# 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_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'T. Punniyamurthy' _publ_contact_author_email tpunni@iitg.ernet.in loop_ _publ_author_name T.Punniyamurthy M.Sengoden data_MSN-92 _database_code_depnum_ccdc_archive 'CCDC 843126' #TrackingRef 'MSN-92-2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H15 N O Se' _chemical_formula_sum 'C13 H15 N O Se' _chemical_formula_weight 280.22 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' Se Se -0.0929 2.2259 '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 6.7304(4) _cell_length_b 7.6804(4) _cell_length_c 23.0785(13) _cell_angle_alpha 90.00 _cell_angle_beta 92.209(4) _cell_angle_gamma 90.00 _cell_volume 1192.09(12) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.77 _cell_measurement_theta_max 19.98 _exptl_crystal_description square _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 3.128 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.298 _exptl_absorpt_correction_T_max 0.391 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 7300 _diffrn_reflns_av_R_equivalents 0.1921 _diffrn_reflns_av_sigmaI/netI 0.0727 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 19.98 _reflns_number_total 1084 _reflns_number_gt 1022 _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^)+(0.1000P)^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 mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1084 _refine_ls_number_parameters 145 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0596 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1223 _refine_ls_wR_factor_gt 0.1110 _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_restrained_S_all 1.030 _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 Se1 Se 0.40605(7) 0.21314(8) 0.00836(2) 0.0257(5) Uani 1 1 d . . . C4 C 0.5343(7) 0.3913(7) 0.1249(2) 0.0231(14) Uani 1 1 d . . . H4 H 0.5431 0.4542 0.0907 0.028 Uiso 1 1 calc R . . C3 C 0.7018(8) 0.3673(7) 0.1613(2) 0.0299(15) Uani 1 1 d . . . H3 H 0.8239 0.4113 0.1507 0.036 Uiso 1 1 calc R . . C1 C 0.3412(10) 0.2376(8) 0.1934(3) 0.0292(15) Uani 1 1 d . . . H1 H 0.2188 0.1974 0.2052 0.035 Uiso 1 1 calc R . . C2 C 0.5073(10) 0.2143(7) 0.2290(3) 0.0337(17) Uani 1 1 d . . . H2 H 0.4980 0.1552 0.2640 0.040 Uiso 1 1 calc R . . C5 C 0.6877(10) 0.2789(7) 0.2127(3) 0.0333(17) Uani 1 1 d . . . H5 H 0.8005 0.2626 0.2367 0.040 Uiso 1 1 calc R . . C6 C 0.3531(8) 0.3203(7) 0.1403(2) 0.0228(14) Uani 1 1 d . . . C10 C -0.0977(9) 0.2059(7) -0.1399(3) 0.0289(16) Uani 1 1 d . . . H10A H -0.2149 0.1630 -0.1611 0.035 Uiso 1 1 calc R . . H10B H -0.0669 0.3202 -0.1550 0.035 Uiso 1 1 calc R . . C12 C 0.0448(8) 0.2738(7) -0.0429(2) 0.0214(16) Uani 1 1 d . . . H12 H 0.0909 0.3851 -0.0582 0.026 Uiso 1 1 calc R . . C7 C 0.2050(7) 0.1396(8) -0.0502(2) 0.0256(14) Uani 1 1 d . . . H7 H 0.1533 0.0255 -0.0391 0.031 Uiso 1 1 calc R . . C11 C -0.1443(9) 0.2231(7) -0.0755(2) 0.0284(16) Uani 1 1 d . . . H11A H -0.2454 0.3113 -0.0706 0.034 Uiso 1 1 calc R . . H11B H -0.1933 0.1133 -0.0610 0.034 Uiso 1 