# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2010 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dhevalapally, B. Ramachary' _publ_contact_author_email ramsc@uohyd.ernet.in _publ_section_title ; Sequential combination of Barbas-Michael and acetalization reactions: direct catalytic asymmetric s ynthesis of functionalized 4-nitromethyl-chromans as drug intermediates ; loop_ _publ_author_name B.R.Dhevalapally S.Rajasekar # Attachment '- 3_methoxy_cis_racemic_SR_III_11_I.CIF' data_dbr77_m _database_code_depnum_ccdc_archive 'CCDC 765267' #TrackingRef '- 3_methoxy_cis_racemic_SR_III_11_I.CIF' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 N O5' _chemical_formula_weight 267.28 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 11.2657(18) _cell_length_b 6.0004(10) _cell_length_c 19.842(3) _cell_angle_alpha 90.00 _cell_angle_beta 94.626(2) _cell_angle_gamma 90.00 _cell_volume 1336.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 6456 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.92 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.102 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9602 _exptl_absorpt_correction_T_max 0.9749 _exptl_absorpt_process_details 'Bruker AXS SADABS program' _exptl_special_details ; Sheldrick,G.M.,(2003),University of gottingen,Germany The values quoted are generated by SHELX based on crystal size and the corrections are not significant for small crystals composed of light atoms. ; _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 14689 _diffrn_reflns_av_R_equivalents 0.0308 _diffrn_reflns_av_sigmaI/netI 0.0219 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 28.18 _reflns_number_total 3178 _reflns_number_gt 2688 _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^)+(0.0907P)^2^+0.1900P] 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 3178 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0632 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1444 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 O3 O 0.22138(8) 0.02149(16) 0.00066(5) 0.0471(3) Uani 1 1 d . . . O1 O 0.52718(8) 0.29584(17) 0.13902(5) 0.0476(3) Uani 1 1 d . . . O2 O 0.36844(8) 0.01889(16) 0.08939(5) 0.0473(3) Uani 1 1 d . . . C5 C 0.33293(10) 0.1563(2) 0.13922(6) 0.0382(3) Uani 1 1 d . . . C1 C 0.22139(11) 0.1512(2) 0.16405(6) 0.0430(3) Uani 1 1 d . . . C6 C 0.42051(10) 0.3042(2) 0.16693(6) 0.0395(3) Uani 1 1 d . . . C9 C 0.28063(11) -0.1124(2) 0.05138(6) 0.0440(3) Uani 1 1 d . . . C2 C 0.19934(12) 0.2908(3) 0.21779(7) 0.0522(4) Uani 1 1 d . . . H2 H 0.1254 0.2864 0.2355 0.063 Uiso 1 1 calc R . . C4 C 0.39561(12) 0.4425(3) 0.21927(7) 0.0487(3) Uani 1 1 d . . . H4 H 0.4531 0.5414 0.2375 0.058 Uiso 1 1 calc R . . C12 C 0.12725(13) -0.0045(3) 0.13273(7) 0.0523(4) Uani 1 1 d . . . H12 H 