#------------------------------------------------------------------------------ #$Date: 2019-11-10 18:57:35 +0200 (Sun, 10 Nov 2019) $ #$Revision: 225967 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/58/4515875.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_4515875 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_iupac 'C7 H7 N O' _chemical_formula_moiety 'C7 H7 N O' _chemical_formula_sum 'C7 H7 N O' _chemical_formula_weight 121.14 _chemical_name_common N-Phenylformamide _chemical_name_systematic ; N-Phenylformamide ; _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_block_doi 10.5517/ccqxjgl _audit_creation_method SHELXL-97 _audit_update_record ; 2008-03-27 deposited with the CCDC. 2016-09-12 downloaded from the CCDC. ; _cell_angle_alpha 90.00 _cell_angle_beta 113.771(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 16 _cell_length_a 31.177(3) _cell_length_b 6.1229(5) _cell_length_c 14.3335(12) _cell_measurement_reflns_used 2001 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.12 _cell_measurement_theta_min 2.85 _cell_volume 2504.0(4) _computing_cell_refinement 'SAINT-Plus (Bruker, 1999)' _computing_data_collection 'SMART-NT (Bruker, 1998)' _computing_data_reduction 'SAINT-Plus (Bruker, 1999)' _computing_molecular_graphics ; PLATON (Spek, 2003) and ORTEP-3 (Farrugia, 1997) ; _computing_publication_material 'WinGX (Farrugia, 1999)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART 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 0.0260 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_h_min -39 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 7327 _diffrn_reflns_theta_full 27.00 _diffrn_reflns_theta_max 27.00 _diffrn_reflns_theta_min 1.43 _exptl_absorpt_coefficient_mu 0.088 _exptl_absorpt_correction_type none _exptl_crystal_colour 'Pale green' _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 1024 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.187 _refine_diff_density_min -0.180 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 163 _refine_ls_number_reflns 2732 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.0628 _refine_ls_R_factor_gt 0.0396 _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^)+(0.0522P)^2^+0.7143P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0967 _refine_ls_wR_factor_ref 0.1099 _reflns_number_gt 1953 _reflns_number_total 2732 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ao8b01801_si_008.cif _cod_data_source_block I _cod_original_cell_volume 2504.1(4) _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 4515875 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_type_symbol _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_symmetry_multiplicity C C11 0.66832(5) 0.7492(2) 0.78636(10) 0.0299(3) Uani d . 