#------------------------------------------------------------------------------ #$Date: 2012-02-03 17:16:24 +0000 (Fri, 03 Feb 2012) $ #$Revision: 32112 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/12/2011207.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_2011207 loop_ _publ_author_name 'Gerkin, Roger E.' _publ_section_title ; C---H···O interactions in diethyl 5,5',6,6'-tetramethylbiphenyl-2,2'-dicarboxylate at 193K ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 1024 _journal_page_last 1025 _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C22 H26 O4' _chemical_formula_sum 'C22 H26 O4' _chemical_formula_weight 354.45 _chemical_name_common ; diethyl 5, 6, 5',6'-tetramethylbiphenyl-2, 2'-dicarboxylate # ; _chemical_name_systematic ' ?' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 92.9965(10) _cell_angle_beta 90.1788(10) _cell_angle_gamma 113.3672(9) _cell_formula_units_Z 2 _cell_length_a 8.9719(2) _cell_length_b 10.7632(2) _cell_length_c 10.8399(2) _cell_measurement_reflns_used 22068 _cell_measurement_temperature 193 _cell_measurement_theta_max 27.52 _cell_measurement_theta_min 2.06 _cell_volume 959.28(3) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1997)' _computing_data_collection ' COLLECT (Nonius, 1999)' _computing_data_reduction DENZO-SMN _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material 'TEXSAN and PLATON (Spek, 1990)' _computing_structure_refinement 'TEXSAN (Molecular Structure Corporation, 1995)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 193 _diffrn_measured_fraction_theta_max .990 _diffrn_measurement_device_type 'Nonius KappaCCD diffractometer' _diffrn_measurement_method 'omega scans with \k offsets' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .024 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 22068 _diffrn_reflns_theta_max 27.52 _exptl_absorpt_coefficient_mu .083 _exptl_absorpt_correction_type none _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.227 _exptl_crystal_density_meas ' not measured' _exptl_crystal_description 'cut slab ' _exptl_crystal_F_000 380 _exptl_crystal_size_max .42 _exptl_crystal_size_mid .35 _exptl_crystal_size_min .27 _refine_diff_density_max .33 _refine_diff_density_min -.24 _refine_ls_goodness_of_fit_ref 1.94 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 323 _refine_ls_number_reflns 4374 _refine_ls_R_factor_gt .050 _refine_ls_shift/su_max .0003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details '1/[\s^2^~cs~ + (0.035I)^2^]' _refine_ls_weighting_scheme sigma _refine_ls_wR_factor_ref .125 _reflns_number_gt 3340 _reflns_number_total 4374 _reflns_threshold_expression 'I >2.00\s~I~' _[local]_cod_data_source_file fr1277.cif _[local]_cod_data_source_block I _cod_database_code 2011207 loop_ _symmetry_equiv_pos_as_xyz ' +x, +y, +z' ' -x, -y, -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 O1 .79720(10) .61284(9) .39659(8) .0355(3) Uani d ? . 