#------------------------------------------------------------------------------ #$Date: 2012-02-28 12:14:52 +0000 (Tue, 28 Feb 2012) $ #$Revision: 35911 $ #$URL: svn://www.crystallography.net/cod/cif/8/10/16/8101690.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_8101690 loop_ _publ_author_name 'M. Polamo' 'M. Talja' 'A. J. Piironen' _publ_section_title ; Crystal structure of 2-[2,6-di(methylethyl)phenylamino]pyridine, C17H22N2 ; _journal_issue 1 _journal_name_full 'Zeitschrift f\"ur Kristallographie - New Crystal Structures' _journal_page_first 41 _journal_volume 220 _journal_year 2005 _chemical_formula_sum 'C17 H22 N2' _chemical_formula_weight 254.37 _chemical_name_systematic ; 2-[2,6-di(methylethyl)phenylamino]pyridine ; _space_group_IT_number 15 _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_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 94.74(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 10.705(2) _cell_length_b 14.654(3) _cell_length_c 19.558(4) _cell_measurement_temperature 173(2) _cell_volume 3057.6(11) _computing_cell_refinement 'COLLECT (Nonius, 2002)' _computing_data_collection 'COLLECT (Nonius, 2002)' _computing_data_reduction 'COLLECT (Nonius, 2002)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997)' _computing_publication_material 'SHELX97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELX97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device 'Nonius 95mm KappaCCD on \k-goniostat' _diffrn_measurement_method CCD _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 0.1087 _diffrn_reflns_av_sigmaI/netI 0.0448 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 26983 _diffrn_reflns_theta_full 26.50 _diffrn_reflns_theta_max 26.50 _diffrn_reflns_theta_min 3.05 _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_T_max 0.9872 _exptl_absorpt_correction_T_min 0.9774 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.105 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.309 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 175 _refine_ls_number_reflns 3161 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.060 _refine_ls_R_factor_all 0.0972 _refine_ls_R_factor_gt 0.0789 _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^)+(0.0700P)^2^+6.5000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1850 _refine_ls_wR_factor_ref 0.1958 _reflns_number_gt 2470 _reflns_number_total 3161 _reflns_threshold_expression >2sigma(I) _[local]_cod_data_source_file 1267-1418.cff _[local]_cod_data_source_block 2-2,6-dmepap2 _[local]_cod_cif_authors_sg_H-M C12/c1 _cod_original_cell_volume 3057.6(10) _cod_database_code 8101690 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_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_Wyckoff_symbol _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group N1 N 0.10902(16) 0.16655(13) 0.17886(9) 0.0306(4) Uani 1 8 f d . . . C2 C 0.20018(19) 0.16742(14) 0.23050(11) 0.0271(5) Uani 1 8 f d . . . C3 C 0.3285(2) 0.16740(18) 0.21752(12) 0.0367(6) Uani 1 8 f d . . . H3A H 