# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2004 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_year ? _journal_page_first ? _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'James D. White' 'Christopher M. Lincoln' 'Alexandre F. T. Yokochi' _publ_contact_author_name 'James D. White' _publ_contact_author_address ; Chemistry Oregon State University 153 Gilbert Hall Corvallis USA ; _publ_contact_author_email JAMES.WHITE@OREGONSTATE.EDU _publ_section_title ; Stereochemistry of Contiguous Cyclopropane Formation from Cascade Cyclization of a Skipped Dienyl Homoallyl Triflate ; data_cl101803 _database_code_depnum_ccdc_archive 'CCDC 249269' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H32 O4' _chemical_formula_weight 324.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.2830(7) _cell_length_b 5.5489(5) _cell_length_c 18.4252(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.844(6) _cell_angle_gamma 90.00 _cell_volume 948.99(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4798 _cell_measurement_theta_min 4.74 _cell_measurement_theta_max 70.85 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.132 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 354 _exptl_absorpt_coefficient_mu 0.621 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Shape and scale corrections using equivalent reflections. Shape function based on spherical harmonics. Highest even and odd order for spherical harmonics: 4 and 1 Laue group: 2/m (b) Friedel opposites are equivalent. ; _exptl_absorpt_correction_T_min 0.6894 _exptl_absorpt_correction_T_max 1.0000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ; R-AXIS-CS3 6.X, c++ ; _diffrn_measurement_method '\w sans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6021 _diffrn_reflns_av_R_equivalents 0.0895 _diffrn_reflns_av_sigmaI/netI 0.0605 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.76 _diffrn_reflns_theta_max 59.99 _reflns_number_total 2220 _reflns_number_gt 2080 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement TwinSolve _computing_data_collection CrystalClear _computing_data_reduction TwinSolve _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0883P)^2^+1.2525P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.4(6) _refine_ls_number_reflns 2220 _refine_ls_number_parameters 219 _refine_ls_number_restraints 8 _refine_ls_R_factor_all 0.0818 _refine_ls_R_factor_gt 0.0784 _refine_ls_wR_factor_ref 0.1972 _refine_ls_wR_factor_gt 0.1933 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group O1A O -0.020(4) 0.735(7) 0.5270(7) 0.114(7) Uani 0.50 1 d PDU A 1 H1A H 0.0355 0.6355 0.5101 0.171 Uiso 0.50 1 calc PR A 1 C1A C -0.0034(8) 0.7407(18) 0.6040(3) 0.089(2) Uani 0.50 1 d PD A 1 H1A1 H -0.0352 0.5884 0.6241 0.107 Uiso 0.50 1 calc PR A 1 H1A2 H -0.0634 0.8673 0.6236 0.107 Uiso 0.50 1 calc PR A 1 O1B O -0.029(4) 0.809(7) 0.5303(7) 0.111(7) Uani 0.50 1 d PDU A 2 H1B H -0.0457 0.9540 0.5283 0.166 Uiso 0.50 1 calc PR A 2 C1B C -0.0034(8) 0.7407(18) 0.6040(3) 0.089(2) Uani 0.50 1 d PD A 2 H1B1 H -0.0258 0.5712 0.6100 0.107 Uiso 0.50 1 calc PR A 2 H1B2 H -0.0661 0.8324 0.6353 