# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email gshyang@mail.ahnu.edu.cn _publ_contact_author_name 'Gaosheng Yang' loop_ _publ_author_name 'Yang Gaosheng' 'Xin-Yuan Liu' data_110321b _database_code_depnum_ccdc_archive 'CCDC 860044' #TrackingRef 'web_deposit_cif_file_0_GaoshengYang_1324910743.110321b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Ethyl 2-amino-6-bromo-4-(nitromethyl)-4H-chromene-3-carboxylate ; _chemical_absolute_configuration S _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H13 Br N2 O5' _chemical_formula_weight 357.16 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' Br Br -0.2901 2.4595 '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) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.413(2) _cell_length_b 17.675(7) _cell_length_c 7.539(3) _cell_angle_alpha 90.00 _cell_angle_beta 96.083(5) _cell_angle_gamma 90.00 _cell_volume 717.3(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.654 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 360 _exptl_absorpt_coefficient_mu 2.889 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.603497 _exptl_absorpt_correction_T_max 1.000000 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5934 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0747 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -22 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 2.30 _diffrn_reflns_theta_max 27.55 _reflns_number_total 2951 _reflns_number_gt 2249 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.0954P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.016(17) _refine_ls_number_reflns 2951 _refine_ls_number_parameters 191 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0736 _refine_ls_R_factor_gt 0.0547 _refine_ls_wR_factor_ref 0.1541 _refine_ls_wR_factor_gt 0.1430 _refine_ls_goodness_of_fit_ref 0.988 _refine_ls_restrained_S_all 0.988 _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 Br1 Br 0.62245(12) 0.43862(5) 0.18284(9) 0.0654(3) Uani 1 1 d . . . O1 O 0.1083(8) 0.3472(3) 0.8169(6) 0.0520(10) Uani 1 1 d . . . C6 C 0.4702(12) 0.4085(4) 0.3854(8) 0.0465(14) Uani 1 1 d . . . C2 C 0.3934(11) 0.2478(4) 0.9016(8) 0.0424(13) Uani 1 1 d . . . C4 C 0.4317(10) 0.3214(3) 0.6252(7) 0.0382(12) Uani 1 1 d . . . C5 C 0.5471(10) 0.3449(3) 0.4800(9) 0.0440(13) Uani 1 1 d . . . H5 H 0.6796 0.3170 0.4455 0.053 Uiso 1 1 calc R . . C9 C 0.2382(11) 0.3658(3) 0.6754(8) 0.0417(13) Uani 1 1 d . . . C3 C 0.5016(10) 0.2497(3) 0.7264(7) 0.0382(12) Uani 1 1 d . . . H3 H 0.6823 0.2514 0.7553 0.046 Uiso 1 1 calc R . . C8 C 0.1576(12) 0.4309(5) 0.5788(8) 0.0519(14) Uani 1 1 d . . . H8 H 0.0235 0.4586 0.6114 0.062 Uiso 1 1 calc R . . C7 C 0.2762(11) 