# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data__Compound8 #TrackingRef '18996_web_deposit_cif_file_0_TakashiOoi_1364535206.CIFforCCDC.txt' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C11 H14 N2 O4 S2 ' _chemical_formula_moiety 'C11 H14 N2 O4 S2 ' _chemical_formula_weight 302.38 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 11.8631(4) _cell_length_b 18.8439(6) _cell_length_c 12.3763(4) _cell_angle_alpha 90 _cell_angle_beta 91.9959(9) _cell_angle_gamma 90 _cell_volume 2765.01(16) _cell_formula_units_Z 8 _cell_measurement_reflns_used 23483 _cell_measurement_theta_min 3.2 _cell_measurement_theta_max 27.4 _cell_measurement_temperature 123.1 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1264.00 _exptl_absorpt_coefficient_mu 0.396 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Higashi, T. (1999). Program for Absorption Correction. Rigaku Corporation, Tokyo, Japan. ; _exptl_absorpt_correction_T_min 0.789 _exptl_absorpt_correction_T_max 0.854 #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123.1 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_measurement_device_type 'Rigaku RAXIS-RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.00 _diffrn_reflns_number 27240 _diffrn_reflns_av_R_equivalents 0.017 _diffrn_reflns_theta_max 27.45 _diffrn_measured_fraction_theta_max 0.9977 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.9977 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -24 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 16 #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 6314 _reflns_number_gt 5498 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0810 _refine_ls_hydrogen_treatment refall _refine_ls_number_reflns 6301 _refine_ls_number_parameters 371 _refine_ls_goodness_of_fit_ref 0.998 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[0.0009Fo^2^ + 1.0000\s(Fo^2^)]/(4Fo^2^)' _refine_ls_shift/su_max 0.0000 _refine_diff_density_max 0.39 _refine_diff_density_min -0.23 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.003 0.002 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.006 0.003 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.011 0.006 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; S S 0.125 0.123 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 S(1) S 0.91941(3) 0.41192(2) 0.55391(2) 0.02379(8) Uani 1.00 1 d . . . S(2) S 0.95461(3) 0.30914(2) 0.59567(2) 0.02338(8) Uani 1.00 1 d . . . S(101) S 0.61903(3) 0.44284(2) 0.45292(2) 0.02383(8) Uani 1.00 1 d . . . S(102) S 0.53231(3) 0.34925(2) 0.44619(2) 0.02440(8) Uani 1.00 1 d . . . O(2) O 1.10778(7) 0.54731(4) 0.72856(7) 0.0217(2) Uani 1.00 1 d . . . O(4) O 0.88059(7) 0.73948(5) 0.67810(8) 0.0274(2) Uani 1.00 1 d . . . O(8) O 0.89121(8) 0.44374(4) 0.87528(6) 0.0234(2) Uani 1.00 1 d . . . O(9) O 0.93329(8) 0.32635(5) 0.85297(7) 0.0244(2) Uani 1.00 1 d . . . O(102) O 0.40789(7) 0.58044(4) 0.28359(7) 0.0206(2) Uani 1.00 1 d . . . O(104) O 0.66469(7) 0.75699(5) 0.25935(7) 0.0255(2) Uani 1.00 1 d . . . O(108) O 0.55967(7) 0.45518(4) 0.12921(6) 0.0200(2) Uani 1.00 1 d . . . O(109) O 0.47686(7) 0.35214(4) 0.18492(6) 0.0207(2) Uani 1.00 1 d . . . N(1) N 0.92267(8) 0.52778(5) 0.67841(8) 0.0168(2) Uani 1.00 1 d . . . N(3) N 0.99232(8) 0.64245(5) 0.70080(8) 0.0182(2) Uani 1.00 1 d . . . N(101) N 0.59429(8) 0.55088(5) 0.31086(8) 0.0174(2) Uani 1.00 1 d . . . N(103) N 0.53945(8) 0.66696(5) 0.27262(7) 0.0174(2) Uani 1.00 1 d . . . C(2) C 1.01464(9) 0.57086(6) 0.70410(9) 0.0165(3) Uani 1.00 1 d . . . C(4) C 0.8904(1) 0.67458(6) 0.67257(9) 0.0199(3) Uani 1.00 1 d . . . C(5) C 0.8018(1) 0.62631(7) 0.6386(1) 0.0234(3) Uani 1.00 1 d . . . C(6) C 0.8206(1) 0.55652(6) 0.6435(1) 0.0211(3) Uani 1.00 1 d . . . C(7) C 0.93612(9) 0.45077(6) 0.68901(9) 0.0169(3) Uani 1.00 1 d . . . C(8) C 0.85125(9) 0.42279(6) 0.76972(9) 0.0179(3) Uani 1.00 1 d . . . C(9) C 0.8396(1) 0.34265(6) 0.7816(1) 0.0207(3) Uani 1.00 1 d . . . C(10) C 0.8371(1) 0.29531(6) 0.6831(1) 0.0228(3) Uani 1.00 1 d . . . C(11) C 0.9379(1) 0.38260(7) 0.9308(1) 0.0274(3) Uani 1.00 1 d . . . C(12) C 1.0596(1) 0.39593(9) 0.9637(1) 0.0430(4) Uani 1.00 1 d . . . C(13) C 0.8645(2) 0.36565(9) 1.0253(1) 0.0477(5) Uani 1.00 1 d . . . C(102) C 0.50625(9) 0.59812(6) 0.28871(9) 0.0161(3) Uani 1.00 1 d . . . C(104) C 0.6479(1) 0.69363(6) 0.27757(9) 0.0198(3) Uani 1.00 1 d . . . C(105) C 0.7339(1) 0.64179(7) 0.3046(1) 0.0255(3) Uani 1.00 1 d . . . C(106) C 0.7048(1) 0.57378(7) 0.3181(1) 0.0234(3) Uani 1.00 1 d . . . C(107) C 0.56666(9) 0.47550(6) 0.32119(9) 0.0165(3) Uani 1.00 1 d . . . C(108) C 0.61540(9) 0.43289(6) 0.22795(9) 0.0173(3) Uani 1.00 1 d . . . C(109) C 0.5905(1) 0.35325(6) 0.22826(9) 0.0194(3) Uani 1.00 1 d . . . C(110) C 0.6020(1) 0.31083(6) 0.33208(9) 0.0224(3) Uani 1.00 1 d . . . C(111) C 0.4714(1) 0.40445(6) 0.10081(9) 0.0204(3) Uani 1.00 1 d . . . C(112) C 0.3570(1) 0.43953(7) 0.1008(1) 0.0286(3) Uani 1.00 1 d . . . C(113) C 0.4976(1) 0.37236(7) -0.0079(1) 0.0318(4) Uani 1.00 1 d . . . H(1) H 1.0504 0.6717 0.7167 0.022 Uiso 1.00 1 c R . . H(2) H 0.7319 0.6456 0.6153 0.028 Uiso 1.00 1 c R . . H(3) H 0.7637 0.5214 0.6260 0.025 Uiso 1.00 1 c R . . H(4) H 1.0105 0.4401 0.7147 0.020 Uiso 1.00 1 c R . . H(5) H 0.7767 0.4447 0.7544 0.021 Uiso 1.00 1 c R . . H(6) H 0.7698 0.3342 0.8188 0.025 Uiso 1.00 1 c R . . H(7) H 0.8407 0.2461 0.7073 0.028 Uiso 1.00 1 c R . . H(8) H 0.7687 0.3031 0.6403 0.027 Uiso 1.00 1 c R . . H(9) H 1.1043 0.4069 0.8992 0.051 Uiso 1.00 1 c R . . H(10) H 1.0643 0.4330 1.0132 0.051 Uiso 1.00 1 c R . . H(11) H 1.0873 0.3529 0.9992 0.051 Uiso 1.00 1 c R . . H(12) H 0.8628 0.4072 1.0732 0.058 Uiso 1.00 1 c R . . H(13) H 0.8918 0.3242 1.0632 0.058 Uiso 1.00 1 c R . . H(14) H 0.7858 0.3582 0.9982 0.057 Uiso 1.00 1 c R . . H(101) H 0.4854 0.6987 0.2512 0.022 Uiso 1.00 1 c R . . H(102) H 0.8089 0.6577 0.3110 0.031 Uiso 1.00 1 c R . . H(103) H 0.7584 0.5355 0.3346 0.028 Uiso 1.00 1 c R . . H(104) H 0.4854 0.4710 0.3190 0.019 Uiso 1.00 1 c R . . H(105) H 0.6963 0.4407 0.2258 0.021 Uiso 1.00 1 c R . . H(106) H 0.6409 0.3293 0.1753 0.023 Uiso 1.00 1 c R . . H(107) H 0.5686 0.2662 0.3209 0.027 Uiso 1.00 1 c R . . H(108) H 0.6816 0.3063 0.3499 0.027 Uiso 1.00 1 c R . . H(109) H 0.3520 0.4736 0.0459 0.034 Uiso 1.00 1 c R . . H(110) H 0.3000 0.4046 0.0879 0.034 Uiso 1.00 1 c R . . H(111) H 0.3460 0.4636 0.1729 0.034 Uiso 1.00 1 c R . . H(112) H 0.5036 0.4102 -0.0564 0.038 Uiso 1.00 1 c R . . H(113) H 0.5666 0.3472 -0.0034 0.038 Uiso 1.00 1 c R . . H(114) H 0.4356 0.3412 -0.0304 0.038 Uiso 1.00 1 c 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S(1) 0.0326(2) 0.0204(2) 0.0184(1) 0.0026(1) 0.0005(1) -0.0019(1) S(2) 0.0255(2) 0.0182(1) 0.0265(2) 0.0024(1) 0.0015(1) -0.0060(1) S(101) 0.0284(2) 0.0238(2) 0.0188(1) 0.0028(1) -0.0058(1) 0.0001(1) S(102) 0.0263(2) 0.0262(2) 0.0208(1) 0.0014(1) 0.0025(1) 0.0063(1) O(2) 0.0138(4) 0.0192(4) 0.0318(5) 0.0021(3) -0.0015(3) -0.0014(3) O(4) 0.0223(4) 0.0165(4) 0.0431(5) 0.0033(3) -0.0056(4) -0.0040(4) O(8) 0.0292(5) 0.0214(4) 0.0197(4) 0.0003(4) 0.0006(4) -0.0040(3) O(9) 0.0292(5) 0.0202(4) 0.0234(4) 0.0021(4) -0.0056(4) -0.0010(3) O(102) 0.0135(4) 0.0211(4) 0.0271(4) 0.0004(3) -0.0018(3) 0.0023(3) O(104) 0.0203(4) 0.0177(4) 0.0387(5) -0.0017(3) 0.0012(4) -0.0014(4) O(108) 0.0246(4) 0.0180(4) 0.0173(4) -0.0044(3) -0.0014(3) 0.0025(3) O(109) 0.0241(4) 0.0184(4) 0.0194(4) -0.0049(3) -0.0031(3) 0.0042(3) N(1) 0.0148(4) 0.0136(5) 0.0217(5) 0.0012(4) -0.0017(4) -0.0008(4) N(3) 0.0151(5) 0.0152(5) 0.0242(5) -0.0007(4) -0.0014(4) -0.0027(4) N(101) 0.0141(4) 0.0150(5) 0.0228(5) 0.0002(4) -0.0025(4) -0.0016(4) N(103) 0.0159(5) 0.0160(5) 0.0202(5) 0.0017(4) -0.0002(4) -0.0003(4) C(2) 0.0147(5) 0.0168(5) 0.0180(5) -0.0001(4) 0.0013(4) -0.0007(4) C(4) 0.0176(5) 0.0184(6) 0.0236(6) 0.0028(4) -0.0013(5) -0.0012(5) C(5) 0.0169(5) 0.0215(6) 0.0313(6) 0.0031(5) -0.0065(5) -0.0012(5) C(6) 0.0166(5) 0.0209(6) 0.0256(6) 0.0007(4) -0.0047(5) -0.0009(5) C(7) 0.0154(5) 0.0142(5) 0.0210(5) 0.0008(4) -0.0014(4) -0.0012(4) C(8) 0.0152(5) 0.0174(5) 0.0210(5) -0.0001(4) 0.0012(4) -0.0035(4) C(9) 0.0186(6) 0.0193(6) 0.0243(6) -0.0014(4) 0.0009(5) 0.0004(5) C(10) 0.0211(6) 0.0184(6) 0.0287(6) -0.0036(5) -0.0017(5) -0.0022(5) C(11) 0.0364(7) 0.0234(6) 0.0221(6) 0.0007(6) -0.0023(5) -0.0021(5) C(12) 0.0438(9) 0.0400(9) 0.0439(9) 0.0056(7) -0.0203(7) -0.0120(7) C(13) 0.075(1) 0.046(1) 0.0234(7) -0.0079(9) 0.0097(8) 0.0030(7) C(102) 0.0168(5) 0.0176(5) 0.0138(5) 0.0015(4) -0.0001(4) -0.0022(4) C(104) 0.0177(5) 0.0200(6) 0.0217(6) -0.0011(4) 0.0013(4) -0.0047(4) C(105) 0.0140(5) 0.0222(6) 0.0402(7) -0.0014(5) -0.0017(5) -0.0044(5) C(106) 0.0149(5) 0.0216(6) 0.0334(7) 0.0026(5) -0.0026(5) -0.0044(5) C(107) 0.0153(5) 0.0156(5) 0.0184(5) 0.0005(4) -0.0023(4) 0.0006(4) C(108) 0.0157(5) 0.0179(6) 0.0183(5) 0.0006(4) 0.0004(4) 0.0013(4) C(109) 0.0205(6) 0.0170(6) 0.0205(5) 0.0006(4) 0.0003(5) -0.0002(4) C(110) 0.0247(6) 0.0177(6) 0.0246(6) 0.0017(5) -0.0003(5) 0.0029(5) C(111) 0.0272(6) 0.0168(6) 0.0168(5) -0.0049(5) -0.0034(5) 0.0022(4) C(112) 0.0265(7) 