#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/34/2203431.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_2203431 loop_ _publ_author_name 'Pavlovi\'c, Gordana' 'Trali\'c-Kulenovi\'c, Vesna' 'Popovi\'c, Zora' _publ_section_title ; 2-Furancarboxanilide ; _journal_issue 4 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o631 _journal_page_last o633 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C11 H9 N O2' _chemical_formula_moiety 'C11 H9 N O2' _chemical_formula_sum 'C11 H9 N O2' _chemical_formula_weight 187.19 _chemical_melting_point 396.5(5) _chemical_name_common N-phenyl-2-furamide _chemical_name_systematic ; N-phenylfuran-2-carboxamide ; _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' _atom_sites_solution_hydrogens 'geom & difmap' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _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 8.699(2) _cell_length_b 12.983(2) _cell_length_c 16.712(2) _cell_measurement_reflns_used 5046 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27 _cell_measurement_theta_min 15 _cell_volume 1887.4(6) _computing_cell_refinement 'CrysAlisRED (Oxford Diffraction, 2003)' _computing_data_collection 'CrysAlisCCD (Oxford Diffraction, 2003)' _computing_data_reduction CrysAlisRED _computing_molecular_graphics 'PLATON98 (Spek, 1998)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.969 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measurement_device_type 'Oxford Diffraction Xcalibur2 diffractometer with Sapphire 3 CCD detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator 'graphite parallel' _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0487 _diffrn_reflns_av_sigmaI/netI 0.0197 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 32112 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 26.50 _diffrn_reflns_theta_min 4.62 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.092 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 784 _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.51 _exptl_crystal_size_min 0.42 _refine_diff_density_max 0.153 _refine_diff_density_min -0.143 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.189 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 131 _refine_ls_number_reflns 1903 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.189 _refine_ls_R_factor_all 0.0580 _refine_ls_R_factor_gt 0.0504 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0753P)^2^+0.0157P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1232 _refine_ls_wR_factor_ref 0.1295 _reflns_number_gt 1758 _reflns_number_total 1903 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fl6090.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '396-397' was changed to '396.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '396-397' was changed to '396.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 1887.4(5) _cod_database_code 2203431 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_type_symbol O1 0.01579(12) 0.23504(9) 0.17519(6) 0.0489(3) Uani d . 1 O O2 0.39457(12) 0.13439(10) 0.16041(7) 0.0551(4) Uani d . 1 O N 0.20672(15) 0.10881(10) 0.25433(7) 0.0425(3) Uani d . 1 N H1N 0.116(2) 0.1250(14) 0.2682(11) 0.054(5) Uiso d . 1 H C1 0.15826(16) 0.21861(11) 0.14299(9) 0.0399(4) Uani d . 1 C C2 0.17223(19) 0.27172(14) 0.07415(10) 0.0527(4) Uani d . 1 C H2 0.2577 0.2735 0.0407 0.063 Uiso calc R 1 H C3 0.0314(2) 0.32436(14) 0.06263(10) 0.0570(5) Uani d . 1 C H3 0.0063 0.3674 0.0201 0.068 Uiso calc R 1 H C4 -0.0578(2) 0.30038(13) 0.12434(10) 0.0538(4) Uani d . 1 C H4 -0.1573 0.3249 0.1318 0.065 Uiso calc R 1 H C5 0.26397(17) 0.14961(11) 0.18630(8) 0.0402(4) Uani d . 1 C C6 0.28327(16) 0.04057(11) 0.30710(9) 0.0397(4) Uani d . 