0.3908 0.1666 0.2536 0.044 Uiso 1 8 f calc R . . C4 C 0.3594(2) 0.1686(2) 0.15093(13) 0.0430(6) Uani 1 8 f d . . . H4A H 0.4432 0.1692 0.1416 0.052 Uiso 1 8 f calc R . . C5 C 0.2658(2) 0.16900(18) 0.09736(12) 0.0409(6) Uani 1 8 f d . . . H5A H 0.2848 0.1705 0.0518 0.049 Uiso 1 8 f calc R . . C6 C 0.1434(2) 0.16705(17) 0.11451(12) 0.0374(5) Uani 1 8 f d . . . H6A H 0.0803 0.1660 0.0789 0.045 Uiso 1 8 f calc R . . N7 N 0.16309(16) 0.16818(14) 0.29510(9) 0.0303(4) Uani 1 8 f d . . . H7 H 0.082(3) 0.1749(18) 0.2976(12) 0.036 Uiso 1 8 f d . . . C8 C 0.24639(18) 0.18066(15) 0.35569(10) 0.0272(5) Uani 1 8 f d . . . C9 C 0.2973(2) 0.26838(16) 0.37043(11) 0.0311(5) Uani 1 8 f d . . . C10 C 0.3748(2) 0.27918(17) 0.43062(12) 0.0369(5) Uani 1 8 f d . . . H10 H 0.4078 0.3364 0.4419 0.044 Uiso 1 8 f calc R . . C11 C 0.4035(2) 0.20596(19) 0.47411(12) 0.0386(6) Uani 1 8 f d . . . H11 H 0.4563 0.2144 0.5138 0.046 Uiso 1 8 f calc R . . C12 C 0.3537(2) 0.12035(17) 0.45863(11) 0.0355(5) Uani 1 8 f d . . . H12 H 0.3739 0.0717 0.4880 0.043 Uiso 1 8 f calc R . . C13 C 0.27361(19) 0.10632(16) 0.39950(11) 0.0293(5) Uani 1 8 f d . . . C14 C 0.2645(2) 0.34926(16) 0.32309(13) 0.0388(6) Uani 1 8 f d . . . H14 H 0.2512 0.3251 0.2763 0.047 Uiso 1 8 f calc R . . C15 C 0.1405(4) 0.3923(3) 0.3405(2) 0.0815(12) Uani 1 8 f d . . . H15A H 0.0764 0.3463 0.3388 0.122 Uiso 1 8 f calc R . . H15B H 0.1169 0.4394 0.3079 0.122 Uiso 1 8 f calc R . . H15C H 0.1505 0.4181 0.3857 0.122 Uiso 1 8 f calc R . . C16 C 0.3671(4) 0.4201(2) 0.3229(2) 0.0788(12) Uani 1 8 f d . . . H16A H 0.4430 0.3917 0.3108 0.118 Uiso 1 8 f calc R . . H16B H 0.3807 0.4468 0.3677 0.118 Uiso 1 8 f calc R . . H16C H 0.3426 0.4667 0.2900 0.118 Uiso 1 8 f calc R . . C17 C 0.2196(2) 0.01171(17) 0.38423(12) 0.0379(6) Uani 1 8 f d . . . H17 H 0.1605 0.0164 0.3434 0.045 Uiso 1 8 f calc R . . C18 C 0.1473(3) -0.0230(2) 0.44307(16) 0.0591(8) Uani 1 8 f d . . . H18A H 0.0827 0.0199 0.4517 0.089 Uiso 1 8 f calc R . . H18B H 0.2037 -0.0296 0.4836 0.089 Uiso 1 8 f calc R . . H18C H 0.1103 -0.0810 0.4309 0.089 Uiso 1 8 f calc R . . C19 C 0.3213(3) -0.0562(2) 0.3685(2) 0.0735(10) Uani 1 8 f d . . . H19A H 0.3654 -0.0337 0.3312 0.110 Uiso 1 8 f calc R . . H19B H 0.2836 -0.1140 0.3562 0.110 Uiso 1 8 f calc R . . H19C H 0.3791 -0.0637 0.4084 0.110 Uiso 1 8 f calc R . . 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 0.0247(9) 0.0306(10) 0.0358(10) 0.0004(7) -0.0021(7) 0.0000(8) C2 0.0230(10) 0.0245(10) 0.0334(11) -0.0002(8) 0.0003(8) -0.0004(8) C3 0.0214(10) 0.0509(15) 0.0377(12) -0.0050(10) 0.0012(8) -0.0044(10) C4 0.0298(12) 0.0569(17) 0.0432(13) -0.0087(12) 0.0090(10) -0.0065(11) C5 0.0447(14) 0.0466(15) 0.0322(11) -0.0015(10) 0.0070(10) -0.0054(11) C6 0.0395(13) 0.0375(13) 0.0336(11) 0.0017(9) -0.0061(9) 0.0015(10) N7 0.0165(8) 0.0398(11) 0.0342(9) 0.0011(8) 0.0004(7) -0.0014(8) C8 0.0176(9) 0.0344(12) 0.0299(10) -0.0005(8) 0.0043(7) 0.0000(8) C9 0.0268(10) 0.0325(12) 0.0350(11) -0.0017(9) 0.0086(8) -0.0007(9) C10 0.0347(12) 0.0369(13) 0.0396(12) -0.0074(10) 