# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Garner, C.' _publ_contact_author_name 'Garner, C.' _publ_contact_author_email dave.garner@nottingham.ac.uk _publ_section_title ; A radical pathway to synthesise Mo and W dithiolene complexes ; # Attachment '1.CIF' data_mos4cp _database_code_depnum_ccdc_archive 'CCDC 798374' #TrackingRef '1.CIF' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H21 Mo N S2' _chemical_formula_sum 'C22 H21 Mo N S2' _chemical_formula_weight 459.46 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Mo Mo -1.6832 0.6857 '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 monoclinic _symmetry_space_group_name_H-M 'P 21/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 11.5767(11) _cell_length_b 11.6673(11) _cell_length_c 14.6500(14) _cell_angle_alpha 90.00 _cell_angle_beta 95.112(2) _cell_angle_gamma 90.00 _cell_volume 1970.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 3798 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 54.9 _exptl_crystal_description 'rhombic plate' _exptl_crystal_colour 'dark red' _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.548 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 936 _exptl_absorpt_coefficient_mu 0.883 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.721 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details 'sadabs v2.05' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 12426 _diffrn_reflns_av_R_equivalents 0.059 _diffrn_reflns_av_sigmaI/netI 0.073 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 4690 _reflns_number_gt 3518 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ' ? ' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2009)' _refine_special_details ; ? ; _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^)+(0.009P)^2^+2.84P] 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 4467 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1032 _refine_ls_wR_factor_gt 0.0910 _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags Mo1 Mo Uani 0.68104(2) 0.14045(2) 0.36808(2) 1.000 0.0166(1) . . S1 S Uani 0.60047(7) 0.17630(7) 0.51255(6) 1.000 0.0210(2) . . S2 S Uani 0.73651(7) 0.33998(7) 0.38750(6) 1.000 0.0201(2) . . N1 N Uani 0.4336(3) 0.2367(3) 0.6936(2) 1.000 0.0359(11) . . C1 C Uani 0.5178(3) 0.2764(3) 0.6731(2) 1.000 0.0246(11) . . C2 C Uani 0.7263(4) 0.2801(5) 0.7114(3) 1.000 0.0556(19) . . C3 C Uani 0.6103(4) 0.4614(4) 0.6823(3) 1.000 0.0480(16) . . C4 C Uani 0.6257(3) 0.3354(3) 0.6520(2) 1.000 0.0281(11) . . C5 C Uani 0.6445(3) 0.3155(3) 0.5509(2) 1.000 0.0189(9) . . C6 C Uani 0.7014(3) 0.3841(3) 0.4978(2) 1.000 0.0198(9) . . C7 C Uani 0.7486(3) 0.5011(3) 0.5174(2) 1.000 0.0190(9) . . C8 C Uani 0.8640(3) 0.5157(3) 0.5514(2) 1.000 0.0226(10) . . C9 C Uani 0.9109(3) 0.6244(3) 0.5648(3) 1.000 0.0278(11) . . C10 C Uani 0.8434(3) 0.7202(3) 0.5441(2) 1.000 0.0249(11) . . C11 C Uani 0.7280(3) 0.7073(3) 0.5113(3) 1.000 0.0259(11) . . C12 C Uani 0.6814(3) 0.5988(3) 0.4979(2) 1.000 0.0237(10) . . C1A C Uani 0.8825(3) 0.1232(3) 0.3721(3) 1.000 0.0245(10) . . C2A C Uani 0.8356(3) 0.0334(3) 0.3169(3) 1.000 0.0267(11) . . C3A C Uani 0.7729(3) -0.0402(3) 0.3718(3) 1.000 0.0305(11) . . C4A C Uani 0.7796(3) 0.0047(3) 0.4611(3) 1.000 0.0303(11) . . C5A C Uani 0.8467(3) 0.1065(3) 0.4615(2) 1.000 0.0255(11) . . C6A C Uani 0.4911(3) 0.1891(4) 0.3167(3) 1.000 0.0340(12) . . C7A C Uani 0.5036(3) 0.0680(4) 0.3192(3) 1.000 0.0342(14) . . C8A C Uani 0.5788(4) 0.0406(4) 0.2516(3) 1.000 0.0363(12) . . C9A C Uani 0.6142(4) 0.1425(4) 0.2115(3) 1.000 0.0360(13) . . C10A C Uani 0.5571(4) 0.2326(4) 0.2510(3) 1.000 0.0368(12) . . H1AA H Uiso 0.75050 -0.03300 0.51590 1.000 0.0360 calc R H2AA H Uiso 0.73570 -0.11440 0.35160 1.000 0.0360 calc R H3AA H Uiso 0.84980 0.01970 0.25150 1.000 0.0320 calc R H4AA H Uiso 0.93740 0.18330 0.35360 1.000 0.0290 calc R H5AA H Uiso 0.87390 0.15210 0.51720 1.000 0.0310 calc R H6AA H Uiso 0.45690 0.01280 0.35310 1.000 0.0410 calc R H7AA H Uiso 0.59720 -0.03860 0.23120 1.000 0.0430 calc R H8AA H Uiso 0.66340 0.14850 0.15900 1.000 0.0430 calc R H9AA H Uiso 0.56130 0.31500 0.23300 1.000 0.0440 calc R H2A H Uiso 0.73560 0.20040 0.69210 1.000 0.0830 calc R H2B H Uiso 0.70960 0.28180 0.77580 1.000 0.0830 calc R H2C H Uiso 0.79790 