# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 1999 # CCDC Number: 188/178 data_ute2 _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural '[Ph--C(.5)-(CH2)2-COC]2' _chemical_formula_analytical ? _chemical_formula_sum 'C20 H18 O4' _chemical_formula_weight 322.36 _chemical_melting_point 218-224 _chemical_compound_source ? 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' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.4970(10) _cell_length_b 8.4210(10) _cell_length_c 10.0870(10) _cell_angle_alpha 90.00 _cell_angle_beta 95.910(10) _cell_angle_gamma 90.00 _cell_volume 802.41(15) _cell_formula_units_Z 2 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 32 _cell_measurement_theta_min 17.8 _cell_measurement_theta_max 19.7 _exptl_crystal_description 'plates' _exptl_crystal_colour 'colourless' _exptl_crystal_size_max 0.760 _exptl_crystal_size_mid 0.475 _exptl_crystal_size_min 0.190 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method ? _exptl_crystal_F_000 340 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type no _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Stoe STADI 4 diffractometer' _diffrn_measurement_method 'omega-2theta-scans' _diffrn_standards_number 4 _diffrn_standards_interval_count ? _diffrn_standards_interval_time 4 _diffrn_standards_decay_% 15 _diffrn_reflns_number 3130 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_sigmaI/netI 0.0192 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 24.94 _reflns_number_total 1401 _reflns_number_observed 1263 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'STADI 4 (STOE, 1995)' _computing_cell_refinement 'STADI 4 (STOE, 1995)' _computing_data_reduction 'X-RED (STOE, 1995)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material '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^)+(0.0370P)^2^+0.1201P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment free _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0333(43) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 1401 _refine_ls_number_parameters 146 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_obs 0.0324 _refine_ls_wR_factor_all 0.0818 _refine_ls_wR_factor_obs 0.0792 _refine_ls_goodness_of_fit_all 1.123 _refine_ls_goodness_of_fit_obs 1.153 _refine_ls_restrained_S_all 1.123 _refine_ls_restrained_S_obs 1.153 _refine_ls_shift/esd_max 0.004 _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 O1 O 0.07496(9) 0.20018(10) 0.01879(8) 0.0436(3) Uani 1 d . . C2 C 0.21441(14) 0.2158(2) 0.00086(14) 0.0489(3) Uani 1 d . . O2 O 0.28411(11) 0.31806(13) 0.05818(12) 0.0683(4) Uani 1 d . . C3 C 0.25687(15) 0.0921(2) -0.0932(2) 0.0549(4) Uani 1 d . . H31 H 0.3067(18) 0.1424(20) -0.1573(18) 0.069(5) Uiso 1 d . . H32 H 0.3210(17) 0.0155(19) -0.0421(16) 0.064(4) Uiso 1 d . . C4 C 0.11937(14) 