#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/60/2236038.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_2236038
loop_
_publ_author_name
'Carreño, Alexander'
'Ladeira, Sonia'
'Castel, Annie'
'Vega, Andres'
'Chavez, Ivonne'
_publ_section_title
;
 (E)-2-{[(2-Aminopyridin-3-yl)imino]methyl}-4,6-di-tert-butylphenol
;
_journal_coeditor_code           YK2062
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2507
_journal_page_last               o2508
_journal_paper_doi               10.1107/S1600536812032060
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C20 H27 N3 O'
_chemical_formula_moiety         'C20 H27 N3 O'
_chemical_formula_sum            'C20 H27 N3 O'
_chemical_formula_weight         325.45
_chemical_name_systematic
;
(E)-2-{[(2-Aminopyridin-3-yl)imino]methyl}-4,6-di-tert-
butylphenol
;
_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
_cell_angle_alpha                90
_cell_angle_beta                 101.268(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8457(12)
_cell_length_b                   10.6227(8)
_cell_length_c                   10.4817(6)
_cell_measurement_reflns_used    4180
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      24.18
_cell_measurement_theta_min      2.28
_cell_volume                     1839.5(2)
_computing_cell_refinement       'SAINT (Bruker, 2009)'
_computing_data_collection       'APEX2 (Bruker, 2009)'
_computing_data_reduction        'SAINT (Bruker, 2009)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker Kappa APEXII Quazar area-detector'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'multilayer optics'
_diffrn_radiation_source         'microfocus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0631
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            29076
_diffrn_reflns_theta_full        28.28
_diffrn_reflns_theta_max         28.28
_diffrn_reflns_theta_min         3.12
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9971
_exptl_absorpt_correction_T_min  0.9572
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2009)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.261
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     230
_refine_ls_number_reflns         4532
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0969
_refine_ls_R_factor_gt           0.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0793P)²+0.3155P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1383
_refine_ls_wR_factor_ref         0.1598
_reflns_number_gt                2875
_reflns_number_total             4532
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            yk2062.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2236038
_cod_database_fobs_code          2236038
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_type_symbol
_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_symmetry_multiplicity
