Supplementary Material for Organic & Biomolecular Chemistry This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Oleg Rakitin' _publ_contact_author_address ; Zelinsky Institute of Organic Chemistry Leninsky Prospekt 47 Moscow 119991 RUSSIAN FEDERATION ; _publ_contact_author_email ORAKITIN@IOC.AC.RU _publ_section_title ; Direct Synthesis of Fused 1,2,3,4,5-Pentathiepins ; loop_ _publ_author_name 'Oleg Rakitin' 'Stanislav A. Amelichev' 'Lidia S. Konstantinova' 'Konstantin Lyssenko' 'Charles Rees' data_ss _database_code_depnum_ccdc_archive 'CCDC 274835' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6,8-Dichloro-7-methyl-7H-[1,2,3,4,5]pentathiepino[6,7-c]pyrrole ; _chemical_name_common ;6,8-Dichloro-7-methyl-7H-(1,2,3,4,5)pentathiepino(6,7- c)pyrrole ; _chemical_melting_point '167-170 deg C' _chemical_formula_moiety 'C5 H3 Cl2 N S5' _chemical_formula_sum 'C5 H3 Cl2 N S5' _chemical_formula_weight 308.28 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.7805(17) _cell_length_b 9.1484(19) _cell_length_c 13.906(3) _cell_angle_alpha 79.210(17) _cell_angle_beta 87.892(17) _cell_angle_gamma 84.473(16) _cell_volume 1092.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 48 _cell_measurement_theta_min 4.20 _cell_measurement_theta_max 14.20 _exptl_crystal_description prizm _exptl_crystal_colour yellow _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.875 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 616 _exptl_absorpt_coefficient_mu 1.500 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 P3/PC' _diffrn_measurement_method '\q/2\q scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 2 _diffrn_standards_interval_count 98 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 2 _diffrn_reflns_number 5037 _diffrn_reflns_av_R_equivalents 0.0178 _diffrn_reflns_av_sigmaI/netI 0.0439 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.48 _diffrn_reflns_theta_max 27.06 _reflns_number_total 4741 _reflns_number_gt 3411 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Siemens P3/PC (Siemens, 1989)' _computing_cell_refinement 'Siemens P3/PC (Siemens, 1989)' _computing_data_reduction 'Siemens P3/PC (Siemens, 1989)' _computing_structure_solution 'SHELXTL PLUS 5 (Sheldrick, 1998)' _computing_structure_refinement 'SHELXTL PLUS 5 (Sheldrick, 1998)' _computing_molecular_graphics 'SHELXTL PLUS 5 (Sheldrick, 1998)' _computing_publication_material 'SHELXTL PLUS 5 (Sheldrick, 1998)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0587P)^2^] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4741 _refine_ls_number_parameters 237 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0673 _refine_ls_R_factor_gt 0.0384 _refine_ls_wR_factor_ref 0.1022 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.002 _refine_ls_restrained_S_all 1.002 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S -0.11715(11) 0.78991(9) 0.14316(6) 0.0565(2) Uani 1 1 d . . . S2 S -0.16068(10) 0.56932(9) 0.17369(6) 0.0566(2) Uani 1 1 d . . . S3 S -0.33355(9) 0.55702(10) 0.08049(7) 0.0623(2) Uani 1 1 d . . . S4 S -0.22854(9) 0.55969(9) -0.05340(6) 0.0555(2) Uani 