#------------------------------------------------------------------------------
#$Date: 2017-10-14 22:58:33 +0300 (Sat, 14 Oct 2017) $
#$Revision: 202018 $
#$URL: file:///home/coder/svn-repositories/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 für Kristallographie - New Crystal Structures'
_journal_page_first              41
_journal_page_last               42
_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 κ-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/[σ²(Fo²)+(0.0700P)²+6.5000P] where P=(Fo²+2Fc²)/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)
_cod_data_source_file            1267-1418.cff
_cod_data_source_block           2-2,6-dmepap2
_cod_original_cell_volume        3057.6(10)
_cod_original_sg_symbol_H-M      C12/c1
_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_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
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9811004
