# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address J.Thomas ;Molecular Design and Synthesis Departement of Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200F B-3001 Leuven Belgium ; 'K.Van Hecke' ;Biomolecular Architecture Departement of Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200F B-3001 Leuven Belgium ; 'W.Van Rossom' ;Molecular Design and Synthesis Departement of Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200F B-3001 Leuven Belgium ; 'L.Van Meervelt' ;Biomolecular Architecture Departement of Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200F B-3001 Leuven Belgium ; M.Smet ;Molecular Design and Synthesis Departement of Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200F B-3001 Leuven Belgium ; ; W.Maes ; ;Institute for Materials Research (IMO) Research Group Organic and (Bio)Polymer Chemistry (OBPC) Hasselt University Universitaire Campus Agoralaan - Building D B-3590 Diepenbeek Belgium ; W.Dehaen ;Molecular Design and Synthesis Departement of Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200F B-3001 Leuven Belgium ; _publ_contact_author_name 'Dr Wim Dehaen' _publ_contact_author_email Wim.Dehaen@chem.kuleuven.be _publ_contact_author_address ;Molecular Design and Synthesis Departement of Chemistry Katholieke Universiteit Leuven Celestijnenlaan 200F B-3001 Leuven Belgium ; _publ_contact_author_phone +3216327439 _publ_contact_author_fax +3216327990 _publ_section_title ; Selenacalix[3]triazines: Synthesis and Host-Guest Chemistry ; # Attachment '- 2c.cif' #TrackingRef '- 2c.cif' data_wim141 _database_code_depnum_ccdc_archive 'CCDC 808717' #TrackingRef '- 2c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H30 N12 Se3, C2 H3 N' _chemical_formula_sum 'C23 H33 N13 Se3' _chemical_formula_weight 728.50 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' 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 16.628(12) _cell_length_b 10.688(5) _cell_length_c 16.662(12) _cell_angle_alpha 90.00 _cell_angle_beta 94.87(3) _cell_angle_gamma 90.00 _cell_volume 2951(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.640 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1456 _exptl_absorpt_coefficient_mu 4.858 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.356 _exptl_absorpt_correction_T_max 0.615 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed G\"obel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27081 _diffrn_reflns_av_R_equivalents 0.0574 _diffrn_reflns_av_sigmaI/netI 0.0369 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.61 _diffrn_reflns_theta_max 70.36 _reflns_number_total 5511 _reflns_number_gt 4792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material Platon _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^+2.9369P] 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 5511 _refine_ls_number_parameters 359 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0465 _refine_ls_R_factor_gt 0.0388 _refine_ls_wR_factor_ref 0.0933 