#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/42/2204211.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_2204211 loop_ _publ_author_name Vasu 'Nirmala, K. A.' 'Chopra, Deepak' 'Mohan, S.' 'Saravanan, J.' _publ_section_title ; 2-(Acetamido)-4,5-dimethyl-N-(2-methylphenyl)thiophene-3-carboxamide ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1554 _journal_page_last o1556 _journal_paper_doi 10.1107/S1600536804018781 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C16 H18 N2 O2 S' _chemical_formula_moiety 'C16 H18 N2 O2 S' _chemical_formula_sum 'C16 H18 N2 O2 S' _chemical_formula_weight 302.39 _chemical_name_systematic ; 2-(acetamido)-4,5-dimethyl-N-(2-methylphenyl)thiophene-3-carboxamide ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90 _cell_angle_beta 94.566(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.416(2) _cell_length_b 8.858(3) _cell_length_c 23.718(8) _cell_measurement_reflns_used 650 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 24.5 _cell_measurement_theta_min 2.5 _cell_volume 1553.1(9) _computing_cell_refinement SMART _computing_data_collection 'SMART (Bruker, 1998)' _computing_data_reduction 'SAINT (Bruker, 1998)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997) and CAMERON (Watkin et al., 1993)' _computing_publication_material 'PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1993)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Bruker SMART APEX 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 0.0183 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_number 11711 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 1.72 _exptl_absorpt_coefficient_mu 0.214 _exptl_absorpt_correction_T_max 0.9584 _exptl_absorpt_correction_T_min 0.9101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.293 _exptl_crystal_density_meas ? _exptl_crystal_density_method . _exptl_crystal_description block _exptl_crystal_F_000 640 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.318 _refine_diff_density_min -0.163 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.061 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 202 _refine_ls_number_reflns 3118 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.061 _refine_ls_R_factor_all 0.0486 _refine_ls_R_factor_gt 0.0420 _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^)+(0.1357P)^2^+0.8P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1176 _refine_ls_wR_factor_ref 0.1226 _reflns_number_gt 2715 _reflns_number_total 3118 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6402.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' 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 'Monoclinic' changed to 'monoclinic' 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_cell_volume 1553.2(9) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2204211 _cod_database_fobs_code 2204211 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-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 S1 0.25473(6) 0.59444(5) -0.056475(17) 0.03998(17) Uani d . 1 S O1 0.2861(2) 0.18448(14) 0.05964(5) 0.0511(4) Uani d . 1 O O2 0.3785(2) 0.38323(16) -0.13044(5) 0.0520(4) Uani d . 1 O N1 0.3368(2) 0.35218(17) 0.13111(6) 0.0437(4) Uani d . 1 N N2 0.3211(2) 0.29163(17) -0.04514(6) 0.0404(3) Uani d . 1 N C1 0.2810(2) 0.42759(17) -0.01966(7) 0.0339(3) Uani d . 