#------------------------------------------------------------------------------ #$Date: 2021-01-03 22:22:59 +0000 (Sun, 03 Jan 2021) $ #$Revision: 260398 $ #$URL: svn://www.crystallography.net/cod/cif/3/50/01/3500117.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_3500117 loop_ _publ_author_name 'Thierry Maris' _publ_section_references ; Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H. (2009), J. Appl. Cryst. 42, 339-341. Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122. ; _publ_section_title ; 3-Thiopheneacetic acid, 2-nitro- ; _journal_name_full 'Personal communication to COD' _journal_year 2021 _chemical_formula_moiety 'C6 H5 N O4 S' _chemical_formula_sum 'C6 H5 N O4 S' _chemical_formula_weight 187.17 _chemical_name_systematic '3-Thiopheneacetic acid, 2-nitro-' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _audit_creation_date 2020-06-03 _audit_creation_method ; Olex2 1.3 (compiled 2020.02.04 svn.rd84adfe8 for OlexSys, GUI svn.r6032) ; _cell_angle_alpha 90 _cell_angle_beta 92.949(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 4.6733(11) _cell_length_b 5.8249(5) _cell_length_c 27.492(4) _cell_measurement_reflns_used 23 _cell_measurement_temperature 190 _cell_measurement_theta_max 17 _cell_measurement_theta_min 8 _cell_volume 747.4(2) _computing_cell_refinement 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_collection 'CAD-4 software (Enraf-Nonius, 1989)' _computing_data_reduction ; RC93 (Watkin, D.J., Prout, C.K., Lilley, P.M.deQ. 1994) ; _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _diffrn_ambient_temperature 190.0 _diffrn_measured_fraction_theta_full 0.960 _diffrn_measured_fraction_theta_max 0.957 _diffrn_measurement_device ' Enraf-nonius CAD4 ' _diffrn_measurement_method \w/2\q _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0295 _diffrn_reflns_av_unetI/netI 0.0228 _diffrn_reflns_Laue_measured_fraction_full 0.960 _diffrn_reflns_Laue_measured_fraction_max 0.957 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 3794 _diffrn_reflns_point_group_measured_fraction_full 0.960 _diffrn_reflns_point_group_measured_fraction_max 0.957 _diffrn_reflns_theta_full 67.680 _diffrn_reflns_theta_max 73.868 _diffrn_reflns_theta_min 6.449 _diffrn_standards_decay_% 2.18 _diffrn_standards_interval_count 200 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 3.694 _exptl_absorpt_correction_T_max 0.62 _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '\y scan,(North et al, 1968)' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.663 _exptl_crystal_description plate _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.45 _exptl_crystal_size_mid 0.42 _exptl_crystal_size_min 0.13 _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. ; _refine_diff_density_max 0.353 _refine_diff_density_min -0.438 _refine_diff_density_rms 0.085 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 112 _refine_ls_number_reflns 1456 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0363 _refine_ls_R_factor_gt 0.0359 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0709P)^2^+0.1262P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0963 _refine_ls_wR_factor_ref 0.0966 _refine_special_details ; _shelx_SHELXL_version_number '2018/3' 1. Fixed Uiso At 1.2 times of: All C(H,H) groups, H2 of C2, H3 of C3 At 1.5 times of: H11 of C10 2.a Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3) ; _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 1433 _reflns_number_total 1456 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file thioact.cif _cod_data_source_block thioact _cod_database_code 3500117 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group S1 S 1.01179(7) 0.11421(5) 0.79270(2) 0.02507(17) Uani 1 1 d . . . . . O6 O 0.6251(2) 0.48603(18) 0.79696(4) 