#------------------------------------------------------------------------------ #$Date: 2019-11-10 18:58:47 +0200 (Sun, 10 Nov 2019) $ #$Revision: 225971 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/58/4515879.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_4515879 loop_ _publ_author_name 'Pagliari, Anderson B.' 'Orlando, Tain\'ara' 'Salbego, Paulo R. S.' 'Zimmer, Ge\'orgia C' 'H\"orner, Manfredo' 'Zanatta, Nilo' 'Bonacorso, Helio G.' 'Martins, Marcos A. P.' _publ_section_title ; Supramolecular Packing of a Series of N-Phenylamides and the Role of NH···O=C Interactions. ; _journal_issue 10 _journal_name_full 'ACS omega' _journal_page_first 13850 _journal_page_last 13861 _journal_paper_doi 10.1021/acsomega.8b01801 _journal_volume 3 _journal_year 2018 _chemical_formula_sum 'C13 H11 N O' _chemical_formula_weight 197.23 _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_block_doi 10.5517/cc11dyzc _audit_creation_method SHELXL-97 _audit_update_record ; 2013-11-19 deposited with the CCDC. 2016-07-31 downloaded from the CCDC. ; _cell_angle_alpha 73.23(2) _cell_angle_beta 79.202(19) _cell_angle_gamma 89.85(2) _cell_formula_units_Z 2 _cell_length_a 5.352(6) _cell_length_b 7.971(8) _cell_length_c 12.471(13) _cell_measurement_reflns_used 863 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 51.794 _cell_measurement_theta_min 6.958 _cell_volume 499.6(9) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.987 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _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 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0619 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 1847 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 25.50 _diffrn_reflns_theta_min 2.73 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.11032 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details sadabs _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prismatic _exptl_crystal_F_000 208 _exptl_crystal_size_max 0.245 _exptl_crystal_size_mid 0.211 _exptl_crystal_size_min 0.147 _refine_diff_density_max 0.447 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.960 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 141 _refine_ls_number_reflns 1849 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 0.963 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0646 _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^)+(0.1227P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1770 _refine_ls_wR_factor_ref 0.1886 _reflns_number_gt 1254 _reflns_number_total 1847 _reflns_threshold_expression >2sigma(I) _cod_data_source_file ao8b01801_si_004.cif _cod_data_source_block cd212428 _cod_depositor_comments ; The following automatic conversions were performed: data item '_symmetry_cell_setting' value 'Triclinic' was changed to 'triclinic' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_original_sg_symbol_H-M P-1 _cod_database_code 4515879 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags N1 N 0.3127(4) 0.2518(3) 0.46428(19) 0.0435(6) Uani 1 1 d D O1 O -0.1191(3) 0.2439(3) 0.50066(15) 0.0560(7) Uani 1 1 d U C1 C 0.0833(5) 0.2459(4) 0.5335(2) 0.0421(7) Uani 1 1 d U C2 C 0.0942(5) 0.2387(3) 0.65440(19) 0.0364(6) Uani 1 1 d . C3 C -0.1088(5) 0.1521(3) 0.7387(2) 0.0413(7) Uani 1 1 d . H3 H -0.2402 0.0977 0.7194 0.050 Uiso 1 1 calc R C4 C -0.1170(5) 0.1462(4) 0.8508(2) 0.0440(7) Uani 1 1 d . H4 H -0.2534 0.0865 0.9067 0.053 Uiso 1 1 calc R C5 C 0.0731(5) 0.2272(4) 0.8813(2) 0.0435(7) Uani 1 1 d . H5 H 0.0649 0.2229 0.9572 0.052 Uiso 1 1 calc R C6 C 0.2769(5) 0.3154(4) 0.7983(2) 0.0452(7) Uani 1 1 d . H6 H 0.4055 0.3715 0.8182 0.054 Uiso 1 1 calc R C7 C 0.2886(5) 0.3196(3) 0.6856(2) 0.0417(7) Uani 1 1 d . H7 H 0.4273 0.3770 0.6301 0.050 Uiso 1 1 calc R C8 C 0.3526(5) 