#------------------------------------------------------------------------------
#$Date: 2008-01-26 13:05:32 +0000 (Sat, 26 Jan 2008) $
#$Revision: 19 $
#$URL: svn://www.crystallography.net/cod/cif/2/2006207.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_2006207
_journal_name_full 'Acta Crystallographica'
_journal_year 1997
_journal_volume C53
_journal_page_first 786
_journal_page_last 787
_publ_section_title
;
 2,13-Dithia[3]orthocyclo[3](2,3)naphthalenophane
;
loop_
_publ_author_name
 'Jones, Peter G.'
 "Ku\'s, Piotr"
_chemical_formula_sum 'C20 H18 S2'
_chemical_formula_weight 322.46
_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 10.646(3)
_cell_length_b 11.286(3)
_cell_length_c 14.205(4)
_cell_angle_alpha 78.20(2)
_cell_angle_beta 80.64(2)
_cell_angle_gamma 71.77(2)
_cell_volume 1577.9(8)
_cell_formula_units_Z 4
_cell_measurement_temperature 143(2)
_exptl_crystal_density_diffrn 1.357
_diffrn_ambient_temperature 143(2)
_refine_ls_R_factor_obs  .0397
_refine_ls_wR_factor_obs  .0916
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_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_group
_atom_site_type_symbol
 C1  .0625(2)  .7744(2)  .37938(17)  .0310(5) Uani d . 1 . C
 H1A  -.0194  .7667  .4212  .037 Uiso calc R 1 . H
 H1B  .0917  .7046  .3411  .037 Uiso calc R 1 . H
 S2  .02374(6)  .92429(6)  .29699(4)  .03095(16) Uani d . 1 . S
 C3  .1834(2)  .9186(2)  .22787(17)  .0301(5) Uani d . 1 . C
 H3A  .1826 1.0061  .1982  .036 Uiso calc R 1 . H
 H3B  .2522  .8872  .2735  .036 Uiso calc R 1 . H
 C4  .2256(2)  .8381(2)  .14839(16)  .0262(5) Uani d . 1 . C
 C5  .1350(2)  .8446(2)  .08750(16)  .0278(5) Uani d . 1 . C
 H5  .0450  .8919  .1009  .033 Uiso calc R 1 . H
 C5A  .1709(2)  .7833(2)  .00569(16)  .0274(5) Uani d . 1 . C
 C6  .0774(2)  .7916(2)  -.05760(17)  .0337(6) Uani d . 1 . C
 H6  -.0127  .8396  -.0452  .040 Uiso calc R 1 . H
 C7  .1155(3)  .7314(3)  -.13625(18)  .0401(6) Uani d . 1 . C
 H7  .0522  .7385  -.1788  .048 Uiso calc R 1 . H
 C8  .2487(3)  .6585(2)  -.15443(18)  .0390(6) Uani d . 1 . C
 H8  .2743  .6156  -.2086  .047 Uiso calc R 1 . H
 C9  .3405(3)  .6490(2)  -.09512(17)  .0321(5) Uani d . 1 . C
 H9  .4299  .6001  -.1087  .039 Uiso calc R 1 . H
 C9A  .3053(2)  .7111(2)  -.01339(16)  .0262(5) Uani d . 1 . C
 C10  .3963(2)  .7046(2)  .05039(16)  .0272(5) Uani d . 1 . C
 H10  .4864  .6570  .0379  .033 Uiso calc R 1 . H
 C11  .3602(2)  .7645(2)  .13012(16)  .0255(5) Uani d . 1 . C
 C12  .4662(2)  .7505(2)  .19408(17)  .0308(5) Uani d . 1 . C