1.000 O2 .87546(13) .62151(12) .59323(9) .0563(4) Uani d ? . 1.000 O3 .74400(11) .50811(9) .88235(9) .0413(3) Uani d ? . 1.000 O4 .55019(11) .56939(10) .81172(9) .0487(3) Uani d ? . 1.000 C1 .67753(14) .78257(12) .65115(11) .0282(3) Uani d ? . 1.000 C2 .67073(14) .70307(12) .54234(10) .0272(3) Uani d ? . 1.000 C3 .54356(15) .67372(13) .45688(11) .0314(3) Uani d ? . 1.000 C4 .42528(15) .72337(13) .47810(12) .0354(4) Uani d ? . 1.000 C5 .42901(15) .80203(13) .58430(12) .0347(4) Uani d ? . 1.000 C6 .55532(15) .83135(13) .67192(11) .0324(4) Uani d ? . 1.000 C7 .79275(15) .64372(13) .51711(11) .0307(3) Uani d ? . 1.000 C8 .2972(2) .8542(2) .60402(17) .0491(5) Uani d ? . 1.000 C9 .5578(2) .9140(2) .78889(16) .0536(5) Uani d ? . 1.000 C10 .90212(18) .54402(16) .36057(13) .0373(4) Uani d ? . 1.000 C11 .8627(2) .4947(2) .22909(15) .0535(5) Uani d ? . 1.000 C12 .81781(14) .82272(12) .74310(10) .0285(3) Uani d ? . 1.000 C13 .82464(14) .73406(12) .83094(11) .0293(3) Uani d ? . 1.000 C14 .95694(15) .77237(13) .91210(11) .0338(4) Uani d ? . 1.000 C15 1.08113(16) .89923(14) .90838(12) .0370(4) Uani d ? . 1.000 C16 1.07725(15) .98923(13) .82362(12) .0344(4) Uani d ? . 1.000 C17 .94439(15) .95155(12) .73983(11) .0312(3) Uani d ? . 1.000 C18 .69047(15) .59783(13) .83866(11) .0321(4) Uani d ? . 1.000 C19 1.2160(2) 1.12663(17) .82153(17) .0476(5) Uani d ? . 1.000 C20 .9400(2) 1.05159(16) .64938(15) .0467(5) Uani d ? . 1.000 C21 .62088(19) .37402(14) .89885(16) .0460(4) Uani d ? . 1.000 C22 .7050(3) .28438(18) .9217(2) .0621(6) Uani d ? . 1.000 H3 .5380 .6176 .3814 .038 Uiso c C3 . 1.000 H4 .3369 .7026 .4168 .043 Uiso c C4 . 1.000 H8C .244(2) .8306(17) .6823(17) .072(6) Uiso d ? . 1.000 H8A .220(2) .8250(17) .5368(17) .072(5) Uiso d ? . 1.000 H8B .3437(19) .9535(18) .6122(14) .058(5) Uiso d ? . 1.000 H9B .447(3) .884(2) .8229(19) .103(7) Uiso d ? . 1.000 H9A .629(3) .919(2) .852(2) .109(8) Uiso d ? . 1.000 H9C .565(3) 1.007(3) .765(2) .122(9) Uiso d ? . 1.000 H10B 1.0119(19) .6040(14) .3742(13) .043(4) Uiso d ? . 1.000 H10A .8839(17) .4727(15) .4156(14) .047(4) Uiso d ? . 1.000 H11B .749(3) .428(2) .2254(18) .087(6) Uiso d ? . 1.000 H11C .886(2) .5759(19) .1766(18) .081(6) Uiso d ? . 1.000 H11A .932(2) .4466(16) .1984(14) .056(4) Uiso d ? . 