#------------------------------------------------------------------------------ #$Date: 2011-09-10 06:16:28 +0300 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/2013980.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_2013980 loop_ _publ_author_name 'Britton, Doyle' 'Sowa, Jr, John R.' 'Mann, Kent R.' _publ_section_title ; p-Decylphenyl isocyanide and p-decylbenzonitrile: isomorphous isonitrile/nitrile isomers ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first o418 _journal_page_last o420 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C17 H25 N' _chemical_formula_moiety 'C17 H25 N' _chemical_formula_sum 'C17 H25 N' _chemical_formula_weight 243.38 _chemical_name_systematic ; p-decylphenyl isocyanide ; _space_group_IT_number 11 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 91.130(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 2 _cell_length_a 4.6642(12) _cell_length_b 7.831(2) _cell_length_c 20.607(5) _cell_measurement_reflns_used 985 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.4 _cell_measurement_theta_min 2.6 _cell_volume 752.5(3) _computing_cell_refinement 'SAINT (Bruker, 2002)' _computing_data_collection 'SMART (Bruker, 2002)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1997)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.990 _diffrn_measurement_device_type ; Siemens SMART area-detector ; _diffrn_measurement_method '\w 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 0.024 _diffrn_reflns_av_sigmaI/netI 0.026 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 6459 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 27.50 _diffrn_reflns_theta_min 1.98 _diffrn_standards_decay_% 'less than 1' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.061 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_correction_T_min 0.83 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS; Sheldrick, 2002; Blessing, 1995 ; _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.074 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 268 _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.17 _refine_diff_density_min -0.18 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.04 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 154 _refine_ls_number_reflns 1827 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.04 _refine_ls_R_factor_all 0.065 _refine_ls_R_factor_gt 0.038 _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^)+(0.054P)^2^+0.023P] where P=(Fo^2^+2Fc^2^)/3' ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.098 _refine_ls_wR_factor_ref 0.106 _reflns_number_gt 1190 _reflns_number_total 1827 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1469.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/m' _cod_database_code 2013980 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -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 C1 0.0163(4) 0.2500 1.03516(8) 0.0444(4) Uani d S 1 C N2 0.1757(3) 0.2500 0.99256(6) 0.0348(3) Uani d S 1 N C3 0.3717(3) 0.2500 0.94150(6) 0.0301(4) Uani d S 1 C C4 0.4675(2) 0.40436(15) 0.91720(5) 0.0333(3) Uani d . 1 C H4 0.394(2) 0.5105(15) 0.9357(4) 0.034(3) Uiso d . 1 H C5 0.6616(2) 0.40270(15) 0.86747(5) 0.0326(3) Uani d . 1 C H5 0.727(2) 0.5103(16) 0.8499(5) 0.039(3) Uiso d . 1 H C6 0.7598(3) 0.2500 0.84119(6) 0.0300(4) Uani d S 1 C C7 0.9508(3) 0.2500 0.78310(7) 0.0343(4) Uani d S 1 C H7 1.076(2) 0.3521(14) 0.7848(5) 0.039(3) Uiso d . 1 H C8 0.7741(3) 0.2500 0.71951(7) 0.0313(4) Uani d S 1 C H8 0.646(2) 0.3515(14) 0.7196(5) 0.037(3) Uiso d . 1 H C9 0.9539(3) 0.2500 0.65875(7) 0.0311(4) Uani d S 1 C H9 1.084(2) 0.3516(14) 0.6590(5) 0.037(3) Uiso d . 1 H C10 0.7736(3) 0.2500 0.59617(7) 0.0324(4) Uani d S 1 C H10 0.643(2) 0.3508(15) 0.5956(5) 0.040(3) Uiso d . 