#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2011549.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_2011549
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2000
_journal_volume  56
_journal_page_first  e529
_journal_page_last  e530
_publ_section_title
;
1,3,5-Tri-p-tolylbiuret
;
loop_
_publ_author_name
  'Roh, Soo-Gyun'
  'Jeong, Jong Hwa'
_chemical_formula_sum  'C23 H23 N3 O2'
_chemical_formula_weight  373.44
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P 21 21 21'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, -y, z+1/2'
  '-x, y+1/2, -z+1/2'
  'x+1/2, -y+1/2, -z'
_cell_length_a  9.7626(6)
_cell_length_b  12.4280(8)
_cell_length_c  16.6770(7)
_cell_angle_alpha  90.00
_cell_angle_beta  90.00
_cell_angle_gamma  90.00
_cell_volume  2023.4(2)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.226
_diffrn_ambient_temperature  293(2)
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
  O1  .17347(19)  .43712(14)  .81849(12)  .0746(5) Uani d . 1 . . O
  O2  .3836(2)  .16374(14)  .88300(14)  .0959(7) Uani d . 1 . . O
  N1  .0323(2)  .40041(16)  .92202(15)  .0655(6) Uani d . 1 . . N
  H1N  .023(4)  .363(2)  .9582(18)  .089(11) Uiso d . 1 . . H
  N2  .3909(2)  .31527(15)  .80727(13)  .0606(5) Uani d . 1 . . N
  H2N  .334(3)  .377(2)  .7930(17)  .097(10) Uiso d . 1 . . H
  N3  .2003(2)  .27766(14)  .88748(12)  .0619(5) Uani d . 1 . . N
  C1  -.0506(2)  .49432(16)  .91564(14)  .0532(5) Uani d . 1 . . C
  C2  -.0793(2)  .55223(18)  .98375(15)  .0577(6) Uani d . 1 . . C
  H2  -.0410  .5319 1.0325  .069 Uiso calc R 1 . . H
  C3  -.1652(3)  .64093(18)  .97990(15)  .0621(6) Uani d . 1 . . C
  H3  -.1851  .6790 1.0265  .074 Uiso calc R 1 . . H
  C4  -.2217(2)  .67354(18)  .90814(15)  .0594(6) Uani d . 1 . . C
  C5  -.1922(3)  .6139(2)  .84004(15)  .0677(7) Uani d . 1 . . C
  H5  -.2306  .6337  .7912  .081 Uiso calc R 1 . . H
  C6  -.1066(3)  .5255(2)  .84382(15)  .0661(7) Uani d . 1 . . C
  H6  -.0868  .4869  .7975  .079 Uiso calc R 1 . . H
  C7  -.3127(3)  .7718(2)  .90410(17)  .0850(8) Uani d . 1 . . C
  H7A  -.3208  .8029  .9566  .127 Uiso calc R 1 . . H
  H7B  -.4018  .7513  .8851  .127 Uiso calc R 1 . . H
  H7C  -.2733  .8235  .8681  .127 Uiso calc R 1 . . H
  C8  .1259(2)  .19601(17)  .93088(15)  .0584(6) Uani d . 1 . . C
  C9  .1623(3)  .1666(2) 1.00739(16)  .0644(7) Uani d . 1 . . C
  H9  .2343  .2010 1.0334  .077 Uiso calc R 1 . . H
  C10  .0908(3)  .0854(2) 1.04500(16)  .0733(7) Uani d . 1 . . C
  H10  .1173  .0644 1.0962  .088 Uiso calc R 1 . . H
  C11  -.0183(3)  .03442(19) 1.00941(19)  .0744(8) Uani d . 1 . . C
  C12  -.0551(3)  .0676(2)  .9340(2)  .0829(8) Uani d . 1 . . C
  H12  -.1304  .0359  .9093  .099 Uiso calc R 1 . . H
  C13  .0162(3)  .1462(2)  .89376(16)  .0723(8) Uani d . 1 . . C
  H13  -.0091  .1658  .8420  .087 Uiso calc R 1 . . H
  C14  -.0927(4)  -.0550(2) 1.0517(2)  .1121(13) Uani d . 1 . . C
  H14A  -.0614  -.1231 1.0315  .168 Uiso calc R 1 . . H
  H14B  -.1893  -.0482 1.0423  .168 Uiso calc R 1 . . H
  H14C  -.0748  -.0509 1.1082  .168 Uiso calc R 1 . . H
  C15  .5221(2)  .30789(17)  .77152(13)  .0550(6) Uani d . 1 . . C
  C16  .5677(2)  .39712(19)  .73023(13)  .0594(6) Uani d . 1 . . C
  H16  .5132  .4584  .7277  .071 Uiso calc R 1 . . H
  C17  .6937(3)  .3961(2)  .69267(14)  .0629(6) Uani d . 1 . . C
  H17  .7236  .4574  .6659  .075 Uiso calc R 1 . . H
  C18  .7762(2)  .3059(2)  .69396(14)  .0629(6) Uani d . 1 . . C
