data_2100458 _publ_contact_author_email S.Parsons@ed.ac.uk _publ_contact_author_name 'Simon Parsons' _journal_coeditor_code WS5036 _journal_date_accepted 2006-01-17 _journal_date_recd_electronic 2005-08-15 _journal_issue 1 _journal_name_full 'Acta Crystallographica, Section B' _journal_page_first 280 _journal_page_last 286 _journal_paper_category FA _journal_volume 62 _journal_year 2006 _chemical_formula_moiety 'C2 H6 O4 S1' _chemical_formula_sum 'C2 H6 O4 S1' _chemical_formula_weight 126.13 _chemical_melting_point ? _chemical_name_systematic dimethylsulfate _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall 'F 2 -2d' _symmetry_space_group_name_H-M 'F d d 2 ' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary Patterson _audit_creation_method CRYSTALS_ver_12.80 _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 12.0568(7) _cell_length_b 15.9176(10) _cell_length_c 5.8001(4) _cell_measurement_reflns_used 1014 _cell_measurement_temperature 220 _cell_measurement_theta_max 25 _cell_measurement_theta_min 3 _cell_volume 1113.13(12) _computing_cell_refinement 'SAINT (Siemens ,1995)' _computing_data_collection 'SMART (Siemens, 1993)' _computing_data_reduction 'SAINT (Siemens ,1995)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'DIRDIF-96 (Beurskens et al., 1996)' _diffrn_ambient_temperature 220 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device_type 'Bruker SMART' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.043 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 2198 _diffrn_reflns_theta_full 27.668 _diffrn_reflns_theta_max 30.405 _diffrn_reflns_theta_min 4.104 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.495 _exptl_absorpt_correction_T_max 0.69 _exptl_absorpt_correction_T_min 0.37 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS version 2004/1' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.505 _exptl_crystal_density_meas ? _exptl_crystal_description cylinder _exptl_crystal_F_000 528 _exptl_crystal_size_max 4.00 _exptl_crystal_size_mid 0.75 _exptl_crystal_size_min 0.75 _refine_diff_density_max 0.17 _refine_diff_density_min -0.11 _refine_ls_abs_structure_details 'Flack, 204 Friedel-pairs' _refine_ls_abs_structure_Flack 0.14(12) _refine_ls_extinction_coef 42(9) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' _refine_ls_goodness_of_fit_ref 0.9311 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 47 _refine_ls_number_reflns 740 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.0407 _refine_ls_R_factor_gt 0.0336 _refine_ls_shift/su_max 0.000165 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w=1/[\s^2^(F^2^) + 0.05 + 0.00P] where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.0864 _refine_ls_wR_factor_gt 0.0842 _refine_ls_wR_factor_ref 0.0864 _reflns_number_gt 594 _reflns_number_total 742 _reflns_threshold_expression I>2.00u(I) loop_ _symmetry_equiv_pos_as_xyz x,y,z x,y+1/2,z+1/2 x+1/2,y,z+1/2 x+1/2,y+1/2,z -x+1/4,y+1/4,z+1/4 -x+1/4,y+3/4,z+3/4 -x+3/4,y+1/4,z+3/4 -x+3/4,y+3/4,z+1/4 x+1/4,-y+1/4,z+1/4 x+1/4,-y+3/4,z+3/4 x+3/4,-y+1/4,z+3/4 x+3/4,-y+3/4,z+1/4 -x+1/2,-y,z+1/2 -x+1/2,-y+1/2,z+1 -x+1,-y,z+1 -x+1,-y+1/2,z+1/2 loop_ _atom_site_type_symbol _atom_site_label _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_disorder_assembly _atom_site_disorder_group S S1 0.2500 0.2500 0.9822(2) 0.0696 Uani 1.0000 . . O O2 0.33323(16) 0.2936(2) 1.1015(4) 0.1247 Uani 1.0000 . . O O3 0.30287(13) 0.18559(10) 0.8202(3) 0.0739 Uani 1.0000 . . C C4 0.3975(2) 0.2129(2) 0.6838(4) 0.0898 Uani 1.0000 . . H H41 0.421(2) 0.1670(14) 0.596(5) 0.160(2) Uiso 1.0000 . . H H42 0.4535(17) 0.2294(18) 0.784(4) 0.161(2) Uiso 1.0000 . . H H43 0.376(2) 0.2570(16) 0.582(5) 0.160(2) Uiso 1.0000 . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 S1 0.0634(4) 0.0963(5) 0.0492(3) 0.0091(5) 0.0000 0.0000 O2 0.0960(13) 0.181(2) 0.0973(16) 0.0163(16) -0.0266(15) -0.0594(18) O3 0.0740(9) 0.0635(8) 0.0841(11) 0.0041(8) 0.0032(8) 0.0017(7) C4 0.0813(14) 0.1009(17) 0.0873(19) 0.0041(14) 0.0248(14) -0.0142(15) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C 0.0033 0.0016 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O3 S1 O2 14_554 . 14_554 109.67(11) yes O3 S1 O2 14_554 . . 105.62(15) yes O2 S1 O2 14_554 . . 120.9(2) yes O3 S1 O3 14_554 . . 104.22(12) yes O2 S1 O3 14_554 . . 105.62(15) yes O2 S1 O3 . . . 109.67(11) yes S1 O3 C4 . . . 117.43(15) yes O3 C4 H41 . . . 107.5(15) no O3 C4 H42 . . . 108.4(15) no H41 C4 H42 . . . 110.1(16) no O3 C4 H43 . . . 109.9(16) no H41 C4 H43 . . . 108.7(16) no H42 C4 H43 . . . 112.2(17) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 O3 . 14_554 1.5297(17) yes S1 O2 . 14_554 1.403(2) yes S1 O2 . . 1.403(2) yes S1 O3 . . 1.5297(17) yes O3 C4 . . 1.455(3) yes C4 H41 . . 0.936(19) no C4 H42 . . 0.928(18) no C4 H43 . . 0.953(19) no