0.32260 0.70420 1.000 0.0830 calc R H3A H Uiso 0.59940 0.46370 0.74780 1.000 0.0720 calc R H3B H Uiso 0.54220 0.49460 0.64740 1.000 0.0720 calc R H3C H Uiso 0.67940 0.50570 0.67070 1.000 0.0720 calc R H8A H Uiso 0.91110 0.45030 0.56550 1.000 0.0270 calc R H9A H Uiso 0.98960 0.63300 0.58840 1.000 0.0330 calc R H10A H Uiso 0.43680 0.23450 0.35200 1.000 0.0410 calc R H10B H Uiso 0.87600 0.79470 0.55220 1.000 0.0300 calc R H11A H Uiso 0.68100 0.77300 0.49810 1.000 0.0310 calc R H12A H Uiso 0.60250 0.59070 0.47500 1.000 0.0280 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 Mo1 0.0182(2) 0.0149(2) 0.0170(2) -0.0011(1) 0.0033(1) -0.0026(1) S1 0.0254(4) 0.0191(4) 0.0195(4) -0.0010(3) 0.0070(3) -0.0058(3) S2 0.0266(4) 0.0160(4) 0.0183(4) 0.0001(3) 0.0056(3) -0.0044(3) N1 0.041(2) 0.036(2) 0.0326(18) -0.0100(15) 0.0147(15) -0.0128(16) C1 0.033(2) 0.0246(19) 0.0170(17) -0.0037(14) 0.0074(14) -0.0055(15) C2 0.033(2) 0.110(5) 0.023(2) 0.004(2) -0.0017(18) 0.001(3) C3 0.062(3) 0.049(3) 0.038(2) -0.028(2) 0.032(2) -0.033(2) C4 0.0241(18) 0.040(2) 0.0210(18) -0.0080(15) 0.0063(14) -0.0098(15) C5 0.0179(16) 0.0212(17) 0.0177(16) -0.0054(13) 0.0028(12) -0.0019(13) C6 0.0192(16) 0.0199(17) 0.0202(16) -0.0030(13) 0.0011(12) 0.0008(13) C7 0.0206(16) 0.0193(17) 0.0177(16) -0.0016(13) 0.0056(13) -0.0022(13) C8 0.0195(17) 0.0199(17) 0.0278(18) -0.0008(14) -0.0005(14) -0.0004(13) C9 0.0198(17) 0.030(2) 0.033(2) -0.0041(16) -0.0006(14) -0.0049(14) C10 0.0297(19) 0.0183(17) 0.0265(19) -0.0074(14) 0.0022(14) -0.0060(14) C11 0.0249(18) 0.0182(18) 0.034(2) -0.0019(15) -0.0011(15) -0.0002(14) C12 0.0188(16) 0.0240(18) 0.0279(18) -0.0021(15) 0.0007(13) -0.0024(14) C1A 0.0155(16) 0.0233(18) 0.035(2) -0.0023(15) 0.0039(14) 0.0001(13) C2A 0.0209(17) 0.0258(19) 0.034(2) -0.0073(16) 0.0052(15) 0.0034(14) C3A 0.0277(19) 0.0142(17) 0.050(2) -0.0032(16) 0.0053(17) 0.0021(14) C4A 0.033(2) 0.0225(19) 0.036(2) 0.0085(16) 0.0064(16) 0.0064(15) C5A 0.0242(18) 0.0267(19) 0.0247(18) -0.0002(15) -0.0032(14) 0.0030(14) C6A 0.027(2) 0.043(2) 0.030(2) -0.0071(18) -0.0080(16) 0.0100(17) C7A 0.027(2) 0.045(3) 0.029(2) 0.0088(18) -0.0071(15) -0.0189(17) C8A 0.043(2) 0.032(2) 0.031(2) -0.0125(17) -0.0122(17) 0.0031(18) C9A 0.033(2) 0.058(3) 0.0170(18) 0.0046(18) 0.0019(15) -0.0046(19) C10A 0.041(2) 0.030(2) 0.035(2) 0.0095(17) -0.0207(18) -0.0063(18) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag Mo1 S1 2.4242(9) . . yes Mo1 S2 2.4249(9) . . yes Mo1 C1A 2.336(4) . . yes Mo1 C2A 2.359(4) . . yes Mo1 C3A 2.359(4) . . yes Mo1 C4A 2.322(4) . . yes Mo1 C5A 2.289(3) . . yes Mo1 C6A 2.330(4) . . yes Mo1 C7A 2.277(4) . . yes Mo1 C8A 2.304(5) . . yes Mo1 C9A 2.355(4) . . yes Mo1 C10A 2.391(5) . . yes S1 C5 1.778(4) . . yes S2 C6 1.777(3) . . yes N1 C1 1.143(5) . . yes C1 C4 1.483(5) . . no C2 C4 1.533(6) . . no C3 C4 1.551(6) . . no C4 C5 1.534(4) . . no C5 C6 1.331(5) . . no C6 C7 1.489(5) . . no C7 C8 1.394(5) . . no C7 C12 1.395(5) . . no C8 C9 1.387(5) . . no C9 C10 1.382(5) . . no C10 C11 1.387(5) . . no C11 C12 1.383(5) . . no C1A C2A 1.403(5) . . no C1A C5A 1.422(5) . . no C2A C3A 1.420(5) . . no C3A C4A 1.405(6) . . no C4A C5A 1.419(5) . . no C6A C7A 1.420(7) . . no C6A C10A 1.378(6) . . no C7A C8A 1.412(6) . . no C8A C9A 1.403(7) . . no C9A C10A 1.395(7) . . no C2 H2A 0.9800 . . no C2 H2B 0.9800 . . no C2 H2C 0.9800 . . no C3 H3A 0.9800 . . no C3 H3B 0.9800 . . no C3 H3C 0.9800 . . no C8 H8A 0.9500 . . no C9 H9A 0.9500 . . no C10 H10B 0.9500 . . no C11 H11A 0.9500 . . no C12 H12A 0.9500 . . no C1A H4AA 1.0000 . . no C2A H3AA 1.0000 . . no C3A H2AA 1.0000 . . no C4A H1AA 1.0000 . . no C5A H5AA 1.0000 . . no C6A H10A 1.0000 . . no C7A H6AA 1.0000 . . no C8A H7AA 1.0000 . . no C9A H8AA 1.0000 . . no C10A H9AA 1.0000 . . no 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag S1 Mo1 S2 81.39(3) . . . yes S1 Mo1 C1A 116.98(11) . . . yes S1 Mo1 C2A 136.95(11) . . . yes S1 Mo1 C3A 109.98(11) . . . yes S1 Mo1 C4A 79.19(10) . . . yes S1 Mo1 C5A 82.81(8) . . . yes S1 Mo1 C6A 79.31(11) . . . yes S1 Mo1 C7A 86.11(11) . . . yes S1 Mo1 C8A 121.44(12) . . . yes S1 Mo1 C9A 136.90(12) . . . yes S1 Mo1 C10A 107.20(11) . . . yes S2 Mo1 C1A 80.00(9) . . . yes S2 Mo1 C2A 110.20(9) . . . yes S2 Mo1 C3A 137.80(9) . . . yes S2 Mo1 