0.4531(3) 0.4378(9) 0.0496(15) Uani 1 1 d . . . H7 H 0.2294 0.4974 0.3766 0.060 Uiso 1 1 calc R . . C1 C 0.2059(12) 0.2944(4) 0.9373(7) 0.0422(13) Uani 1 1 d . . . C10 C 0.4918(13) 0.1971(4) 1.0417(8) 0.0491(15) Uani 1 1 d . . . O2 O 0.6714(9) 0.1519(3) 0.9895(5) 0.0520(10) Uani 1 1 d . . . O3 O 0.4272(11) 0.1918(3) 1.1899(5) 0.0681(14) Uani 1 1 d . . . C11 C 0.7905(16) 0.1010(5) 1.1239(10) 0.065(2) Uani 1 1 d . . . H11A H 0.6690 0.0670 1.1665 0.078 Uiso 1 1 calc R . . H11B H 0.8688 0.1295 1.2245 0.078 Uiso 1 1 calc R . . C13 C 0.4469(11) 0.1783(3) 0.6115(7) 0.0428(13) Uani 1 1 d . . . H13A H 0.5258 0.1832 0.5024 0.051 Uiso 1 1 calc R . . H13B H 0.5185 0.1346 0.6759 0.051 Uiso 1 1 calc R . . N2 N 0.1751(12) 0.1654(4) 0.5652(6) 0.0530(14) Uani 1 1 d . . . O4 O 0.0432(10) 0.2166(4) 0.5105(11) 0.091(2) Uani 1 1 d . . . O5 O 0.103(2) 0.1035(6) 0.5808(18) 0.174(6) Uani 1 1 d . . . N1 N 0.0890(11) 0.2968(4) 1.0843(7) 0.0588(14) Uani 1 1 d . . . H1A H 0.1310 0.2661 1.1709 0.071 Uiso 1 1 calc R . . H1B H -0.0284 0.3290 1.0926 0.071 Uiso 1 1 calc R . . C12 C 0.9803(14) 0.0572(5) 1.0376(11) 0.067(2) Uani 1 1 d . . . H12A H 0.8989 0.0211 0.9561 0.101 Uiso 1 1 calc R . . H12B H 1.0872 0.0311 1.1273 0.101 Uiso 1 1 calc R . . H12C H 1.0773 0.0912 0.9737 0.101 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 Br1 0.0584(4) 0.0712(5) 0.0694(4) 0.0250(4) 0.0191(3) 0.0028(4) O1 0.036(2) 0.063(3) 0.059(3) -0.002(2) 0.0138(19) 0.0084(18) C6 0.041(3) 0.051(3) 0.046(3) 0.005(2) -0.003(3) -0.006(2) C2 0.038(3) 0.055(3) 0.034(3) -0.009(3) 0.006(2) -0.002(3) C4 0.028(2) 0.049(3) 0.038(3) -0.002(2) 0.005(2) -0.002(2) C5 0.031(3) 0.044(3) 0.058(4) 0.003(3) 0.007(2) 0.002(2) C9 0.034(3) 0.048(3) 0.042(3) -0.006(2) 0.002(2) 0.002(2) C3 0.028(2) 0.051(3) 0.035(3) 0.000(2) 0.005(2) 0.006(2) C8 0.050(3) 0.054(4) 0.052(3) -0.002(3) 0.005(2) 0.011(4) C7 0.047(3) 0.042(4) 0.060(3) 0.003(3) 0.005(3) 0.007(3) C1 0.039(3) 0.056(4) 0.032(3) -0.006(2) 0.001(2) 0.000(3) C10 0.047(3) 0.054(4) 0.045(4) -0.011(3) 0.002(3) -0.001(3) O2 0.057(3) 0.067(3) 0.032(2) 0.0040(19) 0.0016(18) 0.012(2) O3 0.082(3) 0.101(4) 0.0228(19) 0.004(2) 0.012(2) 0.020(3) C11 0.062(5) 0.089(6) 0.042(4) 0.008(3) -0.004(3) 0.021(4) C13 0.051(3) 0.050(3) 0.029(2) 0.000(2) 0.011(2) 0.008(3) N2 0.063(3) 0.067(4) 0.029(2) -0.002(2) 0.004(2) -0.022(3) O4 0.041(3) 0.081(4) 0.147(6) -0.034(4) -0.009(3) 0.008(3) O5 0.145(9) 0.126(7) 0.226(12) 0.097(8) -0.100(9) -0.084(7) N1 0.058(3) 0.080(4) 0.040(3) -0.003(3) 0.016(2) 0.014(3) C12 0.064(5) 0.078(5) 0.061(5) 0.015(4) 0.010(3) 0.017(4) _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 Br1 C6 1.888(6) . ? O1 C1 1.369(8) . ? O1 C9 1.378(7) . ? C6 