0.0146(2) -0.15013(13) 0.0456(3) Uani 1 d . . H41 H 0.1251(14) -0.0992(19) -0.1564(14) 0.051(4) Uiso 1 d . . H42 H 0.0899(14) 0.0591(17) -0.2386(15) 0.052(4) Uiso 1 d . . C5 C 0.01072(12) 0.06520(14) -0.05419(11) 0.0379(3) Uani 1 d . . C6 C -0.12972(12) 0.11857(15) -0.12566(11) 0.0396(3) Uani 1 d . . C7 C -0.19867(14) 0.2535(2) -0.08688(14) 0.0468(3) Uani 1 d . . H7 H -0.1554(15) 0.3173(17) -0.0196(15) 0.052(4) Uiso 1 d . . C8 C -0.32974(15) 0.2958(2) -0.1503(2) 0.0558(4) Uani 1 d . . H8 H -0.3746(17) 0.3913(20) -0.1220(15) 0.060(4) Uiso 1 d . . C9 C -0.3932(2) 0.2049(2) -0.2530(2) 0.0580(4) Uani 1 d . . H9 H -0.4839(18) 0.2364(20) -0.2965(16) 0.069(5) Uiso 1 d . . C10 C -0.3250(2) 0.0715(2) -0.29345(14) 0.0554(4) Uani 1 d . . H10 H -0.3644(17) 0.0059(19) -0.3651(17) 0.065(4) Uiso 1 d . . C11 C -0.19362(14) 0.0286(2) -0.23130(13) 0.0471(3) Uani 1 d . . H11 H -0.1452(15) -0.0664(18) -0.2600(15) 0.053(4) Uiso 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 O1 0.0408(5) 0.0461(5) 0.0430(5) -0.0056(4) 0.0001(4) -0.0066(4) C2 0.0422(7) 0.0543(8) 0.0488(8) 0.0099(6) -0.0022(6) -0.0091(6) O2 0.0585(7) 0.0677(7) 0.0753(8) -0.0003(6) -0.0101(5) -0.0244(5) C3 0.0413(8) 0.0716(10) 0.0532(8) 0.0067(7) 0.0120(6) -0.0060(7) C4 0.0433(7) 0.0590(9) 0.0354(7) -0.0008(6) 0.0089(5) -0.0011(6) C5 0.0375(7) 0.0439(7) 0.0319(6) -0.0048(5) 0.0022(5) -0.0041(5) C6 0.0381(7) 0.0486(7) 0.0321(6) 0.0028(5) 0.0046(5) -0.0043(5) C7 0.0441(7) 0.0527(8) 0.0434(7) -0.0017(6) 0.0030(6) -0.0010(6) C8 0.0450(8) 0.0630(9) 0.0594(9) 0.0067(7) 0.0060(6) 0.0073(7) C9 0.0378(7) 0.0821(11) 0.0527(9) 0.0144(8) -0.0017(6) -0.0024(7) C10 0.0491(8) 0.0744(10) 0.0408(8) 0.0019(7) -0.0045(6) -0.0127(7) C11 0.0474(8) 0.0568(8) 0.0364(7) -0.0017(6) 0.0006(5) -0.0042(6) _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 O1 C2 1.361(2) . ? O1 C5 1.4539(14) . ? C2 O2 1.198(2) . ? C2 C3 1.492(2) . ? C3 C4 1.519(2) . ? C3 H31 0.94(2) . ? C3 H32 0.99(2) . ? C4 C5 1.545(2) . ? C4 H41 0.96(2) . ? C4 H42 0.98(2) . ? C5 C6 1.517(2) . ? C5 C5 1.577(2) 3 ? C6 C7 1.387(2) . ? C6 C11 1.394(2) . ? C7 C8 1.386(2) . ? C7 H7 0.93(2) . ? C8 C9 1.376(2) . ? C8 H8 0.97(2) . ? C9 C10 1.379(2) . ? C9 H9 0.96(2) . ? C10 C11 1.385(2) . ? C10 H10 0.95(2) . ? C11 H11 0.981(15) . ? 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 C2 O1 C5 111.80(10) . . ? O2 C2 O1 120.12(14) . . ? O2 C2 C3 129.54(13) . . ? O1 C2 C3 110.33(11) . . ? C2 C3 C4 105.20(11) . . ? C2 C3 H31 108.1(10) . . ? C4 C3 H31 114.1(10) . . ? C2 C3 H32 108.3(9) . . ? C4 C3 H32 112.0(9) . . ? H31 C3 H32 108.9(13) . . ? C3 C4 C5 104.38(11) . . ? C3 C4 H41 113.6(8) . . ? C5 C4 H41 111.2(9) . . ? C3 C4 H42 109.5(8) . . ? C5 C4 H42 108.5(8) . . ? H41 C4 H42 109.5(12) . . ? O1 C5 C6 108.15(10) . . ? O1 C5 C4 105.08(9) . . ? C6 C5 C4 113.27(10) . . ? O1 C5 C5 105.71(11) . 