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#$Date: 2022-09-14 23:33:16 +0300 (Wed, 14 Sep 2022) $
#$Revision: 277842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/08/4020813.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_4020813
loop_
_publ_author_name
'Alexandru T. Balaban'
'Ion Ghiviriga'
'Edmund W. Czerwinski'
'Priyadarsi De'
'Rudolf Faust'
_publ_section_title
;
 Simple Synthesis of a Weak Nucleophilic Base
 (4-Ethyl-2,6-diisopropyl-3,5-dimethylpyridine)
 Evidencing a Double Janus Group Effect
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              536
_journal_page_last               542
_journal_paper_doi               10.1021/jo035416k
_journal_volume                  69
_journal_year                    2004
_chemical_formula_moiety         'C21 H28 N4 O7'
_chemical_formula_sum            'C21 H28 N4 O7'
_chemical_formula_weight         448.47
_space_group_IT_number           33
_space_group_name_Hall           'P -2n -2ac'
_space_group_name_H-M_alt        'P c 21 n'
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      33
_symmetry_space_group_name_Hall  'P -2n -2ac'
_symmetry_space_group_name_H-M   'P c 21 n'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.9690(10)
_cell_length_b                   12.185(2)
_cell_length_c                   20.729(4)
_cell_measurement_temperature    100(2)
_cell_measurement_wavelength     1.5418
_cell_volume                     2265.4(6)
_diffrn_ambient_temperature      100(2)
_exptl_crystal_density_diffrn    1.315
_cod_database_code               4020813
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x+1/2, y+1/2, -z+1/2'
'-x+1/2, y, z+1/2'
'-x, y+1/2, -z'
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_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.5918(4) 1.0586(3) 0.30653(17) 0.0239(7) Uani 1 1 d . . .
O1A O 0.6185(3) 1.0655(2) 0.36505(11) 0.0297(6) Uani 1 1 d . . .
C2A C 0.4777(4) 1.1194(3) 0.27233(17) 0.0245(7) Uani 1 1 d . . .
N21A N 0.3833(4) 1.1959(3) 0.30767(16) 0.0300(7) Uani 1 1 d . . .
O21A O 0.2525(3) 1.2059(3) 0.29034(16) 0.0384(7) Uani 1 1 d . . .
O22A O 0.4387(4) 1.2489(3) 0.35205(15) 0.0422(8) Uani 1 1 d . . .
C3A C 0.4467(4) 1.1069(3) 0.20764(18) 0.0269(8) Uani 1 1 d . . .
H3A H 0.3667 1.1461 0.1884 0.032 Uiso 1 1 calc R . .
C4A C 0.5337(4) 1.0361(3) 0.17079(17) 0.0253(8) Uani 1 1 d . . .
N41A N 0.5052(4) 1.0258(3) 0.10272(15) 0.0271(7) Uani 1 1 d . . .
O41A O 0.3984(3) 1.0762(3) 0.07970(14) 0.0360(7) Uani 1 1 d . . .
O42A O 0.5895(3) 0.9673(2) 0.07025(12) 0.0331(7) Uani 1 1 d . . .
C5A C 0.6477(4) 0.9748(3) 0.19858(17) 0.0261(8) Uani 1 1 d . . .
H5A H 0.7073 0.9271 0.1731 0.031 Uiso 1 1 calc R . .
C6A C 0.6717(4) 0.9848(3) 0.26342(17) 0.0245(8) Uani 1 1 d . . .
N61A N 0.7822(4) 0.9112(3) 0.29279(15) 0.0276(7) Uani 1 1 d . . .
O61A O 0.7421(3) 0.8548(3) 0.33866(14) 0.0361(7) Uani 1 1 d . . .
O62A O 0.9077(3) 0.9077(3) 0.26870(14) 0.0373(7) Uani 1 1 d . . .
N1 N 0.3067(3) 0.6300(3) 0.50860(14) 0.0263(7) Uani 1 1 d . . .
H1 H 0.3195 0.6009 0.5471 0.032 Uiso 1 1 calc R . .
C2 C 0.4005(4) 0.5979(3) 0.46136(18) 0.0283(8) Uani 1 1 d . . .
C3 C 0.3873(4) 0.6469(3) 0.40081(18) 0.0289(8) Uani 1 1 d . . .
C4 C 0.2689(4) 0.7202(3) 0.39057(18) 0.0262(8) Uani 1 1 d . . .
C5 C 0.1736(4) 0.7518(3) 0.44127(17) 0.0252(8) Uani 1 1 d . . .
C6 C 0.1947(4) 0.7030(3) 0.50163(17) 0.0255(8) Uani 1 1 d . . .
C21 C 0.5127(5) 0.5096(4) 0.47783(19) 0.0370(10) Uani 1 1 d . . .
H21 H 0.5608 0.4866 0.4365 0.044 Uiso 1 1 calc R . .
C22 C 0.6361(5) 0.5543(5) 0.5212(2) 0.0431(11) Uani 1 1 d . . .
H22A H 0.6767 0.6216 0.5024 0.065 Uiso 1 1 calc R . .
H22B H 0.7155 0.4994 0.5252 0.065 Uiso 1 1 calc R . .
