#------------------------------------------------------------------------------
#$Date: 2008-01-26 14:05:32 +0100 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2008354.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_2008354
_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  'C16 H13 N O2 S'
_chemical_formula_weight  283.3
_symmetry_cell_setting  triclinic
_symmetry_space_group_name_H-M  'P -1'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  '-x, -y, -z'
_cell_length_a  7.736(6)
_cell_length_b  11.690(4)
_cell_length_c  14.704(5)
_cell_angle_alpha  82.58(4)
_cell_angle_beta  79.28(4)
_cell_angle_gamma  88.56(4)
_cell_volume  1295.6(12)
_cell_formula_units_Z  4
_cell_measurement_temperature  203(2)
_exptl_crystal_density_diffrn  1.453
_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 0.0615(3) 0.40371(17) 0.20668(14) 0.0419(6) Uani d . 1 . . O
  C1 -0.0255(3) 0.3162(2) 0.22454(18) 0.0278(6) Uani d . 1 . . C
  S2 0.11946(10) 0.29322(6) 0.04778(5) 0.03199(19) Uani d . 1 . . S
  C2 -0.0066(4) 0.2347(2) 0.15294(18) 0.0277(6) Uani d . 1 . . C
  C3 -0.0799(4) 0.1298(2) 0.17220(18) 0.0305(6) Uani d . 1 . . C
  O4 -0.2548(3) -0.00500(17) 0.27739(14) 0.0426(5) Uani d . 1 . . O
  C4 -0.1866(4) 0.0895(2) 0.26243(18) 0.0277(6) Uani d . 1 . . C
  C4a -0.2155(3) 0.1707(2) 0.33502(17) 0.0241(5) Uani d . 1 . . C
  C5 -0.4427(4) 0.1501(2) 0.57105(18) 0.0293(6) Uani d . 1 . . C
  C6 -0.4837(4) 0.2168(2) 0.64184(19) 0.0320(6) Uani d . 1 . . C
  C7 -0.4342(4) 0.3326(2) 0.62837(19) 0.0325(6) Uani d . 1 . . C
  C8 -0.3430(4) 0.3823(2) 0.54423(19) 0.0314(6) Uani d . 1 . . C
  C8a -0.2928(3) 0.3156(2) 0.46935(18) 0.0262(5) Uani d . 1 . . C
  C9 -0.1886(3) 0.3603(2) 0.38164(18) 0.0266(5) Uani d . 1 . . C
  C9a -0.1455(3) 0.2842(2) 0.31553(17) 0.0253(5) Uani d . 1 . . C
  N10 -0.3105(3) 0.12740(18) 0.41597(15) 0.0277(5) Uani d . 1 . . N
  C10a -0.3464(3) 0.1985(2) 0.48366(18) 0.0256(5) Uani d . 1 . . C
  C11 -0.1329(4) 0.4845(2) 0.3648(2) 0.0352(7) Uani d . 1 . . C
  H11A -0.0145 0.4903 0.3767 0.053 Uiso calc R 1 . . H
  H11B -0.2129 0.5284 0.4062 0.053 Uiso calc R 1 . . H
  H11C -0.1354 0.5152 0.3005 0.053 Uiso calc R 1 . . H
  C12 0.1182(4) 0.1787(3) -0.0234(2) 0.0359(7) Uani d . 1 . . C