3 ? C6 C5 C5 111.44(12) . 3 ? C4 C5 C5 112.60(13) . 3 ? C7 C6 C11 118.64(12) . . ? C7 C6 C5 121.73(11) . . ? C11 C6 C5 119.62(11) . . ? C8 C7 C6 120.54(13) . . ? C8 C7 H7 119.8(9) . . ? C6 C7 H7 119.6(9) . . ? C9 C8 C7 120.46(15) . . ? C9 C8 H8 120.9(9) . . ? C7 C8 H8 118.7(9) . . ? C8 C9 C10 119.58(14) . . ? C8 C9 H9 119.5(10) . . ? C10 C9 H9 120.9(10) . . ? C9 C10 C11 120.43(14) . . ? C9 C10 H10 122.4(10) . . ? C11 C10 H10 117.1(10) . . ? C10 C11 C6 120.34(14) . . ? C10 C11 H11 120.4(8) . . ? C6 C11 H11 119.2(9) . . ? _refine_diff_density_max 0.196 _refine_diff_density_min -0.100 _refine_diff_density_rms 0.025 data_AZ _audit_creation_date 97-07-03 _audit_creation_method CRYSTALS #========================================================================== _chemical_name_systematic ; # IUPAC name, in full ? ; _cell_length_a 10.118(1) _cell_angle_alpha 90 _cell_length_b 10.114(2) _cell_angle_beta 104.2(3) _cell_length_c 11.853(1) _cell_angle_gamma 90 _cell_volume 1176.0(2) _symmetry_cell_setting 'monoclinic' _symmetry_space_group_name_H-M 'P 21' loop_ _symmetry_equiv_pos_as_xyz 'x,y,z' '-x,y+1/2,-z' loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source 'C ' 0.0170 0.0090 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International_Tables_Vol_IV_Table_2.2B' 'H ' 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7997 0.0030 'International_Tables_Vol_IV_Table_2.2B' 'N ' 0.0290 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International_Tables_Vol_IV_Table_2.2B' 'O ' 0.0470 0.0320 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International_Tables_Vol_IV_Table_2.2B' _chemical_formula_sum ' C26 H32 O4 N2 ' _chemical_formula_moiety ' C26 H32 O4 N2 ' _chemical_compound_source ; ? ; _chemical_formula_weight 436.55 _cell_measurement_reflns_used 24 _cell_measurement_theta_min 19 _cell_measurement_theta_max 43 _cell_measurement_temperature 298 _cell_formula_units_Z 2 _exptl_crystal_description ' prism ' _exptl_crystal_colour ' colourless ' _exptl_crystal_size_min 0.25 _exptl_crystal_size_mid 0.66 _exptl_crystal_size_max 0.70 _exptl_crystal_density_diffrn 1.23 _exptl_crystal_density_meas ? _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.63 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details '\y scan' _exptl_absorpt_correction_T_min 0.77 _exptl_absorpt_correction_T_max 1.00 _diffrn_standards_interval_time 120 _diffrn_standards_interval_count ? _diffrn_standards_number 3 _diffrn_standards_decay_% 4.95 _diffrn_ambient_temperature 298 _diffrn_reflns_number 2663 _reflns_number_total 2535 _diffrn_reflns_av_R_equivalents 0.05 _reflns_number_observed 2371 _diffrn_reflns_theta_min 2.77 _diffrn_reflns_theta_max 74.33 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 0 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _reflns_observed_criterion >3.00\s(I) _refine_diff_density_min -0.14 _refine_diff_density_max 0.19 _refine_ls_number_reflns 2371 _refine_ls_number_parameters 298 _refine_ls_R_factor_obs 0.0400 _refine_ls_wR_factor_obs 0.0482 _refine_ls_goodness_of_fit_obs 0.9783 _refine_ls_shift/esd_max 0.000701 _refine_ls_abs_structure_details 'not refined' _refine_ls_structure_factor_coef F _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_measurement_method 2\q/\w # Uequiv = arithmetic mean of Ui # i.e. Ueqiv = (U1+U2+U3)/3 loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_thermal_displace_type O1 0.6322(2) -0.3685(2) 0.9189(1) 0.0543 1.0000 Uani C1 0.5867(2) -0.3123(2) 0.8061(2) 0.0446 1.0000 Uani C2 0.5508(2) -0.1656(2) 0.8184(2) 0.0505 1.0000 Uani C3 0.6711(2) -0.0875(2) 0.8902(2) 0.0568 1.0000 Uani C4 0.6357(2) 0.0543(2) 0.9109(2) 0.0490 1.0000 Uani O2 0.5189(2) 0.0952(2) 0.9010(2) 0.0724 1.0000 Uani N1 0.7437(2) 0.1339(2) 0.9419(2) 0.0559 1.0000 Uani C5 0.7046(2) -0.3269(2) 0.7474(2) 0.0451 1.0000 Uani C6 0.7213(2) -0.2419(3) 0.6592(2) 0.0568 1.0000 Uani C7 0.8327(3) -0.2556(4) 0.6108(2) 0.0717 1.0000 Uani C8 0.9272(3) -0.3547(4) 0.6472(3) 0.0740 1.0000 Uani C9 0.9107(2) -0.4392(3) 0.7326(3) 0.0698 1.0000 Uani C10 0.8021(2) -0.4249(2) 0.7835(2) 0.0565 1.0000 Uani C11 0.7531(3) 0.2696(2) 0.9845(2) 0.0619 1.0000 Uani C12 0.9073(3) 0.2551(3) 1.0166(4) 0.0863 1.0000 Uani C13 0.8884(3) 0.1088(3) 0.9806(3) 0.0711 1.0000 Uani O21 0.3559(1) -0.3600(2) 0.8043(1) 0.0497 1.0000 Uani C21 0.4535(2) -0.3903(2) 0.7394(2) 0.0424 1.0000 Uani C22 0.4819(2) -0.5399(2) 0.7450(2) 0.0489 1.0000 Uani C23 0.3654(3) -0.6295(2) 0.6806(2) 0.0573 1.0000 Uani C24 0.2624(2) -0.6636(2) 0.7479(2) 0.0498 1.0000 Uani O22 0.2215(2) -0.5823(2) 0.8099(2) 0.0741 1.0000 Uani N21 0.2107(2) -0.7841(2) 0.7343(2) 0.0604 1.0000 Uani C25 0.3995(2) -0.3442(2) 0.6134(2) 0.0463 1.0000 Uani C26 0.4493(2) -0.3946(3) 0.5218(2) 0.0593 1.0000 Uani C27 0.3927(3) -0.3570(4) 0.4079(2) 0.0738 1.0000 Uani C28 0.2872(4) -0.2668(4) 0.3830(3) 0.0821 1.0000 Uani C29 0.2392(3) -0.2150(4) 0.4723(3) 0.0819 1.0000 Uani C30 0.2928(2) -0.2537(3) 0.5862(2) 0.0609 1.0000 Uani C31 0.1190(3) -0.8455(4) 0.7976(3) 0.0834 1.0000 Uani C32 0.1452(5) -0.9776(4) 0.7447(5) 0.1083 1.0000 Uani C33 0.2468(3) -0.9098(2) 0.6857(3) 0.0670 1.0000 Uani H1 0.557(2) -0.366(4) 0.955(2) 0.075(8) 1.0000 Uiso H2 0.308(3) -0.441(2) 0.809(3) 0.08(1) 1.0000 Uiso H21 0.4768 -0.1606 0.8557 0.0494 1.0000 Uiso H22 0.5234 -0.1270 0.7422 0.0494 1.0000 Uiso H31 0.7026 -0.1303 0.9642 0.0542 1.0000 Uiso H32 0.7426 -0.0875 0.8498 0.0542 1.0000 Uiso H61 0.6556 -0.1735 0.6318 0.0570 1.0000 Uiso H71 0.8439 -0.1953 0.5513 0.0730 1.0000 Uiso H81 1.0035 -0.3641 0.6131 0.0729 1.0000 Uiso H91 0.9752 -0.5094 0.7576 0.0670 1.0000 Uiso H101 0.7940 -0.4838 0.8449 0.0547 