#------------------------------------------------------------------------------
#$Date: 2008-04-03 11:11:48 +0100 (Thu, 03 Apr 2008) $
#$Revision: 326 $
#$URL: svn://www.crystallography.net/cod/cif/2/2101204.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_2101204
loop_
_publ_author_name
'Bertolasi, V.'
'Gilli, P.'
'Ferretti, V.'
'Gilli, G.'
_publ_section_title
;
 Intramolecular N--H^···^O hydrogen bonding
 assisted by resonance. III. Structural studies of
 1-ketone-2-arylhydrazone derivatives
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              617
_journal_page_last               625
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C16 H13 N5 O3'
_chemical_formula_weight         323.3
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_beta                 95.740(10)
_cell_formula_units_Z            4
_cell_length_a                   12.8170(10)
_cell_length_b                   7.595(5)
_cell_length_c                   15.652(3)
_cell_volume                     1516.0(10)
_diffrn_radiation_type           Mo
_diffrn_radiation_wavelength     0.71069
_exptl_absorpt_coefficient_mu    0.096
_exptl_crystal_density_diffrn    1.42
_exptl_crystal_F_000             672
_[local]_cod_data_source_file    na0053.cif
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
O(1) .86260(10) .3410(3) -.05790(10)
O(2) .8343(2) -.1832(4) .42950(10)
O(3) 1.0025(2) -.1838(3) .45360(10)
N(1) .9484(2) .1706(3) .09020(10)
N(2) 1.0399(2) .1821(3) .05860(10)
N(3) 1.1120(2) .3734(3) -.12960(10)
N(4) 1.00260(10) .4050(3) -.13830(10)
N(5) .9216(2) -.1482(3) .40900(10)
C(1) 1.0421(2) .2604(3) -.01540(10)
C(2) .9556(2) .3377(3) -.0704(2)
C(3) 1.1345(2) .2899(4) -.0581(2)
C(4) 1.2438(2) .2392(5) -.0269(2)
C(5) .9426(2) .0912(3) .1700(2)
C(6) .8469(2) .0819(4) .2032(2)
C(7) .8395(2) .0028(4) .2816(2)
C(8) .9288(2) -.0632(3) .3262(2)
C(9) 1.0249(2) -.0521(4) .2948(2)
C(10) 1.0319(2) .0237(4) .2161(2)
C(11) .9566(2) .4862(3) -.2150(2)
C(12) 1.0153(2) .5082(4) -.2838(2)
C(13) .9705(2) .5867(4) -.3582(2)
C(14) .8688(2) .6437(4) -.3642(2)
C(15) .8109(2) .6238(4) -.2955(2)
C(16) .8541(2) .5452(4) -.2203(2)
H(1) .893(2) .220(3) .0600(10)
H6 .789(2) .130(3) .1720(10)
H7 .777(2) -.001(3) .3050(10)
H9 1.085(2) -.102(3) .3260(10)
H10 1.0960(10) .030(3) .1950(10)
H12 1.0870(10) .461(3) -.2800(10)
H13 1.011(2) .597(3) -.407(2)
H14 .841(2) .698(4) -.413(2)
H15 .740(2) .659(4) -.302(2)
H16 .814(2) .527(3) -.1730(10)
H41 1.269(3) .310(6) .018(2)
H42 1.248(2) .133(4) -.002(2)
H43 1.290(3) .243(5) -.070(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O(1) C(2) 1.227(3)
O(2) N(5) 1.224(4)
O(3) N(5) 1.221(3)
N(1) N(2) 1.320(4)
N(1) C(5) 1.396(4)
N(2) C(1) 1.305(2)
N(3) N(4) 1.416(3)
N(3) C(3) 1.294(4)
N(4) C(2) 1.372(3)
N(4) C(11) 1.424(3)
N(5) C(8) 1.459(4)
C(1) C(2) 1.457(3)
C(1) C(3) 1.434(4)
C(3) C(4) 1.487(4)
C(5) C(6) 1.381(4)
C(5) C(10) 1.389(4)
C(6) C(7) 1.378(4)
C(7) C(8) 1.374(4)
C(8) C(9) 1.374(4)
C(9) C(10) 1.371(4)
C(12) C(13) 1.381(4)
C(12) C(11) 1.384(4)
C(13) C(14) 1.368(4)
C(14) C(15) 1.375(4)
C(15) C(16) 1.385(4)
C(16) C(11) 1.383(4)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
N(2) N(1) C(5) 119.5(2)
N(1) N(2) C(1) 117.5(2)
N(4) N(3) C(3) 107.4(2)
N(3) N(4) C(11) 118.5(2)
N(3) N(4) C(2) 111.7(2)
C(2) N(4) C(11) 129.6(2)
O(2) N(5) O(3) 123.3(2)
O(3) N(5) C(8) 118.7(2)
O(2) N(5) C(8) 118.0(2)
N(2) C(1) C(3) 125.2(2)
N(2) C(1) C(2) 128.7(2)
C(2) C(1) C(3) 106.1(2)
N(4) C(2) C(1) 103.9(2)
O(1) C(2) C(1) 127.4(2)
O(1) C(2) N(4) 128.7(2)
N(3) C(3) C(1) 110.9(3)
C(1) C(3) C(4) 126.9(3)
N(3) C(3) C(4) 122.1(3)
N(1) C(5) C(10) 120.6(3)
N(1) C(5) C(6) 119.2(3)
C(6) C(5) C(10) 120.2(3)
C(5) C(6) C(7) 120.0(3)
C(6) C(7) C(8) 118.9(3)
N(5) C(8) C(7) 119.3(2)
C(7) C(8) C(9) 121.8(3)
N(5) C(8) C(9) 118.9(3)
C(8) C(9) C(10) 119.3(3)
C(5) C(10) C(9) 119.8(2)
C(13) C(12) C(11) 119.7(3)
C(12) C(13) C(14) 120.5(3)
C(13) C(14) C(15) 119.8(3)
C(14) C(15) C(16) 120.7(3)
C(15) C(16) C(11) 119.2(3)
C(12) C(11) C(16) 120.1(3)
N(4) C(11) C(16) 120.1(3)
N(4) C(11) C(12) 119.8(2)