0.0288(7) 0.0299(7) -0.0036(5) -0.0081(5) 0.0054(5) C(113) 0.0523(9) 0.0250(7) 0.0183(6) -0.0063(6) 0.0008(6) -0.0011(5) #============================================================================== _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction CrystalStructure _computing_structure_solution SIR97 _computing_structure_refinement CRYSTALS _computing_publication_material 'CrystalStructure 3.6.0' _computing_molecular_graphics ? #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 S(1) S(2) 2.0439(5) ? . . S(1) C(7) 1.830(1) ? . . S(2) C(10) 1.814(1) ? . . S(101) S(102) 2.0420(5) ? . . S(101) C(107) 1.831(1) ? . . S(102) C(110) 1.812(1) ? . . O(2) C(2) 1.219(1) ? . . O(4) C(4) 1.231(1) ? . . O(8) C(8) 1.430(1) ? . . O(8) C(11) 1.442(2) ? . . O(9) C(9) 1.429(1) ? . . O(9) C(11) 1.432(2) ? . . O(102) C(102) 1.213(1) ? . . O(104) C(104) 1.233(1) ? . . O(108) C(108) 1.432(1) ? . . O(108) C(111) 1.452(1) ? . . O(109) C(109) 1.434(1) ? . . O(109) C(111) 1.433(1) ? . . N(1) C(2) 1.388(1) ? . . N(1) C(6) 1.382(2) ? . . N(1) C(7) 1.465(1) ? . . N(3) C(2) 1.375(1) ? . . N(3) C(4) 1.386(1) ? . . N(101) C(102) 1.392(1) ? . . N(101) C(106) 1.380(2) ? . . N(101) C(107) 1.464(1) ? . . N(103) C(102) 1.372(1) ? . . N(103) C(104) 1.380(2) ? . . C(4) C(5) 1.441(2) ? . . C(5) C(6) 1.335(2) ? . . C(7) C(8) 1.536(2) ? . . C(8) C(9) 1.524(2) ? . . C(9) C(10) 1.510(2) ? . . C(11) C(12) 1.508(2) ? . . C(11) C(13) 1.516(2) ? . . C(104) C(105) 1.444(2) ? . . C(105) C(106) 1.339(2) ? . . C(107) C(108) 1.535(2) ? . . C(108) C(109) 1.530(2) ? . . C(109) C(110) 1.515(2) ? . . C(111) C(112) 1.510(2) ? . . C(111) C(113) 1.517(2) ? . . N(3) H(1) 0.8987 ? . . N(103) H(101) 0.9093 ? . . C(5) H(2) 0.9412 ? . . C(6) H(3) 0.9648 ? . . C(7) H(4) 0.9493 ? . . C(8) H(5) 0.9885 ? . . C(9) H(6) 0.9744 ? . . C(10) H(7) 0.9745 ? . . C(10) H(8) 0.9645 ? . . C(12) H(9) 0.9957 ? . . C(12) H(10) 0.9285 ? . . C(12) H(11) 0.9727 ? . . C(13) H(12) 0.9820 ? . . C(13) H(13) 0.9611 ? . . C(13) H(14) 0.9915 ? . . C(105) H(102) 0.9398 ? . . C(106) H(103) 0.9791 ? . . C(107) H(104) 0.9673 ? . . C(108) H(105) 0.9728 ? . . C(109) H(106) 1.0090 ? . . C(110) H(107) 0.9371 ? . . C(110) H(108) 0.9659 ? . . C(112) H(109) 0.9349 ? . . C(112) H(110) 0.9528 ? . . C(112) H(111) 1.0143 ? . . C(113) H(112) 0.9364 ? . . C(113) H(113) 0.9463 ? . . C(113) H(114) 0.9736 ? . . loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C(7) S(1) S(2) 97.67(4) ? . . . S(1) S(2) C(10) 97.62(4) ? . . . S(1) C(7) N(1) 107.84(8) ? . . . S(1) C(7) C(8) 113.85(8) ? . . . S(2) C(10) C(9) 113.76(8) ? . . . C(107) S(101) S(102) 95.69(4) ? . . . S(101) S(102) C(110) 97.69(4) ? . . . S(101) C(107) N(101) 109.50(7) ? . . . S(101) C(107) C(108) 111.62(8) ? . . . S(102) C(110) C(109) 114.82(8) ? . . . O(2) C(2) N(1) 122.8(1) ? . . . O(2) C(2) N(3) 122.4(1) ? . . . O(4) C(4) N(3) 120.2(1) ? . . . O(4) C(4) C(5) 125.0(1) ? . . . O(8) C(8) C(7) 107.18(9) ? . . . O(8) C(8) C(9) 102.33(9) ? . . . C(11) O(8) C(8) 108.95(8) ? . . . O(8) C(11) O(9) 