# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_cambridge 1145 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email fraser.white@ed.ac.uk _publ_contact_author_name 'Fraser J. White' loop_ _publ_author_name 'Simon Dalgleish' 'Neil Robertson' data_nr0004 _database_code_depnum_ccdc_archive 'CCDC 828225' #TrackingRef '- NR0004.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_compound_source 'Simon Dalgleish' _exptl_crystal_recrystallization_method 'slow diffusion' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H9 N O S2' _chemical_formula_sum 'C12 H9 N O S2' _chemical_formula_weight 247.32 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' S S 0.3331 0.5567 '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 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' 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 6.6997(3) _cell_length_b 7.3685(4) _cell_length_c 22.4087(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.852(5) _cell_angle_gamma 90.00 _cell_volume 1103.74(10) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 1937 _cell_measurement_theta_min 1.9749 _cell_measurement_theta_max 72.6537 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1690 _exptl_crystal_size_mid 0.1439 _exptl_crystal_size_min 0.0558 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.488 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 512 _exptl_absorpt_coefficient_mu 4.168 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3299 _exptl_absorpt_correction_T_max 0.7900 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'SuperNova (Cu) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3147 _diffrn_reflns_number 3096 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.9749 _diffrn_reflns_theta_max 72.6537 _reflns_number_total 2124 _reflns_number_gt 1795 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) (compiled Jan 5 2010,16:28:46) ; _computing_structure_solution 'Shelxs Sheldrick' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics Shelxp _computing_publication_material 'Platon, encifer' _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 Following Model and Quality ALERTS were generated - (Acta-Mode) <<< #============================================================================== Format: alert-number_ALERT_alert-type_alert-level text 340_ALERT_3_C Low Bond Precision on C-C Bonds (x 1000) Ang ... 6 Noted. 911_ALERT_3_C Missing # FCF Refl Between THmin & STh/L= 0.600 9 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 65 The data collection strategy used was to collect fully complete data to 0.84 Angstroms. Some higher angle data were collected in the process and these have been included in the refinement. Please refer to the completeness statistics below #============================================================================== Resolution & Completeness Statistics (Cumulative and Friedel Pairs Averaged) #============================================================================== Theta sin(th)/Lambda Complete Expected Measured Missing #------------------------------------------------------------------------------ 50.43 0.500 1.000 1153 1153 0 57.99 0.550 1.000 1527 1527 0 67.68 0.600 0.995 1987 1978 9 #----------------------------------------------------------- ACTA Min. Res. --- 72.92 0.620 0.966 2198 2124 74 061_ALERT_4_B Tmax/Tmin Range Test RR' too Large ............. 