#------------------------------------------------------------------------------
#$Date: 2008-01-13 22:15:36 +0000 (Sun, 13 Jan 2008) $
#$Revision: 14 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008355.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_2008355
_journal_name_full  'Acta Crystallographica'
_journal_year  1999
_journal_volume  C55
_journal_page_first  634
_journal_page_last  636
_publ_section_title
;
2-Ethylthio-9-methyl-1,4-dihydroacridine-1,4-dione and
9-methyl-2-(4-tolylthio)-1,4-dihydroacridine-1,4-dione
;
loop_
_publ_author_name
  'Baker, L.-J.'
  'Clark, George R.'
  'Copp, Brent R.'
  'Hansen, Richard P.'
  'Squire, Christopher J.'
_chemical_formula_sum  'C21 H15 N O2 S'
_chemical_formula_weight  345.40
_symmetry_cell_setting  Monoclinic
_symmetry_space_group_name_H-M  'P 21/n'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x+1/2, y+1/2, -z+1/2'
  '-x, -y, -z'
  'x-1/2, -y-1/2, z-1/2'
_cell_length_a  9.2792(2)
_cell_length_b  8.7627(2)
_cell_length_c  20.1726(5)
_cell_angle_alpha  90.00
_cell_angle_beta  98.4450(10)
_cell_angle_gamma  90.00
_cell_volume  1622.47(6)
_cell_formula_units_Z  4
_cell_measurement_temperature  203(2)
_exptl_crystal_density_diffrn  1.414
_diffrn_ambient_temperature  203(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 0.44792(11) 0.69100(13) 0.16313(6) 0.0395(3) Uani d . 1 . . O
  O4 0.82416(11) 0.32426(13) 0.06580(5) 0.0363(3) Uani d . 1 . . O
  N10 0.53843(12) 0.26612(13) 0.02528(5) 0.0244(2) Uani d . 1 . . N
  S2 0.72142(4) 0.72242(5) 0.237659(19) 0.03344(12) Uani d . 1 . . S
  C1 0.52465(14) 0.59212(16) 0.14389(7) 0.0252(3) Uani d . 1 . . C
  C2 0.68416(14) 0.59221(15) 0.17161(6) 0.0245(3) Uani d . 1 . . C
  C3 0.78022(14) 0.50423(16) 0.14570(7) 0.0260(3) Uani d . 1 . . C
  H3A 0.8797 0.5120 0.1630 0.031 Uiso calc R 1 . . H
  C4a 0.57277(14) 0.37584(15) 0.06899(6) 0.0220(3) Uani d . 1 . . C
  C4 0.73444(14) 0.39668(15) 0.09141(6) 0.0245(3) Uani d . 1 . . C
  C5 0.35741(16) 0.11594(17) -0.03989(7) 0.0312(3) Uani d . 1 . . C
  H5A 0.4319 0.0599 -0.0556 0.037 Uiso calc R 1 . . H
  C6 0.21503(17) 0.07753(18) -0.06036(8) 0.0366(3) Uani d . 1 . . C
  H6A 0.1920 -0.0066 -0.0889 0.044 Uiso calc R 1 . . H
  C7 0.10308(17) 0.16424(19) -0.03870(8) 0.0371(3) Uani d . 1 . . C
  H7A 0.0054 0.1380 -0.0533 0.045 Uiso calc R 1 . . H
  C8a 0.28125(14) 0.32734(15) 0.02729(6) 0.0242(3) Uani d . 1 . . C
  C8 0.13438(15) 0.28619(18) 0.00340(7) 0.0312(3) Uani d . 1 . . C
  H8A 0.0579 0.3435 0.0167 0.037 Uiso calc R 1 . . H
  C9a 0.46969(13) 0.47152(14) 0.09468(6) 0.0219(3) Uani d . 1 . . C
  C9 0.32123(14) 0.44973(15) 0.07337(6) 0.0238(3) Uani d . 1 . . C
  C10a 0.39362(14) 0.23950(15) 0.00475(6) 0.0241(3) Uani d . 1 . . C
  C11 0.20621(15) 0.54849(19) 0.09675(8) 0.0349(3) Uani d . 1 . . C
  H11A 0.2110 0.6502 0.0782 0.052 Uiso calc R 1 . . H
  H11B 0.2225 0.5541 0.1453 0.052 Uiso calc R 1 . . H
  H11C 0.1109 0.5049 0.0818 0.052 Uiso calc R 1 . . H
  C12 0.91275(15) 0.69992(16) 0.26136(7) 0.0282(3) Uani d . 1 . . C
  C13 1.00805(17) 0.79496(18) 0.23386(8) 0.0353(3) Uani d . 1 . . C
