(17) Br1 0.0219(3) 0.0274(3) 0.0306(3) 0.00455(16) -0.00005(15) -0.00012(15) Cl1S 0.0351(6) 0.0269(6) 0.0455(7) 0.0054(4) -0.0022(5) -0.0032(4) Cl2S 0.0325(6) 0.0360(6) 0.0388(6) 0.0018(5) -0.0040(4) 0.0072(4) Cl3S 0.0301(6) 0.0244(5) 0.0598(8) 0.0023(5) -0.0038(5) 0.0027(4) C1S 0.028(2) 0.025(2) 0.034(2) 0.0031(17) -0.0007(17) 0.0027(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' N N 0.0061 0.0033 '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' Br Br -0.2901 2.4595 '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 C1 N1 C10 110.3(3) . . C1 N1 C9 110.9(3) . 5_666 C10 N1 C9 108.7(3) . 5_666 C4 N2 C5 108.1(3) . . C4 N2 C3 126.0(4) . . C5 N2 C3 125.6(3) . . C4 N3 C6 108.8(4) . . C4 N3 C7 124.8(3) . . C6 N3 C7 126.2(3) . . N1 C1 C2 112.6(3) . . N1 C1 H1A 109.1 . . C2 C1 H1A 109.1 . . N1 C1 H1B 109.1 . . C2 C1 H1B 109.1 . . H1A C1 H1B 107.8 . . C3 C2 C1 114.7(3) . . C3 C2 H2A 108.6 . . C1 C2 H2A 108.6 . . C3 C2 H2B 108.6 . . C1 C2 H2B 108.6 . . H2A C2 H2B 107.6 . . N2 C3 C2 112.3(3) . . N2 C3 H3A 109.1 . . C2 C3 H3A 109.1 . . N2 C3 H3B 109.1 . . C2 C3 H3B 109.1 . . H3A C3 H3B 107.9 . . N3 C4 N2 109.0(4) . . N3 C4 H4 125.5 . . N2 C4 H4 125.5 . . C6 C5 N2 107.1(4) . . C6 C5 H5 126.5 . . N2 C5 H5 126.5 . . C5 C6 N3 107.0(4) . . C5 C6 H6 126.5 . . N3 C6 H6 126.5 . . N3 C7 C8 111.3(3) . . N3 C7 H7A 109.4 . . C8 C7 H7A 109.4 . . N3 C7 H7B 109.4 . . C8 C7 H7B 109.4 . . H7A C7 H7B 108.0 . . C9 C8 C7 110.8(3) . . C9 C8 H8A 109.5 . . C7 C8 H8A 109.5 . . C9 C8 H8B 109.5 . . C7 C8 H8B 109.5 . . H8A C8 H8B 108.1 . . N1 C9 C8 114.2(3) 5_666 . N1 C9 H9A 108.7 5_666 . C8 C9 H9A 108.7 . . N1 C9 H9B 108.7 5_666 . C8 C9 H9B 108.7 . . H9A C9 H9B 107.6 . . N1 C10 C11 113.0(3) . . N1 C10 H10A 109.0 . . C11 C10 H10A 109.0 . . N1 C10 H10B 109.0 . . C11 C10 H10B 109.0 . . H10A C10 H10B 107.8 . . C12 C11 C16 119.2(4) . . C12 C11 C10 120.8(4) . . C16 C11 C10 119.9(4) . . C11 C12 C13 119.8(4) . . C11 C12 H12 120.1 . . C13 C12 H12 120.1 . . C14 C13 C12 120.7(4) . . C14 C13 H13 119.6 . . C12 C13 H13 119.6 . . C13 C14 C15 119.7(4) . . C13 C14 H14 120.2 . . C15 C14 H14 120.2 . . C14 C15 C16 120.2(4) . . C14 C15 H15 119.9 . . C16 C15 H15 119.9 . . C15 C16 C11 120.4(4) . . C15 C16 H16 119.8 . . C11 C16 H16 119.8 . . Cl2S