# Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is © The Royal Society of Chemistry and Owner Societies 2008 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_Cambridge 0171 _publ_contact_author_name 'Qin-Hua Song' _publ_contact_author_email QHSONG@USTC.EDU.CN _publ_section_title ; Substituent Effects on the Regioselectivity of the Patern\`o-B\"uchi Reaction of 5- or/and 6-Methyl Substituted Uracils with 4,4'-Disubstituted Benzophenones ; loop_ _publ_author_name 'Qin-Hua Song.' 'Feng-Feng Kong.' 'Bao-Chang Zhai.' # Attachment 'crystal_structure_of_3Dd.cif' data_3Dd _database_code_depnum_ccdc_archive 'CCDC 686475' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (Z)-1,2,4,6-tetramethyl-8,8-diphenyl-7-oxa-2,4-diaza-bicyclo (4.2.0)octane-3,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H22 N2 O3' _chemical_formula_sum 'C21 H22 N2 O3' _chemical_formula_weight 350.41 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' N N 0.0061 0.0033 '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 P2(1)/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 16.102(2) _cell_length_b 10.7697(10) _cell_length_c 10.9403(12) _cell_angle_alpha 90.00 _cell_angle_beta 101.787(2) _cell_angle_gamma 90.00 _cell_volume 1857.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1679 _cell_measurement_theta_min 2.298 _cell_measurement_theta_max 19.857 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9670 _exptl_absorpt_correction_T_max 0.9964 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8127 _diffrn_reflns_av_R_equivalents 0.1107 _diffrn_reflns_av_sigmaI/netI 0.2327 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.29 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3060 _reflns_number_gt 1244 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0000P)^2^+1.3136P] 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 constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.015(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3060 _refine_ls_number_parameters 300 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2085 _refine_ls_R_factor_gt 0.0948 _refine_ls_wR_factor_ref 0.3310 _refine_ls_wR_factor_gt 0.2317 _refine_ls_goodness_of_fit_ref 1.099 _refine_ls_restrained_S_all 1.099 _refine_ls_shift/su_max 0.001 _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 N1 N 0.8192(3) -0.0266(5) 0.5725(5) 0.0612(16) Uani 1 1 d . . . N2 N 0.8403(4) -0.1987(6) 0.7127(5) 0.0728(18) Uani 1 1 d . . . O1 O 0.6529(3) -0.0539(5) 0.7142(5) 0.0799(17) Uani 1 1 d . A . O2 O 0.9494(3) -0.1121(5) 0.6404(6) 0.101(2) Uani 1 1 d . . . O3 O 0.7344(5) -0.2931(6) 0.7796(7) 0.135(3) Uani 1 1 d . . . C1 C 0.7074(4) 0.0522(7) 0.7032(6) 0.0548(18) Uani 1 1 d . . . C2 C 0.7302(4) -0.0141(7) 0.5827(6) 0.063(2) Uani 1 1 d . A . C3 C 0.8726(4) -0.1093(7) 0.6409(7) 0.067(2) Uani 1 1 d . . . C4 C 0.7564(6) -0.2132(8) 0.7122(8) 0.086(3) Uani 1 1 d . A . C5 C 0.6926(4) -0.1321(7) 0.6300(7) 0.066(2) Uani 1 1 d . . . C6 C 0.660(19) 0.18(3) 0.68(4) 0.06(3) Uani 0.51(9) 1 d P A 1 C7 C 0.700(3) 0.288(7) 0.646(6) 0.073(11) Uani 0.51(9) 1 d P A 1 H7 H 0.7556 0.2832 0.6347 0.087 Uiso 0.51(9) 1 calc PR A 1 C8 C 0.656(3) 0.402(4) 0.628(3) 0.075(9) Uani 0.51(9) 1 d P A 1 H8 H 0.6818 0.4702 0.5999 0.091 Uiso 0.51(9) 1 calc PR A 1 C9 C 0.574(4) 0.413(6) 0.653(4) 0.076(11) Uani 