Electronic SUpplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2007 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Andrew Burrows' _publ_contact_author_address ; Department of Chemistry University of Bath Claverton Down Bath BA2 7AY UNITED KINGDOM ; _publ_contact_author_email A.D.BURROWS@BATH.AC.UK _publ_section_title ; Isomerism and interpenetration in hydrogen-bonded network structures ; loop_ _publ_author_name 'Andrew Burrows' 'Nichola J. Burke' 'Mary Mahon' 'John E. Warren' data_compound_1_bath47 _database_code_depnum_ccdc_archive 'CCDC 654143' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H13 N3 O3 S' _chemical_formula_weight 231.27 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.8517(7) _cell_length_b 10.8528(7) _cell_length_c 9.1258(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.267(2) _cell_angle_gamma 90.00 _cell_volume 1093.86(11) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 2666 _cell_measurement_theta_min 2.045 _cell_measurement_theta_max 28.69 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.04 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.404 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.288 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min 0.9886 _exptl_absorpt_correction_T_max 0.9914 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.68670 _diffrn_radiation_type Synchrotron _diffrn_radiation_source 'Daresbury SRS station 9.8' _diffrn_radiation_monochromator 'Silicon 111' _diffrn_measurement_device_type 'Bruker SMART CCD diffractometer' _diffrn_measurement_method '\w rotation with narrow frames' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7222 _diffrn_reflns_av_R_equivalents 0.0399 _diffrn_reflns_av_sigmaI/netI 0.0504 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.78 _diffrn_reflns_theta_max 29.25 _reflns_number_total 3028 _reflns_number_gt 2415 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'local programs' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0589P)^2^+0.3094P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3028 _refine_ls_number_parameters 138 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0588 _refine_ls_R_factor_gt 0.0436 _refine_ls_wR_factor_ref 0.1158 _refine_ls_wR_factor_gt 0.1078 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 0.22908(3) 0.08028(4) 0.03358(5) 0.01814(12) Uani 1 1 d . . . O1 O 0.16474(11) -0.02875(11) -0.04914(15) 0.0230(3) Uani 1 1 d . . . O2 O 0.16055(11) 0.19338(11) -0.02834(16) 0.0261(3) Uani 1 1 d . . . O3 O 0.26850(11) 0.06920(12) 0.20367(15) 0.0256(3) Uani 1 1 d . . . N1 N -0.07100(14) 0.01985(15) -0.29003(18) 0.0259(3) Uani 1 1 d . . . H1B