# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Spencer Williams' _publ_contact_author_address ; School of Chemistry University of Melbourne Bio21 Institute 30 Flemington Road Parkville 3010 AUSTRALIA ; _publ_contact_author_email SJWILL@UNIMELB.EDU.AU _publ_section_title ; Ground state structures of sulfate monoesters and sulfamates reveal similar reaction coordinates for sulfuryl and sulfamyl transfer ; loop_ _publ_author_name 'Spencer Williams' 'Emma Denehy' 'Jonathan M. White' # Attachment 'CMPD1.cif' data_jmwsw20 _database_code_depnum_ccdc_archive 'CCDC 285416' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'potassium 4-methoxyphenyl sulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H7 K O5 S' _chemical_formula_weight 242.29 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/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 7.1098(4) _cell_length_b 38.923(2) _cell_length_c 7.1463(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.3540(10) _cell_angle_gamma 90.00 _cell_volume 1974.2(2) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 6470 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 27.45 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.630 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 992 _exptl_absorpt_coefficient_mu 0.741 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12205 _diffrn_reflns_av_R_equivalents 0.0276 _diffrn_reflns_av_sigmaI/netI 0.0317 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -50 _diffrn_reflns_limit_k_max 45 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.09 _diffrn_reflns_theta_max 27.52 _reflns_number_total 4444 _reflns_number_gt 4040 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'WinGX SHELXTL' _computing_structure_refinement 'WinGX SHELXTL' _computing_molecular_graphics 'WinGX Ortep3' _computing_publication_material 'WinGX SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0397P)^2^+0.6599P] 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 SHELXL _refine_ls_extinction_coef 0.0048(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4444 _refine_ls_number_parameters 256 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0806 _refine_ls_wR_factor_gt 0.0784 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 K1 K 0.12029(5) 0.022937(10) 0.83879(5) 0.01661(10) Uani 1 1 d . . . K2 K 0.49160(5) 0.047063(10) 0.35643(5) 0.01680(10) Uani 1 1 d . . . S4 S 0.57876(6) 0.046386(11) 0.85399(6) 0.01374(11) Uani 1 1 d . . . S3 S 0.01888(6) 0.052539(11) 0.37319(6) 0.01441(11) Uani 1 1 d . . . C5 C 0.7965(3) 0.11995(5) 0.8585(3) 0.0233(4) Uani 1 1 d . . . H5 H 0.8809 0.1031 0.9101 0.028 Uiso 1 1 calc R . . O1 O 0.7356(3) 0.21403(4) 0.8302(2) 0.0403(4) Uani 1 1 d . . . C1 C 0.6380(3) 0.11028(5) 0.7514(2) 0.0176(4) Uani 1 1 d . . . C2 C 0.5113(3) 0.13433(5) 0.6780(3) 0.0245(4) Uani 1 1 d . . . H2 H 0.4001 0.1273 0.6083 0.029 Uiso 1 1 calc R . . C3 C 0.5486(3) 0.16893(5) 0.7074(3) 0.0303(5) Uani 1 1 d . . . H3 H 0.4638 0.1858 0.6558 0.036 Uiso 1 1 calc R . . C4 C 0.7098(3) 0.17903(5) 0.8121(3) 0.0269(5) Uani 1 1 d . . . C6 C 0.8999(5) 0.22538(6) 0.9353(4) 0.0556(8) Uani 1 1 d . . . H6A H 0.8997 0.2162 1.0631 0.083 Uiso 1 1 calc R . . H6B H 0.9012 0.2505 0.9398 0.083 Uiso 1 1 calc R . . H6C H 1.0121 0.2172 0.8756 0.083 Uiso 1 1 calc R . . O9 O 0.49913(18) 0.01926(3) 0.73587(17) 0.0174(3) Uani 1 1 d . . . O2 O 0.60646(19) 0.07590(3) 0.69721(17) 0.0179(3) Uani 1 1 d . . . O5 O -0.14009(18) 0.03180(3) 0.42019(18) 0.0199(3) Uani 1 1 d . . . O8 O 0.44833(18) 0.06052(3) 0.98126(17) 0.0201(3) Uani 1 1 d . . . O6 O 0.11556(18) 0.03941(3) 0.21489(17) 0.0187(3) Uani 1 1 d . . . O4 O -0.08233(18) 0.08807(3) 0.30403(18) 0.0197(3) Uani 1 1 d . . . O7 O 0.76215(18) 0.03887(3) 0.94057(19) 0.0213(3) Uani 1 1 d . . . O3 O 0.3134(2) 0.21065(4) 0.3088(2) 0.0398(4) Uani 1 1 d . . . C7 C 0.0295(3) 0.11791(5) 0.3034(3) 0.0189(4) Uani 1 1 d . . . C12 C 0.1828(3) 0.12080(5) 0.1945(3) 0.0207(4) Uani 1 1 d . . . H12 H 0.2200 0.1019 0.1214 0.025 Uiso 1 1 calc R . . C8 C -0.0261(3) 0.14508(5) 0.4112(3) 0.0257(4) Uani 1 1 d . . . H8 H -0.1315 0.1428 0.4860 0.031 Uiso 1 1 calc R . . C11 C 0.2830(3) 0.15167(5) 0.1922(3) 0.0249(4) Uani 1 1 d . . . H11 H 0.3887 0.1539 0.1177 0.030 Uiso 1 1 calc R . . C9 C 0.0728(3) 0.17572(5) 0.4095(3) 0.0303(5) Uani 1 1 d . . . H9 H 0.0353 0.1945 0.4837 0.036 Uiso 1 1 calc R . . C10 C 0.2266(3) 0.17916(5) 0.2999(3) 0.0274(5) Uani 1 1 d . . . C13 C 0.4704(4) 0.21537(7) 0.1945(5) 0.0571(8) Uani 1 1 d . . . H13A H 0.5677 0.1983 0.2286 0.086 Uiso 1 1 calc R . . H13B H 0.5222 0.2385 0.2146 0.086 Uiso 1 1 calc R . . H13C H 0.4286 0.2126 0.0623 0.086 Uiso 1 1 calc R . . C14 C 0.8321(3) 0.15474(5) 0.8906(3) 0.0267(5) Uani 1 1 d . . . H14 H 0.9399 0.1617 0.9659 0.032 Uiso 1 1 calc R . . O10 O 0.14737(18) 0.06186(3) 0.52966(17) 0.0188(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 K1 0.0156(2) 0.0180(2) 0.0166(2) 0.00018(14) 0.00294(14) -0.00127(14) K2 0.0151(2) 0.0194(2) 0.01563(19) -0.00212(14) -0.00091(14) 0.00173(14) S4 0.0129(2) 0.0146(2) 0.0137(2) 0.00022(15) 0.00066(16) -0.00042(16) S3 0.0126(2) 0.0158(2) 0.0147(2) 0.00062(15) 0.00067(16) 0.00106(16) C5 0.0274(11) 0.0183(9) 0.0235(10) 0.0030(7) -0.0054(8) 0.0000(8) O1 0.0584(11) 0.0138(7) 0.0462(10) 0.0014(6) -0.0178(8) -0.0030(7) C1 0.0227(10) 0.0163(9) 0.0143(8) 0.0008(7) 0.0038(7) -0.0030(7) C2 0.0238(11) 0.0235(10) 0.0255(10) -0.0025(8) -0.0045(8) 0.0010(8) C3 0.0359(13) 0.0210(10) 0.0329(12) 0.0001(8) -0.0088(10) 0.0058(9) C4 0.0386(13) 0.0162(9) 0.0255(10) 0.0012(8) -0.0013(9) -0.0026(8) C6 0.080(2) 0.0196(11) 0.0632(18) 0.0024(11) -0.0301(16) -0.0168(12) O9 0.0175(7) 0.0157(6) 0.0188(6) -0.0018(5) 0.0005(5) -0.0014(5) O2 0.0251(7) 0.0145(6) 0.0140(6) -0.0001(5) 0.0013(5) -0.0045(5) O5 0.0155(7) 0.0197(7) 0.0249(7) 0.0011(5) 0.0041(5) -0.0011(5) O8 0.0208(7) 0.0214(7) 0.0188(7) -0.0011(5) 0.0071(5) 0.0008(5) O6 0.0158(7) 0.0223(7) 0.0182(7) -0.0017(5) 0.0026(5) 0.0010(5) O4 0.0157(7) 0.0178(6) 0.0252(7) 0.0023(5) -0.0020(5) 0.0017(5) O7 0.0168(7) 0.0212(7) 0.0251(7) 0.0005(5) -0.0041(5) 0.0009(5) O3 0.0515(11) 0.0203(8) 0.0477(10) -0.0028(7) 0.0047(8) -0.0106(7) C7 0.0207(10) 0.0166(9) 0.0189(9) 0.0030(7) -0.0040(7) 0.0013(7) C12 0.0207(10) 0.0193(9) 0.0220(9) -0.0002(7) -0.0006(7) 0.0016(7) C8 0.0305(12) 0.0237(10) 0.0236(10) 0.0025(8) 0.0076(8) 0.0044(8) C11 0.0246(11) 0.0230(10) 0.0270(11) 0.0026(8) 0.0009(8) -0.0015(8) C9 0.0474(14) 0.0172(10) 0.0265(11) -0.0028(8) 0.0048(10) 0.0048(9) C10 0.0343(12) 0.0176(10) 0.0296(11) 0.0024(8) -0.0026(9) -0.0020(8) C13 0.0592(19) 0.0309(14) 0.083(2) -0.0017(14) 0.0180(16) -0.0213(13) C14 0.0325(12) 0.0211(10) 0.0252(10) -0.0005(8) -0.0091(9) -0.0062(8) O10 0.0202(7) 0.0197(7) 0.0163(6) 0.0011(5) -0.0020(5) 0.0007(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K1 O10 2.6949(13) . ? K1 O7 2.7594(14) 1_455 ? K1 O6 2.7652(13) 1_556 ? K1 O5 2.8309(14) 3_556 ? K1 O9 2.8369(14) . ? K1 O8 2.8876(14) . ? K1 O6 2.9617(13) 3_556 ? K1 O7 2.9694(13) 3_657 ? K1 S4 3.3806(6) . ? K1 S3 3.4247(6) 3_556 ? K1 K1 3.4473(8) 3_557 ? K1 S3 3.5550(6) . ? K2 O9 2.6662(12) 3_656 ? K2 O5 2.6978(14) 1_655 ? K2 O8 2.7314(13) 1_554 ? K2 O2 2.7612(13) . ? K2 O6 2.8185(13) . ? K2 O10 2.8651(14) . ? K2 O9 2.9171(13) . ? K2 S3 3.3768(6) . ? K2 S4 3.5735(6) . ? K2 S4 3.6793(6) 1_554 ? K2 S3 3.7498(6) 1_655 ? K2 K1 4.1754(6) 3_656 ? S4 O7 1.4402(13) . ? S4 O8 1.4452(13) . ? S4 O9 1.4463(13) . ? S4 O2 1.6246(13) . ? S4 K2 3.6793(6) 1_556 ? S3 O5 1.4444(13) . ? S3 O10 1.4481(13) . ? S3 O6 1.4506(13) . ? S3 O4 1.6225(13) . ? S3 K1 3.4247(6) 3_556 ? S3 K2 3.7498(6) 1_455 ? C5 C1 1.377(3) . ? C5 C14 1.394(3) . ? C5 H5 0.9500 . ? O1 C4 1.380(2) . ? O1 C6 1.422(3) . ? C1 C2 1.382(3) . ? C1 O2 1.408(2) . ? C2 C3 1.386(3) . ? C2 H2 0.9500 . ? C3 C4 1.388(3) . ? C3 H3 0.9500 . ? C4 C14 1.381(3) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? O9 K2 2.6662(12) 3_656 ? O5 K2 2.6978(14) 1_455 ? O5 K1 2.8309(14) 3_556 ? O8 K2 2.7314(13) 1_556 ? O6 K1 2.7652(13) 1_554 ? O6 K1 2.9617(13) 3_556 ? O4 C7 1.408(2) . ? O7 K1 2.7594(14) 1_655 ? O7 K1 2.9694(13) 3_657 ? O3 C10 1.372(2) . ? O3 C13 1.433(3) . ? C7 C8 1.380(3) . ? C7 C12 1.380(3) . ? C12 C11 1.397(3) . ? C12 H12 0.9500 . ? C8 C9 1.385(3) . ? C8 H8 0.9500 . ? C11 C10 1.391(3) . ? C11 H11 0.9500 . ? C9 C10 1.388(3) . ? C9 H9 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 H14 0.9500 . ? 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 O10 K1 O7 101.60(4) . 1_455 ? O10 K1 O6 132.22(4) . 1_556 ? O7 K1 O6 68.15(4) 1_455 1_556 ? O10 K1 O5 83.02(4) . 3_556 ? O7 K1 O5 115.05(4) 1_455 3_556 ? O6 K1 O5 144.47(4) 1_556 3_556 ? O10 K1 O9 72.62(4) . . ? O7 K1 O9 169.88(4) 1_455 . ? O6 K1 O9 109.24(4) 1_556 . ? O5 K1 O9 73.04(4) 3_556 . ? O10 K1 O8 84.80(4) . . ? O7 K1 O8 122.14(4) 1_455 . ? O6 K1 O8 66.13(4) 1_556 . ? O5 K1 O8 122.80(4) 3_556 . ? O9 K1 O8 50.02(4) . . ? O10 K1 O6 114.93(4) . 3_556 ? O7 K1 O6 72.19(4) 1_455 3_556 ? O6 K1 O6 106.07(3) 1_556 3_556 ? O5 K1 O6 49.32(4) 3_556 3_556 ? O9 K1 O6 117.65(4) . 3_556 ? O8 K1 O6 154.19(4) . 3_556 ? O10 K1 O7 149.24(4) . 3_657 ? O7 K1 O7 106.11(3) 1_455 3_657 ? O6 K1 O7 71.99(4) 1_556 3_657 ? O5 K1 O7 73.40(4) 3_556 3_657 ? O9 K1 O7 81.65(4) . 3_657 ? O8 K1 O7 91.53(4) . 3_657 ? O6 K1 O7 62.91(4) 3_556 3_657 ? O10 K1 S4 76.09(3) . . ? O7 K1 S4 146.49(3) 1_455 . ? O6 K1 S4 88.44(3) 1_556 . ? O5 K1 S4 98.02(3) 3_556 . ? O9 K1 S4 24.99(3) . . ? O8 K1 S4 25.11(3) . . ? O6 K1 S4 139.72(3) 3_556 . ? O7 K1 S4 87.75(3) 3_657 . ? O10 K1 S3 98.76(3) . 3_556 ? O7 K1 S3 93.56(3) 1_455 3_556 ? O6 K1 S3 127.53(3) 1_556 3_556 ? O5 K1 S3 24.41(3) 3_556 3_556 ? O9 K1 S3 95.52(3) . 3_556 ? O8 K1 S3 142.85(3) . 3_556 ? O6 K1 S3 24.93(3) 3_556 3_556 ? O7 K1 S3 66.73(3) 3_657 3_556 ? S4 K1 S3 119.926(15) . 3_556 ? O10 K1 K1 154.30(3) . 3_557 ? O7 K1 K1 55.85(3) 1_455 3_557 ? O6 K1 K1 55.65(3) 1_556 3_557 ? O5 K1 K1 95.32(3) 3_556 3_557 ? O9 K1 K1 131.52(3) . 3_557 ? O8 K1 K1 116.67(3) . 3_557 ? O6 K1 K1 50.43(3) 3_556 3_557 ? O7 K1 K1 50.27(3) 3_657 3_557 ? S4 K1 K1 129.315(19) . 3_557 ? S3 K1 K1 73.114(15) 3_556 3_557 ? O10 K1 S3 21.69(3) . . ? O7 K1 S3 91.95(3) 1_455 . ? O6 K1 S3 145.21(3) 1_556 . ? O5 K1 S3 69.34(3) 3_556 . ? O9 K1 S3 85.26(3) . . ? O8 K1 S3 106.33(3) . . ? O6 K1 S3 93.55(3) 3_556 . ? O7 K1 S3 142.65(3) 3_657 . ? S4 K1 S3 94.873(14) . . ? S3 K1 S3 80.007(14) 3_556 . ? K1 K1 S3 135.400(19) 3_557 . ? O9 K2 O5 77.92(4) 3_656 1_655 ? O9 K2 O8 86.89(4) 3_656 1_554 ? O5 K2 O8 105.10(4) 1_655 1_554 ? O9 K2 O2 126.97(4) 3_656 . ? O5 K2 O2 72.93(4) 1_655 . ? O8 K2 O2 142.97(4) 1_554 . ? O9 K2 O6 81.11(4) 3_656 . ? O5 K2 O6 158.18(4) 1_655 . ? O8 K2 O6 67.54(4) 1_554 . ? O2 K2 O6 125.79(4) . . ? O9 K2 O10 109.61(4) 3_656 . ? O5 K2 O10 144.74(4) 1_655 . ? O8 K2 O10 109.61(4) 1_554 . ? O2 K2 O10 75.71(4) . . ? O6 K2 O10 50.20(4) . . ? O9 K2 O9 82.61(4) 3_656 . ? O5 K2 O9 78.26(4) 1_655 . ? O8 K2 O9 168.08(4) 1_554 . ? O2 K2 O9 48.90(3) . . ? O6 K2 O9 105.06(4) . . ? O10 K2 O9 69.06(4) . . ? O9 K2 S3 96.25(3) 3_656 . ? O5 K2 S3 165.06(3) 1_655 . ? O8 K2 S3 88.14(3) 1_554 . ? O2 K2 S3 100.76(3) . . ? O6 K2 S3 25.06(3) . . ? O10 K2 S3 25.16(3) . . ? O9 K2 S3 87.40(3) . . ? O9 K2 S4 103.51(3) 3_656 . ? O5 K2 S4 73.75(3) 1_655 . ? O8 K2 S4 168.85(3) 1_554 . ? O2 K2 S4 25.88(3) . . ? O6 K2 S4 117.51(3) . . ? O10 K2 S4 71.00(3) . . ? O9 K2 S4 23.03(2) . . ? S3 K2 S4 94.600(14) . . ? O9 K2 S4 75.14(3) 3_656 1_554 ? O5 K2 S4 86.91(3) 1_655 1_554 ? O8 K2 S4 19.81(3) 1_554 1_554 ? O2 K2 S4 143.67(3) . 1_554 ? O6 K2 S4 81.92(3) . 1_554 ? O10 K2 S4 128.32(3) . 1_554 ? O9 K2 S4 155.44(3) . 1_554 ? S3 K2 S4 105.061(14) . 1_554 ? S4 K2 S4 160.334(18) . 1_554 ? O9 K2 S3 91.36(3) 3_656 1_655 ? O5 K2 S3 17.90(3) 1_655 1_655 ? O8 K2 S3 94.33(3) 1_554 1_655 ? O2 K2 S3 72.86(3) . 1_655 ? O6 K2 S3 160.57(3) . 1_655 ? O10 K2 S3 148.48(3) . 1_655 ? O9 K2 S3 91.57(3) . 1_655 ? S3 K2 S3 172.114(18) . 1_655 ? S4 K2 S3 81.594(12) . 1_655 ? S4 K2 S3 78.838(12) 1_554 1_655 ? O9 K2 K1 42.20(3) 3_656 3_656 ? O5 K2 K1 42.17(3) 1_655 3_656 ? O8 K2 K1 80.55(3) 1_554 3_656 ? O2 K2 K1 113.13(3) . 3_656 ? O6 K2 K1 116.27(3) . 3_656 ? O10 K2 K1 150.86(3) . 3_656 ? O9 K2 K1 95.28(3) . 3_656 ? S3 K2 K1 137.021(14) . 3_656 ? S4 K2 K1 104.368(12) . 3_656 ? S4 K2 K1 61.113(10) 1_554 3_656 ? S3 K2 K1 50.859(10) 1_655 3_656 ? O7 S4 O8 113.90(8) . . ? O7 S4 O9 114.59(8) . . ? O8 S4 O9 113.67(8) . . ? O7 S4 O2 107.26(8) . . ? O8 S4 O2 105.84(7) . . ? O9 S4 O2 99.95(7) . . ? O7 S4 K1 143.70(6) . . ? O8 S4 K1 57.99(5) . . ? O9 S4 K1 55.97(5) . . ? O2 S4 K1 108.92(5) . . ? O7 S4 K2 121.93(6) . . ? O8 S4 K2 122.90(6) . . ? O9 S4 K2 52.08(5) . . ? O2 S4 K2 47.90(4) . . ? K1 S4 K2 81.911(13) . . ? O7 S4 K2 77.41(6) . 1_556 ? O8 S4 K2 39.84(5) . 1_556 ? O9 S4 K2 119.49(6) . 1_556 ? O2 S4 K2 134.59(5) . 1_556 ? K1 S4 K2 79.406(12) . 1_556 ? K2 S4 K2 160.334(18) . 1_556 ? O5 S3 O10 115.30(8) . . ? O5 S3 O6 113.41(8) . . ? O10 S3 O6 112.59(8) . . ? O5 S3 O4 102.01(7) . . ? O10 S3 O4 105.68(7) . . ? O6 S3 O4 106.54(7) . . ? O5 S3 K2 140.08(6) . . ? O10 S3 K2 57.24(5) . . ? O6 S3 K2 55.40(5) . . ? O4 S3 K2 117.88(5) . . ? O5 S3 K1 54.10(5) . 3_556 ? O10 S3 K1 135.18(5) . 3_556 ? O6 S3 K1 59.38(5) . 3_556 ? O4 S3 K1 119.00(5) . 3_556 ? K2 S3 K1 101.104(15) . 3_556 ? O5 S3 K1 73.73(6) . . ? O10 S3 K1 43.47(5) . . ? O6 S3 K1 122.43(5) . . ? O4 S3 K1 128.56(5) . . ? K2 S3 K1 82.237(13) . . ? K1 S3 K1 99.993(14) 3_556 . ? O5 S3 K2 35.04(5) . 1_455 ? O10 S3 K2 128.55(6) . 1_455 ? O6 S3 K2 118.26(5) . 1_455 ? O4 S3 K2 67.29(5) . 1_455 ? K2 S3 K2 172.114(18) . 1_455 ? K1 S3 K2 71.015(12) 3_556 1_455 ? K1 S3 K2 99.155(13) . 1_455 ? C1 C5 C14 119.43(18) . . ? C1 C5 H5 120.3 . . ? C14 C5 H5 120.3 . . ? C4 O1 C6 117.19(18) . . ? C5 C1 C2 121.36(18) . . ? C5 C1 O2 121.66(17) . . ? C2 C1 O2 116.73(16) . . ? C1 C2 C3 119.07(18) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 120.10(19) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? O1 C4 C14 124.11(19) . . ? O1 C4 C3 115.53(18) . . ? C14 C4 C3 120.35(18) . . ? O1 C6 H6A 109.5 . . ? O1 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O1 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? S4 O9 K2 146.79(8) . 3_656 ? S4 O9 K1 99.03(6) . . ? K2 O9 K1 98.66(4) 3_656 . ? S4 O9 K2 104.89(6) . . ? K2 O9 K2 97.39(4) 3_656 . ? K1 O9 K2 104.85(4) . . ? C1 O2 S4 120.41(11) . . ? C1 O2 K2 131.56(10) . . ? S4 O2 K2 106.22(6) . . ? S3 O5 K2 127.05(7) . 1_455 ? S3 O5 K1 101.48(7) . 3_556 ? K2 O5 K1 98.06(4) 1_455 3_556 ? S4 O8 K2 120.34(7) . 1_556 ? S4 O8 K1 96.89(6) . . ? K2 O8 K1 106.93(4) 1_556 . ? S3 O6 K1 150.80(8) . 1_554 ? S3 O6 K2 99.54(6) . . ? K1 O6 K2 107.94(4) 1_554 . ? S3 O6 K1 95.69(6) . 3_556 ? K1 O6 K1 73.93(3) 1_554 3_556 ? K2 O6 K1 130.63(5) . 3_556 ? C7 O4 S3 117.62(11) . . ? S4 O7 K1 139.34(8) . 1_655 ? S4 O7 K1 127.76(7) . 3_657 ? K1 O7 K1 73.89(3) 1_655 3_657 ? C10 O3 C13 116.84(18) . . ? C8 C7 C12 120.94(18) . . ? C8 C7 O4 116.73(17) . . ? C12 C7 O4 122.26(16) . . ? C7 C12 C11 119.77(18) . . ? C7 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C7 C8 C9 119.50(19) . . ? C7 C8 H8 120.2 . . ? C9 C8 H8 120.2 . . ? C10 C11 C12 119.4(2) . . ? C10 C11 H11 120.3 . . ? C12 C11 H11 120.3 . . ? C8 C9 C10 120.36(19) . . ? C8 C9 H9 119.8 . . ? C10 C9 H9 119.8 . . ? O3 C10 C9 115.28(19) . . ? O3 C10 C11 124.7(2) . . ? C9 C10 C11 120.01(19) . . ? O3 C13 H13A 109.5 . . ? O3 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O3 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C4 C14 C5 119.64(19) . . ? C4 C14 H14 120.2 . . ? C5 C14 H14 120.2 . . ? S3 O10 K1 114.84(7) . . ? S3 O10 K2 97.60(6) . . ? K1 O10 K2 110.18(4) . . ? 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 O10 K1 S4 O7 -164.57(10) . . . . ? O7 K1 S4 O7 105.37(12) 1_455 . . . ? O6 K1 S4 O7 61.06(10) 1_556 . . . ? O5 K1 S4 O7 -83.85(10) 3_556 . . . ? O9 K1 S4 O7 -85.92(12) . . . . ? O8 K1 S4 O7 87.48(12) . . . . ? O6 K1 S4 O7 -52.28(11) 3_556 . . . ? O7 K1 S4 O7 -10.97(12) 3_657 . . . ? S3 K1 S4 O7 -72.37(10) 3_556 . . . ? K1 K1 S4 O7 19.82(11) 3_557 . . . ? S3 K1 S4 O7 -153.63(10) . . . . ? O10 K1 S4 O8 107.95(7) . . . . ? O7 K1 S4 O8 17.89(8) 1_455 . . . ? O6 K1 S4 O8 -26.42(7) 1_556 . . . ? O5 K1 S4 O8 -171.33(7) 3_556 . . . ? O9 K1 S4 O8 -173.40(9) . . . . ? O6 K1 S4 O8 -139.76(7) 3_556 . . . ? O7 K1 S4 O8 -98.45(7) 3_657 . . . ? S3 K1 S4 O8 -159.84(6) 3_556 . . . ? K1 K1 S4 O8 -67.66(7) 3_557 . . . ? S3 K1 S4 O8 118.89(6) . . . . ? O10 K1 S4 O9 -78.65(7) . . . . ? O7 K1 S4 O9 -168.71(8) 1_455 . . . ? O6 K1 S4 O9 146.98(7) 1_556 . . . ? O5 K1 S4 O9 2.07(7) 3_556 . . . ? O8 K1 S4 O9 173.40(9) . . . . ? O6 K1 S4 O9 33.64(8) 3_556 . . . ? O7 K1 S4 O9 74.95(7) 3_657 . . . ? S3 K1 S4 O9 13.55(6) 3_556 . . . ? K1 K1 S4 O9 105.74(7) 3_557 . . . ? S3 K1 S4 O9 -67.71(6) . . . . ? O10 K1 S4 O2 10.71(6) . . . . ? O7 K1 S4 O2 -79.35(8) 1_455 . . . ? O6 K1 S4 O2 -123.66(6) 1_556 . . . ? O5 K1 S4 O2 91.43(6) 3_556 . . . ? O9 K1 S4 O2 89.36(8) . . . . ? O8 K1 S4 O2 -97.24(8) . . . . ? O6 K1 S4 O2 123.00(6) 3_556 . . . ? O7 K1 S4 O2 164.31(6) 3_657 . . . ? S3 K1 S4 O2 102.91(5) 3_556 . . . ? K1 K1 S4 O2 -164.90(5) 3_557 . . . ? S3 K1 S4 O2 21.65(5) . . . . ? O10 K1 S4 K2 -29.42(3) . . . . ? O7 K1 S4 K2 -119.48(6) 1_455 . . . ? O6 K1 S4 K2 -163.79(3) 1_556 . . . ? O5 K1 S4 K2 51.30(3) 3_556 . . . ? O9 K1 S4 K2 49.23(6) . . . . ? O8 K1 S4 K2 -137.37(6) . . . . ? O6 K1 S4 K2 82.87(4) 3_556 . . . ? O7 K1 S4 K2 124.18(3) 3_657 . . . ? S3 K1 S4 K2 62.786(17) 3_556 . . . ? K1 K1 S4 K2 154.97(2) 3_557 . . . ? S3 K1 S4 K2 -18.479(13) . . . . ? O10 K1 S4 K2 144.42(3) . . . 