#------------------------------------------------------------------------------ #$Date: 2011-09-10 04:16:28 +0100 (Sat, 10 Sep 2011) $ #$Revision: 25271 $ #$URL: svn://www.crystallography.net/cod/cif/2/2200305.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_2200305 loop_ _publ_author_name 'Bruno, Giuseppe' 'Nicol\'o, Francesco' 'Rotondo, Archimede' 'Foti, Francesco' 'Risitano, Francesco' 'Grassi, Giovanni' 'Bilardo, Cristina' _publ_section_title ; 9-(4-Methylbenzylidene)-4,8-diphenyl-6-p-tolyl-2-oxa-3,7-diazaspiro[4.4]nona-3,7-dien-1-one ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o396 _journal_page_last o398 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C33 H26 N2 O2' _chemical_formula_moiety 'C33 H26 N2 O2' _chemical_formula_sum 'C33 H26 N2 O2' _chemical_formula_weight 482.56 _chemical_name_systematic ; 9-(4-Methyl-benzylidene)-4,8-diphenyl-6-p-tolyl-2-oxa- 3,7-diazaspiro[4.4]nona-3,7-dien-1-one ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90.00 _cell_angle_beta 97.143(12) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.909(3) _cell_length_b 18.502(7) _cell_length_c 13.092(4) _cell_measurement_reflns_used 28 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 12.48 _cell_measurement_theta_min 2.17 _cell_volume 2622.0(15) _computing_cell_refinement XSCANS _computing_data_collection 'XSCANS (Siemens, 1999)' _computing_data_reduction 'SHELXTL-Plus (Sheldrick, 1990)' _computing_molecular_graphics 'XPW (Siemens, 1996)' _computing_publication_material 'PARST97 (Nardelli, 1995) and SHELXL97' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _diffrn_ambient_temperature 298(2) _diffrn_measured_fraction_theta_full .000 _diffrn_measured_fraction_theta_max .998 _diffrn_measurement_device_type 'Siemens P4' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0321 _diffrn_reflns_av_sigmaI/netI .0770 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -1 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_k_min -1 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 5738 _diffrn_reflns_theta_full .50 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 1.88 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 97 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .076 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 1016 _exptl_crystal_size_max .46 _exptl_crystal_size_mid .27 _exptl_crystal_size_min .22 _refine_diff_density_max .209 _refine_diff_density_min -.203 _refine_ls_extinction_coef .0063(6) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.144 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 335 _refine_ls_number_reflns 4602 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.144 _refine_ls_R_factor_all .1629 _refine_ls_R_factor_gt .0493 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0278P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1260 _reflns_number_gt 1712 _reflns_number_total 4602 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na6057.