1 calc R . . C9 C 0.0755(7) 0.0839(7) -0.1501(2) 0.0300(15) Uani 1 1 d . . . H9A H 0.1073 0.0884 -0.1907 0.036 Uiso 1 1 calc R . . H9B H 0.0362 -0.0344 -0.1413 0.036 Uiso 1 1 calc R . . C8 C 0.2631(8) 0.1315(8) -0.1125(2) 0.0287(15) Uani 1 1 d . . . H8A H 0.3656 0.0443 -0.1171 0.034 Uiso 1 1 calc R . . H8B H 0.3148 0.2433 -0.1245 0.034 Uiso 1 1 calc R . . N1 N 0.1774(6) 0.3337(6) 0.1044(2) 0.0245(11) Uani 1 1 d . . . C14 C 0.1841(8) 0.2924(6) 0.0515(3) 0.0202(15) Uani 1 1 d . . . O1 O 0.0116(6) 0.2946(4) 0.01864(16) 0.0255(11) 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 Se1 0.0185(6) 0.0319(7) 0.0270(6) -0.0053(3) 0.0036(3) 0.0035(2) C4 0.026(3) 0.025(3) 0.019(3) 0.003(3) 0.006(3) -0.009(3) C3 0.020(3) 0.034(3) 0.036(4) -0.004(3) 0.007(3) -0.008(3) C1 0.025(4) 0.037(3) 0.026(4) -0.001(3) 0.001(3) -0.011(3) C2 0.040(4) 0.037(4) 0.024(4) 0.002(3) 0.008(4) -0.013(3) C5 0.031(4) 0.041(4) 0.027(4) -0.004(3) -0.004(3) 0.008(3) C6 0.022(4) 0.023(3) 0.023(4) -0.006(3) 0.003(3) 0.004(3) C10 0.029(4) 0.032(4) 0.025(4) 0.003(3) 0.001(3) -0.011(3) C12 0.015(3) 0.027(3) 0.023(4) 0.001(3) 0.011(3) 0.000(3) C7 0.025(3) 0.031(3) 0.021(3) 0.003(3) 0.004(2) -0.007(3) C11 0.023(4) 0.026(3) 0.037(4) -0.003(3) 0.002(3) 0.003(3) C9 0.036(3) 0.029(3) 0.025(3) -0.002(3) 0.004(3) -0.002(3) C8 0.025(3) 0.032(3) 0.030(3) -0.004(3) 0.004(2) 0.002(3) N1 0.021(3) 0.028(2) 0.026(3) -0.005(3) 0.005(2) -0.002(2) C14 0.012(4) 0.019(3) 0.030(5) 0.000(3) 0.005(3) -0.002(2) O1 0.021(3) 0.032(3) 0.024(2) -0.0007(18) 0.003(2) 0.0036(17) _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 Se1 C14 1.926(6) . ? Se1 C7 1.959(5) . ? C4 C3 1.392(7) . ? C4 C6 1.394(8) . ? C3 C5 1.375(9) . ? C1 C2 1.373(9) . ? C1 C6 1.386(9) . ? C2 C5 1.377(9) . ? C6 N1 1.421(7) . ? C10 C9 1.521(8) . ? C10 C11 1.535(9) . ? C12 O1 1.455(7) . ? C12 C11 1.504(8) . ? C12 C7 1.506(8) . ? C7 C8 1.506(9) . ? C9 C8 1.548(7) . ? N1 C14 1.264(7) . ? C14 O1 1.363(7) . ? 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 C14 Se1 C7 85.4(2) . . ? C3 C4 C6 119.5(5) . . ? C5 C3 C4 120.3(5) . . ? C2 C1 C6 121.0(6) . . ? C1 C2 C5 119.7(6) . . ? C3 C5 C2 120.3(5) . . ? C1 C6 C4 119.0(5) . . ? C1 C6 N1 118.2(5) . . ? C4 C6 N1 122.7(5) . . ? C9 C10 C11 112.9(5) . . ? O1 C12 C11 111.0(5) . . ? O1 C12 C7 108.8(4) . . ? C11 C12 C7 111.2(4) . . ? C8 C7 C12 110.4(4) . . ? C8 C7 Se1 118.2(4) . . ? C12 C7 Se1 101.7(4) . . ? C12 C11 C10 107.8(5) . . ? C10 C9 C8 112.4(5) . . ? C7 C8 C9 107.9(5) . . ? C14 N1 C6 118.9(5) . . ? N1 C14 O1 118.2(5) . . ? N1 C14 Se1 129.6(4) . . ? O1 C14 Se1 112.1(4) . . ? C14 O1 C12 112.5(4) . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 19.98 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.391 _refine_diff_density_min -0.610 _refine_diff_density_rms 0.124 # Attachment 'MSN-109.cif' data_MSN-109 _database_code_depnum_ccdc_archive 'CCDC 843127' #TrackingRef 'MSN-109.