0.51(9) 1 d P A 1 H9 H 0.5457 0.4886 0.6394 0.092 Uiso 0.51(9) 1 calc PR A 1 C10 C 0.536(4) 0.312(6) 0.698(5) 0.07(2) Uani 0.51(9) 1 d P A 1 H10 H 0.4837 0.3202 0.7196 0.088 Uiso 0.51(9) 1 calc PR A 1 C11 C 0.579(5) 0.197(7) 0.710(7) 0.072(12) Uani 0.51(9) 1 d P A 1 H11 H 0.5525 0.1281 0.7375 0.086 Uiso 0.51(9) 1 calc PR A 1 C6' C 0.65(2) 0.16(4) 0.69(4) 0.07(4) Uani 0.49(9) 1 d P A 2 C7' C 0.669(4) 0.268(8) 0.629(7) 0.074(13) Uani 0.49(9) 1 d P A 2 H7' H 0.7190 0.2705 0.5984 0.089 Uiso 0.49(9) 1 calc PR A 2 C8' C 0.616(4) 0.370(4) 0.616(3) 0.079(10) Uani 0.49(9) 1 d P A 2 H8' H 0.6290 0.4418 0.5753 0.094 Uiso 0.49(9) 1 calc PR A 2 C9' C 0.544(5) 0.362(7) 0.665(6) 0.07(2) Uani 0.49(9) 1 d P A 2 H9' H 0.5079 0.4304 0.6561 0.085 Uiso 0.49(9) 1 calc PR A 2 C10' C 0.523(4) 0.258(7) 0.726(7) 0.079(13) Uani 0.49(9) 1 d P A 2 H10' H 0.4746 0.2573 0.7588 0.094 Uiso 0.49(9) 1 calc PR A 2 C11' C 0.576(5) 0.154(8) 0.738(8) 0.075(12) Uani 0.49(9) 1 d P A 2 H11' H 0.5632 0.0824 0.7774 0.090 Uiso 0.49(9) 1 calc PR A 2 C12 C 0.7785(4) 0.0627(6) 0.8163(6) 0.0525(16) Uani 1 1 d . A . C13 C 0.8511(4) 0.1365(6) 0.8214(7) 0.067(2) Uani 1 1 d . . . H13 H 0.8572 0.1830 0.7522 0.081 Uiso 1 1 calc R A . C14 C 0.9142(4) 0.1402(8) 0.9301(10) 0.083(3) Uani 1 1 d . A . H14 H 0.9631 0.1866 0.9320 0.099 Uiso 1 1 calc R . . C15 C 0.9041(7) 0.0761(10) 1.0327(11) 0.105(3) Uani 1 1 d . . . H15 H 0.9458 0.0814 1.1051 0.126 Uiso 1 1 calc R A . C16 C 0.8330(8) 0.0028(9) 1.0322(9) 0.121(4) Uani 1 1 d . A . H16 H 0.8269 -0.0411 1.1030 0.145 Uiso 1 1 calc R . . C17 C 0.7722(6) -0.0030(8) 0.9242(8) 0.096(3) Uani 1 1 d . . . H17 H 0.7248 -0.0528 0.9228 0.116 Uiso 1 1 calc R A . C18 C 0.6761(5) 0.0330(9) 0.4587(7) 0.097(3) Uani 1 1 d . . . H18A H 0.6859 -0.0186 0.3914 0.145 Uiso 1 1 calc R A . H18B H 0.6916 0.1170 0.4445 0.145 Uiso 1 1 calc R . . H18C H 0.6172 0.0298 0.4628 0.145 Uiso 1 1 calc R . . C19 C 0.8566(5) 0.0648(8) 0.5004(9) 0.101(3) Uani 1 1 d . . . H19A H 0.8411 0.1469 0.5214 0.152 Uiso 1 1 calc R . . H19B H 0.8360 0.0504 0.4128 0.152 Uiso 1 1 calc R . . H19C H 0.9173 0.0567 0.5196 0.152 Uiso 1 1 calc R . . C20 C 0.9035(6) -0.2774(9) 0.7959(9) 0.119(4) Uani 1 1 d . . . H20A H 0.9184 -0.2395 0.8768 0.179 Uiso 1 1 calc R . . H20B H 0.9534 -0.2855 0.7611 0.179 Uiso 1 1 calc R . . H20C H 0.8797 -0.3580 0.8035 0.179 Uiso 1 1 calc R . . C21 C 0.627(3) -0.195(5) 0.527(5) 0.077(8) Uani 0.54(5) 1 d P A 1 H21A H 0.6003 -0.2615 0.5615 0.116 Uiso 0.54(5) 1 calc PR A 1 H21B H 0.6554 -0.2267 0.4638 0.116 Uiso 0.54(5) 1 calc PR A 1 H21C H 0.5854 -0.1349 0.4896 0.116 Uiso 0.54(5) 1 calc PR A 1 C21' C 0.633(4) -0.235(5) 0.568(5) 0.077(8) Uani 0.46(5) 1 d P A 2 H21D H 0.6249 -0.2948 0.6302 0.116 Uiso 0.46(5) 1 calc PR A 2 H21E H 0.6571 -0.2758 0.5056 0.116 Uiso 0.46(5) 1 calc PR A 2 H21F H 0.5790 -0.2000 0.5300 0.116 Uiso 0.46(5) 1 calc PR A 2 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 N1 0.064(3) 0.065(4) 0.064(4) 0.014(3) 0.036(3) 0.010(3) N2 0.083(4) 0.075(5) 0.061(4) 0.007(3) 0.014(3) -0.013(3) O1 0.064(3) 0.106(4) 0.081(3) -0.034(3) 0.041(3) -0.033(3) O2 0.062(3) 0.103(4) 0.148(6) 0.015(4) 0.040(3) 0.004(3) O3 0.182(6) 0.107(5) 0.143(6) 0.005(4) 0.095(5) -0.059(4) C1 0.046(3) 0.072(5) 0.051(4) -0.002(3) 0.021(3) -0.004(4) C2 0.046(3) 0.099(6) 0.049(4) 0.005(4) 0.019(3) 