#------------------------------------------------------------------------------ #$Date: 2008-03-30 11:21:05 +0100 (Sun, 30 Mar 2008) $ #$Revision: 321 $ #$URL: svn://www.crystallography.net/cod/cif/2/2204301.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204301 loop_ _publ_author_name 'Xiao-Mao Zou' 'Huan-Le Shi' 'Li-Min Yu' 'Hua-Zheng Yang' 'Jiang Pei' 'Pei Liu' _publ_section_title ; Ethyl 5-(3,5-dimethyl-1H-pyrazol-1-ylsulfonyl)-1-methyl-1H-pyrazole- 4-carboxylate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o1812 _journal_page_last o1813 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C12 H16 N4 O4 S' _chemical_formula_moiety 'C12 H16 N4 O4 S' _chemical_formula_sum 'C12 H16 N4 O4 S' _chemical_formula_weight 312.35 _chemical_name_systematic ; Ethyl 5-(3,5-dimethyl-1H-pyrazol-1-ylsulfonyl)-1-methyl-1H-pyrazole- 4-carboxylate ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 21/n' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 93.765(7) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.604(3) _cell_length_b 12.868(5) _cell_length_c 15.732(6) _cell_measurement_reflns_used 1024 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 23.92 _cell_measurement_theta_min 2.60 _cell_volume 1536.0(10) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1999)' _computing_molecular_graphics 'SHELXTL (Bruker, 1999)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0499 _diffrn_reflns_av_sigmaI/netI 0.0642 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 8642 _diffrn_reflns_theta_full 26.44 _diffrn_reflns_theta_max 26.44 _diffrn_reflns_theta_min 2.05 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_T_max 0.944 _exptl_absorpt_correction_T_min 0.800 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.351 _exptl_crystal_density_meas none _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 656 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.216 _refine_diff_density_min -0.250 _refine_ls_extinction_coef 0.116(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.014 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 3156 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.0976 _refine_ls_R_factor_gt 0.0500 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0594P)^2^+0.0685P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1064 _refine_ls_wR_factor_ref 0.1238 _reflns_number_gt 1929 _reflns_number_total 3156 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6444.cif 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' 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' loop_ _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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol S1 1.06599(8) 0.19010(4) 0.48838(4) 0.0477(2) Uani d . 1 S O1 0.9874(2) 0.13070(13) 0.55128(12) 0.0643(5) Uani d . 1 O O2 1.2215(2) 0.15439(13) 0.45288(13) 0.0630(5) Uani d . 1 O O3 0.7358(2) 0.29290(17) 0.59013(14) 0.0778(6) Uani d . 1 O O4 0.8150(2) 0.42382(15) 0.67801(13) 0.0703(6) Uani d . 1 O N1 0.9139(3) 0.20881(15) 0.40946(13) 0.0504(5) Uani d . 1 N N2 0.9647(3) 0.27462(16) 0.34618(14) 0.0583(6) Uani d . 