1.0000 Uiso H111 0.7139 0.2838 1.0495 0.0591 1.0000 Uiso H112 0.7189 0.3348 0.9257 0.0591 1.0000 Uiso H121 0.9494 0.2691 1.0976 0.0787 1.0000 Uiso H122 0.9532 0.3072 0.9702 0.0787 1.0000 Uiso H131 0.9134 0.0473 1.0439 0.0678 1.0000 Uiso H132 0.9311 0.0836 0.9199 0.0678 1.0000 Uiso H221 0.5046 -0.5654 0.8254 0.0480 1.0000 Uiso H222 0.5587 -0.5553 0.7126 0.0480 1.0000 Uiso H231 0.4044 -0.7103 0.6612 0.0576 1.0000 Uiso H232 0.3188 -0.5853 0.6104 0.0576 1.0000 Uiso H261 0.5238 -0.4561 0.5383 0.0607 1.0000 Uiso H271 0.4270 -0.3939 0.3460 0.0736 1.0000 Uiso H281 0.2479 -0.2405 0.3041 0.0783 1.0000 Uiso H291 0.1671 -0.1508 0.4554 0.0780 1.0000 Uiso H301 0.2561 -0.2179 0.6471 0.0595 1.0000 Uiso H311 0.1503 -0.8411 0.8808 0.0845 1.0000 Uiso H312 0.0263 -0.8154 0.7744 0.0845 1.0000 Uiso H321 0.1854 -1.0435 0.8010 0.1038 1.0000 Uiso H322 0.0667 -1.0141 0.6912 0.1038 1.0000 Uiso H331 0.3400 -0.9366 0.7147 0.0628 1.0000 Uiso H332 0.2228 -0.9143 0.6023 0.0628 1.0000 Uiso 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 O1 0.0531(8) 0.0580(9) 0.0511(8) 0.0059(7) 0.0111(6) -0.0014(7) C1 0.0426(9) 0.040(1) 0.050(1) -0.0011(8) 0.0099(7) -0.0017(8) C2 0.047(1) 0.042(1) 0.062(1) -0.0079(9) 0.0110(8) -0.0012(8) C3 0.054(1) 0.045(1) 0.066(1) -0.012(1) 0.0032(9) -0.001(1) C4 0.053(1) 0.047(1) 0.046(1) -0.0066(8) 0.0099(8) -0.0021(9) O2 0.0582(9) 0.064(1) 0.090(1) -0.025(1) 0.0079(8) 0.0049(9) N1 0.059(1) 0.0433(9) 0.065(1) -0.0058(8) 0.0163(8) -0.0046(8) C5 0.0423(9) 0.0379(9) 0.055(1) -0.0029(8) 0.0125(7) -0.0046(7) C6 0.056(1) 0.055(1) 0.060(1) 0.007(1) 0.0158(9) -0.004(1) C7 0.070(1) 0.086(2) 0.065(1) 0.003(1) 0.027(1) -0.015(1) C8 0.049(1) 0.094(2) 0.084(2) -0.014(2) 0.026(1) -0.008(1) C9 0.045(1) 0.071(2) 0.093(2) -0.009(1) 0.017(1) 0.006(1) C10 0.045(1) 0.048(1) 0.076(1) 0.005(1) 0.0134(9) 0.0017(9) C11 0.076(2) 0.038(1) 0.072(1) 0.002(1) 0.018(1) -0.006(1) C12 0.076(2) 0.049(1) 0.130(3) -0.012(2) 0.019(2) -0.019(1) C13 0.058(1) 0.049(1) 0.110(2) -0.008(1) 0.027(1) -0.009(1) O21 0.0494(7) 0.0427(7) 0.0631(8) -0.0072(7) 0.0254(6) -0.0003(6) C21 0.0399(8) 0.0354(9) 0.054(1) -0.0030(7) 0.0165(7) -0.0003(7) C22 0.0439(9) 0.0345(9) 0.073(1) -0.0004(9) 0.0237(9) 0.0005(8) C23 0.067(1) 0.038(1) 0.076(1) -0.009(1) 0.034(1) -0.0120(9) C24 0.0438(9) 0.043(1) 0.064(1) 0.0014(9) 0.0159(8) 0.0004(8) O22 0.068(1) 0.054(1) 0.115(2) -0.013(1) 0.051(1) -0.0074(9) N21 0.059(1) 0.043(1) 0.084(1) 0.0015(9) 0.029(1) -0.0100(9) C25 0.0461(9) 0.0393(9) 0.054(1) -0.0038(8) 0.0126(7) -0.0088(8) C26 0.061(1) 0.057(1) 0.064(1) -0.008(1) 0.024(1) -0.012(1) C27 0.087(2) 0.083(2) 0.055(1) -0.008(1) 0.024(1) -0.035(2) C28 0.091(2) 0.086(2) 0.062(1) 0.014(2) 0.003(1) -0.025(2) C29 0.080(2) 0.076(2) 0.078(2) 0.016(2) -0.003(1) 0.007(2) C30 0.060(1) 0.053(1) 0.066(1) 0.001(1) 0.009(1) 0.005(1) C31 0.073(2) 0.069(2) 0.120(2) 0.005(2) 0.046(2) -0.021(1) C32 0.128(3) 0.058(2) 0.151(4) 0.006(2) 0.057(3) -0.034(2) C33 0.076(2) 0.038(1) 0.086(2) -0.000(1) 0.019(1) -0.007(1) _refine_ls_extinction_coef 29.8(36) _refine_ls_extinction_method 'Larson 1970 Crystallographic Computing eq 22' loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 . C1 . 