# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Ying Cheng' _publ_contact_author_email YCHENG2@BNU.EDU.CN _publ_section_title ; The [3+2] Cycloaddition Reaction of Thiazole Carbene-derived C-C-Se 1,3-Dipoles: a Concise and Highly Efficient Strategy for the Construction of Multifunctional Selenophene and Fused Selenophene Derivatives ; loop_ _publ_author_name 'Ying Cheng.' 'Jian-Hong Zhang.' # Attachment 'Corrected-6a.cif' data_080909a_0m _database_code_depnum_ccdc_archive 'CCDC 721793' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (E)-Dimethyl 1-benzyl-3-(1,2-dimethoxycarbonylvinylthio)-2- methyl-4-phenyl-1,4-dihydroselenopheno(2,3-b)pyrazine-6,7-dicarboxylate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C30 H28 N2 O8 S Se' _chemical_formula_weight 655.56 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' S S 0.1246 0.1234 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.63340(10) _cell_length_b 11.8180(2) _cell_length_c 15.3160(2) _cell_angle_alpha 77.3390(10) _cell_angle_beta 88.8590(10) _cell_angle_gamma 89.6770(10) _cell_volume 1524.38(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 5768 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 27.40 _exptl_crystal_description column _exptl_crystal_colour orange _exptl_crystal_size_max 0.39 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.428 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 1.352 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6207 _exptl_absorpt_correction_T_max 0.8767 _exptl_absorpt_process_details SADABS _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 '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 13248 _diffrn_reflns_av_R_equivalents 0.0161 _diffrn_reflns_av_sigmaI/netI 0.0263 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 27.69 _reflns_number_total 7085 _reflns_number_gt 5540 _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^)+(0.0531P)^2^+0.2054P] 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 7085 _refine_ls_number_parameters 384 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0483 _refine_ls_R_factor_gt 0.0342 _refine_ls_wR_factor_ref 0.0965 _refine_ls_wR_factor_gt 0.0892 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _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 0.5914(5) 0.5749(2) 0.3791(2) 0.1046(11) Uani 1 1 d . . . H1A H 0.4812 0.5797 0.3723 0.157 Uiso 1 1 calc R . . H1B H 0.6379 0.6471 0.3496 0.157 Uiso 1 1 calc R . . H1C H 0.6151 0.5589 0.4416 0.157 Uiso 1 1 calc R . . C2 C 0.5930(3) 0.37837(18) 0.37356(14) 0.0556(5) Uani 1 1 d . . . C3 C 0.6763(2) 0.28604(16) 0.33754(12) 0.0472(4) Uani 1 1 d . . . C4 C 0.8152(2) 0.24163(19) 0.36997(13) 0.0537(5) Uani 1 1 d . . . C5 C 0.9003(3) 0.2731(2) 0.44267(14) 0.0620(5) Uani 1 1 d . . . C6 C 1.1193(4) 0.2265(4) 0.5345(2) 0.1126(12) Uani 1 1 d . . . H6A H 1.1535 0.3057 0.5225 0.169 Uiso 1 1 calc R . . H6B H 1.2077 0.1759 0.5416 0.169 Uiso 1 1 calc R . . H6C H 1.0570 0.2105 0.5884 0.169 Uiso 1 1 calc R . . C7 C 0.70632(19) 0.15191(16) 0.24729(12) 0.0430(4) Uani 1 1 d . . . C8 C 0.61235(19) 0.23361(15) 0.27191(12) 0.0423(4) Uani 1 1 d . . . C9 C 0.4595(2) 0.23995(16) 0.14325(13) 0.0494(4) Uani 1 1 d . . . C10 C 0.3417(3) 0.3108(2) 0.08406(18) 0.0763(7) Uani 1 1 d . . . H10A H 0.3770 0.3895 0.0660 0.114 Uiso 1 1 calc R . . H10B H 0.2449 0.3088 0.1163 0.114 Uiso 1 1 calc R . . H10C H 0.3278 0.2793 0.0320 0.114 Uiso 1 1 calc R . . C11 C 0.5593(2) 0.16663(16) 0.11683(12) 0.0451(4) Uani 1 1 d . . . C12 C 0.7428(2) -0.00033(16) 0.16288(12) 0.0455(4) Uani 1 1 d . . . C13 C 0.6665(3) -0.1029(2) 0.19002(18) 0.0701(6) Uani 1 1 d . . . H13 H 0.5702 -0.1051 0.2187 0.084 Uiso 1 1 calc R . . C14 C 0.7330(3) -0.2041(2) 0.1747(2) 0.0834(8) Uani 1 1 d . . . H14 H 0.6805 -0.2741 0.1925 0.100 Uiso 1 1 calc R . . C15 C 0.8747(3) -0.2015(2) 0.13386(17) 0.0722(7) Uani 1 1 d . . . H15 H 0.9190 -0.2696 0.1238 0.087 Uiso 1 1 calc R . . C16 C 0.9515(3) -0.0992(2) 