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.163 _refine_ls_restrained_S_all 1.163 _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 0.6256(2) 0.8913(3) 0.15148(19) 0.0158(6) Uani 1 1 d . . . C2 C 0.6304(2) 0.8606(3) 0.0181(2) 0.0173(7) Uani 1 1 d . . . C3 C 0.7280(2) 0.9685(3) 0.09090(19) 0.0164(6) Uani 1 1 d . . . C4 C 0.5187(2) 0.7498(3) -0.05573(19) 0.0185(7) Uani 1 1 d . . . H4A H 0.5161 0.7003 -0.0058 0.022 Uiso 1 1 calc R . . H4B H 0.5159 0.6909 -0.1018 0.022 Uiso 1 1 calc R . . C5 C 0.4472(2) 0.8388(4) -0.0652(2) 0.0251(8) Uani 1 1 d . . . H5A H 0.4466 0.8911 -0.0170 0.038 Uiso 1 1 calc R . . H5B H 0.3970 0.7905 -0.0724 0.038 Uiso 1 1 calc R . . H5C H 0.4518 0.8922 -0.1124 0.038 Uiso 1 1 calc R . . C6 C 0.6295(2) 0.8460(4) -0.1295(2) 0.0231(8) Uani 1 1 d . . . H6A H 0.6663 0.9186 -0.1220 0.028 Uiso 1 1 calc R . . H6B H 0.5851 0.8692 -0.1701 0.028 Uiso 1 1 calc R . . C7 C 0.6750(3) 0.7366(5) -0.1605(3) 0.0377(10) Uani 1 1 d . . . H7A H 0.7187 0.7126 -0.1203 0.057 Uiso 1 1 calc R . . H7B H 0.6977 0.7603 -0.2107 0.057 Uiso 1 1 calc R . . H7C H 0.6381 0.6657 -0.1707 0.057 Uiso 1 1 calc R . . C8 C 0.8815(2) 1.0493(3) 0.19392(19) 0.0155(6) Uani 1 1 d . . . C9 C 1.0015(2) 1.0690(3) 0.2652(2) 0.0173(7) Uani 1 1 d . . . C10 C 0.8888(2) 1.0256(3) 0.3265(2) 0.0165(6) Uani 1 1 d . . . C11 C 1.1190(2) 1.1321(4) 0.1955(2) 0.0269(8) Uani 1 1 d . . . H11A H 1.1617 1.1952 0.2090 0.032 Uiso 1 1 calc R . . H11B H 1.0781 1.1706 0.1564 0.032 Uiso 1 1 calc R . . C12 C 1.1559(3) 1.0206(5) 0.1564(3) 0.0402(11) Uani 1 1 d . . . H12A H 1.1957 0.9811 0.1951 0.060 Uiso 1 1 calc R . . H12B H 1.1825 1.0484 0.1092 0.060 Uiso 1 1 calc R . . H12C H 1.1134 0.9602 0.1397 0.060 Uiso 1 1 calc R . . C13 C 1.1299(2) 1.1080(4) 0.3466(2) 0.0235(8) Uani 1 1 d . . . H13A H 1.1851 1.0775 0.3398 0.028 Uiso 1 1 calc R . . H13B H 1.1064 1.0536 0.3867 0.028 Uiso 1 1 calc R . . C14 C 1.1344(2) 1.2413(4) 0.3779(2) 0.0313(9) Uani 1 1 d . . . H14A H 1.1523 1.2968 0.3362 0.047 Uiso 1 1 calc R . . H14B H 1.1728 1.2456 0.4258 0.047 Uiso 1 1 calc R . . H14C H 1.0809 1.2677 0.3920 0.047 Uiso 1 1 calc R . . C15 C 0.7382(2) 0.9371(3) 0.41145(19) 0.0167(6) Uani 1 1 d . . . C16 C 0.6261(2) 0.8865(3) 0.4719(2) 0.0162(6) Uani 1 1 d . . . C17 C 0.6263(2) 0.8909(3) 0.33660(19) 0.0161(6) Uani 1 1 d . . . C18 C 0.6306(2) 0.8645(4) 0.6193(2) 0.0227(7) Uani 1 1 d . . . H18A H 0.6862 0.8329 0.6160 0.027 Uiso 1 1 calc R . . H18B H 0.6030 0.8079 0.6551 0.027 Uiso 1 1 calc R . . C19 C 0.6342(2) 0.9956(4) 0.6552(2) 0.0303(9) Uani 1 1 d . . . H19A H 0.6652 1.0504 0.6221 0.045 Uiso 1 1 calc R . . H19B H 0.6604 0.9923 0.7101 0.045 Uiso 1 1 calc R . . H19C H 0.5793 1.0285 0.6565 0.045 Uiso 1 1 calc R . . C20 C 0.5001(2) 0.8356(3) 0.53259(19) 0.0195(7) Uani 1 1 d . . . H20A H 0.4735 0.8817 0.4862 0.023 Uiso 1 1 calc R . . H20B H 0.4774 0.8665 0.5819 0.023 Uiso 1 1 calc R . . C21 C 0.4811(2) 0.6977(4) 0.5227(2) 0.0279(8) Uani 1 1 d . . . H21A H 0.5025 0.6667 0.4734 0.042 Uiso 1 1 calc R . . H21B H 0.4225 0.6856 0.5191 0.042 Uiso 1 1 calc R . . H21C H 0.5061 0.6516 0.5692 0.042 Uiso 1 1 calc R . . C22 C 0.6850(2) 0.2184(4) 0.2818(2) 0.0267(8) Uani 1 1 d . . . H22A H 0.7117 0.2864 0.2550 0.040 Uiso 1 1 calc R . . H22B H 0.6982 0.1383 0.2576 0.040 Uiso 1 1 calc R . . H22C H 0.7036 0.2178 0.3392 0.040 Uiso 1 1 calc R . . C23 C 0.5962(2) 0.2377(4) 0.2723(2) 0.0247(8) Uani 1 1 d . . . N1 N 0.59131(17) 0.8379(3) 0.08566(16) 0.0174(6) Uani 1 1 d . . . N2 N 0.70251(18) 0.9216(3) 0.01921(16) 0.0195(6) Uani 1 1 d . . . N3 N 0.69196(17) 0.9618(3) 0.15976(16) 0.0175(6) Uani 1 1 d . . . N4 N 0.59536(17) 0.8181(3) -0.05213(16) 0.0192(6) Uani 1 1 d . . . N5 N 0.96044(17) 1.0655(3) 0.19140(17) 0.0182(6) Uani 1 1 d . . . N6 N 0.96789(17) 1.0431(3) 0.33568(17) 0.0176(6) Uani 1 1 d . . . N7 N 0.83950(17) 1.0318(3) 0.25869(16) 0.0167(6) Uani 1 1 d . . . N8 N 1.08065(18) 1.0989(3) 0.26920(17) 0.0212(6) Uani 1 1 d . . . N9 N 0.70542(17) 0.9216(3) 0.48084(16) 0.0178(6) Uani 1 1 d . . . N10 N 0.58234(17) 0.8763(3) 0.39903(16) 0.0169(6) Uani 1 1 d . . . N11 N 0.70495(17) 0.9184(3) 0.33691(16) 0.0173(6) Uani 1 1 d . . . N12 N 0.58740(17) 0.8627(3) 0.53821(17) 0.0198(6) Uani 1 1 d . . . N13 N 0.5302(2) 0.2545(4) 0.26694(19) 0.0336(8) Uani 1 1 d . . . Se1 Se 0.55867(2) 0.86631(4) 0.23907(2) 0.01866(11) Uani 1 1 d . . . Se2 Se 0.82836(2) 1.05707(4) 0.086193(19) 0.01877(11) Uani 1 1 d . . . Se3 Se 0.84802(2) 0.99672(4) 0.43027(2) 0.02023(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 C1 0.0148(16) 0.0201(17) 0.0122(14) 0.0014(12) -0.0006(12) 0.0000(12) C2 0.0170(16) 0.0187(17) 0.0160(15) 0.0010(12) 0.0002(13) -0.0007(12) C3 0.0127(15) 0.0198(17) 0.0160(15) 0.0012(12) -0.0023(12) 0.0017(12) C4 0.0161(16) 0.0233(18) 0.0157(15) -0.0002(13) -0.0009(12) -0.0018(13) C5 0.0208(18) 0.028(2) 0.0266(18) 0.0051(15) 0.0016(14) 0.0015(14) C6 0.0210(18) 0.033(2) 0.0155(16) -0.0007(14) 0.0027(13) -0.0080(14) C7 0.035(2) 0.048(3) 0.032(2) -0.0041(18) 0.0122(18) -0.0006(19) C8 0.0136(16) 0.0172(17) 0.0156(15) 0.0002(12) 0.0001(12) -0.0018(12) C9 0.0142(16) 0.0204(18) 0.0175(15) -0.0004(13) 0.0025(12) 0.0009(12) C10 0.0178(16) 0.0166(17) 0.0154(15) 0.0002(12) 0.0033(12) -0.0037(12) C11 0.0160(17) 0.045(2) 0.0198(17) 0.0058(15) 0.0018(14) -0.0088(15) C12 0.028(2) 0.064(3) 0.030(2) -0.012(2) 0.0082(17) -0.008(2) C13 0.0139(16) 0.036(2) 0.0202(17) 0.0046(14) -0.0003(13) -0.0011(14) C14 0.024(2) 0.043(2) 0.0256(19) -0.0050(17) -0.0041(15) 0.0053(17) C15 0.0130(16) 0.0199(18) 0.0173(16) 0.0011(12) 0.0016(12) 0.0004(12) C16 0.0142(16) 0.0162(17) 0.0185(16) 0.0011(12) 0.0032(12) 0.0005(12) C17 0.0176(16) 0.0160(17) 0.0144(15) -0.0003(12) -0.0007(12) -0.0011(12) C18 0.0164(17) 0.038(2) 0.0134(16) 0.0036(14) 0.0015(13) -0.0029(14) C19 0.024(2) 0.045(3) 0.0216(18) -0.0055(16) -0.0001(15) -0.0016(16) C20 0.0122(16) 0.032(2) 0.0147(15) 0.0019(13) 0.0030(12) 0.0020(13) C21 0.0251(19) 0.031(2) 0.0274(18) 0.0021(15) 0.0030(15) -0.0041(15) C22 0.0256(19) 0.022(2) 