 H12A  .4363  .8208  .2319  .037 Uiso calc R 1 . H
 H12B  .5484  .7582  .1525  .037 Uiso calc R 1 . H
 S13  .50509(6)  .60161(6)  .27737(4)  .03045(16) Uani d . 1 . S
 C14  .3461(2)  .6050(2)  .34663(16)  .0296(5) Uani d . 1 . C
 H14A  .2774  .6346  .3010  .035 Uiso calc R 1 . H
 H14B  .3487  .5172  .3766  .035 Uiso calc R 1 . H
 C15  .3014(2)  .6861(2)  .42571(16)  .0274(5) Uani d . 1 . C
 C16  .3935(3)  .6803(2)  .48764(17)  .0351(6) Uani d . 1 . C
 H16  .4833  .6313  .4760  .042 Uiso calc R 1 . H
 C17  .3566(3)  .7447(3)  .56554(18)  .0417(6) Uani d . 1 . C
 H17  .4206  .7401  .6066  .050 Uiso calc R 1 . H
 C18  .2255(3)  .8159(2)  .58328(18)  .0385(6) Uani d . 1 . C
 H18  .1990  .8592  .6373  .046 Uiso calc R 1 . H
 C19  .1341(3)  .8237(2)  .52230(17)  .0324(6) Uani d . 1 . C
 H19  .0448  .8737  .5344  .039 Uiso calc R 1 . H
 C20  .1694(2)  .7597(2)  .44275(16)  .0282(5) Uani d . 1 . C
 C1'  .2699(2)  .0795(2)  .38326(17)  .0320(5) Uani d . 1 . C
 H1'1  .2026  .1066  .3366  .038 Uiso calc R 1 . H
 H1'2  .2560  .0037  .4277  .038 Uiso calc R 1 . H
 S2'  .43451(6)  .03775(6)  .31786(4)  .03243(16) Uani d . 1 . S
 C3'  .4360(3)  .1851(2)  .23969(17)  .0346(6) Uani d . 1 . C
 H3'1  .4030  .2535  .2793  .042 Uiso calc R 1 . H
 H3'2  .5294  .1808  .2146  .042 Uiso calc R 1 . H
 C4'  .3552(2)  .2217(2)  .15450(16)  .0267(5) Uani d . 1 . C
 C5'  .3622(2)  .1326(2)  .09905(16)  .0262(5) Uani d . 1 . C
 H5'  .4118  .0475  .1190  .031 Uiso calc R 1 . H
 C5A'  .2992(2)  .1621(2)  .01424(15)  .0248(5) Uani d . 1 . C
 C6'  .3052(2)  .0706(2)  -.04316(16)  .0295(5) Uani d . 1 . C
 H6'  .3521  -.0156  -.0237  .035 Uiso calc R 1 . H
 C7'  .2441(2)  .1055(2)  -.12588(17)  .0324(5) Uani d . 1 . C
 H7'  .2485  .0432  -.1633  .039 Uiso calc R 1 . H
 C8'  .1747(2)  .2327(2)  -.15666(17)  .0342(6) Uani d . 1 . C
 H8'  .1339  .2559  -.2151  .041 Uiso calc R 1 . H
 C9'  .1658(2)  .3226(2)  -.10300(17)  .0321(5) Uani d . 1 . C
 H9'  .1181  .4080  -.1241  .038 Uiso calc R 1 . H
 C9A'  .2267(2)  .2905(2)  -.01643(16)  .0262(5) Uani d . 1 . C
 C10'  .2175(2)  .3800(2)  .04242(16)  .0288(5) Uani d . 1 . C
 H10'  .1674  .4652  .0234  .035 Uiso calc R 1 . H
 C11'  .2779(2)  .3492(2)  .12601(16)  .0278(5) Uani d . 1 . C
 C12'  .2571(3)  .4524(2)  .18504(17)  .0332(6) Uani d . 1 . C
 H12C  .2711  .5287  .1413  .040 Uiso calc R 1 . H
 H12D  .3246  .4242  .2316  .040 Uiso calc R 1 . H
 S13'  .09331(6)  .49385(6)  .25086(4)  .03331(16) Uani d . 1 . S
 C14'  .0902(2)  .3462(2)  .32814(17)  .0331(6) Uani d . 1 . C
