# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full 'RSC Advances' _journal_coden_Cambridge 1500 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Wen-Jing Xiao' _publ_contact_author_email wxiao@mail.ccnu.edu.cn _publ_section_title ; Room Temperature Synthesis of Isoquino[2,1-a][3,1]oxazine and Isoquino[2,1-a] pyrimidine Derivatives via Visible Light Photoredox Catalysis ; _publ_author_name 'Wen-Jing Xiao' data_t _database_code_depnum_ccdc_archive 'CCDC 848932' #TrackingRef '- cif.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H15 N O' _chemical_formula_sum 'C16 H15 N O' _chemical_formula_weight 237.29 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 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 10.7911(19) _cell_length_b 8.3666(15) _cell_length_c 6.8985(12) _cell_angle_alpha 90.00 _cell_angle_beta 93.084(3) _cell_angle_gamma 90.00 _cell_volume 621.93(19) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2787 _cell_measurement_theta_min 3.08 _cell_measurement_theta_max 31.87 _exptl_crystal_description block _exptl_crystal_colour clourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 264 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 3322 _diffrn_reflns_av_R_equivalents 0.0207 _diffrn_reflns_av_sigmaI/netI 0.0250 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.50 _reflns_number_total 1143 _reflns_number_gt 1012 _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^)+(0.1255P)^2^+0.0735P] 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 0.18(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1143 _refine_ls_number_parameters 102 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0637 _refine_ls_R_factor_gt 0.0595 _refine_ls_wR_factor_ref 0.1854 _refine_ls_wR_factor_gt 0.1796 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.118 _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 C1 C 0.72988(14) 0.95331(17) 0.0473(2) 0.0495(5) Uani 1 1 d . A . C2 C 0.85393(17) 0.9520(2) 0.1106(3) 0.0650(6) Uani 1 1 d . . . H2 H 0.9106 0.8952 0.0404 0.078 Uiso 1 1 calc R . . C3 C 0.89497(19) 1.0336(3) 0.2762(3) 0.0743(7) Uani 1 1 d . . . H3 H 0.9787 1.0330 0.3160 0.089 Uiso 1 1 calc R . . C4 C 0.8111(2) 1.1154(2) 0.3814(3) 0.0782(7) Uani 1 1 d . . . H4 H 0.8382 1.1705 0.4928 0.094 Uiso 1 1 calc R . . C5 C 0.6871(2) 1.1161(2) 0.3227(3) 0.0704(7) Uani 1 1 d . B . H5 H 0.6307 1.1701 0.3962 0.085 Uiso 1 1 calc R . . C6 C 0.64540(15) 1.03629(16) 0.1532(2) 0.0493(5) Uani 1 1 d . . . C7 C 0.68509(16) 0.8629(3) -0.1311(3) 0.0743(7) Uani 1 1 d D . . H7A H 0.6645 0.7540 -0.0968 0.089 Uiso 1 1 calc R A . H7B H 0.7499 0.8593 -0.2232 0.089 Uiso 1 1 calc R . . N1 N 0.4715(5) 0.9357(5) -0.0813(7) 0.0444(10) Uani 0.50 1 d PD . -1 O1 O 0.44848(19) 1.1702(2) 0.1115(3) 0.0524(6) Uani 0.50 1 d PD . -1 C8 C 0.5660(3) 0.9499(4) -0.2257(4) 0.0512(8) Uani 0.50 1 d PD A -1 H8A H 0.5838 1.0613 -0.2517 0.061 Uiso 0.50 1 calc PR A -1 H8B H 0.5384 0.8984 -0.3465 0.061 Uiso 0.50 1 calc PR A -1 C9 C 0.5005(6) 1.0153(6) 0.1031(9) 0.0431(11) Uani 0.50 1 d PD B -1 H9 H 0.4662 0.9507 0.2059 0.052 Uiso 0.50 1 calc PR B -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0590(10) 0.0460(9) 0.0441(8) 0.0021(5) 0.0074(6) -0.0039(6) C2 0.0588(10) 0.0776(13) 0.0591(10) 0.0041(8) 0.0080(7) -0.0036(8) C3 0.0690(11) 0.0850(14) 0.0669(12) 0.0104(9) -0.0137(9) -0.0104(9) C4 0.1015(16) 0.0720(13) 0.0575(10) -0.0056(9) -0.0280(10) 0.0020(10) C5 0.0953(14) 0.0666(11) 