#------------------------------------------------------------------------------
#$Date: 2011-01-02 22:00:31 +0200 (Sun, 02 Jan 2011) $
#$Revision: 5310 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2013185.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_2013185
loop_
_publ_author_name
'Sivakumar, B.'
'Sethu Sankar, K.'
'Senthil Kumar, U. P.'
'Jeyaraman, R.'
'Velmurugan, D.'
_publ_section_title
;
2-Nitroso-1,3-diphenyl-1,2,3,4-tetrahydrobenzo[b][1,6]naphthyridine
;
_journal_name_full               'Acta Crystallographica, Section C'
_journal_page_first              o153
_journal_page_last               o155
_journal_volume                  59
_journal_year                    2003
_chemical_formula_moiety         'C24 H19 N3 O'
_chemical_formula_sum            'C24 H19 N3 O'
_chemical_formula_weight         365.42
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yab'
_symmetry_space_group_name_H-M   'P 1 21/a 1'
_cell_angle_alpha                90
_cell_angle_beta                 105.74(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.713(6)
_cell_length_b                   19.265(8)
_cell_length_c                   10.450(2)
_cell_measurement_temperature    293(2)
_cell_volume                     1882.1(14)
_diffrn_ambient_temperature      293(2)
_exptl_crystal_density_diffrn    1.290
_[local]_cod_cif_authors_sg_H-M  'P 21/a'
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_database_code               2013185
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x-1/2, -y-1/2, z'
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
O -0.2538(2) 0.74971(9) -0.15540(15) 0.0822(5) Uani d . 1 . . O
N1 0.26428(18) 0.85872(8) 0.22203(15) 0.0560(4) Uani d . 1 . . N
N2 -0.14707(17) 0.81452(8) 0.00869(15) 0.0519(4) Uani d . 1 . . N
N3 -0.2456(2) 0.76712(9) -0.04006(17) 0.0672(5) Uani d . 1 . . N
C1 0.0730(2) 0.88174(11) 0.02359(18) 0.0566(5) Uani d . 1 . . C
H1A 0.1525 0.8831 -0.0160 0.068 Uiso calc R 1 . . H
H1B 0.0397 0.9290 0.0268 0.068 Uiso calc R 1 . . H
C2 -0.0481(2) 0.83912(9) -0.06702(18) 0.0510(4) Uani d . 1 . . C
H2 -0.0053 0.7982 -0.0967 0.061 Uiso calc R 1 . . H
C3 -0.1325(2) 0.83110(10) 0.15039(18) 0.0536(5) Uani d . 1 . . C
H3 -0.1762 0.7925 0.1863 0.064 Uiso calc R 1 . . H
C4 0.0682(2) 0.81396(10) 0.3577(2) 0.0571(5) Uani d . 1 . . C
H4 0.0027 0.7977 0.4010 0.069 Uiso calc R 1 . . H
C5 0.2679(3) 0.80539(12) 0.5640(2) 0.0682(6) Uani d . 1 . . C
H5 0.2064 0.7903 0.6126 0.082 Uiso calc R 1 . . H