1 1 d . . . S5 S -0.19832(8) 0.78102(9) -0.10580(5) 0.04865(19) Uani 1 1 d . . . Cl1 Cl 0.26918(12) 0.81980(11) 0.14516(7) 0.0719(3) Uani 1 1 d . . . Cl2 Cl 0.14741(10) 0.83438(10) -0.22966(5) 0.0611(2) Uani 1 1 d . . . N1 N 0.2244(3) 0.8351(3) -0.04580(17) 0.0440(5) Uani 1 1 d . . . C1 C 0.1609(3) 0.8197(3) 0.0459(2) 0.0448(6) Uani 1 1 d . . . C2 C 0.0089(3) 0.8000(3) 0.04351(19) 0.0406(6) Uani 1 1 d . . . C3 C -0.0237(3) 0.8011(3) -0.05705(19) 0.0384(6) Uani 1 1 d . . . C4 C 0.1109(3) 0.8224(3) -0.10727(19) 0.0402(6) Uani 1 1 d . . . C5 C 0.3839(3) 0.8612(4) -0.0741(3) 0.0626(9) Uani 1 1 d . . . H5A H 0.4429 0.8538 -0.0163 0.094 Uiso 1 1 calc R . . H5B H 0.3871 0.9592 -0.1133 0.094 Uiso 1 1 calc R . . H5C H 0.4258 0.7877 -0.1112 0.094 Uiso 1 1 calc R . . S1' S 0.70495(8) 0.32109(9) 0.46910(6) 0.0566(2) Uani 1 1 d . . . S2' S 0.78294(9) 0.10031(10) 0.47823(6) 0.0568(2) Uani 1 1 d . . . S3' S 0.78935(9) 0.01519(11) 0.62544(7) 0.0613(2) Uani 1 1 d . . . S4' S 0.56497(10) -0.01458(10) 0.66422(6) 0.0592(2) Uani 1 1 d . . . S5' S 0.46642(9) 0.19458(10) 0.67580(5) 0.0536(2) Uani 1 1 d . . . Cl1' Cl 0.45528(12) 0.43161(11) 0.27682(6) 0.0730(3) Uani 1 1 d . . . Cl2' Cl 0.10029(9) 0.25581(11) 0.58799(7) 0.0658(2) Uani 1 1 d . . . N1' N 0.2629(3) 0.3548(3) 0.42628(18) 0.0467(6) Uani 1 1 d . . . C1' C 0.4121(3) 0.3669(3) 0.3964(2) 0.0450(6) Uani 1 1 d . . . C2' C 0.5071(3) 0.3180(3) 0.4735(2) 0.0419(6) Uani 1 1 d . . . C3' C 0.4121(3) 0.2693(3) 0.5563(2) 0.0422(6) Uani 1 1 d . . . C4' C 0.2645(3) 0.2930(3) 0.5243(2) 0.0437(6) Uani 1 1 d . . . C5' C 0.1280(4) 0.3994(4) 0.3641(3) 0.0670(9) Uani 1 1 d . . . H5'C H 0.1386 0.4956 0.3240 0.101 Uiso 1 1 calc R . . H5'A H 0.0376 0.4047 0.4048 0.101 Uiso 1 1 calc R . . H5'B H 0.1198 0.3272 0.3231 0.101 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 S1 0.0757(5) 0.0503(4) 0.0445(4) -0.0143(3) 0.0158(4) -0.0068(4) S2 0.0631(5) 0.0526(5) 0.0491(4) 0.0036(3) 0.0040(4) -0.0083(4) S3 0.0455(4) 0.0656(5) 0.0704(5) 0.0038(4) 0.0059(4) -0.0132(4) S4 0.0551(4) 0.0525(4) 0.0613(5) -0.0108(4) -0.0062(4) -0.0145(4) S5 0.0402(4) 0.0538(4) 0.0481(4) 0.0027(3) -0.0103(3) -0.0048(3) Cl1 0.0879(6) 0.0711(6) 0.0606(5) -0.0116(4) -0.0344(4) -0.0164(5) Cl2 0.0664(5) 0.0770(6) 0.0393(4) -0.0069(4) 0.0088(3) -0.0140(4) N1 0.0406(12) 0.0410(13) 0.0501(13) -0.0057(10) -0.0055(10) -0.0065(10) C1 0.0530(16) 0.0402(15) 0.0427(15) -0.0078(12) -0.0134(12) -0.0067(12) C2 0.0517(15) 0.0340(13) 0.0360(13) -0.0060(10) -0.0020(11) -0.0038(11) C3 0.0374(13) 0.0350(13) 0.0415(14) -0.0039(11) -0.0032(11) -0.0014(11) C4 0.0420(14) 0.0412(14) 0.0363(13) -0.0043(11) -0.0020(11) -0.0029(11) C5 0.0398(16) 0.063(2) 0.083(2) -0.0058(18) -0.0024(16) -0.0097(15) S1' 0.0407(4) 0.0567(5) 0.0740(5) -0.0115(4) 0.0034(4) -0.0148(3) S2' 0.0461(4) 0.0675(5) 0.0597(5) -0.0232(4) -0.0017(3) 0.0030(4) S3' 0.0509(4) 0.0697(5) 0.0633(5) -0.0155(4) -0.0179(4) 0.0080(4) S4' 0.0614(5) 0.0550(5) 0.0576(5) 0.0006(4) -0.0093(4) -0.0052(4) S5' 0.0532(4) 0.0711(5) 0.0382(4) -0.0172(3) -0.0053(3) 0.0006(4) Cl1' 0.0885(6) 0.0718(6) 0.0505(5) 0.0083(4) 0.0036(4) -0.0065(5) Cl2' 