# Electronic Supplementary Material for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Hugo Tlahuext' _publ_contact_author_email TLAHUEXT@CIQ.UAEM.MX _publ_section_title ; Comparative Analysis of M-O, M-S and Cation-pi(arene) Interactions in the Alkali Metal (Na+, K+, Rb+, Cs+) Bis-dithiocarbamate Salts of N,N'-Dibenzyl-1,2-ethylenediamine ; loop_ _publ_author_name 'Hugo Tlahuext' 'Carolina Godoy-Alcantar' 'Herbert Hopfl' 'Felipe Medrano' 'Reyna Reyes-Martinez' # Attachment 'revised_file_Compound_1.cif' data_reyna1m _database_code_depnum_ccdc_archive 'CCDC 721768' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H18 N2 S4, H16 Na2 O8' _chemical_formula_sum 'C18 H34 N2 Na2 O8 S4' _chemical_formula_weight 580.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Na Na 0.0362 0.0249 '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' _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 6.774(3) _cell_length_b 8.264(3) _cell_length_c 12.751(5) _cell_angle_alpha 103.055(9) _cell_angle_beta 91.660(9) _cell_angle_gamma 90.889(10) _cell_volume 695.0(5) _cell_formula_units_Z 1 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 291 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 17.02 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.388 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 306 _exptl_absorpt_coefficient_mu 0.415 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8751 _exptl_absorpt_correction_T_max 0.9178 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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 3523 _diffrn_reflns_av_R_equivalents 0.0507 _diffrn_reflns_av_sigmaI/netI 0.1319 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2415 _reflns_number_gt 1531 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.All O-H hydrogen atoms have been localized by difference Fourier maps. Since during the unrestricted refinement of their coordinates the bond distances and bond angles started to deviate significantly from the expected geometries, the bonding geometries of the water molecules have been restrained during the refinement using DFIX and DANG instructions (Ow-H = 0.840(1) \%A, Hw...Hw 1.35(1) \%A and Na...Hw = 2.73(1) and 2.87(1) \%A for the terminal and bridging water molecules, respectively). The hydrogen atoms of one of the metal-coordinated water molecules (O3) are disordered over three positions (occ: 0.50, 0.75 and 0.75). These hydrogen atoms are involved either in (Na)Ow-H...Ow(Na) or Ow-H...S interactions. ; _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^)+(0.0390P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2415 _refine_ls_number_parameters 181 _refine_ls_number_restraints 26 _refine_ls_R_factor_all 0.1368 _refine_ls_R_factor_gt 0.0894 _refine_ls_wR_factor_ref 0.1823 _refine_ls_wR_factor_gt 0.1601 _refine_ls_goodness_of_fit_ref 1.116 _refine_ls_restrained_S_all 1.146 _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 Na1 Na 0.0126(4) 0.8778(3) 0.0958(2) 0.0521(8) Uani 1 1 d D . . S1 S 0.5688(3) 0.4196(2) 0.15103(15) 0.0501(6) Uani 1 1 d D . . S2 S 0.2342(3) 0.3776(2) 0.29004(15) 0.0468(5) Uani 1 1 d D . . N1 N 0.5704(7) 0.5317(6) 0.3643(4) 0.0316(13) Uani 1 1 d . . . O1 O -0.3235(7) 0.7758(6) 0.0726(4) 0.0609(15) Uani 1 1 d D . . H11 H -0.368(4) 0.746(7) 0.0088(7) 0.091 Uiso 1 1 d D . . H12 H -0.351(3) 0.699(6) 0.103(4) 0.091 Uiso 1 1 d D . . O2 O 0.3348(8) 0.9866(6) 0.1230(5) 0.0792(19) Uani 1 1 d D . . H21 H 0.4142(16) 0.9082(13) 0.117(6) 0.119 Uiso 1 1 d D . . H22 H 0.349(3) 1.044(7) 0.186(2) 0.119 Uiso 1 1 d D . . O3 O 0.1094(8) 0.6064(6) 0.0967(4) 0.084(2) Uani 1 1 d D . . H31 H 0.056(4) 0.5396(13) 0.0437(16) 0.126 Uiso 0.50 1 d PD . . H32 H 0.2325(10) 0.596(2) 0.095(2) 0.126 Uiso 0.75 1 d PD . . H33 H 0.078(4) 0.579(2) 0.1538(13) 0.126 Uiso 0.75 1 d PD . . O4 O -0.0508(7) 1.1634(6) 0.0942(4) 0.0535(14) Uani 1 1 d D . . H41 H -0.1697(12) 1.191(2) 0.099(5) 0.080 Uiso 1 1 d D . . H42 H 0.013(7) 1.2337(13) 0.141(3) 0.080 Uiso 1 1 d D . . C1 C 0.4708(9) 0.4510(7) 0.2756(5) 0.0313(15) Uani 1 1 d . . . C2 C 0.4860(10) 0.5700(7) 0.4713(5) 0.0346(16) Uani 1 1 d . . . H2A H 0.3461 0.5900 0.4642 0.042 Uiso 1 1 calc R . . H2B H 0.5486 0.6707 0.5141 0.042 Uiso 1 1 calc R . . C3 C 0.7719(9) 0.5886(7) 0.3606(6) 0.0395(17) Uani 1 1 d . . . H3A H 0.8321 0.5213 0.2979 0.047 Uiso 1 1 calc R . . H3B H 0.8447 0.5722 0.4239 0.047 Uiso 1 1 calc R . . C4 C 0.7907(10) 0.7706(7) 0.3561(5) 0.0349(16) Uani 1 1 d . . . C5 C 0.6314(10) 0.8706(7) 0.3496(5) 0.0427(18) Uani 1 1 d . . . H5 H 0.5038 0.8266 0.3479 0.051 Uiso 1 1 calc R . . C6 C 0.6589(12) 1.0339(8) 0.3457(6) 0.053(2) Uani 1 1 d . . . H6 H 0.5498 1.0985 0.3397 0.063 Uiso 1 1 calc R . . C7 C 0.8475(13) 1.1038(9) 0.3506(6) 0.057(2) Uani 1 1 d . . . H7 H 0.8649 1.2154 0.3501 0.069 Uiso 1 1 calc R . . C8 C 1.0106(12) 1.0051(9) 0.3564(6) 0.062(2) Uani 1 1 d . . . H8 H 1.1379 1.0499 0.3582 0.075 Uiso 1 1 calc R . . C9 C 0.9817(10) 0.8394(9) 0.3594(6) 0.050(2) Uani 1 1 d . . . H9 H 1.0903 0.7735 0.3636 0.061 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Na1 0.058(2) 0.0451(16) 0.0534(19) 0.0129(15) -0.0038(15) -0.0008(14) S1 0.0618(13) 0.0536(12) 0.0349(10) 0.0081(9) 0.0128(9) 0.0088(10) S2 0.0368(11) 0.0519(11) 0.0494(12) 0.0082(10) -0.0042(9) -0.0120(8) N1 0.037(3) 0.029(3) 0.028(3) 0.006(3) -0.003(2) -0.005(2) O1 0.061(4) 0.073(4) 0.051(3) 0.019(3) -0.001(3) -0.003(3) O2 0.058(4) 0.059(4) 0.107(5) -0.008(4) -0.019(4) 0.004(3) O3 0.123(5) 0.059(3) 0.072(4) 0.021(3) -0.019(4) 0.024(3) O4 0.045(3) 0.056(3) 0.057(3) 0.007(3) -0.006(3) 0.003(2) C1 0.034(4) 0.022(3) 0.040(4) 0.010(3) 0.006(3) 0.010(3) C2 0.046(4) 0.027(3) 0.030(4) 0.003(3) -0.001(3) 0.003(3) C3 0.028(4) 0.038(4) 0.055(5) 0.015(4) 0.002(3) -0.003(3) C4 0.045(4) 0.033(4) 0.027(4) 0.010(3) -0.001(3) -0.009(3) C5 0.044(4) 0.028(4) 0.055(5) 0.006(3) 0.004(4) -0.001(3) C6 0.076(6) 0.031(4) 0.051(5) 0.008(4) -0.003(4) 0.013(4) C7 0.089(7) 0.030(4) 0.051(5) 0.005(4) 0.011(5) -0.010(4) C8 0.060(6) 0.052(5) 0.074(6) 0.013(5) 0.008(5) -0.017(4) C9 0.045(5) 0.047(4) 0.056(5) 0.006(4) -0.002(4) -0.007(4) _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 Na1 O2 2.334(6) . ? Na1 O3 2.349(5) . ? Na1 O4 2.391(6) 2_575 ? Na1 O1 2.402(6) . ? Na1 O4 2.410(5) . ? S1 C1 1.707(6) . ? S2 C1 1.734(6) . ? N1 C1 1.334(7) . ? N1 C3 1.442(7) . ? N1 C2 1.464(7) . ? O4 Na1 2.391(6) 2_575 ? C2 C2 1.515(10) 2_666 ? C3 C4 1.522(8) . ? C4 C5 1.381(9) . ? C4 C9 1.401(8) . ? C5 C6 1.372(8) . ? C6 C7 1.388(10) . ? C7 C8 1.393(10) . ? C8 C9 1.390(9) . ? 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 O2 Na1 O3 93.6(2) . . ? O2 Na1 O4 89.0(2) . 2_575 ? O3 Na1 O4 92.7(2) . 2_575 ? O2 Na1 O1 177.7(2) . . ? O3 Na1 O1 88.1(2) . . ? O4 Na1 O1 92.37(18) 2_575 . ? O2 Na1 O4 80.48(18) . . ? O3 Na1 O4 174.0(2) . . ? O4 Na1 O4 86.18(18) 2_575 . ? O1 Na1 O4 97.75(19) . . ? C1 N1 C3 121.6(6) . . ? C1 N1 C2 123.4(5) . . ? C3 N1 C2 115.0(5) . . ? Na1 O4 Na1 93.82(18) 2_575 . ? N1 C1 S1 122.1(5) . . ? N1 C1 S2 117.8(5) . . ? S1 C1 S2 120.1(4) . . ? N1 C2 C2 111.8(6) . 2_666 ? N1 C3 C4 113.5(5) . . ? C5 C4 C9 118.7(6) . . ? C5 C4 C3 123.9(6) . . ? C9 C4 C3 117.4(6) . . ? C6 C5 C4 120.9(7) . . ? C5 C6 C7 120.8(7) . . ? C6 C7 C8 119.4(6) . . ? C9 C8 C7 119.5(7) . . ? C8 C9 C4 120.7(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 Na1 O4 Na1 89.6(2) . . . 