#------------------------------------------------------------------------------ #$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201973 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/20/40/2204073.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_2204073 loop_ _publ_author_name 'Fei Gao' 'Caixia Yin' 'Pin Yang' 'Gang Xue' _publ_section_title ; 2-[4-(2-Hydroxyethyl)piperazin-1-yl]ethanesulfonic acid ; _journal_issue 8 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o1327 _journal_page_last o1328 _journal_paper_doi 10.1107/S1600536804016587 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C8 H18 N2 O4 S' _chemical_formula_moiety 'C8 H18 N2 O4 S' _chemical_formula_sum 'C8 H18 N2 O4 S' _chemical_formula_weight 238.30 _chemical_name_common ; 2-[4-(2-Hydroxyethyl)piperazin-1-yl]ethanesulfonic acid ; _chemical_name_systematic ; 2-[4-(2-Hydroxyethyl)piperazin-1-yl]ethanesulfonic acid ; _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 8.3813(13) _cell_length_b 9.6623(16) _cell_length_c 27.056(4) _cell_measurement_reflns_used 12566 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 26.96 _cell_measurement_theta_min 2.43 _cell_volume 2191.1(6) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL/PC (Sheldrick, 1999)' _computing_publication_material SHELXTL/PC _computing_structure_refinement 'SHELXL97 (Sheldrick, 2000)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2000)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean '100x100 microns' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'SMART 1K 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 0.0267 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 9743 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.51 _diffrn_standards_decay_% 3.97 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.294 _exptl_absorpt_correction_T_max 0.9826 _exptl_absorpt_correction_T_min 0.8481 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 2000)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_description sheet _exptl_crystal_F_000 1024 _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.58 _exptl_crystal_size_min 0.06 _refine_diff_density_max 0.625 _refine_diff_density_min -0.322 _refine_ls_extinction_coef 0.0033(6) _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 1.064 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 141 _refine_ls_number_reflns 1919 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.064 _refine_ls_R_factor_all 0.0449 _refine_ls_R_factor_gt 0.0406 _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^)+(0.0636P)^2^+1.4035P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1113 _refine_ls_wR_factor_ref 0.1146 _reflns_number_gt 1724 _reflns_number_total 1919 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6390.cif _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius ; _cod_database_code 2204073 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' 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 S 1.04860(6) 0.27595(6) 0.443761(18) 0.0285(2) Uani d . 