0.002(4) C3 0.056(4) 0.075(6) 0.073(5) 0.007(4) 0.024(4) -0.005(4) C4 0.113(7) 0.089(6) 0.067(5) -0.011(5) 0.045(5) -0.044(5) C5 0.050(4) 0.091(6) 0.061(5) -0.028(4) 0.025(4) -0.018(4) C6 0.04(4) 0.09(11) 0.07(4) 0.00(6) 0.02(3) 0.01(6) C7 0.051(17) 0.09(3) 0.08(2) 0.006(15) 0.02(2) 0.02(2) C8 0.050(18) 0.10(2) 0.082(14) 0.004(12) 0.025(14) 0.014(14) C9 0.06(2) 0.10(3) 0.074(14) 0.005(17) 0.023(15) 0.02(2) C10 0.05(2) 0.10(7) 0.07(5) 0.00(4) 0.02(2) 0.01(4) C11 0.047(14) 0.10(4) 0.07(3) 0.002(19) 0.020(16) 0.01(2) C6' 0.05(7) 0.10(9) 0.07(4) 0.00(5) 0.03(4) 0.01(5) C7' 0.05(2) 0.10(4) 0.08(2) 0.001(18) 0.02(2) 0.02(3) C8' 0.05(3) 0.10(2) 0.085(15) 0.002(14) 0.020(16) 0.02(2) C9' 0.04(2) 0.10(6) 0.08(4) 0.00(3) 0.02(2) 0.01(3) C10' 0.055(18) 0.10(4) 0.08(3) 0.00(2) 0.021(13) 0.02(2) C11' 0.049(14) 0.10(4) 0.08(3) 0.00(2) 0.020(17) 0.02(3) C12 0.045(3) 0.059(4) 0.056(4) -0.005(3) 0.016(3) -0.007(3) C13 0.056(4) 0.069(5) 0.082(5) 0.000(4) 0.025(4) -0.006(4) C14 0.041(4) 0.083(6) 0.118(8) -0.032(6) 0.002(5) -0.005(4) C15 0.103(7) 0.086(7) 0.109(9) -0.007(6) -0.021(6) 0.029(6) C16 0.180(10) 0.098(7) 0.071(7) 0.012(5) -0.009(7) -0.022(8) C17 0.117(7) 0.105(7) 0.062(5) 0.005(5) 0.007(5) -0.044(5) C18 0.098(6) 0.139(8) 0.053(5) -0.008(5) 0.013(4) 0.051(5) C19 0.131(7) 0.079(6) 0.122(7) 0.034(5) 0.092(6) 0.013(5) C20 0.140(8) 0.111(7) 0.088(7) 0.029(6) -0.021(6) -0.021(6) C21 0.073(8) 0.08(2) 0.08(2) -0.020(13) 0.017(15) -0.027(14) C21' 0.073(8) 0.08(2) 0.08(2) -0.020(13) 0.017(15) -0.027(14) _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 N1 C3 1.353(8) . ? N1 C2 1.466(7) . ? N1 C19 1.466(8) . ? N2 C4 1.358(9) . ? N2 C3 1.407(8) . ? N2 C20 1.485(10) . ? O1 C1 1.461(7) . ? O1 C5 1.485(7) . ? O2 C3 1.239(7) . ? O3 C4 1.232(9) . ? C1 C6' 1.5(4) . ? C1 C12 1.508(9) . ? C1 C6 1.6(4) . ? C1 C2 1.606(9) . ? C2 C5 1.541(10) . ? C2 C18 1.541(9) . ? C4 C5 1.500(11) . ? C5 C21 1.53(5) . ? C5 C21' 1.53(6) . ? C6 C7 1.4(3) . ? C6 C11 1.4(3) . ? C7 C8 1.40(9) . ? C7 H7 0.9300 . ? C8 C9 1.40(3) . ? C8 H8 0.9300 . ? C9 C10 1.39(6) . ? C9 H9 0.9300 . ? C10 C11 1.41(9) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C6' C7' 1.4(3) . ? C6' C11' 1.4(3) . ? C7' C8' 1.39(8) . ? C7' H7' 0.9300 . ? C8' C9' 1.38(6) . ? C8' H8' 0.9300 . ? C9' C10' 1.38(6) . ? C9' H9' 0.9300 . ? C10' C11' 1.40(11) . ? C10' H10' 0.9300 . ? C11' H11' 0.9300 . ? C12 C17 1.398(10) . ? C12 C13 1.406(8) . ? C13 C14 1.398(11) . ? C13 H13 0.9300 . ? C14 C15 1.355(12) . ? C14 H14 0.9300 . ? C15 C16 1.389(13) . ? C15 H15 0.9300 . ? C16 C17 1.374(12) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C21' H21D 0.9600 . ? C21' H21E 0.9600 . ? C21' H21F 0.9600 . ? 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 C3 N1 C2 122.6(5) . . ? C3 N1 C19 117.1(6) . . ? C2 N1 C19 119.7(6) . . ? C4 N2 C3 123.9(7) . . ? C4 N2 C20 119.6(7) . . ? C3 N2 C20 116.5(6) . . ? C1 O1 C5 92.9(4) . . ? O1 C1 C6' 105(10) . . ? O1 C1 C12 111.0(5) . . ? C6' C1 C12 113(10) . . ? O1 C1 C6 115(10) . . ? C12 C1 C6 109(10) . . ? O1 C1 C2 87.8(5) . . ? C12 C1 C2 116.4(5) . . ? C6 C1 C2 117(10) . . ? N1 C2 C5 114.1(6) . . ? N1 C2 C18 110.4(5) . . ? C5 C2 C18 112.1(6) . . ? N1 C2 C1 119.6(5) . . ? C5 C2 C1 85.4(4) . . ? C18 C2 C1 113.2(5) . . ? O2 C3 N1 122.4(7) . . ? O2 C3 N2 118.0(7) . . ? N1 C3 N2 119.5(6) . . ? O3 C4 