#------------------------------------------------------------------------------
#$Date: 2016-03-21 02:19:39 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178381 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/03/4020367.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_4020367
loop_
_publ_author_name
'Frédéric Boschetti'
'Franck Denat'
'Enrique Espinosa'
'Alain Tabard'
'Yves Dory'
'Roger Guilard'
_publ_section_title
;
Regioselective N-functionalization of tetraazacycloalkanes.
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7042
_journal_page_last               7053
_journal_paper_doi               10.1021/jo050306u
_journal_volume                  70
_journal_year                    2005
_chemical_absolute_configuration syn
_chemical_formula_moiety         'C13 H24 N4'
_chemical_formula_sum            'C13 H24 N4'
_chemical_formula_weight         236.36
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 1'
_cell_angle_alpha                90.00
_cell_angle_beta                 102.184(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   5.9240(2)
_cell_length_b                   14.2360(3)
_cell_length_c                   7.7270(6)
_cell_measurement_temperature    110(2)
_cell_measurement_wavelength     0.71073
_cell_volume                     636.97(6)
_diffrn_ambient_temperature      110(2)
_exptl_crystal_density_diffrn    1.232
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               4020367
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-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
N1A N 0.4278(3) 0.75595(13) 0.2261(2) 0.0296(6) Uani 0.50 1 d P A 1
N2A N 0.2562(3) 0.5780 0.0796(2) 0.0327(6) Uani 0.50 1 d P A 1
N3A N 0.5762(4) 0.50171(15) 0.2739(3) 0.0317(7) Uani 0.50 1 d P A 1
N4A N 0.7376(3) 0.67782(11) 0.4185(3) 0.0278(6) Uani 0.50 1 d P A 1
C1A C 0.1878(5) 0.74463(19) 0.1189(3) 0.0459(9) Uani 0.50 1 d PU A 1
H1A1 H 0.1377 0.8029 0.0576 0.0504(11) Uiso 0.50 1 calc PR A 1
H1A2 H 0.0834 0.7305 0.1967 0.0504(11) Uiso 0.50 1 calc PR A 1
C2A C 0.1798(5) 0.66698(18) -0.0131(4) 0.0482(9) Uani 0.50 1 d PU A 1
H2A1 H 0.0235 0.6600 -0.0818 0.0504(11) Uiso 0.50 1 calc PR A 1
H2A2 H 0.2796 0.6822 -0.0938 0.0504(11) Uiso 0.50 1 calc PR A 1
C3A C 0.2294(5) 0.4997(2) -0.0432(3) 0.0458(9) Uani 0.50 1 d PU A 1
H3A1 H 0.3144 0.5124 -0.1351 0.0504(11) Uiso 0.50 1 calc PR A 1
H3A2 H 0.0676 0.4926 -0.0992 0.0504(11) Uiso 0.50 1 calc PR A 1
C4A C 0.3166(5) 0.41016(19) 0.0509(3) 0.0415(8) Uani 0.50 1 d PU A 1
H4A1 H 0.2185 0.3931 0.1317 0.0504(11) Uiso 0.50 1 calc PR A 1
H4A2 H 0.3093 0.3600 -0.0350 0.0504(11) Uiso 0.50 1 calc PR A 1
C5A C 0.5599(4) 0.42106(17) 0.1519(3) 0.0367(7) Uani 0.50 1 d PU A 1