C4A 118.35(9) . . . yes S2 Mo1 C5A 84.09(9) . . . yes S2 Mo1 C6A 92.09(12) . . . yes S2 Mo1 C7A 127.98(12) . . . yes S2 Mo1 C8A 133.27(12) . . . yes S2 Mo1 C9A 99.51(12) . . . yes S2 Mo1 C10A 77.77(11) . . . yes C1A Mo1 C2A 34.77(13) . . . yes C1A Mo1 C3A 58.37(12) . . . yes C1A Mo1 C4A 59.28(13) . . . yes C1A Mo1 C5A 35.79(13) . . . yes C1A Mo1 C6A 160.11(15) . . . yes C1A Mo1 C7A 147.83(14) . . . yes C1A Mo1 C8A 114.89(15) . . . yes C1A Mo1 C9A 105.43(16) . . . yes C1A Mo1 C10A 126.20(15) . . . yes C2A Mo1 C3A 35.02(13) . . . yes C2A Mo1 C4A 58.55(14) . . . yes C2A Mo1 C5A 58.64(13) . . . yes C2A Mo1 C6A 138.35(15) . . . yes C2A Mo1 C7A 113.09(14) . . . yes C2A Mo1 C8A 81.43(15) . . . yes C2A Mo1 C9A 83.60(15) . . . yes C2A Mo1 C10A 115.71(15) . . . yes C3A Mo1 C4A 34.92(15) . . . yes C3A Mo1 C5A 58.65(13) . . . yes C3A Mo1 C6A 129.46(14) . . . yes C3A Mo1 C7A 93.89(14) . . . yes C3A Mo1 C8A 76.48(15) . . . yes C3A Mo1 C9A 98.04(16) . . . yes C3A Mo1 C10A 131.20(15) . . . yes C4A Mo1 C5A 35.84(12) . . . yes C4A Mo1 C6A 139.12(14) . . . yes C4A Mo1 C7A 108.28(14) . . . yes C4A Mo1 C8A 106.43(15) . . . yes C4A Mo1 C9A 132.87(15) . . . yes C4A Mo1 C10A 163.71(15) . . . yes C5A Mo1 C6A 162.09(13) . . . yes C5A Mo1 C7A 143.90(14) . . . yes C5A Mo1 C8A 134.66(14) . . . yes C5A Mo1 C9A 140.29(14) . . . yes C5A Mo1 C10A 157.49(14) . . . yes C6A Mo1 C7A 35.89(16) . . . yes C6A Mo1 C8A 58.42(16) . . . yes C6A Mo1 C9A 57.60(16) . . . yes C6A Mo1 C10A 33.91(15) . . . yes C7A Mo1 C8A 35.90(16) . . . yes C7A Mo1 C9A 59.24(16) . . . yes C7A Mo1 C10A 58.30(16) . . . yes C8A Mo1 C9A 35.04(16) . . . yes C8A Mo1 C10A 57.34(16) . . . yes C9A Mo1 C10A 34.17(16) . . . yes Mo1 S1 C5 108.16(11) . . . yes Mo1 S2 C6 107.77(12) . . . yes N1 C1 C4 175.3(4) . . . yes Mo1 C1A C2A 73.5(2) . . . yes Mo1 C1A C5A 70.3(2) . . . yes Mo1 C2A C1A 71.8(2) . . . yes Mo1 C2A C3A 72.5(2) . . . yes Mo1 C3A C2A 72.5(2) . . . yes Mo1 C3A C4A 71.1(2) . . . yes Mo1 C4A C3A 74.0(2) . . . yes Mo1 C4A C5A 70.8(2) . . . yes Mo1 C5A C1A 73.92(19) . . . yes Mo1 C5A C4A 73.3(2) . . . yes Mo1 C6A C7A 70.0(2) . . . yes Mo1 C6A C10A 75.5(2) . . . yes Mo1 C6A C7A 70.0(2) . . . yes Mo1 C6A C10A 75.5(2) . . . yes Mo1 C7A C6A 74.1(2) . . . yes Mo1 C7A C8A 73.1(2) . . . yes Mo1 C8A C7A 71.0(2) . . . yes Mo1 C8A C9A 74.4(3) . . . yes Mo1 C9A C8A 70.5(3) . . . yes Mo1 C9A C10A 74.4(3) . . . yes Mo1 C10A C6A 70.6(2) . . . yes Mo1 C10A C9A 71.5(3) . . . yes C1 C4 C2 107.3(3) . . . no C1 C4 C3 105.1(3) . . . no C1 C4 C5 109.0(3) . . . no C2 C4 C3 109.7(3) . . . no C2 C4 C5 108.6(3) . . . no C3 C4 C5 116.7(3) . . . no S1 C5 C4 112.5(2) . . . yes S1 C5 C6 120.5(2) . . . yes C4 C5 C6 126.4(3) . . . no S2 C6 C5 121.5(3) . . . yes S2 C6 C7 109.3(2) . . . yes C5 C6 C7 129.1(3) . . . no C6 C7 C8 120.3(3) . . . no C6 C7 C12 121.4(3) . . . no C8 C7 C12 118.2(3) . . . no C7 C8 C9 120.9(3) . . . no C8 C9 C10 120.1(3) . . . no C9 C10 C11 119.8(3) . . . no C10 C11 C12 120.0(3) . . . no C7 C12 C11 121.0(3) . . . no C1A C2A C3A 108.4(4) . . . no C1A C5A C4A 108.4(3) . . . no C2A C3A C4A 108.3(3) . . . no C2A C1A C5A 107.4(3) . . . no C3A C4A C5A 107.5(3) . . . no C6A C10A C9A 109.0(4) . . . no C6A C7A C8A 106.0(4) . . . no C7A C6A C10A 108.8(4) . . . no C7A C6A C10A 108.8(4) . . . no C7A C8A C9A 108.9(4) . . . no C8A C9A C10A 107.3(4) . . . no Mo1 C2A H3AA 126.00 . . . no Mo1 C1A H4AA 126.00 . . . no Mo1 C3A H2AA 126.00 . . . no Mo1 C4A H1AA 126.00 . . . no Mo1 C5A H5AA 126.00 . . . no Mo1 C6A H10A 125.00 . . . no Mo1 C7A H6AA 127.00 . . . no Mo1 C8A H7AA 125.00 . . . no Mo1 C9A H8AA 126.00 . . . no Mo1 C10A H9AA 126.00 . . . no C4 C2 H2A 109.00 . . . no C4 C2 H2B 109.00 . . . no C4 C2 H2C 109.00 . . . no C4 C3 H3A 110.00 . . . no C4 C3 H3B 109.00 . . . no C4 C3 H3C 110.00 . . . no C7 C8 H8A 120.00 . . . no C7 C12 H12A 119.00 . . . no C8 C9 H9A 120.00 . . . no C9 C8 H8A 120.00 . . . no C9 C10 H10B 120.00 . . . no C10 C9 H9A 120.00 . . . no C10 C11 H11A 120.00 . . . no C11 C10 H10B 120.00 . . . no C11 C12 H12A 119.00 . . . no C12 C11 H11A 120.00 . . . no C1A C2A H3AA 126.00 . . . no C1A C5A H5AA 126.00 . . . no C2A C3A H2AA 126.00 . . . no C2A C1A H4AA 126.00 . . . no C3A C2A H3AA 126.00 . . . no C3A C4A H1AA 126.00 . . . no C4A C3A H2AA 126.00 . . . no