1_556 ? O7 K1 S4 K2 54.36(6) 1_455 . . 1_556 ? O6 K1 S4 K2 10.05(3) 1_556 . . 1_556 ? O5 K1 S4 K2 -134.87(3) 3_556 . . 1_556 ? O9 K1 S4 K2 -136.93(6) . . . 1_556 ? O8 K1 S4 K2 36.46(6) . . . 1_556 ? O6 K1 S4 K2 -103.29(4) 3_556 . . 1_556 ? O7 K1 S4 K2 -61.99(3) 3_657 . . 1_556 ? S3 K1 S4 K2 -123.382(16) 3_556 . . 1_556 ? K1 K1 S4 K2 -31.19(2) 3_557 . . 1_556 ? S3 K1 S4 K2 155.353(13) . . . 1_556 ? O9 K2 S4 O7 72.45(7) 3_656 . . . ? O5 K2 S4 O7 -0.44(7) 1_655 . . . ? O8 K2 S4 O7 -86.12(17) 1_554 . . . ? O2 K2 S4 O7 -84.72(9) . . . . ? O6 K2 S4 O7 159.35(7) . . . . ? O10 K2 S4 O7 178.85(7) . . . . ? O9 K2 S4 O7 97.82(9) . . . . ? S3 K2 S4 O7 170.02(7) . . . . ? S4 K2 S4 O7 -11.18(10) 1_554 . . . ? S3 K2 S4 O7 -16.94(7) 1_655 . . . ? K1 K2 S4 O7 28.91(7) 3_656 . . . ? O9 K2 S4 O8 -121.24(7) 3_656 . . . ? O5 K2 S4 O8 165.87(7) 1_655 . . . ? O8 K2 S4 O8 80.19(17) 1_554 . . . ? O2 K2 S4 O8 81.59(9) . . . . ? O6 K2 S4 O8 -34.34(7) . . . . ? O10 K2 S4 O8 -14.84(7) . . . . ? O9 K2 S4 O8 -95.87(9) . . . . ? S3 K2 S4 O8 -23.67(7) . . . . ? S4 K2 S4 O8 155.14(7) 1_554 . . . ? S3 K2 S4 O8 149.38(7) 1_655 . . . ? K1 K2 S4 O8 -164.77(6) 3_656 . . . ? O9 K2 S4 O9 -25.37(9) 3_656 . . . ? O5 K2 S4 O9 -98.26(7) 1_655 . . . ? O8 K2 S4 O9 176.06(18) 1_554 . . . ? O2 K2 S4 O9 177.46(10) . . . . ? O6 K2 S4 O9 61.54(7) . . . . ? O10 K2 S4 O9 81.03(7) . . . . ? S3 K2 S4 O9 72.20(7) . . . . ? S4 K2 S4 O9 -108.99(8) 1_554 . . . ? S3 K2 S4 O9 -114.75(7) 1_655 . . . ? K1 K2 S4 O9 -68.90(7) 3_656 . . . ? O9 K2 S4 O2 157.17(7) 3_656 . . . ? O5 K2 S4 O2 84.28(7) 1_655 . . . ? O8 K2 S4 O2 -1.40(18) 1_554 . . . ? O6 K2 S4 O2 -115.93(7) . . . . ? O10 K2 S4 O2 -96.43(7) . . . . ? O9 K2 S4 O2 -177.46(10) . . . . ? S3 K2 S4 O2 -105.26(7) . . . . ? S4 K2 S4 O2 73.55(8) 1_554 . . . ? S3 K2 S4 O2 67.79(7) 1_655 . . . ? K1 K2 S4 O2 113.64(7) 3_656 . . . ? O9 K2 S4 K1 -78.09(3) 3_656 . . . ? O5 K2 S4 K1 -150.98(3) 1_655 . . . ? O8 K2 S4 K1 123.35(16) 1_554 . . . ? O2 K2 S4 K1 124.74(7) . . . . ? O6 K2 S4 K1 8.82(3) . . . . ? O10 K2 S4 K1 28.31(3) . . . . ? O9 K2 S4 K1 -52.72(7) . . . . ? S3 K2 S4 K1 19.484(13) . . . . ? S4 K2 S4 K1 -161.71(5) 1_554 . . . ? S3 K2 S4 K1 -167.469(13) 1_655 . . . ? K1 K2 S4 K1 -121.619(12) 3_656 . . . ? O9 K2 S4 K2 -96.38(6) 3_656 . . 1_556 ? O5 K2 S4 K2 -169.27(6) 1_655 . . 1_556 ? O8 K2 S4 K2 105.06(17) 1_554 . . 1_556 ? O2 K2 S4 K2 106.45(8) . . . 1_556 ? O6 K2 S4 K2 -9.47(7) . . . 1_556 ? O10 K2 S4 K2 10.02(6) . . . 1_556 ? O9 K2 S4 K2 -71.01(8) . . . 1_556 ? S3 K2 S4 K2 1.19(6) . . . 1_556 ? S4 K2 S4 K2 180.0 1_554 . . 1_556 ? S3 K2 S4 K2 174.24(5) 1_655 . . 1_556 ? K1 K2 S4 K2 -139.91(5) 3_656 . . 1_556 ? O9 K2 S3 O5 32.81(9) 3_656 . . . ? O5 K2 S3 O5 -33.25(10) 1_655 . . . ? O8 K2 S3 O5 119.48(9) 1_554 . . . ? O2 K2 S3 O5 -96.74(9) . . . . ? O6 K2 S3 O5 85.85(11) . . . . ? O10 K2 S3 O5 -91.31(11) . . . . ? O9 K2 S3 O5 -49.46(9) . . . . ? S4 K2 S3 O5 -71.35(9) . . . . ? S4 K2 S3 O5 109.06(9) 1_554 . . . ? S3 K2 S3 O5 -132.14(14) 1_655 . . . ? K1 K2 S3 O5 45.49(9) 3_656 . . . ? O9 K2 S3 O10 124.12(7) 3_656 . . . ? O5 K2 S3 O10 58.06(14) 1_655 . . . ? O8 K2 S3 O10 -149.21(7) 1_554 . . . ? O2 K2 S3 O10 -5.42(7) . . . . ? O6 K2 S3 O10 177.16(9) . . . . ? O9 K2 S3 O10 41.85(7) . . . . ? S4 K2 S3 O10 19.96(6) . . . . ? S4 K2 S3 O10 -159.62(6) 1_554 . . . ? S3 K2 S3 O10 -40.83(15) 1_655 . . . ? K1 K2 S3 O10 136.80(6) 3_656 . . . ? O9 K2 S3 O6 -53.04(7) 3_656 . . . ? O5 K2 S3 O6 -119.10(14) 1_655 . . . ? O8 K2 S3 O6 33.63(7) 1_554 . . . ? O2 K2 S3 O6 177.41(7) . . . . ? O10 K2 S3 O6 -177.16(9) . . . . ? O9 K2 S3 O6 -135.31(7) . . . . ? S4 K2 S3 O6 -157.20(6) . . . . ? S4 K2 S3 O6 23.21(6) 1_554 . . . ? S3 K2 S3 O6 142.01(14) 1_655 . . . ? K1 K2 S3 O6 -40.36(7) 3_656 . . . ? O9 K2 S3 O4 -144.55(6) 3_656 . . . ? O5 K2 S3 O4 149.39(13) 1_655 . . . ? O8 K2 S3 O4 -57.88(6) 1_554 . . . ? O2 K2 S3 O4 85.90(6) . . . . ? O6 K2 S3 O4 -91.51(9) . . . . ? O10 K2 S3 O4 91.33(8) . . . . ? O9 K2 S3 O4 133.18(6) . . . . ? S4 K2 S3 O4 111.29(6) . . . . ? S4 K2 S3 O4 -68.30(6) 1_554 . . . ? S3 K2 S3 O4 50.50(15) 1_655 . . . ? K1 K2 S3 O4 -131.87(6) 3_656 . . . ? O9 K2 S3 K1 -13.04(3) 3_656 . . 3_556 ? O5 K2 S3 K1 -79.11(12) 1_655 . . 3_556 ? O8 K2 S3 K1 73.63(3) 1_554 . . 3_556 ? O2 K2 S3 K1 -142.59(3) . . . 3_556 ? O6 K2 S3 K1 40.00(6) . . . 3_556 ? O10 K2 S3 K1 -137.16(6) . . . 3_556 ? O9 K2 S3 K1 -95.32(3) . . . 3_556 ? S4 K2 S3 K1 -117.204(14) . . . 3_556 ? S4 K2 S3 K1 63.212(16) 1_554 . . 3_556 ? S3 K2 S3 K1 -177.99(13) 1_655 . . 3_556 ? K1 K2 S3 K1 -0.36(2) 3_656 . . 3_556 ? O9 K2 S3 K1 85.68(3) 3_656 . . . ? O5 K2 S3 K1 19.62(12) 1_655 . . . ? O8 K2 S3 K1 172.35(3) 1_554 . . . ? O2 K2 S3 K1 -43.86(3) . . . . ? O6 K2 S3 K1 138.73(7) . . . . ? O10 K2 S3 K1 -38.44(6) . . . . ? O9 K2 S3 K1 3.41(3) . . . . ? S4 K2 S3 K1 -18.477(13) . . . . ? S4 K2 S3 K1 161.939(13) 1_554 . . . ? S3 K2 S3 K1 -79.27(13) 1_655 . . . ? K1 K2 S3 K1 98.36(2) 3_656 . . . ? O9 K2 S3 K2 -15.05(14) 3_656 . . 1_455 ? O5 K2 S3 K2 -81.11(19) 1_655 . . 1_455 ? O8 K2 S3 K2 71.62(14) 1_554 . . 1_455 ? O2 K2 S3 K2 -144.59(13) . . . 1_455 ? O6 K2 S3 K2 37.99(14) . . . 1_455 ? O10 K2 S3 K2 -139.17(15) . . . 1_455 ? O9 K2 S3 K2 -97.32(13) . . . 1_455 ? S4 K2 S3 K2 -119.21(13) . . . 1_455 ? S4 K2 S3 K2 61.21(14) 1_554 . . 1_455 ? S3 K2 S3 K2 180.000(1) 1_655 . . 1_455 ? K1 K2 S3 K2 -2.37(15) 3_656 . . 1_455 ? O10 K1 S3 O5 -162.75(10) . . . . ? O7 K1 S3 O5 -45.47(6) 1_455 . . . ? O6 K1 S3 O5 -98.34(8) 1_556 . . . ? O5 K1 S3 O5 70.63(7) 3_556 . . . ? O9 K1 S3 O5 144.27(6) . . . . ? O8 K1 S3 O5 -169.85(6) . . . . ? O6 K1 S3 O5 26.80(6) 3_556 . . . ? O7 K1 S3 O5 74.69(8) 3_657 . . . ? S4 K1 S3 O5 167.37(6) . . . . ? S3 K1 S3 O5 47.81(5) 3_556 . . . ? K1 K1 S3 O5 -5.41(6) 3_557 . . . ? O7 K1 S3 O10 117.28(8) 1_455 . . . ? O6 K1 S3 O10 64.41(9) 1_556 . . . ? O5 K1 S3 O10 -126.63(8) 3_556 . . . ? O9 K1 S3 O10 -52.98(8) . . . . ? O8 K1 S3 O10 -7.10(8) . . . . ? O6 K1 S3 O10 -170.45(8) 3_556 . . . ? O7 K1 S3 O10 -122.56(9) 3_657 . . . ? S4 K1 S3 O10 -29.88(8) . . . . ? S3 K1 S3 O10 -149.45(8) 3_556 . . . ? K1 K1 S3 O10 157.34(8) 3_557 . . . ? O10 K1 S3 O6 89.50(10) . . . . ? O7 K1 S3 O6 -153.22(7) 1_455 . . . ? O6 K1 S3 O6 153.91(11) 1_556 . . . ? O5 K1 S3 O6 -37.13(7) 3_556 . . . ? O9 K1 S3 O6 36.52(7) . . . . ? O8 K1 S3 O6 82.40(7) . . . . ? O6 K1 S3 O6 -80.95(7) 3_556 . . . ? O7 K1 S3 O6 -33.06(8) 3_657 . . . ? S4 K1 S3 O6 59.62(7) . . . . ? S3 K1 S3 O6 -59.95(6) 3_556 . . . ? K1 K1 S3 O6 -113.16(7) 3_557 . . . ? O10 K1 S3 O4 -70.20(10) . . . . ? O7 K1 S3 O4 47.08(7) 1_455 . . . ? O6 K1 S3 O4 -5.79(9) 1_556 . . . ? O5 K1 S3 O4 163.18(7) 3_556 . . . ? O9 K1 S3 O4 -123.18(7) . . . . ? O8 K1 S3 O4 -77.30(7) . . . . ? O6 K1 S3 O4 119.35(7) 3_556 . . . ? O7 K1 S3 O4 167.24(8) 3_657 . . . ? S4 K1 S3 O4 -100.08(6) . . . . ? S3 K1 S3 O4 140.36(7) 3_556 . . . ? K1 K1 S3 O4 87.14(7) 3_557 . . . ? O10 K1 S3 K2 49.46(8) . . . . ? O7 K1 S3 K2 166.74(3) 1_455 . . . ? O6 K1 S3 K2 113.87(5) 1_556 . . . ? O5 K1 S3 K2 -77.16(3) 3_556 . . . ? O9 K1 S3 K2 -3.52(3) . . . . ? O8 K1 S3 K2 42.36(3) . . . . ? O6 K1 S3 K2 -120.99(3) 3_556 . . . ? O7 K1 S3 K2 -73.10(5) 3_657 . . . ? S4 K1 S3 K2 19.581(14) . . . . ? S3 K1 S3 K2 -99.982(15) 3_556 . . . ? K1 K1 S3 K2 -153.20(3) 3_557 . . . ? O10 K1 S3 K1 149.45(8) . . . 3_556 ? O7 K1 S3 K1 -93.28(3) 1_455 . . 3_556 ? O6 K1 S3 K1 -146.15(5) 1_556 . . 3_556 ? O5 K1 S3 K1 22.82(3) 3_556 . . 3_556 ? O9 K1 S3 K1 96.47(3) . . . 3_556 ? O8 K1 S3 K1 142.34(3) . . . 3_556 ? O6 K1 S3 K1 -21.01(3) 3_556 . . 3_556 ? O7 K1 S3 K1 26.88(5) 3_657 . . 3_556 ? S4 K1 S3 K1 119.563(16) . . . 3_556 ? S3 K1 S3 K1 0.0 3_556 . . 3_556 ? K1 K1 S3 K1 -53.22(3) 3_557 . . 3_556 ? O10 K1 S3 K2 -138.38(8) . . . 1_455 ? O7 K1 S3 K2 -21.11(3) 1_455 . . 1_455 ? O6 K1 S3 K2 -73.98(5) 1_556 . . 1_455 ? O5 K1 S3 K2 94.99(3) 3_556 . . 1_455 ? O9 K1 S3 K2 168.64(3) . . . 1_455 ? O8 K1 S3 K2 -145.49(3) . . . 1_455 ? O6 K1 S3 K2 51.16(3) 3_556 . . 1_455 ? O7 K1 S3 K2 99.05(5) 3_657 . . 1_455 ? S4 K1 S3 K2 -168.267(13) . . . 1_455 ? S3 K1 S3 K2 72.170(13) 3_556 . . 1_455 ? K1 K1 S3 K2 18.95(3) 3_557 . . 1_455 ? C14 C5 C1 C2 -1.3(3) . . . . ? C14 C5 C1 O2 172.69(18) . . . . ? C5 C1 C2 C3 2.4(3) . . . . ? O2 C1 C2 C3 -171.90(18) . . . . ? C1 C2 C3 C4 -1.1(3) . . . . ? C6 O1 C4 C14 0.5(3) . . . . ? C6 O1 C4 C3 -179.5(2) . . . . ? C2 C3 C4 O1 178.8(2) . . . . ? C2 C3 C4 C14 -1.2(3) . . . . ? O7 S4 O9 K2 18.09(17) . . . 3_656 ? O8 S4 O9 K2 -115.30(14) . . . 3_656 ? O2 S4 O9 K2 132.39(13) . . . 3_656 ? K1 S4 O9 K2 -121.42(15) . . . 3_656 ? K2 S4 O9 K2 130.48(16) . . . 3_656 ? K2 S4 O9 K2 -70.96(15) 1_556 . . 3_656 ? O7 S4 O9 K1 139.51(7) . . . . ? O8 S4 O9 K1 6.11(8) . . . . ? O2 S4 O9 K1 -106.19(6) . . . . ? K2 S4 O9 K1 -108.10(6) . . . . ? K2 S4 O9 K1 50.45(6) 1_556 . . . ? O7 S4 O9 K2 -112.39(8) . . . . ? O8 S4 O9 K2 114.22(7) . . . . ? O2 S4 O9 K2 1.91(7) . . . . ? K1 S4 O9 K2 108.10(6) . . . . ? K2 S4 O9 K2 158.56(3) 1_556 . . . ? O10 K1 O9 S4 94.30(6) . . . . ? O7 K1 O9 S4 38.0(3) 1_455 . . . ? O6 K1 O9 S4 -35.24(7) 1_556 . . . ? O5 K1 O9 S4 -177.86(7) 3_556 . . . ? O8 K1 O9 S4 -3.65(5) . . . . ? O6 K1 O9 S4 -156.15(5) 3_556 . . . ? O7 K1 O9 S4 -102.76(6) 3_657 . . . ? S3 K1 O9 S4 -168.23(5) 3_556 . . . ? K1 K1 O9 S4 -95.94(6) 3_557 . . . ? S3 K1 O9 S4 112.31(6) . . . . ? O10 K1 O9 K2 -113.91(5) . . . 3_656 ? O7 K1 O9 K2 -170.2(2) 1_455 . . 3_656 ? O6 K1 O9 K2 116.55(4) 1_556 . . 3_656 ? O5 K1 O9 K2 -26.08(4) 3_556 . . 3_656 ? O8 K1 O9 K2 148.13(6) . . . 3_656 ? O6 K1 O9 K2 -4.37(5) 3_556 . . 3_656 ? O7 K1 O9 K2 49.02(4) 3_657 . . 3_656 ? S4 K1 O9 K2 151.78(8) . . . 3_656 ? S3 K1 O9 K2 -16.44(4) 3_556 . . 3_656 ? K1 K1 O9 K2 55.85(5) 3_557 . . 3_656 ? S3 K1 O9 K2 -95.90(3) . . . 3_656 ? O10 K1 O9 K2 -13.84(4) . . . . ? O7 K1 O9 K2 -70.2(2) 1_455 . . . ? O6 K1 O9 K2 -143.38(4) 1_556 . . . ? O5 K1 O9 K2 74.00(4) 3_556 . . . ? O8 K1 O9 K2 -111.79(5) . . . . ? O6 K1 O9 K2 95.71(4) 3_556 . . . ? O7 K1 O9 K2 149.10(4) 3_657 . . . ? S4 K1 O9 K2 -108.14(7) . . . . ? S3 K1 O9 K2 83.63(3) 3_556 . . . ? K1 K1 O9 K2 155.92(3) 3_557 . . . ? S3 K1 O9 K2 4.17(3) . . . . ? O9 K2 O9 S4 155.16(9) 3_656 . . . ? O5 K2 O9 S4 76.03(7) 1_655 . . . ? O8 K2 O9 S4 -176.31(16) 1_554 . . . ? O2 K2 O9 S4 -1.47(6) . . . . ? O6 K2 O9 S4 -126.16(6) . . . . ? O10 K2 O9 S4 -90.51(7) . . . . ? S3 K2 O9 S4 -108.19(6) . . . . ? S4 K2 O9 S4 130.05(6) 1_554 . . . ? S3 K2 O9 S4 63.99(6) 1_655 . . . ? K1 K2 O9 S4 114.82(6) 3_656 . . . ? O9 K2 O9 K2 0.0 3_656 . . 3_656 ? O5 K2 O9 K2 -79.13(4) 1_655 . . 3_656 ? O8 K2 O9 K2 28.5(2) 1_554 . . 3_656 ? O2 K2 O9 K2 -156.63(6) . . . 3_656 ? O6 K2 O9 K2 78.68(4) . . . 3_656 ? O10 K2 O9 K2 114.33(5) . . . 3_656 ? S3 K2 O9 K2 96.65(3) . . . 3_656 ? S4 K2 O9 K2 -155.16(9) . . . 3_656 ? S4 K2 O9 K2 -25.11(9) 1_554 . . 3_656 ? S3 K2 O9 K2 -91.17(3) 1_655 . . 3_656 ? K1 K2 O9 K2 -40.34(3) 3_656 . . 3_656 ? O9 K2 O9 K1 -101.04(5) 3_656 . . . ? O5 K2 O9 K1 179.83(5) 1_655 . . . ? O8 K2 O9 K1 -72.5(2) 1_554 . . . ? O2 K2 O9 K1 102.33(6) . . . . ? O6 K2 O9 K1 -22.35(5) . . . . ? O10 K2 O9 K1 13.29(4) . . . . ? S3 K2 O9 K1 -4.38(3) . . . . ? S4 K2 O9 K1 103.80(8) . . . . ? S4 K2 O9 K1 -126.14(6) 1_554 . . . ? S3 K2 O9 K1 167.79(3) 1_655 . . . ? K1 K2 O9 K1 -141.38(3) 3_656 . . . ? C5 C1 O2 S4 63.5(2) . . . . ? C2 C1 O2 S4 -122.23(16) . . . . ? C5 C1 O2 K2 -134.10(15) . . . . ? C2 C1 O2 K2 40.2(2) . . . . ? O7 S4 O2 C1 -75.87(15) . . . . ? O8 S4 O2 C1 46.07(15) . . . . ? O9 S4 O2 C1 164.33(13) . . . . ? K1 S4 O2 C1 107.05(13) . . . . ? K2 S4 O2 C1 166.37(16) . . . . ? K2 S4 O2 C1 13.32(17) 1_556 . . . ? O7 S4 O2 K2 117.76(7) . . . . ? O8 S4 O2 K2 -120.30(7) . . . . ? O9 S4 O2 K2 -2.03(8) . . . . ? K1 S4 O2 K2 -59.32(6) . . . . ? K2 S4 O2 K2 -153.05(3) 1_556 . . . ? O9 K2 O2 C1 167.59(14) 3_656 . . . ? O5 K2 O2 C1 107.92(15) 1_655 . . . ? O8 K2 O2 C1 15.32(18) 1_554 . . . ? O6 K2 O2 C1 -84.69(15) . . . . ? O10 K2 O2 C1 -88.42(15) . . . . ? O9 K2 O2 C1 -162.92(16) . . . . ? S3 K2 O2 C1 -86.04(14) . . . . ? S4 K2 O2 C1 -164.24(19) . . . . ? S4 K2 O2 C1 48.77(17) 1_554 . . . ? S3 K2 O2 C1 89.18(14) 1_655 . . . ? K1 K2 O2 C1 120.96(14) 3_656 . . . ? O9 K2 O2 S4 -28.18(9) 3_656 . . . ? O5 K2 O2 S4 -87.84(7) 1_655 . . . ? O8 K2 O2 S4 179.55(6) 1_554 . . . ? O6 K2 O2 S4 79.54(7) . . . . ? O10 K2 O2 S4 75.82(6) . . . . ? O9 K2 O2 S4 1.32(5) . . . . ? S3 K2 O2 S4 78.19(6) . . . . ? S4 K2 O2 S4 -146.99(4) 1_554 . . . ? S3 K2 O2 S4 -106.58(6) 1_655 . . . ? K1 K2 O2 S4 -74.80(6) 3_656 . . . ? O10 S3 O5 K2 121.78(9) . . . 1_455 ? O6 S3 O5 K2 -106.34(9) . . . 1_455 ? O4 S3 O5 K2 7.82(10) . . . 1_455 ? K2 S3 O5 K2 -169.79(3) . . . 1_455 ? K1 S3 O5 K2 -109.43(10) 3_556 . . 1_455 ? K1 S3 O5 K2 134.82(9) . . . 1_455 ? O10 S3 O5 K1 -128.79(7) . . . 3_556 ? O6 S3 O5 K1 3.09(9) . . . 3_556 ? O4 S3 O5 K1 117.25(6) . . . 3_556 ? K2 S3 O5 K1 -60.36(10) . . . 3_556 ? K1 S3 O5 K1 -115.75(5) . . . 3_556 ? K2 S3 O5 K1 109.43(10) 1_455 . . 3_556 ? O7 S4 O8 K2 -25.45(11) . . . 1_556 ? O9 S4 O8 K2 108.27(8) . . . 1_556 ? O2 S4 O8 K2 -143.04(7) . . . 1_556 ? K1 S4 O8 K2 114.25(8) . . . 1_556 ? K2 S4 O8 K2 167.24(4) . . . 1_556 ? O7 S4 O8 K1 -139.70(7) . . . . ? O9 S4 O8 K1 -5.97(8) . . . . ? O2 S4 O8 K1 102.72(6) . . . . ? K2 S4 O8 K1 52.99(6) . . . . ? K2 S4 O8 K1 -114.25(8) 1_556 . . . ? O10 K1 O8 S4 -68.01(6) . . . . ? O7 K1 O8 S4 -168.44(5) 1_455 . . . ? O6 K1 O8 S4 150.90(7) 1_556 . . . ? O5 K1 O8 S4 10.23(8) 3_556 . . . ? O9 K1 O8 S4 3.64(5) . . . . ? O6 K1 O8 S4 73.58(11) 3_556 . . . ? O7 K1 O8 S4 81.40(6) 3_657 . . . ? S3 K1 O8 S4 29.63(9) 3_556 . . . ? K1 K1 O8 S4 126.79(5) 3_557 . . . ? S3 K1 O8 S4 -65.38(6) . . . . ? O10 K1 O8 K2 167.33(5) . . . 1_556 ? O7 K1 O8 K2 66.90(6) 1_455 . . 1_556 ? O6 K1 O8 K2 26.24(4) 1_556 . . 1_556 ? O5 K1 O8 K2 -114.43(5) 3_556 . . 1_556 ? O9 K1 O8 K2 -121.03(6) . . . 1_556 ? O6 K1 O8 K2 -51.08(10) 3_556 . . 1_556 ? O7 K1 O8 K2 -43.27(5) 3_657 . . 1_556 ? S4 K1 O8 K2 -124.66(8) . . . 1_556 ? S3 K1 O8 K2 -95.03(5) 3_556 . . 1_556 ? K1 K1 O8 K2 2.13(5) 3_557 . . 1_556 ? S3 K1 O8 K2 169.96(3) . . . 1_556 ? O5 S3 O6 K1 64.02(18) . . . 1_554 ? O10 S3 O6 K1 -162.79(14) . . . 1_554 ? O4 S3 O6 K1 -47.39(17) . . . 1_554 ? K2 S3 O6 K1 -160.20(18) . . . 1_554 ? K1 S3 O6 K1 66.93(14) 3_556 . . 1_554 ? K1 S3 O6 K1 149.05(12) . . . 1_554 ? K2 S3 O6 K1 25.30(18) 1_455 . . 1_554 ? O5 S3 O6 K2 -135.77(7) . . . . ? O10 S3 O6 K2 -2.58(8) . . . . ? O4 S3 O6 K2 112.81(6) . . . . ? K1 S3 O6 K2 -132.86(6) 3_556 . . . ? K1 S3 O6 K2 -50.75(7) . . . . ? K2 S3 O6 K2 -174.50(2) 1_455 . . . ? O5 S3 O6 K1 -2.91(8) . . . 3_556 ? O10 S3 O6 K1 130.28(6) . . . 3_556 ? O4 S3 O6 K1 -114.32(6) . . . 3_556 ? K2 S3 O6 K1 132.86(6) . . . 3_556 ? K1 S3 O6 K1 82.12(5) . . . 3_556 ? K2 S3 O6 K1 -41.63(6) 1_455 . . 3_556 ? O9 K2 O6 S3 126.49(7) 3_656 . . . ? O5 K2 O6 S3 142.69(10) 1_655 . . . ? O8 K2 O6 S3 -143.21(7) 1_554 . . . ? O2 K2 O6 S3 -3.13(8) . . . . ? O10 K2 O6 S3 1.57(5) . . . . ? O9 K2 O6 S3 46.67(7) . . . . ? S4 K2 O6 S3 25.81(7) . . . . ? S4 K2 O6 S3 -157.39(6) 1_554 . . . ? S3 K2 O6 S3 -165.29(6) 1_655 . . . ? K1 K2 O6 S3 150.50(5) 3_656 . . . ? O9 K2 O6 K1 -63.51(5) 3_656 . . 1_554 ? O5 K2 O6 K1 -47.31(13) 1_655 . . 1_554 ? O8 K2 O6 K1 26.79(4) 1_554 . . 1_554 ? O2 K2 O6 K1 166.86(4) . . . 1_554 ? O10 K2 O6 K1 171.57(7) . . . 1_554 ? O9 K2 O6 K1 -143.33(4) . . . 1_554 ? S3 K2 O6 K1 170.00(9) . . . 1_554 ? S4 K2 O6 K1 -164.19(3) . . . 1_554 ? S4 K2 O6 K1 12.61(4) 1_554 . . 1_554 ? S3 K2 O6 K1 4.71(12) 1_655 . . 1_554 ? K1 K2 O6 K1 -39.50(5) 3_656 . . 1_554 ? O9 K2 O6 K1 20.43(6) 3_656 . . 3_556 ? O5 K2 O6 K1 36.63(14) 1_655 . . 3_556 ? O8 K2 O6 K1 110.73(7) 1_554 . . 3_556 ? O2 K2 O6 K1 -109.20(6) . . . 3_556 ? O10 K2 O6 K1 -104.49(7) . . . 3_556 ? O9 K2 O6 K1 -59.39(6) . . . 3_556 ? S3 K2 O6 K1 -106.06(9) . . . 3_556 ? S4 K2 O6 K1 -80.25(6) . . . 3_556 ? S4 K2 O6 K1 96.55(6) 1_554 . . 3_556 ? S3 K2 O6 K1 88.65(10) 1_655 . . 3_556 ? K1 K2 O6 K1 44.44(7) 3_656 . . 3_556 ? O5 S3 O4 C7 160.17(13) . . . . ? O10 S3 O4 C7 39.28(14) . . . . ? O6 S3 O4 C7 -80.69(14) . . . . ? K2 S3 O4 C7 -21.56(14) . . . . ? K1 S3 O4 C7 -144.40(11) 3_556 . . . ? K1 S3 O4 C7 81.52(13) . . . . ? K2 S3 O4 C7 165.03(14) 1_455 . . . ? O8 S4 O7 K1 -166.89(10) . . . 1_655 ? O9 S4 O7 K1 59.82(14) . . . 1_655 ? O2 S4 O7 K1 -50.12(13) . . . 1_655 ? K1 S4 O7 K1 125.20(9) . . . 1_655 ? K2 S4 O7 K1 0.56(14) . . . 1_655 ? K2 S4 O7 K1 176.73(12) 1_556 . . 1_655 ? O8 S4 O7 K1 81.83(10) . . . 3_657 ? O9 S4 O7 K1 -51.47(12) . . . 3_657 ? O2 S4 O7 K1 -161.41(8) . . . 3_657 ? K1 S4 O7 K1 13.92(16) . . . 3_657 ? K2 S4 O7 K1 -110.73(7) . . . 3_657 ? K2 S4 O7 K1 65.44(7) 1_556 . . 