1.000 H14 .9624 .7093 .9722 .041 Uiso c C14 . 1.000 H15 1.1735 .9258 .9669 .045 Uiso c C15 . 1.000 H19A 1.273(2) 1.1312(17) .7447(18) .074(6) Uiso d ? . 1.000 H19B 1.284(2) 1.1380(16) .8888(16) .065(5) Uiso d ? . 1.000 H19C 1.181(2) 1.2007(18) .8304(16) .071(6) Uiso d ? . 1.000 H20A .852(2) 1.0110(18) .5876(17) .076(5) Uiso d ? . 1.000 H20B 1.042(2) 1.0925(18) .6054(17) .080(6) Uiso d ? . 1.000 H20C .915(2) 1.122(2) .6891(19) .088(6) Uiso d ? . 1.000 H21B .5546(19) .3758(14) .9659(15) .050(4) Uiso d ? . 1.000 H21A .545(2) .3442(16) .8229(17) .070(5) Uiso d ? . 1.000 H22A .780(3) .319(2) .999(2) .096(7) Uiso d ? . 1.000 H22B .779(3) .280(2) .852(2) .112(8) Uiso d ? . 1.000 H22C .613(2) .1901(19) .9392(15) .070(5) Uiso d ? . 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 O1 .0397(5) .0438(6) .0308(5) .0252(4) .0022(4) -.0003(4) O2 .0649(7) .0871(9) .0408(6) .0586(7) -.0188(5) -.0199(5) O3 .0336(5) .0320(5) .0554(6) .0089(4) -.0046(4) .0111(4) O4 .0277(6) .0487(6) .0649(7) .0086(5) -.0042(5) .0169(5) C1 .0286(7) .0267(7) .0296(6) .0111(5) .0004(5) .0024(5) C2 .0267(7) .0258(7) .0298(6) .0109(5) .0012(5) .0032(5) C3 .0316(7) .0338(7) .0299(6) .0142(6) -.0004(5) .0019(5) C4 .0308(7) .0410(8) .0369(7) .0168(6) -.0048(5) .0041(6) C5 .0312(7) .0337(7) .0435(8) .0168(6) .0025(6) .0062(6) C6 .0340(7) .0302(7) .0363(7) .0165(6) .0020(6) .0006(6) C7 .0290(7) .0314(7) .0318(7) .0126(6) -.0022(5) -.0024(5) C8 .0433(9) .0576(12) .0586(11) .0338(8) -.0048(8) -.0037(9) C9 .0530(11) .0628(12) .0532(10) .0344(9) -.0035(8) -.0186(9) C10 .0339(8) .0422(9) .0412(8) .0218(7) .0021(6) -.0044(7) C11 .0561(11) .0720(12) .0445(9) .0395(10) .0029(8) -.0082(9) C12 .0281(7) .0309(7) .0286(6) .0144(6) .0015(5) -.0025(5) C13 .0274(7) .0313(7) .0298(6) .0125(6) .0006(5) -.0017(5) C14 .0333(7) .0383(8) .0306(7) .0155(6) -.0025(5) .0001(6) C15 .0311(7) .0408(8) .0358(7) .0119(6) -.0060(6) -.0069(6) C16 .0313(7) .0320(7) .0368(7) .0102(6) .0032(6) -.0068(6) C17 .0332(7) .0291(7) .0316(7) .0132(6) .0046(5) -.0015(5) C18 .0305(7) .0362(8) .0300(6) .0135(6) .0003(5) .0032(5) C19 .0383(9) .0375(9) .0554(10) .0036(7) -.0010(8) -.0047(7) C20 .0527(10) .0356(9) .0480(9) .0130(8) -.0011(8) .0066(7) C21 .0419(9) .0345(8) .0540(9) .0059(7) -.0017(8) .0121(7) C22 .0704(12) .0393(10) .0750(13) .0203(9) -.0045(11) .0025(9) 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 O1 C7 . . 1.3357(14) yes O1 C10 . . 1.4534(15) yes O2 C7 . . 1.2025(15) yes O3 C18 . . 1.3422(15) yes O3 C21 . . 1.4487(17) yes O4 C18 . . 1.2024(15) yes C1 C2 . . 1.4070(17) no C1 C6 . . 1.4051(17) no C1 C12 . . 1.5100(16) no C2 C3 . . 