0.0861 -0.0714 0.1694 0.063 Uiso 1 1 calc R . . C3 C 0.28489(13) 0.4343(3) 0.24487(7) 0.0553(4) Uani 1 1 d . . . H3 H 0.2686 0.5266 0.2806 0.066 Uiso 1 1 calc R . . N1 N -0.04330(12) 0.2700(3) 0.12290(9) 0.0754(5) Uani 1 1 d . . . C10 C 0.29247(14) 0.1139(3) -0.04827(8) 0.0567(4) Uani 1 1 d . . . H10A H 0.3208 -0.0034 -0.0757 0.085 Uiso 1 1 calc R . . H10B H 0.3591 0.1910 -0.0258 0.085 Uiso 1 1 calc R . . H10C H 0.2456 0.2166 -0.0764 0.085 Uiso 1 1 calc R . . C7 C 0.61447(13) 0.4542(3) 0.16324(8) 0.0578(4) Uani 1 1 d . . . H7A H 0.6321 0.4346 0.2110 0.087 Uiso 1 1 calc R . . H7B H 0.5845 0.6021 0.1545 0.087 Uiso 1 1 calc R . . H7C H 0.6857 0.4329 0.1405 0.087 Uiso 1 1 calc R . . C11 C 0.18556(14) -0.1920(3) 0.09542(8) 0.0543(4) Uani 1 1 d . . . H11A H 0.2209 -0.2972 0.1283 0.065 Uiso 1 1 calc R . . H11B H 0.1246 -0.2702 0.0674 0.065 Uiso 1 1 calc R . . C13 C 0.03448(12) 0.1190(3) 0.08604(9) 0.0639(4) Uani 1 1 d . . . H13A H 0.0752 0.2062 0.0538 0.077 Uiso 1 1 calc R . . H13B H -0.0151 0.0105 0.0608 0.077 Uiso 1 1 calc R . . C8 C 0.34892(16) -0.3018(3) 0.02240(9) 0.0615(4) Uani 1 1 d . . . H8A H 0.4098 -0.2424 -0.0036 0.092 Uiso 1 1 calc R . . H8B H 0.2954 -0.3919 -0.0062 0.092 Uiso 1 1 calc R . . H8C H 0.3849 -0.3913 0.0586 0.092 Uiso 1 1 calc R . . O5 O -0.08698(13) 0.1994(4) 0.17269(10) 0.1069(6) Uani 1 1 d . . . O4 O -0.06201(16) 0.4545(3) 0.09983(12) 0.1147(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 O3 0.0396(5) 0.0549(6) 0.0461(5) 0.0076(4) -0.0011(4) -0.0049(4) O1 0.0338(4) 0.0628(6) 0.0462(5) -0.0093(4) 0.0034(4) -0.0081(4) O2 0.0360(5) 0.0606(6) 0.0449(5) -0.0132(4) 0.0015(4) -0.0055(4) C5 0.0346(6) 0.0478(7) 0.0316(5) 0.0026(5) -0.0012(4) -0.0002(5) C1 0.0348(6) 0.0570(7) 0.0368(6) 0.0077(5) 0.0000(5) -0.0025(5) C6 0.0334(6) 0.0499(7) 0.0343(6) 0.0018(5) -0.0014(4) 0.0002(5) C9 0.0426(6) 0.0436(7) 0.0442(7) -0.0003(5) -0.0056(5) -0.0055(5) C2 0.0387(7) 0.0764(10) 0.0421(7) 0.0025(6) 0.0074(5) 0.0047(6) C4 0.0446(7) 0.0578(8) 0.0428(7) -0.0082(6) -0.0029(5) -0.0023(6) C12 0.0395(6) 0.0695(9) 0.0482(7) 0.0084(6) 0.0052(5) -0.0149(6) C3 0.0526(8) 0.0715(9) 0.0420(7) -0.0099(7) 0.0056(6) 0.0066(7) N1 0.0314(6) 0.1065(13) 0.0888(11) -0.0023(10) 0.0071(7) -0.0057(7) C10 0.0589(9) 0.0571(8) 0.0551(8) 0.0070(7) 0.0113(7) -0.0035(7) C7 0.0435(7) 0.0700(10) 0.0596(8) -0.0065(7) 0.0028(6) -0.0170(7) C11 0.0536(8) 0.0530(8) 0.0554(8) 0.0091(6) -0.0018(6) -0.0149(6) C13 0.0330(6) 0.0960(12) 0.0616(9) -0.0037(9) -0.0030(6) -0.0047(7) C8 0.0707(10) 0.0497(8) 0.0627(9) -0.0076(7) -0.0038(8) 0.0056(7) O5 0.0570(8) 0.1561(16) 0.1129(12) 0.0134(12) 0.0404(8) 0.0036(9) O4 0.0892(12) 0.1070(13) 0.1511(18) 0.0139(13) 0.0300(11) 0.0192(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 O3 C9 1.4128(16) . ? O3 C10 1.4201(17) . ? O1 C6 