# Copyright The Royal Society of Chemistry, 1998 # CCDC Number: 186/1219 data_ms359 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,13-Dibromo-7,8-diethyl-5,10,15,20-tetraphenyl- porphyrin (orthorhombic modification) ; _chemical_name_common ? _chemical_formula_moiety 'C48 H36 Br2 N4' _chemical_formula_sum 'C48 H36 Br2 N4' _chemical_formula_weight 828.63 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' 'Br' 'Br' -0.2901 2.4595 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_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' _cell_length_a 7.19590(10) _cell_length_b 20.2757(3) _cell_length_c 26.44990(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3859.09(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ; 8192 reflections with I > 10sigma I ; _cell_measurement_theta_min n/a _cell_measurement_theta_max n/a _exptl_crystal_description rhombus _exptl_crystal_colour red _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 2.141 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.2793 _exptl_absorpt_correction_T_max 0.7832 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures; each set had a different &Gf angle for the crystal and each exposure covered 0.3 &^o&0 in &Gw. The crystal-to-detector distance was 4.910 cm. Coverage of the unique set is over 97 % complete to at least 26&^o$0 in &Gq. Crystal decay was monitored by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. No decay was observed. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method &Gw _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% stable _diffrn_reflns_number 24458 _diffrn_reflns_av_R_equivalents 0.0281 _diffrn_reflns_av_sigmaI/netI 0.0350 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.27 _diffrn_reflns_theta_max 28.20 _reflns_number_total 9107 _reflns_number_gt 8435 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; SMART, Software Reference Manual (1994). Siemens Anal. Instr. WI ; _computing_cell_refinement SMART _computing_data_reduction ; SAINT Version 4, Software Reference Manual (1995). Siemens Analytical Instr., WI ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus, Siemens, 1994' _computing_publication_material 'XCIF, Shelxtl-Plus, Siemens, 1994' _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 w=1/[\s^2^(Fo^2^)+(0.0309P)^2^+1.0615P] 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 constr _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 0.000(5) _refine_ls_number_reflns 9107 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0316 _refine_ls_R_factor_gt 0.0275 _refine_ls_wR_factor_ref 0.0646 _refine_ls_wR_factor_gt 0.0628 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N21 N 0.4280(3) 0.62304(8) 0.15163(6) 0.0186(3) Uani 1 d . . . N22 N 0.5077(2) 0.70508(8) 0.24166(7) 0.0176(4) Uani 1 d . . . H22 H 0.4325 0.6726 0.2334 0.021 Uiso 1 calc R . . N23 N 0.1808(3) 0.63557(8) 0.28894(7) 0.0185(4) Uani 1 d . . . N24 N 0.1064(2) 0.56073(8) 0.19807(6) 0.0186(4) Uani 1 d . . . H24 H 0.1995 0.5852 0.2087 0.022 Uiso 1 calc R . . C1 C 0.3817(3) 0.58060(10) 0.11255(7) 0.0183(4) Uani 1 d . . . C2 C 0.5293(3) 0.58234(10) 0.07407(8) 0.0198(4) Uani 1 d . . . C3 C 0.6539(3) 0.62777(10) 0.08854(8) 0.0212(4) Uani 1 d . . . H3 H 0.7631 0.6405 0.0709 0.025 Uiso 1 calc R . . C4 C 0.5888(3) 0.65373(10) 0.13669(8) 0.0188(4) Uani 1 d . . . C5 C 0.6827(3) 0.70617(10) 0.16157(8) 0.0187(4) Uani 1 d . . . C51 C 0.8308(3) 0.73835(10) 0.12931(8) 0.0198(4) Uani 1 d . . . C52 C 0.7786(3) 0.78669(11) 0.09415(10) 0.0283(5) Uani 1 d . . . H52 H 0.6525 0.8003 0.0922 0.034 Uiso 1 calc R . . C53 C 0.9100(4) 0.81483(14) 0.06219(10) 0.0385(6) Uani 1 d . . . H53 H 0.8737 0.8484 0.0392 0.046 Uiso 1 calc R . . C54 C 1.0938(4) 0.79415(14) 0.06375(11) 0.0418(7) Uani 1 d . . . H54 H 1.1831 0.8130 0.0416 0.050 Uiso 1 calc R . . C55 C 1.1459(4) 0.74550(12) 0.09810(10) 0.0348(6) Uani 1 d . . . H55 H 1.2714 0.7310 0.0992 0.042 Uiso 1 calc R . . C56 C 1.0161(3) 0.71802(11) 0.13078(9) 0.0242(5) Uani 1 d . . . H56 H 1.0536 0.6852 0.1543 0.029 Uiso 1 calc R . . C6 C 0.6438(3) 0.73058(10) 0.21011(8) 0.0177(4) Uani 1 d . . . C7 C 0.7326(3) 0.78343(10) 0.23829(8) 0.0188(4) Uani 1 d . . . C71 C 0.8942(3) 0.82668(10) 0.22295(9) 0.0217(4) Uani 1 d . . . H71A H 0.8730 0.8722 0.2353 0.026 Uiso 1 calc R . . H71B H 0.9026 0.8282 0.1856 0.026 Uiso 1 calc R . . C72 C 1.0778(3) 0.80018(12) 0.24481(10) 0.0306(5) Uani 1 d . . . H72A H 1.1803 0.8290 0.2345 0.046 Uiso 1 calc R . . H72B H 1.0998 0.7555 0.2321 0.046 Uiso 1 calc R . . H72C H 1.0700 0.7992 0.2818 0.046 Uiso 1 calc R . . C8 C 0.6483(3) 0.78784(10) 0.28480(8) 0.0194(4) Uani 1 d . . . C81 C 0.6923(3) 0.84245(10) 0.32223(8) 0.0226(5) Uani 1 d . . . H81A H 0.8237 0.8559 0.3184 0.027 Uiso 1 calc R . . H81B H 0.6750 0.8258 0.3571 0.027 Uiso 1 calc R . . C82 C 0.5647(4) 0.90274(11) 0.31351(9) 0.0319(5) Uani 1 d . . . H82A H 0.5955 0.9373 0.3380 0.048 Uiso 1 calc R . . H82B H 0.4347 0.8895 0.3179 0.048 Uiso 1 calc R . . H82C H 0.5831 0.9196 0.2791 0.048 Uiso 1 calc R . . C9 C 0.5053(3) 0.73733(10) 0.28774(8) 0.0175(4) Uani 1 d . . . C10 C 0.3891(3) 0.72045(10) 0.32856(8) 0.0192(4) Uani 1 d . . . C101 C 0.4174(3) 0.75535(10) 0.37848(8) 0.0209(4) Uani 1 d . . . C102 C 0.5562(4) 0.73393(11) 0.41169(9) 0.0296(5) Uani 1 d . . . H102 H 0.6317 0.6972 0.4030 0.036 Uiso 1 calc R . . C103 C 0.5840(4) 0.76656(13) 0.45766(9) 0.0379(6) Uani 1 d . . . H103 H 0.6779 0.7519 0.4802 0.045 Uiso 1 calc R . . C104 C 0.4739(4) 0.82065(14) 0.47034(10) 0.0389(7) Uani 1 d . . . H104 H 0.4957 0.8437 0.5010 0.047 Uiso 1 calc R . . C105 C 0.3335(4) 0.84064(13) 0.43843(10) 0.0352(6) Uani 1 d . . . H105 H 0.2568 0.8768 0.4476 0.042 Uiso 1 calc R . . C106 C 0.3035(3) 0.80804(11) 0.39274(9) 0.0264(5) Uani 1 d . . . H106 H 0.2051 0.8217 0.3712 0.032 Uiso 1 calc R . . C11 C 0.2458(3) 0.67217(10) 0.32888(8) 0.0192(4) Uani 1 d . . . C12 C 0.1452(3) 0.65673(10) 0.37513(8) 0.0220(4) Uani 1 d . . . H12 H 0.1655 0.6753 0.4076 0.026 Uiso 1 calc R . . C13 C 0.0175(3) 0.61082(10) 0.36268(8) 0.0202(4) Uani 1 d . . . C14 C 0.0377(3) 0.59739(10) 0.30810(8) 0.0174(4) Uani 1 d . . . C15 C -0.0703(3) 0.55368(10) 0.27924(8) 0.0190(4) Uani 1 d . . . C151 C -0.2285(3) 0.51522(9) 0.30204(8) 0.0178(4) Uani 1 d . . . C152 C -0.1964(3) 0.45256(11) 0.32220(10) 0.0285(5) Uani 1 d . . . H152 H -0.0731 0.4359 0.3236 0.034 Uiso 1 calc R . . C153 C -0.3427(4) 0.41410(11) 0.34029(10) 0.0332(6) Uani 1 d . . . H153 H -0.3185 0.3716 0.3539 0.040 Uiso 1 calc R . . C154 C -0.5233(3) 0.43780(12) 0.33850(9) 0.0297(5) Uani 1 d . . . H154 H -0.6234 0.4115 0.3504 0.036 Uiso 1 calc R . . C155 C -0.5563(4) 0.50042(13) 0.31905(9) 0.0320(5) Uani 1 d . . . H155 H -0.6796 0.5171 0.3183 0.038 Uiso 1 calc R . . C156 C -0.4109(3) 0.53896(11) 0.30064(9) 0.0275(5) Uani 1 d . . . H156 H -0.4357 0.5815 0.2871 0.033 Uiso 1 calc R . . C16 C -0.0406(3) 0.54061(10) 0.22754(8) 0.0199(4) Uani 1 d . . . C17 C -0.1609(3) 0.50265(11) 0.19538(8) 0.0270(5) Uani 1 d . . . H17 H -0.2735 0.4819 0.2053 0.032 Uiso 1 calc R . . C18 C -0.0845(3) 0.50158(11) 0.14800(8) 0.0256(5) Uani 1 d . . . H18 H -0.1368 0.4807 0.1191 0.031 Uiso 1 calc R . . C19 C 0.0867(3) 0.53700(10) 0.14920(8) 0.0188(4) Uani 1 d . . . C20 C 0.2141(3) 0.54483(10) 0.10935(8) 0.0179(4) Uani 1 d . . . C201 C 0.1589(3) 0.51498(11) 0.05971(8) 0.0210(4) Uani 1 d . . . C202 C 0.1099(3) 0.55723(13) 0.01995(9) 0.0280(5) Uani 1 d . . . H202 H 0.1055 0.6035 0.0254 0.034 Uiso 1 calc R . . C203 C 0.0674(4) 0.53156(16) -0.02783(9) 0.0397(6) Uani 1 d . . . H203 H 0.0344 0.5603 -0.0547 0.048 Uiso 1 calc R . . C204 C 0.0735(4) 0.46374(16) -0.03575(9) 0.0413(7) Uani 1 d . . . H204 H 0.0500 0.4464 -0.0685 0.050 Uiso 1 calc R . . C205 C 0.1134(4) 0.42168(15) 0.00362(10) 0.0393(6) Uani 1 d . . . H205 H 0.1128 0.3754 -0.0018 0.047 Uiso 1 calc R . . C206 C 0.1551(4) 0.44692(12) 0.05168(9) 0.0299(5) Uani 1 d . . . H206 H 0.1807 0.4176 0.0788 0.036 Uiso 1 calc R . . Br1 Br 0.56717(3) 0.527532(12) 0.017140(9) 0.02777(6) Uani 1 d . . . Br2 Br -0.14596(3) 0.573071(12) 0.410410(8) 0.02808(6) Uani 1 d . . . 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 N21 0.0187(8) 0.0187(8) 0.0183(8) -0.0023(7) 0.0006(7) -0.0010(7) N22 0.0187(8) 0.0155(8) 0.0188(9) -0.0018(7) -0.0006(7) -0.0031(7) N23 0.0219(9) 0.0164(8) 0.0173(8) -0.0019(7) 0.0012(7) -0.0008(7) N24 0.0192(9) 0.0213(9) 0.0155(8) -0.0023(7) 0.0008(6) -0.0064(7) C1 0.0241(11) 0.0168(9) 0.0138(9) -0.0004(7) -0.0003(8) -0.0012(8) C2 0.0221(10) 0.0215(10) 0.0159(9) -0.0026(8) 0.0009(8) 0.0014(8) C3 0.0200(10) 0.0227(10) 0.0210(10) -0.0011(8) 0.0028(10) -0.0006(8) C4 0.0193(10) 0.0173(9) 0.0198(10) 0.0002(8) 0.0002(8) 0.0003(8) C5 0.0166(10) 0.0173(10) 0.0221(10) 0.0014(8) -0.0001(8) -0.0021(8) C51 0.0222(11) 0.0180(10) 0.0192(10) -0.0013(8) 0.0020(9) -0.0025(8) C52 0.0241(11) 0.0290(11) 0.0319(13) 0.0066(10) -0.0028(10) 0.0003(9) C53 0.0362(15) 0.0403(14) 0.0390(15) 0.0203(12) 0.0004(12) -0.0023(12) C54 0.0328(14) 0.0489(16) 0.0437(16) 0.0147(13) 0.0078(12) -0.0127(12) C55 0.0212(10) 0.0356(13) 0.0476(16) 0.0032(11) 0.0039(12) -0.0031(10) C56 0.0213(11) 0.0194(10) 0.0319(13) 0.0026(9) -0.0009(9) 0.0004(8) C6 0.0179(9) 0.0145(9) 0.0207(10) 0.0031(7) -0.0017(9) -0.0004(8) C7 0.0188(10) 0.0159(10) 0.0217(10) 0.0012(8) -0.0056(8) 0.0002(8) C71 0.0222(11) 0.0179(10) 0.0249(11) 0.0007(8) -0.0049(8) -0.0045(8) C72 0.0224(11) 0.0316(12) 0.0379(14) 0.0066(10) -0.0085(11) -0.0047(10) C8 0.0215(10) 0.0155(9) 0.0212(10) 0.0004(8) -0.0049(9) 0.0002(9) C81 0.0273(12) 0.0181(10) 0.0223(11) -0.0011(8) -0.0042(9) -0.0047(9) C82 0.0459(14) 0.0183(10) 0.0315(12) -0.0028(9) -0.0040(12) 0.0020(11) C9 0.0208(10) 0.0142(9) 0.0174(10) -0.0018(7) -0.0051(8) 0.0012(8) C10 0.0238(11) 0.0169(9) 0.0169(10) -0.0008(8) -0.0019(8) 0.0031(8) C101 0.0266(11) 0.0194(10) 0.0165(10) -0.0007(8) -0.0005(9) -0.0031(9) C102 0.0388(13) 0.0252(11) 0.0248(11) 0.0011(9) -0.0075(12) 0.0028(10) C103 0.0471(15) 0.0437(14) 0.0230(12) 0.0040(11) -0.0129(12) -0.0073(13) C104 0.0520(17) 0.0445(15) 0.0201(12) -0.0120(10) 0.0024(11) -0.0137(13) C105 0.0384(14) 0.0334(13) 0.0339(13) -0.0150(11) 0.0057(12) -0.0019(12) C106 0.0266(12) 0.0268(11) 0.0258(11) -0.0063(9) -0.0003(9) -0.0010(9) C11 0.0234(11) 0.0167(10) 0.0176(10) -0.0019(8) 0.0016(8) 0.0008(8) C12 0.0290(11) 0.0224(10) 0.0148(9) -0.0017(8) 0.0027(9) -0.0020(9) C13 0.0224(11) 0.0204(10) 0.0176(10) 0.0008(8) 0.0038(8) -0.0004(8) C14 0.0191(10) 0.0155(9) 0.0177(10) -0.0007(7) 0.0027(8) 0.0032(8) C15 0.0189(9) 0.0184(9) 0.0195(10) -0.0004(7) 0.0025(9) 0.0006(8) C151 0.0220(10) 0.0147(10) 0.0167(9) -0.0015(7) 0.0032(8) -0.0024(8) C152 0.0257(12) 0.0222(11) 0.0377(14) 0.0025(10) 0.0102(10) 0.0044(9) C153 0.0419(14) 0.0175(11) 0.0403(14) 0.0052(9) 0.0134(13) 0.0007(10) C154 0.0323(13) 0.0328(13) 0.0239(11) -0.0009(10) 0.0061(10) -0.0139(10) C155 0.0204(11) 0.0425(14) 0.0330(13) 0.0101(11) 0.0015(10) -0.0018(11) C156 0.0244(11) 0.0279(12) 0.0303(12) 0.0100(9) -0.0004(9) 0.0007(9) C16 0.0233(11) 0.0189(10) 0.0175(10) -0.0012(8) 0.0035(8) -0.0038(8) C17 0.0245(11) 0.0317(12) 0.0247(11) -0.0039(9) 0.0024(10) -0.0122(10) C18 0.0266(12) 0.0317(11) 0.0186(10) -0.0064(9) -0.0002(9) -0.0111(10) C19 0.0228(10) 0.0187(10) 0.0150(9) -0.0020(7) -0.0015(8) -0.0042(8) C20 0.0203(10) 0.0186(10) 0.0147(9) -0.0008(7) -0.0016(8) -0.0023(8) C201 0.0164(9) 0.0304(11) 0.0162(10) -0.0022(8) 0.0023(8) -0.0041(9) C202 0.0212(11) 0.0405(13) 0.0224(11) 0.0025(10) 0.0020(9) 0.0013(9) C203 0.0260(11) 0.075(2) 0.0182(11) 0.0020(12) -0.0031(10) 0.0022(14) C204 0.0251(11) 0.078(2) 0.0211(12) -0.0204(13) -0.0012(10) -0.0093(14) C205 0.0329(14) 0.0496(16) 0.0353(14) -0.0224(12) 0.0019(11) -0.0122(12) C206 0.0327(12) 0.0326(12) 0.0244(11) -0.0066(9) -0.0010(11) -0.0073(10) Br1 0.02532(10) 0.03258(12) 0.02541(11) -0.01213(9) 0.00565(10) -0.00212(10) Br2 0.03362(12) 0.03369(12) 0.01692(10) 0.00079(9) 0.00679(10) -0.00703(10) _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 N21 C4 1.371(3) . ? N21 C1 1.386(3) . ? N22 C9 1.383(3) . ? N22 C6 1.387(3) . ? N23 C11 1.373(3) . ? N23 C14 1.384(3) . ? N24 C16 1.376(3) . ? N24 C19 1.387(3) . ? C1 C20 1.409(3) . ? C1 C2 1.472(3) . ? C2 C3 1.341(3) . ? C2 Br1 1.891(2) . ? C3 C4 1.456(3) . ? C4 C5 1.421(3) . ? C5 C6 1.404(3) . ? C5 C51 1.513(3) . ? C51 C56 1.396(3) . ? C51 C52 1.402(3) . ? C52 C53 1.391(3) . ? C53 C54 1.388(4) . ? C54 C55 1.393(4) . ? C55 C56 1.390(3) . ? C6 C7 1.453(3) . ? C7 C8 1.375(3) . ? C7 C71 1.512(3) . ? C71 C72 1.539(3) . ? C8 C9 1.454(3) . ? C8 C81 1.519(3) . ? C81 C82 1.546(3) . ? C9 C10 1.408(3) . ? C10 C11 1.422(3) . ? C10 C101 1.512(3) . ? C101 C106 1.399(3) . ? C101 C102 1.399(3) . ? C102 C103 1.399(3) . ? C103 C104 1.394(4) . ? C104 C105 1.377(4) . ? C105 C106 1.394(3) . ? C11 C12 1.456(3) . ? C12 C13 1.349(3) . ? C13 C14 1.476(3) . ? C13 Br2 1.888(2) . ? C14 C15 1.404(3) . ? C15 C16 1.409(3) . ? C15 C151 1.506(3) . ? C151 C156 1.399(3) . ? C151 C152 1.397(3) . ? C152 C153 1.395(3) . ? C153 C154 1.386(4) . ? C154 C155 1.390(3) . ? C155 C156 1.394(3) . ? C16 C17 1.437(3) . ? C17 C18 1.368(3) . ? C18 C19 1.426(3) . ? C19 C20 1.406(3) . ? C20 C201 1.499(3) . ? C201 C206 1.396(3) . ? C201 C202 1.402(3) . ? C202 C203 1.400(3) . ? C203 C204 1.392(4) . ? C204 C205 1.376(4) . ? C205 C206 1.403(3) . ? 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 C4 N21 C1 105.65(16) . . ? C9 N22 C6 111.26(17) . . ? C11 N23 C14 105.92(17) . . ? C16 N24 C19 110.28(17) . . ? N21 C1 C20 124.77(18) . . ? N21 C1 C2 109.09(17) . . ? C20 C1 C2 126.05(18) . . ? C3 C2 C1 107.56(18) . . ? C3 C2 Br1 122.32(16) . . ? C1 C2 Br1 129.82(15) . . ? C2 C3 C4 106.43(19) . . ? N21 C4 C5 127.38(19) . . ? N21 C4 C3 111.08(17) . . ? C5 C4 C3 121.49(19) . . ? C6 C5 C4 126.32(19) . . ? C6 C5 C51 120.25(18) . . ? C4 C5 C51 113.36(18) . . ? C56 C51 C52 118.7(2) . . ? C56 C51 C5 121.97(19) . . ? C52 C51 C5 119.1(2) . . ? C53 C52 C51 120.5(2) . . ? C54 C53 C52 120.4(2) . . ? C53 C54 C55 119.3(2) . . ? C56 C55 C54 120.6(2) . . ? C55 C56 C51 120.4(2) . . ? N22 C6 C5 124.01(18) . . ? N22 C6 C7 106.07(18) . . ? C5 C6 C7 129.9(2) . . ? C8 C7 C6 108.24(19) . . ? C8 C7 C71 122.82(19) . . ? C6 C7 C71 128.9(2) . . ? C7 C71 C72 110.90(17) . . ? C7 C8 C9 108.34(18) . . ? C7 C8 C81 122.60(19) . . ? C9 C8 C81 128.77(19) . . ? C8 C81 C82 110.82(18) . . ? N22 C9 C10 124.62(18) . . ? N22 C9 C8 106.08(18) . . ? C10 C9 C8 129.25(18) . . ? C9 C10 C11 127.06(18) . . ? C9 C10 C101 118.44(18) . . ? C11 C10 C101 114.49(18) . . ? C106 C101 C102 119.1(2) . . ? C106 C101 C10 120.9(2) . . ? C102 C101 C10 119.94(19) . . ? C101 C102 C103 120.1(2) . . ? C104 C103 C102 120.0(2) . . ? C105 C104 C103 120.1(2) . . ? C104 C105 C106 120.4(2) . . ? C105 C106 C101 120.3(2) . . ? N23 C11 C10 127.93(19) . . ? N23 C11 C12 111.14(18) . . ? C10 C11 C12 120.92(19) . . ? C13 C12 C11 106.38(18) . . ? C12 C13 C14 107.41(18) . . ? C12 C13 Br2 122.75(16) . . ? C14 C13 Br2 129.83(16) . . ? N23 C14 C15 124.44(18) . . ? N23 C14 C13 109.14(17) . . ? C15 C14 C13 126.42(19) . . ? C14 C15 C16 124.22(19) . . ? C14 C15 C151 121.83(18) . . ? C16 C15 C151 113.93(18) . . ? C156 C151 C152 118.6(2) . . ? C156 C151 C15 121.38(18) . . ? C152 C151 C15 119.93(19) . . ? C153 C152 C151 121.0(2) . . ? C154 C153 C152 120.1(2) . . ? C153 C154 C155 119.3(2) . . ? C154 C155 C156 120.8(2) . . ? C155 C156 C151 120.2(2) . . ? N24 C16 C15 127.6(2) . . ? N24 C16 C17 106.64(18) . . ? C15 C16 C17 125.7(2) . . ? C18 C17 C16 108.0(2) . . ? C17 C18 C19 108.56(19) . . ? N24 C19 C20 126.36(19) . . ? N24 C19 C18 106.48(17) . . ? C20 C19 C18 127.13(19) . . ? C19 C20 C1 124.83(18) . . ? C19 C20 C201 115.98(18) . . ? C1 C20 C201 119.13(18) . . ? C206 C201 C202 119.0(2) . . ? C206 C201 C20 122.50(19) . . ? C202 C201 C20 118.50(19) . . ? C203 C202 C201 120.3(2) . . ? C204 C203 C202 119.7(2) . . ? C205 C204 C203 120.3(2) . . ? C204 C205 C206 120.3(3) . . ? C201 C206 C205 120.2(2) . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 28.20 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.411 _refine_diff_density_min -0.573 _refine_diff_density_rms 0.055 #====END data_ms357 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,12-Dibromo-7,8-diethyl-5,10,15,20-tetra- phenylporphyrin ; _chemical_name_common ? _chemical_formula_moiety 'C48 H36 Br2 N4' _chemical_formula_sum 'C48 H36 Br2 N4' _chemical_formula_weight 828.63 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.90770(10) _cell_length_b 14.09330(10) _cell_length_c 15.2952(2) _cell_angle_alpha 102.4510(10) _cell_angle_beta 99.8700(10) _cell_angle_gamma 107.8140(10) _cell_volume 1919.67(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ; 8192 reflections with I > 10sigmaI ; _cell_measurement_theta_min n/a _cell_measurement_theta_max n/a _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas n/d _exptl_crystal_density_diffrn 1.434 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 844 _exptl_absorpt_coefficient_mu 2.152 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.3584 _exptl_absorpt_correction_T_max 0.5646 _exptl_special_details ; The data collection nominally coverd over a hemisphere of reciprocal space, by a combination of three sets of exposure; each set had a different $Gf angle for the crystal and each exposure covers 0.3 &^o&0 in &Gw. The crystal-to-detector distance was 4.910 cm. Coverage of the unique set is over 97% complete to at least 26&^o in &Gq. Crystal decay was monitored by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. No decay was observed. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method &Gw _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% stable _diffrn_reflns_number 13309 _diffrn_reflns_av_R_equivalents 0.0204 _diffrn_reflns_av_sigmaI/netI 0.0421 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 28.23 _reflns_number_total 8520 _reflns_number_gt 7256 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; SMART, Software Reference Manual (1994). Siemens Analytical Inst. WI ; _computing_cell_refinement SMART _computing_data_reduction ; SAINT Version 4, Software Reference Manual (1995). Siemens Analytical Instr., WI. ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus, Siemens, 1994' _computing_publication_material 'XCIF, Shelxtl-Plus, Siemens, 1994' _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 w=1/[\s^2^(Fo^2^)+(0.0576P)^2^+2.0603P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef n/d _refine_ls_number_reflns 8520 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0500 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1116 _refine_ls_wR_factor_gt 0.1063 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N21 N 0.6061(2) 0.35092(16) -0.23175(15) 0.0185(4) Uani 1 d . . . N22 N 0.3780(2) 0.15007(15) -0.35906(15) 0.0184(4) Uani 1 d . . . H22A H 0.4123 0.2127 -0.3690 0.040 Uiso 1 d R . . N23 N 0.4514(2) 0.22721(17) -0.50938(15) 0.0209(4) Uani 1 d . . . N24 N 0.6895(2) 0.41551(17) -0.38522(15) 0.0219(5) Uani 1 d . . . H24A H 0.6157 0.3652 -0.3767 0.040 Uiso 1 d R . . C1 C 0.7033(3) 0.44899(19) -0.18368(18) 0.0180(5) Uani 1 d . . . C2 C 0.6764(3) 0.47959(19) -0.09220(18) 0.0176(5) Uani 1 d . . . C3 C 0.5654(3) 0.39815(19) -0.08577(18) 0.0179(5) Uani 1 d . . . H3 H 0.5227 0.3950 -0.0349 0.022 Uiso 1 calc R . . C4 C 0.5255(3) 0.31730(19) -0.17204(18) 0.0179(5) Uani 1 d . . . C5 C 0.4253(3) 0.21498(18) -0.18853(17) 0.0174(5) Uani 1 d . . . C51 C 0.3591(3) 0.18912(18) -0.11172(18) 0.0181(5) Uani 1 d . . . C52 C 0.2056(3) 0.15068(19) -0.12820(18) 0.0220(5) Uani 1 d . . . H52 H 0.1462 0.1427 -0.1870 0.026 Uiso 1 calc R . . C53 C 0.1399(3) 0.1242(2) -0.0589(2) 0.0285(6) Uani 1 d . . . H53 H 0.0360 0.0979 -0.0710 0.034 Uiso 1 calc R . . C54 C 0.2252(4) 0.1361(2) 0.0275(2) 0.0298(6) Uani 1 d . . . H54 H 0.1801 0.1169 0.0742 0.036 Uiso 1 calc R . . C55 C 0.3766(4) 0.1762(2) 0.0451(2) 0.0289(6) Uani 1 d . . . H55 H 0.4354 0.1858 0.1046 0.035 Uiso 1 calc R . . C56 C 0.4435(3) 0.2026(2) -0.02405(19) 0.0232(5) Uani 1 d . . . H56 H 0.5453 0.2296 -0.0112 0.028 Uiso 1 d R . . C6 C 0.3793(3) 0.13480(19) -0.27312(18) 0.0176(5) Uani 1 d . . . C7 C 0.3261(3) 0.02383(19) -0.28766(19) 0.0223(5) Uani 1 d . . . C71 C 0.3385(4) -0.0305(2) -0.2130(2) 0.0343(7) Uani 1 d . . . H71A H 0.2851 -0.1062 -0.2403 0.041 Uiso 1 calc R . . H71B H 0.2923 -0.0051 -0.1649 0.041 Uiso 1 calc R . . C72 C 0.4984(5) -0.0106(3) -0.1685(3) 0.0549(11) Uani 1 d . . . H72A H 0.5032 -0.0464 -0.1204 0.082 Uiso 1 calc R . . H72B H 0.5510 0.0643 -0.1407 0.082 Uiso 1 calc R . . H72C H 0.5437 -0.0369 -0.2158 0.082 Uiso 1 calc R . . C8 C 0.2896(3) -0.02443(19) -0.38216(19) 0.0220(5) Uani 1 d . . . C81 C 0.2469(4) -0.1402(2) -0.4235(2) 0.0332(7) Uani 1 d . . . H81A H 0.3192 -0.1637 -0.3899 0.040 Uiso 1 calc R . . H81B H 0.2524 -0.1537 -0.4888 0.040 Uiso 1 calc R . . C82 C 0.0928(5) -0.2053(3) -0.4205(3) 0.0542(11) Uani 1 d . . . H82A H 0.0736 -0.2791 -0.4484 0.081 Uiso 1 calc R . . H82B H 0.0198 -0.1842 -0.4552 0.081 Uiso 1 calc R . . H82C H 0.0867 -0.1941 -0.3560 0.081 Uiso 1 calc R . . C9 C 0.3167(3) 0.05678(18) -0.42816(18) 0.0190(5) Uani 1 d . . . C10 C 0.2843(3) 0.05074(19) -0.52303(18) 0.0198(5) Uani 1 d . . . C101 C 0.1972(3) -0.05306(19) -0.59175(18) 0.0212(5) Uani 1 d . . . C102 C 0.2668(3) -0.1020(2) -0.6491(2) 0.0295(6) Uani 1 d . . . H102 H 0.3671 -0.0679 -0.6461 0.035 Uiso 1 calc R . . C103 C 0.1896(4) -0.2004(3) -0.7106(2) 0.0414(8) Uani 1 d . . . H103 H 0.2378 -0.2334 -0.7489 0.050 Uiso 1 calc R . . C104 C 0.0432(4) -0.2508(2) -0.7165(3) 0.0436(8) Uani 1 d . . . H104 H -0.0087 -0.3182 -0.7583 0.052 Uiso 1 calc R . . C105 C -0.0277(4) -0.2023(2) -0.6608(2) 0.0366(7) Uani 1 d . . . H105 H -0.1285 -0.2362 -0.6650 0.044 Uiso 1 calc R . . C106 C 0.0492(3) -0.1040(2) -0.5988(2) 0.0277(6) Uani 1 d . . . H106 H 0.0003 -0.0713 -0.5609 0.033 Uiso 1 calc R . . C11 C 0.3356(3) 0.1370(2) -0.55804(18) 0.0209(5) Uani 1 d . . . C12 C 0.2848(3) 0.1417(2) -0.65240(19) 0.0242(5) Uani 1 d . . . C13 C 0.3755(3) 0.2319(2) -0.66079(19) 0.0249(6) Uani 1 d . . . H13 H 0.3707 0.2566 -0.7139 0.030 Uiso 1 calc R . . C14 C 0.4810(3) 0.2824(2) -0.57158(18) 0.0212(5) Uani 1 d . . . C15 C 0.6060(3) 0.3728(2) -0.55564(18) 0.0209(5) Uani 1 d . . . C151 C 0.6363(3) 0.4084(2) -0.63833(19) 0.0223(5) Uani 1 d . . . C152 C 0.6739(3) 0.3465(2) -0.7076(2) 0.0278(6) Uani 1 d . . . H152 H 0.6794 0.2819 -0.7019 0.033 Uiso 1 calc R . . C153 C 0.7034(4) 0.3780(3) -0.7845(2) 0.0357(7) Uani 1 d . . . H153 H 0.7303 0.3356 -0.8304 0.043 Uiso 1 calc R . . C154 C 0.6936(4) 0.4708(3) -0.7942(2) 0.0408(8) Uani 1 d . . . H154 H 0.7128 0.4921 -0.8471 0.049 Uiso 1 calc R . . C155 C 0.6556(4) 0.5333(3) -0.7266(3) 0.0406(8) Uani 1 d . . . H155 H 0.6481 0.5970 -0.7337 0.049 Uiso 1 calc R . . C156 C 0.6283(3) 0.5029(2) -0.6478(2) 0.0329(7) Uani 1 d . . . H156 H 0.6044 0.5466 -0.6011 0.040 Uiso 1 calc R . . C16 C 0.7053(3) 0.4287(2) -0.47037(19) 0.0225(5) Uani 1 d . . . C17 C 0.8406(3) 0.5139(2) -0.4524(2) 0.0282(6) Uani 1 d . . . H17 H 0.8814 0.5406 -0.4978 0.034 Uiso 1 calc R . . C18 C 0.9006(3) 0.5500(2) -0.3593(2) 0.0277(6) Uani 1 d . . . H18 H 0.9914 0.6050 -0.3287 0.033 Uiso 1 calc R . . C19 C 0.8024(3) 0.4903(2) -0.31513(19) 0.0220(5) Uani 1 d . . . C20 C 0.8101(3) 0.51012(19) -0.22026(18) 0.0195(5) Uani 1 d . . . C201 C 0.9335(3) 0.6027(2) -0.15554(18) 0.0204(5) Uani 1 d . . . C202 C 0.9543(3) 0.7031(2) -0.1642(2) 0.0237(5) Uani 1 d . . . H202 H 0.8923 0.7122 -0.2139 0.028 Uiso 1 calc R . . C203 C 1.0649(3) 0.7893(2) -0.1005(2) 0.0290(6) Uani 1 d . . . H203 H 1.0790 0.8568 -0.1074 0.035 Uiso 1 calc R . . C204 C 1.1550(3) 0.7768(2) -0.0266(2) 0.0323(7) Uani 1 d . . . H204 H 1.2284 0.8358 0.0181 0.039 Uiso 1 calc R . . C205 C 1.1370(3) 0.6776(2) -0.0186(2) 0.0293(6) Uani 1 d . . . H205 H 1.1993 0.6689 0.0311 0.035 Uiso 1 calc R . . C206 C 1.0287(3) 0.5915(2) -0.08284(19) 0.0238(5) Uani 1 d . . . H206 H 1.0189 0.5239 -0.0775 0.029 Uiso 1 calc R . . Br1 Br 0.75797(3) 0.608459(19) -0.000163(19) 0.02320(8) Uani 1 d . . . Br2 Br 0.11483(4) 0.05518(2) -0.74554(2) 0.03776(10) Uani 1 d . . . 