0.107 Uiso 0.50 1 calc PR A 2 O2 O 0.6500(4) 0.7208(6) 0.77965(16) 0.0431(9) Uani 1 1 d . A . O3 O 0.6408(4) 0.9764(6) 0.69256(16) 0.0416(8) Uani 1 1 d . A . O4 O 0.6168(4) 0.5834(7) 0.66482(18) 0.0560(10) Uani 1 1 d . A . C2 C 0.1509(6) 0.7846(14) 0.6260(3) 0.0650(18) Uani 1 1 d . . . H2 H 0.2223 0.6861 0.6010 0.078 Uiso 1 1 calc R A 1 C3 C 0.1860(6) 0.8431(12) 0.7039(3) 0.0609(17) Uani 1 1 d . A . H3A H 0.2745 0.7782 0.7247 0.073 Uiso 1 1 calc R . . H3B H 0.1067 0.8554 0.7374 0.073 Uiso 1 1 calc R . . C4 C 0.1984(6) 1.0355(13) 0.6455(3) 0.0615(17) Uani 1 1 d . A . H4 H 0.1200 1.1538 0.6455 0.074 Uiso 1 1 calc R . . C5 C 0.3430(7) 1.1406(12) 0.6276(3) 0.0604(17) Uani 1 1 d . . . H5 H 0.3764 1.2691 0.6602 0.072 Uiso 1 1 calc R A . C6 C 0.3805(6) 1.1745(11) 0.5494(3) 0.0586(16) Uani 1 1 d . A . H6A H 0.3133 1.1145 0.5128 0.070 Uiso 1 1 calc R . . H6B H 0.4318 1.3198 0.5361 0.070 Uiso 1 1 calc R . . C7 C 0.4572(5) 0.9951(11) 0.5959(2) 0.0482(13) Uani 1 1 d . A . H7 H 0.4318 0.8265 0.5865 0.058 Uiso 1 1 calc R . . C8 C 0.6109(5) 1.0375(9) 0.6167(2) 0.0420(12) Uani 1 1 d . . . H8A H 0.6721 0.9412 0.5858 0.050 Uiso 1 1 calc R A . H8B H 0.6343 1.2057 0.6087 0.050 Uiso 1 1 calc R . . C9 C 0.6331(5) 0.7404(10) 0.7090(3) 0.0424(12) Uani 1 1 d . . . C10 C 0.6436(6) 0.4742(9) 0.8099(2) 0.0413(12) Uani 1 1 d . . . H10 H 0.6660 0.3575 0.7717 0.050 Uiso 1 1 calc R A . C11 C 0.4932(5) 0.4297(9) 0.8363(3) 0.0423(12) Uani 1 1 d . A . H11A H 0.4257 0.4425 0.7958 0.051 Uiso 1 1 calc R . . H11B H 0.4686 0.5521 0.8716 0.051 Uiso 1 1 calc R . . C12 C 0.4795(5) 0.1796(9) 0.8711(3) 0.0446(13) Uani 1 1 d . . . H12 H 0.5003 0.0601 0.8335 0.054 Uiso 1 1 calc R A . C13 C 0.5948(5) 0.1530(9) 0.9305(3) 0.0471(13) Uani 1 1 d . A . H13A H 0.5727 0.2616 0.9701 0.057 Uiso 1 1 calc R . . H13B H 0.5923 -0.0102 0.9493 0.057 Uiso 1 1 calc R . . C14 C 0.7462(5) 0.2071(9) 0.9039(2) 0.0422(12) Uani 1 1 d . . . H14A H 0.7730 0.0867 0.8684 0.051 Uiso 1 1 calc R A . H14B H 0.8136 0.1961 0.9445 0.051 Uiso 1 1 calc R . . C15 C 0.7575(5) 0.4599(9) 0.8694(2) 0.0394(11) Uani 1 1 d . A . H15 H 0.7316 0.5774 0.9066 0.047 Uiso 1 1 calc R . . C16 C 0.3296(6) 0.1295(11) 0.8978(3) 0.0566(15) Uani 1 1 d . A . H16A H 0.3044 0.2476 0.9335 0.085 Uiso 1 1 calc R . . H16B H 0.3267 -0.0282 0.9192 0.085 Uiso 1 1 calc R . . H16C H 0.2624 0.1372 0.8578 0.085 Uiso 1 1 calc R . . C17 C 0.9093(6) 0.5244(9) 0.8437(3) 0.0443(13) Uani 1 1 d . . . H17 H 0.9005 0.6747 0.8161 0.053 Uiso 1 1 calc R A . C18 C 0.9728(6) 0.3369(11) 0.7927(3) 0.0562(15) Uani 1 1 d . A . H18A H 0.9045 0.3016 0.7545 0.084 Uiso 1 1 calc R . . H18B H 0.9942 0.1923 0.8193 0.084 Uiso 1 1 calc R . . H18C H 1.0597 0.3990 0.7721 0.084 Uiso 1 1 calc R . . C19 C 1.0102(6) 0.5753(11) 0.9073(3) 0.0543(14) Uani 1 1 d . A . H19A H 1.0194 0.4333 0.9368 0.081 Uiso 1 1 calc R . . H19B H 0.9720 0.7044 0.9359 0.081 Uiso 1 1 calc R . . H19C H 1.1031 0.6203 0.8896 0.081 Uiso 1 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 O1A 0.094(7) 0.18(2) 0.072(6) -0.010(7) -0.032(6) -0.007(10) C1A 0.079(4) 0.124(7) 0.063(4) 0.007(5) -0.013(3) 0.004(5) O1B 0.086(7) 0.18(2) 