#------------------------------------------------------------------------------ #$Date: 2011-09-28 15:24:46 +0100 (Wed, 28 Sep 2011) $ #$Revision: 26848 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/31/2203176.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_2203176 loop_ _publ_author_name 'Miaoyu Li' 'Caixia Yin' 'Pin Yang' _publ_section_title ; (1-Benzylpiperidin-4-ylidene)acetonitrile ; _journal_issue 2 _journal_name_full 'Acta Crystallographica, Section E' _journal_page_first o250 _journal_page_last o251 _journal_volume 60 _journal_year 2004 _chemical_formula_iupac 'C14 H16 N2' _chemical_formula_moiety 'C14 H16 N2' _chemical_formula_sum 'C14 H16 N2' _chemical_formula_weight 212.29 _chemical_melting_point 363 _chemical_name_common 1-benzylpiperidin-4-ylideneacetonitrile _chemical_name_systematic ; 1-benzylpiperidin-4-ylideneacetonitrile ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.579(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 6.442(2) _cell_length_b 15.681(5) _cell_length_c 12.120(4) _cell_measurement_reflns_used 6062 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 19.07 _cell_measurement_theta_min 3.17 _cell_volume 1220.5(7) _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_collection 'SMART (Bruker, 2000)' _computing_data_reduction 'SAINT and SHELXTL (Bruker, 2000)' _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 298(2) _diffrn_detector_area_resol_mean '100x100 microns' _diffrn_measured_fraction_theta_full 0.995 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method \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 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0917 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 5816 _diffrn_reflns_theta_full 24.99 _diffrn_reflns_theta_max 24.99 _diffrn_reflns_theta_min 2.60 _diffrn_standards_interval_count no _diffrn_standards_number no _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_T_max 0.9931 _exptl_absorpt_correction_T_min 0.9864 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.155 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 456 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.147 _refine_diff_density_min -0.114 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.006 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 145 _refine_ls_number_reflns 2142 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.006 _refine_ls_R_factor_all 0.1309 _refine_ls_R_factor_gt 0.0652 _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^)+(0.047P)^2^+0.039P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1311 _refine_ls_wR_factor_ref 0.1581 _reflns_number_gt 1128 _reflns_number_total 2142 _reflns_threshold_expression I>2\s(I) _[local]_cod_cif_authors_sg_H-M 'P 21/c' _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 ; _cod_database_code 2203176 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, 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 N1 0.3558(3) 0.36478(13) -0.00249(16) 0.0511(6) Uani d . 