1 S O2 0.90393(19) 0.35559(18) 0.43881(6) 0.0446(4) Uani d . 1 O O3 1.0642(2) 0.16138(19) 0.40993(6) 0.0562(5) Uani d . 1 O O1 1.18966(17) 0.36491(16) 0.44371(5) 0.0354(4) Uani d . 1 O H1 1.2620 0.3280 0.4255 0.080 Uiso d . 1 H O4 0.7746(2) 0.33570(17) 0.78314(6) 0.0369(4) Uani d . 1 O H4 0.699(4) 0.300(3) 0.7867(11) 0.055(10) Uiso d . 1 H N1 0.96747(19) 0.25262(17) 0.59097(6) 0.0245(4) Uani d . 1 N N2 0.97735(19) 0.20089(17) 0.69669(6) 0.0243(4) Uani d . 1 N C1 1.0725(2) 0.1432(2) 0.61282(7) 0.0301(5) Uani d . 1 C H1A 1.1774 0.1815 0.6195 0.036 Uiso calc R 1 H H1B 1.0848 0.0676 0.5895 0.036 Uiso calc R 1 H C2 1.0001(3) 0.0900(2) 0.66014(7) 0.0300(5) Uani d . 1 C H2B 0.8979 0.0475 0.6529 0.036 Uiso calc R 1 H H2C 1.0691 0.0194 0.6740 0.036 Uiso calc R 1 H C3 0.8718(3) 0.3058(2) 0.67489(7) 0.0288(5) Uani d . 1 C H3B 0.8547 0.3797 0.6986 0.035 Uiso calc R 1 H H3C 0.7691 0.2643 0.6675 0.035 Uiso calc R 1 H C4 0.9424(3) 0.3651(2) 0.62809(7) 0.0306(5) Uani d . 1 C H4B 0.8711 0.4345 0.6146 0.037 Uiso calc R 1 H H4C 1.0436 0.4093 0.6355 0.037 Uiso calc R 1 H C5 0.9105(3) 0.1406(2) 0.74216(7) 0.0314(5) Uani d . 1 C H5B 0.9753 0.0617 0.7516 0.038 Uiso calc R 1 H H5C 0.8041 0.1067 0.7351 0.038 Uiso calc R 1 H C6 1.0321(3) 0.3104(2) 0.54346(8) 0.0310(5) Uani d . 1 C H6A 1.1375 0.3487 0.5493 0.037 Uiso calc R 1 H H6B 0.9635 0.3848 0.5322 0.037 Uiso calc R 1 H C7 0.9011(3) 0.2390(2) 0.78573(8) 0.0352(5) Uani d . 1 C H7A 0.8892 0.1851 0.8157 0.042 Uiso calc R 1 H H7B 1.0010 0.2892 0.7881 0.042 Uiso calc R 1 H C8 1.0424(2) 0.2005(2) 0.50383(8) 0.0298(5) Uani d . 1 C H8A 0.9505 0.1397 0.5062 0.036 Uiso calc R 1 H H8B 1.1375 0.1451 0.5090 0.036 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 S 0.0287(3) 0.0340(3) 0.0229(3) -0.0010(2) 0.00217(19) 0.0004(2) O2 0.0273(8) 0.0624(11) 0.0441(10) 0.0036(8) -0.0059(6) 0.0122(8) O3 0.0884(14) 0.0468(10) 0.0334(9) -0.0092(10) 0.0119(9) -0.0114(8) O1 0.0263(8) 0.0412(9) 0.0387(8) 0.0008(7) 0.0078(6) 0.0068(7) O4 0.0315(9) 0.0391(9) 0.0400(9) -0.0023(7) 0.0075(7) -0.0035(7) N1 0.0259(9) 0.0277(9) 0.0198(8) 0.0015(6) 0.0011(6) 0.0011(7) N2 0.0250(9) 0.0263(8) 0.0217(9) 0.0016(7) 0.0009(6) 0.0018(6) C1 0.0320(11) 0.0317(11) 0.0266(11) 0.0075(9) 0.0025(8) 0.0008(9) C2 0.0364(11) 0.0254(10) 0.0282(11) 0.0037(9) 0.0028(9) 0.0016(8) C3 0.0306(11) 0.0317(10) 0.0239(10) 0.0070(9) 0.0005(8) -0.0011(8) C4 0.0387(12) 0.0257(10) 0.0273(11) 0.0053(9) -0.0008(8) 0.0008(8) C5 0.0332(11) 0.0326(11) 0.0284(11) -0.0006(9) 0.0045(9) 0.0039(9) C6 0.0384(13) 0.0300(11) 0.0245(10) -0.0039(9) 0.0031(8) 