H -0.1348 -0.0274 -0.3065 0.031 Uiso 1 1 calc R . . H1A H -0.0088 0.0147 -0.2008 0.031 Uiso 1 1 calc R . . N2 N 0.02993(14) 0.16858(15) -0.37136(19) 0.0279(3) Uani 1 1 d . . . H2B H 0.0341 0.2213 -0.4425 0.033 Uiso 1 1 calc R . . H2A H 0.0909 0.1616 -0.2811 0.033 Uiso 1 1 calc R . . N3 N -0.16199(14) 0.10798(14) -0.53585(18) 0.0252(3) Uani 1 1 d . . . C1 C -0.06861(16) 0.09928(15) -0.4004(2) 0.0212(3) Uani 1 1 d . . . C2 C -0.1631(2) 0.20245(17) -0.6514(2) 0.0320(4) Uani 1 1 d . . . H2C H -0.1010 0.1832 -0.6954 0.048 Uiso 1 1 calc R . . H2D H -0.1462 0.2832 -0.5999 0.048 Uiso 1 1 calc R . . H2E H -0.2429 0.2040 -0.7360 0.048 Uiso 1 1 calc R . . C3 C -0.26424(18) 0.0226(2) -0.5719(2) 0.0330(4) Uani 1 1 d . . . H3A H -0.3153 0.0467 -0.5129 0.050 Uiso 1 1 calc R . . H3B H -0.2338 -0.0612 -0.5420 0.050 Uiso 1 1 calc R . . H3C H -0.3120 0.0252 -0.6848 0.050 Uiso 1 1 calc R . . C4 C 0.36294(14) 0.09217(15) -0.01222(19) 0.0175(3) Uani 1 1 d . . . C5 C 0.37873(15) 0.19687(16) -0.0861(2) 0.0228(3) Uani 1 1 d . . . H5 H 0.3213 0.2618 -0.1069 0.027 Uiso 1 1 calc R . . C6 C 0.48036(16) 0.20870(16) -0.1317(2) 0.0254(4) Uani 1 1 d . . . H6 H 0.4903 0.2813 -0.1839 0.030 Uiso 1 1 calc R . . C7 C 0.56416(15) 0.11664(16) -0.1012(2) 0.0222(3) Uani 1 1 d . . . H7 H 0.6320 0.1260 -0.1323 0.027 Uiso 1 1 calc R . . C8 C 0.55135(13) 0.00671(15) -0.02358(19) 0.0167(3) 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 S1 0.01654(19) 0.0193(2) 0.0211(2) -0.00276(15) 0.00979(15) -0.00064(14) O1 0.0190(6) 0.0218(6) 0.0264(6) -0.0051(5) 0.0062(5) -0.0027(5) O2 0.0233(6) 0.0236(6) 0.0356(7) -0.0011(5) 0.0157(5) 0.0051(5) O3 0.0254(6) 0.0344(7) 0.0204(6) -0.0052(5) 0.0124(5) -0.0065(5) N1 0.0208(7) 0.0327(8) 0.0235(8) 0.0053(6) 0.0073(6) -0.0066(6) N2 0.0273(8) 0.0302(8) 0.0291(8) 0.0045(6) 0.0136(7) -0.0056(6) N3 0.0305(8) 0.0220(7) 0.0225(7) 0.0001(6) 0.0088(6) -0.0005(6) C1 0.0242(8) 0.0208(8) 0.0232(8) -0.0023(6) 0.0140(7) 0.0005(6) C2 0.0471(12) 0.0247(9) 0.0243(9) 0.0037(7) 0.0132(9) 0.0036(8) C3 0.0288(9) 0.0354(11) 0.0295(10) -0.0010(8) 0.0042(8) -0.0046(8) C4 0.0162(7) 0.0190(7) 0.0188(7) -0.0004(6) 0.0082(6) 0.0005(6) C5 0.0210(8) 0.0203(8) 0.0284(9) 0.0045(7) 0.0108(7) 0.0041(6) C6 0.0260(8) 0.0213(8) 0.0327(10) 0.0113(7) 0.0152(8) 0.0022(7) C7 0.0207(7) 0.0235(8) 0.0263(9) 0.0076(7) 0.0131(7) 0.0022(6) C8 0.0166(7) 0.0186(7) 0.0164(7) 0.0022(6) 0.0079(6) 0.0007(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O3 1.4546(13) . ? S1 O1 1.4609(12) . ? S1 O2 1.4671(13) . ? S1 C4 1.7859(15) . ? N1 C1 1.334(2) . ? N2 C1 1.332(2) . ? N3 C1 1.330(2) . ? N3 C3 1.465(2) . ? N3 C2 1.467(2) . ? C4 C5 1.369(2) . ? C4 C8 1.432(2) 3_655 ? C5 C6 1.415(2) . ? C6 C7 1.364(2) . ? C7 C8 1.424(2) . ? C8 C4 1.432(2) 3_655 ? C8 C8 1.438(3) 3_655 ? 