C4A C5A H5AA 125.00 . . . no C5A C4A H1AA 126.00 . . . no C5A C1A H4AA 126.00 . . . no C6A C7A H6AA 126.00 . . . no C6A C10A H9AA 126.00 . . . no C7A C6A H10A 125.00 . . . no C7A C8A H7AA 125.00 . . . no C8A C7A H6AA 127.00 . . . no C8A C9A H8AA 126.00 . . . no C9A C8A H7AA 125.00 . . . no C9A C10A H9AA 125.00 . . . no C10A C6A H10A 125.00 . . . no C10A C9A H8AA 126.00 . . . no H2A C2 H2B 109.00 . . . no H2A C2 H2C 109.00 . . . no H2B C2 H2C 110.00 . . . no H3A C3 H3B 109.00 . . . no H3A C3 H3C 110.00 . . . no H3B C3 H3C 109.00 . . . no _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.48 _refine_diff_density_min -0.79 _refine_diff_density_rms 0.11 #===END of CIF # Attachment '2.CIF' data_cpwscn _database_code_depnum_ccdc_archive 'CCDC 798375' #TrackingRef '2.CIF' _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H21 N S2 W' _chemical_formula_sum 'C22 H21 N S2 W' _chemical_formula_weight 547.37 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' W W -0.8490 6.8722 '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/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 11.6111(9) _cell_length_b 11.7045(9) _cell_length_c 14.5830(12) _cell_angle_alpha 90.00 _cell_angle_beta 95.084(1) _cell_angle_gamma 90.00 _cell_volume 1974.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 9093 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.5 _exptl_crystal_description lath _exptl_crystal_colour red _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.842 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1064 _exptl_absorpt_coefficient_mu 6.069 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.514 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS version 2.10; Sheldrick, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 17400 _diffrn_reflns_av_R_equivalents 0.074 _diffrn_reflns_av_sigmaI/netI 0.019 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4498 _reflns_number_gt 3976 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ' ?' _computing_publication_material 'enCIFer(Allen et al.,2004);PLATON(Spek,2009)' _refine_special_details ; ? ; _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^)+(0.025P)^2^+1.554P] 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 4498 _refine_ls_number_parameters 235 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0258 _refine_ls_R_factor_gt 0.0205 _refine_ls_wR_factor_ref 0.0487 _refine_ls_wR_factor_gt 0.0462 _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_restrained_S_all 1.04 _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 W1 W 0.681256(10) 0.140126(9) 0.869317(8) 0.02266(5) Uani 1 1 d . . . S1 S 0.60278(7) 0.17662(6) 1.01408(5) 0.02767(16) Uani 1 1 d . . . S2 S 0.73896(7) 0.33778(6) 0.88770(5) 0.02593(15) Uani 1 1 d . . . N1 N 0.4371(3) 0.2350(3) 1.1955(2) 0.0421(7) Uani 1 1 d . . . C1A C 0.7712(3) -0.0414(3) 0.8699(3) 0.0370(8) Uani 1 1 d . . . H1AA H 0.7332 -0.1145 0.8485 0.044 Uiso 1 1 calc R . . C1 C 0.5188(3) 0.2771(3) 1.1741(2) 0.0317(7) Uani 1 1 d . . . C2A C 0.8349(3) 0.0324(3) 0.8159(2) 0.0352(7) Uani 1 1 d . . . H2AA H 0.8493 0.0202 0.7500 0.042 Uiso 1 1 calc R . . C2 C 0.7272(3) 0.2857(5) 1.2129(2) 0.0618(13) Uani 1 1 d . . . H2A H 0.7380 0.2061 1.1946 0.093 Uiso 1 1 calc R . . H2B H 0.7107 0.2884 1.2776 0.093 Uiso 1 1 calc R . . H2C H 0.7978 0.3292 1.2050 0.093 Uiso 1 1 calc R . . C3 C 0.6085(4) 0.4643(3) 1.1809(3) 0.0518(11) Uani 1 1 d . . . H3A H 0.5435 0.4973 1.1422 0.078 Uiso 1 1 calc R . . H3B H 0.6789 0.5078 1.1725 0.078 Uiso 1 1 calc R . . H3C H 0.5922 0.4676 1.2456 0.078 Uiso 1 1 calc R . . C3A C 0.8820(3) 0.1200(3) 0.8730(2) 0.0327(7) Uani 1 1 d . . . H3AA H 0.9372 0.1799 0.8552 0.039 Uiso 1 1 calc R . . C4A C 0.8459(3) 0.1032(3) 0.9622(2) 0.0339(7) Uani 1 1 d . . . H4AA H 0.8738 0.1471 1.0187 0.041 Uiso 1 1 calc R . . C5A C 0.7775(3) 0.0018(3) 0.9602(2) 0.0389(8) Uani 1 1 d . . . H5AA H 0.7480 -0.0368 1.0146 0.047 Uiso 1 1 calc R . . C5 C 0.6454(2) 0.3167(3) 1.0514(2) 0.0259(6) Uani 1 1 d . . . C6 C 0.7027(2) 0.3849(2) 0.9976(2) 0.0249(6) Uani 1 1 d . . . C6A C 0.4885(3) 0.1862(3) 0.8201(2) 0.0415(8) Uani 1 1 d . . . H6AA H 0.4336 0.2280 0.8572 0.050 Uiso 1 1 calc R . . C7A C 0.5055(3) 0.0651(3) 0.8195(2) 0.0401(8) Uani 1 1 d . . . H7AA H 0.4610 0.0066 0.8519 