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#$Date: 2025-08-19 11:01:59 +0100 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: svn://www.crystallography.net/cod/cif/2/10/12/2101204.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_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_paper_doi               10.1107/S0108768194003034
_journal_volume                  50
_journal_year                    1994
_chemical_formula_sum            'C16 H13 N5 O3'
_chemical_formula_weight         323.3
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_cell_angle_alpha                90
_cell_angle_beta                 95.740(10)
_cell_angle_gamma                90
_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
_cod_data_source_file            na0053.cif
_cod_data_source_block           na0053d
_cod_database_code               2101204
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x+1/2,-y+1/2,z+1/2
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_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)
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_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 3107528