# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2014 ####################################################################### # # 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_datam _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'Cytosine tribromoacetate' _chemical_melting_point ? _chemical_formula_moiety '2(C4 N3 O), C2 Br3 O2' _chemical_formula_sum 'C10 Br3 N6 O4' _chemical_formula_weight 507.86 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' Br Br -0.2901 2.4595 '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 6.0904(15) _cell_length_b 10.3943(15) _cell_length_c 13.5423(19) _cell_angle_alpha 73.19(5) _cell_angle_beta 79.70(5) _cell_angle_gamma 78.31(6) _cell_volume 797.0(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Prism _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_min 0.200 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.116 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 570 _exptl_absorpt_coefficient_mu 7.619 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8346 _diffrn_reflns_av_R_equivalents 0.1699 _diffrn_reflns_av_sigmaI/netI 0.1490 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 27.43 _reflns_number_total 3593 _reflns_number_gt 2796 _reflns_threshold_expression >2\s(I) _computing_data_collection 'Bruker XSCANS' _computing_cell_refinement 'Bruker XSCANS' _computing_data_reduction 'Bruker SHELXTL' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^ > 2\s(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^)+(0.0784P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_hydrogen_treatment none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3593 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0841 _refine_ls_R_factor_gt 0.0703 _refine_ls_wR_factor_ref 0.2127 _refine_ls_wR_factor_gt 0.1747 _refine_ls_goodness_of_fit_ref 1.189 _refine_ls_restrained_S_all 1.189 _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 Br1 Br 0.27902(13) 0.57752(8) 0.91540(6) 0.0249(2) Uani 1 1 d . . . Br2 Br 0.14829(14) 0.81354(7) 0.71730(6) 0.0291(3) Uani 1 1 d . . . Br3 Br -0.10607(13) 0.55653(9) 0.79213(7) 0.0300(3) Uani 1 1 d . . . O4 O 1.3638(10) 0.9185(6) 0.3712(5) 0.0323(14) Uani 1 1 d . . . O3 O 0.8379(12) 0.1948(7) 0.8529(5) 0.0423(17) Uani 1 1 d . . . N2 N 0.7804(12) 0.0671(7) 1.0232(5) 0.0272(15) Uani 1 1 d . . . N6 N 0.6685(12) 0.8427(7) 0.5554(6) 0.0297(15) Uani 1 1 d . . . O1 O 0.4308(11) 0.6035(6) 0.6193(5) 0.0409(17) Uani 1 1 d . . . N1 N 0.4922(12) 0.2328(7) 0.9441(5) 0.0300(16) Uani 1 1 d . . . O2 O 0.4106(11) 0.4110(6) 0.7478(5) 0.0381(15) Uani 1 1 d . . . N3 N 0.7158(13) -0.0655(7) 1.1915(6) 0.0301(16) Uani 1 1 d . . . N5 N 1.0154(11) 0.8850(7) 0.4600(5) 0.0242(14) Uani 1 1 d . . . C001 C 0.6419(13) 0.0342(8) 1.1133(6) 0.0237(16) Uani 1 1 d . . . C002 C 0.1864(13) 0.6166(8) 0.7772(6) 0.0232(15) Uani 1 1 d . . . C003 C 0.3637(13) 0.5367(7) 0.7061(6) 0.0225(16) Uani 1 1 d . . . C004 C 1.2134(14) 0.8468(8) 0.3989(6) 0.0263(17) Uani 1 1 d . . . C005 C 0.7127(15) 0.1667(8) 0.9348(7) 0.0300(18) Uani 1 1 d . . . C006 C 0.8489(13) 0.8059(8) 0.4914(6) 0.0241(16) Uani 1 1 d . . . C007 C 0.8671(16) 0.6876(9) 0.4544(7) 0.035(2) Uani 1 1 d . . . C008 C 0.3486(14) 0.2041(8) 1.0344(7) 0.0294(18) Uani 1 1 d . . . C009 C 1.0656(17) 0.6515(9) 0.3967(7) 0.036(2) Uani 1 1 d . . . N4 N 1.2355(13) 0.7277(7) 0.3719(5) 0.0309(16) Uani 1 1 d . . . C010 C 0.4161(13) 0.1078(8) 1.1210(6) 0.0252(16) 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 Br1 0.0257(4) 0.0261(4) 0.0271(4) -0.0135(3) -0.0046(3) -0.0030(3) Br2 0.0308(5) 0.0185(4) 0.0356(5) -0.0092(3) 0.0021(4) -0.0012(3) Br3 0.0215(4) 0.0379(5) 0.0384(5) -0.0200(4) -0.0005(4) -0.0104(3) O4 0.029(3) 0.032(3) 0.037(3) -0.019(3) 0.009(3) -0.004(2) O3 0.042(4) 0.038(4) 0.033(3) -0.002(3) 0.013(3) -0.002(3) N2 0.034(4) 0.023(3) 0.024(3) -0.011(3) 0.008(3) -0.007(3) N6 0.028(4) 0.030(4) 0.033(4) -0.017(3) 0.004(3) -0.003(3) O1 0.047(4) 0.030(3) 0.043(4) -0.019(3) 0.020(3) -0.009(3) N1 0.034(4) 0.023(3) 0.034(4) -0.012(3) -0.002(3) -0.002(3) O2 0.049(4) 0.027(3) 0.031(3) -0.012(3) 0.004(3) 0.010(3) N3 0.036(4) 0.025(3) 0.029(4) -0.012(3) 0.006(3) -0.007(3) N5 0.028(3) 0.025(3) 0.020(3) -0.010(3) 0.002(3) -0.003(3) C001 0.029(4) 0.021(4) 0.026(4) -0.013(3) 0.002(3) -0.010(3) C002 0.021(4) 0.024(4) 0.027(4) -0.011(3) 0.000(3) -0.006(3) C003 0.022(4) 0.025(4) 0.026(4) -0.019(3) 0.002(3) -0.004(3) C004 0.030(4) 0.026(4) 0.016(4) -0.005(3) 0.006(3) 0.003(3) C005 0.032(4) 0.024(4) 0.035(4) -0.014(3) 0.005(4) -0.005(3) C006 0.028(4) 0.019(4) 0.025(4) -0.010(3) -0.003(3) 0.003(3) C007 0.044(5) 0.026(4) 0.036(5) -0.019(4) 0.007(4) -0.004(4) C008 0.030(4) 0.024(4) 0.037(5) -0.014(3) 0.001(4) -0.007(3) C009 0.050(5) 0.027(4) 0.030(4) -0.017(4) 0.003(4) 0.000(4) N4 0.039(4) 0.025(3) 0.025(3) -0.012(3) 0.005(3) 0.001(3) C010 0.025(4) 0.020(4) 0.036(4) -0.017(3) -0.004(3) -0.004(3) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 Br1 C002 1.956(8) . ? Br2 C002 1.953(8) . ? Br3 C002 1.963(7) . ? O4 C004 1.236(10) . ? O3 C005 1.223(10) . ? N2 C001 1.351(10) . ? N2 C005 1.400(12) . ? N6 C006 1.336(10) . ? O1 C003 1.226(10) . ? N1 C008 1.365(10) . ? N1 C005 1.381(11) . ? O2 C003 1.260(10) . ? N3 C001 1.320(12) . ? N5 C006 1.366(10) . ? N5 C004 1.391(9) . ? C001 C010 1.434(11) . ? C002 C003 1.585(10) . ? C004 N4 1.364(10) . ? C006 C007 1.434(10) . ? C007 C009 1.364(12) . ? C008 C010 1.368(13) . ? C009 N4 1.366(11) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C001 N2 C005 123.4(7) . . ? C008 N1 C005 122.2(8) . . ? C006 N5 C004 121.0(6) . . ? N3 C001 N2 119.6(7) . . ? N3 C001 C010 121.6(7) . . ? N2 C001 C010 118.8(8) . . ? C003 C002 Br2 112.3(5) . . ? C003 C002 Br3 108.0(5) . . ? Br2 C002 Br3 108.6(4) . . ? C003 C002 Br1 111.0(5) . . ? Br2 C002 Br1 108.1(3) . . ? Br3 C002 Br1 108.8(3) . . ? O1 C003 O2 129.5(7) . . ? O1 C003 C002 116.7(7) . . ? O2 C003 C002 113.8(6) . . ? O4 C004 N4 121.7(7) . . ? O4 C004 N5 120.6(7) . . ? N4 