0.064(5) -0.004(7) -0.022(5) -0.009(11) C1B 0.079(4) 0.124(7) 0.063(4) 0.007(5) -0.013(3) 0.004(5) O2 0.069(2) 0.0241(18) 0.0360(17) -0.0030(15) -0.0081(15) 0.0058(17) O3 0.065(2) 0.0245(17) 0.0351(16) -0.0028(14) -0.0053(15) 0.0030(17) O4 0.099(3) 0.0254(19) 0.0431(19) -0.0068(16) -0.0069(19) -0.002(2) C2 0.055(3) 0.084(5) 0.056(3) -0.005(3) -0.005(3) 0.008(4) C3 0.056(3) 0.082(5) 0.045(3) 0.009(3) 0.008(3) 0.003(3) C4 0.054(3) 0.080(5) 0.052(3) 0.016(3) 0.015(3) 0.023(3) C5 0.077(4) 0.066(4) 0.039(3) 0.007(3) 0.007(3) 0.015(3) C6 0.062(3) 0.063(4) 0.050(3) 0.019(3) -0.001(3) 0.008(3) C7 0.055(3) 0.052(4) 0.037(2) 0.002(3) -0.001(2) 0.011(3) C8 0.056(3) 0.034(3) 0.036(2) 0.000(2) 0.002(2) 0.005(3) C9 0.054(3) 0.032(3) 0.041(3) -0.001(2) -0.006(2) 0.001(3) C10 0.060(3) 0.022(2) 0.042(3) -0.001(2) 0.002(2) 0.008(3) C11 0.050(3) 0.035(3) 0.042(3) -0.004(2) -0.003(2) 0.006(2) C12 0.054(3) 0.035(3) 0.045(3) -0.005(2) 0.001(2) 0.006(3) C13 0.055(3) 0.035(3) 0.051(3) 0.003(2) 0.004(2) 0.007(3) C14 0.056(3) 0.032(3) 0.038(2) 0.001(2) -0.001(2) 0.006(2) C15 0.050(3) 0.027(3) 0.041(2) -0.002(2) -0.006(2) 0.011(2) C16 0.051(3) 0.050(4) 0.069(3) -0.001(3) -0.001(3) 0.003(3) C17 0.061(3) 0.028(3) 0.044(3) -0.002(2) 0.003(2) 0.009(3) C18 0.064(3) 0.057(4) 0.048(3) -0.007(3) 0.012(3) 0.010(3) C19 0.056(3) 0.045(3) 0.062(3) -0.011(3) 0.000(3) 0.000(3) _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 O1A C1A 1.426(13) . ? C1A C2 1.502(9) . ? O2 C9 1.313(5) . ? O2 C10 1.479(6) . ? O3 C9 1.346(6) . ? O3 C8 1.461(5) . ? O4 C9 1.201(6) . ? C2 C4 1.502(10) . ? C2 C3 1.503(7) . ? C3 C4 1.522(8) . ? C4 C5 1.505(8) . ? C5 C7 1.461(7) . ? C5 C6 1.500(7) . ? C6 C7 1.489(7) . ? C7 C8 1.490(7) . ? C10 C11 1.505(7) . ? C10 C15 1.514(6) . ? C11 C12 1.535(7) . ? C12 C16 1.508(7) . ? C12 C13 1.526(7) . ? C13 C14 1.525(7) . ? C14 C15 1.545(7) . ? C15 C17 1.535(7) . ? C17 C19 1.516(7) . ? C17 C18 1.527(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 O1A C1A C2 111.1(15) . . ? C9 O2 C10 116.4(4) . . ? C9 O3 C8 115.6(4) . . ? C4 C2 C1A 119.3(6) . . ? C4 C2 C3 60.9(4) . . ? C1A C2 C3 119.0(5) . . ? C2 C3 C4 59.5(4) . . ? C2 C4 C5 124.5(5) . . ? C2 C4 C3 59.6(4) . . ? C5 C4 C3 120.2(5) . . ? C7 C5 C6 60.4(3) . . ? C7 C5 C4 121.9(6) . . ? C6 C5 C4 118.6(5) . . ? C7 C6 C5 58.5(3) . . ? C5 C7 C6 61.1(4) . . ? C5 C7 C8 120.5(5) . . ? C6 C7 C8 119.4(5) . . ? O3 C8 C7 112.1(4) . . ? O4 C9 O2 128.6(5) . . ? O4 C9 O3 124.0(4) . . ? O2 C9 O3 107.3(4) . . ? O2 C10 C11 108.4(4) . . ? O2 C10 C15 106.8(4) . . ? C11 C10 C15 113.5(4) . . ? C10 C11 C12 111.5(4) . . ? C16 C12 C13 112.9(4) . . ? C16 C12 C11 112.7(4) . . ? C13 C12 C11 109.0(4) . . ? C14 C13 C12 113.0(4) . . ? C13 C14 C15 112.3(4) . . ? C10 C15 C17 113.5(4) . . ? C10 C15 C14 107.2(4) . . ? C17 C15 C14 114.0(4) . . ? C19 C17 C18 111.3(4) . . ? C19 C17 C15 111.4(4) . . ? C18 C17 C15 113.3(4) . . ? 