  C13 0.2068(5) 0.2229(3) -0.1233(2) 0.0464(8) Uani d . 1 . . C
  H13A 0.1415 0.2885 -0.1471 0.070 Uiso calc R 1 . . H
  H13B 0.2084 0.1620 -0.1625 0.070 Uiso calc R 1 . . H
  H13C 0.3264 0.2462 -0.1238 0.070 Uiso calc R 1 . . H
  H3 -0.067(5) 0.073(3) 0.128(3) 0.056 Uiso d . 1 . . H
  H5 -0.482(5) 0.074(3) 0.578(3) 0.056 Uiso d . 1 . . H
  H6 -0.545(5) 0.180(3) 0.701(3) 0.056 Uiso d . 1 . . H
  H7 -0.453(5) 0.382(3) 0.675(3) 0.056 Uiso d . 1 . . H
  H8 -0.306(5) 0.464(3) 0.537(3) 0.056 Uiso d . 1 . . H
  H12A -0.007(5) 0.157(3) -0.024(3) 0.056 Uiso d . 1 . . H
  H12B 0.184(5) 0.114(3) 0.008(3) 0.056 Uiso d . 1 . . H
  C1' 0.4047(4) 0.3168(2) 0.28549(18) 0.0278(6) Uani d . 1 . . C
  O1' 0.4247(3) 0.41151(18) 0.30673(15) 0.0471(6) Uani d . 1 . . O
  S2' 0.22098(9) 0.28701(6) 0.46014(4) 0.02982(18) Uani d . 1 . . S
  C2' 0.2965(3) 0.2314(2) 0.35635(17) 0.0264(5) Uani d . 1 . . C
  C3' 0.2649(4) 0.1252(2) 0.33808(19) 0.0306(6) Uani d . 1 . . C
  O4' 0.2904(3) -0.00718(17) 0.23153(14) 0.0449(6) Uani d . 1 . . O
  C4' 0.3288(4) 0.0870(2) 0.24742(19) 0.0308(6) Uani d . 1 . . C
  C4a' 0.4403(4) 0.1692(2) 0.17402(18) 0.0265(5) Uani d . 1 . . C
  C5' 0.6367(4) 0.1589(3) -0.06379(19) 0.0325(6) Uani d . 1 . . C
  C6' 0.7250(4) 0.2291(3) -0.1391(2) 0.0349(7) Uani d . 1 . . C
  C7' 0.7690(4) 0.3420(3) -0.1304(2) 0.0358(7) Uani d . 1 . . C
  C8' 0.7282(4) 0.3836(2) -0.04645(19) 0.0321(6) Uani d . 1 . . C
  C8a' 0.6343(4) 0.3150(2) 0.03319(18) 0.0267(5) Uani d . 1 . . C
  C9' 0.5825(4) 0.3551(2) 0.12204(18) 0.0268(5) Uani d . 1 . . C
  C9a' 0.4803(3) 0.2817(2) 0.19223(17) 0.0251(5) Uani d . 1 . . C
  N10' 0.4936(3) 0.12877(19) 0.09417(15) 0.0286(5) Uani d . 1 . . N
  C10b 0.5876(4) 0.2014(2) 0.02326(18) 0.0274(6) Uani d . 1 . . C
  C11' 0.6434(4) 0.4717(2) 0.1348(2) 0.0368(7) Uani d . 1 . . C
  H11D 0.5557 0.5291 0.1217 0.055 Uiso calc R 1 . . H
  H11E 0.7538 0.4903 0.0924 0.055 Uiso calc R 1 . . H
  H11F 0.6603 0.4711 0.1986 0.055 Uiso calc R 1 . . H
  C12' 0.1060(4) 0.1657(3) 0.53334(19) 0.0313(6) Uani d . 1 . . C
  C13' 0.0278(4) 0.2042(3) 0.6273(2) 0.0390(7) Uani d . 1 . . C
  H13D 0.1218 0.2264 0.6569 0.059 Uiso calc R 1 . . H
  H13E -0.0386 0.1412 0.6668 0.059 Uiso calc R 1 . . H