1 N N2 0.6668(5) 0.4098(2) -0.4414(2) 0.1142(12) Uani d . 1 N C10 -0.0113(5) 0.2740(2) 0.1620(2) 0.0739(9) Uani d . 1 C H10 -0.0571 0.2367 0.1056 0.089 Uiso calc R 1 H C9 0.1809(4) 0.31212(18) 0.1601(2) 0.0528(7) Uani d . 1 C C14 0.2454(5) 0.36650(18) 0.2450(2) 0.0700(9) Uani d . 1 C H14 0.3753 0.3923 0.2453 0.084 Uiso calc R 1 H C13 0.1215(7) 0.3833(2) 0.3294(3) 0.0923(12) Uani d . 1 C H13 0.1665 0.4203 0.3864 0.111 Uiso calc R 1 H C12 -0.0725(7) 0.3442(3) 0.3283(3) 0.1019(15) Uani d . 1 C H12 -0.1589 0.3551 0.3846 0.122 Uiso calc R 1 H C11 -0.1350(5) 0.2903(3) 0.2452(3) 0.0988(13) Uani d . 1 C H11 -0.2645 0.2640 0.2449 0.119 Uiso calc R 1 H C8 0.3189(4) 0.29198(19) 0.0697(2) 0.0664(8) Uani d . 1 C H8B 0.4518 0.2717 0.1029 0.080 Uiso calc R 1 H H8A 0.2563 0.2461 0.0248 0.080 Uiso calc R 1 H C5 0.1667(4) 0.38653(19) -0.0702(2) 0.0621(8) Uani d . 1 C H5B 0.0583 0.4015 -0.0225 0.074 Uiso calc R 1 H H5A 0.1197 0.3373 -0.1137 0.074 Uiso calc R 1 H C4 0.2020(4) 0.4607(2) -0.1473(2) 0.0712(9) Uani d . 1 C H4B 0.0767 0.4706 -0.1955 0.085 Uiso calc R 1 H H4A 0.2317 0.5120 -0.1041 0.085 Uiso calc R 1 H C3 0.3790(4) 0.44206(17) -0.2154(2) 0.0553(7) Uani d . 1 C C2 0.5702(4) 0.4165(2) -0.1480(2) 0.0661(9) Uani d . 1 C H2B 0.6233 0.4644 -0.1036 0.079 Uiso calc R 1 H H2A 0.6762 0.3995 -0.1961 0.079 Uiso calc R 1 H C1 0.5218(4) 0.3429(2) -0.0730(2) 0.0680(9) Uani d . 1 C H1B 0.4799 0.2937 -0.1179 0.082 Uiso calc R 1 H H1A 0.6464 0.3277 -0.0270 0.082 Uiso calc R 1 H C6 0.3615(5) 0.44485(19) -0.3257(2) 0.0700(9) Uani d . 1 C H6 0.2342 0.4601 -0.3619 0.084 Uiso calc R 1 H C7 0.5312(6) 0.4252(2) -0.3901(2) 0.0771(10) Uani d . 1 C 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 N1 0.0458(13) 0.0605(16) 0.0479(12) 0.0057(11) 0.0097(11) 0.0085(11) N2 0.162(3) 0.110(3) 0.079(2) 0.030(2) 0.062(2) 0.0120(18) C10 0.067(2) 0.088(3) 0.066(2) -0.0084(19) -0.0001(17) 0.0214(17) C9 0.0535(17) 0.0553(19) 0.0501(16) 0.0034(15) 0.0072(13) 0.0137(14) C14 0.086(2) 0.062(2) 0.062(2) -0.0039(18) 0.0057(18) 0.0047(16) C13 0.147(4) 0.073(3) 0.058(2) 0.022(3) 0.013(2) 0.0052(18) C12 0.135(4) 0.107(4) 0.072(3) 0.052(3) 0.054(3) 0.039(2) C11 0.075(2) 0.130(4) 0.095(3) 0.008(2) 0.029(2) 0.052(3) C8 0.077(2) 0.064(2) 0.0595(17) 0.0102(16) 0.0121(15) 0.0088(15) C5 0.0510(17) 0.081(2) 0.0551(16) 0.0066(16) 0.0104(14) 0.0093(15) C4 0.073(2) 0.087(3) 0.0556(18) 0.0210(18) 0.0159(16) 0.0174(16) C3 0.0649(19) 0.0502(18) 0.0521(17) -0.0037(14) 0.0128(15) 0.0037(14) C2 0.0578(19) 