C5 1.372(9) . ? C6 C7 1.403(9) . ? C2 C1 1.356(9) . ? C2 C10 1.443(10) . ? C2 C3 1.501(7) . ? C4 C5 1.380(8) . ? C4 C9 1.393(8) . ? C4 C3 1.507(8) . ? C5 H5 0.9300 . ? C9 C8 1.406(10) . ? C3 C13 1.541(8) . ? C3 H3 0.9800 . ? C8 C7 1.357(9) . ? C8 H8 0.9300 . ? C7 H7 0.9300 . ? C1 N1 1.334(8) . ? C10 O3 1.209(8) . ? C10 O2 1.349(8) . ? O2 C11 1.455(9) . ? C11 C12 1.490(11) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C13 N2 1.493(9) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? N2 O5 1.170(9) . ? N2 O4 1.199(9) . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? 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 C1 O1 C9 118.9(5) . . ? C5 C6 C7 120.6(6) . . ? C5 C6 Br1 121.1(5) . . ? C7 C6 Br1 118.2(5) . . ? C1 C2 C10 117.3(5) . . ? C1 C2 C3 122.1(5) . . ? C10 C2 C3 120.6(5) . . ? C5 C4 C9 117.6(5) . . ? C5 C4 C3 123.0(5) . . ? C9 C4 C3 119.4(5) . . ? C4 C5 C6 121.4(6) . . ? C4 C5 H5 119.3 . . ? C6 C5 H5 119.3 . . ? O1 C9 C4 122.4(5) . . ? O1 C9 C8 116.1(5) . . ? C4 C9 C8 121.4(5) . . ? C2 C3 C4 111.3(4) . . ? C2 C3 C13 114.0(5) . . ? C4 C3 C13 112.4(4) . . ? C2 C3 H3 106.1 . . ? C4 C3 H3 106.1 . . ? C13 C3 H3 106.1 . . ? C7 C8 C9 119.7(6) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C7 C6 119.2(6) . . ? C8 C7 H7 120.4 . . ? C6 C7 H7 120.4 . . ? N1 C1 C2 128.0(6) . . ? N1 C1 O1 110.2(5) . . ? C2 C1 O1 121.8(5) . . ? O3 C10 O2 120.8(6) . . ? O3 C10 C2 127.1(6) . . ? O2 C10 C2 112.1(5) . . ? C10 O2 C11 116.3(5) . . ? O2 C11 C12 107.0(6) . . ? O2 C11 H11A 110.3 . . ? C12 C11 H11A 110.3 . . ? O2 C11 H11B 110.3 . . ? C12 C11 H11B 110.3 . . ? H11A C11 H11B 108.6 . . ? N2 C13 C3 112.5(5) . . ? N2 C13 H13A 109.1 . . ? C3 C13 H13A 109.1 . . ? N2 C13 H13B 109.1 . . ? C3 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? O5 N2 O4 123.2(8) . . ? O5 N2 C13 116.7(8) . . ? O4 N2 C13 120.1(6) . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.55 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 1.076 _refine_diff_density_min -0.505 _refine_diff_density_rms 0.100 # Attachment 'web_deposit_cif_file_1_GaoshengYang_1324910743.110427a.cif' data_110427a _database_code_depnum_ccdc_archive 'CCDC 860045' #TrackingRef 'web_deposit_cif_file_1_GaoshengYang_1324910743.110427a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Amino-6-bromo-4-(nitromethyl)-4H-chromene-3-carbonitrile ; _chemical_absolute_configuration R _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C11 H8 Br N3 O3' _chemical_formula_weight 310.11 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' Br Br -0.2901 2.4595 '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) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 