1 H C11 0.9507(3) 0.2500 0.53483(7) 0.0322(4) Uani d S 1 C H11 1.082(2) 0.3521(14) 0.5353(5) 0.039(3) Uiso d . 1 H C12 0.7700(3) 0.2500 0.47233(7) 0.0332(4) Uani d S 1 C H12 0.642(2) 0.3518(15) 0.4721(5) 0.041(3) Uiso d . 1 H C13 0.9488(3) 0.2500 0.41132(7) 0.0322(4) Uani d S 1 C H13 1.079(2) 0.3508(14) 0.4115(5) 0.036(3) Uiso d . 1 H C14 0.7697(3) 0.2500 0.34850(7) 0.0330(4) Uani d S 1 C H14 0.638(2) 0.3502(14) 0.3480(5) 0.038(3) Uiso d . 1 H C15 0.9467(3) 0.2500 0.28737(7) 0.0346(4) Uani d S 1 C H15 1.078(2) 0.3515(14) 0.2881(5) 0.041(3) Uiso d . 1 H C16 0.7633(4) 0.2500 0.22568(8) 0.0461(5) Uani d S 1 C H16B 0.635(3) 0.3539(17) 0.2245(6) 0.066(4) Uiso d . 1 H H16A 0.881(4) 0.2500 0.1867(9) 0.053(5) Uiso d S 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 0.0453(10) 0.0451(10) 0.0430(10) 0.000 0.0078(8) 0.000 N2 0.0316(7) 0.0402(8) 0.0325(7) 0.000 -0.0005(6) 0.000 C3 0.0254(8) 0.0399(9) 0.0248(8) 0.000 -0.0007(6) 0.000 C4 0.0336(6) 0.0349(6) 0.0314(6) 0.0033(5) -0.0010(5) -0.0020(5) C5 0.0321(6) 0.0348(6) 0.0308(6) -0.0021(5) -0.0023(5) 0.0038(5) C6 0.0238(8) 0.0404(9) 0.0256(8) 0.000 -0.0041(6) 0.000 C7 0.0276(9) 0.0456(10) 0.0297(8) 0.000 -0.0005(7) 0.000 C8 0.0277(9) 0.0383(9) 0.0279(8) 0.000 0.0009(6) 0.000 C9 0.0275(9) 0.0376(9) 0.0282(8) 0.000 0.0009(6) 0.000 C10 0.0288(9) 0.0392(9) 0.0292(8) 0.000 0.0019(6) 0.000 C11 0.0290(9) 0.0381(9) 0.0294(8) 0.000 0.0022(6) 0.000 C12 0.0300(9) 0.0397(9) 0.0301(9) 0.000 0.0021(7) 0.000 C13 0.0278(9) 0.0378(9) 0.0310(8) 0.000 0.0015(6) 0.000 C14 0.0307(9) 0.0368(9) 0.0314(8) 0.000 0.0011(7) 0.000 C15 0.0345(10) 0.0382(9) 0.0311(9) 0.000 0.0032(7) 0.000 C16 0.0500(12) 0.0585(12) 0.0298(10) 0.000 0.0006(8) 0.000 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle C1 N2 C3 . . 179.30(15) C4 C3 C4 . 4_565 121.45(14) C4 C3 N2 . . 119.27(7) C4 C3 N2 4_565 . 119.27(7) C5 C4 C3 . . 118.73(11) C5 C4 H4 . . 122.4(6) C3 C4 H4 . . 118.9(6) C4 C5 C6 . . 121.45(12) C4 C5 H5 . . 119.1(6) C6 C5 H5 . . 119.4(6) C5 C6 C5 4_565 . 118.16(14) C5 C6 C7 4_565 . 120.86(7) C5 C6 C7 . . 120.86(7) C6 C7 C8 . . 111.27(12) C6 C7 H7 . . 109.2(6) C8 C7 H7 . . 109.6(6) C9 C8 C7 . . 114.05(12) C9 C8 H8 . . 110.0(6) C7 C8 H8 . . 108.2(6) C8 C9 C10 . . 113.09(12) C8 C9 H9 . . 109.9(6) C10 C9 H9 . . 109.2(6) C11 C10 C9 . . 113.74(13) C11 C10 H10 . . 109.4(6) C9 C10 H10 . . 109.6(6) C10 C11 C12 . . 113.64(13) C10 C11 H11 . . 109.4(6) C12 C11 H11 . . 109.5(6) C13 C12 C11 . . 113.25(13) C13 C12 H12 . . 109.5(6) C11 C12 H12 . . 108.9(6) C12 C13 C14 . . 113.61(13) C12 C13 H13 . . 109.9(6) C14 C13 H13 . . 109.1(6) C15 C14 C13 . . 113.93(13) C15 C14 H14 . . 109.6(6) C13 C14 H14 . . 109.6(6) C16 C15 C14 . . 112.83(14) C16 C15 H15 . . 110.3(6) C14 C15 H15 . . 109.2(6) C15 C16 H16B . . 110.1(7) C15 C16 H16A . . 111.8(10) H7 C7 H7 4_565 . 107.8(9) H8 C8 H8 4_565 . 106.1(9) H9 C9 H9 4_565 . 105.3(9) H10 C10 H10 4_565 . 104.7(9) H11 C11 H11 4_565 . 105.2(9) H12 C12 H12 4_565 . 106.5(9) H13 C13 H13 4_565 . 104.9(9) H14 C14 H14 4_565 . 104.0(9) H15 C15 H15 4_565 . 104.8(9) H16B C16 H16B 4_565 . 107.4(9) H16B C16 H16A . . 108.6(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance C1 N2 . 1.1616(18) N2 C3 . 1.4072(18) C3 C4 . 1.3858(13) C3 C4 4_565 1.3858(13) C4 C5 . 1.3808(15) C4 H4 . 0.979(11) C5 C6 . 1.3939(13) C5 H5 . 0.969(12) C6 C5 4_565 1.3939(13) C6 C7 . 1.506(2) C7 C8 . 1.5342(19) C7 H7 . 0.989(11) C8 C9 . 1.521(2) C8 H8 . 0.995(11) C9 C10 . 1.5255(19) C9 H9 . 1.001(11) C10 C11 . 1.523(2) C10 H10 . 0.997(11) C11 C12 . 1.5252(19) C11 H11 . 1.007(11) C12 C13 . 1.523(2) C12 H12 . 0.995(11) C13 C14 . 1.527(2) C13 H13 . 0.995(11) C14 C15 . 1.520(2) C14 H14 . 0.996(11) C15 C16 . 1.518(2) C15 H15 . 1.003(11) C16 H16B . 1.009(13) C16 H16A . 0.979(18)