1 C C7 0.24840(18) 0.04681(12) 0.38803(9) 0.0483(4) Uani d . 1 C H7 0.1769 0.0949 0.4058 0.058 Uiso calc R 1 H C8 0.3190(2) -0.01771(15) 0.44211(11) 0.0577(5) Uani d . 1 C H8 0.2948 -0.0133 0.4962 0.069 Uiso calc R 1 H C9 0.4255(2) -0.08887(14) 0.41620(11) 0.0609(5) Uani d . 1 C H9 0.4746 -0.1316 0.4528 0.073 Uiso calc R 1 H C10 0.4590(2) -0.09649(14) 0.33579(11) 0.0577(5) Uani d . 1 C H10 0.5302 -0.1450 0.3184 0.069 Uiso calc R 1 H C11 0.38778(18) -0.03252(12) 0.28042(11) 0.0492(4) Uani d . 1 C H11 0.4098 -0.0386 0.2262 0.059 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 O1 0.0375(6) 0.0579(7) 0.0513(7) 0.0089(5) 0.0039(4) 0.0106(5) O2 0.0359(6) 0.0736(8) 0.0558(7) 0.0095(5) 0.0076(5) 0.0099(5) N 0.0312(7) 0.0512(8) 0.0451(7) 0.0068(5) 0.0030(5) 0.0046(5) C1 0.0317(7) 0.0449(8) 0.0432(8) -0.0011(6) -0.0006(6) -0.0030(6) C2 0.0443(9) 0.0667(10) 0.0472(9) 0.0021(7) 0.0051(7) 0.0093(7) C3 0.0541(10) 0.0638(11) 0.0530(9) 0.0072(8) -0.0018(8) 0.0150(8) C4 0.0428(9) 0.0583(10) 0.0604(10) 0.0114(7) -0.0027(7) 0.0098(8) C5 0.0341(8) 0.0446(8) 0.0418(7) 0.0004(6) -0.0012(6) -0.0026(6) C6 0.0326(7) 0.0420(7) 0.0444(8) -0.0023(6) -0.0028(6) 0.0012(6) C7 0.0449(8) 0.0531(9) 0.0470(9) -0.0009(7) -0.0029(6) -0.0039(7) C8 0.0570(10) 0.0687(11) 0.0475(9) -0.0080(9) -0.0104(7) 0.0038(8) C9 0.0514(10) 0.0630(11) 0.0684(11) -0.0034(8) -0.0202(9) 0.0165(9) C10 0.0447(9) 0.0517(9) 0.0767(12) 0.0085(8) -0.0040(8) 0.0064(8) C11 0.0443(8) 0.0493(8) 0.0540(9) 0.0053(7) 0.0017(7) 0.0010(7) 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' 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 C4 O1 C1 106.14(12) no C5 N C6 126.6(2) yes C5 N H1N 118.4(12) no C6 N H1N 114.9(12) no C2 C1 O1 109.75(13) no C2 C1 C5 132.42(14) no O1 C1 C5 117.83(12) no C1 C2 C3 106.58(14) no C1 C2 H2 126.7 no C3 C2 H2 126.7 no C4 C3 C2 106.68(14) no C4 C3 H3 126.7 no C2 C3 H3 126.7 no C3 C4 O1 110.85(14) no C3 C4 H4 124.6 no O1 C4 H4 124.6 no O2 C5 N 124.98(14) no O2 C5 C1 120.04(13) no N C5 C1 114.97(13) no C11 C6 C7 119.74(15) no C11 C6 N 122.38(14) no C7 C6 N 117.87(13) no C8 C7 C6 120.43(16) no C8 C7 H7 119.8 no C6 C7 H7 119.8 no C7 C8 C9 120.09(16) no C7 C8 H8 120.0 no C9 C8 H8 120.0 no C8 C9 C10 119.77(16) no C8 C9 H9 120.1 no C10 C9 H9 120.1 no C9 C10 C11 120.80(17) no C9 C10 H10 119.6 no C11 C10 H10 119.6 no C6 C11 C10 119.14(16) no C6 C11 H11 120.4 no C10 C11 H11 120.4 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag O1 C4 1.361(2) yes O1 C1 1.368(2) yes O2 C5 1.232(2) yes N C5 1.349(2) yes N C6 1.416(2) yes N H1N 0.85(2) yes C1 C2 1.347(2) yes C1 C5 1.474(2) yes C2 C3 1.416(3) yes C2 H2 0.9300 no C3 C4 1.328(2) yes C3 H3 0.9300 no C4 H4 0.9300 no C6 C11 1.388(2) no C6 C7 1.388(2) no C7 C8 1.377(2) no C7 H7 0.9300 no C8 C9 1.378(3) no C8 H8 0.9300 no C9 C10 1.379(3) no C9 H9 0.9300 no C10 C11 1.389(2) no C10 H10 0.9300 no C11 H11 0.9300 no 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 N H1N O1 . 0.85(2) 2.28(2) 2.682(2) 109(2) yes N H1N O2 8_556 0.85(2) 2.27(2) 3.084(2) 161(2) 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 C4 O1 C1 C2 -0.28(17) no C4 O1 C1 C5 -179.91(13) no O1 C1 C2 C3 0.13(18) no C5 C1 C2 C3 179.69(16) no C1 C2 C3 C4 0.1(2) no C2 C3 C4 O1 -0.3(2) no C1 O1 C4 C3 0.33(19) no C6 N C5 O2 -1.2(2) no C6 N C5 C1 -179.99(13) no C2 C1 C5 O2 2.0(3) no O1 C1 C5 O2 -178.42(13) no C2 C1 C5 N -179.13(16) no O1 C1 C5 N 0.40(19) no C5 N C6 C11 -33.7(2) no C5 N C6 C7 147.67(14) no C11 C6 C7 C8 1.2(2) no N C6 C7 C8 179.86(14) no C6 C7 C8 C9 0.3(2) no C7 C8 C9 C10 -1.2(3) no C8 C9 C10 C11 0.6(3) no C7 C6 C11 C10 -1.8(2) no N C6 C11 C10 179.67(14) no C9 C10 C11 C6 0.8(3) no _cod_database_fobs_code 2203431 _journal_paper_doi 10.1107/S1600536804006245