3_657 ? S3 O4 C7 C8 -121.30(16) . . . . ? S3 O4 C7 C12 61.5(2) . . . . ? C8 C7 C12 C11 -0.3(3) . . . . ? O4 C7 C12 C11 176.75(16) . . . . ? C12 C7 C8 C9 0.2(3) . . . . ? O4 C7 C8 C9 -176.95(17) . . . . ? C7 C12 C11 C10 0.0(3) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C13 O3 C10 C9 -178.7(2) . . . . ? C13 O3 C10 C11 1.6(3) . . . . ? C8 C9 C10 O3 179.82(19) . . . . ? C8 C9 C10 C11 -0.5(3) . . . . ? C12 C11 C10 O3 -179.90(19) . . . . ? C12 C11 C10 C9 0.4(3) . . . . ? O1 C4 C14 C5 -177.8(2) . . . . ? C3 C4 C14 C5 2.3(3) . . . . ? C1 C5 C14 C4 -1.0(3) . . . . ? O5 S3 O10 K1 18.35(10) . . . . ? O6 S3 O10 K1 -113.91(8) . . . . ? O4 S3 O10 K1 130.17(7) . . . . ? K2 S3 O10 K1 -116.44(7) . . . . ? K1 S3 O10 K1 -45.26(11) 3_556 . . . ? K2 S3 O10 K1 56.97(9) 1_455 . . . ? O5 S3 O10 K2 134.79(7) . . . . ? O6 S3 O10 K2 2.53(8) . . . . ? O4 S3 O10 K2 -113.39(6) . . . . ? K1 S3 O10 K2 71.18(8) 3_556 . . . ? K1 S3 O10 K2 116.44(7) . . . . ? K2 S3 O10 K2 173.41(3) 1_455 . . . ? O7 K1 O10 S3 -65.06(8) 1_455 . . . ? O6 K1 O10 S3 -135.99(7) 1_556 . . . ? O5 K1 O10 S3 49.16(7) 3_556 . . . ? O9 K1 O10 S3 123.52(8) . . . . ? O8 K1 O10 S3 173.16(8) . . . . ? O6 K1 O10 S3 10.52(9) 3_556 . . . ? O7 K1 O10 S3 88.93(10) 3_657 . . . ? S4 K1 O10 S3 149.24(8) . . . . ? S3 K1 O10 S3 30.43(8) 3_556 . . . ? K1 K1 O10 S3 -38.61(13) 3_557 . . . ? O7 K1 O10 K2 -174.05(4) 1_455 . . . ? O6 K1 O10 K2 115.02(5) 1_556 . . . ? O5 K1 O10 K2 -59.83(4) 3_556 . . . ? O9 K1 O10 K2 14.53(4) . . . . ? O8 K1 O10 K2 64.17(5) . . . . ? O6 K1 O10 K2 -98.47(5) 3_556 . . . ? O7 K1 O10 K2 -20.06(10) 3_657 . . . ? S4 K1 O10 K2 40.25(3) . . . . ? S3 K1 O10 K2 -78.55(4) 3_556 . . . ? K1 K1 O10 K2 -147.60(5) 3_557 . . . ? S3 K1 O10 K2 -108.99(9) . . . . ? O9 K2 O10 S3 -60.88(7) 3_656 . . . ? O5 K2 O10 S3 -157.72(6) 1_655 . . . ? O8 K2 O10 S3 32.90(7) 1_554 . . . ? O2 K2 O10 S3 174.50(7) . . . . ? O6 K2 O10 S3 -1.56(5) . . . . ? O9 K2 O10 S3 -134.47(7) . . . . ? S4 K2 O10 S3 -158.91(6) . . . . ? S4 K2 O10 S3 25.37(8) 1_554 . . . ? S3 K2 O10 S3 170.12(4) 1_655 . . . ? K1 K2 O10 S3 -73.43(8) 3_656 . . . ? O9 K2 O10 K1 59.16(5) 3_656 . . . ? O5 K2 O10 K1 -37.69(9) 1_655 . . . ? O8 K2 O10 K1 152.93(4) 1_554 . . . ? O2 K2 O10 K1 -65.46(5) . . . . ? O6 K2 O10 K1 118.47(6) . . . . ? O9 K2 O10 K1 -14.43(4) . . . . ? S3 K2 O10 K1 120.04(8) . . . . ? S4 K2 O10 K1 -38.87(3) . . . . ? S4 K2 O10 K1 145.41(3) 1_554 . . . ? S3 K2 O10 K1 -69.84(7) 1_655 . . . ? K1 K2 O10 K1 46.61(8) 3_656 . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.413 _refine_diff_density_min -0.406 _refine_diff_density_rms 0.062 # Attachment 'CMPD2.cif' data_jmwsw2 _database_code_depnum_ccdc_archive 'CCDC 285417' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-methoxyphenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H9 N O4 S' _chemical_formula_weight 203.21 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 'P2(1)2(1)2(1) ' 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 4.9816(4) _cell_length_b 7.0344(5) _cell_length_c 25.1874(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 882.63(11) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4343 _cell_measurement_theta_min 3.01 _cell_measurement_theta_max 28.58 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_max 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.529 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.348 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6379 _diffrn_reflns_av_R_equivalents 0.0478 _diffrn_reflns_av_sigmaI/netI 0.0374 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.62 _diffrn_reflns_theta_max 28.78 _reflns_number_total 2110 _reflns_number_gt 2041 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0435P)^2^+0.1837P] 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 SHELXL _refine_ls_extinction_coef 0.015(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.07(7) _refine_ls_number_reflns 2110 _refine_ls_number_parameters 128 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0296 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0739 _refine_ls_wR_factor_gt 0.0733 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.34440(7) 0.56886(5) 0.201455(14) 0.01900(11) Uani 1 1 d . . . O4 O -0.3994(3) 1.06935(19) 0.04234(4) 0.0279(3) Uani 1 1 d . . . O1 O 0.4108(2) 0.70804(18) 0.15358(4) 0.0244(3) Uani 1 1 d . . . N1 N 0.1569(3) 0.6761(2) 0.24238(5) 0.0228(3) Uani 1 1 d . . . C2 C 0.0692(4) 0.7062(3) 0.08493(6) 0.0266(4) Uani 1 1 d . . . H2 H 0.1195 0.5808 0.0751 0.032 Uiso 1 1 calc R . . O3 O 0.6034(2) 0.54225(18) 0.22502(5) 0.0283(3) Uani 1 1 d . . . C5 C -0.0763(4) 1.0734(3) 0.11490(6) 0.0268(3) Uani 1 1 d . . . H5 H -0.1273 1.1980 0.1253 0.032 Uiso 1 1 calc R . . C3 C -0.1294(4) 0.8020(3) 0.05738(6) 0.0259(3) Uani 1 1 d . . . H3 H -0.2163 0.7424 0.0282 0.031 Uiso 1 1 calc R . . C6 C 0.1241(4) 0.9779(2) 0.14217(6) 0.0256(4) Uani 1 1 d . . . H6 H 0.2133 1.0373 0.1711 0.031 Uiso 1 1 calc R . . C4 C -0.2024(3) 0.9857(2) 0.07222(6) 0.0228(3) Uani 1 1 d . . . C1 C 0.1928(3) 0.7964(2) 0.12703(6) 0.0221(3) Uani 1 1 d . . . O2 O 0.2016(3) 0.40861(17) 0.18178(5) 0.0284(3) Uani 1 1 d . . . C7 C -0.4682(4) 1.2613(3) 0.05586(7) 0.0344(4) Uani 1 1 d . . . H7A H -0.5365 1.2654 0.0923 0.052 Uiso 1 1 calc R . . H7B H -0.6067 1.3077 0.0315 0.052 Uiso 1 1 calc R . . H7C H -0.3084 1.3419 0.0530 0.052 Uiso 1 1 calc R . . H1B H 0.013(5) 0.668(4) 0.2353(8) 0.035(7) Uiso 1 1 d . . . H1A H 0.224(5) 0.766(4) 0.2580(8) 0.039(6) Uiso 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 0.01647(18) 0.01614(17) 0.02440(17) 0.00075(14) -0.00057(14) 0.00020(15) O4 0.0296(6) 0.0284(6) 0.0258(5) 0.0014(5) -0.0040(5) 0.0031(6) O1 0.0186(6) 0.0263(6) 0.0283(5) 0.0065(5) 0.0038(4) 0.0011(5) N1 0.0176(7) 0.0236(7) 0.0272(6) -0.0039(5) 0.0003(6) -0.0014(6) C2 0.0320(9) 0.0222(8) 0.0254(7) -0.0025(7) 0.0045(7) 0.0015(7) O3 0.0183(6) 0.0273(6) 0.0395(6) 0.0065(5) -0.0044(5) 0.0024(5) C5 0.0335(9) 0.0198(8) 0.0271(7) -0.0018(7) -0.0022(6) 0.0024(7) C3 0.0299(9) 0.0267(8) 0.0210(6) -0.0031(6) -0.0009(7) -0.0030(8) C6 0.0294(9) 0.0230(8) 0.0246(7) 0.0006(6) -0.0048(6) -0.0022(7) C4 0.0223(8) 0.0255(8) 0.0205(6) 0.0038(6) 0.0015(6) -0.0012(6) C1 0.0216(8) 0.0222(7) 0.0225(6) 0.0058(6) 0.0026(6) -0.0005(6) O2 0.0303(7) 0.0200(6) 0.0350(6) -0.0040(5) -0.0022(5) -0.0041(5) C7 0.0367(10) 0.0319(10) 0.0345(9) 0.0014(8) -0.0037(8) 0.0104(9) _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 1.4220(12) . ? S1 O3 1.4325(11) . ? S1 N1 1.5821(15) . ? S1 O1 1.5881(12) . ? O4 C4 1.370(2) . ? O4 C7 1.434(2) . ? O1 C1 1.4186(19) . ? N1 H1B 0.74(3) . ? N1 H1A 0.82(3) . ? C2 C1 1.381(2) . ? C2 C3 1.384(2) . ? C2 H2 0.9500 . ? C5 C6 1.386(2) . ? C5 C4 1.389(2) . ? C5 H5 0.9500 . ? C3 C4 1.393(2) . ? C3 H3 0.9500 . ? C6 C1 1.376(2) . ? C6 H6 0.9500 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O2 S1 O3 119.42(8) . . ? O2 S1 N1 108.04(8) . . ? O3 S1 N1 108.90(8) . . ? O2 S1 O1 109.17(7) . . ? O3 S1 O1 101.98(7) . . ? N1 S1 O1 108.89(7) . . ? C4 O4 C7 116.45(13) . . ? C1 O1 S1 117.94(9) . . ? S1 N1 H1B 112.3(18) . . ? S1 N1 H1A 116.2(16) . . ? H1B N1 H1A 125(3) . . ? C1 C2 C3 118.69(16) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C6 C5 C4 119.61(16) . . ? C6 C5 H5 120.2 . . ? C4 C5 H5 120.2 . . ? C2 C3 C4 120.25(15) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C1 C6 C5 119.45(16) . . ? C1 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? O4 C4 C5 123.94(16) . . ? O4 C4 C3 115.97(14) . . ? C5 C4 C3 120.09(16) . . ? C6 C1 C2 121.90(16) . . ? C6 C1 O1 117.80(15) . . ? C2 C1 O1 120.14(15) . . ? O4 C7 H7A 109.5 . . ? O4 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O4 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? 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 O2 S1 O1 C1 64.93(13) . . . . ? O3 S1 O1 C1 -167.81(12) . . . . ? N1 S1 O1 C1 -52.81(14) . . . . ? C1 C2 C3 C4 -0.2(3) . . . . ? C4 C5 C6 C1 -0.9(3) . . . . ? C7 O4 C4 C5 2.2(2) . . . . ? C7 O4 C4 C3 -177.49(14) . . . . ? C6 C5 C4 O4 -178.97(15) . . . . ? C6 C5 C4 C3 0.7(3) . . . . ? C2 C3 C4 O4 179.54(15) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C5 C6 C1 C2 0.6(3) . . . . ? C5 C6 C1 O1 175.89(14) . . . . ? C3 C2 C1 C6 0.0(3) . . . . ? C3 C2 C1 O1 -175.24(14) . . . . ? S1 O1 C1 C6 96.70(16) . . . . ? S1 O1 C1 C2 -87.88(16) . . . . ? _diffrn_measured_fraction_theta_max 0.946 _diffrn_reflns_theta_full 28.78 _diffrn_measured_fraction_theta_full 0.946 _refine_diff_density_max 0.350 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.052 # Attachment 'CMPD3.cif' data_jmwsw5 _database_code_depnum_ccdc_archive 'CCDC 285418' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'potassium 4-acetamidophenyl sulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C8 H10 K N O6 S' _chemical_formula_weight 287.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 6.7995(5) _cell_length_b 6.9857(5) _cell_length_c 12.1695(9) _cell_angle_alpha 89.0620(10) _cell_angle_beta 81.3830(10) _cell_angle_gamma 79.6480(10) _cell_volume 562.18(7) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2869 _cell_measurement_theta_min 2.96 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.697 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 296 _exptl_absorpt_coefficient_mu 0.674 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2968 _diffrn_reflns_av_R_equivalents 0.0613 _diffrn_reflns_av_sigmaI/netI 0.0382 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.96 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1957 _reflns_number_gt 1888 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'WinGX SHELXTL' _computing_structure_refinement 'WinGX SHELXTL' _computing_molecular_graphics 'WinGX Ortep3' _computing_publication_material 'WinGX SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _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^)+(0.0354P)^2^+0.3009P] 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 SHELXL _refine_ls_extinction_coef 0.056(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1957 _refine_ls_number_parameters 165 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0326 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0824 _refine_ls_wR_factor_gt 0.0818 _refine_ls_goodness_of_fit_ref 1.185 _refine_ls_restrained_S_all 1.185 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group K1 K 0.20625(6) 1.21233(5) 0.54935(3) 0.01725(17) Uani 1 1 d . . . S1 S 0.23052(7) 0.71292(6) 0.55779(4) 0.01429(17) Uani 1 1 d . . . O1 O 0.1113(2) 1.1330(2) 0.77692(11) 0.0215(3) Uani 1 1 d . . . H1 H 0.2058 1.1517 0.8103 0.032 Uiso 1 1 calc R . . O2 O 0.6163(2) 0.8116(2) 1.08948(11) 0.0211(3) Uani 1 1 d . . . N1 N 0.2865(3) 0.7920(2) 1.08362(13) 0.0182(4) Uani 1 1 d . . . C2 C 0.1016(3) 0.6438(3) 0.83467(16) 0.0200(4) Uani 1 1 d . . . H2 H -0.0227 0.6252 0.8137 0.024 Uiso 1 1 calc R . . C3 C 0.1096(3) 0.7034(3) 0.94191(16) 0.0201(4) Uani 1 1 d . . . H3 H -0.0105 0.7267 0.9945 0.024 Uiso 1 1 calc R . . C5 C 0.4702(3) 0.6937(3) 0.89567(16) 0.0187(4) Uani 1 1 d . . . H5 H 0.5957 0.7094 0.9164 0.022 Uiso 1 1 calc R . . C1 C 0.2780(3) 0.6119(3) 0.75868(15) 0.0168(4) Uani 1 1 d . . . C6 C 0.4610(3) 0.6351(3) 0.78807(16) 0.0188(4) Uani 1 1 d . . . H6 H 0.5803 0.6110 0.7349 0.023 Uiso 1 1 calc R . . C4 C 0.2929(3) 0.7295(3) 0.97322(15) 0.0172(4) Uani 1 1 d . . . C7 C 0.4397(3) 0.8280(3) 1.13497(15) 0.0173(4) Uani 1 1 d . . . C8 C 0.3778(3) 0.8878(3) 1.25589(16) 0.0220(4) Uani 1 1 d . . . H8A H 0.3979 0.7725 1.3027 0.033 Uiso 1 1 calc R . . H8B H 0.2349 0.9494 1.2683 0.033 Uiso 1 1 calc R . . H8C H 0.4605 0.9801 1.2750 0.033 Uiso 1 1 calc R . . O4 O 0.2084(2) 0.59625(18) 0.46533(11) 0.0189(3) Uani 1 1 d . . . O3 O 0.2708(2) 0.54638(17) 0.65056(10) 0.0174(3) Uani 1 1 d . . . O5 O 0.0466(2) 0.84407(19) 0.60396(11) 0.0198(3) Uani 1 1 d . . . O6 O 0.4042(2) 0.80887(19) 0.54254(11) 0.0208(3) Uani 1 1 d . . . H H 0.173(4) 0.811(3) 1.123(2) 0.022(6) Uiso 1 1 d . . . H88 H 0.115(5) 1.015(5) 0.765(3) 0.050(9) Uiso 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 K1 0.0155(2) 0.0148(2) 0.0209(3) -0.00095(16) -0.00323(16) -0.00077(15) S1 0.0132(3) 0.0127(3) 0.0159(3) 0.00032(18) -0.00132(17) -0.00019(17) O1 0.0195(7) 0.0220(8) 0.0234(7) -0.0032(6) -0.0038(6) -0.0036(6) O2 0.0165(7) 0.0266(7) 0.0193(7) -0.0017(5) -0.0013(5) -0.0025(5) N1 0.0144(8) 0.0231(8) 0.0149(8) -0.0008(6) 0.0009(6) -0.0001(6) C2 0.0168(10) 0.0210(9) 0.0223(10) 0.0012(8) -0.0030(8) -0.0033(7) C3 0.0159(10) 0.0233(10) 0.0195(10) 0.0010(8) 0.0005(7) -0.0023(7) C5 0.0150(10) 0.0199(9) 0.0203(9) 0.0005(7) -0.0025(7) -0.0006(7) C1 0.0212(10) 0.0129(8) 0.0161(9) 0.0016(7) -0.0043(7) -0.0011(7) C6 0.0161(10) 0.0175(9) 0.0200(10) 0.0015(7) 0.0006(7) 0.0014(7) C4 0.0177(10) 0.0149(9) 0.0177(9) 0.0020(7) -0.0026(7) 0.0000(7) C7 0.0172(10) 0.0149(8) 0.0186(9) 0.0022(7) -0.0022(7) -0.0006(7) C8 0.0199(10) 0.0260(10) 0.0193(10) -0.0036(8) -0.0015(8) -0.0029(8) O4 0.0211(7) 0.0172(6) 0.0176(7) 0.0001(5) -0.0023(5) -0.0014(5) O3 0.0226(7) 0.0130(6) 0.0164(6) 0.0003(5) -0.0044(5) -0.0013(5) O5 0.0168(7) 0.0175(7) 0.0224(7) -0.0026(5) -0.0016(5) 0.0033(5) O6 0.0167(7) 0.0197(7) 0.0260(7) 0.0021(6) -0.0015(5) -0.0050(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag K1 O6 2.6951(14) 2_676 ? K1 O3 2.7891(13) 1_565 ? K1 O5 2.7967(15) 2_576 ? K1 O1 2.8171(14) . ? K1 O4 2.8562(13) 1_565 ? K1 O6 2.8937(13) . ? K1 O4 2.9250(14) 2_576 ? K1 O5 2.9948(14) . ? K1 S1 3.3725(6) 2_576 ? K1 S1 3.4634(6) . ? K1 S1 3.5342(6) 1_565 ? K1 K1 4.5410(8) 2_676 ? K1 H88 2.98(3) . ? S1 O4 1.4416(14) . ? S1 O6 1.4470(14) . ? S1 O5 1.4536(13) . ? S1 O3 1.6242(13) . ? S1 K1 3.3725(6) 2_576 ? S1 K1 3.5342(6) 1_545 ? O1 H1 0.8400 . ? O1 H88 0.84(3) . ? O2 C7 1.230(2) . ? N1 C7 1.354(3) . ? N1 C4 1.411(2) . ? N1 H 0.84(2) . ? C2 C1 1.386(3) . ? C2 C3 1.388(3) . ? C2 H2 0.9500 . ? C3 C4 1.399(3) . ? C3 H3 0.9500 . ? C5 C6 1.392(3) . ? C5 C4 1.402(3) . ? C5 H5 0.9500 . ? C1 C6 1.382(3) . ? C1 O3 1.411(2) . ? C6 H6 0.9500 . ? C7 C8 1.513(3) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? O4 K1 2.8562(13) 1_545 ? O4 K1 2.9250(14) 2_576 ? O3 K1 2.7891(13) 1_545 ? O5 K1 2.7967(15) 2_576 ? O6 K1 2.6951(14) 2_676 ? 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 O6 K1 O3 83.07(4) 2_676 1_565 ? O6 K1 O5 113.38(4) 2_676 2_576 ? O3 K1 O5 132.23(4) 1_565 2_576 ? O6 K1 O1 119.70(4) 2_676 . ? O3 K1 O1 77.67(4) 1_565 . ? O5 K1 O1 121.83(4) 2_576 . ? O6 K1 O4 77.96(4) 2_676 1_565 ? O3 K1 O4 49.50(4) 1_565 1_565 ? O5 K1 O4 88.70(4) 2_576 1_565 ? O1 K1 O4 123.18(4) . 1_565 ? O6 K1 O6 71.37(4) 2_676 . ? O3 K1 O6 133.57(4) 1_565 . ? O5 K1 O6 93.85(4) 2_576 . ? O1 K1 O6 82.28(4) . . ? O4 K1 O6 147.57(4) 1_565 . ? O6 K1 O4 143.97(4) 2_676 2_576 ? O3 K1 O4 89.47(4) 1_565 2_576 ? O5 K1 O4 50.21(4) 2_576 2_576 ? O1 K1 O4 92.64(4) . 2_576 ? O4 K1 O4 70.60(4) 1_565 2_576 ? O6 K1 O4 133.19(4) . 2_576 ? O6 K1 O5 119.23(4) 2_676 . ? O3 K1 O5 141.11(4) 1_565 . ? O5 K1 O5 71.06(4) 2_576 . ? O1 K1 O5 63.72(4) . . ? O4 K1 O5 157.18(4) 1_565 . ? O6 K1 O5 48.15(4) . . ? O4 K1 O5 87.95(4) 2_576 . ? O6 K1 S1 132.87(3) 2_676 2_576 ? O3 K1 S1 112.29(3) 1_565 2_576 ? O5 K1 S1 25.10(3) 2_576 2_576 ? O1 K1 S1 107.25(3) . 2_576 ? O4 K1 S1 80.15(3) 1_565 2_576 ? O6 K1 S1 113.54(3) . 2_576 ? O4 K1 S1 25.20(3) 2_576 2_576 ? O5 K1 S1 77.06(3) . 2_576 ? O6 K1 S1 94.60(3) 2_676 . ? O3 K1 S1 147.84(3) 1_565 . ? O5 K1 S1 78.09(3) 2_576 . ? O1 K1 S1 75.77(3) . . ? O4 K1 S1 160.95(3) 1_565 . ? O6 K1 S1 24.25(3) . . ? O4 K1 S1 109.47(3) 2_576 . ? O5 K1 S1 24.67(3) . . ? S1 K1 S1 92.803(14) 2_576 . ? O6 K1 S1 81.47(3) 2_676 1_565 ? O3 K1 S1 26.57(3) 1_565 1_565 ? O5 K1 S1 108.43(3) 2_576 1_565 ? O1 K1 S1 101.38(3) . 1_565 ? O4 K1 S1 23.10(3) 1_565 1_565 ? O6 K1 S1 150.16(3) . 1_565 ? O4 K1 S1 76.55(3) 2_576 1_565 ? O5 K1 S1 158.26(3) . 1_565 ? S1 K1 S1 93.851(14) 2_576 1_565 ? S1 K1 S1 173.29(2) . 1_565 ? O6 K1 K1 37.15(3) 2_676 2_676 ? O3 K1 K1 111.57(3) 1_565 2_676 ? O5 K1 K1 106.16(3) 2_576 2_676 ? O1 K1 K1 102.03(3) . 2_676 ? O4 K1 K1 114.46(3) 1_565 2_676 ? O6 K1 K1 34.22(3) . 2_676 ? O4 K1 K1 156.36(3) 2_576 2_676 ? O5 K1 K1 82.22(3) . 2_676 ? S1 K1 K1 131.170(17) 2_576 2_676 ? S1 K1 K1 57.767(11) . 2_676 ? S1 K1 K1 117.691(16) 1_565 2_676 ? O6 K1 H88 118.7(6) 2_676 . ? O3 K1 H88 93.4(7) 1_565 . ? O5 K1 H88 113.2(7) 2_576 . ? O1 K1 H88 16.3(6) . . ? O4 K1 H88 139.3(6) 1_565 . ? O6 K1 H88 68.0(6) . . ? O4 K1 H88 96.8(6) 2_576 . ? O5 K1 H88 48.5(7) . . ? S1 K1 H88 105.1(7) 2_576 . ? S1 K1 H88 59.5(6) . . ? S1 K1 H88 117.6(7) 1_565 . ? K1 K1 H88 92.6(6) 2_676 . ? O4 S1 O6 115.91(8) . . ? O4 S1 O5 114.18(8) . . ? O6 S1 O5 111.93(8) . . ? O4 S1 O3 100.76(7) . . ? O6 S1 O3 106.61(8) . . ? O5 S1 O3 105.97(7) . . ? O4 S1 K1 59.77(5) . 2_576 ? O6 S1 K1 132.98(6) . 2_576 ? O5 S1 K1 54.70(6) . 2_576 ? O3 S1 K1 120.34(5) . 2_576 ? O4 S1 K1 124.20(5) . . ? O6 S1 K1 55.23(5) . . ? O5 S1 K1 59.31(6) . . ? O3 S1 K1 135.03(5) . . ? K1 S1 K1 87.197(14) 2_576 . ? O4 S1 K1 51.01(5) . 1_545 ? O6 S1 K1 129.98(6) . 1_545 ? O5 S1 K1 116.91(6) . 1_545 ? O3 S1 K1 50.19(5) . 1_545 ? K1 S1 K1 86.149(14) 2_576 1_545 ? K1 S1 K1 173.29(2) . 1_545 ? K1 O1 H1 109.5 . . ? K1 O1 H88 93(2) . . ? H1 O1 H88 112.1 . . ? C7 N1 C4 128.86(16) . . ? C7 N1 H 114.7(17) . . ? C4 N1 H 116.4(17) . . ? C1 C2 C3 118.94(18) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 120.60(17) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C6 C5 C4 119.49(18) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C2 C1 C6 121.42(18) . . ? C2 C1 O3 118.89(17) . . ? C6 C1 O3 119.64(16) . . ? C1 C6 C5 119.92(17) . . ? C1 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C5 C4 C3 119.62(18) . . ? C5 C4 N1 123.66(18) . . ? C3 C4 N1 116.73(17) . . ? O2 C7 N1 123.99(18) . . ? O2 C7 C8 121.62(18) . . ? N1 C7 C8 114.38(16) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? S1 O4 K1 105.89(6) . 1_545 ? S1 O4 K1 95.03(6) . 2_576 ? K1 O4 K1 109.40(4) 1_545 2_576 ? C1 O3 S1 116.56(11) . . ? C1 O3 K1 137.95(10) . 1_545 ? S1 O3 K1 103.23(6) . 