1.3640(15) . ? O1 C7 1.4231(16) . ? O2 C5 1.3717(15) . ? O2 C9 1.4311(15) . ? C5 C1 1.3865(17) . ? C5 C6 1.4055(17) . ? C1 C2 1.394(2) . ? C1 C12 1.5091(19) . ? C6 C4 1.3758(19) . ? C9 C8 1.512(2) . ? C9 C11 1.513(2) . ? C2 C3 1.369(2) . ? C2 H2 0.9300 . ? C4 C3 1.385(2) . ? C4 H4 0.9300 . ? C12 C11 1.524(2) . ? C12 C13 1.531(2) . ? C12 H12 0.9800 . ? C3 H3 0.9300 . ? N1 O4 1.210(2) . ? N1 O5 1.215(2) . ? N1 C13 1.492(2) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 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 C9 O3 C10 116.68(11) . . ? C6 O1 C7 116.48(11) . . ? C5 O2 C9 118.78(10) . . ? O2 C5 C1 124.63(11) . . ? O2 C5 C6 115.16(10) . . ? C1 C5 C6 120.18(11) . . ? C5 C1 C2 118.76(12) . . ? C5 C1 C12 119.62(12) . . ? C2 C1 C12 121.62(12) . . ? O1 C6 C4 124.65(12) . . ? O1 C6 C5 115.57(11) . . ? C4 C6 C5 119.77(12) . . ? O3 C9 O2 109.21(10) . . ? O3 C9 C8 112.47(12) . . ? O2 C9 C8 105.24(11) . . ? O3 C9 C11 105.97(11) . . ? O2 C9 C11 111.15(11) . . ? C8 C9 C11 112.85(13) . . ? C3 C2 C1 120.98(12) . . ? C3 C2 H2 119.5 . . ? C1 C2 H2 119.5 . . ? C6 C4 C3 120.00(13) . . ? C6 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C1 C12 C11 109.92(11) . . ? C1 C12 C13 111.86(13) . . ? C11 C12 C13 111.29(13) . . ? C1 C12 H12 107.9 . . ? C11 C12 H12 107.9 . . ? C13 C12 H12 107.9 . . ? C2 C3 C4 120.30(13) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? O4 N1 O5 123.8(2) . . ? O4 N1 C13 117.46(18) . . ? O5 N1 C13 118.65(19) . . ? O3 C10 H10A 109.5 . . ? O3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? O3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C9 C11 C12 113.61(12) . . ? C9 C11 H11A 108.8 . . ? C12 C11 H11A 108.8 . . ? C9 C11 H11B 108.8 . . ? C12 C11 H11B 108.8 . . ? H11A C11 H11B 107.7 . . ? N1 C13 C12 113.35(14) . . ? N1 C13 H13A 108.9 . . ? C12 C13 H13A 108.9 . . ? N1 C13 H13B 108.9 . . ? C12 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C9 C8 H8A 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C9 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 28.18 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.244 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.096 # Attachment '- 5_methoxy_trans_racemic_sr_iii_23_ii.cif' data_dbr76_m _database_code_depnum_ccdc_archive 'CCDC 765268' #TrackingRef '- 5_methoxy_trans_racemic_sr_iii_23_ii.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H17 N O5' _chemical_formula_weight 267.28 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 8.850(3) _cell_length_b 6.326(2) _cell_length_c 23.884(9) _cell_angle_alpha 90.00 _cell_angle_beta 95.201(6) _cell_angle_gamma 90.00 _cell_volume 1331.