0.0321(19) 0.0000(15) 0.0021(15) 0.0010(14) C23 0.034(2) 0.0233(19) 0.0183(17) -0.0011(14) 0.0132(15) -0.0036(15) N1 0.0182(14) 0.0207(15) 0.0131(13) 0.0006(10) 0.0008(11) -0.0017(11) N2 0.0170(14) 0.0257(16) 0.0156(13) -0.0002(11) -0.0002(11) -0.0020(11) N3 0.0157(14) 0.0221(15) 0.0145(13) -0.0005(11) -0.0003(10) -0.0020(11) N4 0.0169(14) 0.0265(16) 0.0140(13) -0.0011(11) 0.0012(11) -0.0037(12) N5 0.0136(14) 0.0239(16) 0.0172(13) -0.0012(11) 0.0021(11) -0.0018(11) N6 0.0137(14) 0.0219(15) 0.0174(13) 0.0025(11) 0.0023(11) -0.0004(11) N7 0.0135(14) 0.0221(15) 0.0146(13) -0.0007(11) 0.0014(11) -0.0020(11) N8 0.0131(14) 0.0342(18) 0.0162(14) 0.0014(12) 0.0006(11) -0.0014(12) N9 0.0138(14) 0.0255(16) 0.0143(13) 0.0010(11) 0.0017(10) 0.0006(11) N10 0.0163(14) 0.0211(15) 0.0136(13) -0.0008(10) 0.0033(11) -0.0014(11) N11 0.0145(14) 0.0223(15) 0.0154(13) -0.0013(11) 0.0031(10) -0.0036(11) N12 0.0141(14) 0.0315(17) 0.0135(13) 0.0016(11) 0.0000(11) -0.0021(11) N13 0.035(2) 0.043(2) 0.0234(16) 0.0009(14) 0.0024(14) -0.0070(16) Se1 0.01427(18) 0.0285(2) 0.01321(17) -0.00109(13) 0.00080(13) -0.00552(13) Se2 0.01493(18) 0.0283(2) 0.01284(17) 0.00172(13) 0.00004(13) -0.00567(13) Se3 0.01316(18) 0.0352(2) 0.01224(17) 0.00150(13) 0.00033(13) -0.00567(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 C1 N1 1.322(4) . ? C1 N3 1.334(5) . ? C1 Se1 1.927(3) . ? C2 N4 1.341(4) . ? C2 N2 1.363(5) . ? C2 N1 1.369(4) . ? C3 N2 1.332(4) . ? C3 N3 1.341(4) . ? C3 Se2 1.925(4) . ? C4 N4 1.466(4) . ? C4 C5 1.521(5) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 N4 1.482(4) . ? C6 C7 1.508(6) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N5 1.327(5) . ? C8 N7 1.348(4) . ? C8 Se2 1.934(3) . ? C9 N8 1.351(5) . ? C9 N5 1.355(4) . ? C9 N6 1.371(4) . ? C10 N6 1.324(5) . ? C10 N7 1.340(4) . ? C10 Se3 1.935(3) . ? C11 N8 1.475(4) . ? C11 C12 1.512(6) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N8 1.472(4) . ? C13 C14 1.517(6) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N9 1.329(4) . ? C15 N11 1.331(4) . ? C15 Se3 1.935(4) . ? C16 N12 1.348(4) . ? C16 N10 1.366(4) . ? C16 N9 1.367(4) . ? C17 N10 1.330(4) . ? C17 N11 1.340(5) . ? C17 Se1 1.914(3) . ? C18 N12 1.475(4) . ? C18 C19 1.523(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N12 1.475(4) . ? C20 C21 1.513(5) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.485(6) . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 0.9800 . ? C23 N13 1.108(5) . ? 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 N3 128.6(3) . . ? N1 C1 Se1 109.4(2) . . ? N3 C1 Se1 121.7(2) . . ? N4 C2 N2 119.4(3) . . ? N4 C2 N1 117.1(3) . . ? N2 C2 N1 123.5(3) . . ? N2 C3 N3 128.0(3) . . ? N2 C3 Se2 111.1(2) . . ? N3 C3 Se2 120.9(2) . . ? N4 C4 C5 111.3(3) . . ? N4 C4 H4A 109.4 . . ? C5 C4 H4A 109.4 . . ? N4 C4 H4B 109.4 . . ? C5 C4 H4B 109.4 . . ? H4A C4 H4B 108.0 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C6 C7 112.5(3) . . ? N4 C6 H6A 109.1 . . ? C7 C6 H6A 109.1 . . ? N4 C6 H6B 109.1 . . ? C7 