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H13 N O2' _chemical_formula_sum 'C15 H13 N O2' _chemical_formula_weight 239.26 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)/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 10.4808(9) _cell_length_b 8.9744(8) _cell_length_c 13.0800(12) _cell_angle_alpha 90.00 _cell_angle_beta 91.143(5) _cell_angle_gamma 90.00 _cell_volume 1230.05(19) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.47 _cell_measurement_theta_max 26.14 _exptl_crystal_description square _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.29 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.973 _exptl_absorpt_correction_T_max 0.978 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 13576 _diffrn_reflns_av_R_equivalents 0.1068 _diffrn_reflns_av_sigmaI/netI 0.0443 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.47 _diffrn_reflns_theta_max 26.14 _reflns_number_total 2401 _reflns_number_gt 1779 _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^)+(0.0868P)^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 none _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.026(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2401 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0654 _refine_ls_R_factor_gt 0.0515 _refine_ls_wR_factor_ref 0.1508 _refine_ls_wR_factor_gt 0.1412 _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_restrained_S_all 1.085 _refine_ls_shift/su_max 0.079 _refine_ls_shift/su_mean 0.018 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 C6 C 0.72157(14) 0.30572(16) 0.58169(11) 0.0557(4) Uani 1 1 d . . . H6 H 0.6798 0.2162 0.5939 0.067 Uiso 1 1 calc R . . C3 C 0.79235(14) 0.37177(17) 0.65904(13) 0.0627(5) Uani 1 1 d . . . H3 H 0.7977 0.3270 0.7231 0.075 Uiso 1 1 calc R . . C5 C 0.71179(12) 0.37055(14) 0.48639(11) 0.0484(4) Uani 1 1 d . . . C2 C 0.85439(15) 0.50222(18) 0.64209(15) 0.0711(5) Uani 1 1 d . . . H2 H 0.9021 0.5466 0.6945 0.085 Uiso 1 1 calc R . . C4 C 0.77565(16) 0.50250(16) 0.46991(14) 0.0671(5) Uani 1 1 d . . . H4 H 0.7711 0.5477 0.4060 0.081 Uiso 1 1 calc R . . C1 C 0.84652(17) 0.56782(19) 0.54839(17) 0.0802(6) Uani 1 1 d . . . H1 H 0.8890 0.6571 0.5370 0.096 Uiso 1 1 calc R . . C10 C 0.77981(13) 0.08730(15) 0.36547(11) 0.0506(4) Uani 1 1 d . . . C9 C 0.85976(15) 0.17184(17) 0.30646(12) 0.0610(5) Uani 1 1 d . . . H9 H 0.8316 0.2621 0.2793 0.073 Uiso 1 1 calc R . . C11 C 0.82173(16) -0.04668(18) 0.40379(13) 0.0718(5) Uani 1 1 d . . . H11 H 0.7685 -0.1042 0.4439 0.086 Uiso 1 1 calc R . . C8 C 0.98144(15) 0.12245(18) 0.28773(14) 0.0675(5) Uani 1 1 d . . . H8 H 1.0356 0.1805 0.2488 0.081 Uiso 1 1 calc R . . C7 C 1.02330(17) -0.00999(19) 0.32545(14) 0.0715(5) Uani 1 1 d . . . H7 H 1.1057 -0.0424 0.3126 0.086 Uiso 1 1 calc R . . C12 C 0.94321(19) -0.0958(2) 0.38271(16) 0.0853(6) Uani 1 1 d . . . H12 H 0.9710 -0.1876 0.4075 0.102 Uiso 1 1 calc R . . C20 C 0.62936(13) 0.30051(15) 0.40306(11) 0.0538(4) Uani 1 1 d . . . H20 H 0.6398 0.3545 0.3387 0.065 Uiso 1 1 calc R . . O1 O 0.53738(11) -0.07007(13) 0.35953(10) 0.0787(4) Uani 1 1 d . . . N1 N 0.65596(10) 0.14253(13) 0.38817(9) 0.0543(4) Uani 1 1 d . . . O2 O 0.44565(10) 0.14797(13) 0.39636(9) 0.0733(4) Uani 1 