1 C C2 0.2575(2) 0.44524(18) 0.03693(7) 0.0339(3) Uani d . 1 C C3 0.2086(2) 0.59902(18) 0.05010(7) 0.0368(4) Uani d . 1 C C4 0.2040(2) 0.68968(19) 0.00397(8) 0.0409(4) Uani d . 1 C C5 0.2921(2) 0.31688(18) 0.07608(7) 0.0374(4) Uani d . 1 C C6 0.3909(3) 0.2442(2) 0.17378(7) 0.0452(4) Uani d . 1 C C7 0.2723(3) 0.1328(2) 0.18960(8) 0.0534(5) Uani d . 1 C C8 0.3383(4) 0.0347(3) 0.23321(10) 0.0732(7) Uani d . 1 C C9 0.5087(5) 0.0495(3) 0.25967(10) 0.0827(9) Uani d . 1 C C10 0.6207(4) 0.1616(4) 0.24427(9) 0.0787(8) Uani d . 1 C C11 0.5626(3) 0.2590(3) 0.20091(9) 0.0627(6) Uani d . 1 C C12 0.0840(4) 0.1182(3) 0.16399(11) 0.0756(7) Uani d . 1 C C13 0.1539(3) 0.6536(2) 0.10626(8) 0.0494(4) Uani d . 1 C C14 0.1594(3) 0.8547(2) -0.00080(10) 0.0619(6) Uani d . 1 C C15 0.3679(2) 0.2755(2) -0.09890(7) 0.0426(4) Uani d . 1 C C16 0.4032(4) 0.1154(3) -0.11619(10) 0.0661(6) Uani d . 1 C H1N 0.373(3) 0.435(2) 0.1359(8) 0.045(6) Uiso d . 1 H H2N 0.315(3) 0.218(2) -0.0238(8) 0.043(5) Uiso d . 1 H H8 0.2641 -0.0425 0.2444 0.088 Uiso calc R 1 H H9 0.5480 -0.0173 0.2883 0.099 Uiso calc R 1 H H10 0.7354 0.1725 0.2627 0.094 Uiso calc R 1 H H11 0.6392 0.3348 0.1899 0.075 Uiso calc R 1 H H12A 0.0333 0.2169 0.1572 0.113 Uiso calc R 1 H H12B 0.0128 0.0640 0.1894 0.113 Uiso calc R 1 H H12C 0.0840 0.0644 0.1289 0.113 Uiso calc R 1 H H13A 0.2598 0.6664 0.1318 0.074 Uiso calc R 1 H H13B 0.0751 0.5809 0.1215 0.074 Uiso calc R 1 H H13C 0.0919 0.7484 0.1013 0.074 Uiso calc R 1 H H14A 0.0382 0.8711 0.0094 0.093 Uiso calc R 1 H H14B 0.1690 0.8875 -0.0390 0.093 Uiso calc R 1 H H14C 0.2424 0.9111 0.0242 0.093 Uiso calc R 1 H H16A 0.2903 0.0656 -0.1262 0.099 Uiso calc R 1 H H16B 0.4668 0.0630 -0.0853 0.099 Uiso calc R 1 H H16C 0.4751 0.1156 -0.1481 0.099 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 0.0439(3) 0.0389(3) 0.0367(3) 0.00068(16) 0.00020(18) 0.00730(16) O1 0.0834(10) 0.0324(7) 0.0375(7) -0.0030(6) 0.0044(6) 0.0004(5) O2 0.0666(9) 0.0555(8) 0.0340(6) -0.0042(6) 0.0047(6) 0.0014(6) N1 0.0641(10) 0.0335(8) 0.0329(7) -0.0023(7) -0.0007(6) 0.0004(6) N2 0.0514(9) 0.0354(8) 0.0347(7) 0.0009(6) 0.0049(6) -0.0002(6) C1 0.0340(8) 0.0334(8) 0.0337(8) -0.0012(6) -0.0005(6) 0.0015(6) C2 0.0354(8) 0.0328(8) 0.0332(8) -0.0023(6) 0.0014(6) -0.0011(6) C3 0.0344(8) 0.0346(8) 0.0410(9) -0.0003(6) -0.0002(7) -0.0020(6) C4 0.0401(9) 0.0356(9) 0.0465(9) 0.0022(7) -0.0007(7) 0.0009(7) C5 0.0433(9) 0.0360(8) 0.0332(8) -0.0031(7) 0.0042(7) 0.0007(6) C6 0.0628(11) 0.0437(9) 0.0297(8) 0.0087(8) 0.0077(7) 0.0009(7) C7 0.0694(13) 0.0515(11) 0.0415(9) 0.0088(9) 0.0188(9) 0.0049(8) C8 0.108(2) 0.0639(14) 0.0525(12) 0.0181(13) 0.0351(13) 0.0195(11) C9 0.114(2) 0.097(2) 0.0391(11) 0.0480(18) 0.0186(13) 0.0226(12) C10 0.0865(18) 0.108(2) 0.0399(11) 0.0297(16) -0.0059(11) 0.0021(13) C11 0.0700(14) 0.0768(15) 0.0400(10) 0.0062(11) -0.0042(9) -0.0004(10) C12 0.0761(17) 0.0783(16) 0.0746(16) -0.0134(13) 0.0209(13) 0.0113(13) C13 0.0536(11) 0.0465(10) 0.0486(10) 0.0062(8) 0.0066(8) -0.0092(8) C14 0.0770(15) 0.0389(10) 0.0687(14) 0.0129(10) -0.0018(11) 0.0037(9) C15 0.0448(9) 0.0481(10) 0.0347(8) -0.0030(7) 0.0010(7) -0.0049(7) C16 0.0947(17) 0.0539(12) 0.0519(12) 0.0000(11) 0.0192(11) -0.0132(10) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 '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' N N 0.0061 