#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008310.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_2008310
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  639
_journal_page_last  642
_publ_section_title
;
2-N,N-Dimethylamino-6-hydroxy-1,4-naphthoquinone
;
loop_
_publ_author_name
  'Doriguetto, Ant\^onio C.'
  "Santos, C\'atia A."
  "Raslan, D\'elio S."
  'Fernandes, Nelson G.'
_chemical_formula_moiety  'C12 H11 N O3'
_chemical_formula_sum  'C12 H11 N O3'
_chemical_formula_weight  217.22
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
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
_cell_length_a  13.6570(10)
_cell_length_b  14.4640(10)
_cell_length_c  11.0140(10)
_cell_angle_alpha  90
_cell_angle_beta  112.104(3)
_cell_angle_gamma  90
_cell_volume  2015.8(3)
_cell_formula_units_Z  8
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.431
_diffrn_ambient_temperature  298(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_thermal_displace_type
_atom_site_occupancy
  O1 -0.2003(2) 0.3997(2) 0.5659(2) 0.0676(11) Uani 1.000
  O2 -0.0656(2) 0.62903(13) 0.2833(2) 0.0520(9) Uani 1.000
  O3 0.0345(2) 0.3134(2) 0.1812(2) 0.0575(10) Uani 1.000
  N1 -0.2746(2) 0.5801(2) 0.5360(3) 0.0518(12) Uani 1.000
  C1 -0.1843(2) 0.4481(2) 0.4843(3) 0.0438(12) Uani 1.000
  C2 -0.2127(2) 0.5498(2) 0.4734(3) 0.0408(12) Uani 1.000
  C3 -0.1661(2) 0.6074(2) 0.4120(3) 0.0425(12) Uani 1.000
  C4 -0.1038(2) 0.5750(2) 0.3418(3) 0.0394(12) Uani 1.000
  C5 -0.0332(2) 0.4390(2) 0.2615(3) 0.0402(12) Uani 1.000
  C6 -0.0200(2) 0.3439(2) 0.2540(3) 0.0427(12) Uani 1.000
  C7 -0.0626(2) 0.2839(2) 0.3192(3) 0.0474(12) Uani 1.000
  C8 -0.1163(2) 0.3181(2) 0.3927(3) 0.0471(12) Uani 1.000
  C9 -0.1302(2) 0.4131(2) 0.4013(3) 0.0384(12) Uani 1.000
  C10 -0.0888(2) 0.4735(2) 0.3338(3) 0.0350(12) Uani 1.000
  C11 -0.3586(3) 0.5245(3) 0.5537(4) 0.0739(16) Uani 1.000
  C12 -0.2855(3) 0.6797(2) 0.5498(4) 0.0704(16) Uani 1.000
  O4 -0.2622(2) 0.1734(2) 0.4820(3) 0.0961(16) Uani 1.000
  O5 -0.4471(2) -0.06609(14) 0.6970(2) 0.0547(9) Uani 1.000
  O6 -0.5484(2) 0.2478(2) 0.8046(2) 0.0608(10) Uani 1.000
  N2 -0.2297(2) -0.0133(2) 0.4557(3) 0.0512(12) Uani 1.000
  C13 -0.2998(2) 0.1192(2) 0.5354(3) 0.0471(12) Uani 1.000
  C14 -0.2880(2) 0.0166(2) 0.5231(3) 0.0411(12) Uani 1.000
  C15 -0.3386(2) -0.0421(2) 0.5791(3) 0.0415(12) Uani 1.000
  C16 -0.4011(2) -0.0109(2) 0.6484(3) 0.0398(12) Uani 1.000
  C17 -0.4740(2) 0.1238(2) 0.7307(3) 0.0419(12) Uani 1.000
  C18 -0.4846(2) 0.2182(2) 0.7432(3) 0.0435(12) Uani 1.000
  C19 -0.4317(3) 0.2797(2) 0.6920(3) 0.0487(12) Uani 1.000