C1S Cl1S 110.6(2) . . Cl2S C1S Cl3S 110.8(2) . . Cl1S C1S Cl3S 109.4(2) . . Cl2S C1S H1S 108.7 . . Cl1S C1S H1S 108.7 . . Cl3S C1S H1S 108.7 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 N1 C1 1.475(5) . N1 C10 1.469(5) . N1 C9 1.472(5) 5_666 N2 C4 1.329(5) . N2 C5 1.380(5) . N2 C3 1.476(5) . N3 C4 1.321(5) . N3 C6 1.372(5) . N3 C7 1.478(5) . C1 C2 1.522(6) . C1 H1A 0.9900 . C1 H1B 0.9900 . C2 C3 1.520(6) . C2 H2A 0.9900 . C2 H2B 0.9900 . C3 H3A 0.9900 . C3 H3B 0.9900 . C4 H4 0.9500 . C5 C6 1.351(6) . C5 H5 0.9500 . C6 H6 0.9500 . C7 C8 1.525(6) . C7 H7A 0.9900 . C7 H7B 0.9900 . C8 C9 1.512(5) . C8 H8A 0.9900 . C8 H8B 0.9900 . C9 H9A 0.9900 . C9 H9B 0.9900 . C10 C11 1.520(6) . C10 H10A 0.9900 . C10 H10B 0.9900 . C11 C12 1.386(6) . C11 C16 1.393(6) . C12 C13 1.394(6) . C12 H12 0.9500 . C13 C14 1.381(6) . C13 H13 0.9500 . C14 C15 1.375(6) . C14 H14 0.9500 . C15 C16 1.393(6) . C15 H15 0.9500 . C16 H16 0.9500 . Cl1S C1S 1.772(4) . Cl2S C1S 1.761(4) . Cl3S C1S 1.772(4) . C1S H1S 1.0000 . 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 C3 H3B Br1 0.99 2.89 3.747(4) 145.1 8_755 yes C4 H4 Br1 0.95 2.70 3.608(4) 159.3 5_666 yes C6 H6 Br1 0.95 2.87 3.739(5) 153.3 5_766 yes C7 H7A Br1 0.99 2.94 3.605(4) 125.7 . yes C8 H8A Br1 0.99 3.12 4.083(4) 163.5 5_666 yes C10 H10A Cl1S 0.99 2.84 3.626(4) 136.9 8_755 yes C1S H1S Br1 1.00 2.59 3.552(4) 160.7 . 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_4 C10 N1 C1 C2 -72.1(4) . . C9 N1 C1 C2 167.5(3) 5_666 . N1 C1 C2 C3 -66.1(5) . . C4 N2 C3 C2 129.6(4) . . C5 N2 C3 C2 -57.3(5) . . C1 C2 C3 N2 -78.5(4) . . C6 N3 C4 N2 0.4(5) . . C7 N3 C4 N2 176.8(4) . . C5 N2 C4 N3 0.1(5) . . C3 N2 C4 N3 174.2(3) . . C4 N2 C5 C6 -0.7(5) . . C3 N2 C5 C6 -174.8(4) . . N2 C5 C6 N3 0.9(5) . . C4 N3 C6 C5 -0.8(5) . . C7 N3 C6 C5 -177.2(4) . . C4 N3 C7 C8 55.0(5) . . C6 N3 C7 C8 -129.2(4) . . N3 C7 C8 C9 176.1(3) . . C7 C8 C9 N1 63.3(4) . 5_666 C1 N1 C10 C11 154.1(3) . . C9 N1 C10 C11 -84.1(4) 5_666 . N1 C10 C11 C12 -36.7(5) . . N1 C10 C11 C16 146.8(4) . . C16 C11 C12 C13 0.7(6) . . C10 C11 C12 C13 -175.8(4) . . C11 C12 C13 C14 0.1(6) . . C12 C13 C14 C15 -0.3(6) . . C13 C14 C15 C16 -0.3(6) . . C14 C15 C16 C11 1.1(6) . . C12 C11 C16 C15 -1.3(6) . . C10 C11 C16 C15 175.3(4) . .