# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 182/1405 data_compound1 _publ_contact_author ; Hawthorne, M. F., Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569. USA ; _publ_contact_author_phone '310-825-7378' _publ_contact_author-fax '310-825-5490' _publ_contact_author-email KNOBLERH@CHEM.UCLA.EDU _publ_requested_journal ; 'J. Chem. Soc., Chem. Comm.' ; _publ_contact_letter ; This CIF submission is for crystallographic data for a paper submitted for publication in Journal of the Chemical Society, Chemical Communications ; _publ_section-title ; An unpaired electron incarcerated within an icosahedral borane cage: synthesis and crystal structure of the blue, air-stable {[closo-B~12~(CH~3~)~12~]^.^}^-^ radical ; loop_ _publ_author_name _publ_author_address 'Peymann, Toralf' ;Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569. USA ; 'Knobler, Carolyn B.' ;Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569. USA ; 'Hawthorne, M. Frederick' ;Department of Chemistry and Biochemistry, University of California, Los Angeles, CA 90095-1569. USA ; _audit_creation_method SHELXL _chemical_name_systematic ; [Ph~3~P=N=PPh~3~]^+^ {[closo-B~12~(CH~3~)~12~]^.^}^-^ ; _chemical_compound_source ; 'crystallized from methylene chloride/ethanol' ; _chemical_formula_sum 'C48 H66 B12 N P2' _chemical_formula_weight 848.68 _cell_measurement_temperature 298 _diffrn_ambient_temperature 298 _exptl_crystal_colour 'blue' _exptl_crystal_description 'plate' _exptl_crystal_size_min 0.20 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_max 0.60 _exptl_crystal_preparation 'fiber' _diffrn_special_details ; \q scan rate 7.5\% per min ; _diffrn_reflns_reduction_process 'modified Lehmann-Larsen algorithm' _computing_data_reduction 'REDUCE (UCLA crystallographic package)' _diffrn_reflns_av_sigmaI/netI .098 _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'graphite' _diffrn_measurement_device 'Huber (Crystal Logic)' _cell_measurement_reflns_used 51 _cell_measurement_theta_min 4.6 _cell_measurement_theta_max 10.1 _symmetry_cell_setting monoclinic _computing_cell_refinement 'LEAST (UCLA crystallographic package)' _diffrn_standards_interval_count 97 _diffrn_measurement_method 'profile data from \q/2\q scans' _diffrn_radiation_detector 'scintillation' _diffrn_radiation_detector_dtime 3.5 _reflns_special_details ; 2 reflections flagged as unreliable because the intensity was greater than the detector maximum ; _diffrn_standards_number 3 _diffrn_standards_decay_% -0.1 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 7 1 -1 2 0 -6 5 -1 1 _diffrn_reflns_number 5281 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.3 _diffrn_reflns_theta_max 27.5 data_shelxl _audit_creation_method SHELXL loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'B' 'B' 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'P' 'P' 