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 N21 0.0192(10) 0.0144(9) 0.0222(11) 0.0072(8) 0.0100(9) 0.0025(8) N22 0.0233(11) 0.0122(9) 0.0188(10) 0.0059(8) 0.0089(9) 0.0025(8) N23 0.0220(11) 0.0182(10) 0.0194(11) 0.0056(9) 0.0085(9) 0.0009(8) N24 0.0218(11) 0.0199(10) 0.0197(11) 0.0071(9) 0.0102(9) -0.0020(8) C1 0.0193(12) 0.0158(11) 0.0199(12) 0.0064(9) 0.0096(10) 0.0040(9) C2 0.0173(11) 0.0167(11) 0.0205(12) 0.0070(9) 0.0072(9) 0.0061(9) C3 0.0186(12) 0.0160(11) 0.0220(12) 0.0078(10) 0.0098(10) 0.0057(9) C4 0.0192(12) 0.0154(11) 0.0230(13) 0.0086(10) 0.0107(10) 0.0066(9) C5 0.0195(12) 0.0152(11) 0.0200(12) 0.0081(9) 0.0102(10) 0.0046(9) C51 0.0240(13) 0.0111(10) 0.0217(12) 0.0062(9) 0.0119(10) 0.0056(9) C52 0.0231(13) 0.0185(12) 0.0197(12) 0.0031(10) 0.0086(10) 0.0005(10) C53 0.0269(14) 0.0222(13) 0.0313(15) 0.0032(11) 0.0162(12) 0.0000(11) C54 0.0435(17) 0.0224(13) 0.0289(15) 0.0119(12) 0.0224(13) 0.0088(12) C55 0.0413(17) 0.0269(14) 0.0242(14) 0.0137(12) 0.0134(12) 0.0128(12) C56 0.0249(13) 0.0218(12) 0.0265(14) 0.0114(11) 0.0100(11) 0.0083(10) C6 0.0189(12) 0.0158(11) 0.0213(12) 0.0091(10) 0.0103(10) 0.0053(9) C7 0.0296(14) 0.0146(11) 0.0245(13) 0.0086(10) 0.0134(11) 0.0049(10) C71 0.064(2) 0.0169(13) 0.0264(15) 0.0087(11) 0.0206(15) 0.0142(13) C72 0.086(3) 0.053(2) 0.041(2) 0.0215(18) 0.009(2) 0.045(2) C8 0.0271(13) 0.0152(11) 0.0253(13) 0.0080(10) 0.0125(11) 0.0049(10) C81 0.057(2) 0.0137(12) 0.0273(15) 0.0064(11) 0.0146(14) 0.0082(12) C82 0.071(3) 0.0252(16) 0.048(2) 0.0110(15) 0.019(2) -0.0106(17) C9 0.0198(12) 0.0132(11) 0.0230(13) 0.0052(10) 0.0090(10) 0.0027(9) C10 0.0194(12) 0.0168(11) 0.0208(12) 0.0037(10) 0.0080(10) 0.0026(9) C101 0.0230(13) 0.0160(11) 0.0221(13) 0.0049(10) 0.0063(10) 0.0037(10) C102 0.0286(15) 0.0306(15) 0.0283(15) 0.0037(12) 0.0078(12) 0.0121(12) C103 0.047(2) 0.0352(17) 0.0384(18) -0.0056(14) 0.0074(15) 0.0223(15) C104 0.048(2) 0.0195(14) 0.047(2) -0.0066(14) -0.0012(16) 0.0085(14) C105 0.0278(15) 0.0205(14) 0.051(2) 0.0065(13) 0.0039(14) -0.0001(11) C106 0.0242(14) 0.0205(13) 0.0339(16) 0.0042(11) 0.0092(12) 0.0034(11) C11 0.0202(12) 0.0203(12) 0.0201(12) 0.0061(10) 0.0077(10) 0.0026(10) C12 0.0223(13) 0.0233(13) 0.0206(13) 0.0057(10) 0.0045(10) 0.0004(10) C13 0.0251(14) 0.0260(13) 0.0214(13) 0.0108(11) 0.0073(11) 0.0025(11) C14 0.0214(13) 0.0178(12) 0.0215(13) 0.0066(10) 0.0078(10) 0.0013(10) C15 0.0223(13) 0.0181(12) 0.0219(13) 0.0080(10) 0.0103(10) 0.0026(10) C151 0.0200(13) 0.0221(12) 0.0237(13) 0.0110(10) 0.0062(10) 0.0024(10) C152 0.0304(15) 0.0268(14) 0.0259(14) 0.0117(12) 0.0117(12) 0.0045(11) C153 0.0351(17) 0.0436(18) 0.0235(15) 0.0114(13) 0.0129(13) 0.0033(14) C154 0.0318(17) 0.055(2) 0.0331(17) 0.0294(16) 0.0084(13) 0.0005(15) C155 0.0365(18) 0.0408(18) 0.050(2) 0.0329(17) 0.0073(15) 0.0101(14) C156 0.0335(16) 0.0286(15) 0.0430(18) 0.0189(14) 0.0145(14) 0.0112(12) C16 0.0251(13) 0.0209(12) 0.0216(13) 0.0094(10) 0.0121(11) 0.0027(10) C17 0.0277(14) 0.0270(14) 0.0244(14) 0.0087(11) 0.0135(11) -0.0022(11) C18 0.0241(14) 0.0267(14) 0.0241(14) 0.0082(11) 0.0104(11) -0.0052(11) C19 0.0207(13) 0.0190(12) 0.0221(13) 0.0050(10) 0.0105(10) -0.0009(10) C20 0.0198(12) 0.0168(11) 0.0220(13) 0.0075(10) 0.0090(10) 0.0032(9) C201 0.0175(12) 0.0210(12) 0.0220(13) 0.0074(10) 0.0098(10) 0.0025(10) C202 0.0223(13) 0.0221(13) 0.0253(14) 0.0090(11) 0.0076(11) 0.0036(10) C203 0.0261(14) 0.0183(12) 0.0386(16) 0.0064(12) 0.0121(12) 0.0016(11) C204 0.0196(13) 0.0301(15) 0.0337(16) -0.0022(12) 0.0050(12) -0.0007(11) C205 0.0206(13) 0.0413(17) 0.0244(14) 0.0074(12) 0.0059(11) 0.0102(12) C206 0.0215(13) 0.0278(13) 0.0250(14) 0.0098(11) 0.0114(11) 0.0081(11) Br1 0.02477(14) 0.01566(12) 0.02599(14) 0.00169(10) 0.01299(11) 0.00223(10) Br2 0.03384(17) 0.03289(17) 0.03025(17) 0.01195(13) -0.00313(13) -0.00638(13) _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 N21 C1 1.372(3) . ? N21 C4 1.379(3) . ? N22 C6 1.376(3) . ? N22 C9 1.381(3) . ? N23 C14 1.368(3) . ? N23 C11 1.376(3) . ? N24 C19 1.375(3) . ? N24 C16 1.383(3) . ? C1 C20 1.424(3) . ? C1 C2 1.467(3) . ? C2 C3 1.360(3) . ? C2 Br1 1.882(2) . ? C3 C4 1.447(3) . ? C4 C5 1.418(3) . ? C5 C6 1.418(3) . ? C5 C51 1.498(3) . ? C51 C56 1.393(4) . ? C51 C52 1.406(4) . ? C52 C53 1.394(4) . ? C53 C54 1.388(5) . ? C54 C55 1.385(4) . ? C55 C56 1.399(4) . ? C6 C7 1.442(3) . ? C7 C8 1.389(4) . ? C7 C71 1.514(4) . ? C71 C72 1.526(6) . ? C8 C9 1.450(3) . ? C8 C81 1.511(4) . ? C81 C82 1.536(5) . ? C9 C10 1.409(4) . ? C10 C11 1.420(3) . ? C10 C101 1.498(3) . ? C101 C106 1.395(4) . ? C101 C102 1.400(4) . ? C102 C103 1.391(4) . ? C103 C104 1.383(5) . ? C104 C105 1.391(5) . ? C105 C106 1.392(4) . ? C11 C12 1.467(4) . ? C12 C13 1.361(4) . ? C12 Br2 1.878(3) . ? C13 C14 1.448(4) . ? C14 C15 1.418(3) . ? C15 C16 1.390(4) . ? C15 C151 1.501(3) . ? C151 C156 1.395(4) . ? C151 C152 1.399(4) . ? C152 C153 1.390(4) . ? C153 C154 1.378(5) . ? C154 C155 1.389(5) . ? C155 C156 1.404(4) . ? C16 C17 1.436(3) . ? C17 C18 1.361(4) . ? C18 C19 1.442(3) . ? C19 C20 1.401(4) . ? C20 C201 1.493(3) . ? C201 C206 1.400(4) . ? C201 C202 1.404(4) . ? C202 C203 1.391(4) . ? C203 C204 1.393(5) . ? C204 C205 1.388(4) . ? C205 C206 1.385(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 C1 N21 C4 106.0(2) . . ? C6 N22 C9 111.2(2) . . ? C14 N23 C11 105.9(2) . . ? C19 N24 C16 110.5(2) . . ? N21 C1 C20 123.8(2) . . ? N21 C1 C2 109.5(2) . . ? C20 C1 C2 126.7(2) . . ? C3 C2 C1 107.3(2) . . ? C3 C2 Br1 122.59(19) . . ? C1 C2 Br1 129.88(18) . . ? C2 C3 C4 106.1(2) . . ? N21 C4 C5 125.3(2) . . ? N21 C4 C3 111.0(2) . . ? C5 C4 C3 123.6(2) . . ? C4 C5 C6 125.2(2) . . ? C4 C5 C51 118.0(2) . . ? C6 C5 C51 116.8(2) . . ? C56 C51 C52 118.4(2) . . ? C56 C51 C5 122.7(2) . . ? C52 C51 C5 118.8(2) . . ? C53 C52 C51 120.5(3) . . ? C54 C53 C52 120.4(3) . . ? C55 C54 C53 119.5(3) . . ? C54 C55 C56 120.5(3) . . ? C51 C56 C55 120.6(3) . . ? N22 C6 C5 125.2(2) . . ? N22 C6 C7 106.4(2) . . ? C5 C6 C7 128.4(2) . . ? C8 C7 C6 108.3(2) . . ? C8 C7 C71 124.9(2) . . ? C6 C7 C71 125.6(2) . . ? C7 C71 C72 111.2(3) . . ? C7 C8 C9 107.4(2) . . ? C7 C8 C81 123.7(2) . . ? C9 C8 C81 128.6(2) . . ? C8 C81 C82 114.5(3) . . ? N22 C9 C10 122.9(2) . . ? N22 C9 C8 106.4(2) . . ? C10 C9 C8 130.6(2) . . ? C9 C10 C11 123.7(2) . . ? C9 C10 C101 118.6(2) . . ? C11 C10 C101 117.6(2) . . ? C106 C101 C102 118.7(2) . . ? C106 C101 C10 122.0(2) . . ? C102 C101 C10 119.2(2) . . ? C103 C102 C101 120.2(3) . . ? C104 C103 C102 120.7(3) . . ? C103 C104 C105 119.6(3) . . ? C104 C105 C106 119.9(3) . . ? C105 C106 C101 120.8(3) . . ? N23 C11 C10 124.2(2) . . ? N23 C11 C12 109.1(2) . . ? C10 C11 C12 126.5(2) . . ? C13 C12 C11 107.6(2) . . ? C13 C12 Br2 121.9(2) . . ? C11 C12 Br2 129.97(19) . . ? C12 C13 C14 105.4(2) . . ? N23 C14 C15 125.4(2) . . ? N23 C14 C13 111.7(2) . . ? C15 C14 C13 122.7(2) . . ? C16 C15 C14 125.3(2) . . ? C16 C15 C151 117.4(2) . . ? C14 C15 C151 117.2(2) . . ? C156 C151 C152 118.7(3) . . ? C156 C151 C15 121.3(3) . . ? C152 C151 C15 120.0(2) . . ? C153 C152 C151 121.1(3) . . ? C154 C153 C152 120.0(3) . . ? C153 C154 C155 120.0(3) . . ? C154 C155 C156 120.3(3) . . ? C151 C156 C155 119.8(3) . . ? N24 C16 C15 126.3(2) . . ? N24 C16 C17 106.4(2) . . ? C15 C16 C17 127.3(2) . . ? C18 C17 C16 108.5(2) . . ? C17 C18 C19 108.2(2) . . ? N24 C19 C20 125.8(2) . . ? N24 C19 C18 106.4(2) . . ? C20 C19 C18 127.5(2) . . ? C19 C20 C1 123.2(2) . . ? C19 C20 C201 117.7(2) . . ? C1 C20 C201 119.0(2) . . ? C206 C201 C202 118.5(2) . . ? C206 C201 C20 120.4(2) . . ? C202 C201 C20 121.1(2) . . ? C203 C202 C201 120.6(3) . . ? C202 C203 C204 120.1(3) . . ? C205 C204 C203 119.7(3) . . ? C206 C205 C204 120.4(3) . . ? C205 C206 C201 120.8(3) . . ? _diffrn_measured_fraction_theta_max 0.898 _diffrn_reflns_theta_full 28.23 _diffrn_measured_fraction_theta_full 0.898 _refine_diff_density_max 0.992 _refine_diff_density_min -1.240 _refine_diff_density_rms 0.083 #====END data_ms413 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,7,8,12,13-Hexabromo-17,18-diethyl-5,10,15,20- tetraphenylporphyrin ; _chemical_name_common ? _chemical_melting_point n/d _chemical_formula_moiety ; C48 H32 Br6 N4.1(C6 H12) ; _chemical_formula_sum 'C54 H44 Br6 N4' _chemical_formula_weight 1228.39 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' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.309(10) _cell_length_b 14.037(12) _cell_length_c 14.053(11) _cell_angle_alpha 105.43(6) _cell_angle_beta 93.42(6) _cell_angle_gamma 108.46(6) _cell_volume 2370(3) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 34 _cell_measurement_theta_min 41 _cell_measurement_theta_max 46 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'metallic lustrous green' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.721 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1212 _exptl_absorpt_coefficient_mu 6.444 _exptl_absorpt_correction_type 'empirical, XABS2' _exptl_absorpt_correction_T_min 0.2656 _exptl_absorpt_correction_T_max 0.7826 _exptl_absorpt_process_details '(Parkins et al., 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Ni-filter _diffrn_measurement_device_type 'Siemens P4/RA' _diffrn_measurement_method '2theta-theta' _diffrn_detector_area_resol_mean n/a _diffrn_standards_number 2 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 6247 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0499 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.30 _diffrn_reflns_theta_max 55.06 _reflns_number_total 5935 _reflns_number_gt 4530 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3' _computing_cell_refinement 'Siemens P3' _computing_data_reduction 'XDISK, Shelxtl-Plus, (Siemens, 1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus, (Siemens, 1994)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The phenyl rings were refined as rigid hexagons with isotropic thermal parameters. Except for the disordered positions, hydrogen atoms were placed in calculated positions and refined with a standard riding model. Hydrogen atoms were added to all four pyrrole nitrogen atoms and refined with 50 % occupancy, each. Considerable disorder was found for the side chain bromine atoms and ethyl groups. This disorder could be modeled by using a "brute force" approach. Three different sets of side chain placements were refined with the following occupancies: C21, C22, C31, C32 each 40 % and Br2, Br3 each 60 % at C2 and C3 C71, C72, C81, C82 each 30 % and Br7, Br8 each 70 % at C7 and C8 C171, C172, C181, C182 each 40 % and Br17, Br18 each 60 % at C17 and C18. In order to get a somewhat stable refinement all C-C unit involving disordered groups were refined as rigid groups with fixed isotropic thermal parameters (0.03 for methylene groups, 0.04 for methyl groups). Nevertheless, despite all attempts significant shifts were always observed for the disordered carbon atoms. At best, the present structure can serve to illustrate the overall conformation of the macrocycle. No significance should be attributed to any individual geometrical parameters. ; _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^)+(0.1183P)^2^+34.5099P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef n/d _refine_ls_number_reflns 5935 _refine_ls_number_parameters 398 _refine_ls_number_restraints 18 _refine_ls_R_factor_all 0.1182 _refine_ls_R_factor_gt 0.0932 _refine_ls_wR_factor_ref 0.2487 _refine_ls_wR_factor_gt 0.2308 _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_restrained_S_all 1.040 _refine_ls_shift/su_max 0.878 _refine_ls_shift/su_mean 0.014 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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N21 N 1.2842(8) 0.4723(7) 0.7523(7) 0.037(2) Uani 1 1 d . A . H21 H 1.2225 0.4759 0.7691 0.045 Uiso 0.50 1 calc PR . . N22 N 1.0729(8) 0.3111(8) 0.7034(8) 0.043(3) Uani 1 1 d . A . H22 H 1.0978 0.3635 0.6782 0.051 Uiso 0.50 1 calc PR . . N23 N 0.9758(8) 0.4610(8) 0.6683(7) 0.038(2) Uani 1 1 d . A . H23 H 1.0335 0.4701 0.7087 0.046 Uiso 0.50 1 calc PR . . N24 N 1.1820(8) 0.6249(8) 0.7400(7) 0.039(2) Uani 1 1 d . A . H24 H 1.1640 0.5571 0.7092 0.046 Uiso 0.50 1 calc PR . . C1 C 1.3682(9) 0.5541(10) 0.7492(9) 0.037(3) Uani 1 1 d . A . C2 C 1.4541(10) 0.5167(11) 0.7119(10) 0.047(3) Uani 1 1 d D . . C3 C 1.4148(10) 0.4100(10) 0.6980(10) 0.046(3) Uani 1 1 d D A . C4 C 1.3091(9) 0.3812(9) 0.7250(9) 0.038(3) Uani 1 1 d . . . C5 C 1.2450(9) 0.2871(9) 0.7385(10) 0.040(3) Uani 1 1 d . A . C6 C 1.1350(9) 0.2664(9) 0.7448(9) 0.036(3) Uani 1 1 d . . . C7 C 1.0652(10) 0.1918(10) 0.7868(10) 0.047(3) Uani 1 1 d D A . C8 C 0.9619(10) 0.1907(10) 0.7641(10) 0.045(3) Uani 1 1 d D . . C9 C 0.9685(10) 0.2636(10) 0.7066(10) 0.045(3) Uani 1 1 d . A . C10 C 0.8833(10) 0.2774(9) 0.6539(9) 0.040(3) Uani 1 1 d . . . C11 C 0.8938(9) 0.3666(10) 0.6257(9) 0.038(3) Uani 1 1 d . A . C12 C 0.8207(10) 0.3893(10) 0.5613(10) 0.045(3) Uani 1 1 d . . . C13 C 0.8577(10) 0.4907(10) 0.5671(10) 0.043(3) Uani 1 1 d . A . C14 C 0.9548(10) 0.5368(9) 0.6391(9) 0.039(3) Uani 1 1 d . . . C15 C 1.0144(10) 0.6473(10) 0.6832(10) 0.042(3) Uani 1 1 d . A . C16 C 1.1159(10) 0.6817(10) 0.7415(11) 0.047(3) Uani 1 1 d . . . C17 C 1.1723(10) 0.7848(10) 0.8141(11) 0.050(3) Uani 1 1 d D A . C18 C 1.2740(12) 0.7883(11) 0.8432(11) 0.056(4) Uani 1 1 d D . . C19 C 1.2808(9) 0.6887(10) 0.7936(9) 0.040(3) Uani 1 1 d . A . C20 C 1.3739(10) 0.6603(9) 0.7858(9) 0.039(3) Uani 1 1 d . . . C51 C 1.2914(6) 0.2081(5) 0.7490(6) 0.044(3) Uiso 1 1 d G . . C52 C 1.3768(6) 0.2341(5) 0.8242(6) 0.046(3) Uiso 1 1 d G A . H52 H 1.4078 0.3043 0.8671 0.055 Uiso 1 1 calc R . . C53 C 1.4168(6) 0.1572(6) 0.8367(6) 0.056(4) Uiso 1 1 d G A . H53 H 1.4752 0.1749 0.8881 0.067 Uiso 1 1 calc R . . C54 C 1.3715(7) 0.0544(6) 0.7739(7) 0.056(4) Uiso 1 1 d G A . H54 H 1.3989 0.0019 0.7825 0.067 Uiso 1 1 calc R . . C55 C 1.2861(7) 0.0285(5) 0.6987(6) 0.062(4) Uiso 1 1 d G A . H55 H 1.2551 -0.0418 0.6558 0.074 Uiso 1 1 calc R . . C56 C 1.2460(6) 0.1053(6) 0.6862(6) 0.048(3) Uiso 1 1 d G A . H56 H 1.1877 0.0876 0.6347 0.058 Uiso 1 1 calc R . . C101 C 0.7767(5) 0.1895(5) 0.6308(6) 0.038(3) Uiso 1 1 d G A . C102 C 0.7707(5) 0.0886(6) 0.5771(6) 0.047(3) Uiso 1 1 d G . . H102 H 0.8319 0.0771 0.5521 0.056 Uiso 1 1 calc R A . C103 C 0.6749(6) 0.0046(5) 0.5600(7) 0.058(4) Uiso 1 1 d G A . H103 H 0.6708 -0.0643 0.5234 0.070 Uiso 1 1 calc R . . C104 C 0.5853(5) 0.0215(5) 0.5966(7) 0.054(4) Uiso 1 1 d G . . H104 H 0.5199 -0.0359 0.5849 0.065 Uiso 1 1 calc R A . C105 C 0.5913(5) 0.1224(6) 0.6503(7) 0.049(3) Uiso 1 1 d G A . H105 H 0.5300 0.1339 0.6753 0.059 Uiso 1 1 calc R . . C106 C 0.6870(6) 0.2064(5) 0.6673(6) 0.047(3) Uiso 1 1 d G . . H106 H 0.6911 0.2753 0.7040 0.057 Uiso 1 1 calc R A . C151 C 0.9696(6) 0.7250(6) 0.6629(7) 0.042(3) Uiso 1 1 d G . . C152 C 0.8783(6) 0.7356(7) 0.7009(6) 0.050(3) Uiso 1 1 d G A . H152 H 0.8444 0.6928 0.7400 0.060 Uiso 1 1 calc R . . C153 C 0.8368(6) 0.8090(7) 0.6816(7) 0.065(4) Uiso 1 1 d G A . H153 H 0.7744 0.8163 0.7075 0.078 Uiso 1 1 calc R . . C154 C 0.8865(7) 0.8717(7) 0.6243(8) 0.070(4) Uiso 1 1 d G A . H154 H 0.8580 0.9219 0.6111 0.084 Uiso 1 1 calc R . . C155 C 0.9777(7) 0.8610(7) 0.5863(7) 0.062(4) Uiso 1 1 d G A . H155 H 1.0117 0.9039 0.5472 0.075 Uiso 1 1 calc R . . C156 C 1.0193(6) 0.7877(7) 0.6056(7) 0.058(4) Uiso 1 1 d G A . H156 H 1.0816 0.7804 0.5797 0.069 Uiso 1 1 calc R . . C201 C 1.4813(5) 0.7431(6) 0.8178(6) 0.040(3) Uiso 1 1 d G A . C202 C 1.5118(6) 0.8230(6) 0.7731(6) 0.046(3) Uiso 1 1 d G . . H202 H 1.4632 0.8254 0.7222 0.055 Uiso 1 1 calc R A . C203 C 1.6135(6) 0.8995(6) 0.8030(6) 0.052(3) Uiso 1 1 d G A . H203 H 1.6343 0.9541 0.7726 0.063 Uiso 1 1 calc R . . C204 C 1.6846(5) 0.8961(6) 0.8776(7) 0.051(3) Uiso 1 1 d G . . H204 H 1.7541 0.9483 0.8980 0.061 Uiso 1 1 calc R A . C205 C 1.6541(6) 0.8162(7) 0.9222(6) 0.056(4) Uiso 1 1 d G A . H205 H 1.7027 0.8138 0.9731 0.067 Uiso 1 1 calc R . . C206 C 1.5524(6) 0.7397(6) 0.8923(6) 0.046(3) Uiso 1 1 d G . . H206 H 1.5315 0.6851 0.9228 0.055 Uiso 1 1 calc R A . Br2 Br 1.5748(2) 0.5862(2) 0.6662(2) 0.0506(8) Uani 0.60 1 d P A 1 Br3 Br 1.4804(2) 0.3172(2) 0.6299(2) 0.0462(7) Uani 0.60 1 d P A 1 Br7 Br 1.10284(15) 0.13073(17) 0.8771(2) 0.0450(5) Uani 0.70 1 d P A 1 Br8 Br 0.84736(16) 0.13083(19) 0.8220(2) 0.0487(6) Uani 0.70 1 d P A 1 Br12 Br 0.70587(12) 0.28516(12) 0.46246(11) 0.0539(5) Uani 1 1 d . A 1 Br13 Br 0.79414(12) 0.54924(12) 0.48597(11) 0.0560(5) Uani 1 1 d . A 1 Br17 Br 1.1164(2) 0.8853(2) 0.8803(2) 0.0576(8) Uani 0.60 1 d P A 1 Br18 Br 1.3691(2) 0.88994(18) 0.95839(19) 0.0499(6) Uani 0.60 1 d P A 1 C21 C 1.5642(17) 0.561(3) 0.686(3) 0.030 Uiso 0.40 1 d PD A 2 C22 C 1.547(2) 0.618(2) 0.612(2) 0.030 Uiso 0.40 1 d PD A 2 C31 C 1.486(2) 0.346(2) 0.673(2) 0.030 Uiso 0.40 1 d PD A 2 C32 C 1.448(2) 0.291(2) 0.562(2) 0.030 Uiso 0.40 1 d PD A 2 C71 C 1.091(4) 0.109(2) 0.824(3) 0.030 Uiso 0.30 1 d PD A 2 C72 C 1.106(3) 0.162(3) 0.935(3) 0.030 Uiso 0.30 1 d PD A 2 C81 C 0.876(3) 0.106(2) 0.789(3) 0.030 Uiso 0.30 1 d PD A 2 C82 C 0.826(3) 0.169(3) 0.864(3) 0.030 Uiso 0.30 1 d PD A 2 C171 C 1.123(3) 0.870(2) 0.836(2) 0.030 Uiso 0.40 1 d PD A 2 C172 C 1.046(2) 0.850(2) 0.9101(19) 0.030 Uiso 0.40 1 d PD A 2 C181 H 1.34(2) 0.893(11) 0.922(7) 0.030 Uiso 0.40 1 d PD B 2 C182 C 1.351(2) 0.842(2) 1.008(2) 0.030 Uiso 0.40 1 d PD C 2 C1S C 0.7632(18) 0.566(2) 0.890(2) 0.151(10) Uiso 1 1 d D . . H1S1 H 0.7305 0.5165 0.8224 0.181 Uiso 1 1 calc R . . H1S2 H 0.7678 0.6373 0.8891 0.181 Uiso 1 1 calc R . . C2S C 0.8737(19) 0.5648(18) 0.915(2) 0.132(9) Uiso 1 1 d D . . H2S1 H 0.9181 0.5850 0.8646 0.158 Uiso 1 1 calc R . . H2S2 H 0.9083 0.6157 0.9813 0.158 Uiso 1 1 calc R . . C3S C 0.865(2) 0.4565(18) 0.915(2) 0.130(9) Uiso 1 1 d D . . H3S1 H 0.9367 0.4541 0.9332 0.156 Uiso 1 1 calc R . . H3S2 H 0.8331 0.4063 0.8480 0.156 Uiso 1 1 calc R . . C4S C 0.7948(17) 0.426(2) 0.990(2) 0.139(9) Uiso 1 1 d D . . H4S1 H 0.7908 0.3548 0.9920 0.167 Uiso 1 1 calc R . . H4S2 H 0.8266 0.4760 1.0572 0.167 Uiso 1 1 calc R . . C5S C 0.6845(19) 0.4256(19) 0.962(2) 0.139(9) Uiso 1 1 d D . . H5S1 H 0.6524 0.3762 0.8946 0.167 Uiso 1 1 calc R . . H5S2 H 0.6381 0.4028 1.0103 0.167 Uiso 1 1 calc R . . C6S C 0.693(2) 0.5345(19) 0.964(2) 0.145(10) Uiso 1 1 d D . . H6S1 H 0.7242 0.5838 1.0320 0.174 Uiso 1 1 calc R . . H6S2 H 0.6207 0.5369 0.9466 0.174 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 N21 0.040(6) 0.035(6) 0.035(6) 0.005(5) 0.007(5) 0.014(5) N22 0.043(6) 0.035(6) 0.048(7) 0.015(5) 0.007(5) 0.009(5) N23 0.037(6) 0.040(6) 0.033(6) 0.006(5) 0.002(5) 0.012(5) N24 0.045(6) 0.038(6) 0.033(6) 0.008(5) 0.009(5) 0.018(5) C1 0.038(7) 0.046(8) 0.024(7) 0.007(6) 0.008(5) 0.014(6) C2 0.044(7) 0.057(9) 0.049(9) 0.021(7) 0.015(6) 0.025(7) C3 0.047(8) 0.040(8) 0.051(9) 0.014(7) 0.005(6) 0.016(6) C4 0.036(7) 0.040(7) 0.031(7) 0.006(6) 0.002(5) 0.010(6) C5 0.038(7) 0.033(7) 0.046(8) 0.011(6) 0.005(6) 0.008(6) C6 0.040(7) 0.031(7) 0.039(8) 0.013(6) 0.007(6) 0.015(6) C7 0.048(8) 0.045(8) 0.047(9) 0.004(7) 0.001(6) 0.023(6) C8 0.046(8) 0.047(8) 0.038(8) 0.009(7) 0.003(6) 0.014(6) C9 0.042(8) 0.046(8) 0.045(9) 0.014(7) 0.013(6) 0.013(6) C10 0.045(7) 0.035(7) 0.037(8) 0.001(6) 0.011(6) 0.017(6) C11 0.036(7) 0.045(8) 0.032(7) 0.008(6) 0.003(5) 0.016(6) C12 0.049(8) 0.048(8) 0.034(8) 0.013(7) 0.011(6) 0.011(6) C13 0.043(7) 0.039(8) 0.047(9) 0.008(7) 0.012(6) 0.016(6) C14 0.046(7) 0.025(7) 0.040(8) -0.002(6) 0.010(6) 0.014(6) C15 0.040(7) 0.050(8) 0.039(8) 0.014(7) 0.011(6) 0.021(6) C16 0.042(8) 0.041(8) 0.057(9) 0.008(7) 0.016(7) 0.015(6) C17 0.044(8) 0.044(8) 0.048(9) -0.009(7) 0.011(6) 0.016(6) C18 0.062(9) 0.051(9) 0.044(9) -0.007(7) 0.007(7) 0.020(7) C19 0.040(7) 0.045(8) 0.029(7) -0.005(6) 0.002(6) 0.021(6) C20 0.044(7) 0.033(7) 0.028(7) 0.002(6) -0.004(5) 0.005(6) Br2 0.0478(13) 0.0399(17) 0.067(2) 0.0167(13) 0.0323(13) 0.0137(12) Br3 0.0524(14) 0.0412(15) 0.0468(19) 0.0043(13) 0.0239(14) 0.0230(12) Br7 0.0418(11) 0.0519(13) 0.0498(13) 0.0301(12) 0.0038(12) 0.0159(10) Br8 0.0316(11) 0.0590(15) 0.0636(18) 0.0383(14) 0.0096(9) 0.0098(9) Br12 0.0556(9) 0.0576(9) 0.0408(9) 0.0111(7) 0.0023(7) 0.0134(7) Br13 0.0668(10) 0.0596(10) 0.0458(9) 0.0148(8) 0.0081(7) 0.0283(8) Br17 0.0712(18) 0.0483(15) 0.0476(17) -0.0073(14) -0.0032(16) 0.0331(13) Br18 0.0578(15) 0.0373(13) 0.0434(15) -0.0014(12) -0.0039(12) 0.0147(11) _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 N21 C1 1.338(15) . ? N21 C4 1.385(15) . ? N22 C9 1.346(16) . ? N22 C6 1.371(15) . ? N23 C14 1.337(15) . ? N23 C11 1.375(15) . ? N24 C16 1.360(16) . ? N24 C19 1.369(16) . ? C1 C20 1.417(17) . ? C1 C2 1.471(17) . ? C2 C3 1.375(18) . ? C2 C21 1.509(10) . ? C2 Br2 1.846(13) . ? C3 C4 1.439(17) . ? C3 C31 1.503(10) . ? C3 Br3 1.879(13) . ? C4 C5 1.396(17) . ? C5 C6 1.413(17) . ? C5 C51 1.463(13) . ? C6 C7 1.444(18) . ? C7 C8 1.387(18) . ? C7 C71 1.511(10) . ? C7 Br7 1.836(13) . ? C8 C9 1.448(18) . ? C8 C81 1.508(10) . ? C8 Br8 1.842(13) . ? C9 C10 1.410(18) . ? C10 C11 1.379(17) . ? C10 C101 1.505(13) . ? C11 C12 1.454(17) . ? C12 C13 1.328(18) . ? C12 Br12 1.912(13) . ? C13 C14 1.442(18) . ? C13 Br13 1.874(13) . ? C14 C15 1.439(17) . ? C15 C16 1.405(18) . ? C15 C151 1.477(13) . ? C16 C17 1.460(18) . ? C17 C18 1.371(19) . ? C17 C171 1.504(10) . ? C17 Br17 1.859(12) . ? C18 C19 1.421(18) . ? C18 Br18 1.908(14) . ? C19 C20 1.418(17) . ? C20 C201 1.480(13) . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C52 C53 1.3900 . ? C53 C54 1.3900 . ? C54 C55 1.3900 . ? C55 C56 1.3900 . ? C101 C102 1.3900 . ? C101 C106 1.3900 . ? C102 C103 1.3900 . ? C103 C104 1.3900 . ? C104 C105 1.3900 . ? C105 C106 1.3900 . ? C151 C152 1.3900 . ? C151 C156 1.3900 . ? C152 C153 1.3900 . ? C153 C154 1.3900 . ? C154 C155 1.3900 . ? C155 C156 1.3900 . ? C201 C202 1.3900 . ? C201 C206 1.3900 . ? C202 C203 1.3900 . ? C203 C204 1.3900 . ? C204 C205 1.3900 . ? C205 C206 1.3900 . ? C21 C22 1.510(10) . ? C31 C32 1.511(10) . ? C71 C72 1.508(10) . ? C81 C82 1.507(10) . ? C171 C172 1.525(10) . ? C1S C2S 1.497(15) . ? C1S C6S 1.502(15) . ? C2S C3S 1.488(15) . ? C3S C4S 1.498(15) . ? C4S C5S 1.496(15) . ? C5S C6S 1.489(15) . ? 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 N21 C4 109.5(10) . . ? C9 N22 C6 110.5(10) . . ? C14 N23 C11 109.8(10) . . ? C16 N24 C19 109.9(10) . . ? N21 C1 C20 123.4(11) . . ? N21 C1 C2 109.6(11) . . ? C20 C1 C2 126.7(11) . . ? C3 C2 C1 104.5(11) . . ? C3 C2 C21 117.0(19) . . ? C1 C2 C21 139(2) . . ? C3 C2 Br2 125.1(10) . . ? C1 C2 Br2 129.2(10) . . ? C21 C2 Br2 12.4(12) . . ? C2 C3 C4 109.5(11) . . ? C2 C3 C31 120.1(18) . . ? C4 C3 C31 129.8(18) . . ? C2 C3 Br3 123.1(10) . . ? C4 C3 Br3 126.3(9) . . ? C31 C3 Br3 16.6(12) . . ? N21 C4 C5 122.3(11) . . ? N21 C4 C3 106.7(10) . . ? C5 C4 C3 130.3(11) . . ? C4 C5 C6 121.4(11) . . ? C4 C5 C51 120.3(10) . . ? C6 C5 C51 118.3(10) . . ? N22 C6 C5 124.1(10) . . ? N22 C6 C7 107.2(10) . . ? C5 C6 C7 128.6(10) . . ? C8 C7 C6 107.1(11) . . ? C8 C7 C71 124(2) . . ? C6 C7 C71 127(2) . . ? C8 C7 Br7 123.5(10) . . ? C6 C7 Br7 128.1(9) . . ? C71 C7 Br7 22.0(14) . . ? C7 C8 C9 106.9(11) . . ? C7 C8 C81 114(2) . . ? C9 C8 C81 138(2) . . ? C7 C8 Br8 124.4(10) . . ? C9 C8 Br8 127.3(9) . . ? C81 C8 Br8 21.5(14) . . ? N22 C9 C10 124.2(12) . . ? N22 C9 C8 107.8(11) . . ? C10 C9 C8 127.8(11) . . ? C11 C10 C9 123.2(11) . . ? C11 C10 C101 120.4(10) . . ? C9 C10 C101 116.4(10) . . ? N23 C11 C10 123.4(11) . . ? N23 C11 C12 105.1(10) . . ? C10 C11 C12 130.9(11) . . ? C13 C12 C11 109.9(12) . . ? C13 C12 Br12 124.1(10) . . ? C11 C12 Br12 124.7(10) . . ? C12 C13 C14 105.9(11) . . ? C12 C13 Br13 123.2(10) . . ? C14 C13 Br13 130.7(9) . . ? N23 C14 C15 123.7(11) . . ? N23 C14 C13 109.2(10) . . ? C15 C14 C13 126.7(11) . . ? C16 C15 C14 120.9(11) . . ? C16 C15 C151 120.0(11) . . ? C14 C15 C151 119.1(10) . . ? N24 C16 C15 126.2(12) . . ? N24 C16 C17 106.3(11) . . ? C15 C16 C17 127.5(12) . . ? C18 C17 C16 107.5(11) . . ? C18 C17 C171 130.6(18) . . ? C16 C17 C171 121.5(18) . . ? C18 C17 Br17 122.5(10) . . ? C16 C17 Br17 128.7(10) . . ? C171 C17 Br17 17.9(12) . . ? C17 C18 C19 107.3(12) . . ? C17 C18 Br18 124.4(10) . . ? C19 C18 Br18 125.6(10) . . ? N24 C19 C20 123.1(11) . . ? N24 C19 C18 108.1(11) . . ? C20 C19 C18 128.1(12) . . ? C1 C20 C19 122.2(11) . . ? C1 C20 C201 118.1(10) . . ? C19 C20 C201 119.7(10) . . ? C52 C51 C56 120.0 . . ? C52 C51 C5 120.4(7) . . ? C56 C51 C5 119.5(7) . . ? C53 C52 C51 120.0 . . ? C52 C53 C54 120.0 . . ? C53 C54 C55 120.0 . . ? C54 C55 C56 120.0 . . ? C55 C56 C51 120.0 . . ? C102 C101 C106 120.0 . . ? C102 C101 C10 118.7(7) . . ? C106 C101 C10 121.2(7) . . ? C101 C102 C103 120.0 . . ? C102 C103 C104 120.0 . . ? C105 C104 C103 120.0 . . ? C104 C105 C106 120.0 . . ? C105 C106 C101 120.0 . . ? C152 C151 C156 120.0 . . ? C152 C151 C15 120.3(7) . . ? C156 C151 C15 119.7(7) . . ? C151 C152 C153 120.0 . . ? C154 C153 C152 120.0 . . ? C155 C154 C153 120.0 . . ? C154 C155 C156 120.0 . . ? C155 C156 C151 120.0 . . ? C202 C201 C206 120.0 . . ? C202 C201 C20 120.6(6) . . ? C206 C201 C20 119.4(7) . . ? C201 C202 C203 120.0 . . ? C204 C203 C202 120.0 . . ? C205 C204 C203 120.0 . . ? C204 C205 C206 120.0 . . ? C205 C206 C201 120.0 . . ? C2 C21 C22 104(2) . . ? C3 C31 C32 102(2) . . ? C72 C71 C7 99(3) . . ? C82 C81 C8 102(3) . . ? C17 C171 C172 108.8(19) . . ? C2S C1S C6S 112(2) . . ? C3S C2S C1S 108(2) . . ? C2S C3S C4S 109(2) . . ? C5S C4S C3S 110(2) . . ? C6S C5S C4S 108(2) . . ? C5S C6S C1S 108(2) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 55.06 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.975 _refine_diff_density_min -1.337 _refine_diff_density_rms 0.159 #====END data_ms408 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2,3,12,13-Tetraethyl-7-formyl-5,10,15,20- tetraphenylporphyrinato)nickel(II) ; _chemical_name_common ? _chemical_formula_moiety ; C53 H44 N4 Ni1 O1.0.75(C1 H1 Cl3).0.25(H2 O1) ; _chemical_formula_sum 'C53.75 H45.25 Cl2.25 N4 Ni O1.25' _chemical_formula_weight 905.66 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' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 12.579(3) _cell_length_b 13.882(3) _cell_length_c 14.383(3) _cell_angle_alpha 86.401(17) _cell_angle_beta 73.099(16) _cell_angle_gamma 69.047(17) _cell_volume 2241.9(8) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 42 _cell_measurement_theta_min 41 _cell_measurement_theta_max 55 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.342 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 944 _exptl_absorpt_coefficient_mu 2.207 _exptl_absorpt_correction_type 'empirical, XABS2' _exptl_absorpt_correction_T_min 0.7331 _exptl_absorpt_correction_T_max 0.9368 _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Ni-filter _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method '2theta-theta' _diffrn_detector_area_resol_mean n/a _diffrn_standards_number 2 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% stable _diffrn_reflns_number 6107 _diffrn_reflns_av_R_equivalents 0.0599 _diffrn_reflns_av_sigmaI/netI 0.0807 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.21 _diffrn_reflns_theta_max 56.45 _reflns_number_total 5935 _reflns_number_gt 3725 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3' _computing_cell_refinement 'Siemens P3' _computing_data_reduction 'XDISK, Shelxtl-Plus, Siemens 1994' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus, Siemens 1994' _computing_publication_material 'XCIF, Shelxtl-Plus, Siemens 1994' _refine_special_details ; The compound crystallized with solvate molecule which were located in close vicinity to each other. One was refined as a chloroform with 75 % occupancy and one refined as a water with 25 % occupancy. No hydrogen atoms were included in the refinement for the water molecule. One ethyl side chain was disordered. C122 was refined as disordered over two positions with occupancies of 0.7 (C122) and 0.3 C12B. C12B was refined with isotropic thermal parameters only. Residual electron density is located in the solvent region. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1788P)^2^+11.6405P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef n/d _refine_ls_number_reflns 5935 _refine_ls_number_parameters 403 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.1640 _refine_ls_R_factor_gt 0.1105 _refine_ls_wR_factor_ref 0.3280 _refine_ls_wR_factor_gt 0.2818 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.020 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.14559(13) 0.22235(10) 0.29316(10) 0.0337(5) Uani 1 d . . . N21 N 0.1247(6) 0.0939(5) 0.2773(5) 0.0339(17) Uani 1 d . . . N22 N -0.0180(7) 0.2835(5) 0.3619(5) 0.0380(18) Uani 1 d . . . N23 N 0.1646(6) 0.3558(5) 0.2920(5) 0.0345(17) Uani 1 d . . . N24 N 0.3131(6) 0.1572(5) 0.2419(5) 0.0363(18) Uani 1 d . . . C1 C 0.2076(8) 0.0085(6) 0.2163(6) 0.035(2) Uani 1 d . . . C2 C 0.1468(9) -0.0594(6) 0.2018(7) 0.038(2) Uani 1 d . . . C3 C 0.0332(8) -0.0217(7) 0.2603(7) 0.037(2) Uani 1 d . . . C4 C 0.0204(8) 0.0722(6) 0.3084(6) 0.035(2) Uani 1 d . . . C5 C -0.0786(8) 0.1327(6) 0.3807(6) 0.035(2) Uani 1 d . . . C6 C -0.0929(8) 0.2313(6) 0.4093(7) 0.038(2) Uani 1 d . . . C7 C -0.1991(8) 0.3033(7) 0.4746(7) 0.043(2) Uani 1 d . . . C8 C -0.1919(9) 0.3974(7) 0.4591(8) 0.051(3) Uani 1 d . . . H8 H -0.2504 0.4605 0.4898 0.061 Uiso 1 calc R . . C9 C -0.0814(8) 0.3865(6) 0.3888(7) 0.039(2) Uani 1 d . . . C10 C -0.0434(9) 0.4669(6) 0.3531(7) 0.038(2) Uani 1 d . . . C11 C 0.0730(8) 0.4526(6) 0.3032(7) 0.038(2) Uani 1 d . . . C12 C 0.1247(9) 0.5315(6) 0.2711(7) 0.040(2) Uani 1 d . . . C13 C 0.2431(9) 0.4861(7) 0.2551(7) 0.039(2) Uani 1 d . . . C14 C 0.2682(8) 0.3762(6) 0.2685(7) 0.039(2) Uani 1 d . . . C15 C 0.3786(8) 0.3015(7) 0.2603(7) 0.043(2) Uani 1 d . . . C16 C 0.3985(8) 0.1975(7) 0.2499(7) 0.040(2) Uani 1 d . . . C17 C 0.5121(8) 0.1170(7) 0.2277(7) 0.044(2) Uani 1 d . . . H17 H 0.5841 0.1230 0.2302 0.053 Uiso 1 calc R . . C18 C 0.4992(8) 0.0305(7) 0.2025(7) 0.041(2) Uani 1 d . . . H18 H 0.5605 -0.0350 0.1833 0.049 Uiso 1 calc R . . C19 C 0.3770(8) 0.0557(6) 0.2098(6) 0.034(2) Uani 1 d . . . C20 C 0.3282(8) -0.0144(6) 0.1890(6) 0.036(2) Uani 1 d . . . C21 C 0.1950(9) -0.1450(7) 0.1253(6) 0.048(2) Uani 1 d D . . H21A H 0.1427 -0.1863 0.1390 0.057 Uiso 1 calc R . . H21B H 0.2750 -0.1911 0.1276 0.057 Uiso 1 calc R . . C22 C 0.2029(10) -0.1024(8) 0.0226(7) 0.062(3) Uani 1 d D . . H22A H 0.2341 -0.1600 -0.0256 0.093 Uiso 1 calc R . . H22B H 0.2561 -0.0628 0.0083 0.093 Uiso 1 calc R . . H22C H 0.1236 -0.0574 0.0200 0.093 Uiso 1 calc R . . C31 C -0.0624(9) -0.0646(7) 0.2639(8) 0.051(3) Uani 1 d D . . H31A H -0.1157 -0.0562 0.3311 0.061 Uiso 1 calc R . . H31B H -0.0254 -0.1393 0.2454 0.061 Uiso 1 calc R . . C32 C -0.1362(10) -0.0085(10) 0.1938(9) 0.074(3) Uani 1 d D . . H32A H -0.1967 -0.0385 0.1966 0.111 Uiso 1 calc R . . H32B H -0.0835 -0.0166 0.1272 0.111 Uiso 1 calc R . . H32C H -0.1751 0.0651 0.2133 0.111 Uiso 1 calc R . . C51 C -0.1805(4) 0.0963(4) 0.4276(4) 0.038(2) Uiso 1 d G . . C52 C -0.2869(5) 0.1415(4) 0.4043(4) 0.041(2) Uiso 1 d G . . H52 H -0.2929 0.1909 0.3555 0.049 Uiso 1 calc R . . C53 C -0.3846(4) 0.1144(4) 0.4524(4) 0.048(2) Uiso 1 d G . . H53 H -0.4573 0.1454 0.4364 0.058 Uiso 1 calc R . . C54 C -0.3758(4) 0.0421(4) 0.5238(4) 0.047(2) Uiso 1 d G . . H54 H -0.4426 0.0236 0.5566 0.056 Uiso 1 calc R . . C55 C -0.2694(5) -0.0031(4) 0.5471(4) 0.047(2) Uiso 1 d G . . H55 H -0.2634 -0.0525 0.5959 0.057 Uiso 1 calc R . . C56 C -0.1718(4) 0.0240(4) 0.4990(4) 0.038(2) Uiso 1 d G . . H56 H -0.0991 -0.0069 0.5150 0.046 Uiso 1 calc R . . C71 C -0.2928(12) 0.2863(10) 0.5538(11) 0.082(4) Uani 1 d . . . H71 H -0.2774 0.2196 0.5797 0.098 Uiso 1 calc R . . O1 O -0.3897(9) 0.3527(8) 0.5887(8) 0.103(3) Uani 1 d . . . C101 C -0.1352(5) 0.5735(4) 0.3794(5) 0.042(2) Uiso 1 d G . . C102 C -0.2121(6) 0.6169(5) 0.3231(4) 0.064(3) Uiso 1 d G . . H102 H -0.2100 0.5776 0.2704 0.077 Uiso 1 calc R . . C103 C -0.2920(6) 0.7178(5) 0.3438(5) 0.074(3) Uiso 1 d G . . H103 H -0.3445 0.7475 0.3053 0.089 Uiso 1 calc R . . C104 C -0.2950(6) 0.7753(4) 0.4209(5) 0.070(3) Uiso 1 d G . . H104 H -0.3497 0.8442 0.4351 0.084 Uiso 1 calc R . . C105 C -0.2182(6) 0.7319(4) 0.4773(4) 0.062(3) Uiso 1 d G . . H105 H -0.2203 0.7712 0.5299 0.074 Uiso 1 calc R . . C106 C -0.1383(6) 0.6310(5) 0.4565(4) 0.055(3) Uiso 1 d G . . H106 H -0.0857 0.6013 0.4950 0.066 Uiso 1 calc R . . C121 C 0.0624(11) 0.6410(8) 0.2497(9) 0.072(4) Uani 1 d D . . H12A H 0.1142 0.6817 0.2440 0.086 Uiso 1 calc R A 1 H12B H -0.0115 0.6729 0.3030 0.086 Uiso 1 calc R A 1 C122 C 0.0320(19) 0.6396(13) 0.1512(12) 0.084(6) Uani 0.70 d PD B 1 H12C H -0.0094 0.7105 0.1359 0.126 Uiso 0.70 calc PR B 1 H12D H -0.0192 0.5990 0.1575 0.126 Uiso 0.70 calc PR B 1 H12E H 0.1056 0.6086 0.0989 0.126 Uiso 0.70 calc PR B 1 C12B C 0.071(6) 0.691(5) 0.340(3) 0.14(2) Uiso 0.30 d PD B 2 H12F H 0.0333 0.7665 0.3408 0.208 Uiso 0.30 calc PR B 2 H12G H 0.1547 0.6733 0.3374 0.208 Uiso 0.30 calc PR B 2 H12H H 0.0303 0.6655 0.4000 0.208 Uiso 0.30 calc PR B 2 C131 C 0.3297(10) 0.5409(7) 0.2153(7) 0.054(3) Uani 1 d D . . H13A H 0.4009 0.5085 0.2384 0.065 Uiso 1 calc R . . H13B H 0.2925 0.6141 0.2394 0.065 Uiso 1 calc R . . C132 C 0.3672(13) 0.5353(10) 0.1030(8) 0.086(4) Uani 1 d D . . H13C H 0.4234 0.5712 0.0782 0.129 Uiso 1 calc R . . H13D H 0.2968 0.5681 0.0802 0.129 Uiso 1 calc R . . H13E H 0.4051 0.4628 0.0793 0.129 Uiso 1 calc R . . C151 C 0.4816(4) 0.3291(2) 0.2641(4) 0.052(3) Uiso 1 d G . . C152 C 0.4796(5) 0.3711(3) 0.3501(4) 0.058(3) Uiso 1 d G . . H152 H 0.4158 0.3772 0.4072 0.070 Uiso 1 calc R . . C153 C 0.5708(5) 0.4041(3) 0.3526(4) 0.072(3) Uiso 1 d G . . H153 H 0.5694 0.4329 0.4113 0.086 Uiso 1 calc R . . C154 C 0.6642(5) 0.3952(3) 0.2690(5) 0.075(3) Uiso 1 d G . . H154 H 0.7265 0.4178 0.2707 0.090 Uiso 1 calc R . . C155 C 0.6662(5) 0.3532(3) 0.1830(4) 0.080(4) Uiso 1 d G . . H155 H 0.7300 0.3471 0.1259 0.096 Uiso 1 calc R . . C156 C 0.5750(5) 0.3201(3) 0.1805(3) 0.066(3) Uiso 1 d G . . H156 H 0.5764 0.2914 0.1218 0.079 Uiso 1 calc R . . C201 C 0.4143(3) -0.1189(3) 0.1494(3) 0.039(2) Uiso 1 d G . . C202 C 0.4775(5) -0.1361(3) 0.0513(3) 0.049(2) Uiso 1 d G . . H202 H 0.4639 -0.0815 0.0080 0.059 Uiso 1 calc R . . C203 C 0.5605(5) -0.2333(3) 0.0167(3) 0.061(3) Uiso 1 d G . . H203 H 0.6036 -0.2450 -0.0503 0.073 Uiso 1 calc R . . C204 C 0.5804(4) -0.3132(3) 0.0801(4) 0.064(3) Uiso 1 d G . . H204 H 0.6371 -0.3796 0.0564 0.077 Uiso 1 calc R . . C205 C 0.5173(5) -0.2960(3) 0.1781(4) 0.054(3) Uiso 1 d G . . H205 H 0.5309 -0.3506 0.2215 0.065 Uiso 1 calc R . . C206 C 0.4342(4) -0.1988(3) 0.2128(3) 0.049(2) Uiso 1 d G . . H206 H 0.3911 -0.1871 0.2798 0.059 Uiso 1 calc R . . C1S C -0.1357(19) 0.7598(12) -0.0489(12) 0.091(6) Uani 0.75 d P . . H1S H -0.1843 0.7908 -0.0946 0.110 Uiso 0.75 calc PR . . Cl1S Cl 0.0099(4) 0.7986(4) -0.0877(3) 0.0907(15) Uani 0.75 d P . . Cl2S Cl -0.0829(6) 0.6317(4) -0.0660(4) 0.118(2) Uani 0.75 d P . . Cl3S Cl -0.2045(5) 0.8163(5) 0.0547(6) 0.128(2) Uani 0.75 d P . . O1S O 0.0591(19) 0.5888(15) -0.1001(15) 0.028(5) Uiso 0.25 d P . . 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 Ni 0.0351(9) 0.0339(8) 0.0338(9) 0.0032(6) -0.0107(7) -0.0139(6) N21 0.033(4) 0.039(4) 0.027(4) 0.004(3) -0.007(3) -0.011(3) N22 0.043(5) 0.036(4) 0.036(4) 0.005(3) -0.011(4) -0.016(4) N23 0.029(4) 0.040(4) 0.032(4) 0.000(3) -0.007(3) -0.010(3) N24 0.038(5) 0.036(4) 0.037(4) 0.009(3) -0.011(4) -0.016(3) C1 0.051(6) 0.035(4) 0.025(5) 0.009(4) -0.014(4) -0.021(4) C2 0.048(6) 0.037(5) 0.039(6) 0.004(4) -0.023(5) -0.018(4) C3 0.038(6) 0.049(5) 0.036(5) 0.011(4) -0.019(5) -0.023(4) C4 0.043(6) 0.035(4) 0.031(5) 0.007(4) -0.015(5) -0.016(4) C5 0.030(5) 0.039(5) 0.033(5) 0.007(4) -0.010(4) -0.009(4) C6 0.034(5) 0.037(5) 0.043(6) 0.007(4) -0.009(5) -0.015(4) C7 0.032(6) 0.048(5) 0.046(6) 0.000(4) -0.005(5) -0.014(4) C8 0.039(6) 0.043(5) 0.065(7) -0.014(5) -0.010(6) -0.009(4) C9 0.035(6) 0.037(5) 0.047(6) -0.007(4) -0.017(5) -0.010(4) C10 0.052(7) 0.027(4) 0.041(6) 0.000(4) -0.027(5) -0.011(4) C11 0.039(6) 0.037(5) 0.040(6) 0.001(4) -0.018(5) -0.011(4) C12 0.055(7) 0.036(5) 0.036(6) 0.012(4) -0.016(5) -0.024(5) C13 0.047(6) 0.041(5) 0.038(6) 0.007(4) -0.017(5) -0.023(5) C14 0.042(6) 0.037(5) 0.038(6) 0.001(4) -0.007(5) -0.017(4) C15 0.035(6) 0.043(5) 0.055(6) 0.006(4) -0.013(5) -0.020(4) C16 0.034(5) 0.049(5) 0.042(6) 0.008(4) -0.014(5) -0.019(4) C17 0.019(5) 0.045(5) 0.066(7) 0.002(5) -0.010(5) -0.009(4) C18 0.040(6) 0.039(5) 0.037(6) -0.001(4) -0.006(5) -0.011(4) C19 0.042(6) 0.034(5) 0.022(5) 0.003(4) -0.007(4) -0.011(4) C20 0.038(6) 0.027(4) 0.038(5) 0.001(4) -0.011(4) -0.007(4) C21 0.057(7) 0.051(5) 0.039(6) -0.010(4) -0.010(5) -0.026(5) C22 0.068(8) 0.068(7) 0.050(7) -0.011(5) -0.025(6) -0.017(6) C31 0.046(6) 0.046(5) 0.065(7) -0.002(5) -0.016(5) -0.022(5) C32 0.055(8) 0.104(9) 0.068(8) -0.013(7) -0.021(7) -0.028(7) C71 0.062(9) 0.065(8) 0.107(11) -0.002(7) -0.006(8) -0.025(7) O1 0.073(7) 0.088(6) 0.125(9) -0.018(6) 0.010(6) -0.027(6) C121 0.064(8) 0.044(6) 0.104(11) 0.020(6) -0.027(7) -0.017(5) C122 0.126(17) 0.061(10) 0.076(13) 0.026(9) -0.060(13) -0.026(11) C131 0.061(7) 0.040(5) 0.062(7) 0.003(5) -0.016(6) -0.021(5) C132 0.097(11) 0.075(8) 0.078(10) -0.004(7) 0.006(8) -0.046(8) C1S 0.148(19) 0.068(10) 0.059(11) -0.003(8) -0.065(12) -0.010(11) Cl1S 0.073(3) 0.106(3) 0.081(3) 0.043(3) -0.010(2) -0.032(3) Cl2S 0.187(6) 0.082(3) 0.096(4) -0.014(3) -0.073(4) -0.032(3) Cl3S 0.088(4) 0.126(4) 0.168(6) -0.029(4) -0.024(4) -0.040(3) _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 Ni N22 1.899(8) . ? Ni N24 1.903(7) . ? Ni N21 1.930(7) . ? Ni N23 1.949(7) . ? N21 C4 1.392(11) . ? N21 C1 1.405(11) . ? N22 C9 1.380(11) . ? N22 C6 1.390(11) . ? N23 C14 1.374(11) . ? N23 C11 1.404(11) . ? N24 C19 1.378(10) . ? N24 C16 1.411(11) . ? C1 C20 1.372(12) . ? C1 C2 1.465(12) . ? C2 C3 1.359(13) . ? C2 C21 1.501(12) . ? C3 C4 1.450(12) . ? C3 C31 1.508(12) . ? C4 C5 1.395(12) . ? C5 C6 1.388(12) . ? C5 C51 1.507(9) . ? C6 C7 1.448(13) . ? C7 C8 1.342(13) . ? C7 C71 1.459(16) . ? C8 C9 1.425(14) . ? C9 C10 1.381(12) . ? C10 C11 1.377(13) . ? C10 C101 1.504(10) . ? C11 C12 1.451(12) . ? C12 C13 1.347(13) . ? C12 C121 1.500(13) . ? C13 C14 1.456(12) . ? C13 C131 1.506(13) . ? C14 C15 1.381(12) . ? C15 C16 1.384(12) . ? C15 C151 1.493(10) . ? C16 C17 1.425(12) . ? C17 C18 1.353(12) . ? C18 C19 1.422(13) . ? C19 C20 1.409(12) . ? C20 C201 1.491(9) . ? C21 C22 1.546(10) . ? C31 C32 1.554(11) . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C52 C53 1.3900 . ? C53 C54 1.3900 . ? C54 C55 1.3900 . ? C55 C56 1.3900 . ? C71 O1 1.220(14) . ? C101 C102 1.3900 . ? C101 C106 1.3900 . ? C102 C103 1.3900 . ? C103 C104 1.3900 . ? C104 C105 1.3900 . ? C105 C106 1.3900 . ? C121 C12B 1.567(14) . ? C121 C122 1.574(12) . ? C131 C132 1.544(11) . ? C151 C152 1.3900 . ? C151 C156 1.3900 . ? C152 C153 1.3900 . ? C153 C154 1.3900 . ? C154 C155 1.3900 . ? C155 C156 1.3900 . ? C201 C202 1.3900 . ? C201 C206 1.3901 . ? C202 C203 1.3899 . ? C203 C204 1.3902 . ? C204 C205 1.3898 . ? C205 C206 1.3900 . ? C1S Cl3S 1.580(18) . ? C1S Cl2S 1.667(17) . ? C1S Cl1S 2.01(2) . ? 