#------------------------------------------------------------------------------ #$Date: 2020-02-14 12:27:31 +0200 (Fri, 14 Feb 2020) $ #$Revision: 248154 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557318.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_1557318 loop_ _publ_author_name 'Kolsaker, Per' 'Songe, Pal' 'Romming, Christian' _publ_section_title ; Dimerization of Cyclopropanecarbonitrile Mediated by Grignard Reagents. Formation of Highly Substituted Pyridines ; _journal_name_full 'Acta Chemica Scandinavica' _journal_page_first 1104 _journal_page_last 1111 _journal_paper_doi 10.3891/acta.chem.scand.51-1104 _journal_volume 51 _journal_year 1997 _chemical_formula_sum 'C16 H17 N5' _chemical_formula_weight 279.34 _chemical_name_common ; 2-Amino-3-cyano-5-(3,3-dicyanopropyl)-6-cyclopropyl-4-ethylpyridine ; _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 98.31(1) _cell_angle_beta 99.77(1) _cell_angle_gamma 109.24(2) _cell_formula_units_Z 2 _cell_length_a 8.118(1) _cell_length_b 9.890(2) _cell_length_c 10.266(2) _cell_volume 748.9(3) _diffrn_ambient_temperature 138 _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _exptl_absorpt_coefficient_mu 0.073 _exptl_crystal_density_diffrn 1.239 _exptl_crystal_F_000 296 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_number_parameters 258 _refine_ls_number_reflns 3603 _refine_ls_R_factor_gt 0.047 _refine_ls_wR_factor_ref 0.135 _cod_data_source_file Acta-Chem-Scand-1997-51-1104-1.cif _cod_data_source_block 1 _cod_original_cell_volume 748.9(2) _cod_database_code 1557318 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 x,y,z 2 -x,-y,-z loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N Uiso 0.12810(10) 0.66750(10) 0.72520(10) 1.000 0.0230(10) . . . . N2 N Uiso 0.37810(10) 0.67050(10) 0.64880(10) 1.000 0.0340(10) . . . . N3 N Uiso 0.34980(10) 0.31790(10) 0.53670(10) 1.000 0.0350(10) . . . . N4 N Uiso -0.4751(2) -0.01180(10) 0.82340(10) 1.000 0.0420(10) . . . . N5 N Uiso -0.67670(10) 0.33420(10) 0.91850(10) 1.000 0.0400(10) . . . . C2 C Uiso 0.21680(10) 0.59180(10) 0.66880(10) 1.000 0.0220(10) . . . . C3 C Uiso 0.14990(10) 0.43690(10) 0.63970(10) 1.000 0.0220(10) . . . . C4 C Uiso -0.00830(10) 0.35990(10) 0.67490(10) 1.000 0.0220(10) . . . . C5 C Uiso -0.10280(10) 0.44050(10) 0.73030(10) 1.000 0.0210(10) . . . . C6 C Uiso -0.02810(10) 0.59420(10) 0.75330(10) 1.000 0.0210(10) . . . . C7 C Uiso 0.25640(10) 0.36560(10) 0.58240(10) 1.000 0.0260(10) . . . . C8 C Uiso -0.06670(10) 0.19520(10) 0.65790(10) 1.000 0.0270(10) . . . . C9 C Uiso -0.2069(2) 0.10790(10) 0.52730(10) 1.000 0.0370(10) . . . . C10 C Uiso -0.27360(10) 0.36380(10) 0.77190(10) 1.000 0.0230(10) . . . . C11 C Uiso -0.23670(10) 0.35840(10) 0.92210(10) 1.000 0.0220(10) . . . . C12 C Uiso -0.11520(10) 0.68820(10) 0.81670(10) 1.000 0.0260(10) . . . . C13 C Uiso -0.0006(2) 0.83720(10) 0.90620(10) 1.000 0.0310(10) . . . . C14 C Uiso -0.1106(2) 0.82780(10) 0.77120(10) 1.000 0.0310(10) . . . . C15 C Uiso -0.39980(10) 0.25310(10) 0.96110(10) 1.000 0.0240(10) . . . . C16 C Uiso -0.44700(10) 0.10270(10) 0.88420(10) 1.000 0.0290(10) . . . . C17 C Uiso -0.55690(10) 0.29720(10) 0.93680(10) 1.000 0.0280(10) . . . . 