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 O1A C1A C2 C4 97.6(18) . . . . ? O1A C1A C2 C3 168.5(18) . . . . ? C1A C2 C3 C4 -109.4(7) . . . . ? C1A C2 C4 C5 -143.4(6) . . . . ? C3 C2 C4 C5 107.7(6) . . . . ? C1A C2 C4 C3 108.9(6) . . . . ? C2 C3 C4 C5 -114.8(6) . . . . ? C2 C4 C5 C7 -6.8(8) . . . . ? C3 C4 C5 C7 65.2(7) . . . . ? C2 C4 C5 C6 64.3(8) . . . . ? C3 C4 C5 C6 136.3(6) . . . . ? C4 C5 C6 C7 -112.5(6) . . . . ? C4 C5 C7 C6 107.1(6) . . . . ? C6 C5 C7 C8 109.0(6) . . . . ? C4 C5 C7 C8 -143.9(5) . . . . ? C5 C6 C7 C8 -110.8(6) . . . . ? C9 O3 C8 C7 68.1(5) . . . . ? C5 C7 C8 O3 66.6(6) . . . . ? C6 C7 C8 O3 138.5(5) . . . . ? C10 O2 C9 O4 -2.3(8) . . . . ? C10 O2 C9 O3 179.3(4) . . . . ? C8 O3 C9 O4 7.0(7) . . . . ? C8 O3 C9 O2 -174.5(4) . . . . ? C9 O2 C10 C11 -96.4(4) . . . . ? C9 O2 C10 C15 140.9(4) . . . . ? O2 C10 C11 C12 -177.9(3) . . . . ? C15 C10 C11 C12 -59.4(5) . . . . ? C10 C11 C12 C16 -179.7(4) . . . . ? C10 C11 C12 C13 54.2(5) . . . . ? C16 C12 C13 C14 -179.2(4) . . . . ? C11 C12 C13 C14 -53.2(5) . . . . ? C12 C13 C14 C15 55.7(5) . . . . ? O2 C10 C15 C17 -56.1(5) . . . . ? C11 C10 C15 C17 -175.5(4) . . . . ? O2 C10 C15 C14 177.1(3) . . . . ? C11 C10 C15 C14 57.7(5) . . . . ? C13 C14 C15 C10 -55.0(5) . . . . ? C13 C14 C15 C17 178.4(4) . . . . ? C10 C15 C17 C19 164.2(4) . . . . ? C14 C15 C17 C19 -72.7(5) . . . . ? C10 C15 C17 C18 -69.4(5) . . . . ? C14 C15 C17 C18 53.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1A H1A O1A 0.82 2.33 2.972(14) 136.0 2_546 O1B H1B O1B 0.82 2.36 3.044(17) 141.8 2_556 _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 59.99 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.242 _refine_diff_density_min -0.305 _refine_diff_density_rms 0.058 data_cl021904 _database_code_depnum_ccdc_archive 'CCDC 249270' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H34 N2 O9' _chemical_formula_weight 518.55 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 7.5080(3) _cell_length_b 8.6340(3) _cell_length_c 40.4790(15) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2624.01(17) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 20771 _cell_measurement_theta_min 3.13 _cell_measurement_theta_max 71.10 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.313 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 0.830 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; Shape and scale corrections using equivalent reflections. Shape function based on spherical harmonics. Highest even and odd order for spherical harmonics: 4 and 1 Laue group: mmm Friedel opposites are equivalent. ; _exptl_absorpt_correction_T_min 0.5340 _exptl_absorpt_correction_T_max 1.0000 _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54180 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'R-AXIS-CS3 6.X, c++' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27905 _diffrn_reflns_av_sigmaI/netI 0.004 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 71.31 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -48 _diffrn_reflns_limit_l_max 49 _reflns_number_total 3925 _reflns_number_gt 3822 _reflns_threshold_expression >2sigma(I) _computing_data_collection TwinSolve _computing_cell_refinement TwinSolve _computing_data_reduction TwinSolve _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III for windows (Farrugia, 1997)' _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness 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 threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) 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 _refine_ls_weighting_details 'calc w==1/[\s^2^(Fo^2^)+(0.0360P)^2^+3.6243P] 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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.0(3) _refine_ls_number_reflns 3925 _refine_ls_number_parameters 337 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.1190 _refine_ls_wR_factor_gt 0.1180 _refine_ls_goodness_of_fit_ref 1.087 _refine_ls_restrained_S_all 1.087 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5265(5) 0.4383(4) 0.18637(7) 0.0277(7) Uani 1 1 d . . . H1A H 0.4207 0.4963 0.1786 0.033 Uiso 1 1 calc R . . H1B H 0.6118 0.5129 0.1961 0.033 Uiso 1 1 calc R . . C2 C 0.4730(5) 0.3216(4) 0.21151(8) 0.0301(8) Uani 1 1 d . . . H2 H 0.5731 0.2724 0.2240 0.036 Uiso 1 1 calc R . . C3 C 0.3172(5) 0.2189(4) 0.20470(9) 0.0355(9) Uani 1 1 d . . . H3A H 0.2517 0.2349 0.1837 0.043 Uiso 1 1 calc R . . H3B H 0.3248 0.1098 0.2121 0.043 Uiso 1 1 calc R . . C4 C 0.3009(5) 0.3409(4) 0.23067(8) 0.0318(8) Uani 1 1 d . . . H4 H 0.3079 0.2983 0.2536 0.038 Uiso 1 1 calc R . . C5 C 0.1764(5) 0.4752(4) 0.22784(7) 0.0283(8) Uani 1 1 d . . . H5 H 0.2162 0.5689 0.2403 0.034 Uiso 1 1 calc R . . C6 C -0.0202(5) 0.4488(4) 0.22903(8) 0.0320(8) Uani 1 1 d . . . H6A H -0.0926 0.5203 0.2426 0.038 Uiso 1 1 calc R . . H6B H -0.0631 0.3404 0.2287 0.038 Uiso 1 1 calc R . . C7 C 0.0623(5) 0.5122(4) 0.19791(8) 0.0287(8) Uani 1 1 d . . . H7 H 0.0717 0.4384 0.1789 0.034 Uiso 1 1 calc R . . C8 C 0.0234(5) 0.6761(4) 0.18926(8) 0.0280(7) Uani 1 1 d . . . H8A H -0.0922 0.6816 0.1776 0.034 Uiso 1 1 calc R . . H8B H 0.0134 0.7380 0.2098 0.034 Uiso 1 1 calc R . . N21 N 0.8863(4) 1.0461(3) 0.16583(7) 0.0314(7) Uani 1 1 d . . . N22 N 0.5387(5) 0.8863(3) 0.06977(7) 0.0365(8) Uani 1 1 d . . . O21 O 0.1635(3) 0.7421(2) 0.16819(5) 0.0287(5) Uani 1 1 d . . . O22 O 0.3141(4) 0.8242(3) 0.21309(5) 0.0336(6) Uani 1 1 d . . . O23 O 1.0145(4) 1.0658(3) 0.14723(6) 0.0419(6) Uani 1 1 d . . . O24 O 0.8902(4) 1.0723(3) 0.19558(6) 0.0461(7) Uani 1 1 d . . . O25 O 0.6604(4) 0.9344(4) 0.05235(6) 0.0535(8) Uani 1 1 d . . . O26 O 0.4034(4) 0.8210(3) 0.05931(6) 0.0455(7) Uani 1 1 d . . . C21 C 0.2998(5) 0.8114(3) 0.18352(7) 0.0258(7) Uani 1 1 d . . . C22 C 0.4350(5) 0.8704(3) 0.15973(7) 0.0251(7) Uani 1 1 d . . . C23 C 0.4153(5) 0.8562(3) 0.12578(8) 0.0265(7) Uani 1 1 d . . . H23 H 0.3098 0.8135 0.1166 0.032 Uiso 1 1 calc R . . C24 C 0.5534(5) 0.9060(3) 0.10568(7) 0.0267(8) Uani 1 1 d . . . C25 C 0.7100(5) 0.9688(3) 0.11790(8) 0.0280(8) Uani 1 1 d . . . H25 H 0.8039 1.0006 0.1037 0.034 Uiso 1 1 calc R . . C26 C 0.7224(5) 0.9824(3) 0.15181(8) 0.0263(7) Uani 1 1 d . . . C27 C 0.5887(5) 0.9363(3) 0.17296(7) 0.0263(7) Uani 1 1 d . . . H27 H 0.6011 0.9492 0.1962 0.032 Uiso 1 1 calc R . . C31 C 0.6719(4) 0.4490(3) 0.13492(7) 0.0221(7) Uani 1 1 d . . . C32 C 0.7999(5) 0.4413(4) 0.08093(7) 0.0270(7) Uani 1 1 d . . . H32 H 0.8394 0.5480 0.0872 0.032 Uiso 1 1 calc R . . C33 C 0.6490(5) 0.4515(4) 