2_575 ? O4 Na1 O4 Na1 0.0 2_575 . . 2_575 ? O1 Na1 O4 Na1 -91.88(19) . . . 2_575 ? C3 N1 C1 S1 -3.8(8) . . . . ? C2 N1 C1 S1 175.9(4) . . . . ? C3 N1 C1 S2 176.4(4) . . . . ? C2 N1 C1 S2 -3.9(7) . . . . ? C1 N1 C2 C2 88.1(8) . . . 2_666 ? C3 N1 C2 C2 -92.3(7) . . . 2_666 ? C1 N1 C3 C4 97.4(7) . . . . ? C2 N1 C3 C4 -82.3(7) . . . . ? N1 C3 C4 C5 -3.6(9) . . . . ? N1 C3 C4 C9 176.0(6) . . . . ? C9 C4 C5 C6 0.5(11) . . . . ? C3 C4 C5 C6 -180.0(6) . . . . ? C4 C5 C6 C7 -1.5(11) . . . . ? C5 C6 C7 C8 1.9(12) . . . . ? C6 C7 C8 C9 -1.3(12) . . . . ? C7 C8 C9 C4 0.3(12) . . . . ? C5 C4 C9 C8 0.1(11) . . . . ? C3 C4 C9 C8 -179.5(7) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.344 _refine_diff_density_min -0.281 _refine_diff_density_rms 0.073 # Attachment 'revised_file_Compound_2.cif' data_ebdtckm _database_code_depnum_ccdc_archive 'CCDC 721769' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H26 K2 N2 O4 S4' _chemical_formula_sum 'C18 H26 K2 N2 O4 S4' _chemical_formula_weight 540.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 '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 6.4276(10) _cell_length_b 8.0682(12) _cell_length_c 12.1202(19) _cell_angle_alpha 101.826(2) _cell_angle_beta 104.093(3) _cell_angle_gamma 92.107(3) _cell_volume 594.19(16) _cell_formula_units_Z 1 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2699 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.55 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.511 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 282 _exptl_absorpt_coefficient_mu 0.778 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7618 _exptl_absorpt_correction_T_max 0.9263 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 '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 3046 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0318 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1992 _reflns_number_gt 1883 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All O-H hydrogen atoms have been localized by difference Fourier maps. Since during the unrestricted refinement of their coordinates the bond distances and bond angles started to deviate significantly from the expected geometries, the bonding geometries of the water molecules have been restrained during the refinement using DFIX and DANG instructions (Ow-H = 0.840(1) \%A, Hw...Hw = 1.35(1) \%A). ; _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^)+(0.0447P)^2^+0.5987P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1992 _refine_ls_number_parameters 148 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0419 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.0955 _refine_ls_wR_factor_gt 0.0937 _refine_ls_goodness_of_fit_ref 1.120 _refine_ls_restrained_S_all 1.119 _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 K1 K 0.41628(9) 0.81719(7) 0.58982(5) 0.01687(18) Uani 1 1 d . . . S1 S 0.62511(10) 0.47140(8) 0.63980(6) 0.01494(19) Uani 1 1 d . . . S2 S 1.06578(10) 0.37700(8) 0.74177(6) 0.01449(19) Uani 1 1 d . . . N1 N 0.8217(3) 0.5490(3) 0.86456(18) 0.0104(4) Uani 1 1 d . . . O1 O -0.0228(3) 0.7053(2) 0.53975(17) 0.0204(4) Uani 1 1 d D . . H11 H -0.089(4) 0.636(3) 0.565(2) 0.031 Uiso 1 1 d D . . H12 H -0.051(5) 0.671(3) 0.4670(4) 0.031 Uiso 1 1 d D . . O2 O 0.2223(3) 0.9941(2) 0.43423(17) 0.0200(4) Uani 1 1 d D . . H21 H 0.153(4) 0.911(2) 0.383(2) 0.030 Uiso 1 1 d D . . H22 H 0.144(4) 1.075(2) 0.435(3) 0.030 Uiso 1 1 d D . . C1 C 0.8368(4) 0.4713(3) 0.7573(2) 0.0118(5) Uani 1 1 d . . . C2 C 1.0024(4) 0.5727(3) 0.9680(2) 0.0133(5) Uani 1 1 d . . . H2A H 0.9968 0.6821 1.0215 0.016 Uiso 1 1 calc R . . H2B H 1.1392 0.5780 0.9445 0.016 Uiso 1 1 calc R . . C3 C 0.6226(4) 0.6157(3) 0.8852(2) 0.0119(5) Uani 1 1 d . . . H3A H 0.6221 0.6173 0.9670 0.014 Uiso 1 1 calc R . . H3B H 0.4993 0.5365 0.8343 0.014 Uiso 1 1 calc R . . C4 C 0.5884(4) 0.7918(3) 0.8637(2) 0.0117(5) Uani 1 1 d . . . C5 C 0.7509(4) 0.8983(3) 0.8506(2) 0.0128(5) Uani 1 1 d . . . H5 H 0.9001 0.8618 0.8605 0.015 Uiso 1 1 calc R . . C6 C 0.7114(4) 1.0595(3) 0.8306(2) 0.0151(6) Uani 1 1 d . . . H6 H 0.8329 1.1380 0.8276 0.018 Uiso 1 1 calc R . . C7 C 0.5100(4) 1.1176(3) 0.8255(2) 0.0173(6) Uani 1 1 d . . . H7 H 0.4867 1.2378 0.8199 0.021 Uiso 1 1 calc R . . C8 C 0.3462(4) 1.0124(3) 0.8388(2) 0.0185(6) Uani 1 1 d . . . H8 H 0.2045 1.0570 0.8428 0.022 Uiso 1 1 calc R . . C9 C 0.3856(4) 0.8507(3) 0.8575(2) 0.0153(6) Uani 1 1 d . . . H9 H 0.2705 0.7797 0.8737 0.018 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 K1 0.0195(3) 0.0155(3) 0.0149(3) 0.0041(2) 0.0023(2) 0.0030(2) S1 0.0149(3) 0.0160(3) 0.0122(4) 0.0029(3) 0.0001(3) 0.0050(3) S2 0.0117(3) 0.0152(3) 0.0172(4) 0.0038(3) 0.0046(3) 0.0035(2) N1 0.0106(10) 0.0104(10) 0.0114(11) 0.0064(8) 0.0013(8) 0.0034(8) O1 0.0257(11) 0.0169(10) 0.0207(11) 0.0050(8) 0.0090(9) 0.0017(8) O2 0.0200(10) 0.0160(10) 0.0236(11) 0.0048(8) 0.0039(8) 0.0045(8) C1 0.0136(12) 0.0075(11) 0.0160(14) 0.0066(10) 0.0039(11) 0.0004(9) C2 0.0139(12) 0.0120(12) 0.0126(13) 0.0031(10) 0.0007(10) -0.0004(10) C3 0.0124(12) 0.0127(12) 0.0129(13) 0.0045(10) 0.0061(10) 0.0019(10) C4 0.0139(12) 0.0122(12) 0.0084(12) 0.0023(10) 0.0012(10) 0.0023(10) C5 0.0113(12) 0.0156(13) 0.0109(13) 0.0019(10) 0.0025(10) 0.0011(10) C6 0.0183(13) 0.0117(12) 0.0140(13) 0.0016(10) 0.0034(11) -0.0015(10) C7 0.0238(14) 0.0116(13) 0.0166(14) 0.0034(11) 0.0049(12) 0.0035(11) C8 0.0162(13) 0.0199(14) 0.0218(15) 0.0054(11) 0.0082(12) 0.0064(11) C9 0.0150(13) 0.0170(13) 0.0179(14) 0.0064(11) 0.0089(11) 0.0037(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K1 O2 2.690(2) . ? K1 O1 2.811(2) . ? K1 O2 2.838(2) 2_676 ? K1 S1 3.1898(9) 2_666 ? K1 S1 3.2441(10) . ? K1 C8 3.249(3) . ? K1 C9 3.255(3) . ? K1 C7 3.258(3) . ? K1 C6 3.261(3) . ? K1 C5 3.284(3) . ? K1 C4 3.286(3) . ? S1 C1 1.714(3) . ? S2 C1 1.714(3) . ? N1 C1 1.351(3) . ? N1 C2 1.460(3) . ? N1 C3 1.463(3) . ? C2 C2 1.537(5) 2_767 ? C3 C4 1.510(3) . ? C4 C5 1.388(4) . ? C4 C9 1.394(3) . ? C5 C6 1.392(4) . ? C6 C7 1.384(4) . ? C7 C8 1.388(4) . ? C8 C9 1.391(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 O2 K1 O1 76.00(6) . . ? O2 K1 O2 79.23(6) . 2_676 ? O1 K1 O2 155.19(6) . 2_676 ? O2 K1 S1 82.56(5) . 2_666 ? O1 K1 S1 80.14(4) . 2_666 ? O2 K1 S1 95.41(4) 2_676 2_666 ? O2 K1 S1 148.63(5) . . ? O1 K1 S1 99.48(5) . . ? O2 K1 S1 100.94(4) 2_676 . ? S1 K1 S1 66.13(2) 2_666 . ? O2 K1 C8 105.60(7) . . ? O1 K1 C8 84.17(6) . . ? O2 K1 C8 103.96(6) 2_676 . ? S1 K1 C8 160.02(5) 2_666 . ? S1 K1 C8 104.76(5) . . ? O2 K1 C9 128.19(7) . . ? O1 K1 C9 82.47(6) . . ? O2 K1 C9 114.63(6) 2_676 . ? S1 K1 C9 139.05(5) 2_666 . ? S1 K1 C9 80.72(5) . . ? C8 K1 C9 24.70(7) . . ? O2 K1 C7 98.89(7) . . ? O1 K1 C7 105.64(6) . . ? O2 K1 C7 79.42(6) 2_676 . ? S1 K1 C7 174.22(5) 2_666 . ? S1 K1 C7 112.07(5) . . ? C8 K1 C7 24.64(7) . . ? C9 K1 C7 43.37(7) . . ? O2 K1 C6 113.01(7) . . ? O1 K1 C6 127.30(6) . . ? O2 K1 C6 64.73(6) 2_676 . ? S1 K1 C6 150.09(5) 2_666 . ? S1 K1 C6 94.61(5) . . ? C8 K1 C6 43.14(7) . . ? C9 K1 C6 50.16(7) . . ? C7 K1 C6 24.52(7) . . ? O2 K1 C5 137.52(6) . . ? O1 K1 C5 124.92(6) . . ? O2 K1 C5 75.62(6) 2_676 . ? S1 K1 C5 133.11(5) 2_666 . ? S1 K1 C5 70.60(5) . . ? C8 K1 C5 50.21(7) . . ? C9 K1 C5 42.87(6) . . ? C7 K1 C5 43.25(6) . . ? C6 K1 C5 24.56(6) . . ? O2 K1 C4 148.48(6) . . ? O1 K1 C4 101.89(6) . . ? O2 K1 C4 99.89(6) 2_676 . ? S1 K1 C4 128.55(5) 2_666 . ? S1 K1 C4 62.83(4) . . ? C8 K1 C4 43.56(7) . . ? C9 K1 C4 24.62(6) . . ? C7 K1 C4 50.74(7) . . ? C6 K1 C4 43.31(6) . . ? C5 K1 C4 24.39(6) . . ? C1 S1 K1 117.38(9) . 