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' 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_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 N1 C6 118.98(9) . . . yes N1 C2 N2 116.78(9) . . . yes N1 C2 C3 121.31(9) . . . yes N2 C2 C3 121.79(9) . . . yes C2 C3 C4 120.00(9) . . . no C2 C3 C7 117.27(8) . . . no C4 C3 C7 122.60(9) . . . no C3 C4 C5 118.01(9) . . . no C3 C4 C8 119.31(8) . . . no C5 C4 C8 122.63(8) . . . no C4 C5 C6 118.02(8) . . . no C4 C5 C10 120.55(9) . . . no C6 C5 C10 121.32(8) . . . no N1 C6 C5 123.54(9) . . . yes N1 C6 C12 114.80(9) . . . yes C5 C6 C12 121.62(8) . . . no N3 C7 C3 175.29(10) . . . yes C4 C8 C9 114.38(8) . . . no C5 C10 C11 111.48(8) . . . no C10 C11 C15 112.78(8) . . . no C6 C12 C13 119.69(9) . . . no C6 C12 C14 120.43(9) . . . no C13 C12 C14 58.91(7) . . . no C12 C13 C14 60.41(7) . . . no C12 C14 C13 60.68(7) . . . no C11 C15 C16 109.94(8) . . . no C11 C15 C17 112.06(8) . . . no C16 C15 C17 109.52(8) . . . no N4 C16 C15 176.54(12) . . . yes N5 C17 C15 178.68(10) . . . yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C2 1.3363(13) . . yes N1 C6 1.3399(13) . . yes N2 C2 1.3522(13) . . yes N3 C7 1.1446(13) . . yes N4 C16 1.1407(14) . . yes N5 C17 1.1434(13) . . yes C2 C3 1.4126(14) . . no C3 C4 1.3973(13) . . no C3 C7 1.4301(13) . . no C4 C5 1.4027(13) . . no C4 C8 1.5130(14) . . no C5 C6 1.4051(14) . . no C5 C10 1.5106(13) . . no C6 C12 1.4840(13) . . no C8 C9 1.5291(15) . . no C10 C11 1.5323(14) . . no C11 C15 1.5458(14) . . no C12 C13 1.5153(14) . . no C12 C14 1.5113(14) . . no C13 C14 1.4882(16) . . no C15 C16 1.4714(14) . . no C15 C17 1.4728(13) . . 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 N1 C2 N2 -176.68(10) . . . . no C6 N1 C2 C3 -0.60(15) . . . . no C2 N1 C6 C5 1.91(16) . . . . no C2 N1 C6 C12 179.54(9) . . . . no N1 C2 C3 C4 -2.59(15) . . . . no N1 C2 C3 C7 -178.51(10) . . . . no N2 C2 C3 C4 173.30(10) . . . . no N2 C2 C3 C7 -2.62(15) . . . . no C2 C3 C4 C5 4.38(14) . . . . no C2 C3 C4 C8 -172.99(9) . . . . no C7 C3 C4 C5 -179.93(9) . . . . no C7 C3 C4 C8 2.71(15) . . . . no C3 C4 C5 C6 -3.11(14) . . . . no C3 C4 C5 C10 -179.29(9) . . . . no C8 C4 C5 C6 174.16(9) . . . . no C8 C4 C5 C10 -2.03(15) . . . . no C3 C4 C8 C9 -97.69(12) . . . . no C5 C4 C8 C9 85.08(13) . . . . no C4 C5 C6 N1 -0.02(15) . . . . no C4 C5 C6 C12 -177.48(9) . . . . no C10 C5 C6 N1 176.14(10) . . . . no C10 C5 C6 C12 -1.33(15) . . . . no C4 C5 C10 C11 93.69(11) . . . . no C6 C5 C10 C11 -82.37(11) . . . . no N1 C6 C12 C13 -30.49(13) . . . . no N1 C6 C12 C14 38.75(14) . . . . no C5 C6 C12 C13 147.19(10) . . . . no C5 C6 C12 C14 -143.58(10) . . . . no C5 C10 C11 C15 -167.68(8) . . . . no C10 C11 C15 C16 61.09(10) . . . . no C10 C11 C15 C17 -60.95(11) . . . . no C6 C12 C13 C14 109.70(12) . . . . no C6 C12 C14 C13 -108.46(11) . . . . no