0.70 The crystal was a shard and measurement of its dimension or indeed face indexing proved difficult. 920_ALERT_1_C Theta(Max) in CIF and FCF Differ by ........... 0.27 Deg. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? Noted, no action taken ; _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^)+(0.0519P)^2^+4.9536P] 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 2124 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0674 _refine_ls_wR_factor_ref 0.1799 _refine_ls_wR_factor_gt 0.1751 _refine_ls_goodness_of_fit_ref 1.161 _refine_ls_restrained_S_all 1.161 _refine_ls_shift/su_max 0.005 _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 O1 O 0.0418(5) 0.7436(6) -0.02615(16) 0.0481(11) Uani 1 1 d . . . C2 C 0.2054(7) 0.7524(7) 0.0001(2) 0.0320(11) Uani 1 1 d . . . S3 S 0.43333(17) 0.73537(16) -0.03436(5) 0.0287(3) Uani 1 1 d . . . C4 C 0.5883(7) 0.7653(6) 0.0302(2) 0.0278(10) Uani 1 1 d . . . H4 H 0.7296 0.7656 0.0286 0.033 Uiso 1 1 calc R . . C5 C 0.5043(7) 0.7881(6) 0.0821(2) 0.0256(9) Uani 1 1 d . . . S6 S 0.24307(17) 0.7863(2) 0.07803(5) 0.0371(4) Uani 1 1 d . . . C7 C 0.6084(6) 0.8216(6) 0.1415(2) 0.0250(9) Uani 1 1 d . . . C8 C 0.7930(6) 0.9182(6) 0.1454(2) 0.0270(10) Uani 1 1 d . . . H8 H 0.8440 0.9650 0.1100 0.032 Uiso 1 1 calc R . . C9 C 0.8992(7) 0.9453(6) 0.1994(2) 0.0272(10) Uani 1 1 d . . . H9 H 1.0239 1.0072 0.2017 0.033 Uiso 1 1 calc R . . C10 C 0.8173(6) 0.8786(6) 0.2509(2) 0.0242(9) Uani 1 1 d . . . C11 C 0.6302(6) 0.7843(6) 0.2485(2) 0.0239(9) Uani 1 1 d . . . C12 C 0.5273(6) 0.7593(5) 0.19280(19) 0.0215(9) Uani 1 1 d . . . H12 H 0.4014 0.6994 0.1902 0.026 Uiso 1 1 calc R . . C13 C 0.5966(6) 0.7380(6) 0.3085(2) 0.0251(9) Uani 1 1 d . . . H13 H 0.4815 0.6786 0.3216 0.030 Uiso 1 1 calc R . . C14 C 0.7570(6) 0.7932(6) 0.3439(2) 0.0265(10) Uani 1 1 d . . . H14 H 0.7754 0.7732 0.3858 0.032 Uiso 1 1 calc R . . N15 N 0.8903(5) 0.8833(5) 0.30948(17) 0.0254(8) Uani 1 1 d . . . C16 C 1.0857(7) 0.9521(7) 0.3315(2) 0.0315(11) Uani 1 1 d . . . H16A H 1.1903 0.8691 0.3196 0.047 Uiso 1 1 calc R . . H16B H 1.0912 0.9609 0.3752 0.047 Uiso 1 1 calc R . . H16C H 1.1070 1.0724 0.3144 0.047 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 O1 0.0274(18) 0.086(3) 0.0302(19) -0.0047(19) -0.0044(15) 0.0015(19) C2 0.027(2) 0.040(3) 0.029(2) 0.000(2) 0.0009(19) 0.002(2) S3 0.0279(6) 0.0327(6) 0.0258(6) -0.0008(4) 0.0036(4) 0.0024(5) C4 0.025(2) 0.030(2) 0.029(2) 0.0013(18) 0.0029(18) 0.0022(19) C5 0.023(2) 0.023(2) 0.030(2) 0.0017(18) 0.0013(17) 0.0030(18) S6 0.0199(5) 0.0647(9) 0.0267(6) -0.0018(6) 0.0024(4) 0.0025(5) C7 0.024(2) 0.018(2) 0.033(2) 0.0011(17) 0.0035(17) 0.0060(17) C8 0.024(2) 0.023(2) 0.035(2) 0.0039(19) 0.0068(18) 0.0042(18) C9 0.023(2) 0.019(2) 0.039(3) 0.0014(18) 0.0050(18) -0.0006(17) C10 0.023(2) 0.018(2) 0.031(2) -0.0005(17) 0.0026(17) 0.0017(17) C11 0.021(2) 0.020(2) 0.031(2) 0.0018(17) 0.0058(17) 