  C19  .7288(3)  .2174(2)  .73444(16)  .0698(7) Uani d . 1 . . C
  H19  .7827  .1557  .7357  .084 Uiso calc R 1 . . H
  C20  .6039(3)  .21652(18)  .77351(15)  .0653(6) Uani d . 1 . . C
  H20  .5749  .1554  .8008  .078 Uiso calc R 1 . . H
  C21  .9147(3)  .3042(3)  .65307(19)  .0928(9) Uani d . 1 . . C
  H21A  .9327  .2333  .6329  .139 Uiso calc R 1 . . H
  H21B  .9845  .3238  .6910  .139 Uiso calc R 1 . . H
  H21C  .9149  .3546  .6094  .139 Uiso calc R 1 . . H
  C22  .1373(2)  .37676(18)  .87179(16)  .0597(6) Uani d . 1 . . C
  C23  .3332(3)  .24727(19)  .85904(16)  .0637(6) Uani d . 1 . . C
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
  O1  .0643(10)  .0632(10)  .0962(13)  .0121(9)  .0121(10)  .0172(10)
  O2  .0777(13)  .0605(10)  .1496(19)  .0179(10)  .0339(14)  .0286(12)
  N1  .0618(13)  .0520(11)  .0826(15)  .0053(10)  .0027(13)  .0093(12)
  N2  .0548(11)  .0518(10)  .0752(13)  .0053(10)  .0017(11)  .0010(10)
  N3  .0554(11)  .0470(10)  .0834(13)  .0006(9)  .0012(11)  .0012(10)
  C1  .0436(11)  .0461(11)  .0701(14)  -.0022(10)  -.0007(12)  .0026(11)
  C2  .0560(14)  .0589(13)  .0582(14)  -.0036(12)  -.0036(12)  .0067(11)
  C3  .0655(14)  .0573(13)  .0634(14)  .0009(12)  .0082(13)  .0003(11)
  C4  .0510(12)  .0580(13)  .0693(15)  .0038(11)  -.0038(12)  .0052(12)
  C5  .0619(15)  .0784(15)  .0629(14)  .0099(15)  -.0144(12)  -.0021(13)
  C6  .0633(14)  .0678(14)  .0673(15)  .0035(14)  -.0057(13)  -.0120(12)
  C7  .0828(19)  .0784(17)  .0936(19)  .0265(16)  -.0028(17)  .0044(16)
  C8  .0545(12)  .0463(11)  .0744(15)  .0040(11)  .0038(12)  -.0021(11)
  C9  .0595(14)  .0649(14)  .0688(16)  .0106(13)  -.0030(13)  -.0053(12)
  C10  .0795(18)  .0716(16)  .0688(15)  .0239(16)  .0136(15)  .0047(13)
  C11  .0790(19)  .0502(13)  .094(2)  .0099(14)  .0283(17)  -.0018(13)
  C12  .0793(18)  .0633(15)  .106(2)  -.0180(15)  -.0040(18)  -.0015(15)
  C13  .0768(18)  .0625(15)  .0775(17)  -.0115(14)  -.0097(15)  .0065(13)
  C14  .129(3)  .0682(17)  .139(3)  -.005(2)  .057(3)  .0152(18)
  C15  .0533(13)  .0541(12)  .0575(13)  -.0009(11)  -.0036(11)  -.0083(11)
  C16  .0610(14)  .0554(13)  .0618(13)  .0060(12)  -.0041(13)  -.0043(12)
  C17  .0649(15)  .0648(14)  .0591(13)  -.0026(13)  -.0020(13)  -.0029(12)
  C18  .0565(14)  .0717(15)  .0605(13)  .0025(13)  .0004(12)  -.0095(13)
  C19  .0633(15)  .0668(15)  .0794(16)  .0162(14)  -.0035(14)  -.0114(15)
  C20  .0663(15)  .0492(12)  .0803(16)  .0053(12)  .0031(14)  -.0036(12)
  C21  .0671(18)  .113(2)  .098(2)  .0086(19)  .0165(17)  -.0054(18)
  C22  .0525(14)  .0489(12)  .0778(15)  -.0012(11)  -.0051(13)  -.0005(12)
  C23  .0595(14)  .0483(12)  .0833(17)  .0031(12)  .0062(14)  -.0009(12)
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
  O1 C22 . 1.215(3) ?
  O2 C23 . 1.216(3) ?
  N1 C22 . 1.357(3) ?
  N1 C1 . 1.424(3) ?
  N2 C23 . 1.333(3) ?
  N2 C15 . 1.417(3) ?
  N3 C22 . 1.401(3) ?
  N3 C23 . 1.432(3) ?
  N3 C8 . 1.442(3) ?
  C1 C6 . 1.372(3) ?
  C1 C2 . 1.373(3) ?
  C2 C3 . 1.387(3) ?
  C3 C4 . 1.378(3) ?
  C4 C5 . 1.386(3) ?
  C4 C7 . 1.512(3) ?
  C5 C6 . 1.382(3) ?
  C8 C9 . 1.374(4) ?
  C8 C13 . 1.383(4) ?
  C9 C10 . 1.378(4) ?
  C10 C11 . 1.374(4) ?
  C11 C12 . 1.372(4) ?
  C11 C14 . 1.503(4) ?
  C12 C13 . 1.375(4) ?
  C15 C16 . 1.379(3) ?
  C15 C20 . 1.388(3) ?
  C16 C17 . 1.380(4) ?
  C17 C18 . 1.380(3) ?
  C18 C19 . 1.371(4) ?
  C18 C21 . 1.515(3) ?
  C19 C20 . 1.383(4) ?