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3720 _cell_measurement_theta_min 2.31 _cell_measurement_theta_max 27.57 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.130125 _exptl_absorpt_correction_T_max 1.0000 _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 14516 _diffrn_reflns_av_R_equivalents 0.0321 _diffrn_reflns_av_sigmaI/netI 0.0248 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 1.71 _diffrn_reflns_theta_max 28.15 _reflns_number_total 3150 _reflns_number_gt 2629 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.0511P)^2^+0.4880P] 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 3150 _refine_ls_number_parameters 175 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0798 _refine_ls_R_factor_gt 0.0656 _refine_ls_wR_factor_ref 0.1493 _refine_ls_wR_factor_gt 0.1424 _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_restrained_S_all 1.181 _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 O2 O 0.15457(14) 0.6286(2) 0.06966(6) 0.0476(4) Uani 1 1 d . . . O1 O 0.24041(16) 1.3100(2) 0.21258(6) 0.0557(4) Uani 1 1 d . . . O5 O 0.33711(16) 0.7103(2) 0.00905(5) 0.0495(4) Uani 1 1 d . . . C1 C 0.32237(19) 0.8437(3) 0.13244(7) 0.0349(4) Uani 1 1 d . . . C2 C 0.3345(2) 1.0180(3) 0.16755(7) 0.0397(4) Uani 1 1 d . . . H2 H 0.4293 1.0540 0.1850 0.048 Uiso 1 1 calc R . . C3 C 0.2108(2) 1.1402(3) 0.17750(7) 0.0405(4) Uani 1 1 d . . . C6 C 0.1799(2) 0.7967(3) 0.10587(7) 0.0372(4) Uani 1 1 d . . . C4 C 0.0697(2) 1.0893(3) 0.15171(8) 0.0425(4) Uani 1 1 d . . . H4 H -0.0149 1.1696 0.1582 0.051 Uiso 1 1 calc R . . C5 C 0.0562(2) 0.9177(3) 0.11612(8) 0.0435(5) Uani 1 1 d . . . H5 H -0.0387 0.8828 0.0986 0.052 Uiso 1 1 calc R . . C8 C 0.45863(19) 0.7094(3) 0.12221(7) 0.0378(4) Uani 1 1 d . . . H8 H 0.5279 0.7929 0.1013 0.045 Uiso 1 1 calc R . . C10 C 0.4121(2) 0.5114(3) 0.08849(8) 0.0422(4) Uani 1 1 d . . . H10A H 0.4989 0.4584 0.0708 0.051 Uiso 1 1 calc R . . H10B H 0.3814 0.4030 0.1139 0.051 Uiso 1 1 calc R . . N1 N 0.6763(2) 0.5174(4) 0.17064(8) 0.0593(5) Uani 1 1 d . . . C11 C 0.2839(2) 0.5527(3) 0.04397(8) 0.0416(4) Uani 1 1 d . . . C13 C 0.2322(3) 0.3536(4) 0.01307(10) 0.0597(6) Uani 1 1 d . . . H13A H 0.1457 0.3845 -0.0128 0.090 Uiso 1 1 calc R . . H13B H 0.2052 0.2493 0.0396 0.090 Uiso 1 1 calc R . . H13C H 0.3130 0.3003 -0.0072 0.090 Uiso 1 1 calc R . . O4 O 0.77560(19) 0.5971(4) 0.14629(9) 0.0912(7) Uani 1 1 d . . . C9 C 0.5398(2) 0.6474(4) 0.17888(8) 0.0515(5) Uani 1 1 d . . . H9A H 0.5701 0.7738 0.2000 0.062 Uiso 1 1 calc R . . H9B H 0.4713 0.5675 0.2003 0.062 Uiso 1 1 calc R . . C7 C 0.1181(3) 1.4434(4) 0.22352(11) 0.0622(6) Uani 1 1 d . . . H7A H 0.0700 1.4961 0.1887 0.093 Uiso 1 1 calc R . . H7B H 0.1556 1.5598 0.2466 0.093 Uiso 1 1 calc R . . H7C H 0.0459 1.3647 0.2428 0.093 Uiso 1 1 calc R . . O3 O 0.6806(2) 0.3381(3) 0.18797(10) 0.0966(7) Uani 1 1 d . . . C12 C 0.2293(3) 0.7914(4) -0.03333(10) 0.0704(7) Uani 1 1 d . . . H12A H 0.1929 0.6787 -0.0579 0.106 Uiso 1 