#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/05/2200561.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_2200561 loop_ _publ_author_name 'Popovi\'c, Jasminka' 'Mrvo\N,2-Dimethyl-3-furanthiocarboxanilide ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o893 _journal_page_last o894 _journal_paper_doi 10.1107/S1600536801013472 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C13 H13 N1 O1 S1' _chemical_formula_moiety 'C13 H13 N1 O1 S1' _chemical_formula_sum 'C13 H13 N O S' _chemical_formula_weight 231.30 _chemical_name_systematic ; N-methyl-2-methyl-3-furanthiocarboxanilyd ; _space_group_IT_number 61 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 9.577(3) _cell_length_b 16.039(3) _cell_length_c 16.127(2) _cell_measurement_reflns_used 33 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 16.4 _cell_measurement_theta_min 11.9 _cell_volume 2477.2(10) _computing_cell_refinement STADI4 _computing_data_collection 'STADI4 (Stoe & Cie, 1995)' _computing_data_reduction 'X-RED (Stoe & Cie, 1995)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _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 .99 _diffrn_measured_fraction_theta_max .99 _diffrn_measurement_device_type 'Philips PW1100 updated by Stoe' _diffrn_measurement_method \q/2\q _diffrn_radiation_monochromator 'planar graphite' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0525 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2671 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 2.53 _diffrn_standards_decay_% 2.4 _diffrn_standards_interval_time 90 _diffrn_standards_number 4 _exptl_absorpt_coefficient_mu .240 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.240 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 976 _exptl_crystal_size_max .34 _exptl_crystal_size_mid .26 _exptl_crystal_size_min .11 _refine_diff_density_max .354 _refine_diff_density_min -.173 _refine_ls_extinction_coef .015(2) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref .965 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2671 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all .965 _refine_ls_R_factor_all .1336 _refine_ls_R_factor_gt .0531 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0849P)^2^+0.4315P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1667 _reflns_number_gt 1280 _reflns_number_total 2671 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6043.cif _cod_data_source_block I _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 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_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_formula_sum 'C13 H13 N1 O1 S1' _cod_database_code 2200561 _cod_database_fobs_code 2200561 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' 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_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 .1588(5) .2353(2) .6408(2) .0767(10) Uani d . 1 . . C C2 .0677(5) .2584(3) .6967(3) .0924(12) Uani d . 1 . . C O1 -.0628(2) .22716(15) .67979(14) .0785(7) Uani d . 1 . . O C3 -.0517(4) .1839(2) .6076(2) .0762(9) Uani d . 1 . . C C4 -.1787(4) .1443(3) .5778(3) .1054(14) Uani d . 1 . . C H41 -.2551 .1587 .6137 .158 Uiso calc R 1 . . H H42 -.1666 .0849 .5775 .158 Uiso calc R 1 . . H H43 -.1985 .1633 .5226 .158 Uiso calc R 1 . . H C5 .0803(3) .18494(19) .58081(18) .0605(8) Uani d . 1 . . C C6 .1366(3) .14937(16) .50283(15) .0529(7) Uani d . 1 . . C S1 .05308(9) .16177(6) .41301(5) .0778(4) Uani d . 1 . . S N1 .2614(2) .11279(14) .50910(12) .0545(6) Uani d . 1 . . N C7 .3426(4) .0903(2) .43517(18) .0846(11) Uani d . 1 . . C H71 .4288 .0648 .4518 .127 Uiso calc R 1 . . H H72 .3620 .1396 .4034 .127 Uiso calc R 1 . . H H73 .2900 .0519 .4019 .127 Uiso calc R 1 . . H C8 .3100(3) .07707(16) .58597(15) .0503(6) Uani d . 