N2 119.0(9) . . ? O3 C4 C5 121.4(8) . . ? N2 C4 C5 119.6(7) . . ? O1 C5 C4 106.7(6) . . ? O1 C5 C21 112.9(17) . . ? C4 C5 C21 117.9(19) . . ? O1 C5 C21' 112(2) . . ? C4 C5 C21' 98(2) . . ? O1 C5 C2 89.4(5) . . ? C4 C5 C2 114.4(5) . . ? C21' C5 C2 135(2) . . ? C7 C6 C1 121(10) . . ? C11 C6 C1 120(10) . . ? C6 C7 C8 120(10) . . ? C8 C7 H7 120.1 . . ? C9 C8 C7 121(4) . . ? C9 C8 H8 119.5 . . ? C7 C8 H8 119.5 . . ? C10 C9 C8 120(4) . . ? C10 C9 H9 120.1 . . ? C9 C10 C11 119(5) . . ? C9 C10 H10 120.4 . . ? C11 C10 H10 120.4 . . ? C10 C11 C6 122(10) . . ? C10 C11 H11 119.2 . . ? C7' C6' C11' 121(10) . . ? C7' C6' C1 121(10) . . ? C6' C7' C8' 121(10) . . ? C6' C7' H7' 119.3 . . ? C8' C7' H7' 119.3 . . ? C9' C8' C7' 117(5) . . ? C9' C8' H8' 121.4 . . ? C7' C8' H8' 121.4 . . ? C8' C9' C10' 123(7) . . ? C8' C9' H9' 118.4 . . ? C10' C9' H9' 118.4 . . ? C9' C10' C11' 119(7) . . ? C9' C10' H10' 120.3 . . ? C11' C10' H10' 120.3 . . ? C10' C11' C6' 118(10) . . ? C10' C11' H11' 121.0 . . ? C6' C11' H11' 121.0 . . ? C17 C12 C13 117.1(6) . . ? C17 C12 C1 118.8(6) . . ? C13 C12 C1 124.1(6) . . ? C14 C13 C12 120.3(7) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C15 C14 C13 120.0(8) . . ? C15 C14 H14 120.0 . . ? C13 C14 H14 120.0 . . ? C14 C15 C16 121.6(9) . . ? C14 C15 H15 119.2 . . ? C16 C15 H15 119.2 . . ? C17 C16 C15 118.1(9) . . ? C17 C16 H16 120.9 . . ? C15 C16 H16 120.9 . . ? C16 C17 C12 122.8(8) . . ? C16 C17 H17 118.6 . . ? C12 C17 H17 118.6 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 C21 H21A 109.5 . . ? C5 C21 H21B 109.5 . . ? C5 C21 H21C 109.5 . . ? C5 C21' H21D 109.5 . . ? C5 C21' H21E 109.5 . . ? H21D C21' H21E 109.5 . . ? C5 C21' H21F 109.5 . . ? H21D C21' H21F 109.5 . . ? H21E C21' H21F 109.5 . . ? 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 C5 O1 C1 C6' 137(17) . . . . ? C5 O1 C1 C12 -101.3(5) . . . . ? C5 O1 C1 C6 135(16) . . . . ? C5 O1 C1 C2 16.2(5) . . . . ? C3 N1 C2 C5 -24.7(9) . . . . ? C19 N1 C2 C5 164.6(6) . . . . ? C3 N1 C2 C18 -152.0(7) . . . . ? C19 N1 C2 C18 37.3(9) . . . . ? C3 N1 C2 C1 74.1(9) . . . . ? C19 N1 C2 C1 -96.6(8) . . . . ? O1 C1 C2 N1 -130.7(6) . . . . ? C6' C1 C2 N1 124(14) . . . . ? C12 C1 C2 N1 -18.3(9) . . . . ? C6 C1 C2 N1 112(12) . . . . ? O1 C1 C2 C5 -15.6(4) . . . . ? C6' C1 C2 C5 -121(14) . . . . ? C12 C1 C2 C5 96.9(6) . . . . ? C6 C1 C2 C5 -133(12) . . . . ? O1 C1 C2 C18 96.5(7) . . . . ? C6' C1 C2 C18 -9(14) . . . . ? C12 C1 C2 C18 -151.0(6) . . . . ? C6 C1 C2 C18 -20(12) . . . . ? C2 N1 C3 O2 -173.4(7) . . . . ? C19 N1 C3 O2 -2.4(11) . . . . ? C2 N1 C3 N2 8.6(10) . . . . ? C19 N1 C3 N2 179.6(6) . . . . ? C4 N2 C3 O2 -173.6(7) . . . . ? C20 N2 C3 O2 8.4(10) . . . . ? C4 N2 C3 N1 4.5(10) . . . . ? C20 N2 C3 N1 -173.5(7) . . . . ? C3 N2 C4 O3 -179.1(7) . . . . ? C20 N2 C4 O3 -1.1(11) . . . . ? C3 N2 C4 C5 0.9(11) . . . . ? C20 N2 C4 C5 178.8(7) . . . . ? C1 O1 C5 C4 98.5(6) . . . . ? C1 O1 C5 C21 -130(2) . . . . ? C1 O1 C5 C21' -156(2) . . . . ? C1 O1 C5 C2 -16.9(5) . . . . ? O3 C4 C5 O1 65.6(9) . . . . ? N2 C4 C5 O1 -114.4(7) . . . . ? O3 C4 C5 C21 -63(2) . . . . ? N2 C4 C5 C21 117(2) . . . . ? O3 C4 C5 C21' -50(2) . . . . ? N2 C4 C5 C21' 130(2) . . . . ? O3 C4 C5 C2 162.7(7) . . . . ? N2 C4 C5 C2 -17.2(9) . . . . ? N1 C2 C5 O1 135.8(5) . . . . ? C18 C2 C5 O1 -97.8(6) . . . . ? C1 