C C1 0.33157(10) 0.86007(16) 0.29538(16) 0.0257(4) Uani d . 1 1
H H1 0.3674 0.8829 0.3736 0.031 Uiso calc R 1 1
C C2 0.28038(10) 0.95302(16) 0.23052(16) 0.0249(4) Uani d . 1 1
C C3 0.22810(10) 0.91744(16) 0.11465(16) 0.0257(4) Uani d . 1 1
C C4 0.22863(10) 0.79318(16) 0.06788(16) 0.0245(4) Uani d . 1 1
C C5 0.28054(10) 0.70461(16) 0.13891(17) 0.0266(4) Uani d . 1 1
H H5 0.2794 0.6204 0.108 0.032 Uiso calc R 1 1
C C6 0.33349(10) 0.73537(16) 0.25259(16) 0.0253(4) Uani d . 1 1
C C7 0.28219(12) 1.08949(17) 0.28088(17) 0.0320(4) Uani d . 1 1
C C8 0.34609(13) 1.10793(19) 0.40455(18) 0.0390(5) Uani d . 1 1
H H8A 0.3332 1.0544 0.4739 0.058 Uiso calc R 1 1
H H8B 0.3467 1.1963 0.4315 0.058 Uiso calc R 1 1
H H8C 0.3994 1.0849 0.3876 0.058 Uiso calc R 1 1
C C9 0.19959(13) 1.1247(2) 0.3122(2) 0.0461(5) Uani d . 1 1
H H9A 0.157 1.1094 0.2357 0.069 Uiso calc R 1 1
H H9B 0.1997 1.2139 0.336 0.069 Uiso calc R 1 1
H H9C 0.1894 1.0733 0.385 0.069 Uiso calc R 1 1
C C10 0.30327(16) 1.17916(19) 0.1770(2) 0.0478(6) Uani d . 1 1
H H10A 0.355 1.154 0.1554 0.072 Uiso calc R 1 1
H H10B 0.3075 1.2654 0.2109 0.072 Uiso calc R 1 1
H H10C 0.2607 1.1752 0.0987 0.072 Uiso calc R 1 1
C C11 0.39232(11) 0.63577(17) 0.32438(16) 0.0304(4) Uani d . 1 1
C C12 0.43933(14) 0.6829(2) 0.4540(2) 0.0479(6) Uani d . 1 1
H H12A 0.4739 0.6152 0.4976 0.072 Uiso calc R 1 1
H H12B 0.4014 0.7094 0.5088 0.072 Uiso calc R 1 1
H H12C 0.4731 0.7546 0.4394 0.072 Uiso calc R 1 1
C C13 0.34424(14) 0.5187(2) 0.3506(2) 0.0473(6) Uani d . 1 1
H H13A 0.3133 0.4864 0.2681 0.071 Uiso calc R 1 1
H H13B 0.307 0.5414 0.408 0.071 Uiso calc R 1 1
H H13C 0.3818 0.4537 0.3923 0.071 Uiso calc R 1 1
C C14 0.45191(13) 0.5987(2) 0.2383(2) 0.0484(6) Uani d . 1 1
H H14A 0.422 0.5655 0.1555 0.073 Uiso calc R 1 1
H H14B 0.4889 0.534 0.2823 0.073 Uiso calc R 1 1
H H14C 0.4831 0.6728 0.2218 0.073 Uiso calc R 1 1
C C15 0.17797(10) 0.75478(17) -0.05444(16) 0.0275(4) Uani d . 1 1
H H15 0.1788 0.6688 -0.079 0.033 Uiso calc R 1 1
C C16 0.05978(11) 0.86736(18) -0.35148(17) 0.0299(4) Uani d . 1 1
C C17 0.08167(10) 0.78338(17) -0.24490(16) 0.0281(4) Uani d . 1 1
C C18 0.04954(11) 0.66344(19) -0.25690(18) 0.0335(4) Uani d . 1 1
H H18 0.0632 0.605 -0.1874 0.04 Uiso calc R 1 1
C C19 -0.00259(12) 0.6285(2) -0.37037(18) 0.0383(5) Uani d . 1 1
H H19 -0.0231 0.5451 -0.3819 0.046 Uiso calc R 1 1
C C20 -0.02377(12) 0.7174(2) -0.46567(18) 0.0397(5) Uani d . 1 1
H H20 -0.0615 0.6942 -0.5417 0.048 Uiso calc R 1 1
N N1 0.13236(9) 0.83038(15) -0.13087(14) 0.0289(4) Uani d . 1 1
N N2 0.00551(10) 0.83493(16) -0.45811(14) 0.0355(4) Uani d . 1 1
N N3 0.09503(10) 0.98206(16) -0.35261(16) 0.0369(4) Uani d D 1 1
H H103 0.1261(11) 1.010(2) -0.2805(14) 0.044 Uiso d D 1 1
H H203 0.0683(12) 1.0386(16) -0.4065(17) 0.044 Uiso d D 1 1
O O1 0.17780(8) 1.00391(12) 0.04615(12) 0.0353(3) Uani d . 1 1