105.38(9) ? . . . O(8) C(11) C(12) 110.1(1) ? . . . O(8) C(11) C(13) 108.3(1) ? . . . O(9) C(9) C(8) 101.63(9) ? . . . O(9) C(9) C(10) 111.41(9) ? . . . C(11) O(9) C(9) 105.51(9) ? . . . O(9) C(11) C(12) 108.6(1) ? . . . O(9) C(11) C(13) 110.7(1) ? . . . O(102) C(102) N(101) 123.3(1) ? . . . O(102) C(102) N(103) 122.2(1) ? . . . O(104) C(104) N(103) 120.1(1) ? . . . O(104) C(104) C(105) 125.5(1) ? . . . O(108) C(108) C(107) 108.26(9) ? . . . O(108) C(108) C(109) 101.92(8) ? . . . C(111) O(108) C(108) 108.73(8) ? . . . O(108) C(111) O(109) 105.26(8) ? . . . O(108) C(111) C(112) 110.64(9) ? . . . O(108) C(111) C(113) 108.0(1) ? . . . O(109) C(109) C(108) 101.10(8) ? . . . O(109) C(109) C(110) 111.45(9) ? . . . C(111) O(109) C(109) 106.24(8) ? . . . O(109) C(111) C(112) 108.6(1) ? . . . O(109) C(111) C(113) 111.38(9) ? . . . C(6) N(1) C(2) 121.04(9) ? . . . C(7) N(1) C(2) 118.46(9) ? . . . N(1) C(2) N(3) 114.71(9) ? . . . C(7) N(1) C(6) 120.50(9) ? . . . N(1) C(6) C(5) 122.9(1) ? . . . N(1) C(7) C(8) 109.05(9) ? . . . C(4) N(3) C(2) 127.0(1) ? . . . N(3) C(4) C(5) 114.7(1) ? . . . C(106) N(101) C(102) 121.2(1) ? . . . C(107) N(101) C(102) 117.95(9) ? . . . N(101) C(102) N(103) 114.57(9) ? . . . C(107) N(101) C(106) 120.8(1) ? . . . N(101) C(106) C(105) 122.7(1) ? . . . N(101) C(107) C(108) 110.51(9) ? . . . C(104) N(103) C(102) 127.6(1) ? . . . N(103) C(104) C(105) 114.5(1) ? . . . C(4) C(5) C(6) 119.3(1) ? . . . C(7) C(8) C(9) 117.8(1) ? . . . C(8) C(9) C(10) 120.4(1) ? . . . C(13) C(11) C(12) 113.4(1) ? . . . C(104) C(105) C(106) 119.5(1) ? . . . C(107) C(108) C(109) 115.68(9) ? . . . C(108) C(109) C(110) 120.52(9) ? . . . C(113) C(111) C(112) 112.7(1) ? . . . S(1) C(7) H(4) 106.8943 ? . . . S(2) C(10) H(8) 107.4029 ? . . . S(2) C(10) H(7) 107.0348 ? . . . S(101) C(107) H(104) 107.5968 ? . . . S(102) C(110) H(108) 109.0867 ? . . . S(102) C(110) H(107) 105.7279 ? . . . O(8) C(8) H(5) 109.0110 ? . . . O(9) C(9) H(6) 109.1867 ? . . . O(108) C(108) H(105) 111.0545 ? . . . O(109) C(109) H(106) 108.7292 ? . . . N(1) C(6) H(3) 113.5676 ? . . . N(1) C(7) H(4) 109.7175 ? . . . H(1) N(3) C(2) 116.6877 ? . . . H(1) N(3) C(4) 116.3216 ? . . . N(101) C(106) H(103) 113.0993 ? . . . N(101) C(107) H(104) 107.9914 ? . . . H(101) N(103) C(102) 117.4555 ? . . . H(101) N(103) C(104) 114.8163 ? . . . C(4) C(5) H(2) 118.0575 ? . . . C(5) C(6) H(3) 123.4827 ? . . . H(2) C(5) C(6) 122.5964 ? . . . H(4) C(7) C(8) 109.4180 ? . . . C(7) C(8) H(5) 109.4796 ? . . . H(5) C(8) C(9) 110.4759 ? . . . C(8) C(9) H(6) 106.8169 ? . . . C(9) C(10) H(8) 110.2629 ? . . . C(9) C(10) H(7) 108.3487 ? . . . H(6) C(9) C(10) 106.9396 ? . . . H(8) C(10) H(7) 109.9584 ? . . . C(11) C(12) H(9) 110.4738 ? . . . C(11) C(12) H(10) 109.7262 ? . . . C(11) C(12) H(11) 106.7305 ? . . . C(11) C(13) H(12) 108.7582 ? . . . C(11) C(13) H(13) 110.7528 ? . . . C(11) C(13) H(14) 109.1274 ? . . . H(10) C(12) H(9) 110.5538 ? . . . H(11) C(12) H(9) 110.7961 ? . . . H(11) C(12) H(10) 108.4653 ? . . . H(13) C(13) H(12) 