# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_jof882c_sp #TrackingRef 'jof822c_joe_124.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C33 H33 Cl2 F3 N2 O5 S' _chemical_formula_weight 697.57 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P na2(1)' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' '-x+1/2, y+1/2, z+1/2' _cell_length_a 17.0215(8) _cell_length_b 12.1750(5) _cell_length_c 15.8959(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3294.2(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9984 _cell_measurement_theta_min 2.39 _cell_measurement_theta_max 27.56 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.01 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.407 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1448 _exptl_absorpt_coefficient_mu 0.321 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8521 _exptl_absorpt_correction_T_max 0.9010 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'high brilliance microfocus sealed tube MoK\a' _diffrn_radiation_source 'high brilliance microfocus sealed tube' _diffrn_radiation_monochromator multilayer _diffrn_measurement_device_type 'Bruker D8 QUEST' _diffrn_measurement_method 'omega + phi scans' _diffrn_detector_area_resol_mean 10.4167 _diffrn_reflns_number 84946 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.06 _diffrn_reflns_theta_max 28.35 _reflns_number_total 8153 _reflns_number_gt 7244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 201?.? (Bruker AXS Inc.)' _computing_cell_refinement 'SAINT V8.1????C (Bruker AXS Inc., 2011)' _computing_data_reduction 'SAINT V8.1????C (Bruker AXS Inc., 2011)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. One Me group is disordered over two positions, ca. 71:29%. The triflate anion is also disordered over two positions, ca. 56:44%. The dichloromethane is disordered over two positions, ca. 75:25%. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0823P)^2^+2.1920P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'The NH hydrogens free, ordered methyl groups rigid, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.12(7) _refine_ls_number_reflns 8153 _refine_ls_number_parameters 442 _refine_ls_number_restraints 54 _refine_ls_R_factor_all 0.0635 _refine_ls_R_factor_gt 0.0548 _refine_ls_wR_factor_ref 0.1515 _refine_ls_wR_factor_gt 0.1439 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 1.06375(13) 0.42475(19) 0.56139(16) 0.0298(4) Uani 1 1 d . . . H01 H 1.105(2) 0.390(3) 0.549(2) 0.027(7) Uiso 1 1 d . . . N2 N 1.13034(13) 0.5670(2) 0.62394(16) 0.0311(5) Uani 1 1 d . . . H02 H 1.1233(19) 0.618(3) 0.651(2) 0.030(8) Uiso 1 1 d . . . C1 C 0.98891(15) 0.5723(2) 0.62528(17) 0.0292(5) Uani 1 1 d . . . C2 C 1.06440(14) 0.5174(2) 0.60278(17) 0.0279(5) Uani 1 1 d . . . C4 C 0.99517(15) 0.3767(2) 0.51896(17) 0.0299(5) Uani 1 1 d . . . H4A H 1.0100 0.3571 0.4606 0.036 Uiso 1 1 calc R . . H4B H 0.9531 0.4327 0.5159 0.036 Uiso 1 1 calc R . . C5 C 0.96264(14) 0.2740(2) 0.56301(19) 0.0298(5) Uani 1 1 d . . . H5A H 0.9666 0.2109 0.5239 0.036 Uiso 1 1 calc R . . H5B H 0.9960 0.2575 0.6125 0.036 Uiso 1 1 calc R . . C6 C 0.87862(14) 0.2843(2) 0.59180(18) 0.0271(5) Uani 1 1 d . . . C7 C 0.85864(15) 0.3096(2) 0.67479(18) 0.0291(5) Uani 1 1 d . . . C8 C 0.91895(16) 0.3340(2) 0.74048(18) 0.0325(5) Uani 1 1 d . . . C9 C 0.95966(15) 0.4341(2) 0.74039(17) 0.0300(5) Uani 1 1 d . . . C10 C 0.93780(15) 0.5275(2) 0.68414(17) 0.0286(5) Uani 1 1 d . . . C11 C 0.77939(17) 0.3094(2) 0.69851(18) 0.0331(6) Uani 1 1 d . . . H11 H 0.7657 0.3255 0.7551 0.040 Uiso 1 1 calc R . . C12 C 0.72089(15) 0.2863(2) 0.64119(19) 0.0318(5) Uani 1 1 d . A . C13 C 0.74093(15) 0.2624(2) 0.55763(18) 0.0281(5) Uani 1 1 d . . . C14 C 0.81884(14) 0.2627(2) 0.53366(16) 0.0270(5) Uani 1 1 d . . . H14 H 0.8321 0.2479 0.4767 0.032 Uiso 1 1 calc R . . C15 C 0.6243(3) 0.3285(5) 0.7422(4) 0.0386(15) Uiso 0.71(2) 1 d PD A 1 H15A H 0.5674 0.3249 0.7513 0.046 Uiso 0.71(2) 1 calc PR A 1 H15B H 0.6417 0.4051 0.7456 0.046 Uiso 0.71(2) 1 calc PR A 1 H15C H 0.6511 0.2851 0.7855 0.046 Uiso 0.71(2) 1 calc PR A 1 C15' C 0.6122(7) 0.3628(12) 0.7176(9) 0.038(4) Uiso 0.29(2) 1 d PD A 2 H15D H 0.5555 0.3513 0.7239 0.046 Uiso 0.29(2) 1 calc PR A 2 H15E H 0.6219 0.4371 0.6963 0.046 Uiso 0.29(2) 1 calc PR A 2 H15F H 0.6379 0.3538 0.7723 0.046 Uiso 0.29(2) 1 calc PR A 2 O1 O 0.64291(12) 0.28483(19) 0.66006(14) 0.0408(5) Uani 1 1 d D . . C16 C 0.69465(18) 0.2329(3) 0.41710(18) 0.0402(7) Uani 1 1 d . . . H16A H 0.7199 0.3013 0.3989 0.060 Uiso 1 1 calc R . . H16B H 0.6453 0.2228 0.3862 0.060 Uiso 1 1 calc R . . H16C H 0.7297 0.1709 0.4057 0.060 Uiso 1 1 calc R . . O2 O 0.67864(11) 0.23840(16) 0.50528(13) 0.0330(4) Uani 1 1 d . . . C21 C 1.01795(17) 0.4529(3) 0.80159(19) 0.0358(6) Uani 1 1 d . . . H21 H 1.0464 0.5200 0.8013 0.043 Uiso 1 1 calc R . . C22 C 1.03413(19) 0.3744(3) 0.8622(2) 0.0423(7) Uani 1 1 d . . . H22 H 1.0743 0.3873 0.9025 0.051 Uiso 1 1 calc R . . C23 C 0.9918(2) 0.2769(3) 0.8641(2) 0.0431(7) Uani 1 1 d . . . H23 H 1.0017 0.2242 0.9070 0.052 Uiso 1 1 calc R . . C24 C 0.93476(19) 0.2565(2) 0.80282(19) 0.0385(6) Uani 1 1 d . . . H24 H 0.9065 0.1892 0.8036 0.046 Uiso 1 1 calc R . . C31 C 0.97040(18) 0.6700(2) 0.5836(2) 0.0350(6) Uani 1 1 d . . . H31 H 1.0069 0.7020 0.5456 0.042 Uiso 1 1 calc R . . C32 C 0.89854(18) 0.7198(2) 0.5980(2) 0.0404(6) Uani 1 1 d . . . H32 H 0.8854 0.7858 0.5694 0.048 Uiso 1 1 calc R . . C33 C 0.84624(16) 0.6739(2) 0.6536(2) 0.0391(7) Uani 1 1 d . . . H33 H 0.7965 0.7074 0.6622 0.047 Uiso 1 1 calc R . . C34 C 0.86543(16) 0.5797(2) 0.69698(19) 0.0341(6) Uani 1 1 d . . . H34 H 0.8291 0.5497 0.7361 0.041 Uiso 1 1 calc R . . C41 C 1.20883(14) 0.5359(2) 0.59898(19) 0.0304(5) Uani 1 1 d . . . C42 C 1.23097(17) 0.5453(2) 0.5139(2) 0.0367(6) Uani 1 1 d . . . C43 C 1.30904(17) 0.5222(2) 0.4933(2) 0.0390(6) Uani 1 1 d . . . H43 H 1.3256 0.5259 0.4363 0.047 Uiso 1 1 calc R . . C44 C 1.36254(16) 0.4939(2) 0.5552(2) 0.0391(7) Uani 1 1 d . . . H44 H 1.4157 0.4802 0.5405 0.047 Uiso 1 1 calc R . . C45 C 1.33929(17) 0.4855(2) 0.6380(2) 0.0380(6) Uani 1 1 d . . . H45 H 1.3767 0.4658 0.6797 0.046 Uiso 1 1 calc R . . C46 C 1.26147(16) 0.5056(2) 0.66155(19) 0.0333(6) Uani 1 1 d . . . C47 C 1.23586(19) 0.4944(3) 0.7512(2) 0.0446(7) Uani 1 1 d . . . H47A H 1.2802 0.4691 0.7855 0.067 Uiso 1 1 calc R . . H47B H 1.1929 0.4409 0.7548 0.067 Uiso 1 1 calc R . . H47C H 1.2177 0.5657 0.7721 0.067 Uiso 1 1 calc R . . C48 C 1.1753(2) 0.5823(4) 0.4464(2) 0.0543(9) Uani 1 1 d . . . H48A