0.048 Uiso 1 1 calc R . . C7 C 0.7496(3) 0.5017(2) 1.01676(19) 0.0256(6) Uani 1 1 d . . . C8 C 0.8644(3) 0.5164(3) 1.0511(2) 0.0297(6) Uani 1 1 d . . . H8A H 0.9115 0.4514 1.0657 0.036 Uiso 1 1 calc R . . C8A C 0.5818(3) 0.0444(3) 0.7505(2) 0.0422(8) Uani 1 1 d . . . H8AA H 0.6024 -0.0325 0.7270 0.051 Uiso 1 1 calc R . . C9A C 0.6126(3) 0.1497(4) 0.7135(2) 0.0468(9) Uani 1 1 d . . . H9AA H 0.6612 0.1603 0.6608 0.056 Uiso 1 1 calc R . . C9 C 0.9107(3) 0.6251(3) 1.0644(2) 0.0333(7) Uani 1 1 d . . . H9A H 0.9888 0.6344 1.0886 0.040 Uiso 1 1 calc R . . C10 C 0.8426(3) 0.7201(3) 1.0424(2) 0.0317(7) Uani 1 1 d . . . H10A H 0.8744 0.7946 1.0504 0.038 Uiso 1 1 calc R . . C10A C 0.5531(3) 0.2348(3) 0.7548(3) 0.0451(9) Uani 1 1 d . . . H10B H 0.5551 0.3179 0.7392 0.054 Uiso 1 1 calc R . . C11 C 0.7287(3) 0.7067(3) 1.0088(2) 0.0321(7) Uani 1 1 d . . . H11A H 0.6819 0.7720 0.9947 0.039 Uiso 1 1 calc R . . C12 C 0.6824(3) 0.5985(3) 0.9956(2) 0.0306(6) Uani 1 1 d . . . H12A H 0.6040 0.5900 0.9719 0.037 Uiso 1 1 calc R . . C023 C 0.6258(3) 0.3380(3) 1.1526(2) 0.0324(7) Uani 1 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 W1 0.02419(7) 0.02051(7) 0.02363(7) -0.00133(4) 0.00409(4) -0.00298(4) S1 0.0325(4) 0.0257(4) 0.0258(4) -0.0005(3) 0.0077(3) -0.0064(3) S2 0.0326(4) 0.0216(3) 0.0243(3) -0.0004(3) 0.0066(3) -0.0048(3) N1 0.0487(18) 0.0408(17) 0.0394(16) -0.0098(13) 0.0185(14) -0.0137(14) C1A 0.0314(16) 0.0211(15) 0.058(2) -0.0061(14) 0.0039(15) 0.0004(13) C1 0.0386(18) 0.0318(17) 0.0254(15) -0.0045(12) 0.0075(13) -0.0036(14) C2A 0.0287(16) 0.0359(18) 0.0419(18) -0.0079(14) 0.0079(14) 0.0040(13) C2 0.039(2) 0.119(4) 0.0271(18) 0.006(2) -0.0026(15) -0.004(2) C3 0.063(2) 0.052(2) 0.044(2) -0.0248(18) 0.0266(19) -0.031(2) C3A 0.0238(15) 0.0303(16) 0.0447(19) -0.0032(14) 0.0072(13) 0.0007(12) C4A 0.0348(17) 0.0310(16) 0.0349(17) -0.0022(13) -0.0031(14) 0.0025(14) C5A 0.0422(19) 0.0295(17) 0.046(2) 0.0086(15) 0.0079(16) 0.0052(14) C5 0.0252(14) 0.0271(15) 0.0253(15) -0.0044(12) 0.0020(11) -0.0022(12) C6 0.0235(14) 0.0242(14) 0.0267(15) -0.0043(11) 0.0007(11) -0.0006(11) C6A 0.0315(17) 0.058(2) 0.0338(18) -0.0104(16) -0.0067(14) 0.0078(16) C7A 0.0336(17) 0.048(2) 0.0370(18) 0.0057(16) -0.0042(14) -0.0170(15) C7 0.0260(14) 0.0261(15) 0.0251(14) -0.0032(11) 0.0040(11) -0.0035(11) C8 0.0247(15) 0.0274(15) 0.0369(17) 0.0003(13) 0.0010(13) 0.0009(12) C8A 0.048(2) 0.043(2) 0.0337(18) -0.0135(15) -0.0085(15) 0.0026(16) C9A 0.040(2) 0.072(3) 0.0285(18) 0.0076(17) 0.0024(15) -0.0037(18) C9 0.0279(16) 0.0321(17) 0.0391(18) -0.0044(13) -0.0008(13) -0.0048(13) C10 0.0353(17) 0.0262(15) 0.0334(16) -0.0049(13) 0.0022(13) -0.0056(13) C10A 0.048(2) 0.0369(19) 0.046(2) 0.0099(16) -0.0205(17) -0.0062(16) C11 0.0328(16) 0.0266(16) 0.0372(17) 0.0011(13) 0.0047(13) 0.0036(13) C12 0.0252(15) 0.0295(16) 0.0371(17) -0.0019(13) 0.0019(13) -0.0002(12) C023 0.0300(16) 0.0437(19) 0.0243(15) -0.0054(13) 0.0058(12) -0.0100(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 W1 S1 2.4105(7) . ? W1 S2 2.4168(7) . ? W1 C1A 2.367(3) . ? W1 C2A 2.372(3) . ? W1 C3A 2.338(3) . ? W1 C4A 2.284(3) . ? W1 C5A 2.316(3) . ? W1 C6A 2.352(3) . ? W1 C7A 2.281(3) . ? W1 C8A 2.288(3) . ? W1 C9A 2.343(4) . ? W1 C10A 2.407(3) . ? S1 C5 1.784(3) . ? S2 C6 1.780(3) . ? N1 C1 1.137(4) . ? C1A C5A 1.406(5) . ? C1A C2A 1.419(5) . ? C1A H1AA 1.0000 . ? C1 C023 1.489(4) . ? C2A C3A 1.401(4) . ? C2A H2AA 1.0000 . ? C2 C023 1.533(5) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C023 1.553(5) . ? C3 H3A 0.9800 . ? C3 H3B 0.9800 . ? C3 H3C 0.9800 . ? C3A C4A 1.416(5) . ? C3A H3AA 1.0000 . ? C4A C5A 1.427(5) . ? C4A H4AA 1.0000 . ? C5A H5AA 1.0000 . ? C5 C6 1.337(4) . ? C5 C023 1.534(4) . ? C6 C7 1.488(4) . ? C6A C10A 1.386(5) . ? C6A C7A 1.431(6) . ? C6A H6AA 1.0000 . ? C7A C8A 1.420(5) . ? C7A H7AA 1.0000 . ? C7 C8 1.392(4) . ? C7 C12 1.395(4) . ? C8 C9 1.388(4) . ? C8 H8A 0.9500 . ? C8A C9A 1.405(5) . ? C8A H8AA 1.0000 . ? C9A C10A 1.380(5) . ? C9A H9AA 1.0000 . ? C9 C10 1.385(4) . ? C9 H9A 0.9500 . ? C10 C11 1.377(4) . ? C10 H10A 0.9500 . ? C10A H10B 1.0000 . ? C11 C12 1.382(4) . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? 