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'C2/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' '-x, -y, -z' '-x, y, -z-1/2' '-x+1/2, -y+1/2, -z' '-x+1/2, y+1/2, -z-1/2' _cell_length_a 34.660(29) _cell_length_b 9.342(8) _cell_length_c 18.693(15) _cell_angle_alpha 90.00 _cell_angle_beta 122.22(2) _cell_angle_gamma 90.00 _cell_volume 5120.3(74) _cell_formula_units_Z 4 _exptl_crystal_density_diffrn 1.101 _exptl_crystal_F_000 1804 _exptl_absorpt_coefficient_mu 0.118 _diffrn_reflns_number 4900 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0967 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 41 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4900 _reflns_number_observed 2489 _reflns_observed_criterion 2sigma(I) _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ 2sigma(F^2^) is used only for calculating _R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme 'calc w=1/[\s^2^(Fo^2^)+(0.0743P)^2^+11.6448P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment ; H in calculated positions with displacement parameter based on that for the attached atom. ; _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0006(3) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 4900 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1512 _refine_ls_R_factor_obs 0.0708 _refine_ls_wR_factor_all 0.2266 _refine_ls_wR_factor_obs 0.1783 _refine_ls_goodness_of_fit_all 1.013 _refine_ls_goodness_of_fit_obs 1.139 _refine_ls_restrained_S_all 1.013 _refine_ls_restrained_S_obs 1.139 _refine_ls_shift/esd_max 0.008 _refine_ls_shift/esd_mean 0.001 loop_ _atom_site_label _atom_site_type_symbol _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 _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group P1 P 0.49845(3) 0.08966(12) 0.66737(7) 0.0453(3) Uani 1 d . . N1 N 0.5000 0.1338(5) 0.7500 0.0510(12) Uani 1 d S . C11 C 0.44633(13) 0.1480(5) 0.5752(3) 0.0488(10) Uani 1 d . . C12 C 0.42528(15) 0.0716(5) 0.5002(3) 0.0620(12) Uani 1 d . . H12 H 0.43791(15) -0.0140(5) 0.4967(3) 0.074 Uiso 1 calc R . C13 C 0.3855(2) 0.1224(6) 0.4305(3) 0.0745(15) Uani 1 d . . H13 H 0.3712(2) 0.0700(6) 0.3805(3) 0.089 Uiso 1 calc R . C14 C 0.3671(2) 0.2489(7) 0.4345(3) 0.081(2) Uani 1 d . . H14 H 0.3404(2) 0.2826(7) 0.3872(3) 0.097 Uiso 1 calc R . C15 C 0.3880(2) 0.3262(6) 0.5081(3) 0.081(2) Uani 1 d . . H15 H 0.3754(2) 0.4128(6) 0.5104(3) 0.097 Uiso 1 calc R . C16 C 0.4273(2) 0.2771(5) 0.5786(3) 0.0671(13) Uani 1 d . . H16 H 0.4411(2) 0.3299(5) 0.6284(3) 0.080 Uiso 1 calc R . C21 C 0.50305(13) -0.0991(4) 0.6555(2) 0.0488(10) Uani 1 d . . C22 C 0.46793(15) -0.1898(5) 0.6436(3) 0.0625(12) Uani 1 d . . H22 H 0.44207(15) -0.1511(5) 0.6393(3) 0.075 Uiso 1 calc R . C23 C 0.4713(2) -0.3356(5) 0.6380(3) 0.079(2) Uani 1 d . . H23 H 0.4480(2) -0.3955(5) 0.6307(3) 0.095 Uiso 1 calc R . C24 C 0.5094(2) -0.3919(6) 0.6434(4) 0.083(2) Uani 1 d . . H24 H 0.5115(2) -0.4904(6) 0.6392(4) 0.100 Uiso 1 calc R . C25 C 0.5440(2) -0.3060(6) 0.6547(3) 0.079(2) Uani 1 d . . H25 H 0.5694(2) -0.3462(6) 