1 calc R . . H12B H 0.2765 0.8974 -0.0546 0.106 Uiso 1 1 calc R . . H12C H 0.1458 0.8528 -0.0161 0.106 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 O2 0.0367(7) 0.0520(8) 0.0530(8) -0.0128(7) -0.0020(6) -0.0042(6) O1 0.0509(8) 0.0570(9) 0.0576(9) -0.0193(7) -0.0028(7) 0.0111(7) O5 0.0588(9) 0.0497(8) 0.0392(7) 0.0043(6) 0.0005(6) 0.0032(7) C1 0.0330(9) 0.0390(10) 0.0323(8) 0.0045(7) 0.0015(7) 0.0006(7) C2 0.0326(9) 0.0462(11) 0.0392(10) 0.0007(8) -0.0029(7) -0.0005(8) C3 0.0450(10) 0.0434(10) 0.0329(9) 0.0012(8) 0.0023(7) 0.0031(8) C6 0.0359(9) 0.0411(10) 0.0342(9) 0.0022(7) 0.0010(7) -0.0020(8) C4 0.0353(9) 0.0515(11) 0.0409(10) 0.0027(9) 0.0049(7) 0.0079(8) C5 0.0299(9) 0.0542(12) 0.0453(10) 0.0022(9) -0.0021(8) -0.0003(8) C8 0.0324(9) 0.0431(10) 0.0377(9) 0.0010(8) 0.0019(7) 0.0032(8) C10 0.0437(10) 0.0383(10) 0.0440(10) 0.0016(8) 0.0015(8) 0.0043(8) N1 0.0423(10) 0.0716(14) 0.0608(12) -0.0065(10) -0.0126(9) 0.0134(10) C11 0.0443(10) 0.0403(10) 0.0398(10) -0.0039(8) 0.0019(8) -0.0001(8) C13 0.0641(14) 0.0525(13) 0.0609(14) -0.0144(11) -0.0035(11) -0.0051(11) O4 0.0420(9) 0.1126(17) 0.1200(17) 0.0012(14) 0.0131(10) 0.0090(10) C9 0.0405(10) 0.0676(14) 0.0447(11) -0.0049(10) -0.0060(8) 0.0144(10) C7 0.0601(14) 0.0552(14) 0.0725(15) -0.0167(12) 0.0126(12) 0.0081(11) O3 0.0871(14) 0.0765(14) 0.1226(18) 0.0181(13) -0.0093(12) 0.0310(11) C12 0.0983(19) 0.0632(15) 0.0463(12) 0.0034(11) -0.0127(12) 0.0183(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 O2 C6 1.376(2) . ? O2 C11 1.430(2) . ? O1 C3 1.373(2) . ? O1 C7 1.415(2) . ? O5 C11 1.408(2) . ? O5 C12 1.422(3) . ? C1 C2 1.384(3) . ? C1 C6 1.391(2) . ? C1 C8 1.513(2) . ? C2 C3 1.378(3) . ? C2 H2 0.9300 . ? C3 C4 1.379(3) . ? C6 C5 1.376(3) . ? C4 C5 1.377(3) . ? C4 H4 0.9300 . ? C5 H5 0.9300 . ? C8 C9 1.525(3) . ? C8 C10 1.526(3) . ? C8 H8 0.9800 . ? C10 C11 1.506(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? N1 O4 1.207(3) . ? N1 O3 1.207(3) . ? N1 C9 1.489(3) . ? C11 C13 1.510(3) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 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 C6 O2 C11 115.97(14) . . ? C3 O1 C7 118.18(16) . . ? C11 O5 C12 115.99(18) . . ? C2 C1 C6 117.66(16) . . ? C2 C1 C8 121.74(16) . . ? C6 C1 C8 120.60(16) . . ? C3 C2 C1 122.14(17) . . ? C3 C2 H2 118.9 . . ? C1 C2 H2 118.9 . . ? O1 C3 C2 115.67(17) . . ? O1 C3 C4 124.76(17) . . ? C2 C3 C4 119.56(18) . . ? C5 C6 O2 117.05(16) . . ? C5 C6 C1 120.18(17) . . ? O2 C6 C1 122.75(16) . . ? C5 C4 C3 118.95(17) . . ? C5 C4 H4 120.5 . . ? C3 C4 H4 120.5 . . ? C6 C5 C4 121.49(17) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C1 C8 C9 108.63(15) . . ? C1 C8 C10 111.44(15) . . ? C9 C8 C10 109.88(16) . . ? C1 C8 H8 108.9 . . ? C9 C8 H8 108.9 . . ? C10 C8 H8 108.9 . . ? C11 C10 C8 112.33(15) . . ? C11 C10 H10A 109.1 . . ? C8 C10 H10A 109.1 . . ? C11 C10 H10B 109.1 . . ? C8 C10 H10B 109.1 . . ? H10A C10 H10B 107.9 . . ? O4 N1 O3 123.8(2) . . ? O4 N1 C9 117.9(2) . . ? O3 N1 C9 118.3(2) . . ? O5 C11 O2 109.89(15) . . ? O5 C11 C10 105.68(15) . . ? O2 C11 C10 109.67(15) . . ? O5 C11 C13 113.82(16) . . ? O2 C11 C13 105.72(16) . . ? C10 C11 C13 112.06(17) . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? N1 C9 C8 110.33(16) . . ? N1 C9 H9A 109.6 . . ? C8 C9 H9A 109.6 . . ? N1 C9 H9B 109.6 . . ? C8 C9 H9B 109.6 . . ? H9A C9 H9B 108.1 . . ? O1 C7 H7A 109.5 . . ? O1 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? O1 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? O5 C12 H12A 109.5 . . ? O5 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O5 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.963 _diffrn_reflns_theta_full 28.15 _diffrn_measured_fraction_theta_full 0.963 _refine_diff_density_max 0.245 _refine_diff_density_min -0.292 _refine_diff_density_rms 0.042 # Attachment '- 3-Methoxy-3-methyl-1-nitromethyl- # 2,3-dihydro-1H-benzo[f]chromene.cif' data_dbr11 _database_code_depnum_ccdc_archive 'CCDC 777137' #TrackingRef '- # 3-Methoxy-3-methyl-1-nitromethyl-2,3-dihydro-1H-benzo[f]chromene.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H17 N O4' _chemical_formula_weight 287.31 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 P21/n 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 10.7266(17) _cell_length_b 11.6724(15) _cell_length_c 11.4931(13) _cell_angle_alpha 90.00 _cell_angle_beta 93.195(15) _cell_angle_gamma 90.00 _cell_volume 1436.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2139 _cell_measurement_theta_min 3.0660 _cell_measurement_theta_max 28.9589 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.328 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 608 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.83374 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Eos, Gemini' _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 5258 _diffrn_reflns_av_R_equivalents 0.0166 _diffrn_reflns_av_sigmaI/netI 0.0266 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.07 _diffrn_reflns_theta_max 26.37 _reflns_number_total 2939 _reflns_number_gt 2042 _reflns_threshold_expression >2sigma(I) _computing_data_collection CrysAlisPro _computing_cell_refinement CrysAlisPro _computing_data_reduction CrysAlisPro _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^)+(0.0844P)^2^+0.0000P] 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 2939 _refine_ls_number_parameters 192 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0694 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1317 _refine_ls_wR_factor_gt 0.1240 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 O1 O 0.80304(9) -0.01304(9) 