#------------------------------------------------------------------------------
#$Date: 2011-09-17 23:27:16 +0300 (Sat, 17 Sep 2011) $
#$Revision: 26029 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/2008116.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_2008116
_journal_name_full 'Acta Crystallographica Section C'
_journal_year  1999
_journal_volume 55
_journal_page_first  114
_journal_page_last  116
_publ_section_title
;
9-Acetonyl-3-ethylidene-1,2,3,4-tetrahydrospiro[carbazole-1,2'-
[1,3]dithiolan]-4-one
;
loop_
_publ_author_name
  'H\"okelek*, Tuncer'
  'Pat\?ir, S\"uleyman'
  "Uluda\(g, Nes\.im\.i"
_chemical_formula_moiety  'C18 H19 N O2 S2'
_chemical_formula_sum  'C18 H19 N O2 S2'
_chemical_formula_weight  345.49
_symmetry_cell_setting  orthorhombic
_symmetry_space_group_name_H-M  'P b c a'
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'
  '-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  9.2020(10)
_cell_length_b  18.870(3)
_cell_length_c  19.138(2)
_cell_angle_alpha  90
_cell_angle_beta  90
_cell_angle_gamma  90
_cell_volume  3323.2(7)
_cell_formula_units_Z  8
_cell_measurement_temperature  298
_exptl_crystal_density_diffrn  1.381
_refine_ls_R_factor_obs  0.038
_refine_ls_wR_factor_obs  0.048
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
  S1 0.30269(6) 0.12239(3) 0.11505(3) 0.0384(9)
  S2 0.04751(6) 0.02854(3) 0.09304(3) 0.0390(9)
  O1 -0.2189(2) 0.22746(8) -0.02959(8) 0.0501(3)
  O2 0.4394(2) 0.06024(9) -0.07971(8) 0.0479(3)
  C1 0.1189(2) 0.11736(9) 0.07541(9) 0.0294(3)
  C2 0.0275(2) 0.17570(10)
  0.11090(10)
  0.0346(4)
  C3 -0.1198(2) 0.18690(10)
  0.07890(10)
  0.0346(4)
  C4 -0.1197(2) 0.19780(10)
  0.00150(10)
  0.0335(3)
  C4a 0.0029(2) 0.16656(9) -0.03462(9) 0.0294(3)
  C5 -0.0492(2) 0.18690(10)
  -0.16720(10)
  0.0371(4)
  C5a 0.0241(2) 0.16042(9) -0.10888(9) 0.0299(3)
  C6 0.0011(3) 0.16820(10)
  -0.23270(10)
  0.0427(4)
  C7 0.1214(3) 0.12450(10)
  -0.24080(10)
  0.0451(4)
  C8 0.1959(2) 0.09780(10)
  -0.18420(10)
  0.0413(4)
  C8a 0.1460(2) 0.11670(10)
  -0.11810(10)
  0.0321(3)
  N9 0.1994(2) 0.09748(8) -0.05250(8) 0.0311(3)
  C9a 0.1118(2) 0.12791(9) -0.00247(9) 0.0281(3)
  C10 0.2990(3) 0.03840(10)
  0.16120(10)
  0.0460(4)
  C11 0.1438(3) 0.01750(10)
  0.17410(10)
  0.0442(4)
  C12 0.3109(2) 0.04310(10)
  -0.04410(10)
  0.0390(4)
  C13 0.5168(3) 0.11790(10)
  -0.0504(2) 0.0615(6)
  C14 -0.2458(3) 0.18730(10)
  0.11230(10)
  0.0473(4)
  C15 -0.2714(3) 0.1730(2) 0.18800(10)
  0.0733(7)
  H5 -0.132(2) 0.2170(10)
  -0.1620(10)
  0.0418(5)
  H6 -0.050(3) 0.1870(10)
  -0.2700(10)
  0.0558(5)
  H7 0.154(2) 0.1150(10)
  -0.2870(10)
  0.0520(5)
  H8 0.274(2) 0.0690(10)
  -0.1900(10)
  0.0482(5)
  H21 0.086(2) 0.2180(10)
  0.1080(10)
  0.0456(5)
  H22 0.018(2) 0.1630(10)
  0.1570(10)
  0.0456(5)
  H101 0.346(3) 0.0450(10)
  0.2030(10)
  0.0583(6)
  H102 0.346(2) 0.0060(10)
  0.1340(10)
  0.0507(5)
  H111 0.105(2) 0.0470(10)
  0.2100(10)
  0.0406(5)
  H112 0.138(2) -0.0300(10)
  0.1850(10)
  0.0469(5)
  H121 0.277(2) 0.0010(10)
  -0.0670(10)
  0.0368(4)
  H122 0.327(2) 0.0350(10)
  0.0050(10)
  0.0368(4)