0.6580(3) 0.094 Uiso 1 calc R . C26 C 0.5414(2) -0.1590(5) 0.6613(3) 0.0635(13) Uani 1 d . . H26 H 0.5652(2) -0.1006(5) 0.6695(3) 0.076 Uiso 1 calc R . C31 C 0.54476(13) 0.1779(4) 0.6675(3) 0.0477(10) Uani 1 d . . C32 C 0.5860(2) 0.1905(6) 0.7428(3) 0.0687(13) Uani 1 d . . H32 H 0.5895(2) 0.1540(6) 0.7922(3) 0.082 Uiso 1 calc R . C33 C 0.6224(2) 0.2573(7) 0.7454(4) 0.086(2) Uani 1 d . . H33 H 0.6505(2) 0.2639(7) 0.7962(4) 0.103 Uiso 1 calc R . C34 C 0.6172(2) 0.3132(7) 0.6736(4) 0.089(2) Uani 1 d . . H34 H 0.6415(2) 0.3587(7) 0.6754(4) 0.107 Uiso 1 calc R . C35 C 0.5762(2) 0.3027(6) 0.5988(4) 0.085(2) Uani 1 d . . H35 H 0.5728(2) 0.3416(6) 0.5499(4) 0.102 Uiso 1 calc R . C36 C 0.5397(2) 0.2348(5) 0.5949(3) 0.0652(13) Uani 1 d . . H36 H 0.5119(2) 0.2275(5) 0.5436(3) 0.078 Uiso 1 calc R . B1 B 0.2415(2) 0.0791(7) 0.0213(4) 0.0663(14) Uiso 1 d . . C1M C 0.2341(2) -0.0804(6) 0.0435(5) 0.114(2) Uani 1 d G . H1M1 H 0.2620(2) -0.1151(6) 0.0914(5) 0.171 Uiso 1 calc R . H1M2 H 0.2250(2) -0.1418(6) -0.0042(5) 0.171 Uiso 1 calc R . H1M3 H 0.2107(2) -0.0799(6) 0.0564(5) 0.171 Uiso 1 calc R . B2 B 0.2452(2) 0.1202(6) -0.0686(4) 0.0665(15) Uiso 1 d . . C2M C 0.2402(2) -0.0006(8) -0.1342(4) 0.116(2) Uani 1 d G . H2M1 H 0.2113(2) 0.0096(8) -0.1863(4) 0.174 Uiso 1 calc R . H2M2 H 0.2421(2) -0.0936(8) -0.1108(4) 0.174 Uiso 1 calc R . H2M3 H 0.2643(2) 0.0100(8) -0.1449(4) 0.174 Uiso 1 calc R . B3 B 0.1970(2) 0.1793(6) -0.0647(4) 0.0656(15) Uiso 1 d . . C3M C 0.1465(2) 0.1140(8) -0.1264(4) 0.115(2) Uani 1 d G . H3M1 H 0.1420(2) 0.0929(8) -0.1805(4) 0.172 Uiso 1 calc R . H3M2 H 0.1241(2) 0.1826(8) -0.1332(4) 0.172 Uiso 1 calc R . H3M3 H 0.1433(2) 0.0278(8) -0.1021(4) 0.172 Uiso 1 calc R . B4 B 0.2167(2) 0.2314(6) 0.0417(4) 0.0640(14) Uiso 1 d . . C4M C 0.1858(2) 0.2122(7) 0.0814(4) 0.103(2) Uani 1 d G . H4M1 H 0.2023(2) 0.2458(7) 0.1388(4) 0.154 Uiso 1 calc R . H4M2 H 0.1785(2) 0.1128(7) 0.0803(4) 0.154 Uiso 1 calc R . H4M3 H 0.1582(2) 0.2664(7) 0.0489(4) 0.154 Uiso 1 calc R . B5 B 0.2778(2) 0.2037(7) 0.1042(4) 0.069(2) Uiso 1 d . . C5M C 0.3036(2) 0.1577(9) 0.2011(4) 0.130(3) Uani 1 d G . H5M1 H 0.2844(2) 0.0951(9) 0.2096(4) 0.195 Uiso 1 calc R . H5M2 H 0.3105(2) 0.2414(9) 0.2357(4) 0.195 Uiso 1 calc R . H5M3 H 0.3313(2) 0.1089(9) 0.2165(4) 0.195 Uiso 1 calc R . B6 B 0.2948(2) 0.1351(6) 0.0356(4) 0.0651(15) Uiso 1 d . . C6M C 0.3367(2) 0.0258(7) 0.0687(5) 0.115(2) Uani 1 d G . H6M1 H 0.3374(2) -0.0378(7) 0.1097(5) 0.173 Uiso 1 calc R . H6M2 H 0.3648(2) 0.0785(7) 0.0942(5) 0.173 Uiso 1 calc R . H6M3 H 0.3330(2) -0.0289(7) 0.0219(5) 0.173 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 P1 0.0429(6) 0.0438(6) 0.0486(6) -0.0002(5) 0.0240(5) 0.0012(5) N1 0.058(3) 0.047(3) 0.050(3) 0.000 0.031(2) 0.000 C11 0.044(2) 0.055(3) 0.045(2) 0.005(2) 0.022(2) 0.004(2) C12 0.059(3) 0.068(3) 0.052(3) 0.002(2) 0.025(2) 0.012(2) C13 0.063(3) 0.095(4) 0.050(3) -0.006(3) 0.020(2) 0.002(3) C14 0.058(3) 0.102(5) 0.064(3) 