1.422(3) yes O1 . H1 . 0.95(1) no C1 . C2 . 1.543(3) yes C1 . C5 . 1.529(3) yes C1 . C21 . 1.594(3) yes C2 . C3 . 1.523(3) yes C2 . H21 . 0.960(2) no C2 . H22 . 0.960(2) no C3 . C4 . 1.512(3) yes C3 . H31 . 0.960(3) no C3 . H32 . 0.960(3) no C4 . O2 . 1.231(3) yes C4 . N1 . 1.334(3) yes N1 . C11 . 1.458(3) yes N1 . C13 . 1.446(3) yes C5 . C6 . 1.395(3) yes C5 . C10 . 1.390(3) yes C6 . C7 . 1.390(3) yes C6 . H61 . 0.960(3) no C7 . C8 . 1.380(5) yes C7 . H71 . 0.960(3) no C8 . C9 . 1.365(5) yes C8 . H81 . 0.960(2) no C9 . C10 . 1.384(3) yes C9 . H91 . 0.960(3) no C10 . H101 . 0.960(2) no C11 . C12 . 1.520(4) yes C11 . H111 . 0.960(3) no C11 . H112 . 0.960(3) no C12 . C13 . 1.540(4) yes C12 . H121 . 0.960(4) no C12 . H122 . 0.960(4) no C13 . H131 . 0.960(3) no C13 . H132 . 0.960(3) no O21 . C21 . 1.427(2) yes O21 . H2 . 0.96(1) no C21 . C22 . 1.539(3) yes C21 . C25 . 1.531(3) yes C22 . C23 . 1.534(3) yes C22 . H221 . 0.960(2) no C22 . H222 . 0.960(2) no C23 . C24 . 1.500(3) yes C23 . H231 . 0.960(2) no C23 . H232 . 0.960(3) no C24 . O22 . 1.240(3) yes C24 . N21 . 1.321(3) yes N21 . C31 . 1.466(3) yes N21 . C33 . 1.478(3) yes C25 . C26 . 1.401(3) yes C25 . C30 . 1.391(3) yes C26 . C27 . 1.384(4) yes C26 . H261 . 0.960(3) no C27 . C28 . 1.381(5) yes C27 . H271 . 0.960(3) no C28 . C29 . 1.372(5) yes C28 . H281 . 0.960(3) no C29 . C30 . 1.383(4) yes C29 . H291 . 0.960(3) no C30 . H301 . 0.960(3) no C31 . C32 . 1.527(6) yes C31 . H311 . 0.960(4) no C31 . H312 . 0.960(3) no C32 . C33 . 1.539(5) yes C32 . H321 . 0.960(5) no C32 . H322 . 0.960(5) no C33 . H331 . 0.960(3) no C33 . H332 . 0.960(3) no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O1 . H1 . 107.5(20) no O1 . C1 . C2 . 109.0(2) no O1 . C1 . C5 . 106.3(2) no C2 . C1 . C5 . 111.3(2) no O1 . C1 . C21 . 108.0(2) no C2 . C1 . C21 . 109.5(2) no C5 . C1 . C21 . 112.7(2) no C1 . C2 . C3 . 112.2(2) no C1 . C2 . H21 . 108.8(2) no C3 . C2 . H21 . 108.8(2) no C1 . C2 . H22 . 108.8(2) no C3 . C2 . H22 . 108.8(2) no H21 . C2 . H22 . 109.5(2) no C2 . C3 . C4 . 113.2(2) no C2 . C3 . H31 . 108.5(2) no C4 . C3 . H31 . 108.5(2) no C2 . C3 . H32 . 108.5(2) no C4 . C3 . H32 . 108.5(2) no H31 . C3 . H32 . 109.5(2) no C3 . C4 . O2 . 124.3(2) no C3 . C4 . N1 . 114.0(2) no O2 . C4 . N1 . 121.7(2) no C4 . N1 . C11 . 130.1(2) no C4 . N1 . C13 . 132.7(2) no C11 . N1 . C13 . 94.6(2) no C1 . C5 . C6 . 122.2(2) no C1 . C5 . C10 . 120.2(2) no C6 . C5 . C10 . 117.6(2) no C5 . C6 . C7 . 