1 d . . . C14 C 0.54751(15) 0.0595(2) 0.38003(11) 0.0601(4) Uani 1 1 d . . . C16 C 0.48816(15) 0.29223(18) 0.42907(14) 0.0686(5) Uani 1 1 d . . . H16A H 0.4769 0.3042 0.5020 0.082 Uiso 1 1 calc R . . H16B H 0.4404 0.3697 0.3935 0.082 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 C6 0.0571(9) 0.0500(8) 0.0599(10) 0.0007(7) -0.0016(7) -0.0015(6) C3 0.0612(10) 0.0656(10) 0.0610(11) 0.0007(8) -0.0078(8) 0.0048(8) C5 0.0454(8) 0.0435(8) 0.0565(9) -0.0013(6) 0.0009(6) 0.0061(6) C2 0.0631(10) 0.0647(11) 0.0847(14) -0.0099(9) -0.0183(9) -0.0025(8) C4 0.0688(10) 0.0595(9) 0.0729(12) 0.0126(8) -0.0019(9) -0.0045(8) C1 0.0779(12) 0.0633(11) 0.0987(16) 0.0034(10) -0.0145(10) -0.0210(9) C10 0.0537(9) 0.0483(8) 0.0497(9) -0.0056(6) -0.0019(7) -0.0009(6) C9 0.0655(10) 0.0493(9) 0.0685(11) 0.0031(7) 0.0101(8) 0.0030(7) C11 0.0712(11) 0.0682(11) 0.0765(13) 0.0208(9) 0.0123(9) 0.0065(8) C8 0.0660(10) 0.0599(10) 0.0773(12) -0.0017(8) 0.0154(9) -0.0054(8) C7 0.0612(10) 0.0749(12) 0.0787(12) -0.0008(9) 0.0079(9) 0.0112(8) C12 0.0821(13) 0.0787(12) 0.0954(15) 0.0243(10) 0.0126(11) 0.0239(10) C20 0.0544(9) 0.0561(9) 0.0506(9) 0.0014(7) -0.0033(7) 0.0074(6) O1 0.0802(8) 0.0706(8) 0.0848(9) -0.0135(6) -0.0109(6) -0.0210(6) N1 0.0507(7) 0.0504(8) 0.0617(8) -0.0066(5) -0.0015(6) -0.0038(5) O2 0.0511(7) 0.0942(9) 0.0740(9) -0.0148(6) -0.0110(6) -0.0058(6) C14 0.0583(10) 0.0701(11) 0.0514(10) -0.0055(8) -0.0092(7) -0.0067(8) C16 0.0530(10) 0.0809(12) 0.0716(11) -0.0081(9) -0.0088(8) 0.0082(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 C6 C3 1.377(2) . ? C6 C5 1.378(2) . ? C3 C2 1.360(2) . ? C5 C4 1.379(2) . ? C5 C20 1.5139(19) . ? C2 C1 1.361(3) . ? C4 C1 1.385(2) . ? C10 C11 1.371(2) . ? C10 C9 1.378(2) . ? C10 N1 1.4263(17) . ? C9 C8 1.377(2) . ? C11 C12 1.380(2) . ? C8 C7 1.356(2) . ? C7 C12 1.373(2) . ? C20 N1 1.4587(18) . ? C20 C16 1.527(2) . ? O1 C14 1.1978(18) . ? N1 C14 1.3614(18) . ? O2 C14 1.3508(19) . ? O2 C16 1.4317(18) . ? 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 C3 C6 C5 120.83(15) . . ? C2 C3 C6 120.23(16) . . ? C6 C5 C4 118.45(14) . . ? C6 C5 C20 120.48(13) . . ? C4 C5 C20 121.04(13) . . ? C3 C2 C1 119.92(16) . . ? C5 C4 C1 120.14(16) . . ? C2 C1 C4 120.43(16) . . ? C11 C10 C9 119.56(14) . . ? C11 C10 N1 120.98(13) . . ? C9 C10 N1 119.43(13) . . ? C8 C9 C10 119.88(14) . . ? C10 C11 C12 119.81(15) . . ? C7 C8 C9 120.76(16) . . ? C8 C7 C12 119.56(16) . . ? C7 C12 C11 120.42(16) . . ? N1 C20 C5 113.07(11) . . ? N1 C20 C16 99.85(11) . . ? C5 C20 C16 113.67(12) . . ? C14 N1 C10 123.74(13) . . ? C14 N1 C20 112.38(12) . . ? C10 N1 C20 122.87(11) . . ? C14 O2 C16 109.66(12) . . ? O1 C14 O2 122.63(14) . . ? O1 C14 N1 128.24(15) . . ? O2 C14 N1 109.11(14) . . ? O2 C16 C20 105.94(11) . . ? _diffrn_measured_fraction_theta_max 0.978 _diffrn_reflns_theta_full 26.14 _diffrn_measured_fraction_theta_full 0.978 _refine_diff_density_max 0.191 _refine_diff_density_min -0.190 _refine_diff_density_rms 0.045 # Attachment 'MSN-147.cif' data_msn-147 _database_code_depnum_ccdc_archive 'CCDC 843128' #TrackingRef 'MSN-147.