0.10769(18) 0.0783(7) Uani 1 1 d . . . H16 H 1.0486 -0.0976 0.0801 0.094 Uiso 1 1 calc R . . C17 C 0.8867(3) 0.0023(2) 0.12176(16) 0.0654(6) Uani 1 1 d . . . H17 H 0.9397 0.0721 0.1036 0.079 Uiso 1 1 calc R . . C18 C 0.3307(2) 0.21109(18) 0.29038(15) 0.0569(5) Uani 1 1 d . . . H18A H 0.2357 0.2406 0.2608 0.068 Uiso 1 1 calc R . . H18B H 0.3350 0.2382 0.3456 0.068 Uiso 1 1 calc R . . C19 C 0.2490(2) 0.0203(2) 0.25838(17) 0.0641(6) Uani 1 1 d . . . H19 H 0.2024 0.0607 0.2065 0.077 Uiso 1 1 calc R . . C20 C 0.2420(3) -0.0997(2) 0.2804(2) 0.0766(7) Uani 1 1 d . . . H20 H 0.1885 -0.1387 0.2439 0.092 Uiso 1 1 calc R . . C21 C 0.3123(4) -0.1612(2) 0.3547(2) 0.0844(8) Uani 1 1 d . . . H21 H 0.3071 -0.2417 0.3689 0.101 Uiso 1 1 calc R . . C22 C 0.3902(4) -0.1037(3) 0.4079(2) 0.0983(9) Uani 1 1 d . . . H22 H 0.4402 -0.1452 0.4581 0.118 Uiso 1 1 calc R . . C23 C 0.3955(3) 0.0167(2) 0.38758(18) 0.0805(7) Uani 1 1 d . . . H23 H 0.4477 0.0549 0.4251 0.097 Uiso 1 1 calc R . . C24 C 0.3247(2) 0.08041(18) 0.31279(15) 0.0552(5) Uani 1 1 d . . . C25 C 0.6842(2) 0.27303(16) -0.04765(12) 0.0462(4) Uani 1 1 d . . . C26 C 0.7867(2) 0.32549(16) 0.01173(13) 0.0505(4) Uani 1 1 d . . . C27 C 0.8039(4) 0.4657(2) 0.09763(18) 0.0865(8) Uani 1 1 d . . . H27A H 0.8483 0.4068 0.1437 0.130 Uiso 1 1 calc R . . H27B H 0.7364 0.5139 0.1244 0.130 Uiso 1 1 calc R . . H27C H 0.8852 0.5123 0.0643 0.130 Uiso 1 1 calc R . . C28 C 0.6854(2) 0.30729(17) -0.13636(13) 0.0528(5) Uani 1 1 d . . . H28 H 0.6186 0.2713 -0.1686 0.063 Uiso 1 1 calc R . . C29 C 0.7874(2) 0.39922(18) -0.18568(14) 0.0541(5) Uani 1 1 d . . . C30 C 0.8835(4) 0.4877(3) -0.33039(19) 0.0969(9) Uani 1 1 d . . . H30A H 0.8546 0.5646 -0.3254 0.145 Uiso 1 1 calc R . . H30B H 0.8738 0.4808 -0.3913 0.145 Uiso 1 1 calc R . . H30C H 0.9889 0.4729 -0.3124 0.145 Uiso 1 1 calc R . . N1 N 0.67252(18) 0.10552(14) 0.17567(10) 0.0484(4) Uani 1 1 d . . . N2 N 0.46485(17) 0.26022(13) 0.23184(11) 0.0474(4) Uani 1 1 d . . . O1 O 0.6523(2) 0.48227(13) 0.33956(11) 0.0724(4) Uani 1 1 d . . . O2 O 0.4868(2) 0.35991(15) 0.42570(12) 0.0763(5) Uani 1 1 d . . . O3 O 1.0284(2) 0.20773(19) 0.46049(12) 0.0873(6) Uani 1 1 d . . . O4 O 0.8623(2) 0.34682(16) 0.48114(11) 0.0773(5) Uani 1 1 d . . . O5 O 0.71628(18) 0.41161(12) 0.03796(10) 0.0608(4) Uani 1 1 d . . . O6 O 0.91259(19) 0.28769(15) 0.03379(12) 0.0745(4) Uani 1 1 d . . . O7 O 0.7826(2) 0.40404(15) -0.27306(10) 0.0794(5) Uani 1 1 d . . . O8 O 0.8668(2) 0.46090(15) -0.15324(11) 0.0735(4) Uani 1 1 d . . . S1 S 0.57241(6) 0.15202(4) 0.00453(3) 0.05433(13) Uani 1 1 d . . . Se1 Se 0.88801(2) 0.12606(2) 0.312963(14) 0.05906(9) 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 C1 0.157(3) 0.0596(16) 0.110(2) -0.0458(16) 0.003(2) 0.0017(17) C2 0.0645(12) 0.0560(12) 0.0538(11) -0.0282(10) 0.0009(9) -0.0044(9) C3 0.0478(10) 0.0499(10) 0.0478(10) -0.0199(8) 0.0068(8) -0.0071(8) C4 0.0480(10) 0.0670(13) 0.0520(11) -0.0262(9) 0.0026(8) -0.0072(9) C5 0.0572(12) 0.0820(15) 0.0492(11) -0.0196(11) 0.0020(9) -0.0203(11) C6 0.0833(19) 0.181(4) 0.0784(19) -0.035(2) -0.0322(15) -0.016(2) C7 0.0392(8) 0.0496(10) 0.0441(9) -0.0185(8) -0.0009(7) 0.0029(7) C8 0.0398(8) 0.0426(9) 0.0473(9) -0.0163(7) 0.0024(7) 0.0008(7) C9 0.0497(10) 0.0455(10) 0.0551(11) -0.0154(8) -0.0076(8) 0.0049(8) C10 0.0809(16) 0.0708(15) 0.0801(16) -0.0213(13) -0.0264(13) 0.0289(12) C11 0.0463(9) 0.0464(10) 0.0451(9) -0.0155(8) -0.0048(7) 0.0010(8) C12 0.0449(9) 0.0504(10) 0.0456(10) -0.0202(8) -0.0043(7) 0.0102(8) C13 0.0584(12) 0.0608(14) 0.0947(18) -0.0260(12) 0.0118(12) 0.0017(10) C14 0.0831(18) 0.0531(14) 0.118(2) -0.0282(14) 0.0005(16) 0.0001(12) C15 0.0837(16) 0.0616(14) 0.0795(16) -0.0330(12) -0.0133(13) 0.0261(12) C16 0.0718(15) 0.0823(18) 0.0819(17) -0.0229(13) 0.0165(12) 0.0260(13) C17 0.0595(12) 0.0591(13) 0.0783(15) -0.0179(11) 0.0139(11) 0.0099(10) C18 0.0397(9) 0.0639(13) 0.0762(14) -0.0358(11) 0.0062(9) 0.0023(8) C19 0.0451(10) 0.0724(14) 