0.0033 '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' C C 0.0033 0.0016 '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 C1 S1 C4 91.25(8) C15 N2 C1 125.44(16) C15 N2 H2N 121.5(14) C1 N2 H2N 113.1(14) C5 N1 C6 124.12(15) C5 N1 H1N 114.1(15) C6 N1 H1N 116.8(15) C1 C2 C3 111.72(14) C1 C2 C5 119.77(14) C3 C2 C5 128.42(15) C4 C3 C2 111.93(15) C4 C3 C13 122.24(16) C2 C3 C13 125.66(15) C2 C1 N2 124.79(15) C2 C1 S1 112.30(12) N2 C1 S1 122.91(13) C3 C4 C14 129.00(18) C3 C4 S1 112.74(13) C14 C4 S1 118.25(15) O1 C5 N1 121.47(15) O1 C5 C2 122.14(15) N1 C5 C2 116.35(14) O2 C15 N2 121.92(17) O2 C15 C16 123.32(16) N2 C15 C16 114.76(17) C11 C6 C7 121.21(19) C11 C6 N1 117.49(19) C7 C6 N1 121.22(18) C3 C13 H13A 109.5 C3 C13 H13B 109.5 H13A C13 H13B 109.5 C3 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C6 C7 C8 116.4(2) C6 C7 C12 123.03(19) C8 C7 C12 120.5(2) C4 C14 H14A 109.5 C4 C14 H14B 109.5 H14A C14 H14B 109.5 C4 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C15 C16 H16A 109.5 C15 C16 H16B 109.5 H16A C16 H16B 109.5 C15 C16 H16C 109.5 H16A C16 H16C 109.5 H16B C16 H16C 109.5 C10 C11 C6 120.4(3) C10 C11 H11 119.8 C6 C11 H11 119.8 C9 C8 C7 122.1(2) C9 C8 H8 119.0 C7 C8 H8 119.0 C7 C12 H12A 109.5 C7 C12 H12B 109.5 H12A C12 H12B 109.5 C7 C12 H12C 109.5 H12A C12 H12C 109.5 H12B C12 H12C 109.5 C9 C10 C11 119.5(3) C9 C10 H10 120.2 C11 C10 H10 120.2 C10 C9 C8 120.4(2) C10 C9 H9 119.8 C8 C9 H9 119.8 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance S1 C1 1.7199(16) S1 C4 1.7306(19) O1 C5 1.236(2) O2 C15 1.219(2) N2 C15 1.355(2) N2 C1 1.390(2) N2 H2N 0.83(2) N1 C5 1.357(2) N1 C6 1.427(2) N1 H1N 0.79(2) C2 C1 1.376(2) C2 C3 1.450(2) C2 C5 1.478(2) C3 C4 1.355(3) C3 C13 1.503(2) C4 C14 1.501(3) C15 C16 1.505(3) C6 C11 1.387(3) C6 C7 1.393(3) C13 H13A 0.9600 C13 H13B 0.9600 C13 H13C 0.9600 C7 C8 1.409(3) C7 C12 1.484(4) C14 H14A 0.9600 C14 H14B 0.9600 C14 H14C 0.9600 C16 H16A 0.9600 C16 H16B 0.9600 C16 H16C 0.9600 C11 C10 1.385(3) C11 H11 0.9300 C8 C9 1.372(4) C8 H8 0.9300 C12 H12A 0.9600 C12 H12B 0.9600 C12 H12C 0.9600 C10 C9 1.363(5) C10 H10 0.9300 C9 H9 0.9300 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 N1 H1N O2 3_665 0.786(19) 2.46(2) 3.155(2) 148(2) yes N2 H2N O1 . 0.829(18) 2.029(19) 2.692(2) 137(2) yes C14 H14C O1 1_565 0.96 2.575 3.355(3) 138 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_publ_flag C1 C2 C3 C4 -2.1(2) ? C5 C2 C3 C4 174.31(15) ? C1 C2 C3 C13 173.14(16) ? C5 C2 C3 C13 -10.4(3) ? C3 C2 C1 N2 -177.25(15) ? C5 C2 C1 N2 6.0(2) ? C3 C2 C1 S1 2.59(17) ? C5 C2 C1 S1 -174.21(12) ? C15 N2 C1 C2 -170.81(16) yes C15 N2 C1 S1 9.4(2) ? C4 S1 C1 C2 -1.86(13) ? C4 S1 C1 N2 177.98(14) ? C2 C3 C4 C14 179.87(18) ? C13 C3 C4 C14 4.4(3) ? C2 C3 C4 S1 0.73(19) ? C13 C3 C4 S1 -174.73(13) ? C1 S1 C4 C3 0.62(14) ? C1 S1 C4 C14 -178.63(16) ? C6 N1 C5 O1 4.0(3) ? C6 N1 C5 C2 -174.04(16) yes C1 C2 C5 O1 -23.2(2) ? C3 C2 C5 O1 160.59(17) ? C1 C2 C5 N1 154.78(15) yes C3 C2 C5 N1 -21.4(2) ? C1 N2 C15 O2 -0.2(3) ? C1 N2 C15 C16 -179.62(17) ? C5 N1 C6 C11 118.8(2) yes C5 N1 C6 C7 -64.4(2) ? C11 C6 C7 C8 -1.7(3) ? N1 C6 C7 C8 -178.39(17) ? C11 C6 C7 C12 176.4(2) ? N1 C6 C7 C12 -0.2(3) ? C7 C6 C11 C10 0.7(3) ? N1 C6 C11 C10 177.46(18) ? C6 C7 C8 C9 1.5(3) ? C12 C7 C8 C9 -176.8(2) ? C6 C11 C10 C9 0.8(3) ? C11 C10 C9 C8 -1.1(4) ? C7 C8 C9 C10 -0.1(4) ?