C004 N5 117.7(7) . . ? O3 C005 N1 120.7(9) . . ? O3 C005 N2 123.1(8) . . ? N1 C005 N2 116.1(7) . . ? N6 C006 N5 118.6(7) . . ? N6 C006 C007 121.2(7) . . ? N5 C006 C007 120.2(7) . . ? C009 C007 C006 116.9(8) . . ? N1 C008 C010 121.5(8) . . ? C007 C009 N4 121.5(7) . . ? C009 N4 C004 122.3(7) . . ? C008 C010 C001 117.9(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 C005 N2 C001 N3 176.8(7) . . . . ? C005 N2 C001 C010 -2.4(11) . . . . ? Br2 C002 C003 O1 -9.0(9) . . . . ? Br3 C002 C003 O1 110.8(7) . . . . ? Br1 C002 C003 O1 -130.1(7) . . . . ? Br2 C002 C003 O2 172.6(6) . . . . ? Br3 C002 C003 O2 -67.7(8) . . . . ? Br1 C002 C003 O2 51.5(8) . . . . ? C006 N5 C004 O4 -179.7(8) . . . . ? C006 N5 C004 N4 -0.3(12) . . . . ? C008 N1 C005 O3 -179.8(8) . . . . ? C008 N1 C005 N2 0.7(11) . . . . ? C001 N2 C005 O3 -179.0(8) . . . . ? C001 N2 C005 N1 0.6(11) . . . . ? C004 N5 C006 N6 175.9(8) . . . . ? C004 N5 C006 C007 -5.3(12) . . . . ? N6 C006 C007 C009 -174.5(9) . . . . ? N5 C006 C007 C009 6.7(13) . . . . ? C005 N1 C008 C010 0.0(12) . . . . ? C006 C007 C009 N4 -2.7(15) . . . . ? C007 C009 N4 C004 -3.0(14) . . . . ? O4 C004 N4 C009 -176.1(9) . . . . ? N5 C004 N4 C009 4.6(12) . . . . ? N1 C008 C010 C001 -1.8(11) . . . . ? N3 C001 C010 C008 -176.2(7) . . . . ? N2 C001 C010 C008 2.9(10) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.43 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.620 _refine_diff_density_min -1.974 _refine_diff_density_rms 0.350 _database_code_depnum_ccdc_archive 'CCDC 965966' ####################################################################### # # 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_p2 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 N3 O3 S), 2(C2 O4), O' _chemical_formula_sum 'C20 N6 O15 S2' _chemical_formula_weight 628.3712 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' _cell_length_a 12.8936(11) _cell_length_b 6.6821(5) _cell_length_c 17.1763(13) _cell_angle_alpha 90.00 _cell_angle_beta 108.031(2) _cell_angle_gamma 90.00 _cell_volume 1407.17(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.483 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 684 _exptl_absorpt_coefficient_mu 0.270 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 42195 _diffrn_reflns_av_R_equivalents 0.0326 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.63 _reflns_number_total 6484 _reflns_number_gt 5629 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.2000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.2(2) _refine_ls_number_reflns 6484 _refine_ls_number_parameters 388 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1282 _refine_ls_R_factor_gt 0.1174 _refine_ls_wR_factor_ref 0.3622 _refine_ls_wR_factor_gt 0.3467 _refine_ls_goodness_of_fit_ref 1.687 _refine_ls_restrained_S_all 1.687 _refine_ls_shift/su_max 0.005 _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 O15 O 0.2147(3) 0.5034(6) 0.1751(2) 0.0400(8) Uani 1 1 d . . . S1 S 0.01458(16) 0.0801(4) 0.10154(10) 0.0662(6) Uani 1 1 d . . . N5 N -0.1399(4) 0.0150(7) 0.4028(3) 0.0403(10) Uani 1 1 d . . . C001 C -0.1065(5) 0.3002(8) 0.3036(3) 0.0366(11) Uani 1 1 d . . . N6 N -0.1383(4) 0.2536(7) 0.5015(3) 0.0379(10) Uani 1 1 d . . . N4 N -0.1193(4) 0.1049(7) 0.2783(3) 0.0390(10) Uani 1 1 d . . . O12 O -0.1489(6) -0.2207(7) 0.3075(3) 0.0716(18) Uani 1 1 d . . . C002 C -0.1128(5) 0.3561(8) 0.3758(3) 0.0371(11) Uani 1 1 d . . . O11 O -0.1565(3) 0.1948(8) 0.1437(2) 0.0459(10) Uani 1 1 d . . . C003 C -0.1312(4) 0.2117(7) 0.4290(3) 0.0302(9) Uani 1 1 d . . . C004 C -0.1382(5) -0.0463(8) 0.3265(3) 0.0404(12) Uani 1 1 d . . . C005 C -0.1021(5) 0.2440(12) 0.0855(3) 0.0471(15) Uani 1 1 d . . . C006 C 0.0218(7) 0.0469(15) 0.2071(4) 0.068(2) Uani 1 1 d . . . C007 C -0.1027(6) 0.0454(10) 0.2002(3) 0.0459(13) Uani 1 1 d . . . O14 O -0.0059(5) 0.5269(11) 0.1674(4) 0.0719(16) Uani 1 1 d . . . C008 C -0.0791(6) 0.4638(15) 0.0911(5) 0.065(2) Uani 1 1 d . . . S2 S 0.59954(19) 0.3561(6) 0.41900(15) 0.0846(8) Uani 1 1 d . . . N3 N 0.6082(4) 0.6161(6) 0.1066(2) 0.0297(8) Uani 1 1 d . . . O7 O 0.6804(5) 0.6787(7) -0.0720(3) 0.0595(14) Uani 1 1 d . . . O9 O 0.6875(4) 1.1837(6) -0.1148(3) 0.0482(11) Uani 1 1 d . . . O10 O 0.7012(5) 0.9168(7) -0.1860(3) 0.0540(12) Uani 1 1 d . . . O8 O 0.6450(4) 0.9266(6) 0.0010(3) 0.0453(10) Uani 1 1 d . . . N2 N 0.6353(3) 0.3806(6) 0.0178(2) 0.0315(8) Uani 1 1 d . . . C009 C 0.5671(4) 0.3308(7) 0.2028(3) 0.0331(10) Uani 1 1 d . . . N1 N 0.5578(3) 0.5269(6) 0.2209(2) 0.0300(8) Uani 1 1 d . . . O13 O 0.2946(5) 0.1278(7) 0.3119(3) 0.0579(12) Uani 1 1 d . . . C010 C 0.6888(4) 1.0070(7) -0.1222(3) 0.0310(9) Uani 1 1 d . . . O2 O 0.5742(5) 0.8547(6) 0.1910(3) 0.0547(12) Uani 1 1 d . . . C011 C 0.5166(5) 0.5889(10) 0.2884(3) 0.0405(12) Uani 1 1 d . . . C012 C 0.6148(4) 0.4242(7) 0.0854(3) 0.0274(9) Uani 1 1 d . . . C013 C 0.6688(4) 0.8555(8) -0.0584(3) 0.0344(10) Uani 1 1 d . . . C014 C 0.5972(4) 0.2733(7) 0.1380(3) 0.0337(10) Uani 1 1 d . . . O1 O 0.4439(4) 0.4380(8) 0.2948(3) 0.0534(11) Uani 1 1 d . . . C015 C 0.5782(4) 0.6785(7) 0.1743(3) 0.0334(10) Uani 1 1 d . . . C016 C 0.6079(8) 0.622(2) 0.3643(5) 0.093(4) Uani 1 1 d . . . C017 C 0.4620(9) 0.3606(15) 0.3752(6) 0.081(3) Uani 1 1 d . . . C018 C 0.4152(10) 0.1330(17) 0.3578(8) 0.088(3) Uani 1 1 d . . . O5 O 0.2018(8) 0.9497(8) 0.4145(4) 0.088(2) Uani 1 1 d . . . O6 O 0.1535(5) 0.7072(7) 0.4864(3) 0.0512(11) Uani 1 1 d . . . O3 O 0.2350(5) 0.6973(8) 0.3120(3) 0.0571(13) Uani 1 1 d . . . O4 O 0.1568(7) 0.4497(8) 0.3610(4) 0.081(2) Uani 1 1 d . . . C019 C 0.1808(6) 0.7747(9) 0.4283(3) 0.0431(13) Uani 1 1 d . . . C020 C 0.1912(5) 0.6216(8) 0.3635(3) 0.0405(12) 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 O15 0.053(2) 0.0335(18) 0.0427(19) -0.0020(15) 0.0289(17) 0.0001(16) S1 0.0717(11) 0.0917(15) 0.0465(9) 0.0008(9) 0.0349(8) 0.0118(10) N5 0.067(3) 0.024(2) 0.035(2) -0.0001(17) 0.024(2) -0.007(2) C001 0.052(3) 0.027(2) 0.034(2) 0.010(2) 0.017(2) -0.001(2) N6 