1_545 ? S1 O5 K1 100.19(7) . 2_576 ? S1 O5 K1 96.02(7) . . ? K1 O5 K1 108.94(4) 2_576 . ? S1 O6 K1 146.20(8) . 2_676 ? S1 O6 K1 100.51(6) . . ? K1 O6 K1 108.63(4) 2_676 . ? 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 O6 K1 S1 O4 -83.41(8) 2_676 . . . ? O3 K1 S1 O4 -167.70(8) 1_565 . . . ? O5 K1 S1 O4 29.54(7) 2_576 . . . ? O1 K1 S1 O4 157.10(8) . . . . ? O4 K1 S1 O4 -17.48(7) 1_565 . . . ? O6 K1 S1 O4 -99.87(10) . . . . ? O4 K1 S1 O4 69.35(8) 2_576 . . . ? O5 K1 S1 O4 99.94(10) . . . . ? S1 K1 S1 O4 50.00(7) 2_576 . . . ? S1 K1 S1 O4 -137.29(15) 1_565 . . . ? K1 K1 S1 O4 -88.44(7) 2_676 . . . ? O6 K1 S1 O6 16.46(10) 2_676 . . . ? O3 K1 S1 O6 -67.83(9) 1_565 . . . ? O5 K1 S1 O6 129.41(7) 2_576 . . . ? O1 K1 S1 O6 -103.03(7) . . . . ? O4 K1 S1 O6 82.39(12) 1_565 . . . ? O4 K1 S1 O6 169.22(7) 2_576 . . . ? O5 K1 S1 O6 -160.19(10) . . . . ? S1 K1 S1 O6 149.87(7) 2_576 . . . ? S1 K1 S1 O6 -37.42(17) 1_565 . . . ? K1 K1 S1 O6 11.43(7) 2_676 . . . ? O6 K1 S1 O5 176.65(7) 2_676 . . . ? O3 K1 S1 O5 92.36(9) 1_565 . . . ? O5 K1 S1 O5 -70.40(8) 2_576 . . . ? O1 K1 S1 O5 57.16(7) . . . . ? O4 K1 S1 O5 -117.42(11) 1_565 . . . ? O6 K1 S1 O5 160.19(10) . . . . ? O4 K1 S1 O5 -30.59(7) 2_576 . . . ? S1 K1 S1 O5 -49.93(7) 2_576 . . . ? S1 K1 S1 O5 122.77(16) 1_565 . . . ? K1 K1 S1 O5 171.62(7) 2_676 . . . ? O6 K1 S1 O3 94.78(8) 2_676 . . . ? O3 K1 S1 O3 10.49(5) 1_565 . . . ? O5 K1 S1 O3 -152.27(8) 2_576 . . . ? O1 K1 S1 O3 -24.71(8) . . . . ? O4 K1 S1 O3 160.71(11) 1_565 . . . ? O6 K1 S1 O3 78.32(10) . . . . ? O4 K1 S1 O3 -112.46(8) 2_576 . . . ? O5 K1 S1 O3 -81.87(10) . . . . ? S1 K1 S1 O3 -131.80(7) 2_576 . . . ? S1 K1 S1 O3 40.90(19) 1_565 . . . ? K1 K1 S1 O3 89.75(7) 2_676 . . . ? O6 K1 S1 K1 -133.41(3) 2_676 . . 2_576 ? O3 K1 S1 K1 142.29(6) 1_565 . . 2_576 ? O5 K1 S1 K1 -20.46(3) 2_576 . . 2_576 ? O1 K1 S1 K1 107.09(3) . . . 2_576 ? O4 K1 S1 K1 -67.49(9) 1_565 . . 2_576 ? O6 K1 S1 K1 -149.87(7) . . . 2_576 ? O4 K1 S1 K1 19.34(3) 2_576 . . 2_576 ? O5 K1 S1 K1 49.93(6) . . . 2_576 ? S1 K1 S1 K1 0.0 2_576 . . 2_576 ? S1 K1 S1 K1 172.70(15) 1_565 . . 2_576 ? K1 K1 S1 K1 -138.443(18) 2_676 . . 2_576 ? O6 K1 S1 K1 -126.12(15) 2_676 . . 1_545 ? O3 K1 S1 K1 149.59(14) 1_565 . . 1_545 ? O5 K1 S1 K1 -13.17(16) 2_576 . . 1_545 ? O1 K1 S1 K1 114.39(15) . . . 1_545 ? O4 K1 S1 K1 -60.2(2) 1_565 . . 1_545 ? O6 K1 S1 K1 -142.58(17) . . . 1_545 ? O4 K1 S1 K1 26.64(16) 2_576 . . 1_545 ? O5 K1 S1 K1 57.23(16) . . . 1_545 ? S1 K1 S1 K1 7.30(15) 2_576 . . 1_545 ? S1 K1 S1 K1 180.000(2) 1_565 . . 1_545 ? K1 K1 S1 K1 -131.15(15) 2_676 . . 1_545 ? C1 C2 C3 C4 -0.5(3) . . . . ? C3 C2 C1 C6 1.1(3) . . . . ? C3 C2 C1 O3 178.35(16) . . . . ? C2 C1 C6 C5 -0.7(3) . . . . ? O3 C1 C6 C5 -177.96(15) . . . . ? C4 C5 C6 C1 -0.2(3) . . . . ? C6 C5 C4 C3 0.8(3) . . . . ? C6 C5 C4 N1 -179.07(16) . . . . ? C2 C3 C4 C5 -0.4(3) . . . . ? C2 C3 C4 N1 179.45(16) . . . . ? C7 N1 C4 C5 -0.2(3) . . . . ? C7 N1 C4 C3 179.95(18) . . . . ? C4 N1 C7 O2 0.7(3) . . . . ? C4 N1 C7 C8 -178.31(17) . . . . ? O6 S1 O4 K1 121.72(7) . . . 1_545 ? O5 S1 O4 K1 -105.95(7) . . . 1_545 ? O3 S1 O4 K1 7.15(7) . . . 1_545 ? K1 S1 O4 K1 -111.82(6) 2_576 . . 1_545 ? K1 S1 O4 K1 -174.15(2) . . . 1_545 ? O6 S1 O4 K1 -126.45(7) . . . 2_576 ? O5 S1 O4 K1 5.87(8) . . . 2_576 ? O3 S1 O4 K1 118.97(6) . . . 2_576 ? K1 S1 O4 K1 -62.33(6) . . . 2_576 ? K1 S1 O4 K1 111.82(6) 1_545 . . 2_576 ? C2 C1 O3 S1 91.73(18) . . . . ? C6 C1 O3 S1 -90.94(18) . . . . ? C2 C1 O3 K1 -67.7(2) . . . 1_545 ? C6 C1 O3 K1 109.63(18) . . . 1_545 ? O4 S1 O3 C1 -173.25(13) . . . . ? O6 S1 O3 C1 65.36(14) . . . . ? O5 S1 O3 C1 -54.03(14) . . . . ? K1 S1 O3 C1 -112.11(12) 2_576 . . . ? K1 S1 O3 C1 8.27(16) . . . . ? K1 S1 O3 C1 -166.01(15) 1_545 . . . ? O4 S1 O3 K1 -7.24(7) . . . 1_545 ? O6 S1 O3 K1 -128.63(7) . . . 1_545 ? O5 S1 O3 K1 111.98(7) . . . 1_545 ? K1 S1 O3 K1 53.91(6) 2_576 . . 1_545 ? K1 S1 O3 K1 174.29(3) . . . 1_545 ? O4 S1 O5 K1 -6.22(9) . . . 2_576 ? O6 S1 O5 K1 127.98(7) . . . 2_576 ? O3 S1 O5 K1 -116.18(6) . . . 2_576 ? K1 S1 O5 K1 110.52(6) . . . 2_576 ? K1 S1 O5 K1 -63.16(6) 1_545 . . 2_576 ? O4 S1 O5 K1 -116.74(7) . . . . ? O6 S1 O5 K1 17.46(8) . . . . ? O3 S1 O5 K1 133.30(6) . . . . ? K1 S1 O5 K1 -110.52(6) 2_576 . . . ? K1 S1 O5 K1 -173.68(2) 1_545 . . . ? O6 K1 O5 S1 -3.82(8) 2_676 . . . ? O3 K1 O5 S1 -122.08(7) 1_565 . . . ? O5 K1 O5 S1 102.96(8) 2_576 . . . ? O1 K1 O5 S1 -114.73(8) . . . . ? O4 K1 O5 S1 131.69(9) 1_565 . . . ? O6 K1 O5 S1 -10.77(5) . . . . ? O4 K1 O5 S1 151.31(7) 2_576 . . . ? S1 K1 O5 S1 128.34(6) 2_576 . . . ? S1 K1 O5 S1 -164.62(5) 1_565 . . . ? K1 K1 O5 S1 -7.15(6) 2_676 . . . ? O6 K1 O5 K1 -106.79(5) 2_676 . . 2_576 ? O3 K1 O5 K1 134.95(6) 1_565 . . 2_576 ? O5 K1 O5 K1 0.0 2_576 . . 2_576 ? O1 K1 O5 K1 142.30(6) . . . 2_576 ? O4 K1 O5 K1 28.72(12) 1_565 . . 2_576 ? O6 K1 O5 K1 -113.74(6) . . . 2_576 ? O4 K1 O5 K1 48.34(4) 2_576 . . 2_576 ? S1 K1 O5 K1 25.38(3) 2_576 . . 2_576 ? S1 K1 O5 K1 -102.96(8) . . . 2_576 ? S1 K1 O5 K1 92.42(8) 1_565 . . 2_576 ? K1 K1 O5 K1 -110.11(4) 2_676 . . 2_576 ? O4 S1 O6 K1 -34.44(17) . . . 2_676 ? O5 S1 O6 K1 -167.79(12) . . . 2_676 ? O3 S1 O6 K1 76.76(15) . . . 2_676 ? K1 S1 O6 K1 -106.23(13) 2_576 . . 2_676 ? K1 S1 O6 K1 -149.48(17) . . . 2_676 ? K1 S1 O6 K1 25.20(18) 1_545 . . 2_676 ? O4 S1 O6 K1 115.05(7) . . . . ? O5 S1 O6 K1 -18.31(9) . . . . ? O3 S1 O6 K1 -133.76(6) . . . . ? K1 S1 O6 K1 43.26(9) 2_576 . . . ? K1 S1 O6 K1 174.68(3) 1_545 . . . ? O6 K1 O6 S1 -162.66(10) 2_676 . . . ? O3 K1 O6 S1 137.12(6) 1_565 . . . ? O5 K1 O6 S1 -49.26(7) 2_576 . . . ? O1 K1 O6 S1 72.36(7) . . . . ? O4 K1 O6 S1 -142.90(7) 1_565 . . . ? O4 K1 O6 S1 -14.00(9) 2_576 . . . ? O5 K1 O6 S1 10.95(5) . . . . ? S1 K1 O6 S1 -33.15(7) 2_576 . . . ? S1 K1 O6 S1 171.80(4) 1_565 . . . ? K1 K1 O6 S1 -162.66(10) 2_676 . . . ? O6 K1 O6 K1 0.0 2_676 . . 2_676 ? O3 K1 O6 K1 -60.22(7) 1_565 . . 2_676 ? O5 K1 O6 K1 113.40(5) 2_576 . . 2_676 ? O1 K1 O6 K1 -124.98(5) . . . 2_676 ? O4 K1 O6 K1 19.76(10) 1_565 . . 2_676 ? O4 K1 O6 K1 148.66(5) 2_576 . . 2_676 ? O5 K1 O6 K1 173.60(7) . . . 2_676 ? S1 K1 O6 K1 129.51(4) 2_576 . . 2_676 ? S1 K1 O6 K1 162.66(10) . . . 2_676 ? S1 K1 O6 K1 -25.54(9) 1_565 . . 2_676 ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.317 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.077 # Attachment 'CMPD4.cif' data_jmwsw6 _database_code_depnum_ccdc_archive 'CCDC 285419' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'potassium 4-nitrophenyl sulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H4 K N O6 S' _chemical_formula_weight 257.26 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pbca ' 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' '-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 6.9153(4) _cell_length_b 13.1212(7) _cell_length_c 18.9869(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1722.82(16) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 6385 _cell_measurement_theta_min 3.11 _cell_measurement_theta_max 27.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.984 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1040 _exptl_absorpt_coefficient_mu 0.867 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8048 _diffrn_reflns_av_R_equivalents 0.0999 _diffrn_reflns_av_sigmaI/netI 0.0512 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 24.99 _reflns_number_total 1514 _reflns_number_gt 1446 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0279P)^2^+0.7794P] 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 SHELXL _refine_ls_extinction_coef 0.0018(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1514 _refine_ls_number_parameters 137 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0275 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0743 _refine_ls_wR_factor_gt 0.0734 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N N 0.3489(2) 0.67091(13) 0.65224(8) 0.0217(4) Uani 1 1 d . . . O3 O 0.4044(2) 0.63786(11) 0.59531(6) 0.0314(3) Uani 1 1 d . . . O2 O 0.2643(2) 0.75271(10) 0.65925(6) 0.0281(3) Uani 1 1 d . . . K K 0.14671(5) 0.64643(3) 1.029624(19) 0.01931(16) Uani 1 1 d . . . C3 C 0.3558(2) 0.65243(13) 0.78084(9) 0.0180(4) Uani 1 1 d . . . H3 H 0.3107 0.7205 0.7851 0.022 Uiso 1 1 calc R . . C2 C 0.3951(3) 0.59443(13) 0.84007(8) 0.0174(4) Uani 1 1 d . . . H2 H 0.3804 0.6228 0.8858 0.021 Uiso 1 1 calc R . . C1 C 0.4561(2) 0.49459(13) 0.83182(8) 0.0166(4) Uani 1 1 d . . . C6 C 0.4813(3) 0.45103(13) 0.76566(8) 0.0192(4) Uani 1 1 d . . . H6 H 0.5209 0.3820 0.7613 0.023 Uiso 1 1 calc R . . C5 C 0.4481(2) 0.50946(13) 0.70651(8) 0.0198(4) Uani 1 1 d . . . H5 H 0.4690 0.4822 0.6608 0.024 Uiso 1 1 calc R . . C4 C 0.3837(3) 0.60869(13) 0.71507(9) 0.0176(4) Uani 1 1 d . . . S S 0.34005(6) 0.38801(3) 0.93998(2) 0.01558(16) Uani 1 1 d . . . O6 O 0.21887(19) 0.47095(9) 0.96227(6) 0.0231(3) Uani 1 1 d . . . O5 O 0.45766(18) 0.34235(9) 0.99410(6) 0.0214(3) Uani 1 1 d . . . O4 O 0.2371(2) 0.31618(9) 0.89649(7) 0.0285(3) Uani 1 1 d . . . O1 O 0.50916(17) 0.43739(9) 0.89067(6) 0.0192(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 N 0.0170(8) 0.0263(8) 0.0217(8) 0.0036(6) -0.0025(6) -0.0087(6) O3 0.0348(8) 0.0440(9) 0.0153(6) 0.0013(5) 0.0014(6) -0.0035(7) O2 0.0335(8) 0.0214(7) 0.0295(7) 0.0075(5) -0.0056(6) -0.0042(6) K 0.0167(3) 0.0184(2) 0.0228(2) -0.00192(14) -0.00052(14) 0.00077(14) C3 0.0150(9) 0.0162(8) 0.0227(8) -0.0009(7) 0.0019(7) -0.0023(6) C2 0.0152(8) 0.0194(8) 0.0176(8) -0.0024(7) 0.0021(7) -0.0027(7) C1 0.0115(8) 0.0191(8) 0.0191(8) 0.0025(6) 0.0002(6) -0.0019(7) C6 0.0147(8) 0.0178(8) 0.0249(9) -0.0033(6) 0.0009(7) -0.0004(7) C5 0.0175(9) 0.0241(9) 0.0179(8) -0.0054(7) 0.0010(7) -0.0040(7) C4 0.0131(8) 0.0222(9) 0.0174(8) 0.0023(7) -0.0014(7) -0.0049(7) S 0.0143(3) 0.0134(2) 0.0191(2) 0.00060(15) 0.00038(15) -0.00091(14) O6 0.0220(7) 0.0190(6) 0.0281(6) 0.0025(5) 0.0065(6) 0.0040(6) O5 0.0190(6) 0.0218(6) 0.0234(6) 0.0062(5) 0.0005(5) 0.0020(5) O4 0.0282(7) 0.0242(7) 0.0331(7) -0.0060(5) -0.0042(6) -0.0082(6) O1 0.0148(6) 0.0219(6) 0.0209(6) 0.0058(5) 0.0009(5) 0.0007(5) _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 N O3 1.226(2) . ? N O2 1.230(2) . ? N C4 1.465(2) . ? O3 K 2.9067(13) 6_657 ? O2 K 2.9103(12) 7_575 ? K O6 2.6806(12) . ? K O5 2.7540(13) 8_665 ? K O5 2.7766(14) 5_667 ? K O3 2.9067(13) 6_557 ? K O2 2.9103(12) 7_576 ? K O6 2.9644(14) 5_567 ? K O1 3.0271(12) 5_667 ? K O4 3.0420(14) 5_567 ? K S 3.4450(6) 5_567 ? K S 3.5990(6) 8_665 ? K S 3.6241(6) 5_667 ? K K 4.4888(8) 5_567 ? C3 C2 1.385(2) . ? C3 C4 1.388(2) . ? C3 H3 0.9500 . ? C2 C1 1.385(2) . ? C2 H2 0.9500 . ? C1 C6 1.391(2) . ? C1 O1 1.3950(19) . ? C6 C5 1.379(2) . ? C6 H6 0.9500 . ? C5 C4 1.386(3) . ? C5 H5 0.9500 . ? S O6 1.4374(12) . ? S O5 1.4409(13) . ? S O4 1.4411(13) . ? S O1 1.6322(12) . ? S K 3.4450(6) 5_567 ? S K 3.5990(6) 8_655 ? S K 3.6241(6) 5_667 ? O6 K 2.9644(14) 5_567 ? O5 K 2.7540(12) 8_655 ? O5 K 2.7766(13) 5_667 ? O4 K 3.0420(14) 5_567 ? O1 K 3.0271(12) 5_667 ? 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 N O2 123.57(15) . . ? O3 N C4 117.98(15) . . ? O2 N C4 118.44(14) . . ? N O3 K 152.38(12) . 6_657 ? N O2 K 116.00(10) . 7_575 ? O6 K O5 137.20(4) . 8_665 ? O6 K O5 77.57(4) . 5_667 ? O5 K O5 99.73(3) 8_665 5_667 ? O6 K O3 71.63(4) . 6_557 ? O5 K O3 71.65(4) 8_665 6_557 ? O5 K O3 115.96(4) 5_667 6_557 ? O6 K O2 137.90(4) . 7_576 ? O5 K O2 81.72(4) 8_665 7_576 ? O5 K O2 80.66(4) 5_667 7_576 ? O3 K O2 150.33(4) 6_557 7_576 ? O6 K O6 74.77(4) . 5_567 ? O5 K O6 105.91(4) 8_665 5_567 ? O5 K O6 151.20(4) 5_667 5_567 ? O3 K O6 62.00(4) 6_557 5_567 ? O2 K O6 115.51(4) 7_576 5_567 ? O6 K O1 77.29(4) . 5_667 ? O5 K O1 131.89(4) 8_665 5_667 ? O5 K O1 47.60(3) 5_667 5_667 ? O3 K O1 147.91(4) 6_557 5_667 ? O2 K O1 61.49(3) 7_576 5_667 ? O6 K O1 117.11(3) 5_567 5_667 ? O6 K O4 121.40(4) . 5_567 ? O5 K O4 74.56(4) 8_665 5_567 ? O5 K O4 157.82(4) 5_667 5_567 ? O3 K O4 83.08(4) 6_557 5_567 ? O2 K O4 77.32(4) 7_576 5_567 ? O6 K O4 46.82(3) 5_567 5_567 ? O1 K O4 120.93(3) 5_667 5_567 ? O6 K S 98.58(3) . 5_567 ? O5 K S 84.69(3) 8_665 5_567 ? O5 K S 175.49(3) 5_667 5_567 ? O3 K S 64.42(3) 6_557 5_567 ? O2 K S 101.01(3) 7_576 5_567 ? O6 K S 24.47(2) 5_567 5_567 ? O1 K S 129.55(3) 5_667 5_567 ? O4 K S 24.68(2) 5_567 5_567 ? O6 K S 121.75(3) . 8_665 ? O5 K S 21.36(3) 8_665 8_665 ? O5 K S 81.46(3) 5_667 8_665 ? O3 K S 70.29(3) 6_557 8_665 ? O2 K S 89.56(3) 7_576 8_665 ? O6 K S 120.25(3) 5_567 8_665 ? O1 K S 122.44(3) 5_667 8_665 ? O4 K S 95.64(3) 5_567 8_665 ? S K S 102.686(14) 5_567 8_665 ? O6 K S 77.68(3) . 5_667 ? O5 K S 114.34(3) 8_665 5_667 ? O5 K S 21.17(3) 5_667 5_667 ? O3 K S 133.62(3) 6_557 5_667 ? O2 K S 69.41(3) 7_576 5_667 ? O6 K S 139.66(3) 5_567 5_667 ? O1 K S 26.51(2) 5_667 5_667 ? O4 K S 143.24(3) 5_567 5_667 ? S K S 156.045(18) 5_567 5_667 ? S K S 99.220(13) 8_665 5_667 ? O6 K K 39.58(3) . 5_567 ? O5 K K 128.26(3) 8_665 5_567 ? O5 K K 116.75(3) 5_667 5_567 ? O3 K K 60.11(3) 6_557 5_567 ? O2 K K 136.68(3) 7_576 5_567 ? O6 K K 35.18(2) 5_567 5_567 ? O1 K K 99.77(3) 5_667 5_567 ? O4 K K 81.91(3) 5_567 5_567 ? S K K 59.204(11) 5_567 5_567 ? S K K 130.311(15) 8_665 5_567 ? S K K 112.079(15) 5_667 5_567 ? C2 C3 C4 118.43(16) . . ? C2 C3 H3 120.8 . . ? C4 C3 H3 120.8 . . ? C3 C2 C1 119.19(15) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C2 C1 C6 121.93(15) . . ? C2 C1 O1 119.89(14) . . ? C6 C1 O1 117.98(14) . . ? C5 C6 C1 119.08(15) . . ? C5 C6 H6 120.5 . . ? C1 C6 H6 120.5 . . ? C6 C5 C4 118.72(15) . . ? C6 C5 H5 120.6 . . ? C4 C5 H5 120.6 . . ? C5 C4 C3 122.60(15) . . ? C5 C4 N 118.74(15) . . ? C3 C4 N 118.64(16) . . ? O6 S O5 115.71(7) . . ? O6 S O4 112.08(8) . . ? O5 S O4 114.56(8) . . ? O6 S O1 106.62(7) . . ? O5 S O1 99.77(7) . . ? O4 S O1 106.55(7) . . ? O6 S K 58.69(5) . 5_567 ? O5 S K 112.18(5) . 5_567 ? O4 S K 61.80(6) . 5_567 ? O1 S K 148.02(5) . 5_567 ? O6 S K 122.85(5) . 8_655 ? O5 S K 44.13(5) . 8_655 ? O4 S K 73.00(5) . 8_655 ? O1 S K 127.07(4) . 8_655 ? K S K 80.217(11) 5_567 8_655 ? O6 S K 128.20(6) . 5_667 ? O5 S K 44.09(5) . 5_667 ? O4 S K 119.57(6) . 5_667 ? O1 S K 55.89(4) . 5_667 ? K S K 156.045(18) 5_567 5_667 ? K S K 77.875(11) 8_655 5_667 ? S O6 K 154.08(8) . . ? S O6 K 96.84(6) . 5_567 ? K O6 K 105.23(4) . 5_567 ? S O5 K 114.51(7) . 8_655 ? S O5 K 114.74(6) . 5_667 ? K O5 K 110.33(4) 8_655 5_667 ? S O4 K 93.52(6) . 5_567 ? C1 O1 S 118.98(10) . . ? C1 O1 K 143.38(9) . 5_667 ? S O1 K 97.60(5) . 5_667 ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 N O3 K 65.4(3) . . . 6_657 ? C4 N O3 K -115.4(2) . . . 6_657 ? O3 N O2 K 9.0(2) . . . 7_575 ? C4 N O2 K -170.23(11) . . . 7_575 ? C4 C3 C2 C1 -1.5(2) . . . . ? C3 C2 C1 C6 0.8(3) . . . . ? C3 C2 C1 O1 175.56(15) . . . . ? C2 C1 C6 C5 1.2(3) . . . . ? O1 C1 C6 C5 -173.66(15) . . . . ? C1 C6 C5 C4 -2.4(3) . . . . ? C6 C5 C4 C3 1.6(3) . . . . ? C6 C5 C4 N 179.83(15) . . . . ? C2 C3 C4 C5 0.4(3) . . . . ? C2 C3 C4 N -177.85(15) . . . . ? O3 N C4 C5 -10.3(2) . . . . ? O2 N C4 C5 168.99(15) . . . . ? O3 N C4 C3 168.01(16) . . . . ? O2 N C4 C3 -12.7(2) . . . . ? O5 S O6 K 47.07(18) . . . . ? O4 S O6 K -179.06(14) . . . . ? O1 S O6 K -62.83(17) . . . . ? K S O6 K 148.46(18) 5_567 . . . ? K S O6 K 97.47(16) 8_655 . . . ? K S O6 K -3.5(2) 5_667 . . . ? O5 S O6 K -101.39(7) . . . 5_567 ? O4 S O6 K 32.48(8) . . . 5_567 ? O1 S O6 K 148.71(5) . . . 5_567 ? K S O6 K -50.99(6) 8_655 . . 5_567 ? K S O6 K -151.94(3) 5_667 . . 5_567 ? O5 K O6 S 115.43(16) 8_665 . . . ? O5 K O6 S 24.48(16) 5_667 . . . ? O3 K O6 S 147.54(17) 6_557 . . . ? O2 K O6 S -36.06(19) 7_576 . . . ? O6 K O6 S -147.44(18) 5_567 . . . ? O1 K O6 S -24.37(16) 5_667 . . . ? O4 K O6 S -143.03(15) 5_567 . . . ? S K O6 S -153.13(16) 5_567 . . . ? S K O6 S 96.11(16) 8_665 . . . ? S K O6 S 2.80(16) 5_667 . . . ? K K O6 S -147.44(18) 5_567 . . . ? O5 K O6 K -97.13(6) 8_665 . . 5_567 ? O5 K O6 K 171.91(4) 5_667 . . 5_567 ? O3 K O6 K -65.02(4) 6_557 . . 5_567 ? O2 K O6 K 111.37(6) 7_576 . . 5_567 ? O6 K O6 K 0.0 5_567 . . 5_567 ? O1 K O6 K 123.06(4) 5_667 . . 5_567 ? O4 K O6 K 4.40(5) 5_567 . . 5_567 ? S K O6 K -5.70(3) 5_567 . . 5_567 ? S K O6 K -116.46(3) 8_665 . . 5_567 ? S K O6 K 150.23(4) 5_667 . . 5_567 ? O6 S O5 K 111.61(8) . . . 8_655 ? O4 S O5 K -21.14(10) . . . 8_655 ? O1 S O5 K -134.50(6) . . . 8_655 ? K S O5 K 46.86(7) 5_567 . . 8_655 ? K S O5 K -129.09(9) 5_667 . . 8_655 ? O6 S O5 K -119.31(7) . . . 5_667 ? O4 S O5 K 107.95(8) . . . 5_667 ? O1 S O5 K -5.41(7) . . . 5_667 ? K S O5 K 175.94(3) 5_567 . . 5_667 ? K S O5 K 129.09(9) 8_655 . . 5_667 ? O6 S O4 K -31.37(7) . . . 5_567 ? O5 S O4 K 103.06(7) . . . 5_567 ? O1 S O4 K -147.64(5) . . . 5_567 ? K S O4 K 87.84(3) 8_655 . . 5_567 ? K S O4 K 152.62(3) 5_667 . . 5_567 ? C2 C1 O1 S 78.67(17) . . . . ? C6 C1 O1 S -106.34(15) . . . . ? C2 C1 O1 K -104.16(18) . . . 5_667 ? C6 C1 O1 K 70.8(2) . . . 5_667 ? O6 S O1 C1 -56.44(12) . . . . ? O5 S O1 C1 -177.16(11) . . . . ? O4 S O1 C1 63.43(13) . . . . ? K S O1 C1 0.47(16) 5_567 . . . ? K S O1 C1 144.35(9) 8_655 . . . ? K S O1 C1 178.30(13) 5_667 . . . ? O6 S O1 K 125.26(6) . . . 5_667 ? O5 S O1 K 4.55(6) . . . 5_667 ? O4 S O1 K -114.87(6) . . . 5_667 ? K S O1 K -177.83(5) 5_567 . . 5_667 ? K S O1 K -33.95(6) 8_655 . . 