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 O3 S1 O1 112.95(8) . . ? O3 S1 O2 113.50(8) . . ? O1 S1 O2 111.49(8) . . ? O3 S1 C4 106.68(7) . . ? O1 S1 C4 106.20(7) . . ? O2 S1 C4 105.32(7) . . ? C1 N3 C3 120.36(15) . . ? C1 N3 C2 120.33(16) . . ? C3 N3 C2 119.31(16) . . ? N3 C1 N2 121.25(16) . . ? N3 C1 N1 120.61(16) . . ? N2 C1 N1 118.14(16) . . ? C5 C4 C8 121.49(14) . 3_655 ? C5 C4 S1 117.86(12) . . ? C8 C4 S1 120.63(11) 3_655 . ? C4 C5 C6 120.21(15) . . ? C7 C6 C5 120.53(15) . . ? C6 C7 C8 120.92(15) . . ? C7 C8 C4 123.15(13) . 3_655 ? C7 C8 C8 119.24(18) . 3_655 ? C4 C8 C8 117.60(17) 3_655 3_655 ? _diffrn_measured_fraction_theta_max 0.919 _diffrn_reflns_theta_full 29.25 _diffrn_measured_fraction_theta_full 0.919 _refine_diff_density_max 0.455 _refine_diff_density_min -0.329 _refine_diff_density_rms 0.069 #===END data_compound_2_h02njb3 _database_code_depnum_ccdc_archive 'CCDC 654144' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H13 N3 O3 S' _chemical_formula_weight 231.27 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 P21/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.2870(6) _cell_length_b 19.4830(12) _cell_length_c 14.679(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.837(5) _cell_angle_gamma 90.00 _cell_volume 2076.6(4) _cell_formula_units_Z 8 _cell_measurement_temperature 170(2) _cell_measurement_reflns_used 18347 _cell_measurement_theta_min 3.780 _cell_measurement_theta_max 27.440 _exptl_crystal_description Needle _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 976 _exptl_absorpt_coefficient_mu 0.304 _exptl_absorpt_correction_type Multi-Scan _exptl_absorpt_correction_T_min 0.87 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ; ? ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 170(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 '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 36141 _diffrn_reflns_av_R_equivalents 0.1151 _diffrn_reflns_av_sigmaI/netI 0.0877 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.78 _diffrn_reflns_theta_max 27.44 _reflns_number_total 4724 _reflns_number_gt 2886 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Bruker AXS BV, 1997-2004)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'Denzo & Scalepack (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEX (P.McArdle, 1995)' _computing_publication_material 'SHELXL-97/2 (Sheldrick,1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0659P)^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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0052(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4724 _refine_ls_number_parameters 276 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1136 _refine_ls_R_factor_gt 0.0517 _refine_ls_wR_factor_ref 0.1236 _refine_ls_wR_factor_gt 0.1091 _refine_ls_goodness_of_fit_ref 0.994 _refine_ls_restrained_S_all 0.994 _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 1.13376(8) 0.21276(3) 0.00205(4) 0.02322(18) Uani 1 1 d . . . S2 S -0.57491(9) 0.02083(4) 0.28352(4) 0.0299(2) Uani 1 1 d . . . O1 O 1.0868(3) 0.24656(9) -0.08449(11) 0.0349(5) Uani 1 1 d . . . O2 O 1.3294(2) 0.21498(9) 0.02838(12) 0.0316(4) Uani 1 1 d . . . O3 O 1.0251(2) 0.23730(9) 0.07378(11) 0.0340(5) Uani 1 1 d . . . O4 O -0.7157(3) 0.07336(12) 0.28181(12) 0.0516(6) Uani 1 1 d . . . O5 O -0.3980(3) 0.04564(12) 0.32226(12) 0.0495(6) Uani 1 1 d . . . O6 O -0.6279(3) -0.04209(11) 0.32612(12) 0.0502(6) Uani 1 1 d . . . N1 N 0.8836(3) 0.23178(12) 0.24844(14) 0.0382(6) Uani 1 1 d . . . H1A H 0.9187 0.2282 0.3071 0.046 Uiso 1 1 calc R . . H1B H 0.9658 0.2298 0.2079 0.046 Uiso 1 1 calc R . . N2 N 0.6602(3) 0.24642(13) 0.13152(14) 0.0413(6) Uani 1 1 d . . . H2A H 0.5444 0.2528 0.1111 0.050 Uiso 1 1 calc R . . H2B H 0.7459 0.2442 0.0928 0.050 Uiso 1 1 calc R . . N3 N 0.5801(3) 0.24316(11) 0.28052(13) 0.0295(5) Uani 1 1 d . . . N4 N -0.0244(3) 0.08088(11) 0.39078(13) 0.0299(5) Uani 1 1 d . . . H4B H 0.0871 0.0842 0.3724 0.036 Uiso 1 1 calc R . . H4A H -0.1199 0.0762 0.3504 0.036 Uiso 1 1 calc R . . N5 N -0.2203(3) 0.07716(11) 0.50392(13) 0.0300(5) Uani 1 1 d . . . H5A H -0.3126 0.0721 0.4618 0.036 Uiso 1 1 calc R . . H5B H -0.2412 0.0784 0.5621 0.036 Uiso 1 1 calc R . . N6 N 0.0941(3) 0.09014(11) 0.54177(13) 0.0272(5) Uani 1 1 d . . . C1 C 0.7058(3) 0.24010(14) 0.22096(16) 0.0285(6) Uani 1 1 d . . . C2 C 0.6243(4) 0.22738(17) 0.37697(17) 0.0447(8) Uani 1 1 d . . . H2C H 0.6475 0.1780 0.3842 0.067 Uiso 1 1 calc R . . H2D H 0.5208 0.2405 0.4117 0.067 Uiso 1 1 calc R . . H2E H 0.7345 0.2530 0.3999 0.067 Uiso 1 1 calc R . . C3 C 0.3857(4) 0.25263(18) 0.24993(19) 0.0499(8) Uani 1 1 d . . . H3A H 0.3738 0.2879 0.2022 0.075 Uiso 1 1 calc R . . H3B H 0.3184 0.2671 0.3017 0.075 Uiso 1 1 calc R . . H3C H 0.3345 0.2093 0.2253 0.075 Uiso 1 1 calc R . . C4 C -0.0487(4) 0.08302(12) 0.47965(16) 0.0263(6) Uani 1 1 d . . . C5 C 0.2798(3) 0.10131(15) 0.51385(18) 0.0346(6) Uani 1 1 d . . . H5C H 0.3130 0.0634 0.4745 0.052 Uiso 1 1 calc R . . H5D H 0.3676 0.1033 0.5682 0.052 Uiso 1 1 calc R . . H5E H 0.2833 0.1447 0.4802 0.052 Uiso 1 1 calc R . . C6 C 0.0679(4) 0.09601(14) 0.63880(16) 0.0345(6) Uani 1 1 d . . . H6A H 0.0363 0.1435 0.6529 0.052 Uiso 1 1 calc