0.0472(9) -0.0121(7) -0.0160(8) 0.0251(9) C6 0.0653(10) 0.0437(8) 0.0384(8) 0.0010(5) -0.0023(6) 0.0074(6) C7 0.0566(10) 0.0959(14) 0.0711(12) -0.0371(10) 0.0103(8) 0.0051(8) N1 0.057(2) 0.043(2) 0.0332(16) -0.0045(17) 0.0039(14) 0.0023(16) O1 0.0600(13) 0.0420(11) 0.0551(12) -0.0090(9) 0.0023(9) 0.0025(9) C8 0.0629(18) 0.0599(17) 0.0316(13) -0.0069(11) 0.0100(12) -0.0068(13) C9 0.054(3) 0.040(3) 0.0347(19) -0.0029(18) 0.0027(16) 0.0003(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.385(2) . ? C1 C2 1.386(2) . ? C1 C7 1.503(2) . ? C2 C3 1.383(3) . ? C2 H2 0.9300 . ? C3 C4 1.372(3) . ? C3 H3 0.9300 . ? C4 C5 1.377(3) . ? C4 H4 0.9300 . ? C5 C6 1.400(2) . ? C5 H5 0.9300 . ? C6 N1 1.351(6) 3_675 ? C6 C9 1.593(6) . ? C7 O1 1.481(3) 3_675 ? C7 C8 1.586(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? N1 C6 1.351(6) 3_675 ? N1 C9 1.455(3) . ? N1 C8 1.469(5) . ? O1 C9 1.415(6) . ? O1 C7 1.481(3) 3_675 ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9 0.9800 . ? 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 C1 C2 119.36(15) . . ? C6 C1 C7 119.52(15) . . ? C2 C1 C7 121.11(15) . . ? C3 C2 C1 121.13(17) . . ? C3 C2 H2 119.4 . . ? C1 C2 H2 119.4 . . ? C4 C3 C2 119.48(18) . . ? C4 C3 H3 120.3 . . ? C2 C3 H3 120.3 . . ? C3 C4 C5 120.30(17) . . ? C3 C4 H4 119.9 . . ? C5 C4 H4 119.9 . . ? C4 C5 C6 120.49(18) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? N1 C6 C1 121.4(2) 3_675 . ? N1 C6 C5 118.4(2) 3_675 . ? C1 C6 C5 119.23(17) . . ? N1 C6 C9 18.8(2) 3_675 . ? C1 C6 C9 119.8(2) . . ? C5 C6 C9 120.1(3) . . ? O1 C7 C1 106.91(14) 3_675 . ? O1 C7 C8 49.66(15) 3_675 . ? C1 C7 C8 108.87(16) . . ? O1 C7 H7A 64.2 3_675 . ? C1 C7 H7A 109.9 . . ? C8 C7 H7A 109.9 . . ? O1 C7 H7B 142.5 3_675 . ? C1 C7 H7B 109.9 . . ? C8 C7 H7B 109.9 . . ? H7A C7 H7B 108.3 . . ? C6 N1 C9 113.3(3) 3_675 . ? C6 N1 C8 113.9(4) 3_675 . ? C9 N1 C8 115.5(4) . . ? C9 O1 C7 102.9(3) . 3_675 ? N1 C8 C7 105.1(3) . . ? N1 C8 H8A 110.7 . . ? C7 C8 H8A 110.7 . . ? N1 C8 H8B 110.7 . . ? C7 C8 H8B 110.7 . . ? H8A C8 H8B 108.8 . . ? O1 C9 N1 112.8(3) . . ? O1 C9 C6 106.1(3) . . ? N1 C9 C6 113.8(3) . . ? O1 C9 H9 108.0 . . ? N1 C9 H9 108.0 . . ? C6 C9 H9 108.0 . . ? 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 C6 C1 C2 C3 -0.8(2) . . . . ? C7 C1 C2 C3 -179.18(17) . . . . ? C1 C2 C3 C4 1.0(3) . . . . ? C2 C3 C4 C5 0.1(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C2 C1 C6 N1 168.5(2) . . . 3_675 ? C7 C1 C6 N1 -13.1(3) . . . 3_675 ? C2 C1 C6 C5 -0.4(2) . . . . ? C7 C1 C6 C5 178.00(16) . . . . ? C2 C1 C6 C9 -169.8(2) . . . . ? C7 C1 C6 C9 8.7(3) . . . . ? C4 C5 C6 N1 -167.8(2) . . . 3_675 ? C4 C5 C6 C1 1.5(3) . . . . ? C4 C5 C6 C9 170.8(3) . . . . ? C6 C1 C7 O1 -22.5(2) . . . 3_675 ? C2 C1 C7 O1 155.96(17) . . . 3_675 ? C6 C1 C7 C8 29.9(2) . . . . ? C2 C1 C7 C8 -151.71(18) . . . . ? C6 N1 C8 C7 -163.2(3) 3_675 . . . ? C9 N1 C8 C7 63.2(3) . . . . ? O1 C7 C8 N1 32.1(2) 3_675 . . . ? C1 C7 C8 N1 -64.4(3) . . . . ? C7 O1 C9 N1 73.4(4) 3_675 . . . ? C7 O1 C9 C6 -161.4(3) 3_675 . . . ? C6 N1 C9 O1 -38.6(5) 3_675 . . . ? C8 N1 C9 O1 95.4(3) . . . . ? C6 N1 C9 C6 -159.5(3) 3_675 . . . ? C8 N1 C9 C6 -25.5(4) . . . . ? N1 C6 C9 O1 -37.2(10) 3_675 . . . ? C1 C6 C9 O1 -137.7(3) . . . . ? C5 C6 C9 O1 53.0(4) . . . . ? N1 C6 C9 N1 87.4(13) 3_675 . . . ? C1 C6 C9 N1 -13.1(4) . . . . ? C5 C6 C9 N1 177.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.215 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.061