5_667 ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.234 _refine_diff_density_min -0.391 _refine_diff_density_rms 0.064 # Attachment 'CMPD5.cif' data_jmwsw22 _database_code_depnum_ccdc_archive 'CCDC 285420' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'potassium 2,2,2-trifluoroethyl sulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H2 F3 K O4 S' _chemical_formula_weight 218.20 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/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 11.862(3) _cell_length_b 7.0333(16) _cell_length_c 9.150(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.962(4) _cell_angle_gamma 90.00 _cell_volume 726.1(3) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2441 _cell_measurement_theta_min 3.41 _cell_measurement_theta_max 27.41 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_min 0.12 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.996 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 1.042 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.74 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3536 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1271 _reflns_number_gt 1199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0670P)^2^+1.3590P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1271 _refine_ls_number_parameters 100 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0473 _refine_ls_R_factor_gt 0.0451 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1220 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 K K 0.93132(7) 1.16462(10) 0.28232(8) 0.0314(3) Uani 1 1 d . . . S2 S 0.84955(7) 0.64912(11) 0.38957(9) 0.0268(3) Uani 1 1 d . . . O2 O 0.9281(2) 0.8127(3) 0.4117(3) 0.0357(6) Uani 1 1 d . . . O3 O 0.8570(2) 0.5281(3) 0.2655(3) 0.0360(6) Uani 1 1 d . . . O4 O 0.8571(2) 0.5550(4) 0.5317(3) 0.0441(7) Uani 1 1 d . . . O1 O 0.7167(2) 0.7290(4) 0.3222(3) 0.0386(6) Uani 1 1 d . . . C1 C 0.6697(4) 0.8333(5) 0.4247(5) 0.0409(9) Uani 1 1 d . . . H1A H 0.7312 0.8475 0.5257 0.049 Uiso 1 1 calc R . . H1B H 0.6018 0.7636 0.4403 0.049 Uiso 1 1 calc R . . F1 F 0.5826(3) 1.1213(5) 0.4481(5) 0.1032(14) Uani 1 1 d . . . F2 F 0.5497(5) 1.0079(8) 0.2214(5) 0.153(2) Uani 1 1 d . . . C2 C 0.6305(5) 1.0231(8) 0.3583(8) 0.0718(16) Uani 1 1 d . . . F3 F 0.7167(5) 1.1244(5) 0.3429(9) 0.181(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 K 0.0452(5) 0.0184(4) 0.0324(4) -0.0023(3) 0.0146(3) 0.0003(3) S2 0.0334(5) 0.0188(4) 0.0276(5) 0.0031(3) 0.0086(3) 0.0024(3) O2 0.0459(14) 0.0232(12) 0.0383(14) -0.0022(10) 0.0136(11) -0.0039(10) O3 0.0440(14) 0.0245(13) 0.0384(13) -0.0055(10) 0.0111(11) 0.0025(10) O4 0.0510(16) 0.0437(16) 0.0387(14) 0.0182(12) 0.0155(12) 0.0064(12) O1 0.0370(14) 0.0426(15) 0.0333(13) -0.0044(11) 0.0066(10) 0.0099(12) C1 0.041(2) 0.040(2) 0.045(2) -0.0033(16) 0.0188(17) 0.0037(16) F1 0.104(3) 0.0551(19) 0.185(4) -0.008(2) 0.095(3) 0.0227(19) F2 0.170(5) 0.149(5) 0.122(3) 0.047(3) 0.019(3) 0.107(4) C2 0.069(3) 0.049(3) 0.115(5) 0.010(3) 0.054(3) 0.021(3) F3 0.197(5) 0.0370(17) 0.410(10) 0.036(3) 0.241(7) 0.019(2) _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 K O4 2.679(3) 4_575 ? K O3 2.693(3) 1_565 ? K O2 2.749(3) . ? K F3 2.781(4) . ? K O2 2.786(3) 3_776 ? K O3 2.845(3) 2_755 ? K O2 2.974(3) 2_755 ? K O4 3.233(3) 3_776 ? K S2 3.4297(13) 2_755 ? K S2 3.5598(12) 3_776 ? K S2 3.7553(12) 1_565 ? K K 3.9957(10) 2_755 ? S2 O4 1.437(2) . ? S2 O3 1.443(2) . ? S2 O2 1.455(3) . ? S2 O1 1.606(3) . ? S2 K 3.4297(13) 2_745 ? S2 K 3.5598(12) 3_776 ? S2 K 3.7553(12) 1_545 ? O2 K 2.786(3) 3_776 ? O2 K 2.974(3) 2_745 ? O3 K 2.693(3) 1_545 ? O3 K 2.845(3) 2_745 ? O4 K 2.679(3) 4_576 ? O4 K 3.233(3) 3_776 ? O1 C1 1.432(4) . ? C1 C2 1.481(7) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? F1 C2 1.328(6) . ? F2 C2 1.326(8) . ? C2 F3 1.289(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 O4 K O3 118.89(9) 4_575 1_565 ? O4 K O2 78.74(8) 4_575 . ? O3 K O2 146.26(8) 1_565 . ? O4 K F3 91.87(16) 4_575 . ? O3 K F3 78.71(9) 1_565 . ? O2 K F3 71.80(10) . . ? O4 K O2 146.10(9) 4_575 3_776 ? O3 K O2 94.99(7) 1_565 3_776 ? O2 K O2 72.69(8) . 3_776 ? F3 K O2 96.11(18) . 3_776 ? O4 K O3 75.31(8) 4_575 2_755 ? O3 K O3 126.90(8) 1_565 2_755 ? O2 K O3 83.82(8) . 2_755 ? F3 K O3 154.36(9) . 2_755 ? O2 K O3 83.73(7) 3_776 2_755 ? O4 K O2 77.74(8) 4_575 2_755 ? O3 K O2 82.38(7) 1_565 2_755 ? O2 K O2 131.09(7) . 2_755 ? F3 K O2 150.54(15) . 2_755 ? O2 K O2 107.93(9) 3_776 2_755 ? O3 K O2 48.89(7) 2_755 2_755 ? O4 K O4 143.07(4) 4_575 3_776 ? O3 K O4 68.80(7) 1_565 3_776 ? O2 K O4 115.73(7) . 3_776 ? F3 K O4 124.53(15) . 3_776 ? O2 K O4 46.31(7) 3_776 3_776 ? O3 K O4 73.03(7) 2_755 3_776 ? O2 K O4 67.25(7) 2_755 3_776 ? O4 K S2 71.62(6) 4_575 2_755 ? O3 K S2 106.56(6) 1_565 2_755 ? O2 K S2 106.38(6) . 2_755 ? F3 K S2 163.28(16) . 2_755 ? O2 K S2 99.16(6) 3_776 2_755 ? O3 K S2 24.39(5) 2_755 2_755 ? O2 K S2 24.98(5) 2_755 2_755 ? O4 K S2 71.67(5) 3_776 2_755 ? O4 K S2 153.64(7) 4_575 3_776 ? O3 K S2 80.78(6) 1_565 3_776 ? O2 K S2 94.11(6) . 3_776 ? F3 K S2 110.14(16) . 3_776 ? O2 K S2 22.56(5) 3_776 3_776 ? O3 K S2 78.72(6) 2_755 3_776 ? O2 K S2 88.66(6) 2_755 3_776 ? O4 K S2 23.81(4) 3_776 3_776 ? S2 K S2 86.50(3) 2_755 3_776 ? O4 K S2 134.73(7) 4_575 1_565 ? O3 K S2 17.67(5) 1_565 1_565 ? O2 K S2 131.72(6) . 1_565 ? F3 K S2 73.39(8) . 1_565 ? O2 K S2 78.95(5) 3_776 1_565 ? O3 K S2 131.13(6) 2_755 1_565 ? O2 K S2 94.35(5) 2_755 1_565 ? O4 K S2 61.98(5) 3_776 1_565 ? S2 K S2 116.23(3) 2_755 1_565 ? S2 K S2 68.04(3) 3_776 1_565 ? O4 K K 114.98(7) 4_575 2_755 ? O3 K K 45.36(6) 1_565 2_755 ? O2 K K 156.43(7) . 2_755 ? F3 K K 123.98(7) . 2_755 ? O2 K K 87.32(6) 3_776 2_755 ? O3 K K 81.65(6) 2_755 2_755 ? O2 K K 43.46(5) 2_755 2_755 ? O4 K K 41.86(5) 3_776 2_755 ? S2 K K 63.82(3) 2_755 2_755 ? S2 K K 64.91(3) 3_776 2_755 ? S2 K K 52.41(2) 1_565 2_755 ? O4 S2 O3 116.00(16) . . ? O4 S2 O2 112.31(16) . . ? O3 S2 O2 112.59(15) . . ? O4 S2 O1 106.75(15) . . ? O3 S2 O1 101.27(14) . . ? O2 S2 O1 106.70(15) . . ? O4 S2 K 125.82(12) . 2_745 ? O3 S2 K 54.49(10) . 2_745 ? O2 S2 K 59.69(10) . 2_745 ? O1 S2 K 127.26(10) . 2_745 ? O4 S2 K 65.22(12) . 3_776 ? O3 S2 K 132.41(11) . 3_776 ? O2 S2 K 47.29(10) . 3_776 ? O1 S2 K 124.73(10) . 3_776 ? K S2 K 85.15(3) 2_745 3_776 ? O4 S2 K 82.51(12) . 1_545 ? O3 S2 K 34.49(10) . 1_545 ? O2 S2 K 123.23(11) . 1_545 ? O1 S2 K 121.27(10) . 1_545 ? K S2 K 67.400(19) 2_745 1_545 ? K S2 K 111.96(3) 3_776 1_545 ? S2 O2 K 138.18(15) . . ? S2 O2 K 110.15(13) . 3_776 ? K O2 K 107.31(8) . 3_776 ? S2 O2 K 95.33(11) . 2_745 ? K O2 K 88.47(7) . 2_745 ? K O2 K 110.36(9) 3_776 2_745 ? S2 O3 K 127.84(14) . 1_545 ? S2 O3 K 101.12(12) . 2_745 ? K O3 K 92.32(7) 1_545 2_745 ? S2 O4 K 162.26(17) . 4_576 ? S2 O4 K 90.97(13) . 3_776 ? K O4 K 84.50(7) 4_576 3_776 ? C1 O1 S2 117.5(2) . . ? O1 C1 C2 109.2(3) . . ? O1 C1 H1A 109.8 . . ? C2 C1 H1A 109.8 . . ? O1 C1 H1B 109.8 . . ? C2 C1 H1B 109.8 . . ? H1A C1 H1B 108.3 . . ? F3 C2 F2 108.0(6) . . ? F3 C2 F1 106.5(5) . . ? F2 C2 F1 107.7(5) . . ? F3 C2 C1 112.6(5) . . ? F2 C2 C1 111.0(5) . . ? F1 C2 C1 110.8(4) . . ? C2 F3 K 152.0(3) . . ? 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 O4 S2 O2 K -146.8(2) . . . . ? O3 S2 O2 K 80.1(2) . . . . ? O1 S2 O2 K -30.2(2) . . . . ? K S2 O2 K 93.7(2) 2_745 . . . ? K S2 O2 K -152.3(3) 3_776 . . . ? K S2 O2 K 117.45(17) 1_545 . . . ? O4 S2 O2 K 5.55(19) . . . 3_776 ? O3 S2 O2 K -127.59(14) . . . 3_776 ? O1 S2 O2 K 122.18(13) . . . 3_776 ? K S2 O2 K -113.98(13) 2_745 . . 3_776 ? K S2 O2 K -90.22(12) 1_545 . . 3_776 ? O4 S2 O2 K 119.53(14) . . . 2_745 ? O3 S2 O2 K -13.61(15) . . . 2_745 ? O1 S2 O2 K -123.84(11) . . . 2_745 ? K S2 O2 K 113.98(13) 3_776 . . 2_745 ? K S2 O2 K 23.77(13) 1_545 . . 2_745 ? O4 K O2 S2 -45.6(2) 4_575 . . . ? O3 K O2 S2 80.5(3) 1_565 . . . ? F3 K O2 S2 50.1(3) . . . . ? O2 K O2 S2 152.8(3) 3_776 . . . ? O3 K O2 S2 -121.8(2) 2_755 . . . ? O2 K O2 S2 -108.2(2) 2_755 . . . ? O4 K O2 S2 170.39(19) 3_776 . . . ? S2 K O2 S2 -112.5(2) 2_755 . . . ? S2 K O2 S2 160.0(2) 3_776 . . . ? S2 K O2 S2 96.0(2) 1_565 . . . ? K K O2 S2 -174.00(12) 2_755 . . . ? O4 K O2 K 161.54(10) 4_575 . . 3_776 ? O3 K O2 K -72.38(16) 1_565 . . 3_776 ? F3 K O2 K -102.70(19) . . . 3_776 ? O2 K O2 K 0.0 3_776 . . 3_776 ? O3 K O2 K 85.34(9) 2_755 . . 3_776 ? O2 K O2 K 98.97(10) 2_755 . . 3_776 ? O4 K O2 K 17.55(11) 3_776 . . 3_776 ? S2 K O2 K 94.71(8) 2_755 . . 3_776 ? S2 K O2 K 7.16(8) 3_776 . . 3_776 ? S2 K O2 K -56.84(11) 1_565 . . 3_776 ? K K O2 K 33.17(19) 2_755 . . 3_776 ? O4 K O2 K 50.67(7) 4_575 . . 2_745 ? O3 K O2 K 176.75(12) 1_565 . . 2_745 ? F3 K O2 K 146.43(18) . . . 2_745 ? O2 K O2 K -110.87(11) 3_776 . . 2_745 ? O3 K O2 K -25.53(7) 2_755 . . 2_745 ? O2 K O2 K -11.90(5) 2_755 . . 2_745 ? O4 K O2 K -93.32(8) 3_776 . . 2_745 ? S2 K O2 K -16.16(6) 2_755 . . 2_745 ? S2 K O2 K -103.71(6) 3_776 . . 2_745 ? S2 K O2 K -167.71(5) 1_565 . . 2_745 ? K K O2 K -77.70(15) 2_755 . . 2_745 ? O4 S2 O3 K -15.0(2) . . . 1_545 ? O2 S2 O3 K 116.27(18) . . . 1_545 ? O1 S2 O3 K -130.14(17) . . . 1_545 ? K S2 O3 K 101.82(18) 2_745 . . 1_545 ? K S2 O3 K 64.2(2) 3_776 . . 1_545 ? O4 S2 O3 K -116.87(15) . . . 2_745 ? O2 S2 O3 K 14.45(16) . . . 2_745 ? O1 S2 O3 K 128.04(12) . . . 2_745 ? K S2 O3 K -37.59(16) 3_776 . . 2_745 ? K S2 O3 K -101.82(18) 1_545 . . 2_745 ? O3 S2 O4 K 52.1(6) . . . 4_576 ? O2 S2 O4 K -79.3(6) . . . 4_576 ? O1 S2 O4 K 164.1(6) . . . 4_576 ? K S2 O4 K -11.5(7) 2_745 . . 4_576 ? K S2 O4 K -74.9(6) 3_776 . . 4_576 ? K S2 O4 K 43.6(6) 1_545 . . 4_576 ? O3 S2 O4 K 126.96(13) . . . 3_776 ? O2 S2 O4 K -4.49(15) . . . 3_776 ? O1 S2 O4 K -121.09(12) . . . 3_776 ? K S2 O4 K 63.38(13) 2_745 . . 3_776 ? K S2 O4 K 118.43(6) 1_545 . . 3_776 ? O4 S2 O1 C1 48.6(3) . . . . ? O3 S2 O1 C1 170.4(3) . . . . ? O2 S2 O1 C1 -71.7(3) . . . . ? K S2 O1 C1 -136.0(2) 2_745 . . . ? K S2 O1 C1 -22.5(3) 3_776 . . . ? K S2 O1 C1 139.9(2) 1_545 . . . ? S2 O1 C1 C2 123.9(4) . . . . ? O1 C1 C2 F3 -62.9(7) . . . . ? O1 C1 C2 F2 58.3(5) . . . . ? O1 C1 C2 F1 177.9(4) . . . . ? F2 C2 F3 K -88.3(12) . . . . ? F1 C2 F3 K 156.2(10) . . . . ? C1 C2 F3 K 34.6(15) . . . . ? O4 K F3 C2 47.4(13) 4_575 . . . ? O3 K F3 C2 166.6(13) 1_565 . . . ? O2 K F3 C2 -30.1(12) . . . . ? O2 K F3 C2 -99.6(13) 3_776 . . . ? O3 K F3 C2 -11.3(16) 2_755 . . . ? O2 K F3 C2 115.5(11) 2_755 . . . ? O4 K F3 C2 -139.2(12) 3_776 . . . ? S2 K F3 C2 56.3(15) 2_755 . . . ? S2 K F3 C2 -117.8(12) 3_776 . . . ? S2 K F3 C2 -176.1(13) 1_565 . . . ? K K F3 C2 169.6(12) 2_755 . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.654 _refine_diff_density_min -0.488 _refine_diff_density_rms 0.086 # Attachment 'CMPD6.cif' data_jmwsw28 _database_code_depnum_ccdc_archive 'CCDC 285421' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'potassium methyl sulfate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C H3 K O4 S' _chemical_formula_weight 150.19 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' K K 0.2009 0.2494 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1)/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 9.1599(13) _cell_length_b 6.9471(10) _cell_length_c 7.3311(10) _cell_angle_alpha 90.00 _cell_angle_beta 93.147(2) _cell_angle_gamma 90.00 _cell_volume 465.81(11) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2205 _cell_measurement_theta_min 2.23 _cell_measurement_theta_max 27.50 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.142 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 304 _exptl_absorpt_coefficient_mu 1.482 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.76 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2711 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_sigmaI/netI 0.0239 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1045 _reflns_number_gt 1015 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0505P)^2^+0.2365P] 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 SHELXL _refine_ls_extinction_coef 0.005(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1045 _refine_ls_number_parameters 66 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0299 _refine_ls_R_factor_gt 0.0292 _refine_ls_wR_factor_ref 0.0818 _refine_ls_wR_factor_gt 0.0811 _refine_ls_goodness_of_fit_ref 1.110 _refine_ls_restrained_S_all 1.110 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.9487(2) 0.1571(3) 0.2906(3) 0.0249(4) Uani 1 1 d . . . H1A H 0.9242 0.0545 0.3753 0.037 Uiso 1 1 calc R . . H1B H 1.0001 0.2607 0.3583 0.037 Uiso 1 1 calc R . . H1C H 1.0117 0.1053 0.1986 0.037 Uiso 1 1 calc R . . O1 O 0.76707(15) -0.04964(19) 0.00729(17) 0.0197(3) Uani 1 1 d . . . O2 O 0.81685(14) 0.23168(18) 0.20182(18) 0.0193(3) Uani 1 1 d . . . O3 O 0.65969(14) -0.03035(19) 0.29748(17) 0.0197(3) Uani 1 1 d . . . O4 O 0.58232(14) 0.19449(19) 0.05923(18) 0.0211(3) Uani 1 1 d . . . S1 S 0.69829(5) 0.07460(6) 0.13576(6) 0.01413(18) Uani 1 1 d . . . K2 K 0.36678(4) 0.09104(5) 0.33345(5) 0.01694(17) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0233(9) 0.0234(11) 0.0271(10) -0.0011(8) -0.0066(7) -0.0019(8) O1 0.0251(7) 0.0174(7) 0.0166(6) -0.0035(5) 0.0012(5) 0.0014(5) O2 0.0225(6) 0.0117(6) 0.0234(6) -0.0011(5) -0.0026(5) -0.0026(5) O3 0.0299(7) 0.0131(6) 0.0163(6) 0.0017(5) 0.0037(5) -0.0017(5) O4 0.0227(7) 0.0133(6) 0.0271(7) 0.0032(5) -0.0018(5) 0.0018(5) S1 0.0190(3) 0.0088(3) 0.0145(3) 0.00040(13) 0.00026(17) -0.00021(13) K2 0.0226(3) 0.0121(3) 0.0160(2) 0.00111(12) -0.00089(15) 0.00030(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O2 1.437(2) . ? C1 H1A 0.9800 . ? C1 H1B 0.9800 . ? C1 H1C 0.9800 . ? O1 S1 1.4471(13) . ? O1 K2 2.7368(14) 3_655 ? O1 K2 3.0422(14) 2_645 ? O2 S1 1.5959(13) . ? O2 K2 3.0135(14) 2_655 ? O3 S1 1.4520(13) . ? O3 K2 2.7621(13) 3_656 ? O3 K2 2.8059(14) 2_645 ? O3 K2 2.8384(14) . ? O4 S1 1.4392(13) . ? O4 K2 2.8958(14) 2_655 ? O4 K2 2.9152(13) 4_565 ? O4 K2 2.9819(14) . ? S1 K2 3.4214(7) 2_645 ? S1 K2 3.4376(7) . ? S1 K2 3.6451(7) 3_655 ? S1 K2 3.6459(7) 2_655 ? K2 O1 2.7368(14) 3_655 ? K2 O3 2.7621(13) 3_656 ? K2 O3 2.8059(14) 2_655 ? K2 O4 2.8958(14) 2_645 ? K2 O4 2.9152(13) 4_566 ? K2 O2 3.0135(14) 2_645 ? K2 O1 3.0422(14) 2_655 ? K2 S1 3.4214(7) 2_655 ? K2 K2 3.5868(8) 3_656 ? 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 C1 H1A 109.5 . . ? O2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? S1 O1 K2 117.87(7) . 3_655 ? S1 O1 K2 92.33(6) . 2_645 ? K2 O1 K2 95.41(4) 3_655 2_645 ? C1 O2 S1 115.59(12) . . ? C1 O2 K2 142.09(11) . 2_655 ? S1 O2 K2 99.97(6) . 2_655 ? S1 O3 K2 156.19(8) . 3_656 ? S1 O3 K2 102.22(6) . 2_645 ? K2 O3 K2 100.45(4) 3_656 2_645 ? S1 O3 K2 101.56(6) . . ? K2 O3 K2 79.64(3) 3_656 . ? K2 O3 K2 104.24(4) 2_645 . ? S1 O4 K2 109.89(7) . 2_655 ? S1 O4 K2 168.36(8) . 4_565 ? K2 O4 K2 76.23(3) 2_655 4_565 ? S1 O4 K2 95.71(6) . . ? K2 O4 K2 98.56(4) 2_655 . ? K2 O4 K2 93.05(4) 4_565 . ? O4 S1 O1 115.46(8) . . ? O4 S1 O3 113.66(8) . . ? O1 S1 O3 111.48(8) . . ? O4 S1 O2 101.42(7) . . ? O1 S1 O2 106.98(8) . . ? O3 S1 O2 106.72(7) . . ? O4 S1 K2 117.80(6) . 2_645 ? O1 S1 K2 62.67(6) . 2_645 ? O3 S1 K2 53.27(5) . 2_645 ? O2 S1 K2 140.30(5) . 2_645 ? O4 S1 K2 59.67(6) . . ? O1 S1 K2 136.09(6) . . ? O3 S1 K2 53.99(5) . . ? O2 S1 K2 116.84(5) . . ? K2 S1 K2 81.007(12) 2_645 . ? O4 S1 K2 74.68(6) . 3_655 ? O1 S1 K2 41.58(5) . 3_655 ? O3 S1 K2 125.28(6) . 3_655 ? O2 S1 K2 125.13(5) . 3_655 ? K2 S1 K2 74.469(11) 2_645 3_655 ? K2 S1 K2 107.812(14) . 3_655 ? O4 S1 K2 48.32(5) . 2_655 ? O1 S1 K2 134.89(6) . 2_655 ? O3 S1 K2 113.30(6) . 2_655 ? O2 S1 K2 54.49(5) . 2_655 ? K2 S1 K2 158.818(19) 2_645 2_655 ? K2 S1 K2 77.879(12) . 2_655 ? K2 S1 K2 110.503(14) 3_655 2_655 ? O1 K2 O3 144.99(4) 3_655 3_656 ? O1 K2 O3 76.13(4) 3_655 2_655 ? O3 K2 O3 117.88(4) 3_656 2_655 ? O1 K2 O3 105.21(4) 3_655 . ? O3 K2 O3 100.36(3) 3_656 . ? O3 K2 O3 108.13(3) 2_655 . ? O1 K2 O4 101.85(4) 3_655 2_645 ? O3 K2 O4 67.05(4) 3_656 2_645 ? O3 K2 O4 173.91(4) 2_655 2_645 ? O3 K2 O4 66.65(4) . 2_645 ? O1 K2 O4 145.84(4) 3_655 4_566 ? O3 K2 O4 67.35(4) 3_656 4_566 ? O3 K2 O4 76.01(4) 2_655 4_566 ? O3 K2 O4 65.82(4) . 4_566 ? O4 K2 O4 103.77(3) 2_645 4_566 ? O1 K2 O4 71.94(4) 3_655 . ? O3 K2 O4 142.58(4) 3_656 . ? O3 K2 O4 65.88(4) 2_655 . ? O3 K2 O4 49.06(4) . . ? O4 K2 O4 108.05(3) 2_645 . ? O4 K2 O4 78.86(3) 4_566 . ? O1 K2 O2 67.33(4) 3_655 2_645 ? O3 K2 O2 83.05(4) 3_656 2_645 ? O3 K2 O2 135.23(4) 2_655 2_645 ? O3 K2 O2 105.78(4) . 2_645 ? O4 K2 O2 46.84(4) 2_645 2_645 ? O4 K2 O2 146.05(4) 4_566 2_645 ? O4 K2 O2 121.93(4) . 2_645 ? O1 K2 O1 105.47(4) 3_655 2_655 ? O3 K2 O1 71.97(4) 3_656 2_655 ? O3 K2 O1 48.17(4) 2_655 2_655 ? O3 K2 O1 133.03(4) . 2_655 ? O4 K2 O1 137.61(4) 2_645 2_655 ? O4 K2 O1 68.74(4) 4_566 2_655 ? O4 K2 O1 110.90(4) . 2_655 ? O2 K2 O1 118.55(4) 2_645 2_655 ? O1 K2 S1 95.30(3) 3_655 2_655 ? O3 K2 S1 93.46(3) 3_656 2_655 ? O3 K2 S1 24.50(3) 2_655 2_655 ? O3 K2 S1 117.83(3) . 2_655 ? O4 K2 S1 160.42(3) 2_645 2_655 ? O4 K2 S1 64.90(3) 4_566 2_655 ? O4 K2 S1 86.10(3) . 2_655 ? O2 K2 S1 136.11(3) 2_645 2_655 ? O1 K2 S1 25.00(2) 2_655 2_655 ? O1 K2 S1 88.48(3) 3_655 . ? O3 K2 S1 122.34(3) 3_656 . ? O3 K2 S1 87.06(3) 2_655 . ? O3 K2 S1 24.44(3) . . ? O4 K2 S1 87.14(3) 2_645 . ? O4 K2 S1 70.73(3) 4_566 . ? O4 K2 S1 24.62(3) . . ? O2 K2 S1 115.98(3) 2_645 . ? O1 K2 S1 124.96(3) 2_655 . ? S1 K2 S1 102.799(14) 2_655 . ? O1 K2 K2 146.97(3) 3_655 3_656 ? O3 K2 K2 51.12(3) 3_656 3_656 ? O3 K2 K2 127.32(3) 2_655 3_656 ? O3 K2 K2 49.25(3) . 3_656 ? O4 K2 K2 52.13(3) 2_645 3_656 ? O4 K2 K2 51.64(3) 4_566 3_656 ? O4 K2 K2 95.34(3) . 3_656 ? O2 K2 K2 97.01(3) 2_645 3_656 ? O1 K2 K2 107.55(3) 2_655 3_656 ? S1 K2 K2 114.572(17) 2_655 3_656 ? S1 K2 K2 72.035(17) . 