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 C7A W1 C4A 142.58(13) . . ? C7A W1 C8A 36.21(13) . . ? C4A W1 C8A 134.10(12) . . ? C7A W1 C5A 106.60(13) . . ? C4A W1 C5A 36.13(12) . . ? C8A W1 C5A 106.03(13) . . ? C7A W1 C3A 146.16(13) . . ? C4A W1 C3A 35.66(12) . . ? C8A W1 C3A 113.77(12) . . ? C5A W1 C3A 59.15(12) . . ? C7A W1 C9A 59.45(13) . . ? C4A W1 C9A 141.20(13) . . ? C8A W1 C9A 35.29(13) . . ? C5A W1 C9A 133.92(13) . . ? C3A W1 C9A 106.25(13) . . ? C7A W1 C6A 35.95(14) . . ? C4A W1 C6A 161.48(12) . . ? C8A W1 C6A 58.56(13) . . ? C5A W1 C6A 137.13(14) . . ? C3A W1 C6A 161.74(13) . . ? C9A W1 C6A 57.32(13) . . ? C7A W1 C1A 92.17(13) . . ? C4A W1 C1A 58.81(12) . . ? C8A W1 C1A 75.88(13) . . ? C5A W1 C1A 34.91(12) . . ? C3A W1 C1A 58.06(11) . . ? C9A W1 C1A 99.12(14) . . ? C6A W1 C1A 127.93(13) . . ? C7A W1 C2A 111.65(13) . . ? C4A W1 C2A 58.65(12) . . ? C8A W1 C2A 80.50(12) . . ? C5A W1 C2A 58.47(12) . . ? C3A W1 C2A 34.59(11) . . ? C9A W1 C2A 84.75(13) . . ? C6A W1 C2A 138.15(12) . . ? C1A W1 C2A 34.85(11) . . ? C7A W1 C10A 58.37(13) . . ? C4A W1 C10A 158.80(12) . . ? C8A W1 C10A 57.36(14) . . ? C5A W1 C10A 163.00(13) . . ? C3A W1 C10A 128.01(13) . . ? C9A W1 C10A 33.75(13) . . ? C6A W1 C10A 33.84(13) . . ? C1A W1 C10A 131.39(13) . . ? C2A W1 C10A 116.99(13) . . ? C7A W1 S1 87.12(9) . . ? C4A W1 S1 82.84(9) . . ? C8A W1 S1 123.04(10) . . ? C5A W1 S1 79.85(9) . . ? C3A W1 S1 116.82(9) . . ? C9A W1 S1 135.91(10) . . ? C6A W1 S1 78.66(9) . . ? C1A W1 S1 110.91(9) . . ? C2A W1 S1 137.34(9) . . ? C10A W1 S1 105.54(10) . . ? C7A W1 S2 129.45(10) . . ? C4A W1 S2 84.62(9) . . ? C8A W1 S2 132.00(10) . . ? C5A W1 S2 119.40(9) . . ? C3A W1 S2 80.09(8) . . ? C9A W1 S2 97.41(10) . . ? C6A W1 S2 93.52(10) . . ? C1A W1 S2 137.80(8) . . ? C2A W1 S2 109.64(8) . . ? C10A W1 S2 77.55(9) . . ? S1 W1 S2 81.71(2) . . ? C5 S1 W1 108.28(10) . . ? C6 S2 W1 108.14(10) . . ? C5A C1A C2A 108.3(3) . . ? C5A C1A W1 70.57(18) . . ? C2A C1A W1 72.75(18) . . ? C5A C1A H1AA 125.8 . . ? C2A C1A H1AA 125.8 . . ? W1 C1A H1AA 125.8 . . ? N1 C1 C023 175.5(3) . . ? C3A C2A C1A 108.1(3) . . ? C3A C2A W1 71.40(18) . . ? C1A C2A W1 72.39(18) . . ? C3A C2A H2AA 125.8 . . ? C1A C2A H2AA 125.8 . . ? W1 C2A H2AA 125.8 . . ? C023 C2 H2A 109.5 . . ? C023 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C023 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C023 C3 H3A 109.5 . . ? C023 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C023 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C2A C3A C4A 108.2(3) . . ? C2A C3A W1 74.01(18) . . ? C4A C3A W1 70.10(18) . . ? C2A C3A H3AA 125.8 . . ? C4A C3A H3AA 125.8 . . ? W1 C3A H3AA 125.8 . . ? C3A C4A C5A 107.8(3) . . ? C3A C4A W1 74.24(19) . . ? C5A C4A W1 73.15(19) . . ? C3A C4A H4AA 125.8 . . ? C5A C4A H4AA 125.8 . . ? W1 C4A H4AA 125.8 . . ? C1A C5A C4A 107.5(3) . . ? C1A C5A W1 74.5(2) . . ? C4A C5A W1 70.72(18) . . ? C1A C5A H5AA 126.0 . . ? C4A C5A H5AA 126.0 . . ? W1 C5A H5AA 126.0 . . ? C6 C5 C023 126.3(3) . . ? C6 C5 S1 120.6(2) . . ? C023 C5 S1 112.4(2) . . ? C5 C6 C7 129.1(3) . . ? C5 C6 S2 120.8(2) . . ? C7 C6 S2 110.0(2) . . ? C10A C6A C7A 108.6(3) . . ? C10A C6A W1 75.3(2) . . ? C7A C6A W1 69.32(18) . . ? C10A C6A H6AA 125.6 . . ? C7A C6A H6AA 125.6 . . ? W1 C6A H6AA 125.6 . . ? C8A C7A C6A 105.5(3) . . ? C8A C7A W1 72.18(19) . . ? C6A C7A W1 74.73(19) . . ? C8A C7A H7AA 126.7 . . ? C6A C7A H7AA 126.7 . . ? W1 C7A H7AA 126.7 . . ? C8 C7 C12 118.5(3) . . ? C8 C7 C6 120.3(3) . . ? C12 C7 C6 121.1(3) . . ? C9 C8 C7 120.7(3) . . ? C9 C8 H8A 119.7 . . ? C7 C8 H8A 119.7 . . ? C9A C8A C7A 108.6(3) . . ? C9A C8A W1 74.5(2) . . ? C7A C8A W1 71.62(19) . . ? C9A C8A H8AA 125.5 . . ? C7A C8A H8AA 125.5 . . ? W1 C8A H8AA 125.5 . . ? C10A C9A C8A 108.2(3) . . ? C10A C9A W1 75.6(2) . . ? C8A C9A W1 70.20(19) . . ? C10A C9A H9AA 125.7 . . ? C8A C9A H9AA 125.7 . . ? W1 C9A H9AA 125.7 . . ? C10 C9 C8 119.8(3) . . ? C10 C9 H9A 120.1 . . ? C8 C9 H9A 120.1 . . ? C11 C10 C9 120.1(3) . . ? C11 C10 H10A 120.0 . . ? C9 C10 H10A 120.0 . . ? C9A C10A C6A 109.0(3) . . ? C9A C10A W1 70.6(2) . . ? C6A C10A W1 70.91(19) . . ? C9A C10A H10B 125.5 . . ? C6A C10A H10B 125.5 . . ? W1 C10A H10B 125.5 . . ? C10 C11 C12 120.2(3) . . ? C10 C11 H11A 119.9 . . ? C12 C11 H11A 119.9 . . ? C11 C12 C7 120.7(3) . . ? C11 C12 H12A 119.6 . . ? C7 C12 H12A 119.6 . . ? C1 C023 