0.05597(8) 0.0331(8) Uani 1 1 d . . . H33A H 0.5514 0.5150 0.0653 0.040 Uiso 1 1 calc R . . H33B H 0.6017 0.3464 0.0517 0.040 Uiso 1 1 calc R . . C34 C 0.7121(5) 0.5233(4) 0.02342(8) 0.0371(9) Uani 1 1 d . . . H34 H 0.7555 0.6307 0.0281 0.044 Uiso 1 1 calc R . . C35 C 0.5581(6) 0.5337(5) -0.00153(10) 0.0518(11) Uani 1 1 d . . . H35A H 0.6006 0.5824 -0.0219 0.078 Uiso 1 1 calc R . . H35B H 0.4615 0.5960 0.0079 0.078 Uiso 1 1 calc R . . H35C H 0.5141 0.4294 -0.0064 0.078 Uiso 1 1 calc R . . C36 C 0.8668(5) 0.4290(5) 0.01035(8) 0.0385(9) Uani 1 1 d . . . H36A H 0.9108 0.4760 -0.0104 0.046 Uiso 1 1 calc R . . H36B H 0.8257 0.3226 0.0053 0.046 Uiso 1 1 calc R . . C37 C 1.0188(5) 0.4220(4) 0.03555(8) 0.0317(8) Uani 1 1 d . . . H37A H 1.0640 0.5280 0.0397 0.038 Uiso 1 1 calc R . . H37B H 1.1179 0.3597 0.0264 0.038 Uiso 1 1 calc R . . C38 C 0.9572(5) 0.3498(4) 0.06847(7) 0.0272(7) Uani 1 1 d . . . H38 H 0.9146 0.2424 0.0636 0.033 Uiso 1 1 calc R . . C39 C 1.1067(5) 0.3370(4) 0.09455(8) 0.0292(8) Uani 1 1 d . . . H39 H 1.0495 0.3000 0.1154 0.035 Uiso 1 1 calc R . . C310 C 1.1941(5) 0.4923(4) 0.10244(9) 0.0375(9) Uani 1 1 d . . . H31D H 1.2850 0.4776 0.1195 0.056 Uiso 1 1 calc R . . H31E H 1.1035 0.5650 0.1104 0.056 Uiso 1 1 calc R . . H31F H 1.2498 0.5340 0.0824 0.056 Uiso 1 1 calc R . . C311 C 1.2453(5) 0.2153(4) 0.08493(9) 0.0380(9) Uani 1 1 d . . . H31A H 1.3053 0.2474 0.0645 0.057 Uiso 1 1 calc R . . H31B H 1.1863 0.1155 0.0814 0.057 Uiso 1 1 calc R . . H31C H 1.3333 0.2051 0.1027 0.057 Uiso 1 1 calc R . . O31 O 0.6098(3) 0.3558(2) 0.15865(5) 0.0275(5) Uani 1 1 d . . . O32 O 0.6753(3) 0.5877(2) 0.13595(5) 0.0301(5) Uani 1 1 d . . . O33 O 0.7314(3) 0.3604(2) 0.11048(5) 0.0298(6) Uani 1 1 d . . . 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 C1 0.024(2) 0.0312(17) 0.0276(15) -0.0026(13) 0.0056(14) 0.0023(14) C2 0.027(2) 0.0316(17) 0.0317(15) -0.0002(14) 0.0055(14) 0.0013(15) C3 0.039(3) 0.0272(17) 0.0405(18) -0.0001(14) 0.0072(17) -0.0017(16) C4 0.032(2) 0.0301(17) 0.0334(16) 0.0033(14) 0.0124(15) 0.0024(15) C5 0.026(2) 0.0305(17) 0.0283(15) -0.0008(13) 0.0083(14) 0.0015(14) C6 0.027(2) 0.0308(17) 0.0380(17) 0.0000(14) 0.0089(15) 0.0002(15) C7 0.026(2) 0.0310(17) 0.0288(15) -0.0063(13) 0.0043(14) -0.0007(14) C8 0.019(2) 0.0261(16) 0.0392(17) 0.0000(13) 0.0029(14) -0.0003(13) N21 0.028(2) 0.0269(14) 0.0397(15) 0.0083(12) -0.0020(13) -0.0060(12) N22 0.045(2) 0.0322(16) 0.0325(14) 0.0066(12) -0.0022(15) -0.0008(14) O21 0.0249(15) 0.0263(11) 0.0349(11) 0.0011(9) 0.0012(10) -0.0028(10) O22 0.0351(17) 0.0354(13) 0.0304(11) -0.0040(10) 0.0034(10) -0.0080(11) O23 0.0271(17) 0.0473(15) 0.0514(14) 0.0127(12) 0.0030(12) -0.0097(12) O24 0.0435(19) 0.0561(16) 0.0389(14) -0.0006(12) -0.0037(12) -0.0165(14) O25 0.051(2) 0.074(2) 0.0348(13) 0.0090(13) 0.0092(13) -0.0072(16) O26 0.056(2) 0.0459(16) 0.0345(13) 0.0019(11) -0.0072(12) -0.0127(14) C21 0.025(2) 0.0177(14) 0.0344(17) -0.0023(12) 0.0016(14) 0.0000(13) C22 0.026(2) 0.0189(14) 0.0305(15) -0.0018(12) -0.0003(14) -0.0004(13) C23 0.025(2) 0.0187(14) 0.0359(16) 0.0007(12) -0.0018(15) 0.0032(13) C24 0.030(2) 0.0203(14) 0.0296(15) 