1.3917(17) no C2 C7 . . 1.4899(17) no C3 C4 . . 1.3795(18) no C3 H3 . . .98 no C4 C5 . . 1.3851(18) no C4 H4 . . .98 no C5 C6 . . 1.4015(18) no C5 C8 . . 1.5085(19) no C6 C9 . . 1.5051(19) no C8 H8C . . .970(19) no C8 H8A . . .951(18) no C8 H8B . . .979(17) no C9 H9B . . 1.00(2) no C9 H9A . . .92(3) no C9 H9C . . 1.03(3) no C10 C11 . . 1.485(2) no C10 H10B . . .945(15) no C10 H10A . . .959(16) no C11 H11B . . .98(2) no C11 H11C . . 1.02(2) no C11 H11A . . 1.002(17) no C12 C13 . . 1.4007(17) no C12 C17 . . 1.4035(17) no C13 C14 . . 1.3857(17) no C13 C18 . . 1.4897(18) no C14 C15 . . 1.3808(18) no C14 H14 . . .98 no C15 C16 . . 1.3797(19) no C15 H15 . . .98 no C16 C17 . . 1.4077(18) no C16 C19 . . 1.5102(19) no C17 C20 . . 1.5052(19) no C19 H19A . . .971(19) no C19 H19B . . .923(18) no C19 H19C . . .966(19) no C20 H20A . . .977(19) no C20 H20B . . .98(2) no C20 H20C . . .95(2) no C21 C22 . . 1.470(2) no C21 H21B . . .945(16) no C21 H21A . . 1.019(18) no C22 H22A . . 1.03(2) no C22 H22B . . 1.02(3) no C22 H22C . . 1.050(19) no loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H 0 0 'Stewart et al. (1965)' C .003 .002 'Creagh & McAuley (1992)' O .011 .006 '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 C7 O1 C10 116.83(10) yes C18 O3 C21 115.79(10) yes C2 C1 C6 119.35(10) no C2 C1 C12 121.45(11) no C6 C1 C12 119.13(10) no C1 C2 C3 119.78(11) no C1 C2 C7 122.00(10) no C3 C2 C7 118.18(10) no C2 C3 C4 120.18(11) no C2 C3 H3 119.9 no C4 C3 H3 119.9 no C3 C4 C5 121.29(11) no C3 C4 H4 119.4 no C5 C4 H4 119.3 no C4 C5 C6 119.25(11) no C4 C5 C8 119.63(12) no C6 C5 C8 121.12(12) no C1 C6 C5 120.15(11) no C1 C6 C9 120.36(12) no C5 C6 C9 119.48(12) no O1 C7 O2 122.64(11) yes O1 C7 C2 111.33(10) yes O2 C7 C2 126.00(11) yes C5 C8 H8C 112.9(11) no C5 C8 H8A 110.8(11) no C5 C8 H8B 110.6(9) no H8C C8 H8A 111.2(15) no H8C C8 H8B 102.1(14) no H8A C8 H8B 108.9(14) no C6 C9 H9B 110.2(11) no C6 C9 H9A 118.4(13) no C6 C9 H9C 107.8(13) no H9B C9 H9A 108.5(17) no H9B C9 H9C 96.1(16) no H9A C9 H9C 113.6(17) no O1 C10 C11 107.50(12) yes O1 C10 H10B 109.5(8) no O1 C10 H10A 107.8(9) no C11 C10 H10B 112.9(9) no C11 C10 H10A 113.4(8) no H10B C10 H10A 105.5(12) no C10 C11 H11B 106.8(12) no C10 C11 H11C 108.9(10) no C10 C11 H11A 111.4(9) no H11B C11 H11C 115.0(15) no H11B C11 H11A 107.4(14) no H11C C11 H11A 107.4(14) no C1 C12 C13 121.46(11) no C1 C12 C17 119.13(11) no C13 C12 C17 119.41(11) no C12 C13 C14 120.18(11) no C12 C13 C18 120.72(10) no C14 C13 C18 119.10(11) no C13 C14 C15 120.13(12) no C13 C14 H14 119.9 no C15 C14 H14 119.9 no C14 C15 C16 121.04(12) no C14 C15 H15 