1 1 C C12 0.70000(5) 0.9093(2) 0.78800(11) 0.0377(4) Uani d . 1 1 H H12 0.6890 1.0435 0.7534 0.045 Uiso calc R 1 1 C C13 0.74744(5) 0.8749(3) 0.83952(12) 0.0454(4) Uani d . 1 1 H H13 0.7689 0.9853 0.8398 0.054 Uiso calc R 1 1 C C14 0.76399(5) 0.6826(3) 0.89039(12) 0.0470(4) Uani d . 1 1 H H14 0.7967 0.6602 0.9268 0.056 Uiso calc R 1 1 C C15 0.73264(6) 0.5229(3) 0.88795(13) 0.0513(4) Uani d . 1 1 H H15 0.7440 0.3892 0.9228 0.062 Uiso calc R 1 1 C C16 0.68483(5) 0.5527(3) 0.83581(12) 0.0438(4) Uani d . 1 1 H H16 0.6636 0.4399 0.8340 0.053 Uiso calc R 1 1 C C17 0.58388(5) 0.6706(3) 0.72146(12) 0.0404(4) Uani d . 1 1 H H17 0.5896 0.5306 0.7527 0.048 Uiso calc R 1 1 N N11 0.62025(4) 0.7959(2) 0.73282(8) 0.0331(3) Uani d . 1 1 H H11 0.6136 0.9247 0.7032 0.040 Uiso calc R 1 1 O O11 0.54320(4) 0.7262(2) 0.67274(9) 0.0529(3) Uani d . 1 1 C C21 0.57124(5) 1.5283(2) 0.46422(10) 0.0300(3) Uani d . 1 1 C C22 0.54546(5) 1.6725(3) 0.38727(11) 0.0368(3) Uani d . 1 1 H H22 0.5131 1.6466 0.3482 0.044 Uiso calc R 1 1 C C23 0.56680(6) 1.8534(3) 0.36752(11) 0.0451(4) Uani d . 1 1 H H23 0.5491 1.9513 0.3145 0.054 Uiso calc R 1 1 C C24 0.61379(6) 1.8928(3) 0.42463(11) 0.0452(4) Uani d . 1 1 H H24 0.6285 2.0182 0.4116 0.054 Uiso calc R 1 1 C C25 0.63909(5) 1.7487(3) 0.50050(12) 0.0425(4) Uani d . 1 1 H H25 0.6714 1.7757 0.5397 0.051 Uiso calc R 1 1 C C26 0.61848(5) 1.5657(2) 0.52082(11) 0.0357(3) Uani d . 1 1 H H26 0.6365 1.4667 0.5730 0.043 Uiso calc R 1 1 C C27 0.56217(5) 1.2025(2) 0.55652(12) 0.0405(4) Uani d . 1 1 H H27 0.5413 1.0870 0.5538 0.049 Uiso calc R 1 1 N N21 0.54716(4) 1.34647(19) 0.48004(9) 0.0362(3) Uani d . 1 1 H H21 0.5186 1.3252 0.4336 0.043 Uiso calc R 1 1 O O21 0.60001(4) 1.20441(18) 0.62962(8) 0.0472(3) Uani d . 1 1 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 C11 0.0314(7) 0.0311(7) 0.0275(6) -0.0010(6) 0.0123(5) -0.0024(6) C12 0.0356(7) 0.0301(8) 0.0446(8) -0.0001(6) 0.0132(6) 0.0023(6) C13 0.0335(8) 0.0425(9) 0.0559(9) -0.0047(7) 0.0138(7) -0.0059(8) C14 0.0342(8) 0.0512(10) 0.0493(9) 0.0097(7) 0.0101(7) -0.0023(8) C15 0.0504(9) 0.0457(10) 0.0538(10) 0.0154(8) 0.0171(8) 0.0143(8) C16 0.0448(9) 0.0351(9) 0.0523(9) 0.0015(7) 0.0204(7) 0.0105(7) C17 0.0380(8) 0.0368(8) 0.0455(8) -0.0071(7) 0.0160(7) -0.0078(7) N11 0.0309(6) 0.0310(6) 0.0352(6) -0.0015(5) 0.0110(5) 0.0034(5) O11 0.0314(5) 0.0608(8) 0.0588(7) -0.0083(5) 0.0102(5) -0.0108(6) C21 0.0319(7) 0.0278(7) 0.0312(7) -0.0006(6) 0.0137(6) -0.0031(5) C22 0.0346(7) 0.0380(8) 0.0340(7) -0.0005(6) 0.0098(6) 0.0003(6) C23 0.0528(9) 0.0395(9) 0.0379(8) 0.0014(7) 0.0129(7) 0.0084(7) C24 0.0531(9) 0.0406(9) 0.0435(8) -0.0122(8) 0.0210(7) 0.0037(7) C25 0.0347(7) 0.0473(10) 