0.020(3) 0.019(3) 0.025(3) C15 0.073(3) 0.076(4) 0.078(4) 0.008(3) 0.030(3) 0.027(3) C16 0.065(3) 0.061(3) 0.064(3) -0.001(2) 0.026(3) 0.011(2) C21 0.048(2) 0.046(2) 0.046(2) -0.001(2) 0.020(2) 0.002(2) C22 0.053(3) 0.053(3) 0.077(3) -0.009(2) 0.031(2) -0.001(2) C23 0.081(4) 0.053(3) 0.098(4) -0.010(3) 0.044(3) -0.013(3) C24 0.095(4) 0.045(3) 0.102(4) -0.008(3) 0.047(3) 0.006(3) C25 0.081(4) 0.064(3) 0.087(4) -0.004(3) 0.042(3) 0.020(3) C26 0.056(3) 0.060(3) 0.070(3) -0.001(2) 0.031(2) 0.008(2) C31 0.045(2) 0.047(2) 0.053(3) -0.001(2) 0.027(2) 0.000(2) C32 0.054(3) 0.078(3) 0.072(3) 0.006(3) 0.032(3) -0.003(3) C33 0.055(3) 0.117(5) 0.091(4) -0.012(4) 0.041(3) -0.018(3) C34 0.085(4) 0.102(5) 0.110(5) -0.035(4) 0.073(4) -0.040(4) C35 0.107(5) 0.095(4) 0.085(4) -0.005(3) 0.073(4) -0.020(4) C36 0.072(3) 0.074(3) 0.059(3) -0.009(2) 0.042(3) -0.011(3) C1M 0.124(5) 0.072(4) 0.175(7) 0.017(4) 0.099(5) 0.002(4) C2M 0.121(5) 0.115(6) 0.133(6) -0.051(5) 0.082(5) -0.024(4) C3M 0.063(3) 0.138(6) 0.115(5) -0.028(5) 0.029(3) -0.031(4) C4M 0.100(4) 0.112(5) 0.135(5) -0.003(4) 0.089(4) -0.003(4) C5M 0.116(5) 0.190(8) 0.065(4) 0.026(5) 0.035(4) 0.015(5) C6M 0.084(4) 0.110(5) 0.156(6) 0.037(5) 0.067(4) 0.042(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag P1 N1 1.572(2) . ? P1 C11 1.792(4) . ? P1 C21 1.795(5) . ? P1 C31 1.803(4) . ? N1 P1 1.572(2) 6_657 ? C11 C12 1.385(6) . ? C11 C16 1.393(6) . ? C12 C13 1.381(6) . ? C13 C14 1.364(7) . ? C14 C15 1.370(7) . ? C15 C16 1.373(6) . ? C21 C26 1.392(6) . ? C21 C22 1.400(6) . ? C22 C23 1.376(7) . ? C23 C24 1.373(7) . ? C24 C25 1.362(7) . ? C25 C26 1.387(7) . ? C31 C32 1.376(6) . ? C31 C36 1.380(6) . ? C32 C33 1.387(7) . ? C33 C34 1.358(8) . ? C34 C35 1.365(8) . ? C35 C36 1.382(7) . ? B1 C1M 1.604(8) . ? B1 B3 1.788(8) . ? B1 B2 1.795(8) . ? B1 B6 1.798(8) . ? B1 B4 1.804(8) . ? B1 B5 1.805(8) . ? B2 C2M 1.606(8) . ? B2 B6 1.789(8) . ? B2 B4 1.790(8) 7 ? B2 B5 1.794(8) 7 ? B2 B3 1.800(8) . ? B3 C3M 1.616(8) . ? B3 B4 1.791(8) . ? B3 B6 1.794(8) 7 ? B3 B5 1.788(8) 7 ? B4 C4M 1.607(7) . ? B4 B6 1.785(8) 7 ? B4 B2 1.790(8) 7 ? B4 B5 1.809(8) . ? B5 C5M 1.594(8) . ? B5 B3 1.788(8) 7 ? B5 B6 1.792(8) . ? B5 B2 1.794(9) 7 ? B6 C6M 1.605(8) . ? B6 B4 1.785(8) 7 ? B6 B3 1.794(8) 7 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 P1 C11 110.7(2) . . ? N1 P1 C21 114.9(2) . . ? C11 P1 C21 106.9(2) . . ? N1 P1 C31 108.3(2) . . ? C11 P1 C31 107.6(2) . . ? C21 P1 C31 108.2(2) . . ? P1 N1 P1 149.6(3) . 6_657 ? C12 C11 C16 119.1(4) . . ? C12 C11 P1 122.3(3) . . ? C16 C11 P1 118.6(3) . . ? C13 C12 C11 120.0(5) . . ? C14 C13 C12 120.5(5) . . ? C13 C14 C15 120.0(5) . . ? C14 C15 C16 120.6(5) . . ? C15 C16 C11 119.8(5) . . ? C26 C21 C22 118.8(4) . . ? C26 C21 P1 122.0(3) . . ? C22 C21 P1 119.2(3) . . ? C23 C22 C21 120.7(4) . . ? C24 C23 C22 119.3(5) . . ? C25 C24 C23 121.2(5) . . ? C24 C25 C26 120.2(5) . . ? C25 C26 C21 119.7(5) . . ? C32 C31 C36 119.4(4) . . ? C32 