0.0039(12) 0.0026(14) 0.0019(13) C25 0.029(2) 0.0197(15) 0.0353(16) 0.0071(13) 0.0081(14) 0.0046(14) C26 0.023(2) 0.0208(15) 0.0353(16) 0.0026(12) -0.0014(14) -0.0022(13) C27 0.032(2) 0.0169(14) 0.0297(15) 0.0000(12) 0.0026(14) -0.0003(13) C31 0.0155(19) 0.0210(15) 0.0297(15) 0.0013(12) 0.0032(13) 0.0020(13) C32 0.023(2) 0.0257(16) 0.0320(15) 0.0025(13) 0.0105(14) -0.0032(14) C33 0.024(2) 0.0313(18) 0.0438(19) 0.0004(15) 0.0054(15) 0.0066(15) C34 0.033(3) 0.044(2) 0.0344(17) 0.0041(15) 0.0012(16) 0.0038(17) C35 0.044(3) 0.063(3) 0.048(2) 0.001(2) -0.0073(19) 0.007(2) C36 0.037(3) 0.051(2) 0.0276(16) 0.0030(15) 0.0042(16) 0.0037(17) C37 0.027(2) 0.0384(19) 0.0295(15) 0.0018(13) 0.0093(14) -0.0032(15) C38 0.024(2) 0.0290(16) 0.0291(15) 0.0002(13) 0.0063(14) -0.0026(14) C39 0.025(2) 0.0311(17) 0.0318(16) 0.0029(13) 0.0043(14) -0.0016(15) C310 0.033(3) 0.0390(19) 0.0409(18) -0.0065(15) 0.0022(16) -0.0003(17) C311 0.031(3) 0.0364(19) 0.0470(19) 0.0043(16) 0.0015(17) 0.0062(16) O31 0.0288(14) 0.0234(11) 0.0302(11) 0.0037(9) 0.0095(10) 0.0050(9) O32 0.0330(16) 0.0238(11) 0.0337(11) 0.0000(9) 0.0089(10) 0.0005(10) O33 0.0335(16) 0.0219(11) 0.0341(11) 0.0005(9) 0.0159(10) -0.0010(10) _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 C1 O31 1.469(3) . ? C1 C2 1.487(4) . ? C2 C3 1.493(5) . ? C2 C4 1.516(5) . ? C3 C4 1.493(5) . ? C4 C5 1.494(5) . ? C5 C6 1.494(5) . ? C5 C7 1.517(5) . ? C6 C7 1.507(4) . ? C7 C8 1.487(4) . ? C8 O21 1.469(4) . ? N21 O24 1.225(3) . ? N21 O23 1.234(4) . ? N21 C26 1.463(4) . ? N22 O25 1.227(4) . ? N22 O26 1.236(4) . ? N22 C24 1.467(4) . ? O21 C21 1.338(4) . ? O22 C21 1.207(4) . ? C21 C22 1.489(4) . ? C22 C23 1.388(4) . ? C22 C27 1.393(5) . ? C23 C24 1.386(5) . ? C24 C25 1.386(5) . ? C25 C26 1.381(4) . ? C26 C27 1.378(5) . ? C31 O32 1.199(4) . ? C31 O33 1.328(3) . ? C31 O31 1.337(4) . ? C32 O33 1.478(3) . ? C32 C38 1.508(5) . ? C32 C33 1.520(5) . ? C33 C34 1.531(5) . ? C34 C36 1.514(5) . ? C34 C35 1.538(5) . ? C36 C37 1.532(5) . ? C37 C38 1.542(4) . ? C38 C39 1.545(5) . ? C39 C310 1.527(5) . ? C39 C311 1.529(5) . ? 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 O31 C1 C2 108.0(2) . . ? C1 C2 C3 119.2(3) . . ? C1 C2 C4 120.4(3) . . ? C3 C2 C4 59.5(2) . . ? C4 C3 C2 61.0(2) . . ? C3 C4 C5 123.0(3) . . ? C3 C4 C2 59.5(2) . . ? C5 C4 C2 125.4(3) . . ? C6 C5 C4 119.8(3) . . ? C6 C5 C7 60.0(2) . . ? C4 C5 C7 125.3(3) . . ? C5 C6 C7 60.7(2) . . ? C8 C7 C6 117.5(3) . . ? C8 C7 C5 119.9(3) . . ? C6 C7 C5 59.2(2) . . ? O21 C8 C7 111.4(3) . . ? O24 N21 O23 123.8(3) . . ? O24 N21 C26 118.1(3) . . ? O23 N21 C26 118.1(3) . . ? O25 N22 O26 124.7(3) . . ? O25 N22 C24 118.3(3) . . ? O26 N22 C24 117.0(3) . . ? C21 O21 C8 116.8(2) . . ? O22 C21 O21 124.7(3) . . ? O22 C21 C22 123.3(3) . . ? O21 C21 C22 112.0(3) . . ? C23 C22 C27 120.3(3) . . ? C23 C22 C21 122.5(3) . . ? C27 C22 C21 117.1(3) . . ? C24 C23 C22 118.3(3) . . ? C23 C24 C25 123.1(3) . . ? C23 C24 N22 119.3(3) . . ? C25 C24 N22 117.6(3) . . ? C26 C25 C24 116.4(3) . . ? C27 C26 C25 122.9(3) . . ? C27 C26 N21 118.7(3) . . ? C25 C26 N21 118.3(3) . . ? C26 C27 C22 118.8(3) . . ? O32 C31 O33 