0.0844(15) -0.0384(12) 0.0000(10) 0.0013(10) C20 0.0608(14) 0.0737(16) 0.110(2) -0.0527(16) 0.0125(13) -0.0106(12) C21 0.0909(19) 0.0633(15) 0.101(2) -0.0248(15) 0.0263(16) -0.0143(14) C22 0.135(3) 0.0747(18) 0.0790(19) -0.0021(15) -0.0018(18) -0.0166(18) C23 0.100(2) 0.0744(16) 0.0683(16) -0.0183(13) -0.0050(14) -0.0198(14) C24 0.0419(10) 0.0629(12) 0.0675(13) -0.0298(10) 0.0109(9) -0.0068(9) C25 0.0499(10) 0.0431(10) 0.0502(10) -0.0201(8) -0.0049(8) 0.0032(8) C26 0.0610(12) 0.0428(10) 0.0501(10) -0.0147(8) -0.0055(8) -0.0050(8) C27 0.129(2) 0.0688(16) 0.0724(16) -0.0371(13) -0.0148(15) -0.0201(15) C28 0.0574(11) 0.0551(11) 0.0503(11) -0.0209(9) -0.0064(8) -0.0038(9) C29 0.0612(12) 0.0521(11) 0.0518(11) -0.0176(9) -0.0021(9) 0.0009(9) C30 0.132(3) 0.0867(19) 0.0671(16) -0.0079(14) 0.0223(16) -0.0322(18) N1 0.0476(8) 0.0542(9) 0.0499(8) -0.0253(7) -0.0072(6) 0.0117(7) N2 0.0423(8) 0.0467(8) 0.0578(9) -0.0211(7) -0.0031(6) 0.0073(6) O1 0.1071(13) 0.0504(9) 0.0655(9) -0.0256(7) 0.0084(9) -0.0096(8) O2 0.0766(10) 0.0757(11) 0.0895(12) -0.0485(9) 0.0267(9) -0.0100(8) O3 0.0593(10) 0.1371(17) 0.0758(11) -0.0437(11) -0.0178(8) -0.0028(10) O4 0.0951(12) 0.0853(11) 0.0599(9) -0.0336(9) -0.0061(8) -0.0199(10) O5 0.0778(10) 0.0483(8) 0.0638(9) -0.0280(7) -0.0059(7) -0.0025(7) O6 0.0624(9) 0.0749(10) 0.0929(12) -0.0309(9) -0.0258(8) 0.0055(8) O7 0.1090(14) 0.0782(11) 0.0515(9) -0.0147(8) 0.0042(9) -0.0302(10) O8 0.0846(11) 0.0727(10) 0.0680(10) -0.0255(8) -0.0004(8) -0.0228(9) S1 0.0699(3) 0.0505(3) 0.0466(3) -0.0184(2) -0.0069(2) -0.0103(2) Se1 0.04197(11) 0.08263(17) 0.06005(14) -0.03152(11) -0.00770(8) 0.01126(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 C1 O1 1.453(3) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 O2 1.193(3) . ? C2 O1 1.326(3) . ? C2 C3 1.501(3) . ? C3 C4 1.365(3) . ? C3 C8 1.413(2) . ? C4 C5 1.461(3) . ? C4 Se1 1.875(2) . ? C5 O4 1.195(3) . ? C5 O3 1.343(3) . ? C6 O3 1.448(3) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C7 N1 1.366(2) . ? C7 C8 1.368(2) . ? C7 Se1 1.8677(17) . ? C8 N2 1.428(2) . ? C9 C11 1.337(2) . ? C9 N2 1.430(2) . ? C9 C10 1.501(3) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 N1 1.425(2) . ? C11 S1 1.7672(18) . ? C12 C13 1.361(3) . ? C12 C17 1.379(3) . ? C12 N1 1.437(2) . ? C13 C14 1.388(3) . ? C13 H13 0.9300 . ? C14 C15 1.361(4) . ? C14 H14 0.9300 . ? C15 C16 1.360(4) . ? C15 H15 0.9300 . ? C16 C17 1.378(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 N2 1.490(3) . ? C18 C24 1.508(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C24 1.383(3) . ? C19 C20 1.385(3) . ? C19 H19 0.9300 . ? C20 C21 1.360(4) . ? C20 H20 0.9300 . ? C21 C22 1.359(4) . ? C21 H21 0.9300 . ? C22 C23 1.389(4) . ? C22 H22 0.9300 . ? C23 C24 1.377(3) . ? C23 H23 0.9300 . ? C25 C28 1.330(3) . ? C25 C26 1.510(2) . ? C25 S1 1.760(2) . ? C26 O6 1.199(2) . ? C26 O5 1.315(2) . ? C27 O5 1.451(3) . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? C28 C29 1.467(3) . ? C28 H28 0.9300 . ? C29 O8 1.194(2) . ? C29 O7 1.329(3) . ? C30 O7 1.451(3) . ? C30 H30A 0.9600 . ? C30 H30B 0.9600 . ? C30 H30C 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 O1 C1 H1A 109.5 . . ? O1 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? O1 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O2 C2 O1 124.82(19) . . ? O2 C2 C3 123.97(19) . . ? O1 C2 C3 111.20(17) . . ? C4 C3 C8 115.16(16) . . ? C4 C3 C2 122.15(17) . . ? C8 C3 C2 122.57(17) . . ? C3 C4 C5 126.49(19) . . ? C3 C4 Se1 112.10(14) . . ? C5 C4 Se1 121.36(16) . . ? O4 C5 O3 124.3(2) . . ? O4 C5 C4 125.1(2) . . ? O3 C5 C4 110.6(2) . . ? O3 C6 H6A 109.5 . . ? O3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? O3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? N1 C7 C8 121.16(16) . . ? N1 C7 Se1 125.60(12) . . ? C8 C7 Se1 112.92(13) . . ? C7 C8 C3 113.84(16) . . ? C7 C8 N2 120.57(15) . . ? C3 C8 N2 125.60(15) . . ? C11 C9 N2 120.55(16) . . ? C11 C9 C10 