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 N22 Ni N24 171.9(3) . . ? N22 Ni N21 90.4(3) . . ? N24 Ni N21 90.3(3) . . ? N22 Ni N23 90.5(3) . . ? N24 Ni N23 89.8(3) . . ? N21 Ni N23 172.4(3) . . ? C4 N21 C1 105.0(7) . . ? C4 N21 Ni 128.0(6) . . ? C1 N21 Ni 126.1(6) . . ? C9 N22 C6 105.6(7) . . ? C9 N22 Ni 127.4(6) . . ? C6 N22 Ni 126.2(6) . . ? C14 N23 C11 105.5(7) . . ? C14 N23 Ni 128.3(6) . . ? C11 N23 Ni 125.7(6) . . ? C19 N24 C16 105.0(7) . . ? C19 N24 Ni 128.2(6) . . ? C16 N24 Ni 125.4(6) . . ? C20 C1 N21 124.2(7) . . ? C20 C1 C2 125.9(8) . . ? N21 C1 C2 109.1(8) . . ? C3 C2 C1 107.8(8) . . ? C3 C2 C21 125.5(8) . . ? C1 C2 C21 126.1(9) . . ? C2 C3 C4 106.5(7) . . ? C2 C3 C31 125.3(8) . . ? C4 C3 C31 127.8(9) . . ? N21 C4 C5 122.1(7) . . ? N21 C4 C3 111.1(8) . . ? C5 C4 C3 126.7(8) . . ? C6 C5 C4 122.7(8) . . ? C6 C5 C51 116.1(7) . . ? C4 C5 C51 121.1(7) . . ? C5 C6 N22 123.5(8) . . ? C5 C6 C7 125.8(8) . . ? N22 C6 C7 109.2(7) . . ? C8 C7 C6 106.7(8) . . ? C8 C7 C71 121.6(10) . . ? C6 C7 C71 131.2(9) . . ? C7 C8 C9 108.3(8) . . ? N22 C9 C10 125.1(9) . . ? N22 C9 C8 109.8(8) . . ? C10 C9 C8 125.1(8) . . ? C11 C10 C9 123.0(8) . . ? C11 C10 C101 121.1(7) . . ? C9 C10 C101 115.7(8) . . ? C10 C11 N23 122.5(8) . . ? C10 C11 C12 127.5(8) . . ? N23 C11 C12 109.1(8) . . ? C13 C12 C11 107.3(7) . . ? C13 C12 C121 125.0(8) . . ? C11 C12 C121 127.5(9) . . ? C12 C13 C14 107.2(8) . . ? C12 C13 C131 123.7(8) . . ? C14 C13 C131 128.4(9) . . ? N23 C14 C15 123.7(7) . . ? N23 C14 C13 110.1(8) . . ? C15 C14 C13 126.2(8) . . ? C16 C15 C14 121.7(8) . . ? C16 C15 C151 116.8(7) . . ? C14 C15 C151 121.5(7) . . ? C15 C16 N24 124.7(8) . . ? C15 C16 C17 125.2(8) . . ? N24 C16 C17 109.1(7) . . ? C18 C17 C16 107.9(8) . . ? C17 C18 C19 107.3(8) . . ? N24 C19 C20 125.0(8) . . ? N24 C19 C18 110.7(7) . . ? C20 C19 C18 124.4(8) . . ? C1 C20 C19 121.0(8) . . ? C1 C20 C201 122.2(7) . . ? C19 C20 C201 116.3(7) . . ? C2 C21 C22 111.4(8) . . ? C3 C31 C32 111.1(8) . . ? C52 C51 C56 120.0 . . ? C52 C51 C5 119.3(4) . . ? C56 C51 C5 120.5(4) . . ? C51 C52 C53 120.0 . . ? C52 C53 C54 120.0 . . ? C55 C54 C53 120.0 . . ? C54 C55 C56 120.0 . . ? C55 C56 C51 120.0 . . ? O1 C71 C7 123.8(12) . . ? C102 C101 C106 120.0 . . ? C102 C101 C10 120.0(5) . . ? C106 C101 C10 119.9(5) . . ? C101 C102 C103 120.0 . . ? C104 C103 C102 120.0 . . ? C103 C104 C105 120.0 . . ? C106 C105 C104 120.0 . . ? C105 C106 C101 120.0 . . ? C12 C121 C12B 96(3) . . ? C12 C121 C122 107.9(10) . . ? C12B C121 C122 156(3) . . ? C13 C131 C132 110.4(8) . . ? C152 C151 C156 120.0 . . ? C152 C151 C15 119.5(4) . . ? C156 C151 C15 120.3(4) . . ? C153 C152 C151 120.0 . . ? C152 C153 C154 120.0 . . ? C153 C154 C155 120.0 . . ? C156 C155 C154 120.0 . . ? C155 C156 C151 120.0 . . ? C202 C201 C206 120.0 . . ? C202 C201 C20 121.0(4) . . ? C206 C201 C20 119.0(4) . . ? C203 C202 C201 120.0 . . ? C202 C203 C204 120.0 . . ? C205 C204 C203 120.0 . . ? C204 C205 C206 120.0 . . ? C205 C206 C201 120.0 . . ? Cl3S C1S Cl2S 122.8(11) . . ? Cl3S C1S Cl1S 102.6(9) . . ? Cl2S C1S Cl1S 104.3(11) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 56.45 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.106 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.117 #====END data_ms405 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,7,8,12,13-Hexabromo-17,18-diethyl-22,24-dihydro- 5,10,15,20-tetraphenylporphyrin ditrifluoroacetate ; _chemical_name_common ? _chemical_melting_point n/d _chemical_formula_moiety ; [C48 H34 Br6 N4]2[C2 F3 O2].2(C1 H1 Cl3) ; _chemical_formula_sum 'C54 H36 Br6 Cl6 F6 N4 O4' _chemical_formula_weight 1611.03 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' 'F' 'F' 0.0727 0.0534 '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' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pnma loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z' 'x+1/2, -y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z' '-x-1/2, y-1/2, z-1/2' _cell_length_a 15.803(9) _cell_length_b 19.024(5) _cell_length_c 19.652(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 5908(5) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 45 _cell_measurement_theta_min 41 _cell_measurement_theta_max 45 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'metallic green' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas n/d _exptl_crystal_density_diffrn 1.811 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3144 _exptl_absorpt_coefficient_mu 7.990 _exptl_absorpt_correction_type 'empirical, XABS2' _exptl_absorpt_correction_T_min 0.1423 _exptl_absorpt_correction_T_max 0.3803 _exptl_absorpt_process_details '(Parkin et al., 1994)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator Ni-filter _diffrn_measurement_device_type 'Siemens P4/RA' _diffrn_measurement_method '2theta-theta' _diffrn_detector_area_resol_mean n/a _diffrn_standards_number 2 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 4370 _diffrn_reflns_av_R_equivalents 0.0784 _diffrn_reflns_av_sigmaI/netI 0.0416 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.23 _diffrn_reflns_theta_max 56.44 _reflns_number_total 4046 _reflns_number_gt 2994 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3' _computing_cell_refinement 'Siemens P3' _computing_data_reduction 'XDISK, Shelxtl-Plus (Siemens, 1994)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus (Siemens, 1994)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. The phenyl rings were refined as rigid hexagons with isotropic thermal parameters. With the exception of C31, C32, CL1S, CL1', C2A, F2A and F1A all other nonhydrogen atoms were refined with anisotropic thermal parameters. There is considerable disorder in the counteranions and solvate molecules. For the chloroform containing C1S one chlorine atoms was refined as disordered over two split positions (Cl1S and Cl1') with equal occupancy. In addition, there was crystallographically required disorder in all counteranions and solvate molecules. A further problem was encountered with the two ethyl groups. Potentially a small amount of bromine ethyl disorder is encountered here since the large residual electron density is located about 1.8 \%A away from C2. In addition all attempts to refine the ethyl carbon atoms by conventional means failed. In the end the only practical course was ignoring the residual electron density and refining the ethyl carbon atoms with a common isotropic thermal parameter. All other attempts to model this situation failed. ; _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^)+(0.0929P)^2^+59.7290P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4046 _refine_ls_number_parameters 318 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1020 _refine_ls_R_factor_gt 0.0764 _refine_ls_wR_factor_ref 0.2106 _refine_ls_wR_factor_gt 0.1953 _refine_ls_goodness_of_fit_ref 1.182 _refine_ls_restrained_S_all 1.185 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N21 N -0.0468(8) 0.2500 0.9130(6) 0.022(3) Uani 1 2 d S . . H21 H -0.1025 0.2500 0.9139 0.026 Uiso 1 2 calc SR . . N22 N -0.1481(5) 0.1347(4) 0.9781(4) 0.0222(19) Uani 1 1 d . . . H22 H -0.1248 0.1691 1.0014 0.027 Uiso 1 1 calc R . . N23 N -0.2574(8) 0.2500 1.0411(6) 0.027(3) Uani 1 2 d S . . H23 H -0.2425 0.2500 0.9979 0.032 Uiso 1 2 calc SR . . C3 C 0.0886(7) 0.2137(5) 0.9181(5) 0.025(2) Uani 1 1 d . . . C4 C 0.0028(6) 0.1910(5) 0.9123(5) 0.022(2) Uani 1 1 d . . . C5 C -0.0312(7) 0.1230(5) 0.8996(5) 0.023(2) Uani 1 1 d . . . C6 C -0.1133(7) 0.1048(5) 0.9223(5) 0.023(2) Uani 1 1 d . . . C7 C -0.1712(7) 0.0532(5) 0.8982(5) 0.026(2) Uani 1 1 d . . . C8 C -0.2392(7) 0.0540(5) 0.9419(5) 0.024(2) Uani 1 1 d . . . C9 C -0.2246(7) 0.1042(5) 0.9939(5) 0.025(2) Uani 1 1 d . . . C10 C -0.2727(7) 0.1217(5) 1.0517(5) 0.024(2) Uani 1 1 d . . . C11 C -0.2703(6) 0.1905(5) 1.0785(5) 0.024(2) Uani 1 1 d . . . C12 C -0.2857(7) 0.2133(5) 1.1469(5) 0.025(2) Uani 1 1 d . . . C31 C 0.1699(8) 0.1638(6) 0.9408(6) 0.039(2) Uiso 1 1 d . . . H31A H 0.1811 0.1289 0.9045 0.047 Uiso 1 1 calc R . . H31B H 0.2209 0.1936 0.9456 0.047 Uiso 1 1 calc R . . C32 C 0.1554(8) 0.1300(6) 0.9998(6) 0.039(2) Uiso 1 1 d . . . H32A H 0.2048 0.1012 1.0115 0.059 Uiso 1 1 calc R . . H32B H 0.1056 0.0996 0.9949 0.059 Uiso 1 1 calc R . . H32C H 0.1452 0.1644 1.0360 0.059 Uiso 1 1 calc R . . Br7 Br -0.16698(8) 0.00668(6) 0.81541(6) 0.0350(4) Uani 1 1 d . . . Br8 Br -0.34118(7) 0.00617(6) 0.92778(6) 0.0324(4) Uani 1 1 d . . . Br12 Br -0.28653(8) 0.15916(6) 1.22463(6) 0.0356(4) Uani 1 1 d . . . C51 C 0.0215(7) 0.0754(5) 0.8590(5) 0.024(2) Uiso 1 1 d . . . C52 C 0.0299(7) 0.0045(6) 0.8767(5) 0.032(3) Uiso 1 1 d . . . H52 H 0.0022 -0.0134 0.9160 0.038 Uiso 1 1 calc R . . C53 C 0.0788(7) -0.0393(6) 0.8368(6) 0.035(3) Uiso 1 1 d . . . H53 H 0.0847 -0.0873 0.8491 0.042 Uiso 1 1 calc R . . C54 C 0.1189(8) -0.0148(6) 0.7797(6) 0.038(3) Uiso 1 1 d . . . H54 H 0.1529 -0.0455 0.7531 0.046 Uiso 1 1 calc R . . C55 C 0.1096(7) 0.0544(6) 0.7611(6) 0.034(3) Uiso 1 1 d . . . H55 H 0.1361 0.0712 0.7209 0.041 Uiso 1 1 calc R . . C56 C 0.0624(7) 0.0994(6) 0.8001(5) 0.028(3) Uiso 1 1 d . . . H56 H 0.0572 0.1473 0.7871 0.034 Uiso 1 1 calc R . . C101 C -0.3258(7) 0.0685(5) 1.0851(5) 0.026(2) Uiso 1 1 d . . . C102 C -0.4077(7) 0.0853(6) 1.1054(5) 0.030(3) Uiso 1 1 d . . . H102 H -0.4301 0.1307 1.0966 0.036 Uiso 1 1 calc R . . C103 C -0.4564(8) 0.0354(6) 1.1387(6) 0.034(3) Uiso 1 1 d . . . H103 H -0.5117 0.0469 1.1541 0.041 Uiso 1 1 calc R . . C104 C -0.4242(8) -0.0309(6) 1.1492(6) 0.037(3) Uiso 1 1 d . . . H104 H -0.4587 -0.0657 1.1698 0.044 Uiso 1 1 calc R . . C105 C -0.3427(7) -0.0476(6) 1.1303(5) 0.031(3) Uiso 1 1 d . . . H105 H -0.3205 -0.0930 1.1398 0.038 Uiso 1 1 calc R . . C106 C -0.2938(7) 0.0017(5) 1.0978(5) 0.025(2) Uiso 1 1 d . . . H106 H -0.2379 -0.0099 1.0840 0.031 Uiso 1 1 calc R . . C1S C 0.0029(13) 0.2500 0.5864(8) 0.096(9) Uani 1 2 d SD . . Cl1S Cl 0.0470(9) 0.1776(6) 0.5541(6) 0.127(4) Uiso 0.50 1 d PD . . Cl1' Cl -0.0426(12) 0.1923(9) 0.5287(9) 0.191(7) Uiso 0.50 1 d PD . . Cl2S Cl -0.0612(8) 0.2500 0.6551(7) 0.180(6) Uani 1 2 d SD . . C2S C -0.6278(8) 0.2500 1.1529(12) 0.096(10) Uani 1 2 d SD . . Cl3S Cl -0.6632(5) 0.1746(3) 1.1140(4) 0.149(3) Uani 1 1 d D . . Cl4S Cl -0.5195(6) 0.2500 1.1493(4) 0.117(3) Uani 1 2 d SD . . C1A C -0.2706(14) 0.2265(11) 0.8531(11) 0.051(8) Uani 0.50 1 d PD . . C2A C -0.2343(14) 0.2500 0.7819(13) 0.095(9) Uiso 1 2 d SD . . O1A O -0.3327(13) 0.1873(12) 0.8563(12) 0.083(7) Uani 0.50 1 d PD . . O2A O -0.2272(9) 0.2500 0.8997(6) 0.051(3) Uani 1 2 d SD . . F1A F -0.2860(16) 0.2198(14) 0.7379(11) 0.140(12) Uani 0.50 1 d PD . . F2A F -0.230(2) 0.1861(9) 0.7587(16) 0.148(11) Uiso 0.50 1 d PD . . F3A F -0.1675(13) 0.2080(11) 0.7777(11) 0.098(7) Uiso 0.50 1 d PD . . C3A C 0.4649(10) 0.2500 0.4023(8) 0.031(4) Uani 1 2 d SD . . C4A C 0.5250(13) 0.2500 0.3442(9) 0.062(6) Uani 1 2 d SD . . O3A O 0.4453(6) 0.1917(4) 0.4247(4) 0.049(2) Uani 1 1 d D . . F4A F 0.6049(11) 0.2500 0.3632(9) 0.128(7) Uani 1 2 d SD . . F5A F 0.5186(8) 0.1950(4) 0.3041(4) 0.102(4) Uani 1 1 d D . . 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 N21 0.016(7) 0.021(7) 0.029(7) 0.000 0.004(5) 0.000 N22 0.022(5) 0.018(4) 0.027(5) -0.004(4) 0.001(4) -0.001(4) N23 0.030(8) 0.022(7) 0.029(7) 0.000 0.012(6) 0.000 C3 0.026(6) 0.020(5) 0.030(6) 0.003(5) 0.000(5) 0.001(5) C4 0.020(6) 0.020(5) 0.025(5) 0.000(4) 0.001(5) 0.000(5) C5 0.024(6) 0.018(6) 0.029(6) 0.001(4) -0.004(5) 0.002(5) C6 0.027(6) 0.013(5) 0.030(6) 0.000(4) -0.004(5) 0.000(5) C7 0.024(6) 0.022(6) 0.031(6) 0.004(5) 0.002(5) 0.001(5) C8 0.022(6) 0.017(5) 0.033(6) -0.001(5) -0.011(5) -0.005(5) C9 0.019(6) 0.022(5) 0.034(6) 0.005(5) -0.003(5) 0.001(5) C10 0.022(6) 0.024(6) 0.025(5) 0.000(5) -0.001(5) -0.002(5) C11 0.018(6) 0.019(5) 0.035(6) 0.004(5) 0.000(5) -0.001(5) C12 0.020(6) 0.024(5) 0.030(6) -0.003(5) 0.004(5) 0.004(5) Br7 0.0322(7) 0.0390(7) 0.0339(7) -0.0120(5) -0.0004(5) -0.0040(6) Br8 0.0272(7) 0.0348(7) 0.0352(7) -0.0021(5) -0.0031(5) -0.0110(5) Br12 0.0459(8) 0.0285(6) 0.0326(6) 0.0033(5) 0.0075(6) 0.0005(6) C1S 0.14(3) 0.10(2) 0.053(14) 0.000 -0.013(16) 0.000 Cl2S 0.189(11) 0.108(7) 0.244(12) 0.000 0.149(10) 0.000 C2S 0.11(2) 0.050(14) 0.13(2) 0.000 0.05(2) 0.000 Cl3S 0.154(6) 0.107(4) 0.185(7) -0.062(5) 0.047(5) -0.055(4) Cl4S 0.124(7) 0.126(7) 0.101(6) 0.000 -0.021(5) 0.000 C1A 0.055(18) 0.040(19) 0.057(16) -0.004(11) -0.046(14) -0.001(12) O1A 0.056(15) 0.084(16) 0.109(18) -0.028(14) -0.009(13) -0.012(13) O2A 0.058(9) 0.045(7) 0.050(8) 0.000 0.000(7) 0.000 F1A 0.14(2) 0.18(3) 0.097(16) -0.024(15) -0.083(16) -0.033(19) C3A 0.025(10) 0.043(11) 0.026(9) 0.000 0.008(7) 0.000 C4A 0.083(19) 0.033(11) 0.069(15) 0.000 0.021(14) 0.000 O3A 0.064(6) 0.038(5) 0.044(5) -0.003(4) 0.023(5) -0.015(5) F4A 0.087(13) 0.187(19) 0.109(13) 0.000 0.053(11) 0.000 F5A 0.178(11) 0.053(5) 0.074(6) -0.017(5) 0.073(7) -0.022(6) _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 N21 C4 1.370(12) 7_565 ? N21 C4 1.370(12) . ? N22 C6 1.353(13) . ? N22 C9 1.376(13) . ? N23 C11 1.365(12) . ? N23 C11 1.365(12) 7_565 ? C3 C3 1.38(2) 7_565 ? C3 C4 1.428(15) . ? C3 C31 1.658(15) . ? C4 C5 1.422(14) . ? C5 C6 1.415(15) . ? C5 C51 1.467(14) . ? C6 C7 1.423(14) . ? C7 C8 1.376(15) . ? C7 Br7 1.853(10) . ? C8 C9 1.418(14) . ? C8 Br8 1.871(10) . ? C9 C10 1.407(14) . ? C10 C11 1.412(15) . ? C10 C101 1.469(14) . ? C11 C12 1.434(14) . ? C12 C12 1.39(2) 7_565 ? C12 Br12 1.843(10) . ? C31 C32 1.346(16) . ? C51 C52 1.399(15) . ? C51 C56 1.402(14) . ? C52 C53 1.380(15) . ? C53 C54 1.370(16) . ? C54 C55 1.373(16) . ? C55 C56 1.370(15) . ? C101 C102 1.393(15) . ? C101 C106 1.391(15) . ? C102 C103 1.385(16) . ? C103 C104 1.375(16) . ? C104 C105 1.377(16) . ? C105 C106 1.372(15) . ? C1S Cl1S 1.670(9) 7_565 ? C1S Cl1S 1.670(9) . ? C1S Cl2S 1.687(11) . ? C1S Cl1' 1.734(12) 7_565 ? C1S Cl1' 1.734(12) . ? Cl1S Cl1' 1.53(2) . ? Cl1' Cl1' 2.19(4) 7_565 ? C2S Cl4S 1.713(11) . ? C2S Cl3S 1.719(10) 7_565 ? C2S Cl3S 1.719(10) . ? C1A C1A 0.90(4) 7_565 ? C1A O2A 1.228(13) . ? C1A O1A 1.235(14) . ? C1A C2A 1.58(3) . ? C1A O1A 1.91(3) 7_565 ? C2A F1A 1.321(13) 7_565 ? C2A F1A 1.321(13) . ? C2A F2A 1.301(14) 7_565 ? C2A F2A 1.301(14) . ? C2A F3A 1.326(13) . ? C2A F3A 1.326(13) 7_565 ? C2A C1A 1.58(3) 7_565 ? O1A C1A 1.91(3) 7_565 ? O2A C1A 1.228(13) 7_565 ? F1A F1A 1.15(5) 7_565 ? F1A F2A 1.17(3) . ? F2A F3A 1.13(3) . ? F3A F3A 1.60(4) 7_565 ? C3A O3A 1.232(9) 7_565 ? C3A O3A 1.232(9) . ? C3A C4A 1.49(2) . ? C4A F4A 1.316(13) . ? C4A F5A 1.313(10) 7_565 ? C4A F5A 1.313(10) . ? 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 C4 N21 C4 110.2(12) 7_565 . ? C6 N22 C9 111.2(8) . . ? C11 N23 C11 112.0(12) . 7_565 ? C3 C3 C4 107.6(6) 7_565 . ? C3 C3 C31 124.9(6) 7_565 . ? C4 C3 C31 125.7(9) . . ? N21 C4 C5 122.1(9) . . ? N21 C4 C3 107.1(9) . . ? C5 C4 C3 130.4(10) . . ? C6 C5 C4 120.9(9) . . ? C6 C5 C51 122.7(9) . . ? C4 C5 C51 116.3(9) . . ? N22 C6 C5 121.7(9) . . ? N22 C6 C7 107.3(9) . . ? C5 C6 C7 130.9(10) . . ? C8 C7 C6 106.7(9) . . ? C8 C7 Br7 125.5(8) . . ? C6 C7 Br7 126.7(8) . . ? C7 C8 C9 109.2(9) . . ? C7 C8 Br8 125.1(8) . . ? C9 C8 Br8 125.1(8) . . ? N22 C9 C10 123.8(9) . . ? N22 C9 C8 105.4(9) . . ? C10 C9 C8 130.8(10) . . ? C9 C10 C11 120.4(9) . . ? C9 C10 C101 120.4(9) . . ? C11 C10 C101 119.2(9) . . ? N23 C11 C10 124.9(9) . . ? N23 C11 C12 106.2(9) . . ? C10 C11 C12 128.8(9) . . ? C12 C12 C11 107.6(6) 7_565 . ? C12 C12 Br12 124.0(3) 7_565 . ? C11 C12 Br12 127.5(8) . . ? C32 C31 C3 111.9(10) . . ? C52 C51 C56 118.5(10) . . ? C52 C51 C5 120.9(9) . . ? C56 C51 C5 120.6(9) . . ? C53 C52 C51 119.5(10) . . ? C54 C53 C52 121.3(11) . . ? C53 C54 C55 119.6(11) . . ? C56 C55 C54 120.6(11) . . ? C55 C56 C51 120.6(10) . . ? C102 C101 C106 119.7(10) . . ? C102 C101 C10 120.1(10) . . ? C106 C101 C10 120.2(10) . . ? C103 C102 C101 119.7(10) . . ? C104 C103 C102 119.5(11) . . ? C103 C104 C105 121.2(11) . . ? C106 C105 C104 119.6(11) . . ? C105 C106 C101 120.2(10) . . ? Cl1S C1S Cl1S 111.2(12) 7_565 . ? Cl1S C1S Cl2S 123.7(6) 7_565 . ? Cl1S C1S Cl2S 123.7(6) . . ? Cl1S C1S Cl1' 53.3(7) 7_565 7_565 ? Cl1S C1S Cl1' 116.5(11) . 7_565 ? Cl2S C1S Cl1' 105.9(12) . 7_565 ? Cl1S C1S Cl1' 116.5(11) 7_565 . ? Cl1S C1S Cl1' 53.3(7) . . ? Cl2S C1S Cl1' 105.9(12) . . ? Cl1' C1S Cl1' 78.5(15) 7_565 . ? Cl1' Cl1S C1S 65.5(6) . . ? Cl1S Cl1' C1S 61.2(5) . . ? Cl1S Cl1' Cl1' 100.6(8) . 7_565 ? C1S Cl1' Cl1' 50.7(8) . 7_565 ? Cl4S C2S Cl3S 107.9(8) . 7_565 ? Cl4S C2S Cl3S 107.9(8) . . ? Cl3S C2S Cl3S 113.1(12) 7_565 . ? C1A C1A O2A 68.6(11) 7_565 . ? C1A C1A O1A 127.2(16) 7_565 . ? O2A C1A O1A 129(2) . . ? C1A C1A C2A 73.5(8) 7_565 . ? O2A C1A C2A 110.8(17) . . ? O1A C1A C2A 120.4(18) . . ? C1A C1A O1A 30.9(8) 7_565 7_565 ? O2A C1A O1A 87.0(15) . 7_565 ? O1A C1A O1A 96(2) . 7_565 ? C2A C1A O1A 88.4(13) . 7_565 ? F1A C2A F1A 52(3) 7_565 . ? F1A C2A F2A 53.1(16) 7_565 7_565 ? F1A C2A F2A 102(3) . 7_565 ? F1A C2A F2A 102(3) 7_565 . ? F1A C2A F2A 53.1(16) . . ? F2A C2A F2A 138(4) 7_565 . ? F1A C2A F3A 136(3) 7_565 . ? F1A C2A F3A 100.9(19) . . ? F2A C2A F3A 120(3) 7_565 . ? F2A C2A F3A 50.8(17) . . ? F1A C2A F3A 100.9(19) 7_565 7_565 ? F1A C2A F3A 136(3) . 7_565 ? F2A C2A F3A 50.8(17) 7_565 7_565 ? F2A C2A F3A 120(3) . 7_565 ? F3A C2A F3A 74(2) . 7_565 ? F1A C2A C1A 103.4(18) 7_565 7_565 ? F1A C2A C1A 119(2) . 7_565 ? F2A C2A C1A 93.8(19) 7_565 7_565 ? F2A C2A C1A 127(2) . 7_565 ? F3A C2A C1A 121.0(19) . 7_565 ? F3A C2A C1A 99.9(17) 7_565 7_565 ? F1A C2A C1A 119(2) 7_565 . ? F1A C2A C1A 103.4(18) . . ? F2A C2A C1A 127(2) 7_565 . ? F2A C2A C1A 93.8(19) . . ? F3A C2A C1A 99.9(17) . . ? F3A C2A C1A 121.0(19) 7_565 . ? C1A C2A C1A 33.0(17) 7_565 . ? C1A O1A C1A 21.9(12) . 7_565 ? C1A O2A C1A 43(2) 7_565 . ? F1A F1A F2A 123.1(16) 7_565 . ? F1A F1A C2A 64.2(13) 7_565 . ? F2A F1A C2A 62.5(9) . . ? F3A F2A F1A 125.1(19) . . ? F3A F2A C2A 65.8(11) . . ? F1A F2A C2A 64.3(11) . . ? F2A F3A C2A 63.4(10) . . ? F2A F3A F3A 111.7(15) . 7_565 ? C2A F3A F3A 52.9(11) . 7_565 ? O3A C3A O3A 128.3(14) 7_565 . ? O3A C3A C4A 115.8(7) 7_565 . ? O3A C3A C4A 115.8(7) . . ? F4A C4A F5A 104.2(14) . 7_565 ? F4A C4A F5A 104.2(14) . . ? F5A C4A F5A 105.6(14) 7_565 . ? F4A C4A C3A 113.2(14) . . ? F5A C4A C3A 114.3(12) 7_565 . ? F5A C4A C3A 114.3(12) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 56.44 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 2.233 _refine_diff_density_min -1.289 _refine_diff_density_rms 0.168 #====END data_ms400 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,12-Dibromo-5,10,15,20-tetraphenylporphyrin ; _chemical_name_common 2,12-DiBr-TPP _chemical_formula_moiety ? _chemical_formula_sum 'C44 H28 Br2 N4' _chemical_formula_weight 772.52 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' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 13.993(15) _cell_length_b 6.699(5) _cell_length_c 18.832(17) _cell_angle_alpha 90.00 _cell_angle_beta 100.41(8) _cell_angle_gamma 90.00 _cell_volume 1736(3) _cell_formula_units_Z 2 _cell_measurement_temperature 129(2) _cell_measurement_reflns_used 37 _cell_measurement_theta_min 41 _cell_measurement_theta_max 52 _exptl_crystal_description plate _exptl_crystal_colour brown _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas n/d _exptl_crystal_density_diffrn 1.478 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 780 _exptl_absorpt_coefficient_mu 3.256 _exptl_absorpt_correction_type 'empirical, XABS2' _exptl_absorpt_correction_T_min 0.2928 _exptl_absorpt_correction_T_max 0.7366 _exptl_special_details ; ? ; _diffrn_ambient_temperature 129(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Syntex P21' _diffrn_measurement_method '2theta-theta' _diffrn_detector_area_resol_mean n/a _diffrn_standards_number 2 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% stable _diffrn_reflns_number 2691 _diffrn_reflns_av_R_equivalents 0.1280 _diffrn_reflns_av_sigmaI/netI 0.0716 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.77 _diffrn_reflns_theta_max 56.84 _reflns_number_total 2321 _reflns_number_gt 1875 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3' _computing_cell_refinement 'Siemens P3' _computing_data_reduction 'XDISK, Shelxtl-Plus, Siemens, 1994' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus, Siemens, 1994' _computing_publication_material 'XCIF, Shelxtl-Plus, Siemens, 1994' _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. The phenyl rings were refined as rigid hexagons with isotropic thermal parameters. The bromine substituents were disordered over three sets of positions and refined with the following occupancies: Br1 0.36, Br2 0.56, Br3 0.08. No hydrogen atoms were included in the refinement for the disordered positions. Hydrogens were added to all four pyrrole nitrogens and refined with occupancies of 0.5, each. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1272P)^2^+19.5854P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef n/d _refine_ls_number_reflns 2321 _refine_ls_number_parameters 165 _refine_ls_number_restraints 16 _refine_ls_R_factor_all 0.1306 _refine_ls_R_factor_gt 0.1102 _refine_ls_wR_factor_ref 0.2771 _refine_ls_wR_factor_gt 0.2638 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.120 _refine_ls_shift/su_max 0.000 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N21 N 0.8868(5) 0.7942(13) 0.9776(4) 0.030(2) Uani 1 d D . . H21 H 0.9336 0.8835 0.9867 0.036 Uiso 1 calc R . . N22 N 1.0804(5) 0.8415(13) 0.9352(5) 0.031(2) Uani 1 d D . . H22 H 1.0537 0.8922 0.9701 0.037 Uiso 1 calc R . . C1 C 0.8037(6) 0.7902(14) 1.0061(5) 0.028(2) Uani 1 d D . . C2 C 0.7461(6) 0.6208(14) 0.9786(5) 0.030(2) Uani 1 d D . . C3 C 0.7982(6) 0.5206(14) 0.9351(6) 0.036(3) Uani 1 d D . . C4 C 0.8839(6) 0.6352(14) 0.9327(5) 0.030(2) Uani 1 d D . . C5 C 0.9537(6) 0.5879(15) 0.8902(6) 0.030(3) Uani 1 d D . . C6 C 1.0419(6) 0.6856(15) 0.8915(5) 0.028(2) Uani 1 d D . . C7 C 1.1087(7) 0.6485(16) 0.8447(6) 0.034(3) Uani 1 d D . . H7 H 1.1022 0.5473 0.8088 0.041 Uiso 1 calc R . . C8 C 1.1847(7) 0.7822(15) 0.8594(6) 0.038(3) Uani 1 d D . . C9 C 1.1661(6) 0.9076(15) 0.9173(5) 0.030(3) Uani 1 d D . . C10 C 1.2214(7) 1.0717(15) 0.9443(6) 0.029(2) Uani 1 d D . . Br1 Br 0.61708(17) 0.5411(4) 0.98217(14) 0.0190(7) Uani 0.36 d PD . . Br2 Br 0.75773(11) 0.2632(2) 0.89828(8) 0.0146(5) Uani 0.56 d PD . . Br3 Br 1.2925(13) 0.781(3) 0.8091(12) 0.068(6) Uani 0.08 d PD . . C51 C 0.9300(5) 0.4355(9) 0.8328(3) 0.027(2) Uiso 1 d G . . C52 C 0.8621(4) 0.4789(8) 0.7712(3) 0.034(3) Uiso 1 d G . . H52 H 0.8295 0.6039 0.7670 0.040 Uiso 1 calc R . . C53 C 0.8419(5) 0.3394(10) 0.7159(3) 0.036(3) Uiso 1 d G . . H53 H 0.7955 0.3691 0.6739 0.044 Uiso 1 calc R . . C54 C 0.8896(5) 0.1565(9) 0.7221(3) 0.044(3) Uiso 1 d G . . H54 H 0.8758 0.0612 0.6843 0.053 Uiso 1 calc R . . C55 C 0.9575(5) 0.1131(8) 0.7837(4) 0.041(3) Uiso 1 d G . . H55 H 0.9901 -0.0119 0.7879 0.049 Uiso 1 calc R . . C56 C 0.9777(4) 0.2526(9) 0.8390(3) 0.034(3) Uiso 1 d G . . H56 H 1.0242 0.2230 0.8810 0.041 Uiso 1 calc R . . C101 C 1.3099(4) 1.1088(11) 0.9123(4) 0.032(3) Uiso 1 d G . . C102 C 1.3896(5) 0.9819(10) 0.9267(4) 0.046(3) Uiso 1 d G . . H102 H 1.3883 0.8698 0.9574 0.055 Uiso 1 calc R . . C103 C 1.4712(4) 1.0190(12) 0.8963(5) 0.058(4) Uiso 1 d G . . H103 H 1.5257 0.9323 0.9062 0.070 Uiso 1 calc R . . C104 C 1.4731(5) 1.1831(13) 0.8514(5) 0.052(3) Uiso 1 d G . . H104 H 1.5289 1.2085 0.8305 0.062 Uiso 1 calc R . . C105 C 1.3934(6) 1.3100(11) 0.8369(4) 0.062(4) Uiso 1 d G . . H105 H 1.3946 1.4221 0.8062 0.075 Uiso 1 calc R . . C106 C 1.3117(5) 1.2728(11) 0.8674(4) 0.047(3) Uiso 1 d G . . H106 H 1.2572 1.3595 0.8575 0.056 Uiso 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 N21 0.022(4) 0.037(5) 0.033(5) -0.005(4) 0.006(4) -0.003(4) N22 0.029(5) 0.039(5) 0.026(5) -0.002(4) 0.007(4) -0.004(4) C1 0.024(5) 0.032(6) 0.025(6) -0.002(5) 0.002(4) 0.001(5) C2 0.029(5) 0.029(6) 0.031(6) 0.000(5) 0.004(5) 0.004(5) C3 0.022(5) 0.037(6) 0.047(7) -0.003(6) 0.000(5) -0.002(5) C4 0.033(6) 0.019(5) 0.032(6) -0.001(5) -0.003(5) 0.005(4) C5 0.026(5) 0.028(6) 0.035(6) -0.003(5) 0.002(5) 0.008(5) C6 0.025(5) 0.032(6) 0.026(6) -0.002(5) 0.003(4) -0.001(5) C7 0.033(6) 0.032(6) 0.041(7) -0.013(5) 0.016(5) -0.008(5) C8 0.036(6) 0.032(6) 0.047(7) -0.016(6) 0.008(5) 0.006(5) C9 0.022(5) 0.038(6) 0.032(6) 0.010(5) 0.007(4) 0.006(5) C10 0.024(5) 0.031(6) 0.031(6) 0.000(5) 0.003(4) -0.002(5) Br1 0.0127(12) 0.0228(14) 0.0233(14) -0.0056(12) 0.0082(10) -0.0101(11) Br2 0.0183(9) 0.0135(9) 0.0116(9) -0.0019(7) 0.0014(6) -0.0062(7) Br3 0.069(11) 0.048(10) 0.105(16) 0.000(11) 0.060(12) 0.019(9) _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 N21 C4 1.356(12) . ? N21 C1 1.366(11) . ? N22 C9 1.376(11) . ? N22 C6 1.377(12) . ? C1 C10 1.403(14) 3_777 ? C1 C2 1.434(10) . ? C2 C3 1.368(12) . ? C2 Br1 1.895(8) . ? C3 C4 1.432(10) . ? C3 Br2 1.905(9) . ? C4 C5 1.407(12) . ? C5 C6 1.394(12) . ? C5 C51 1.480(11) . ? C6 C7 1.419(10) . ? C7 C8 1.380(13) . ? C8 C9 1.437(11) . ? C8 Br3 1.921(12) . ? C9 C10 1.387(13) . ? C10 C1 1.403(14) 3_777 ? C10 C101 1.492(11) . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C52 C53 1.3900 . ? C53 C54 1.3900 . ? C54 C55 1.3900 . ? C55 C56 1.3900 . ? C101 C102 1.3900 . ? C101 C106 1.3900 . ? C102 C103 1.3900 . ? C103 C104 1.3900 . ? C104 C105 1.3900 . ? C105 C106 1.3900 . ? 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 C4 N21 C1 107.3(8) . . ? C9 N22 C6 111.2(8) . . ? N21 C1 C10 125.6(8) . 3_777 ? N21 C1 C2 109.7(8) . . ? C10 C1 C2 124.7(9) 3_777 . ? C3 C2 C1 106.2(7) . . ? C3 C2 Br1 119.8(6) . . ? C1 C2 Br1 133.5(7) . . ? C2 C3 C4 107.2(7) . . ? C2 C3 Br2 120.4(6) . . ? C4 C3 Br2 132.0(7) . . ? N21 C4 C5 125.9(8) . . ? N21 C4 C3 109.5(8) . . ? C5 C4 C3 124.6(9) . . ? C6 C5 C4 126.0(9) . . ? C6 C5 C51 114.7(8) . . ? C4 C5 C51 119.0(8) . . ? N22 C6 C5 128.1(8) . . ? N22 C6 C7 105.9(8) . . ? C5 C6 C7 126.0(9) . . ? C6 C7 C8 109.4(8) . . ? C7 C8 C9 107.1(8) . . ? C7 C8 Br3 122.9(9) . . ? C9 C8 Br3 130.0(10) . . ? C10 C9 N22 128.2(9) . . ? C10 C9 C8 125.2(9) . . ? N22 C9 C8 106.4(8) . . ? C9 C10 C1 125.2(9) . 3_777 ? C9 C10 C101 115.6(9) . . ? C1 C10 C101 119.0(8) 3_777 . ? C52 C51 C56 120.0 . . ? C52 C51 C5 119.6(5) . . ? C56 C51 C5 120.4(5) . . ? C51 C52 C53 120.0 . . ? C54 C53 C52 120.0 . . ? C53 C54 C55 120.0 . . ? C54 C55 C56 120.0 . . ? C55 C56 C51 120.0 . . ? C102 C101 C106 120.0 . . ? C102 C101 C10 120.9(6) . . ? C106 C101 C10 119.1(6) . . ? C103 C102 C101 120.0 . . ? C102 C103 C104 120.0 . . ? C105 C104 C103 120.0 . . ? C106 C105 C104 120.0 . . ? C105 C106 C101 120.0 . . ? _diffrn_measured_fraction_theta_max 0.901 _diffrn_reflns_theta_full 56.84 _diffrn_measured_fraction_theta_full 0.901 _refine_diff_density_max 0.574 _refine_diff_density_min -0.876 _refine_diff_density_rms 0.148 #====END data_MS386 _audit_creation_method SHELXL-97 _chemical_name_systematic ; (2,3,12,13-Tetraethyl-7-formyl-5,10,15,20-tetra- phenylporphyrinato)nickel(II) ; _chemical_name_common Ni(II)CHOtTETPP _chemical_formula_moiety 'C53 H44 N4 Ni O.1(C1 H2 Cl2)' _chemical_formula_sum 'C54 H46 Cl2 N4 Ni O' _chemical_formula_weight 896.56 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' 'Ni' 'Ni' -3.0029 0.5091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 14.346(5) _cell_length_b 13.803(5) _cell_length_c 22.890(10) _cell_angle_alpha 90.00 _cell_angle_beta 104.43(3) _cell_angle_gamma 90.00 _cell_volume 4390(3) _cell_formula_units_Z 4 _cell_measurement_temperature 129(2) _cell_measurement_reflns_used 41 _cell_measurement_theta_min 41 _cell_measurement_theta_max 49 _exptl_crystal_description parallelepiped _exptl_crystal_colour red _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas n/d _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1872 _exptl_absorpt_coefficient_mu 2.107 _exptl_absorpt_correction_type 'empirical, XABS2' _exptl_absorpt_correction_T_min 0.3458 _exptl_absorpt_correction_T_max 0.8840 _exptl_special_details ; Crystals grown from methylene chloride/methanol. ; _diffrn_ambient_temperature 129(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator none _diffrn_measurement_device_type 'Siemens P4/RA' _diffrn_measurement_method '2theta-theta' _diffrn_detector_area_resol_mean n/a _diffrn_standards_number 2 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% stable _diffrn_reflns_number 6375 _diffrn_reflns_av_R_equivalents 0.0843 _diffrn_reflns_av_sigmaI/netI 0.1125 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 3.18 _diffrn_reflns_theta_max 56.35 _reflns_number_total 5792 _reflns_number_gt 3375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3' _computing_cell_refinement 'Siemens P3' _computing_data_reduction 'XDISK, Shelxtl-Plus, Siemens, 1994' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus, Siemens, 1994' _computing_publication_material 'XCIF, Shelxtl-Plus, Siemens, 1994' _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. The formyl group was found to be disordered over two positions (at C7 and C17) and was refined as disordered over two positions with occupancies of 0.8 and 0.2, respectively. The nonhydrogen atoms of the minor compo- nent were refined with isotropic thermal parameters only. No hydrogen atoms were included in the riding model for the Cb-position at which the minor formyl component was located. C1S in the solvate molecule showed relatively high thermal parameters. The meso-phenyl groups were refined as rigid hexagons with isotropic thermal parameters. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1102P)^2^+10.5020P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary Patterson _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef n/a _refine_ls_number_reflns 5792 _refine_ls_number_parameters 381 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1578 _refine_ls_R_factor_gt 0.0876 _refine_ls_wR_factor_ref 0.2399 _refine_ls_wR_factor_gt 0.1965 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Ni Ni 0.79075(9) 0.92119(8) 0.17999(5) 0.0268(4) Uani 1 d . . . N21 N 0.8106(4) 0.7823(4) 0.1802(3) 0.0292(15) Uani 1 d . . . N22 N 0.8640(4) 0.9300(4) 0.2620(3) 0.0290(15) Uani 1 d . . . N23 N 0.7539(4) 1.0559(4) 0.1828(3) 0.0249(14) Uani 1 d . . . N24 N 0.7361(4) 0.9187(4) 0.0948(3) 0.0269(15) Uani 1 d . . . C1 C 0.7849(5) 0.7181(5) 0.1327(3) 0.0281(19) Uani 1 d . . . C2 C 0.7846(5) 0.6199(5) 0.1545(4) 0.0288(19) Uani 1 d . . . C3 C 0.8118(6) 0.6240(5) 0.2159(4) 0.033(2) Uani 1 d . . . C4 C 0.8349(5) 0.7245(5) 0.2320(3) 0.0285(19) Uani 1 d . . . C5 C 0.8900(5) 0.7581(5) 0.2865(4) 0.0295(19) Uani 1 d . . . C6 C 0.9124(5) 0.8558(5) 0.2976(3) 0.0260(18) Uani 1 d . . . C7 C 0.9825(5) 0.8959(5) 0.3485(3) 0.0262(18) Uani 1 d . . . C8 C 0.9731(5) 0.9939(5) 0.3449(3) 0.0263(18) Uani 1 d . . . H8 H 1.0100 1.0398 0.3719 0.032 Uiso 1 calc R . . C9 C 0.8966(6) 1.0148(5) 0.2927(3) 0.0273(18) Uani 1 d . . . C10 C 0.8513(5) 1.1039(5) 0.2811(3) 0.0246(17) Uani 1 d . . . C11 C 0.7734(5) 1.1182(5) 0.2318(3) 0.0273(18) Uani 1 d . . . C12 C 0.7077(6) 1.2012(5) 0.2208(3) 0.0296(19) Uani 1 d . . . C13 C 0.6525(6) 1.1913(5) 0.1641(3) 0.033(2) Uani 1 d . . . C14 C 0.6861(5) 1.1055(5) 0.1383(3) 0.0270(18) Uani 1 d . . . C15 C 0.6695(5) 1.0829(5) 0.0775(3) 0.0263(17) Uani 1 d . . . C16 C 0.7009(5) 0.9966(5) 0.0580(3) 0.0261(18) Uani 1 d . . . C17 C 0.6994(5) 0.9739(5) -0.0045(3) 0.0281(19) Uani 1 d . . . C18 C 0.7275(5) 0.8809(5) -0.0047(3) 0.0315(19) Uani 1 d . . . H18 H 0.7325 0.8450 -0.0392 0.038 Uiso 1 calc R . . C19 C 0.7490(5) 0.8448(5) 0.0566(3) 0.0297(19) Uani 1 d . . . C20 C 0.7667(5) 0.7483(5) 0.0727(3) 0.0285(18) Uani 1 d . . . C21 C 0.7487(6) 0.5286(5) 0.1187(4) 0.036(2) Uani 1 d . . . H21A H 0.7695 0.5299 0.0805 0.044 Uiso 1 calc R . . H21B H 0.7788 0.4714 0.1421 0.044 Uiso 1 calc R . . C22 C 0.6402(7) 0.5177(6) 0.1040(4) 0.055(3) Uani 1 d . . . H22A H 0.6213 0.4580 0.0809 0.083 Uiso 1 calc R . . H22B H 0.6099 0.5734 0.0801 0.083 Uiso 1 calc R . . H22C H 0.6192 0.5145 0.1416 0.083 Uiso 1 calc R . . C31 C 0.8045(7) 0.5419(5) 0.2582(4) 0.044(2) Uani 1 d . . . H31A H 0.8666 0.5358 0.2888 0.052 Uiso 1 calc R . . H31B H 0.7933 0.4807 0.2350 0.052 Uiso 1 calc R . . C32 C 0.7242(8) 0.5552(6) 0.2905(5) 0.063(3) Uani 1 d . . . H32A H 0.7233 0.4997 0.3171 0.095 Uiso 1 calc R . . H32B H 0.6621 0.5598 0.2607 0.095 Uiso 1 calc R . . H32C H 0.7356 0.6148 0.3146 0.095 Uiso 1 calc R . . C71 C 1.0592(7) 0.8495(7) 0.3949(5) 0.038(3) Uani 0.80 d P . . H71 H 1.0821 0.7877 0.3866 0.046 Uiso 0.80 calc PR . . O1 O 1.0946(5) 0.8871(5) 0.4435(3) 0.047(2) Uani 0.80 d P . . C71' C 0.685(2) 1.036(2) -0.0501(15) 0.022(8) Uiso 0.20 d P . . H71' H 0.7018 1.1011 -0.0398 0.027 Uiso 0.20 calc PR . . O1' O 0.651(3) 1.018(2) -0.1074(16) 0.068(9) Uiso 0.20 d P . . C121 C 0.6949(6) 1.2759(5) 0.2661(4) 0.037(2) Uani 1 d . . . H12A H 0.6585 1.3315 0.2444 0.044 Uiso 1 calc R . . H12B H 0.7590 1.2999 0.2883 0.044 Uiso 1 calc R . . C122 C 0.6421(7) 1.2371(7) 0.3114(4) 0.057(3) Uani 1 d . . . H12C H 0.6360 1.2887 0.3397 0.086 Uiso 1 calc R . . H12D H 0.6785 1.1829 0.3338 0.086 Uiso 1 calc R . . H12E H 0.5779 1.2147 0.2899 0.086 Uiso 1 calc R . . C131 C 0.5592(6) 1.2451(6) 0.1368(4) 0.039(2) Uani 1 d . . . H13A H 0.5561 1.3043 0.1607 0.047 Uiso 1 calc R . . H13B H 0.5581 1.2652 0.0951 0.047 Uiso 1 calc R . . C132 C 0.4731(6) 1.1822(6) 0.1360(4) 0.048(2) Uani 1 d . . . H13C H 0.4140 1.2185 0.1185 0.072 Uiso 1 calc R . . H13D H 0.4737 1.1630 0.1773 0.072 Uiso 1 calc R . . H13E H 0.4754 1.1243 0.1117 0.072 Uiso 1 calc R . . C51 C 0.93382(17) 0.69050(12) 0.33870(8) 0.0301(18) Uiso 1 d G . . C52 C 1.01196(17) 0.63178(12) 0.33733(9) 0.038(2) Uiso 1 d G . . H52 H 1.0333 0.6265 0.3014 0.045 Uiso 1 calc R . . C53 C 1.0589(2) 0.58077(14) 0.38860(10) 0.0334(19) Uiso 1 d G . . H53 H 1.1123 0.5406 0.3877 0.040 Uiso 1 calc R . . C54 C 1.0277(2) 0.58848(14) 0.44123(9) 0.0309(18) Uiso 1 d G . . H54 H 1.0597 0.5536 0.4763 0.037 Uiso 1 calc R . . C55 C 0.9495(2) 0.64720(15) 0.44259(9) 0.0312(18) Uiso 1 d G . . H55 H 0.9282 0.6525 0.4786 0.037 Uiso 1 calc R . . C56 C 0.90260(18) 0.69821(13) 0.39133(8) 0.0332(19) Uiso 1 d G . . H56 H 0.8492 0.7383 0.3923 0.040 Uiso 1 calc R . . C101 C 0.88938(16) 1.18574(12) 0.32460(9) 0.0287(18) Uiso 1 d G . . C102 C 0.87549(18) 1.18685(13) 0.38256(8) 0.0340(19) Uiso 1 d G . . H102 H 0.8451 1.1336 0.3965 0.041 Uiso 1 calc R . . C103 C 0.9060(2) 1.26591(14) 0.42006(9) 0.042(2) Uiso 1 d G . . H103 H 0.8965 1.2667 0.4597 0.050 Uiso 1 calc R . . C104 C 0.9504(2) 1.34387(13) 0.39958(10) 0.040(2) Uiso 1 d G . . H104 H 0.9713 1.3979 0.4252 0.048 Uiso 1 calc R . . C105 C 0.9643(2) 1.34276(12) 0.34162(10) 0.036(2) Uiso 1 d G . . H105 H 0.9947 1.3960 0.3276 0.043 Uiso 1 calc R . . C106 C 0.93380(17) 1.26369(12) 0.30412(9) 0.039(2) Uiso 1 d G . . H106 H 0.9433 1.2629 0.2645 0.047 Uiso 1 calc R . . C151 C 0.62978(17) 1.15917(13) 0.03005(9) 0.0328(19) Uiso 1 d G . . C152 C 0.68672(18) 1.23952(13) 0.02683(9) 0.037(2) Uiso 1 d G . . H152 H 0.7477 1.2465 0.0547 0.045 Uiso 1 calc R . . C153 C 0.6545(2) 1.30965(14) -0.01714(10) 0.046(2) Uiso 1 d G . . H153 H 0.6933 1.3646 -0.0193 0.055 Uiso 1 calc R . . C154 C 0.5653(2) 1.29941(15) -0.05792(10) 0.053(2) Uiso 1 d G . . H154 H 0.5432 1.3473 -0.0880 0.063 Uiso 1 calc R . . C155 C 0.5084(2) 1.21904(16) -0.05471(10) 0.040(2) Uiso 1 d G . . H155 H 0.4474 1.2120 -0.0826 0.048 Uiso 1 calc R . . C156 C 0.54062(17) 1.14893(15) -0.01072(9) 0.0341(19) Uiso 1 d G . . H156 H 0.5017 1.0940 -0.0085 0.041 Uiso 1 calc R . . C201 C 0.76497(19) 0.67811(13) 0.02159(8) 0.0347(19) Uiso 1 d G . . C202 C 0.6791(2) 0.65503(14) -0.01968(9) 0.040(2) Uiso 1 d G . . H202 H 0.6200 0.6804 -0.0147 0.048 Uiso 1 calc R . . C203 C 0.6796(2) 0.59477(15) -0.06826(9) 0.052(2) Uiso 1 d G . . H203 H 0.6209 0.5790 -0.0965 0.062 Uiso 1 calc R . . C204 C 0.7660(2) 0.55760(16) -0.07558(9) 0.054(2) Uiso 1 d G . . H204 H 0.7664 0.5164 -0.1088 0.065 Uiso 1 calc R . . C205 C 0.8519(2) 0.58070(15) -0.03431(9) 0.047(2) Uiso 1 d G . . H205 H 0.9110 0.5553 -0.0393 0.056 Uiso 1 calc R . . C206 C 0.8514(2) 0.64094(14) 0.01427(9) 0.043(2) Uiso 1 d G . . H206 H 0.9101 0.6567 0.0425 0.052 Uiso 1 calc R . . C1S C 0.5628(12) 0.9226(10) 0.2191(9) 0.162(8) Uani 1 d . . . H1S1 H 0.5018 0.9113 0.1883 0.194 Uiso 1 calc R . . H1S2 H 0.6063 0.9598 0.2000 0.194 Uiso 1 calc R . . Cl1S Cl 0.5399(3) 0.9898(3) 0.27932(18) 0.1301(17) Uani 1 d . . . Cl2S Cl 0.6156(3) 0.8118(3) 0.2447(2) 0.1364(17) Uani 1 d . . . 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 Ni 0.0296(8) 0.0252(6) 0.0245(7) 0.0008(5) 0.0049(6) 0.0008(5) N21 0.032(4) 0.029(3) 0.027(4) 0.001(3) 0.010(3) 0.003(3) N22 0.033(4) 0.033(3) 0.020(3) -0.002(3) 0.005(3) 0.000(3) N23 0.025(4) 0.028(3) 0.023(3) -0.002(3) 0.008(3) -0.003(3) N24 0.021(4) 0.033(3) 0.026(4) -0.004(3) 0.005(3) -0.003(3) C1 0.025(5) 0.024(4) 0.034(5) -0.007(3) 0.005(4) 0.006(3) C2 0.018(4) 0.034(4) 0.036(5) -0.006(4) 0.009(4) 0.000(3) C3 0.039(5) 0.022(4) 0.036(5) 0.004(3) 0.004(4) 0.004(3) C4 0.031(5) 0.029(4) 0.027(5) 0.007(3) 0.010(4) 0.007(3) C5 0.025(5) 0.033(4) 0.034(5) 0.007(4) 0.013(4) 0.008(3) C6 0.025(5) 0.029(4) 0.030(5) 0.000(3) 0.018(4) -0.003(3) C7 0.028(5) 0.033(4) 0.020(4) 0.005(3) 0.011(4) 0.005(3) C8 0.023(5) 0.027(4) 0.030(5) 0.003(3) 0.009(4) 0.004(3) C9 0.032(5) 0.031(4) 0.024(4) 0.004(3) 0.014(4) -0.003(3) C10 0.030(5) 0.024(4) 0.024(4) 0.004(3) 0.013(4) 0.000(3) C11 0.033(5) 0.021(4) 0.027(4) -0.003(3) 0.007(4) -0.001(3) C12 0.031(5) 0.028(4) 0.029(5) 0.006(3) 0.007(4) 0.003(3) C13 0.038(5) 0.028(4) 0.033(5) 0.002(3) 0.010(4) 0.000(3) C14 0.035(5) 0.024(4) 0.023(4) 0.003(3) 0.009(4) 0.001(3) C15 0.028(4) 0.029(4) 0.021(4) 0.003(3) 0.003(3) -0.001(3) C16 0.029(5) 0.022(4) 0.026(4) 0.001(3) 0.005(4) -0.003(3) C17 0.030(5) 0.030(4) 0.021(4) -0.002(3) -0.001(4) -0.005(3) C18 0.029(5) 0.037(4) 0.026(5) -0.006(3) 0.004(4) -0.002(3) C19 0.019(4) 0.038(4) 0.029(5) -0.002(4) 0.001(4) -0.003(3) C20 0.027(5) 0.028(4) 0.033(5) -0.005(3) 0.013(4) 0.000(3) C21 0.044(6) 0.028(4) 0.038(5) 0.002(4) 0.013(4) 0.001(4) C22 0.055(7) 0.046(5) 0.066(7) -0.017(5) 0.016(5) -0.015(5) C31 0.054(6) 0.032(4) 0.041(5) 0.005(4) 0.004(5) -0.001(4) C32 0.076(8) 0.052(6) 0.068(7) 0.002(5) 0.030(6) -0.015(5) C71 0.032(6) 0.030(5) 0.048(7) -0.011(5) 0.003(6) 0.004(4) O1 0.048(5) 0.041(4) 0.046(5) 0.003(4) 0.000(4) -0.002(3) C121 0.037(5) 0.039(4) 0.038(5) -0.007(4) 0.014(4) 0.010(4) C122 0.045(6) 0.070(6) 0.057(7) -0.023(5) 0.015(5) -0.001(5) C131 0.044(6) 0.041(5) 0.030(5) 0.002(4) 0.005(4) 0.009(4) C132 0.035(5) 0.056(5) 0.049(6) 0.009(4) 0.004(5) 0.011(4) C1S 0.137(15) 0.101(11) 0.29(3) 0.066(14) 0.146(17) 0.027(10) Cl1S 0.153(4) 0.108(3) 0.100(3) 0.016(2) -0.024(3) 0.030(3) Cl2S 0.079(3) 0.135(3) 0.220(5) 0.045(3) 0.085(3) 0.017(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 Ni N22 1.913(6) . ? Ni N24 1.913(6) . ? Ni N21 1.938(6) . ? Ni N23 1.939(6) . ? N21 C1 1.381(9) . ? N21 C4 1.398(9) . ? N22 C6 1.383(9) . ? N22 C9 1.385(9) . ? N23 C11 1.384(9) . ? N23 C14 1.400(9) . ? N24 C16 1.381(9) . ? N24 C19 1.386(9) . ? C1 C20 1.396(10) . ? C1 C2 1.446(10) . ? C2 C3 1.364(10) . ? C2 C21 1.521(10) . ? C3 C4 1.452(10) . ? C3 C31 1.511(10) . ? C4 C5 1.381(10) . ? C5 C6 1.395(10) . ? C5 C51 1.523(7) . ? C6 C7 1.446(10) . ? C7 C8 1.360(9) . ? C7 C71 1.472(12) . ? C8 C9 1.436(10) . ? C9 C10 1.385(10) . ? C10 C11 1.389(10) . ? C10 C101 1.516(7) . ? C11 C12 1.466(10) . ? C12 C13 1.348(10) . ? C12 C121 1.506(10) . ? C13 C14 1.457(10) . ? C13 C131 1.522(11) . ? C14 C15 1.389(10) . ? C15 C16 1.385(10) . ? C15 C151 1.517(7) . ? C16 C17 1.461(10) . ? C17 C71' 1.32(3) . ? C17 C18 1.346(10) . ? C18 C19 1.448(10) . ? C19 C20 1.389(10) . ? C20 C201 1.513(7) . ? C21 C22 1.516(11) . ? C31 C32 1.527(13) . ? C71 O1 1.216(11) . ? C71' O1' 1.30(4) . ? C121 C122 1.526(12) . ? C131 C132 1.506(11) . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C52 C53 1.3900 . ? C53 C54 1.3900 . ? C54 C55 1.3900 . ? C55 C56 1.3900 . ? C101 C102 1.3899 . ? C101 C106 1.3901 . ? C102 C103 1.3900 . ? C103 C104 1.3903 . ? C104 C105 1.3901 . ? C105 C106 1.3900 . ? C151 C156 1.3899 . ? C151 C152 1.3903 . ? C152 C153 1.3899 . ? C153 C154 1.3900 . ? C154 C155 1.3901 . ? C155 C156 1.3901 . ? C201 C206 1.3899 . ? C201 C202 1.3902 . ? C202 C203 1.3902 . ? C203 C204 1.3902 . ? C204 C205 1.3901 . ? C205 C206 1.3899 . ? C1S Cl2S 1.742(14) . ? C1S Cl1S 1.760(18) . ? 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 N22 Ni N24 170.8(3) . . ? N22 Ni N21 90.9(2) . . ? N24 Ni N21 90.4(3) . . ? N22 Ni N23 89.6(2) . . ? N24 Ni N23 90.3(2) . . ? N21 Ni N23 171.8(3) . . ? C1 N21 C4 105.3(6) . . ? C1 N21 Ni 128.5(5) . . ? C4 N21 Ni 124.9(5) . . ? C6 N22 C9 105.7(6) . . ? C6 N22 Ni 127.1(5) . . ? C9 N22 Ni 125.8(5) . . ? C11 N23 C14 104.5(5) . . ? C11 N23 Ni 128.4(5) . . ? C14 N23 Ni 126.2(4) . . ? C16 N24 C19 106.0(6) . . ? C16 N24 Ni 127.0(5) . . ? C19 N24 Ni 124.9(5) . . ? N21 C1 C20 122.2(6) . . ? N21 C1 C2 110.6(6) . . ? C20 C1 C2 127.1(6) . . ? C3 C2 C1 107.0(6) . . ? C3 C2 C21 124.2(7) . . ? C1 C2 C21 128.3(7) . . ? C2 C3 C4 106.8(6) . . ? C2 C3 C31 125.6(7) . . ? C4 C3 C31 127.1(7) . . ? C5 C4 N21 122.7(6) . . ? C5 C4 C3 126.4(6) . . ? N21 C4 C3 109.8(6) . . ? C4 C5 C6 122.9(7) . . ? C4 C5 C51 122.3(6) . . ? C6 C5 C51 114.7(6) . . ? N22 C6 C5 123.3(7) . . ? N22 C6 C7 109.8(6) . . ? C5 C6 C7 126.8(7) . . ? C8 C7 C6 107.1(6) . . ? C8 C7 C71 121.4(7) . . ? C6 C7 C71 131.3(7) . . ? C7 C8 C9 107.1(6) . . ? C10 C9 N22 124.7(7) . . ? C10 C9 C8 124.3(6) . . ? N22 C9 C8 110.1(6) . . ? C9 C10 C11 121.7(6) . . ? C9 C10 C101 117.4(6) . . ? C11 C10 C101 120.8(5) . . ? N23 C11 C10 121.9(6) . . ? N23 C11 C12 110.7(6) . . ? C10 C11 C12 127.1(6) . . ? C13 C12 C11 106.5(6) . . ? C13 C12 C121 126.2(7) . . ? C11 C12 C121 126.9(7) . . ? C12 C13 C14 107.3(6) . . ? C12 C13 C131 126.1(7) . . ? C14 C13 C131 125.2(7) . . ? C15 C14 N23 122.3(6) . . ? C15 C14 C13 126.7(6) . . ? N23 C14 C13 110.0(6) . . ? C16 C15 C14 121.8(6) . . ? C16 C15 C151 117.5(6) . . ? C14 C15 C151 120.1(5) . . ? N24 C16 C15 125.0(7) . . ? N24 C16 C17 110.1(6) . . ? C15 C16 C17 124.9(6) . . ? C71' C17 C18 126.8(16) . . ? C71' C17 C16 126.7(16) . . ? C18 C17 C16 106.0(6) . . ? C17 C18 C19 108.5(7) . . ? N24 C19 C20 125.7(7) . . ? N24 C19 C18 109.1(6) . . ? C20 C19 C18 124.6(7) . . ? C1 C20 C19 121.6(6) . . ? C1 C20 C201 122.2(5) . . ? C19 C20 C201 116.3(6) . . ? C22 C21 C2 113.1(7) . . ? C3 C31 C32 113.7(7) . . ? O1 C71 C7 122.8(8) . . ? O1' C71' C17 128(3) . . ? C12 C121 C122 113.2(7) . . ? C132 C131 C13 111.0(7) . . ? C52 C51 C56 120.0 . . ? C52 C51 C5 121.2(3) . . ? C56 C51 C5 118.3(3) . . ? C51 C52 C53 120.0 . . ? C54 C53 C52 120.0 . . ? C55 C54 C53 120.0 . . ? C54 C55 C56 120.0 . . ? C55 C56 C51 120.0 . . ? C102 C101 C106 120.0 . . ? C102 C101 C10 121.5(3) . . ? C106 C101 C10 118.4(3) . . ? C101 C102 C103 120.0 . . ? C102 C103 C104 120.0 . . ? C105 C104 C103 120.0 . . ? C106 C105 C104 120.0 . . ? C105 C106 C101 120.0 . . ? C156 C151 C152 120.0 . . ? C156 C151 C15 121.9(3) . . ? C152 C151 C15 118.1(3) . . ? C153 C152 C151 120.0 . . ? C152 C153 C154 120.0 . . ? C153 C154 C155 120.0 . . ? C156 C155 C154 120.0 . . ? C151 C156 C155 120.0 . . ? C206 C201 C202 120.0 . . ? C206 C201 C20 119.1(3) . . ? C202 C201 C20 120.8(3) . . ? C203 C202 C201 120.0 . . ? C202 C203 C204 120.0 . . ? C205 C204 C203 120.0 . . ? C206 C205 C204 120.0 . . ? C201 C206 C205 120.0 . . ? Cl2S C1S Cl1S 110.5(11) . . ? _diffrn_measured_fraction_theta_max 0.951 _diffrn_reflns_theta_full 56.35 _diffrn_measured_fraction_theta_full 0.951 _refine_diff_density_max 0.582 _refine_diff_density_min -0.534 _refine_diff_density_rms 0.095 #====END data_ms372 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,7,8,12,13-Hexabromo-17,18-diethyl- 