0.0013(17) C12 0.0190(19) 0.015(2) 0.031(2) 0.0006(16) 0.0043(16) 0.0010(16) C13 0.022(2) 0.027(2) 0.027(2) 0.0012(17) 0.0040(17) -0.0025(18) C14 0.024(2) 0.027(2) 0.030(2) 0.0022(18) 0.0067(17) 0.0030(18) N15 0.0223(18) 0.0194(19) 0.034(2) 0.0012(15) 0.0024(15) -0.0020(15) C16 0.024(2) 0.027(2) 0.043(3) -0.001(2) -0.0002(19) -0.0033(19) _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 O1 C2 1.211(6) . ? C2 S3 1.762(5) . ? C2 S6 1.764(5) . ? S3 C4 1.736(5) . ? C4 C5 1.337(6) . ? C4 H4 0.9500 . ? C5 C7 1.481(6) . ? C5 S6 1.746(4) . ? C7 C12 1.383(6) . ? C7 C8 1.425(6) . ? C8 C9 1.377(6) . ? C8 H8 0.9500 . ? C9 C10 1.400(6) . ? C9 H9 0.9500 . ? C10 N15 1.370(6) . ? C10 C11 1.431(6) . ? C11 C12 1.396(6) . ? C11 C13 1.420(6) . ? C12 H12 0.9500 . ? C13 C14 1.354(6) . ? C13 H13 0.9500 . ? C14 N15 1.388(6) . ? C14 H14 0.9500 . ? N15 C16 1.458(6) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? 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 O1 C2 S3 124.4(4) . . ? O1 C2 S6 123.6(4) . . ? S3 C2 S6 111.9(3) . . ? C4 S3 C2 96.5(2) . . ? C5 C4 S3 118.6(4) . . ? C5 C4 H4 120.7 . . ? S3 C4 H4 120.7 . . ? C4 C5 C7 127.1(4) . . ? C4 C5 S6 115.6(4) . . ? C7 C5 S6 117.3(3) . . ? C5 S6 C2 97.4(2) . . ? C12 C7 C8 120.2(4) . . ? C12 C7 C5 120.3(4) . . ? C8 C7 C5 119.5(4) . . ? C9 C8 C7 121.4(4) . . ? C9 C8 H8 119.3 . . ? C7 C8 H8 119.3 . . ? C8 C9 C10 117.7(4) . . ? C8 C9 H9 121.1 . . ? C10 C9 H9 121.1 . . ? N15 C10 C9 130.2(4) . . ? N15 C10 C11 107.7(4) . . ? C9 C10 C11 122.0(4) . . ? C12 C11 C13 135.6(4) . . ? C12 C11 C10 118.5(4) . . ? C13 C11 C10 105.9(4) . . ? C7 C12 C11 120.1(4) . . ? C7 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C14 C13 C11 108.2(4) . . ? C14 C13 H13 125.9 . . ? C11 C13 H13 125.9 . . ? C13 C14 N15 109.5(4) . . ? C13 C14 H14 125.3 . . ? N15 C14 H14 125.3 . . ? C10 N15 C14 108.6(4) . . ? C10 N15 C16 125.9(4) . . ? C14 N15 C16 125.1(4) . . ? N15 C16 H16A 109.5 . . ? N15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.962 _diffrn_reflns_theta_full 67.68 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.749 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.093 _diffrn_orient_matrix_UB_11 -0.1444373000 _diffrn_orient_matrix_UB_12 -0.0222305000 _diffrn_orient_matrix_UB_13 -0.0559847000 _diffrn_orient_matrix_UB_21 -0.1788740000 _diffrn_orient_matrix_UB_22 0.0367057000 _diffrn_orient_matrix_UB_23 0.0380334000 _diffrn_orient_matrix_UB_31 0.0165220000 _diffrn_orient_matrix_UB_32 0.2047854000 _diffrn_orient_matrix_UB_33 -0.0127575000 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -115.00 -19.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -39.8164 -37.0000 -180.0000 96 #__ type_ start__ end____ width___ exp.time_ 2 omega -114.00 -24.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - -39.8164 -37.0000 90.0000 90 #__ type_ start__ end____ width___ exp.time_ 3 omega 89.00 117.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ frames - 39.8164 179.0000 -180.0000 28 #__ type_ start__ end____ width___ exp.time_ 4 omega -114.00 -87.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - -61.5000 -113.0000 168.0000 27 #__ type_ start__ end____ width___ exp.time_ 5 omega 32.00 69.