C6 0.4089(3) 0.81350(11) 0.6254(2) 0.0716(6) Uani d . 1 . . C
H6 0.4427 0.8043 0.7159 0.086 Uiso calc R 1 . . H
C7 0.5048(3) 0.83554(11) 0.5549(2) 0.0681(6) Uani d . 1 . . C
H7 0.6014 0.8407 0.5983 0.082 Uiso calc R 1 . . H
C8 0.4556(2) 0.84951(11) 0.4216(2) 0.0636(5) Uani d . 1 . . C
H8 0.5194 0.8643 0.3751 0.076 Uiso calc R 1 . . H
C9 0.3103(2) 0.84176(9) 0.35445(19) 0.0538(5) Uani d . 1 . . C
C10 0.2133(2) 0.81961(9) 0.42672(19) 0.0561(5) Uani d . 1 . . C
C11 0.1265(2) 0.85525(10) 0.16292(18) 0.0518(4) Uani d . 1 . . C
C12 0.0236(2) 0.83237(9) 0.22719(18) 0.0515(4) Uani d . 1 . . C
C13 -0.2166(2) 0.89604(10) 0.16495(17) 0.0532(5) Uani d . 1 . . C
C14 -0.3646(2) 0.89194(13) 0.1294(2) 0.0685(6) Uani d . 1 . . C
H14 -0.4091 0.8505 0.0961 0.082 Uiso calc R 1 . . H
C15 -0.4473(3) 0.94873(15) 0.1426(3) 0.0781(7) Uani d . 1 . . C
H15 -0.5466 0.9454 0.1186 0.094 Uiso calc R 1 . . H
C16 -0.3817(3) 1.00969(14) 0.1911(3) 0.0796(7) Uani d . 1 . . C
H16 -0.4367 1.0480 0.2001 0.095 Uiso calc R 1 . . H
C17 -0.2354(3) 1.01483(13) 0.2266(2) 0.0729(6) Uani d . 1 . . C
H17 -0.1918 1.0567 0.2588 0.087 Uiso calc R 1 . . H
C18 -0.1518(2) 0.95774(11) 0.2149(2) 0.0613(5) Uani d . 1 . . C
H18 -0.0526 0.9612 0.2406 0.074 Uiso calc R 1 . . H
C19 -0.12092(19) 0.88110(9) -0.18879(17) 0.0487(4) Uani d . 1 . . C
C20 -0.0778(2) 0.87241(11) -0.30400(19) 0.0610(5) Uani d . 1 . . C
H20 -0.0128 0.8377 -0.3084 0.073 Uiso calc R 1 . . H
C21 -0.1313(3) 0.91526(13) -0.4122(2) 0.0713(6) Uani d . 1 . . C
H21 -0.1010 0.9093 -0.4887 0.086 Uiso calc R 1 . . H
C22 -0.2287(3) 0.96660(12) -0.4083(2) 0.0689(6) Uani d . 1 . . C
H22 -0.2635 0.9955 -0.4813 0.083 Uiso calc R 1 . . H
C23 -0.2742(2) 0.97476(11) -0.2953(2) 0.0634(5) Uani d . 1 . . C
H23 -0.3417 1.0085 -0.2925 0.076 Uiso calc R 1 . . H
C24 -0.2195(2) 0.93276(10) -0.18588(19) 0.0558(5) Uani d . 1 . . C
H24 -0.2492 0.9393 -0.1093 0.067 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
O 0.0965(13) 0.0837(11) 0.0689(10) -0.0292(9) 0.0266(9) -0.0193(8)
N1 0.0563(10) 0.0551(9) 0.0562(9) -0.0051(7) 0.0148(7) 0.0006(7)
N2 0.0516(9) 0.0517(8) 0.0536(8) -0.0102(7) 0.0163(7) -0.0031(6)
N3 0.0756(12) 0.0641(10) 0.0609(10) -0.0189(9) 0.0168(9) -0.0077(8)
C1 0.0520(11) 0.0630(11) 0.0554(10) -0.0091(9) 0.0156(9) 0.0051(8)
C2 0.0517(11) 0.0504(9) 0.0540(10) -0.0011(8) 0.0196(8) -0.0020(7)
C3 0.0583(12) 0.0568(10) 0.0494(10) -0.0075(8) 0.0207(8) 0.0039(8)
C4 0.0651(12) 0.0527(10) 0.0556(10) -0.0024(9) 0.0196(9) 0.0070(8)
C5 0.0779(15) 0.0669(13) 0.0562(11) 0.0001(11) 0.0121(10) 0.0109(9)