9.397(6) _cell_length_b 5.142(3) _cell_length_c 12.852(8) _cell_angle_alpha 90.00 _cell_angle_beta 109.634(7) _cell_angle_gamma 90.00 _cell_volume 585.0(7) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.761 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 308 _exptl_absorpt_coefficient_mu 3.517 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5397 _exptl_absorpt_correction_T_max 0.6205 _exptl_absorpt_process_details ? _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 '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 4955 _diffrn_reflns_av_R_equivalents 0.1052 _diffrn_reflns_av_sigmaI/netI 0.1256 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 27.74 _reflns_number_total 2349 _reflns_number_gt 1294 _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^)+(0.1394P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.03(3) _refine_ls_number_reflns 2349 _refine_ls_number_parameters 163 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1457 _refine_ls_R_factor_gt 0.0811 _refine_ls_wR_factor_ref 0.2211 _refine_ls_wR_factor_gt 0.1854 _refine_ls_goodness_of_fit_ref 0.889 _refine_ls_restrained_S_all 0.889 _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 Br1 Br -0.17099(11) 0.9077(4) 0.42094(9) 0.0724(5) Uani 1 1 d . . . C1 C 0.2164(11) 0.537(2) 0.0856(9) 0.045(2) Uani 1 1 d . . . C2 C 0.2932(10) 0.739(2) 0.1439(8) 0.041(2) Uani 1 1 d . . . C3 C 0.2662(9) 0.8446(17) 0.2442(7) 0.038(2) Uani 1 1 d . . . H3 H 0.2576 1.0338 0.2350 0.045 Uiso 1 1 calc R . . C4 C 0.1143(10) 0.748(2) 0.2463(8) 0.042(2) Uani 1 1 d . . . C5 C 0.0486(10) 0.859(3) 0.3175(8) 0.049(3) Uani 1 1 d . . . H5 H 0.0948 1.0000 0.3611 0.059 Uiso 1 1 calc R . . C6 C -0.0841(11) 0.762(2) 0.3236(9) 0.052(3) Uani 1 1 d . . . C7 C -0.1524(11) 0.552(2) 0.2590(9) 0.053(3) Uani 1 1 d . . . H7 H -0.2418 0.4846 0.2640 0.063 Uiso 1 1 calc R . . C8 C -0.0894(10) 0.441(2) 0.1876(8) 0.048(3) Uani 1 1 d . . . H8 H -0.1354 0.3002 0.1436 0.058 Uiso 1 1 calc R . . C9 C 0.0418(10) 0.542(2) 0.1829(8) 0.042(2) Uani 1 1 d . . . C10 C 0.4153(12) 0.841(2) 0.1153(8) 0.054(3) Uani 1 1 d . . . C11 C 0.3956(10) 0.7941(17) 0.3504(8) 0.042(2) Uani 1 1 d . . . H11A H 0.4867 0.8766 0.3467 0.051 Uiso 1 1 calc R . . H11B H 0.3724 0.8688 0.4121 0.051 Uiso 1 1 calc R . . N1 N 0.2419(9) 0.415(3) 0.0018(6) 0.060(2) Uani 1 1 d . . . H1A H 0.3146 0.4648 -0.0201 0.072 Uiso 1 1 calc R . . H1B H 0.1856 0.2866 -0.0304 0.072 Uiso 1 1 calc R . . N2 N 0.5140(11) 0.920(3) 0.0945(8) 0.082(3) Uani 1 1 d . . . N3 N 0.4216(8) 0.5099(16) 0.3680(7) 0.046(2) Uani 1 1 d . . . O1 O 0.0989(7) 0.4283(19) 0.1079(5) 0.0493(16) Uani 1 1 d . . . O2 O 0.5086(9) 0.411(3) 0.3317(8) 0.087(2) Uani 1 1 d . . . O3 