H 1.1330 0.5283 0.4402 0.081 Uiso 1 1 calc R . . H48B H 1.2038 0.5892 0.3930 0.081 Uiso 1 1 calc R . . H48C H 1.1529 0.6537 0.4618 0.081 Uiso 1 1 calc R . . C98 C 0.6858(5) 0.5575(9) 0.5342(5) 0.061(2) Uani 0.750(6) 1 d PD B 1 H98A H 0.6747 0.6046 0.5835 0.073 Uiso 0.750(6) 1 calc PR B 1 H98B H 0.7156 0.4925 0.5537 0.073 Uiso 0.750(6) 1 calc PR B 1 Cl1 Cl 0.59673(18) 0.5151(3) 0.48728(18) 0.1004(9) Uani 0.750(6) 1 d PD B 1 Cl2 Cl 0.74126(14) 0.6303(3) 0.46093(12) 0.1085(13) Uani 0.750(6) 1 d PD B 1 C98' C 0.6705(9) 0.539(3) 0.5416(13) 0.040(5) Uiso 0.250(6) 1 d PD B 2 H98C H 0.6700 0.4634 0.5642 0.048 Uiso 0.250(6) 1 calc PR B 2 H98D H 0.6758 0.5901 0.5897 0.048 Uiso 0.250(6) 1 calc PR B 2 Cl1' Cl 0.5827(4) 0.5640(8) 0.4919(5) 0.088(2) Uiso 0.250(6) 1 d PD B 2 Cl2' Cl 0.7525(3) 0.5544(5) 0.4756(4) 0.0685(17) Uiso 0.250(6) 1 d PD B 2 C99 C 0.9740(3) 0.1424(5) 0.2965(4) 0.0377(14) Uiso 0.560(9) 1 d PD C 1 F1 F 1.0255(2) 0.2211(4) 0.2874(3) 0.0478(11) Uiso 0.560(9) 1 d PD C 1 F2 F 0.9917(3) 0.0586(4) 0.2456(4) 0.0672(14) Uiso 0.560(9) 1 d PD C 1 F3 F 0.9785(3) 0.1037(5) 0.3742(3) 0.0679(15) Uiso 0.560(9) 1 d PD C 1 S1 S 0.87454(16) 0.1890(3) 0.27537(16) 0.0208(5) Uani 0.560(9) 1 d PD C 1 O3 O 0.8699(3) 0.2847(4) 0.3325(3) 0.0420(13) Uiso 0.560(9) 1 d PD C 1 O4 O 0.8696(3) 0.2274(4) 0.1913(3) 0.0292(13) Uiso 0.560(9) 1 d PD C 1 O5 O 0.8265(3) 0.1019(4) 0.3021(4) 0.0359(14) Uiso 0.560(9) 1 d PD C 1 C99' C 0.9727(4) 0.1148(7) 0.2752(5) 0.0432(18) Uiso 0.440(9) 1 d PD C 2 F1' F 1.0330(3) 0.1813(5) 0.2703(4) 0.0477(13) Uiso 0.440(9) 1 d PD C 2 F2' F 0.9804(4) 0.0489(4) 0.2089(5) 0.0562(16) Uiso 0.440(9) 1 d PD C 2 F3' F 0.9791(3) 0.0538(5) 0.3438(4) 0.0613(18) Uiso 0.440(9) 1 d PD C 2 S1' S 0.8793(4) 0.1823(5) 0.2704(5) 0.064(2) Uani 0.440(9) 1 d PD C 2 O3' O 0.8884(5) 0.2651(7) 0.3376(5) 0.055(2) Uiso 0.440(9) 1 d PD C 2 O4' O 0.8800(5) 0.2136(7) 0.1827(5) 0.051(3) Uiso 0.440(9) 1 d PD C 2 O5' O 0.8202(3) 0.0946(4) 0.2836(4) 0.0281(14) Uiso 0.440(9) 1 d PD C 2 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 0.0200(9) 0.0309(11) 0.0385(12) -0.0050(9) 0.0014(8) 0.0011(8) N2 0.0282(11) 0.0283(11) 0.0368(12) -0.0058(10) -0.0029(9) -0.0003(8) C1 0.0270(12) 0.0283(12) 0.0323(13) -0.0048(10) -0.0026(10) 0.0030(9) C2 0.0222(11) 0.0291(12) 0.0322(13) 0.0006(10) -0.0006(9) 0.0016(9) C4 0.0266(11) 0.0327(13) 0.0303(13) -0.0071(10) 0.0003(10) 0.0004(10) C5 0.0237(11) 0.0292(12) 0.0364(13) -0.0048(10) -0.0035(10) 0.0019(9) C6 0.0264(11) 0.0216(10) 0.0334(13) -0.0004(9) 0.0008(10) -0.0021(9) C7 0.0293(12) 0.0250(12) 0.0329(13) -0.0020(10) -0.0025(10) -0.0021(9) C8 0.0333(13) 0.0318(13) 0.0324(13) -0.0071(10) -0.0012(10) -0.0006(10) C9 0.0284(12) 0.0328(13) 0.0287(12) -0.0066(10) 0.0015(10) 0.0002(10) C10 0.0268(12) 0.0267(11) 0.0324(13) -0.0068(10) -0.0036(10) -0.0008(9) C11 0.0350(14) 0.0330(13) 0.0311(13) -0.0070(10) 0.0041(11) -0.0039(11) C12 0.0288(12) 0.0260(11) 0.0406(15) -0.0042(11) 0.0047(11) -0.0025(10) C13 0.0269(11) 0.0241(11) 0.0334(12) 0.0008(10) -0.0034(10) -0.0022(9) C14 0.0255(11) 0.0263(12) 0.0292(12) 0.0005(9) -0.0013(9) -0.0002(9) O1 0.0287(9) 0.0481(12) 0.0454(12) -0.0090(9) 0.0087(8) -0.0090(8) C16 0.0315(13) 0.0588(18) 0.0303(14) 0.0051(13) -0.0027(11) -0.0031(13) O2 0.0254(8) 