3_656 ? _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.470 _refine_diff_density_min -0.469 _refine_diff_density_rms 0.096 # Attachment 'CMPD7.cif' data_jmwsw1 _database_code_depnum_ccdc_archive 'CCDC 285422' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-nitrophenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 N2 O5 S' _chemical_formula_weight 218.19 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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 9.9687(10) _cell_length_b 6.9592(7) _cell_length_c 12.2538(12) _cell_angle_alpha 90.00 _cell_angle_beta 98.383(2) _cell_angle_gamma 90.00 _cell_volume 841.01(15) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4281 _cell_measurement_theta_min 2.46 _cell_measurement_theta_max 28.49 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.723 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.384 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5625 _diffrn_reflns_av_R_equivalents 0.0848 _diffrn_reflns_av_sigmaI/netI 0.0595 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.46 _diffrn_reflns_theta_max 28.49 _reflns_number_total 1963 _reflns_number_gt 1845 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0476P)^2^+0.3166P] 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 SHELXL _refine_ls_extinction_coef 0.053(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1963 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0348 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_restrained_S_all 1.057 _refine_ls_shift/su_max 0.053 _refine_ls_shift/su_mean 0.012 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 0.57815(4) 0.26297(5) 0.62609(3) 0.01981(15) Uani 1 1 d . . . O1 O 0.44999(11) 0.12166(15) 0.62617(7) 0.0238(3) Uani 1 1 d . . . O2 O 0.56427(13) 0.41363(15) 0.70261(9) 0.0289(3) Uani 1 1 d . . . O3 O 0.57634(13) 0.29845(17) 0.51183(8) 0.0291(3) Uani 1 1 d . . . O5 O 0.28965(15) -0.1466(2) 1.07767(9) 0.0419(4) Uani 1 1 d . . . O4 O 0.34684(15) -0.41793(19) 1.01217(10) 0.0385(3) Uani 1 1 d . . . C2 C 0.36546(16) 0.1404(2) 0.80088(11) 0.0242(3) Uani 1 1 d . . . H2 H 0.3432 0.2720 0.7878 0.029 Uiso 1 1 calc R . . C1 C 0.42892(15) 0.0368(2) 0.72634(10) 0.0206(3) Uani 1 1 d . . . N2 N 0.71012(15) 0.1448(2) 0.67264(11) 0.0281(3) Uani 1 1 d . . . C4 C 0.37168(15) -0.1430(2) 0.91034(10) 0.0229(3) Uani 1 1 d . . . C6 C 0.46716(16) -0.1540(2) 0.74328(11) 0.0227(3) Uani 1 1 d . . . H6 H 0.5123 -0.2204 0.6915 0.027 Uiso 1 1 calc R . . C3 C 0.33488(17) 0.0491(2) 0.89488(11) 0.0254(3) Uani 1 1 d . . . H3 H 0.2903 0.1156 0.9470 0.030 Uiso 1 1 calc R . . C5 C 0.43783(18) -0.2458(2) 0.83791(12) 0.0235(3) Uani 1 1 d . . . H5 H 0.4628 -0.3761 0.8523 0.028 Uiso 1 1 calc R . . N1 N 0.33356(15) -0.2424(2) 1.00725(11) 0.0280(3) Uani 1 1 d . . . H2A H 0.731(2) 0.133(3) 0.741(2) 0.040(6) Uiso 1 1 d . . . H1 H 0.735(3) 0.063(3) 0.6288(19) 0.048(6) Uiso 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 0.0235(3) 0.0184(2) 0.0177(2) -0.00015(10) 0.00358(14) -0.00043(12) O1 0.0247(6) 0.0272(5) 0.0188(4) 0.0033(4) 0.0011(4) -0.0056(4) O2 0.0378(7) 0.0209(5) 0.0287(5) -0.0047(4) 0.0077(4) -0.0010(5) O3 0.0377(7) 0.0303(6) 0.0197(5) 0.0041(4) 0.0057(4) -0.0045(5) O5 0.0477(9) 0.0568(8) 0.0235(5) 0.0079(5) 0.0128(5) 0.0126(7) O4 0.0418(8) 0.0378(7) 0.0374(6) 0.0149(5) 0.0110(5) 0.0002(6) C2 0.0216(8) 0.0243(7) 0.0265(7) 0.0009(5) 0.0033(5) 0.0018(6) C1 0.0190(7) 0.0244(7) 0.0180(6) 0.0018(5) 0.0013(5) -0.0037(5) N2 0.0244(8) 0.0354(7) 0.0244(6) 0.0000(5) 0.0037(5) 0.0065(6) C4 0.0191(8) 0.0306(7) 0.0186(6) 0.0037(5) 0.0015(5) -0.0022(6) C6 0.0230(8) 0.0240(7) 0.0213(6) -0.0019(5) 0.0037(5) -0.0008(6) C3 0.0234(8) 0.0308(7) 0.0226(6) -0.0014(5) 0.0055(5) 0.0031(6) C5 0.0234(8) 0.0229(7) 0.0236(7) 0.0014(5) 0.0012(6) -0.0006(5) N1 0.0230(8) 0.0397(8) 0.0213(6) 0.0069(5) 0.0026(5) 0.0011(5) _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 1.4192(11) . ? S1 O2 1.4267(11) . ? S1 N2 1.5854(14) . ? S1 O1 1.6124(11) . ? O1 C1 1.4052(15) . ? O5 N1 1.2209(19) . ? O4 N1 1.2293(18) . ? C2 C3 1.388(2) . ? C2 C1 1.387(2) . ? C1 C6 1.389(2) . ? C4 C5 1.380(2) . ? C4 C3 1.392(2) . ? C4 N1 1.4713(18) . ? C6 C5 1.392(2) . ? 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 O2 122.14(7) . . ? O3 S1 N2 109.62(8) . . ? O2 S1 N2 107.44(7) . . ? O3 S1 O1 102.16(6) . . ? O2 S1 O1 107.15(7) . . ? N2 S1 O1 107.42(7) . . ? C1 O1 S1 118.44(8) . . ? C3 C2 C1 119.01(13) . . ? C6 C1 C2 122.72(13) . . ? C6 C1 O1 117.37(12) . . ? C2 C1 O1 119.82(13) . . ? C5 C4 C3 123.46(13) . . ? C5 C4 N1 118.63(13) . . ? C3 C4 N1 117.87(13) . . ? C1 C6 C5 118.47(14) . . ? C2 C3 C4 117.86(14) . . ? C4 C5 C6 118.44(13) . . ? O5 N1 O4 123.71(15) . . ? O5 N1 C4 118.37(13) . . ? O4 N1 C4 117.91(14) . . ? _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 28.49 _diffrn_measured_fraction_theta_full 0.918 _refine_diff_density_max 0.413 _refine_diff_density_min -0.402 _refine_diff_density_rms 0.063 # Attachment 'CMPD8.cif' data_jmwsw15 _database_code_depnum_ccdc_archive 'CCDC 285423' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3-nitrophenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 N2 O5 S' _chemical_formula_weight 218.19 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 'P2(1)/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 10.8417(13) _cell_length_b 8.2431(10) _cell_length_c 10.2599(13) _cell_angle_alpha 90.00 _cell_angle_beta 116.410(2) _cell_angle_gamma 90.00 _cell_volume 821.22(17) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3355 _cell_measurement_theta_min 3.32 _cell_measurement_theta_max 27.50 _exptl_crystal_description dagger _exptl_crystal_colour colourless _exptl_crystal_size_min 0.10 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.765 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.393 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5011 _diffrn_reflns_av_R_equivalents 0.0157 _diffrn_reflns_av_sigmaI/netI 0.0194 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 2.10 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1862 _reflns_number_gt 1764 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0529P)^2^+0.3332P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1862 _refine_ls_number_parameters 135 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0333 _refine_ls_R_factor_gt 0.0315 _refine_ls_wR_factor_ref 0.0911 _refine_ls_wR_factor_gt 0.0896 _refine_ls_goodness_of_fit_ref 1.109 _refine_ls_restrained_S_all 1.109 _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 0.96356(3) 0.22797(4) 0.05240(4) 0.01549(13) Uani 1 1 d . . . O1 O 0.80621(11) 0.17043(13) -0.03255(11) 0.0197(2) Uani 1 1 d . . . O2 O 0.99015(12) 0.28618(13) -0.06369(12) 0.0207(3) Uani 1 1 d . . . O4 O 0.70298(13) -0.40196(14) 0.02958(13) 0.0288(3) Uani 1 1 d . . . O3 O 1.04176(11) 0.09782(12) 0.14240(11) 0.0201(2) Uani 1 1 d . . . O5 O 0.60631(14) -0.39522(16) 0.17375(15) 0.0356(3) Uani 1 1 d . . . N2 N 0.65992(13) -0.32836(17) 0.10477(14) 0.0229(3) Uani 1 1 d . . . C2 C 0.73734(14) -0.07580(19) 0.03872(15) 0.0182(3) Uani 1 1 d . . . H2 H 0.7733 -0.1365 -0.0154 0.022 Uiso 1 1 calc R . . C1 C 0.74677(14) 0.09121(19) 0.04720(15) 0.0181(3) Uani 1 1 d . . . C6 C 0.69389(15) 0.1819(2) 0.12408(17) 0.0232(3) Uani 1 1 d . . . H6 H 0.7004 0.2969 0.1266 0.028 Uiso 1 1 calc R . . C4 C 0.62018(15) -0.0661(2) 0.19293(16) 0.0231(3) Uani 1 1 d . . . H4 H 0.5776 -0.1212 0.2435 0.028 Uiso 1 1 calc R . . C3 C 0.67288(14) -0.15084(19) 0.11288(15) 0.0193(3) Uani 1 1 d . . . N1 N 0.97130(14) 0.37433(17) 0.15446(16) 0.0209(3) Uani 1 1 d . . . C5 C 0.63103(16) 0.1016(2) 0.19750(18) 0.0259(4) Uani 1 1 d . . . H5 H 0.5950 0.1622 0.2515 0.031 Uiso 1 1 calc R . . H1B H 0.975(2) 0.352(3) 0.232(3) 0.036(6) Uiso 1 1 d . . . H1A H 0.937(2) 0.458(3) 0.117(3) 0.036(6) Uiso 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 0.0191(2) 0.0143(2) 0.0156(2) 0.00026(11) 0.00998(15) -0.00006(12) O1 0.0201(5) 0.0221(6) 0.0159(5) 0.0010(4) 0.0070(4) -0.0030(4) O2 0.0283(6) 0.0188(5) 0.0201(5) 0.0016(4) 0.0153(5) -0.0011(4) O4 0.0361(6) 0.0231(6) 0.0312(6) -0.0018(5) 0.0186(5) -0.0007(5) O3 0.0231(5) 0.0181(5) 0.0208(5) 0.0033(4) 0.0113(4) 0.0032(4) O5 0.0424(7) 0.0308(7) 0.0441(7) 0.0060(6) 0.0287(6) -0.0058(5) N2 0.0206(6) 0.0240(7) 0.0232(7) 0.0029(5) 0.0090(5) -0.0022(5) C2 0.0167(6) 0.0223(7) 0.0157(6) -0.0002(5) 0.0074(5) 0.0012(5) C1 0.0153(6) 0.0224(7) 0.0161(6) 0.0011(5) 0.0065(5) -0.0012(5) C6 0.0195(7) 0.0230(7) 0.0268(8) -0.0057(6) 0.0101(6) -0.0013(6) C4 0.0201(7) 0.0316(8) 0.0203(7) -0.0028(6) 0.0113(6) -0.0062(6) C3 0.0164(6) 0.0218(7) 0.0183(7) 0.0005(5) 0.0064(5) -0.0022(5) N1 0.0298(7) 0.0158(6) 0.0196(7) -0.0017(5) 0.0134(6) 0.0004(5) C5 0.0220(7) 0.0325(9) 0.0274(8) -0.0100(7) 0.0147(6) -0.0041(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 1.4234(11) . ? S1 O2 1.4274(11) . ? S1 N1 1.5751(13) . ? S1 O1 1.6038(11) . ? O1 C1 1.4072(17) . ? O4 N2 1.2254(18) . ? O5 N2 1.2282(18) . ? N2 C3 1.469(2) . ? C2 C1 1.380(2) . ? C2 C3 1.387(2) . ? C1 C6 1.383(2) . ? C6 C5 1.388(2) . ? C4 C3 1.381(2) . ? C4 C5 1.386(2) . ? 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 O2 120.77(7) . . ? O3 S1 N1 107.81(7) . . ? O2 S1 N1 109.05(7) . . ? O3 S1 O1 108.20(6) . . ? O2 S1 O1 101.93(6) . . ? N1 S1 O1 108.49(7) . . ? C1 O1 S1 118.22(9) . . ? O4 N2 O5 123.43(14) . . ? O4 N2 C3 118.38(12) . . ? O5 N2 C3 118.18(13) . . ? C1 C2 C3 116.85(14) . . ? C2 C1 C6 122.51(14) . . ? C2 C1 O1 117.80(13) . . ? C6 C1 O1 119.60(14) . . ? C1 C6 C5 118.65(15) . . ? C3 C4 C5 118.25(14) . . ? C4 C3 C2 122.91(15) . . ? C4 C3 N2 118.91(13) . . ? C2 C3 N2 118.18(13) . . ? C4 C5 C6 120.82(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 O1 C1 46.15(12) . . . . ? O2 S1 O1 C1 174.46(11) . . . . ? N1 S1 O1 C1 -70.55(12) . . . . ? C3 C2 C1 C6 -0.7(2) . . . . ? C3 C2 C1 O1 -177.20(12) . . . . ? S1 O1 C1 C2 -100.33(14) . . . . ? S1 O1 C1 C6 83.04(15) . . . . ? C2 C1 C6 C5 1.1(2) . . . . ? O1 C1 C6 C5 177.59(13) . . . . ? C5 C4 C3 C2 0.8(2) . . . . ? C5 C4 C3 N2 -178.89(13) . . . . ? C1 C2 C3 C4 -0.3(2) . . . . ? C1 C2 C3 N2 179.38(12) . . . . ? O4 N2 C3 C4 177.64(13) . . . . ? O5 N2 C3 C4 -2.3(2) . . . . ? O4 N2 C3 C2 -2.07(19) . . . . ? O5 N2 C3 C2 177.99(14) . . . . ? C3 C4 C5 C6 -0.3(2) . . . . ? C1 C6 C5 C4 -0.6(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.381 _refine_diff_density_min -0.420 _refine_diff_density_rms 0.063 # Attachment 'CMPD9.cif' data_jmwsw19 _database_code_depnum_ccdc_archive 'CCDC 285424' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-iodophenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 I N O3 S' _chemical_formula_weight 299.08 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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'Pna2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 22.457(6) _cell_length_b 8.135(2) _cell_length_c 4.7648(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 870.5(4) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3902 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 27.51 _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_min 0.14 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 3.884 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.59 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5030 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0319 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 29 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_limit_l_max 5 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1751 _reflns_number_gt 1737 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0423P)^2^+0.4276P] 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 0.04(3) _refine_ls_number_reflns 1751 _refine_ls_number_parameters 117 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0289 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0730 _refine_ls_wR_factor_gt 0.0727 _refine_ls_goodness_of_fit_ref 1.131 _refine_ls_restrained_S_all 1.131 _refine_ls_shift/su_max 0.002 _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 I I 0.542720(11) -0.34662(3) 0.32361(12) 0.03103(12) Uani 1 1 d . . . S S 0.71228(4) 0.38398(11) 0.0530(2) 0.01683(18) Uani 1 1 d . . . O3 O 0.71762(13) 0.5415(3) -0.0746(6) 0.0234(6) Uani 1 1 d . . . O2 O 0.71240(13) 0.3708(3) 0.3482(7) 0.0232(6) Uani 1 1 d . . . O1 O 0.64932(14) 0.3216(4) -0.0631(7) 0.0217(6) Uani 1 1 d . . . N1 N 0.76285(16) 0.2647(5) -0.0660(9) 0.0201(7) Uani 1 1 d D . . C1 C 0.62910(18) 0.1690(4) 0.0320(10) 0.0204(8) Uani 1 1 d . . . C2 C 0.64453(18) 0.0282(5) -0.1079(8) 0.0216(9) Uani 1 1 d . . . H2 H 0.6707 0.0326 -0.2589 0.026 Uiso 1 1 calc R . . C3 C 0.62072(19) -0.1209(5) -0.0225(9) 0.0228(9) Uani 1 1 d . . . H3 H 0.6314 -0.2179 -0.1125 0.027 Uiso 1 1 calc R . . C5 C 0.56506(16) 0.0178(5) 0.3384(12) 0.0227(7) Uani 1 1 d . . . H5 H 0.5382 0.0130 0.4867 0.027 Uiso 1 1 calc R . . C6 C 0.58948(19) 0.1680(5) 0.2572(8) 0.0224(10) Uani 1 1 d . . . H6 H 0.5796 0.2646 0.3506 0.027 Uiso 1 1 calc R . . C4 C 0.58099(17) -0.1234(4) 0.1976(10) 0.0208(8) Uani 1 1 d . . . H1A H 0.762(3) 0.262(10) -0.250(19) 0.06(2) Uiso 1 1 d . . . H1B H 0.770(4) 0.187(7) 0.064(13) 0.08(3) Uiso 1 1 d 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 I 0.04118(18) 0.01327(15) 0.03863(19) 0.00166(16) 0.00083(16) -0.00640(8) S 0.0304(4) 0.0079(3) 0.0122(4) -0.0005(4) 0.0000(4) -0.0009(3) O3 0.0427(16) 0.0105(13) 0.0171(12) 0.0017(11) 0.0000(11) -0.0022(11) O2 0.0383(15) 0.0181(12) 0.0131(15) -0.0024(13) 0.0004(14) -0.0009(10) O1 0.0302(15) 0.0128(12) 0.0222(14) 0.0047(12) -0.0021(12) -0.0016(11) N1 0.0295(19) 0.0142(16) 0.0165(15) -0.0022(15) 0.0032(13) 0.0034(13) C1 0.026(2) 0.0126(17) 0.022(2) 0.0042(16) -0.0070(16) -0.0018(13) C2 0.0268(18) 0.019(2) 0.019(2) -0.0035(14) 0.0040(13) 0.0014(14) C3 0.031(2) 0.0104(17) 0.027(3) -0.0041(16) -0.0008(16) 0.0019(15) C5 0.0273(16) 0.0196(17) 0.0214(19) 0.004(2) 0.003(2) -0.0008(13) C6 0.030(2) 0.0158(18) 0.021(3) -0.0038(13) 0.0017(14) 0.0029(14) C4 0.0239(19) 0.0123(16) 0.026(2) 0.0030(17) -0.0037(17) -0.0033(14) _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 I C4 2.097(4) . ? S O2 1.411(4) . ? S O3 1.423(3) . ? S N1 1.598(4) . ? S O1 1.601(3) . ? O1 C1 1.397(4) . ? N1 H1A 0.88(9) . ? N1 H1B 0.900(5) . ? C1 C2 1.370(5) . ? C1 C6 1.394(6) . ? C2 C3 1.387(6) . ? C2 H2 0.9300 . ? C3 C4 1.377(6) . ? C3 H3 0.9300 . ? C5 C4 1.378(6) . ? C5 C6 1.394(5) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? 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 S O3 119.59(18) . . ? O2 S N1 107.8(2) . . ? O3 S N1 109.6(2) . . ? O2 S O1 108.79(18) . . ? O3 S O1 102.26(17) . . ? N1 S O1 108.2(2) . . ? C1 O1 S 117.2(3) . . ? S N1 H1A 110(5) . . ? S N1 H1B 108(6) . . ? H1A N1 H1B 132(7) . . ? C2 C1 C6 122.1(4) . . ? C2 C1 O1 120.2(4) . . ? C6 C1 O1 117.5(3) . . ? C1 C2 C3 119.4(4) . . ? C1 C2 H2 120.3 . . ? C3 C2 H2 120.3 . . ? C4 C3 C2 119.1(4) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C4 C5 C6 119.6(4) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C6 C1 118.0(4) . . ? C5 C6 H6 121.0 . . ? C1 C6 H6 121.0 . . ? C3 C4 C5 121.8(4) . . ? C3 C4 I 119.8(3) . . ? C5 C4 I 118.4(3) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S O1 C1 -50.4(3) . . . . ? O3 S O1 C1 -177.8(3) . . . . ? N1 S O1 C1 66.5(4) . . . . ? S O1 C1 C2 -88.5(4) . . . . ? S O1 C1 C6 96.4(4) . . . . ? C6 C1 C2 C3 -0.7(6) . . . . ? O1 C1 C2 C3 -175.5(4) . . . . ? C1 C2 C3 C4 1.5(6) . . . . ? C4 C5 C6 C1 0.6(6) . . . . ? C2 C1 C6 C5 -0.3(6) . . . . ? O1 C1 C6 C5 174.6(4) . . . . ? C2 C3 C4 C5 -1.2(6) . . . . ? C2 C3 C4 I 178.4(3) . . . . ? C6 C5 C4 C3 0.1(7) . . . . ? C6 C5 C4 I -179.