  H13F -0.0496 0.2695 0.6182 0.059 Uiso calc R 1 . . H
  H3' 0.187(4) 0.070(3) 0.381(2) 0.047 Uiso d . 1 . . H
  H5' 0.612(4) 0.086(3) -0.070(2) 0.047 Uiso d . 1 . . H
  H6' 0.753(5) 0.199(3) -0.195(3) 0.047 Uiso d . 1 . . H
  H7' 0.816(5) 0.398(3) -0.178(3) 0.047 Uiso d . 1 . . H
  H8' 0.761(4) 0.464(3) -0.042(2) 0.047 Uiso d . 1 . . H
  H12C 0.020(5) 0.141(3) 0.499(2) 0.047 Uiso d . 1 . . H
  H12D 0.195(5) 0.102(3) 0.543(2) 0.047 Uiso d . 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 0.0521(13) 0.0317(11) 0.0346(11) -0.0172(10) 0.0156(10) -0.0084(8)
  C1 0.0272(14) 0.0300(14) 0.0241(13) -0.0023(11) -0.0002(10) -0.0022(10)
  S2 0.0361(4) 0.0336(4) 0.0228(3) -0.0076(3) 0.0049(3) -0.0041(3)
  C2 0.0272(14) 0.0319(14) 0.0217(12) 0.0021(11) 0.0000(10) -0.0022(10)
  C3 0.0370(15) 0.0294(13) 0.0224(13) -0.0022(11) 0.0041(11) -0.0069(11)
  O4 0.0616(15) 0.0304(11) 0.0318(11) -0.0155(10) 0.0079(10) -0.0102(8)
  C4 0.0324(14) 0.0267(13) 0.0223(12) -0.0028(11) 0.0000(11) -0.0032(10)
  C4a 0.0245(13) 0.0249(12) 0.0223(12) -0.0025(10) -0.0001(10) -0.0060(10)
  C5 0.0330(15) 0.0287(13) 0.0237(13) -0.0030(11) 0.0013(11) -0.0026(10)
  C6 0.0343(15) 0.0374(15) 0.0211(13) -0.0040(12) 0.0026(11) -0.0023(11)
  C7 0.0363(16) 0.0343(15) 0.0254(14) -0.0015(12) 0.0027(12) -0.0096(11)
  C8 0.0377(16) 0.0280(14) 0.0281(14) -0.0017(12) -0.0006(12) -0.0091(11)
  C8a 0.0259(13) 0.0275(13) 0.0236(13) -0.0018(10) 0.0000(10) -0.0041(10)
  C9 0.0280(14) 0.0246(13) 0.0266(13) -0.0017(10) -0.0031(11) -0.0039(10)
  C9a 0.0268(13) 0.0258(12) 0.0219(12) -0.0025(10) 0.0003(10) -0.0046(10)
  N10 0.0317(12) 0.0249(11) 0.0249(11) -0.0032(9) 0.0002(9) -0.0043(8)
  C10a 0.0256(13) 0.0274(13) 0.0226(12) -0.0022(10) -0.0004(10) -0.0043(10)
  C11 0.0471(18) 0.0259(14) 0.0291(14) -0.0073(12) 0.0049(13) -0.0064(11)
  C12 0.0402(17) 0.0415(16) 0.0242(13) -0.0064(14) 0.0046(12) -0.0117(12)
  C13 0.0476(19) 0.059(2) 0.0294(15) -0.0101(16) 0.0091(14) -0.0139(14)
  C1' 0.0306(14) 0.0279(13) 0.0252(13) -0.0028(11) -0.0043(11) -0.0054(10)
  O1' 0.0666(15) 0.0350(11) 0.0343(11) -0.0197(10) 0.0150(10) -0.0150(9)
  S2' 0.0349(4) 0.0306(3) 0.0222(3) -0.0034(3) 0.0021(3) -0.0068(2)
  C2' 0.0251(13) 0.0320(13) 0.0201(12) -0.0011(11) 0.0007(10) -0.0031(10)