0.0043(8) C7 0.0314(11) 0.0488(13) 0.0256(11) 0.0011(10) 0.0012(9) -0.0007(9) C8 0.0332(12) 0.0316(11) 0.0245(11) -0.0007(9) 0.0037(8) 0.0027(9) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O2 S O3 115.27(11) no O2 S O1 111.48(10) no O3 S O1 112.17(10) no O2 S C8 106.17(10) no O3 S C8 105.49(10) no O1 S C8 105.38(9) no S O1 H1 109.09 ? C7 O4 H4 110(2) ? C4 N1 C1 109.28(15) no C4 N1 C6 110.82(16) no C1 N1 C6 112.84(15) no C3 N2 C2 108.12(15) no C3 N2 C5 112.30(16) no C2 N2 C5 108.86(16) no N1 C1 C2 109.85(16) no N1 C1 H1A 109.7 ? C2 C1 H1A 109.7 ? N1 C1 H1B 109.7 ? C2 C1 H1B 109.7 ? H1A C1 H1B 108.2 ? N2 C2 C1 112.00(17) no N2 C2 H2B 109.2 ? C1 C2 H2B 109.2 ? N2 C2 H2C 109.2 ? C1 C2 H2C 109.2 ? H2B C2 H2C 107.9 ? N2 C3 C4 111.22(17) no N2 C3 H3B 109.4 ? C4 C3 H3B 109.4 ? N2 C3 H3C 109.4 ? C4 C3 H3C 109.4 ? H3B C3 H3C 108.0 ? N1 C4 C3 110.04(16) no N1 C4 H4B 109.7 ? C3 C4 H4B 109.7 ? N1 C4 H4C 109.7 ? C3 C4 H4C 109.7 ? H4B C4 H4C 108.2 ? N2 C5 C7 114.95(17) no N2 C5 H5B 108.5 ? C7 C5 H5B 108.5 ? N2 C5 H5C 108.5 ? C7 C5 H5C 108.5 ? H5B C5 H5C 107.5 ? N1 C6 C8 111.47(17) no N1 C6 H6A 109.3 ? C8 C6 H6A 109.3 ? N1 C6 H6B 109.3 ? C8 C6 H6B 109.3 ? H6A C6 H6B 108.0 ? O4 C7 C5 114.50(17) no O4 C7 H7A 108.6 ? C5 C7 H7A 108.6 ? O4 C7 H7B 108.6 ? C5 C7 H7B 108.6 ? H7A C7 H7B 107.6 ? C6 C8 S 111.14(14) no C6 C8 H8A 109.4 ? S C8 H8A 109.4 ? C6 C8 H8B 109.4 ? S C8 H8B 109.4 ? H8A C8 H8B 108.0 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag S O2 1.4424(17) y S O3 1.4424(18) y S O1 1.4617(16) y S C8 1.782(2) y O1 H1 0.859 ? O4 C7 1.415(3) y O4 H4 0.73(3) ? N1 C4 1.495(3) y N1 C1 1.498(3) y N1 C6 1.503(3) y N2 C3 1.469(2) y N2 C2 1.471(3) y N2 C5 1.472(3) y C1 C2 1.507(3) y C1 H1A 0.9700 ? C1 H1B 0.9700 ? C2 H2B 0.9700 ? C2 H2C 0.9700 ? C3 C4 1.511(3) y C3 H3B 0.9700 ? C3 H3C 0.9700 ? C4 H4B 0.9700 ? C4 H4C 0.9700 ? C5 C7 1.516(3) y C5 H5B 0.9700 ? C5 H5C 0.9700 ? C6 C8 1.512(3) y C6 H6A 0.9700 ? C6 H6B 0.9700 ? C7 H7A 0.9700 ? C7 H7B 0.9700 ? C8 H8A 0.9700 ? C8 H8B 0.9700 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1 N1 4_556 0.86 1.94 2.755(2) 158 y O4 H4 N2 6_557 0.73(3) 2.14(3) 2.864(2) 175(3) y C1 H1A O2 4_556 0.97 2.49 3.109(3) 121 y C3 H3B O4 . 0.97 2.42 3.054(2) 122 y 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_publ_flag C4 N1 C1 C2 56.4(2) yes C6 N1 C1 C2 -179.83(17) ? C3 N2 C2 C1 59.3(2) yes C5 N2 C2 C1 -178.49(17) ? N1 C1 C2 N2 -58.8(2) yes C2 N2 C3 C4 -59.4(2) yes C5 N2 C3 C4 -179.54(17) ? C1 N1 C4 C3 -57.1(2) yes C6 N1 C4 C3 177.92(17) ? N2 C3 C4 N1 59.8(2) yes C3 N2 C5 C7 -68.2(2) ? C2 N2 C5 C7 172.14(17) ? C4 N1 C6 C8 -174.23(16) ? C1 N1 C6 C8 62.8(2) ? N2 C5 C7 O4 76.5(2) ? N1 C6 C8 S 159.09(14) ? O2 S C8 C6 -59.31(17) ? O3 S C8 C6 177.90(15) ? O1 S C8 C6 59.06(16) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 22278