0.051(2) 0.034(2) 0.039(2) -0.0035(19) 0.0292(19) -0.0017(19) N4 0.065(3) 0.031(2) 0.028(2) 0.0049(17) 0.0249(19) -0.002(2) O12 0.154(6) 0.025(2) 0.052(3) -0.0019(19) 0.056(3) -0.006(3) C002 0.054(3) 0.023(2) 0.041(3) 0.003(2) 0.024(2) -0.002(2) O11 0.0424(19) 0.068(3) 0.0295(18) 0.0134(18) 0.0148(15) -0.0010(19) C003 0.036(2) 0.030(2) 0.027(2) 0.0016(18) 0.0122(17) 0.0035(17) C004 0.076(4) 0.021(2) 0.031(2) -0.0005(18) 0.027(2) -0.002(2) C005 0.047(3) 0.076(4) 0.024(2) 0.002(2) 0.020(2) 0.002(3) C006 0.084(5) 0.086(6) 0.039(3) 0.016(3) 0.026(3) 0.038(5) C007 0.079(4) 0.039(3) 0.030(2) -0.002(2) 0.033(3) 0.000(3) O14 0.068(3) 0.083(4) 0.072(4) 0.006(3) 0.032(3) -0.010(3) C008 0.057(3) 0.087(6) 0.057(4) 0.035(4) 0.025(3) 0.003(4) S2 0.0712(12) 0.112(2) 0.0643(12) 0.0171(13) 0.0122(9) 0.0059(13) N3 0.048(2) 0.0225(17) 0.0257(18) 0.0030(15) 0.0218(16) -0.0008(16) O7 0.116(4) 0.032(2) 0.052(3) -0.0025(19) 0.057(3) -0.003(2) O9 0.079(3) 0.0289(18) 0.048(2) 0.0005(17) 0.037(2) -0.0034(18) O10 0.103(4) 0.035(2) 0.043(2) -0.0043(17) 0.051(2) -0.010(2) O8 0.071(2) 0.039(2) 0.040(2) 0.0017(17) 0.0366(19) -0.0011(18) N2 0.045(2) 0.029(2) 0.0267(18) 0.0047(15) 0.0204(16) 0.0004(16) C009 0.044(2) 0.027(2) 0.036(2) 0.0077(19) 0.024(2) 0.0007(18) N1 0.043(2) 0.0296(19) 0.0235(18) 0.0034(15) 0.0195(16) 0.0027(16) O13 0.092(4) 0.038(2) 0.053(3) -0.009(2) 0.035(2) -0.009(2) C010 0.040(2) 0.028(2) 0.031(2) 0.0006(18) 0.0186(19) -0.0013(18) O2 0.107(4) 0.0265(19) 0.046(2) -0.0003(17) 0.047(2) 0.000(2) C011 0.053(3) 0.051(3) 0.025(2) 0.008(2) 0.024(2) 0.006(2) C012 0.032(2) 0.025(2) 0.030(2) 0.0018(17) 0.0163(17) -0.0002(16) C013 0.055(3) 0.031(2) 0.026(2) 0.0003(19) 0.027(2) 0.003(2) C014 0.053(3) 0.022(2) 0.035(2) 0.0032(18) 0.026(2) -0.0047(19) O1 0.058(2) 0.058(3) 0.061(3) 0.018(2) 0.041(2) 0.001(2) C015 0.052(3) 0.020(2) 0.034(2) 0.0037(17) 0.022(2) 0.0002(19) C016 0.079(5) 0.157(11) 0.035(3) -0.029(5) 0.007(3) 0.002(6) C017 0.115(6) 0.075(5) 0.083(5) 0.055(5) 0.078(5) 0.046(5) C018 0.095(7) 0.072(6) 0.107(8) 0.011(6) 0.043(6) -0.002(5) O5 0.191(8) 0.037(3) 0.073(4) -0.021(2) 0.096(5) -0.022(3) O6 0.092(3) 0.038(2) 0.036(2) 0.0039(17) 0.038(2) 0.010(2) O3 0.095(4) 0.049(3) 0.046(2) -0.012(2) 0.050(3) -0.019(2) O4 0.161(6) 0.046(3) 0.063(3) -0.005(2) 0.074(4) -0.016(3) C019 0.073(4) 0.040(3) 0.024(2) 0.005(2) 0.026(2) 0.006(3) C020 0.072(3) 0.030(2) 0.025(2) 0.0081(19) 0.023(2) 0.004(2) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C005 1.811(7) . ? S1 C006 1.800(7) . ? N5 C003 1.382(7) . ? N5 C004 1.380(7) . ? C001 C002 1.322(8) . ? C001 N4 1.369(7) . ? N6 C003 1.307(6) . ? N4 C004 1.376(7) . ? N4 C007 1.477(6) . ? O12 C004 1.207(7) . ? C002 C003 1.398(7) . ? O11 C007 1.415(8) . ? O11 C005 1.426(6) . ? C005 C008 1.495(13) . ? C006 C007 1.572(11) . ? O14 C008 1.420(11) . ? S2 C017 1.698(11) . ? S2 C016 2.029(16) . ? N3 C012 1.343(6) . ? N3 C015 1.399(6) . ? O7 C013 1.222(7) . ? O9 C010 1.188(7) . ? O10 C010 1.304(6) . ? O8 C013 1.247(6) . ? N2 C012 1.301(6) . ? C009 C014 1.343(7) . ? C009 N1 1.361(7) . ? N1 C015 1.365(6) . ? N1 C011 1.477(6) . ? O13 C018 1.511(13) . ? C010 C013 1.571(7) . ? O2 C015 1.216(7) . ? C011 O1 1.404(7) . ? C011 C016 1.478(10) . ? C012 C014 1.418(6) . ? O1 C017 1.425(8) . ? C017 C018 1.630(17) . ? O5 C019 1.240(8) . ? O6 C019 1.241(7) . ? O3 C020 1.292(7) . ? O4 C020 1.227(8) . ? C019 C020 1.548(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 C005 S1 C006 90.5(3) . . ? C003 N5 C004 124.6(4) . . ? C002 C001 N4 122.0(5) . . ? C001 N4 C004 122.4(4) . . ? C001 N4 C007 120.5(5) . . ? C004 N4 C007 116.9(5) . . ? C001 C002 C003 119.4(5) . . ? C007 O11 C005 113.6(5) . . ? N6 C003 N5 119.4(5) . . ? N6 C003 C002 123.4(5) . . ? N5 C003 C002 117.2(4) . . ? O12 C004 N4 125.0(5) . . ? O12 C004 N5 120.7(5) . . ? N4 C004 N5 114.3(5) . . ? O11 C005 C008 108.2(6) . . ? O11 C005 S1 108.7(5) . . ? C008 C005 S1 116.5(5) . . ? C007 C006 S1 101.0(5) . . ? O11 C007 N4 104.8(5) . . ? O11 C007 C006 108.7(5) . . ? N4 C007 C006 111.2(5) . . ? O14 C008 C005 114.4(6) . . ? C017 S2 C016 88.7(4) . . ? C012 N3 C015 124.5(4) . . ? C014 C009 N1 122.2(4) . . ? C009 N1 C015 122.3(4) . . ? C009 N1 C011 121.9(4) . . ? C015 N1 C011 115.7(4) . . ? O9 C010 O10 124.0(5) . . ? O9 C010 C013 123.7(5) . . ? O10 C010 C013 112.2(4) . . ? O1 C011 N1 105.7(5) . . ? O1 C011 C016 114.1(7) . . ? N1 C011 C016 110.7(5) . . ? N2 C012 N3 120.2(4) . . ? N2 C012 C014 121.7(4) . . ? N3 C012 C014 118.1(4) . . ? O7 C013 O8 126.9(5) . . ? O7 C013 C010 115.7(4) . . ? O8 C013 C010 117.4(5) . . ? C009 C014 C012 117.9(5) . . ? C011 O1 C017 115.0(7) . . ? O2 C015 N1 123.4(5) . . ? O2 C015 N3 121.8(5) . . ? N1 C015 N3 114.8(4) . . ? C011 C016 S2 97.7(8) . . ? O1 C017 C018 102.8(9) . . ? O1 C017 S2 105.7(5) . . ? C018 C017 S2 110.0(6) . . ? O13 C018 C017 112.3(8) . . ? O5 C019 O6 129.1(6) . . ? O5 C019 C020 114.4(5) . . ? O6 C019 C020 116.6(5) . . ? O4 C020 O3 124.9(5) . . ? O4 C020 C019 122.2(5) . . ? O3 C020 C019 112.8(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 C002 C001 N4 C004 -0.8(9) . . . . ? C002 C001 N4 C007 -174.9(5) . . . . ? N4 C001 C002 C003 1.2(9) . . . . ? C004 N5 C003 N6 177.1(5) . . . . ? C004 N5 C003 C002 -4.1(8) . . . . ? C001 C002 C003 N6 179.9(5) . . . . ? C001 C002 C003 N5 1.1(8) . . . . ? C001 N4 C004 O12 -179.2(7) . . . . ? C007 N4 C004 O12 -4.9(10) . . . . ? C001 N4 C004 N5 -1.8(9) . . . . ? C007 N4 C004 N5 172.5(5) . . . . ? C003 N5 C004 O12 -178.2(7) . . . . ? C003 N5 C004 N4 4.3(9) . . . . ? C007 O11 C005 C008 -123.3(6) . . . . ? C007 O11 C005 S1 4.0(7) . . . . ? C006 S1 C005 O11 -25.7(6) . . . . ? C006 S1 C005 C008 96.7(6) . . . . ? C005 S1 C006 C007 36.5(6) . . . . ? C005 O11 C007 N4 143.6(5) . . . . ? C005 O11 C007 C006 24.7(7) . . . . ? C001 N4 C007 O11 -44.1(7) . . . . ? C004 N4 C007 O11 141.5(5) . . . . ? C001 N4 C007 C006 73.1(7) . . . . ? C004 N4 C007 C006 -101.3(7) . . . . ? S1 C006 C007 O11 -41.2(7) . . . . ? S1 C006 C007 