data_2011117 _journal_name_full 'Acta Crystallographica, Section C' _journal_year 2000 _journal_volume 56 _journal_page_first 843 _journal_page_last 845 _publ_section_title ; Hydrogen bonds and C-H...O interactions in the enol tautomer of 4-(phenylsulfonyl)-spiro[cyclopentane-1,9'-[9H]fluorene]-2,3-dione ; loop_ _publ_author_name 'Gerkin, Roger E.' _chemical_name_common ; enol tautomer of 4-(phenylsulfonyl)-spiro[cyclopentane-1, 9'-[9H]fluorene]-2, 3- dione ; _chemical_formula_moiety 'C23 H16 O4 S ' _chemical_formula_sum 'C23 H16 O4 S' _chemical_formula_weight 388.44 _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' '1/2-x,1/2+y,1/2-z' ' -x, -y, -z' '1/2+x,1/2-y,1/2+z' _cell_length_a 8.4780(10) _cell_length_b 10.4060(10) _cell_length_c 21.3360(10) _cell_angle_alpha 90 _cell_angle_beta 95.701(9) _cell_angle_gamma 90 _cell_volume 1873.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 296 _exptl_crystal_density_diffrn 1.377 _diffrn_ambient_temperature 296 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_calc_attached_atom _atom_site_refinement_flags _atom_site_occupancy S1 .17658(5) .18786(5) .55526(2) .04190(10) Uani d ? . 1.000 O1 .0276(2) -.07170(10) .61194(7) .0575(5) Uani d ? . 1.000 O2 .1509(2) .07500(10) .51599(6) .0618(5) Uani d ? . 1.000 O3 .08700(10) .30210(10) .53870(6) .0584(4) Uani d ? . 1.000 O4 .0327(2) -.06930(10) .74399(6) .0606(5) Uani d ? . 1.000 C1 .4418(2) .0642(2) .77549(9) .0491(6) Uani d ? . 1.000 C2 .5588(2) .0450(2) .82510(10) .0599(7) Uani d ? . 1.000 C3 .5309(3) .0739(2) .88600(10) .0613(7) Uani d ? . 1.000 C4 .3885(2) .1241(2) .89966(9) .0520(6) Uani d ? . 1.000 C5 .0316(3) .2487(2) .89869(9) .0554(7) Uani d ? . 1.000 C6 -.1195(3) .2971(2) .88420(10) .0633(7) Uani d ? . 1.000 C7 -.1888(2) .2992(2) .82330(10) .0581(7) Uani d ? . 1.000 C8 -.1082(2) .2527(2) .77468(9) .0486(6) Uani d ? . 1.000 C9 .1518(2) .1454(2) .74426(7) .0346(5) Uani d ? . 1.000 C10 .2985(2) .1146(2) .78904(8) .0356(5) Uani d ? . 1.000 C11 .2713(2) .1456(2) .85065(8) .0384(5) Uani d ? . 1.000 C12 .1132(2) .2013(2) .85033(8) .0393(5) Uani d ? . 1.000 C13 .0428(2) .2044(2) .78847(7) .0360(5) Uani d ? . 1.000 C14 .0808(2) .0201(2) .71580(8) .0382(5) Uani d ? . 1.000 C15 .0837(2) .0283(2) .64629(8) .0372(5) Uani d ? . 1.000 C16 .1443(2) .1410(2) .63130(7) .0329(5) Uani d ? . 1.000 C17 .1850(2) .2282(2) .68670(8) .0403(5) Uani d ? . 1.000 C18 .3794(2) .2269(2) .56277(8) .0378(5) Uani d ? . 1.000 C19 .4904(2) .1303(2) .56594(9) .0524(6) Uani d ? . 1.000 C20 .6499(2) .1627(2) .57450(10) .0635(7) Uani d ? . 1.000 C21 .6948(2) .2891(2) .58030(10) .0641(7) Uani d ? . 1.000 C22 .5830(3) .3844(2) .57750(10) .0691(8) Uani d ? . 1.000 C23 .4233(2) .3539(2) .56880(10) .0542(6) Uani d ? . 1.000 H1 .4606 .0425 .7322 .059 Uiso c ? . 1.000 H1O1 .039(3) -.059(2) .5710(10) .110(10) Uiso d ? . 1.000 H2 .6622 .0105 .8166 .072 Uiso c ? . 1.000 H3 .6144 .0584 .9203 .074 Uiso c ? . 1.000 H4 .3700 .1444 .9432 .062 Uiso c ? . 1.000 H5 .0802 .2478 .9423 .067 Uiso c ? . 1.000 H6 -.1781 .3306 .9180 .076 Uiso c ? . 1.000 H7 -.2961 .3338 .8142 .070 Uiso c ? . 1.000 H8 -.1577 .2540 .7312 .058 Uiso c ? . 1.000 H17B .1178 .3051 .6837 .048 Uiso c ? . 