H H1A 0.1527 0.9712 -0.023 0.053 Uiso calc R 1 1
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 0 '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'
O O 0.0106 0.006 '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
C2 C1 C6 124.28(15)
C2 C1 H1 117.9
C6 C1 H1 117.9
C1 C2 C3 116.96(15)
C1 C2 C7 121.96(15)
C3 C2 C7 121.07(15)
O1 C3 C2 119.77(15)
O1 C3 C4 119.75(15)
C2 C3 C4 120.47(15)
C5 C4 C3 119.45(15)
C5 C4 C15 118.68(15)
C3 C4 C15 121.84(15)
C6 C5 C4 122.16(16)
C6 C5 H5 118.9
C4 C5 H5 118.9
C5 C6 C1 116.65(15)
C5 C6 C11 120.27(15)
C1 C6 C11 123.06(15)
C8 C7 C9 107.74(16)
C8 C7 C10 107.40(17)
C9 C7 C10 110.13(17)
C8 C7 C2 112.01(15)
C9 C7 C2 110.13(16)
C10 C7 C2 109.38(15)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C7 C10 H10A 109.5
C7 C10 H10B 109.5
H10A C10 H10B 109.5
C7 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C12 C11 C14 109.03(17)
C12 C11 C13 107.93(17)
C14 C11 C13 109.08(17)
C12 C11 C6 112.56(15)
C14 C11 C6 108.83(15)
C13 C11 C6 109.36(15)
C11 C12 H12A 109.5
C11 C12 H12B 109.5
H12A C12 H12B 109.5
C11 C12 H12C 109.5
H12A C12 H12C 109.5
H12B C12 H12C 109.5
C11 C13 H13A 109.5
C11 C13 H13B 109.5
H13A C13 H13B 109.5
C11 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C11 C14 H14A 109.5
C11 C14 H14B 109.5
H14A C14 H14B 109.5
C11 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
N1 C15 C4 123.62(16)
N1 C15 H15 118.2
C4 C15 H15 118.2
N2 C16 N3 116.81(16)
N2 C16 C17 121.54(17)
N3 C16 C17 121.60(16)
C18 C17 N1 124.26(16)
C18 C17 C16 118.10(16)
N1 C17 C16 117.58(16)
C17 C18 C19 119.84(18)
C17 C18 H18 120.1
C19 C18 H18 120.1
C20 C19 C18 118.20(19)
C20 C19 H19 120.9
C18 C19 H19 120.9
N2 C20 C19 123.99(17)
N2 C20 H20 118
C19 C20 H20 118
C15 N1 C17 119.76(16)
C20 N2 C16 118.12(17)
C16 N3 H103 118.8(14)
C16 N3 H203 116.5(14)
H103 N3 H203 118(2)
C3 O1 H1A 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
C1 C2 1.397(2)
C1 C6 1.401(2)
C1 H1 0.95
C2 C3 1.406(2)
C2 C7 1.541(2)
C3 O1 1.356(2)
C3 C4 1.409(2)
C4 C5 1.396(2)
C4 C15 1.453(2)
C5 C6 1.381(2)
C5 H5 0.95
C6 C11 1.541(2)
C7 C8 1.527(2)
C7 C9 1.537(3)
C7 C10 1.539(3)
C8 H8A 0.98
C8 H8B 0.98
C8 H8C 0.98
C9 H9A 0.98
C9 H9B 0.98
C9 H9C 0.98
C10 H10A 0.98
C10 H10B 0.98
C10 H10C 0.98
C11 C12 1.518(3)
C11 C14 1.527(3)
C11 C13 1.538(3)
C12 H12A 0.98
C12 H12B 0.98
C12 H12C 0.98
C13 H13A 0.98
C13 H13B 0.98
C13 H13C 0.98
C14 H14A 0.98
C14 H14B 0.98
C14 H14C 0.98
C15 N1 1.279(2)
C15 H15 0.95
C16 N2 1.343(2)
C16 N3 1.357(3)
C16 C17 1.421(2)
C17 C18 1.380(3)
C17 N1 1.417(2)
C18 C19 1.384(3)
C18 H18 0.95
C19 C20 1.370(3)
C19 H19 0.95
C20 N2 1.339(3)
C20 H20 0.95
N3 H103 0.882(9)
N3 H203 0.885(9)
O1 H1A 0.84
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
O1 H1A N1 . 0.84 1.87 2.6214(19) 149
N3 H203 N2 3_574 0.885(9) 2.162(10) 3.045(2) 175(2)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658015