1 N N3 1.2505(2) 0.37153(16) 0.50783(13) 0.0472(5) Uani d . 1 N N4 1.2571(3) 0.46337(16) 0.54896(15) 0.0604(6) Uani d . 1 N C1 0.7505(3) 0.1650(2) 0.39076(19) 0.0583(7) Uani d . 1 C C2 0.6986(4) 0.2057(2) 0.3140(2) 0.0752(10) Uani d . 1 C H2 0.5926 0.1919 0.2832 0.090 Uiso calc R 1 H C3 0.8314(4) 0.2723(2) 0.28871(18) 0.0670(8) Uani d . 1 C C4 0.6637(4) 0.0902(2) 0.4466(2) 0.0801(10) Uani d . 1 C H4A 0.5486 0.0735 0.4217 0.120 Uiso calc R 1 H H4B 0.6533 0.1209 0.5017 0.120 Uiso calc R 1 H H4C 0.7332 0.0281 0.4525 0.120 Uiso calc R 1 H C5 0.8409(5) 0.3349(3) 0.2087(2) 0.1048(13) Uani d . 1 C H5A 0.9317 0.3865 0.2169 0.157 Uiso calc R 1 H H5B 0.7297 0.3685 0.1955 0.157 Uiso calc R 1 H H5C 0.8674 0.2899 0.1626 0.157 Uiso calc R 1 H C6 1.1054(3) 0.31688(17) 0.52560(14) 0.0405(6) Uani d . 1 C C7 1.0134(3) 0.37614(18) 0.58128(15) 0.0440(6) Uani d . 1 C C8 1.1148(3) 0.46572(19) 0.59302(17) 0.0544(7) Uani d . 1 C H8 1.0860 0.5208 0.6278 0.065 Uiso calc R 1 H C9 1.3913(4) 0.3487(2) 0.4510(2) 0.0687(8) Uani d . 1 C H9A 1.4643 0.2939 0.4750 0.103 Uiso calc R 1 H H9B 1.4614 0.4099 0.4445 0.103 Uiso calc R 1 H H9C 1.3401 0.3275 0.3964 0.103 Uiso calc R 1 H C10 0.8405(3) 0.3568(2) 0.61544(17) 0.0533(6) Uani d . 1 C C11 0.6476(4) 0.4165(3) 0.7172(2) 0.0911(11) Uani d . 1 C H11A 0.6403 0.3511 0.7473 0.109 Uiso calc R 1 H H11B 0.5510 0.4197 0.6738 0.109 Uiso calc R 1 H C12 0.6362(6) 0.5042(3) 0.7771(3) 0.1136(14) Uani d . 1 C H12A 0.7311 0.4998 0.8203 0.170 Uiso calc R 1 H H12B 0.5257 0.5013 0.8033 0.170 Uiso calc R 1 H H12C 0.6444 0.5686 0.7468 0.170 Uiso calc R 1 H 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 0.0494(4) 0.0417(4) 0.0506(4) 0.0017(3) -0.0085(3) 0.0002(3) O1 0.0783(12) 0.0487(10) 0.0649(12) -0.0094(9) -0.0035(10) 0.0160(9) O2 0.0508(10) 0.0578(11) 0.0793(13) 0.0131(8) -0.0043(10) -0.0121(10) O3 0.0599(12) 0.0836(14) 0.0909(16) -0.0181(11) 0.0125(11) -0.0185(12) O4 0.0740(13) 0.0764(13) 0.0627(13) -0.0034(10) 0.0220(10) -0.0132(11) N1 0.0507(12) 0.0480(11) 0.0507(13) -0.0037(9) -0.0093(10) -0.0032(10) N2 0.0702(14) 0.0590(13) 0.0438(13) 0.0013(11) -0.0109(11) -0.0030(11) N3 0.0475(12) 0.0491(12) 0.0446(12) -0.0036(9) -0.0007(10) -0.0008(10) N4 0.0622(14) 0.0544(14) 0.0640(15) -0.0123(11) -0.0010(12) -0.0064(11) C1 0.0452(14) 0.0514(16) 0.076(2) 0.0050(12) -0.0111(14) -0.0216(14) C2 0.0611(18) 0.080(2) 0.080(2) 0.0056(16) -0.0299(17) -0.0179(17) C3 0.077(2) 0.0699(18) 0.0503(18) 0.0200(16) -0.0209(16) -0.0139(14) C4 0.0541(17) 0.0636(18) 0.122(3) -0.0117(14) -0.0005(18) -0.0052(19) C5 0.136(3) 0.120(3) 0.054(2) 0.019(2) -0.027(2) 0.005(2) C6 0.0414(12) 0.0417(13) 0.0373(13) -0.0022(10) -0.0051(10) 0.0020(11) C7 0.0479(14) 0.0478(14) 0.0355(13) -0.0012(11) -0.0044(11) 0.0005(11) C8 0.0613(16) 0.0497(15) 0.0513(16) 0.0006(12) -0.0028(14) -0.0094(12) C9 0.0581(17) 0.0772(19) 0.072(2) -0.0123(14) 0.0158(16) -0.0071(16) C10 0.0560(16) 0.0556(15) 0.0480(16) 0.0063(13) 0.0014(13) 0.0028(13) C11 0.083(2) 0.111(3) 0.083(3) 0.0027(19) 0.037(2) 0.000(2) C12 0.145(4) 0.114(3) 0.089(3) 0.033(3) 0.059(3) 0.001(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S1 