N4 -155.9(5) . . . . ? O11 C005 C008 O14 64.3(7) . . . . ? S1 C005 C008 O14 -58.4(7) . . . . ? C014 C009 N1 C015 0.2(8) . . . . ? C014 C009 N1 C011 175.3(5) . . . . ? C009 N1 C011 O1 -29.9(7) . . . . ? C015 N1 C011 O1 145.6(5) . . . . ? C009 N1 C011 C016 94.1(9) . . . . ? C015 N1 C011 C016 -90.4(8) . . . . ? C015 N3 C012 N2 174.7(4) . . . . ? C015 N3 C012 C014 -4.3(7) . . . . ? O9 C010 C013 O7 -175.0(7) . . . . ? O10 C010 C013 O7 8.3(7) . . . . ? O9 C010 C013 O8 3.7(8) . . . . ? O10 C010 C013 O8 -173.0(5) . . . . ? N1 C009 C014 C012 -2.9(8) . . . . ? N2 C012 C014 C009 -174.2(5) . . . . ? N3 C012 C014 C009 4.8(7) . . . . ? N1 C011 O1 C017 129.5(5) . . . . ? C016 C011 O1 C017 7.6(9) . . . . ? C009 N1 C015 O2 -177.3(6) . . . . ? C011 N1 C015 O2 7.3(8) . . . . ? C009 N1 C015 N3 0.6(7) . . . . ? C011 N1 C015 N3 -174.8(4) . . . . ? C012 N3 C015 O2 179.5(6) . . . . ? C012 N3 C015 N1 1.5(7) . . . . ? O1 C011 C016 S2 19.5(7) . . . . ? N1 C011 C016 S2 -99.6(5) . . . . ? C017 S2 C016 C011 -33.9(6) . . . . ? C011 O1 C017 C018 -152.1(6) . . . . ? C011 O1 C017 S2 -36.8(8) . . . . ? C016 S2 C017 O1 39.3(7) . . . . ? C016 S2 C017 C018 149.6(7) . . . . ? O1 C017 C018 O13 -62.6(9) . . . . ? S2 C017 C018 O13 -174.8(6) . . . . ? O5 C019 C020 O4 -168.1(8) . . . . ? O6 C019 C020 O4 12.2(10) . . . . ? O5 C019 C020 O3 9.3(10) . . . . ? O6 C019 C020 O3 -170.4(6) . . . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.63 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.600 _refine_diff_density_min -0.841 _refine_diff_density_rms 0.158 _database_code_depnum_ccdc_archive 'CCDC 965967' ####################################################################### # # 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_datam _audit_creation_method SHELXL-97 _chemical_absolute_configuration ad _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H12 N3 O3 S), C2 O4' _chemical_formula_sum 'C18 H24 N6 O10 S2' _chemical_formula_weight 548.57 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 6.7021(15) _cell_length_b 9.134(2) _cell_length_c 37.734(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2309.9(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.577 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1140 _exptl_absorpt_coefficient_mu 0.299 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20786 _diffrn_reflns_av_R_equivalents 0.1426 _diffrn_reflns_av_sigmaI/netI 0.0971 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -49 _diffrn_reflns_limit_l_max 49 _diffrn_reflns_theta_min 1.08 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5279 _reflns_number_gt 4720 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.0616P)^2^+1.3062P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(11) _refine_ls_number_reflns 5279 _refine_ls_number_parameters 326 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0672 _refine_ls_R_factor_gt 0.0588 _refine_ls_wR_factor_ref 0.1631 _refine_ls_wR_factor_gt 0.1465 _refine_ls_goodness_of_fit_ref 1.092 _refine_ls_restrained_S_all 1.092 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.23709(15) 0.56472(11) 0.11359(2) 0.0261(2) Uani 1 1 d . . . O3 O 0.0678(4) 1.3318(3) 0.04406(7) 0.0224(5) Uani 1 1 d . . . O1 O 0.0970(4) 1.1619(3) 0.12801(6) 0.0226(5) Uani 1 1 d . . . O4 O -0.1683(4) 1.3049(3) 0.08580(7) 0.0251(6) Uani 1 1 d . . . O2 O 0.3163(4) 1.1632(3) 0.08307(7) 0.0245(6) Uani 1 1 d . . . O10 O 0.0934(4) 0.8302(3) 0.10436(7) 0.0265(6) Uani 1 1 d . . . N2 N 0.2615(4) 1.0369(3) -0.00227(8) 0.0210(6) Uani 1 1 d . . . H20 H 0.3511 1.0747 -0.0158 0.025 Uiso 1 1 calc R . . O6 O -0.2080(5) 0.6139(3) 0.08464(8) 0.0322(7) Uani 1 1 d . . . H25 H -0.2177 0.5244 0.0838 0.048 Uiso 1 1 calc R . . N1 N 0.1737(5) 0.8904(3) 0.04592(8) 0.0216(6) Uani 1 1 d . . . C7 C 0.3242(5) 0.9448(5) 0.02468(10) 0.0224(7) Uani 1 1 d . . . O7 O 0.4994(4) 0.9153(4) 0.02897(8) 0.0336(7) Uani 1 1 d . . . C2 C 0.0050(5) 1.2857(4) 0.07341(10) 0.0210(7) Uani 1 1 d . . . C1 C 0.1522(5) 1.1956(4) 0.09690(9) 0.0194(7) Uani 1 1 d . . . C9 C -0.0803(6) 1.0068(4) 0.01296(10) 0.0226(8) Uani 1 1 d . . . H22 H -0.2147 1.0261 0.0091 0.027 Uiso 1 1 calc R . . C6 C 0.2637(6) 0.6461(4) 0.07054(9) 0.0229(7) Uani 1 1 d . . . H17 H 0.3939 0.6251 0.0605 0.027 Uiso 1 1 calc R . . H18 H 0.1614 0.6111 0.0544 0.027 Uiso 1 1 calc R . . N3 N 0.0232(5) 1.1613(4) -0.03508(8) 0.0243(7) Uani 1 1 d . . . H24 H 0.1171 1.1974 -0.0479 0.029 Uiso 1 1 calc R . . H23 H -0.0991 1.1837 -0.0394 0.029 Uiso 1 1 calc R . . C10 C -0.0244(5) 0.9171(4) 0.03930(10) 0.0225(8) Uani 1 1 d . . . H21 H -0.1212 0.8723 0.0533 0.027 Uiso 1 1 calc R . . C8 C 0.0668(5) 1.0717(4) -0.00883(9) 0.0205(7) Uani 1 1 d . . . C4 C 0.0509(6) 0.7029(4) 0.12520(10) 0.0249(8) Uani 1 1 d . . . H16 H 0.0688 0.7285 0.1502 0.030 Uiso 1 1 calc R . . C5 C 0.2397(6) 0.8079(4) 0.07774(9) 0.0225(7) Uani 1 1 d . . . H19 H 0.3673 0.8478 0.0859 0.027 Uiso 1 1 calc R . . C3 C -0.1648(6) 0.6574(5) 0.11975(11) 0.0313(9) Uani 1 1 d . . . H14 H -0.1950 0.5769 0.1356 0.038 Uiso 1 1 calc R . . H15 H -0.2509 0.7386 0.1261 0.038 Uiso 1 1 calc R . . S2 S 0.31623(15) 0.55594(11) 0.20650(2) 0.0268(2) Uani 1 1 d . . . O9 O 0.3844(4) 0.2865(3) 0.22721(7) 0.0203(5) Uani 1 1 d . . . O8 O 0.8253(4) 0.4400(3) 0.29050(7) 0.0251(6) Uani 1 1 d . . . N4 N 0.4927(4) 0.4123(3) 0.27855(8) 0.0196(6) Uani 1 1 d . . . N5 N 0.6019(4) 0.5086(3) 0.33286(8) 0.0195(6) Uani 1 1 d . . . H3 H 0.6973 0.5287 0.3473 0.023 Uiso 1 1 calc R . . O5 O -0.0607(4) 0.3680(4) 0.17418(7) 0.0317(7) Uani 1 1 d . . . H12 H -0.0164 0.3344 0.1556 0.048 Uiso 1 1 calc R . . C12 C 0.2712(6) 0.3621(4) 0.19997(9) 0.0218(7) Uani 1 1 d . . . H9 H 0.3221 0.3333 0.1766 0.026 Uiso 1 1 calc R . . C11 C 0.0549(5) 0.3171(5) 0.20286(10) 0.0260(8) Uani 1 1 d . . . H11 H 0.0469 0.2111 0.2038 0.031 Uiso 1 1 calc R . . H10 H 0.0000 0.3553 0.2248 0.031 Uiso 1 1 calc R . . N6 N 0.3787(5) 0.5957(4) 0.37449(9) 0.0284(8) Uani 1 1 d . . . H1 H 0.4774 0.6204 0.3878 0.034 Uiso 1 1 calc R . . H2 H 0.2584 0.6116 0.3814 0.034 Uiso 1 1 calc R . . C16 C 0.4115(5) 0.5340(4) 0.34390(9) 0.0200(7) Uani 1 1 d . . . C15 C 0.6521(5) 0.4527(4) 0.30002(9) 0.0194(7) Uani 1 1 d . . . C18 C 0.2967(5) 0.4306(4) 0.28959(9) 0.0221(7) Uani 1 1 d . . . H5 H 0.1937 0.4017 0.2746 0.027 Uiso 1 1 calc R . . C17 C 0.2514(5) 0.4887(4) 0.32124(9) 0.0228(8) Uani 1 1 d . . . H4 H 0.1193 0.4994 0.3283 0.027 Uiso 1 1 calc R . . C13 C 0.5431(6) 0.3707(4) 0.24130(9) 0.0215(7) Uani 1 1 d . . . H7 H 0.6659 0.3124 0.2411 0.026 Uiso 1 1 calc R . . C14 C 0.5709(6) 0.5066(4) 0.21792(10) 0.0250(8) Uani 1 1 d . . . H8 H 0.6483 0.4838 0.1969 0.030 Uiso 1 1 calc R . . H6 H 0.6364 0.5848 0.2309 0.030 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0343(5) 0.0230(5) 0.0209(4) 0.0061(4) 0.0024(4) 0.0043(4) O3 0.0241(12) 0.0237(14) 0.0194(12) 0.0059(11) 0.0007(10) 0.0009(11) O1 0.0312(13) 0.0227(13) 0.0140(12) 0.0043(10) 0.0042(10) -0.0011(11) O4 0.0219(12) 0.0307(15) 0.0227(13) 0.0058(12) 0.0026(11) 0.0017(11) O2 0.0241(12) 0.0317(15) 0.0176(12) 0.0072(11) 0.0016(10) 0.0034(11) O10 0.0423(15) 0.0182(13) 0.0190(13) 0.0031(10) 0.0068(12) 0.0014(12) N2 0.0215(14) 0.0225(16) 0.0191(14) 0.0063(12) 0.0021(12) 0.0006(13) O6 0.0348(15) 0.0274(15) 0.0344(16) -0.0002(13) -0.0043(13) 0.0015(14) N1 0.0237(15) 0.0219(15) 0.0191(15) 0.0047(12) 0.0015(12) -0.0029(13) C7 0.0230(16) 0.0225(17) 0.0215(17) 0.0070(15) -0.0010(14) 0.0000(16) O7 0.0212(13) 0.0406(19) 0.0389(17) 0.0190(15) 0.0014(12) 0.0030(12) C2 0.0245(17) 0.0191(18) 0.0193(18) -0.0006(14) -0.0006(14) -0.0032(15) C1 0.0245(17) 0.0186(17) 0.0153(16) 0.0015(14) -0.0041(13) -0.0025(14) C9 0.0189(16) 0.0272(19) 0.0218(18) 0.0025(15) -0.0010(14) -0.0002(15) C6 0.0276(17) 0.0227(18) 0.0184(17) 0.0013(14) 0.0007(14) 0.0020(16) N3 0.0236(15) 0.0274(18) 0.0221(16) 0.0049(14) 0.0013(13) 0.0038(13) C10 0.0212(16) 0.025(2) 0.0218(18) 0.0001(15) 0.0022(13) -0.0053(14) C8 0.0205(16) 0.0212(18) 0.0198(17) 0.0021(15) -0.0028(13) -0.0001(15) C4 0.037(2) 0.0203(19) 0.0172(17) 0.0035(15) 0.0052(15) 0.0019(16) C5 0.0284(18) 0.0241(18) 0.0150(16) 0.0026(14) -0.0011(14) -0.0026(16) C3 0.036(2) 0.028(2) 0.029(2) 0.0056(18) 0.0070(16) 0.0041(18) S2 0.0411(5) 0.0187(4) 0.0206(4) 0.0001(4) -0.0039(4) 0.0044(4) O9 0.0241(12) 0.0201(13) 0.0168(12) -0.0017(10) -0.0053(10) -0.0004(10) O8 0.0202(12) 0.0328(15) 0.0223(13) -0.0080(12) 0.0018(10) 0.0001(12) N4 0.0214(14) 0.0237(17) 0.0136(14) -0.0020(12) 0.0011(11) -0.0009(12) N5 0.0185(14) 0.0244(16) 0.0156(14) -0.0026(12) -0.0009(12) -0.0010(12) O5 0.0323(15) 0.0450(18) 0.0179(13) -0.0080(13) -0.0074(11) 0.0119(14) C12 0.0313(19) 0.0204(18) 0.0137(16) -0.0015(14) -0.0032(14) 0.0059(16) C11 0.0249(18) 0.031(2) 0.0224(19) -0.0050(17) -0.0036(15) 0.0025(16) N6 0.0233(15) 0.040(2) 0.0218(16) -0.0094(15) 0.0012(13) 0.0016(14) C16 0.0218(16) 0.0211(18) 0.0170(16) -0.0012(14) -0.0028(13) 0.0001(15) C15 0.0242(17) 0.0163(16) 0.0177(16) -0.0013(14) -0.0023(13) 0.0013(15) C18 0.0217(16) 0.0256(19) 0.0191(16) 0.0005(15) -0.0037(13) 0.0010(15) C17 0.0160(15) 0.031(2) 0.0214(18) -0.0012(15) -0.0014(14) 0.0014(15) C13 0.0269(18) 0.0225(18) 0.0152(17) -0.0066(14) -0.0021(13) 0.0005(15) C14 0.038(2) 0.0214(18) 0.0151(17) -0.0014(14) 0.0047(15) -0.0016(17) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C6 1.796(4) . ? S1 C4 1.828(4) . ? O3 C2 1.258(4) . ? O1 C1 1.269(4) . ? O4 C2 1.264(4) . ? O2 C1 1.253(4) . ? O10 C5 1.419(5) . ? O10 C4 1.432(5) . ? N2 C8 1.365(4) . ? N2 C7 1.386(5) . ? N2 H20 0.8600 . ? O6 C3 1.413(5) . ? O6 H25 0.8200 . ? N1 C10 1.373(5) . ? N1 C7 1.381(5) . ? N1 C5 1.485(4) . ? C7 O7 1.215(4) . ? C2 C1 1.561(5) . ? C9 C10 1.341(5) . ? C9 C8 1.414(5) . ? C9 H22 0.9300 . ? C6 C5 1.511(5) . ? C6 H17 0.9700 . ? C6 H18 0.9700 . ? N3 C8 1.317(5) . ? N3 H24 0.8600 . ? N3 H23 0.8600 . ? C10 H21 0.9300 . ? C4 C3 1.518(6) . ? C4 H16 0.9800 . ? C5 H19 0.9800 . ? C3 H14 0.9700 . ? C3 H15 0.9700 . ? S2 C12 1.813(4) . ? S2 C14 1.817(4) . ? O9 C13 1.416(4) . ? O9 C12 1.452(4) . ? O8 C15 1.221(4) . ? N4 C18 1.389(4) . ? N4 C15 1.390(4) . ? N4 C13 1.495(4) . ? N5 C16 1.362(5) . ? N5 C15 1.382(4) . ? N5 H3 0.8600 . ? O5 C11 1.410(5) . ? O5 H12 0.8200 . ? C12 C11 1.511(5) . ? C12 H9 0.9800 . ? C11 H11 0.9700 . ? C11 H10 0.9700 . ? N6 C16 1.303(5) . ? N6 H1 0.8600 . ? N6 H2 0.8600 . ? C16 C17 1.433(5) . ? C18 C17 1.341(5) . ? C18 H5 0.9300 . ? C17 H4 0.9300 . ? C13 C14 1.534(5) . ? C13 H7 0.9800 . ? C14 H8 0.9700 . ? C14 H6 0.9700 . ? 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 C6 S1 C4 89.93(18) . . ? C5 O10 C4 114.2(3) . . ? C8 N2 C7 124.4(3) . . ? C8 N2 H20 117.8 . . ? C7 N2 H20 117.8 . . ? C3 O6 H25 109.5 . . ? C10 N1 C7 122.5(3) . . ? C10 N1 C5 121.7(3) . . ? C7 N1 C5 115.7(3) . . ? O7 C7 N1 123.3(3) . . ? O7 C7 N2 121.7(3) . . ? N1 C7 N2 115.0(3) . . ? O3 C2 O4 125.9(4) . . ? O3 C2 C1 117.7(3) . . ? O4 C2 C1 116.3(3) . . ? O2 C1 O1 125.7(3) . . ? O2 C1 C2 116.3(3) . . ? O1 C1 C2 118.0(3) . . ? C10 C9 C8 119.5(3) . . ? C10 C9 H22 120.2 . . ? C8 C9 H22 120.2 . . ? C5 C6 S1 103.4(2) . . ? C5 C6 H17 111.1 . . ? S1 C6 H17 111.1 . . ? C5 C6 H18 111.1 . . ? S1 C6 H18 111.1 . . ? H17 C6 H18 109.0 . . ? C8 N3 H24 120.0 . . ? C8 N3 H23 120.0 . . ? H24 N3 H23 120.0 . . ? C9 C10 N1 120.9(3) . . ? C9 C10 H21 119.6 . . ? N1 C10 H21 119.6 . . ? N3 C8 N2 119.5(3) . . ? N3 C8 C9 122.9(3) . . ? N2 C8 C9 117.6(3) . . ? O10 C4 C3 109.7(3) . . ? O10 C4 S1 107.0(3) . . ? C3 C4 S1 115.3(3) . . ? O10 C4 H16 108.2 . . ? C3 C4 H16 108.2 . . ? S1 C4 H16 108.2 . . ? O10 C5 N1 107.1(3) . . ? O10 C5 C6 109.9(3) . . ? N1 C5 C6 112.5(3) . . ? O10 C5 H19 109.1 . . ? N1 C5 H19 109.1 . . ? C6 C5 H19 109.1 . . ? O6 C3 C4 113.5(3) . . ? O6 C3 H14 108.9 . . ? C4 C3 H14 108.9 . . ? O6 C3 H15 108.9 . . ? C4 C3 H15 108.9 . . ? H14 C3 H15 107.7 . . ? C12 S2 C14 86.92(18) . . ? C13 O9 C12 113.5(3) . . ? C18 N4 C15 121.3(3) . . ? C18 N4 C13 121.8(3) . . ? C15 N4 C13 116.2(3) . . ? C16 N5 C15 124.4(3) . . ? C16 N5 H3 117.8 . . ? C15 