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 107.1667 -45.0000 -120.0000 37 #__ type_ start__ end____ width___ exp.time_ 6 omega 37.00 72.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 107.1667 -45.0000 120.0000 35 #__ type_ start__ end____ width___ exp.time_ 7 omega 100.00 160.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 107.1667 125.0000 -30.0000 60 #__ type_ start__ end____ width___ exp.time_ 8 omega 89.00 157.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 107.1667 45.0000 -120.0000 68 #__ type_ start__ end____ width___ exp.time_ 9 omega 120.00 176.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 107.1667 125.0000 -150.0000 56 #__ type_ start__ end____ width___ exp.time_ 10 omega 87.00 112.00 1.0000 15.0000 omega____ theta____ kappa____ phi______ frames - 107.1667 45.0000 -30.0000 25 ; loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 4 1 7 0.0279 3.7125 0.6010 6.8782 -0.9398 -0.3780 0.0978 -4 -1 -7 0.0279 -3.7125 -0.6010 -6.8782 0.9398 0.3780 -0.0978 -2 -4 -1 0.0492 -1.9788 -4.2642 -0.8076 0.4268 0.1683 -0.8935 2 4 1 0.0492 1.9788 4.2642 0.8076 -0.4268 -0.1683 0.8935 2 4 -2 0.0506 2.0697 4.1880 -1.7212 -0.2967 -0.2839 0.9116 -2 -4 2 0.0506 -2.0697 -4.1880 1.7212 0.2967 0.2839 -0.9116 -4 0 -3 0.0476 -4.1521 0.0871 -2.9214 0.7671 0.6324 -0.0149 4 0 3 0.0281 4.1263 0.1975 2.5621 -0.7494 -0.6312 0.0771 4 0 -3 0.0361 4.2891 -0.4365 -3.4119 -0.4244 -0.9114 0.0263 -4 1 3 0.0443 -4.3149 0.7211 3.0526 0.4421 0.9125 0.0360 4 1 -4 0.0301 4.2052 1.1836 -3.9329 -0.4183 -0.8578 0.3622 -2 0 14 0.0894 -1.5253 -0.2792 13.9809 -0.5553 0.7961 -0.2601 -2 1 13 0.0771 -1.9960 0.9895 13.0550 -0.4625 0.8905 0.0028 # Attachment '- NR0007.CIF' data_NR0007 _database_code_depnum_ccdc_archive 'CCDC 828226' #TrackingRef '- NR0007.CIF' _audit_creation_date 10-07-06 _audit_creation_method CRYSTALS_ver_12.85 _oxford_structure_analysis_title 'NR0007 in P2(1)/c' _chemical_name_systematic ? _chemical_melting_point ? _publ_section_exptl_refinement ; #============================================================================== The Following Model and Quality ALERTS were generated - (Acta-Mode) <<< #============================================================================== Format: alert-number_ALERT_alert-type_alert-level text 910_ALERT_3_B Missing # of FCF Reflections Below Th(Min) ..... 11 912_ALERT_4_C Missing # of FCF Reflections Above STh/L= 0.600 470 Completeness and resolution meet IUCr limits. 952_ALERT_1_C Reported and Calculated Lmax Values Differ by .. 2 Values supplied are calculated by crystals. 760_ALERT_1_G CIF Contains no Torsion Angles ................. ? Noted, no action taken. 808_ALERT_5_G No Parseable SHELXL Style Weighting Scheme Found ! 