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_cell_volume 2621.9(15) _cod_database_code 2200305 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_type_symbol C3 .8696(4) .23869(19) .2732(3) .0657(10) Uani d . 1 C O2 .9447(2) .20392(13) .23488(18) .0828(8) Uani d . 1 O C1 .8783(3) .27669(17) .3770(2) .0542(8) Uani d . 1 C C2 .7621(3) .31989(18) .3618(2) .0568(9) Uani d . 1 C N1 .6886(3) .30278(16) .2801(2) .0752(9) Uani d . 1 N O1 .7530(2) .25016(13) .22350(17) .0810(8) Uani d . 1 O C14 .7272(3) .38018(18) .4265(3) .0585(9) Uani d . 1 C C15 .6598(3) .4372(2) .3791(3) .0773(11) Uani d . 1 C H15 .6331 .4353 .3089 .093 Uiso calc R 1 H C16 .6323(4) .4968(2) .4353(4) .0946(14) Uani d . 1 C H16 .5887 .5352 .4025 .113 Uiso calc R 1 H C17 .6688(4) .4997(2) .5397(4) .0980(14) Uani d . 1 C H17 .6487 .5397 .5774 .118 Uiso calc R 1 H C18 .7351(4) .4437(2) .5881(3) .0891(12) Uani d . 1 C H18 .7592 .4455 .6587 .107 Uiso calc R 1 H C19 .7664(3) .38412(19) .5317(3) .0732(11) Uani d . 1 C H19 .8135 .3469 .5643 .088 Uiso calc R 1 H C4 .8801(3) .21671(17) .4665(2) .0591(9) Uani d . 1 C H4 .8351 .2367 .5203 .071 Uiso calc R 1 H N2 1.0105(3) .20973(15) .5103(2) .0646(8) Uani d . 1 N C5 1.0739(3) .26304(19) .4793(2) .0587(9) Uani d . 1 C C6 1.0018(3) .31331(19) .4075(2) .0563(9) Uani d . 1 C C7 .8206(3) .14485(19) .4336(2) .0609(9) Uani d . 1 C C8 .8888(3) .0855(2) .4104(2) .0710(10) Uani d . 1 C H8 .9743 .0889 .4148 .085 Uiso calc R 1 H C9 .8309(4) .0207(2) .3805(3) .0811(12) Uani d . 1 C H9 .8786 -.0186 .3653 .097 Uiso calc R 1 H C10 .7049(5) .0133(3) .3730(3) .0932(14) Uani d . 1 C C11 .6373(4) .0725(3) .3966(3) .1070(16) Uani d . 1 C H11 .5518 .0687 .3922 .128 Uiso calc R 1 H C12 .6935(4) .1377(2) .4267(3) .0927(13) Uani d . 1 C H12 .6455 .1768 .4424 .111 Uiso calc R 1 H C13 .6431(4) -.0589(2) .3402(3) .143(2) Uani d . 1 C H13A .5552 -.0542 .3379 .171 Uiso calc R 1 H H13B .6724 -.0957 .3890 .171 Uiso calc R 1 H H13C .6631 -.0719 .2733 .171 Uiso calc R 1 H C20 1.2067(3) .27094(17) .5154(3) .0611(9) Uani d . 1 C C21 1.2897(3) .29086(18) .4488(3) .0756(11) Uani d . 1 C H21 1.2612 .3009 .3804 .091 Uiso calc R 1 H C22 1.4142(4) .2960(2) .4825(4) .0928(13) Uani d . 1 C H22 1.4693 .3082 .4365 .111 Uiso calc R 1 H C23 1.4565(4) .2833(2) .5838(4) .1046(16) Uani d . 