#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/11/2011117.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2011117 loop_ _publ_author_name 'Gerkin, Roger E.' _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 ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 843 _journal_page_last 845 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C23 H16 O4 S ' _chemical_formula_sum 'C23 H16 O4 S' _chemical_formula_weight 388.44 _chemical_name_common ;enol tautomer of 4-(phenylsulfonyl)-spiro[cyclopentane-1, 9'-[9H]fluorene]-2, 3- dione ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 95.701(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.4780(10) _cell_length_b 10.4060(10) _cell_length_c 21.3360(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 296 _cell_measurement_theta_max 17.5 _cell_measurement_theta_min 16.1 _cell_volume 1873.0(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1988) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'TEXSAN and PLATON (Spek, 1990)' _computing_structure_refinement TEXSAN _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 296 _diffrn_measurement_device_type AFC5S _diffrn_measurement_method 'omega scans ' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .010 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 4618 _diffrn_reflns_theta_max 27.55 _diffrn_reflns_theta_min 2.8 _diffrn_standards_decay_% -1.8 _diffrn_standards_interval_count 150 _diffrn_standards_number 6 _exptl_absorpt_coefficient_mu .200 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.377 _exptl_crystal_description 'cut plate' _exptl_crystal_F_000 808 _exptl_crystal_size_max .42 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .27 _refine_diff_density_max .39 _refine_diff_density_min -.47 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.44 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 257 _refine_ls_number_reflns 4331 _refine_ls_R_factor_gt .046 _refine_ls_shift/su_max .001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_scheme 'w = 1/[\s^2^~cs~ + (0.012I)^2^]' _refine_ls_wR_factor_ref .083 _reflns_number_gt 3246 _reflns_number_total 4333 _reflns_threshold_expression 'I > 2.0\s~I~' _[local]_cod_data_source_file fr1267.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/n' _cod_original_cell_volume 1873.2(4) _cod_database_code 2011117 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 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 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart, Davidson & Simpson (1965)' C .003 .002 'Creagh & McAuley (1992)' O .011 .006 'Creagh & McAuley (1992)' S .125 .123 'Creagh & McAuley (1992)' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag O2 S1 O3 118.96(8) yes O2 S1 C16 106.50(8) yes O2 S1 C18 109.26(8) yes O3 S1 C16 109.44(8) yes O3 S1 C18 108.63(9) yes C16 S1 C18 102.85(8) yes C15 O1 H1O1 111(2) no C2 C1 C10 118.1(2) no C2 C1 H1 120.9 no C10 C1 H1 120.9 no C1 C2 C3 120.6(2) no C1 C2 H2 119.7 no C3 C2 H2 119.7 no C2 C3 C4 121.4(2) no C2 C3 H3 119.3 no C4 C3 H3 119.3 no C3 C4 C11 118.7(2) no C3 C4 H4 120.7 no C11 C4 H4 120.7 no C6 C5 C12 118.8(2) no C6 C5 H5 120.6 no C12 C5 H5 120.6 no C5 C6 C7 121.2(2) no C5 C6 H6 119.4 no C7 C6 H6 119.4 no C6 C7 C8 120.5(2) no C6 C7 H7 119.7 no C8 C7 H7 119.7 no C7 C8 C13 118.9(2) no C7 C8 H8 120.5 no C13 C8 H8 120.5 no C10 C9 C13 101.83(13) yes C10 C9 C14 109.41(14) yes C10 C9 C17 114.39(14) yes C13 C9 C14 110.53(14) yes C13 C9 C17 116.01(14) yes C14 C9 C17 104.70(13) yes C1 C10 C9 129.0(2) no C1 C10 C11 121.1(2) no C9 C10 C11 110.00(10) no C4 C11 C10 120.0(2) no C4 C11 C12 131.0(2) no C10 C11 C12 109.00(10) no C5 C12 C11 131.5(2) no C5 C12 C13 119.8(2) no C11 C12 C13 108.70(10) no C8 C13 C9 128.7(2) no C8 C13 C12 120.8(2) no C9 C13 C12 110.50(10) no O4 C14 C9 126.8(2) yes O4 C14 C15 125.7(2) yes C9 C14 C15 107.51(14) yes O1 C15 C14 117.6(2) yes O1 C15 