929_ALERT_5_G No Weight Pars,Obs and Calc R1,wR2,S not checked ! Crystals auto-statistical weights were used. ; #end of refcif _cell_length_a 4.31010(13) _cell_length_b 15.6910(4) _cell_length_c 21.4795(7) _cell_angle_alpha 90 _cell_angle_beta 91.526(3) _cell_angle_gamma 90 _cell_volume 1452.14(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Ni 0.3393 1.1124 12.8376 3.8785 7.2920 0.2565 4.4438 12.1763 2.3800 66.3421 1.0341 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C45 H51 N3 Ni1.50 S6 # Dc = 2.09 Fooo = 640.00 Mu = 14.68 M = 457.19 # Found Formula = C30 H34 N2 Ni1 S4 # Dc = 1.39 FOOO = 640.00 Mu = 9.78 M = 304.79 _chemical_formula_sum 'C30 H34 N2 Ni1 S4' _chemical_formula_moiety 'C30 H34 N2 Ni1 S4' _chemical_compound_source ? _chemical_formula_weight 609.59 _cell_measurement_reflns_used 5598 _cell_measurement_theta_min 2 _cell_measurement_theta_max 28 _cell_measurement_temperature 100 _exptl_crystal_description plate _exptl_crystal_colour 'dark green' _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_max 0.25 _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.978 # Sheldrick geometric approximatio 0.83 0.94 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.62 _exptl_absorpt_correction_T_max 0.94 _diffrn_measurement_device 'Oxford Diffraction XCALIBUR' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 100 _diffrn_reflns_number 8971 _reflns_number_total 3166 _diffrn_reflns_av_R_equivalents 0.046 # Number of reflections with Friedels Law is 0 # Number of reflections without Friedels Law is 3166 # Theoretical number of reflections is about 7347 _diffrn_reflns_theta_min 2.299 _diffrn_reflns_theta_max 28.478 _diffrn_measured_fraction_theta_max 0.862 _diffrn_reflns_theta_full 25.345 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -5 _reflns_limit_h_max 5 _reflns_limit_k_min 0 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 26 _oxford_diffrn_Wilson_B_factor 2.07 _oxford_diffrn_Wilson_scale 0.32 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.01 _refine_diff_density_max 0.67 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 3157 _refine_ls_number_restraints 0 _refine_ls_number_parameters 169 _oxford_refine_ls_R_factor_ref 0.0592 _refine_ls_wR_factor_ref 0.1299 _refine_ls_goodness_of_fit_ref 1.0064 _refine_ls_shift/su_max 0.000681 # The values computed from all data _oxford_reflns_number_all 3157 _refine_ls_R_factor_all 0.0592 _refine_ls_wR_factor_all 0.1299 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2449 _refine_ls_R_factor_gt 0.0458 _refine_ls_wR_factor_gt 0.1257 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment noref # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.07P)^2^ + 2.52P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, G., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Oxford Diffraction, (2002). CrysAlis RED. Oxford Diffraction, (2002). Xcalibur User Manual. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Ni1 Ni 1.0000 0.5000 0.5000 0.0234 1.0000 Uani S . . . . . . S2 S 1.21810(18) 0.60214(5) 0.45305(4) 0.0256 1.0000 Uani . . . . . . . C3 C 1.2998(7) 0.67647(19) 0.50915(15) 0.0241 1.0000 Uani . . . . . . . C4 C 1.4714(7) 0.7558(2) 0.48876(16) 0.0278 1.0000 Uani . . . . . . . C5 C 1.2745(7) 0.8198(2) 0.45195(17) 0.0318 1.0000 Uani . . . . . . . C6 C 1.4582(8) 0.8979(2) 0.43295(19) 0.0372 1.0000 Uani . . . . . . . C7 C 1.2639(9) 0.9648(3) 0.3982(2) 0.0536 1.0000 Uani . . . . . . . C8 C 1.2192(7) 0.66064(19) 0.56964(15) 0.0246 1.0000 Uani . . . . . . . S9 S 1.03738(19) 