0.54933(8) 0.0412(3) Uani 1 1 d . . . O2 O 0.87206(10) -0.00017(9) 0.74285(9) 0.0451(3) Uani 1 1 d . . . C C 0.70434(13) -0.08711(13) 0.55750(12) 0.0364(3) Uani 1 1 d . . . C0AA C 0.60482(13) -0.06825(12) 0.62614(12) 0.0354(3) Uani 1 1 d . . . C1AA C 0.70724(15) 0.12055(12) 0.67710(13) 0.0423(4) Uani 1 1 d . . . H1AA H 0.6764 0.1683 0.6127 0.051 Uiso 1 1 calc R . . H1AB H 0.7246 0.1700 0.7439 0.051 Uiso 1 1 calc R . . C2AA C 0.50475(13) -0.14921(13) 0.62169(12) 0.0383(4) Uani 1 1 d . . . C3AA C 0.51405(14) -0.25200(13) 0.55599(13) 0.0424(4) Uani 1 1 d . . . C4AA C 0.71171(14) -0.18706(15) 0.48935(13) 0.0468(4) Uani 1 1 d . . . H4A H 0.7794 -0.1978 0.4433 0.056 Uiso 1 1 calc R . . N2 N 0.58791(14) 0.08181(12) 0.91916(13) 0.0519(4) Uani 1 1 d . . . C1 C 0.60508(14) 0.03514(12) 0.70618(12) 0.0388(4) Uani 1 1 d . . . H1 H 0.5241 0.0736 0.6951 0.047 Uiso 1 1 calc R . . C5AA C 0.82771(14) 0.06425(13) 0.64491(12) 0.0394(4) Uani 1 1 d . . . O3 O 0.63164(14) 0.06833(12) 1.01845(11) 0.0756(5) Uani 1 1 d . . . C6AA C 0.39258(14) -0.13281(16) 0.68134(14) 0.0501(4) Uani 1 1 d . . . H6A H 0.3820 -0.0658 0.7234 0.060 Uiso 1 1 calc R . . C7AA C 0.98144(18) -0.06703(18) 0.72805(17) 0.0641(5) Uani 1 1 d . . . H7AA H 0.9894 -0.1239 0.7883 0.096 Uiso 1 1 calc R . . H7AC H 1.0535 -0.0181 0.7325 0.096 Uiso 1 1 calc R . . H7AB H 0.9750 -0.1040 0.6533 0.096 Uiso 1 1 calc R . . C8AA C 0.41695(16) -0.33402(15) 0.55587(15) 0.0537(4) Uani 1 1 d . . . H8A H 0.4244 -0.4016 0.5139 0.064 Uiso 1 1 calc R . . C9AA C 0.62084(15) -0.26755(15) 0.49052(14) 0.0489(4) Uani 1 1 d . . . H9A H 0.6287 -0.3344 0.4475 0.059 Uiso 1 1 calc R . . C0BA C 0.30067(16) -0.21412(17) 0.67744(16) 0.0591(5) Uani 1 1 d . . . H0B H 0.2285 -0.2011 0.7167 0.071 Uiso 1 1 calc R . . C1BA C 0.61930(16) -0.00752(13) 0.83205(13) 0.0438(4) Uani 1 1 d . . . H1BA H 0.5653 -0.0733 0.8406 0.053 Uiso 1 1 calc R . . H1BB H 0.7047 -0.0325 0.8484 0.053 Uiso 1 1 calc R . . C2BA C 0.92312(17) 0.14856(15) 0.60436(16) 0.0575(5) Uani 1 1 d . . . H2BB H 0.9922 0.1075 0.5749 0.086 Uiso 1 1 calc R . . H2BC H 0.9523 0.1958 0.6687 0.086 Uiso 1 1 calc R . . H2BA H 0.8855 0.1959 0.5438 0.086 Uiso 1 1 calc R . . O4 O 0.51830(15) 0.15967(12) 0.88970(14) 0.0840(5) Uani 1 1 d . . . C3BA C 0.31278(16) -0.31623(17) 0.61591(17) 0.0607(5) Uani 1 1 d . . . H3B H 0.2504 -0.3715 0.6159 0.073 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 O1 0.0395(6) 0.0515(6) 0.0335(5) -0.0042(5) 0.0087(4) -0.0068(5) O2 0.0440(6) 0.0557(6) 0.0354(6) 0.0019(5) 0.0023(4) 0.0096(5) C 0.0337(7) 0.0440(8) 0.0315(7) 0.0011(6) 0.0010(6) -0.0010(7) C0AA 0.0356(8) 0.0389(8) 0.0320(7) 0.0029(6) 0.0030(6) 0.0057(7) C1AA 0.0502(9) 0.0346(8) 0.0425(8) 0.0037(7) 0.0056(7) 0.0052(7) C2AA 0.0337(8) 0.0450(8) 0.0360(7) 0.0077(7) 0.0015(6) 0.0037(7) C3AA 