C31 P1 118.6(3) . . ? C36 C31 P1 121.9(3) . . ? C31 C32 C33 120.3(5) . . ? C34 C33 C32 119.9(5) . . ? C33 C34 C35 120.3(5) . . ? C34 C35 C36 120.6(5) . . ? C31 C36 C35 119.5(5) . . ? C1M B1 B3 122.5(5) . . ? C1M B1 B2 122.8(5) . . ? B3 B1 B2 60.3(3) . . ? C1M B1 B6 121.7(5) . . ? B3 B1 B6 108.0(4) . . ? B2 B1 B6 59.7(3) . . ? C1M B1 B4 121.2(4) . . ? B3 B1 B4 59.8(3) . . ? B2 B1 B4 108.0(4) . . ? B6 B1 B4 107.8(4) . . ? C1M B1 B5 120.8(5) . . ? B3 B1 B5 107.9(4) . . ? B2 B1 B5 107.6(4) . . ? B6 B1 B5 59.7(3) . . ? B4 B1 B5 60.1(3) . . ? C2M B2 B6 122.4(5) . . ? C2M B2 B4 121.5(5) . 7 ? B6 B2 B4 59.8(3) . 7 ? C2M B2 B5 121.0(5) . 7 ? B6 B2 B5 108.1(4) . 7 ? B4 B2 B5 60.6(3) 7 7 ? C2M B2 B1 122.2(5) . . ? B6 B2 B1 60.2(3) . . ? B4 B2 B1 108.1(4) 7 . ? B5 B2 B1 107.7(4) 7 . ? C2M B2 B3 121.5(5) . . ? B6 B2 B3 107.8(4) . . ? B4 B2 B3 108.2(4) 7 . ? B5 B2 B3 59.7(3) 7 . ? B1 B2 B3 59.7(3) . . ? C3M B3 B4 121.5(5) . . ? C3M B3 B1 122.1(5) . . ? B4 B3 B1 60.5(3) . . ? C3M B3 B6 121.1(5) . 7 ? B4 B3 B6 59.7(3) . 7 ? B1 B3 B6 108.2(4) . 7 ? C3M B3 B5 121.2(5) . 7 ? B4 B3 B5 108.1(4) . 7 ? B1 B3 B5 108.2(4) . 7 ? B6 B3 B5 60.0(3) 7 7 ? C3M B3 B2 122.1(5) . . ? B4 B3 B2 108.4(4) . . ? B1 B3 B2 60.0(3) . . ? B6 B3 B2 108.0(4) 7 . ? B5 B3 B2 60.0(3) 7 . ? C4M B4 B3 121.9(5) . . ? C4M B4 B6 122.4(5) . 7 ? B3 B4 B6 60.2(3) . 7 ? C4M B4 B2 121.9(5) . 7 ? B3 B4 B2 108.2(4) . 7 ? B6 B4 B2 60.1(3) 7 7 ? C4M B4 B1 121.3(5) . . ? B3 B4 B1 59.6(3) . . ? B6 B4 B1 107.9(4) 7 . ? B2 B4 B1 108.0(4) 7 . ? C4M B4 B5 121.6(5) . . ? B3 B4 B5 107.6(4) . . ? B6 B4 B5 107.7(4) 7 . ? B2 B4 B5 59.8(3) 7 . ? B1 B4 B5 59.9(3) . . ? C5M B5 B3 122.2(5) . 7 ? C5M B5 B6 121.2(5) . . ? B3 B5 B6 60.2(3) 7 . ? C5M B5 B2 122.5(5) . 7 ? B3 B5 B2 60.3(3) 7 7 ? B6 B5 B2 108.3(4) . 7 ? C5M B5 B1 120.9(5) . . ? B3 B5 B1 108.0(4) 7 . ? B6 B5 B1 60.0(3) . . ? B2 B5 B1 107.8(4) 7 . ? C5M B5 B4 121.8(5) . . ? B3 B5 B4 107.9(4) 7 . ? B6 B5 B4 107.9(4) . . ? B2 B5 B4 59.6(3) 7 . ? B1 B5 B4 59.9(3) . . ? C6M B6 B4 121.5(5) . 7 ? C6M B6 B3 122.3(5) . 7 ? B4 B6 B3 60.1(3) 7 7 ? C6M B6 B2 121.1(5) . . ? B4 B6 B2 60.1(3) 7 . ? B3 B6 B2 108.1(4) 7 . ? C6M B6 B5 121.9(5) . . ? B4 B6 B5 108.1(4) 7 . ? B3 B6 B5 59.8(3) 7 . ? B2 B6 B5 108.4(4) . . ? C6M B6 B1 121.3(5) . . ? B4 B6 B1 108.2(4) 7 . ? B3 B6 B1 108.1(4) 7 . ? B2 B6 B1 60.0(3) . . ? B5 B6 B1 60.4(3) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C11 P1 N1 P1 116.1(2) . . . 6_657 ? C21 P1 N1 P1 -5.08(15) . . . 6_657 ? C31 P1 N1 P1 -126.1(2) . . . 6_657 ? N1 P1 C11 C12 -147.2(4) . . . . ? C21 P1 C11 C12 -21.4(4) . . . . ? C31 P1 C11 C12 94.6(4) . . . . ? N1 P1 C11 C16 34.9(4) . . . . ? C21 P1 C11 C16 160.7(4) . . . . ? C31 P1 C11 C16 -83.4(4) . . . . ? C16 C11 C12 C13 -1.0(7) . . . . ? P1 C11 C12 C13 -179.0(4) . . . . ? C11 C12 C13 C14 1.0(8) . . . . ? C12 C13 C14 C15 -0.3(8) . . . . ? C13 C14 C15 C16 -0.5(9) . . . . ? C14 C15 C16 C11 0.5(8) . . . . ? C12 C11 C16 C15 0.3(7) . . . . ? P1 