O1 1.4135(19) yes S1 O2 1.4171(18) yes S1 N1 1.658(2) yes S1 C6 1.753(2) yes O3 C10 1.195(3) yes O4 C10 1.332(3) yes O4 C11 1.453(3) yes N1 C1 1.378(3) yes N1 N2 1.382(3) yes N2 C3 1.314(3) Yes N3 N4 1.347(3) Yes N3 C6 1.353(3) Yes N3 C9 1.469(3) Yes N4 C8 1.323(3) Yes C1 C2 1.351(4) Yes C1 C4 1.487(4) Yes C2 C3 1.402(4) Yes C2 H2 0.93 ? C3 C5 1.500(5) Yes C4 H4A 0.96 ? C4 H4B 0.96 ? C4 H4C 0.96 ? C5 H5A 0.96 ? C5 H5B 0.96 ? C5 H5C 0.96 ? C6 C7 1.385(3) Yes C7 C8 1.392(3) Yes C7 C10 1.474(3) Yes C8 H8 0.93 ? C9 H9A 0.96 ? C9 H9B 0.96 ? C9 H9C 0.96 ? C11 C12 1.477(5) Yes C11 H11A 0.97 ? C11 H11B 0.97 ? C12 H12A 0.96 ? C12 H12B 0.96 ? C12 H12C 0.96 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O1 S1 O2 120.17(11) yes O1 S1 N1 107.25(11) yes O2 S1 N1 108.14(11) yes O1 S1 C6 109.90(11) yes O2 S1 C6 107.74(11) yes N1 S1 C6 102.16(10) yes C10 O4 C11 116.5(2) yes C1 N1 N2 112.8(2) yes C1 N1 S1 132.5(2) yes N2 N1 S1 114.45(15) Yes C3 N2 N1 104.0(2) Yes N4 N3 C6 111.2(2) Yes N4 N3 C9 117.5(2) Yes C6 N3 C9 131.2(2) Yes C8 N4 N3 105.4(2) Yes C2 C1 N1 103.8(3) Yes C2 C1 C4 131.6(3) Yes N1 C1 C4 124.6(3) Yes C1 C2 C3 108.5(3) Yes C1 C2 H2 125.8 ? C3 C2 H2 125.8 ? N2 C3 C2 110.9(3) Yes N2 C3 C5 119.2(3) Yes C2 C3 C5 130.0(3) Yes C1 C4 H4A 109.5 ? C1 C4 H4B 109.5 ? H4A C4 H4B 109.5 ? C1 C4 H4C 109.5 ? H4A C4 H4C 109.5 ? H4B C4 H4C 109.5 ? C3 C5 H5A 109.5 ? C3 C5 H5B 109.5 ? H5A C5 H5B 109.5 ? C3 C5 H5C 109.5 ? H5A C5 H5C 109.5 ? H5B C5 H5C 109.5 ? N3 C6 C7 107.3(2) Yes N3 C6 S1 122.59(18) Yes C7 C6 S1 129.90(18) Yes C6 C7 C8 104.0(2) Yes C6 C7 C10 129.6(2) Yes C8 C7 C10 126.2(2) Yes N4 C8 C7 112.1(2) Yes N4 C8 H8 123.9 ? C7 C8 H8 123.9 ? N3 C9 H9A 109.5 ? N3 C9 H9B 109.5 ? H9A C9 H9B 109.5 ? N3 C9 H9C 109.5 ? H9A C9 H9C 109.5 ? H9B C9 H9C 109.5 ? O3 C10 O4 124.4(3) Yes O3 C10 C7 125.8(3) Yes O4 C10 C7 109.7(2) Yes O4 C11 C12 108.1(3) Yes O4 C11 H11A 110.1 ? C12 C11 H11A 110.1 ? O4 C11 H11B 110.1 ? C12 C11 H11B 110.1 ? H11A C11 H11B 108.4 ? C11 C12 H12A 109.5 ? C11 C12 H12B 109.5 ? H12A C12 H12B 109.5 ? C11 C12 H12C 109.5 ? H12A C12 H12C 109.5 ? H12B C12 H12C 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 O1 S1 N1 C1 -12.2(3) O2 S1 N1 C1 118.7(2) C6 S1 N1 C1 -127.8(2) O1 S1 N1 N2 173.91(17) O2 S1 N1 N2 -55.13(19) C6 S1 N1 N2 58.36(19) C1 N1 N2 C3 0.7(3) S1 N1 N2 C3 175.78(17) C6 N3 N4 C8 0.2(3) C9 N3 N4 C8 178.1(2) N2 N1 C1 C2 -0.5(3) S1 N1 C1 C2 -174.4(2) N2 N1 C1 C4 179.1(2) S1 N1 C1 C4 5.2(4) N1 C1 C2 C3 0.1(3) C4 C1 C2 C3 -179.5(3) N1 N2 C3 C2 -0.6(3) N1 N2 C3 C5 -179.3(3) C1 C2 C3 N2 0.3(3) C1 C2 C3 C5 178.9(3) N4 N3 C6 C7 -0.2(3) C9 N3 C6 C7 -177.7(2) N4 N3 C6 S1 -175.23(16) C9 N3 C6 S1 7.2(3) O1 S1 C6 N3 142.70(18) O2 S1 C6 N3 10.1(2) N1 S1 C6 N3 -103.7(2) O1 S1 C6 C7 -31.1(2) O2 S1 C6 C7 -163.7(2) N1 S1 C6 C7 82.5(2) N3 C6 C7 C8 0.1(2) S1 C6 C7 C8 174.63(18) N3 C6 C7 C10 174.9(2) S1 C6 C7 C10 -10.6(4) N3 N4 C8 C7 -0.2(3) C6 C7 C8 N4 0.1(3) C10 C7 C8 N4 -175.0(2) C11 O4 C10 O3 0.3(4) C11 O4 C10 C7 178.5(2) C6 C7 C10 O3 -12.5(4) C8 C7 C10 O3 161.3(3) C6 C7 C10 O4 169.3(2) C8 C7 C10 O4 -17.0(3) C10 O4 C11 C12 -173.4(3)