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#$Date: 2016-02-20 02:53:41 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176768 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/12/2101231.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_2101231
loop_
_publ_author_name
'Llamas-Saiz, A. L.'
'Foces-Foces, C.'
'Cano, F. H.'
'Jiménez, 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-tert-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            'C15 H11 N3 O2'
_chemical_formula_weight         265.27
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_cell_angle_alpha                90
_cell_angle_beta                 99.339(7)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   18.1399(16)
_cell_length_b                   12.0814(9)
_cell_length_c                   11.5184(7)
_cell_volume                     2490.9(3)
_diffrn_radiation_type           Cu
_diffrn_radiation_wavelength     1.54184
_exptl_absorpt_coefficient_mu    0.756
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             1104
_cod_data_source_file            he0089.cif
_cod_data_source_block           he0089c
_cod_database_code               2101231
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
N(101) .0111(3) .3725(3) .0517(4) .056(2)
N(102) -.0402(3) .3818(4) -.0467(4) .060(2)
C(103) -.0418(3) .2831(4) -.0997(4) .0410(10)
C(104) .0109(3) .2113(3) -.0289(4) .0370(10)
C(105) .0453(3) .2778(3) .0660(4) .0400(10)
C(106) -.0964(3) .2565(4) -.2057(4) .044(2)
C(107) -.1084(3) .3375(5) -.2933(5) .053(2)
C(108) -.1619(3) .3216(5) -.3903(5) .053(2)
C(109) -.2043(4) .2283(5) -.3986(5) .063(2)
C(110) -.1956(3) .1562(5) -.3165(5) .053(2)
C(111) -.1432(3) .1597(4) -.2106(5) .048(2)
C(112) .1017(2) .2586(4) .1720(4) .0420(10)
C(113) .1004(3) .1606(4) .2393(4) .047(2)
C(114) .1502(3) .1550(5) .3457(5) .053(2)
C(115) .1981(4) .2407(7) .3825(6) .075(3)
C(116) .2002(3) .3271(5) .3203(5) .053(2)
C(117) .1539(3) .3443(4) .2051(5) .046(2)
N(118) .0361(2) .1101(3) -.0624(3) .0390(10)
O(119) .0122(2) .0734(3) -.1637(4) .0610(10)
O(120) .0839(3) .0577(3) .0048(4) .0660(10)
N(201) .5108(6) -.1203(7) .5521(9) .056(3)
N(202) .4575(5) -.1257(6) .4525(7) .046(3)
C(203) .4565(3) -.0041(7) .4183(5) .069(2)
C(204) .5123(5) .0380(7) .4714(8) .035(3)
C(206) .4007(3) -.0049(4) .3115(5) .044(2)
C(207) .3918(3) -.0902(5) .2309(7) .068(2)
C(208) .3392(5) -.0823(9) .1313(8) .099(4)
C(209) .2943(4) .0066(7) .1073(5) .070(3)
C(210) .3031(4) .1010(5) .1894(5) .060(2)
C(211) .3579(3) .0868(4) .2819(4) .044(2)
N(218) .5405(5) .1438(6) .4327(7) .038(3)
O(219) .5157(4) .1749(5) .3359(6) .046(2)
O(220) .5878(4) .1923(5) .5025(6) .052(2)
N(301) .4803(5) -.1267(7) -.0472(9) .1053(3)
N(302) .5367(5) -.1325(6) .0513(7) .048(3)
C(303) .5435(4) -.0048(10) .0807(6) .107(4)
C(304) .4882(5) .0350(6) .0263(8) .033(3)
C(306) .6000(3) -.0072(4) .1884(5) .051(2)
C(307) .6468(4) .0783(4) .2113(5) .055(2)
C(308) .7031(3) .0922(5) .3034(5) .057(2)
C(309) .7064(3) .0027(6) .3907(5) .062(2)
C(310) .6551(4) -.0835(7) .3704(8) .086(3)
C(311) .6044(3) -.0885(5) .2714(7) .068(2)
N(318) .4651(6) .1429(6) .0625(9) .111(4)
O(319) .4898(4) .1761(5) .1610(6) .048(2)
O(320) .4170(5) .1945(5) -.0070(6) .054(2)
H(101) .015(4) .440(6) .105(6) .037(16)
H(107) -.082(3) .401(5) -.300(5) .014(13)
H(108) -.169(6) .381(9) -.446(10) .09(3)
H(109) -.246(6) .213(8) -.466(9) .08(3)
H(110) -.229(5) .092(7) -.324(7) .07(2)
H(111) -.128(4) .105(6) -.140(6) .047(18)
H(113) .060(3) .097(5) .213(5) .025(14)
H(114) .146(3) .088(5) .383(5) .010(11)
H(115) .232(5) .234(8) .456(8) .07(3)
H(116) .247(5) .381(7) .329(7) .06(2)
H(117) .157(5) .416(7) .158(8) .06(2)
H(201) .527 -.181 .597 .053
H(207) .422(5) -.154(7) .244(8) .048
H(208) .335(7) -.132(10) .073(11) .079
H(209) .258(5) .008(8) .040(8) .062
H(210) .273(4) .174(6) .175(6) .041(17)
H(211) .359(3) .155(5) .336(5) .025(14)
H(301) .459 -.187 -.087 .052
H(307) .640(3) .136(5) .157(5) .012
H(308) .735(4) .160(7) .313(6) .049(19)
H(309) .739(4) .009(6) .455(7) .040(18)
H(310) .657(4) -.125(7) .434(8) .05(2)
H(311) .572(5) -.149(8) .260(8) .028
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C(105) N(101) N(102) 115.4(4)
N(101) N(102) C(103) 105.7(4)
N(102) C(103) C(104) 108.3(4)
C(103) C(104) C(105) 105.3(4)
C(104) C(105) N(101) 105.1(4)
N(102) C(103) C(106) 122.2(4)
C(104) C(103) C(106) 129.1(4)
N(101) C(105) C(112) 119.7(4)
C(104) C(105) C(112) 135.0(4)
C(103) C(104) N(118) 126.3(4)
C(105) C(104) N(118) 126.4(4)
C(104) N(118) O(119) 119.4(4)
C(104) N(118) O(120) 120.4(4)
O(119) N(118) O(120) 120.1(4)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N(101) N(102) 1.350(6)
N(102) C(103) 1.339(6)
C(103) C(104) 1.443(6)
C(104) C(105) 1.417(6)
C(105) N(101) 1.299(6)
C(103) C(106) 1.477(6)
C(105) C(112) 1.479(6)
C(104) N(118) 1.382(6)
N(118) O(119) 1.257(5)
N(118) O(120) 1.239(5)