C11 C16 C15 178.3(4) . . . . ? N1 P1 C21 C26 -111.0(3) . . . . ? C11 P1 C21 C26 125.7(4) . . . . ? C31 P1 C21 C26 10.1(4) . . . . ? N1 P1 C21 C22 66.3(4) . . . . ? C11 P1 C21 C22 -56.9(4) . . . . ? C31 P1 C21 C22 -172.5(3) . . . . ? C26 C21 C22 C23 0.3(7) . . . . ? P1 C21 C22 C23 -177.1(4) . . . . ? C21 C22 C23 C24 -0.7(8) . . . . ? C22 C23 C24 C25 0.5(9) . . . . ? C23 C24 C25 C26 0.2(9) . . . . ? C24 C25 C26 C21 -0.6(8) . . . . ? C22 C21 C26 C25 0.4(7) . . . . ? P1 C21 C26 C25 177.7(4) . . . . ? N1 P1 C31 C32 38.6(4) . . . . ? C11 P1 C31 C32 158.4(4) . . . . ? C21 P1 C31 C32 -86.5(4) . . . . ? N1 P1 C31 C36 -140.3(4) . . . . ? C11 P1 C31 C36 -20.5(4) . . . . ? C21 P1 C31 C36 94.6(4) . . . . ? C36 C31 C32 C33 -1.3(7) . . . . ? P1 C31 C32 C33 179.8(4) . . . . ? C31 C32 C33 C34 1.3(9) . . . . ? C32 C33 C34 C35 -0.6(9) . . . . ? C33 C34 C35 C36 -0.3(9) . . . . ? C32 C31 C36 C35 0.4(7) . . . . ? P1 C31 C36 C35 179.3(4) . . . . ? C34 C35 C36 C31 0.4(8) . . . . ? C1M B1 B2 C2M 1.3(8) . . . . ? B3 B1 B2 C2M -110.3(6) . . . . ? B6 B1 B2 C2M 111.7(6) . . . . ? B4 B1 B2 C2M -147.7(5) . . . . ? B5 B1 B2 C2M 148.8(5) . . . . ? C1M B1 B2 B6 -110.4(6) . . . . ? B3 B1 B2 B6 138.0(4) . . . . ? B6 B1 B2 B6 0.0 . . . . ? B4 B1 B2 B6 100.6(4) . . . . ? B5 B1 B2 B6 37.1(4) . . . . ? C1M B1 B2 B4 -147.5(5) . . . 7 ? B3 B1 B2 B4 100.9(4) . . . 7 ? B6 B1 B2 B4 -37.2(4) . . . 7 ? B4 B1 B2 B4 63.4(5) . . . 7 ? B5 B1 B2 B4 -0.1(5) . . . 7 ? C1M B1 B2 B5 148.4(5) . . . 7 ? B3 B1 B2 B5 36.8(4) . . . 7 ? B6 B1 B2 B5 -101.2(4) . . . 7 ? B4 B1 B2 B5 -0.6(5) . . . 7 ? B5 B1 B2 B5 -64.1(5) . . . 7 ? C1M B1 B2 B3 111.6(6) . . . . ? B3 B1 B2 B3 0.0 . . . . ? B6 B1 B2 B3 -138.0(4) . . . . ? B4 B1 B2 B3 -37.4(4) . . . . ? B5 B1 B2 B3 -100.9(4) . . . . ? C1M B1 B3 C3M -0.9(8) . . . . ? B2 B1 B3 C3M 111.3(6) . . . . ? B6 B1 B3 C3M 148.7(5) . . . . ? B4 B1 B3 C3M -110.7(6) . . . . ? B5 B1 B3 C3M -148.3(5) . . . . ? C1M B1 B3 B4 109.9(6) . . . . ? B2 B1 B3 B4 -138.0(4) . . . . ? B6 B1 B3 B4 -100.6(4) . . . . ? B4 B1 B3 B4 0.0 . . . . ? B5 B1 B3 B4 -37.6(4) . . . . ? C1M B1 B3 B6 147.2(5) . . . 7 ? B2 B1 B3 B6 -100.7(4) . . . 7 ? B6 B1 B3 B6 -63.3(5) . . . 7 ? B4 B1 B3 B6 37.3(4) . . . 7 ? B5 B1 B3 B6 -0.2(5) . . . 7 ? C1M B1 B3 B5 -149.2(5) . . . 7 ? B2 B1 B3 B5 -37.1(4) . . . 7 ? B6 B1 B3 B5 0.3(5) . . . 7 ? B4 B1 B3 B5 100.9(4) . . . 7 ? B5 B1 B3 B5 63.3(5) . . . 7 ? C1M B1 B3 B2 -112.1(6) . . . . ? B2 B1 B3 B2 0.0 . . . . ? B6 B1 B3 B2 37.4(4) . . . . ? B4 B1 B3 B2 138.0(4) . . . . ? B5 B1 B3 B2 100.4(4) . . . . ? C2M B2 B3 C3M 0.2(8) . . . . ? B6 B2 B3 C3M -148.8(5) . . . . ? B4 B2 B3 C3M 147.9(5) 7 . . . ? B5 B2 B3 C3M 110.1(6) 7 . . . ? B1 B2 B3 C3M -111.3(6) . . . . ? C2M B2 B3 B4 149.3(5) . . . . ? B6 B2 B3 B4 0.3(5) . . . . ? B4 B2 B3 B4 -62.9(5) 7 . . . ? B5 B2 B3 B4 -100.7(4) 7 . . . ? B1 B2 B3 B4 37.9(4) . . . . ? C2M B2 B3 B1 111.4(6) . . . . ? B6 B2 B3 B1 -37.6(4) . . . . ? B4 B2 B3 B1 -100.8(4) 7 . . . ? B5 B2 B3 B1 -138.6(4) 7 . . . ? B1 B2 B3 B1 0.0 . . . . ? C2M B2 B3 B6 -147.5(5) . . . 