#------------------------------------------------------------------------------
#$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $
#$Revision: 32112 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/04/2000444.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_2000444
loop_
_publ_author_name
'Vaughan, K.'
'Cameron, L. M.'
'Christie, S.'
'Zaworotko, M. J.'
_publ_section_title
;
 Structures of the isomeric triazene 1-oxides
 3-(4-ethoxycarbonylphenyl)-1-methyltriazene 1-oxide (1) and
 3-(2-ethoxycarbonylphenyl)-1-methyltriazene 1-oxide (2)
;
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1985
_journal_page_last               1988
_journal_volume                  48
_journal_year                    1992
_chemical_formula_sum            'C10 H13 N3 O3'
_chemical_formula_weight         223.2
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 100.434(11)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.5055(13)
_cell_length_b                   25.201(3)
_cell_length_c                   8.1241(19)
_cell_volume                     1108.5(4)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.70926
_exptl_absorpt_coefficient_mu    0.09
_exptl_crystal_density_diffrn    1.34
_exptl_crystal_F_000             472
_[local]_cod_data_source_file    br0018.cif
_[local]_cod_data_source_block   br0018a
_[local]_cod_cif_authors_sg_H-M  'P 21/c'
_cod_original_cell_volume        1108.5
_cod_database_code               2000444
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) .8705(4) .85919(9) 1.7009(3)
O(2) 1.1266(4) .81044(9) 1.5749(3)
O(3) .3164(4) .94548(9) .6393(3)
N(1) .5085(5) .91827(11) .9296(3)
N(2) .2988(5) .94732(10) .9143(3)
N(3) .2159(5) .95955(10) .7617(3)
C(1) .6133(6) .90004(12) 1.0883(4)
C(2) .5079(6) .91192(12) 1.2270(4)
C(3) .6180(6) .89372(13) 1.3832(4)
C(4) .8328(6) .86365(12) 1.4042(4)
C(5) .9361(6) .85196(12) 1.2643(4)
C(6) .8284(6) .87000(13) 1.1068(4)
C(7) .9410(6) .84557(13) 1.5742(4)
C(8) 1.2418(7) .79028(13) 1.7382(4)
C(9) 1.4411(6) .75254(16) 1.7085(5)
C(10) -.0118(6) .99109(13) .7298(4)
H(N) .565(5) .9089(12) .831(4)
H(2) .337 .936 1.212
H(3) .536 .902 1.494
H(5) 1.106 .828 1.281
H(6) .910 .861 .996
H(8A) 1.320 .823 1.822
H(8B) 1.108 .769 1.800
H(9A) 1.534 .742 1.827
H(9B) 1.579 .765 1.650
H(9C) 1.311 .718 1.617
H(10A) -.060 .999 .852
H(10B) -.147 .971 .644
H(10C) .011 1.028 .644
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(1) C(7) 1.213(4)
O(2) C(7) 1.351(4)
O(2) C(8) 1.454(4)
O(3) N(3) 1.272(3)
N(1) N(2) 1.354(4)
N(1) C(1) 1.391(4)
N(1) H(N) .94(3)
N(2) N(3) 1.279(4)
N(3) C(10) 1.467(4)
C(1) C(2) 1.390(4)
C(1) C(6) 1.390(4)
C(2) C(3) 1.382(4)
C(2) H(2) 1.105(3)
C(3) C(4) 1.389(4)
C(3) H(3) 1.103(3)
C(4) C(5) 1.392(4)
C(4) C(7) 1.474(4)
C(5) C(6) 1.386(4)
C(5) H(5) 1.096(3)
C(6) H(6) 1.104(3)
C(8) C(9) 1.504(5)
C(8) H(8A) 1.099(3)
C(8) H(8B) 1.100(4)
C(9) H(9A) 1.040(3)
C(9) H(9B) 1.015(4)
C(9) H(9C) 1.279(4)
C(10) H(10A) 1.088(3)
C(10) H(10B) 1.048(3)
C(10) H(10C) 1.180(3)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(7) O(2) C(8) 115.9(3)
N(2) N(1) C(1) 117.9(3)
N(1) N(2) N(3) 111.6(2)
O(3) N(3) N(2) 124.1(3)
O(3) N(3) C(10) 119.4(2)
N(2) N(3) C(10) 116.4(3)
N(1) C(1) C(2) 121.0(3)
N(1) C(1) C(6) 118.8(3)
C(2) C(1) C(6) 120.1(3)
C(1) C(2) C(3) 119.7(3)
N(1) H(N) O(3) 105.(2)
C(2) C(3) C(4) 121.1(3)
C(3) C(4) C(5) 118.7(3)
C(3) C(4) C(7) 118.4(3)
C(5) C(4) C(7) 123.0(3)
C(4) C(5) C(6) 121.0(3)
C(1) C(6) C(5) 119.5(3)
O(1) C(7) O(2) 122.7(3)
O(1) C(7) C(4) 124.8(3)
O(2) C(7) C(4) 112.6(3)
O(2) C(8) C(9) 106.6(3)