N5 H3 117.8 . . ? C11 O5 H12 109.5 . . ? O9 C12 C11 108.7(3) . . ? O9 C12 S2 106.4(2) . . ? C11 C12 S2 114.6(3) . . ? O9 C12 H9 109.0 . . ? C11 C12 H9 109.0 . . ? S2 C12 H9 109.0 . . ? O5 C11 C12 112.4(3) . . ? O5 C11 H11 109.1 . . ? C12 C11 H11 109.1 . . ? O5 C11 H10 109.1 . . ? C12 C11 H10 109.1 . . ? H11 C11 H10 107.8 . . ? C16 N6 H1 120.0 . . ? C16 N6 H2 120.0 . . ? H1 N6 H2 120.0 . . ? N6 C16 N5 120.2(3) . . ? N6 C16 C17 121.8(3) . . ? N5 C16 C17 118.0(3) . . ? O8 C15 N5 122.0(3) . . ? O8 C15 N4 122.3(3) . . ? N5 C15 N4 115.7(3) . . ? C17 C18 N4 121.9(3) . . ? C17 C18 H5 119.0 . . ? N4 C18 H5 119.0 . . ? C18 C17 C16 118.5(3) . . ? C18 C17 H4 120.8 . . ? C16 C17 H4 120.8 . . ? O9 C13 N4 108.8(3) . . ? O9 C13 C14 108.4(3) . . ? N4 C13 C14 111.3(3) . . ? O9 C13 H7 109.5 . . ? N4 C13 H7 109.5 . . ? C14 C13 H7 109.5 . . ? C13 C14 S2 102.9(3) . . ? C13 C14 H8 111.2 . . ? S2 C14 H8 111.2 . . ? C13 C14 H6 111.2 . . ? S2 C14 H6 111.2 . . ? H8 C14 H6 109.1 . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.399 _refine_diff_density_min -0.399 _refine_diff_density_rms 0.109 _database_code_depnum_ccdc_archive 'CCDC 965968' ####################################################################### # # 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_datam _audit_creation_method SHELXL-97 _chemical_absolute_configuration ad _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety '2(C8 H11 N3 O3 S), C7 H12 O4' _chemical_formula_sum 'C23 H34 N6 O10 S2' _chemical_formula_weight 618.68 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.9440(7) _cell_length_b 28.891(3) _cell_length_c 6.9559(8) _cell_angle_alpha 90.00 _cell_angle_beta 95.357(4) _cell_angle_gamma 90.00 _cell_volume 1389.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.258 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13530 _diffrn_reflns_av_R_equivalents 0.0653 _diffrn_reflns_av_sigmaI/netI 0.0648 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 27.50 _reflns_number_total 6245 _reflns_number_gt 5969 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _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^ > 2\s(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^)+(0.0606P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.00(6) _refine_ls_number_reflns 6245 _refine_ls_number_parameters 426 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0452 _refine_ls_R_factor_gt 0.0412 _refine_ls_wR_factor_ref 0.1176 _refine_ls_wR_factor_gt 0.1043 _refine_ls_goodness_of_fit_ref 1.105 _refine_ls_restrained_S_all 1.105 _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 H10 H -0.650(4) 0.5678(10) 0.487(4) 0.017(6) Uiso 1 1 d . . . H6 H -0.603(4) 0.4813(11) 0.929(4) 0.026(8) Uiso 1 1 d . . . H13 H -0.040(5) 0.2056(11) 0.398(4) 0.027(8) Uiso 1 1 d . . . H2 H -0.540(5) 0.3062(13) 1.064(5) 0.034(9) Uiso 1 1 d . . . H3 H -0.195(4) 0.3173(10) 0.444(4) 0.018(7) Uiso 1 1 d . . . H1 H -0.551(5) 0.3425(13) 1.242(5) 0.040(9) Uiso 1 1 d . . . H5 H -0.071(5) 0.2999(13) -0.008(4) 0.028(8) Uiso 1 1 d . . . H14 H -0.732(4) 0.4583(9) 0.463(4) 0.014(6) Uiso 1 1 d . . . H12 H 0.150(6) 0.2284(13) -0.049(5) 0.037(10) Uiso 1 1 d . . . H7 H -0.566(4) 0.4261(10) 1.178(4) 0.017(7) Uiso 1 1 d . . . H4 H -0.047(5) 0.3565(13) -0.239(5) 0.039(9) Uiso 1 1 d . . . H11 H -0.912(7) 0.5792(18) 0.833(7) 0.071(15) Uiso 1 1 d . . . H9 H -0.051(6) 0.4388(14) -0.293(6) 0.047(11) Uiso 1 1 d . . . H8 H -0.027(5) 0.4736(14) -0.129(5) 0.033(9) Uiso 1 1 d . . . S1 S 0.22255(9) 0.25286(2) 0.36066(8) 0.02495(14) Uani 1 1 d . . . S2 S -0.36406(10) 0.53659(2) 0.62387(9) 0.02870(15) Uani 1 1 d . . . O1 O -0.5657(3) 0.38344(6) 0.4800(2) 0.0256(4) Uani 1 1 d . . . N4 N -0.5341(3) 0.33658(7) 1.1111(3) 0.0236(4) Uani 1 1 d . . . O8 O -0.5905(3) 0.78074(6) 0.3255(3) 0.0267(4) Uani 1 1 d . . . H8A H -0.5434 0.8046 0.2794 0.040 Uiso 1 1 calc R . . N2 N -0.0462(3) 0.42090(7) 0.1452(3) 0.0209(4) Uani 1 1 d . . . O7 O -0.4306(3) 0.74624(6) 0.1021(2) 0.0292(4) Uani 1 1 d . . . O10 O -0.8527(4) 0.59906(7) 0.7645(3) 0.0389(5) Uani 1 1 d . . . N5 N -0.5473(3) 0.35925(7) 0.7930(3) 0.0195(4) Uani 1 1 d . . . O4 O -0.7239(3) 0.51150(6) 0.6304(2) 0.0244(4) Uani 1 1 d . . . O9 O 0.0375(3) 0.22565(7) -0.0597(3) 0.0278(4) Uani 1 1 d . . . N1 N -0.0612(3) 0.34098(7) 0.2180(3) 0.0197(4) Uani 1 1 d . . . O5 O -0.0681(3) 0.50322(7) 0.2817(3) 0.0323(4) Uani 1 1 d . . . H5A H -0.0418 0.4782 0.2287 0.049 Uiso 1 1 calc R . . O3 O -0.1497(3) 0.26332(6) 0.2687(2) 0.0237(4) Uani 1 1 d . . . C001 C -0.5478(3) 0.37030(8) 0.9811(3) 0.0192(4) Uani 1 1 d . . . C002 C -0.0538(4) 0.38658(8) 0.2805(3) 0.0201(4) Uani 1 1 d . . . C003 C -0.0572(4) 0.36395(9) -0.1075(3) 0.0226(5) Uani 1 1 d . . . O2 O -0.0573(3) 0.39574(6) 0.4543(2) 0.0274(4) Uani 1 1 d . . . C004 C -0.0146(4) 0.53742(9) 0.1801(4) 0.0252(5) Uani 1 1 d . . . N3 N -0.0479(3) 0.44525(8) -0.1711(3) 0.0255(4) Uani 1 1 d . . . C005 C -0.5682(3) 0.39249(8) 0.6541(3) 0.0194(4) Uani 1 1 d . . . C006 C -0.5863(4) 0.44992(9) 0.9022(3) 0.0233(5) Uani 1 1 d . . . C007 C -0.5604(4) 0.41737(9) 1.0401(3) 0.0228(5) Uani 1 1 d . . . C008 C -0.0490(3) 0.41068(8) -0.0455(3) 0.0203(5) Uani 1 1 d . . . C009 C -0.0097(4) 0.19907(9) 0.1008(4) 0.0285(5) Uani 1 1 d . . . H00A H 0.0840 0.1733 0.1210 0.034 Uiso 1 1 calc R . . H00B H -0.1396 0.1853 0.0702 0.034 Uiso 1 1 calc R . . C010 C -0.3241(4) 0.64293(8) 0.2920(4) 0.0236(5) Uani 1 1 d . . . H01A H -0.2361 0.6688 0.2682 0.028 Uiso 1 1 calc R . . H01B H -0.3166 0.6375 0.4330 0.028 Uiso 1 1 calc R . . C011 C -0.5315(3) 0.74403(8) 0.2363(3) 0.0210(5) Uani 1 1 d . . . O6 O 0.0572(4) 0.53216(8) 0.0251(3) 0.0438(5) Uani 1 1 d . . . C012 C -0.2594(4) 0.59939(8) 0.1910(4) 0.0236(5) Uani 1 1 d . . . H01C H -0.3482 0.5737 0.2152 0.028 Uiso 1 1 calc R . . H01D H -0.2690 0.6050 0.0500 0.028 Uiso 1 1 calc R . . N6 N -0.5946(3) 0.43822(7) 0.7105(3) 0.0206(4) Uani 1 1 d . . . C013 C -0.6092(4) 0.69937(9) 0.3104(4) 0.0236(5) Uani 1 1 d . . . H01E H -0.7520 0.6996 