124.45(19) . . ? N2 C9 C10 114.93(17) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 N1 121.49(16) . . ? C9 C11 S1 122.03(14) . . ? N1 C11 S1 116.13(13) . . ? C13 C12 C17 119.99(18) . . ? C13 C12 N1 120.08(17) . . ? C17 C12 N1 119.92(18) . . ? C12 C13 C14 119.7(2) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.4(2) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C16 C15 C14 119.8(2) . . ? C16 C15 H15 120.1 . . ? C14 C15 H15 120.1 . . ? C15 C16 C17 120.6(2) . . ? C15 C16 H16 119.7 . . ? C17 C16 H16 119.7 . . ? C16 C17 C12 119.5(2) . . ? C16 C17 H17 120.2 . . ? C12 C17 H17 120.2 . . ? N2 C18 C24 114.15(15) . . ? N2 C18 H18A 108.7 . . ? C24 C18 H18A 108.7 . . ? N2 C18 H18B 108.7 . . ? C24 C18 H18B 108.7 . . ? H18A C18 H18B 107.6 . . ? C24 C19 C20 120.6(2) . . ? C24 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C21 C20 C19 121.0(2) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C22 C21 C20 119.3(3) . . ? C22 C21 H21 120.3 . . ? C20 C21 H21 120.3 . . ? C21 C22 C23 120.4(3) . . ? C21 C22 H22 119.8 . . ? C23 C22 H22 119.8 . . ? C24 C23 C22 121.1(2) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C19 117.7(2) . . ? C23 C24 C18 121.26(19) . . ? C19 C24 C18 121.1(2) . . ? C28 C25 C26 123.24(18) . . ? C28 C25 S1 119.55(14) . . ? C26 C25 S1 116.94(14) . . ? O6 C26 O5 126.20(18) . . ? O6 C26 C25 122.62(17) . . ? O5 C26 C25 111.10(16) . . ? O5 C27 H27A 109.5 . . ? O5 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? O5 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C25 C28 C29 123.04(18) . . ? C25 C28 H28 118.5 . . ? C29 C28 H28 118.5 . . ? O8 C29 O7 123.6(2) . . ? O8 C29 C28 125.79(19) . . ? O7 C29 C28 110.60(17) . . ? O7 C30 H30A 109.5 . . ? O7 C30 H30B 109.5 . . ? H30A C30 H30B 109.5 . . ? O7 C30 H30C 109.5 . . ? H30A C30 H30C 109.5 . . ? H30B C30 H30C 109.5 . . ? C7 N1 C11 115.58(14) . . ? C7 N1 C12 121.84(15) . . ? C11 N1 C12 122.54(14) . . ? C8 N2 C9 112.80(14) . . ? C8 N2 C18 114.29(15) . . ? C9 N2 C18 113.98(15) . . ? C2 O1 C1 114.8(2) . . ? C5 O3 C6 116.1(2) . . ? C26 O5 C27 115.29(19) . . ? C29 O7 C30 116.90(19) . . ? C25 S1 C11 102.88(8) . . ? C7 Se1 C4 85.84(8) . . ? 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 O2 C2 C3 C4 -100.5(3) . . . . ? O1 C2 C3 C4 79.8(2) . . . . ? O2 C2 C3 C8 75.3(3) . . . . ? O1 C2 C3 C8 -104.4(2) . . . . ? C8 C3 C4 C5 -174.81(19) . . . . ? C2 C3 C4 C5 1.3(3) . . . . ? C8 C3 C4 Se1 2.9(2) . . . . ? C2 C3 C4 Se1 178.96(15) . . . . ? C3 C4 C5 O4 -3.7(4) . . . . ? Se1 C4 C5 O4 178.85(18) . . . . ? C3 C4 C5 O3 176.5(2) . . . . ? Se1 C4 C5 O3 -1.0(3) . . . . ? N1 C7 C8 C3 -170.22(17) . . . . ? Se1 C7 C8 C3 3.7(2) . . . . ? N1 C7 C8 N2 9.3(3) . . . . ? Se1 C7 C8 N2 -176.84(13) . . . . ? C4 C3 C8 C7 -4.3(3) . . . . ? C2 C3 C8 C7 179.61(18) . . . . ? C4 C3 C8 N2 176.23(18) . . . . ? C2 C3 C8 N2 0.1(3) . . . . ? N2 C9 C11 N1 0.7(3) . . . . ? C10 C9 C11 N1 177.4(2) . . . . ? N2 C9 C11 S1 -172.25(14) . . . . ? C10 C9 C11 S1 4.5(3) . . . . ? C17 C12 C13 C14 -1.1(4) . . . . ? N1 C12 C13 C14 177.9(2) . . . . ? C12 C13 C14 C15 0.8(4) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C14 C15 C16 C17 -0.3(4) . . . . ? C15 C16 C17 C12 0.1(4) . . . . ? C13 C12 C17 C16 0.6(4) . . . . ? N1 C12 C17 C16 -178.3(2) . . . . ? C24 C19 C20 C21 -1.6(4) . . . . ? C19 C20 C21 C22 0.1(4) . . . . ? C20 C21 C22 C23 1.2(5) . . . . ? C21 C22 C23 C24 -1.1(5) . . . . ? C22 C23 C24 C19 -0.4(4) . . . . ? C22 C23 C24 C18 -179.8(3) . . . . ? C20 C19 C24 C23 1.7(3) . . . . ? C20 C19 C24 C18 -178.92(19) . . . . ? N2 C18 C24 C23 90.5(3) . . . . ? N2 C18 C24 C19 -88.8(2) . . . . ? C28 C25 C26 O6 -91.1(3) . . . . ? S1 C25 C26 O6 82.9(2) . . . . ? C28 C25 C26 O5 92.0(2) . . . . ? S1 C25 C26 O5 -94.05(18) . . . . ? C26 C25 C28 C29 0.4(3) . . . . ? S1 C25 C28 C29 -173.42(15) . . . . ? C25 C28 C29 O8 -8.3(3) . . . . ? C25 C28 C29 O7 170.5(2) . . . . ? C8 C7 N1 C11 14.9(3) . . . . ? Se1 C7 N1 C11 -158.12(14) . . . . ? C8 C7 N1 C12 -162.82(18) . . . . ? Se1 C7 N1 C12 24.1(3) . . . . ? C9 C11 N1 C7 -20.2(3) . . . . ? S1 C11 N1 C7 153.15(14) . . . . ? C9 C11 N1 C12 157.56(18) . . . . ? S1 C11 N1 C12 -29.1(2) . . . . ? C13 C12 N1 C7 97.0(2) . . . . ? C17 C12 N1 C7 -84.1(2) . . . . ? C13 C12 N1 C11 -80.6(3) . . . . ? C17 C12 N1 C11 98.3(2) . . . . ? C7 C8 N2 C9 -27.6(2) . . . . ? C3 C8 N2 C9 151.79(18) . . . . ? C7 C8 N2 C18 104.68(19) . . . . ? C3 C8 N2 C18 -75.9(2) . . . . ? C11 C9 N2 C8 22.5(2) . . . . ? C10 C9 N2 C8 -154.55(19) . . . . ? C11 C9 N2 C18 -110.0(2) . . . . ? C10 C9 N2 C18 73.0(2) . . . . ? C24 C18 N2 C8 -65.0(2) . . . . ? C24 C18 N2 C9 66.8(2) . . . . ? O2 C2 O1 C1 7.6(4) . . . . ? C3 C2 O1 C1 -172.7(2) . . . . ? O4 C5 O3 C6 3.1(4) . . . . ? C4 C5 O3 C6 -177.1(2) . . . . ? O6 C26 O5 C27 1.5(3) . . . . ? C25 C26 O5 C27 178.28(18) . . . . ? O8 C29 O7 C30 1.6(3) . . . . ? C28 C29 O7 C30 -177.2(2) . . . . ? C28 C25 S1 C11 -162.96(16) . . . . ? C26 C25 S1 C11 22.85(16) . . . . ? C9 C11 S1 C25 79.43(18) . . . . ? N1 C11 S1 C25 -93.88(15) . . . . ? N1 C7 Se1 C4 171.86(18) . . . . ? C8 C7 Se1 C4 -1.70(15) . . . . ? C3 C4 Se1 C7 -0.66(16) . . . . ? C5 C4 Se1 C7 177.14(18) . . . . ? _diffrn_measured_fraction_theta_max 0.992 _diffrn_reflns_theta_full 27.69 _diffrn_measured_fraction_theta_full 0.992 _refine_diff_density_max 0.416 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.043 # Attachment '8j-Y._Cheng_and_J.H.Zhang.cif' data_r80413e _database_code_depnum_ccdc_archive 'CCDC 721794' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ; (2Z,5Z)-Methyl 4-(4-bromobenzylamino)-5-(3,4- dichlorophenylimino)-2-(2-phenylethylidene)-2,5-dihydroselenophene-3- carboxylate ; _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H21 Br Cl2 N2 O2 Se' _chemical_formula_weight 635.23 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' Cl Cl 0.1484 0.1585 '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' Br Br -0.2901 2.4595 '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 9.781(2) _cell_length_b 11.518(2) _cell_length_c 11.812(2) _cell_angle_alpha 88.96(3) _cell_angle_beta 72.07(3) _cell_angle_gamma 80.99(3) _cell_volume 1249.8(4) _cell_formula_units_Z 2 _cell_measurement_temperature 113(2) _cell_measurement_reflns_used 3641 _cell_measurement_theta_min 2.508 _cell_measurement_theta_max 27.876 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.688 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 3.343 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_correction_T_min 0.6168 _exptl_absorpt_correction_T_max 0.7310 _exptl_absorpt_process_details crystalclear _exptl_special_details ; ? ; _diffrn_ambient_temperature 113(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Rotating anode' _diffrn_radiation_monochromator confocal _diffrn_measurement_device_type 'rigaku saturn' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 7.31 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 9144 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_sigmaI/netI 0.0798 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.51 _diffrn_reflns_theta_max 27.87 _reflns_number_total 5860 _reflns_number_gt 3612 _reflns_threshold_expression >2sigma(I) _computing_data_collection crystalclear _computing_cell_refinement crystalclear _computing_data_reduction crystalclear _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^)+(0.0434P)^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 5860 _refine_ls_number_parameters 321 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0579 _refine_ls_R_factor_gt 0.0367 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0852 _refine_ls_goodness_of_fit_ref 0.946 _refine_ls_restrained_S_all 0.946 _refine_ls_shift/su_max 0.001 _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 1.10363(3) 0.24579(3) 0.37834(3) 0.02424(10) Uani 1 1 d . . . Br1 Br 0.65616(4) -0.20558(3) 0.94542(3) 0.03573(11) Uani 1 1 d . . . Cl1 Cl 1.61971(8) -0.00200(7) 0.24160(7) 