7 ? B6 B2 B3 B6 63.5(5) . . . 7 ? B4 B2 B3 B6 0.2(5) 7 . . 7 ? B5 B2 B3 B6 -37.5(4) 7 . . 7 ? B1 B2 B3 B6 101.1(4) . . . 7 ? C2M B2 B3 B5 -110.0(6) . . . 7 ? B6 B2 B3 B5 101.0(4) . . . 7 ? B4 B2 B3 B5 37.8(4) 7 . . 7 ? B5 B2 B3 B5 0.0 7 . . 7 ? B1 B2 B3 B5 138.6(4) . . . 7 ? C3M B3 B4 C4M 1.6(8) . . . . ? B1 B3 B4 C4M -110.1(6) . . . . ? B6 B3 B4 C4M 111.7(6) 7 . . . ? B5 B3 B4 C4M 148.7(5) 7 . . . ? B2 B3 B4 C4M -147.8(5) . . . . ? C3M B3 B4 B6 -110.1(6) . . . 7 ? B1 B3 B4 B6 138.1(4) . . . 7 ? B6 B3 B4 B6 0.0 7 . . 7 ? B5 B3 B4 B6 37.0(4) 7 . . 7 ? B2 B3 B4 B6 100.5(4) . . . 7 ? C3M B3 B4 B2 -147.7(5) . . . 7 ? B1 B3 B4 B2 100.6(4) . . . 7 ? B6 B3 B4 B2 -37.6(4) 7 . . 7 ? B5 B3 B4 B2 -0.6(5) 7 . . 7 ? B2 B3 B4 B2 62.9(5) . . . 7 ? C3M B3 B4 B1 111.7(6) . . . . ? B1 B3 B4 B1 0.0 . . . . ? B6 B3 B4 B1 -138.1(4) 7 . . . ? B5 B3 B4 B1 -101.2(4) 7 . . . ? B2 B3 B4 B1 -37.6(4) . . . . ? C3M B3 B4 B5 149.1(5) . . . . ? B1 B3 B4 B5 37.4(4) . . . . ? B6 B3 B4 B5 -100.7(4) 7 . . . ? B5 B3 B4 B5 -63.8(5) 7 . . . ? B2 B3 B4 B5 -0.2(5) . . . . ? C1M B1 B4 C4M -0.9(8) . . . . ? B3 B1 B4 C4M 111.1(6) . . . . ? B2 B1 B4 C4M 148.8(5) . . . . ? B6 B1 B4 C4M -148.1(5) . . . . ? B5 B1 B4 C4M -110.9(6) . . . . ? C1M B1 B4 B3 -112.0(6) . . . . ? B3 B1 B4 B3 0.0 . . . . ? B2 B1 B4 B3 37.7(4) . . . . ? B6 B1 B4 B3 100.8(4) . . . . ? B5 B1 B4 B3 138.0(4) . . . . ? C1M B1 B4 B6 -149.5(5) . . . 7 ? B3 B1 B4 B6 -37.5(4) . . . 7 ? B2 B1 B4 B6 0.2(5) . . . 7 ? B6 B1 B4 B6 63.3(5) . . . 7 ? B5 B1 B4 B6 100.5(4) . . . 7 ? C1M B1 B4 B2 147.0(5) . . . 7 ? B3 B1 B4 B2 -101.0(4) . . . 7 ? B2 B1 B4 B2 -63.3(5) . . . 7 ? B6 B1 B4 B2 -0.2(5) . . . 7 ? B5 B1 B4 B2 37.0(4) . . . 7 ? C1M B1 B4 B5 110.0(6) . . . . ? B3 B1 B4 B5 -138.0(4) . . . . ? B2 B1 B4 B5 -100.3(4) . . . . ? B6 B1 B4 B5 -37.2(4) . . . . ? B5 B1 B4 B5 0.0 . . . . ? C1M B1 B5 C5M 0.6(8) . . . . ? B3 B1 B5 C5M 148.7(5) . . . . ? B2 B1 B5 C5M -147.6(5) . . . . ? B6 B1 B5 C5M -110.5(6) . . . . ? B4 B1 B5 C5M 111.3(6) . . . . ? C1M B1 B5 B3 148.7(5) . . . 7 ? B3 B1 B5 B3 -63.2(5) . . . 7 ? B2 B1 B5 B3 0.4(5) . . . 7 ? B6 B1 B5 B3 37.5(4) . . . 7 ? B4 B1 B5 B3 -100.6(4) . . . 7 ? C1M B1 B5 B6 111.1(5) . . . . ? B3 B1 B5 B6 -100.8(4) . . . . ? B2 B1 B5 B6 -37.1(4) . . . . ? B6 B1 B5 B6 0.0 . . . . ? B4 B1 B5 B6 -138.2(4) . . . . ? C1M B1 B5 B2 -147.6(5) . . . 7 ? B3 B1 B5 B2 0.5(5) . . . 7 ? B2 B1 B5 B2 64.2(5) . . . 7 ? B6 B1 B5 B2 101.3(4) . . . 7 ? B4 B1 B5 B2 -36.9(4) . . . 7 ? C1M B1 B5 B4 -110.7(5) . . . . ? B3 B1 B5 B4 37.4(4) . . . . ? B2 B1 B5 B4 101.1(4) . . . . ? B6 B1 B5 B4 138.2(4) . . . . ? B4 B1 B5 B4 0.0 . . . . ? C4M B4 B5 C5M 0.6(8) . . . . ? B3 B4 B5 C5M -147.1(6) . . . . ? B6 B4 B5 C5M 149.4(6) 7 . . . ? B2 B4 B5 C5M 111.7(6) 7 . . . ? B1 B4 B5 C5M -109.8(6) . . . . ? C4M B4 B5 B3 -148.7(5) . . . 7 ? B3 B4 B5 B3 63.6(5) . . . 7 ? B6 B4 B5 B3 0.1(5) 7 . . 