 H14C  -.0034  .3512  .3531  .040 Uiso calc R 1 . H
 H14D  .1225  .2781  .2881  .040 Uiso calc R 1 . H
 C15'  .1711(2)  .3083(2)  .41332(16)  .0265(5) Uani d . 1 . C
 C16'  .1625(2)  .3991(2)  .47021(16)  .0295(5) Uani d . 1 . C
 H16'  .1114  .4840  .4515  .035 Uiso calc R 1 . H
 C17'  .2266(2)  .3677(2)  .55296(17)  .0345(6) Uani d . 1 . C
 H17'  .2189  .4305  .5908  .041 Uiso calc R 1 . H
 C18'  .3020(2)  .2445(3)  .58039(18)  .0362(6) Uani d . 1 . C
 H18'  .3459  .2219  .6373  .043 Uiso calc R 1 . H
 C19'  .3128(2)  .1542(2)  .52413(17)  .0326(6) Uani d . 1 . C
 H19'  .3651  .0698  .5430  .039 Uiso calc R 1 . H
 C20'  .2490(2)  .1840(2)  .44084(16)  .0275(5) 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
 C1  .0268(12)  .0325(13)  .0350(13)  -.0112(10)  .0018(10)  -.0086(10)
 S2  .0266(3)  .0320(3)  .0311(3)  -.0021(3)  .0002(2)  -.0108(3)
 C3  .0319(13)  .0298(13)  .0310(13)  -.0131(10)  .0015(10)  -.0077(10)
 C4  .0298(12)  .0237(12)  .0247(11)  -.0111(10)  .0022(9)  -.0022(9)
 C5  .0249(12)  .0293(12)  .0293(12)  -.0091(10)  .0029(10)  -.0074(10)
 C5A  .0292(12)  .0267(12)  .0269(12)  -.0105(10)  .0001(10)  -.0038(10)
 C6  .0299(13)  .0383(14)  .0324(13)  -.0089(11)  -.0036(10)  -.0060(11)
 C7  .0448(16)  .0466(16)  .0321(14)  -.0137(13)  -.0105(12)  -.0080(12)
 C8  .0498(16)  .0384(15)  .0301(13)  -.0124(13)  .0019(12)  -.0140(11)
 C9  .0360(14)  .0280(13)  .0296(13)  -.0082(11)  .0045(10)  -.0069(10)
 C9A  .0306(12)  .0212(11)  .0252(12)  -.0096(10)  .0033(9)  -.0017(9)
 C10  .0262(12)  .0231(12)  .0298(12)  -.0086(10)  .0023(10)  -.0010(10)
 C11  .0270(12)  .0226(11)  .0271(12)  -.0109(9)  -.0015(9)  .0006(9)
 C12  .0274(13)  .0320(13)  .0360(13)  -.0127(10)  -.0008(10)  -.0076(11)
 S13  .0251(3)  .0316(3)  .0305(3)  -.0009(2)  -.0014(2)  -.0084(2)
 C14  .0309(13)  .0301(13)  .0290(12)  -.0113(10)  .0010(10)  -.0070(10)
 C15  .0316(13)  .0261(12)  .0256(12)  -.0130(10)  .0024(10)  -.0034(9)
 C16  .0334(14)  .0379(14)  .0324(13)  -.0066(11)  -.0053(11)  -.0068(11)
 C17  .0481(17)  .0467(16)  .0326(14)  -.0117(13)  -.0103(12)  -.0101(12)
 C18  .0499(17)  .0369(14)  .0286(13)  -.0122(13)  .0015(12)  -.0101(11)
 C19  .0362(14)  .0286(13)  .0301(13)  -.0090(11)  .0046(10)  -.0065(10)
 C20  .0312(13)  .0248(12)  .0284(12)  -.0128(10)  .0026(10)  -.0012(10)
 C1'  .0397(14)  .0296(13)  .0302(13)  -.0155(11)  -.0028(11)  -.0045(10)
 S2'  .0362(3)  .0263(3)  .0296(3)  .0021(3)  -.0116(3)  -.0042(2)
 C3'  .0361(14)  .0423(15)  .0300(13)  -.0193(12)  -.0061(11)  -.0016(11)