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 1.414 _refine_diff_density_min -0.825 _refine_diff_density_rms 0.129 # Attachment 'CMPD13.cif' data_jmwsw16 _database_code_depnum_ccdc_archive 'CCDC 285425' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'phenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H7 N O3 S' _chemical_formula_weight 173.19 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 'Pca2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y, z' '-x+1/2, y, z+1/2' _cell_length_a 8.0387(6) _cell_length_b 5.3810(4) _cell_length_c 16.5114(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 714.22(9) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3123 _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 27.51 _exptl_crystal_description triangular _exptl_crystal_colour colourless _exptl_crystal_size_min 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.611 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 0.405 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4026 _diffrn_reflns_av_R_equivalents 0.0533 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 27.51 _reflns_number_total 1611 _reflns_number_gt 1590 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0555P)^2^+0.0634P] 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(7) _refine_ls_number_reflns 1611 _refine_ls_number_parameters 108 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0315 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0826 _refine_ls_wR_factor_gt 0.0824 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.062 _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 0.42645(5) 0.80931(8) 0.83939(3) 0.01864(14) Uani 1 1 d . . . O1 O 0.35059(19) 0.6731(2) 0.91665(8) 0.0211(3) Uani 1 1 d . . . C5 C 0.4388(2) 0.9370(4) 1.11759(12) 0.0234(4) Uani 1 1 d . . . H5 H 0.4074 1.0744 1.1503 0.028 Uiso 1 1 calc R . . C1 C 0.4244(2) 0.7120(4) 0.99347(11) 0.0187(4) Uani 1 1 d . . . O2 O 0.44632(17) 1.0664(3) 0.85827(8) 0.0256(3) Uani 1 1 d . . . O3 O 0.31600(18) 0.7339(3) 0.77686(9) 0.0256(3) Uani 1 1 d . . . C4 C 0.5467(3) 0.7583(4) 1.14801(12) 0.0237(4) Uani 1 1 d . . . H4 H 0.5894 0.7747 1.2014 0.028 Uiso 1 1 calc R . . C6 C 0.3768(2) 0.9150(3) 1.03922(12) 0.0218(4) Uani 1 1 d . . . H6 H 0.3034 1.0366 1.0177 0.026 Uiso 1 1 calc R . . C3 C 0.5925(2) 0.5550(4) 1.10072(12) 0.0233(4) Uani 1 1 d . . . H3 H 0.6655 0.4326 1.1221 0.028 Uiso 1 1 calc R . . C2 C 0.5314(2) 0.5314(3) 1.02221(11) 0.0209(4) Uani 1 1 d . . . H2 H 0.5626 0.3945 0.9892 0.025 Uiso 1 1 calc R . . N1 N 0.6055(2) 0.6969(4) 0.82218(12) 0.0257(4) Uani 1 1 d . . . H1B H 0.688(3) 0.767(5) 0.846(2) 0.030(6) Uiso 1 1 d . . . H1A H 0.608(4) 0.577(5) 0.8153(16) 0.027(8) Uiso 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 0.0183(2) 0.0214(2) 0.0163(2) 0.00107(17) 0.00029(18) 0.00104(13) O1 0.0194(7) 0.0266(7) 0.0172(6) 0.0006(5) 0.0011(5) -0.0040(5) C5 0.0256(10) 0.0223(9) 0.0224(9) -0.0044(7) 0.0032(7) -0.0015(7) C1 0.0188(9) 0.0221(9) 0.0151(9) 0.0012(6) 0.0009(6) -0.0047(6) O2 0.0310(7) 0.0220(7) 0.0238(7) 0.0018(5) 0.0011(5) 0.0010(5) O3 0.0232(7) 0.0342(7) 0.0195(6) 0.0007(6) -0.0031(6) -0.0003(6) C4 0.0216(8) 0.0298(9) 0.0197(9) -0.0007(8) -0.0003(7) -0.0025(8) C6 0.0206(8) 0.0211(9) 0.0236(9) 0.0020(7) 0.0017(7) 0.0012(7) C3 0.0219(9) 0.0260(10) 0.0219(9) 0.0031(7) -0.0002(7) 0.0023(7) C2 0.0202(8) 0.0221(9) 0.0204(8) -0.0011(7) 0.0038(7) -0.0002(7) N1 0.0202(8) 0.0258(10) 0.0310(12) -0.0029(7) 0.0020(7) 0.0014(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 1.4209(15) . ? S1 O2 1.4272(15) . ? S1 N1 1.5865(19) . ? S1 O1 1.5926(14) . ? O1 C1 1.416(2) . ? C5 C4 1.389(3) . ? C5 C6 1.392(3) . ? C5 H5 0.9500 . ? C1 C2 1.382(3) . ? C1 C6 1.382(3) . ? C4 C3 1.393(3) . ? C4 H4 0.9500 . ? C6 H6 0.9500 . ? C3 C2 1.392(3) . ? C3 H3 0.9500 . ? C2 H2 0.9500 . ? N1 H1B 0.86(3) . ? N1 H1A 0.66(3) . ? 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 O2 120.36(9) . . ? O3 S1 N1 109.13(10) . . ? O2 S1 N1 107.88(10) . . ? O3 S1 O1 102.20(8) . . ? O2 S1 O1 108.31(8) . . ? N1 S1 O1 108.38(9) . . ? C1 O1 S1 119.28(12) . . ? C4 C5 C6 120.08(19) . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C2 C1 C6 122.72(18) . . ? C2 C1 O1 117.68(17) . . ? C6 C1 O1 119.36(17) . . ? C5 C4 C3 120.39(19) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C1 C6 C5 118.42(18) . . ? C1 C6 H6 120.8 . . ? C5 C6 H6 120.8 . . ? C2 C3 C4 120.02(18) . . ? C2 C3 H3 120.0 . . ? C4 C3 H3 120.0 . . ? C1 C2 C3 118.37(17) . . ? C1 C2 H2 120.8 . . ? C3 C2 H2 120.8 . . ? S1 N1 H1B 117.0(17) . . ? S1 N1 H1A 116(3) . . ? H1B N1 H1A 119(3) . . ? 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 O3 S1 O1 C1 -177.39(14) . . . . ? O2 S1 O1 C1 -49.35(15) . . . . ? N1 S1 O1 C1 67.45(16) . . . . ? S1 O1 C1 C2 -99.91(17) . . . . ? S1 O1 C1 C6 85.49(19) . . . . ? C6 C5 C4 C3 -0.5(3) . . . . ? C2 C1 C6 C5 -0.3(3) . . . . ? O1 C1 C6 C5 173.98(17) . . . . ? C4 C5 C6 C1 0.3(3) . . . . ? C5 C4 C3 C2 0.6(3) . . . . ? C6 C1 C2 C3 0.5(3) . . . . ? O1 C1 C2 C3 -173.95(16) . . . . ? C4 C3 C2 C1 -0.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.51 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.412 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.055 # Attachment 'CMPD10.cif' data_jmwsw21 _database_code_depnum_ccdc_archive 'CCDC 285426' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-cyanophenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C7 H6 N2 O3 S' _chemical_formula_weight 198.20 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 'P2(1)/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 4.9239(5) _cell_length_b 14.8822(14) _cell_length_c 11.2090(11) _cell_angle_alpha 90.00 _cell_angle_beta 96.432(2) _cell_angle_gamma 90.00 _cell_volume 816.21(14) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2929 _cell_measurement_theta_min 2.28 _cell_measurement_theta_max 27.47 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_max 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.613 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 408 _exptl_absorpt_coefficient_mu 0.369 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5030 _diffrn_reflns_av_R_equivalents 0.0342 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.28 _diffrn_reflns_theta_max 27.48 _reflns_number_total 1863 _reflns_number_gt 1690 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^+0.2476P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1863 _refine_ls_number_parameters 126 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0375 _refine_ls_wR_factor_ref 0.1035 _refine_ls_wR_factor_gt 0.1008 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_restrained_S_all 1.108 _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 0.03731(8) 0.48929(3) 0.78145(3) 0.01588(15) Uani 1 1 d . . . O1 O -0.0432(2) 0.57382(8) 0.69612(11) 0.0191(3) Uani 1 1 d . . . O2 O 0.1666(3) 0.42447(8) 0.71396(12) 0.0229(3) Uani 1 1 d . . . O3 O -0.2157(3) 0.46884(9) 0.82476(11) 0.0225(3) Uani 1 1 d . . . N1 N 0.2511(3) 0.52273(11) 0.88807(14) 0.0202(3) Uani 1 1 d . . . C7 C 0.7368(4) 0.78278(12) 0.50224(16) 0.0226(4) Uani 1 1 d . . . C4 C 0.5415(4) 0.72720(12) 0.55405(15) 0.0189(4) Uani 1 1 d . . . N2 N 0.8910(4) 0.82751(12) 0.46179(15) 0.0301(4) Uani 1 1 d . . . C6 C 0.2471(4) 0.70225(12) 0.70685(16) 0.0213(4) Uani 1 1 d . . . H6 H 0.1732 0.7204 0.7778 0.026 Uiso 1 1 calc R . . C5 C 0.4379(4) 0.75506(12) 0.65826(16) 0.0219(4) Uani 1 1 d . . . H5 H 0.4976 0.8099 0.6958 0.026 Uiso 1 1 calc R . . C3 C 0.4592(4) 0.64657(12) 0.49850(16) 0.0207(4) Uani 1 1 d . . . H3 H 0.5322 0.6281 0.4275 0.025 Uiso 1 1 calc R . . C2 C 0.2697(4) 0.59364(12) 0.54782(15) 0.0201(4) Uani 1 1 d . . . H2 H 0.2118 0.5381 0.5116 0.024 Uiso 1 1 calc R . . C1 C 0.1661(3) 0.62276(12) 0.65066(15) 0.0170(3) Uani 1 1 d . . . H1B H 0.191(5) 0.5636(16) 0.928(2) 0.028(6) Uiso 1 1 d . . . H1A H 0.409(5) 0.5235(16) 0.874(2) 0.030(6) Uiso 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 0.0138(2) 0.0164(2) 0.0180(2) 0.00105(14) 0.00423(16) 0.00077(14) O1 0.0139(6) 0.0207(7) 0.0232(6) 0.0060(5) 0.0037(5) -0.0005(4) O2 0.0242(7) 0.0220(7) 0.0233(7) -0.0032(5) 0.0066(5) 0.0029(5) O3 0.0168(6) 0.0230(7) 0.0288(7) 0.0045(5) 0.0075(5) -0.0010(5) N1 0.0156(8) 0.0266(9) 0.0189(8) -0.0022(6) 0.0038(6) 0.0027(6) C7 0.0249(9) 0.0222(9) 0.0210(9) 0.0019(7) 0.0041(7) 0.0009(7) C4 0.0180(8) 0.0196(8) 0.0195(9) 0.0047(6) 0.0033(6) 0.0006(7) N2 0.0336(9) 0.0282(9) 0.0299(9) 0.0030(7) 0.0105(7) -0.0071(7) C6 0.0252(9) 0.0212(9) 0.0186(8) -0.0015(6) 0.0069(7) 0.0001(7) C5 0.0258(9) 0.0177(9) 0.0226(9) -0.0017(7) 0.0037(7) -0.0022(7) C3 0.0224(9) 0.0232(9) 0.0175(8) 0.0000(6) 0.0065(7) 0.0001(7) C2 0.0223(9) 0.0185(8) 0.0194(8) -0.0015(6) 0.0017(7) -0.0018(7) C1 0.0137(7) 0.0188(8) 0.0184(8) 0.0042(6) 0.0021(6) 0.0000(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 1.4199(13) . ? S1 O2 1.4199(13) . ? S1 N1 1.5820(16) . ? S1 O1 1.6030(12) . ? O1 C1 1.4037(19) . ? N1 H1B 0.83(2) . ? N1 H1A 0.81(3) . ? C7 N2 1.141(2) . ? C7 C4 1.439(2) . ? C4 C5 1.389(2) . ? C4 C3 1.391(3) . ? C6 C1 1.378(2) . ? C6 C5 1.382(2) . ? C6 H6 0.9500 . ? C5 H5 0.9500 . ? C3 C2 1.383(2) . ? C3 H3 0.9500 . ? C2 C1 1.382(2) . ? C2 H2 0.9500 . ? 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 O2 119.98(8) . . ? O3 S1 N1 110.14(8) . . ? O2 S1 N1 108.42(9) . . ? O3 S1 O1 101.78(7) . . ? O2 S1 O1 108.12(7) . . ? N1 S1 O1 107.64(8) . . ? C1 O1 S1 118.76(10) . . ? S1 N1 H1B 113.1(17) . . ? S1 N1 H1A 115.6(17) . . ? H1B N1 H1A 120(2) . . ? N2 C7 C4 179.4(2) . . ? C5 C4 C3 121.17(16) . . ? C5 C4 C7 119.52(16) . . ? C3 C4 C7 119.31(16) . . ? C1 C6 C5 118.86(16) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C6 C5 C4 119.43(16) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C2 C3 C4 119.23(16) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C1 C2 C3 118.92(16) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C6 C1 C2 122.38(16) . . ? C6 C1 O1 117.79(15) . . ? C2 C1 O1 119.67(15) . . ? 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 O3 S1 O1 C1 170.04(12) . . . . ? O2 S1 O1 C1 -62.71(14) . . . . ? N1 S1 O1 C1 54.22(14) . . . . ? N2 C7 C4 C5 -16(21) . . . . ? N2 C7 C4 C3 163(21) . . . . ? C1 C6 C5 C4 0.4(3) . . . . ? C3 C4 C5 C6 -0.8(3) . . . . ? C7 C4 C5 C6 179.01(17) . . . . ? C5 C4 C3 C2 0.3(3) . . . . ? C7 C4 C3 C2 -179.44(17) . . . . ? C4 C3 C2 C1 0.4(3) . . . . ? C5 C6 C1 C2 0.4(3) . . . . ? C5 C6 C1 O1 -175.07(16) . . . . ? C3 C2 C1 C6 -0.8(3) . . . . ? C3 C2 C1 O1 174.56(15) . . . . ? S1 O1 C1 C6 -100.18(17) . . . . ? S1 O1 C1 C2 84.25(17) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.391 _refine_diff_density_min -0.376 _refine_diff_density_rms 0.077 # Attachment 'CMPD11.cif' data_jmwsw27 _database_code_depnum_ccdc_archive 'CCDC 285427' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '4-chlorophenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 Cl N O3 S' _chemical_formula_weight 207.63 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' Cl Cl 0.1484 0.1585 '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 'P2(1)/n ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.8116(3) _cell_length_b 20.2367(14) _cell_length_c 8.5704(6) _cell_angle_alpha 90.00 _cell_angle_beta 94.7730(10) _cell_angle_gamma 90.00 _cell_volume 831.61(10) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3810 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 424 _exptl_absorpt_coefficient_mu 0.673 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5148 _diffrn_reflns_av_R_equivalents 0.0145 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 27.50 _reflns_number_total 1876 _reflns_number_gt 1780 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0673P)^2^+0.2726P] 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 SHELXL _refine_ls_extinction_coef 0.006(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1876 _refine_ls_number_parameters 118 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0298 _refine_ls_R_factor_gt 0.0286 _refine_ls_wR_factor_ref 0.0894 _refine_ls_wR_factor_gt 0.0883 _refine_ls_goodness_of_fit_ref 0.945 _refine_ls_restrained_S_all 0.945 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.79781(6) 0.236888(18) 0.22532(4) 0.02449(14) Uani 1 1 d . . . Cl1 Cl 0.06034(9) 0.52387(2) 0.26642(5) 0.04446(16) Uani 1 1 d . . . O2 O 0.6133(2) 0.22989(5) 0.08703(11) 0.0301(3) Uani 1 1 d . . . O1 O 0.8931(2) 0.31236(6) 0.24032(12) 0.0308(2) Uani 1 1 d . . . N1 N 0.6303(2) 0.21946(6) 0.37196(13) 0.0254(3) Uani 1 1 d . . . O3 O 1.0587(2) 0.20306(6) 0.23699(12) 0.0343(3) Uani 1 1 d . . . C2 C 0.6034(3) 0.38023(7) 0.38997(16) 0.0319(3) Uani 1 1 d . . . H2 H 0.6843 0.3603 0.4833 0.038 Uiso 1 1 calc R . . C5 C 0.3704(3) 0.43774(8) 0.11333(18) 0.0351(3) Uani 1 1 d . . . H5 H 0.2885 0.4574 0.0199 0.042 Uiso 1 1 calc R . . C1 C 0.6809(3) 0.36042(7) 0.24537(17) 0.0290(3) Uani 1 1 d . . . C3 C 0.4053(3) 0.42975(8) 0.39626(17) 0.0342(3) Uani 1 1 d . . . H3 H 0.3466 0.4438 0.4940 0.041 Uiso 1 1 calc R . . C6 C 0.5672(3) 0.38805(8) 0.10641(17) 0.0331(3) Uani 1 1 d . . . H6 H 0.6229 0.3732 0.0086 0.040 Uiso 1 1 calc R . . C4 C 0.2942(3) 0.45848(8) 0.25802(19) 0.0332(3) Uani 1 1 d . . . H1A H 0.719(4) 0.2263(9) 0.459(2) 0.037(5) Uiso 1 1 d . . . H1B H 0.451(5) 0.2263(9) 0.352(2) 0.039(5) Uiso 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 0.0149(2) 0.0413(2) 0.0170(2) -0.00149(12) -0.00046(12) -0.00163(11) Cl1 0.0466(3) 0.0390(2) 0.0456(3) -0.00050(16) -0.00928(19) 0.00196(17) O2 0.0221(5) 0.0483(6) 0.0191(5) -0.0018(4) -0.0035(4) -0.0026(4) O1 0.0210(5) 0.0433(6) 0.0278(5) 0.0018(4) -0.0003(4) -0.0085(4) N1 0.0160(5) 0.0409(6) 0.0191(6) 0.0033(5) -0.0004(4) -0.0007(5) O3 0.0174(5) 0.0580(7) 0.0271(5) -0.0083(5) -0.0001(4) 0.0043(4) C2 0.0372(8) 0.0343(7) 0.0233(7) 0.0024(5) -0.0033(6) -0.0082(6) C5 0.0367(8) 0.0393(8) 0.0277(7) 0.0069(6) -0.0075(6) -0.0109(6) C1 0.0249(7) 0.0348(7) 0.0267(7) 0.0022(5) -0.0009(5) -0.0106(5) C3 0.0409(8) 0.0347(7) 0.0264(7) -0.0011(6) -0.0014(6) -0.0073(6) C6 0.0341(7) 0.0414(8) 0.0236(7) 0.0031(6) -0.0002(5) -0.0108(6) C4 0.0329(8) 0.0312(7) 0.0340(8) 0.0021(6) -0.0049(6) -0.0084(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 1.4259(11) . ? S1 O2 1.4276(10) . ? S1 N1 1.5881(12) . ? S1 O1 1.5968(11) . ? Cl1 C4 1.7426(17) . ? O1 C1 1.4134(19) . ? N1 H1A 0.84(2) . ? N1 H1B 0.88(2) . ? C2 C1 1.383(2) . ? C2 C3 1.387(2) . ? C2 H2 0.9500 . ? C5 C6 1.386(2) . ? C5 C4 1.387(2) . ? C5 H5 0.9500 . ? C1 C6 1.386(2) . ? C3 C4 1.386(2) . ? C3 H3 0.9500 . ? C6 H6 0.9500 . ? 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 O2 119.58(6) . . ? O3 S1 N1 109.86(7) . . ? O2 S1 N1 108.27(6) . . ? O3 S1 O1 102.02(6) . . ? O2 S1 O1 108.44(6) . . ? N1 S1 O1 108.06(6) . . ? C1 O1 S1 117.22(8) . . ? S1 N1 H1A 114.1(14) . . ? S1 N1 H1B 111.5(13) . . ? H1A N1 H1B 124.7(19) . . ? C1 C2 C3 118.79(14) . . ? C1 C2 H2 120.6 . . ? C3 C2 H2 120.6 . . ? C6 C5 C4 119.35(14) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C2 C1 C6 122.44(15) . . ? C2 C1 O1 118.44(13) . . ? C6 C1 O1 119.06(13) . . ? C2 C3 C4 119.15(14) . . ? C2 C3 H3 120.4 . . ? C4 C3 H3 120.4 . . ? C5 C6 C1 118.57(14) . . ? C5 C6 H6 120.7 . . ? C1 C6 H6 120.7 . . ? C3 C4 C5 121.69(15) . . ? C3 C4 Cl1 119.18(13) . . ? C5 C4 Cl1 119.10(12) . . ? 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 O3 S1 O1 C1 -175.30(9) . . . . ? O2 S1 O1 C1 57.61(11) . . . . ? N1 S1 O1 C1 -59.53(11) . . . . ? C3 C2 C1 C6 -0.3(2) . . . . ? C3 C2 C1 O1 176.79(12) . . . . ? S1 O1 C1 C2 92.53(14) . . . . ? S1 O1 C1 C6 -90.32(14) . . . . ? C1 C2 C3 C4 -0.9(2) . . . . ? C4 C5 C6 C1 0.3(2) . . . . ? C2 C1 C6 C5 0.6(2) . . . . ? O1 C1 C6 C5 -176.45(12) . . . . ? C2 C3 C4 C5 1.8(2) . . . . ? C2 C3 C4 Cl1 -176.38(11) . . . . ? C6 C5 C4 C3 -1.4(2) . . . . ? C6 C5 C4 Cl1 176.70(11) . . . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.490 _refine_diff_density_min -0.335 _refine_diff_density_rms 0.056 # Attachment 'CMPD12.cif' data_jmwsw3 _database_code_depnum_ccdc_archive 'CCDC 285428' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3-chlorophenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H6 Cl N O3 S' _chemical_formula_weight 207.63 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.0414(9) _cell_length_b 6.9625(13) _cell_length_c 11.813(2) _cell_angle_alpha 90.00 _cell_angle_beta 92.276(4) _cell_angle_gamma 90.00 _cell_volume 414.30(13) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 2104 _cell_measurement_theta_min 3.40 _cell_measurement_theta_max 28.46 _exptl_crystal_description rod _exptl_crystal_colour COLOURLESS _exptl_crystal_size_min 0.07 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_max 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.664 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 212 _exptl_absorpt_coefficient_mu 0.676 _exptl_absorpt_correction_type multiscan _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details SADABS _exptl_special_details ; ? ; _diffrn_ambient_temperature 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 2988 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 28.46 _reflns_number_total 1796 _reflns_number_gt 1758 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0335P)^2^+0.0782P] 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 -0.04(7) _refine_ls_number_reflns 1796 _refine_ls_number_parameters 117 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0265 _refine_ls_R_factor_gt 0.0258 _refine_ls_wR_factor_ref 0.0677 _refine_ls_wR_factor_gt 0.0673 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _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 S S 0.66307(7) 0.23818(6) 0.59342(4) 0.02567(11) Uani 1 1 d . . . Cl Cl 1.34458(13) 0.86319(10) 0.81005(6) 0.05324(18) Uani 1 1 d . . . O2 O 0.3996(2) 0.2237(3) 0.54530(12) 0.0368(3) Uani 1 1 d . . . O1 O 0.6229(2) 0.3836(2) 0.69596(11) 0.0313(3) Uani 1 1 d . . . N1 N 0.8449(3) 0.3400(3) 0.50495(15) 0.0303(4) Uani 1 1 d . . . O3 O 0.7965(3) 0.0716(2) 0.63528(13) 0.0359(3) Uani 1 1 d . . . C2 C 0.9678(4) 0.6020(3) 0.75277(17) 0.0314(4) Uani 1 1 d . . . H2 H 0.9079 0.6891 0.6953 0.038 Uiso 1 1 calc R . . C3 C 1.1818(4) 0.6452(3) 0.82641(17) 0.0322(4) Uani 1 1 d . . . C1 C 0.8470(4) 0.4268(3) 0.76723(16) 0.0296(4) Uani 1 1 d . . . C4 C 1.2666(4) 0.5213(4) 0.91149(18) 0.0368(5) Uani 1 1 d . . . H4 H 1.4130 0.5542 0.9608 0.044 Uiso 1 1 calc R . . C5 C 1.1359(4) 0.3491(4) 0.92389(18) 0.0401(5) Uani 1 1 d . . . H5 H 1.1912 0.2638 0.9830 0.048 Uiso 1 1 calc R . . C6 C 0.9245(4) 0.2989(3) 0.85105(18) 0.0375(5) Uani 1 1 d . . . H6 H 0.8357 0.1796 0.8588 0.045 Uiso 1 1 calc R . . H1B H 0.993(6) 0.332(4) 0.524(2) 0.050(8) Uiso 1 1 d . . . H1A H 0.787(5) 0.444(4) 0.474(2) 0.034(6) Uiso 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 S 0.01811(17) 0.0250(2) 0.0339(2) -0.00043(19) 0.00057(14) -0.00045(18) Cl 0.0563(4) 0.0427(3) 0.0596(4) -0.0006(3) -0.0103(3) -0.0158(3) O2 0.0194(5) 0.0392(8) 0.0514(8) -0.0039(8) -0.0035(5) -0.0015(7) O1 0.0226(6) 0.0377(8) 0.0339(7) -0.0049(6) 0.0022(5) 0.0037(6) N1 0.0209(8) 0.0339(10) 0.0363(9) 0.0057(7) 0.0022(6) 0.0017(7) O3 0.0350(7) 0.0282(7) 0.0443(8) 0.0037(6) -0.0012(6) 0.0021(6) C2 0.0330(9) 0.0319(11) 0.0294(9) -0.0011(8) 0.0015(7) 0.0055(8) C3 0.0313(9) 0.0331(11) 0.0324(10) -0.0055(8) 0.0044(8) -0.0013(8) C1 0.0242(8) 0.0377(11) 0.0269(9) -0.0041(8) 0.0030(7) 0.0035(8) C4 0.0328(10) 0.0464(13) 0.0312(10) -0.0061(9) -0.0002(8) 0.0032(9) C5 0.0411(11) 0.0457(13) 0.0333(10) 0.0058(9) -0.0013(8) 0.0074(10) C6 0.0373(11) 0.0387(11) 0.0367(11) 0.0042(8) 0.0048(9) -0.0003(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag S O3 1.4195(15) . ? S O2 1.4273(12) . ? S N1 1.5844(17) . ? S O1 1.5977(15) . ? Cl C3 1.740(2) . ? O1 C1 1.415(2) . ? N1 H1B 0.77(3) . ? N1 H1A 0.86(3) . ? C2 C1 1.377(3) . ? C2 C3 1.392(3) . ? C2 H2 0.9500 . ? C3 C4 1.379(3) . ? C1 C6 1.377(3) . ? C4 C5 1.379(4) . ? C4 H4 0.9500 . ? C5 C6 1.388(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? 