C16 132.9(2) yes C14 C15 C16 109.53(15) yes S1 C16 C15 124.75(13) yes S1 C16 C17 121.25(13) yes C15 C16 C17 114.00(14) yes C9 C17 C16 104.02(14) yes C9 C17 H17B 110.8 no C9 C17 H17A 110.8 no C16 C17 H17B 110.8 no C16 C17 H17A 110.8 no H17B C17 H17A 109.5 no S1 C18 C19 119.60(10) no S1 C18 C23 118.90(10) no C19 C18 C23 121.4(2) no C18 C19 C20 118.8(2) no C18 C19 H19 120.6 no C20 C19 H19 120.6 no C19 C20 C21 120.2(2) no C19 C20 H20 119.9 no C21 C20 H20 119.9 no C20 C21 C22 120.4(2) no C20 C21 H21 119.8 no C22 C21 H21 119.8 no C21 C22 C23 120.2(2) no C21 C22 H22 119.9 no C23 C22 H22 119.9 no C18 C23 C22 119.0(2) no C18 C23 H23 120.5 no C22 C23 H23 120.5 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 H7 2.8146 2_446 no O1 O2 2.987(2) 3_556 no O1 C4 3.258(2) 2_546 no O1 C11 3.453(2) 2_546 no O1 C7 3.572(2) 2_446 no O2 H1O1 2.34(3) 3_556 no O2 H6 2.8357 4_554 no O2 H20 2.9011 3_656 no O2 O2 3.018(2) 3_556 no O3 H4 2.6652 4_454 no O3 H21 2.6716 1_455 no O3 H3 2.9433 4_454 no O3 C4 3.351(2) 4_454 no O3 C3 3.451(3) 2_556 no O3 C3 3.493(3) 4_454 no O3 C21 3.528(2) 1_455 no O3 C4 3.599(2) 2_556 no O4 H7 2.4674 2_446 no O4 H17A 2.6625 2_546 no O4 C7 3.407(2) 2_446 no O4 C17 3.413(2) 2_546 no C1 H17B 2.8929 2_546 no C2 H17B 2.9078 2_546 no C2 C7 3.405(3) 1_655 no C4 H23 3.0107 2_546 no C6 H19 3.0460 2_556 no C20 H5 2.9727 4_554 no C21 H5 3.0310 4_554 no H3 H22 2.4506 2_646 no H3 H21 2.6624 2_646 no H1O1 O1 .90(2) . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O1 H1O1 O2 ? .90(2) 2.11(2) 2.836(2) 137(2) yes O1 H1O1 O2 3_556 .90(2) 2.34(3) 2.987(2) 129(2) yes C7 H7 O4 2_456 .98 2.47 3.407(3) 161 yes C17 H17A O4 2_556 .98 2.66 3.413(2) 134 yes C4 H4 O3 4_555 .98 2.67 3.351(2) 127 yes C21 H21 O3 1_655 .98 2.67 3.528(3) 146 yes C7 H7 O1 2_456 .98 2.81 3.572(3) 135 yes C6 H6 O2 4_455 .98 2.84 3.816(2) 179 yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag S1 C16 C15 O1 -3.2(3) no S1 C16 C15 C14 177.30(10) no S1 C16 C17 C9 -175.20(10) no S1 C18 C19 C20 -177.4(2) no S1 C18 C23 C22 177.2(2) no O1 C15 C14 O4 .3(3) no O1 C15 C14 C9 179.7(2) no O1 C15 C16 C17 177.0(2) no O2 S1 C16 C15 -9.5(2) no O2 S1 C16 C17 170.30(10) no O2 S1 C18 C19 -35.8(2) no O2 S1 C18 C23 147.7(2) no O3 S1 C16 C15 120.3(2) no O3 S1 C16 C17 -59.9(2) no O3 S1 C18 C19 -167.00(10) no O3 S1 C18 C23 16.5(2) no O4 C14 C9 C10 59.8(2) no O4 C14 C9 C13 -51.5(2) no O4 C14 C9 C17 -177.1(2) no O4 C14 C15 C16 179.8(2) no C1 C2 C3 C4 -1.0(3) no C1 C10 C9 C13 -176.8(2) no C1 C10 C9 C14 66.2(2) no C1 C10 C9 C17 -50.9(2) no C1 C10 C11 C4 -.9(3) no C1 C10 C11 C12 177.8(2) no C2 C1 C10 C9 179.8(2) no C2 C1 C10 C11 .0(3) no C2 C3 C4 C11 .0(3) no C3 C2 C1 C10 .9(3) no C3 C4 C11 C10 .9(3) no C3 C4 C11 C12 -177.5(2) no C4 C11 C10 C9 179.2(2) no C4 C11 C12 C5 -.6(4) no C4 C11 C12 C13 178.6(2) no C5 C6 C7 C8 -.1(4) no C5 C12 C11 C10 -179.1(2) no C5 C12 C13 C8 -.8(3) no C5 C12 C13 C9 -178.8(2) no C6 C5 C12 C11 179.7(2) no C6 C5 C12 C13 .6(3) no C6 C7 C8 C13 -.1(3) no C7 C6 C5 C12 -.1(3) no C7 C8 C13 C9 178.2(2) no C7 C8 C13 C12 .5(3) no C8 C13 C9 C10 179.2(2) no C8 C13 C9 C14 -64.6(2) no C8 C13 C9 C17 54.4(3) no C8 C13 C12 C11 179.9(2) no C9 C10 C11 C12 -2.0(2) no C9 C13 C12 C11 1.9(2) no C9 C14 C15 C16 -.8(2) no C9 C17 C16 C15 4.6(2) no C10 C9 C13 C12 -2.9(2) no C10 C9 C14 C15 -119.5(2) no C10 C9 C17 C16 115.1(2) no C10 C11 C12 C13 .1(2) no C11 C10 C9 C13 3.0(2) no C11 C10 C9 C14 -114.0(2) no C11 C10 C9 C17 128.9(2) no C12 C13 C9 C14 113.2(2) no C12 C13 C9 C17 -127.8(2) no C13 C9 C14 C15 129.10(10) no C13 C9 C17 C16 -126.80(10) no C14 C9 C17 C16 -4.7(2) no C14 C15 C16 C17 -2.5(2) no C15 C14 C9 C17 3.5(2) no C15 C16 S1 C18 -124.3(2) no C16 S1 C18 C19 77.0(2) no C16 S1 C18 C23 -99.4(2) no C17 C16 S1 C18 55.5(2) no C18 C19 C20 C21 .7(3) no C18 C23 C22 C21 -.3(3) no C19 C18 C23 C22 .8(3) no C19 C20 C21 C22 -.2(4) no C20 C19 C18 C23 -1.0(3) no C20 C21 C22 C23 .0(4) no