1 C H23 1.5404 .2877 .6067 .125 Uiso calc R 1 H C24 1.3756(4) .2639(2) .6521(4) .1035(15) Uani d . 1 C H24 1.4048 .2551 .7208 .124 Uiso calc R 1 H C25 1.2506(4) .25749(19) .6180(3) .0821(12) Uani d . 1 C H25 1.1959 .2442 .6638 .099 Uiso calc R 1 H C26 1.0358(3) .38088(18) .3855(2) .0609(9) Uani d . 1 C H26 1.1133 .3954 .4164 .073 Uiso calc R 1 H C27 .9665(3) .43470(19) .3192(3) .0589(9) Uani d . 1 C C28 .9031(3) .41793(18) .2233(3) .0675(10) Uani d . 1 C H28 .9081 .3714 .1974 .081 Uiso calc R 1 H C29 .8324(3) .4695(2) .1655(3) .0721(11) Uani d . 1 C H29 .7890 .4567 .1024 .087 Uiso calc R 1 H C30 .8260(3) .5397(2) .2010(3) .0688(10) Uani d . 1 C C31 .8929(3) .55711(19) .2943(3) .0741(11) Uani d . 1 C H31 .8911 .6043 .3186 .089 Uiso calc R 1 H C32 .9623(3) .50596(19) .3519(3) .0676(10) Uani d . 1 C H32 1.0073 .5194 .4140 .081 Uiso calc R 1 H C33 .7501(4) .5968(2) .1383(3) .1054(14) Uani d . 1 C H33A .7104 .5755 .0759 .127 Uiso calc R 1 H H33B .8033 .6352 .1217 .127 Uiso calc R 1 H H33C .6887 .6156 .1776 .127 Uiso calc 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 C3 .072(3) .063(3) .060(2) -.005(2) .001(2) .005(2) O2 .097(2) .0794(18) .0742(17) -.0003(16) .0208(16) -.0103(14) C1 .050(2) .063(2) .0482(19) -.0031(19) -.0004(16) -.0003(17) C2 .050(2) .063(2) .056(2) -.0063(19) -.0007(18) .0039(19) N1 .064(2) .085(2) .072(2) -.0039(18) -.0083(17) -.0061(18) O1 .0822(19) .0867(18) .0686(16) -.0029(16) -.0127(14) -.0155(14) C14 .045(2) .066(2) .064(2) -.0017(19) .0048(18) .004(2) C15 .067(3) .083(3) .084(3) .013(2) .019(2) .008(2) C16 .072(3) .090(4) .125(4) .020(3) .028(3) .015(3) C17 .077(3) .078(3) .144(5) .007(3) .034(3) -.018(3) C18 .083(3) .094(3) .093(3) -.008(3) .020(3) -.027(3) C19 .072(3) .072(3) .074(3) -.001(2) .002(2) -.007(2) C4 .058(2) .062(2) .057(2) -.001(2) .0095(18) .0007(18) N2 .060(2) .0633(19) .0672(18) -.0036(17) -.0049(15) .0037(15) C5 .059(2) .060(2) .056(2) .005(2) .0009(18) -.0042(18) C6 .054(2) .062(2) .052(2) .000(2) .0038(17) .0001(18) C7 .057(2) .058(2) .066(2) -.005(2) .0022(19) .0050(19) C8 .075(3) .069(3) .071(2) -.006(2) .019(2) -.005(2) C9 .107(4) .066(3) .072(3) -.008(3) .018(3) -.011(2) C10 .106(4) .084(3) .082(3) -.027(3) -.015(3) .004(3) C11 .066(3) .100(4) .148(4) -.025(3) -.016(3) .020(3) C12 .071(3) .073(3) .131(4) -.002(3) .000(3) .015(3) C13 .189(5) .108(4) .119(4) -.068(4) -.035(3) .000(3) C20 .056(2) .056(2) .067(2) .0028(19) -.008(2) -.0018(19) C21 .059(3) .078(3) .086(3) .002(2) -.003(2) -.001(2) C22 .062(3) .095(3) .119(4) .003(3) .002(3) .007(3) C23 .058(3) .097(3) .149(5) .003(3) -.025(3) -.002(3) C24 .082(3) .111(4) .107(4) .000(3) -.029(3) .010(3) C25 .071(3) .092(3) .078(3) .000(2) -.013(2) .008(2) C26 .054(2) .068(2) .060(2) -.004(2) .0043(18) .0003(19) C27 .056(2) .064(2) .057(2) -.005(2) .0061(18) .0035(19) C28 .080(3) .059(2) .064(2) -.004(2) .012(2) .003(2) C29 .079(3) .079(3) .058(2) -.003(2) .006(2) .004(2) C30 .069(3) .067(3) .071(3) .003(2) .011(2) .016(2) C31 .085(3) .059(2) .080(3) -.002(2) .015(2) .005(2) C32 .076(3) .063(2) .065(2) -.012(2) .012(2) .002(2) C33 .107(3) .099(3) .110(3) .023(3) .011(3) .030(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 1 3 -5 -1 3 5 2 1 1 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 C3 O1 121.7(3) yes O2 C3 C1 130.7(4) yes O1 C3 C1 107.6(3) ? C2 C1 C6 120.6(3) yes C2 C1 C3 99.9(3) yes C6 C1 C3 113.3(3) yes C2 C1 C4 113.6(3) yes C6 C1 C4 100.7(2) ? C3 C1 C4 108.9(3) yes N1 C2 C14 118.7(3) ? N1 C2 C1 114.1(3) ? C14 C2 C1 127.1(3) ? C2 N1 O1 107.2(3) ? C3 O1 N1 109.9(3) ? C15 C14 C19 118.9(3) ? C15 C14 C2 118.5(3) ? C19 C14 C2 122.5(3) ? C16 C15 C14 120.5(4) ? C17 C16 C15 120.4(4) ? C18 C17 C16 119.9(4) ? C17 C18 C19 120.2(4) ? C14 C19 C18 120.0(4) ? N2 C4 C7 113.1(3) ? N2 C4 C1 105.5(2) ? C7 C4 C1 115.5(3) ? C5 N2 C4 109.8(3) ? N2 C5 C20 121.0(3) ? N2 C5 C6 114.5(3) ? C20 C5 C6 124.4(3) ? C26 C6 C5 125.6(3) ? C26 C6 C1 128.2(3) ? C5 C6 C1 105.7(3) ? C8 C7 C12 118.2(4) ? C8 C7 C4 122.4(3) ? C12 C7 C4 119.4(4) ? C7 C8 C9 120.6(4) ? C10 C9 C8 121.5(4) ? C9 C10 C11 117.6(4) ? C9 C10 C13 120.6(5) ? C11 C10 C13 121.8(5) ? C10 C11 C12 121.7(4) ? C7 C12 C11 120.3(4) ? C21 C20 C25 118.9(3) ? C21 C20 C5 121.3(3) ? C25 C20 C5 119.8(3) ? C22 C21 C20 120.9(4) ? C23 C22 C21 119.9(4) ? C22 C23 C24 120.4(4) ? C23 C24 C25 119.7(4) ? C24 C25 C20 120.2(4) ? C6 C26 C27 128.4(3) yes C32 C27 C28 117.3(3) ? C32 C27 C26 119.7(3) ? C28 C27 C26 123.0(3) ? C27 C28 C29 121.2(3) ? C30 C29 C28 120.6(3) ? C31 C30 C29 118.2(3) ? C31 C30 C33 120.6(4) ? C29 C30 C33 121.2(3) ? C32 C31 C30 121.3(3) ? C31 C32 C27 121.3(3) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C3 O2 1.199(4) yes C3 O1 1.372(4) yes C3 C1 1.522(4) yes C1 C2 1.490(4) yes C1 C6 1.517(4) yes C1 C4 1.612(4) yes C2 N1 1.293(3) yes C2 C14 1.479(4) yes N1 O1 1.456(3) yes C14 C15 1.388(4) ? C14 C19 1.392(4) ? C15 C16 1.378(5) ? C16 C17 1.376(5) ? C17 C18 1.373(5) ? C18 C19 1.393(4) ? C4 N2 1.471(4) yes C4 C7 1.518(4) ? N2 C5 1.298(4) yes C5 C20 1.475(4) ? C5 C6 1.477(4) yes C6 C26 1.345(4) yes C7 C8 1.382(4) ? C7 C12 1.384(4) ? C8 C9 1.388(4) ? C9 C10 1.373(5) ? C10 C11 1.377(5) ? C10 C13 1.532(5) ? C11 C12 1.389(5) ? C20 C21 1.382(4) ? C20 C25 1.392(4) ? C21 C22 1.378(5) ? C22 C23 1.369(5) ? C23 C24 1.381(5) ? C24 C25 1.386(5) ? C26 C27 1.468(4) yes C27 C32 1.389(4) ? C27 C28 1.390(4) ? C28 C29 1.390(4) ? C29 C30 1.384(4) ? C30 C31 1.381(4) ? C30 C33 1.517(4) ? C31 C32 1.377(4) ? 