0.0383(8) 0.0467(9) 0.0414(8) 0.0018(7) -0.0058(7) 0.0010(7) C4AA 0.0409(9) 0.0606(10) 0.0391(8) -0.0144(8) 0.0055(7) 0.0007(8) N2 0.0583(9) 0.0483(8) 0.0516(9) -0.0102(7) 0.0269(7) -0.0151(7) C1 0.0386(8) 0.0368(8) 0.0417(8) 0.0013(7) 0.0081(6) 0.0091(7) C5AA 0.0429(8) 0.0421(8) 0.0334(8) 0.0000(6) 0.0046(6) -0.0015(7) O3 0.1030(11) 0.0825(10) 0.0433(7) -0.0135(7) 0.0199(7) -0.0322(9) C6AA 0.0378(9) 0.0592(10) 0.0539(9) 0.0059(8) 0.0078(7) 0.0067(8) C7AA 0.0550(11) 0.0771(13) 0.0599(11) 0.0002(10) 0.0000(9) 0.0224(10) C8AA 0.0505(10) 0.0510(9) 0.0586(10) 0.0005(8) -0.0067(8) -0.0058(9) C9AA 0.0463(9) 0.0525(9) 0.0475(9) -0.0156(8) -0.0003(7) -0.0011(8) C0BA 0.0364(9) 0.0776(13) 0.0640(11) 0.0156(11) 0.0097(8) 0.0002(9) C1BA 0.0510(9) 0.0422(8) 0.0397(8) -0.0032(7) 0.0164(7) 0.0055(8) C2BA 0.0581(11) 0.0581(10) 0.0571(10) -0.0014(9) 0.0119(8) -0.0174(9) O4 0.1018(11) 0.0600(8) 0.0936(11) -0.0176(8) 0.0370(9) 0.0235(9) C3BA 0.0455(10) 0.0627(12) 0.0732(12) 0.0126(10) -0.0019(9) -0.0117(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 C 1.3741(17) . ? O1 C5AA 1.4346(17) . ? O2 C5AA 1.4139(17) . ? O2 C7AA 1.427(2) . ? C C0AA 1.380(2) . ? C C4AA 1.410(2) . ? C0AA C2AA 1.429(2) . ? C0AA C1 1.517(2) . ? C1AA C5AA 1.514(2) . ? C1AA C1 1.532(2) . ? C2AA C3AA 1.424(2) . ? C2AA C6AA 1.431(2) . ? C3AA C8AA 1.415(2) . ? C3AA C9AA 1.417(2) . ? C4AA C9AA 1.354(2) . ? N2 O4 1.2124(19) . ? N2 O3 1.2196(19) . ? N2 C1BA 1.497(2) . ? C1 C1BA 1.530(2) . ? C5AA C2BA 1.512(2) . ? C6AA C0BA 1.367(2) . ? C8AA C3BA 1.361(2) . ? C0BA C3BA 1.396(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 C O1 C5AA 116.96(10) . . ? C5AA O2 C7AA 115.99(12) . . ? O1 C C0AA 124.21(13) . . ? O1 C C4AA 114.55(12) . . ? C0AA C C4AA 121.24(14) . . ? C C0AA C2AA 118.52(13) . . ? C C0AA C1 119.87(13) . . ? C2AA C0AA C1 121.58(12) . . ? C5AA C1AA C1 113.68(11) . . ? C3AA C2AA C0AA 120.10(13) . . ? C3AA C2AA C6AA 116.91(15) . . ? C0AA C2AA C6AA 122.99(14) . . ? C8AA C3AA C9AA 121.99(15) . . ? C8AA C3AA C2AA 119.82(14) . . ? C9AA C3AA C2AA 118.17(14) . . ? C9AA C4AA C 120.39(14) . . ? O4 N2 O3 123.84(16) . . ? O4 N2 C1BA 119.56(15) . . ? O3 N2 C1BA 116.54(15) . . ? C0AA C1 C1BA 108.13(11) . . ? C0AA C1 C1AA 111.25(11) . . ? C1BA C1 C1AA 112.54(13) . . ? O2 C5AA O1 108.34(11) . . ? O2 C5AA C2BA 112.83(13) . . ? O1 C5AA C2BA 105.82(11) . . ? O2 C5AA C1AA 106.86(11) . . ? O1 C5AA C1AA 109.66(12) . . ? C2BA C5AA C1AA 113.23(12) . . ? C0BA C6AA C2AA 121.03(17) . . ? C3BA C8AA C3AA 121.42(17) . . ? C4AA C9AA C3AA 121.34(15) . . ? C6AA C0BA C3BA 121.47(16) . . ? N2 C1BA C1 113.05(12) . . ? C8AA C3BA C0BA 119.30(17) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.37 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.258 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.112