1.000 H17A .2966 .2539 .6894 .048 Uiso c ? . 1.000 H19 .4575 .0401 .5622 .063 Uiso c ? . 1.000 H20 .7307 .0951 .5764 .076 Uiso c ? . 1.000 H21 .8076 .3113 .5864 .077 Uiso c ? . 1.000 H22 .6160 .4745 .5817 .083 Uiso c ? . 1.000 H23 .3429 .4218 .5670 .065 Uiso c ? . 1.000 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 .0340(2) .0635(3) .0276(2) -.0106(2) .0011(2) -.0022(2) O1 .0740(10) .0521(9) .0457(8) -.0240(8) .0036(8) -.0164(7) O2 .0617(9) .0860(10) .0385(7) -.0310(8) .0077(7) -.0234(7) O3 .0416(7) .0830(10) .0485(8) .0071(8) -.0041(6) .0234(8) O4 .0800(10) .0500(9) .0493(8) -.0252(8) -.0052(7) .0105(7) C1 .0450(10) .0440(10) .0590(10) -.0020(10) .0080(10) -.0060(10) C2 .0380(10) .0460(10) .094(2) .0030(10) -.0030(10) -.0040(10) C3 .0520(10) .0510(10) .075(2) .0020(10) -.0240(10) -.0020(10) C4 .0570(10) .0510(10) .0440(10) .0020(10) -.0140(10) -.0020(10) C5 .0660(10) .0640(10) .0370(10) .0040(10) .0090(10) -.0050(10) C6 .067(2) .066(2) .0610(10) .0100(10) .0260(10) -.0030(10) C7 .0440(10) .0570(10) .075(2) .0100(10) .0130(10) .0080(10) C8 .0430(10) .0520(10) .0490(10) .0020(10) -.0021(9) .0070(10) C9 .0400(10) .0350(10) .0285(8) -.0041(8) .0006(7) -.0007(7) C10 .0351(9) .0310(10) .0397(9) -.0046(8) .0000(8) -.0010(8) C11 .0430(10) .0340(10) .0360(9) -.0038(8) -.0048(8) -.0004(8) C12 .0430(10) .0410(10) .0335(9) -.0022(9) .0028(8) .0005(8) C13 .0383(9) .0360(10) .0332(9) -.0012(8) .0021(7) .0032(8) C14 .0380(10) .0380(10) .0370(10) -.0037(8) -.0029(8) .0023(8) C15 .0360(10) .0400(10) .0354(9) -.0038(8) .0005(8) -.0067(8) C16 .0308(9) .0410(10) .0266(8) -.0023(8) .0022(7) -.0025(7) C17 .0510(10) .0380(10) .0318(9) -.0057(9) .0044(8) -.0020(8) C18 .0313(9) .0520(10) .0308(9) -.0057(9) .0057(7) -.0052(8) C19 .0450(10) .0500(10) .0620(10) -.0020(10) .0070(10) -.0080(10) C20 .0400(10) .070(2) .080(2) .0090(10) .0040(10) -.0090(10) C21 .0360(10) .083(2) .074(2) -.0110(10) .0040(10) -.0120(10) C22 .0490(10) .0590(10) .099(2) -.0180(10) .0060(10) -.0120(10) C23 .0420(10) .0500(10) .0710(10) -.0030(10) .0060(10) -.0070(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 O2 . . 1.4462(13) yes S1 O3 . . 1.4358(14) yes S1 C16 . . 1.742(2) yes S1 C18 . . 1.759(2) yes O1 C15 . . 1.333(2) yes O1 H1O1 . . .90(2) no O4 C14 . . 1.201(2) yes C1 C2 . . 1.391(3) no C1 C10 . . 1.380(2) no C1 H1 . . .98 no C2 C3 . . 1.377(3) no C2 H2 . . .98 no C3 C4 . . 1.373(3) no C3 H3 . . .98 no C4 C11 . . 1.387(2) no C4 H4 . . .98 no C5 C6 . . 1.383(3) no C5 C12 . . 1.389(2) no C5 H5 . . .98 no C6 C7 . . 1.371(3) no C6 H6 . . .98 no C7 C8 . . 1.385(3) no C7 H7 . . .98 no C8 C13 . . 1.380(2) no C8 H8 . . .98 no C9 C10 . . 1.525(2) no C9 C13 . . 1.515(2) no C9 C14 . . 1.536(2) yes C9 C17 . . 1.549(2) yes C10 C11 . . 1.395(2) no C11 C12 . . 1.460(2) no C12 C13 . . 1.394(2) no C14 C15 . . 1.488(2) yes C15 C16 . . 1.332(2) yes C16 C17 . . 1.503(2) yes C17 H17B . . .98 no C17 H17A . . .98 no C18 C19 . . 1.374(2) no C18 C23 . . 1.376(2) no C19 C20 . . 1.388(3) no C19 H19 . . .98 no C20 C21 . . 1.371(3) no C20 H20 . . .98 no C21 C22 . . 1.369(3) no C21 H21 . . .98 no C22 C23 . . 1.385(3) no C22 H22 . . .98 no C23 H23 . . .98 no