0.56638(5) 0.58593(4) 0.0258 1.0000 Uani . . . . . . . C10 C 1.2846(7) 0.7183(2) 0.62312(15) 0.0258 1.0000 Uani . . . . . . . C11 C 1.4625(8) 0.6894(2) 0.67369(16) 0.0293 1.0000 Uani . . . . . . . C12 C 1.5270(8) 0.7440(2) 0.72380(16) 0.0303 1.0000 Uani . . . . . . . C13 C 1.4048(8) 0.8271(2) 0.72198(15) 0.0287 1.0000 Uani . . . . . . . N14 N 1.5010(7) 0.86844(19) 0.77540(14) 0.0331 1.0000 Uani . . . . . . . C15 C 1.4276(10) 0.9557(2) 0.79085(18) 0.0417 1.0000 Uani . . . . . . . C16 C 1.6804(9) 0.8127(3) 0.81059(17) 0.0386 1.0000 Uani . . . . . . . C17 C 1.7027(9) 0.7368(2) 0.78100(17) 0.0382 1.0000 Uani . . . . . . . C18 C 1.2198(8) 0.8569(2) 0.67227(17) 0.0312 1.0000 Uani . . . . . . . C19 C 1.1645(8) 0.8017(2) 0.62321(16) 0.0305 1.0000 Uani . . . . . . . H41 H 1.5640 0.7834 0.5260 0.0348 1.0000 Uiso . . . . . . . H42 H 1.6376 0.7367 0.4616 0.0339 1.0000 Uiso . . . . . . . H51 H 1.0999 0.8367 0.4770 0.0391 1.0000 Uiso . . . . . . . H52 H 1.1924 0.7913 0.4142 0.0386 1.0000 Uiso . . . . . . . H61 H 1.5450 0.9232 0.4715 0.0446 1.0000 Uiso . . . . . . . H62 H 1.6229 0.8783 0.4058 0.0441 1.0000 Uiso . . . . . . . H71 H 1.3870 1.0142 0.3877 0.0800 1.0000 Uiso . . . . . . . H72 H 1.0911 0.9825 0.4231 0.0811 1.0000 Uiso . . . . . . . H73 H 1.1870 0.9386 0.3597 0.0804 1.0000 Uiso . . . . . . . H111 H 1.5416 0.6338 0.6727 0.0353 1.0000 Uiso . . . . . . . H151 H 1.5289 0.9700 0.8293 0.0625 1.0000 Uiso . . . . . . . H152 H 1.4887 0.9936 0.7583 0.0630 1.0000 Uiso . . . . . . . H153 H 1.2064 0.9610 0.7954 0.0633 1.0000 Uiso . . . . . . . H161 H 1.7711 0.8273 0.8498 0.0468 1.0000 Uiso . . . . . . . H171 H 1.8160 0.6889 0.7945 0.0471 1.0000 Uiso . . . . . . . H181 H 1.1329 0.9126 0.6720 0.0382 1.0000 Uiso . . . . . . . H191 H 1.0423 0.8215 0.5890 0.0366 1.0000 Uiso . . . . . . . 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 Ni1 0.0238(3) 0.0197(3) 0.0265(3) -0.0006(2) -0.0017(2) -0.0028(2) S2 0.0264(4) 0.0227(4) 0.0276(4) 0.0002(3) -0.0010(3) -0.0032(3) C3 0.0196(14) 0.0183(14) 0.0341(17) 0.0005(12) -0.0046(12) 0.0024(12) C4 0.0232(15) 0.0253(16) 0.0348(18) 0.0021(13) -0.0010(13) -0.0041(13) C5 0.0224(16) 0.0279(17) 0.045(2) 0.0084(15) -0.0020(14) -0.0032(14) C6 0.0263(18) 0.0297(18) 0.055(2) 0.0131(16) -0.0006(15) -0.0033(15) C7 0.033(2) 0.041(2) 0.086(3) 0.029(2) -0.006(2) -0.0062(18) C8 0.0224(15) 0.0154(13) 0.0357(18) -0.0002(13) -0.0048(12) 0.0014(12) S9 0.0296(4) 0.0204(4) 0.0274(4) -0.0004(3) -0.0003(3) -0.0039(3) C10 0.0264(16) 0.0214(15) 0.0294(17) 0.0010(13) -0.0010(12) -0.0047(13) C11 0.0303(17) 0.0239(16) 0.0334(18) 0.0006(13) -0.0011(13) 0.0010(14) C12 0.0302(17) 0.0323(18) 0.0282(17) 0.0015(14) -0.0013(13) -0.0032(15) C13 0.0297(17) 0.0265(16) 0.0298(17) -0.0025(14) 0.0012(13) -0.0049(14) N14 0.0363(16) 0.0315(15) 0.0314(16) -0.0056(12) -0.0008(12) -0.0047(13) C15 0.056(2) 0.0308(19) 0.038(2) -0.0104(16) -0.0024(17) -0.0035(18) C16 0.041(2) 0.043(2) 0.0308(19) -0.0024(16) -0.0066(15) -0.0017(17) C17 0.044(2) 0.037(2) 0.034(2) 0.0003(16) -0.0077(16) 0.0053(17) C18 0.0309(18) 0.0229(16) 0.040(2) -0.0010(14) -0.0018(14) 0.0002(14) C19 0.0306(17) 0.0244(16) 0.0361(19) 0.0014(14) -0.0067(14) -0.0018(14) _refine_ls_extinction_method None _oxford_refine_ls_scale 2.10(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Ni1 . S2 2_766 2.1259(8) yes Ni1 . S9 2_766 2.1216(8) yes Ni1 . S2 . 