2_666 ? C1 S1 K1 122.41(8) . . ? K1 S1 K1 113.87(2) 2_666 . ? C1 N1 C2 122.5(2) . . ? C1 N1 C3 122.2(2) . . ? C2 N1 C3 115.3(2) . . ? K1 O2 K1 100.77(6) . 2_676 ? N1 C1 S1 118.60(19) . . ? N1 C1 S2 119.62(19) . . ? S1 C1 S2 121.78(15) . . ? N1 C2 C2 111.6(2) . 2_767 ? N1 C3 C4 115.2(2) . . ? C5 C4 C9 118.4(2) . . ? C5 C4 C3 122.8(2) . . ? C9 C4 C3 118.8(2) . . ? C5 C4 K1 77.74(15) . . ? C9 C4 K1 76.45(15) . . ? C3 C4 K1 116.16(15) . . ? C4 C5 C6 120.7(2) . . ? C4 C5 K1 77.87(15) . . ? C6 C5 K1 76.79(15) . . ? C7 C6 C5 120.5(2) . . ? C7 C6 K1 77.63(15) . . ? C5 C6 K1 78.65(14) . . ? C6 C7 C8 119.3(2) . . ? C6 C7 K1 77.85(15) . . ? C8 C7 K1 77.32(16) . . ? C7 C8 C9 120.0(2) . . ? C7 C8 K1 78.04(16) . . ? C9 C8 K1 77.87(15) . . ? C8 C9 C4 121.1(2) . . ? C8 C9 K1 77.43(16) . . ? C4 C9 K1 78.93(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 K1 S1 C1 147.32(13) . . . . ? O1 K1 S1 C1 -134.06(11) . . . . ? O2 K1 S1 C1 60.11(11) 2_676 . . . ? S1 K1 S1 C1 151.23(11) 2_666 . . . ? C8 K1 S1 C1 -47.64(11) . . . . ? C9 K1 S1 C1 -53.38(11) . . . . ? C7 K1 S1 C1 -22.80(12) . . . . ? C6 K1 S1 C1 -5.02(11) . . . . ? C5 K1 S1 C1 -10.25(11) . . . . ? C4 K1 S1 C1 -35.48(11) . . . . ? K1 K1 S1 C1 86.22(11) 2_676 . . . ? O2 K1 S1 K1 -3.91(9) . . . 2_666 ? O1 K1 S1 K1 74.71(5) . . . 2_666 ? O2 K1 S1 K1 -91.12(5) 2_676 . . 2_666 ? S1 K1 S1 K1 0.0 2_666 . . 2_666 ? C8 K1 S1 K1 161.13(5) . . . 2_666 ? C9 K1 S1 K1 155.39(5) . . . 2_666 ? C7 K1 S1 K1 -174.03(6) . . . 2_666 ? C6 K1 S1 K1 -156.25(5) . . . 2_666 ? C5 K1 S1 K1 -161.48(5) . . . 2_666 ? C4 K1 S1 K1 173.29(5) . . . 2_666 ? K1 K1 S1 K1 -65.01(4) 2_676 . . 2_666 ? O1 K1 O2 K1 -178.63(7) . . . 2_676 ? O2 K1 O2 K1 0.0 2_676 . . 2_676 ? S1 K1 O2 K1 -96.99(5) 2_666 . . 2_676 ? S1 K1 O2 K1 -93.38(9) . . . 2_676 ? C8 K1 O2 K1 101.64(7) . . . 2_676 ? C9 K1 O2 K1 112.97(8) . . . 2_676 ? C7 K1 O2 K1 77.36(7) . . . 2_676 ? C6 K1 O2 K1 56.43(8) . . . 2_676 ? C5 K1 O2 K1 54.41(11) . . . 2_676 ? C4 K1 O2 K1 91.39(12) . . . 2_676 ? C2 N1 C1 S1 -172.76(17) . . . . ? C3 N1 C1 S1 7.2(3) . . . . ? C2 N1 C1 S2 6.7(3) . . . . ? C3 N1 C1 S2 -173.30(17) . . . . ? K1 S1 C1 N1 -157.79(16) 2_666 . . . ? K1 S1 C1 N1 51.9(2) . . . . ? K1 S1 C1 S2 22.72(18) 2_666 . . . ? K1 S1 C1 S2 -127.57(12) . . . . ? C1 N1 C2 C2 -93.6(3) . . . 2_767 ? C3 N1 C2 C2 86.4(3) . . . 2_767 ? C1 N1 C3 C4 -84.1(3) . . . . ? C2 N1 C3 C4 95.8(3) . . . . ? N1 C3 C4 C5 -13.6(3) . . . . ? N1 C3 C4 C9 166.8(2) . . . . ? N1 C3 C4 K1 78.4(2) . . . . ? O2 K1 C4 C5 -79.62(19) . . . . ? O1 K1 C4 C5 -162.18(14) . . . . ? O2 K1 C4 C5 5.87(15) 2_676 . . . ? S1 K1 C4 C5 111.02(14) 2_666 . . . ? S1 K1 C4 C5 103.17(15) . . . . ? C8 K1 C4 C5 -94.03(17) . . . . ? C9 K1 C4 C5 -123.6(2) . . . . ? C7 K1 C4 C5 -61.60(15) . . . . ? C6 K1 C4 C5 -29.38(14) . . . . ? K1 K1 C4 C5 -19.88(17) 2_676 . . . ? O2 K1 C4 C9 43.9(2) . . . . ? O1 K1 C4 C9 -38.62(15) . . . . ? O2 K1 C4 C9 129.44(15) 2_676 . . . ? S1 K1 C4 C9 -125.41(14) 2_666 . . . ? S1 K1 C4 C9 -133.27(15) . . . . ? C8 K1 C4 C9 29.54(14) . . . . ? C7 K1 C4 C9 61.96(15) . . . . ? C6 K1 C4 C9 94.18(16) . . . . ? C5 K1 C4 C9 123.6(2) . . . . ? K1 K1 C4 C9 103.68(14) 2_676 . . . ? O2 K1 C4 C3 159.65(15) . . . . ? O1 K1 C4 C3 77.09(17) . . . . ? O2 K1 C4 C3 -114.85(16) 2_676 . . . ? S1 K1 C4 C3 -9.71(19) 2_666 . . . ? S1 K1 C4 C3 -17.56(14) . . . . ? C8 K1 C4 C3 145.2(2) . . . . ? C9 K1 C4 C3 115.7(2) . . . . ? C7 K1 C4 C3 177.7(2) . . . . ? C6 K1 C4 C3 -150.1(2) . . . . ? C5 K1 C4 C3 -120.7(2) . . . . ? K1 K1 C4 C3 -140.61(14) 2_676 . . . ? C9 C4 C5 C6 -0.6(4) . . . . ? C3 C4 C5 C6 179.8(2) . . . . ? K1 C4 C5 C6 66.5(2) . . . . ? C9 C4 C5 K1 -67.0(2) . . . . ? C3 C4 C5 K1 113.4(2) . . . . ? O2 K1 C5 C4 130.42(15) . . . . ? O1 K1 C5 C4 21.42(17) . . . . ? O2 K1 C5 C4 -174.03(16) 2_676 . . . ? S1 K1 C5 C4 -90.14(15) 2_666 . . . ? S1 K1 C5 C4 -66.69(14) . . . . ? C8 K1 C5 C4 63.46(15) . . . . ? C9 K1 C5 C4 30.67(14) . . . . ? C7 K1 C5 C4 96.21(17) . . . . ? C6 K1 C5 C4 125.9(2) . . . . ? K1 K1 C5 C4 164.33(14) 2_676 . . . ? O2 K1 C5 C6 4.49(19) . . . . ? O1 K1 C5 C6 -104.51(15) . . . . ? O2 K1 C5 C6 60.04(15) 2_676 . . . ? S1 K1 C5 C6 143.93(13) 2_666 . . . ? S1 K1 C5 C6 167.38(15) . . . . ? C8 K1 C5 C6 -62.47(15) . . . . ? C9 K1 C5 C6 -95.26(17) . . . . ? C7 K1 C5 C6 -29.72(14) . . . . ? C4 K1 C5 C6 -125.9(2) . . . . ? K1 K1 C5 C6 38.40(15) 2_676 . . . ? C4 C5 C6 C7 1.1(4) . . . . ? K1 C5 C6 C7 68.2(2) . . . . ? C4 C5 C6 K1 -67.0(2) . . . . ? O2 K1 C6 C7 58.22(17) . . . . ? O1 K1 C6 C7 -31.38(18) . . . . ? O2 K1 C6 C7 123.07(17) 2_676 . . . ? S1 K1 C6 C7 175.38(13) 2_666 . . . ? S1 K1 C6 C7 -137.00(15) . . . . ? C8 K1 C6 C7 -30.28(15) . . . . ? C9 K1 C6 C7 -63.13(16) . . . . ? C5 K1 C6 C7 -125.1(2) . . . . ? C4 K1 C6 C7 -95.89(17) . . . . ? K1 K1 C6 C7 91.30(15) 2_676 . . . ? O2 K1 C6 C5 -176.71(14) . . . . ? O1 K1 C6 C5 93.68(16) . . . . ? O2 K1 C6 C5 -111.86(16) 2_676 . . . ? S1 K1 C6 C5 -59.56(19) 2_666 . . . ? S1 K1 C6 C5 -11.93(15) . . . . ? C8 K1 C6 C5 94.78(17) . . . . ? C9 K1 C6 C5 61.93(15) . . . . ? C7 K1 C6 C5 125.1(2) . . . . ? C4 K1 C6 C5 29.18(14) . . . . ? K1 K1 C6 C5 -143.64(15) 2_676 . . . ? C5 C6 C7 C8 -1.0(4) . . . . ? K1 C6 C7 C8 67.8(2) . . . . ? C5 C6 C7 K1 -68.7(2) . . . . ? O2 K1 C7 C6 -127.63(15) . . . . ? O1 K1 C7 C6 154.52(15) . . . . ? O2 K1 C7 C6 -50.43(15) 2_676 . . . ? S1 K1 C7 C6 47.18(16) . . . . ? C8 K1 C7 C6 124.2(2) . . . . ? C9 K1 C7 C6 94.16(18) . . . . ? C5 K1 C7 C6 29.77(14) . . . . ? C4 K1 C7 C6 61.79(15) . . . . ? K1 K1 C7 C6 -87.93(15) 2_676 . . . ? O2 K1 C7 C8 108.16(17) . . . . ? O1 K1 C7 C8 30.31(18) . . . . ? O2 K1 C7 C8 -174.64(17) 2_676 . . . ? S1 K1 C7 C8 -77.02(17) . . . . ? C9 K1 C7 C8 -30.05(15) . . . . ? C6 K1 C7 C8 -124.2(2) . . . . ? C5 K1 C7 C8 -94.44(18) . . . . ? C4 K1 C7 C8 -62.42(16) . . . . ? K1 K1 C7 C8 147.87(16) 2_676 . . . ? C6 C7 C8 C9 0.2(4) . . . . ? K1 C7 C8 C9 68.3(2) . . . . ? C6 C7 C8 K1 -68.0(2) . . . . ? O2 K1 C8 C7 -77.07(17) . . . . ? O1 K1 C8 C7 -150.75(17) . . . . ? O2 K1 C8 C7 5.43(17) 2_676 . . . ? S1 K1 C8 C7 170.94(14) 2_666 . . . ? S1 K1 C8 C7 110.95(16) . . . . ? C9 K1 C8 C7 124.6(2) . . . . ? C6 K1 C8 C7 30.13(15) . . . . ? C5 K1 C8 C7 62.75(16) . . . . ? C4 K1 C8 C7 95.17(18) . . . . ? K1 K1 C8 C7 -34.29(17) 2_676 . . . ? O2 K1 C8 C9 158.32(15) . . . . ? O1 K1 C8 C9 84.64(15) . . . . ? O2 K1 C8 C9 -119.18(15) 2_676 . . . ? S1 K1 C8 C9 46.3(3) 2_666 . . . ? S1 K1 C8 C9 -13.66(16) . . . . ? C7 K1 C8 C9 -124.6(2) . . . . ? C6 K1 C8 C9 -94.48(18) . . . . ? C5 K1 C8 C9 -61.86(15) . . . . ? C4 K1 C8 C9 -29.44(14) . . . . ? K1 K1 C8 C9 -158.90(14) 2_676 . . . ? C7 C8 C9 C4 0.3(4) . . . . ? K1 C8 C9 C4 68.7(2) . . . . ? C7 C8 C9 K1 -68.4(2) . . . . ? C5 C4 C9 C8 -0.1(4) . . . . ? C3 C4 C9 C8 179.5(2) . . . . ? K1 C4 C9 