0.090(3) 0.0518(16) -0.0054(16) 0.0150(14) -0.0014(16) C1 0.0550(18) 0.089(2) 0.0619(18) 0.0165(16) 0.0141(15) 0.0070(17) C6 0.086(2) 0.070(2) 0.0548(18) 0.0048(18) 0.0135(16) 0.0065(16) C7 0.123(3) 0.063(2) 0.0487(18) 0.006(2) 0.0258(19) 0.0057(16) 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 _geom_angle_publ_flag C5 N1 C1 110.1(2) y C5 N1 C8 110.5(2) y C1 N1 C8 109.1(2) ? C11 C10 C9 120.9(3) ? C11 C10 H10 119.6 ? C9 C10 H10 119.6 ? C14 C9 C10 118.3(3) ? C14 C9 C8 121.1(3) ? C10 C9 C8 120.5(3) ? C13 C14 C9 121.2(3) ? C13 C14 H14 119.4 ? C9 C14 H14 119.4 ? C14 C13 C12 118.9(3) ? C14 C13 H13 120.6 ? C12 C13 H13 120.6 ? C11 C12 C13 119.8(4) ? C11 C12 H12 120.1 ? C13 C12 H12 120.1 ? C12 C11 C10 120.8(4) ? C12 C11 H11 119.6 ? C10 C11 H11 119.6 ? N1 C8 C9 113.9(2) y N1 C8 H8B 108.8 ? C9 C8 H8B 108.8 ? N1 C8 H8A 108.8 ? C9 C8 H8A 108.8 ? H8B C8 H8A 107.7 ? N1 C5 C4 111.5(2) y N1 C5 H5B 109.3 ? C4 C5 H5B 109.3 ? N1 C5 H5A 109.3 ? C4 C5 H5A 109.3 ? H5B C5 H5A 108.0 ? C3 C4 C5 110.4(2) y C3 C4 H4B 109.6 ? C5 C4 H4B 109.6 ? C3 C4 H4A 109.6 ? C5 C4 H4A 109.6 ? H4B C4 H4A 108.1 ? C6 C3 C2 124.3(3) y C6 C3 C4 122.8(3) y C2 C3 C4 112.8(2) y C3 C2 C1 109.6(2) y C3 C2 H2B 109.8 ? C1 C2 H2B 109.8 ? C3 C2 H2A 109.8 ? C1 C2 H2A 109.8 ? H2B C2 H2A 108.2 ? N1 C1 C2 111.5(2) y N1 C1 H1B 109.3 ? C2 C1 H1B 109.3 ? N1 C1 H1A 109.3 ? C2 C1 H1A 109.3 ? H1B C1 H1A 108.0 ? C3 C6 C7 122.3(3) y C3 C6 H6 118.8 ? C7 C6 H6 118.8 ? N2 C7 C6 179.8(4) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 1.454(3) ? N1 C1 1.462(3) ? N1 C8 1.469(3) y N2 C7 1.138(4) y C10 C11 1.358(4) ? C10 C9 1.377(4) ? C10 H10 0.9300 ? C9 C14 1.375(4) ? C9 C8 1.498(3) y C14 C13 1.372(4) ? C14 H14 0.9300 ? C13 C12 1.391(5) ? C13 H13 0.9300 ? C12 C11 1.351(5) ? C12 H12 0.9300 ? C11 H11 0.9300 ? C8 H8B 0.9700 ? C8 H8A 0.9700 ? C5 C4 1.520(4) ? C5 H5B 0.9700 ? C5 H5A 0.9700 ? C4 C3 1.489(3) ? C4 H4B 0.9700 ? C4 H4A 0.9700 ? C3 C6 1.333(3) y C3 C2 1.478(4) ? C2 C1 1.516(4) ? C2 H2B 0.9700 ? C2 H2A 0.9700 ? C1 H1B 0.9700 ? C1 H1A 0.9700 ? C6 C7 1.427(4) y C6 H6 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 C12 H12 N2 1_456 0.93 2.61 3.524(5) 167 no 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 C11 C10 C9 C14 0.6(4) C11 C10 C9 C8 178.3(3) C10 C9 C14 C13 -0.6(4) C8 C9 C14 C13 -178.3(3) C9 C14 C13 C12 0.1(5) C14 C13 C12 C11 0.4(5) C13 C12 C11 C10 -0.4(6) C9 C10 C11 C12 -0.1(5) C5 N1 C8 C9 -69.6(3) C1 N1 C8 C9 169.2(2) C14 C9 C8 N1 -67.6(3) C10 C9 C8 N1 114.8(3) C1 N1 C5 C4 -58.4(3) C8 N1 C5 C4 -178.9(2) N1 C5 C4 C3 54.6(3) C5 C4 C3 C6 124.6(3) C5 C4 C3 C2 -52.7(3) C6 C3 C2 C1 -123.7(3) C4 C3 C2 C1 53.6(3) C5 N1 C1 C2 59.8(3) C8 N1 C1 C2 -178.8(2) C3 C2 C1 N1 -56.9(3) C2 C3 C6 C7 -1.8(5) C4 C3 C6 C7 -178.7(3) C3 C6 C7 N2 -8E1(10)