2.1259(8) yes Ni1 . S9 . 2.1216(8) yes S2 . C3 . 1.707(3) yes C3 . C4 . 1.518(4) yes C3 . C8 . 1.376(5) yes C4 . C5 . 1.522(5) yes C4 . H41 . 0.985 no C4 . H42 . 0.983 no C5 . C6 . 1.521(5) yes C5 . H51 . 0.974 no C5 . H52 . 0.983 no C6 . C7 . 1.526(5) yes C6 . H61 . 0.984 no C6 . H62 . 0.980 no C7 . H71 . 0.968 no C7 . H72 . 0.969 no C7 . H73 . 0.974 no C8 . S9 . 1.714(3) yes C8 . C10 . 1.483(4) yes C10 . C11 . 1.389(4) yes C10 . C19 . 1.408(5) yes C11 . C12 . 1.398(5) yes C11 . H111 . 0.938 no C12 . C13 . 1.406(5) yes C12 . C17 . 1.430(5) yes C13 . N14 . 1.372(4) yes C13 . C18 . 1.396(5) yes N14 . C15 . 1.445(5) yes N14 . C16 . 1.379(5) yes C15 . H151 . 0.951 no C15 . H152 . 0.960 no C15 . H153 . 0.965 no C16 . C17 . 1.355(5) yes C16 . H161 . 0.947 no C17 . H171 . 0.938 no C18 . C19 . 1.380(5) yes C18 . H181 . 0.950 no C19 . H191 . 0.946 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag S2 2_766 Ni1 . S9 2_766 91.05(3) yes S2 2_766 Ni1 . S2 . 179.995 yes S9 2_766 Ni1 . S2 . 88.95(3) yes S2 2_766 Ni1 . S9 . 88.95(3) yes S9 2_766 Ni1 . S9 . 179.995 yes S2 . Ni1 . S9 . 91.05(3) yes Ni1 . S2 . C3 . 105.41(11) yes S2 . C3 . C4 . 116.7(2) yes S2 . C3 . C8 . 119.4(2) yes C4 . C3 . C8 . 123.9(3) yes C3 . C4 . C5 . 114.9(3) yes C3 . C4 . H41 . 108.5 no C5 . C4 . H41 . 109.8 no C3 . C4 . H42 . 106.8 no C5 . C4 . H42 . 107.3 no H41 . C4 . H42 . 109.3 no C4 . C5 . C6 . 112.6(3) yes C4 . C5 . H51 . 108.7 no C6 . C5 . H51 . 110.1 no C4 . C5 . H52 . 108.2 no C6 . C5 . H52 . 108.9 no H51 . C5 . H52 . 108.3 no C5 . C6 . C7 . 113.8(3) yes C5 . C6 . H61 . 106.8 no C7 . C6 . H61 . 109.0 no C5 . C6 . H62 . 107.3 no C7 . C6 . H62 . 108.8 no H61 . C6 . H62 . 111.2 no C6 . C7 . H71 . 111.5 no C6 . C7 . H72 . 110.3 no H71 . C7 . H72 . 109.4 no C6 . C7 . H73 . 107.1 no H71 . C7 . H73 . 108.5 no H72 . C7 . H73 . 109.9 no C3 . C8 . S9 . 118.5(2) yes C3 . C8 . C10 . 125.0(3) yes S9 . C8 . C10 . 116.5(2) yes C8 . S9 . Ni1 . 105.70(12) yes C8 . C10 . C11 . 119.8(3) yes C8 . C10 . C19 . 120.4(3) yes C11 . C10 . C19 . 119.8(3) yes C10 . C11 . C12 . 119.8(3) yes C10 . C11 . H111 . 118.7 no C12 . C11 . H111 . 121.6 no C11 . C12 . C13 . 118.7(3) yes C11 . C12 . C17 . 134.6(3) yes C13 . C12 . C17 . 106.7(3) yes C12 . C13 . N14 . 108.1(3) yes C12 . C13 . C18 . 122.5(3) yes N14 . C13 . C18 . 129.4(3) yes C13 . N14 . C15 . 125.2(3) yes C13 . N14 . C16 . 108.1(3) yes C15 . N14 . C16 . 126.7(3) yes N14 . C15 . H151 . 109.0 no N14 . C15 . H152 . 110.7 no H151 . C15 . H152 . 110.9 no N14 . C15 . H153 . 109.2 no H151 . C15 . H153 . 108.8 no H152 . C15 . H153 . 108.2 no N14 . C16 . C17 . 110.3(3) yes N14 . C16 . H161 . 123.1 no C17 . C16 . H161 . 126.6 no C12 . C17 . C16 . 106.9(3) yes C12 . C17 . H171 . 126.1 no C16 . C17 . H171 . 127.0 no C13 . C18 . C19 . 117.2(3) yes C13 . C18 . H181 . 121.9 no C19 . C18 . H181 . 120.9 no C10 . C19 . C18 . 121.9(3) yes C10 . C19 . H191 . 120.1 no C18 . C19 . H191 . 117.9 no