119.5 no C16 C15 H15 119.5 no C15 C16 C17 119.57(12) no C15 C16 C19 119.56(13) no C17 C16 C19 120.87(13) no C12 C17 C16 119.66(12) no C12 C17 C20 121.27(12) no C16 C17 C20 119.07(12) no O3 C18 O4 122.86(12) yes O3 C18 C13 111.66(10) yes O4 C18 C13 125.47(12) yes C16 C19 H19A 108.8(10) no C16 C19 H19B 108.8(10) no C16 C19 H19C 113.0(10) no H19A C19 H19B 110.9(15) no H19A C19 H19C 110.1(15) no H19B C19 H19C 105.3(14) no C17 C20 H20A 112.4(11) no C17 C20 H20B 112.8(11) no C17 C20 H20C 111.3(12) no H20A C20 H20B 107.8(15) no H20A C20 H20C 102.7(16) no H20B C20 H20C 109.3(16) no O3 C21 C22 107.50(14) yes O3 C21 H21B 110.7(9) no O3 C21 H21A 108.8(9) no C22 C21 H21B 110.4(9) no C22 C21 H21A 113.8(9) no H21B C21 H21A 105.6(13) no C21 C22 H22A 110.7(12) no C21 C22 H22B 113.1(13) no C21 C22 H22C 105.7(10) no H22A C22 H22B 105.1(17) no H22A C22 H22C 108.2(15) no H22B C22 H22C 114.1(16) 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 H20B 2.918(18) 2_776 no O1 C20 3.5060(18) 2_776 no O2 H10A 2.725(15) 2_766 no O2 H10B 3.012(14) 2_766 no O2 C10 3.2117(17) 2_766 no O3 H11A 2.897(17) 2_766 no O4 H21B 2.711(16) 2_667 no O4 H3 2.7105 2_666 no O4 H11B 2.73(2) 2_666 no O4 C11 3.511(2) 2_666 no C3 C7 3.5757(18) 2_666 no C4 H10A 3.018(15) 2_666 no C7 H20B 3.015(19) 2_776 no C11 H22A 2.95(2) 1_554 no C15 C15 3.584(3) 2_777 no C15 C16 3.5936(17) 2_777 no C16 H8C 3.045(18) 1_655 no C19 H21A 2.952(17) 1_665 no H3 H21A 2.4412 2_666 no H8A H20A 2.55(3) 2_676 no H8B H19A 2.61(2) 1_455 no H9A H15 2.6634 2_777 no H9C H22C 2.56(3) 1_565 no H10A H10A 2.63(3) 2_766 no H11C H14 2.6460 1_554 no H11A H22A 2.57(3) 1_554 no H14 H22A 2.4711 2_767 no H19A H21A 2.70(2) 1_665 no H19B H21A 2.64(2) 1_665 no H20A H20B 2.67(3) 2_776 no H3 C3 .9800 . no H3 C4 2.0522 . no H3 C2 2.0633 . no H3 O1 2.3518 . no H3 C7 2.6253 . no H4 C4 .9799 . no H4 C3 2.0466 . no H4 C5 2.0517 . no H4 C8 2.6509 . no H8C C8 .970(19) . no H8C C5 2.087(19) . no H8A C8 .951(18) . no H8A C5 2.050(19) . no H8A C4 2.551(18) . no H8B C8 .979(17) . no H8B C5 2.067(17) . no H9B C9 1.00(2) . no H9B C6 2.07(2) . no H9B C8 2.66(2) . no H9B C5 2.67(2) . no H9A C9 .92(3) . no H9A C6 2.10(2) . no H9A C12 2.57(2) . no H9A C1 2.69(2) . no H9C C9 1.03(3) . no H9C C6 2.07(3) . no H10B C10 .945(15) . no H10B O1 1.981(15) . no H10B C11 2.048(15) . no H10B C7 2.658(14) . no H10A C10 .959(16) . no H10A O1 1.971(16) . no H10A C11 2.064(15) . no H10A O2 2.461(14) . no H10A C7 2.501(14) . no H11B C11 .98(2) . no H11B C10 2.00(2) . no H11B O1 2.551(19) . no H11C C11 1.02(2) . no H11C C10 2.06(2) . no H11C O1 2.578(19) . no H11A C11 1.002(17) . no