#------------------------------------------------------------------------------ #$Date: 2015-04-02 12:22:18 +0100 (Thu, 02 Apr 2015) $ #$Revision: 134621 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/82/2008298.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_2008298 loop_ _publ_author_name 'Meetsma, Auke' 'Keller, Erik' 'Feringa, Ben L.' _publ_section_title ; (+-)-6,6'-Dinitro-1,1'-binaphthyl 2,2'-diacetate ; _journal_issue 3 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 450 _journal_page_last 452 _journal_paper_doi 10.1107/S0108270198013109 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C24 H16 N2 O8' _chemical_formula_sum 'C24 H16 N2 O8' _chemical_formula_weight 460.40 _chemical_name_systematic ; ? ; _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'I -2ya' _symmetry_space_group_name_H-M 'I 1 a 1' _cell_angle_alpha 90 _cell_angle_beta 99.040(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.5060(10) _cell_length_b 29.143(2) _cell_length_c 9.8320(10) _cell_measurement_reflns_used 22 _cell_measurement_temperature 130 _cell_measurement_theta_max 21.85 _cell_measurement_theta_min 15.14 _cell_volume 2124.0(4) _computing_cell_refinement 'SET4 (de Boer & Duisenberg, 1984)' _computing_data_collection 'CAD4-UNIX Software (Enraf-Nonius, 1994)' _computing_data_reduction 'HELENA (Spek, 1993)' _computing_molecular_graphics 'PLUTO (Meetsma, 1997), ORTEP (Johnson, 1965) and PLATON (Spek, 1994)' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 130 _diffrn_measurement_device_type ; CAD-4F Enraf Nonius single-crystal diffractometer ; _diffrn_measurement_method ' \w/2\q' _diffrn_radiation_monochromator 'perpendicular mounted graphite' _diffrn_radiation_source 'fine focus sealed Philips Mo tube' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0177 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 36 _diffrn_reflns_limit_k_min -36 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3625 _diffrn_reflns_reduction_process ; Intensity data were corrected for Lorentz and polarization effects, scale variation, but not for absorption and reduced to F~o~^2^ ; _diffrn_reflns_theta_max 26.48 _diffrn_reflns_theta_min 1.40 _diffrn_standards_decay_% 4.0 _diffrn_standards_interval_time 180 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .11 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.440 _exptl_crystal_density_meas ? _exptl_crystal_description 'rectangular block' _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _refine_diff_density_max .161 _refine_diff_density_min -.154 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.8(7) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 371 _refine_ls_number_reflns 3625 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.041 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0321 