C2 C5 O1 15.3(4) . . . . ? N1 C2 C5 C4 27.7(8) . . . . ? C18 C2 C5 C4 154.1(6) . . . . ? C1 C2 C5 C4 -92.8(6) . . . . ? N1 C2 C5 C21 -109.7(19) . . . . ? C18 C2 C5 C21 17(2) . . . . ? C1 C2 C5 C21 129.9(19) . . . . ? N1 C2 C5 C21' -103(3) . . . . ? C18 C2 C5 C21' 23(3) . . . . ? C1 C2 C5 C21' 136(3) . . . . ? O1 C1 C6 C7 -168(22) . . . . ? C1 C6 C7 C8 -179(18) . . . . ? C7 C8 C9 C10 1(6) . . . . ? C8 C9 C10 C11 -4(8) . . . . ? C9 C10 C11 C6 2(22) . . . . ? C1 C6 C11 C10 177(17) . . . . ? C2 C1 C6' C11' 123(26) . . . . ? C1 C6' C7' C8' -179(19) . . . . ? C6' C7' C8' C9' 1(23) . . . . ? C7' C8' C9' C10' 0(11) . . . . ? C8' C9' C10' C11' -1(14) . . . . ? C9' C10' C11' C6' 1(24) . . . . ? C1 C6' C11' C10' 178(20) . . . . ? O1 C1 C12 C17 -15.9(8) . . . . ? C6' C1 C12 C17 101(12) . . . . ? C6 C1 C12 C17 111(11) . . . . ? C2 C1 C12 C17 -114.3(7) . . . . ? O1 C1 C12 C13 165.1(5) . . . . ? C6' C1 C12 C13 -78(12) . . . . ? C6 C1 C12 C13 -68(11) . . . . ? C2 C1 C12 C13 66.8(8) . . . . ? C17 C12 C13 C14 1.4(10) . . . . ? C1 C12 C13 C14 -179.6(6) . . . . ? C12 C13 C14 C15 -2.5(11) . . . . ? C13 C14 C15 C16 1.9(14) . . . . ? C14 C15 C16 C17 -0.3(15) . . . . ? C15 C16 C17 C12 -0.8(15) . . . . ? C13 C12 C17 C16 0.3(12) . . . . ? C1 C12 C17 C16 -178.8(8) . . . . ? _diffrn_measured_fraction_theta_max 0.937 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.937 _refine_diff_density_max 0.198 _refine_diff_density_min -0.198 _refine_diff_density_rms 0.050 # Attachment 'crystal_structure_of_4Dd.cif' data_4Dd _database_code_depnum_ccdc_archive 'CCDC 686476' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (Z)-1,2,4,6-tetramethyl-7,7-diphenyl-8-oxa-2,4-diaza-bicyclo (4.2.0)octane-3,5-dione ; _chemical_melting_point ? _chemical_formula_moiety 'C21 H22 N2 O3' _chemical_formula_sum 'C21 H22 N2 O3' _chemical_formula_weight 350.41 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' N N 0.0061 0.0033 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7039(8) _cell_length_b 9.8680(12) _cell_length_c 12.6926(18) _cell_angle_alpha 105.832(3) _cell_angle_beta 93.959(2) _cell_angle_gamma 96.639(2) _cell_volume 917.0(2) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1818 _cell_measurement_theta_min 2.677 _cell_measurement_theta_max 25.022 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.49 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 372 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9561 _exptl_absorpt_correction_T_max 0.9593 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 4770 _diffrn_reflns_av_R_equivalents 0.0210 _diffrn_reflns_av_sigmaI/netI 0.0414 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 25.01 _reflns_number_total 3182 _reflns_number_gt 2164 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0447P)^2^+0.2169P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3182 _refine_ls_number_parameters 239 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0698 _refine_ls_R_factor_gt 0.0417 _refine_ls_wR_factor_ref 0.1153 _refine_ls_wR_factor_gt 0.0959 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_restrained_S_all 1.044 _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 N1 N 0.3317(2) 0.02037(18) 0.19061(14) 0.0524(5) Uani 1 1 d . . . N2 N 0.4161(2) 0.18649(18) 0.36472(12) 0.0427(4) Uani 1 1 d . . . O1 O 0.29147(16) 