0.0393(10) 0.0344(10) 0.0037(8) -0.0041(7) -0.0017(7) C21 0.0313(13) 0.0407(14) 0.0355(14) -0.0076(11) -0.0046(11) -0.0023(11) C22 0.0396(15) 0.0515(17) 0.0359(14) -0.0090(13) -0.0094(12) 0.0029(14) C23 0.0507(18) 0.0440(16) 0.0347(15) -0.0020(13) -0.0058(13) 0.0050(14) C24 0.0458(17) 0.0325(14) 0.0372(14) -0.0047(11) -0.0033(12) -0.0005(12) C31 0.0359(14) 0.0299(13) 0.0390(15) -0.0015(11) -0.0021(11) 0.0013(11) C32 0.0414(15) 0.0319(14) 0.0479(17) -0.0044(12) -0.0075(13) 0.0096(12) C33 0.0261(12) 0.0369(14) 0.0543(18) -0.0119(13) -0.0074(12) 0.0079(11) C34 0.0253(12) 0.0353(13) 0.0419(15) -0.0082(11) 0.0004(10) 0.0004(10) C41 0.0214(11) 0.0281(12) 0.0416(14) -0.0072(11) -0.0027(10) -0.0004(9) C42 0.0298(13) 0.0375(14) 0.0426(16) 0.0013(12) -0.0031(11) -0.0036(11) C43 0.0318(13) 0.0321(14) 0.0533(17) -0.0022(13) 0.0055(12) -0.0034(11) C44 0.0257(12) 0.0260(13) 0.065(2) -0.0064(13) -0.0005(12) -0.0039(10) C45 0.0272(12) 0.0285(12) 0.0584(19) -0.0053(12) -0.0100(12) 0.0000(10) C46 0.0333(13) 0.0245(12) 0.0421(15) -0.0039(10) -0.0058(11) 0.0008(10) C47 0.0432(16) 0.0485(17) 0.0421(17) -0.0038(13) -0.0087(13) 0.0055(14) C48 0.0392(17) 0.079(3) 0.0448(19) 0.0120(18) -0.0011(14) 0.0014(16) C98 0.067(4) 0.058(5) 0.057(4) 0.002(3) -0.029(3) 0.009(4) Cl1 0.0964(15) 0.0783(16) 0.1266(19) 0.0091(13) -0.0508(13) -0.0300(13) Cl2 0.1022(15) 0.168(4) 0.0550(10) 0.0008(12) -0.0190(9) -0.0317(17) S1 0.0155(8) 0.0269(11) 0.0200(9) 0.0067(7) -0.0012(7) -0.0004(7) S1' 0.053(3) 0.053(3) 0.086(4) 0.021(2) 0.014(2) -0.003(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N1 C2 1.306(3) . ? N1 C4 1.470(3) . ? N2 C2 1.318(3) . ? N2 C41 1.444(3) . ? C1 C10 1.389(4) . ? C1 C31 1.397(4) . ? C1 C2 1.492(3) . ? C4 C5 1.537(4) . ? C5 C6 1.507(3) . ? C6 C7 1.397(4) . ? C6 C14 1.399(4) . ? C7 C11 1.401(4) . ? C7 C8 1.494(4) . ? C8 C24 1.395(4) . ? C8 C9 1.401(4) . ? C9 C21 1.408(4) . ? C9 C10 1.494(4) . ? C10 C34 1.401(4) . ? C11 C12 1.379(4) . ? C12 O1 1.361(3) . ? C12 C13 1.402(4) . ? C13 O2 1.379(3) . ? C13 C14 1.380(3) . ? C15 O1 1.445(5) . ? C15' O1 1.417(10) . ? C16 O2 1.429(4) . ? C21 C22 1.384(5) . ? C22 C23 1.389(5) . ? C23 C24 1.398(4) . ? C31 C32 1.384(4) . ? C32 C33 1.373(5) . ? C33 C34 1.378(4) . ? C41 C46 1.388(4) . ? C41 C42 1.409(4) . ? C42 C43 1.397(4) . ? C42 C48 1.501(5) . ? C43 C44 1.385(5) . ? C44 C45 1.378(5) . ? C45 C46 1.398(4) . ? C46 C47 1.497(5) . ? C98 Cl2 1.742(9) . ? C98 Cl1 1.767(7) . ? C98' Cl1' 1.719(16) . ? C98' Cl2' 1.755(16) . ? C99 F1 1.307(6) . ? C99 F3 1.325(7) . ? C99 F2 1.336(7) . ? C99 S1 1.816(6) . ? S1 O5 1.405(5) . ? S1 O4 1.419(5) . ? S1 O3 1.479(5) . ? C99' F1' 1.310(8) . ? C99' F3' 1.325(8) . ? C99' F2' 1.330(9) . ? C99' S1' 1.792(9) . ? S1' O4' 1.444(9) . ? S1' O3' 1.477(8) . ? S1' O5' 1.483(7) . ? 