  C3' 0.0356(15) 0.0287(13) 0.0247(13) -0.0043(12) 0.0030(11) -0.0044(11)
  O4' 0.0642(15) 0.0317(11) 0.0336(11) -0.0178(10) 0.0114(10) -0.0113(9)
  C4' 0.0375(15) 0.0273(13) 0.0257(13) -0.0045(11) 0.0003(11) -0.0047(10)
  C4a' 0.0285(13) 0.0255(12) 0.0238(12) -0.0018(10) -0.0001(10) -0.0033(10)
  C5' 0.0373(16) 0.0298(14) 0.0285(14) -0.0051(12) 0.0023(12) -0.0075(11)
  C6' 0.0411(17) 0.0375(15) 0.0246(14) -0.0048(13) 0.0016(12) -0.0084(11)
  C7' 0.0415(17) 0.0365(15) 0.0260(14) -0.0080(13) 0.0020(12) -0.0013(12)
  C8' 0.0369(16) 0.0289(14) 0.0286(14) -0.0053(12) -0.0007(12) -0.0036(11)
  C8a' 0.0278(13) 0.0266(13) 0.0249(13) -0.0009(10) -0.0026(11) -0.0032(10)
  C9' 0.0305(14) 0.0260(12) 0.0234(12) -0.0009(10) -0.0035(10) -0.0032(10)
  C9a' 0.0294(14) 0.0236(12) 0.0223(12) -0.0014(10) -0.0033(10) -0.0043(10)
  N10' 0.0357(13) 0.0248(11) 0.0232(11) -0.0035(9) 0.0016(9) -0.0053(8)
  C10b 0.0325(14) 0.0269(13) 0.0208(12) -0.0021(11) -0.0010(10) -0.0012(10)
  C11' 0.0462(18) 0.0307(14) 0.0319(15) -0.0108(13) -0.0006(13) -0.0054(11)
  C12' 0.0319(15) 0.0366(15) 0.0221(13) -0.0029(12) 0.0036(11) -0.0030(11)
  C13' 0.0407(17) 0.0447(17) 0.0271(14) -0.0045(13) 0.0069(12) -0.0054(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 C1 . 1.212(3) ?
  C1 C9a . 1.489(3) ?
  C1 C2 . 1.494(4) ?
  S2 C2 . 1.735(3) ?
  S2 C12 . 1.804(3) ?
  C2 C3 . 1.339(4) ?
  C3 C4 . 1.454(4) ?
  O4 C4 . 1.212(3) ?
  C4 C4a . 1.501(3) ?
  C4a N10 . 1.323(3) ?
  C4a C9a . 1.420(4) ?
  C5 C6 . 1.366(4) ?
  C5 C10a . 1.416(4) ?
  C6 C7 . 1.395(4) ?
  C7 C8 . 1.370(4) ?
  C8 C8a . 1.420(4) ?
  C8a C10a . 1.419(4) ?
  C8a C9 . 1.430(4) ?
  C9 C9a . 1.391(3) ?
  C9 C11 . 1.502(4) ?
  N10 C10a . 1.363(3) ?
  C12 C13 . 1.531(4) ?
  C1' O1' . 1.209(3) ?
  C1' C9a' . 1.492(3) ?
  C1' C2' . 1.494(4) ?
  S2' C2' . 1.731(3) ?
  S2' C12' . 1.809(3) ?
  C2' C3' . 1.341(4) ?
  C3' C4' . 1.456(4) ?
  O4' C4' . 1.209(3) ?
  C4' C4a' . 1.504(4) ?
  C4a' N10' . 1.314(3) ?
  C4a' C9a' . 1.428(3) ?
  C5' C6' . 1.371(4) ?
  C5' C10b . 1.415(4) ?
  C6' C7' . 1.399(4) ?
  C7' C8' . 1.365(4) ?
  C8' C8a' . 1.418(4) ?
  C8a' C10b . 1.418(4) ?
  C8a' C9' . 1.429(4) ?
  C9' C9a' . 1.389(4) ?
  C9' C11' . 1.498(4) ?
  N10' C10b . 1.362(3) ?
  C12' C13' . 1.521(4) ?