126.5(3) . . ? O32 C31 O31 125.7(3) . . ? O33 C31 O31 107.8(2) . . ? O33 C32 C38 107.2(2) . . ? O33 C32 C33 107.8(3) . . ? C38 C32 C33 113.0(3) . . ? C32 C33 C34 111.4(3) . . ? C36 C34 C33 108.7(3) . . ? C36 C34 C35 112.3(3) . . ? C33 C34 C35 110.9(3) . . ? C34 C36 C37 111.1(3) . . ? C36 C37 C38 111.6(3) . . ? C32 C38 C37 108.2(3) . . ? C32 C38 C39 112.2(3) . . ? C37 C38 C39 113.7(3) . . ? C310 C39 C311 111.4(3) . . ? C310 C39 C38 113.1(3) . . ? C311 C39 C38 111.7(3) . . ? C31 O31 C1 113.9(2) . . ? C31 O33 C32 116.6(2) . . ? 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 O31 C1 C2 C3 -72.8(4) . . . . ? O31 C1 C2 C4 -142.5(3) . . . . ? C1 C2 C3 C4 -110.1(3) . . . . ? C2 C3 C4 C5 114.8(4) . . . . ? C1 C2 C4 C3 108.1(4) . . . . ? C1 C2 C4 C5 -2.9(5) . . . . ? C3 C2 C4 C5 -110.9(4) . . . . ? C3 C4 C5 C6 67.8(4) . . . . ? C2 C4 C5 C6 141.5(3) . . . . ? C3 C4 C5 C7 -4.8(5) . . . . ? C2 C4 C5 C7 68.9(5) . . . . ? C4 C5 C6 C7 -116.0(3) . . . . ? C5 C6 C7 C8 -110.2(3) . . . . ? C6 C5 C7 C8 106.1(3) . . . . ? C4 C5 C7 C8 -146.7(3) . . . . ? C4 C5 C7 C6 107.2(4) . . . . ? C6 C7 C8 O21 155.6(3) . . . . ? C5 C7 C8 O21 87.1(3) . . . . ? C7 C8 O21 C21 -90.1(3) . . . . ? C8 O21 C21 O22 -0.7(4) . . . . ? C8 O21 C21 C22 178.7(2) . . . . ? O22 C21 C22 C23 -179.2(3) . . . . ? O21 C21 C22 C23 1.4(4) . . . . ? O22 C21 C22 C27 3.3(5) . . . . ? O21 C21 C22 C27 -176.1(3) . . . . ? C27 C22 C23 C24 1.4(5) . . . . ? C21 C22 C23 C24 -176.0(3) . . . . ? C22 C23 C24 C25 0.2(5) . . . . ? C22 C23 C24 N22 177.5(3) . . . . ? O25 N22 C24 C23 178.3(3) . . . . ? O26 N22 C24 C23 -2.1(4) . . . . ? O25 N22 C24 C25 -4.2(5) . . . . ? O26 N22 C24 C25 175.4(3) . . . . ? C23 C24 C25 C26 -1.0(5) . . . . ? N22 C24 C25 C26 -178.4(3) . . . . ? C24 C25 C26 C27 0.4(5) . . . . ? C24 C25 C26 N21 179.2(3) . . . . ? O24 N21 C26 C27 -8.3(4) . . . . ? O23 N21 C26 C27 169.6(3) . . . . ? O24 N21 C26 C25 172.9(3) . . . . ? O23 N21 C26 C25 -9.3(4) . . . . ? C25 C26 C27 C22 1.1(5) . . . . ? N21 C26 C27 C22 -177.7(3) . . . . ? C23 C22 C27 C26 -2.0(4) . . . . ? C21 C22 C27 C26 175.5(3) . . . . ? O33 C32 C33 C34 -175.8(3) . . . . ? C38 C32 C33 C34 -57.5(4) . . . . ? C32 C33 C34 C36 56.5(4) . . . . ? C32 C33 C34 C35 -179.7(3) . . . . ? C33 C34 C36 C37 -57.6(4) . . . . ? C35 C34 C36 C37 179.4(3) . . . . ? C34 C36 C37 C38 59.0(4) . . . . ? O33 C32 C38 C37 174.1(3) . . . . ? C33 C32 C38 C37 55.4(4) . . . . ? O33 C32 C38 C39 -59.7(3) . . . . ? C33 C32 C38 C39 -178.4(3) . . . . ? C36 C37 C38 C32 -55.8(4) . . . . ? C36 C37 C38 C39 178.9(3) . . . . ? C32 C38 C39 C310 -66.3(4) . . . . ? C37 C38 C39 C310 56.8(4) . . . . ? C32 C38 C39 C311 167.1(3) . . . . ? C37 C38 C39 C311 -69.7(4) . . . . ? O32 C31 O31 C1 5.6(5) . . . . ? O33 C31 O31 C1 -175.5(3) . . . . ? C2 C1 O31 C31 -177.0(3) . . . . ? O32 C31 O33 C32 -3.4(5) . . . . ? O31 C31 O33 C32 177.7(3) . . . . ? C38 C32 O33 C31 143.0(3) . . . . ? C33 C32 O33 C31 -95.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.858 _diffrn_reflns_theta_full 67.48 _diffrn_measured_fraction_theta_full 0.858 _refine_diff_density_max 0.310 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.047