0.02942(19) Uani 1 1 d . . . Cl2 Cl 1.57762(10) -0.26624(8) 0.30198(9) 0.0396(2) Uani 1 1 d . . . O1 O 0.7246(3) 0.47691(19) 0.73743(19) 0.0287(5) Uani 1 1 d . . . O2 O 0.6723(2) 0.5059(2) 0.5672(2) 0.0317(6) Uani 1 1 d . . . N1 N 0.9387(3) 0.3056(2) 0.7385(2) 0.0224(6) Uani 1 1 d . . . N2 N 1.1428(3) 0.1231(2) 0.5830(2) 0.0219(6) Uani 1 1 d . . . C1 C 0.7649(4) 0.1215(3) 0.8364(3) 0.0253(7) Uani 1 1 d . . . H1 H 0.7179 0.1929 0.8143 0.030 Uiso 1 1 calc R . . C2 C 0.6896(3) 0.0272(3) 0.8685(3) 0.0242(7) Uani 1 1 d . . . H2 H 0.5919 0.0334 0.8678 0.029 Uiso 1 1 calc R . . C3 C 0.7590(3) -0.0758(3) 0.9014(3) 0.0223(7) Uani 1 1 d . . . C4 C 0.9001(3) -0.0875(3) 0.9014(3) 0.0241(7) Uani 1 1 d . . . H4 H 0.9466 -0.1590 0.9236 0.029 Uiso 1 1 calc R . . C5 C 0.9746(3) 0.0078(3) 0.8682(3) 0.0228(7) Uani 1 1 d . . . H5 H 1.0730 0.0003 0.8675 0.027 Uiso 1 1 calc R . . C6 C 0.9090(3) 0.1125(3) 0.8364(3) 0.0198(7) Uani 1 1 d . . . C7 C 0.9877(4) 0.2173(3) 0.8143(3) 0.0225(7) Uani 1 1 d . . . H7A H 0.9755 0.2555 0.8919 0.027 Uiso 1 1 calc R . . H7B H 1.0929 0.1891 0.7769 0.027 Uiso 1 1 calc R . . C8 C 0.9646(3) 0.3009(3) 0.6187(3) 0.0201(7) Uani 1 1 d . . . C9 C 1.0788(3) 0.2117(3) 0.5417(3) 0.0204(7) Uani 1 1 d . . . C10 C 0.9400(3) 0.3680(3) 0.4296(3) 0.0200(7) Uani 1 1 d . . . C11 C 0.8873(3) 0.3780(3) 0.5605(3) 0.0189(6) Uani 1 1 d . . . C12 C 0.7587(4) 0.4564(3) 0.6298(3) 0.0220(7) Uani 1 1 d . . . C13 C 0.5421(4) 0.5819(3) 0.6345(3) 0.0386(9) Uani 1 1 d . . . H13A H 0.4829 0.5373 0.6970 0.058 Uiso 1 1 calc R . . H13B H 0.4863 0.6129 0.5814 0.058 Uiso 1 1 calc R . . H13C H 0.5685 0.6473 0.6710 0.058 Uiso 1 1 calc R . . C14 C 0.8934(3) 0.4324(3) 0.3488(3) 0.0214(7) Uani 1 1 d . . . H14 H 0.8115 0.4924 0.3782 0.026 Uiso 1 1 calc R . . C15 C 0.9592(3) 0.4178(3) 0.2166(3) 0.0244(7) Uani 1 1 d . . . H15A H 1.0365 0.3479 0.1981 0.029 Uiso 1 1 calc R . . H15B H 1.0054 0.4874 0.1859 0.029 Uiso 1 1 calc R . . C16 C 0.8492(3) 0.4031(3) 0.1527(3) 0.0185(6) Uani 1 1 d . . . C17 C 0.8136(3) 0.4901(3) 0.0785(3) 0.0203(7) Uani 1 1 d . . . H17 H 0.8558 0.5600 0.0698 0.024 Uiso 1 1 calc R . . C18 C 0.7163(3) 0.4750(3) 0.0170(3) 0.0236(7) Uani 1 1 d . . . H18 H 0.6926 0.5344 -0.0338 0.028 Uiso 1 1 calc R . . C19 C 0.6543(3) 0.3736(3) 0.0300(3) 0.0239(7) Uani 1 1 d . . . H19 H 0.5888 0.3632 -0.0125 0.029 Uiso 1 1 calc R . . C20 C 0.6870(3) 0.2876(3) 0.1043(3) 0.0241(7) Uani 1 1 d . . . H20 H 0.6439 0.2182 0.1133 0.029 Uiso 1 1 calc R . . C21 C 0.7838(3) 0.3028(3) 0.1663(3) 0.0204(6) Uani 1 1 d . . . H21 H 0.8052 0.2439 0.2184 0.024 Uiso 1 1 calc R . . C22 C 1.2464(3) 0.0357(3) 0.5100(3) 0.0197(6) Uani 1 1 d . . . C23 C 1.3686(3) 0.0581(3) 0.4180(3) 0.0216(7) Uani 1 1 d . . . H23 H 1.3814 0.1370 0.3989 0.026 Uiso 1 1 calc R . . C24 C 1.4699(3) -0.0330(3) 0.3551(3) 0.0217(7) Uani 1 1 d . . . C25 C 1.4523(3) -0.1498(3) 0.3801(3) 0.0248(7) Uani 1 1 d . . . C26 C 1.3317(3) -0.1731(3) 0.4715(3) 0.0249(7) Uani 1 1 d . . . H26 H 1.3191 -0.2522 0.4895 0.030 Uiso 1 1 calc R . . C27 C 1.2298(4) -0.0819(3) 0.5365(3) 0.0242(7) Uani 1 1 d . . . H27 H 1.1483 -0.0988 0.5993 0.029 Uiso 1 1 calc R . . H1A H 0.870(4) 0.349(3) 0.769(3) 0.020(10) 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 Se1 0.02415(18) 0.03101(19) 0.01547(17) -0.00003(13) -0.00555(14) 0.00081(14) Br1 0.0307(2) 0.02809(19) 0.0421(2) -0.00549(16) 0.00090(18) -0.01006(16) Cl1 0.0212(4) 0.0363(5) 0.0286(5) 0.0046(4) -0.0045(4) -0.0049(4) Cl2 0.0399(5) 0.0269(4) 0.0428(6) -0.0063(4) -0.0033(5) 0.0035(4) O1 0.0362(13) 0.0293(13) 0.0182(12) -0.0031(10) -0.0098(11) 0.0048(11) O2 0.0299(13) 0.0418(14) 0.0188(12) -0.0017(11) -0.0094(11) 0.0123(11) N1 0.0289(16) 0.0238(15) 0.0132(14) -0.0010(12) -0.0073(14) 0.0009(14) N2 0.0269(14) 0.0218(14) 0.0175(14) 0.0005(11) -0.0077(12) -0.0033(12) C1 0.0287(18) 0.0248(17) 0.0239(18) -0.0003(14) -0.0131(16) 0.0012(14) C2 0.0196(16) 0.0293(17) 0.0243(18) -0.0041(14) -0.0082(15) -0.0022(14) C3 