H5A1 H 0.6087 0.3642 0.2187 0.0504(11) Uiso 0.50 1 calc PR A 1
H5A2 H 0.6615 0.4310 0.0702 0.0504(11) Uiso 0.50 1 calc PR A 1
C6A C 0.8067(5) 0.51124(19) 0.3767(3) 0.0367(8) Uani 0.50 1 d PU A 1
H6A1 H 0.9120 0.5226 0.2984 0.0504(11) Uiso 0.50 1 calc PR A 1
H6A2 H 0.8526 0.4533 0.4405 0.0504(11) Uiso 0.50 1 calc PR A 1
C7A C 0.8222(6) 0.5918(2) 0.5076(3) 0.0460(9) Uani 0.50 1 d PU A 1
H7A1 H 0.7320 0.5768 0.5951 0.0504(11) Uiso 0.50 1 calc PR A 1
H7A2 H 0.9815 0.6002 0.5688 0.0504(11) Uiso 0.50 1 calc PR A 1
C8A C 0.7675(5) 0.75653(19) 0.5468(3) 0.0401(8) Uani 0.50 1 d PU A 1
H8A1 H 0.9287 0.7614 0.6061 0.0504(11) Uiso 0.50 1 calc PR A 1
H8A2 H 0.6774 0.7447 0.6358 0.0504(11) Uiso 0.50 1 calc PR A 1
C9A C 0.6890(5) 0.84817(19) 0.4505(3) 0.0393(8) Uani 0.50 1 d PU A 1
H9A1 H 0.6938 0.8987 0.5354 0.0504(11) Uiso 0.50 1 calc PR A 1
H9A2 H 0.7907 0.8643 0.3717 0.0504(11) Uiso 0.50 1 calc PR A 1
C10A C 0.4432(5) 0.8350(2) 0.3448(3) 0.0433(8) Uani 0.50 1 d PU A 1
H10A H 0.3404 0.8252 0.4255 0.0504(11) Uiso 0.50 1 calc PR A 1
H10B H 0.3940 0.8915 0.2770 0.0504(11) Uiso 0.50 1 calc PR A 1
C14A C 0.5013(4) 0.66794(16) 0.3180(3) 0.0281(6) Uani 0.50 1 d PU A 1
C23A C 0.4984(5) 0.58989(18) 0.1776(3) 0.0309(7) Uani 0.50 1 d PU A 1
H23A H 0.5993 0.6064 0.0967 0.0504(11) Uiso 0.50 1 calc PR A 1
C30A C 0.3530(8) 0.6399(4) 0.4583(6) 0.0334(12) Uani 0.50 1 d PU A 1
H30A H 0.3817 0.6839 0.5546 0.0504(11) Uiso 0.50 1 calc PR A 1
H30B H 0.3954 0.5780 0.5025 0.0504(11) Uiso 0.50 1 calc PR A 1
H30C H 0.1920 0.6409 0.4028 0.0504(11) Uiso 0.50 1 calc PR A 1
N1B N 0.5762(4) 0.50171(15) 0.2739(3) 0.0317(7) Uani 0.50 1 d P B 2
N2B N 0.7376(3) 0.67782(11) 0.4185(3) 0.0278(6) Uani 0.50 1 d P B 2
N3B N 0.4278(3) 0.75595(13) 0.2261(2) 0.0296(6) Uani 0.50 1 d P B 2
N4B N 0.2562(3) 0.5780 0.0796(2) 0.0327(6) Uani 0.50 1 d P B 2
C1B C 0.8067(5) 0.51124(19) 0.3767(3) 0.0367(8) Uani 0.50 1 d PU B 2
H1B1 H 0.9120 0.5226 0.2984 0.0504(11) Uiso 0.50 1 calc PR B 2
H1B2 H 0.8526 0.4533 0.4405 0.0504(11) Uiso 0.50 1 calc PR B 2
C2B C 0.8222(6) 0.5918(2) 0.5076(3) 0.0460(9) Uani 0.50 1 d PU B 2
H2B1 H 0.7320 0.5768 0.5951 0.0504(11) Uiso 0.50 1 calc PR B 2
H2B2 H 0.9815 0.6002 0.5688 0.0504(11) Uiso 0.50 1 calc PR B 2
C3B C 0.7675(5) 0.75653(19) 0.5468(3) 0.0401(8) Uani 0.50 1 d PU B 2
H3B1 H 0.9287 0.7614 0.6061 0.0504(11) Uiso 0.50 1 calc PR B 2
H3B2 H 0.6774 0.7447 0.6358 0.0504(11) Uiso 0.50 1 calc PR B 2
C4B C 0.6890(5) 0.84817(19) 0.4505(3) 0.0393(8) Uani 0.50 1 d PU B 2
H4B1 H 0.6938 0.8987 0.5354 0.0504(11) Uiso 0.50 1 calc PR B 2
H4B2 H 0.7907 0.8643 0.3717 0.0504(11) Uiso 0.50 1 calc PR B 2