C8 -67.9(2) . . . . ? C5 C4 C9 K1 67.8(2) . . . . ? C3 C4 C9 K1 -112.6(2) . . . . ? O2 K1 C9 C8 -26.91(18) . . . . ? O1 K1 C9 C8 -92.43(16) . . . . ? O2 K1 C9 C8 68.78(16) 2_676 . . . ? S1 K1 C9 C8 -157.85(13) 2_666 . . . ? S1 K1 C9 C8 166.63(16) . . . . ? C7 K1 C9 C8 29.98(15) . . . . ? C6 K1 C9 C8 62.60(16) . . . . ? C5 K1 C9 C8 95.22(17) . . . . ? C4 K1 C9 C8 125.6(2) . . . . ? K1 K1 C9 C8 27.18(18) 2_676 . . . ? O2 K1 C9 C4 -152.51(13) . . . . ? O1 K1 C9 C4 141.97(15) . . . . ? O2 K1 C9 C4 -56.83(16) 2_676 . . . ? S1 K1 C9 C4 76.55(16) 2_666 . . . ? S1 K1 C9 C4 41.02(14) . . . . ? C8 K1 C9 C4 -125.6(2) . . . . ? C7 K1 C9 C4 -95.62(17) . . . . ? C6 K1 C9 C4 -63.00(15) . . . . ? C5 K1 C9 C4 -30.38(14) . . . . ? K1 K1 C9 C4 -98.43(15) 2_676 . . . ? _diffrn_measured_fraction_theta_max 0.949 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.949 _refine_diff_density_max 0.478 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.077 # Attachment 'revised_file_Compound_3.cif' data_3reynam _database_code_depnum_ccdc_archive 'CCDC 721770' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 N2 O Rb2 S4' _chemical_formula_sum 'C18 H20 N2 O Rb2 S4' _chemical_formula_weight 579.54 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Rb Rb -0.9393 2.9676 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 21.895(2) _cell_length_b 6.4024(7) _cell_length_c 17.4640(19) _cell_angle_alpha 90.00 _cell_angle_beta 108.530(2) _cell_angle_gamma 90.00 _cell_volume 2321.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2779 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 25.31 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.48 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_absorpt_coefficient_mu 4.587 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.195 _exptl_absorpt_correction_T_max 0.459 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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 8289 _diffrn_reflns_av_R_equivalents 0.0426 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2051 _reflns_number_gt 1757 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All O-H hydrogen atoms have been localized by difference Fourier maps. Since during the unrestricted refinement of their coordinates the bond distances and bond angles started to deviate significantly from the expected geometries, the bonding geometries of the water molecules have been restrained during the refinement using DFIX and DANG instructions (Ow-H = 0.840(1) \%A, Hw...Hw 1.35(1) \%A and Rb...Hw = 3.00(1), 3.10(1), 3.40(1) and 3.55(1) \%A, respectively). ; _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^)+(0.0426P)^2^+6.3074P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2051 _refine_ls_number_parameters 141 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0769 _refine_ls_R_factor_gt 0.0652 _refine_ls_wR_factor_ref 0.1263 _refine_ls_wR_factor_gt 0.1216 _refine_ls_goodness_of_fit_ref 1.237 _refine_ls_restrained_S_all 1.234 _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 C1 C 0.1154(3) 0.7108(8) 0.4520(3) 0.0394(13) Uani 1 1 d . . . C2 C 0.2295(3) 0.7184(9) 0.4584(3) 0.0448(14) Uani 1 1 d . . . H2A H 0.2499 0.7640 0.4195 0.054 Uiso 1 1 calc R . . H2B H 0.2262 0.5673 0.4556 0.054 Uiso 1 1 calc R . . C3 C 0.1599(3) 1.0164(8) 0.4007(3) 0.0467(14) Uani 1 1 d . . . H3A H 0.1955 1.1013 0.4330 0.056 Uiso 1 1 calc R . . H3B H 0.1203 1.0816 0.4020 0.056 Uiso 1 1 calc R . . C4 C 0.1609(3) 1.0134(9) 0.3146(3) 0.0436(14) Uani 1 1 d . . . C5 C 0.1385(3) 0.8479(10) 0.2635(4) 0.0558(17) Uani 1 1 d . . . H5 H 0.1229 0.7293 0.2818 0.067 Uiso 1 1 calc R . . C6 C 0.1391(3) 0.8575(12) 0.1849(4) 0.0644(19) Uani 1 1 d . . . H6 H 0.1235 0.7449 0.1506 0.077 Uiso 1 1 calc R . . C7 C 0.1619(3) 1.0268(13) 0.1566(4) 0.066(2) Uani 1 1 d . . . H7 H 0.1625 1.0299 0.1036 0.079 Uiso 1 1 calc R . . C8 C 0.1840(3) 1.1934(12) 0.2067(4) 0.069(2) Uani 1 1 d . . . H8 H 0.1991 1.3117 0.1876 0.082 Uiso 1 1 calc R . . C9 C 0.1841(3) 1.1865(10) 0.2853(4) 0.0564(16) Uani 1 1 d . . . H9 H 0.1999 1.2996 0.3192 0.068 Uiso 1 1 calc R . . N1 N 0.1648(2) 0.8078(7) 0.4371(3) 0.0420(11) Uani 1 1 d . . . Rb1 Rb 0.02257(3) 0.68956(10) 0.60242(4) 0.0613(3) Uani 1 1 d D . . S1 S 0.12887(7) 0.4811(2) 0.50467(10) 0.0478(4) Uani 1 1 d . . . S2 S 0.03912(7) 0.8151(3) 0.41819(11) 0.0559(4) Uani 1 1 d . . . O1 O 0.0000 0.4648(19) 0.7500 0.082(4) Uani 0.608(13) 2 d SPD . 1 H11 H -0.029(3) 0.555(10) 0.734(4) 0.124 Uiso 0.304(7) 1 d PD . 1 H12 H -0.018(4) 0.347(6) 0.7389(16) 0.124 Uiso 0.304(7) 1 d PD . 1 O1B O 0.0000 0.872(3) 0.7500 0.085(7) Uani 0.392(13) 2 d SPD . 2 H11B H 0.009(12) 1.000(10) 0.754(9) 0.128 Uiso 0.196(7) 1 d PD . 2 H12B H -0.03975(13) 0.86(4) 0.726(6) 0.128 Uiso 0.196(7) 1 d PD . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.046(3) 0.041(3) 0.036(3) -0.010(2) 0.020(3) -0.007(3) C2 0.052(4) 0.049(3) 0.044(3) -0.011(3) 0.031(3) -0.009(3) C3 0.064(4) 0.035(3) 0.052(4) -0.003(3) 0.032(3) -0.008(3) C4 0.038(3) 0.050(4) 0.047(3) 0.003(3) 0.019(3) -0.001(3) C5 0.067(4) 0.056(4) 0.051(4) -0.009(3) 0.029(3) -0.017(3) C6 0.066(4) 0.083(5) 0.048(4) -0.009(4) 0.022(3) -0.006(4) C7 0.057(4) 0.103(6) 0.040(4) 0.014(4) 0.021(3) 0.003(4) C8 0.069(5) 0.079(5) 0.066(5) 0.022(4) 0.033(4) -0.009(4) C9 0.062(4) 0.052(4) 0.061(4) 0.007(3) 0.029(3) -0.010(3) N1 0.046(3) 0.046(3) 0.041(3) -0.006(2) 0.023(2) -0.005(2) Rb1 0.0560(4) 0.0557(4) 0.0780(5) 0.0010(3) 0.0294(3) 0.0007(3) S1 0.0498(9) 0.0399(8) 0.0581(10) 0.0055(7) 0.0235(7) 0.0007(7) S2 0.0478(9) 0.0514(9) 0.0713(11) 0.0077(8) 0.0230(8) 0.0070(7) O1 0.077(8) 0.102(10) 0.069(8) 0.000 0.023(6) 0.000 O1B 0.055(11) 0.16(2) 0.034(10) 0.000 0.002(8) 0.000 _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 C1 N1 1.342(7) . ? C1 S1 1.710(6) . ? C1 S2 1.720(6) . ? C2 N1 1.461(7) . ? C2 C2 1.502(11) 7_566 ? C3 N1 1.468(7) . ? C3 C4 1.511(8) . ? C4 C5 1.372(8) . ? C4 C9 1.384(8) . ? C5 C6 1.377(9) . ? C6 C7 1.352(9) . ? C7 C8 1.368(10) . ? C7 Rb1 3.415(7) 6_575 ? C8 C9 1.372(9) . ? C8 Rb1 3.505(7) 6_575 ? Rb1 O1B 3.011(8) . ? Rb1 O1 3.125(6) . ? Rb1 S2 3.4209(17) 5_576 ? Rb1 S1 3.4269(17) 5_566 ? Rb1 S2 3.4452(18) . ? Rb1 S2 3.4763(18) 5_566 ? Rb1 S1 3.5550(16) . ? 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 N1 C1 S1 119.3(4) . . ? N1 C1 S2 120.5(4) . . ? S1 C1 S2 120.1(3) . . ? N1 C2 C2 112.0(5) . 7_566 ? N1 C3 C4 113.4(4) . . ? C5 C4 C9 118.4(6) . . ? C5 C4 C3 122.9(5) . . ? C9 C4 C3 118.7(5) . . ? C4 C5 C6 120.0(6) . . ? C7 C6 C5 121.5(7) . . ? C6 C7 C8 119.2(6) . . ? C6 C7 Rb1 97.3(4) . 6_575 ? C8 C7 Rb1 82.3(4) . 6_575 ? C7 C8 C9 120.2(6) . . ? C7 C8 Rb1 74.9(4) . 6_575 ? C9 C8 Rb1 101.9(4) . 6_575 ? C8 C9 C4 120.8(6) . . ? C1 N1 C2 123.0(5) . . ? C1 N1 C3 123.6(5) . . ? C2 N1 C3 113.4(4) . . ? O1B Rb1 O1 50.3(4) . . ? O1B Rb1 C7 86.1(2) . 6_576 ? O1 Rb1 C7 112.20(15) . 6_576 ? O1B Rb1 S2 64.1(3) . 5_576 ? O1 Rb1 S2 110.67(19) . 5_576 ? C7 Rb1 S2 79.87(14) 6_576 5_576 ? O1B Rb1 S1 101.39(10) . 5_566 ? O1 Rb1 S1 85.65(7) . 5_566 ? C7 Rb1 S1 160.87(14) 6_576 5_566 ? S2 Rb1 S1 87.53(4) 5_576 5_566 ? O1B Rb1 S2 143.5(3) . . ? O1 Rb1 S2 165.6(2) . . ? C7 Rb1 S2 77.57(12) 6_576 . ? S2 Rb1 S2 80.83(5) 5_576 . ? S1 Rb1 S2 86.30(4) 5_566 . ? O1B Rb1 S2 106.6(3) . 