  C20 -0.3710(2) 0.2465(2) 0.6269(3) 0.0464(12) Uani 1.000
  C21 -0.3614(2) 0.1518(2) 0.6113(3) 0.0388(12) Uani 1.000
  C22 -0.4124(2) 0.0904(2) 0.6646(3) 0.0368(12) Uani 1.000
  C23 -0.1655(3) 0.0445(3) 0.4024(4) 0.0867(19) Uani 1.000
  C24 -0.2168(3) -0.1134(2) 0.4444(4) 0.0711(16) Uani 1.000
  H3A -0.1753(4) 0.674(2) 0.4173(3) 0.048(3) Uiso 1.000
  H3B 0.046(3) 0.249(3) 0.194(3) 0.099(10) Uiso 1.000
  H5A -0.0026(9) 0.4809(13) 0.2167(14) 0.048(3) Uiso 1.000
  H7A -0.0542(4) 0.217(2) 0.3123(4) 0.048(3) Uiso 1.000
  H8A -0.1428(9) 0.2773(13) 0.4389(15) 0.048(3) Uiso 1.000
  H11A -0.3464(3) 0.4602(3) 0.5431(4) 0.226(9) Uiso 1.000
  H11B -0.3587(3) 0.5346(3) 0.6398(4) 0.226(9) Uiso 1.000
  H11C -0.4257(3) 0.5425(3) 0.4893(4) 0.226(9) Uiso 1.000
  H12A -0.2280(3) 0.7111(2) 0.5375(4) 0.226(9) Uiso 1.000
  H12B -0.3512(3) 0.7006(2) 0.4853(4) 0.226(9) Uiso 1.000
  H12C -0.2842(3) 0.6928(2) 0.6358(4) 0.226(9) Uiso 1.000
  H6A -0.547(2) 0.313(3) 0.809(3) 0.099(10) Uiso 1.000
  H15A -0.3308(3) -0.109(2) 0.5702(4) 0.048(3) Uiso 1.000
  H17A -0.5097(11) 0.0811(13) 0.7674(12) 0.048(3) Uiso 1.000
  H19A -0.4372(3) 0.347(2) 0.7035(5) 0.048(3) Uiso 1.000
  H20A -0.3338(11) 0.2902(13) 0.5888(11) 0.048(3) Uiso 1.000
  H23A -0.1780(3) 0.1087(3) 0.4134(4) 0.226(9) Uiso 1.000
  H23B -0.0921(3) 0.0307(3) 0.4488(4) 0.226(9) Uiso 1.000
  H23C -0.1846(3) 0.0313(3) 0.3110(4) 0.226(9) Uiso 1.000
  H24A -0.2609(3) -0.1459(2) 0.4804(4) 0.226(9) Uiso 1.000
  H24B -0.2369(3) -0.1295(2) 0.3537(4) 0.226(9) Uiso 1.000
  H24C -0.1443(3) -0.1301(2) 0.4915(4) 0.226(9) Uiso 1.000
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 0.100(2) 0.0490(14) 0.084(2) -0.0006(13) 0.069(2) 0.0103(13)
  O2 0.0695(15) 0.0327(11) 0.071(2) -0.0044(11) 0.0462(13) 0.0068(11)
  O3 0.080(2) 0.0381(13) 0.078(2) 0.0026(12) 0.0567(15) -0.0025(12)
  N1 0.054(2) 0.045(2) 0.071(2) 0.0017(13) 0.040(2) -0.0001(14)
  C1 0.047(2) 0.038(2) 0.055(2) -0.0073(14) 0.029(2) 0.0004(15)
  C2 0.041(2) 0.040(2) 0.047(2) 0.0003(14) 0.0229(15) -0.0032(14)
  C3 0.052(2) 0.029(2) 0.052(2) 0.0031(14) 0.026(2) 0.0015(14)
  C4 0.042(2) 0.034(2) 0.045(2) -0.0037(13) 0.0196(15) -0.0007(14)
  C5 0.048(2) 0.034(2) 0.046(2) -0.0038(14) 0.026(2) 0.0017(14)
  C6 0.050(2) 0.037(2) 0.050(2) -0.0027(15) 0.029(2) -0.0040(14)
  C7 0.059(2) 0.031(2) 0.062(2) -0.0013(15) 0.034(2) -0.0004(15)
  C8 0.060(2) 0.032(2) 0.061(2) -0.0055(15) 0.036(2) 0.0038(15)
  C9 0.043(2) 0.032(2) 0.046(2) -0.0034(13) 0.0234(15) 0.0004(13)
  C10 0.038(2) 0.030(2) 0.040(2) -0.0019(13) 0.0180(14) 0.0002(13)
  C11 0.063(2) 0.078(3) 0.104(3) -0.006(2) 0.058(2) 0.001(2)