0.39577(13) 0.36670(10) 0.0418(3) Uani 1 1 d . . . O2 O 0.2569(2) 0.08455(19) 0.03857(12) 0.0746(5) Uani 1 1 d . . . O3 O 0.3501(2) -0.04734(17) 0.34804(14) 0.0709(5) Uani 1 1 d . . . C1 C 0.1652(2) 0.3266(2) 0.27026(14) 0.0365(4) Uani 1 1 d . . . C2 C 0.3245(2) 0.2720(2) 0.20552(15) 0.0402(5) Uani 1 1 d . . . C3 C 0.3015(3) 0.1189(2) 0.13729(17) 0.0490(5) Uani 1 1 d . . . C4 C 0.3641(3) 0.0495(2) 0.30590(18) 0.0488(5) Uani 1 1 d . . . C5 C 0.4236(2) 0.3084(2) 0.32099(15) 0.0407(5) Uani 1 1 d . . . C6 C 0.0687(2) 0.4336(2) 0.23338(15) 0.0397(5) Uani 1 1 d . . . C7 C 0.0723(3) 0.5694(2) 0.30114(19) 0.0598(6) Uani 1 1 d . . . H7 H 0.1409 0.5981 0.3687 0.072 Uiso 1 1 calc R . . C8 C -0.0254(4) 0.6634(3) 0.2696(2) 0.0767(8) Uani 1 1 d . . . H8 H -0.0232 0.7544 0.3165 0.092 Uiso 1 1 calc R . . C9 C -0.1254(3) 0.6236(3) 0.1699(2) 0.0657(7) Uani 1 1 d . . . H9 H -0.1905 0.6875 0.1490 0.079 Uiso 1 1 calc R . . C10 C -0.1293(3) 0.4898(3) 0.10133(19) 0.0561(6) Uani 1 1 d . . . H10 H -0.1972 0.4623 0.0335 0.067 Uiso 1 1 calc R . . C11 C -0.0325(3) 0.3956(2) 0.13264(17) 0.0505(5) Uani 1 1 d . . . H11 H -0.0353 0.3048 0.0852 0.061 Uiso 1 1 calc R . . C12 C 0.0338(2) 0.2136(2) 0.29364(14) 0.0371(4) Uani 1 1 d . . . C13 C 0.0057(3) 0.2182(2) 0.40116(16) 0.0454(5) Uani 1 1 d . . . H13 H 0.0696 0.2893 0.4592 0.055 Uiso 1 1 calc R . . C14 C -0.1171(3) 0.1177(3) 0.42294(18) 0.0554(6) Uani 1 1 d . . . H14 H -0.1335 0.1208 0.4954 0.067 Uiso 1 1 calc R . . C15 C -0.2144(3) 0.0138(2) 0.33838(19) 0.0561(6) Uani 1 1 d . . . H15 H -0.2969 -0.0531 0.3534 0.067 Uiso 1 1 calc R . . C16 C -0.1896(3) 0.0088(2) 0.23082(18) 0.0511(5) Uani 1 1 d . . . H16 H -0.2562 -0.0611 0.1732 0.061 Uiso 1 1 calc R . . C17 C -0.0660(3) 0.1074(2) 0.20860(16) 0.0437(5) Uani 1 1 d . . . H17 H -0.0492 0.1029 0.1359 0.052 Uiso 1 1 calc R . . C18 C 0.3926(3) 0.3672(3) 0.13674(18) 0.0580(6) Uani 1 1 d . . . H18A H 0.5075 0.3479 0.1179 0.087 Uiso 1 1 calc R . . H18B H 0.3987 0.4651 0.1783 0.087 Uiso 1 1 calc R . . H18C H 0.3143 0.3487 0.0706 0.087 Uiso 1 1 calc R . . C19 C 0.3021(4) -0.1309(3) 0.1261(2) 0.0867(9) Uani 1 1 d . . . H19A H 0.1784 -0.1648 0.1148 0.130 Uiso 1 1 calc R . . H19B H 0.3615 -0.1855 0.1654 0.130 Uiso 1 1 calc R . . H19C H 0.3470 -0.1407 0.0561 0.130 Uiso 1 1 calc R . . C20 C 0.4456(3) 0.2146(3) 0.48422(16) 0.0580(6) Uani 1 1 d . . . H20A H 0.3368 0.1914 0.5122 0.087 Uiso 1 1 calc R . . H20B H 0.4895 0.3134 0.5172 0.087 Uiso 1 1 calc R . . H20C H 0.5298 0.1574 0.5018 0.087 Uiso 1 1 calc R . . C21 C 0.6052(3) 0.3925(2) 0.34524(18) 0.0545(6) Uani 1 1 d . . . H21A H 0.6054 0.4748 0.3188 0.082 Uiso 1 1 calc R . . H21B H 0.6874 0.3343 0.3091 0.082 Uiso 1 1 calc R . . H21C H 0.6384 0.4219 0.4233 0.082 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 N1 0.0547(11) 0.0448(11) 0.0503(10) 0.0012(8) -0.0002(8) 0.0108(8) N2 0.0466(10) 0.0457(10) 0.0376(9) 0.0132(8) 0.0009(7) 0.0122(8) O1 0.0410(7) 0.0456(8) 0.0360(7) 0.0064(6) -0.0015(6) 0.0106(6) O2 0.0885(13) 0.0872(13) 0.0376(9) -0.0013(8) 0.0018(8) 0.0187(10) O3 0.0736(11) 0.0559(10) 0.0879(12) 0.0339(9) -0.0049(9) 0.0036(8) C1 0.0380(11) 0.0414(11) 0.0299(9) 0.0095(8) 0.0007(8) 0.0075(8) C2 0.0379(11) 0.0495(12) 0.0341(10) 0.0121(9) 0.0052(8) 0.0081(9) C3 0.0431(12) 0.0605(15) 0.0382(12) 0.0030(10) 0.0058(9) 0.0126(10) C4 