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 N1 C4 125.6(2) . . ? C2 N2 C41 126.7(2) . . ? C10 C1 C31 120.8(2) . . ? C10 C1 C2 121.7(2) . . ? C31 C1 C2 117.5(2) . . ? N1 C2 N2 122.1(2) . . ? N1 C2 C1 120.0(2) . . ? N2 C2 C1 117.9(2) . . ? N1 C4 C5 113.6(2) . . ? C6 C5 C4 114.4(2) . . ? C7 C6 C14 119.2(2) . . ? C7 C6 C5 122.4(2) . . ? C14 C6 C5 118.3(2) . . ? C6 C7 C11 119.2(2) . . ? C6 C7 C8 122.5(2) . . ? C11 C7 C8 118.3(2) . . ? C24 C8 C9 119.6(3) . . ? C24 C8 C7 119.6(2) . . ? C9 C8 C7 120.8(2) . . ? C8 C9 C21 119.3(3) . . ? C8 C9 C10 122.6(2) . . ? C21 C9 C10 117.7(2) . . ? C1 C10 C34 118.1(2) . . ? C1 C10 C9 123.1(2) . . ? C34 C10 C9 118.5(2) . . ? C12 C11 C7 121.2(3) . . ? O1 C12 C11 124.2(3) . . ? O1 C12 C13 116.3(2) . . ? C11 C12 C13 119.5(2) . . ? O2 C13 C14 124.9(2) . . ? O2 C13 C12 115.4(2) . . ? C14 C13 C12 119.7(2) . . ? C13 C14 C6 121.1(2) . . ? C12 O1 C15' 119.6(5) . . ? C12 O1 C15 114.1(3) . . ? C15' O1 C15 24.5(6) . . ? C13 O2 C16 117.1(2) . . ? C22 C21 C9 120.5(3) . . ? C21 C22 C23 120.2(3) . . ? C22 C23 C24 119.8(3) . . ? C8 C24 C23 120.6(3) . . ? C32 C31 C1 119.6(3) . . ? C33 C32 C31 120.1(3) . . ? C32 C33 C34 120.5(3) . . ? C33 C34 C10 120.9(3) . . ? C46 C41 C42 122.5(2) . . ? C46 C41 N2 118.0(3) . . ? C42 C41 N2 119.3(2) . . ? C43 C42 C41 117.6(3) . . ? C43 C42 C48 119.5(3) . . ? C41 C42 C48 122.8(3) . . ? C44 C43 C42 120.6(3) . . ? C45 C44 C43 120.6(3) . . ? C44 C45 C46 121.0(3) . . ? C41 C46 C45 117.8(3) . . ? C41 C46 C47 121.2(3) . . ? C45 C46 C47 121.0(3) . . ? Cl2 C98 Cl1 109.4(4) . . ? Cl1' C98' Cl2' 113.5(11) . . ? F1 C99 F3 108.9(5) . . ? F1 C99 F2 110.0(5) . . ? F3 C99 F2 106.2(5) . . ? F1 C99 S1 112.1(4) . . ? F3 C99 S1 109.7(4) . . ? F2 C99 S1 109.7(4) . . ? O5 S1 O4 120.0(3) . . ? O5 S1 O3 112.2(4) . . ? O4 S1 O3 108.4(4) . . ? O5 S1 C99 104.5(3) . . ? O4 S1 C99 109.4(3) . . ? O3 S1 C99 100.5(3) . . ? F1' C99' F3' 109.3(6) . . ? F1' C99' F2' 104.4(6) . . ? F3' C99' F2' 107.8(7) . . ? F1' C99' S1' 114.2(6) . . ? F3' C99' S1' 111.4(6) . . ? F2' C99' S1' 109.3(6) . . ? O4' S1' O3' 121.2(6) . . ? O4' S1' O5' 109.4(6) . . ? O3' S1' O5' 117.4(6) . . ? O4' S1' C99' 98.9(6) . . ? O3' S1' C99' 100.8(5) . . ? O5' S1' C99' 105.4(5) . . ? 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 N1 H01 O2 0.84(3) 2.12(4) 2.927(3) 160(3) 3 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.763 _refine_diff_density_min -0.484 _refine_diff_density_rms 0.060 _database_code_depnum_ccdc_archive 'CCDC 928374' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_joe124_1 #TrackingRef 'jof822c_joe_124.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C28 H29 Br N2 O2 Pd' _chemical_formula_weight 611.84 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Pd Pd 0.1215 3.9337 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 29.001(2) _cell_length_b 9.2274(7) _cell_length_c 19.9745(16) _cell_angle_alpha 90.00 _cell_angle_beta 102.373(7) _cell_angle_gamma 90.00 _cell_volume 5221.1(7) _cell_formula_units_Z 8 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3426 _cell_measurement_theta_min 3.1175 _cell_measurement_theta_max 74.6252 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.557 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2464 _exptl_absorpt_coefficient_mu 7.736 _exptl_absorpt_correction_T_max 0.837 _exptl_absorpt_correction_T_min 0.524 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET) (compiled Jun 5 2012,17:40:27) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54184 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9964 _diffrn_reflns_av_R_equivalents 0.0419 _diffrn_reflns_av_sigmaI/netI 0.0505 _diffrn_reflns_limit_h_min -35 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 74.80 _reflns_number_total 5145 _reflns_number_gt 4453 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET) (compiled Jun 5 2012,17:40:27) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET) (compiled Jun 5 2012,17:40:27) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.18t (release 05-06-2012 CrysAlis171 .NET) (compiled Jun 5 2012,17:40:27) ; _computing_structure_solution ; olex2.solve (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard, H. Puschmann, in preparation, 2011) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics Shelxtl _computing_publication_material Shelxtl _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0862P)^2^+9.0565P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment 'NH2 free with SADI, rigid methyls, others riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5145 _refine_ls_number_parameters 318 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1370 _refine_ls_wR_factor_gt 0.1280 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Pd1 Pd 0.450307(10) 0.44385(3) 0.663698(15) 0.01998(13) Uani 1 1 d . . . N1 N 0.41342(14) 0.2825(4) 0.7013(2) 0.0277(8) Uani 1 1 d D . . H01A H 0.4313(18) 0.261(6) 0.739(2) 0.023(13) Uiso 1 1 d D . . H01B H 0.3889(15) 0.324(5) 0.706(3) 0.016(12) Uiso 1 1 d D . . N2 N 0.48562(13) 0.6140(4) 0.62927(19) 0.0206(7) Uani 1 1 d . . . Br1 Br 0.511746(17) 0.25819(5) 0.64510(3) 0.02888(15) Uani 1 1 d . . . C1 C 0.40181(16) 0.5850(5) 0.6809(2) 0.0235(8) Uani 1 1 d . . . C2 C 0.40228(15) 0.6245(5) 0.7483(2) 0.0232(8) Uani 1 1 d . . . H2 H 0.4236 0.5782 0.7848 0.028 Uiso 1 1 calc R . . C3 C 0.37212(16) 0.7304(5) 0.7626(2) 0.0263(9) Uani 1 1 d . . . H3 H 0.3730 0.7574 0.8088 0.032 Uiso 1 1 calc R . . C4 C 0.34078(17) 0.7970(5) 0.7098(3) 0.0289(9) Uani 1 1 d . . . H4 H 0.3202 0.8705 0.7194 0.035 Uiso 1 1 calc R . . C5 C 0.33960(16) 0.7558(5) 0.6426(3) 0.0268(9) Uani 1 1 d . . . H5 H 0.3181 0.8021 0.6063 0.032 Uiso 1 1 calc R . . C6 C 0.36936(15) 0.6478(4) 0.6273(2) 0.0208(8) Uani 1 1 d . . . C7 C 0.36659(14) 0.6006(5) 0.5551(2) 0.0223(8) Uani 1 1 d . . . C8 C 0.39032(15) 0.6768(5) 0.5127(2) 0.0257(9) Uani 1 1 d . . . H8 H 0.4072 0.7622 0.5296 0.031 Uiso 1 1 calc R . . C9 C 0.39005(16) 0.6314(5) 0.4466(2) 0.0281(9) Uani 1 1 d . . . H9 H 0.4067 0.6844 0.4185 0.034 Uiso 1 1 calc R . . C10 C 0.36511(17) 0.5071(6) 0.4220(2) 0.0305(10) Uani 1 1 d . . . H10 H 0.3646 0.4750 0.3766 0.037 Uiso 1 1 calc R . . C11 C 0.34094(19) 0.4296(6) 0.4630(3) 0.0336(11) Uani 1 1 d . . . H11 H 0.3241 0.3445 0.4456 0.040 Uiso 1 1 calc R . . C12 C 0.34104(15) 0.4749(5) 0.5295(2) 0.0229(8) Uani 1 1 d . . . C13 C 0.31240(16) 0.3952(5) 0.5713(2) 0.0241(8) Uani 1 1 d . . . C14 C 0.27040(16) 0.4614(5) 0.5809(2) 0.0249(9) Uani 1 1 d . . . H14 H 0.2618 0.5537 0.5610 0.030 Uiso 1 1 calc R . . C15 C 0.24157(15) 0.3949(5) 0.6185(2) 0.0255(9) Uani 1 1 d . . . C16 C 0.25415(16) 0.2575(5) 0.6474(2) 0.0231(9) Uani 1 1 d . . . C17 C 0.29455(15) 0.1917(5) 0.6367(2) 0.0255(9) Uani 1 1 d . . . H17 H 0.3025 0.0980 0.6554 0.031 Uiso 1 1 calc R . . C18 C 0.32439(16) 0.2584(5) 0.5990(2) 0.0247(9) Uani 1 1 d . . . C19 C 0.1884(2) 0.5934(6) 0.6054(4) 0.0429(13) Uani 1 1 d . . . H19A H 0.2142 0.6604 0.6240 0.064 Uiso 1 1 calc R . . H19B H 0.1596 0.6248 0.6194 0.064 Uiso 1 1 