C6 H6B 109.1 . . ? H6A C6 H6B 107.8 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N5 C8 N7 128.6(3) . . ? N5 C8 Se2 109.9(2) . . ? N7 C8 Se2 121.5(2) . . ? N8 C9 N5 117.7(3) . . ? N8 C9 N6 118.1(3) . . ? N5 C9 N6 124.1(3) . . ? N6 C10 N7 128.4(3) . . ? N6 C10 Se3 109.9(2) . . ? N7 C10 Se3 121.7(3) . . ? N8 C11 C12 112.9(3) . . ? N8 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N8 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? 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 . . ? N8 C13 C14 111.7(3) . . ? N8 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? N8 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N9 C15 N11 128.7(3) . . ? N9 C15 Se3 110.5(2) . . ? N11 C15 Se3 120.8(2) . . ? N12 C16 N10 117.3(3) . . ? N12 C16 N9 119.1(3) . . ? N10 C16 N9 123.7(3) . . ? N10 C17 N11 128.6(3) . . ? N10 C17 Se1 109.0(2) . . ? N11 C17 Se1 122.4(2) . . ? N12 C18 C19 111.8(3) . . ? N12 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? N12 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N12 C20 C21 113.2(3) . . ? N12 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? N12 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C23 C22 H22A 109.5 . . ? C23 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C23 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? N13 C23 C22 178.0(4) . . ? C1 N1 C2 113.9(3) . . ? C3 N2 C2 113.9(3) . . ? C1 N3 C3 111.6(3) . . ? C2 N4 C4 121.1(3) . . ? C2 N4 C6 121.4(3) . . ? C4 N4 C6 117.4(3) . . ? C8 N5 C9 113.5(3) . . ? C10 N6 C9 113.7(3) . . ? C10 N7 C8 111.1(3) . . ? C9 N8 C13 121.8(3) . . ? C9 N8 C11 120.3(3) . . ? C13 N8 C11 117.8(3) . . ? C15 N9 C16 113.7(3) . . ? C17 N10 C16 113.5(3) . . ? C15 N11 C17 111.3(3) . . ? C16 N12 C20 121.4(3) . . ? C16 N12 C18 121.2(3) . . ? C20 N12 C18 117.4(3) . . ? C17 Se1 C1 106.76(15) . . ? C3 Se2 C8 105.69(14) . . ? C10 Se3 C15 107.80(15) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 70.36 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 1.501 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.124 # Attachment '- 3c.cif' #TrackingRef '- 3c.cif' data_wim142 _database_code_depnum_ccdc_archive 'CCDC 808718' #TrackingRef '- 3c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H30 Br2 Cu N12 Se3, C2 H3 N' _chemical_formula_sum 'C23 H33 Br2 Cu N13 Se3' _chemical_formula_weight 951.85 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.0691(15) _cell_length_b 24.187(3) _cell_length_c 12.665(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.014(7) _cell_angle_gamma 90.00 _cell_volume 3242.4(8) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description rod _exptl_crystal_colour yellow-green _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.950 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1852 _exptl_absorpt_coefficient_mu 8.007 _exptl_absorpt_correction_type refdelf _exptl_absorpt_correction_T_min 0.0672 _exptl_absorpt_correction_T_max 0.1055 _exptl_absorpt_process_details 'WinGX