111.5926 ? . . . H(14) C(13) H(12) 106.1616 ? . . . H(14) C(13) H(13) 110.3129 ? . . . C(104) C(105) H(102) 117.6051 ? . . . C(105) C(106) H(103) 124.2432 ? . . . H(102) C(105) C(106) 122.8512 ? . . . H(104) C(107) C(108) 109.5104 ? . . . C(107) C(108) H(105) 109.8030 ? . . . H(105) C(108) C(109) 109.8755 ? . . . C(108) C(109) H(106) 108.5309 ? . . . C(109) C(110) H(108) 107.4224 ? . . . C(109) C(110) H(107) 108.8003 ? . . . H(106) C(109) C(110) 106.1015 ? . . . H(108) C(110) H(107) 111.0182 ? . . . C(111) C(112) H(111) 109.8200 ? . . . C(111) C(112) H(109) 109.5988 ? . . . C(111) C(112) H(110) 109.3111 ? . . . C(111) C(113) H(112) 106.6986 ? . . . C(111) C(113) H(113) 110.5131 ? . . . C(111) C(113) H(114) 108.5546 ? . . . H(111) C(112) H(109) 108.9538 ? . . . H(110) C(112) H(109) 109.0565 ? . . . H(111) C(112) H(110) 110.0845 ? . . . H(113) C(113) H(112) 109.5009 ? . . . H(114) C(113) H(112) 110.4914 ? . . . H(114) C(113) H(113) 110.9897 ? . . . 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_publ_flag _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C(7) S(1) S(2) C(10) 63.09(4) ? . . . . S(2) S(1) C(7) N(1) 175.81(7) ? . . . . S(2) S(1) C(7) C(8) -63.05(8) ? . . . . S(2) S(1) C(7) H(4) 57.9 ? . . . . S(1) S(2) C(10) C(9) -63.07(8) ? . . . . S(1) S(2) C(10) H(7) 177.3 ? . . . . S(1) S(2) C(10) H(8) 59.2 ? . . . . C(107) S(101) S(102) C(110) 64.60(4) ? . . . . S(102) S(101) C(107) N(101) 167.31(7) ? . . . . S(102) S(101) C(107) C(108) -69.99(8) ? . . . . S(102) S(101) C(107) H(104) 50.2 ? . . . . S(101) S(102) C(110) C(109) -60.23(9) ? . . . . S(101) S(102) C(110) H(107) 179.8 ? . . . . S(101) S(102) C(110) H(108) 60.4 ? . . . . C(11) O(8) C(8) C(7) -105.31(9) ? . . . . C(11) O(8) C(8) C(9) 19.3(1) ? . . . . C(11) O(8) C(8) H(5) 136.3 ? . . . . C(8) O(8) C(11) O(9) 4.6(1) ? . . . . C(8) O(8) C(11) C(12) 121.6(1) ? . . . . C(8) O(8) C(11) C(13) -113.9(1) ? . . . . C(11) O(9) C(9) C(8) 40.0(1) ? . . . . C(11) O(9) C(9) C(10) 169.46(9) ? . . . . C(11) O(9) C(9) H(6) -72.7 ? . . . . C(9) O(9) C(11) O(8) -28.7(1) ? . . . . C(9) O(9) C(11) C(12) -146.7(1) ? . . . . C(9) O(9) C(11) C(13) 88.2(1) ? . . . . C(111) O(108) C(108) C(107) -98.86(9) ? . . . . C(111) O(108) C(108) C(109) 23.6(1) ? . . . . C(111) O(108) C(108) H(105) 140.5 ? . . . . C(108) O(108) C(111) O(109) -0.03(9) ? . . . . C(108) O(108) C(111) C(112) 117.11(9) ? . . . . C(108) O(108) C(111) C(113) -119.11(9) ? . . . . C(111) O(109) C(109) C(108) 39.54(9) ? . . . . C(111) O(109) C(109) C(110) 168.82(8) ? . . . . C(111) O(109) C(109) H(106) -74.6 ? . . . . C(109) O(109) C(111) O(108) -25.7(1) ? . . . . C(109) O(109) C(111) C(112) -144.22(9) ? . . . . C(109) O(109) C(111) C(113) 91.1(1) ? . . . . C(6) N(1) C(2) O(2) -175.2(1) ? . . . . C(6) N(1) C(2) N(3) 5.3(2) ? . . . . C(7) N(1) C(2) O(2) 4.7(2) ? . . . . C(7) N(1) C(2) N(3) -174.74(9) ? . . . . C(2) N(1) C(6) C(5) -4.2(2) ? . . . . C(2) N(1) C(6) H(3) 178.2 ? . . . . C(7) N(1) C(6) C(5) 175.9(1) ? . . . . C(7) N(1) C(6) H(3) -1.7 ? . . . . C(2) N(1) C(7) S(1) -115.22(9) ? . . . . C(2) N(1) C(7) C(8) 120.7(1) ? . . . . C(2) N(1) C(7) H(4) 0.9 ? . . . . C(6) N(1) C(7) S(1) 64.7(1) ? . . . . C(6) N(1) C(7) C(8) -59.4(1) ? . . . . C(6) N(1) C(7) H(4) -179.2 ? . . . . C(4) N(3) C(2) O(2) 178.9(1) ? . . . . C(4) N(3) C(2) N(1) -1.6(2) ? . . . . H(1) N(3) C(2) O(2) 0.9 ? . . . . H(1) N(3) C(2) N(1) -179.7 ? . . . . C(2) N(3) C(4) O(4) 176.5(1) ? . . . . C(2) N(3) C(4) C(5) -3.2(2) ? . . . . H(1) N(3) C(4) O(4) -5.5 ? . . . . H(1) N(3) C(4) C(5) 174.9 ? . . . . C(106) N(101) C(102) O(102) -178.6(1) ? . . . . C(106) N(101) C(102) N(103) 1.6(1) ? . . . . C(107) N(101) C(102) O(102) 4.2(2) ? . . . . C(107) N(101) C(102) N(103) -175.61(9) ? . . . . C(102) N(101) C(106) C(105) -0.0(1) ? . . . . C(102) N(101) C(106) H(103) 179.5 ? . . . . C(107) N(101) C(106) C(105) 177.1(1) ? . . . . C(107) N(101) C(106) H(103) -3.4 ? . . . . C(102) N(101) C(107) S(101) -123.76(9) ? . . . . C(102) N(101) C(107) C(108) 112.9(1) ? . . . . C(102) N(101) C(107) H(104) -6.9 ? . . . . C(106) N(101) C(107) S(101) 59.0(1) ? . . . . C(106) N(101) C(107) C(108) -64.3(1) ? . . . . C(106) N(101) C(107) H(104) 175.9 ? . . . . C(104) N(103) C(102) O(102) 179.1(1) ? . . . . C(104) N(103) C(102) N(101) -1.0(2) ? . . . . H(101) N(103) C(102) O(102) -6.0 ? . . . . H(101) N(103) C(102) N(101) 173.9 ? . . . . C(102) N(103) C(104) O(104) 178.8(1) ? . . . . C(102) N(103) C(104) C(105) -1.0(2) ? . . . . H(101) N(103) C(104) O(104) 3.8 ? . . . . H(101) N(103) C(104) C(105) -176.0 ? . . . . O(4) C(4) C(5) C(6) -175.2(1) ? . . . . O(4) C(4) C(5) H(2) 3.3 ? . . . . N(3) C(4) C(5) C(6) 4.5(2) ? . . . . N(3) C(4) C(5) H(2) -177.1 ? . . . . C(4) C(5) C(6) N(1) -1.1(2) ? . . . . C(4) C(5) C(6) H(3) 176.3 ? . . . . H(2) C(5) C(6) N(1) -179.4 ? . . . . H(2) C(5) C(6) H(3) -2.1 ? . . . . S(1) C(7) C(8) O(8) 166.03(8) ? . . . . S(1) C(7) C(8) C(9) 51.5(1) ? . . . . S(1) C(7) C(8) H(5) -75.9 ? . . . . N(1) C(7) C(8) O(8) -73.5(1) ? . . . . N(1) C(7) C(8) C(9) 171.92(9) ? . . . . N(1) C(7) C(8) H(5) 44.6 ? . . . . H(4) C(7) C(8) O(8) 46.5 ? . . . . H(4) C(7) C(8) C(9) -68.1 ? . . . . H(4) C(7) C(8) H(5) 164.6 ? . . . . O(8) C(8) C(9) O(9) -36.0(1) ? . . . . O(8) C(8) C(9) C(10) -159.6(1) ? . . . . O(8) C(8) C(9) H(6) 78.4 ? . . . . C(7) C(8) C(9) O(9) 81.2(1) ? . . . . C(7) C(8) C(9) C(10) -42.3(1) ? . . . . C(7) C(8) C(9) H(6) -164.4 ? . . . . H(5) C(8) C(9) O(9) -151.9 ? . . . . H(5) C(8) C(9) C(10) 84.5 ? . . . . H(5) C(8) C(9) H(6) -37.5 ? . . . . O(9) C(9) C(10) S(2) -66.1(1) ? . . . . O(9) C(9) C(10) H(7) 52.8 ? . . . . O(9) C(9) C(10) H(8) 173.2 ? . . . . C(8) C(9) C(10) S(2) 52.7(1) ? . . . . C(8) C(9) C(10) H(7) 171.6 ? . . . . C(8) C(9) C(10) H(8) -68.0 ? . . . . H(6) C(9) C(10) S(2) 174.7 ? . . . . H(6) C(9) C(10) H(7) -66.4 ? . . . . H(6) C(9) C(10) H(8) 53.9 ? . . . . O(8) C(11) C(12) H(9) -58.2 ? . . . . O(8) C(11) C(12) H(10) 63.9 ? . . . . O(8) C(11) C(12) H(11) -178.8 ? . . . . O(9) C(11) C(12) H(9) 56.7 ? . . . . O(9) C(11) C(12) H(10) 