0.2863 0.028 Uiso 1 1 calc R . . H01F H -0.5763 0.6978 0.4518 0.028 Uiso 1 1 calc R . . C014 C -0.0632(4) 0.33047(9) 0.0259(3) 0.0224(5) Uani 1 1 d . . . C015 C -0.6165(4) 0.55345(8) 0.6137(4) 0.0251(5) Uani 1 1 d . . . C016 C -0.6320(4) 0.47289(8) 0.5542(3) 0.0217(5) Uani 1 1 d . . . C017 C -0.4455(4) 0.48811(9) 0.4738(4) 0.0256(5) Uani 1 1 d . . . H01G H -0.4700 0.4976 0.3369 0.031 Uiso 1 1 calc R . . H01H H -0.3486 0.4629 0.4836 0.031 Uiso 1 1 calc R . . C018 C -0.0528(4) 0.58490(9) 0.2586(4) 0.0252(5) Uani 1 1 d . . . H01I H 0.0398 0.6075 0.2123 0.030 Uiso 1 1 calc R . . H01J H -0.0350 0.5843 0.4015 0.030 Uiso 1 1 calc R . . C019 C 0.0962(4) 0.29455(9) 0.4949(3) 0.0250(5) Uani 1 1 d . . . H01K H 0.0663 0.2816 0.6205 0.030 Uiso 1 1 calc R . . H01L H 0.1739 0.3231 0.5184 0.030 Uiso 1 1 calc R . . C020 C -0.0094(4) 0.22651(9) 0.2878(4) 0.0251(5) Uani 1 1 d . . . C021 C -0.0889(4) 0.30442(9) 0.3653(3) 0.0214(5) Uani 1 1 d . . . C022 C -0.5313(4) 0.65604(9) 0.2181(4) 0.0259(5) Uani 1 1 d . . . H02A H -0.5370 0.6609 0.0768 0.031 Uiso 1 1 calc R . . H02B H -0.6173 0.6297 0.2413 0.031 Uiso 1 1 calc R . . C023 C -0.6571(5) 0.58656(9) 0.7722(4) 0.0315(6) Uani 1 1 d . . . H02C H -0.6181 0.5720 0.8987 0.038 Uiso 1 1 calc R . . H02D H -0.5780 0.6148 0.7618 0.038 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0263(3) 0.0225(3) 0.0252(3) 0.0010(2) -0.0020(2) 0.0001(2) S2 0.0307(3) 0.0230(3) 0.0322(3) -0.0011(2) 0.0025(2) -0.0037(2) O1 0.0418(11) 0.0193(9) 0.0162(8) -0.0003(7) 0.0058(7) -0.0021(8) N4 0.0336(12) 0.0196(10) 0.0177(10) 0.0003(8) 0.0032(8) -0.0009(8) O8 0.0348(10) 0.0175(8) 0.0292(9) -0.0004(7) 0.0107(7) 0.0017(7) N2 0.0291(11) 0.0175(9) 0.0163(9) -0.0003(7) 0.0034(8) 0.0025(8) O7 0.0375(10) 0.0243(9) 0.0273(9) 0.0029(7) 0.0114(7) 0.0071(8) O10 0.0503(14) 0.0256(10) 0.0425(12) 0.0004(9) 0.0136(10) 0.0103(9) N5 0.0258(10) 0.0175(9) 0.0154(9) -0.0006(7) 0.0022(7) -0.0010(7) O4 0.0294(9) 0.0158(8) 0.0283(9) -0.0021(6) 0.0039(7) -0.0003(7) O9 0.0326(11) 0.0259(10) 0.0248(9) -0.0024(7) 0.0022(8) -0.0035(8) N1 0.0249(10) 0.0190(10) 0.0151(9) 0.0015(7) 0.0017(7) 0.0008(8) O5 0.0467(12) 0.0212(9) 0.0304(10) -0.0006(7) 0.0105(8) 0.0018(8) O3 0.0248(9) 0.0204(8) 0.0257(8) -0.0008(6) 0.0009(7) -0.0035(6) C001 0.0176(11) 0.0217(12) 0.0183(10) 0.0002(8) 0.0022(8) -0.0015(8) C002 0.0232(11) 0.0199(11) 0.0171(10) -0.0009(9) 0.0005(8) 0.0024(9) C003 0.0277(12) 0.0234(12) 0.0165(11) -0.0013(9) 0.0017(9) 0.0024(9) O2 0.0427(11) 0.0253(9) 0.0146(8) -0.0021(7) 0.0048(7) 0.0024(7) C004 0.0224(12) 0.0254(12) 0.0276(11) 0.0004(10) 0.0017(9) 0.0034(10) N3 0.0345(12) 0.0238(11) 0.0185(10) 0.0033(8) 0.0036(8) 0.0036(9) C005 0.0228(12) 0.0155(10) 0.0194(10) -0.0008(8) 0.0006(9) -0.0022(8) C006 0.0308(13) 0.0199(12) 0.0191(11) -0.0037(9) 0.0017(9) -0.0001(9) C007 0.0310(13) 0.0205(12) 0.0167(11) -0.0028(9) 0.0015(9) -0.0015(9) C008 0.0178(11) 0.0223(12) 0.0211(11) 0.0017(9) 0.0036(8) 0.0041(9) C009 0.0345(14) 0.0195(12) 0.0315(13) -0.0019(10) 0.0027(11) -0.0042(10) C010 0.0247(12) 0.0164(11) 0.0291(12) 0.0013(9) -0.0010(9) 0.0004(8) C011 0.0231(11) 0.0182(11) 0.0211(10) 0.0022(9) -0.0010(8) 0.0028(8) O6 0.0621(15) 0.0275(11) 0.0465(12) -0.0008(9) 0.0301(11) 0.0015(10) C012 0.0248(13) 0.0181(11) 0.0275(12) -0.0002(9) 0.0010(9) 0.0033(9) N6 0.0276(11) 0.0174(10) 0.0168(9) -0.0003(7) 0.0018(7) -0.0002(8) C013 0.0237(12) 0.0187(11) 0.0280(12) -0.0012(9) 0.0008(9) 0.0016(9) C014 0.0277(13) 0.0214(12) 0.0177(11) -0.0034(9) 0.0011(9) 0.0013(9) C015 0.0332(14) 0.0154(11) 0.0262(12) 0.0027(9) 0.0010(10) -0.0012(9) C016 0.0317(13) 0.0145(10) 0.0189(10) 0.0013(8) 0.0024(9) 0.0012(9) C017 0.0327(14) 0.0208(12) 0.0242(12) 0.0027(9) 0.0066(10) 0.0006(9) C018 0.0221(12) 0.0229(12) 0.0308(12) -0.0014(10) 0.0033(10) 0.0004(9) C019 0.0341(14) 0.0218(12) 0.0184(10) 0.0025(9) -0.0014(9) 0.0000(10) C020 0.0299(13) 0.0187(11) 0.0267(12) 0.0045(9) 0.0029(10) -0.0036(10) C021 0.0263(12) 0.0205(11) 0.0176(10) 0.0016(9) 0.0024(9) -0.0033(9) C022 0.0244(13) 0.0176(11) 0.0352(13) -0.0037(10) 0.0002(10) -0.0006(9) C023 0.0446(17) 0.0197(12) 0.0307(13) -0.0039(10) 0.0064(11) -0.0028(11) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C019 1.802(3) . ? S1 C020 1.810(3) . ? S2 C017 1.806(3) . ? S2 C015 1.814(3) . ? O1 C005 1.241(3) . ? N4 C001 1.326(3) . ? N4 H2 0.94(4) . ? N4 H1 0.95(4) . ? O8 C011 1.313(3) . ? O8 H8A 0.8400 . ? N2 C008 1.358(3) . ? N2 C002 1.371(3) . ? O7 C011 1.220(3) . ? O10 C023 1.402(4) . ? O10 H11 0.87(5) . ? N5 C001 1.347(3) . ? N5 C005 1.360(3) . ? O4 C016 1.413(3) . ? O4 C015 1.433(3) . ? O9 C009 1.418(3) . ? O9 H12 0.78(4) . ? N1 C014 1.370(3) . ? N1 C002 1.387(3) . ? N1 C021 1.497(3) . ? O5 C004 1.290(3) . ? O5 H5A 0.8400 . ? O3 C021 1.410(3) . ? O3 C020 1.440(3) . ? C001 C007 1.426(3) . ? C002 O2 1.240(3) . ? C003 C014 1.344(4) . ? C003 C008 1.417(4) . ? C003 H4 0.95(4) . ? C004 O6 1.239(3) . ? C004 C018 1.509(4) . ? N3 C008 1.327(3) . ? N3 H9 0.86(4) . ? N3 H8 0.88(4) . ? C005 N6 1.395(3) . ? C006 C007 1.343(4) . ? C006 N6 1.372(3) . ? C006 H6 0.93(3) . ? C007 H7 1.00(3) . ? C009 C020 1.523(4) . ? C009 H00A 0.9900 . ? C009 H00B 0.9900 . ? C010 C012 1.529(3) . ? C010 C022 1.529(3) . ? C010 H01A 0.9900 . ? C010 H01B 0.9900 . ? C011 C013 1.508(3) . ? C012 C018 1.526(4) . ? C012 H01C 0.9900 . ? C012 H01D 0.9900 . ? N6 C016 1.483(3) . ? C013 C022 1.529(3) . ? C013 H01E 0.9900 . ? C013 H01F 0.9900 . ? C014 H5 0.91(4) . ? C015 C023 1.506(4) . ? C015 H10 0.98(3) . ? C016 C017 1.523(4) . ? C016 H14 0.99(3) . ? C017 H01G 0.9900 . ? C017 H01H 0.9900 . ? C018 H01I 0.9900 . ? C018 H01J 0.9900 . ? C019 C021 1.526(3) . ? C019 H01K 0.9900 . ? C019 H01L 0.9900 . ? C020 H13 1.01(3) . ? C021 H3 1.03(3) . ? C022 H02A 0.9900 . ? C022 H02B 0.9900 . ? C023 H02C 0.9900 . ? C023 H02D 0.9900 . ? 