5_566 ? O1 Rb1 S2 59.96(19) . 5_566 ? C7 Rb1 S2 143.74(14) 6_576 5_566 ? S2 Rb1 S2 136.33(5) 5_576 5_566 ? S1 Rb1 S2 50.99(4) 5_566 5_566 ? S2 Rb1 S2 105.83(4) . 5_566 ? O1B Rb1 C8 83.38(13) . 6_576 ? O1 Rb1 C8 93.86(14) . 6_576 ? C7 Rb1 C8 22.76(16) 6_576 6_576 ? S2 Rb1 C8 98.96(13) 5_576 6_576 ? S1 Rb1 C8 173.20(12) 5_566 6_576 ? S2 Rb1 C8 92.72(13) . 6_576 ? S2 Rb1 C8 123.16(14) 5_566 6_576 ? O1B Rb1 S1 150.17(5) . . ? O1 Rb1 S1 121.49(17) . . ? C7 Rb1 S1 70.68(12) 6_576 . ? S2 Rb1 S1 126.47(4) 5_576 . ? S1 Rb1 S1 106.61(3) 5_566 . ? S2 Rb1 S1 50.21(4) . . ? S2 Rb1 S1 83.88(4) 5_566 . ? C8 Rb1 S1 67.90(11) 6_576 . ? C1 S1 Rb1 90.51(19) . 5_566 ? C1 S1 Rb1 84.72(18) . . ? Rb1 S1 Rb1 73.39(3) 5_566 . ? C1 S2 Rb1 134.8(2) . 5_576 ? C1 S2 Rb1 88.15(19) . . ? Rb1 S2 Rb1 99.17(4) 5_576 . ? C1 S2 Rb1 88.71(19) . 5_566 ? Rb1 S2 Rb1 136.33(5) 5_576 5_566 ? Rb1 S2 Rb1 74.17(4) . 5_566 ? Rb1 O1 Rb1 125.2(4) 2_556 . ? Rb1 O1B Rb1 134.3(7) . 2_556 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 C5 29.0(8) . . . . ? N1 C3 C4 C9 -152.5(5) . . . . ? C9 C4 C5 C6 -0.4(9) . . . . ? C3 C4 C5 C6 178.2(6) . . . . ? C4 C5 C6 C7 0.5(11) . . . . ? C5 C6 C7 C8 -0.9(11) . . . . ? C5 C6 C7 Rb1 -86.1(7) . . . 6_575 ? C6 C7 C8 C9 1.2(11) . . . . ? Rb1 C7 C8 C9 95.2(7) 6_575 . . . ? C6 C7 C8 Rb1 -94.1(6) . . . 6_575 ? C7 C8 C9 C4 -1.1(10) . . . . ? Rb1 C8 C9 C4 78.3(6) 6_575 . . . ? C5 C4 C9 C8 0.7(9) . . . . ? C3 C4 C9 C8 -178.0(6) . . . . ? S1 C1 N1 C2 5.0(7) . . . . ? S2 C1 N1 C2 -174.8(4) . . . . ? S1 C1 N1 C3 -172.8(4) . . . . ? S2 C1 N1 C3 7.5(7) . . . . ? C2 C2 N1 C1 -90.4(7) 7_566 . . . ? C2 C2 N1 C3 87.6(7) 7_566 . . . ? C4 C3 N1 C1 -107.8(6) . . . . ? C4 C3 N1 C2 74.2(6) . . . . ? N1 C1 S1 Rb1 -147.7(4) . . . 5_566 ? S2 C1 S1 Rb1 32.0(3) . . . 5_566 ? N1 C1 S1 Rb1 139.0(4) . . . . ? S2 C1 S1 Rb1 -41.3(3) . . . . ? O1B Rb1 S1 C1 -108.7(7) . . . . ? O1 Rb1 S1 C1 -172.7(2) . . . . ? C7 Rb1 S1 C1 -68.0(2) 6_576 . . . ? S2 Rb1 S1 C1 -7.4(2) 5_576 . . . ? S1 Rb1 S1 C1 92.11(19) 5_566 . . . ? S2 Rb1 S1 C1 21.76(19) . . . . ? S2 Rb1 S1 C1 138.28(19) 5_566 . . . ? C8 Rb1 S1 C1 -92.1(2) 6_576 . . . ? Rb1 Rb1 S1 C1 92.11(19) 5_566 . . . ? Rb1 Rb1 S1 C1 6.91(19) 5_576 . . . ? O1B Rb1 S1 Rb1 159.1(7) . . . 5_566 ? O1 Rb1 S1 Rb1 95.16(14) . . . 5_566 ? C7 Rb1 S1 Rb1 -160.08(15) 6_576 . . 5_566 ? S2 Rb1 S1 Rb1 -99.47(5) 5_576 . . 5_566 ? S1 Rb1 S1 Rb1 0.0 5_566 . . 5_566 ? S2 Rb1 S1 Rb1 -70.36(5) . . . 5_566 ? S2 Rb1 S1 Rb1 46.16(3) 5_566 . . 5_566 ? C8 Rb1 S1 Rb1 175.75(15) 6_576 . . 5_566 ? Rb1 Rb1 S1 Rb1 -85.20(3) 5_576 . . 5_566 ? N1 C1 S2 Rb1 -36.5(6) . . . 5_576 ? S1 C1 S2 Rb1 143.8(2) . . . 5_576 ? N1 C1 S2 Rb1 -137.6(4) . . . . ? S1 C1 S2 Rb1 42.7(3) . . . . ? N1 C1 S2 Rb1 148.2(4) . . . 5_566 ? S1 C1 S2 Rb1 -31.5(3) . . . 5_566 ? O1B Rb1 S2 C1 119.0(2) . . . . ? O1 Rb1 S2 C1 -80.8(3) . . . . ? C7 Rb1 S2 C1 53.5(2) 6_576 . . . ? S2 Rb1 S2 C1 135.1(2) 5_576 . . . ? S1 Rb1 S2 C1 -136.80(19) 5_566 . . . ? S2 Rb1 S2 C1 -89.18(19) 5_566 . . . ? C8 Rb1 S2 C1 36.5(2) 6_576 . . . ? S1 Rb1 S2 C1 -21.54(18) . . . . ? Rb1 Rb1 S2 C1 -89.18(19) 5_566 . . . ? Rb1 Rb1 S2 C1 135.1(2) 5_576 . . . ? O1B Rb1 S2 Rb1 -16.09(10) . . . 5_576 ? O1 Rb1 S2 Rb1 144.1(2) . . . 5_576 ? C7 Rb1 S2 Rb1 -81.56(14) 6_576 . . 5_576 ? S2 Rb1 S2 Rb1 0.0 5_576 . . 5_576 ? S1 Rb1 S2 Rb1 88.09(4) 5_566 . . 5_576 ? S2 Rb1 S2 Rb1 135.71(5) 5_566 . . 5_576 ? C8 Rb1 S2 Rb1 -98.65(13) 6_576 . . 5_576 ? S1 Rb1 S2 Rb1 -156.65(7) . . . 5_576 ? Rb1 Rb1 S2 Rb1 135.71(5) 5_566 . . 5_576 ? O1B Rb1 S2 Rb1 -151.80(8) . . . 5_566 ? O1 Rb1 S2 Rb1 8.4(3) . . . 5_566 ? C7 Rb1 S2 Rb1 142.73(14) 6_576 . . 5_566 ? S2 Rb1 S2 Rb1 -135.71(5) 5_576 . . 5_566 ? S1 Rb1 S2 Rb1 -47.62(3) 5_566 . . 5_566 ? S2 Rb1 S2 Rb1 0.0 5_566 . . 5_566 ? C8 Rb1 S2 Rb1 125.64(13) 6_576 . . 5_566 ? S1 Rb1 S2 Rb1 67.64(4) . . . 5_566 ? Rb1 Rb1 S2 Rb1 -135.71(5) 5_576 . . 5_566 ? O1B Rb1 O1 Rb1 0.000(1) . . . 2_556 ? C7 Rb1 O1 Rb1 64.19(16) 6_576 . . 2_556 ? S2 Rb1 O1 Rb1 -23.00(5) 5_576 . . 2_556 ? S1 Rb1 O1 Rb1 -108.70(3) 5_566 . . 2_556 ? S2 Rb1 O1 Rb1 -164.8(3) . . . 2_556 ? S2 Rb1 O1 Rb1 -155.45(6) 5_566 . . 2_556 ? C8 Rb1 O1 Rb1 78.09(12) 6_576 . . 2_556 ? S1 Rb1 O1 Rb1 144.46(8) . . . 2_556 ? Rb1 Rb1 O1 Rb1 -157.52(4) 5_566 . . 2_556 ? Rb1 Rb1 O1 Rb1 -34.8(2) 5_576 . . 2_556 ? O1 Rb1 O1B Rb1 0.0 . . . 2_556 ? C7 Rb1 O1B Rb1 -123.34(14) 6_576 . . 2_556 ? S2 Rb1 O1B Rb1 156.02(8) 5_576 . . 2_556 ? S1 Rb1 O1B Rb1 74.46(7) 5_566 . . 2_556 ? S2 Rb1 O1B Rb1 173.73(8) . . . 2_556 ? S2 Rb1 O1B Rb1 22.05(5) 5_566 . . 2_556 ? C8 Rb1 O1B Rb1 -100.64(15) 6_576 . . 2_556 ? S1 Rb1 O1B Rb1 -85.2(6) . . . 2_556 ? Rb1 Rb1 O1B Rb1 54.6(6) 5_566 . . 2_556 ? Rb1 Rb1 O1B Rb1 163.09(4) 5_576 . . 2_556 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.514 _refine_diff_density_min -0.461 _refine_diff_density_rms 0.084 # Attachment 'revised_file_Compound_4.cif' data_dtccs2m _database_code_depnum_ccdc_archive 'CCDC 721771' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C18 H20 Cs2 N2 O S4' _chemical_formula_sum 'C18 H20 Cs2 N2 O S4' _chemical_formula_weight 674.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cs Cs -0.3680 2.1192 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 22.4220(19) _cell_length_b 6.5428(6) _cell_length_c 17.4010(15) _cell_angle_alpha 90.00 _cell_angle_beta 110.7110(10) _cell_angle_gamma 90.00 _cell_volume 2387.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 9075 _cell_measurement_theta_min 2.50 _cell_measurement_theta_max 28.26 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.876 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1296 _exptl_absorpt_coefficient_mu 3.414 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3828 _exptl_absorpt_correction_T_max 0.6206 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 '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 11021 _diffrn_reflns_av_R_equivalents 0.0367 _diffrn_reflns_av_sigmaI/netI 0.0242 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_h_max 26 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2105 _reflns_number_gt 2046 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. All O-H hydrogen atoms have been localized by difference Fourier maps. Since during the unrestricted refinement of their coordinates the bond distances and bond angles started to deviate significantly from the expected geometries, the bonding geometries of the water molecules have been restrained during the refinement using DFIX and DANG instructions (Ow-H = 0.840(1) \%A, Hw...Hw 1.35(1) \%A and Cs...Hw = 3.15(1), 3.25(1), 3.50(1) and 3.65(1) \%A, respectively. ; _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^)+(0.0277P)^2^+5.4038P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2105 _refine_ls_number_parameters 141 _refine_ls_number_restraints 10 _refine_ls_R_factor_all 0.0304 _refine_ls_R_factor_gt 0.0291 _refine_ls_wR_factor_ref 0.0718 _refine_ls_wR_factor_gt 0.0710 _refine_ls_goodness_of_fit_ref 1.174 _refine_ls_restrained_S_all 1.171 _refine_ls_shift/su_max 0.030 _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 C1 C 0.11751(16) 0.7129(5) 0.4516(2) 0.0360(7) Uani 1 1 d . . . C2 C 0.22858(17) 0.7198(6) 0.4573(2) 0.0433(8) Uani 1 1 d . . . H2A H 0.2248 0.5721 