  H131 0.602 0.127 -0.077 0.0735
  H132 0.457 0.159 -0.050 0.0735
  H133 0.543 0.106 -0.004 0.0735
  H141 -0.330 0.198 0.085 0.0583
  H151 -0.372 0.176 0.199 0.1014
  H152 -0.238 0.127 0.199 0.1014
  H153 -0.219 0.207 0.215 0.1014
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
  S1 0.0333(2) 0.0423(3) 0.0395(2) -0.0035(2) -0.0088(2) 0.0003(2)
  S2 0.0450(3) 0.0309(2) 0.0411(2) -0.0077(2) -0.0081(2) 0.0055(2)
  O1 0.0449(8) 0.0607(9) 0.0445(8) 0.0221(7) 0.0010(7) 0.0092(7)
  O2 0.0328(7) 0.0554(8) 0.0554(8) 0.0061(7) 0.0049(7) -0.0132(7)
  C1 0.0290(8) 0.0275(8) 0.0315(8) -0.0025(7) -0.0025(7) 0.0005(7)
  C2 0.0400(10)
  0.0339(9) 0.0298(8) 0.0019(8) 0.0005(8) -0.0018(8)
  C3 0.0379(9) 0.0306(8) 0.0351(9) 0.0063(8) 0.0034(8) -0.0002(8)
  C4 0.0336(9) 0.0301(8) 0.0369(9) 0.0028(8) 0.0010(8) 0.0018(8)
  C4a 0.0301(8) 0.0271(8) 0.0309(8) -0.0014(7) -0.0007(7) -0.0003(7)
  C5 0.0380(10)
  0.0369(9) 0.0362(9) 0.0010(9) -0.0028(8) 0.0027(8)
  C5a 0.0319(9) 0.0269(8) 0.0308(8) -0.0028(7) -0.0006(7) -0.0005(7)
  C6 0.0500(10)
  0.0450(10)
  0.0320(10)
  -0.0040(10)
  -0.0060(9) 0.0039(8)
  C7 0.0530(10)
  0.0520(10)
  0.0308(9) -0.0040(10)
  0.0056(9) -0.0047(9)
  C8 0.0410(10)
  0.0450(10)
  0.0380(10)
  0.0029(9) 0.0059(9) -0.0051(9)
  C8a 0.0328(9) 0.0315(8) 0.0317(8) -0.0038(8) 0.0009(8) -0.0019(7)
  N9 0.0288(7) 0.0313(7) 0.0328(7) 0.0027(6) -0.0004(6) -0.0027(6)
  C9a 0.0282(8) 0.0260(8) 0.0301(8) -0.0025(7) -0.0003(7) -0.0023(7)
  C10 0.0470(10)
  0.0470(10)
  0.0440(10)
  0.0110(10)
  -0.0085(9) 0.0059(9)
  C11 0.0540(10)
  0.0400(10)
  0.0380(10)
  0.0020(10)
  -0.0050(10)
  0.0092(9)
  C12 0.0350(9) 0.0366(9) 0.0450(10)
  0.0083(8) -0.0010(9) -0.0052(9)
  C13 0.0460(10)
  0.0610(10)
  0.077(2) -0.0070(10)
  0.0080(10)
  -0.0090(10)
  C14 0.0440(10)
  0.0530(10)
  0.0440(10)
  0.0120(10)
  0.0090(10)
  0.0070(10)
  C15 0.066(2) 0.100(2) 0.0530(10)
  0.021(2) 0.0220(10)
  0.0160(10)
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
  S1 C1 . . 1.856(2) yes
  S1 C10 . . 1.815(2) yes
  S2 C1 . . 1.832(2) yes
  S2 C11 . . 1.799(2) yes
  O1 C4 . . 1.224(2) yes
  O2 C12 . . 1.403(3) no
  O2 C13 . . 1.417(3) no
  C1 C2 . . 1.543(3) no
  C1 C9a . . 1.505(3) no
  C2 C3 . . 1.503(3) no
  C3 C4 . . 1.495(3) yes
  C3 C14 . . 1.325(3) no
  C4 C4a . . 1.449(3) yes
  C4a C5a . . 1.439(3) yes
  C4a C9a . . 1.384(2) yes
  C5 C5a . . 1.397(3) no
  C5 C6 . . 1.382(3) no
  C5a C8a . . 1.404(3) no
  C6 C7 . . 1.390(3) no
  C7 C8 . . 1.378(3) no
  C8 C8a . . 1.393(3) no
  C8a N9 . . 1.396(2) no
  N9 C9a . . 1.377(2) no
  N9 C12 . . 1.460(3) no
  C10 C11 . . 1.502(3) no
  C14 C15 . . 1.492(3) no
  C2 H21 . . 0.97(2) no
  C2 H22 . . 0.92(2) no
  C5 H5 . . 0.96(2) no
  C6 H6 . . 0.92(2) no
  C7 H7 . . 0.95(2) no
  C8 H8 . . 0.92(2) no
  C10 H101 . . 0.92(2) no
  C10 H102 . . 0.91(2) no
  C11 H111 . . 0.95(2) no
  C11 H112 . . 0.93(2) no
  C12 H121 . . 0.96(2) no
  C12 H122 . . 0.96(2) no
  C13 H131 . . 0.950 no
  C13 H132 . . 0.950 no
  C13 H133 . . 0.950 no
  C14 H141 . . 0.950 no
  C15 H151 . . 0.950 no
  C15 H152 . . 0.950 no
  C15 H153 . . 0.950 no
_cod_database_code 2008116