0.0397(12) 0.0508(14) 0.0573(13) 0.0170(11) 0.0026(10) 0.0092(10) C5 0.0381(11) 0.0458(12) 0.0378(10) 0.0095(9) 0.0027(8) 0.0102(9) C6 0.0383(11) 0.0423(12) 0.0401(10) 0.0153(9) 0.0036(8) 0.0035(9) C7 0.0665(15) 0.0503(14) 0.0583(14) 0.0110(11) -0.0132(12) 0.0128(11) C8 0.094(2) 0.0483(15) 0.0839(19) 0.0108(13) -0.0139(16) 0.0248(14) C9 0.0671(16) 0.0599(16) 0.0794(17) 0.0330(14) -0.0050(13) 0.0217(12) C10 0.0547(14) 0.0629(16) 0.0554(13) 0.0285(12) -0.0068(11) 0.0061(11) C11 0.0581(13) 0.0483(13) 0.0463(12) 0.0174(10) -0.0037(10) 0.0081(10) C12 0.0365(10) 0.0415(11) 0.0367(10) 0.0130(9) 0.0049(8) 0.0135(9) C13 0.0416(12) 0.0577(13) 0.0403(11) 0.0164(10) 0.0063(9) 0.0126(10) C14 0.0531(13) 0.0768(17) 0.0499(13) 0.0338(12) 0.0168(11) 0.0180(12) C15 0.0484(13) 0.0579(15) 0.0731(16) 0.0345(13) 0.0139(12) 0.0097(11) C16 0.0481(13) 0.0444(13) 0.0613(14) 0.0170(11) 0.0037(10) 0.0047(10) C17 0.0470(12) 0.0463(12) 0.0394(11) 0.0133(9) 0.0064(9) 0.0100(10) C18 0.0502(13) 0.0815(17) 0.0495(13) 0.0304(12) 0.0093(10) 0.0069(12) C19 0.101(2) 0.0519(16) 0.088(2) -0.0090(14) -0.0056(17) 0.0125(15) C20 0.0655(15) 0.0692(16) 0.0434(12) 0.0199(11) 0.0004(10) 0.0190(12) C21 0.0438(12) 0.0609(14) 0.0562(13) 0.0150(11) -0.0008(10) 0.0038(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 N1 C3 1.359(3) . ? N1 C4 1.411(3) . ? N1 C19 1.476(3) . ? N2 C4 1.352(3) . ? N2 C5 1.453(2) . ? N2 C20 1.462(2) . ? O1 C5 1.459(2) . ? O1 C1 1.462(2) . ? O2 C3 1.219(2) . ? O3 C4 1.214(2) . ? C1 C6 1.514(3) . ? C1 C12 1.522(3) . ? C1 C2 1.588(3) . ? C2 C3 1.506(3) . ? C2 C18 1.522(3) . ? C2 C5 1.535(3) . ? C5 C21 1.508(3) . ? C6 C7 1.377(3) . ? C6 C11 1.384(3) . ? C7 C8 1.382(3) . ? C7 H7 0.9300 . ? C8 C9 1.369(3) . ? C8 H8 0.9300 . ? C9 C10 1.364(3) . ? C9 H9 0.9300 . ? C10 C11 1.378(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C13 1.386(3) . ? C12 C17 1.391(3) . ? C13 C14 1.387(3) . ? C13 H13 0.9300 . ? C14 C15 1.369(3) . ? C14 H14 0.9300 . ? C15 C16 1.380(3) . ? C15 H15 0.9300 . ? C16 C17 1.381(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 C3 N1 C4 124.64(18) . . ? C3 N1 C19 117.94(19) . . ? C4 N1 C19 116.7(2) . . ? C4 N2 C5 125.56(16) . . ? C4 N2 C20 116.42(18) . . ? C5 N2 C20 117.54(16) . . ? C5 O1 C1 91.54(12) . . ? O1 C1 C6 111.38(15) . . ? O1 C1 C12 110.92(14) . . ? C6 C1 C12 109.85(15) . . ? O1 C1 C2 88.30(12) . . ? C6 C1 C2 117.97(15) . . ? C12 C1 C2 116.52(15) . . ? C3 C2 C18 109.45(16) . . ? C3 C2 C5 117.12(17) . . ? C18 C2 C5 113.85(16) . . ? C3 C2 C1 117.59(16) . . ? C18 C2 C1 112.89(16) . . ? C5 C2 C1 84.14(13) . . ? O2 C3 N1 121.4(2) . . ? O2 C3 C2 121.5(2) . . ? N1 C3 C2 117.15(17) . . ? O3 C4 N2 122.7(2) . . ? O3 C4 N1 119.9(2) . . ? N2 C4 N1 117.36(19) . . ? N2 C5 O1 109.03(15) . . ? N2 C5 C21 111.02(17) . . ? O1 C5 C21 111.60(16) . . ? N2 C5 C2 112.40(16) . . ? O1 C5 C2 90.50(13) . . ? C21 C5 C2 120.25(17) . . ? C7 C6 C11 118.11(19) . . ? C7 C6 C1 120.97(17) . . ? C11 C6 C1 120.85(17) . . ? C6 C7 C8 120.5(2) . . ? C6 C7 H7 119.8 . . ? C8 C7 H7 119.8 . . ? C9 C8 C7 120.5(2) . . ? C9 C8 H8 119.7 . . ? C7 C8 H8 119.7 . . ? C10 C9 C8 119.7(2) . . ? C10 C9 H9 120.1 . . ? C8 C9 H9 120.1 . . ? C9 C10 C11 119.9(2) . . ? C9 C10 H10 120.0 . . ? C11 C10 H10 120.0 . . ? C10 C11 C6 121.2(2) . . ? C10 C11 H11 119.4 . . ? C6 C11 H11 119.4 . . ? C13 C12 