  H13A 0.9719 0.8669 0.2010 0.042 Uiso calc R 1 . . H
  C14 1.15661(17) 0.78344(19) 0.25494(8) 0.0369(3) Uani d . 1 . . C
  H14A 1.2206 0.8475 0.2358 0.044 Uiso calc R 1 . . H
  C15 1.21302(16) 0.67886(17) 0.30388(7) 0.0313(3) Uani d . 1 . . C
  C16 1.11620(17) 0.58404(18) 0.33057(8) 0.0347(3) Uani d . 1 . . C
  H16A 1.1522 0.5119 0.3634 0.042 Uiso calc R 1 . . H
  C17 0.96698(16) 0.59396(18) 0.30963(7) 0.0332(3) Uani d . 1 . . C
  H17A 0.9030 0.5289 0.3282 0.040 Uiso calc R 1 . . H
  C18 1.37464(17) 0.6695(2) 0.32687(9) 0.0444(4) Uani d . 1 . . C
  H18A 1.3946 0.5901 0.3605 0.067 Uiso calc R 1 . . H
  H18B 1.4095 0.7666 0.3460 0.067 Uiso calc R 1 . . H
  H18C 1.4240 0.6457 0.2890 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
  O1 0.0286(5) 0.0408(6) 0.0475(6) 0.0076(5) 0.0007(5) -0.0191(5)
  O4 0.0231(5) 0.0441(6) 0.0420(6) 0.0052(4) 0.0062(4) -0.0123(5)
  N10 0.0238(5) 0.0254(6) 0.0237(5) 0.0033(4) 0.0024(4) 0.0001(4)
  S2 0.02592(19) 0.0391(2) 0.0343(2) 0.00037(15) 0.00093(14) -0.01384(15)
  C1 0.0228(6) 0.0275(7) 0.0253(6) 0.0023(5) 0.0039(5) -0.0009(5)
  C2 0.0239(6) 0.0256(7) 0.0233(6) -0.0018(5) 0.0012(5) 0.0004(5)
  C3 0.0199(6) 0.0309(7) 0.0266(6) -0.0005(5) 0.0014(5) 0.0002(5)
  C4a 0.0213(6) 0.0239(6) 0.0207(6) 0.0016(5) 0.0030(5) 0.0030(5)
  C4 0.0214(6) 0.0271(7) 0.0253(6) 0.0021(5) 0.0045(5) 0.0020(5)
  C5 0.0328(7) 0.0296(7) 0.0296(7) 0.0050(6) -0.0010(6) -0.0041(6)
  C6 0.0370(8) 0.0323(8) 0.0371(8) -0.0022(6) -0.0059(6) -0.0074(6)
  C7 0.0277(7) 0.0405(8) 0.0405(8) -0.0054(6) -0.0033(6) -0.0033(7)
  C8a 0.0229(6) 0.0268(7) 0.0224(6) 0.0003(5) 0.0023(5) 0.0026(5)
  C8 0.0237(7) 0.0377(8) 0.0315(7) 0.0001(6) 0.0016(5) -0.0006(6)
  C9A 0.0220(6) 0.0232(6) 0.0206(6) 0.0024(5) 0.0037(5) 0.0017(5)
  C9 0.0223(6) 0.0269(7) 0.0222(6) 0.0030(5) 0.0037(5) 0.0017(5)
  C10a 0.0253(6) 0.0250(6) 0.0211(6) 0.0017(5) 0.0006(5) 0.0031(5)
  C11 0.0223(7) 0.0422(8) 0.0398(8) 0.0060(6) 0.0028(6) -0.0100(7)
  C12 0.0257(7) 0.0323(7) 0.0259(6) -0.0030(5) 0.0015(5) -0.0084(5)
  C13 0.0366(8) 0.0372(8) 0.0308(7) -0.0056(6) 0.0000(6) 0.0041(6)
  C14 0.0329(8) 0.0435(9) 0.0350(8) -0.0107(7) 0.0070(6) -0.0010(7)
  C15 0.0279(7) 0.0369(8) 0.0290(7) -0.0003(6) 0.0033(5) -0.0121(6)
  C16 0.0362(8) 0.0350(8) 0.0320(7) 0.0022(6) 0.0019(6) 0.0008(6)
  C17 0.0329(7) 0.0348(8) 0.0319(7) -0.0067(6) 0.0049(6) 0.0003(6)
  C18 0.0281(8) 0.0575(11) 0.0465(9) 0.0032(7) 0.0016(7) -0.0145(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
  O1 C1 . 1.2204(16) ?
  O4 C4 . 1.2204(16) ?
  N10 C4A . 1.3118(17) ?
  N10 C10A . 1.3667(17) ?
  S2 C2 . 1.7497(13) ?
  S2 C12 . 1.7804(14) ?
  C1 C9A . 1.4878(18) ?
  C1 C2 . 1.5034(18) ?
  C2 C3 . 1.3412(19) ?
  C3 C4 . 1.4599(19) ?
  C4A C9A . 1.4254(17) ?
  C4A C4 . 1.5130(17) ?
  C5 C6 . 1.367(2) ?
  C5 C10A . 1.4168(19) ?
  C6 C7 . 1.407(2) ?
  C7 C8 . 1.369(2) ?
  C8A C10A . 1.4233(18) ?
  C8A C8 . 1.4236(19) ?
  C8A C9 . 1.4320(19) ?
  C9A C9 . 1.3947(17) ?
  C9 C11 . 1.5027(18) ?
  C12 C17 . 1.386(2) ?
  C12 C13 . 1.388(2) ?
  C13 C14 . 1.385(2) ?
  C14 C15 . 1.392(2) ?
  C15 C16 . 1.389(2) ?
  C15 C18 . 1.506(2) ?
  C16 C17 . 1.390(2) ?