R . . H6B H 0.1818 0.0830 0.6749 0.052 Uiso 1 1 calc R . . H6C H -0.0321 0.0655 0.6538 0.052 Uiso 1 1 calc R . . C12 C -0.5664(4) -0.08439(14) 0.04760(17) 0.0332(6) Uani 1 1 d . . . H12 H -0.5883 -0.1302 0.0275 0.040 Uiso 1 1 calc R . . C13 C -0.5817(3) -0.06745(15) 0.13645(17) 0.0330(6) Uani 1 1 d . . . H13 H -0.6160 -0.1016 0.1780 0.040 Uiso 1 1 calc R . . C14 C -0.5475(3) 0.00022(14) 0.16786(16) 0.0279(6) Uani 1 1 d . . . C15 C -0.4991(3) 0.05009(15) 0.10905(16) 0.0310(6) Uani 1 1 d . . . H15 H -0.4767 0.0955 0.1306 0.037 Uiso 1 1 calc R . . C16 C -0.4820(3) 0.03402(13) 0.01457(16) 0.0273(6) Uani 1 1 d . . . C17 C 1.0466(4) 0.02795(14) -0.11754(17) 0.0335(6) Uani 1 1 d . . . H17 H 1.0503 0.0088 -0.1769 0.040 Uiso 1 1 calc R . . C18 C 1.0841(3) 0.09634(14) -0.10322(16) 0.0302(6) Uani 1 1 d . . . H18 H 1.1143 0.1245 -0.1526 0.036 Uiso 1 1 calc R . . C19 C 1.0776(3) 0.12482(13) -0.01502(16) 0.0262(6) Uani 1 1 d . . . C20 C 1.0361(3) 0.08549(14) 0.05674(17) 0.0309(6) Uani 1 1 d . . . H20 H 1.0325 0.1056 0.1155 0.037 Uiso 1 1 calc R . . C21 C 0.9974(3) 0.01368(14) 0.04433(16) 0.0276(6) 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 S1 0.0177(3) 0.0310(4) 0.0208(3) 0.0004(3) 0.0010(2) -0.0012(3) S2 0.0228(4) 0.0490(5) 0.0181(3) -0.0007(3) 0.0032(2) -0.0004(3) O1 0.0386(11) 0.0395(12) 0.0254(10) 0.0052(8) -0.0048(8) -0.0013(9) O2 0.0174(9) 0.0378(11) 0.0387(10) -0.0009(8) -0.0023(7) -0.0025(8) O3 0.0315(11) 0.0381(11) 0.0341(10) -0.0047(8) 0.0136(8) -0.0029(8) O4 0.0462(13) 0.0806(17) 0.0289(11) -0.0042(10) 0.0095(9) 0.0272(11) O5 0.0310(12) 0.0893(17) 0.0278(10) -0.0143(10) 0.0007(8) -0.0165(11) O6 0.0623(15) 0.0614(15) 0.0287(11) 0.0071(9) 0.0141(9) -0.0129(11) N1 0.0195(12) 0.0729(18) 0.0223(11) -0.0001(11) 0.0011(9) 0.0031(11) N2 0.0201(12) 0.0817(19) 0.0217(12) -0.0009(11) -0.0009(9) 0.0003(12) N3 0.0190(11) 0.0468(15) 0.0229(11) -0.0004(9) 0.0034(9) 0.0019(10) N4 0.0265(12) 0.0417(14) 0.0215(11) 0.0000(9) 0.0027(9) 0.0002(10) N5 0.0244(12) 0.0441(15) 0.0215(11) -0.0002(9) 0.0023(9) -0.0002(10) N6 0.0242(12) 0.0341(13) 0.0229(11) -0.0024(9) 0.0007(9) 0.0008(10) C1 0.0229(14) 0.0394(17) 0.0231(13) -0.0018(11) 0.0016(10) -0.0037(12) C2 0.0413(18) 0.068(2) 0.0256(15) 0.0077(13) 0.0077(12) 0.0116(15) C3 0.0248(16) 0.088(3) 0.0371(17) -0.0031(16) 0.0043(12) 0.0064(16) C4 0.0295(15) 0.0220(14) 0.0277(14) 0.0014(10) 0.0033(11) 0.0017(11) C5 0.0248(14) 0.0405(17) 0.0386(16) -0.0010(12) 0.0024(11) -0.0029(12) C6 0.0397(16) 0.0405(17) 0.0225(14) -0.0016(11) -0.0016(11) 0.0002(13) C12 0.0300(15) 0.0375(17) 0.0324(15) 0.0006(12) 0.0049(11) 0.0017(12) C13 0.0278(15) 0.0440(18) 0.0276(15) 0.0008(12) 0.0043(11) 