C5B C 0.4432(5) 0.8350(2) 0.3448(3) 0.0433(8) Uani 0.50 1 d PU B 2
H5B1 H 0.3404 0.8252 0.4255 0.0504(11) Uiso 0.50 1 calc PR B 2
H5B2 H 0.3940 0.8915 0.2770 0.0504(11) Uiso 0.50 1 calc PR B 2
C6B C 0.1878(5) 0.74463(19) 0.1189(3) 0.0459(9) Uani 0.50 1 d PU B 2
H6B1 H 0.1377 0.8029 0.0576 0.0504(11) Uiso 0.50 1 calc PR B 2
H6B2 H 0.0834 0.7305 0.1967 0.0504(11) Uiso 0.50 1 calc PR B 2
C7B C 0.1798(5) 0.66698(18) -0.0131(4) 0.0482(9) Uani 0.50 1 d PU B 2
H7B1 H 0.0235 0.6600 -0.0818 0.0504(11) Uiso 0.50 1 calc PR B 2
H7B2 H 0.2796 0.6822 -0.0938 0.0504(11) Uiso 0.50 1 calc PR B 2
C8B C 0.2294(5) 0.4997(2) -0.0432(3) 0.0458(9) Uani 0.50 1 d PU B 2
H8B1 H 0.3144 0.5124 -0.1351 0.0504(11) Uiso 0.50 1 calc PR B 2
H8B2 H 0.0676 0.4926 -0.0992 0.0504(11) Uiso 0.50 1 calc PR B 2
C9B C 0.3166(5) 0.41016(19) 0.0509(3) 0.0415(8) Uani 0.50 1 d PU B 2
H9B1 H 0.2185 0.3931 0.1317 0.0504(11) Uiso 0.50 1 calc PR B 2
H9B2 H 0.3093 0.3600 -0.0350 0.0504(11) Uiso 0.50 1 calc PR B 2
C10B C 0.5599(4) 0.42106(17) 0.1519(3) 0.0367(7) Uani 0.50 1 d PU B 2
H10C H 0.6087 0.3642 0.2187 0.0504(11) Uiso 0.50 1 calc PR B 2
H10D H 0.6615 0.4310 0.0702 0.0504(11) Uiso 0.50 1 calc PR B 2
C14B C 0.4984(5) 0.58989(18) 0.1776(3) 0.0309(7) Uani 0.50 1 d PU B 2
C23B C 0.5013(4) 0.66794(16) 0.3180(3) 0.0281(6) Uani 0.50 1 d PU B 2
H23B H 0.3980 0.6514 0.3970 0.0504(11) Uiso 0.50 1 calc PR B 2
C30B C 0.6497(9) 0.6098(3) 0.0374(6) 0.0256(12) Uani 0.50 1 d PU B 2
H30D H 0.6082 0.5666 -0.0596 0.0504(11) Uiso 0.50 1 calc PR B 2
H30E H 0.8100 0.6019 0.0916 0.0504(11) Uiso 0.50 1 calc PR B 2
H30F H 0.6235 0.6729 -0.0057 0.0504(11) Uiso 0.50 1 calc PR B 2
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
N1A C10A 1.443(3) . ?
N1A C14A 1.461(3) . ?
N1A C1A 1.495(3) . ?
N2A C3A 1.451(3) . ?
N2A C2A 1.478(3) . ?
N2A C23A 1.484(3) . ?
N3A C6A 1.434(3) . ?
N3A C5A 1.476(3) . ?
N3A C23A 1.482(3) . ?
N4A C7A 1.441(3) . ?
N4A C14A 1.457(3) . ?
N4A C8A 1.482(3) . ?
C1A C2A 1.498(4) . ?
C1A H1A1 0.9700 . ?
C1A H1A2 0.9700 . ?
C2A H2A1 0.9700 . ?
C2A H2A2 0.9700 . ?
C3A C4A 1.504(4) . ?
C3A H3A1 0.9700 . ?
C3A H3A2 0.9700 . ?
C4A C5A 1.495(3) . ?
C4A H4A1 0.9700 . ?
C4A H4A2 0.9700 . ?
C5A H5A1 0.9700 . ?
C5A H5A2 0.9700 . ?
C6A C7A 1.519(4) . ?
C6A H6A1 0.9700 . ?
C6A H6A2 0.9700 . ?
C7A H7A1 0.9700 . ?
C7A H7A2 0.9700 . ?
C8A C9A 1.525(4) . ?
C8A H8A1 0.9700 . ?
C8A H8A2 0.9700 . ?
C9A C10A 1.523(4) . ?
C9A H9A1 0.9700 . ?
C9A H9A2 0.9700 . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C14A C23A 1.551(2) . ?
C14A C30A 1.583(5) . ?
C23A H23A 0.9800 . ?
C30A H30A 0.9600 . ?
C30A H30B 0.9600 . ?
C30A H30C 0.9600 . ?
C30B H30D 0.9600 . ?
C30B H30E 0.9600 . ?
C30B H30F 0.9600 . ?