178.8 ? . . . . O(9) C(11) C(12) H(11) -63.9 ? . . . . C(13) C(11) C(12) H(9) -179.8 ? . . . . C(13) C(11) C(12) H(10) -57.7 ? . . . . C(13) C(11) C(12) H(11) 59.6 ? . . . . O(8) C(11) C(13) H(12) -58.8 ? . . . . O(8) C(11) C(13) H(13) 178.3 ? . . . . O(8) C(11) C(13) H(14) 56.6 ? . . . . O(9) C(11) C(13) H(12) -173.8 ? . . . . O(9) C(11) C(13) H(13) 63.2 ? . . . . O(9) C(11) C(13) H(14) -58.4 ? . . . . C(12) C(11) C(13) H(12) 63.8 ? . . . . C(12) C(11) C(13) H(13) -59.2 ? . . . . C(12) C(11) C(13) H(14) 179.2 ? . . . . O(104) C(104) C(105) C(106) -177.3(1) ? . . . . O(104) C(104) C(105) H(102) 2.0 ? . . . . N(103) C(104) C(105) C(106) 2.6(2) ? . . . . N(103) C(104) C(105) H(102) -178.2 ? . . . . C(104) C(105) C(106) N(101) -2.2(2) ? . . . . C(104) C(105) C(106) H(103) 178.3 ? . . . . H(102) C(105) C(106) N(101) 178.6 ? . . . . H(102) C(105) C(106) H(103) -0.9 ? . . . . S(101) C(107) C(108) O(108) 172.52(8) ? . . . . S(101) C(107) C(108) C(109) 58.9(1) ? . . . . S(101) C(107) C(108) H(105) -66.1 ? . . . . N(101) C(107) C(108) O(108) -65.4(1) ? . . . . N(101) C(107) C(108) C(109) -178.94(9) ? . . . . N(101) C(107) C(108) H(105) 56.0 ? . . . . H(104) C(107) C(108) O(108) 53.5 ? . . . . H(104) C(107) C(108) C(109) -60.1 ? . . . . H(104) C(107) C(108) H(105) 174.9 ? . . . . O(108) C(108) C(109) O(109) -38.2(1) ? . . . . O(108) C(108) C(109) C(110) -161.4(1) ? . . . . O(108) C(108) C(109) H(106) 76.1 ? . . . . C(107) C(108) C(109) O(109) 79.0(1) ? . . . . C(107) C(108) C(109) C(110) -44.2(1) ? . . . . C(107) C(108) C(109) H(106) -166.7 ? . . . . H(105) C(108) C(109) O(109) -156.0 ? . . . . H(105) C(108) C(109) C(110) 80.8 ? . . . . H(105) C(108) C(109) H(106) -41.7 ? . . . . O(109) C(109) C(110) S(102) -68.8(1) ? . . . . O(109) C(109) C(110) H(107) 49.4 ? . . . . O(109) C(109) C(110) H(108) 169.6 ? . . . . C(108) C(109) C(110) S(102) 49.3(1) ? . . . . C(108) C(109) C(110) H(107) 167.5 ? . . . . C(108) C(109) C(110) H(108) -72.2 ? . . . . H(106) C(109) C(110) S(102) 173.0 ? . . . . H(106) C(109) C(110) H(107) -68.8 ? . . . . H(106) C(109) C(110) H(108) 51.5 ? . . . . O(108) C(111) C(112) H(109) 65.3 ? . . . . O(108) C(111) C(112) H(110) -175.2 ? . . . . O(108) C(111) C(112) H(111) -54.3 ? . . . . O(109) C(111) C(112) H(109) -179.6 ? . . . . O(109) C(111) C(112) H(110) -60.1 ? . . . . O(109) C(111) C(112) H(111) 60.7 ? . . . . C(113) C(111) C(112) H(109) -55.7 ? . . . . C(113) C(111) C(112) H(110) 63.8 ? . . . . C(113) C(111) C(112) H(111) -175.4 ? . . . . O(108) C(111) C(113) H(112) -56.3 ? . . . . O(108) C(111) C(113) H(113) 62.7 ? . . . . O(108) C(111) C(113) H(114) -175.3 ? . . . . O(109) C(111) C(113) H(112) -171.4 ? . . . . O(109) C(111) C(113) H(113) -52.4 ? . . . . O(109) C(111) C(113) H(114) 69.5 ? . . . . C(112) C(111) C(113) H(112) 66.3 ? . . . . C(112) C(111) C(113) H(113) -174.8 ? . . . . C(112) C(111) C(113) H(114) -52.8 ? . . . . #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== _database_code_depnum_ccdc_archive 'CCDC 931650'