Supplementary Material (ESI) for Chemical Communications This journal is © The Royal Society of Chemistry 2001 data_ic7242 _database_code_CSD 166074 _journal_coden_Cambridge 182 _publ_requested_journal 'Chemical Communications' loop_ _publ_author_name 'Liao, Chun-Chen' 'Lin, Ken-Ching' _publ_contact_author_name 'Prof Chun-Chen Liao' _publ_contact_author_address ; Prof Chun-Chen Liao Department of Chemistry National Tsing Hua University Hsinchu TAIWAN ; _publ_contact_author_email 'CCLIAO@MX.NTHU.EDU.TW' _publ_section_title ; The hetero Diels-Alder reactions of masked o-benzoquinones with nitroso compounds ; _audit_creation_method SHELXL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C13 H19 N O6' _chemical_formula_weight 285.29 _chemical_melting_point ? _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' '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 ? _symmetry_space_group_name_H-M ? loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 12.035(2) _cell_length_b 6.288(2) _cell_length_c 19.541(4) _cell_angle_alpha 90.00 _cell_angle_beta 100.71(2) _cell_angle_gamma 90.00 _cell_volume 1453.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method ? _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 295(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 ? _diffrn_measurement_method ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 3344 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0173 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 27.50 _reflns_number_total 3344 _reflns_number_observed 2361 _reflns_observed_criterion >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement on F^2^ for ALL reflections except for 4 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^)+(0.0681P)^2^+0.1571P] 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 ? _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0068(18) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3340 _refine_ls_number_parameters 182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0617 _refine_ls_R_factor_obs 0.0418 _refine_ls_wR_factor_all 0.1348 _refine_ls_wR_factor_obs 0.1249 _refine_ls_goodness_of_fit_all 1.134 _refine_ls_goodness_of_fit_obs 1.264 _refine_ls_restrained_S_all 1.135 _refine_ls_restrained_S_obs 1.264 _refine_ls_shift/esd_max 0.001 _refine_ls_shift/esd_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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.77171(9) 0.9555(2) 0.12644(7) 0.0631(4) Uani 1 d . . O2 O 1.00759(9) 0.8074(2) 0.07144(5) 0.0499(3) Uani 1 d . . O3 O 1.27422(11) 0.7254(3) 0.17354(7) 0.0784(5) Uani 1 d . . O4 O 1.19978(9) 0.6760(2) 0.05931(5) 0.0488(3) Uani 1 d . . O5 O 0.92230(9) 0.6662(2) 0.21254(6) 0.0445(3) Uani 1 d . . O6 O 0.94404(9) 1.0082(2) 0.25975(5) 0.0427(3) Uani 1 d . . N1 N 1.08751(10) 0.7659(2) 0.13410(6) 0.0418(3) Uani 1 d . . C1 C 0.87265(12) 0.9450(2) 0.13462(8) 0.0408(3) Uani 1 d . . C2 C 0.94188(13) 0.9987(3) 0.07930(8) 0.0461(4) Uani 1 d . . H2A H 0.89265(13) 1.0365(3) 0.03520(8) 0.055 Uiso 1 calc R . C3 C 1.0171(2) 1.1787(3) 0.10634(9) 0.0543(4) Uani 1 d . . H3A H 1.0168(2) 1.3088(3) 0.08371(9) 0.065 Uiso 1 calc R . C4 C 1.08468(14) 1.1342(3) 0.16607(9) 0.0489(4) Uani 1 d . . H4A H 1.13477(14) 1.2323(3) 0.19051(9) 0.059 Uiso 1 calc R . C5 C 1.07307(11) 0.9115(2) 0.19064(7) 0.0382(3) Uani 1 d . . H5A H 1.12863(11) 0.8819(2) 0.23297(7) 0.046 Uiso 1 calc R . C6 C 0.95144(11) 0.8765(2) 0.20302(7) 0.0359(3) Uani 1 d . . C7 C 1.19681(13) 0.7263(3) 0.12468(8) 0.0456(4) Uani 1 d . . C8 C 1.30457(13) 0.5870(3) 0.04066(8) 0.0497(4) Uani 1 d . . C9 C 1.3382(2) 0.3876(4) 0.08192(13) 0.0941(9) Uani 1 d . . H9A H 1.2773(2) 0.2868(4) 0.07307(13) 0.141 Uiso 1 calc R . H9B H 1.3546(2) 0.4213(4) 0.13068(13) 0.141 Uiso 1 calc R . H9C H 1.4041(2) 0.3275(4) 0.06832(13) 