0.0029(13) C14 0.0181(13) 0.0436(18) 0.0219(13) 0.0016(11) 0.0010(10) 0.0062(11) C15 0.0260(14) 0.0404(17) 0.0276(14) -0.0003(12) 0.0070(11) 0.0039(12) C16 0.0184(13) 0.0345(15) 0.0286(14) 0.0022(11) -0.0007(10) 0.0046(11) C17 0.0331(16) 0.0437(18) 0.0236(13) -0.0026(12) 0.0022(11) -0.0022(13) C18 0.0283(15) 0.0369(17) 0.0253(14) 0.0000(11) 0.0020(11) -0.0017(12) C19 0.0161(12) 0.0340(16) 0.0278(14) 0.0024(11) -0.0015(10) -0.0007(11) C20 0.0204(14) 0.0411(18) 0.0310(15) -0.0036(12) 0.0004(11) -0.0014(12) C21 0.0174(13) 0.0400(17) 0.0251(12) 0.0009(11) -0.0003(10) 0.0006(11) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 O2 1.4460(17) . ? S1 O1 1.4460(17) . ? S1 O3 1.4510(17) . ? S1 C19 1.774(3) . ? S2 O6 1.444(2) . ? S2 O5 1.4476(19) . ? S2 O4 1.448(2) . ? S2 C14 1.772(2) . ? N1 C1 1.335(3) . ? N2 C1 1.332(3) . ? N3 C1 1.320(3) . ? N3 C2 1.458(3) . ? N3 C3 1.461(3) . ? N4 C4 1.332(3) . ? N5 C4 1.334(3) . ? N6 C4 1.332(3) . ? N6 C6 1.457(3) . ? N6 C5 1.463(3) . ? C12 C13 1.359(3) . ? C12 C16 1.405(4) 3_455 ? C13 C14 1.412(4) . ? C14 C15 1.366(4) . ? C15 C16 1.437(3) . ? C16 C12 1.405(4) 3_455 ? C16 C16 1.411(5) 3_455 ? C17 C18 1.373(4) . ? C17 C21 1.405(4) 3_755 ? C18 C19 1.413(3) . ? C19 C20 1.357(3) . ? C20 C21 1.436(4) . ? C21 C17 1.405(4) 3_755 ? C21 C21 1.410(5) 3_755 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O1 112.09(11) . . ? O2 S1 O3 112.48(10) . . ? O1 S1 O3 112.61(11) . . ? O2 S1 C19 106.08(11) . . ? O1 S1 C19 106.32(11) . . ? O3 S1 C19 106.68(11) . . ? O6 S2 O5 112.04(13) . . ? O6 S2 O4 113.13(13) . . ? O5 S2 O4 112.16(13) . . ? O6 S2 C14 106.16(12) . . ? O5 S2 C14 106.47(11) . . ? O4 S2 C14 106.29(11) . . ? C1 N3 C2 121.6(2) . . ? C1 N3 C3 120.7(2) . . ? C2 N3 C3 117.0(2) . . ? C4 N6 C6 121.2(2) . . ? C4 N6 C5 120.8(2) . . ? C6 N6 C5 117.6(2) . . ? N3 C1 N2 121.3(2) . . ? N3 C1 N1 121.1(2) . . ? N2 C1 N1 117.6(2) . . ? N4 C4 N6 120.9(2) . . ? N4 C4 N5 117.7(2) . . ? N6 C4 N5 121.5(2) . . ? C13 C12 C16 120.0(3) . 3_455 ? C12 C13 C14 120.9(2) . . ? C15 C14 C13 120.4(2) . . ? C15 C14 S2 120.0(2) . . ? C13 C14 S2 119.56(19) . . ? C14 C15 C16 120.2(3) . . ? C12 C16 C16 120.6(3) 3_455 3_455 ? C12 C16 C15 121.4(2) 3_455 . ? C16 C16 C15 117.9(3) 3_455 . ? C18 C17 C21 119.9(2) . 3_755 ? C17 C18 C19 120.0(2) . . ? C20 C19 C18 121.1(2) . . ? C20 C19 S1 119.96(19) . . ? C18 C19 S1 118.91(19) . . ? C19 C20 C21 120.4(2) . . ? C17 C21 C21 120.9(3) 3_755 3_755 ? C17 C21 C20 121.4(2) 3_755 . ? C21 C21 C20 117.7(3) 3_755 . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.44 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.660 _refine_diff_density_min -0.521 _refine_diff_density_rms 0.126