# Electronic Supplementary Material (ESI) for RSC Advances # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_e113_0m _database_code_depnum_ccdc_archive 'CCDC 870509' _audit_creation_method SHELXL-97 _chemical_name_systematic (2-Amino-3-cyano-4H-chromene-4-yl)malononitrile _chemical_name_common ? _chemical_melting_point 152 _chemical_formula_moiety 'C13 H8 N4 O' _chemical_formula_sum 'C13 H8 N4 O' _chemical_formula_weight 236.23 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 5.6073(8) _cell_length_b 8.1748(11) _cell_length_c 12.5000(17) _cell_angle_alpha 103.057(7) _cell_angle_beta 90.883(8) _cell_angle_gamma 96.555(8) _cell_volume 554.02(13) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.416 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 244 _exptl_absorpt_coefficient_mu 0.096 _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3766 _diffrn_reflns_av_R_equivalents 0.1222 _diffrn_reflns_av_sigmaI/netI 0.0804 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.67 _diffrn_reflns_theta_max 25.02 _reflns_number_total 1846 _reflns_number_gt 1594 _reflns_threshold_expression >2sigma(I) _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1063P)^2^+0.0153P] 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 mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.11(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 1846 _refine_ls_number_parameters 196 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0586 _refine_ls_R_factor_gt 0.0540 _refine_ls_wR_factor_ref 0.1526 _refine_ls_wR_factor_gt 0.1463 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _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 0.41443(19) 0.57512(15) 0.73927(9) 0.0374(4) Uani 1 1 d . . . N2 N 1.1156(3) 0.67296(19) 0.97428(13) 0.0456(5) Uani 1 1 d . . . N4 N 1.0030(3) 1.2257(2) 0.73645(15) 0.0574(5) Uani 1 1 d . . . N3 N 0.3738(3) 1.0210(2) 0.87717(14) 0.0504(5) Uani 1 1 d . . . N1 N 0.5371(3) 0.44621(19) 0.86439(13) 0.0416(4) Uani 1 1 d . . . C2 C 0.3391(4) 0.6963(2) 0.48126(15) 0.0469(5) Uani 1 1 d . . . C3 C 0.5537(4) 0.7961(2) 0.47714(14) 0.0481(5) Uani 1 1 d . . . C4 C 0.7205(4) 0.8309(2) 0.56466(14) 0.0399(5) Uani 1 1 d . . . C9 C 0.6769(3) 0.76567(18) 0.65739(12) 0.0310(4) Uani 1 1 d . . . C5 C 0.8448(3) 0.80915(19) 0.75768(12) 0.0290(4) Uani 1 1 d . . . C6 C 0.8011(3) 0.67711(19) 0.82414(12) 0.0301(4) Uani 1 1 d . . . C10 C 0.9745(3) 0.67174(18) 0.90582(13) 0.0331(4) Uani 1 1 d . . . C13 C 0.9191(3) 1.1252(2) 0.77824(14) 0.0359(5) Uani 1 1 d . . . C11 C 0.8196(3) 0.99019(18) 0.83088(13) 0.0289(4) Uani 1 1 d . . . C12 C 0.5686(3) 1.00948(19) 0.85770(13) 0.0325(4) Uani 1 1 d . . . C7 C 0.5935(3) 0.56912(19) 0.81151(12) 0.0306(4) Uani 1 1 d . . . C8 C 0.4656(3) 0.65940(19) 0.65576(12) 0.0313(4) Uani 1 1 d . . . C1 C 0.2951(3) 0.6267(2) 0.57054(14) 0.0407(5) Uani 1 1 d . . . H4 H 0.863(4) 0.905(3) 0.5640(15) 0.044(5) Uiso 1 1 d . . . H1 H 0.153(4) 0.550(3) 0.5724(18) 0.059(6) Uiso 1 1 d . . . H3 H 0.592(4) 0.838(3) 0.4132(19) 0.059(6) Uiso 1 1 d . . . H2 H 0.218(4) 0.670(2) 0.4229(18) 0.052(5) Uiso 1 1 d . . . H5 H 1.010(3) 0.818(2) 0.7383(13) 0.032(4) Uiso 1 1 d . . . H8 H 0.907(3) 1.001(2) 0.8964(15) 0.031(4) Uiso 1 1 d . . . H6 H 0.643(5) 0.430(3) 0.917(2) 