calc R . . H19C H 0.1830 0.5927 0.5553 0.064 Uiso 1 1 calc R . . O1 O 0.20056(12) 0.4524(4) 0.6308(2) 0.0299(7) Uani 1 1 d . . . C20 C 0.23489(18) 0.0630(6) 0.7139(3) 0.0337(11) Uani 1 1 d . . . H20A H 0.2342 -0.0092 0.6777 0.051 Uiso 1 1 calc R . . H20B H 0.2117 0.0368 0.7411 0.051 Uiso 1 1 calc R . . H20C H 0.2665 0.0656 0.7437 0.051 Uiso 1 1 calc R . . O2 O 0.22372(11) 0.2010(4) 0.68401(18) 0.0285(7) Uani 1 1 d . . . C21 C 0.36915(16) 0.1808(5) 0.5928(3) 0.0288(10) Uani 1 1 d . . . H21A H 0.3865 0.2410 0.5654 0.035 Uiso 1 1 calc R . . H21B H 0.3608 0.0884 0.5679 0.035 Uiso 1 1 calc R . . C22 C 0.40128(16) 0.1490(5) 0.6622(3) 0.0302(10) Uani 1 1 d . . . H22A H 0.3851 0.0818 0.6883 0.036 Uiso 1 1 calc R . . H22B H 0.4305 0.1013 0.6554 0.036 Uiso 1 1 calc R . . C23 C 0.48693(16) 0.7481(5) 0.6541(2) 0.0247(9) Uani 1 1 d . . . H23 H 0.4707 0.7681 0.6897 0.030 Uiso 1 1 calc R . . C24 C 0.51090(16) 0.8593(5) 0.6303(3) 0.0281(9) Uani 1 1 d . . . H24 H 0.5117 0.9528 0.6504 0.034 Uiso 1 1 calc R . . C25 C 0.53411(16) 0.8353(5) 0.5765(3) 0.0293(10) Uani 1 1 d . . . C26 C 0.53213(15) 0.6941(5) 0.5510(2) 0.0257(9) Uani 1 1 d . . . H26 H 0.5472 0.6713 0.5145 0.031 Uiso 1 1 calc R . . C27 C 0.50848(15) 0.5882(5) 0.5782(2) 0.0236(8) Uani 1 1 d . . . H27 H 0.5082 0.4927 0.5604 0.028 Uiso 1 1 calc R . . C28 C 0.5603(2) 0.9521(6) 0.5479(3) 0.0404(13) Uani 1 1 d . . . H28A H 0.5941 0.9299 0.5584 0.061 Uiso 1 1 calc R . . H28B H 0.5550 1.0454 0.5685 0.061 Uiso 1 1 calc R . . H28C H 0.5489 0.9573 0.4981 0.061 Uiso 1 1 calc R . . 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 Pd1 0.01586(18) 0.01686(19) 0.02950(19) 0.00220(10) 0.00998(12) 0.00083(10) N1 0.0182(18) 0.0249(19) 0.043(2) 0.0098(17) 0.0140(16) 0.0031(15) N2 0.0189(17) 0.0146(16) 0.0308(18) 0.0011(13) 0.0106(13) -0.0001(13) Br1 0.0267(3) 0.0236(3) 0.0398(3) 0.00143(18) 0.0149(2) 0.00217(17) C1 0.019(2) 0.021(2) 0.032(2) -0.0005(17) 0.0110(16) -0.0022(17) C2 0.021(2) 0.023(2) 0.027(2) 0.0032(17) 0.0101(15) 0.0008(16) C3 0.023(2) 0.026(2) 0.034(2) -0.0052(18) 0.0153(17) -0.0051(17) C4 0.026(2) 0.023(2) 0.043(3) 0.0004(19) 0.0208(19) 0.0017(18) C5 0.023(2) 0.021(2) 0.038(2) 0.0055(17) 0.0112(18) 0.0026(16) C6 0.0204(19) 0.0156(18) 0.028(2) 0.0026(15) 0.0097(15) -0.0040(15) C7 0.0153(19) 0.020(2) 0.033(2) 0.0040(17) 0.0073(15) 0.0049(16) C8 0.020(2) 0.024(2) 0.035(2) 0.0075(18) 0.0095(16) 0.0032(17) C9 0.020(2) 0.033(2) 0.033(2) 0.0070(19) 0.0106(16) 0.0070(18) C10 0.030(2) 0.032(2) 0.032(2) -0.0008(19) 0.0122(18) 0.003(2) C11 0.031(3) 0.028(2) 0.043(3) -0.003(2) 0.011(2) -0.0002(19) C12 0.0182(19) 0.023(2) 0.029(2) 0.0014(17) 0.0081(16) -0.0010(16) C13 0.022(2) 0.022(2) 0.030(2) -0.0016(17) 0.0083(16) -0.0049(17) C14 0.023(2) 0.021(2) 0.031(2) 0.0019(16) 0.0060(17) -0.0009(16) C15 0.018(2) 0.027(2) 0.032(2) -0.0018(18) 0.0061(16) 0.0001(17) C16 0.019(2) 0.023(2) 0.029(2) -0.0006(16) 0.0102(16) -0.0030(16) C17 0.019(2) 0.023(2) 0.037(2) -0.0001(18) 0.0114(17) 0.0002(16) C18 0.020(2) 0.019(2) 0.037(2) -0.0049(17) 0.0122(17) -0.0010(16) C19 0.031(3) 0.027(3) 0.074(4) 0.011(3) 0.021(3) 0.009(2) O1 0.0183(15) 0.0262(17) 0.0473(19) 0.0038(14) 0.0115(13) 0.0046(12) C20 0.027(2) 0.034(3) 0.046(3) 0.012(2) 0.020(2) 0.0076(19) O2 0.0199(15) 0.0294(17) 