0.0062(9) -0.0102(10) C11 0.0301(11) 0.0534(15) 0.0318(11) -0.0030(10) -0.0011(9) -0.0087(11) C12 0.0319(12) 0.0420(14) 0.0325(11) 0.0038(9) 0.0023(9) 0.0002(10) C13 0.0226(10) 0.0336(12) 0.0320(11) 0.0007(8) 0.0044(8) -0.0025(9) C14 0.0480(14) 0.0268(12) 0.0421(13) 0.0003(9) 0.0069(10) 0.0006(10) C15 0.091(3) 0.078(3) 0.079(2) 0.0247(19) 0.028(2) 0.048(2) C16 0.091(3) 0.052(2) 0.092(3) 0.0257(18) -0.008(2) -0.0287(19) C17 0.0380(13) 0.0336(13) 0.0412(13) 0.0030(10) -0.0018(10) -0.0050(10) C18 0.0578(18) 0.0572(19) 0.0625(18) 0.0092(14) 0.0055(14) -0.0246(15) C19 0.068(2) 0.0448(19) 0.109(3) -0.0217(18) 0.016(2) 0.0031(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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C2 117.80(19) . . ? N1 C2 N7 116.73(18) . . ? N1 C2 C3 121.3(2) . . ? N7 C2 C3 122.00(19) . . ? C4 C3 C2 119.0(2) . . ? C4 C3 H3A 120.5 . . ? C2 C3 H3A 120.5 . . ? C3 C4 C5 120.1(2) . . ? C3 C4 H4A 120.0 . . ? C5 C4 H4A 120.0 . . ? C6 C5 C4 117.2(2) . . ? C6 C5 H5A 121.4 . . ? C4 C5 H5A 121.4 . . ? N1 C6 C5 124.7(2) . . ? N1 C6 H6A 117.7 . . ? C5 C6 H6A 117.7 . . ? C2 N7 C8 124.13(17) . . ? C2 N7 H7 114.8(16) . . ? C8 N7 H7 119.3(16) . . ? C13 C8 C9 121.58(19) . . ? C13 C8 N7 119.31(19) . . ? C9 C8 N7 119.10(19) . . ? C10 C9 C8 117.9(2) . . ? C10 C9 C14 121.1(2) . . ? C8 C9 C14 121.0(2) . . ? C11 C10 C9 121.1(2) . . ? C11 C10 H10 119.4 . . ? C9 C10 H10 119.4 . . ? C12 C11 C10 120.3(2) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? C11 C12 C13 120.8(2) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? C12 C13 C8 118.3(2) . . ? C12 C13 C17 119.6(2) . . ? C8 C13 C17 122.10(19) . . ? C16 C14 C9 113.8(2) . . ? C16 C14 C15 111.2(3) . . ? C9 C14 C15 110.2(2) . . ? C16 C14 H14 107.1 . . ? C9 C14 H14 107.1 . . ? C15 C14 H14 107.1 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 C19 111.6(2) . . ? C13 C17 C18 111.3(2) . . ? C19 C17 C18 110.5(3) . . ? C13 C17 H17 107.8 . . ? C19 C17 H17 107.8 . . ? C18 C17 H17 107.8 . . ? C17 C18 H18A 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C17 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C17 C19 H19A 109.5 . . ? C17 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C17 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N1 C6 1.340(3) . ? N1 C2 1.345(3) . ? C2 N7 1.355(3) . ? C2 C3 1.418(3) . ? C3 C4 1.370(3) . ? C3 H3A 0.9300 . ? C4 C5 1.389(3) . ? C4 H4A 0.9300 . ? C5 C6 1.379(4) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? N7 C8 1.435(3) . ? N7 H7 0.88(3) . ? C8 C13 1.402(3) . ? C8 C9 1.417(3) . ? C9 C10 1.392(3) . ? C9 C14 1.527(3) . ? C10 C11 1.388(4) . ? C10 H10 0.9300 . ? C11 C12 1.387(3) . ? C11 H11 0.9300 . ? C12 C13 1.397(3) . ? C12 H12 0.9300 . ? C13 C17 1.522(3) . ? C14 C16 1.511(4) . ? C14 C15 1.534(4) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C19 1.525(4) . ? C17 C18 1.526(4) . ? C17 H17 0.9800 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? 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 N7 H7 N1 0.88(3) 2.14(3) 2.998(3) 167(2) 2