0.0238(16) 0.0230(16) 0.0156(16) -0.0074(13) 0.0004(14) -0.0032(14) C4 0.0247(17) 0.0225(16) 0.0238(17) 0.0008(14) -0.0073(15) -0.0008(14) C5 0.0208(16) 0.0268(17) 0.0202(17) 0.0010(14) -0.0069(15) -0.0008(14) C6 0.0236(16) 0.0252(16) 0.0113(15) -0.0004(13) -0.0069(14) -0.0030(14) C7 0.0299(17) 0.0236(16) 0.0180(17) 0.0030(13) -0.0139(15) -0.0032(14) C8 0.0229(16) 0.0221(15) 0.0164(16) 0.0002(13) -0.0061(14) -0.0071(13) C9 0.0213(16) 0.0227(16) 0.0188(16) 0.0011(13) -0.0071(14) -0.0061(13) C10 0.0229(16) 0.0213(15) 0.0194(16) 0.0011(13) -0.0109(14) -0.0058(13) C11 0.0238(16) 0.0202(15) 0.0128(15) -0.0016(12) -0.0054(14) -0.0039(13) C12 0.0273(17) 0.0204(16) 0.0185(17) 0.0021(13) -0.0081(15) -0.0026(14) C13 0.034(2) 0.046(2) 0.027(2) -0.0027(17) -0.0079(18) 0.0174(18) C14 0.0231(16) 0.0261(16) 0.0142(15) -0.0020(13) -0.0048(14) -0.0038(14) C15 0.0247(17) 0.0329(18) 0.0183(16) 0.0034(14) -0.0098(15) -0.0071(15) C16 0.0190(15) 0.0228(15) 0.0117(15) -0.0022(12) -0.0033(13) 0.0001(13) C17 0.0246(16) 0.0195(15) 0.0170(16) -0.0006(13) -0.0067(14) -0.0037(13) C18 0.0268(17) 0.0230(16) 0.0208(17) 0.0069(14) -0.0104(15) 0.0026(14) C19 0.0217(16) 0.0327(18) 0.0180(16) -0.0049(14) -0.0071(14) -0.0039(14) C20 0.0255(17) 0.0202(16) 0.0265(18) 0.0006(14) -0.0074(15) -0.0046(14) C21 0.0224(16) 0.0184(15) 0.0177(16) 0.0022(12) -0.0041(14) 0.0003(13) C22 0.0213(15) 0.0213(15) 0.0187(16) 0.0018(13) -0.0112(14) 0.0006(13) C23 0.0258(17) 0.0184(15) 0.0231(17) 0.0031(13) -0.0116(15) -0.0035(13) C24 0.0220(16) 0.0279(17) 0.0179(16) 0.0025(13) -0.0096(14) -0.0059(14) C25 0.0252(17) 0.0233(16) 0.0277(18) -0.0048(14) -0.0123(16) -0.0004(14) C26 0.0284(18) 0.0204(16) 0.0271(19) 0.0003(14) -0.0101(16) -0.0040(14) C27 0.0255(17) 0.0260(17) 0.0220(17) 0.0038(14) -0.0082(15) -0.0050(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 Se1 C10 1.908(3) . ? Se1 C9 1.910(3) . ? Br1 C3 1.907(3) . ? Cl1 C24 1.735(3) . ? Cl2 C25 1.728(4) . ? O1 C12 1.228(4) . ? O2 C12 1.343(3) . ? O2 C13 1.440(4) . ? N1 C8 1.359(4) . ? N1 C7 1.464(4) . ? N1 H1A 0.77(3) . ? N2 C9 1.281(4) . ? N2 C22 1.399(4) . ? C1 C2 1.389(4) . ? C1 C6 1.397(4) . ? C1 H1 0.9500 . ? C2 C3 1.383(4) . ? C2 H2 0.9500 . ? C3 C4 1.365(4) . ? C4 C5 1.396(4) . ? C4 H4 0.9500 . ? C5 C6 1.377(4) . ? C5 H5 0.9500 . ? C6 C7 1.508(4) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C11 1.386(4) . ? C8 C9 1.476(5) . ? C10 C14 1.343(4) . ? C10 C11 1.472(4) . ? C11 C12 1.451(5) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 C15 1.496(4) . ? C14 H14 0.9500 . ? C15 C16 1.522(4) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.390(4) . ? C16 C17 1.393(4) . ? C17 C18 1.395(4) . ? C17 H17 0.9500 . ? C18 C19 1.384(4) . ? C18 H18 0.9500 . ? C19 C20 1.376(4) . ? C19 H19 0.9500 . ? C20 C21 1.395(4) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.401(4) . ? C22 C27 1.408(4) . ? C23 C24 1.372(5) . ? C23 H23 0.9500 . ? C24 C25 1.398(4) . ? C25 C26 1.390(4) . ? C26 C27 1.384(5) . ? C26 H26 0.9500 . ? C27 H27 0.9500 . ? 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 C10 Se1 C9 88.44(13) . . ? C12 O2 C13 115.7(3) . . ? C8 N1 C7 128.8(3) . . ? C8 N1 H1A 111(2) . . ? C7 N1 H1A 116(3) . . ? C9 N2 C22 122.9(3) . . ? C2 C1 C6 120.7(3) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C3 C2 C1 119.0(3) . . ? C3 C2 H2 120.5 . . ? C1 C2 H2 120.5 . . ? C4 C3 C2 121.6(3) . . ? C4 C3 Br1 119.1(2) . . ? C2 C3 Br1 119.2(2) . . ? C3 C4 C5 118.6(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C6 C5 C4 121.6(3) . . ? C6 C5 H5 119.2 . . ? C4 C5 H5 119.2 . . ? C5 C6 C1 118.4(3) . . ? C5 C6 C7 119.8(2) . . ? C1 C6 C7 121.5(3) . . ? N1 C7 C6 114.8(2) . . ? N1 C7 H7A 108.6 . . ? C6 C7 H7A 108.6 . . ? N1 C7 H7B 108.6 . . ? C6 C7 H7B 108.6 . . ? H7A C7 H7B 107.5 . . ? N1 C8 C11 123.1(3) . . ? N1 C8 C9 121.4(3) . . ? C11 C8 C9 115.5(3) . . ? N2 C9 C8 122.8(3) . . ? N2 C9 Se1 127.4(3) . . ? C8 C9 Se1 109.73(19) . . ? C14 C10 C11 130.0(3) . . ? C14 