1 . . C C9 .4345(3) .1038(2) .6219(2) .0647(8) Uani d . 1 . . C C10 .4806(4) .0663(2) .6938(2) .0722(9) Uani d . 1 . . C C11 .4074(4) .0035(2) .7287(2) .0755(10) Uani d . 1 . . C C12 .2849(4) -.0237(2) .6942(2) .0708(9) Uani d . 1 . . C C13 .2370(3) .01352(18) .62140(18) .0582(7) Uani d . 1 . . C H1 .248(4) .253(3) .642(2) .108(14) Uiso d . 1 . . H H2 .086(4) .294(2) .752(3) .111(12) Uiso d . 1 . . H H9 .472(3) .1471(17) .5983(16) .049(8) Uiso d . 1 . . H H10 .561(3) .087(2) .717(2) .081(11) Uiso d . 1 . . H H11 .443(3) -.015(2) .780(2) .093(11) Uiso d . 1 . . H H12 .229(3) -.0723(19) .7174(17) .069(8) Uiso d . 1 . . H H13 .154(3) -.0021(16) .5985(15) .057(8) Uiso d . 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 C1 .089(3) .075(2) .067(2) .011(2) .006(2) -.0139(17) C2 .123(3) .083(2) .071(2) .013(2) -.004(2) -.014(2) O1 .0851(17) .0807(16) .0697(14) .0220(13) .0199(12) -.0006(12) C3 .077(2) .075(2) .076(2) .0172(18) .0041(17) .0131(17) C4 .074(3) .111(3) .131(4) -.005(2) .001(2) .018(3) C5 .0632(19) .0608(17) .0576(17) .0095(15) .0010(14) .0059(14) C6 .0606(18) .0457(15) .0523(16) -.0044(13) .0024(13) .0022(12) S1 .0928(7) .0837(6) .0567(5) .0011(5) -.0162(4) .0045(4) N1 .0607(14) .0569(13) .0459(12) .0039(12) .0059(11) .0014(10) C7 .095(3) .094(2) .0645(19) .015(2) .0309(18) .0064(18) C8 .0537(16) .0466(14) .0506(14) .0058(12) .0064(12) -.0030(12) C9 .0557(19) .0580(18) .080(2) -.0021(16) .0011(17) .0026(16) C10 .066(2) .074(2) .077(2) .0130(19) -.0141(18) -.0068(19) C11 .080(2) .084(2) .063(2) .026(2) .0002(18) .0061(18) C12 .074(2) .066(2) .072(2) .0093(17) .0159(18) .0149(17) C13 .0565(18) .0562(17) .0618(17) .0006(15) .0036(15) -.0003(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' S S .1246 .1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 2 4 4 2 1 5 3 0 8 1 9 1 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 C2 C1 C5 105.6(4) no C2 C1 H1 122(3) no C5 C1 H1 132(2) no C1 C2 O1 111.5(4) no C1 C2 H2 128(2) no O1 C2 H2 120(2) no C3 O1 C2 106.6(3) no C5 C3 O1 110.1(3) no C5 C3 C4 133.7(4) no O1 C3 C4 116.1(3) no C3 C4 H41 109.5 no C3 C4 H42 109.5 no H41 C4 H42 109.5 no C3 C4 H43 109.5 no H41 C4 H43 109.5 no H42 C4 H43 109.5 no C3 C5 C1 106.2(3) no C3 C5 C6 127.9(3) no C1 C5 C6 125.7(3) no N1 C6 C5 115.5(2) yes N1 C6 S1 123.2(2) yes C5 C6 S1 121.1(2) yes C6 N1 C8 121.9(2) yes C6 N1 C7 121.3(2) yes C8 N1 C7 115.4(2) yes N1 C7 H71 109.5 no N1 C7 H72 109.5 no H71 C7 H72 109.5 no N1 C7 H73 109.5 no H71 C7 H73 109.5 no H72 C7 H73 109.5 no C13 C8 C9 119.7(3) no C13 C8 N1 119.5(3) no C9 C8 N1 120.8(3) no C10 C9 C8 119.3(3) no C10 C9 H9 125.7(18) no C8 C9 H9 114.8(18) no C11 C10 C9 120.7(4) no C11 C10 H10 123(2) no C9 C10 H10 116(2) no C10 C11 C12 120.8(3) no C10 C11 H11 114(2) no C12 C11 H11 125(2) no C11 C12 C13 119.2(3) no C11 C12 H12 123.0(16) no C13 C12 H12 117.7(16) no C8 C13 C12 120.3(3) no C8 C13 H13 118.9(17) no C12 C13 H13 120.7(17) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.308(5) no C1 C5 . 1.467(5) no C1 H1 . .90(4) no C2 O1 . 1.374(5) no C2 H2 . 1.08(4) no O1 C3 . 1.360(4) no C3 C5 . 1.336(4) no C3 C4 . 1.454(5) no C4 H41 . .9600 no C4 H42 . .9600 no C4 H43 . .9600 no C5 C6 . 1.483(4) yes C6 N1 . 1.335(3) yes C6 S1 . 1.667(3) yes N1 C8 . 1.443(3) yes N1 C7 . 1.468(3) yes C7 H71 . .9600 no C7 H72 . .9600 no C7 H73 . .9600 no C8 C13 . 1.362(4) no C8 C9 . 1.393(4) no C9 C10 . 1.379(5) no C9 H9 . .87(3) no C10 C11 . 1.350(5) no C10 H10 . .92(3) no C11 C12 . 1.370(5) no C11 H11 . .95(4) no C12 C13 . 1.395(4) no C12 H12 . 1.02(3) no C13 H13 . .91(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 4425354 2 PubChem 5260209