 C4'  .0278(12)  .0318(13)  .0226(11)  -.0151(10)  -.0017(9)  .0001(9)
 C5'  .0243(12)  .0248(12)  .0266(12)  -.0070(9)  -.0005(9)  .0002(9)
 C5A'  .0233(11)  .0291(12)  .0213(11)  -.0102(10)  .0021(9)  -.0020(9)
 C6'  .0277(12)  .0300(13)  .0294(12)  -.0086(10)  .0021(10)  -.0055(10)
 C7'  .0333(13)  .0397(14)  .0278(12)  -.0143(11)  .0015(10)  -.0115(11)
 C8'  .0315(13)  .0452(15)  .0269(12)  -.0112(12)  -.0079(10)  -.0041(11)
 C9'  .0278(13)  .0344(13)  .0311(13)  -.0062(10)  -.0054(10)  -.0016(10)
 C9A'  .0240(12)  .0275(12)  .0262(12)  -.0086(10)  -.0007(9)  -.0023(9)
 C10'  .0288(13)  .0243(12)  .0311(12)  -.0069(10)  -.0010(10)  -.0023(10)
 C11'  .0300(12)  .0272(12)  .0281(12)  -.0138(10)  .0014(10)  -.0036(10)
 C12'  .0418(15)  .0300(13)  .0316(13)  -.0178(11)  -.0007(11)  -.0043(10)
 S13'  .0374(4)  .0241(3)  .0328(3)  .0024(3)  -.0109(3)  -.0041(2)
 C14'  .0327(13)  .0373(14)  .0310(13)  -.0137(11)  -.0048(10)  -.0027(11)
 C15'  .0239(12)  .0324(13)  .0259(12)  -.0143(10)  .0005(9)  -.0037(10)
 C16'  .0280(12)  .0271(12)  .0315(13)  -.0091(10)  .0020(10)  -.0026(10)
 C17'  .0367(14)  .0394(15)  .0315(13)  -.0145(12)  .0010(11)  -.0133(11)
 C18'  .0332(14)  .0473(16)  .0291(13)  -.0102(12)  -.0079(11)  -.0069(11)
 C19'  .0304(13)  .0322(13)  .0323(13)  -.0050(11)  -.0051(10)  -.0040(11)
 C20'  .0256(12)  .0295(12)  .0282(12)  -.0111(10)  .0006(9)  -.0047(10)
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
 C1 C20 . 1.512(3) y
 C1 S2 . 1.820(3) y
 S2 C3 . 1.809(2) y
 C3 C4 . 1.517(3) y
 C4 C5 . 1.373(3) ?
 C4 C11 . 1.426(3) y
 C5 C5A . 1.412(3) ?
 C5A C6 . 1.416(3) ?
 C5A C9A . 1.421(3) ?
 C6 C7 . 1.366(4) ?
 C7 C8 . 1.412(4) ?
 C8 C9 . 1.358(4) ?
 C9 C9A . 1.416(3) ?
 C9A C10 . 1.407(3) ?
 C10 C11 . 1.377(3) ?
 C11 C12 . 1.513(3) y
 C12 S13 . 1.818(3) y
 S13 C14 . 1.807(2) y
 C14 C15 . 1.516(3) y
 C15 C16 . 1.399(3) ?
 C15 C20 . 1.402(3) y
 C16 C17 . 1.384(4) ?
 C17 C18 . 1.387(4) ?
 C18 C19 . 1.377(4) ?
 C19 C20 . 1.402(3) ?
 C1' C20' . 1.511(3) y
 C1' S2' . 1.814(3) y
 S2' C3' . 1.804(3) y
 C3' C4' . 1.512(3) y
 C4' C5' . 1.377(3) ?
 C4' C11' . 1.429(3) y
 C5' C5A' . 1.404(3) ?
 C5A' C6' . 1.422(3) ?
 C5A' C9A' . 1.426(3) ?
 C6' C7' . 1.363(3) ?
 C7' C8' . 1.409(4) ?
 C8' C9' . 1.361(4) ?
 C9' C9A' . 1.412(3) ?
 C9A' C10' . 1.409(3) ?
 C10' C11' . 1.373(3) ?
 C11' C12' . 1.512(3) y
 C12' S13' . 1.809(3) y
 S13' C14' . 1.805(3) y
 C14' C15' . 1.512(3) y
 C15' C20' . 1.401(3) y
 C15' C16' . 1.402(3) ?
 C16' C17' . 1.383(3) ?
 C17' C18' . 1.382(4) ?
 C18' C19' . 1.386(4) ?
 C19' C20' . 1.389(3) ?