C10 Se1 119.9(3) . . ? C11 C10 Se1 110.07(19) . . ? C8 C11 C12 119.4(3) . . ? C8 C11 C10 115.7(3) . . ? C12 C11 C10 124.8(2) . . ? O1 C12 O2 120.2(3) . . ? O1 C12 C11 125.2(3) . . ? O2 C12 C11 114.6(3) . . ? O2 C13 H13A 109.5 . . ? O2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C10 C14 C15 125.6(3) . . ? C10 C14 H14 117.2 . . ? C15 C14 H14 117.2 . . ? C14 C15 C16 113.3(3) . . ? C14 C15 H15A 108.9 . . ? C16 C15 H15A 108.9 . . ? C14 C15 H15B 108.9 . . ? C16 C15 H15B 108.9 . . ? H15A C15 H15B 107.7 . . ? C21 C16 C17 118.9(2) . . ? C21 C16 C15 120.8(2) . . ? C17 C16 C15 120.2(2) . . ? C16 C17 C18 120.2(3) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 120.0(3) . . ? C19 C18 H18 120.0 . . ? C17 C18 H18 120.0 . . ? C20 C19 C18 120.4(3) . . ? C20 C19 H19 119.8 . . ? C18 C19 H19 119.8 . . ? C19 C20 C21 119.7(3) . . ? C19 C20 H20 120.2 . . ? C21 C20 H20 120.2 . . ? C16 C21 C20 120.8(3) . . ? C16 C21 H21 119.6 . . ? C20 C21 H21 119.6 . . ? N2 C22 C23 124.2(3) . . ? N2 C22 C27 117.1(3) . . ? C23 C22 C27 118.6(3) . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 120.8(3) . . ? C23 C24 Cl1 119.3(2) . . ? C25 C24 Cl1 119.9(3) . . ? C26 C25 C24 119.1(3) . . ? C26 C25 Cl2 119.0(2) . . ? C24 C25 Cl2 121.8(3) . . ? C27 C26 C25 120.5(3) . . ? C27 C26 H26 119.7 . . ? C25 C26 H26 119.7 . . ? C26 C27 C22 120.3(3) . . ? C26 C27 H27 119.8 . . ? C22 C27 H27 119.8 . . ? 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 0.5(5) . . . . ? C1 C2 C3 C4 -1.0(5) . . . . ? C1 C2 C3 Br1 -180.0(2) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? Br1 C3 C4 C5 179.5(2) . . . . ? C3 C4 C5 C6 0.4(5) . . . . ? C4 C5 C6 C1 -0.8(5) . . . . ? C4 C5 C6 C7 173.3(3) . . . . ? C2 C1 C6 C5 0.4(5) . . . . ? C2 C1 C6 C7 -173.6(3) . . . . ? C8 N1 C7 C6 -74.5(4) . . . . ? C5 C6 C7 N1 157.1(3) . . . . ? C1 C6 C7 N1 -29.0(4) . . . . ? C7 N1 C8 C11 165.5(3) . . . . ? C7 N1 C8 C9 -14.6(5) . . . . ? C22 N2 C9 C8 177.1(2) . . . . ? C22 N2 C9 Se1 0.9(4) . . . . ? N1 C8 C9 N2 11.8(4) . . . . ? C11 C8 C9 N2 -168.2(3) . . . . ? N1 C8 C9 Se1 -171.4(2) . . . . ? C11 C8 C9 Se1 8.5(3) . . . . ? C10 Se1 C9 N2 170.1(3) . . . . ? C10 Se1 C9 C8 -6.43(19) . . . . ? C9 Se1 C10 C14 -178.8(2) . . . . ? C9 Se1 C10 C11 3.38(19) . . . . ? N1 C8 C11 C12 -9.7(4) . . . . ? C9 C8 C11 C12 170.4(2) . . . . ? N1 C8 C11 C10 173.8(2) . . . . ? C9 C8 C11 C10 -6.2(4) . . . . ? C14 C10 C11 C8 -176.8(3) . . . . ? Se1 C10 C11 C8 0.7(3) . . . . ? C14 C10 C11 C12 6.9(5) . . . . ? Se1 C10 C11 C12 -175.6(2) . . . . ? C13 O2 C12 O1 0.1(4) . . . . ? C13 O2 C12 C11 178.6(3) . . . . ? C8 C11 C12 O1 14.1(4) . . . . ? C10 C11 C12 O1 -169.7(3) . . . . ? C8 C11 C12 O2 -164.4(2) . . . . ? C10 C11 C12 O2 11.9(4) . . . . ? C11 C10 C14 C15 177.3(3) . . . . ? Se1 C10 C14 C15 0.0(4) . . . . ? C10 C14 C15 C16 126.9(3) . . . . ? C14 C15 C16 C21 -67.9(4) . . . . ? C14 C15 C16 C17 112.7(3) . . . . ? C21 C16 C17 C18 -1.4(5) . . . . ? C15 C16 C17 C18 178.0(3) . . . . ? C16 C17 C18 C19 0.3(5) . . . . ? C17 C18 C19 C20 0.6(5) . . . . ? C18 C19 C20 C21 -0.3(5) . . . . ? C17 C16 C21 C20 1.8(5) . . . . ? C15 C16 C21 C20 -177.7(3) . . . . ? C19 C20 C21 C16 -0.9(5) . . . . ? C9 N2 C22 C23 52.1(4) . . . . ? C9 N2 C22 C27 -131.8(3) . . . . ? N2 C22 C23 C24 176.0(2) . . . . ? C27 C22 C23 C24 0.0(4) . . . . ? C22 C23 C24 C25 1.1(4) . . . . ? C22 C23 C24 Cl1 179.9(2) . . . . ? C23 C24 C25 C26 -1.3(4) . . . . ? Cl1 C24 C25 C26 179.9(2) . . . . ? C23 C24 C25 Cl2 179.7(2) . . . . ? Cl1 C24 C25 Cl2 0.9(3) . . . . ? C24 C25 C26 C27 0.4(4) . . . . ? Cl2 C25 C26 C27 179.5(2) . . . . ? C25 C26 C27 C22 0.6(4) . . . . ? N2 C22 C27 C26 -177.1(2) . . . . ? C23 C22 C27 C26 -0.8(4) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1A O1 0.77(3) 1.99(3) 2.646(4) 143(3) . _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 27.87 _diffrn_measured_fraction_theta_full 0.983 _refine_diff_density_max 0.966 _refine_diff_density_min -0.979 _refine_diff_density_rms 0.105