120.4(2) no C5 . C6 . H61 . 119.8(2) no C7 . C6 . H61 . 119.8(3) no C6 . C7 . C8 . 120.9(3) no C6 . C7 . H71 . 119.6(3) no C8 . C7 . H71 . 119.6(3) no C7 . C8 . C9 . 119.0(2) no C7 . C8 . H81 . 120.5(3) no C9 . C8 . H81 . 120.5(3) no C8 . C9 . C10 . 120.8(3) no C8 . C9 . H91 . 119.6(3) no C10 . C9 . H91 . 119.6(3) no C5 . C10 . C9 . 121.3(2) no C5 . C10 . H101 . 119.3(2) no C9 . C10 . H101 . 119.3(2) no N1 . C11 . C12 . 88.4(2) no N1 . C11 . H111 . 114.5(2) no C12 . C11 . H111 . 114.5(3) no N1 . C11 . H112 . 114.5(2) no C12 . C11 . H112 . 114.5(3) no H111 . C11 . H112 . 109.5(3) no C11 . C12 . C13 . 88.5(2) no C11 . C12 . H121 . 114.4(3) no C13 . C12 . H121 . 114.4(3) no C11 . C12 . H122 . 114.4(3) no C13 . C12 . H122 . 114.4(4) no H121 . C12 . H122 . 109.5(3) no N1 . C13 . C12 . 88.1(2) no N1 . C13 . H131 . 114.5(2) no C12 . C13 . H131 . 114.5(3) no N1 . C13 . H132 . 114.5(3) no C12 . C13 . H132 . 114.5(3) no H131 . C13 . H132 . 109.5(3) no C21 . O21 . H2 . 106.0(21) no C1 . C21 . O21 . 103.8(2) no C1 . C21 . C22 . 109.8(2) no O21 . C21 . C22 . 109.6(2) no C1 . C21 . C25 . 112.9(2) no O21 . C21 . C25 . 109.3(2) no C22 . C21 . C25 . 111.1(2) no C21 . C22 . C23 . 116.5(2) no C21 . C22 . H221 . 107.7(2) no C23 . C22 . H221 . 107.7(2) no C21 . C22 . H222 . 107.7(2) no C23 . C22 . H222 . 107.7(2) no H221 . C22 . H222 . 109.5(2) no C22 . C23 . C24 . 114.9(2) no C22 . C23 . H231 . 108.1(2) no C24 . C23 . H231 . 108.1(2) no C22 . C23 . H232 . 108.1(2) no C24 . C23 . H232 . 108.1(2) no H231 . C23 . H232 . 109.5(2) no C23 . C24 . O22 . 122.6(2) no C23 . C24 . N21 . 117.0(2) no O22 . C24 . N21 . 120.3(2) no C24 . N21 . C31 . 127.6(2) no C24 . N21 . C33 . 135.5(2) no C31 . N21 . C33 . 94.8(2) no C21 . C25 . C26 . 122.3(2) no C21 . C25 . C30 . 119.9(2) no C26 . C25 . C30 . 117.7(2) no C25 . C26 . C27 . 121.0(3) no C25 . C26 . H261 . 119.5(2) no C27 . C26 . H261 . 119.5(3) no C26 . C27 . C28 . 120.2(3) no C26 . C27 . H271 . 119.9(4) no C28 . C27 . H271 . 119.9(3) no C27 . C28 . C29 . 119.3(3) no C27 . C28 . H281 . 120.3(4) no C29 . C28 . H281 . 120.3(4) no C28 . C29 . C30 . 121.1(3) no C28 . C29 . H291 . 119.5(3) no C30 . C29 . H291 . 119.5(4) no C25 . C30 . C29 . 120.7(3) no C25 . C30 . H301 . 119.7(2) no C29 . C30 . H301 . 119.7(3) no N21 . C31 . C32 . 88.0(2) no N21 . C31 . H311 . 114.5(3) no C32 . C31 . H311 . 114.5(4) no N21 . C31 . H312 . 114.5(3) no C32 . C31 . H312 . 114.5(4) no H311 . C31 . H312 . 109.5(3) no C31 . C32 . C33 . 89.9(2) no C31 . C32 . H321 . 114.1(5) no C33 . C32 . H321 . 114.1(4) no C31 . C32 . H322 . 114.1(4) no C33 . C32 . H322 . 114.1(4) no H321 . C32 . H322 . 109.5(3) no N21 . C33 . C32 . 87.1(2) no N21 . C33 . H331 . 114.7(2) no C32 . C33 . H331 . 114.7(3) no N21 . C33 . H332 . 114.7(2) no C32 . C33 . H332 . 114.7(3) no H331 . C33 . H332 . 109.5(3) no