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H12 I N O Se' _chemical_formula_sum 'C15 H12 I N O Se' _chemical_formula_weight 429.12 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' Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 12.7577(7) _cell_length_b 10.0993(6) _cell_length_c 11.6512(7) _cell_angle_alpha 90.00 _cell_angle_beta 94.400(3) _cell_angle_gamma 90.00 _cell_volume 1496.76(15) _cell_formula_units_Z 4 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 1.60 _cell_measurement_theta_max 28.54 _exptl_crystal_description square _exptl_crystal_colour colorless _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.904 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 4.563 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.231 _exptl_absorpt_correction_T_max 0.292 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1997)' _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 13382 _diffrn_reflns_av_R_equivalents 0.0311 _diffrn_reflns_av_sigmaI/netI 0.0503 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.60 _diffrn_reflns_theta_max 28.54 _reflns_number_total 3709 _reflns_number_gt 3585 _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^)+(0.1000P)^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 none _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3398 _refine_ls_number_parameters 172 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1363 _refine_ls_R_factor_gt 0.0532 _refine_ls_wR_factor_ref 0.2460 _refine_ls_wR_factor_gt 0.1609 _refine_ls_goodness_of_fit_ref 1.420 _refine_ls_restrained_S_all 1.420 _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 Se1 Se 0.03895(8) 0.15682(9) 0.40312(8) 0.0734(5) Uani 1 1 d . . . I1 I 0.49517(6) 0.34366(10) 0.75746(5) 0.0949(5) Uani 1 1 d . . . C1 C 0.3657(7) 0.3597(9) 0.6367(7) 0.068(3) Uani 1 1 d . . . C6 C 0.2647(9) 0.3629(10) 0.6727(8) 0.078(3) Uani 1 1 d . . . H6 H 0.2546 0.3536 0.7504 0.094 Uiso 1 1 calc R . . C2 C 0.3807(8) 0.3723(9) 0.5209(8) 0.074(3) Uani 1 1 d . . . H2 H 0.4478 0.3668 0.4952 0.089 Uiso 1 1 calc R . . C5 C 0.1798(9) 0.3796(10) 0.5952(8) 0.078(3) Uani 1 1 d . . . H5 H 0.1124 0.3805 0.6204 0.094 Uiso 1 1 calc R . . C4 C 0.1937(7) 0.3952(10) 0.4797(7) 0.070(2) Uani 1 1 d . . . C3 C 0.2932(7) 0.3934(9) 0.4430(7) 0.071(2) Uani 1 1 d . . . H3 H 0.3028 0.4062 0.3654 0.085 Uiso 1 1 calc R . . N1 N 0.1076(6) 0.4281(9) 0.3994(6) 0.084(2) Uani 1 1 d . . . C7 C 0.0424(8) 0.3408(9) 0.3685(7) 0.065(3) Uani 1 1 d . . . C11 C -0.2283(7) 0.2478(8) 0.4439(7) 0.065(2) Uani 1 1 d . . . H11 H -0.1993 0.3309 0.4331 0.078 Uiso 1 1 calc R . . C15 C -0.2330(9) 0.0223(13) 0.4099(9) 0.086(3) Uani 1 1 d . . . H15 H -0.2079 -0.0521 0.3738 0.104 Uiso 1 1 calc R . . O1 O -0.0413(5) 0.3796(7) 0.2963(6) 0.090(2) Uani 1 1 d . . . C10 C -0.1891(8) 0.1385(13) 0.3908(8) 0.076(3) Uani 1 1 d . . . C8 C -0.0948(9) 0.2725(15) 0.2378(8) 0.104(4) Uani 1 1 d . . . H8A H -0.0597 0.2513 0.1692 0.125 Uiso 1 1 calc R . . H8B H -0.1660 0.2997 0.2137 0.125 Uiso 1 1 calc R . . C14 C -0.3134(9) 