0.2580(3) 0.34684(19) 0.0365(6) Uani 1 1 d . C9 C 0.5661(5) 0.1828(4) 0.3051(2) 0.0422(7) Uani 1 1 d . H9 H 0.6712 0.1253 0.3540 0.051 Uiso 1 1 calc R C10 C 0.6251(5) 0.1920(4) 0.1911(2) 0.0443(7) Uani 1 1 d . H10 H 0.7696 0.1403 0.1639 0.053 Uiso 1 1 calc R C11 C 0.4724(5) 0.2770(4) 0.1171(2) 0.0435(7) Uani 1 1 d . H11 H 0.5137 0.2827 0.0402 0.052 Uiso 1 1 calc R C12 C 0.2589(5) 0.3531(3) 0.1576(2) 0.0420(7) Uani 1 1 d . H12 H 0.1554 0.4105 0.1078 0.050 Uiso 1 1 calc R C13 C 0.1963(5) 0.3450(3) 0.27228(19) 0.0409(7) Uani 1 1 d . H13 H 0.0517 0.3970 0.2993 0.049 Uiso 1 1 calc R H1 H 0.428(6) 0.246(5) 0.505(3) 0.109(16) Uiso 1 1 d D 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 N1 0.0421(13) 0.0556(16) 0.0341(12) -0.0156(11) -0.0068(9) 0.0042(10) O1 0.0324(10) 0.1021(18) 0.0346(10) -0.0223(10) -0.0057(7) -0.0014(10) C1 0.0372(13) 0.0454(17) 0.0433(15) -0.0132(12) -0.0065(10) 0.0001(12) C2 0.0411(14) 0.0363(15) 0.0310(13) -0.0100(11) -0.0049(10) 0.0079(11) C3 0.0419(14) 0.0462(17) 0.0362(14) -0.0123(12) -0.0081(11) -0.0006(12) C4 0.0432(14) 0.0492(17) 0.0333(14) -0.0091(12) 0.0031(11) 0.0024(12) C5 0.0524(15) 0.0514(18) 0.0293(13) -0.0155(12) -0.0083(11) 0.0129(13) C6 0.0438(14) 0.0491(18) 0.0482(16) -0.0202(13) -0.0127(12) 0.0023(12) C7 0.0386(14) 0.0446(17) 0.0375(14) -0.0105(12) 0.0011(11) -0.0005(12) C8 0.0445(14) 0.0367(15) 0.0274(12) -0.0094(10) -0.0048(10) -0.0040(11) C9 0.0433(14) 0.0437(17) 0.0425(15) -0.0145(12) -0.0124(11) 0.0028(12) C10 0.0399(14) 0.0514(18) 0.0436(15) -0.0215(13) -0.0008(11) 0.0026(12) C11 0.0483(15) 0.0528(18) 0.0300(13) -0.0175(12) -0.0005(11) -0.0062(13) C12 0.0447(14) 0.0468(17) 0.0341(14) -0.0091(11) -0.0108(11) -0.0009(12) C13 0.0396(13) 0.0467(17) 0.0352(14) -0.0134(12) -0.0021(11) 0.0046(12) 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_ _citation_id _citation_doi _citation_year 1 10.1039/C3CE42060D 2014 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 N1 C8 125.6(2) C1 N1 H1 108(2) C8 N1 H1 127(2) O1 C1 N1 122.7(3) O1 C1 C2 122.3(2) N1 C1 C2 115.0(2) C3 C2 C7 118.6(2) C3 C2 C1 117.1(2) C7 C2 C1 124.2(2) C4 C3 C2 120.4(2) C4 C3 H3 119.8 C2 C3 H3 119.8 C5 C4 C3 121.0(2) C5 C4 H4 119.5 C3 C4 H4 119.5 C4 C5 C6 119.6(2) C4 C5 H5 120.2 C6 C5 H5 120.2 C5 C6 C7 119.8(3) C5 C6 H6 120.1 C7 C6 H6 120.1 C6 C7 C2 120.6(2) C6 C7 H7 119.7 C2 C7 H7 119.7 C9 C8 C13 119.4(2) C9 C8 N1 117.0(2) C13 C8 N1 123.5(2) C8 C9 C10 120.3(2) C8 C9 H9 119.8 C10 C9 H9 119.8 C9 C10 C11 120.8(2) C9 C10 H10 119.6 C11 C10 H10 119.6 C12 C11 C10 119.5(2) C12 C11 H11 120.3 C10 C11 H11 120.3 C11 C12 C13 120.5(2) C11 C12 H12 119.7 C13 C12 H12 119.7 C12 C13 C8 119.4(2) C12 C13 H13 120.3 C8 C13 H13 120.3 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance N1 C1 1.354(3) N1 C8 1.426(3) N1 H1 0.857(19) O1 C1 1.229(3) C1 C2 1.505(4) C2 C3 1.385(4) C2 C7 1.397(4) C3 C4 1.378(3) C3 H3 0.9300 C4 C5 1.373(4) C4 H4 0.9300 C5 C6 1.384(4) C5 H5 0.9300 C6 C7 1.386(3) C6 H6 0.9300 C7 H7 0.9300 C8 C9 1.374(4) C8 C13 1.401(4) C9 C10 1.377(3) C9 H9 0.9300 C10 C11 1.378(4) C10 H10 0.9300 C11 C12 1.373(4) C11 H11 0.9300 C12 C13 1.389(3) C12 H12 0.9300 C13 H13 0.9300 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 N1 H1 O1 0.857(19) 2.42(3) 3.155(4) 145(3) 1_655 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 C8 N1 C1 O1 0.6(4) C8 N1 C1 C2 179.5(2) O1 C1 C2 C3 28.9(4) N1 C1 C2 C3 -150.0(3) O1 C1 C2 C7 -148.1(3) N1 C1 C2 C7 32.9(4) C7 C2 C3 C4 -0.2(4) C1 C2 C3 C4 -177.4(2) C2 C3 C4 C5 0.8(4) C3 C4 C5 C6 -0.4(4) C4 C5 C6 C7 -0.6(4) C5 C6 C7 C2 1.2(4) C3 C2 C7 C6 -0.8(4) C1 C2 C7 C6 176.2(2) C1 N1 C8 C9 -150.0(3) C1 N1 C8 C13 34.1(4) C13 C8 C9 C10 -0.4(4) N1 C8 C9 C10 -176.4(2) C8 C9 C10 C11 0.2(4) C9 C10 C11 C12 -0.1(4) C10 C11 C12 C13 0.0(4) C11 C12 C13 C8 -0.1(4) C9 C8 C13 C12 0.3(4) N1 C8 C13 C12 176.1(2)