O 0.3441(7) 0.388(3) 0.4096(6) 0.065(2) 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 Br1 0.0632(7) 0.0813(9) 0.0942(9) -0.0117(10) 0.0549(6) 0.0027(8) C1 0.040(5) 0.041(6) 0.059(6) 0.006(5) 0.023(5) 0.007(5) C2 0.038(5) 0.044(6) 0.053(6) 0.010(5) 0.030(4) 0.006(4) C3 0.041(5) 0.027(6) 0.057(5) -0.002(4) 0.031(4) -0.005(4) C4 0.034(5) 0.037(6) 0.060(6) 0.006(5) 0.023(4) 0.005(4) C5 0.048(5) 0.045(9) 0.061(6) 0.000(5) 0.028(4) 0.001(5) C6 0.042(5) 0.055(7) 0.071(7) 0.008(6) 0.033(5) -0.004(5) C7 0.036(5) 0.054(7) 0.075(8) 0.005(6) 0.028(5) -0.007(5) C8 0.043(4) 0.036(7) 0.071(6) -0.002(6) 0.025(4) 0.000(5) C9 0.040(5) 0.030(5) 0.060(6) -0.002(5) 0.024(5) 0.001(4) C10 0.068(6) 0.046(8) 0.063(6) 0.005(5) 0.043(5) 0.004(5) C11 0.045(5) 0.022(5) 0.064(7) -0.007(4) 0.025(5) -0.009(4) N1 0.069(5) 0.063(6) 0.065(5) 0.000(7) 0.043(4) -0.007(7) N2 0.087(6) 0.078(7) 0.112(7) 0.019(10) 0.072(6) 0.017(9) N3 0.034(4) 0.033(4) 0.072(6) -0.002(4) 0.021(4) -0.002(3) O1 0.052(3) 0.042(4) 0.068(4) -0.009(5) 0.038(3) -0.011(4) O2 0.088(5) 0.055(5) 0.151(7) 0.015(10) 0.083(5) 0.021(7) O3 0.075(5) 0.045(5) 0.090(5) 0.014(6) 0.046(4) 0.005(5) _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 Br1 C6 1.864(11) . ? C1 N1 1.337(15) . ? C1 C2 1.339(15) . ? C1 O1 1.352(11) . ? C2 C10 1.418(13) . ? C2 C3 1.497(12) . ? C3 C11 1.515(13) . ? C3 C4 1.520(11) . ? C3 H3 0.9800 . ? C4 C9 1.370(14) . ? C4 C5 1.388(13) . ? C5 C6 1.369(13) . ? C5 H5 0.9300 . ? C6 C7 1.385(16) . ? C7 C8 1.372(15) . ? C7 H7 0.9300 . ? C8 C9 1.358(12) . ? C8 H8 0.9300 . ? C9 O1 1.380(11) . ? C10 N2 1.124(13) . ? C11 N3 1.486(12) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? N1 H1A 0.8600 . ? N1 H1B 0.8600 . ? N3 O2 1.183(11) . ? N3 O3 1.213(12) . ? 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 C1 C2 127.3(10) . . ? N1 C1 O1 110.8(10) . . ? C2 C1 O1 121.8(9) . . ? C1 C2 C10 118.2(9) . . ? C1 C2 C3 123.2(8) . . ? C10 C2 C3 118.4(9) . . ? C11 C3 C2 113.3(7) . . ? C11 C3 C4 113.7(7) . . ? C2 C3 C4 109.1(8) . . ? C11 C3 H3 106.7 . . ? C2 C3 H3 106.7 . . ? C4 C3 H3 106.7 . . ? C9 C4 C5 117.9(9) . . ? C9 C4 C3 121.7(8) . . ? C5 C4 C3 120.3(9) . . ? C6 C5 C4 120.3(11) . . ? C6 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C5 C6 C7 119.8(10) . . ? C5 C6 Br1 120.4(9) . . ? C7 C6 Br1 119.8(7) . . ? C8 C7 C6 120.6(9) . . ? C8 C7 H7 119.7 . . ? C6 C7 H7 119.7 . . ? C9 C8 C7 118.3(10) . . ? C9 C8 H8 120.9 . . ? C7 C8 H8 120.9 . . ? C8 C9 C4 123.1(9) . . ? C8 C9 O1 116.2(9) . . ? C4 C9 O1 120.7(8) . . ? N2 C10 C2 178.6(12) . . ? N3 C11 C3 110.3(7) . . ? N3 C11 H11A 109.6 . . ? C3 C11 H11A 109.6 . . ? N3 C11 H11B 109.6 . . ? C3 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? C1 