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#$Date: 2022-09-28 16:08:17 +0100 (Wed, 28 Sep 2022) $
#$Revision: 278247 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/12/2101229.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_2101229
loop_
_publ_author_name
'Llamas-Saiz, A. L.'
'Foces-Foces, C.'
'Cano, F. H.'
'Jim\'enez, P.'
'Laynez, J.'
'Meutermans, W.'
'Elguero, J.'
'Limbach, H.-H.'
'Aguilar-Parrilla, F.'
_publ_section_title
;
 The influence of the nitro group on the solid-state structure of
 4-nitropyrazoles: the cases of pyrazole, 3,5-dimethylpyrazole,
 3,5-di-<i>tert</i>-butylpyrazole and 3,5-diphenylpyrazole. I. Static
 aspects (crystallography and thermodynamics)
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              746
_journal_page_last               762
_journal_paper_doi               10.1107/S0108768194004180
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C3 H3 N3 O2'
_chemical_formula_weight         113.08
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_cell_angle_alpha                81.139(4)
_cell_angle_beta                 100.076(4)
_cell_angle_gamma                105.966(6)
_cell_formula_units_Z            6
_cell_length_a                   9.8831(7)
_cell_length_b                   9.6688(7)
_cell_length_c                   8.3417(4)
_cell_volume                     749.81(9)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    1.071
_exptl_crystal_density_diffrn    1.503
_cod_data_source_file            he0089.cif
_cod_data_source_block           he0089a
_cod_original_cell_volume        749.80(10)
_cod_database_code               2101229
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(1A) .0375(3) .3279(3) -.0574(4) .0530(10)
N(2A) .1002(3) .4612(3) -.1237(3) .0520(10)
C(3A) .0139(3) .5006(3) -.2498(4) .0530(10)
C(4A) -.1074(3) .3895(3) -.2653(3) .0470(10)
C(5A) -.0887(3) .2832(3) -.1425(4) .0520(10)
N(6A) -.2303(3) .3848(4) -.3837(4) .0700(10)
O(7A) -.3288(3) .2741(4) -.3770(4) .099(2)
O(8A) -.2322(4) .4897(5) -.4850(4) .114(2)
N(1B) .3096(3) .2559(3) .2909(3) .0530(10)
N(2B) .1740(3) .1941(3) .2316(3) .0540(10)
C(3B) .1318(3) .0688(3) .3199(4) .0530(10)
C(4B) .2420(3) .0490(3) .4374(3) .0460(10)
C(5B) .3532(3) .1702(3) .4151(4) .0540(10)
N(6B) .2441(4) -.0686(3) .5593(4) .0640(10)
O(7B) .3543(4) -.0673(4) .6540(4) .0950(10)
O(8B) .1340(4) -.1671(3) .5638(4) .0960(10)
N(1C) .3742(3) .6109(3) .0312(3) .0500(10)
N(2C) .4432(3) .5436(3) .1582(3) .0490(10)
C(3C) .5695(3) .6305(3) .2011(4) .0500(10)
C(4C) .5803(3) .7566(3) .0968(4) .0450(10)
C(5C) .4547(3) .7403(3) -.0085(4) .0510(10)
N(6C) .6989(3) .8796(3) .0952(4) .0670(10)
O(7C) .6886(4) .9823(3) -.0079(5) .0990(10)
O(8C) .8028(3) .8753(4) .1975(5) .101(2)
H(1A) .072(8) .272(9) .046(12) .030(16)
H(2A) .186(10) .511(9) -.074(9) .036(17)
H(3A) .035(4) .580(5) -.310(5) .036(10)
H(5A) -.143(5) .196(5) -.118(5) .051(11)
H(1B) .368(10) .342(11) .270(10) .05(2)
H(2B) .142(7) .234(8) .164(11) .047(17)
H(3B) .042(5) .015(5) .296(5) .045(11)
H(5B) .438(4) .197(4) .465(4) .031(8)
H(1C) .288(11) .574(9) -.032(10) .04(2)
H(2C) .421(7) .471(10) .199(9) .036(18)
H(3C) .635(4) .603(4) .290(5) .030(8)
H(5C) .427(4) .804(4) -.099(5) .028(8)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(5A) N(1A) N(2A) 108.8(3)
N(1A) N(2A) C(3A) 108.9(3)
N(2A) C(3A) C(4A) 107.8(3)
C(3A) C(4A) C(5A) 106.6(3)
C(4A) C(5A) N(1A) 108.0(3)
C(3A) C(4A) N(6A) 127.5(3)
C(5A) C(4A) N(6A) 125.9(3)
C(4A) N(6A) O(8A) 118.3(4)
C(4A) N(6A) O(7A) 117.6(3)
O(8A) N(6A) O(7A) 124.2(4)
C(5B) N(1B) N(2B) 109.2(3)
N(1B) N(2B) C(3B) 108.5(3)
N(2B) C(3B) C(4B) 108.4(3)
C(3B) C(4B) C(5B) 106.2(3)
C(4B) C(5B) N(1B) 107.8(3)
C(3B) C(4B) N(6B) 127.9(3)
C(5B) C(4B) N(6B) 126.0(3)
C(4B) N(6B) O(8B) 117.5(3)
C(4B) N(6B) O(7B) 118.3(3)
O(8B) N(6B) O(7B) 124.2(3)
C(5C) N(1C) N(2C) 109.4(3)
N(1C) N(2C) C(3C) 109.0(3)
N(2C) C(3C) C(4C) 107.3(3)
C(3C) C(4C) C(5C) 106.7(3)
C(4C) C(5C) N(1C) 107.5(3)
C(3C) C(4C) N(6C) 127.0(3)
C(5C) C(4C) N(6C) 126.3(3)
C(4C) N(6C) O(8C) 117.5(3)
C(4C) N(6C) O(7C) 117.5(3)
O(8C) N(6C) O(7C) 125.0(3)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(1A) N(2A) 1.345(3)
N(2A) C(3A) 1.312(4)
C(3A) C(4A) 1.374(4)
C(4A) C(5A) 1.362(4)
C(5A) N(1A) 1.317(4)
C(4A) N(6A) 1.420(4)
N(6A) O(8A) 1.217(5)
N(6A) O(7A) 1.235(4)
N(1B) N(2B) 1.348(3)
N(2B) C(3B) 1.318(4)
C(3B) C(4B) 1.367(4)
C(4B) C(5B) 1.382(4)
C(5B) N(1B) 1.312(4)
C(4B) N(6B) 1.407(4)
N(6B) O(8B) 1.235(4)
N(6B) O(7B) 1.226(5)
N(1C) N(2C) 1.339(4)
N(2C) C(3C) 1.323(4)
C(3C) C(4C) 1.375(4)
C(4C) C(5C) 1.375(4)
C(5C) N(1C) 1.314(4)
C(4C) N(6C) 1.422(4)
N(6C) O(8C) 1.221(4)
N(6C) O(7C) 1.224(4)