C6 0.0878(17) 0.0592(12) 0.0579(12) -0.0039(11) 0.0029(11) 0.0046(9)
C7 0.0636(13) 0.0549(11) 0.0753(13) 0.0004(9) 0.0005(11) 0.0001(9)
C8 0.0603(13) 0.0588(11) 0.0673(12) -0.0019(9) 0.0097(10) 0.0008(9)
C9 0.0573(11) 0.0432(9) 0.0585(10) -0.0005(8) 0.0117(9) -0.0008(7)
C10 0.0635(12) 0.0467(9) 0.0563(11) -0.0020(8) 0.0134(9) 0.0048(8)
C11 0.0541(11) 0.0490(9) 0.0534(10) -0.0029(8) 0.0167(8) 0.0003(7)
C12 0.0549(11) 0.0479(9) 0.0521(10) -0.0045(8) 0.0153(8) 0.0012(7)
C13 0.0539(11) 0.0636(11) 0.0475(9) -0.0037(8) 0.0231(8) 0.0041(8)
C14 0.0547(12) 0.0814(14) 0.0752(13) -0.0093(10) 0.0274(10) -0.0064(11)
C15 0.0491(12) 0.1019(18) 0.0882(16) 0.0055(12) 0.0269(11) -0.0037(14)
C16 0.0764(16) 0.0807(16) 0.0917(16) 0.0113(13) 0.0399(13) -0.0009(13)
C17 0.0743(15) 0.0663(13) 0.0873(15) 0.0003(11) 0.0376(13) -0.0034(11)
C18 0.0534(11) 0.0657(12) 0.0686(12) -0.0046(9) 0.0228(9) -0.0019(9)
C19 0.0461(10) 0.0514(9) 0.0494(9) -0.0049(7) 0.0144(8) -0.0027(7)
C20 0.0687(13) 0.0633(11) 0.0575(11) -0.0006(10) 0.0281(10) -0.0051(9)
C21 0.0887(17) 0.0784(14) 0.0544(11) -0.0057(12) 0.0322(11) 0.0018(10)
C22 0.0809(15) 0.0644(12) 0.0605(12) -0.0058(11) 0.0176(11) 0.0099(10)
C23 0.0666(13) 0.0534(11) 0.0700(12) 0.0066(9) 0.0180(10) 0.0060(9)
C24 0.0574(11) 0.0573(11) 0.0556(10) 0.0024(8) 0.0204(9) -0.0024(8)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O N3 . 1.233(2) y
N1 C11 . 1.315(3) y
N1 C9 . 1.373(2) y
N2 N3 . 1.321(2) y
N2 C2 . 1.479(2) y
N2 C3 . 1.484(2) y
C1 C11 . 1.497(3) y
C1 C2 . 1.533(3) ?
C1 H1A . 0.9700 ?
C1 H1B . 0.9700 ?
C2 C19 . 1.512(3) y
C2 H2 . 0.9800 ?
C3 C12 . 1.511(3) ?
C3 C13 . 1.524(3) y
C3 H3 . 0.9800 ?
C4 C12 . 1.361(3) ?
C4 C10 . 1.402(3) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.355(4) ?
C5 C10 . 1.414(3) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.401(4) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.371(3) ?
C7 H7 . 0.9300 ?
C8 C9 . 1.404(3) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.423(3) ?
C11 C12 . 1.417(3) ?
C13 C18 . 1.380(3) ?
C13 C14 . 1.386(3) ?
C14 C15 . 1.386(3) ?
C14 H14 . 0.9300 ?
C15 C16 . 1.366(4) ?
C15 H15 . 0.9300 ?
C16 C17 . 1.372(4) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.392(3) ?
C17 H17 . 0.9300 ?
C18 H18 . 0.9300 ?
C19 C24 . 1.387(3) ?
C19 C20 . 1.388(2) ?
C20 C21 . 1.383(3) ?
C20 H20 . 0.9300 ?
C21 C22 . 1.377(3) ?
C21 H21 . 0.9300 ?
C22 C23 . 1.377(3) ?
C22 H22 . 0.9300 ?
C23 C24 . 1.384(3) ?
C23 H23 . 0.9300 ?
C24 H24 . 0.9300 ?