N1 H1A 120.0 . . ? C1 N1 H1B 120.0 . . ? H1A N1 H1B 120.0 . . ? O2 N3 O3 123.3(11) . . ? O2 N3 C11 117.4(10) . . ? O3 N3 C11 119.0(9) . . ? C1 O1 C9 120.6(9) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 27.74 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 1.330 _refine_diff_density_min -0.729 _refine_diff_density_rms 0.149 # Attachment 'web_deposit_cif_file_2_GaoshengYang_1324910743.110419a.cif' data_110419a _database_code_depnum_ccdc_archive 'CCDC 860046' #TrackingRef 'web_deposit_cif_file_2_GaoshengYang_1324910743.110419a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-Imino-2H-chromene-3-carbonitrile ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C10 H6 N2 O' _chemical_formula_weight 170.17 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 '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 11.833(4) _cell_length_b 9.268(3) _cell_length_c 7.280(2) _cell_angle_alpha 90.00 _cell_angle_beta 95.842(4) _cell_angle_gamma 90.00 _cell_volume 794.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.423 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9811 _exptl_absorpt_correction_T_max 0.9839 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5907 _diffrn_reflns_av_R_equivalents 0.0200 _diffrn_reflns_av_sigmaI/netI 0.0190 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.73 _diffrn_reflns_theta_max 25.99 _reflns_number_total 1562 _reflns_number_gt 1262 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _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^)+(0.1062P)^2^+0.1573P] 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 1562 _refine_ls_number_parameters 120 _refine_ls_number_restraints 19 _refine_ls_R_factor_all 0.0623 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1717 _refine_ls_wR_factor_gt 0.1600 _refine_ls_goodness_of_fit_ref 1.063 _refine_ls_restrained_S_all 1.066 _refine_ls_shift/su_max 0.003 _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 0.87138(10) 0.51709(15) 0.10058(18) 0.0556(4) Uani 1 1 d . . . C7 C 0.65653(14) 0.5708(2) -0.0735(2) 0.0491(5) Uani 1 1 d . . . H7 H 0.5848 0.5883 -0.1342 0.059 Uiso 1 1 calc R . . N2 N 0.83688(14) 0.28329(16) 0.0967(3) 0.0617(5) Uani 1 1 d U . . H2A H 0.8957 0.2883 0.1456 0.093 Uiso 1 1 calc R . . C5 C 0.83643(15) 0.6580(2) 0.0691(2) 0.0475(5) Uani 1 1 d . . . C1 C 0.69704(18) 0.8337(2) -0.0431(3) 0.0571(5) Uani 1 1 d . . . H1 H 0.6254 0.8572 -0.0996 0.069 Uiso 1 1 calc R . . C10 C 0.62307(16) 0.3117(2) -0.1006(3) 0.0567(5) Uani 1 1 d . . . C6 C 0.72825(15) 0.6888(2) -0.0163(2) 0.0477(5) Uani 1 1 d . . . C8 C 0.69121(15) 0.4338(2) -0.0408(2) 0.0487(5) Uani 1 1 d . . . C9 C 0.80263(15) 0.4023(2) 