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 S O2 120.11(10) . . ? O3 S N1 108.46(9) . . ? O2 S N1 108.80(9) . . ? O3 S O1 109.03(9) . . ? O2 S O1 101.69(8) . . ? N1 S O1 108.10(9) . . ? C1 O1 S 117.62(11) . . ? S N1 H1B 111(2) . . ? S N1 H1A 117.4(16) . . ? H1B N1 H1A 120(3) . . ? C1 C2 C3 116.71(19) . . ? C1 C2 H2 121.6 . . ? C3 C2 H2 121.6 . . ? C4 C3 C2 122.0(2) . . ? C4 C3 Cl 119.49(17) . . ? C2 C3 Cl 118.47(17) . . ? C2 C1 C6 123.24(19) . . ? C2 C1 O1 117.47(18) . . ? C6 C1 O1 119.19(19) . . ? C5 C4 C3 119.05(19) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C4 C5 C6 120.8(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 118.2(2) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? 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 O3 S O1 C1 49.75(16) . . . . ? O2 S O1 C1 177.59(14) . . . . ? N1 S O1 C1 -67.96(16) . . . . ? C1 C2 C3 C4 -1.3(3) . . . . ? C1 C2 C3 Cl 178.94(14) . . . . ? C3 C2 C1 C6 1.5(3) . . . . ? C3 C2 C1 O1 177.64(16) . . . . ? S O1 C1 C2 103.49(18) . . . . ? S O1 C1 C6 -80.2(2) . . . . ? C2 C3 C4 C5 0.2(3) . . . . ? Cl C3 C4 C5 179.87(16) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C2 C1 C6 C5 -0.4(3) . . . . ? O1 C1 C6 C5 -176.51(17) . . . . ? C4 C5 C6 C1 -0.8(3) . . . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 28.46 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.204 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.045 # Attachment 'CMPD14.cif' data_jmwsw8 _database_code_depnum_ccdc_archive 'CCDC 285429' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '3,4-dinitrophenyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C6 H5 N3 O7 S' _chemical_formula_weight 263.19 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 'P2(1)/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 14.7131(8) _cell_length_b 6.9420(4) _cell_length_c 9.7229(6) _cell_angle_alpha 90.00 _cell_angle_beta 103.8040(10) _cell_angle_gamma 90.00 _cell_volume 964.40(10) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 4352 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 27.52 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.813 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 536 _exptl_absorpt_coefficient_mu 0.369 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4515 _diffrn_reflns_av_R_equivalents 0.0286 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.43 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1694 _reflns_number_gt 1639 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0460P)^2^+0.4790P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1694 _refine_ls_number_parameters 162 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0301 _refine_ls_R_factor_gt 0.0296 _refine_ls_wR_factor_ref 0.0819 _refine_ls_wR_factor_gt 0.0815 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group S1 S 0.89857(3) 0.10479(5) 0.70898(4) 0.01653(15) Uani 1 1 d . . . O4 O 0.84212(8) 0.83009(17) 0.38985(12) 0.0234(3) Uani 1 1 d . . . O1 O 0.84587(7) 0.29853(15) 0.73634(11) 0.0177(3) Uani 1 1 d . . . O5 O 0.69784(9) 0.92308(18) 0.35769(14) 0.0318(3) Uani 1 1 d . . . O2 O 0.96812(8) 0.08702(18) 0.83807(12) 0.0250(3) Uani 1 1 d . . . O6 O 0.59652(9) 0.6389(2) 0.17690(13) 0.0344(3) Uani 1 1 d . . . O3 O 0.83021(8) -0.04115(16) 0.66620(12) 0.0225(3) Uani 1 1 d . . . N3 N 0.57661(10) 0.6251(2) 0.29112(15) 0.0249(3) Uani 1 1 d . . . N2 N 0.76030(10) 0.80433(19) 0.39329(14) 0.0207(3) Uani 1 1 d . . . C2 C 0.80356(10) 0.5367(2) 0.55756(15) 0.0173(3) Uani 1 1 d . . . H2 H 0.8649 0.5886 0.5859 0.021 Uiso 1 1 calc R . . N1 N 0.94567(11) 0.1477(2) 0.58169(16) 0.0229(3) Uani 1 1 d . . . C6 C 0.69025(11) 0.2944(2) 0.58251(17) 0.0203(3) Uani 1 1 d . . . H6 H 0.6752 0.1825 0.6288 0.024 Uiso 1 1 calc R . . C1 C 0.77851(11) 0.3744(2) 0.62146(15) 0.0166(3) Uani 1 1 d . . . C5 C 0.62392(11) 0.3806(2) 0.47448(18) 0.0219(4) Uani 1 1 d . . . H5 H 0.5628 0.3277 0.4455 0.026 Uiso 1 1 calc R . . C4 C 0.64731(11) 0.5431(2) 0.40959(16) 0.0194(3) Uani 1 1 d . . . O7 O 0.50194(9) 0.6705(3) 0.31399(15) 0.0480(4) Uani 1 1 d . . . C3 C 0.73659(11) 0.6213(2) 0.45112(16) 0.0176(3) Uani 1 1 d . . . H1A H 0.9145(17) 0.120(3) 0.504(3) 0.039(7) Uiso 1 1 d . . . H1B H 0.9852(17) 0.239(4) 0.593(2) 0.038(6) Uiso 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 0.0183(2) 0.0170(2) 0.0142(2) 0.00091(13) 0.00389(16) 0.00253(14) O4 0.0258(6) 0.0246(6) 0.0214(6) -0.0011(5) 0.0087(5) -0.0051(5) O1 0.0200(6) 0.0179(6) 0.0143(5) -0.0006(4) 0.0020(4) 0.0031(4) O5 0.0334(7) 0.0246(7) 0.0353(7) 0.0099(5) 0.0040(6) 0.0074(5) O2 0.0235(6) 0.0308(7) 0.0186(6) 0.0017(5) 0.0005(5) 0.0076(5) O6 0.0360(7) 0.0481(8) 0.0181(6) 0.0037(6) 0.0045(5) 0.0105(6) O3 0.0277(6) 0.0179(6) 0.0226(6) 0.0002(5) 0.0073(5) -0.0019(5) N3 0.0208(7) 0.0311(8) 0.0210(8) 0.0024(6) 0.0014(6) 0.0026(6) N2 0.0270(8) 0.0190(7) 0.0153(7) 0.0003(5) 0.0035(5) 0.0004(6) C2 0.0165(7) 0.0181(8) 0.0172(7) -0.0029(6) 0.0039(6) 0.0003(6) N1 0.0231(7) 0.0286(8) 0.0189(8) -0.0019(6) 0.0084(6) -0.0022(6) C6 0.0217(8) 0.0198(8) 0.0201(8) 0.0013(6) 0.0066(6) -0.0015(6) C1 0.0182(8) 0.0179(8) 0.0137(7) -0.0015(6) 0.0038(6) 0.0035(6) C5 0.0164(8) 0.0262(9) 0.0231(8) -0.0026(7) 0.0044(6) -0.0027(6) C4 0.0174(8) 0.0246(8) 0.0154(7) -0.0003(6) 0.0021(6) 0.0048(6) O7 0.0221(7) 0.0838(12) 0.0395(8) 0.0237(8) 0.0099(6) 0.0208(7) C3 0.0206(8) 0.0172(8) 0.0156(7) -0.0006(6) 0.0056(6) 0.0010(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 1.4182(12) . ? S1 O2 1.4230(12) . ? S1 N1 1.5842(14) . ? S1 O1 1.6060(11) . ? O4 N2 1.2253(18) . ? O1 C1 1.4068(18) . ? O5 N2 1.2215(19) . ? O6 N3 1.218(2) . ? N3 O7 1.213(2) . ? N3 C4 1.470(2) . ? N2 C3 1.465(2) . ? C2 C3 1.378(2) . ? C2 C1 1.379(2) . ? C2 H2 0.9500 . ? N1 H1A 0.80(3) . ? N1 H1B 0.85(3) . ? C6 C1 1.380(2) . ? C6 C5 1.387(2) . ? C6 H6 0.9500 . ? C5 C4 1.376(2) . ? C5 H5 0.9500 . ? C4 C3 1.389(2) . ? 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 O2 120.47(7) . . ? O3 S1 N1 108.48(8) . . ? O2 S1 N1 110.42(8) . . ? O3 S1 O1 108.07(6) . . ? O2 S1 O1 101.56(6) . . ? N1 S1 O1 106.89(7) . . ? C1 O1 S1 117.29(9) . . ? O7 N3 O6 124.89(15) . . ? O7 N3 C4 117.33(14) . . ? O6 N3 C4 117.76(14) . . ? O5 N2 O4 124.84(14) . . ? O5 N2 C3 117.53(13) . . ? O4 N2 C3 117.55(13) . . ? C3 C2 C1 117.80(14) . . ? C3 C2 H2 121.1 . . ? C1 C2 H2 121.1 . . ? S1 N1 H1A 115.3(17) . . ? S1 N1 H1B 116.6(15) . . ? H1A N1 H1B 121(2) . . ? C1 C6 C5 118.72(15) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? C2 C1 C6 122.72(14) . . ? C2 C1 O1 116.76(13) . . ? C6 C1 O1 120.40(14) . . ? C4 C5 C6 119.54(15) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C5 C4 C3 120.65(15) . . ? C5 C4 N3 117.98(14) . . ? C3 C4 N3 121.30(15) . . ? C2 C3 C4 120.58(14) . . ? C2 C3 N2 117.68(14) . . ? C4 C3 N2 121.51(14) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O3 S1 O1 C1 -59.91(12) . . . . ? O2 S1 O1 C1 172.41(11) . . . . ? N1 S1 O1 C1 56.67(12) . . . . ? C3 C2 C1 C6 0.4(2) . . . . ? C3 C2 C1 O1 -175.66(13) . . . . ? C5 C6 C1 C2 0.1(2) . . . . ? C5 C6 C1 O1 175.99(14) . . . . ? S1 O1 C1 C2 -105.48(13) . . . . ? S1 O1 C1 C6 78.38(16) . . . . ? C1 C6 C5 C4 -0.3(2) . . . . ? C6 C5 C4 C3 0.1(2) . . . . ? C6 C5 C4 N3 177.19(15) . . . . ? O7 N3 C4 C5 57.4(2) . . . . ? O6 N3 C4 C5 -121.19(17) . . . . ? O7 N3 C4 C3 -125.57(18) . . . . ? O6 N3 C4 C3 55.9(2) . . . . ? C1 C2 C3 C4 -0.6(2) . . . . ? C1 C2 C3 N2 173.95(13) . . . . ? C5 C4 C3 C2 0.4(2) . . . . ? N3 C4 C3 C2 -176.60(14) . . . . ? C5 C4 C3 N2 -173.95(14) . . . . ? N3 C4 C3 N2 9.0(2) . . . . ? O5 N2 C3 C2 -144.61(15) . . . . ? O4 N2 C3 C2 32.4(2) . . . . ? O5 N2 C3 C4 29.9(2) . . . . ? O4 N2 C3 C4 -153.13(15) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.280 _refine_diff_density_min -0.576 _refine_diff_density_rms 0.085 # Attachment 'CMPD15.cif' data_jmwsw14 _database_code_depnum_ccdc_archive 'CCDC 285430' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common 'ethyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H7 N O3 S' _chemical_formula_weight 125.15 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 'Pbca ' 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' '-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 8.9053(11) _cell_length_b 8.2409(11) _cell_length_c 14.2486(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1045.7(2) _cell_formula_units_Z 8 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 3517 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 27.50 _exptl_crystal_description slab _exptl_crystal_colour colourless _exptl_crystal_size_min 0.15 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_max 0.50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.590 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 528 _exptl_absorpt_coefficient_mu 0.518 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5622 _diffrn_reflns_av_R_equivalents 0.0519 _diffrn_reflns_av_sigmaI/netI 0.0276 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.86 _diffrn_reflns_theta_max 27.52 _reflns_number_total 1202 _reflns_number_gt 1126 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0459P)^2^+0.3978P] 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 SHELXL _refine_ls_extinction_coef 0.0014(11) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1202 _refine_ls_number_parameters 74 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0323 _refine_ls_R_factor_gt 0.0304 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 -0.02886(3) 1.06444(4) 0.31218(2) 0.01779(16) Uani 1 1 d . . . O3 O -0.11435(11) 0.91780(12) 0.31653(7) 0.0239(3) Uani 1 1 d . . . O1 O 0.09084(12) 1.06285(10) 0.39302(7) 0.0232(3) Uani 1 1 d . . . O2 O -0.10398(11) 1.21611(13) 0.32407(7) 0.0252(3) Uani 1 1 d . . . N1 N 0.05720(15) 1.06642(15) 0.21381(10) 0.0211(3) Uani 1 1 d . . . C2 C 0.30111(17) 0.94823(19) 0.47283(11) 0.0288(3) Uani 1 1 d . . . H2A H 0.3726 1.0154 0.4379 0.043 Uiso 1 1 calc R . . H2B H 0.3504 0.8475 0.4925 0.043 Uiso 1 1 calc R . . H2C H 0.2664 1.0076 0.5283 0.043 Uiso 1 1 calc R . . C1 C 0.16939(17) 0.90870(17) 0.41128(11) 0.0264(3) Uani 1 1 d . . . H1A H 0.2038 0.8595 0.3516 0.032 Uiso 1 1 calc R . . H1B H 0.1016 0.8311 0.4432 0.032 Uiso 1 1 calc R . . H1 H 0.091(2) 0.979(3) 0.1972(13) 0.037(5) Uiso 1 1 d . . . H2 H 0.106(2) 1.139(3) 0.2050(15) 0.047(6) Uiso 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 0.0135(2) 0.0141(2) 0.0258(2) -0.00009(11) 0.00117(11) 0.00045(11) O3 0.0162(5) 0.0169(5) 0.0386(6) -0.0002(4) 0.0033(4) -0.0021(4) O1 0.0255(5) 0.0179(5) 0.0262(5) -0.0024(4) -0.0049(4) 0.0024(4) O2 0.0204(5) 0.0172(5) 0.0379(6) 0.0006(4) 0.0050(4) 0.0039(4) N1 0.0223(6) 0.0152(6) 0.0256(6) 0.0002(5) 0.0032(5) -0.0006(5) C2 0.0237(7) 0.0355(8) 0.0271(7) 0.0005(6) -0.0021(6) 0.0023(6) C1 0.0281(7) 0.0194(6) 0.0317(7) -0.0001(6) -0.0065(6) 0.0045(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 O2 1.4278(10) . ? S1 O3 1.4296(10) . ? S1 O1 1.5695(10) . ? S1 N1 1.5976(14) . ? O1 C1 1.4733(16) . ? N1 H1 0.81(2) . ? N1 H2 0.75(2) . ? C2 C1 1.500(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C1 H1A 0.9900 . ? C1 H1B 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 O2 S1 O3 119.03(6) . . ? O2 S1 O1 103.80(6) . . ? O3 S1 O1 108.83(6) . . ? O2 S1 N1 108.66(6) . . ? O3 S1 N1 107.59(7) . . ? O1 S1 N1 108.55(7) . . ? C1 O1 S1 117.34(8) . . ? S1 N1 H1 115.0(14) . . ? S1 N1 H2 115.5(17) . . ? H1 N1 H2 116(2) . . ? C1 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C1 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? O1 C1 C2 106.69(11) . . ? O1 C1 H1A 110.4 . . ? C2 C1 H1A 110.4 . . ? O1 C1 H1B 110.4 . . ? C2 C1 H1B 110.4 . . ? H1A C1 H1B 108.6 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O2 S1 O1 C1 168.99(10) . . . . ? O3 S1 O1 C1 41.27(11) . . . . ? N1 S1 O1 C1 -75.55(11) . . . . ? S1 O1 C1 C2 166.18(10) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.396 _refine_diff_density_min -0.289 _refine_diff_density_rms 0.057 # Attachment 'CMPD16.cif' data_jmwsw12 _database_code_depnum_ccdc_archive 'CCDC 285431' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common '2,2,2-trifluoroethyl sulfamate' _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C2 H4 F3 N O3 S' _chemical_formula_weight 179.12 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8598(12) _cell_length_b 4.9203(12) _cell_length_c 13.834(4) _cell_angle_alpha 83.262(4) _cell_angle_beta 87.319(4) _cell_angle_gamma 64.377(4) _cell_volume 296.21(13) _cell_formula_units_Z 2 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 1140 _cell_measurement_theta_min 2.97 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.05 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_max 0.45 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.008 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 180 _exptl_absorpt_coefficient_mu 0.560 _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 130(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 1508 _diffrn_reflns_av_R_equivalents 0.0989 _diffrn_reflns_av_sigmaI/netI 0.0704 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.48 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1020 _reflns_number_gt 932 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _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^ > 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^)+(0.0738P)^2^+0.1625P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1020 _refine_ls_number_parameters 107 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0524 _refine_ls_R_factor_gt 0.0487 _refine_ls_wR_factor_ref 0.1288 _refine_ls_wR_factor_gt 0.1269 _refine_ls_goodness_of_fit_ref 1.140 _refine_ls_restrained_S_all 1.140 _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 0.98448(16) 0.23342(16) 0.35889(5) 0.0182(3) Uani 1 1 d . . . O3 O 0.9609(5) -0.0438(5) 0.38140(16) 0.0235(6) Uani 1 1 d . . . O1 O 0.9285(5) 0.2968(5) 0.24433(16) 0.0237(6) Uani 1 1 d . . . F3 F 0.7971(5) 0.9263(5) 0.06975(16) 0.0420(6) Uani 1 1 d . . . O2 O 1.2600(5) 0.2512(5) 0.37775(17) 0.0265(6) Uani 1 1 d . . . F2 F 0.7047(6) 0.5415(5) 0.06109(17) 0.0481(7) Uani 1 1 d . . . N1 N 0.7130(6) 0.4926(7) 0.4079(2) 0.0218(7) Uani 1 1 d . . . F1 F 0.4755(5) 0.8452(6) 0.1669(2) 0.0559(8) Uani 1 1 d . . . C1 C 0.9954(8) 0.5325(8) 0.1932(3) 0.0261(8) Uani 1 1 d . . . C2 C 0.7416(8) 0.7105(8) 0.1223(3) 0.0297(8) Uani 1 1 d . . . H4 H 0.728(7) 0.636(9) 0.408(2) 0.009(9) Uiso 1 1 d . . . H1 H 1.001(8) 0.673(9) 0.236(3) 0.023(9) Uiso 1 1 d . . . H3 H 0.527(9) 0.500(9) 0.403(3) 0.023(9) Uiso 1 1 d . . . H2 H 1.186(13) 0.422(13) 0.161(4) 0.069(16) Uiso 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 0.0141(5) 0.0137(5) 0.0258(5) -0.0015(3) 0.0014(3) -0.0052(3) O3 0.0215(12) 0.0161(12) 0.0324(13) -0.0010(9) 0.0003(9) -0.0080(9) O1 0.0279(13) 0.0195(12) 0.0280(13) -0.0026(9) 0.0042(9) -0.0145(10) F3 0.0518(15) 0.0291(12) 0.0463(13) 0.0124(10) -0.0068(10) -0.0220(11) O2 0.0181(12) 0.0201(12) 0.0396(14) -0.0037(10) 0.0011(9) -0.0067(9) F2 0.0705(17) 0.0379(14) 0.0426(14) 0.0047(11) -0.0193(12) -0.0300(13) N1 0.0178(15) 0.0170(15) 0.0330(16) -0.0054(12) 0.0054(11) -0.0095(12) F1 0.0267(13) 0.0362(14) 0.0863(19) 0.0018(13) 0.0145(11) 0.0002(10) C1 0.0270(18) 0.0257(18) 0.0310(18) -0.0010(14) 0.0039(14) -0.0171(15) C2 0.0308(19) 0.0193(17) 0.0362(19) 0.0007(14) 0.0011(14) -0.0093(14) _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 1.415(2) . ? S1 O2 1.417(2) . ? S1 N1 1.579(3) . ? S1 O1 1.592(2) . ? O1 C1 1.436(4) . ? F3 C2 1.333(4) . ? F2 C2 1.323(4) . ? N1 H4 0.74(4) . ? N1 H3 0.89(4) . ? F1 C2 1.331(4) . ? C1 C2 1.492(5) . ? C1 H1 0.97(4) . ? C1 H2 0.97(6) . ? 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 O2 120.11(13) . . ? O3 S1 N1 109.54(15) . . ? O2 S1 N1 108.70(16) . . ? O3 S1 O1 102.13(13) . . ? O2 S1 O1 107.80(13) . . ? N1 S1 O1 107.83(14) . . ? C1 O1 S1 117.2(2) . . ? S1 N1 H4 116(3) . . ? S1 N1 H3 117(3) . . ? H4 N1 H3 119(4) . . ? O1 C1 C2 107.2(3) . . ? O1 C1 H1 112(2) . . ? C2 C1 H1 107(2) . . ? O1 C1 H2 104(3) . . ? C2 C1 H2 112(3) . . ? H1 C1 H2 115(4) . . ? F2 C2 F1 106.7(3) . . ? F2 C2 F3 107.6(3) . . ? F1 C2 F3 107.6(3) . . ? F2 C2 C1 112.8(3) . . ? F1 C2 C1 111.9(3) . . ? F3 C2 C1 110.0(3) . . ? 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 O3 S1 O1 C1 -168.0(2) . . . . ? O2 S1 O1 C1 -40.6(2) . . . . ? N1 S1 O1 C1 76.6(2) . . . . ? S1 O1 C1 C2 -137.1(2) . . . . ? O1 C1 C2 F2 -57.4(4) . . . . ? O1 C1 C2 F1 62.9(4) . . . . ? O1 C1 C2 F3 -177.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.413 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.102