7 ? B2 B4 B5 B3 -37.6(4) 7 . . 7 ? B1 B4 B5 B3 100.9(4) . . . 7 ? C4M B4 B5 B6 147.7(5) . . . . ? B3 B4 B5 B6 0.1(5) . . . . ? B6 B4 B5 B6 -63.5(5) 7 . . . ? B2 B4 B5 B6 -101.1(4) 7 . . . ? B1 B4 B5 B6 37.3(4) . . . . ? C4M B4 B5 B2 -111.1(6) . . . 7 ? B3 B4 B5 B2 101.2(4) . . . 7 ? B6 B4 B5 B2 37.7(4) 7 . . 7 ? B2 B4 B5 B2 0.0 7 . . 7 ? B1 B4 B5 B2 138.5(4) . . . 7 ? C4M B4 B5 B1 110.4(6) . . . . ? B3 B4 B5 B1 -37.3(4) . . . . ? B6 B4 B5 B1 -100.8(4) 7 . . . ? B2 B4 B5 B1 -138.5(4) 7 . . . ? B1 B4 B5 B1 0.0 . . . . ? C2M B2 B6 C6M -0.7(8) . . . . ? B4 B2 B6 C6M -111.0(6) 7 . . . ? B5 B2 B6 C6M -149.0(5) 7 . . . ? B1 B2 B6 C6M 110.6(6) . . . . ? B3 B2 B6 C6M 148.0(5) . . . . ? C2M B2 B6 B4 110.3(6) . . . 7 ? B4 B2 B6 B4 0.0 7 . . 7 ? B5 B2 B6 B4 -38.0(4) 7 . . 7 ? B1 B2 B6 B4 -138.4(4) . . . 7 ? B3 B2 B6 B4 -101.1(4) . . . 7 ? C2M B2 B6 B3 147.8(5) . . . 7 ? B4 B2 B6 B3 37.5(4) 7 . . 7 ? B5 B2 B6 B3 -0.5(5) 7 . . 7 ? B1 B2 B6 B3 -100.9(4) . . . 7 ? B3 B2 B6 B3 -63.6(5) . . . 7 ? C2M B2 B6 B5 -148.9(5) . . . . ? B4 B2 B6 B5 100.8(4) 7 . . . ? B5 B2 B6 B5 62.8(5) 7 . . . ? B1 B2 B6 B5 -37.6(4) . . . . ? B3 B2 B6 B5 -0.3(5) . . . . ? C2M B2 B6 B1 -111.3(6) . . . . ? B4 B2 B6 B1 138.4(4) 7 . . . ? B5 B2 B6 B1 100.4(4) 7 . . . ? B1 B2 B6 B1 0.0 . . . . ? B3 B2 B6 B1 37.3(4) . . . . ? C5M B5 B6 C6M -0.4(8) . . . . ? B3 B5 B6 C6M 111.4(6) 7 . . . ? B2 B5 B6 C6M 149.2(5) 7 . . . ? B1 B5 B6 C6M -110.5(6) . . . . ? B4 B5 B6 C6M -147.8(5) . . . . ? C5M B5 B6 B4 -148.8(5) . . . 7 ? B3 B5 B6 B4 -37.0(4) 7 . . 7 ? B2 B5 B6 B4 0.7(5) 7 . . 7 ? B1 B5 B6 B4 101.1(4) . . . 7 ? B4 B5 B6 B4 63.8(5) . . . 7 ? C5M B5 B6 B3 -111.8(6) . . . 7 ? B3 B5 B6 B3 0.0 7 . . 7 ? B2 B5 B6 B3 37.7(4) 7 . . 7 ? B1 B5 B6 B3 138.1(4) . . . 7 ? B4 B5 B6 B3 100.8(4) . . . 7 ? C5M B5 B6 B2 147.5(5) . . . . ? B3 B5 B6 B2 -100.7(4) 7 . . . ? B2 B5 B6 B2 -62.9(5) 7 . . . ? B1 B5 B6 B2 37.4(4) . . . . ? B4 B5 B6 B2 0.1(5) . . . . ? C5M B5 B6 B1 110.1(6) . . . . ? B3 B5 B6 B1 -138.1(4) 7 . . . ? B2 B5 B6 B1 -100.4(4) 7 . . . ? B1 B5 B6 B1 0.0 . . . . ? B4 B5 B6 B1 -37.3(4) . . . . ? C1M B1 B6 C6M 1.8(8) . . . . ? B3 B1 B6 C6M -148.0(5) . . . . ? B2 B1 B6 C6M -110.3(6) . . . . ? B4 B1 B6 C6M 148.8(5) . . . . ? B5 B1 B6 C6M 111.4(6) . . . . ? C1M B1 B6 B4 149.5(5) . . . 7 ? B3 B1 B6 B4 -0.3(5) . . . 7 ? B2 B1 B6 B4 37.3(4) . . . 7 ? B4 B1 B6 B4 -63.5(5) . . . 7 ? B5 B1 B6 B4 -100.9(4) . . . 7 ? C1M B1 B6 B3 -147.0(5) . . . 7 ? B3 B1 B6 B3 63.2(5) . . . 7 ? B2 B1 B6 B3 100.9(4) . . . 7 ? B4 B1 B6 B3 0.0(5) . . . 7 ? B5 B1 B6 B3 -37.4(4) . . . 7 ? C1M B1 B6 B2 112.2(6) . . . . ? B3 B1 B6 B2 -37.7(4) . . . . ? B2 B1 B6 B2 0.0 . . . . ? B4 B1 B6 B2 -100.8(4) . . . . ? B5 B1 B6 B2 -138.3(4) . . . . ? C1M B1 B6 B5 -109.6(6) . . . . ? B3 B1 B6 B5 100.6(4) . . . . ? B2 B1 B6 B5 138.3(4) . . . . ? B4 B1 B6 B5 37.4(4) . . . . ? B5 B1 B6 B5 0.0 . . . . ? _refine_diff_density_max 0.340 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.049