0.0405(4) 0.0886(6) 0.0701(5) -0.0223(5) 0.0102(4) -0.0039(4) N1' 0.0457(13) 0.0445(13) 0.0502(14) -0.0116(11) -0.0087(11) 0.0034(10) C1' 0.0505(16) 0.0390(15) 0.0439(15) -0.0054(12) 0.0010(12) -0.0022(12) C2' 0.0391(13) 0.0384(14) 0.0494(16) -0.0098(12) 0.0000(12) -0.0057(11) C3' 0.0414(14) 0.0432(15) 0.0444(15) -0.0149(12) -0.0041(11) -0.0023(12) C4' 0.0389(14) 0.0463(16) 0.0479(15) -0.0158(12) 0.0017(12) -0.0011(12) C5' 0.059(2) 0.073(2) 0.066(2) -0.0134(18) -0.0219(17) 0.0167(17) _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 S1 C2 1.736(3) . ? S1 S2 2.0530(12) . ? S2 S3 2.0564(13) . ? S3 S4 2.0440(13) . ? S4 S5 2.0587(12) . ? S5 C3 1.738(3) . ? Cl1 C1 1.705(3) . ? Cl2 C4 1.705(3) . ? N1 C1 1.361(4) . ? N1 C4 1.363(3) . ? N1 C5 1.470(4) . ? C1 C2 1.366(4) . ? C2 C3 1.436(4) . ? C3 C4 1.362(4) . ? S1' C2' 1.739(3) . ? S1' S2' 2.0514(13) . ? S2' S3' 2.0501(13) . ? S3' S4' 2.0536(13) . ? S4' S5' 2.0548(13) . ? S5' C3' 1.740(3) . ? Cl1' C1' 1.700(3) . ? Cl2' C4' 1.693(3) . ? N1' C1' 1.368(4) . ? N1' C4' 1.374(4) . ? N1' C5' 1.472(4) . ? C1' C2' 1.363(4) . ? C2' C3' 1.425(4) . ? C3' C4' 1.370(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 C2 S1 S2 103.78(10) . . ? S1 S2 S3 104.14(5) . . ? S4 S3 S2 105.04(5) . . ? S3 S4 S5 104.86(5) . . ? C3 S5 S4 102.69(9) . . ? C1 N1 C4 106.7(2) . . ? C1 N1 C5 127.1(2) . . ? C4 N1 C5 126.2(2) . . ? N1 C1 C2 110.5(2) . . ? N1 C1 Cl1 121.1(2) . . ? C2 C1 Cl1 128.4(2) . . ? C1 C2 C3 106.2(2) . . ? C1 C2 S1 125.2(2) . . ? C3 C2 S1 128.5(2) . . ? C4 C3 C2 105.7(2) . . ? C4 C3 S5 126.7(2) . . ? C2 C3 S5 127.5(2) . . ? C3 C4 N1 110.9(2) . . ? C3 C4 Cl2 128.6(2) . . ? N1 C4 Cl2 120.5(2) . . ? C2' S1' S2' 103.29(10) . . ? S3' S2' S1' 104.72(5) . . ? S2' S3' S4' 104.04(5) . . ? S3' S4' S5' 104.91(5) . . ? C3' S5' S4' 102.67(10) . . ? C1' N1' C4' 106.8(2) . . ? C1' N1' C5' 126.0(3) . . ? C4' N1' C5' 127.2(3) . . ? C2' C1' N1' 110.3(2) . . ? C2' C1' Cl1' 129.6(2) . . ? N1' C1' Cl1' 120.1(2) . . ? C1' C2' C3' 106.6(2) . . ? C1' C2' S1' 125.5(2) . . ? C3' C2' S1' 127.9(2) . . ? C4' C3' C2' 106.4(2) . . ? C4' C3' S5' 125.2(2) . . ? C2' C3' S5' 128.4(2) . . ? C3' C4' N1' 109.8(2) . . ? C3' C4' Cl2' 129.0(2) . . ? N1' C4' Cl2' 121.2(2) . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.06 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.427 _refine_diff_density_min -0.417 _refine_diff_density_rms 0.075 _publ_section_references ; Sheldrick G.M. (1998). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. Siemens (1989). P3 and XDISK. Release 4.1. Siemens AXS, Madison, Wisconsin, USA. ; data_asam _database_code_depnum_ccdc_archive 'CCDC 274836' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 6,8-Dichloro-7-t-butyl-7H-[1,2,3,4,5]pentathiepino[6,7-c]pyrrole ; _chemical_name_common ;6,8-Dichloro-7-t-butyl-7H-(1,2,3,4,5)pentathiepino(6,7- c)pyrrole ; _chemical_melting_point '102-104 deg. C' _chemical_formula_moiety 'C8 H9 Cl2 N S5' _chemical_formula_sum 'C8 H9 Cl2 N S5' _chemical_formula_weight 350.36 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/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 