5,10,15,20-tetraphenylporphyrin ; _chemical_name_common ? _chemical_melting_point n/d _chemical_formula_moiety 'C48 H32 Br6 N4.2(C1 H2 Cl2)' _chemical_formula_sum 'C50 H36 Br6 Cl4 N4' _chemical_formula_weight 1314.09 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' 'Br' 'Br' -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 13.299(3) _cell_length_b 17.047(4) _cell_length_c 22.967(5) _cell_angle_alpha 100.051(18) _cell_angle_beta 90.482(19) _cell_angle_gamma 106.561(17) _cell_volume 4905(2) _cell_formula_units_Z 4 _cell_measurement_temperature 129(2) _cell_measurement_reflns_used 26 _cell_measurement_theta_min 41 _cell_measurement_theta_max 48 _exptl_crystal_description parallelepiped _exptl_crystal_colour 'metallic lustrous green' _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas n/d _exptl_crystal_density_diffrn 1.780 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2568 _exptl_absorpt_coefficient_mu 8.235 _exptl_absorpt_correction_type 'empirical, XABS2' _exptl_absorpt_correction_T_min 0.1373 _exptl_absorpt_correction_T_max 0.4931 _exptl_absorpt_process_details '(Parkin et al., 1995)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 129(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotaiting anode' _diffrn_radiation_monochromator Ni-filter _diffrn_measurement_device_type 'Siemens P4/RA' _diffrn_measurement_method '2theta-theta' _diffrn_detector_area_resol_mean n/a _diffrn_standards_number 2 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% <1 _diffrn_reflns_number 13486 _diffrn_reflns_av_R_equivalents 0.0471 _diffrn_reflns_av_sigmaI/netI 0.0729 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 56.07 _reflns_number_total 12817 _reflns_number_gt 9332 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3' _computing_cell_refinement 'Siemens P3' _computing_data_reduction 'XDISK, Shelxtl-Plus (Siemens, 1995)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus (Siemens, 1995)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Two of the four methylene chlorides of solvation exhibited disorder. Cl6S was refined as disordered over two split positions with occupancies of 0.75 (Cl6S) and 0.25 (Cl6'), respectively. Similarly, Cl8S was refined as disordered over two positions with occupancies of 0.8 (Cl8S) and 0.2 (Cl8'), respectively. One of the two porphyrin macrocycles in the asymmetric unit showed disorder of beta-bromo and beta-ethyl substituents. This disorder was modeled by employing two different sets of substiuents: Br37, Br38, C271, C272, C281, and C282 were refined with occupancies of 0.2, each while Br27, Br28, C371, C372, C381, and C382 were refined with occupancies of 0.8 each. This model employed severe constrained on the disordered ethyl groups which were refined with isotropic thermal parameters of 0.03 for the methylene groups and 0.04 for the methyl groups. The residual electron density was located in the disordered substituent region. Due to this disorder and the contraints imposed on molecule 2 only molecule 1 (containing N21) should be used for geometrical analyses. ; _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^)+(0.0756P)^2^+27.0970P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef n/d _refine_ls_number_reflns 12817 _refine_ls_number_parameters 1143 _refine_ls_number_restraints 202 _refine_ls_R_factor_all 0.0913 _refine_ls_R_factor_gt 0.0602 _refine_ls_wR_factor_ref 0.1557 _refine_ls_wR_factor_gt 0.1386 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.018 _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_multiplicit _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N21 N -1.0822(5) 0.0079(4) -0.1280(3) 0.0176(18) Uani 1 1 d D . . H21 H -1.0475 0.0572 -0.1351 0.021 Uiso 0.50 1 calc PR . . N22 N -0.9227(5) 0.0478(4) -0.2133(3) 0.0181(18) Uani 1 1 d D . . H22 H -0.9251 0.0614 -0.1747 0.022 Uiso 0.50 1 calc PR . . N23 N -0.8233(5) 0.2000(4) -0.1314(3) 0.0160(17) Uani 1 1 d D . . H23 H -0.8897 0.1723 -0.1411 0.019 Uiso 0.50 1 calc PR . . N24 N -0.9958(6) 0.1684(4) -0.0546(3) 0.0187(18) Uani 1 1 d D . . H24 H -0.9656 0.1363 -0.0780 0.022 Uiso 0.50 1 calc PR . . C1 C -1.1282(7) -0.0081(5) -0.0770(4) 0.016(2) Uani 1 1 d D . . C2 C -1.1692(7) -0.0984(5) -0.0809(4) 0.019(2) Uani 1 1 d D . . C3 C -1.1526(8) -0.1339(6) -0.1362(4) 0.028(2) Uani 1 1 d D . . C4 C -1.0993(7) -0.0661(5) -0.1661(4) 0.020(2) Uani 1 1 d D . . C5 C -1.0777(7) -0.0738(5) -0.2265(4) 0.017(2) Uani 1 1 d D . . C6 C -0.9988(7) -0.0151(5) -0.2492(4) 0.021(2) Uani 1 1 d D . . C7 C -0.9716(7) -0.0086(6) -0.3084(4) 0.017(2) Uani 1 1 d D . . C8 C -0.8768(7) 0.0511(6) -0.3066(4) 0.022(2) Uani 1 1 d D . . C9 C -0.8426(7) 0.0869(5) -0.2455(4) 0.022(2) Uani 1 1 d D . . C10 C -0.7484(7) 0.1448(5) -0.2208(4) 0.019(2) Uani 1 1 d D . . C11 C -0.7386(7) 0.1889(6) -0.1620(4) 0.024(2) Uani 1 1 d D . . C12 C -0.6425(7) 0.2395(6) -0.1269(4) 0.023(2) Uani 1 1 d D . . C13 C -0.6709(7) 0.2855(6) -0.0796(4) 0.022(2) Uani 1 1 d D . . C14 C -0.7863(6) 0.2609(5) -0.0837(4) 0.019(2) Uani 1 1 d D . . C15 C -0.8527(7) 0.2969(5) -0.0472(4) 0.017(2) Uani 1 1 d D . . C16 C -0.9568(7) 0.2538(5) -0.0398(4) 0.015(2) Uani 1 1 d D . . C17 C -1.0381(7) 0.2820(5) -0.0083(4) 0.019(2) Uani 1 1 d D . . C18 C -1.1157(7) 0.2128(6) 0.0014(4) 0.023(2) Uani 1 1 d D . . C19 C -1.0883(7) 0.1399(5) -0.0280(4) 0.024(2) Uani 1 1 d D . . C20 C -1.1409(7) 0.0550(5) -0.0309(4) 0.019(2) Uani 1 1 d D . . C51 C -1.1336(6) -0.1526(5) -0.2669(4) 0.020(2) Uani 1 1 d D . . C52 C -1.2424(6) -0.1767(5) -0.2760(4) 0.029(3) Uani 1 1 d D . . H52 H -1.2813 -0.1418 -0.2569 0.035 Uiso 1 1 calc R . . C53 C -1.2949(8) -0.2515(5) -0.3127(4) 0.038(3) Uani 1 1 d D . . H53 H -1.3694 -0.2682 -0.3180 0.045 Uiso 1 1 calc R . . C54 C -1.2383(8) -0.3015(6) -0.3414(5) 0.041(3) Uani 1 1 d D . . H54 H -1.2739 -0.3523 -0.3670 0.049 Uiso 1 1 calc R . . C55 C -1.1305(8) -0.2782(5) -0.3331(4) 0.037(3) Uani 1 1 d D . . H55 H -1.0918 -0.3129 -0.3527 0.044 Uiso 1 1 calc R . . C56 C -1.0785(7) -0.2039(5) -0.2960(4) 0.031(3) Uani 1 1 d D . . H56 H -1.0040 -0.1880 -0.2904 0.038 Uiso 1 1 calc R . . C101 C -0.6565(7) 0.1616(5) -0.2577(4) 0.028(2) Uani 1 1 d D . . C102 C -0.6058(7) 0.1018(6) -0.2758(5) 0.041(3) Uani 1 1 d D . . H102 H -0.6339 0.0475 -0.2671 0.049 Uiso 1 1 calc R . . C103 C -0.5149(8) 0.1196(9) -0.3062(5) 0.065(5) Uani 1 1 d D . . H103 H -0.4787 0.0789 -0.3164 0.078 Uiso 1 1 calc R . . C104 C -0.4773(9) 0.1973(9) -0.3217(5) 0.067(5) Uani 1 1 d D . . H104 H -0.4160 0.2097 -0.3434 0.081 Uiso 1 1 calc R . . C105 C -0.5290(9) 0.2568(9) -0.3057(5) 0.059(4) Uani 1 1 d D . . H105 H -0.5041 0.3097 -0.3169 0.071 Uiso 1 1 calc R . . C106 C -0.6170(8) 0.2391(6) -0.2732(4) 0.037(3) Uani 1 1 d D . . H106 H -0.6510 0.2808 -0.2613 0.044 Uiso 1 1 calc R . . C151 C -0.8059(7) 0.3824(5) -0.0111(3) 0.023(2) Uani 1 1 d D . . C152 C -0.7594(7) 0.4486(5) -0.0392(4) 0.026(2) Uani 1 1 d D . . H152 H -0.7615 0.4409 -0.0812 0.031 Uiso 1 1 calc R . . C153 C -0.7099(7) 0.5259(5) -0.0051(3) 0.025(2) Uani 1 1 d D . . H153 H -0.6770 0.5712 -0.0239 0.030 Uiso 1 1 calc R . . C154 C -0.7079(8) 0.5380(5) 0.0558(4) 0.029(2) Uani 1 1 d D . . H154 H -0.6746 0.5915 0.0786 0.035 Uiso 1 1 calc R . . C155 C -0.7544(7) 0.4722(5) 0.0841(4) 0.022(2) Uani 1 1 d D . . H155 H -0.7518 0.4802 0.1261 0.027 Uiso 1 1 calc R . . C156 C -0.8047(7) 0.3948(5) 0.0505(3) 0.021(2) Uani 1 1 d D . . H156 H -0.8386 0.3499 0.0695 0.025 Uiso 1 1 calc R . . C201 C -1.2149(6) 0.0322(6) 0.0165(4) 0.026(2) Uani 1 1 d D . . C202 C -1.3225(6) -0.0009(6) 0.0035(4) 0.029(2) Uani 1 1 d D . . H202 H -1.3507 -0.0081 -0.0359 0.035 Uiso 1 1 calc R . . C203 C -1.3890(8) -0.0235(7) 0.0480(4) 0.040(3) Uani 1 1 d D . . H203 H -1.4625 -0.0475 0.0390 0.048 Uiso 1 1 calc R . . C204 C -1.3470(8) -0.0107(7) 0.1058(4) 0.042(3) Uani 1 1 d D . . H204 H -1.3924 -0.0255 0.1364 0.050 Uiso 1 1 calc R . . C205 C -1.2406(7) 0.0232(6) 0.1192(4) 0.037(3) Uani 1 1 d D . . H205 H -1.2127 0.0321 0.1588 0.044 Uiso 1 1 calc R . . C206 C -1.1746(7) 0.0443(6) 0.0747(3) 0.030(3) Uani 1 1 d D . . H206 H -1.1011 0.0672 0.0838 0.036 Uiso 1 1 calc R . . N25 N -0.6643(6) -0.3473(4) -0.3637(3) 0.0165(17) Uani 1 1 d D . . H25 H -0.7211 -0.3322 -0.3546 0.020 Uiso 0.50 1 calc PR . . N26 N -0.8495(5) -0.4422(5) -0.3117(3) 0.0178(18) Uani 1 1 d D B . H26 H -0.8410 -0.4391 -0.3492 0.021 Uiso 0.50 1 calc PR . . N27 N -0.9824(5) -0.4064(4) -0.3998(3) 0.0137(17) Uani 1 1 d D B . H27 H -0.9190 -0.3781 -0.3842 0.016 Uiso 0.50 1 calc PR . . N28 N -0.7999(5) -0.3001(4) -0.4447(3) 0.0153(17) Uani 1 1 d D A . H28 H -0.8093 -0.3417 -0.4254 0.018 Uiso 0.50 1 calc PR . . C21 C -0.5988(6) -0.3228(5) -0.4062(4) 0.017(2) Uani 1 1 d D . . C22 C -0.5211(6) -0.3687(5) -0.4121(4) 0.0128(19) Uiso 1 1 d D . . C23 C -0.5362(7) -0.4154(5) -0.3700(4) 0.016(2) Uiso 1 1 d D . . C24 C -0.6254(7) -0.4002(5) -0.3373(4) 0.015(2) Uani 1 1 d D . . C25 C -0.6644(6) -0.4276(5) -0.2856(4) 0.013(2) Uani 1 1 d D . . C26 C -0.7675(6) -0.4321(5) -0.2700(4) 0.016(2) Uani 1 1 d D B . C27 C -0.8146(7) -0.4338(6) -0.2148(4) 0.020(2) Uani 1 1 d D . . C28 C -0.9205(7) -0.4499(6) -0.2242(4) 0.020(2) Uani 1 1 d D B . C29 C -0.9450(6) -0.4577(5) -0.2867(4) 0.014(2) Uani 1 1 d D . . C30 C -1.0422(6) -0.4834(5) -0.3188(4) 0.018(2) Uani 1 1 d D B . C31 C -1.0537(7) -0.4671(5) -0.3765(4) 0.015(2) Uani 1 1 d D . . C32 C -1.1438(7) -0.5035(5) -0.4187(4) 0.014(2) Uani 1 1 d D B . C33 C -1.1283(7) -0.4610(5) -0.4643(4) 0.016(2) Uani 1 1 d D . . C34 C -1.0260(6) -0.3979(5) -0.4506(3) 0.0124(19) Uani 1 1 d D B . C35 C -0.9839(6) -0.3325(5) -0.4819(4) 0.017(2) Uani 1 1 d D . . C36 C -0.8790(6) -0.2805(5) -0.4727(4) 0.016(2) Uani 1 1 d D A . C37 C -0.8318(7) -0.2020(5) -0.4909(4) 0.020(2) Uani 1 1 d D . . C38 C -0.7250(6) -0.1802(5) -0.4775(4) 0.016(2) Uiso 1 1 d D A . C39 C -0.7029(6) -0.2447(5) -0.4513(4) 0.015(2) Uani 1 1 d D . . C40 C -0.6081(6) -0.2607(5) -0.4383(4) 0.019(2) Uani 1 1 d D A . C251 C -0.5996(6) -0.4527(5) -0.2425(4) 0.019(2) Uani 1 1 d D . . C252 C -0.6337(7) -0.5302(5) -0.2262(4) 0.023(2) Uani 1 1 d D . . H252 H -0.6923 -0.5714 -0.2475 0.027 Uiso 1 1 calc R . . C253 C -0.5836(7) -0.5485(6) -0.1792(4) 0.029(3) Uani 1 1 d D . . H253 H -0.6082 -0.6015 -0.1680 0.035 Uiso 1 1 calc R . . C254 C -0.4972(7) -0.4883(5) -0.1488(4) 0.031(3) Uani 1 1 d D . . H254 H -0.4643 -0.4995 -0.1156 0.037 Uiso 1 1 calc R . . C255 C -0.4582(7) -0.4120(6) -0.1662(4) 0.029(3) Uani 1 1 d D . . H255 H -0.3979 -0.3715 -0.1458 0.035 Uiso 1 1 calc R . . C256 C -0.5087(6) -0.3956(6) -0.2139(4) 0.024(2) Uani 1 1 d D . . H256 H -0.4806 -0.3444 -0.2272 0.028 Uiso 1 1 calc R . . C301 C -1.1356(6) -0.5290(5) -0.2906(4) 0.019(2) Uani 1 1 d D . . C302 C -1.1377(7) -0.6041(5) -0.2743(4) 0.027(2) Uani 1 1 d D B . H302 H -1.0806 -0.6265 -0.2823 0.033 Uiso 1 1 calc R . . C303 C -1.2230(7) -0.6465(6) -0.2464(5) 0.036(3) Uani 1 1 d D . . H303 H -1.2247 -0.6982 -0.2357 0.043 Uiso 1 1 calc R B . C304 C -1.3054(7) -0.6130(6) -0.2343(4) 0.033(3) Uani 1 1 d D B . H304 H -1.3640 -0.6424 -0.2155 0.039 Uiso 1 1 calc R . . C305 C -1.3039(7) -0.5374(6) -0.2491(4) 0.028(2) Uani 1 1 d D . . H305 H -1.3600 -0.5141 -0.2398 0.033 Uiso 1 1 calc R B . C306 C -1.2189(6) -0.4964(6) -0.2779(4) 0.021(2) Uani 1 1 d D B . H306 H -1.2179 -0.4451 -0.2891 0.026 Uiso 1 1 calc R . . C351 C -1.0545(6) -0.3192(5) -0.5281(3) 0.0106(19) Uani 1 1 d D B . C352 C -1.1395(6) -0.2901(6) -0.5123(4) 0.023(2) Uani 1 1 d D . . H352 H -1.1507 -0.2743 -0.4717 0.028 Uiso 1 1 calc R B . C353 C -1.2084(7) -0.2842(6) -0.5560(3) 0.028(2) Uani 1 1 d D B . H353 H -1.2665 -0.2641 -0.5452 0.034 Uiso 1 1 calc R . . C354 C -1.1926(7) -0.3077(6) -0.6154(4) 0.032(3) Uani 1 1 d D . . H354 H -1.2401 -0.3039 -0.6452 0.038 Uiso 1 1 calc R B . C355 C -1.1078(7) -0.3366(6) -0.6312(4) 0.028(2) Uani 1 1 d D B . H355 H -1.0973 -0.3535 -0.6718 0.034 Uiso 1 1 calc R . . C356 C -1.0378(7) -0.3409(6) -0.5872(3) 0.024(2) Uani 1 1 d D . . H356 H -0.9780 -0.3590 -0.5980 0.029 Uiso 1 1 calc R B . C401 C -0.5073(6) -0.2086(5) -0.4574(3) 0.019(2) Uani 1 1 d D . . C402 C -0.4293(6) -0.1636(5) -0.4137(4) 0.026(2) Uani 1 1 d D A . H402 H -0.4404 -0.1671 -0.3733 0.031 Uiso 1 1 calc R . . C403 C -0.3354(6) -0.1138(6) -0.4293(4) 0.028(2) Uani 1 1 d D . . H403 H -0.2825 -0.0824 -0.3994 0.034 Uiso 1 1 calc R A . C404 C -0.3181(7) -0.1095(6) -0.4884(4) 0.030(3) Uani 1 1 d D A . H404 H -0.2536 -0.0751 -0.4988 0.036 Uiso 1 1 calc R . . C405 C -0.3949(6) -0.1554(5) -0.5320(4) 0.026(2) Uani 1 1 d D . . H405 H -0.3831 -0.1531 -0.5725 0.031 Uiso 1 1 calc R A . C406 C -0.48855(4) -0.20447(3) -0.51627(2) 0.019(2) Uani 1 1 d D A . H406 H -0.5412 -0.2360 -0.5463 0.022 Uiso 1 1 calc R . . Br2 Br -1.22459(4) -0.15925(3) -0.02248(2) 0.0301(3) Uani 1 1 d R . . Br3 Br -1.17448(4) -0.24832(3) -0.16050(2) 0.0419(3) Uani 1 1 d R . . Br7 Br -1.05162(4) -0.06283(3) -0.37866(2) 0.0308(3) Uani 1 1 d R . . Br8 Br -0.81633(4) 0.08816(3) -0.37320(2) 0.0341(3) Uani 1 1 d R . . Br12 Br -0.50455(4) 0.23514(3) -0.13875(2) 0.0296(3) Uani 1 1 d R . . Br13 Br -0.57671(4) 0.35408(3) -0.01783(2) 0.0292(3) Uani 1 1 d R . . C171 C -1.04623(4) 0.37128(3) 0.00097(2) 0.022(2) Uani 1 1 d R . . H17A H -1.1080 0.3747 0.0240 0.026 Uiso 1 1 calc R . . H17B H -0.9826 0.4097 0.0240 0.026 Uiso 1 1 calc R . . C172 C -1.0567(9) 0.3968(7) -0.0563(5) 0.038(3) Uani 1 1 d . . . H17C H -1.0616 0.4539 -0.0494 0.056 Uiso 1 1 calc R . . H17D H -1.1203 0.3593 -0.0788 0.056 Uiso 1 1 calc R . . H17E H -0.9951 0.3941 -0.0789 0.056 Uiso 1 1 calc R . . C181 C -1.2183(8) 0.2166(6) 0.0300(5) 0.029(3) Uani 1 1 d . . . H18A H -1.2429 0.1682 0.0501 0.035 Uiso 1 1 calc R . . H18B H -1.2029 0.2675 0.0609 0.035 Uiso 1 1 calc R . . C182 C -1.3028(10) 0.2169(9) -0.0095(6) 0.056(4) Uani 1 1 d . . . H18C H -1.3647 0.2188 0.0129 0.085 Uiso 1 1 calc R . . H18D H -1.3203 0.1662 -0.0399 0.085 Uiso 1 1 calc R . . H18E H -1.2810 0.2658 -0.0285 0.085 Uiso 1 1 calc R . . Br22 Br -0.42892(8) -0.37509(6) -0.47240(5) 0.0255(3) Uani 1 1 d . . . Br23 Br -0.46922(8) -0.49616(6) -0.36115(5) 0.0262(3) Uani 1 1 d . . . Br32 Br -1.25670(8) -0.59955(6) -0.41744(4) 0.0225(2) Uani 1 1 d . . . Br33 Br -1.22125(8) -0.49227(6) -0.53150(4) 0.0207(2) Uani 1 1 d . B . Br37 Br -0.9011(6) -0.1402(5) -0.5227(4) 0.0376(17) Uani 0.20 1 d P A 1 Br38 Br -0.6371(7) -0.0796(4) -0.4827(4) 0.0369(16) Uani 0.20 1 d P A 1 C271 C -0.751(5) -0.408(4) -0.1566(17) 0.030 Uiso 0.20 1 d PD B 1 H27A H -0.7064 -0.4449 -0.1555 0.036 Uiso 0.20 1 calc PR B 1 H27B H -0.8001 -0.4158 -0.1244 0.036 Uiso 0.20 1 calc PR B 1 C272 C -0.683(4) -0.319(3) -0.144(3) 0.040 Uiso 0.20 1 d PD B 1 H27C H -0.6446 -0.3076 -0.1057 0.060 Uiso 0.20 1 calc PR B 1 H27D H -0.7261 -0.2816 -0.1445 0.060 Uiso 0.20 1 calc PR B 1 H27E H -0.6321 -0.3108 -0.1753 0.060 Uiso 0.20 1 calc PR B 1 C281 C -1.000(4) -0.457(3) -0.178(2) 0.030 Uiso 0.20 1 d PD B 1 H28A H -1.0662 -0.4994 -0.1940 0.036 Uiso 0.20 1 calc PR B 1 H28B H -0.9731 -0.4731 -0.1431 0.036 Uiso 0.20 1 calc PR B 1 C282 C -1.020(5) -0.374(3) -0.160(3) 0.040 Uiso 0.20 1 d PD B 1 H28C H -1.0722 -0.3773 -0.1302 0.060 Uiso 0.20 1 calc PR B 1 H28D H -1.0458 -0.3574 -0.1949 0.060 Uiso 0.20 1 calc PR B 1 H28E H -0.9540 -0.3317 -0.1436 0.060 Uiso 0.20 1 calc PR B 1 Br27 Br -0.74731(12) -0.40607(9) -0.13980(5) 0.0206(3) Uani 0.80 1 d P B 2 Br28 Br -1.01467(12) -0.44473(9) -0.16389(6) 0.0256(3) Uani 0.80 1 d P B 2 C371 C -0.8808(19) -0.1461(14) -0.5173(6) 0.030 Uiso 0.80 1 d PD A 2 H37A H -0.9571 -0.1632 -0.5115 0.036 Uiso 0.80 1 calc PR A 2 H37B H -0.8513 -0.0885 -0.4950 0.036 Uiso 0.80 1 calc PR A 2 C372 C -0.8663(12) -0.1449(9) -0.5819(5) 0.040 Uiso 0.80 1 d PD A 2 H37C H -0.9016 -0.1071 -0.5947 0.060 Uiso 0.80 1 calc PR A 2 H37D H -0.8968 -0.2012 -0.6049 0.060 Uiso 0.80 1 calc PR A 2 H37E H -0.7912 -0.1257 -0.5882 0.060 Uiso 0.80 1 calc PR A 2 C381 C -0.650(2) -0.0966(9) -0.4802(6) 0.030 Uiso 0.80 1 d PD A 2 H38A H -0.6864 -0.0664 -0.5021 0.036 Uiso 0.80 1 calc PR A 2 H38B H -0.5904 -0.1052 -0.5033 0.036 Uiso 0.80 1 calc PR A 2 C382 C -0.6072(11) -0.0426(9) -0.4215(6) 0.040 Uiso 0.80 1 d PD A 2 H38C H -0.5593 0.0104 -0.4278 0.060 Uiso 0.80 1 calc PR A 2 H38D H -0.5690 -0.0709 -0.3997 0.060 Uiso 0.80 1 calc PR A 2 H38E H -0.6653 -0.0319 -0.3985 0.060 Uiso 0.80 1 calc PR A 2 C1S C 0.8112(9) 0.2327(5) 0.2965(4) 0.037(3) Uani 1 1 d D . . H1S1 H 0.8727 0.2704 0.3217 0.044 Uiso 1 1 calc R . . H1S2 H 0.7504 0.2545 0.3052 0.044 Uiso 1 1 calc R . . Cl1S Cl 0.8377(3) 0.2314(2) 0.22111(14) 0.0557(9) Uani 1 1 d D . . Cl2S Cl 0.7834(3) 0.13200(19) 0.31372(17) 0.0587(9) Uani 1 1 d D . . C2S C 0.9961(8) 0.7400(5) 0.1961(4) 0.040(3) Uani 1 1 d D . . H2S1 H 1.0564 0.7239 0.1782 0.048 Uiso 1 1 calc R . . H2S2 H 0.9728 0.7733 0.1705 0.048 Uiso 1 1 calc R . . Cl3S Cl 1.0374(3) 0.80159(19) 0.26642(13) 0.0474(8) Uani 1 1 d D . . Cl4S Cl 0.8931(3) 0.64971(19) 0.19867(13) 0.0481(8) Uani 1 1 d D . . C3S C -0.2523(13) 0.0612(8) -0.2080(4) 0.131(9) Uani 1 1 d D . . H3S1 H -0.2848 0.0150 -0.1871 0.157 Uiso 1 1 calc R C 1 H3S2 H -0.1753 0.0708 -0.2045 0.157 Uiso 1 1 calc R C 1 Cl5S Cl -0.2946(5) 0.0272(4) -0.2847(3) 0.132(2) Uani 1 1 d D D . Cl6S Cl -0.2793(6) 0.1508(5) -0.1705(3) 0.118(3) Uani 0.75 1 d PD D 1 Cl6' Cl -0.3508(10) 0.0031(9) -0.1714(8) 0.073(5) Uani 0.25 1 d PD D 2 C4S C -0.5660(9) -0.1828(11) -0.1695(5) 0.091(6) Uani 1 1 d D . . H4S1 H -0.6022 -0.1418 -0.1520 0.109 Uiso 1 1 calc R E 1 H4S2 H -0.6174 -0.2387 -0.1736 0.109 Uiso 1 1 calc R E 1 Cl7S Cl -0.5338(4) -0.1652(5) -0.2407(3) 0.142(3) Uani 1 1 d D D . Cl8S Cl -0.4643(5) -0.1777(4) -0.1190(3) 0.0862(17) Uani 0.80 1 d PD F 1 Cl8' Cl -0.4317(11) -0.130(2) -0.1482(9) 0.111(12) Uani 0.20 1 d PD D 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 N21 0.008(4) 0.018(4) 0.029(5) 0.007(4) 0.007(3) 0.006(3) N22 0.015(4) 0.012(4) 0.027(5) 0.003(3) -0.001(4) 0.002(3) N23 0.010(4) 0.015(4) 0.022(4) 0.003(3) 0.004(3) 0.003(3) N24 0.017(4) 0.023(5) 0.019(4) 0.008(4) 0.004(3) 0.008(4) C1 0.019(5) 0.017(5) 0.017(5) 0.009(4) 0.000(4) 0.009(4) C2 0.016(5) 0.015(5) 0.028(6) 0.012(4) -0.003(4) 0.000(4) C3 0.030(6) 0.016(5) 0.029(6) 0.004(5) -0.003(5) -0.004(5) C4 0.017(5) 0.009(5) 0.036(6) 0.003(4) 0.004(4) 0.005(4) C5 0.020(5) 0.008(5) 0.027(6) 0.005(4) -0.002(4) 0.008(4) C6 0.016(5) 0.020(5) 0.029(6) 0.003(4) 0.002(4) 0.008(4) C7 0.011(5) 0.020(5) 0.017(5) -0.001(4) 0.004(4) 0.003(4) C8 0.020(5) 0.022(5) 0.025(6) 0.010(4) 0.008(4) 0.005(4) C9 0.020(5) 0.014(5) 0.029(6) 0.000(4) 0.006(4) 0.005(4) C10 0.022(5) 0.012(5) 0.026(5) 0.008(4) -0.002(4) 0.007(4) C11 0.028(6) 0.022(5) 0.026(6) 0.014(5) 0.002(5) 0.009(5) C12 0.021(5) 0.022(5) 0.027(6) 0.017(5) 0.014(4) 0.003(4) C13 0.025(6) 0.018(5) 0.024(6) 0.007(4) 0.003(4) 0.004(4) C14 0.016(5) 0.017(5) 0.017(5) 0.002(4) -0.015(4) -0.004(4) C15 0.022(5) 0.010(5) 0.017(5) 0.003(4) -0.004(4) 0.003(4) C16 0.026(5) 0.011(5) 0.012(5) 0.004(4) -0.002(4) 0.009(4) C17 0.024(5) 0.016(5) 0.018(5) 0.000(4) -0.004(4) 0.008(4) C18 0.024(6) 0.023(6) 0.025(5) 0.005(4) -0.005(4) 0.009(5) C19 0.025(6) 0.025(6) 0.026(6) 0.004(5) -0.005(5) 0.014(5) C20 0.013(5) 0.020(5) 0.027(6) 0.008(4) 0.000(4) 0.007(4) C51 0.022(5) 0.017(5) 0.020(5) 0.004(4) 0.001(4) 0.006(4) C52 0.023(6) 0.018(5) 0.039(6) 0.000(5) -0.001(5) -0.002(5) C53 0.033(6) 0.030(6) 0.039(7) 0.014(5) -0.019(5) -0.012(5) C54 0.064(9) 0.022(6) 0.032(7) 0.000(5) -0.014(6) 0.008(6) C55 0.060(8) 0.017(6) 0.030(6) -0.008(5) 0.010(6) 0.012(6) C56 0.034(6) 0.022(6) 0.038(7) -0.001(5) 0.007(5) 0.012(5) C101 0.024(6) 0.043(7) 0.012(5) -0.001(5) -0.004(4) 0.008(5) C102 0.019(6) 0.047(8) 0.048(8) -0.002(6) -0.003(5) 0.005(5) C103 0.032(8) 0.112(14) 0.040(8) -0.031(8) 0.001(6) 0.032(8) C104 0.020(7) 0.125(15) 0.027(7) 0.001(9) -0.004(6) -0.018(9) C105 0.050(9) 0.084(11) 0.019(6) 0.015(7) -0.004(6) -0.021(8) C106 0.033(7) 0.034(7) 0.028(6) 0.002(5) -0.003(5) -0.010(5) C151 0.030(6) 0.022(5) 0.017(5) 0.001(4) 0.005(4) 0.009(5) C152 0.031(6) 0.020(6) 0.026(6) 0.007(5) -0.008(5) 0.005(5) C153 0.018(5) 0.020(5) 0.033(6) 0.006(5) -0.002(4) -0.001(4) C154 0.024(6) 0.026(6) 0.033(6) -0.005(5) -0.008(5) 0.007(5) C155 0.009(5) 0.035(6) 0.016(5) 0.002(4) -0.001(4) -0.003(4) C156 0.013(5) 0.019(5) 0.025(5) 0.002(4) -0.004(4) -0.001(4) C201 0.027(6) 0.020(5) 0.034(6) 0.007(5) 0.005(5) 0.010(5) C202 0.021(6) 0.021(6) 0.040(7) 0.006(5) 0.005(5) 0.000(5) C203 0.028(6) 0.035(7) 0.060(8) 0.014(6) 0.013(6) 0.011(5) C204 0.050(8) 0.036(7) 0.042(7) 0.016(6) 0.020(6) 0.010(6) C205 0.057(8) 0.031(6) 0.031(6) 0.015(5) 0.010(6) 0.022(6) C206 0.030(6) 0.032(6) 0.028(6) 0.009(5) -0.002(5) 0.006(5) N25 0.017(4) 0.017(4) 0.018(4) -0.001(3) -0.001(3) 0.011(3) N26 0.015(4) 0.025(4) 0.016(4) 0.004(3) 0.000(3) 0.008(4) N27 0.009(4) 0.014(4) 0.017(4) 0.003(3) -0.002(3) 0.001(3) N28 0.016(4) 0.018(4) 0.015(4) 0.005(3) -0.001(3) 0.009(3) C21 0.009(5) 0.015(5) 0.025(5) 0.004(4) -0.004(4) 0.000(4) C24 0.014(5) 0.007(4) 0.024(5) 0.003(4) 0.006(4) 0.005(4) C25 0.008(5) 0.010(5) 0.022(5) -0.002(4) -0.001(4) 0.006(4) C26 0.019(5) 0.011(5) 0.016(5) 0.002(4) -0.001(4) 0.003(4) C27 0.026(6) 0.020(5) 0.016(5) 0.006(4) 0.003(4) 0.009(4) C28 0.016(5) 0.021(5) 0.023(5) -0.001(4) 0.004(4) 0.010(4) C29 0.018(5) 0.012(5) 0.014(5) 0.003(4) 0.001(4) 0.008(4) C30 0.018(5) 0.014(5) 0.024(5) 0.006(4) 0.004(4) 0.009(4) C31 0.019(5) 0.012(5) 0.019(5) 0.001(4) 0.005(4) 0.013(4) C32 