H11A C10 2.073(16) . no H14 C14 .9799 . no H14 C15 2.0536 . no H14 C13 2.0581 . no H14 O3 2.4248 . no H14 C18 2.6385 . no H15 C15 .9800 . no H15 C16 2.0480 . no H15 C14 2.0491 . no H15 C19 2.6473 . no H19A C19 .971(19) . no H19A C16 2.042(19) . no H19B C19 .923(18) . no H19B C16 2.008(17) . no H19B C15 2.513(16) . no H19C C19 .966(19) . no H19C C16 2.086(18) . no H20A C20 .977(19) . no H20A C17 2.08(2) . no H20A C1 2.471(18) . no H20A C12 2.629(19) . no H20B C20 .98(2) . no H20B C17 2.09(2) . no H20C C20 .95(2) . no H20C C17 2.05(2) . no H21B C21 .945(16) . no H21B O3 1.990(16) . no H21B C22 2.006(16) . no H21B C18 2.673(15) . no H21A C21 1.019(18) . no H21A O3 2.022(17) . no H21A C22 2.100(18) . no H21A O4 2.416(16) . no H21A C18 2.511(16) . no H22A C22 1.03(2) . no H22A C21 2.07(2) . no H22A O3 2.57(2) . no H22B C22 1.02(3) . no H22B C21 2.09(2) . no H22B O3 2.60(2) . no H22C C22 1.050(19) . no H22C C21 2.024(18) . 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 C3 H3 O4 2_666 .98 2.71 3.671(2) 167 yes C11 H11B O4 2_666 .98(2) 2.73(2) 3.511(2) 137.0(15) yes C21 H21B O4 2_667 .94(2) 2.71(2) 3.625(2) 163.1(12) 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 O1 C7 C2 C1 -159.11(11) no O1 C7 C2 C3 23.34(16) no O2 C7 O1 C10 2.93(18) no O2 C7 C2 C1 22.8(2) no O2 C7 C2 C3 -154.72(14) no O3 C18 C13 C12 151.71(11) no O3 C18 C13 C14 -28.33(16) no O4 C18 O3 C21 -1.70(18) no O4 C18 C13 C12 -29.45(19) no O4 C18 C13 C14 150.50(13) no C1 C2 C3 C4 .59(19) no C1 C6 C5 C4 .7(2) no C1 C6 C5 C8 -179.48(13) no C1 C12 C13 C14 178.33(11) no C1 C12 C13 C18 -1.72(17) no C1 C12 C17 C16 -178.86(10) no C1 C12 C17 C20 2.02(18) no C2 C1 C6 C5 -.64(19) no C2 C1 C6 C9 178.63(13) no C2 C1 C12 C13 -81.64(15) no C2 C1 C12 C17 98.02(14) no C2 C3 C4 C5 -.5(2) no C2 C7 O1 C10 -175.21(11) no C3 C2 C1 C6 -.02(19) no C3 C2 C1 C12 -176.83(11) no C3 C4 C5 C6 -.2(2) no C3 C4 C5 C8 -179.94(14) no C4 C3 C2 C7 178.20(11) no C4 C5 C6 C9 -178.54(14) no C5 C6 C1 C12 176.25(11) no C6 C1 C2 C7 -177.53(11) no C6 C1 C12 C13 101.54(14) no C6 C1 C12 C17 -78.80(15) no C7 O1 C10 C11 168.43(13) no C7 C2 C1 C12 5.66(18) no C8 C5 C6 C9 1.2(2) no C9 C6 C1 C12 -4.5(2) no C12 C13 C14 C15 1.31(19) no C12 C17 C16 C15 -.27(18) no C12 C17 C16 C19 179.41(12) no C13 C12 C17 C16 .81(18) no C13 C12 C17 C20 -178.31(12) no C13 C14 C15 C16 -.8(2) no C13 C18 O3 C21 177.16(11) no C14 C13 C12 C17 -1.33(18) no C14 C15 C16 C17 .2(2) no C14 C15 C16 C19 -179.44(13) no C15 C14 C13 C18 -178.64(11) no C15 C16 C17 C20 178.87(13) no C17 C12 C13 C18 178.62(10) no C18 O3 C21 C22 168.42(13) no C19 C16 C17 C20 -1.45(19) no