H22C H 0.5951 0.5703 0.564 0.065 Uiso 1 1 calc R . .
C23 C 0.4373(5) 0.4077(4) 0.5063(2) 0.0404(10) Uani 1 1 d . . .
H23A H 0.3885 0.427 0.547 0.061 Uiso 1 1 calc R . .
H23B H 0.5125 0.3509 0.5142 0.061 Uiso 1 1 calc R . .
H23C H 0.3628 0.3799 0.4758 0.061 Uiso 1 1 calc R . .
C31 C 0.4994(5) 0.6185(4) 0.34817(19) 0.0363(9) Uani 1 1 d . . .
H31A H 0.5989 0.6109 0.3672 0.054 Uiso 1 1 calc R . .
H31B H 0.5008 0.6771 0.3158 0.054 Uiso 1 1 calc R . .
H31C H 0.4706 0.5493 0.3276 0.054 Uiso 1 1 calc R . .
C41 C 0.2439(4) 0.7676(3) 0.32383(19) 0.0295(8) Uani 1 1 d . . .
H41A H 0.1359 0.7801 0.3173 0.035 Uiso 1 1 calc R . .
H41B H 0.2778 0.714 0.2911 0.035 Uiso 1 1 calc R . .
C42 C 0.3276(5) 0.8759(4) 0.3143(2) 0.0419(11) Uani 1 1 d . . .
H42A H 0.2961 0.9286 0.3474 0.063 Uiso 1 1 calc R . .
H42B H 0.3053 0.9055 0.2715 0.063 Uiso 1 1 calc R . .
H42C H 0.4351 0.863 0.3181 0.063 Uiso 1 1 calc R . .
C51 C 0.0488(5) 0.8324(4) 0.4315(2) 0.0334(9) Uani 1 1 d . . .
H51A H -0.0451 0.7926 0.4255 0.05 Uiso 1 1 calc R . .
H51B H 0.0693 0.8771 0.3931 0.05 Uiso 1 1 calc R . .
H51C H 0.041 0.8802 0.4694 0.05 Uiso 1 1 calc R . .
C61 C 0.0994(4) 0.7257(3) 0.56018(17) 0.0272(8) Uani 1 1 d . . .
H61 H 0.0136 0.7718 0.5454 0.033 Uiso 1 1 calc R . .
C622 C 0.1866(5) 0.7943(3) 0.61004(19) 0.0333(9) Uani 1 1 d . . .
H62A H 0.2745 0.7531 0.6243 0.05 Uiso 1 1 calc R . .
H62B H 0.1225 0.8097 0.6472 0.05 Uiso 1 1 calc R . .
H62C H 0.2183 0.8635 0.5903 0.05 Uiso 1 1 calc R . .
C623 C 0.0333(5) 0.6202(4) 0.58907(19) 0.0327(9) Uani 1 1 d . . .
H62D H -0.0188 0.5791 0.5553 0.049 Uiso 1 1 calc R . .
H62E H -0.0372 0.6393 0.6234 0.049 Uiso 1 1 calc R . .
H62F H 0.1137 0.575 0.6069 0.049 Uiso 1 1 calc R . .
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
C1A O1A 1.239(4) . ?
C1A C2A 1.449(5) . ?
C1A C6A 1.456(5) . ?
C2A C3A 1.378(5) . ?
C2A N21A 1.456(5) . ?
N21A O22A 1.229(5) . ?
N21A O21A 1.233(5) . ?
C3A C4A 1.392(6) . ?
C3A H3A 0.95 . ?
C4A C5A 1.391(5) . ?
C4A N41A 1.439(5) . ?
N41A O41A 1.234(4) . ?
N41A O42A 1.238(5) . ?
C5A C6A 1.367(5) . ?
C5A H5A 0.95 . ?
C6A N61A 1.469(5) . ?
N61A O61A 1.227(4) . ?
N61A O62A 1.232(4) . ?
N1 C2 1.349(5) . ?
N1 C6 1.350(5) . ?
N1 H1 0.88 . ?
C2 C3 1.395(5) . ?
C2 C21 1.512(5) . ?
C3 C4 1.403(6) . ?
C3 C31 1.523(5) . ?
C4 C5 1.409(5) . ?
C4 C41 1.516(5) . ?
C5 C6 1.398(5) . ?
C5 C51 1.503(5) . ?
C6 C61 1.510(5) . ?
C21 C22 1.526(6) . ?
C21 C23 1.533(7) . ?
C21 H21 1 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C31 H31A 0.98 . ?
C31 H31B 0.98 . ?
C31 H31C 0.98 . ?
C41 C42 1.532(6) . ?
C41 H41A 0.99 . ?
C41 H41B 0.99 . ?
C42 H42A 0.98 . ?
C42 H42B 0.98 . ?
C42 H42C 0.98 . ?
C51 H51A 0.98 . ?
C51 H51B 0.98 . ?
C51 H51C 0.98 . ?
C61 C623 1.537(6) . ?
C61 C622 1.542(5) . ?
C61 H61 1 . ?
C622 H62A 0.98 . ?
C622 H62B 0.98 . ?
C622 H62C 0.98 . ?
C623 H62D 0.98 . ?
C623 H62E 0.98 . ?
C623 H62F 0.98 . ?