0.0404(17) 0.0067(14) 0.0157(13) 0.0037(13) C21 0.023(2) 0.020(2) 0.048(3) -0.0054(19) 0.0174(19) -0.0029(17) C22 0.020(2) 0.017(2) 0.057(3) 0.009(2) 0.0172(19) 0.0000(17) C23 0.025(2) 0.018(2) 0.034(2) -0.0006(16) 0.0132(17) 0.0038(16) C24 0.025(2) 0.020(2) 0.041(2) -0.0046(18) 0.0119(18) -0.0020(17) C25 0.021(2) 0.024(2) 0.045(3) 0.0028(19) 0.0111(18) -0.0018(17) C26 0.021(2) 0.027(2) 0.032(2) -0.0002(18) 0.0119(16) -0.0002(17) C27 0.020(2) 0.022(2) 0.029(2) 0.0021(17) 0.0079(16) 0.0006(17) C28 0.045(3) 0.029(3) 0.056(3) -0.002(2) 0.030(3) -0.008(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Pd1 C1 2.000(5) . ? Pd1 N1 2.067(4) . ? Pd1 N2 2.071(4) . ? Pd1 Br1 2.5557(6) . ? N1 C22 1.461(7) . ? N2 C23 1.331(6) . ? N2 C27 1.351(6) . ? C1 C6 1.391(6) . ? C1 C2 1.392(6) . ? C2 C3 1.382(6) . ? C3 C4 1.381(7) . ? C4 C5 1.389(7) . ? C5 C6 1.394(6) . ? C6 C7 1.492(6) . ? C7 C8 1.391(6) . ? C7 C12 1.412(6) . ? C8 C9 1.385(7) . ? C9 C10 1.388(7) . ? C10 C11 1.387(7) . ? C11 C12 1.393(7) . ? C12 C13 1.491(6) . ? C13 C18 1.392(6) . ? C13 C14 1.412(7) . ? C14 C15 1.382(7) . ? C15 O1 1.371(6) . ? C15 C16 1.408(6) . ? C16 O2 1.364(5) . ? C16 C17 1.377(6) . ? C17 C18 1.405(6) . ? C18 C21 1.511(6) . ? C19 O1 1.413(6) . ? C20 O2 1.415(6) . ? C21 C22 1.525(7) . ? C23 C24 1.380(7) . ? C24 C25 1.401(7) . ? C25 C26 1.396(7) . ? C25 C28 1.501(7) . ? C26 C27 1.372(6) . ? 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 C1 Pd1 N1 88.20(17) . . ? C1 Pd1 N2 88.82(17) . . ? N1 Pd1 N2 176.71(16) . . ? C1 Pd1 Br1 178.03(13) . . ? N1 Pd1 Br1 90.08(11) . . ? N2 Pd1 Br1 92.88(10) . . ? C22 N1 Pd1 119.8(3) . . ? C23 N2 C27 117.8(4) . . ? C23 N2 Pd1 123.9(3) . . ? C27 N2 Pd1 118.3(3) . . ? C6 C1 C2 120.0(4) . . ? C6 C1 Pd1 121.6(3) . . ? C2 C1 Pd1 118.4(3) . . ? C3 C2 C1 120.7(4) . . ? C4 C3 C2 119.9(4) . . ? C3 C4 C5 119.5(4) . . ? C4 C5 C6 121.3(4) . . ? C1 C6 C5 118.6(4) . . ? C1 C6 C7 120.6(4) . . ? C5 C6 C7 120.8(4) . . ? C8 C7 C12 119.0(4) . . ? C8 C7 C6 120.7(4) . . ? C12 C7 C6 120.3(4) . . ? C9 C8 C7 121.7(5) . . ? C8 C9 C10 118.9(4) . . ? C11 C10 C9 120.5(5) . . ? C10 C11 C12 120.8(5) . . ? C11 C12 C7 119.0(4) . . ? C11 C12 C13 119.9(4) . . ? C7 C12 C13 121.0(4) . . ? C18 C13 C14 119.2(4) . . ? C18 C13 C12 123.2(4) . . ? C14 C13 C12 117.5(4) . . ? C15 C14 C13 121.4(4) . . ? O1 C15 C14 125.0(4) . . ? O1 C15 C16 115.7(4) . . ? C14 C15 C16 119.3(4) . . ? O2 C16 C17 125.8(4) . . ? O2 C16 C15 115.0(4) . . ? C17 C16 C15 119.2(4) . . ? C16 C17 C18 122.2(4) . . ? C13 C18 C17 118.7(4) . . ? C13 C18 C21 122.9(4) . . ? C17 C18 C21 118.3(4) . . ? C15 O1 C19 116.9(4) . . ? C16 O2 C20 117.0(4) . . ? C18 C21 C22 112.6(4) . . ? N1 C22 C21 110.8(4) . . ? N2 C23 C24 122.6(4) . . ? C23 C24 C25 120.5(4) . . ? C26 C25 C24 116.1(4) . . ? C26 C25 C28 121.0(5) . . ? C24 C25 C28 122.9(5) . . ? C27 C26 C25 120.3(4) . . ? N2 C27 C26 122.8(4) . . ? 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 N1 H01A Br1 0.84(4) 2.54(4) 3.364(4) 167(5) 2_656 C24 H24 Br1 0.95 2.82 3.692(5) 153.1 1_565 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 70.00 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 1.616 _refine_diff_density_min -1.495 _refine_diff_density_rms 0.151 #==END _database_code_depnum_ccdc_archive 'CCDC 928375'