0.0061(13) 0.4802(10) 0.093(3) Uani 1 1 d . . . H14 H -0.3409 -0.0778 0.4914 0.112 Uiso 1 1 calc R . . C12 C -0.3102(7) 0.2340(9) 0.5128(7) 0.069(2) Uani 1 1 d . . . H12 H -0.3374 0.3088 0.5463 0.083 Uiso 1 1 calc R . . C13 C -0.3530(9) 0.1123(14) 0.5336(9) 0.086(3) Uani 1 1 d . . . H13 H -0.4070 0.1031 0.5823 0.103 Uiso 1 1 calc R . . C9 C -0.0986(8) 0.1493(11) 0.3121(9) 0.097(4) Uani 1 1 d . . . H9 H -0.0998 0.0712 0.2621 0.117 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 Se1 0.0498(7) 0.0903(9) 0.0783(7) -0.0184(4) -0.0058(5) 0.0098(5) I1 0.0647(6) 0.1563(10) 0.0628(5) -0.0132(3) -0.0007(4) -0.0066(3) C1 0.039(5) 0.115(7) 0.051(5) -0.011(4) 0.001(4) -0.012(5) C6 0.069(7) 0.117(9) 0.049(5) 0.005(4) 0.007(5) -0.006(6) C2 0.051(6) 0.112(7) 0.060(6) -0.012(5) 0.009(5) -0.003(5) C5 0.062(7) 0.105(7) 0.069(6) 0.020(5) 0.014(5) 0.001(6) C4 0.047(6) 0.100(7) 0.062(5) 0.021(5) 0.000(4) -0.007(5) C3 0.071(7) 0.087(6) 0.054(5) 0.001(4) 0.005(5) -0.016(5) N1 0.065(6) 0.100(6) 0.088(5) 0.042(5) 0.004(4) -0.004(5) C7 0.057(6) 0.083(7) 0.055(5) 0.014(4) 0.003(4) 0.007(5) C11 0.061(6) 0.060(6) 0.077(5) -0.011(4) 0.012(5) -0.008(5) C15 0.061(7) 0.097(9) 0.097(8) -0.026(6) -0.026(6) 0.015(7) O1 0.062(4) 0.134(6) 0.073(4) 0.035(4) -0.004(4) 0.006(4) C10 0.052(6) 0.117(9) 0.057(6) -0.027(5) -0.018(5) -0.013(6) C8 0.065(7) 0.204(13) 0.044(5) 0.000(7) 0.005(5) 0.019(9) C14 0.075(8) 0.104(9) 0.096(8) 0.019(7) -0.023(6) -0.011(7) C12 0.056(6) 0.069(7) 0.083(6) -0.007(5) 0.017(5) -0.006(5) C13 0.062(7) 0.119(10) 0.077(7) 0.009(7) -0.001(5) -0.005(7) C9 0.042(6) 0.173(12) 0.075(7) -0.061(7) -0.006(5) 0.006(6) _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 Se1 C7 1.903(9) . ? Se1 C9 1.981(10) . ? I1 C1 2.092(8) . ? C1 C2 1.382(12) . ? C1 C6 1.385(13) . ? C6 C5 1.366(14) . ? C2 C3 1.400(12) . ? C5 C4 1.379(12) . ? C4 C3 1.371(11) . ? C4 N1 1.426(10) . ? N1 C7 1.246(10) . ? C7 O1 1.365(10) . ? C11 C12 1.373(11) . ? C11 C10 1.378(13) . ? C15 C10 1.327(15) . ? C15 C14 1.371(16) . ? O1 C8 1.425(13) . ? C10 C9 1.532(15) . ? C8 C9 1.518(15) . ? C14 C13 1.356(15) . ? C12 C13 1.374(13) . ? 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 Se1 C9 87.6(5) . . ? C2 C1 C6 119.6(8) . . ? C2 C1 I1 120.2(6) . . ? C6 C1 I1 120.2(6) . . ? C5 C6 C1 120.8(8) . . ? C1 C2 C3 119.0(8) . . ? C6 C5 C4 120.3(9) . . ? C3 C4 C5 119.6(8) . . ? C3 C4 N1 118.9(7) . . ? C5 C4 N1 121.1(8) . . ? C4 C3 C2 120.7(8) . . ? C7 N1 C4 119.2(8) . . ? N1 C7 O1 116.6(8) . . ? N1 C7 Se1 130.9(7) . . ? O1 C7 Se1 112.4(7) . . ? C12 C11 C10 120.0(9) . . ? C10 C15 C14 123.4(11) . . ? C7 O1 C8 113.6(8) . . ? C15 C10 C11 117.4(10) . . ? C15 C10 C9 120.7(11) . . ? C11 C10 C9 121.9(11) . . ? O1 C8 C9 112.6(8) . . ? C13 C14 C15 120.1(11) . . ? C11 C12 C13 121.7(9) . . ? C14 C13 C12 117.4(10) . . ? C8 C9 C10 117.3(9) . . ? C8 C9 Se1 102.0(7) . . ? C10 C9 Se1 111.0(7) . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 28.54 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.963 _refine_diff_density_min -1.528 _refine_diff_density_rms 0.225