0.141 Uiso 1 calc R . C10 C 1.2667(2) 0.5366(4) -0.03531(10) 0.0772(7) Uani 1 d . . H10A H 1.2090(2) 0.4292(4) -0.04051(10) 0.116 Uiso 1 calc R . H10B H 1.3299(2) 0.4855(4) -0.05417(10) 0.116 Uiso 1 calc R . H10C H 1.2370(2) 0.6627(4) -0.05976(10) 0.116 Uiso 1 calc R . C11 C 1.3947(2) 0.7539(5) 0.0512(2) 0.1005(9) Uani 1 d . . H11A H 1.4171(2) 0.7829(5) 0.1001(2) 0.151 Uiso 1 calc R . H11B H 1.3659(2) 0.8816(5) 0.0274(2) 0.151 Uiso 1 calc R . H11C H 1.4588(2) 0.7044(5) 0.0330(2) 0.151 Uiso 1 calc R . C12 C 0.9909(2) 0.5591(3) 0.26968(10) 0.0624(5) Uani 1 d . . H12A H 0.9645(2) 0.4157(3) 0.27210(10) 0.094 Uiso 1 calc R . H12B H 0.9862(2) 0.6321(3) 0.31220(10) 0.094 Uiso 1 calc R . H12C H 1.0680(2) 0.5575(3) 0.26315(10) 0.094 Uiso 1 calc R . C13 C 0.8399(2) 1.0029(3) 0.28525(11) 0.0608(5) Uani 1 d . . H13A H 0.8444(2) 1.0988(3) 0.32391(11) 0.091 Uiso 1 calc R . H13B H 0.8265(2) 0.8612(3) 0.30011(11) 0.091 Uiso 1 calc R . H13C H 0.7789(2) 1.0452(3) 0.24883(11) 0.091 Uiso 1 calc R . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0385(6) 0.0892(10) 0.0625(8) 0.0117(7) 0.0115(5) 0.0082(6) O2 0.0416(6) 0.0718(8) 0.0350(5) -0.0125(5) 0.0034(4) 0.0108(5) O3 0.0505(7) 0.1378(14) 0.0447(7) -0.0192(8) 0.0029(5) 0.0324(8) O4 0.0446(6) 0.0665(8) 0.0373(5) -0.0066(5) 0.0128(4) 0.0165(5) O5 0.0532(6) 0.0351(6) 0.0466(6) -0.0003(5) 0.0127(5) -0.0022(4) O6 0.0505(6) 0.0413(6) 0.0419(5) -0.0065(4) 0.0229(4) -0.0005(4) N1 0.0377(6) 0.0569(8) 0.0310(6) -0.0065(5) 0.0072(5) 0.0070(6) C1 0.0388(7) 0.0428(8) 0.0417(7) 0.0005(6) 0.0098(6) 0.0028(6) C2 0.0429(8) 0.0606(10) 0.0359(7) 0.0074(7) 0.0100(6) 0.0105(7) C3 0.0599(10) 0.0516(10) 0.0573(10) 0.0111(8) 0.0267(8) 0.0002(8) C4 0.0502(9) 0.0515(9) 0.0501(9) -0.0076(7) 0.0225(7) -0.0106(7) C5 0.0363(7) 0.0479(8) 0.0317(6) -0.0065(6) 0.0093(5) 0.0019(6) C6 0.0397(7) 0.0350(7) 0.0357(7) -0.0017(6) 0.0136(5) 0.0018(6) C7 0.0433(8) 0.0584(10) 0.0364(7) -0.0040(7) 0.0107(6) 0.0107(7) C8 0.0487(9) 0.0591(10) 0.0454(8) -0.0030(7) 0.0195(7) 0.0185(8) C9 0.118(2) 0.092(2) 0.083(2) 0.0257(14) 0.0475(14) 0.060(2) C10 0.0841(14) 0.102(2) 0.0499(10) -0.0142(11) 0.0229(10) 0.0338(13) C11 0.0682(14) 0.111(2) 0.135(2) -0.042(2) 0.052(2) -0.0129(14) C12 0.0867(13) 0.0381(9) 0.0605(11) 0.0082(8) 0.0089(9) 0.0074(9) C13 0.0644(11) 0.0620(11) 0.0666(11) -0.0101(9) 0.0399(9) 0.0023(9) _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 C1 1.197(2) . ? O2 N1 1.433(2) . ? O2 C2 1.463(2) . ? O3 C7 1.204(2) . ? O4 C7 1.323(2) . ? O4 C8 1.486(2) . ? O5 C6 1.390(2) . ? O5 C12 1.428(2) . ? O6 C6 1.400(2) . ? O6 C13 1.433(2) . ? N1 C7 1.384(2) . ? N1 C5 1.470(2) . ? C1 C2 1.520(2) . ? C1 C6 1.549(2) . ? C2 C3 1.484(3) . ? C3 C4 1.322(3) . ? C4 C5 1.495(2) . ? C5 C6 1.543(2) . ? C8 C11 1.495(3) . ? C8 C10 1.504(3) . ? C8 C9 1.505(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O2 C2 110.48(10) . . ? C7 O4 C8 120.22(12) . . ? C6 O5 C12 115.46(12) . . ? C6 O6 C13 116.76(12) . . ? C7 N1 O2 115.00(11) . . ? C7 N1 C5 117.39(12) . . ? O2 N1 C5 112.00(11) . . ? O1 C1 C2 124.72(14) . . ? O1 C1 C6 125.00(14) . . ? C2 C1 C6 110.28(12) . . ? O2 C2 C3 111.01(13) . . ? O2 C2 C1 105.70(13) . . ? C3 C2 C1 107.14(13) . . ? C4 C3 C2 112.8(2) . . ? C3 C4 C5 113.75(15) . . ? N1 C5 C4 108.09(12) . . ? N1 C5 C6 106.11(11) . . ? C4 C5 C6 109.37(12) . . ? O5 C6 O6 113.72(11) . . ? O5 C6 C5 115.27(11) . . ? O6 C6 C5 104.00(11) . . ? O5 C6 C1 104.52(11) . . ? O6 C6 C1 113.58(12) . . ? C5 C6 C1 105.75(11) . . ? O3 C7 O4 127.52(14) . . ? O3 C7 N1 120.66(14) . . ? O4 C7 N1 111.60(13) . . ? O4 C8 C11 109.2(2) . . ? O4 C8 C10 101.91(13) . . ? C11 C8 C10 111.3(2) . . ? O4 C8 C9 109.76(14) . . ? C11 C8 C9 113.3(2) . . ? C10 C8 C9 110.8(2) . . ? _refine_diff_density_max 0.261 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.038