8.7306(12) _cell_length_b 9.4354(13) _cell_length_c 16.064(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.761(3) _cell_angle_gamma 90.00 _cell_volume 1320.5(3) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1024 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 29.45 _exptl_crystal_description prizm _exptl_crystal_colour yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.762 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 1.252 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.797 _exptl_absorpt_correction_T_max 0.826 _exptl_absorpt_process_details 'SADABS(Sheldrick, 1998a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'Bruker SMART 1000 CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6930 _diffrn_reflns_av_R_equivalents 0.0136 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3674 _reflns_number_gt 3192 _reflns_threshold_expression I>2/s(I) _computing_data_collection 'SMART (Bruker, 1998b)' _computing_cell_refinement 'SMART (Bruker, 1998b)' _computing_data_reduction 'SAINTPlus (Bruker, 1998a)' _computing_structure_solution 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_structure_refinement 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_molecular_graphics 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _computing_publication_material 'SHELXTL ver. 5.1 (Sheldrick, 1998b)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+2.5767P] 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 refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3674 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0416 _refine_ls_R_factor_gt 0.0362 _refine_ls_wR_factor_ref 0.0876 _refine_ls_wR_factor_gt 0.0841 _refine_ls_goodness_of_fit_ref 0.978 _refine_ls_restrained_S_all 0.978 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.22771(6) 1.22489(5) -0.13169(3) 0.02023(11) Uani 1 1 d . . . S2 S 0.02237(6) 1.27268(6) -0.08301(3) 0.02281(12) Uani 1 1 d . . . S3 S 0.07993(7) 1.32669(6) 0.03904(3) 0.02496(12) Uani 1 1 d . . . S4 S 0.10847(6) 1.13391(6) 0.09795(3) 0.02172(12) Uani 1 1 d . . . S5 S 0.32442(6) 1.07013(5) 0.06952(3) 0.01887(11) Uani 1 1 d . . . Cl1 Cl 0.20255(6) 0.95537(6) -0.26671(3) 0.02301(11) Uani 1 1 d . . . Cl2 Cl 0.35993(6) 0.72505(5) 0.03871(3) 0.02202(11) Uani 1 1 d . . . N1 N 0.30224(19) 0.81143(17) -0.12468(10) 0.0157(3) Uani 1 1 d . . . C1 C 0.2596(2) 0.9384(2) -0.16337(12) 0.0163(3) Uani 1 1 d . . . C2 C 0.2588(2) 1.0470(2) -0.10658(12) 0.0167(3) Uani 1 1 d . . . C3 C 0.2970(2) 0.9853(2) -0.02689(11) 0.0158(3) Uani 1 1 d . . . C4 C 0.3201(2) 0.8433(2) -0.04040(12) 0.0156(3) Uani 1 1 d . . . C5 C 0.3419(2) 0.6770(2) -0.17157(12) 0.0183(4) Uani 1 1 d . . . C6 C 0.4608(3) 0.7143(2) -0.23468(13) 0.0222(4) Uani 1 1 d . . . H6A H 0.5512 0.7522 -0.2056 0.033 Uiso 1 1 calc R . . H6B H 0.4182 0.7835 -0.2734 0.033 Uiso 1 1 calc R . . H6D H 0.4871 0.6304 -0.2644 0.033 Uiso 1 1 calc R . . C7 C 0.1939(3) 0.6156(2) -0.21394(14) 0.0261(4) Uani 1 1 d . . . H7A H 0.1233 0.5939 -0.1724 0.039 Uiso 1 1 calc R . . H7D H 0.2175 0.5307 -0.2435 0.039 Uiso 1 1 calc R . . H7B H 0.1485 0.6838 -0.2524 0.039 Uiso 1 1 calc R . . C8 C 0.4156(3) 0.5634(2) -0.11413(14) 0.0255(4) Uani 1 1 d . . . H8D H 0.3453 0.5365 -0.0734 0.038 Uiso 1 1 calc R . . H8A H 0.5078 0.6002 -0.0863 0.038 Uiso 1 1 calc R . . H8B H 0.4400 0.4819 -0.1466 0.038 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 S1 0.0245(3) 0.0144(2) 0.0223(2) 0.00185(17) 0.00583(19) 0.00104(17) S2 0.0226(3) 0.0224(2) 0.0234(2) 0.00114(18) 0.00138(19) 0.00683(19) S3 0.0303(3) 0.0202(2) 0.0247(2) -0.00326(19) 0.0042(2) 0.0061(2) S4 0.0215(3) 0.0241(2) 0.0201(2) -0.00020(18) 0.00512(18) 0.00274(18) S5 0.0176(2) 0.0218(2) 0.0169(2) -0.00499(17) -0.00083(17) 0.00088(17) Cl1 0.0289(3) 0.0245(2) 0.0150(2) -0.00013(17) -0.00305(18) 0.00306(19) Cl2 0.0280(3) 0.0203(2) 0.0175(2) 0.00303(16) -0.00071(18) 0.00520(18) N1 0.0172(8) 0.0146(7) 0.0151(7) -0.0011(6) 0.0000(6) 0.0006(6) C1 0.0149(9) 0.0188(9) 0.0150(8) -0.0006(7) 0.0000(6) -0.0001(6) C2 0.0160(9) 0.0155(8) 0.0186(8) -0.0010(7) 0.0019(7) -0.0010(6) C3 0.0162(9) 0.0175(8) 0.0137(8) -0.0020(6) 0.0005(6) -0.0017(7) C4 0.0144(8) 0.0158(8) 0.0165(8) 0.0004(6) -0.0002(6) 0.0008(6) C5 0.0215(10) 0.0149(8) 0.0187(8) -0.0043(7) 0.0026(7) -0.0014(7) C6 0.0247(11) 0.0229(10) 0.0193(9) -0.0024(7) 0.0043(8) 0.0002(8) C7 0.0265(11) 0.0242(10) 0.0278(10) -0.0083(8) 0.0019(8) -0.0065(8) C8 0.0353(12) 0.0151(9) 0.0263(10) -0.0007(8) 0.0044(9) 0.0044(8) _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 S1 C2 1.743(2) . ? S1 S2 2.0526(8) . ? S2 S3 2.0559(8) . ? S3 S4 2.0580(8) . ? S4 S5 2.0587(7) . ? S5 C3 1.7460(19) . ? Cl1 C1 1.709(2) . ? Cl2 C4 1.710(2) . ? N1 C4 1.386(2) . ? N1 C1 1.389(2) . ? N1 C5 1.526(2) . ? C1 C2 1.372(3) . ? C2 C3 1.426(3) . ? C3 C4 1.374(3) . ? C5 C8 1.529(3) . ? C5 C7 1.534(3) . ? C5 C6 1.538(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 C2 S1 S2 104.47(7) . . ? S1 S2 S3 104.65(3) . . ? S2 S3 S4 103.54(3) . . ? S3 S4 S5 103.97(3) . . ? C3 S5 S4 104.85(7) . . ? C4 N1 C1 105.06(15) . . ? C4 N1 C5 130.37(16) . . ? C1 N1 C5 123.96(16) . . ? C2 C1 N1 111.07(17) . . ? C2 C1 Cl1 124.18(16) . . ? N1 C1 Cl1 124.59(14) . . ? C1 C2 C3 106.30(17) . . ? C1 C2 S1 124.93(16) . . ? C3 C2 S1 128.66(15) . . ? C4 C3 C2 106.54(16) . . ? C4 C3 S5 125.03(15) . . ? C2 C3 S5 128.28(15) . . ? C3 C4 N1 110.94(17) . . ? C3 C4 Cl2 122.93(15) . . ? N1 C4 Cl2 126.11(14) . . ? N1 C5 C8 112.66(16) . . ? N1 C5 C7 108.73(17) . . ? C8 C5 C7 108.15(18) . . ? N1 C5 C6 108.67(15) . . ? C8 C5 C6 106.42(17) . . ? C7 C5 C6 112.26(17) . . ? _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.512 _refine_diff_density_min -0.446 _refine_diff_density_rms 0.093 _publ_section_references ; Bruker (1998a) SAINTPlus Data Reduction and Correction Program v. 6.01, Bruker AXS, Madison, Wisconsin, USA. Bruker (1998b) SMART. Bruker Molecular Analysis Research Tool, v. 5.059. Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (1998a). SADABS v.2.01, Bruker/Siemens Area Detector Absorption Correction Program, Bruker AXS, Madison, Wisconsin, USA. Sheldrick G.M. (1998b). SHELXTL v. 5.10, Structure Determination Software Suite, Bruker AXS, Madison, Wisconsin, USA. ;