0.067(7) Uiso 1 1 d . . . H7 H 0.395(4) 0.394(3) 0.8508(17) 0.048(6) Uiso 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 0.0277(7) 0.0472(7) 0.0374(7) 0.0135(5) -0.0059(5) -0.0016(5) N2 0.0449(10) 0.0466(9) 0.0456(9) 0.0140(7) -0.0159(7) 0.0031(6) N4 0.0583(12) 0.0499(10) 0.0668(11) 0.0242(9) 0.0048(9) -0.0044(8) N3 0.0297(9) 0.0563(10) 0.0644(11) 0.0109(8) 0.0029(7) 0.0077(7) N1 0.0375(9) 0.0417(9) 0.0475(9) 0.0180(7) -0.0033(7) -0.0016(7) C2 0.0556(12) 0.0504(11) 0.0330(9) 0.0012(8) -0.0154(9) 0.0179(9) C3 0.0690(14) 0.0470(11) 0.0316(9) 0.0105(8) -0.0016(9) 0.0180(9) C4 0.0481(11) 0.0390(9) 0.0333(9) 0.0090(7) 0.0005(8) 0.0069(8) C9 0.0345(9) 0.0295(8) 0.0287(8) 0.0034(6) -0.0006(7) 0.0100(6) C5 0.0236(8) 0.0318(9) 0.0313(8) 0.0061(6) 0.0004(6) 0.0047(6) C6 0.0288(9) 0.0294(8) 0.0313(8) 0.0052(6) -0.0056(7) 0.0053(6) C10 0.0338(9) 0.0294(8) 0.0363(9) 0.0080(7) -0.0027(7) 0.0041(6) C13 0.0297(9) 0.0329(9) 0.0435(9) 0.0075(7) -0.0023(7) -0.0002(7) C11 0.0244(8) 0.0304(9) 0.0309(8) 0.0064(6) -0.0035(6) 0.0019(6) C12 0.0314(9) 0.0294(8) 0.0350(8) 0.0047(6) -0.0036(7) 0.0024(6) C7 0.0301(8) 0.0315(8) 0.0291(8) 0.0033(6) -0.0018(6) 0.0072(6) C8 0.0313(9) 0.0335(8) 0.0283(8) 0.0028(6) -0.0018(6) 0.0097(6) C1 0.0380(10) 0.0426(10) 0.0380(9) 0.0002(7) -0.0101(8) 0.0105(8) _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 C7 1.3526(19) . ? O1 C8 1.3913(19) . ? N2 C10 1.154(2) . ? N4 C13 1.133(2) . ? N3 C12 1.133(2) . ? N1 C7 1.334(2) . ? N1 H6 0.92(3) . ? N1 H7 0.86(2) . ? C2 C1 1.376(3) . ? C2 C3 1.383(3) . ? C2 H2 0.96(2) . ? C3 C4 1.385(3) . ? C3 H3 0.96(2) . ? C4 C9 1.395(2) . ? C4 H4 0.95(2) . ? C9 C8 1.384(3) . ? C9 C5 1.507(2) . ? C5 C6 1.505(2) . ? C5 C11 1.577(2) . ? C5 H5 0.958(19) . ? C6 C7 1.362(2) . ? C6 C10 1.411(2) . ? C13 C11 1.470(2) . ? C11 C12 1.469(2) . ? C11 H8 0.930(19) . ? C8 C1 1.379(2) . ? C1 H1 0.96(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 C7 O1 C8 118.78(12) . . ? C7 N1 H6 119.8(16) . . ? C7 N1 H7 115.5(14) . . ? H6 N1 H7 124(2) . . ? C1 C2 C3 119.98(18) . . ? C1 C2 H2 117.5(12) . . ? C3 C2 H2 122.5(12) . . ? C2 C3 C4 119.97(17) . . ? C2 C3 H3 120.8(14) . . ? C4 C3 H3 119.2(14) . . ? C3 C4 C9 121.05(19) . . ? C3 C4 H4 120.1(12) . . ? C9 C4 H4 118.8(12) . . ? C8 C9 C4 117.10(16) . . ? C8 C9 C5 119.85(14) . . ? C4 C9 C5 123.04(15) . . ? C6 C5 C9 110.23(13) . . ? C6 C5 C11 110.42(12) . . ? C9 C5 C11 111.82(12) . . ? C6 C5 H5 109.4(9) . . ? C9 C5 H5 111.6(10) . . ? C11 C5 H5 103.2(10) . . ? C7 C6 C10 119.27(14) . . ? C7 C6 C5 121.80(14) . . ? C10 C6 C5 118.84(14) . . ? N2 C10 C6 177.69(17) . . ? N4 C13 C11 177.34(17) . . ? C12 C11 C13 110.10(12) . . ? C12 C11 C5 111.66(13) . . ? C13 C11 C5 111.73(13) . . ? C12 C11 H8 107.9(10) . . ? C13 C11 H8 108.1(10) . . ? C5 C11 H8 107.2(10) . . ? N3 C12 C11 178.59(18) . . ? N1 C7 O1 111.07(14) . . ? N1 C7 C6 126.94(15) . . ? O1 C7 C6 121.99(14) . . ? C1 C8 C9 122.52(16) . . ? C1 C8 O1 115.61(15) . . ? C9 C8 O1 121.85(14) . . ? C2 C1 C8 119.24(18) . . ? C2 C1 H1 121.3(13) . . ? C8 C1 H1 119.4(13) . . ? _diffrn_measured_fraction_theta_max 0.938 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.938 _refine_diff_density_max 0.273 _refine_diff_density_min -0.272 _refine_diff_density_rms 0.068