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.2418P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref 0.0825 _reflns_number_gt 3319 _reflns_number_total 3625 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file sk1240.cif _[local]_cod_data_source_block c24h16n2O8 _[local]_cod_cif_authors_sg_H-M 'I a' _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: '_exptl_crystal_density_meas' value 'Not measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value ' calc w = 1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.2418P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+(0.0565P)^2^+0.2418P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2008298 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2+x,-y,z 1/2+x,1/2+y,1/2+z x,1/2-y,1/2+z 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 .0300(7) .0229(6) .0169(6) -.0021(5) .0038(5) -.0030(5) O2 .0239(7) .0217(6) .0297(7) -.0021(5) .0096(6) -.0050(5) O3 .0514(10) .0226(7) .0374(8) -.0005(7) .0033(8) -.0083(6) O4 .1072(18) .0440(10) .0252(8) .0133(11) -.0197(10) -.0112(7) O5 .0953(19) .0677(13) .0847(16) -.0203(13) .0625(16) .0101(12) O6 .0617(13) .0513(11) .0614(12) -.0198(10) .0030(10) .0309(9) O7 .0482(9) .0368(8) .0285(7) -.0022(7) .0166(7) .0041(6) O8 .0410(9) .0268(7) .0332(7) -.0036(6) .0084(7) -.0073(6) N1 .0423(10) .0268(9) .0251(8) -.0033(8) .0040(8) -.0056(7) N2 .0526(12) .0462(12) .0359(10) -.0264(10) .0087(10) .0087(9) C1 .0206(8) .0205(8) .0190(8) -.0027(7) .0049(7) -.0017(7) C2 .0256(10) .0249(9) .0159(8) .0012(8) -.0006(7) .0056(7) C3 .0266(9) .0179(8) .0237(8) .0032(7) .0039(7) .0025(7) C4 .0180(9) .0176(8) .0214(8) -.0014(6) .0050(7) .0024(7) C5 .0232(9) .0165(8) .0245(9) -.0005(7) .0064(7) -.0013(7) C6 .0232(9) .0208(8) .0225(8) -.0031(7) .0041(8) -.0050(7) C7 .0269(10) .0244(9) .0180(8) -.0017(7) .0029(8) -.0003(7) C8 .0246(9) .0184(8) .0198(8) .0020(7) .0035(8) .0026(7) C9 .0185(8) .0177(8) .0181(8) -.0015(7) .0055(7) .0007(6) C10 .0170(8) .0170(8) .0193(8) .0000(6) .0053(7) .0011(6) C11 .0240(9) .0165(8) .0166(7) -.0009(7) .0024(7) -.0024(6) C12 .0272(9) .0182(8) .0175(8) -.0032(7) .0010(7) -.0014(6) C13 .0273(10) .0217(9) .0228(9) -.0026(8) .0067(8) -.0013(7) C14 .0306(11) .0336(10) .0231(9) -.0104(9) .0078(8) -.0035(8) C15 .0428(13) .0332(10) .0239(10) -.0192(9) .0068(9) .0017(8) C16 .0457(13) .0221(9) .0274(10) -.0070(9) .0009(9) .0072(8) C17 .0341(10) .0199(9) .0245(9) -.0019(8) .0014(8) .0032(7) C18 .0389(12) .0181(9) .0390(11) .0046(9) .0017(10) .0073(8) C19 .0293(11) .0239(9) .0367(11) .0066(8) .0051(9) -.0034(9) C20 .0252(10) .0199(8) .0226(9) -.0024(7) .0041(8) -.0030(7) C21 .0348(11) .0308(10) .0185(9) .0044(9) .0058(8) .0017(8) C22 .0520(15) .0454(13) .0249(10) .0026(12) .0045(10) -.0087(10) C23 .0261(10) .0241(9) .0314(10) .0022(8) .0106(9) -.0046(8) C24 .0407(14) .0399(13) .0523(15) -.0073(11) .0257(13) -.0070(11) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_occupancy O1 .77772(18) .10867(4) .98581(13) .0233(4) Uani 1.000 O2 .37187(17) .12749(4) .81868(14) .0245(4) Uani 1.000 O3 .6869(2) -.09097(5) .37833(17) .0375(5) Uani 1.000 O4 .5428(3) -.04402(6) .23338(16) .0620(7) Uani 1.000 O5 1.1620(4) .22331(7) .3454(3) .0774(9) Uani 1.000 O6 1.0103(3) .28357(7) .3803(2) .0588(7) Uani 1.000 O7 .5903(2) .07331(5) 1.10919(15) .0367(5) Uani 1.000 O8 .4260(2) .17496(5) 1.00062(16) .0334(4) Uani 1.000 N1 .6229(3) -.05334(6) .34759(17) .0315(5) Uani 1.000 N2 1.0463(3) .24333(7) .3977(2) .0447(7) Uani 1.000 C1 .7531(2) .07403(6) .88593(18) .0198(5) Uani 1.000 C2 .8113(3) .02909(6) .92360(18) .0225(5) Uani 1.000 C3 .7998(3) -.00406(6) .82547(19) .0227(5) Uani 1.000 C4 .7273(2) .00611(6) .68678(18) .0188(5) Uani 1.000 C5 .7081(3) -.02845(6) .58523(19) .0211(5) Uani 1.000 C6 .6409(3) -.01694(6) .45222(19) .0221(5) Uani 1.000 C7 .5906(3) .02787(6) .41170(19) .0232(5) Uani 1.000 C8 .6070(3) .06152(6) .50857(18) .0209(5) Uani 1.000 C9 .6747(2) .05193(6) .64929(17) .0178(5) Uani 1.000 C10 .6886(2) .08669(6) .75296(18) .0175(5) Uani 1.000 C11 .6379(3) .13514(6) .71595(18) .0191(5) Uani 1.000 C12 .7453(3) .16243(6) .63961(18) .0212(5) Uani 1.000 C13 .9095(3) .14608(6) .60311(19) .0236(5) Uani 1.000 C14 1.0077(3) .17260(7) .5264(2) .0287(6) Uani 1.000 C15 .9435(3) .21601(7) .4849(2) .0331(6) Uani 1.000 C16 .7892(3) .23405(7) .5185(2) .0323(6) Uani 1.000 C17 .6867(3) .20746(6) .5983(2) .0265(5) Uani 1.000 C18 .5257(3) .22504(7) .6366(2) .0325(6) Uani 1.000 C19 .4282(3) .19920(7) .7129(2) .0300(6) Uani 1.000 C20 .4850(3) .15441(6) .75050(19) .0225(5) Uani 1.000 C21 .6978(3) .10294(7) 1.10057(19) .0279(6) Uani 1.000 C22 .7628(4) .13839(9) 1.2057(2) .0409(7) Uani 1.000 C23 .3422(3) .14375(6) .9444(2) .0265(6) Uani 1.000 C24 .1975(4) .11749(9) .9968(3) .0423(8) Uani 1.000 H2 .864(3) .0228(7) 1.010(2) .018(5) Uiso 1.000 H3 .844(3) -.0344(8) .854(2) .022(5) Uiso 1.000 H5 .742(3) -.0584(8) .611(2) .014(5) Uiso 1.000 H7 .539(4) .0344(8) .317(3) .035(6) Uiso 1.000 H8 .570(3) .0930(8) .485(2) .028(6) Uiso 1.000 H13 .953(3) .1166(7) .635(2) .012(4) Uiso 1.000 H14 1.109(3) .1620(7) .503(2) .018(5) Uiso 1.000 H16 .761(4) .2662(9) .487(3) .043(7) Uiso 1.000 H18 .488(3) .2557(8) .605(2) .029(6) Uiso 1.000 H19 .325(4) .2093(9) .745(3) .038(7) Uiso 1.000 H22 .702(6) .1410(12) 1.280(4) .078(11) Uiso 1.000 H22' .737(7) .1682(18) 1.161(6) .117(16) Uiso 1.000 H22" .882(8) .1449(16) 1.211(5) .112(16) Uiso 1.000 H24 .170(6) .1277(14) 1.087(4) .090(12) Uiso 1.000 H24' .222(5) .0897(13) 1.010(4) .063(9) Uiso 1.000 H24" .087(9) .1169(18) .930(6) .14(2) Uiso 1.000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source O O .0106 .0060 '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' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0033 .0016 '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 0 -4 2 2 -4 0 2 -2 2 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 C1 O1 C21 117.62(14) yes C20 O2 C23 115.67(14) yes O3 N1 O4 123.27(18) yes O3 N1 C6 119.20(17) yes O4 N1 C6 117.53(17) yes O5 N2 O6 124.1(2) yes O5 N2 C15 117.2(2) yes O6 N2 C15 118.7(2) yes O1 C1 C2 118.92(15) yes O1 C1 C10 117.55(15) yes C2 C1 C10 123.24(16) no C1 C2 C3 119.40(17) no C2 C3 C4 120.42(17) no C3 C4 C5 120.86(16) no C3 C4 C9 119.59(16) no C5 C4 C9 119.55(16) no C4 C5 C6 118.91(16) no N1 C6 C5 118.17(16) yes N1 C6 C7 118.90(16) yes C5 C6 C7 122.92(17) no C6 C7 C8 118.88(17) no C7 C8 C9 121.21(17) no C4 C9 C8 118.51(15) no C4 C9 C10 119.58(15) no C8 C9 C10 121.90(16) no C1 C10 C9 117.68(16) no C1 C10 C11 121.68(16) no C9 C10 C11 120.63(15) no C10 C11 C12 120.80(18) no C10 C11 C20 121.31(17) no C12 C11 C20 117.86(17) no C11 C12 C13 122.06(17) no C11 C12 C17 119.30(19) no C13 C12 C17 118.64(18) no C12 C13 C14 120.84(17) no C13 C14 C15 118.8(2) no N2 C15 C14 118.2(2) yes N2 C15 C16 118.45(19) yes C14 C15 C16 123.3(2) no C15 C16 C17 118.80(19) no C12 C17 C16 119.6(2) no C12 C17 C18 119.73(19) no C16 C17 C18 120.71(18) no C17 C18 C19 120.22(19) no C18 C19 C20 119.6(2) no O2 C20 C11 118.95(16) yes O2 C20 C19 117.67(19) yes C11 C20 C19 123.24(19) no O1 C21 O7 122.37(18) yes O1 C21 C22 110.46(18) yes O7 C21 C22 127.2(2) yes O2 C23 O8 122.16(19) yes O2 C23 C24 111.41(17) yes O8 C23 C24 126.4(2) yes C1 C2 H2 120.7(13) no C3 C2 H2 119.7(13) no C2 C3 H3 117.5(12) no C4 C3 H3 122.1(12) no C4 C5 H5 118.9(12) no C6 C5 H5 122.2(12) no C6 C7 H7 120.4(14) no C8 C7 H7 120.7(14) no C7 C8 H8 121.4(12) no C9 C8 H8 117.4(12) no C12 C13 H13 119.0(13) no C14 C13 H13 120.1(13) no C13 C14 H14 120.3(13) no C15 C14 H14 120.9(13) no C15 C16 H16 115.8(17) no C17 C16 H16 125.4(17) no C17 C18 H18 117.7(13) no C19 C18 H18 122.1(13) no C18 C19 H19 124.3(17) no C20 C19 H19 116.1(17) no C21 C22 H22 117(2) no C21 C22 H22' 107(3) no C21 C22 H22" 113(3) no H22 C22 H22' 101(4) no H22 C22 H22" 123(4) no H22' C22 H22" 88(4) no C23 C24 H24 115(3) no C23 C24 H24' 113(3) no C23 C24 H24" 112(4) no H24 C24 H24' 103(4) no H24 C24 H24" 110(4) no H24' C24 H24" 103(4) no 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 C1 . . 1.400(2) yes O1 C21 . . 1.369(2) yes O2 C20 . . 1.402(2) yes O2 C23 . . 1.374(2) yes O3 N1 . . 1.216(2) yes O4 N1 . . 1.218(2) yes O5 N2 . . 1.224(4) yes O6 N2 . . 1.210(3) yes O7 C21 . . 1.194(3) yes O8 C23 . . 1.191(2) yes N1 C6 . . 1.469(2) yes N2 C15 . . 1.474(3) yes C1 C2 . . 1.412(2) no C1 C10 . . 1.371(2) no C2 C3 . . 1.358(3) no C3 C4 . . 1.418(3) no C4 C5 . . 1.410(3) no C4 C9 . . 1.424(2) no C5 C6 . . 1.367(3) no C6 C7 . . 