data_2012288
_journal_name_full  'Acta Crystallographica, Section C'
_journal_year  2001
_journal_volume  57
_journal_page_first  1313
_journal_page_last  1315
_publ_section_title
;
Diethyl 2-[cyano(toluene-4-sulfinyl)methylene]propanedioate and its Diels-Alder
adduct with cyclopentadiene
;
loop_
_publ_author_name
  "Toscano, Rub\'en A."
  "Hern\'andez-Ortega, Sim\'on"
  "Ortiz, Benjam\'in"
  "S\'anchez-Obreg\'on, Rub\'en"
  'Walls, Fernando'
  'Yuste, Francisco'
_chemical_name_common
;
3,3-Diethoxycarbonyl-2-(p-tolylsulfinyl)bicyclo[2.2.1]hept-
5-ene-2-carbonitrile
;
_chemical_formula_moiety  'C21 H23 N O5 S'
_chemical_formula_sum  'C21 H23 N O5 S'
_chemical_formula_weight  401.46
_symmetry_cell_setting  'Monoclinic'
_symmetry_space_group_name_H-M  'C c'
loop_
_symmetry_equiv_pos_as_xyz
  'x, y, z'
  'x, -y, z+1/2'
  'x+1/2, y+1/2, z'
  'x+1/2, -y+1/2, z+1/2'
_cell_length_a  8.4580(10)
_cell_length_b  15.137(2)
_cell_length_c  15.930(3)
_cell_angle_alpha  90
_cell_angle_beta  95.98(2)
_cell_angle_gamma  90
_cell_volume  2028.4(5)
_cell_formula_units_Z  4
_cell_measurement_temperature  293(2)
_exptl_crystal_density_diffrn  1.315
_diffrn_ambient_temperature  293(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
  S1  .2756(2)  .28889(15)  .30155(14)  .0502(6) Uani d . 1 . . S
  O1  .5745(6)  .4888(4)  .2581(4)  .0500(15) Uani d . 1 . . O
  O2  .7800(7)  .4779(4)  .3604(4)  .0584(17) Uani d . 1 . . O
  O3  .7475(7)  .3444(4)  .1938(4)  .0611(17) Uani d . 1 . . O
  O4  .5284(7)  .2582(4)  .1959(4)  .0611(18) Uani d . 1 . . O
  O5  .1643(6)  .2887(4)  .3700(4)  .0703(19) Uani d . 1 . . O
  N1  .3755(10)  .4899(6)  .4233(5)  .075(3) Uani d . 1 . . N
  C1  .7407(10)  .2922(6)  .3787(5)  .055(2) Uani d . 1 . . C
  H1  .8543  .3030  .3760  .066 Uiso d R 1 . . H
  C2  .6220(9)  .3492(5)  .3166(5)  .041(2) Uani d . 1 . . C
  C3  .4566(9)  .3383(5)  .3598(5)  .042(2) Uani d . 1 . . C
  C4  .5113(12)  .2750(6)  .4380(5)  .063(3) Uani d . 1 . . C
  H4  .4387  .2727  .4821  .076 Uiso d R 1 . . H
  C5  .5540(12)  .1867(6)  .4027(7)  .068(3) Uani d . 1 . . C
  H5  .4963  .1346  .4049  .081 Uiso d R 1 . . H
  C6  .6805(13)  .1964(6)  .3668(6)  .072(3) Uani d . 1 . . C
  H6  .7326  .1527  .3393  .087 Uiso d R 1 . . H
  C7  .6781(10)  .3130(7)  .4655(5)  .062(3) Uani d . 1 . . C
  H7A  .7337  .2809  .5124  .074 Uiso d R 1 . . H
