#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200305.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_enum 1527 2010-12-29 10:47:43Z saulius 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_disorder_assembly _atom_site_disorder_group _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_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_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_ _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_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) ? _cod_database_fobs_code 2200305