1.400(3) no C7 C8 . . 1.359(3) no C8 C9 . . 1.425(2) no C9 C10 . . 1.429(2) no C10 C11 . . 1.492(2) no C11 C12 . . 1.427(3) no C11 C20 . . 1.368(3) no C12 C13 . . 1.419(3) no C12 C17 . . 1.423(3) no C13 C14 . . 1.373(3) no C14 C15 . . 1.392(3) no C15 C16 . . 1.359(3) no C16 C17 . . 1.413(3) no C17 C18 . . 1.417(3) no C18 C19 . . 1.356(3) no C19 C20 . . 1.405(3) no C21 C22 . . 1.488(3) no C23 C24 . . 1.485(4) no C2 H2 . . .90(2) no C3 H3 . . .97(2) no C5 H5 . . .93(2) no C7 H7 . . .97(3) no C8 H8 . . .98(2) no C13 H13 . . .95(2) no C14 H14 . . .88(2) no C16 H16 . . 1.00(3) no C18 H18 . . .97(2) no C19 H19 . . .93(3) no C22 H22 . . .92(4) no C22 H22' . . .98(5) no C22 H22" . . .91(6) no C24 H24 . . .99(4) no C24 H24' . . .84(4) no C24 H24" . . .97(6) 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 C20 3.219(2) . no O1 C23 3.388(3) . no O1 C24 3.146(3) 1_655 no O2 C1 3.234(2) . no O3 C14 3.194(3) 2_455 no O3 C8 3.324(3) 2_555 no O4 C21 3.209(3) 2_454 no O4 C2 3.290(3) 2_454 no O5 C19 3.407(3) 4_654 no O6 C13 3.399(3) 4_554 no O6 C17 3.397(3) 4_554 no O6 C23 3.255(3) 4_654 no O6 C24 3.331(3) 4_654 no O6 C12 3.249(3) 4_554 no O7 C7 3.255(2) 1_556 no O7 C24 3.248(3) . no O7 C2 2.948(3) . no O7 C23 3.059(2) . no O8 C21 2.984(3) . no O8 C22 3.161(3) . no O8 C19 2.918(3) . no O8 C18 3.244(3) 4_555 no C1 C24 3.574(3) 1_655 no C1 O2 3.234(2) . no C2 O4 3.290(3) 2_556 no C2 O7 2.948(3) . no C5 C8 3.342(3) 2_555 no C5 C7 3.563(3) 2_555 no C5 C9 3.527(3) 2_555 no C6 C7 3.475(3) 2_555 no C7 C6 3.475(3) 2_455 no C7 O7 3.255(2) 1_554 no C7 C5 3.563(3) 2_455 no C8 C5 3.342(3) 2_455 no C8 O3 3.324(3) 2_455 no C8 C13 3.381(3) . no C8 C12 3.311(3) . no C9 C13 3.330(3) . no C9 C5 3.527(3) 2_455 no C12 O6 3.249(3) 4_555 no C12 C8 3.311(3) . no C13 C8 3.381(3) . no C13 O6 3.399(3) 4_555 no C13 C9 3.330(3) . no C14 C22 3.535(3) 1_554 no C14 O3 3.194(3) 2_555 no C14 C19 3.479(3) 1_655 no C17 O6 3.397(3) 4_555 no C18 O8 3.244(3) 4_554 no C19 O8 2.918(3) . no C19 C14 3.479(3) 1_455 no C19 O5 3.407(3) 4_455 no C20 O1 3.219(2) . no C21 O8 2.984(3) . no C21 O4 3.209(3) 2_556 no C21 C23 3.100(3) . no C22 O8 3.161(3) . no C22 C14 3.535(3) 1_556 no C23 O1 3.388(3) . no C23 O7 3.059(2) . no C23 O6 3.255(3) 4_455 no C23 C21 3.100(3) . no C24 C1 3.574(3) 1_455 no C24 O1 3.146(3) 1_455 no C24 O6 3.331(3) 4_455 no C24 O7 3.248(3) . no O1 H24" 2.48(7) 1_655 no O2 H3 2.75(2) 2_455 no O3 H14 2.52(2) 2_455 no O3 H8 2.90(2) 2_555 no O3 H5 2.45(2) . no O4 H7 2.43(2) . no O4 H2 2.47(2) 2_454 no O5 H14 2.44(2) . no O5 H19 2.59(3) 4_654 no O6 H19 2.89(3) 4_654 no O6 H16 2.34(3) . no O7 H2 2.82(2) . no O7 H24' 2.82(4) . no O7 H7 2.42(3) 1_556 no O8 H22' 2.61(6) . no O8 H18 2.28(2) 4_555 no O8 H19 2.70(3) . no C1 H24" 2.77(7) 1_655 no C8 H5 3.07(2) 2_455 no C9 H13 2.83(2) . no C10 H13 2.60(2) . no C11 H8 2.56(2) . no