0.0357(3) Uani 1 1 d . . . . . O7 O 0.5194(2) 0.45482(19) 0.87270(4) 0.0387(3) Uani 1 1 d . . . . . O11 O 0.7108(2) 0.2862(2) 1.00042(3) 0.0383(3) Uani 1 1 d . . . . . O12 O 1.0460(3) 0.37123(19) 0.94878(4) 0.0353(3) Uani 1 1 d . . . . . N8 N 0.6442(3) 0.38900(17) 0.83688(4) 0.0258(3) Uani 1 1 d . . . . . C2 C 1.1474(3) -0.1152(2) 0.82430(5) 0.0277(3) Uani 1 1 d . . . . . H2 H 1.279423 -0.220401 0.811499 0.033 Uiso 1 1 calc R U . . . C3 C 1.0472(3) -0.1332(2) 0.87021(5) 0.0241(3) Uani 1 1 d . . . . . H3 H 1.101689 -0.252042 0.892458 0.029 Uiso 1 1 calc R U . . . C4 C 0.8528(3) 0.04560(19) 0.88080(4) 0.0196(3) Uani 1 1 d . . . . . C5 C 0.8180(3) 0.18980(19) 0.84141(4) 0.0197(3) Uani 1 1 d . . . . . C9 C 0.7141(3) 0.0676(2) 0.92845(4) 0.0240(3) Uani 1 1 d . . . . . H9A H 0.734390 -0.079397 0.946361 0.029 Uiso 1 1 calc R U . . . H9B H 0.506866 0.097352 0.922179 0.029 Uiso 1 1 calc R U . . . C10 C 0.8417(3) 0.2575(2) 0.95974(4) 0.0228(3) Uani 1 1 d . . . . . H11 H 0.774(4) 0.414(3) 1.0134(7) 0.034 Uiso 1 1 d . U . . . 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 0.0330(3) 0.0229(2) 0.0201(2) -0.00128(10) 0.00871(16) 0.00712(11) O6 0.0439(7) 0.0295(5) 0.0346(5) 0.0116(4) 0.0099(4) 0.0123(5) O7 0.0477(7) 0.0316(5) 0.0389(6) 0.0022(4) 0.0221(5) 0.0181(5) O11 0.0513(7) 0.0402(6) 0.0255(5) -0.0110(4) 0.0216(5) -0.0173(5) O12 0.0364(7) 0.0440(6) 0.0271(5) -0.0128(4) 0.0158(5) -0.0165(4) N8 0.0311(7) 0.0184(5) 0.0289(6) 0.0023(4) 0.0113(5) 0.0061(4) C2 0.0336(8) 0.0218(7) 0.0278(7) -0.0053(5) 0.0025(6) 0.0119(5) C3 0.0314(8) 0.0163(6) 0.0244(6) -0.0022(4) 0.0019(6) 0.0030(5) C4 0.0245(6) 0.0147(5) 0.0198(5) -0.0016(4) 0.0038(4) -0.0013(4) C5 0.0232(6) 0.0143(5) 0.0222(6) -0.0024(4) 0.0072(5) 0.0031(4) C9 0.0312(7) 0.0211(6) 0.0203(6) 0.0008(4) 0.0079(5) -0.0039(5) C10 0.0283(7) 0.0234(6) 0.0174(5) 0.0008(4) 0.0073(5) 0.0012(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S 0.3331 0.5567 '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_site_symmetry_1 _geom_angle_site_symmetry_3 C2 S1 C5 90.04(6) . . C10 O11 H11 107.1(12) . . O6 N8 C5 117.91(10) . . O7 N8 O6 123.60(11) . . O7 N8 C5 118.49(11) . . S1 C2 H2 123.4 . . C3 C2 S1 113.23(9) . . C3 C2 H2 123.4 . . C2 C3 H3 123.7 . . C2 C3 C4 112.60(11) . . C4 C3 H3 123.7 . . C3 C4 C9 123.52(11) . . C5 C4 C3 109.71(10) . . C5 C4 C9 126.77(11) . . N8 C5 S1 117.72(9) . . C4 C5 S1 114.42(9) . . C4 C5 N8 127.86(10) . . C4 C9 H9A 109.0 . . C4 C9 H9B 109.0 . . C4 C9 C10 112.73(11) . . H9A C9 H9B 107.8 . . C10 C9 H9A 109.0 . . C10 C9 H9B 109.0 . . O11 C10 C9 113.08(11) . . O12 C10 O11 123.33(12) . . O12 C10 C9 123.59(11) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 S1 C2 1.6986(14) . S1 C5 1.7124(11) . O6 N8 1.2335(15) . O7 N8 1.2314(15) . O11 C10 1.3130(14) . O11 H11 0.87(2) . O12 C10 1.2125(17) . N8 C5 1.4181(15) . C2 H2 0.9500 . C2 C3 1.3725(19) . C3 H3 0.9500 . C3 C4 1.4219(17) . C4 C5 1.3735(17) . C4 C9 1.4967(16) . C9 H9A 0.9900 . C9 H9B 0.9900 . C9 C10 1.5055(18) . loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag C2 H2 O6 0.95 2.40 3.3343(16) 167.7 1_645 yes O11 H11 O12 0.87(2) 1.81(2) 2.6571(15) 164.9(19) 3_767 yes 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 S1 C2 C3 C4 -0.20(16) . . . . O6 N8 C5 S1 5.52(17) . . . . O6 N8 C5 C4 -174.57(13) . . . . O7 N8 C5 S1 -174.96(11) . . . . O7 N8 C5 C4 4.9(2) . . . . C2 S1 C5 N8 179.71(11) . . . . C2 S1 C5 C4 -0.20(11) . . . . C2 C3 C4 C5 0.04(17) . . . . C2 C3 C4 C9 -179.44(13) . . . . C3 C4 C5 S1 0.13(14) . . . . C3 C4 C5 N8 -179.78(13) . . . . C3 C4 C9 C10 105.32(14) . . . . C4 C9 C10 O11 176.45(12) . . . . C4 C9 C10 O12 -4.14(19) . . . . C5 S1 C2 C3 0.23(12) . . . . C5 C4 C9 C10 -74.07(17) . . . . C9 C4 C5 S1 179.59(11) . . . . C9 C4 C5 N8 -0.3(2) . . . . _cod_database_fobs_code 3500117