C17 118.41(18) . . ? C13 C12 C1 120.22(17) . . ? C17 C12 C1 121.31(16) . . ? C12 C13 C14 120.5(2) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C14 C15 C16 119.8(2) . . ? C14 C15 H15 120.1 . . ? C16 C15 H15 120.1 . . ? C15 C16 C17 120.1(2) . . ? C15 C16 H16 120.0 . . ? C17 C16 H16 120.0 . . ? C16 C17 C12 120.78(19) . . ? C16 C17 H17 119.6 . . ? C12 C17 H17 119.6 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N2 C20 H20A 109.5 . . ? N2 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? N2 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C5 C21 H21A 109.5 . . ? C5 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C5 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 C5 O1 C1 C6 -137.39(15) . . . . ? C5 O1 C1 C12 99.92(16) . . . . ? C5 O1 C1 C2 -17.91(14) . . . . ? O1 C1 C2 C3 134.69(17) . . . . ? C6 C1 C2 C3 -111.9(2) . . . . ? C12 C1 C2 C3 22.1(2) . . . . ? O1 C1 C2 C18 -96.37(16) . . . . ? C6 C1 C2 C18 17.0(2) . . . . ? C12 C1 C2 C18 151.03(16) . . . . ? O1 C1 C2 C5 17.08(13) . . . . ? C6 C1 C2 C5 130.49(17) . . . . ? C12 C1 C2 C5 -95.52(16) . . . . ? C4 N1 C3 O2 -172.47(19) . . . . ? C19 N1 C3 O2 -2.4(3) . . . . ? C4 N1 C3 C2 7.2(3) . . . . ? C19 N1 C3 C2 177.29(19) . . . . ? C18 C2 C3 O2 -33.7(3) . . . . ? C5 C2 C3 O2 -165.17(18) . . . . ? C1 C2 C3 O2 96.9(2) . . . . ? C18 C2 C3 N1 146.65(18) . . . . ? C5 C2 C3 N1 15.1(3) . . . . ? C1 C2 C3 N1 -82.8(2) . . . . ? C5 N2 C4 O3 -175.34(19) . . . . ? C20 N2 C4 O3 -3.5(3) . . . . ? C5 N2 C4 N1 7.0(3) . . . . ? C20 N2 C4 N1 178.84(17) . . . . ? C3 N1 C4 O3 163.2(2) . . . . ? C19 N1 C4 O3 -7.0(3) . . . . ? C3 N1 C4 N2 -19.0(3) . . . . ? C19 N1 C4 N2 170.8(2) . . . . ? C4 N2 C5 O1 112.60(19) . . . . ? C20 N2 C5 O1 -59.2(2) . . . . ? C4 N2 C5 C21 -124.1(2) . . . . ? C20 N2 C5 C21 64.2(2) . . . . ? C4 N2 C5 C2 13.9(3) . . . . ? C20 N2 C5 C2 -157.92(17) . . . . ? C1 O1 C5 N2 -95.41(15) . . . . ? C1 O1 C5 C21 141.59(16) . . . . ? C1 O1 C5 C2 18.55(14) . . . . ? C3 C2 C5 N2 -24.3(2) . . . . ? C18 C2 C5 N2 -153.78(17) . . . . ? C1 C2 C5 N2 93.76(16) . . . . ? C3 C2 C5 O1 -135.18(16) . . . . ? C18 C2 C5 O1 95.35(18) . . . . ? C1 C2 C5 O1 -17.11(13) . . . . ? C3 C2 C5 C21 109.3(2) . . . . ? C18 C2 C5 C21 -20.2(3) . . . . ? C1 C2 C5 C21 -132.65(19) . . . . ? O1 C1 C6 C7 -15.1(2) . . . . ? C12 C1 C6 C7 108.2(2) . . . . ? C2 C1 C6 C7 -115.0(2) . . . . ? O1 C1 C6 C11 168.03(16) . . . . ? C12 C1 C6 C11 -68.7(2) . . . . ? C2 C1 C6 C11 68.1(2) . . . . ? C11 C6 C7 C8 1.1(3) . . . . ? C1 C6 C7 C8 -175.8(2) . . . . ? C6 C7 C8 C9 -0.8(4) . . . . ? C7 C8 C9 C10 0.3(4) . . . . ? C8 C9 C10 C11 -0.1(4) . . . . ? C9 C10 C11 C6 0.4(3) . . . . ? C7 C6 C11 C10 -0.9(3) . . . . ? C1 C6 C11 C10 176.01(19) . . . . ? O1 C1 C12 C13 21.2(2) . . . . ? C6 C1 C12 C13 -102.35(19) . . . . ? C2 C1 C12 C13 120.15(18) . . . . ? O1 C1 C12 C17 -161.61(16) . . . . ? C6 C1 C12 C17 74.8(2) . . . . ? C2 C1 C12 C17 -62.7(2) . . . . ? C17 C12 C13 C14 1.1(3) . . . . ? C1 C12 C13 C14 178.34(18) . . . . ? C12 C13 C14 C15 -1.1(3) . . . . ? C13 C14 C15 C16 0.3(3) . . . . ? C14 C15 C16 C17 0.6(3) . . . . ? C15 C16 C17 C12 -0.6(3) . . . . ? C13 C12 C17 C16 -0.2(3) . . . . ? C1 C12 C17 C16 -177.46(18) . . . . ? _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.233 _refine_diff_density_min -0.147 _refine_diff_density_rms 0.036