C12 H8 2.74(2) . no C13 H8 3.05(2) . no C21 H2 2.86(2) . no C23 H19 2.73(3) . no C24 H3 3.09(2) 2_455 no H2 O7 2.82(2) . no H2 C21 2.86(2) . no H2 O4 2.47(2) 2_556 no H3 H5 2.49(3) . no H3 O2 2.75(2) 2_555 no H3 C24 3.09(2) 2_555 no H3 H24' 2.50(4) 2_555 no H5 O3 2.45(2) . no H5 H3 2.49(3) . no H5 C8 3.07(2) 2_555 no H7 O4 2.43(2) . no H7 O7 2.42(3) 1_554 no H8 C11 2.56(2) . no H8 C12 2.74(2) . no H8 C13 3.05(2) . no H8 O3 2.90(2) 2_455 no H13 C9 2.83(2) . no H13 C10 2.60(2) . no H14 O5 2.44(2) . no H14 O3 2.52(2) 2_555 no H16 O6 2.34(3) . no H16 H18 2.53(4) . no H16 H22' 2.59(6) 4_554 no H18 H16 2.53(4) . no H18 O8 2.28(2) 4_554 no H19 O8 2.70(3) . no H19 C23 2.73(3) . no H19 O5 2.59(3) 4_455 no H19 O6 2.89(3) 4_455 no H22' O8 2.61(6) . no H22' H16 2.59(6) 4_555 no H24' O7 2.82(4) . no H24' H3 2.50(4) 2_455 no H24" O1 2.48(7) 1_455 no H24" C1 2.77(6) 1_455 no 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 C21 O1 C1 C2 -59.3(2) no C21 O1 C1 C10 126.70(17) no C1 O1 C21 O7 -10.4(3) no C1 O1 C21 C22 170.26(17) no C23 O2 C20 C11 121.86(19) no C23 O2 C20 C19 -62.4(2) no C20 O2 C23 O8 -10.1(3) no C20 O2 C23 C24 170.25(18) no O3 N1 C6 C5 -8.5(3) no O3 N1 C6 C7 170.9(2) no O4 N1 C6 C5 171.2(2) no O4 N1 C6 C7 -9.4(3) no O5 N2 C15 C14 13.5(3) no O5 N2 C15 C16 -165.3(2) no O6 N2 C15 C14 -167.6(2) no O6 N2 C15 C16 13.6(3) no O1 C1 C2 C3 -175.37(18) no C10 C1 C2 C3 -1.7(3) no O1 C1 C10 C9 175.92(14) no O1 C1 C10 C11 -2.8(2) no C2 C1 C10 C9 2.2(2) no C2 C1 C10 C11 -176.54(18) no C1 C2 C3 C4 -1.0(3) no C2 C3 C4 C5 -177.4(2) no C2 C3 C4 C9 3.1(3) no C3 C4 C5 C6 -178.7(2) no C9 C4 C5 C6 .7(3) no C3 C4 C9 C8 178.25(18) no C3 C4 C9 C10 -2.6(2) no C5 C4 C9 C8 -1.2(2) no C5 C4 C9 C10 177.96(16) no C4 C5 C6 N1 179.62(19) no C4 C5 C6 C7 .3(3) no N1 C6 C7 C8 179.9(2) no C5 C6 C7 C8 -.8(3) no C6 C7 C8 C9 .3(3) no C7 C8 C9 C4 .7(3) no C7 C8 C9 C10 -178.42(19) no C4 C9 C10 C1 .0(2) no C4 C9 C10 C11 178.75(16) no C8 C9 C10 C1 179.12(17) no C8 C9 C10 C11 -2.1(3) no C1 C10 C11 C12 109.0(2) no C1 C10 C11 C20 -72.8(2) no C9 C10 C11 C12 -69.7(2) no C9 C10 C11 C20 108.5(2) no C10 C11 C12 C13 -4.0(3) no C10 C11 C12 C17 175.90(17) no C20 C11 C12 C13 177.75(18) no C20 C11 C12 C17 -2.3(3) no C10 C11 C20 O2 -1.8(3) no C10 C11 C20 C19 -177.30(18) no C12 C11 C20 O2 176.44(16) no C12 C11 C20 C19 .9(3) no C11 C12 C13 C14 178.22(18) no C17 C12 C13 C14 -1.7(3) no C11 C12 C17 C16 -177.77(18) no C11 C12 C17 C18 1.7(3) no C13 C12 C17 C16 2.2(3) no C13 C12 C17 C18 -178.33(18) no C12 C13 C14 C15 .1(3) no C13 C14 C15 N2 -177.47(18) no C13 C14 C15 C16 1.2(3) no N2 C15 C16 C17 177.94(18) no C14 C15 C16 C17 -.7(3) no C15 C16 C17 C12 -1.0(3) no C15 C16 C17 C18 179.5(2) no C12 C17 C18 C19 .3(3) no C16 C17 C18 C19 179.9(2) no C17 C18 C19 C20 -1.8(3) no C18 C19 C20 O2 -174.41(18) no C18 C19 C20 C11 1.2(3) no