0.0560(3) 0.0530(5) Uani 1 1 d U . . C2 C 0.7728(2) 0.9412(2) 0.0144(3) 0.0647(6) Uani 1 1 d . . . H2 H 0.7521 1.0373 -0.0036 0.078 Uiso 1 1 calc R . . C3 C 0.87871(19) 0.9071(2) 0.0983(3) 0.0648(6) Uani 1 1 d . . . H3 H 0.9287 0.9810 0.1369 0.078 Uiso 1 1 calc R . . C4 C 0.91272(17) 0.7655(2) 0.1266(3) 0.0585(5) Uani 1 1 d . . . H4 H 0.9848 0.7434 0.1827 0.070 Uiso 1 1 calc R . . N1 N 0.56830(17) 0.2154(2) -0.1507(3) 0.0783(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 O1 0.0414(7) 0.0565(8) 0.0660(8) -0.0032(6) -0.0087(5) 0.0025(6) C7 0.0414(9) 0.0557(11) 0.0484(9) 0.0032(7) -0.0038(7) 0.0009(8) N2 0.0485(9) 0.0436(9) 0.0870(12) -0.0009(7) -0.0226(8) 0.0089(7) C5 0.0459(9) 0.0506(10) 0.0458(9) -0.0022(7) 0.0033(7) -0.0028(7) C1 0.0618(11) 0.0535(11) 0.0557(11) 0.0043(8) 0.0038(8) 0.0035(9) C10 0.0505(10) 0.0580(11) 0.0595(11) -0.0016(8) -0.0050(8) -0.0028(9) C6 0.0470(9) 0.0511(10) 0.0444(9) 0.0018(7) 0.0025(7) 0.0001(8) C8 0.0442(9) 0.0511(10) 0.0493(9) 0.0003(7) -0.0023(7) -0.0008(7) C9 0.0475(10) 0.0522(10) 0.0574(10) -0.0047(8) -0.0046(8) 0.0007(8) C2 0.0853(15) 0.0483(11) 0.0616(12) -0.0001(8) 0.0124(10) -0.0051(10) C3 0.0737(14) 0.0605(13) 0.0613(11) -0.0094(9) 0.0112(10) -0.0211(10) C4 0.0502(10) 0.0675(12) 0.0569(10) -0.0057(9) 0.0012(8) -0.0104(9) N1 0.0714(12) 0.0708(13) 0.0883(14) -0.0098(10) -0.0133(10) -0.0163(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 C9 1.358(2) . ? O1 C5 1.382(2) . ? C7 C8 1.348(3) . ? C7 C6 1.420(3) . ? C7 H7 0.9300 . ? N2 C9 1.202(2) . ? N2 H2A 0.7500 . ? C5 C4 1.381(3) . ? C5 C6 1.394(3) . ? C1 C2 1.376(3) . ? C1 C6 1.402(3) . ? C1 H1 0.9300 . ? C10 N1 1.140(3) . ? C10 C8 1.432(3) . ? C8 C9 1.460(3) . ? C2 C3 1.374(3) . ? C2 H2 0.9300 . ? C3 C4 1.381(3) . ? C3 H3 0.9300 . ? C4 H4 0.9300 . ? 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 O1 C5 122.59(14) . . ? C8 C7 C6 120.75(16) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C9 N2 H2A 109.5 . . ? C4 C5 O1 117.15(16) . . ? C4 C5 C6 122.00(18) . . ? O1 C5 C6 120.85(16) . . ? C2 C1 C6 119.80(19) . . ? C2 C1 H1 120.1 . . ? C6 C1 H1 120.1 . . ? N1 C10 C8 179.0(2) . . ? C5 C6 C1 118.36(18) . . ? C5 C6 C7 117.87(16) . . ? C1 C6 C7 123.77(17) . . ? C7 C8 C10 122.63(16) . . ? C7 C8 C9 121.14(17) . . ? C10 C8 C9 116.22(16) . . ? N2 C9 O1 118.77(16) . . ? N2 C9 C8 124.59(17) . . ? O1 C9 C8 116.64(16) . . ? C3 C2 C1 120.4(2) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C2 C3 C4 121.56(19) . . ? C2 C3 H3 119.2 . . ? C4 C3 H3 119.2 . . ? C5 C4 C3 117.93(19) . . ? C5 C4 H4 121.0 . . ? C3 C4 H4 121.0 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.324 _refine_diff_density_min -0.396 _refine_diff_density_rms 0.058