0.4540 0.052 Uiso 1 1 calc R . . H2B H 0.2476 0.7642 0.4180 0.052 Uiso 1 1 calc R . . C3 C 0.1593(2) 1.0130(6) 0.3996(2) 0.0475(9) Uani 1 1 d . . . H3A H 0.1937 1.0982 0.4344 0.057 Uiso 1 1 calc R . . H3B H 0.1194 1.0735 0.3979 0.057 Uiso 1 1 calc R . . C4 C 0.16153(16) 1.0113(6) 0.3137(2) 0.0412(8) Uani 1 1 d . . . C5 C 0.1366(2) 0.8535(6) 0.2590(3) 0.0527(9) Uani 1 1 d . . . H5 H 0.1173 0.7434 0.2747 0.063 Uiso 1 1 calc R . . C6 C 0.1399(2) 0.8574(7) 0.1815(3) 0.0580(10) Uani 1 1 d . . . H6 H 0.1233 0.7492 0.1456 0.070 Uiso 1 1 calc R . . C7 C 0.16731(19) 1.0189(7) 0.1569(2) 0.0580(11) Uani 1 1 d . . . H7 H 0.1689 1.0218 0.1042 0.070 Uiso 1 1 calc R . . C8 C 0.1925(2) 1.1764(7) 0.2102(3) 0.0630(12) Uani 1 1 d . . . H8 H 0.2117 1.2859 0.1940 0.076 Uiso 1 1 calc R . . C9 C 0.1894(2) 1.1731(6) 0.2883(3) 0.0543(10) Uani 1 1 d . . . H9 H 0.2064 1.2813 0.3240 0.065 Uiso 1 1 calc R . . N1 N 0.16506(14) 0.8098(4) 0.43575(18) 0.0390(7) Uani 1 1 d . . . Cs1 Cs 0.027354(12) 0.69113(4) 0.610069(16) 0.05427(12) Uani 1 1 d D . . S1 S 0.13186(4) 0.48625(14) 0.50316(6) 0.0467(2) Uani 1 1 d . . . S2 S 0.04247(5) 0.81862(14) 0.41933(7) 0.0484(2) Uani 1 1 d . . . O1 O 0.0000 0.4440(9) 0.7500 0.0711(17) Uani 0.864(8) 2 d SPD . 1 H11 H -0.0317(19) 0.522(8) 0.737(3) 0.107 Uiso 0.432(4) 1 d PD . 1 H12 H -0.014(3) 0.324(4) 0.7408(16) 0.107 Uiso 0.432(4) 1 d PD . 1 O1B O 0.0000 0.914(4) 0.7500 0.048(8) Uani 0.136(8) 2 d SPD . 2 H11B H 0.031(3) 0.995(12) 0.759(5) 0.072 Uiso 0.068(4) 1 d PD . 2 H12B H -0.033(3) 0.985(14) 0.7337(15) 0.072 Uiso 0.068(4) 1 d PD . 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0383(18) 0.0378(18) 0.0375(17) -0.0057(14) 0.0203(14) 0.0003(14) C2 0.0399(19) 0.052(2) 0.047(2) -0.0089(16) 0.0276(16) -0.0043(16) C3 0.061(2) 0.0411(19) 0.053(2) -0.0029(16) 0.0351(19) -0.0071(17) C4 0.0372(17) 0.047(2) 0.0458(19) 0.0020(15) 0.0221(15) -0.0016(15) C5 0.059(2) 0.053(2) 0.055(2) -0.0050(18) 0.031(2) -0.0149(19) C6 0.055(2) 0.073(3) 0.048(2) -0.011(2) 0.0210(19) -0.006(2) C7 0.048(2) 0.086(3) 0.042(2) 0.012(2) 0.0197(18) 0.006(2) C8 0.062(3) 0.074(3) 0.060(3) 0.018(2) 0.030(2) -0.007(2) C9 0.053(2) 0.058(2) 0.055(2) 0.0031(18) 0.0234(19) -0.0143(19) N1 0.0410(16) 0.0430(17) 0.0415(16) -0.0027(12) 0.0252(13) -0.0028(12) Cs1 0.05145(18) 0.05224(18) 0.0651(2) 0.00095(11) 0.02807(13) -0.00150(10) S1 0.0446(5) 0.0402(5) 0.0594(6) 0.0078(4) 0.0235(4) 0.0021(4) S2 0.0403(5) 0.0483(5) 0.0606(6) 0.0055(4) 0.0227(4) 0.0069(4) O1 0.078(4) 0.077(4) 0.062(3) 0.000 0.029(3) 0.000 O1B 0.042(14) 0.071(19) 0.033(13) 0.000 0.016(11) 0.000 _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 C1 N1 1.350(4) . ? C1 S1 1.704(3) . ? C1 S2 1.720(3) . ? C2 C2 1.510(7) 7_566 ? C2 N1 1.462(5) . ? C3 N1 1.457(5) . ? C3 C4 1.513(5) . ? C4 C5 1.381(5) . ? C4 C9 1.380(5) . ? C5 C6 1.377(6) . ? C6 C7 1.365(6) . ? C6 Cs1 3.797(5) 6_575 ? C7 C8 1.368(7) . ? C7 Cs1 3.508(4) 6_575 ? C8 C9 1.384(6) . ? C8 Cs1 3.596(5) 6_575 ? Cs1 O1B 3.080(12) . ? Cs1 O1 3.159(3) . ? Cs1 S1 3.6053(10) 5_566 ? Cs1 S2 3.5528(11) . ? Cs1 S2 3.5263(10) 5_576 ? Cs1 S2 3.6428(11) 5_566 ? Cs1 S1 3.7192(10) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 S1 120.0(3) . . ? N1 C1 S2 119.8(3) . . ? S1 C1 S2 120.2(2) . . ? N1 C1 Cs1 142.6(2) . . ? S1 C1 Cs1 69.49(11) . . ? S2 C1 Cs1 63.90(10) . . ? N1 C1 Cs1 151.0(2) . 5_566 ? S1 C1 Cs1 63.48(11) . 5_566 ? S2 C1 Cs1 64.74(11) . 5_566 ? Cs1 C1 Cs1 66.39(5) . 5_566 ? C2 C2 N1 111.7(4) 7_566 . ? N1 C3 C4 113.0(3) . . ? C5 C4 C9 118.2(3) . . ? C5 C4 C3 122.6(3) . . ? C9 C4 C3 119.2(3) . . ? C6 C5 C4 120.8(4) . . ? C5 C6 C7 120.5(4) . . ? C5 C6 Cs1 94.3(3) . 6_575 ? C7 C6 Cs1 67.4(3) . 6_575 ? C8 C7 C6 119.7(4) . . ? C8 C7 Cs1 82.6(3) . 6_575 ? C6 C7 Cs1 91.5(3) . 6_575 ? C9 C8 C7 120.1(4) . . ? C9 C8 Cs1 94.6(3) . 6_575 ? C7 C8 Cs1 75.3(3) . 6_575 ? C8 C9 C4 120.7(4) . . ? C1 N1 C2 121.8(3) . . ? C1 N1 C3 124.1(3) . . ? C2 N1 C3 114.0(3) . . ? O1B Cs1 O1 59.1(4) . . ? O1B Cs1 S1 98.56(13) . 5_566 ? O1 Cs1 S1 80.32(3) . 5_566 ? O1B Cs1 S2 137.6(4) . . ? O1 Cs1 S2 161.64(9) . . ? S1 Cs1 S2 88.18(2) 5_566 . ? O1B Cs1 C7 88.4(3) . 6_576 ? O1 Cs1 C7 119.96(8) . 6_576 ? S1 Cs1 C7 158.87(8) 5_566 6_576 ? S2 Cs1 C7 73.56(7) . 6_576 ? O1B Cs1 S2 58.8(4) . 5_576 ? O1 Cs1 S2 112.35(8) . 5_576 ? S1 Cs1 S2 84.87(2) 5_566 5_576 ? S2 Cs1 S2 80.51(3) . 5_576 ? C7 Cs1 S2 81.75(8) 6_576 5_576 ? O1B Cs1 C8 87.80(13) . 6_576 ? O1 Cs1 C8 101.37(8) . 6_576 ? S1 Cs1 C8 173.30(7) 5_566 6_576 ? S2 Cs1 C8 88.51(8) . 6_576 ? C7 Cs1 C8 22.15(11) 6_576 6_576 ? S2 Cs1 C8 100.33(8) 5_576 6_576 ? O1B Cs1 S2 110.4(4) . 5_566 ? O1 Cs1 S2 56.53(8) . 5_566 ? S1 Cs1 S2 48.33(2) 5_566 5_566 ? S2 Cs1 S2 105.19(2) . 5_566 ? C7 Cs1 S2 146.37(8) 6_576 5_566 ? S2 Cs1 S2 131.74(3) 5_576 5_566 ? C8 Cs1 S2 127.33(8) 6_576 5_566 ? O1B Cs1 S1 154.54(8) . . ? O1 Cs1 S1 121.98(8) . . ? S1 Cs1 S1 106.730(19) 5_566 . ? S2 Cs1 S1 48.10(2) . . ? C7 Cs1 S1 68.97(7) 6_576 . ? S2 Cs1 S1 125.54(2) 5_576 . ? C8 Cs1 S1 66.82(7) 6_576 . ? S2 Cs1 S1 85.14(2) 5_566 . ? O1B Cs1 C6 70.6(3) . 6_576 ? O1 Cs1 C6 115.70(9) . 6_576 ? S1 Cs1 C6 147.59(7) 5_566 6_576 ? S2 Cs1 C6 81.44(7) . 6_576 ? C7 Cs1 C6 21.06(10) 6_576 6_576 ? S2 Cs1 C6 63.22(7) 5_576 6_576 ? C8 Cs1 C6 37.14(10) 6_576 6_576 ? S2 Cs1 C6 163.95(7) 5_566 6_576 ? S1 Cs1 C6 88.90(7) . 6_576 ? O1B Cs1 C1 145.8(4) . . ? O1 Cs1 C1 147.36(9) . . ? S1 Cs1 C1 106.38(5) 5_566 . ? S2 Cs1 C1 25.76(5) . . ? C7 Cs1 C1 60.46(8) 6_576 . ? S2 Cs1 C1 100.15(5) 5_576 . ? C8 Cs1 C1 68.70(9) 6_576 . ? S2 Cs1 C1 103.60(5) 5_566 . ? S1 Cs1 C1 25.41(5) . . ? C6 Cs1 C1 75.87(8) 6_576 . ? O1B Cs1 C1 98.9(3) . 5_566 ? O1 Cs1 C1 60.75(7) . 5_566 ? S1 Cs1 C1 25.01(5) 5_566 5_566 ? S2 Cs1 C1 103.86(5) . 5_566 ? C7 Cs1 C1 171.05(9) 6_576 5_566 ? S2 Cs1 C1 106.47(5) 5_576 5_566 ? C8 Cs1 C1 151.92(9) 6_576 5_566 ? S2 Cs1 C1 25.27(5) 5_566 5_566 ? S1 Cs1 C1 102.80(5) . 5_566 ? C6 Cs1 C1 167.86(8) 6_576 5_566 ? C1 Cs1 C1 113.61(5) . 5_566 ? C1 S1 Cs1 91.51(12) . 5_566 ? C1 S1 Cs1 85.10(11) . . ? Cs1 S1 Cs1 73.270(19) 5_566 . ? C1 S2 Cs1 90.34(12) . . ? C1 S2 Cs1 138.28(12) . 5_576 ? Cs1 S2 Cs1 99.49(3) . 5_576 ? C1 S2 Cs1 89.99(12) . 5_566 ? Cs1 S2 Cs1 74.81(2) . 5_566 ? Cs1 S2 Cs1 131.74(3) 5_576 5_566 ? Cs1 O1 Cs1 118.41(18) 2_556 . ? Cs1 O1B Cs1 123.5(8) . 2_556 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 C5 33.9(5) . . . . ? N1 C3 C4 C9 -146.1(4) . . . . ? C9 C4 C5 C6 0.4(6) . . . . ? C3 C4 C5 C6 -179.6(4) . . . . ? C4 C5 C6 C7 -0.8(7) . . . . ? C4 C5 C6 Cs1 -67.1(4) . . . 6_575 ? C5 C6 C7 C8 1.0(7) . . . . ? Cs1 C6 C7 C8 82.3(4) 6_575 . . . ? C5 C6 C7 Cs1 -81.3(4) . . . 6_575 ? C6 C7 C8 C9 -0.8(7) . . . . ? Cs1 C7 C8 C9 86.7(4) 6_575 . . . ? C6 C7 C8 Cs1 -87.5(4) . . . 6_575 ? C7 C8 C9 C4 0.5(7) . . . . ? Cs1 C8 C9 C4 76.1(4) 6_575 . . . ? C5 C4 C9 C8 -0.3(6) . . . . ? C3 C4 C9 C8 179.8(4) . . . . ? S1 C1 N1 C2 3.7(4) . . . . ? S2 C1 N1 C2 -176.0(2) . . . . ? Cs1 C1 N1 C2 98.9(4) . . . . ? Cs1 C1 N1 C2 -85.0(5) 5_566 . . . ? S1 C1 N1 C3 -173.6(3) . . . . ? S2 C1 N1 C3 6.6(5) . . . . ? Cs1 C1 N1 C3 -78.4(5) . . . . ? Cs1 C1 N1 C3 97.6(5) 5_566 . . . ? C2 C2 N1 C1 -90.0(5) 7_566 . . . ? C2 C2 N1 C3 87.6(4) 7_566 . . . ? C4 C3 N1 C1 -111.8(4) . . . . ? C4 C3 N1 C2 70.7(4) . . . . ? N1 C1 Cs1 O1B 17.2(6) . . . . ? S1 C1 Cs1 O1B 130.2(4) . . . . ? S2 C1 Cs1 O1B -88.5(4) . . . . ? Cs1 C1 Cs1 O1B -160.7(4) 5_566 . . . ? N1 C1 Cs1 O1 -109.9(4) . . . . ? S1 C1 Cs1 O1 3.1(2) . . . . ? S2 C1 Cs1 O1 144.44(12) . . . . ? Cs1 C1 Cs1 O1 72.16(13) 5_566 . . . ? N1 C1 Cs1 S1 152.4(4) . . . 