0.020(5) 0.013(5) 0.013(5) -0.001(4) 0.005(4) 0.013(4) C33 0.018(5) 0.022(5) 0.015(5) 0.004(4) 0.007(4) 0.015(4) C34 0.012(5) 0.018(5) 0.011(5) 0.002(4) 0.001(4) 0.009(4) C35 0.018(5) 0.024(5) 0.015(5) 0.002(4) 0.005(4) 0.017(4) C36 0.019(5) 0.013(5) 0.018(5) 0.001(4) 0.001(4) 0.011(4) C37 0.018(5) 0.020(5) 0.025(5) 0.007(4) -0.008(4) 0.010(4) C39 0.024(5) 0.014(5) 0.009(4) 0.003(4) 0.005(4) 0.011(4) C40 0.018(5) 0.012(5) 0.028(5) 0.001(4) -0.004(4) 0.008(4) C251 0.013(5) 0.026(6) 0.019(5) 0.010(4) -0.001(4) 0.004(4) C252 0.024(5) 0.019(5) 0.025(6) -0.002(4) 0.006(4) 0.010(4) C253 0.032(6) 0.032(6) 0.036(6) 0.021(5) 0.010(5) 0.023(5) C254 0.025(6) 0.057(8) 0.016(5) 0.006(5) -0.005(4) 0.023(6) C255 0.012(5) 0.033(6) 0.042(7) 0.007(5) -0.002(5) 0.005(5) C256 0.022(6) 0.030(6) 0.026(6) 0.011(5) 0.009(5) 0.017(5) C301 0.025(5) 0.024(5) 0.004(4) -0.002(4) 0.000(4) 0.005(4) C302 0.029(6) 0.020(5) 0.031(6) 0.006(5) -0.001(5) 0.003(5) C303 0.042(7) 0.023(6) 0.042(7) 0.020(5) -0.005(6) 0.001(5) C304 0.009(5) 0.045(7) 0.032(6) 0.011(5) -0.004(4) -0.012(5) C305 0.022(6) 0.038(7) 0.020(5) 0.003(5) 0.006(4) 0.006(5) C306 0.021(5) 0.028(6) 0.021(5) 0.007(4) 0.001(4) 0.015(5) C351 0.011(5) 0.012(4) 0.008(4) 0.001(4) -0.008(4) 0.003(4) C352 0.018(5) 0.024(6) 0.034(6) 0.011(5) 0.003(5) 0.012(4) C353 0.025(6) 0.037(6) 0.034(6) 0.018(5) 0.008(5) 0.021(5) C354 0.030(6) 0.038(7) 0.034(6) 0.013(5) -0.006(5) 0.017(5) C355 0.030(6) 0.032(6) 0.024(6) 0.009(5) -0.005(5) 0.010(5) C356 0.018(5) 0.030(6) 0.031(6) 0.014(5) 0.006(4) 0.013(5) C401 0.016(5) 0.016(5) 0.028(6) 0.006(4) -0.004(4) 0.012(4) C402 0.023(6) 0.023(6) 0.030(6) 0.010(5) 0.002(5) 0.003(5) C403 0.011(5) 0.024(6) 0.049(7) 0.004(5) -0.003(5) 0.006(4) C404 0.024(6) 0.024(6) 0.049(7) 0.017(5) 0.012(5) 0.010(5) C405 0.025(6) 0.023(6) 0.033(6) 0.015(5) 0.011(5) 0.006(5) C406 0.017(5) 0.018(5) 0.023(5) 0.007(4) 0.001(4) 0.008(4) Br2 0.0386(7) 0.0216(6) 0.0316(6) 0.0141(5) 0.0044(5) 0.0055(5) Br3 0.0738(9) 0.0127(6) 0.0367(7) 0.0064(5) 0.0037(6) 0.0075(6) Br7 0.0278(6) 0.0326(6) 0.0259(6) 0.0014(5) -0.0027(5) 0.0018(5) Br8 0.0303(6) 0.0394(7) 0.0256(6) 0.0062(5) 0.0058(5) -0.0010(5) Br12 0.0171(5) 0.0332(6) 0.0352(6) 0.0036(5) -0.0001(5) 0.0040(5) Br13 0.0219(6) 0.0310(6) 0.0279(6) -0.0009(5) -0.0060(5) 0.0011(5) C171 0.008(5) 0.028(6) 0.019(5) -0.010(4) -0.001(4) -0.001(4) C172 0.035(7) 0.022(6) 0.062(8) 0.008(6) 0.014(6) 0.017(5) C181 0.035(6) 0.018(5) 0.033(6) -0.005(5) 0.022(5) 0.009(5) C182 0.044(8) 0.054(9) 0.078(10) 0.020(8) 0.013(7) 0.020(7) Br22 0.0275(6) 0.0273(6) 0.0275(6) 0.0075(5) 0.0113(5) 0.0156(5) Br23 0.0284(6) 0.0251(6) 0.0339(6) 0.0095(5) 0.0064(5) 0.0192(5) Br32 0.0202(5) 0.0196(5) 0.0252(6) 0.0023(4) 0.0026(4) 0.0030(4) Br33 0.0203(5) 0.0206(5) 0.0211(5) 0.0011(4) -0.0036(4) 0.0079(4) Br37 0.019(4) 0.026(3) 0.077(5) 0.029(3) 0.000(3) 0.010(3) Br38 0.019(4) 0.023(4) 0.073(4) 0.028(3) 0.004(3) 0.004(3) Br27 0.0229(7) 0.0301(7) 0.0125(7) 0.0018(6) -0.0013(6) 0.0147(6) Br28 0.0208(7) 0.0437(10) 0.0152(8) 0.0057(6) 0.0062(5) 0.0137(6) C1S 0.035(7) 0.028(6) 0.047(7) -0.002(5) 0.003(6) 0.012(5) Cl1S 0.066(2) 0.056(2) 0.0485(19) 0.0001(16) -0.0005(16) 0.0288(18) Cl2S 0.051(2) 0.0347(17) 0.095(3) 0.0176(17) 0.0212(19) 0.0153(15) C2S 0.049(8) 0.039(7) 0.034(7) 0.009(5) -0.009(6) 0.016(6) Cl3S 0.059(2) 0.0444(18) 0.0379(17) 0.0024(14) -0.0069(14) 0.0168(16) Cl4S 0.062(2) 0.0427(17) 0.0357(16) 0.0143(13) -0.0047(14) 0.0048(16) C3S 0.099(16) 0.22(3) 0.118(18) 0.094(19) 0.007(14) 0.078(18) Cl5S 0.155(6) 0.119(5) 0.132(5) 0.014(4) -0.017(4) 0.063(4) Cl6S 0.135(6) 0.173(7) 0.099(5) 0.052(5) 0.066(5) 0.112(6) Cl6' 0.038(8) 0.049(8) 0.126(14) 0.017(9) 0.021(8) 0.003(7) C4S 0.052(10) 0.095(14) 0.127(17) 0.010(12) 0.007(10) 0.031(10) Cl7S 0.068(3) 0.239(8) 0.142(5) 0.068(5) 0.013(3) 0.063(4) Cl8S 0.077(4) 0.085(4) 0.086(4) -0.014(3) -0.030(3) 0.025(3) Cl8' 0.042(12) 0.20(3) 0.041(12) -0.032(15) -0.015(9) -0.007(15) _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 N21 C1 1.359(10) . ? N21 C4 1.363(10) . ? N22 C9 1.380(10) . ? N22 C6 1.382(10) . ? N23 C14 1.350(10) . ? N23 C11 1.373(11) . ? N24 C16 1.377(10) . ? N24 C19 1.377(11) . ? C1 C20 1.419(11) . ? C1 C2 1.467(11) . ? C2 C3 1.356(12) . ? C2 Br2 1.866(8) . ? C3 C4 1.459(11) . ? C3 Br3 1.869(9) . ? C4 C5 1.410(11) . ? C5 C6 1.403(11) . ? C5 C51 1.484(11) . ? C6 C7 1.426(11) . ? C7 C8 1.372(11) . ? C7 Br7 1.865(8) . ? C8 C9 1.443(11) . ? C8 Br8 1.858(8) . ? C9 C10 1.398(11) . ? C10 C11 1.412(11) . ? C10 C101 1.484(11) . ? C11 C12 1.461(12) . ? C12 C13 1.347(12) . ? C12 Br12 1.878(9) . ? C13 C14 1.468(11) . ? C13 Br13 1.873(9) . ? C14 C15 1.414(11) . ? C15 C16 1.397(11) . ? C15 C151 1.500(10) . ? C16 C17 1.453(11) . ? C17 C18 1.381(12) . ? C17 C171 1.535(9) . ? C18 C19 1.449(12) . ? C18 C181 1.534(13) . ? C19 C20 1.407(11) . ? C20 C201 1.501(11) . ? C51 C56 1.384(8) . ? C51 C52 1.390(8) . ? C52 C53 1.390(8) . ? C53 C54 1.381(8) . ? C54 C55 1.376(8) . ? C55 C56 1.386(8) . ? C101 C102 1.384(8) . ? C101 C106 1.384(8) . ? C102 C103 1.387(8) . ? C103 C104 1.386(9) . ? C104 C105 1.381(9) . ? C105 C106 1.382(8) . ? C151 C152 1.391(8) . ? C151 C156 1.392(7) . ? C152 C153 1.386(8) . ? C153 C154 1.376(8) . ? C154 C155 1.389(8) . ? C155 C156 1.384(8) . ? C201 C202 1.389(8) . ? C201 C206 1.394(8) . ? C202 C203 1.390(8) . ? C203 C204 1.394(8) . ? C204 C205 1.378(8) . ? C205 C206 1.382(8) . ? N25 C21 1.355(10) . ? N25 C24 1.378(10) . ? N26 C29 1.373(10) . ? N26 C26 1.397(10) . ? N27 C34 1.346(10) . ? N27 C31 1.377(10) . ? N28 C36 1.377(10) . ? N28 C39 1.392(10) . ? C21 C40 1.422(11) . ? C21 C22 1.458(11) . ? C22 C23 1.339(11) . ? C22 Br22 1.866(8) . ? C23 C24 1.471(11) . ? C23 Br23 1.877(9) . ? C24 C25 1.401(11) . ? C25 C26 1.404(11) . ? C25 C251 1.498(10) . ? C26 C27 1.422(11) . ? C27 C28 1.363(11) . ? C27 C271 1.5000(11) . ? C27 Br27 1.854(9) . ? C28 C29 1.443(11) . ? C28 C281 1.5000(11) . ? C28 Br28 1.883(8) . ? C29 C30 1.399(11) . ? C30 C31 1.417(11) . ? C30 C301 1.485(11) . ? C31 C32 1.451(11) . ? C32 C33 1.359(11) . ? C32 Br32 1.885(8) . ? C33 C34 1.466(11) . ? C33 Br33 1.870(8) . ? C34 C35 1.416(11) . ? C35 C36 1.414(11) . ? C35 C351 1.499(10) . ? C36 C37 1.444(11) . ? C37 C38 1.378(11) . ? C37 C371 1.5001(11) . ? C37 Br37 1.817(10) . ? C38 C39 1.439(11) . ? C38 C381 1.5001(11) . ? C38 Br38 1.803(10) . ? C39 C40 1.404(11) . ? C40 C401 1.499(11) . ? C251 C252 1.387(8) . ? C251 C256 1.391(8) . ? C252 C253 1.390(8) . ? C253 C254 1.387(8) . ? C254 C255 1.386(8) . ? C255 C256 1.390(8) . ? C301 C306 1.386(8) . ? C301 C302 1.388(8) . ? C302 C303 1.387(8) . ? C303 C304 1.383(8) . ? C304 C305 1.384(8) . ? C305 C306 1.388(8) . ? C351 C356 1.381(7) . ? C351 C352 1.385(7) . ? C352 C353 1.388(8) . ? C353 C354 1.389(8) . ? C354 C355 1.381(8) . ? C355 C356 1.393(8) . ? C401 C406 1.388(6) . ? C401 C402 1.389(8) . ? C402 C403 1.385(8) . ? C403 C404 1.389(8) . ? C404 C405 1.382(8) . ? C405 C406 1.379(7) . ? C171 C172 1.473(11) . ? C181 C182 1.441(16) . ? C271 C272 1.5000(11) . ? C281 C282 1.5000(11) . ? C371 C372 1.5001(11) . ? C381 C382 1.5001(11) . ? C1S Cl2S 1.765(8) . ? C1S Cl1S 1.768(8) . ? C2S Cl3S 1.753(8) . ? C2S Cl4S 1.755(8) . ? C3S Cl6' 1.725(10) . ? C3S Cl6S 1.751(10) . ? C3S Cl5S 1.789(9) . ? Cl6' Cl8' 2.37(4) . ? C4S Cl8S 1.747(9) . ? C4S Cl7S 1.749(9) . ? C4S Cl8' 1.777(11) . ? Cl7S Cl8' 2.40(2) . ? 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 N21 C4 107.8(7) . . ? C9 N22 C6 111.7(7) . . ? C14 N23 C11 107.7(7) . . ? C16 N24 C19 111.0(7) . . ? N21 C1 C20 123.4(7) . . ? N21 C1 C2 109.1(7) . . ? C20 C1 C2 127.2(7) . . ? C3 C2 C1 106.7(7) . . ? C3 C2 Br2 123.5(7) . . ? C1 C2 Br2 129.6(7) . . ? C2 C3 C4 106.8(8) . . ? C2 C3 Br3 123.7(7) . . ? C4 C3 Br3 128.7(7) . . ? N21 C4 C5 124.3(7) . . ? N21 C4 C3 109.4(7) . . ? C5 C4 C3 126.0(8) . . ? C6 C5 C4 123.6(8) . . ? C6 C5 C51 118.1(8) . . ? C4 C5 C51 118.0(7) . . ? N22 C6 C5 122.7(8) . . ? N22 C6 C7 105.6(7) . . ? C5 C6 C7 131.5(8) . . ? C8 C7 C6 108.6(7) . . ? C8 C7 Br7 123.1(6) . . ? C6 C7 Br7 128.1(6) . . ? C7 C8 C9 108.6(7) . . ? C7 C8 Br8 123.7(7) . . ? C9 C8 Br8 127.0(6) . . ? N22 C9 C10 124.7(8) . . ? N22 C9 C8 104.9(7) . . ? C10 C9 C8 130.3(8) . . ? C9 C10 C11 122.0(8) . . ? C9 C10 C101 119.1(8) . . ? C11 C10 C101 118.9(8) . . ? N23 C11 C10 122.9(8) . . ? N23 C11 C12 108.4(7) . . ? C10 C11 C12 128.1(8) . . ? C13 C12 C11 107.5(8) . . ? C13 C12 Br12 124.4(7) . . ? C11 C12 Br12 127.7(7) . . ? C12 C13 C14 106.2(8) . . ? C12 C13 Br13 123.9(7) . . ? C14 C13 Br13 129.3(7) . . ? N23 C14 C15 122.8(7) . . ? N23 C14 C13 109.7(7) . . ? C15 C14 C13 127.4(7) . . ? C16 C15 C14 122.8(7) . . ? C16 C15 C151 119.0(7) . . ? C14 C15 C151 118.0(7) . . ? N24 C16 C15 122.9(8) . . ? N24 C16 C17 105.9(7) . . ? C15 C16 C17 130.5(8) . . ? C18 C17 C16 108.2(8) . . ? C18 C17 C171 125.8(7) . . ? C16 C17 C171 125.0(7) . . ? C17 C18 C19 107.4(8) . . ? C17 C18 C181 123.8(8) . . ? C19 C18 C181 128.1(8) . . ? N24 C19 C20 123.5(8) . . ? N24 C19 C18 106.8(7) . . ? C20 C19 C18 129.7(8) . . ? C19 C20 C1 122.6(8) . . ? C19 C20 C201 117.4(8) . . ? C1 C20 C201 120.0(7) . . ? C56 C51 C52 118.7(8) . . ? C56 C51 C5 120.6(7) . . ? C52 C51 C5 120.7(7) . . ? C53 C52 C51 120.6(9) . . ? C54 C53 C52 119.7(9) . . ? C55 C54 C53 120.3(9) . . ? C54 C55 C56 119.9(9) . . ? C51 C56 C55 120.9(9) . . ? C102 C101 C106 118.4(9) . . ? C102 C101 C10 121.1(8) . . ? C106 C101 C10 120.4(8) . . ? C101 C102 C103 121.2(10) . . ? C104 C103 C102 119.4(11) . . ? C105 C104 C103 120.0(11) . . ? C104 C105 C106 119.8(11) . . ? C105 C106 C101 121.1(10) . . ? C152 C151 C156 120.0(8) . . ? C152 C151 C15 119.8(7) . . ? C156 C151 C15 120.1(7) . . ? C153 C152 C151 119.1(8) . . ? C154 C153 C152 120.9(8) . . ? C153 C154 C155 120.3(8) . . ? C156 C155 C154 119.3(8) . . ? C155 C156 C151 120.3(8) . . ? C202 C201 C206 119.5(8) . . ? C202 C201 C20 121.3(7) . . ? C206 C201 C20 119.2(7) . . ? C201 C202 C203 120.1(9) . . ? C202 C203 C204 119.4(9) . . ? C205 C204 C203 120.8(9) . . ? C204 C205 C206 119.6(9) . . ? C205 C206 C201 120.6(9) . . ? C21 N25 C24 107.3(7) . . ? C29 N26 C26 111.6(7) . . ? C34 N27 C31 108.4(7) . . ? C36 N28 C39 110.2(7) . . ? N25 C21 C40 122.8(8) . . ? N25 C21 C22 109.6(7) . . ? C40 C21 C22 127.6(8) . . ? C23 C22 C21 107.2(7) . . ? C23 C22 Br22 124.5(6) . . ? C21 C22 Br22 127.8(6) . . ? C22 C23 C24 107.0(7) . . ? C22 C23 Br23 126.4(7) . . ? C24 C23 Br23 126.1(6) . . ? N25 C24 C25 122.7(7) . . ? N25 C24 C23 108.4(7) . . ? C25 C24 C23 128.7(7) . . ? C24 C25 C26 121.8(7) . . ? C24 C25 C251 123.0(7) . . ? C26 C25 C251 115.2(7) . . ? N26 C26 C25 123.0(7) . . ? N26 C26 C27 105.3(7) . . ? C25 C26 C27 131.6(8) . . ? C28 C27 C26 108.9(8) . . ? C28 C27 C271 128(3) . . ? C26 C27 C271 123(3) . . ? C28 C27 Br27 123.1(7) . . ? C26 C27 Br27 127.5(7) . . ? C271 C27 Br27 5(3) . . ? C27 C28 C29 108.9(7) . . ? C27 C28 C281 127(3) . . ? C29 C28 C281 125(3) . . ? C27 C28 Br28 124.7(7) . . ? C29 C28 Br28 125.8(6) . . ? C281 C28 Br28 7(2) . . ? N26 C29 C30 124.5(7) . . ? N26 C29 C28 105.0(7) . . ? C30 C29 C28 130.2(8) . . ? C29 C30 C31 122.2(7) . . ? C29 C30 C301 118.0(7) . . ? C31 C30 C301 119.8(7) . . ? N27 C31 C30 124.2(7) . . ? N27 C31 C32 108.0(7) . . ? C30 C31 C32 127.5(7) . . ? C33 C32 C31 107.8(7) . . ? C33 C32 Br32 124.1(6) . . ? C31 C32 Br32 127.8(6) . . ? C32 C33 C34 106.1(7) . . ? C32 C33 Br33 122.1(7) . . ? C34 C33 Br33 131.5(6) . . ? N27 C34 C35 124.7(7) . . ? N27 C34 C33 109.3(7) . . ? C35 C34 C33 125.7(7) . . ? C36 C35 C34 123.7(7) . . ? C36 C35 C351 118.6(7) . . ? C34 C35 C351 117.7(7) . . ? N28 C36 C35 123.6(7) . . ? N28 C36 C37 106.7(7) . . ? C35 C36 C37 129.7(7) . . ? C38 C37 C36 107.9(7) . . ? C38 C37 C371 121.5(13) . . ? C36 C37 C371 130.6(12) . . ? C38 C37 Br37 126.0(7) . . ? C36 C37 Br37 126.1(7) . . ? C371 C37 Br37 4.5(12) . . ? C37 C38 C39 108.3(7) . . ? C37 C38 C381 124.4(14) . . ? C39 C38 C381 126.6(13) . . ? C37 C38 Br38 123.0(7) . . ? C39 C38 Br38 128.0(7) . . ? C381 C38 Br38 1.6(11) . . ? N28 C39 C40 121.6(7) . . ? N28 C39 C38 106.2(7) . . ? C40 C39 C38 131.9(8) . . ? C39 C40 C21 124.8(8) . . ? C39 C40 C401 119.4(7) . . ? C21 C40 C401 115.8(7) . . ? C252 C251 C256 118.4(7) . . ? C252 C251 C25 121.1(7) . . ? C256 C251 C25 120.2(7) . . ? C251 C252 C253 121.2(8) . . ? C254 C253 C252 119.0(8) . . ? C255 C254 C253 121.0(8) . . ? C254 C255 C256 118.9(8) . . ? C255 C256 C251 121.2(8) . . ? C306 C301 C302 119.2(8) . . ? C306 C301 C30 121.3(7) . . ? C302 C301 C30 119.4(7) . . ? C303 C302 C301 120.3(8) . . ? C304 C303 C302 119.6(8) . . ? C303 C304 C305 121.0(8) . . ? C304 C305 C306 118.7(8) . . ? C301 C306 C305 121.1(8) . . ? C356 C351 C352 119.8(7) . . ? C356 C351 C35 119.2(7) . . ? C352 C351 C35 120.9(7) . . ? C351 C352 C353 119.8(8) . . ? C352 C353 C354 120.3(8) . . ? C355 C354 C353 119.9(8) . . ? C354 C355 C356 119.6(8) . . ? C351 C356 C355 120.5(8) . . ? C406 C401 C402 119.2(7) . . ? C406 C401 C40 122.9(6) . . ? C402 C401 C40 117.8(6) . . ? C403 C402 C401 119.8(8) . . ? C402 C403 C404 120.4(8) . . ? C405 C404 C403 120.0(8) . . ? C406 C405 C404 119.5(7) . . ? C405 C406 C401 121.2(5) . . ? C172 C171 C17 110.8(5) . . ? C182 C181 C18 115.9(9) . . ? C27 C271 C272 115(4) . . ? C282 C281 C28 109(3) . . ? C372 C371 C37 116.0(11) . . ? C38 C381 C382 115.4(11) . . ? Cl2S C1S Cl1S 111.2(5) . . ? Cl3S C2S Cl4S 112.6(5) . . ? Cl6' C3S Cl6S 88.3(8) . . ? Cl6' C3S Cl5S 104.7(10) . . ? Cl6S C3S Cl5S 117.8(8) . . ? C3S Cl6' Cl8' 146.1(11) . . ? Cl8S C4S Cl7S 118.1(7) . . ? Cl8S C4S Cl8' 37.7(11) . . ? Cl7S C4S Cl8' 85.8(10) . . ? C4S Cl7S Cl8' 47.6(5) . . ? C4S Cl8' Cl6' 121.1(19) . . ? C4S Cl8' Cl7S 46.6(5) . . ? Cl6' Cl8' Cl7S 88.4(12) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 56.07 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.645 _refine_diff_density_min -1.241 _refine_diff_density_rms 0.146 #====END data_ms360 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,13-Dibromo-7,8-diethyl-5,10,15,20-tetra- phenylporphyrin (monoclinic modification) ; _chemical_name_common ? _chemical_formula_moiety 'C48 H36 Br2 N4' _chemical_formula_sum 'C48 H36 Br2 N4' _chemical_formula_weight 828.63 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' 'Br' 'Br' -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 11.8426(2) _cell_length_b 14.1555(3) _cell_length_c 22.6044(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.19 _cell_angle_gamma 90.00 _cell_volume 3717.33(12) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ; 6744 reflections with I > 10 sigma I ; _cell_measurement_theta_min n/a _cell_measurement_theta_max n/a _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas n/d _exptl_crystal_density_diffrn 1.481 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1688 _exptl_absorpt_coefficient_mu 2.222 _exptl_absorpt_correction_type SADABS _exptl_absorpt_correction_T_min 0.3911 _exptl_absorpt_correction_T_max 0.6176 _exptl_special_details ; The data collection nominally covered over a hemisphere of reciprocal space, by a combination of three sets of exposures; each set had a different &Gf angle for the crystal and each exposure covered 0.3 &^o&0 in &Gw. The crystal-to-detector distance was 4.910 cm. Coverage of the unique set is over 97 % complete to at least 26&^o&0 in &Gq. Crystal decay was monitored by repeating the initial frames at the end of data collection and analyzing the duplicate reflections. No decay was observed. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Siemens SMART CCD' _diffrn_measurement_method &Gw _diffrn_standards_number n/a _diffrn_standards_interval_count n/a _diffrn_standards_interval_time n/a _diffrn_standards_decay_% stable _diffrn_reflns_number 22596 _diffrn_reflns_av_R_equivalents 0.0376 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.32 _reflns_number_total 8740 _reflns_number_gt 6693 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; SMART, Software Reference Manual (1994). Siemens Anal. Instr. WI ; _computing_cell_refinement SMART _computing_data_reduction ; SAINT Version 4, Software Reference Manual (1995). Siemens Analystical Instr. WI ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus, Siemens, 1994' _computing_publication_material 'XCIF, Shelxtl-Plus, Siemens, 1994' _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. The residual electron density is located close to Br1 (0.97 A). ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0767P)^2^+0.1430P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef n/d _refine_ls_number_reflns 8740 _refine_ls_number_parameters 487 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0681 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1242 _refine_ls_wR_factor_gt 0.1148 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.002 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N21 N 0.18250(19) 1.51146(16) 0.02889(10) 0.0208(5) Uani 1 d . . . N22 N 0.3120(2) 1.39824(16) -0.04668(10) 0.0218(5) Uani 1 d . . . H22 H 0.2752 1.3881 -0.0170 0.026 Uiso 1 calc R . . N23 N 0.2505(2) 1.23092(16) 0.02183(10) 0.0206(5) Uani 1 d . . . N24 N 0.1423(2) 1.34883(16) 0.09916(10) 0.0220(5) Uani 1 d . . . H24 H 0.1659 1.3578 0.0650 0.026 Uiso 1 calc R . . C1 C 0.1217(2) 1.55636(18) 0.06643(12) 0.0199(5) Uani 1 d . . . C2 C 0.0990(2) 1.65433(19) 0.04605(13) 0.0235(6) Uani 1 d . . . C3 C 0.1500(3) 1.6674(2) -0.00151(13) 0.0259(6) Uani 1 d . . . H3 H 0.1500 1.7236 -0.0245 0.031 Uiso 1 calc R . . C4 C 0.2053(3) 1.57801(19) -0.01081(13) 0.0231(6) Uani 1 d . . . C5 C 0.2772(2) 1.56907(19) -0.05389(13) 0.0232(6) Uani 1 d . . . C51 C 0.2952(3) 1.66138(19) -0.08464(13) 0.0248(6) Uani 1 d . . . C52 C 0.3872(3) 1.7199(2) -0.06049(15) 0.0336(7) Uani 1 d . . . H52 H 0.4417 1.7003 -0.0261 0.040 Uiso 1 calc R . . C53 C 0.3989(4) 1.8077(2) -0.08715(17) 0.0452(9) Uani 1 d . . . H53 H 0.4622 1.8474 -0.0712 0.054 Uiso 1 calc R . . C54 C 0.3195(4) 1.8364(2) -0.13596(17) 0.0447(9) Uani 1 d . . . H54 H 0.3271 1.8967 -0.1533 0.054 Uiso 1 calc R . . C55 C 0.2275(3) 1.7785(2) -0.16054(17) 0.0384(8) Uani 1 d . . . H55 H 0.1732 1.7984 -0.1949 0.046 Uiso 1 calc R . . C56 C 0.2159(3) 1.6910(2) -0.13443(14) 0.0308(7) Uani 1 d . . . H56 H 0.1530 1.6513 -0.1509 0.037 Uiso 1 calc R . . C6 C 0.3288(2) 1.48662(19) -0.06999(12) 0.0216(6) Uani 1 d . . . C7 C 0.3978(2) 1.4716(2) -0.11564(12) 0.0235(6) Uani 1 d . . . C71 C 0.4419(3) 1.5451(2) -0.15435(13) 0.0273(6) Uani 1 d . . . H71A H 0.3884 1.5995 -0.1598 0.033 Uiso 1 calc R . . H71B H 0.4416 1.5176 -0.1946 0.033 Uiso 1 calc R . . C72 C 0.5633(3) 1.5808(3) -0.12817(18) 0.0427(9) Uani 1 d . . . H72A H 0.5860 1.6279 -0.1554 0.064 Uiso 1 calc R . . H72B H 0.6174 1.5277 -0.1237 0.064 Uiso 1 calc R . . H72C H 0.5642 1.6096 -0.0887 0.064 Uiso 1 calc R . . C8 C 0.4184(2) 1.3765(2) -0.11903(12) 0.0231(6) Uani 1 d . . . C81 C 0.4959(3) 1.3333(2) -0.15779(14) 0.0298(7) Uani 1 d . . . H81A H 0.5011 1.3768 -0.1914 0.036 Uiso 1 calc R . . H81B H 0.4611 1.2735 -0.1754 0.036 Uiso 1 calc R . . C82 C 0.6169(3) 1.3132(3) -0.12224(18) 0.0423(9) Uani 1 d . . . H82A H 0.6636 1.2854 -0.1491 0.063 Uiso 1 calc R . . H82B H 0.6124 1.2691 -0.0894 0.063 Uiso 1 calc R . . H82C H 0.6523 1.3724 -0.1054 0.063 Uiso 1 calc R . . C9 C 0.3606(2) 1.32838(19) -0.07615(12) 0.0214(6) Uani 1 d . . . C10 C 0.3475(2) 1.23134(19) -0.06682(12) 0.0208(6) Uani 1 d . . . C101 C 0.3900(2) 1.16276(19) -0.10821(12) 0.0220(6) Uani 1 d . . . C102 C 0.3254(3) 1.1443(2) -0.16564(13) 0.0257(6) Uani 1 d . . . H102 H 0.2544 1.1762 -0.1790 0.031 Uiso 1 calc R . . C103 C 0.3642(3) 1.0796(2) -0.20338(13) 0.0287(7) Uani 1 d . . . H103 H 0.3199 1.0676 -0.2424 0.034 Uiso 1 calc R . . C104 C 0.4677(3) 1.0325(2) -0.18415(14) 0.0290(7) Uani 1 d . . . H104 H 0.4951 0.9894 -0.2103 0.035 Uiso 1 calc R . . C105 C 0.5306(3) 1.0485(2) -0.12697(15) 0.0318(7) Uani 1 d . . . H105 H 0.6007 1.0154 -0.1136 0.038 Uiso 1 calc R . . C106 C 0.4918(2) 1.1128(2) -0.08885(14) 0.0274(6) Uani 1 d . . . H106 H 0.5350 1.1227 -0.0493 0.033 Uiso 1 calc R . . C11 C 0.2911(2) 1.18821(19) -0.02364(12) 0.0205(5) Uani 1 d . . . C12 C 0.2696(2) 1.08661(19) -0.02481(13) 0.0227(6) Uani 1 d . . . H12 H 0.2901 1.0419 -0.0523 0.027 Uiso 1 calc R . . C13 C 0.2149(2) 1.06916(19) 0.02094(13) 0.0226(6) Uani 1 d . . . C14 C 0.2032(2) 1.15917(19) 0.05111(12) 0.0218(6) Uani 1 d . . . C15 C 0.1544(2) 1.17336(19) 0.10214(12) 0.0199(5) Uani 1 d . . . C151 C 0.1135(2) 1.09221(19) 0.13517(12) 0.0216(6) Uani 1 d . . . C152 C 0.1906(3) 1.0346(2) 0.17371(13) 0.0259(6) Uani 1 d . . . H152 H 0.2710 1.0464 0.1795 0.031 Uiso 1 calc R . . C153 C 0.1499(3) 0.9603(2) 0.20363(15) 0.0347(7) Uani 1 d . . . H153 H 0.2026 0.9215 0.2300 0.042 Uiso 1 calc R . . C154 C 0.0337(3) 0.9423(2) 0.19534(15) 0.0352(8) Uani 1 d . . . H154 H 0.0067 0.8907 0.2156 0.042 Uiso 1 calc R . . C155 C -0.0441(3) 0.9994(2) 0.15750(15) 0.0328(7) Uani 1 d . . . H155 H -0.1244 0.9872 0.1519 0.039 Uiso 1 calc R . . C156 C -0.0039(3) 1.0744(2) 0.12798(14) 0.0269(6) Uani 1 d . . . H156 H -0.0571 1.1141 0.1026 0.032 Uiso 1 calc R . . C16 C 0.1343(2) 1.26271(19) 0.12567(13) 0.0207(5) Uani 1 d . . . C17 C 0.0980(2) 1.2798(2) 0.18136(13) 0.0238(6) Uani 1 d . . . H17 H 0.0862 1.2333 0.2098 0.029 Uiso 1 calc R . . C18 C 0.0832(2) 1.37533(19) 0.18645(13) 0.0236(6) Uani 1 d . . . H18 H 0.0604 1.4068 0.2194 0.028 Uiso 1 calc R . . C19 C 0.1082(2) 1.41913(19) 0.13359(12) 0.0199(5) Uani 1 d . . . C20 C 0.0937(2) 1.51540(19) 0.11839(12) 0.0207(6) Uani 1 d . . . C201 C 0.0494(2) 1.57689(18) 0.16329(12) 0.0205(5) Uani 1 d . . . C202 C 0.1244(2) 1.6323(2) 0.20368(13) 0.0250(6) Uani 1 d . . . H202 H 0.2046 1.6297 0.2038 0.030 Uiso 1 calc R . . C203 C 0.0839(3) 1.6917(2) 0.24402(14) 0.0293(7) Uani 1 d . . . H203 H 0.1362 1.7289 0.2717 0.035 Uiso 1 calc R . . C204 C -0.0336(3) 1.6963(2) 0.24354(14) 0.0288(7) Uani 1 d . . . H204 H -0.0620 1.7379 0.2702 0.035 Uiso 1 calc R . . C205 C -0.1095(3) 1.6399(2) 0.20394(14) 0.0291(7) Uani 1 d . . . H205 H -0.1897 1.6424 0.2040 0.035 Uiso 1 calc R . . C206 C -0.0683(3) 1.5798(2) 0.16420(13) 0.0246(6) Uani 1 d . . . H206 H -0.1202 1.5407 0.1376 0.030 Uiso 1 calc R . . Br1 Br 0.01489(3) 1.75061(2) 0.074922(15) 0.03144(10) Uani 1 d . . . Br2 Br 0.15870(3) 0.948255(19) 0.034710(13) 0.02806(10) Uani 1 d . . . 