  C12 0.086(3) 0.051(2) 0.096(3) 0.016(2) 0.059(2) -0.001(2)
  O4 0.142(3) 0.046(2) 0.163(3) 0.000(2) 0.129(3) 0.012(2)
  O5 0.0668(15) 0.0331(12) 0.081(2) -0.0031(11) 0.0471(14) 0.0064(11)
  O6 0.080(2) 0.0386(13) 0.090(2) -0.0004(12) 0.062(2) -0.0048(13)
  N2 0.059(2) 0.046(2) 0.062(2) -0.0002(13) 0.0380(15) -0.0044(13)
  C13 0.053(2) 0.037(2) 0.062(2) -0.0034(15) 0.034(2) 0.003(2)
  C14 0.042(2) 0.040(2) 0.045(2) 0.0001(14) 0.0206(15) -0.0006(14)
  C15 0.048(2) 0.030(2) 0.052(2) 0.0021(14) 0.025(2) -0.0022(14)
  C16 0.042(2) 0.033(2) 0.046(2) -0.0019(13) 0.0183(15) 0.0060(13)
  C17 0.049(2) 0.034(2) 0.053(2) -0.0050(14) 0.031(2) 0.0017(14)
  C18 0.049(2) 0.036(2) 0.054(2) -0.0003(14) 0.029(2) -0.0026(14)
  C19 0.060(2) 0.028(2) 0.067(2) -0.0027(15) 0.034(2) -0.0024(15)
  C20 0.054(2) 0.032(2) 0.065(2) -0.0053(15) 0.036(2) 0.003(2)
  C21 0.043(2) 0.031(2) 0.048(2) -0.0020(13) 0.0236(15) 0.0023(13)
  C22 0.039(2) 0.031(2) 0.042(2) -0.0029(13) 0.0171(14) 0.0027(13)
  C23 0.110(3) 0.074(3) 0.119(4) -0.008(2) 0.092(3) -0.005(3)
  C24 0.092(3) 0.047(2) 0.099(3) 0.006(2) 0.064(3) -0.012(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
  O1 C1 . . 1.222(4) yes
  O2 C4 . . 1.245(4) yes
  O3 C6 . . 1.357(4) yes
  O3 H3B . . 0.95(4) no
  O4 C13 . . 1.205(4) yes
  O5 C16 . . 1.254(4) yes
  O6 C18 . . 1.358(4) yes
  O6 H6A . . 0.94(4) ?
  N1 C11 . . 1.473(5) ?
  N1 C12 . . 1.462(4) ?
  N1 C2 . . 1.349(4) yes
  N2 C24 . . 1.469(4) ?
  N2 C14 . . 1.348(4) yes
  N2 C23 . . 1.483(5) ?
  C1 C2 . . 1.514(4) yes
  C1 C9 . . 1.465(4) yes
  C2 C3 . . 1.371(4) yes
  C3 C4 . . 1.427(4) yes
  C4 C10 . . 1.490(4) yes
  C5 C10 . . 1.384(4) no
  C5 C6 . . 1.394(4) no
  C6 C7 . . 1.386(4) no
  C7 C8 . . 1.373(4) no
  C8 C9 . . 1.395(4) no
  C9 C10 . . 1.397(4) yes
  C3 H3A . . 0.98(3) no
  C5 H5A . . 0.970(16) no
  C7 H7A . . 0.98(3) no
  C8 H8A . . 0.936(17) no
  C11 H11B . . 0.960(6) no
  C11 H11A . . 0.960(6) no
  C11 H11C . . 0.960(6) no
  C12 H12C . . 0.960(6) no
  C12 H12B . . 0.960(6) no
  C12 H12A . . 0.960(6) no
  C13 C14 . . 1.504(4) yes
  C13 C21 . . 1.469(4) yes
  C14 C15 . . 1.378(4) yes
  C15 C16 . . 1.416(4) yes
  C16 C22 . . 1.491(4) yes
  C17 C22 . . 1.390(4) no
  C17 C18 . . 1.385(4) no
  C18 C19 . . 1.392(5) no
  C19 C20 . . 1.371(5) no
  C20 C21 . . 1.393(4) no
  C21 C22 . . 1.388(4) yes
  C15 H15A . . 0.98(3) no
  C17 H17A . . 0.965(17) no
  C19 H19A . . 0.99(3) no
  C20 H20A . . 0.997(17) no
  C23 H23A . . 0.960(6) no
  C23 H23B . . 0.959(6) no
  C23 H23C . . 0.959(6) no
  C24 H24A . . 0.959(6) no
  C24 H24B . . 0.960(6) no
  C24 H24C . . 0.960(6) no