5_566 ? S1 C1 Cs1 S1 -94.62(11) . . . 5_566 ? S2 C1 Cs1 S1 46.75(12) . . . 5_566 ? Cs1 C1 Cs1 S1 -25.53(5) 5_566 . . 5_566 ? N1 C1 Cs1 S2 105.6(4) . . . . ? S1 C1 Cs1 S2 -141.4(2) . . . . ? Cs1 C1 Cs1 S2 -72.28(10) 5_566 . . . ? N1 C1 Cs1 C7 -9.6(4) . . . 6_576 ? S1 C1 Cs1 C7 103.40(15) . . . 6_576 ? S2 C1 Cs1 C7 -115.22(15) . . . 6_576 ? Cs1 C1 Cs1 C7 172.50(11) 5_566 . . 6_576 ? N1 C1 Cs1 S2 64.8(4) . . . 5_576 ? S1 C1 Cs1 S2 177.79(10) . . . 5_576 ? S2 C1 Cs1 S2 -40.83(12) . . . 5_576 ? Cs1 C1 Cs1 S2 -113.11(4) 5_566 . . 5_576 ? N1 C1 Cs1 C8 -32.4(4) . . . 6_576 ? S1 C1 Cs1 C8 80.57(14) . . . 6_576 ? S2 C1 Cs1 C8 -138.05(15) . . . 6_576 ? Cs1 C1 Cs1 C8 149.67(10) 5_566 . . 6_576 ? N1 C1 Cs1 S2 -157.6(4) . . . 5_566 ? S1 C1 Cs1 S2 -44.55(12) . . . 5_566 ? S2 C1 Cs1 S2 96.83(11) . . . 5_566 ? Cs1 C1 Cs1 S2 24.55(5) 5_566 . . 5_566 ? N1 C1 Cs1 S1 -113.0(4) . . . . ? S2 C1 Cs1 S1 141.4(2) . . . . ? Cs1 C1 Cs1 S1 69.10(10) 5_566 . . . ? N1 C1 Cs1 C6 5.9(4) . . . 6_576 ? S1 C1 Cs1 C6 118.93(13) . . . 6_576 ? S2 C1 Cs1 C6 -99.70(13) . . . 6_576 ? Cs1 C1 Cs1 C6 -171.98(8) 5_566 . . 6_576 ? N1 C1 Cs1 C1 177.9(4) . . . 5_566 ? S1 C1 Cs1 C1 -69.10(10) . . . 5_566 ? S2 C1 Cs1 C1 72.28(10) . . . 5_566 ? Cs1 C1 Cs1 C1 0.0 5_566 . . 5_566 ? N1 C1 S1 Cs1 -147.2(3) . . . 5_566 ? S2 C1 S1 Cs1 32.6(2) . . . 5_566 ? Cs1 C1 S1 Cs1 73.07(2) . . . 5_566 ? N1 C1 S1 Cs1 139.8(3) . . . . ? S2 C1 S1 Cs1 -40.43(19) . . . . ? Cs1 C1 S1 Cs1 -73.07(2) 5_566 . . . ? O1B Cs1 S1 C1 -93.7(10) . . . . ? O1 Cs1 S1 C1 -178.05(13) . . . . ? S1 Cs1 S1 C1 93.06(12) 5_566 . . . ? S2 Cs1 S1 C1 21.38(12) . . . . ? C7 Cs1 S1 C1 -65.05(14) 6_576 . . . ? S2 Cs1 S1 C1 -2.67(12) 5_576 . . . ? C8 Cs1 S1 C1 -88.88(15) 6_576 . . . ? S2 Cs1 S1 C1 136.82(12) 5_566 . . . ? C6 Cs1 S1 C1 -58.09(13) 6_576 . . . ? C1 Cs1 S1 C1 118.62(10) 5_566 . . . ? O1B Cs1 S1 Cs1 173.2(9) . . . 5_566 ? O1 Cs1 S1 Cs1 88.89(6) . . . 5_566 ? S1 Cs1 S1 Cs1 0.0 5_566 . . 5_566 ? S2 Cs1 S1 Cs1 -71.68(3) . . . 5_566 ? C7 Cs1 S1 Cs1 -158.11(8) 6_576 . . 5_566 ? S2 Cs1 S1 Cs1 -95.73(3) 5_576 . . 5_566 ? C8 Cs1 S1 Cs1 178.06(9) 6_576 . . 5_566 ? S2 Cs1 S1 Cs1 43.76(2) 5_566 . . 5_566 ? C6 Cs1 S1 Cs1 -151.16(7) 6_576 . . 5_566 ? C1 Cs1 S1 Cs1 -93.06(12) . . . 5_566 ? C1 Cs1 S1 Cs1 25.56(5) 5_566 . . 5_566 ? N1 C1 S2 Cs1 -137.6(3) . . . . ? S1 C1 S2 Cs1 42.57(19) . . . . ? Cs1 C1 S2 Cs1 74.81(2) 5_566 . . . ? N1 C1 S2 Cs1 -32.9(4) . . . 5_576 ? S1 C1 S2 Cs1 147.31(13) . . . 5_576 ? Cs1 C1 S2 Cs1 104.75(14) . . . 5_576 ? Cs1 C1 S2 Cs1 179.56(15) 5_566 . . 5_576 ? N1 C1 S2 Cs1 147.6(3) . . . 5_566 ? S1 C1 S2 Cs1 -32.24(19) . . . 5_566 ? Cs1 C1 S2 Cs1 -74.81(2) . . . 5_566 ? O1B Cs1 S2 C1 123.63(16) . . . . ? O1 Cs1 S2 C1 -84.69(17) . . . . ? S1 Cs1 S2 C1 -135.64(12) 5_566 . . . ? C7 Cs1 S2 C1 55.14(14) 6_576 . . . ? S2 Cs1 S2 C1 139.27(12) 5_576 . . . ? C8 Cs1 S2 C1 38.54(14) 6_576 . . . ? S2 Cs1 S2 C1 -89.89(11) 5_566 . . . ? S1 Cs1 S2 C1 -21.09(11) . . . . ? C6 Cs1 S2 C1 75.16(13) 6_576 . . . ? C1 Cs1 S2 C1 -115.98(11) 5_566 . . . ? O1B Cs1 S2 Cs1 -15.64(11) . . . 5_576 ? O1 Cs1 S2 Cs1 136.05(12) . . . 5_576 ? S1 Cs1 S2 Cs1 85.10(3) 5_566 . . 5_576 ? C7 Cs1 S2 Cs1 -84.13(8) 6_576 . . 5_576 ? S2 Cs1 S2 Cs1 0.0 5_576 . . 5_576 ? C8 Cs1 S2 Cs1 -100.73(8) 6_576 . . 5_576 ? S2 Cs1 S2 Cs1 130.84(3) 5_566 . . 5_576 ? S1 Cs1 S2 Cs1 -160.35(4) . . . 5_576 ? C6 Cs1 S2 Cs1 -64.10(7) 6_576 . . 5_576 ? C1 Cs1 S2 Cs1 -139.27(12) . . . 5_576 ? C1 Cs1 S2 Cs1 104.76(5) 5_566 . . 5_576 ? O1B Cs1 S2 Cs1 -146.48(11) . . . 5_566 ? O1 Cs1 S2 Cs1 5.21(12) . . . 5_566 ? S1 Cs1 S2 Cs1 -45.745(19) 5_566 . . 5_566 ? C7 Cs1 S2 Cs1 145.03(8) 6_576 . . 5_566 ? S2 Cs1 S2 Cs1 -130.84(3) 5_576 . . 5_566 ? C8 Cs1 S2 Cs1 128.43(7) 6_576 . . 5_566 ? S2 Cs1 S2 Cs1 0.0 5_566 . . 5_566 ? S1 Cs1 S2 Cs1 68.80(3) . . . 5_566 ? C6 Cs1 S2 Cs1 165.06(7) 6_576 . . 5_566 ? C1 Cs1 S2 Cs1 89.89(11) . . . 5_566 ? C1 Cs1 S2 Cs1 -26.08(5) 5_566 . . 5_566 ? O1B Cs1 O1 Cs1 0.0 . . . 2_556 ? S1 Cs1 O1 Cs1 -106.17(2) 5_566 . . 2_556 ? S2 Cs1 O1 Cs1 -158.11(12) . . . 2_556 ? C7 Cs1 O1 Cs1 67.46(10) 6_576 . . 2_556 ? S2 Cs1 O1 Cs1 -25.86(3) 5_576 . . 2_556 ? C8 Cs1 O1 Cs1 80.43(7) 6_576 . . 2_556 ? S2 Cs1 O1 Cs1 -152.09(3) 5_566 . . 2_556 ? S1 Cs1 O1 Cs1 150.08(4) . . . 2_556 ? C6 Cs1 O1 Cs1 44.10(8) 6_576 . . 2_556 ? C1 Cs1 O1 Cs1 148.53(12) . . . 2_556 ? C1 Cs1 O1 Cs1 -122.81(7) 5_566 . . 2_556 ? O1 Cs1 O1B Cs1 0.0 . . . 2_556 ? S1 Cs1 O1B Cs1 73.22(6) 5_566 . . 2_556 ? S2 Cs1 O1B Cs1 169.97(9) . . . 2_556 ? C7 Cs1 O1B Cs1 -126.82(8) 6_576 . . 2_556 ? S2 Cs1 O1B Cs1 151.86(13) 5_576 . . 2_556 ? C8 Cs1 O1B Cs1 -104.66(8) 6_576 . . 2_556 ? S2 Cs1 O1B Cs1 24.62(7) 5_566 . . 2_556 ? S1 Cs1 O1B Cs1 -100.2(9) . . . 2_556 ? C6 Cs1 O1B Cs1 -138.34(12) 6_576 . . 2_556 ? C1 Cs1 O1B Cs1 -149.9(3) . . . 2_556 ? C1 Cs1 O1B Cs1 47.92(7) 5_566 . . 2_556 ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.549 _refine_diff_density_min -0.678 _refine_diff_density_rms 0.088 # Attachment 'revised_file_Compound_5.cif' data_sad _database_code_depnum_ccdc_archive 'CCDC 721772' _audit_update_record ; 2009-02-25 # Formatted by publCIF ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point 471.6 _chemical_formula_moiety 'C18 H18 N2 S4, 2(C6 H16 N)' _chemical_formula_sum 'C30 H50 N4 S4' _chemical_formula_weight 594.98 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M C2/c _symmetry_space_group_name_Hall '-C 2yc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 15.677(3) _cell_length_b 10.452(2) _cell_length_c 20.855(4) _cell_angle_alpha 90.00 _cell_angle_beta 103.12(3) _cell_angle_gamma 90.00 _cell_volume 3328.1(12) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1447 _cell_measurement_theta_min 2.3 _cell_measurement_theta_max 25.6 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.22 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.187 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1288 _exptl_absorpt_coefficient_mu 0.310 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9099 _exptl_absorpt_correction_T_max 0.9349 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 APEX CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.3 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8095 _diffrn_reflns_av_R_equivalents 0.0479 _diffrn_reflns_av_sigmaI/netI 0.0643 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2932 _reflns_number_gt 2168 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT-Plus NT (Bruker, 2001)' _computing_data_reduction 'SAINT-Plus NT' _computing_structure_solution 'SHELXTL-NT (Sheldrick, 2008)' _computing_structure_refinement SHELXTL-NT _computing_molecular_graphics SHELXTL-NT _computing_publication_material ? _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^)+(0.1051P)^2^+5.3494P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2932 _refine_ls_number_parameters 179 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1304 _refine_ls_R_factor_gt 0.1008 _refine_ls_wR_factor_ref 