C2 107.5(3) . . ? C1 C023 C5 108.8(2) . . ? C2 C023 C5 108.3(3) . . ? C1 C023 C3 105.7(3) . . ? C2 C023 C3 109.8(3) . . ? C5 C023 C3 116.3(3) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.07 _refine_diff_density_min -0.36 _refine_diff_density_rms 0.10 #=== END of CIF # Attachment '3.CIF' data_cpmohx _database_code_depnum_ccdc_archive 'CCDC 798376' #TrackingRef '3.CIF' _refine_special_details ; One of the Cp rings is disordered by rotation. The major amd minor components were treated as rigid groups which their geometries linked by similarity restraints. Their occupancies refined to 0.633(18) and 0.367(18), respectively. The structure exhibits strong pseudosymmetry which is broken only by the inequivalence of the phenyl and 1-cyanocyclohexyl rings. ; _audit_creation_method 'enCIFer editing of SHELXL97 CIF output' _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H25 Mo N S2' _chemical_formula_sum 'C25 H25 Mo N S2' _chemical_formula_weight 499.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' Mo Mo -1.6832 0.6857 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'C m c 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, 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' '-x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 11.509(5) _cell_length_b 15.496(7) _cell_length_c 12.056(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2150(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2920 _cell_measurement_theta_min 4.4 _cell_measurement_theta_max 52.6 _exptl_crystal_description column _exptl_crystal_colour red _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_min 0.34 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.543 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1024 _exptl_absorpt_coefficient_mu 0.816 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.819 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details '(SADABS version 2.05; Bruker, 2003)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART1000 CCD area detector' _diffrn_measurement_method omega _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 6628 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_av_sigmaI/netI 0.017 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 27.46 _reflns_number_total 2532 _reflns_number_gt 2246 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART version 5.624 (Bruker, 2001)' _computing_cell_refinement 'Bruker SAINT version 6.36A (Bruker, 2002)' _computing_data_reduction 'Bruker SAINT; SHELXTL (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_molecular_graphics ' ? ' _computing_publication_material 'enCIFer (Allen et al., 2004); PLATON (Spek, 2009)' _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^)+(0.038P)^2^+12.212P] 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 0.54(11) _refine_ls_number_reflns 2435 _refine_ls_number_parameters 127 _refine_ls_number_restraints 15 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0403 _refine_ls_wR_factor_ref 0.100 _refine_ls_wR_factor_gt 0.0945 _refine_ls_goodness_of_fit_ref 1.02 _refine_ls_restrained_S_all 1.03 _refine_ls_shift/su_max 0.004 _refine_ls_shift/su_mean 0.001 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 Mo1 Mo 1.0000 -0.01890(3) 0.2214(3) 0.02956(13) Uani 1 2 d S . . C1A C 0.8662 -0.11098(3) 0.1183(3) 0.027(3) Uiso 0.367(18) 1 d PRD A 1 H1AA H 0.8854 -0.1453 0.0505 0.032 Uiso 0.367(18) 1 calc PR A 1 C2A C 0.8194 -0.02619(3) 0.1199(3) 0.033(4) Uiso 0.367(18) 1 d PRD A 1 H2AA H 0.7985 0.0092 0.0535 0.039 Uiso 0.367(18) 1 calc PR A 1 C3A C 0.8043 -0.00152(3) 0.2324(3) 0.039(4) Uiso 0.367(18) 1 d PRD A 1 H3AA H 0.7633 0.0515 0.2589 0.047 Uiso 0.367(18) 1 calc PR A 1 C4A C 0.8417 -0.07106(3) 0.3003(3) 0.044(5) Uiso 0.367(18) 1 d PRD A 1 H4AA H 0.8283 -0.0761 0.3820 0.052 Uiso 0.367(18) 1 calc PR A 1 C5A C 0.8800 -0.13871(3) 0.2297(3) 0.039(3) Uiso 0.367(18) 1 d PRD A 1 H5AA H 0.9036 -0.1979 0.2541 0.047 Uiso 0.367(18) 1 calc PR A 1 C1B C 0.8782(8) -0.1358(5) 0.1793(9) 0.053(3) Uiso 0.633(18) 1 d PD A 2 H1BA H 0.9033 -0.1929 0.1492 0.064 Uiso 0.633(18) 1 calc PR A 2 C2B C 0.8433(7) -0.0651(5) 0.1176(8) 0.042(2) Uiso 0.633(18) 1 d PD A 2 H2BA H 0.8390 -0.0634 0.0348 0.051 Uiso 0.633(18) 1 calc PR A 2 C3B C 0.7982(9) -0.0028(6) 