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#$Date: 2018-06-14 13:53:24 +0100 (Thu, 14 Jun 2018) $
#$Revision: 208377 $
#$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_paper_doi               10.1107/S0108270192003329
_journal_volume                  48
_journal_year                    1992
_chemical_formula_sum            'C10 H13 N3 O3'
_chemical_formula_weight         223.2
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        '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
_cod_data_source_file            br0018.cif
_cod_data_source_block           br0018a
_cod_depositor_comments
;
 Updating space group information and adding the symmetry operation list.

 Antanas Vaitkus,
 2018-06-15
;
_cod_original_cell_volume        1108.5
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2000444
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y+1/2,z+1/2
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_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)
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)