  H7B  .6757  .3756  .4783  .074 Uiso d R 1 . . H
  C8  .4104(10)  .4224(5)  .3947(5)  .042(2) Uani d . 1 . . C
  C9  .6725(9)  .4469(5)  .3154(5)  .0401(19) Uani d . 1 . . C
  C10  .6204(11)  .3108(6)  .2276(5)  .048(2) Uani d . 1 . . C
  C11  .6047(12)  .5826(5)  .2527(7)  .068(3) Uani d . 1 . . C
  H11A  .7147  .5940  .2440  .082 Uiso d R 1 . . H
  H11B  .5826  .6111  .3048  .082 Uiso d R 1 . . H
  C12  .4915(14)  .6182(6)  .1785(8)  .110(5) Uani d . 1 . . C
  H12A  .3832  .6053  .1870  .132 Uiso d R 1 . . H
  H12B  .5167  .5911  .1271  .132 Uiso d R 1 . . H
  H12C  .5051  .6810  .1749  .132 Uiso d R 1 . . H
  C13  .7615(13)  .3213(6)  .1040(5)  .075(3) Uani d . 1 . . C
  H13A  .8724  .3254  .0939  .090 Uiso d R 1 . . H
  H13B  .7279  .2606  .0941  .090 Uiso d R 1 . . H
  C14  .6730(15)  .3782(8)  .0456(6)  .108(5) Uani d . 1 . . C
  H14A  .7355  .3954  .0013  .130 Uiso d R 1 . . H
  H14B  .6415  .4299  .0745  .130 Uiso d R 1 . . H
  H14C  .5802  .3470  .0218  .130 Uiso d R 1 . . H
  C15  .2076(10)  .3775(5)  .2309(5)  .044(2) Uani d . 1 . . C
  C16  .1144(10)  .4442(6)  .2573(5)  .048(2) Uani d . 1 . . C
  H16  .0870  .4457  .3123  .058 Uiso d R 1 . . H
  C17  .0567(10)  .5095(6)  .2002(6)  .056(2) Uani d . 1 . . C
  H17  -.0051  .5552  .2182  .067 Uiso d R 1 . . H
  C18  .0922(11)  .5078(6)  .1176(6)  .057(2) Uani d . 1 . . C
  C19  .1821(10)  .4408(6)  .0907(5)  .056(2) Uani d . 1 . . C
  H19  .2064  .4399  .0351  .067 Uiso d R 1 . . H
  C20  .2398(10)  .3722(6)  .1462(5)  .051(2) Uani d . 1 . . C
  H20  .2961  .3250  .1268  .061 Uiso d R 1 . . H
  C21  .0345(12)  .5785(7)  .0549(6)  .080(3) Uani d . 1 . . C
  H21A  .0859  .6338  .0692  .095 Uiso d R 1 . . H
  H21B  -.0782  .5850  .0557  .095 Uiso d R 1 . . H
  H21C  .0571  .5608  -.0005  .095 Uiso d 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
  S1  .0501(13)  .0473(13)  .0544(15)  -.0108(12)  .0104(11)  .0012(13)
  O1  .037(3)  .044(4)  .066(4)  .000(3)  -.008(3)  .006(3)
  O2  .054(4)  .057(4)  .062(4)  -.004(3)  -.006(3)  -.006(3)
  O3  .055(4)  .075(5)  .056(4)  -.007(3)  .021(3)  .000(4)
  O4  .062(4)  .054(4)  .069(4)  -.013(3)  .016(3)  -.025(3)
  O5  .047(4)  .091(5)  .074(5)  -.030(4)  .016(3)  .014(4)
  N1  .089(7)  .072(6)  .068(6)  .003(5)  .025(5)  -.022(5)
  C1  .040(5)  .056(6)  .068(7)  -.002(4)  -.003(4)  .025(5)