0.1875(8) 0.060(3) Uiso 0.633(18) 1 d PD A 2 H3BA H 0.7584 0.0516 0.1638 0.072 Uiso 0.633(18) 1 calc PR A 2 C4B C 0.8081(7) -0.0331(4) 0.2966(7) 0.034(2) Uiso 0.633(18) 1 d PD A 2 H4BA H 0.7782 -0.0031 0.3643 0.041 Uiso 0.633(18) 1 calc PR A 2 C5B C 0.8641(7) -0.1141(4) 0.2947(8) 0.037(2) Uiso 0.633(18) 1 d PD A 2 H5BA H 0.8758 -0.1537 0.3593 0.044 Uiso 0.633(18) 1 calc PR A 2 S1 S 1.0000 0.0998(2) 0.3512(4) 0.0460(9) Uani 1 2 d S . . S2 S 1.0000 0.0983(2) 0.0897(3) 0.0438(9) Uani 1 2 d S . . C1 C 1.0000 0.3710(10) 0.5597(10) 0.071(5) Uani 1 2 d S . . H1A H 1.0000 0.3242 0.6157 0.085 Uiso 1 2 calc SR . . H1B H 1.0000 0.4268 0.5996 0.085 Uiso 1 2 calc SR . . C4 C 1.0000 0.2836(8) 0.3394(13) 0.060(3) Uani 1 2 d S . . C5 C 1.0000 0.1954(6) 0.2749(12) 0.050(4) Uani 1 2 d S . . C6 C 1.0000 0.1995(7) 0.1639(9) 0.041(3) Uiso 1 2 d SD . . C7 C 1.0000 0.2626(6) 0.0736(7) 0.063(4) Uani 1 2 d SD . . C8 C 0.8931(8) 0.2902(4) 0.4131(7) 0.043(2) Uani 1 1 d . . . H8A H 0.8235 0.2970 0.3657 0.051 Uiso 1 1 calc R . . H8B H 0.8844 0.2357 0.4552 0.051 Uiso 1 1 calc R . . C9 C 0.8989(11) 0.3647(7) 0.4937(8) 0.068(3) Uani 1 1 d . . . H9A H 0.8909 0.4189 0.4510 0.081 Uiso 1 1 calc R . . H9B H 0.8309 0.3607 0.5438 0.081 Uiso 1 1 calc R . . C10 C 1.0000 0.3645(5) 0.2621(6) 0.0424(16) Uani 1 2 d S . . C13 C 1.0000 0.3823(8) -0.0997(10) 0.064(4) Uani 1 2 d SD . . H13A H 1.0000 0.4215 -0.1603 0.077 Uiso 1 2 calc SR . . C14 C 1.1115(11) 0.3534(7) -0.0550(8) 0.069(3) Uani 1 1 d D . . H14A H 1.1833 0.3748 -0.0825 0.082 Uiso 1 1 calc R . . C15 C 1.1065(9) 0.2934(6) 0.0293(7) 0.054(3) Uani 1 1 d D . . H15A H 1.1773 0.2717 0.0589 0.065 Uiso 1 1 calc R . . N1 N 1.0000 0.4317(4) 0.2125(10) 0.0555(18) Uani 1 2 d S . . 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 Mo1 0.0371(2) 0.0267(2) 0.0249(2) 0.0002(4) 0.000 0.000 S1 0.065(3) 0.0458(18) 0.0275(15) -0.0087(14) 0.000 0.000 S2 0.065(3) 0.0402(17) 0.0265(14) 0.0109(13) 0.000 0.000 C1 0.148(15) 0.050(6) 0.014(4) -0.005(4) 0.000 0.000 N1 0.111(5) 0.033(2) 0.023(4) -0.006(4) 0.000 0.000 C4 0.032(5) 0.040(5) 0.108(9) -0.043(5) 0.000 0.000 C5 0.033(4) 0.021(3) 0.096(8) -0.023(3) 0.000 0.000 C7 0.042(6) 0.039(6) 0.109(10) 0.032(6) 0.000 0.000 C8 0.047(5) 0.024(3) 0.057(5) -0.008(3) 0.015(5) -0.007(3) C9 0.100(8) 0.033(4) 0.071(7) -0.023(4) 0.052(6) -0.009(4) C10 0.060(4) 0.036(4) 0.031(3) -0.003(3) 0.000 0.000 C13 0.116(12) 0.046(6) 0.029(5) 0.014(5) 0.000 0.000 C14 0.062(5) 0.071(8) 0.073(7) 0.028(5) 0.009(4) -0.011(5) C15 0.045(6) 0.075(6) 0.043(5) -0.007(5) 0.007(5) -0.022(5) _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 Mo1 C4A 2.2084 . ? Mo1 C3A 2.2724 . ? Mo1 C2B 2.309(8) . ? Mo1 C5A 2.3164 . ? Mo1 C5B 2.325(8) . ? Mo1 C1B 2.346(10) . ? C1A C5A 1.4199 . ? C1A C2A 1.4200 . ? C2A C3A 1.4200 . ? C3A C4A 1.4200 . ? C4A C5A 1.4201 . ? C1B C2B 1.383(8) . ? C1B C5B 1.440(8) . ? C2B C3B 1.382(8) . ? C3B C4B 1.401(8) . ? C4B C5B 1.412(7) . ? S1 C5 1.745(14) . ? S2 C6 1.805(11) . ? C6 C5 1.339(10) . ? C6 C7 1.464(18) . ? C7 C15 1.420(11) . ? C13 C14 1.462(13) . ? C14 C15 1.379(15) . ? C4 C8 1.520(12) . ? C4 C10 1.561(17) . ? C4 C5 1.573(15) . ? C8 C9 1.511(12) . ? C9 C1 1.414(14) . ? N1 C10 1.202(11) . ? 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 C5A C1A C2A 108.0 . . ? C3A C2A C1A 108.0 . . ? C2A C3A C4A 108.0 . . ? C3A C4A C5A 108.0 . . ? C1A C5A C4A 108.0 . . ? C2B C1B C5B 107.6(7) . . ? C3B C2B C1B 109.5(7) . . ? C2B C3B C4B 107.9(7) . . ? C3B C4B C5B 108.7(7) . . ? C4B C5B C1B 105.9(7) . . ? C5 S1 Mo1 107.8(5) . . ? C6 S2 Mo1 109.2(4) . . ? C5 C6 C7 140.8(10) . . ? C5 C6 S2 117.0(11) . . ? C7 C6 S2 102.2(5) . . ? C15 C7 C15 119.5(14) 3_755 . ? C15 C7 C6 120.3(7) 3_755 . ? C15 C7 C6 120.3(7) . . ? C14 C13 C14 122.8(12) . 3_755 ? C15 C14 C13 116.2(10) . . ? C14 C15 C7 122.6(11) . . ? C8 C4 C8 108.0(12) 3_755 . ? C8 C4 C10 107.2(6) 3_755 . ? C8 C4 C10 107.2(6) . . ? C8 C4 C5 110.3(7) 3_755 . ? C8 C4 C5 110.3(7) . . ? C10 C4 C5 113.7(11) . . ? C6 C5 C4 116.9(12) . . ? C6 C5 S1 124.5(10) . . ? C4 C5 S1 118.5(10) . . ? C9 C8 C4 113.0(8) . . ? C1 C9 C8 116.8(10) . . ? C9 C1 C9 110.8(11) . 3_755 ? N1 C10 C4 173.3(9) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.95 _refine_diff_density_min -0.58 _refine_diff_density_rms 0.10 #===END of CIF