0.0435(8) -0.0091(7) 0.0137(6) 0.0018(7) C26 0.0311(7) 0.0358(8) 0.0382(7) 0.0005(6) 0.0119(6) 0.0031(6) C27 0.0382(8) 0.0310(8) 0.0484(9) -0.0049(6) 0.0133(7) 0.0039(7) N21 0.0281(6) 0.0331(7) 0.0406(7) -0.0050(5) 0.0066(5) 0.0022(5) O21 0.0424(6) 0.0397(6) 0.0478(6) -0.0048(5) 0.0060(5) 0.0114(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 10.1107/S0108270108002746 2008 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C12 C11 C16 119.35(13) C12 C11 N11 117.40(12) C16 C11 N11 123.24(13) C13 C12 C11 120.35(14) C13 C12 H12 119.8 C11 C12 H12 119.8 C14 C13 C12 120.60(15) C14 C13 H13 119.7 C12 C13 H13 119.7 C13 C14 C15 119.10(15) C13 C14 H14 120.4 C15 C14 H14 120.4 C14 C15 C16 121.37(15) C14 C15 H15 119.3 C16 C15 H15 119.3 C15 C16 C11 119.20(15) C15 C16 H16 120.4 C11 C16 H16 120.4 O11 C17 N11 123.25(15) O11 C17 H17 118.4 N11 C17 H17 118.4 C17 N11 C11 128.26(13) C17 N11 H11 115.9 C11 N11 H11 115.9 C26 C21 C22 119.90(13) C26 C21 N21 123.06(12) C22 C21 N21 117.03(12) C23 C22 C21 120.10(13) C23 C22 H22 120.0 C21 C22 H22 120.0 C22 C23 C24 120.18(14) C22 C23 H23 119.9 C24 C23 H23 119.9 C25 C24 C23 119.33(15) C25 C24 H24 120.3 C23 C24 H24 120.3 C24 C25 C26 121.35(14) C24 C25 H25 119.3 C26 C25 H25 119.3 C25 C26 C21 119.12(13) C25 C26 H26 120.4 C21 C26 H26 120.4 O21 C27 N21 126.51(14) O21 C27 H27 116.7 N21 C27 H27 116.7 C27 N21 C21 128.27(12) C27 N21 H21 115.9 C21 N21 H21 115.9 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C11 C12 1.385(2) C11 C16 1.386(2) C11 N11 1.4103(17) C12 C13 1.377(2) C12 H12 0.9500 C13 C14 1.371(2) C13 H13 0.9500 C14 C15 1.373(2) C14 H14 0.9500 C15 C16 1.384(2) C15 H15 0.9500 C16 H16 0.9500 C17 O11 1.2239(17) C17 N11 1.3238(18) C17 H17 0.9500 N11 H11 0.8800 C21 C26 1.3846(18) C21 C22 1.3884(19) C21 N21 1.4114(18) C22 C23 1.379(2) C22 H22 0.9500 C23 C24 1.381(2) C23 H23 0.9500 C24 C25 1.375(2) C24 H24 0.9500 C25 C26 1.380(2) C25 H25 0.9500 C26 H26 0.9500 C27 O21 1.2219(17) C27 N21 1.3359(19) C27 H27 0.9500 N21 H21 0.8800 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 N11 H11 O21 1_555 0.88 1.97 2.8444(16) 176.0 N21 H21 O11 5_676 0.88 1.94 2.8206(15) 177.6 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 C16 C11 C12 C13 -0.9(2) N11 C11 C12 C13 179.53(13) C11 C12 C13 C14 -0.4(2) C12 C13 C14 C15 1.0(3) C13 C14 C15 C16 -0.4(3) C14 C15 C16 C11 -1.0(3) C12 C11 C16 C15 1.6(2) N11 C11 C16 C15 -178.91(14) O11 C17 N11 C11 -179.64(14) C12 C11 N11 C17 -179.39(14) C16 C11 N11 C17 1.1(2) C26 C21 C22 C23 -0.3(2) N21 C21 C22 C23 -179.86(14) C21 C22 C23 C24 -0.5(2) C22 C23 C24 C25 0.7(3) C23 C24 C25 C26 -0.1(3) C24 C25 C26 C21 -0.7(2) C22 C21 C26 C25 0.9(2) N21 C21 C26 C25 -179.59(14) O21 C27 N21 C21 1.7(3) C26 C21 N21 C27 10.2(2) C22 C21 N21 C27 -170.34(15)