  C2  .049(5)  .031(4)  .045(5)  .007(4)  .009(4)  .002(4)
  C3  .037(4)  .047(5)  .041(5)  .002(4)  -.005(4)  .005(4)
  C4  .083(7)  .062(7)  .047(6)  -.026(6)  .013(5)  .004(5)
  C5  .071(7)  .059(7)  .075(7)  .017(5)  .015(6)  .035(6)
  C6  .100(9)  .050(6)  .066(7)  .026(6)  .002(6)  .013(5)
  C7  .068(6)  .068(7)  .049(6)  .009(5)  .009(5)  .015(5)
  C8  .054(5)  .030(4)  .045(5)  -.007(4)  .019(4)  .002(4)
  C9  .042(5)  .041(5)  .038(5)  -.011(4)  .009(4)  -.005(4)
  C10  .054(5)  .039(5)  .054(6)  .020(4)  .015(5)  .012(4)
  C11  .060(6)  .037(6)  .104(9)  .003(5)  -.006(6)  .006(6)
  C12  .111(10)  .044(6)  .172(14)  -.023(6)  .002(9)  .037(8)
  C13  .076(7)  .104(9)  .050(6)  -.004(6)  .033(5)  -.012(6)
  C14  .126(11)  .149(13)  .047(7)  .042(10)  -.005(7)  .016(8)
  C15  .047(5)  .044(5)  .041(5)  -.005(4)  .005(4)  .001(4)
  C16  .041(5)  .055(6)  .047(6)  .003(4)  .003(4)  -.003(5)
  C17  .045(5)  .060(6)  .065(6)  .004(5)  .012(5)  -.011(5)
  C18  .061(6)  .053(6)  .055(6)  -.014(5)  -.002(5)  -.006(5)
  C19  .052(6)  .076(7)  .040(5)  -.011(5)  .001(5)  -.004(5)
  C20  .046(5)  .056(6)  .050(6)  .004(4)  .001(4)  -.018(5)
  C21  .075(7)  .085(7)  .073(7)  .023(6)  -.022(6)  .006(6)
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
  S1 O5 . 1.513(6) ?
  S1 C15 . 1.807(8) Y
  S1 C3 . 1.863(8) Y
  O1 C9 . 1.328(9) ?
  O1 C11 . 1.446(9) ?
  O2 C9 . 1.194(8) ?
  O3 C10 . 1.351(10) ?
  O3 C13 . 1.490(10) ?
  O4 C10 . 1.188(10) ?
  N1 C8 . 1.170(10) ?
  C1 C6 . 1.541(12) ?
  C1 C7 . 1.565(12) ?
  C1 C2 . 1.588(10) ?
  C2 C10 . 1.532(11) ?
  C2 C9 . 1.540(10) ?
  C2 C3 . 1.630(10) Y
  C3 C8 . 1.458(11) ?
  C3 C4 . 1.602(11) ?
  C4 C5 . 1.508(12) ?
  C4 C7 . 1.545(12) ?
  C5 C6 . 1.274(12) Y
  C11 C12 . 1.539(13) ?
  C13 C14 . 1.422(13) ?
  C15 C16 . 1.374(11) ?
  C15 C20 . 1.405(10) ?
  C16 C17 . 1.396(11) ?
  C17 C18 . 1.380(11) ?
  C18 C19 . 1.365(12) ?
  C18 C21 . 1.509(12) ?
  C19 C20 . 1.417(11) ?
  C1 H1 .  .98 ?
  C4 H4 .  .98 ?
  C5 H5 .  .93 ?
  C6 H6 .  .93 ?
  C7 H7A .  .97 ?
  C7 H7B .  .97 ?
  C11 H11A .  .97 ?
  C11 H11B .  .97 ?
  C12 H12A .  .96 ?
  C12 H12B .  .96 ?
  C12 H12C .  .96 ?
  C13 H13A .  .97 ?
  C13 H13B .  .97 ?
  C14 H14A .  .96 ?
  C14 H14B .  .96 ?
  C14 H14C .  .96 ?
  C16 H16 .  .93 ?
  C17 H17 .  .93 ?
  C19 H19 .  .93 ?
  C20 H20 .  .93 ?
  C21 H21A .  .96 ?
  C21 H21B .  .96 ?
  C21 H21C .  .96 ?