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 C8 H8 N2 . .93 2.57 2.886(5) 100 yes C15 H15 N1 . .93 2.56 2.840(5) 97 yes C25 H25 N2 . .93 2.74 2.951(5) 94 ? C31 H31 O2 2_755 .93 2.72 3.290(4) 120 ? 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 O2 C3 C1 C2 169.0(4) ? O1 C3 C1 C2 -11.2(3) ? O2 C3 C1 C6 39.4(5) ? O1 C3 C1 C6 -140.7(3) ? O2 C3 C1 C4 -71.8(5) ? O1 C3 C1 C4 108.1(3) ? C6 C1 C2 N1 135.3(3) ? C3 C1 C2 N1 10.6(4) ? C4 C1 C2 N1 -105.2(3) ? C6 C1 C2 C14 -41.9(5) ? C3 C1 C2 C14 -166.6(3) ? C4 C1 C2 C14 77.6(4) ? C14 C2 N1 O1 171.6(3) ? C1 C2 N1 O1 -5.9(4) ? O2 C3 O1 N1 -171.3(3) ? C1 C3 O1 N1 8.8(3) ? C2 N1 O1 C3 -2.1(3) ? N1 C2 C14 C15 -32.1(5) yes C1 C2 C14 C15 145.0(3) ? N1 C2 C14 C19 152.3(3) ? C1 C2 C14 C19 -30.6(5) ? C19 C14 C15 C16 .0(5) ? C2 C14 C15 C16 -175.7(3) ? C14 C15 C16 C17 -1.5(6) ? C15 C16 C17 C18 1.2(6) ? C16 C17 C18 C19 .6(6) ? C15 C14 C19 C18 1.7(5) ? C2 C14 C19 C18 177.3(3) ? C17 C18 C19 C14 -2.0(6) ? C2 C1 C4 N2 -148.9(3) ? C6 C1 C4 N2 -18.7(3) ? C3 C1 C4 N2 100.7(3) ? C2 C1 C4 C7 85.4(3) ? C6 C1 C4 C7 -144.3(3) ? C3 C1 C4 C7 -25.0(4) ? C7 C4 N2 C5 140.7(3) ? C1 C4 N2 C5 13.5(3) ? C4 N2 C5 C20 177.4(3) ? C4 N2 C5 C6 -2.2(4) ? N2 C5 C6 C26 161.9(3) ? C20 C5 C6 C26 -17.7(5) ? N2 C5 C6 C1 -10.9(4) ? C20 C5 C6 C1 169.6(3) ? C2 C1 C6 C26 -29.6(5) ? C3 C1 C6 C26 88.5(4) ? C4 C1 C6 C26 -155.3(3) ? C2 C1 C6 C5 142.9(3) ? C3 C1 C6 C5 -99.0(3) ? C4 C1 C6 C5 17.2(3) ? N2 C4 C7 C8 -23.0(4) yes C1 C4 C7 C8 98.7(4) ? N2 C4 C7 C12 156.7(3) ? C1 C4 C7 C12 -81.6(4) ? C12 C7 C8 C9 .3(5) ? C4 C7 C8 C9 -180.0(3) ? C7 C8 C9 C10 .0(6) ? C8 C9 C10 C11 -.2(6) ? C8 C9 C10 C13 -179.8(3) ? C9 C10 C11 C12 .1(7) ? C13 C10 C11 C12 179.7(4) ? C8 C7 C12 C11 -.4(6) ? C4 C7 C12 C11 179.9(3) ? C10 C11 C12 C7 .2(7) ? N2 C5 C20 C21 138.5(3) ? C6 C5 C20 C21 -42.0(5) yes N2 C5 C20 C25 -40.9(5) ? C6 C5 C20 C25 138.7(3) ? C25 C20 C21 C22 1.3(5) ? C5 C20 C21 C22 -178.1(3) ? C20 C21 C22 C23 -1.8(6) ? C21 C22 C23 C24 1.2(7) ? C22 C23 C24 C25 -.1(7) ? C23 C24 C25 C20 -.3(6) ? C21 C20 C25 C24 -.2(5) ? C5 C20 C25 C24 179.1(3) ? C5 C6 C26 C27 -176.8(3) ? C1 C6 C26 C27 -5.7(6) ? C6 C26 C27 C32 135.8(4) ? C6 C26 C27 C28 -44.1(5) yes C32 C27 C28 C29 -3.8(5) ? C26 C27 C28 C29 176.1(3) ? C27 C28 C29 C30 1.7(5) ? C28 C29 C30 C31 .9(5) ? C28 C29 C30 C33 179.5(3) ? C29 C30 C31 C32 -1.3(5) ? C33 C30 C31 C32 -179.9(3) ? C30 C31 C32 C27 -.9(5) ? C28 C27 C32 C31 3.4(5) ? C26 C27 C32 C31 -176.5(3) ?