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 C019 S1 C020 87.87(12) . . ? C017 S2 C015 86.35(12) . . ? C001 N4 H2 117(2) . . ? C001 N4 H1 121(2) . . ? H2 N4 H1 120(3) . . ? C011 O8 H8A 109.5 . . ? C008 N2 C002 121.0(2) . . ? C023 O10 H11 108(3) . . ? C001 N5 C005 120.8(2) . . ? C016 O4 C015 112.37(19) . . ? C009 O9 H12 106(3) . . ? C014 N1 C002 120.9(2) . . ? C014 N1 C021 121.4(2) . . ? C002 N1 C021 117.36(19) . . ? C004 O5 H5A 109.5 . . ? C021 O3 C020 114.08(18) . . ? N4 C001 N5 118.8(2) . . ? N4 C001 C007 120.4(2) . . ? N5 C001 C007 120.8(2) . . ? O2 C002 N2 121.3(2) . . ? O2 C002 N1 120.3(2) . . ? N2 C002 N1 118.3(2) . . ? C014 C003 C008 118.6(2) . . ? C014 C003 H4 121(2) . . ? C008 C003 H4 120(2) . . ? O6 C004 O5 122.9(3) . . ? O6 C004 C018 121.7(2) . . ? O5 C004 C018 115.4(2) . . ? C008 N3 H9 119(3) . . ? C008 N3 H8 120(2) . . ? H9 N3 H8 121(3) . . ? O1 C005 N5 122.3(2) . . ? O1 C005 N6 119.2(2) . . ? N5 C005 N6 118.5(2) . . ? C007 C006 N6 120.8(2) . . ? C007 C006 H6 123.3(18) . . ? N6 C006 H6 115.8(17) . . ? C006 C007 C001 118.0(2) . . ? C006 C007 H7 119.8(16) . . ? C001 C007 H7 121.8(16) . . ? N3 C008 N2 118.6(2) . . ? N3 C008 C003 121.3(2) . . ? N2 C008 C003 120.1(2) . . ? O9 C009 C020 114.1(2) . . ? O9 C009 H00A 108.7 . . ? C020 C009 H00A 108.7 . . ? O9 C009 H00B 108.7 . . ? C020 C009 H00B 108.7 . . ? H00A C009 H00B 107.6 . . ? C012 C010 C022 110.9(2) . . ? C012 C010 H01A 109.5 . . ? C022 C010 H01A 109.5 . . ? C012 C010 H01B 109.5 . . ? C022 C010 H01B 109.5 . . ? H01A C010 H01B 108.0 . . ? O7 C011 O8 123.1(2) . . ? O7 C011 C013 123.8(2) . . ? O8 C011 C013 113.1(2) . . ? C018 C012 C010 113.1(2) . . ? C018 C012 H01C 109.0 . . ? C010 C012 H01C 109.0 . . ? C018 C012 H01D 109.0 . . ? C010 C012 H01D 109.0 . . ? H01C C012 H01D 107.8 . . ? C006 N6 C005 120.8(2) . . ? C006 N6 C016 122.3(2) . . ? C005 N6 C016 116.88(18) . . ? C011 C013 C022 113.9(2) . . ? C011 C013 H01E 108.8 . . ? C022 C013 H01E 108.8 . . ? C011 C013 H01F 108.8 . . ? C022 C013 H01F 108.8 . . ? H01E C013 H01F 107.7 . . ? C003 C014 N1 121.1(2) . . ? C003 C014 H5 121.6(19) . . ? N1 C014 H5 117.4(19) . . ? O4 C015 C023 110.1(2) . . ? O4 C015 S2 106.15(16) . . ? C023 C015 S2 112.85(19) . . ? O4 C015 H10 110.4(17) . . ? C023 C015 H10 110.0(17) . . ? S2 C015 H10 107.3(17) . . ? O4 C016 N6 108.21(18) . . ? O4 C016 C017 109.8(2) . . ? N6 C016 C017 111.6(2) . . ? O4 C016 H14 105.3(17) . . ? N6 C016 H14 104.3(15) . . ? C017 C016 H14 117.1(17) . . ? C016 C017 S2 104.05(17) . . ? C016 C017 H01G 110.9 . . ? S2 C017 H01G 110.9 . . ? C016 C017 H01H 110.9 . . ? S2 C017 H01H 110.9 . . ? H01G C017 H01H 109.0 . . ? C004 C018 C012 109.3(2) . . ? C004 C018 H01I 109.8 . . ? C012 C018 H01I 109.8 . . ? C004 C018 H01J 109.8 . . ? C012 C018 H01J 109.8 . . ? H01I C018 H01J 108.3 . . ? C021 C019 S1 104.05(16) . . ? C021 C019 H01K 110.9 . . ? S1 C019 H01K 110.9 . . ? C021 C019 H01L 110.9 . . ? S1 C019 H01L 110.9 . . ? H01K C019 H01L 109.0 . . ? O3 C020 C009 111.0(2) . . ? O3 C020 S1 106.97(16) . . ? C009 C020 S1 112.87(19) . . ? O3 C020 H13 108.8(18) . . ? C009 C020 H13 110.7(17) . . ? S1 C020 H13 106.3(17) . . ? O3 C021 N1 108.67(17) . . ? O3 C021 C019 108.8(2) . . ? N1 C021 C019 112.4(2) . . ? O3 C021 H3 111.2(16) . . ? N1 C021 H3 104.8(16) . . ? C019 C021 H3 110.9(15) . . ? C013 C022 C010 114.9(2) . . ? C013 C022 H02A 108.5 . . ? C010 C022 H02A 108.5 . . ? C013 C022 H02B 108.5 . . ? C010 C022 H02B 108.5 . . ? H02A C022 H02B 107.5 . . ? O10 C023 C015 112.5(2) . . ? O10 C023 H02C 109.1 . . ? C015 C023 H02C 109.1 . . ? O10 C023 H02D 109.1 . . ? C015 C023 H02D 109.1 . . ? H02C C023 H02D 107.8 . . ? 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 C005 N5 C001 N4 177.6(2) . . . . ? C005 N5 C001 C007 -3.2(3) . . . . ? C008 N2 C002 O2 -177.8(2) . . . . ? C008 N2 C002 N1 1.1(3) . . . . ? C014 N1 C002 O2 178.1(2) . . . . ? C021 N1 C002 O2 4.7(3) . . . . ? C014 N1 C002 N2 -0.8(3) . . . . ? C021 N1 C002 N2 -174.2(2) . . . . ? C001 N5 C005 O1 179.0(2) . . . . ? C001 N5 C005 N6 -1.4(3) . . . . ? N6 C006 C007 C001 -1.9(4) . . . . ? N4 C001 C007 C006 -175.9(2) . . . . ? N5 C001 C007 C006 4.9(4) . . . . ? C002 N2 C008 N3 177.7(2) . . . . ? C002 N2 C008 C003 -0.9(3) . . . . ? C014 C003 C008 N3 -178.2(2) . . . . ? C014 C003 C008 N2 0.3(4) . . . . ? C022 C010 C012 C018 179.7(2) . . . . ? C007 C006 N6 C005 -2.8(4) . . . . ? C007 C006 N6 C016 177.1(2) . . . . ? O1 C005 N6 C006 -175.9(2) . . . . ? N5 C005 N6 C006 4.5(3) . . . . ? O1 C005 N6 C016 4.2(3) . . . . ? N5 C005 N6 C016 -175.4(2) . . . . ? O7 C011 C013 C022 6.8(3) . . . . ? O8 C011 C013 C022 -176.0(2) . . . . ? C008 C003 C014 N1 0.0(4) . . . . ? C002 N1 C014 C003 0.3(4) . . . . ? C021 N1 C014 C003 173.4(2) . . . . ? C016 O4 C015 C023 -152.1(2) . . . . ? C016 O4 C015 S2 -29.7(2) . . . . ? C017 S2 C015 O4 40.56(17) . . . . ? C017 S2 C015 C023 161.2(2) . . . . ? C015 O4 C016 N6 121.2(2) . . . . ? C015 O4 C016 C017 -0.8(3) . . . . ? C006 N6 C016 O4 -21.5(3) . . . . ? C005 N6 C016 O4 158.4(2) . . . . ? C006 N6 C016 C017 99.5(3) . . . . ? C005 N6 C016 C017 -80.7(3) . . . . ? O4 C016 C017 S2 30.8(2) . . . . ? N6 C016 C017 S2 -89.2(2) . . . . ? C015 S2 C017 C016 -39.74(17) . . . . ? O6 C004 C018 C012 92.5(3) . . . . ? O5 C004 C018 C012 -85.1(3) . . . . ? C010 C012 C018 C004 169.6(2) . . . . ? C020 S1 C019 C021 -38.77(17) . . . . ? C021 O3 C020 C009 -142.5(2) . . . . ? C021 O3 C020 S1 -18.9(2) . . . . ? O9 C009 C020 O3 60.9(3) . . . . ? O9 C009 C020 S1 -59.2(3) . . . . ? C019 S1 C020 O3 33.91(17) . . . . ? C019 S1 C020 C009 156.30(19) . . . . ? C020 O3 C021 N1 112.0(2) . . . . ? C020 O3 C021 C019 -10.7(3) . . . . ? C014 N1 C021 O3 -10.7(3) . . . . ? C002 N1 C021 O3 162.7(2) . . . . ? C014 N1 C021 C019 109.8(3) . . . . ? C002 N1 C021 C019 -76.8(3) . . . . ? S1 C019 C021 O3 35.2(2) . . . . ? S1 C019 C021 N1 -85.2(2) . . . . ? C011 C013 C022 C010 76.1(3) . . . . ? C012 C010 C022 C013 -179.9(2) . . . . ? O4 C015 C023 O10 -61.0(3) . . . . ? S2 C015 C023 O10 -179.41(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.291 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.092 _database_code_depnum_ccdc_archive 'CCDC 965969'