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 N21 0.0261(12) 0.0169(12) 0.0215(11) -0.0006(9) 0.0098(9) -0.0035(9) N22 0.0292(12) 0.0159(12) 0.0238(12) 0.0016(9) 0.0141(10) -0.0021(9) N23 0.0276(12) 0.0152(11) 0.0225(12) -0.0001(9) 0.0135(10) -0.0017(9) N24 0.0330(13) 0.0146(11) 0.0227(12) 0.0010(9) 0.0157(10) -0.0002(10) C1 0.0237(13) 0.0122(13) 0.0248(14) 0.0004(10) 0.0069(11) -0.0003(10) C2 0.0277(14) 0.0161(13) 0.0296(15) 0.0003(11) 0.0130(12) 0.0012(11) C3 0.0358(16) 0.0175(14) 0.0272(15) 0.0051(11) 0.0128(13) 0.0007(12) C4 0.0305(14) 0.0152(13) 0.0251(14) -0.0008(11) 0.0089(12) 0.0011(11) C5 0.0310(15) 0.0150(13) 0.0253(14) 0.0022(11) 0.0099(12) -0.0040(11) C51 0.0375(16) 0.0148(13) 0.0267(14) 0.0002(11) 0.0174(13) -0.0018(12) C52 0.0493(19) 0.0253(16) 0.0294(16) -0.0005(13) 0.0154(15) -0.0101(14) C53 0.071(3) 0.0245(17) 0.048(2) -0.0085(16) 0.031(2) -0.0196(17) C54 0.072(3) 0.0196(16) 0.055(2) 0.0110(15) 0.043(2) 0.0018(17) C55 0.0464(19) 0.0320(18) 0.0438(19) 0.0176(15) 0.0258(16) 0.0120(15) C56 0.0343(16) 0.0272(16) 0.0347(17) 0.0053(13) 0.0158(14) 0.0005(13) C6 0.0276(14) 0.0174(13) 0.0217(14) 0.0023(11) 0.0095(11) -0.0043(11) C7 0.0278(14) 0.0229(15) 0.0212(14) -0.0012(11) 0.0080(12) -0.0041(11) C71 0.0347(15) 0.0251(15) 0.0250(15) 0.0021(12) 0.0131(12) -0.0022(12) C72 0.0353(18) 0.0314(18) 0.064(2) 0.0179(17) 0.0164(17) -0.0059(15) C8 0.0268(14) 0.0230(15) 0.0226(14) -0.0007(11) 0.0120(11) -0.0061(11) C81 0.0427(17) 0.0222(15) 0.0301(16) -0.0046(12) 0.0210(14) -0.0062(13) C82 0.0351(18) 0.0342(19) 0.064(2) -0.0091(17) 0.0244(17) -0.0069(15) C9 0.0265(14) 0.0189(14) 0.0210(13) -0.0021(11) 0.0106(11) -0.0018(11) C10 0.0254(13) 0.0184(14) 0.0203(13) -0.0012(10) 0.0089(11) -0.0004(11) C101 0.0299(14) 0.0153(13) 0.0248(14) 0.0008(11) 0.0150(12) -0.0041(11) C102 0.0326(15) 0.0185(14) 0.0279(15) 0.0035(11) 0.0104(12) -0.0007(12) C103 0.0422(17) 0.0229(15) 0.0236(15) -0.0024(12) 0.0130(13) -0.0079(13) C104 0.0424(17) 0.0183(14) 0.0328(16) -0.0065(12) 0.0232(14) -0.0041(13) C105 0.0314(15) 0.0288(17) 0.0399(18) -0.0010(14) 0.0183(14) 0.0047(13) C106 0.0288(15) 0.0301(16) 0.0252(15) -0.0021(12) 0.0097(12) 0.0005(12) C11 0.0275(14) 0.0130(13) 0.0223(13) -0.0007(10) 0.0084(11) -0.0006(11) C12 0.0319(15) 0.0140(13) 0.0248(14) -0.0039(11) 0.0117(12) -0.0018(11) C13 0.0303(14) 0.0150(13) 0.0242(14) 0.0005(11) 0.0094(12) -0.0020(11) C14 0.0285(14) 0.0150(13) 0.0242(14) -0.0005(11) 0.0107(11) -0.0014(11) C15 0.0222(13) 0.0160(13) 0.0231(13) 0.0020(10) 0.0087(11) 0.0000(10) C151 0.0330(15) 0.0135(13) 0.0220(13) -0.0012(10) 0.0142(12) -0.0002(11) C152 0.0293(15) 0.0229(15) 0.0271(15) 0.0006(12) 0.0092(12) 0.0062(12) C153 0.053(2) 0.0224(16) 0.0313(17) 0.0081(13) 0.0133(15) 0.0092(14) C154 0.060(2) 0.0156(15) 0.0363(17) 0.0036(12) 0.0238(16) -0.0037(14) C155 0.0361(17) 0.0248(16) 0.0427(18) -0.0007(14) 0.0204(15) -0.0073(13) C156 0.0335(16) 0.0195(14) 0.0300(16) 0.0021(12) 0.0123(13) 0.0017(12) C16 0.0261(13) 0.0154(13) 0.0232(14) 0.0026(10) 0.0111(11) -0.0005(11) C17 0.0308(15) 0.0188(14) 0.0251(14) 0.0010(11) 0.0137(12) 0.0007(11) C18 0.0328(15) 0.0157(13) 0.0259(14) -0.0007(11) 0.0149(12) 0.0004(11) C19 0.0238(13) 0.0150(13) 0.0233(14) -0.0028(10) 0.0108(11) -0.0007(10) C20 0.0240(13) 0.0154(13) 0.0246(14) 0.0010(11) 0.0092(11) 0.0008(11) C201 0.0287(14) 0.0120(12) 0.0239(14) 0.0011(10) 0.0124(11) 0.0010(11) C202 0.0286(14) 0.0192(14) 0.0301(15) 0.0019(11) 0.0131(12) 0.0009(11) C203 0.0416(17) 0.0174(14) 0.0313(16) -0.0037(12) 0.0133(14) -0.0014(13) C204 0.0458(18) 0.0140(13) 0.0322(16) 0.0025(12) 0.0219(14) 0.0057(12) C205 0.0310(15) 0.0214(15) 0.0401(17) 0.0069(13) 0.0196(13) 0.0071(12) C206 0.0293(15) 0.0176(13) 0.0288(15) 0.0014(11) 0.0103(12) 0.0005(11) Br1 0.04239(18) 0.01722(16) 0.04043(19) 0.00659(12) 0.02221(14) 0.00890(12) Br2 0.04501(19) 0.01362(15) 0.02964(16) -0.00178(11) 0.01742(13) -0.00454(12) _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 N21 C4 1.364(4) . ? N21 C1 1.371(3) . ? N22 C9 1.379(3) . ? N22 C6 1.387(3) . ? N23 C11 1.359(3) . ? N23 C14 1.388(3) . ? N24 C16 1.370(3) . ? N24 C19 1.372(3) . ? C1 C20 1.406(4) . ? C1 C2 1.470(4) . ? C2 C3 1.344(4) . ? C2 Br1 1.878(3) . ? C3 C4 1.459(4) . ? C4 C5 1.418(4) . ? C5 C6 1.398(4) . ? C5 C51 1.514(4) . ? C51 C56 1.383(4) . ? C51 C52 1.393(4) . ? C52 C53 1.400(5) . ? C53 C54 1.365(6) . ? C54 C55 1.390(5) . ? C55 C56 1.390(4) . ? C6 C7 1.451(4) . ? C7 C8 1.374(4) . ? C7 C71 1.516(4) . ? C71 C72 1.530(4) . ? C8 C9 1.460(4) . ? C8 C81 1.515(4) . ? C81 C82 1.528(5) . ? C9 C10 1.403(4) . ? C10 C11 1.423(4) . ? C10 C101 1.501(4) . ? C101 C106 1.393(4) . ? C101 C102 1.398(4) . ? C102 C103 1.389(4) . ? C103 C104 1.389(5) . ? C104 C105 1.379(5) . ? C105 C106 1.392(4) . ? C11 C12 1.460(4) . ? C12 C13 1.346(4) . ? C13 C14 1.464(4) . ? C13 Br2 1.884(3) . ? C14 C15 1.402(4) . ? C15 C16 1.410(4) . ? C15 C151 1.500(4) . ? C151 C156 1.391(4) . ? C151 C152 1.395(4) . ? C152 C153 1.387(4) . ? C153 C154 1.376(5) . ? C154 C155 1.389(5) . ? C155 C156 1.387(4) . ? C16 C17 1.427(4) . ? C17 C18 1.371(4) . ? C18 C19 1.427(4) . ? C19 C20 1.408(4) . ? C20 C201 1.506(4) . ? C201 C202 1.387(4) . ? C201 C206 1.398(4) . ? C202 C203 1.392(4) . ? C203 C204 1.391(4) . ? C204 C205 1.391(4) . ? C205 C206 1.393(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 C4 N21 C1 106.4(2) . . ? C9 N22 C6 111.1(2) . . ? C11 N23 C14 105.7(2) . . ? C16 N24 C19 110.1(2) . . ? N21 C1 C20 124.3(2) . . ? N21 C1 C2 109.2(2) . . ? C20 C1 C2 126.3(2) . . ? C3 C2 C1 107.3(2) . . ? C3 C2 Br1 121.9(2) . . ? C1 C2 Br1 130.8(2) . . ? C2 C3 C4 106.2(2) . . ? N21 C4 C5 127.7(3) . . ? N21 C4 C3 110.7(2) . . ? C5 C4 C3 121.5(3) . . ? C6 C5 C4 127.2(3) . . ? C6 C5 C51 119.6(2) . . ? C4 C5 C51 113.3(2) . . ? C56 C51 C52 119.6(3) . . ? C56 C51 C5 120.1(3) . . ? C52 C51 C5 120.1(3) . . ? C51 C52 C53 119.6(3) . . ? C54 C53 C52 120.1(3) . . ? C53 C54 C55 120.7(3) . . ? C56 C55 C54 119.4(3) . . ? C51 C56 C55 120.5(3) . . ? N22 C6 C5 123.5(2) . . ? N22 C6 C7 106.3(2) . . ? C5 C6 C7 130.0(3) . . ? C8 C7 C6 108.3(2) . . ? C8 C7 C71 123.7(3) . . ? C6 C7 C71 128.0(3) . . ? C7 C71 C72 114.0(3) . . ? C7 C8 C9 108.0(2) . . ? C7 C8 C81 124.2(2) . . ? C9 C8 C81 127.6(3) . . ? C8 C81 C82 112.5(3) . . ? N22 C9 C10 124.1(2) . . ? N22 C9 C8 106.3(2) . . ? C10 C9 C8 129.5(2) . . ? C9 C10 C11 127.1(2) . . ? C9 C10 C101 118.6(2) . . ? C11 C10 C101 114.1(2) . . ? C106 C101 C102 118.8(3) . . ? C106 C101 C10 120.5(3) . . ? C102 C101 C10 120.7(3) . . ? C103 C102 C101 120.5(3) . . ? C104 C103 C102 120.1(3) . . ? C105 C104 C103 119.8(3) . . ? C104 C105 C106 120.3(3) . . ? C101 C106 C105 120.5(3) . . ? N23 C11 C10 127.6(2) . . ? N23 C11 C12 111.5(2) . . ? C10 C11 C12 120.9(2) . . ? C13 C12 C11 106.0(2) . . ? C12 C13 C14 107.5(2) . . ? C12 C13 Br2 122.1(2) . . ? C14 C13 Br2 130.2(2) . . ? N23 C14 C15 123.8(2) . . ? N23 C14 C13 109.4(2) . . ? C15 C14 C13 126.8(2) . . ? C14 C15 C16 124.5(2) . . ? C14 C15 C151 121.6(2) . . ? C16 C15 C151 113.9(2) . . ? C156 C151 C152 119.0(3) . . ? C156 C151 C15 119.5(3) . . ? C152 C151 C15 121.5(3) . . ? C153 C152 C151 120.0(3) . . ? C154 C153 C152 120.5(3) . . ? C153 C154 C155 120.2(3) . . ? C154 C155 C156 119.5(3) . . ? C155 C156 C151 120.8(3) . . ? N24 C16 C15 127.0(2) . . ? N24 C16 C17 107.0(2) . . ? C15 C16 C17 125.9(2) . . ? C18 C17 C16 107.9(2) . . ? C17 C18 C19 107.9(2) . . ? N24 C19 C20 126.8(2) . . ? N24 C19 C18 106.9(2) . . ? C20 C19 C18 126.1(2) . . ? C19 C20 C1 124.4(2) . . ? C19 C20 C201 115.9(2) . . ? C1 C20 C201 119.6(2) . . ? C202 C201 C206 119.1(3) . . ? C202 C201 C20 120.5(2) . . ? C206 C201 C20 120.4(3) . . ? C201 C202 C203 121.0(3) . . ? C204 C203 C202 119.6(3) . . ? C203 C204 C205 119.9(3) . . ? C204 C205 C206 120.1(3) . . ? C205 C206 C201 120.2(3) . . ? _diffrn_measured_fraction_theta_max 0.907 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.907 _refine_diff_density_max 1.438 _refine_diff_density_min -0.976 _refine_diff_density_rms 0.104 #====END data_ms401 _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2,3,7,8-Tetrabromo-12,13,17,18-tetraethylporphyrin di trifluoroacetate ; _chemical_name_common ? _chemical_formula_moiety '[C52H44N4Br4][C2F3O2]2.2(C1H1Cl3).2(C1H4O1)' _chemical_formula_sum 'C60 H54 Br4 Cl6 F6 N4 O6' _chemical_formula_weight 1573.41 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' 'F' 'F' 0.0727 0.0534 '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' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c 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 16.859(6) _cell_length_b 19.710(11) _cell_length_c 20.042(7) _cell_angle_alpha 90.00 _cell_angle_beta 103.27(3) _cell_angle_gamma 90.00 _cell_volume 6482(5) _cell_formula_units_Z 4 _cell_measurement_temperature 129(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 41 _cell_measurement_theta_max 51 _exptl_crystal_description cube _exptl_crystal_colour green _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas n/d _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3144 _exptl_absorpt_coefficient_mu 5.898 _exptl_absorpt_correction_type 'empirical, XABS2' _exptl_absorpt_correction_T_min 0.55 _exptl_absorpt_correction_T_max 0.55 _exptl_special_details ; ? ; _diffrn_ambient_temperature 129(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Syntex P21' _diffrn_measurement_method '2theta-theta' _diffrn_detector_area_resol_mean n/a _diffrn_standards_number 2 _diffrn_standards_interval_count 198 _diffrn_standards_interval_time ? _diffrn_standards_decay_% stable _diffrn_reflns_number 4003 _diffrn_reflns_av_R_equivalents 0.1180 _diffrn_reflns_av_sigmaI/netI 0.0848 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 3.50 _diffrn_reflns_theta_max 56.97 _reflns_number_total 3754 _reflns_number_gt 2619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Siemens P3' _computing_cell_refinement 'Siemens P3' _computing_data_reduction 'XDISK, Shelxtl-Plus, Siemens, 1994' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XP, Shelxtl-Plus, Siemens, 1994' _computing_publication_material 'XCIF, Shelxtl-Plus, Siemens, 1994' _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. The structure contained severely disordered trifluoroacetate anions, for which the fluorine atoms refined with three split positions of equal occupancy. Due to limited number of reflections, phenyl C5 was refined as a ridgid hexagon and only some side chain atoms were refined with anisotropic thermal parameters. All problems together gave a somewhat unsatisfactory refinement with R1 > 0.10. The residual electron density is located near the bromine atoms. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.1494P)^2^+116.1698P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens constr _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3754 _refine_ls_number_parameters 325 _refine_ls_number_restraints 202 _refine_ls_R_factor_all 0.1394 _refine_ls_R_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.2720 _refine_ls_wR_factor_gt 0.2428 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 0.999 _refine_ls_shift/su_max 0.004 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N21 N 0.9684(6) 0.5403(5) 0.8138(5) 0.033(3) Uani 1 d DU . . H21 H 1.0101 0.5645 0.8079 0.039 Uiso 1 calc R . . N22 N 0.9699(6) 0.6917(5) 0.8130(5) 0.029(3) Uani 1 d DU . . H22 H 0.9509 0.6661 0.7769 0.035 Uiso 1 calc R . . C1 C 0.9489(6) 0.4773(6) 0.7854(6) 0.037(4) Uani 1 d DU . . C2 C 0.8725(6) 0.4611(6) 0.7996(5) 0.035(3) Uani 1 d DU . . C3 C 0.8524(6) 0.5122(6) 0.8395(6) 0.037(3) Uiso 1 d D . . C4 C 0.9150(6) 0.5611(6) 0.8526(6) 0.034(3) Uani 1 d DU . . C5 C 0.9290(7) 0.6175(7) 0.8965(5) 0.030(3) Uani 1 d DU . . C6 C 0.9713(7) 0.6753(6) 0.8801(5) 0.027(3) Uani 1 d DU . . C7 C 1.0153(7) 0.7257(6) 0.9242(5) 0.033(3) Uani 1 d DU . . C8 C 1.0347(7) 0.7750(6) 0.8821(5) 0.033(3) Uani 1 d DU . . C9 C 1.0037(7) 0.7555(6) 0.8126(6) 0.034(3) Uani 1 d DU . . C10 C 1.0000 0.7897(7) 0.7500 0.030(4) Uani 1 d SDU . . C20 C 1.0000 0.4440(8) 0.7500 0.034(5) Uani 1 d SDU . . Br1 Br 0.80432(8) 0.38808(8) 0.76358(7) 0.0417(5) Uani 1 d DU . . Br2 Br 0.75045(9) 0.51732(9) 0.86257(8) 0.0472(5) Uani 1 d DU . . C71 C 1.0532(8) 0.7202(6) 1.0033(5) 0.031(3) Uani 1 d DU . . H71A H 1.0871 0.7608 1.0182 0.037 Uiso 1 calc R . . H71B H 1.0085 0.7201 1.0279 0.037 Uiso 1 calc R . . C72 C 1.0996(9) 0.6639(10) 1.0216(8) 0.069(6) Uani 1 d DU . . H72A H 1.1216 0.6639 1.0713 0.103 Uiso 1 calc R . . H72B H 1.1446 0.6638 0.9981 0.103 Uiso 1 calc R . . H72C H 1.0660 0.6233 1.0085 0.103 Uiso 1 calc R . . C81 C 1.0933(7) 0.8362(7) 0.9054(7) 0.037(3) Uiso 1 d D . . H81A H 1.0724 0.8762 0.8768 0.044 Uiso 1 calc R . . H81B H 1.0933 0.8476 0.9535 0.044 Uiso 1 calc R . . C82 C 1.1704(10) 0.8240(9) 0.9007(8) 0.075(6) Uani 1 d DU . . H82A H 1.2039 0.8643 0.9154 0.113 Uiso 1 calc R . . H82B H 1.1711 0.8132 0.8531 0.113 Uiso 1 calc R . . H82C H 1.1924 0.7856 0.9303 0.113 Uiso 1 calc R . . C51 C 0.8937(5) 0.6173(4) 0.9581(3) 0.030(3) Uiso 1 d GD . . C52 C 0.8989(5) 0.5588(4) 0.9977(4) 0.035(3) Uiso 1 d GD . . H52 H 0.9246 0.5194 0.9852 0.041 Uiso 1 calc R . . C53 C 0.8665(5) 0.5580(4) 1.0555(4) 0.049(4) Uiso 1 d GD . . H53 H 0.8701 0.5181 1.0826 0.058 Uiso 1 calc R . . C54 C 0.8289(5) 0.6156(5) 1.0737(4) 0.048(4) Uiso 1 d GD . . H54 H 0.8067 0.6151 1.1132 0.058 Uiso 1 calc R . . C55 C 0.8236(5) 0.6741(4) 1.0341(4) 0.050(4) Uiso 1 d GD . . H55 H 0.7979 0.7135 1.0466 0.060 Uiso 1 calc R . . C56 C 0.8560(5) 0.6749(4) 0.9763(4) 0.042(3) Uiso 1 d GD . . H56 H 0.8525 0.7148 0.9492 0.050 Uiso 1 calc R . . C101 C 1.0000 0.8651(7) 0.7500 0.039(5) Uiso 1 d SD . . C102 C 0.9415(8) 0.8999(6) 0.7752(7) 0.049(4) Uiso 1 d D . . H102 H 0.9019 0.8757 0.7927 0.058 Uiso 1 calc R . . C103 C 0.9411(9) 0.9704(7) 0.7747(8) 0.061(4) Uiso 1 d D . . H103 H 0.9010 0.9948 0.7912 0.073 Uiso 1 calc R . . C104 C 1.0000 1.0043(12) 0.7500 0.070(7) Uiso 1 d SD . . H104 H 1.0000 1.0525 0.7500 0.084 Uiso 1 calc SR . . C201 C 1.0000 0.3688(7) 0.7500 0.029(4) Uiso 1 d SD . . C202 C 0.9941(7) 0.3324(6) 0.8085(6) 0.038(3) Uiso 1 d D . . H202 H 0.9910 0.3562 0.8490 0.046 Uiso 1 calc R . . C203 C 0.9928(9) 0.2621(6) 0.8083(7) 0.054(4) Uiso 1 d D . . H203 H 0.9871 0.2380 0.8480 0.064 Uiso 1 calc R . . C204 C 1.0000 0.2271(12) 0.7500 0.064(7) Uiso 1 d SD . . H204 H 1.0000 0.1789 0.7500 0.077 Uiso 1 calc SR . . C1S C 0.8651(10) 0.0818(9) 0.5151(9) 0.063(5) Uani 1 d U . . Cl1S Cl 0.8911(4) 0.1461(4) 0.5790(4) 0.120(2) Uani 1 d U . . Cl2S Cl 0.9155(4) 0.0080(3) 0.5467(3) 0.1029(19) Uani 1 d U . . Cl3S Cl 0.8943(3) 0.1114(4) 0.4416(3) 0.112(2) Uani 1 d U . . C1A C 0.3260(7) 0.1197(8) 0.6676(6) 0.038(4) Uani 1 d U . . C2A C 0.2334(10) 0.1133(6) 0.6264(6) 0.057(4) Uani 1 d DU . . O1A O 0.3391(6) 0.1634(5) 0.7116(5) 0.049(3) Uani 1 d U . . O2A O 0.3713(6) 0.0769(5) 0.6503(5) 0.053(3) Uani 1 d U . . F1A F 0.2096(15) 0.0485(9) 0.628(2) 0.049(7) Uiso 0.33 d PD A 1 F2A F 0.2263(14) 0.135(2) 0.5620(10) 0.051(8) Uiso 0.33 d PD A 1 F3A F 0.1797(18) 0.142(3) 0.657(2) 0.091(13) Uiso 0.33 d PD A 1 F1A' F 0.1942(17) 0.068(2) 0.6568(18) 0.054(8) Uiso 0.33 d PD A 2 F2A' F 0.2277(13) 0.096(2) 0.5605(9) 0.037(6) Uiso 0.33 d PD A 2 F3A' F 0.1839(16) 0.104(3) 0.6693(13) 0.059(9) Uiso 0.33 d PD A 2 F1A" F 0.2209(19) 0.0602(19) 0.584(2) 0.079(10) Uiso 0.33 d PD A 3 F2A" F 0.2109(18) 0.1738(11) 0.599(2) 0.071(9) Uiso 0.33 d PD A 3 F3A" F 0.1940(14) 0.1717(10) 0.6308(16) 0.037(6) Uiso 0.33 d PD A 3 C2S C 0.7776(12) 0.2265(10) 0.6932(9) 0.075(5) Uani 1 d U . . O2S O 0.7138(6) 0.2642(6) 0.7117(6) 0.065(3) Uani 1 d 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 N21 0.037(6) 0.016(8) 0.046(7) -0.001(5) 0.009(5) -0.008(5) N22 0.039(6) 0.017(8) 0.031(6) -0.008(5) 0.006(5) 0.000(5) C1 0.024(7) 0.047(11) 0.037(8) 0.007(7) 0.004(6) -0.002(6) C2 0.033(7) 0.042(10) 0.018(6) 0.007(6) -0.017(5) -0.019(6) C4 0.030(7) 0.034(10) 0.037(8) 0.005(7) 0.005(6) -0.004(6) C5 0.045(8) 0.021(9) 0.021(7) -0.005(6) -0.002(5) 0.002(6) C6 0.033(7) 0.020(9) 0.031(7) -0.001(6) 0.010(5) 0.002(6) C7 0.050(8) 0.020(9) 0.024(7) -0.001(6) 0.001(6) -0.005(6) C8 0.027(7) 0.031(9) 0.034(7) -0.002(6) -0.006(5) -0.001(6) C9 0.035(7) 0.026(10) 0.040(8) -0.001(6) 0.003(6) 0.005(6) C10 0.042(10) 0.010(12) 0.036(11) 0.000 0.000(8) 0.000 C20 0.026(10) 0.035(14) 0.034(11) 0.000 -0.004(8) 0.000 Br1 0.0456(9) 0.0388(11) 0.0403(8) -0.0045(7) 0.0088(6) -0.0095(7) Br2 0.0397(9) 0.0538(12) 0.0502(10) -0.0112(8) 0.0147(7) -0.0055(7) C71 0.069(9) 0.005(8) 0.024(7) -0.003(5) 0.023(6) -0.008(6) C72 0.041(9) 0.125(19) 0.036(9) 0.003(10) 0.000(7) -0.013(10) C82 0.127(16) 0.046(13) 0.044(10) -0.012(8) 0.002(10) -0.063(11) C1S 0.074(11) 0.054(13) 0.059(11) 0.003(9) 0.010(9) 0.008(9) Cl1S 0.132(5) 0.101(5) 0.134(5) -0.051(4) 0.041(4) -0.026(4) Cl2S 0.118(4) 0.065(4) 0.135(5) 0.025(3) 0.049(4) 0.023(3) Cl3S 0.083(4) 0.178(7) 0.083(4) 0.056(4) 0.032(3) 0.000(4) C1A 0.027(7) 0.055(12) 0.023(7) 0.008(7) -0.009(5) 0.005(7) C2A 0.075(11) 0.023(11) 0.070(11) -0.013(8) 0.012(9) 0.009(8) O1A 0.051(6) 0.043(7) 0.046(6) -0.022(5) 0.000(5) 0.006(5) O2A 0.043(6) 0.052(8) 0.057(7) -0.015(5) -0.001(5) 0.005(5) C2S 0.107(15) 0.068(14) 0.058(11) 0.002(10) 0.038(10) -0.008(11) O2S 0.064(7) 0.048(8) 0.081(8) 0.005(6) 0.013(6) -0.013(6) _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 N21 C1 1.374(11) . ? N21 C4 1.380(11) . ? N22 C6 1.379(10) . ? N22 C9 1.382(11) . ? C1 C20 1.398(14) . ? C1 C2 1.419(12) . ? C2 C3 1.375(14) . ? C2 Br1 1.880(9) . ? C3 C4 1.410(12) . ? C3 Br2 1.882(9) . ? C4 C5 1.403(16) . ? C5 C6 1.422(17) . ? C5 C51 1.488(11) . ? C6 C7 1.420(11) . ? C7 C8 1.375(14) . ? C7 C71 1.571(13) . ? C8 C9 1.424(12) . ? C8 C81 1.562(13) . ? C9 C10 1.412(13) . ? C10 C9 1.412(13) 2_756 ? C10 C101 1.485(15) . ? C20 C1 1.398(14) 2_756 ? C20 C201 1.482(15) . ? C71 C72 1.358(16) . ? C81 C82 1.346(16) . ? C51 C52 1.3900 . ? C51 C56 1.3900 . ? C52 C53 1.3900 . ? C53 C54 1.3900 . ? C54 C55 1.3900 . ? C55 C56 1.3900 . ? C101 C102 1.389(9) . ? C101 C102 1.389(9) 2_756 ? C102 C103 1.388(10) . ? C103 C104 1.380(10) . ? C104 C103 1.380(9) 2_756 ? C201 C202 1.396(9) . ? C201 C202 1.396(9) 2_756 ? C202 C203 1.387(9) . ? C203 C204 1.386(9) . ? C204 C203 1.386(9) 2_756 ? C1S Cl2S 1.729(18) . ? C1S Cl3S 1.756(17) . ? C1S Cl1S 1.783(18) . ? C1A O1A 1.216(16) . ? C1A O2A 1.239(16) . ? C1A C2A 1.60(2) . ? C2A F2A" 1.334(13) . ? C2A F3A 1.337(13) . ? C2A F1A' 1.339(12) . ? C2A F1A" 1.341(13) . ? C2A F3A' 1.341(12) . ? C2A F2A 1.341(12) . ? C2A F3A" 1.342(12) . ? C2A F1A 1.343(13) . ? C2A F2A' 1.345(12) . ? C2S O2S 1.42(2) . ? 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 N21 C4 112.2(10) . . ? C6 N22 C9 107.7(10) . . ? N21 C1 C20 121.2(10) . . ? N21 C1 C2 105.1(9) . . ? C20 C1 C2 133.6(11) . . ? C3 C2 C1 108.0(8) . . ? C3 C2 Br1 124.9(7) . . ? C1 C2 Br1 126.8(9) . . ? C2 C3 C4 109.6(8) . . ? C2 C3 Br2 122.9(7) . . ? C4 C3 Br2 127.2(8) . . ? N21 C4 C5 123.5(10) . . ? N21 C4 C3 104.4(9) . . ? C5 C4 C3 132.0(10) . . ? C4 C5 C6 120.6(10) . . ? C4 C5 C51 118.5(10) . . ? C6 C5 C51 120.8(10) . . ? N22 C6 C5 121.0(10) . . ? N22 C6 C7 109.4(9) . . ? C5 C6 C7 129.4(10) . . ? C8 C7 C6 106.0(8) . . ? C8 C7 C71 124.7(9) . . ? C6 C7 C71 127.8(10) . . ? C7 C8 C9 108.9(9) . . ? C7 C8 C81 125.9(9) . . ? C9 C8 C81 124.4(10) . . ? N22 C9 C10 120.4(10) . . ? N22 C9 C8 107.4(10) . . ? C10 C9 C8 132.2(11) . . ? C9 C10 C9 122.9(14) 2_756 . ? C9 C10 C101 118.5(7) 2_756 . ? C9 C10 C101 118.5(7) . . ? C1 C20 C1 124.0(15) . 2_756 ? C1 C20 C201 118.0(7) . . ? C1 C20 C201 118.0(7) 2_756 . ? C72 C71 C7 113.8(11) . . ? C82 C81 C8 113.3(11) . . ? C52 C51 C56 120.0 . . ? C52 C51 C5 119.4(7) . . ? C56 C51 C5 120.6(7) . . ? C53 C52 C51 120.0 . . ? C52 C53 C54 120.0 . . ? C55 C54 C53 120.0 . . ? C56 C55 C54 120.0 . . ? C55 C56 C51 120.0 . . ? C102 C101 C102 120.7(16) . 2_756 ? C102 C101 C10 119.6(8) . . ? C102 C101 C10 119.6(8) 2_756 . ? C103 C102 C101 119.6(14) . . ? C104 C103 C102 119.1(17) . . ? C103 C104 C103 122(2) . 2_756 ? C202 C201 C202 118.2(15) . 2_756 ? C202 C201 C20 120.9(7) . . ? C202 C201 C20 120.9(7) 2_756 . ? C203 C202 C201 121.0(13) . . ? C204 C203 C202 119.7(17) . . ? C203 C204 C203 120(2) . 2_756 ? Cl2S C1S Cl3S 112.2(10) . . ? Cl2S C1S Cl1S 108.5(9) . . ? Cl3S C1S Cl1S 107.2(10) . . ? O1A C1A O2A 131.6(12) . . ? O1A C1A C2A 115.1(12) . . ? O2A C1A C2A 113.2(12) . . ? _diffrn_measured_fraction_theta_max 0.414 _diffrn_reflns_theta_full 56.97 _diffrn_measured_fraction_theta_full 0.414 _refine_diff_density_max 1.205 _refine_diff_density_min -0.931 _refine_diff_density_rms 0.160 #====END