0.2585 _refine_ls_wR_factor_gt 0.2410 _refine_ls_goodness_of_fit_ref 1.183 _refine_ls_restrained_S_all 1.183 _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 C1 C 0.0854(3) 0.6143(5) 0.1176(2) 0.0464(12) Uani 1 1 d . . . C2 C 0.0411(3) 0.5404(5) 0.0032(2) 0.0456(12) Uani 1 1 d . . . H2A H 0.0923 0.4855 0.0140 0.055 Uiso 1 1 calc R . . H2B H 0.0405 0.5813 -0.0387 0.055 Uiso 1 1 calc R . . C3 C 0.0070(3) 0.7602(5) 0.0294(3) 0.0506(13) Uani 1 1 d . . . H3A H 0.0028 0.8134 0.0666 0.061 Uiso 1 1 calc R . . H3B H -0.0519 0.7449 0.0037 0.061 Uiso 1 1 calc R . . C4 C 0.0578(3) 0.8305(5) -0.0123(2) 0.0460(12) Uani 1 1 d . . . C5 C 0.0161(4) 0.8861(6) -0.0708(3) 0.0678(17) Uani 1 1 d . . . H5 H -0.0445 0.8799 -0.0843 0.081 Uiso 1 1 calc R . . C6 C 0.0613(6) 0.9504(7) -0.1099(4) 0.082(2) Uani 1 1 d . . . H6 H 0.0311 0.9872 -0.1491 0.098 Uiso 1 1 calc R . . C7 C 0.1488(6) 0.9607(6) -0.0920(4) 0.080(2) Uani 1 1 d . . . H7 H 0.1796 1.0030 -0.1188 0.097 Uiso 1 1 calc R . . C8 C 0.1920(5) 0.9081(7) -0.0336(4) 0.089(2) Uani 1 1 d . . . H8 H 0.2526 0.9156 -0.0206 0.106 Uiso 1 1 calc R . . C9 C 0.1469(4) 0.8437(7) 0.0066(3) 0.0723(18) Uani 1 1 d . . . H9 H 0.1772 0.8094 0.0464 0.087 Uiso 1 1 calc R . . C10 C 0.1135(6) 0.4993(8) 0.3319(6) 0.133(4) Uani 1 1 d D . . H10A H 0.1251 0.5103 0.3793 0.159 Uiso 1 1 calc R . . H10B H 0.0560 0.5351 0.3138 0.159 Uiso 1 1 calc R . . C11 C 0.1091(10) 0.3586(8) 0.3179(8) 0.206(7) Uani 1 1 d D . . H11A H 0.0930 0.3450 0.2712 0.309 Uiso 1 1 calc R . . H11B H 0.0661 0.3201 0.3381 0.309 Uiso 1 1 calc R . . H11C H 0.1653 0.3207 0.3356 0.309 Uiso 1 1 calc R . . C12 C 0.1808(5) 0.7022(6) 0.3413(3) 0.0706(18) Uani 1 1 d . . . H12A H 0.1208 0.7313 0.3358 0.085 Uiso 1 1 calc R . . H12B H 0.2117 0.7650 0.3209 0.085 Uiso 1 1 calc R . . C13 C 0.2225(6) 0.6969(8) 0.4137(3) 0.096(3) Uani 1 1 d . . . H13A H 0.1893 0.6410 0.4352 0.144 Uiso 1 1 calc R . . H13B H 0.2236 0.7812 0.4322 0.144 Uiso 1 1 calc R . . H13C H 0.2813 0.6652 0.4199 0.144 Uiso 1 1 calc R . . C14 C 0.2642(5) 0.5208(8) 0.3079(4) 0.094(2) Uani 1 1 d . . . H14A H 0.2551 0.4395 0.2850 0.113 Uiso 1 1 calc R . . H14B H 0.2941 0.5043 0.3532 0.113 Uiso 1 1 calc R . . C15 C 0.3214(5) 0.6054(9) 0.2759(4) 0.113(3) Uani 1 1 d . . . H15A H 0.2888 0.6323 0.2334 0.169 Uiso 1 1 calc R . . H15B H 0.3721 0.5583 0.2711 0.169 Uiso 1 1 calc R . . H15C H 0.3394 0.6791 0.3030 0.169 Uiso 1 1 calc R . . H2 H 0.154(5) 0.596(7) 0.264(4) 0.10(2) Uiso 1 1 d . . . N1 N 0.0471(3) 0.6375(4) 0.05373(18) 0.0427(10) Uani 1 1 d . . . N2 N 0.1805(3) 0.5794(5) 0.3065(2) 0.0610(13) Uani 1 1 d . . . S1 S 0.12759(10) 0.46633(14) 0.14027(7) 0.0603(5) Uani 1 1 d . . . S2 S 0.08806(11) 0.73296(15) 0.17467(7) 0.0648(5) 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 C1 0.042(3) 0.049(3) 0.048(3) 0.001(2) 0.009(2) -0.011(2) C2 0.049(3) 0.059(3) 0.032(2) -0.009(2) 0.014(2) -0.008(2) C3 0.046(3) 0.056(3) 0.047(3) -0.005(2) 0.005(2) 0.005(3) C4 0.056(3) 0.041(3) 0.042(3) -0.003(2) 0.012(2) 0.004(2) C5 0.057(4) 0.080(4) 0.065(4) 0.014(3) 0.012(3) 0.007(3) C6 0.101(6) 0.072(5) 0.077(5) 0.023(4) 0.032(4) 0.014(4) C7 0.112(6) 0.044(4) 0.097(5) 0.002(4) 0.049(5) -0.016(4) C8 0.065(4) 0.087(5) 0.117(6) -0.009(5) 0.027(4) -0.030(4) C9 0.057(4) 0.085(5) 0.069(4) 0.009(3) 0.003(3) -0.017(3) C10 0.118(7) 0.123(8) 0.162(10) 0.033(7) 0.042(7) -0.028(6) C11 0.236(15) 0.133(10) 0.308(19) 0.053(12) 0.187(14) -0.007(10) C12 0.092(5) 0.065(4) 0.053(3) -0.001(3) 0.011(3) 0.009(4) C13 0.139(7) 0.090(5) 0.054(4) -0.004(4) 0.013(4) 0.017(5) C14 0.102(6) 0.092(6) 0.078(5) -0.006(4) -0.001(4) 0.025(5) C15 0.066(5) 0.154(9) 0.108(6) 0.020(6) -0.002(4) -0.020(5) N1 0.046(2) 0.044(2) 0.036(2) -0.0031(18) 0.0056(18) -0.0063(19) N2 0.070(3) 0.061(3) 0.047(3) 0.001(2) 0.003(2) 0.012(3) S1 0.0667(10) 0.0513(9) 0.0594(9) 0.0055(7) 0.0072(7) 0.0044(7) S2 0.0857(12) 0.0582(10) 0.0434(8) -0.0133(6) -0.0004(7) 0.0029(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 C1 N1 1.354(6) . ? C1 S1 1.706(5) . ? C1 S2 1.713(5) . ? C2 N1 1.452(6) . ? C2 C2 1.522(9) 5_565 ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N1 1.466(6) . ? C3 C4 1.498(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C9 1.369(8) . ? C4 C5 1.376(7) . ? C5 C6 1.371(9) . ? C5 H5 0.9300 . ? C6 C7 1.341(10) . ? C6 H6 0.9300 . ? C7 C8 1.366(10) . ? C7 H7 0.9300 . ? C8 C9 1.388(9) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.4979(11) . ? C10 N2 1.529(10) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 N2 1.473(7) . ? C12 C13 1.504(8) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 N2 1.443(8) . ? C14 C15 1.516(11) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? N2 H2 0.91(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 S1 119.5(4) . . ? N1 C1 S2 119.3(4) . . ? S1 C1 S2 121.2(3) . . ? N1 C2 C2 111.3(5) . 5_565 ? N1 C2 H2A 109.4 . . ? C2 C2 H2A 109.4 5_565 . ? N1 C2 H2B 109.4 . . ? C2 C2 H2B 109.4 5_565 . ? H2A C2 H2B 108.0 . . ? N1 C3 C4 112.8(4) . . ? N1 C3 H3A 109.0 . . ? C4 C3 H3A 109.0 . . ? N1 C3 H3B 109.0 . . ? C4 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C9 C4 C5 117.4(5) . . ? C9 C4 C3 121.6(5) . . ? C5 C4 C3 121.0(5) . . ? C6 C5 C4 122.0(6) . . ? C6 C5 H5 119.0 . . ? C4 C5 H5 119.0 . . ? C7 C6 C5 120.5(7) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 119.0(7) . . ? C6 C7 H7 120.5 . . ? C8 C7 H7 120.5 . . ? C7 C8 C9 121.1(7) . . ? C7 C8 H8 119.5 . . ? C9 C8 H8 119.5 . . ? C4 C9 C8 120.1(6) . . ? C4 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C11 C10 N2 118.4(8) . . ? C11 C10 H10A 107.7 . . ? N2 C10 H10A 107.7 . . ? C11 C10 H10B 107.7 . . ? N2 C10 H10B 107.7 . . ? H10A C10 H10B 107.1 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? N2 C12 C13 114.5(6) . . ? N2 C12 H12A 108.6 . . ? C13 C12 H12A 108.6 . . ? N2 C12 H12B 108.6 . . ? C13 C12 H12B 108.6 . . ? H12A C12 H12B 107.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N2 C14 C15 111.7(7) . . ? N2 C14 H14A 109.3 . . ? C15 C14 H14A 109.3 . . ? N2 C14 H14B 109.3 . . ? C15 C14 H14B 109.3 . . ? H14A C14 H14B 107.9 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C1 N1 C2 122.0(4) . . ? C1 N1 C3 123.9(4) . . ? C2 N1 C3 114.1(4) . . ? C14 N2 C12 117.3(5) . . ? C14 N2 C10 117.0(6) . . ? C12 N2 C10 103.4(6) . . ? C14 N2 H2 108(4) . . ? C12 N2 H2 105(5) . . ? C10 N2 H2 104(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C3 C4 C9 -46.2(7) . . . . ? N1 C3 C4 C5 134.8(5) . . . . ? C9 C4 C5 C6 1.3(9) . . . . ? C3 C4 C5 C6 -179.7(6) . . . . ? C4 C5 C6 C7 0.2(11) . . . . ? C5 C6 C7 C8 -1.2(11) . . . . ? C6 C7 C8 C9 0.7(11) . . . . ? C5 C4 C9 C8 -1.7(9) . . . . ? C3 C4 C9 C8 179.2(6) . . . . ? C7 C8 C9 C4 0.8(11) . . . . ? S1 C1 N1 C2 -0.6(6) . . . . ? S2 C1 N1 C2 -178.8(3) . . . . ? S1 C1 N1 C3 178.5(4) . . . . ? S2 C1 N1 C3 0.3(6) . . . . ? C2 C2 N1 C1 87.9(7) 5_565 . . . ? C2 C2 N1 C3 -91.3(6) 5_565 . . . ? C4 C3 N1 C1 110.4(5) . . . . ? C4 C3 N1 C2 -70.4(5) . . . . ? C15 C14 N2 C12 -61.3(8) . . . . ? C15 C14 N2 C10 174.9(7) . . . . ? C13 C12 N2 C14 -59.4(9) . . . . ? C13 C12 N2 C10 71.0(8) . . . . ? C11 C10 N2 C14 -36.9(13) . . . . ? C11 C10 N2 C12 -167.5(11) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.567 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.074