v1.70.01' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed G\"obel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27249 _diffrn_reflns_av_R_equivalents 0.0916 _diffrn_reflns_av_sigmaI/netI 0.0614 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.65 _diffrn_reflns_theta_max 66.59 _reflns_number_total 5637 _reflns_number_gt 4963 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material Platon _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^)+(0.0163P)^2^+151.2514P] 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 5637 _refine_ls_number_parameters 386 _refine_ls_number_restraints 210 _refine_ls_R_factor_all 0.0950 _refine_ls_R_factor_gt 0.0850 _refine_ls_wR_factor_ref 0.1855 _refine_ls_wR_factor_gt 0.1803 _refine_ls_goodness_of_fit_ref 1.045 _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 0.6915(8) 0.4246(4) 0.4148(7) 0.0146(17) Uani 1 1 d U . . C2 C 0.5883(8) 0.3667(4) 0.2766(7) 0.0151(17) Uani 1 1 d U . . C3 C 0.5298(8) 0.3745(4) 0.4326(7) 0.0135(17) Uani 1 1 d U . . C4 C 0.6597(8) 0.3616(4) 0.1142(8) 0.0176(18) Uani 1 1 d U . . H4A H 0.6715 0.3303 0.0677 0.021 Uiso 1 1 calc R . . H4B H 0.7436 0.3713 0.1649 0.021 Uiso 1 1 calc R . . C5 C 0.6085(9) 0.4110(4) 0.0401(8) 0.023(2) Uani 1 1 d U . . H5A H 0.5323 0.4000 -0.0181 0.035 Uiso 1 1 calc R . . H5B H 0.6725 0.4240 0.0064 0.035 Uiso 1 1 calc R . . H5C H 0.5876 0.4408 0.0842 0.035 Uiso 1 1 calc R . . C6 C 0.4806(9) 0.3014(4) 0.1357(8) 0.0203(19) Uani 1 1 d U . . H6A H 0.4639 0.2813 0.1979 0.024 Uiso 1 1 calc R . . H6B H 0.5141 0.2745 0.0924 0.024 Uiso 1 1 calc R . . C7 C 0.3575(10) 0.3246(5) 0.0628(9) 0.031(3) Uani 1 1 d U . . H7A H 0.3158 0.3459 0.1080 0.047 Uiso 1 1 calc R . . H7B H 0.3024 0.2942 0.0267 0.047 Uiso 1 1 calc R . . H7C H 0.3744 0.3487 0.0067 0.047 Uiso 1 1 calc R . . C8 C 0.4173(8) 0.3966(4) 0.6216(7) 0.0140(17) Uani 1 1 d U . . C9 C 0.3113(8) 0.4255(3) 0.7382(7) 0.0119(16) Uani 1 1 d U . . C10 C 0.4987(8) 0.4616(4) 0.7436(7) 0.0135(17) Uani 1 1 d U . . C11 C 0.1055(8) 0.3853(4) 0.7237(8) 0.0181(19) Uani 1 1 d U . . H11A H 0.0942 0.3851 0.6433 0.022 Uiso 1 1 calc R . . H11B H 0.0272 0.4002 0.7356 0.022 Uiso 1 1 calc R . . C12 C 0.1248(10) 0.3268(4) 0.7665(10) 0.031(3) Uani 1 1 d U . . H12A H 0.2063 0.3130 0.7618 0.046 Uiso 1 1 calc R . . H12B H 0.0568 0.3033 0.7218 0.046 Uiso 1 1 calc R . . H12C H 0.1237 0.3260 0.8435 0.046 Uiso 1 1 calc R . . C13 C 0.2029(8) 0.4535(4) 0.8726(7) 0.0150(18) Uani 1 1 d U . . H13A H 0.2892 0.4638 0.9174 0.018 Uiso 1 1 calc R . . H13B H 0.1653 0.4301 0.9189 0.018 Uiso 1 1 calc R . . C14 C 0.1254(10) 0.5048(4) 0.8408(8) 0.026(2) Uani 1 1 d U . . H14A H 0.1649 0.5292 0.7987 0.039 Uiso 1 1 calc R . . H14B H 0.1203 0.5240 0.9076 0.039 Uiso 1 1 calc R . . H14C H 0.0401 0.4950 0.7954 0.039 Uiso 1 1 calc R . . C15 C 0.7220(8) 0.5318(4) 0.7174(7) 0.0132(17) Uani 1 1 d U . . C16 C 0.8609(8) 0.5911(4) 0.6844(7) 0.0151(16) Uani 1 1 d U . . C17 C 0.8076(8) 0.5145(4) 0.5820(7) 0.0144(17) Uani 1 1 d U . . C18 C 0.9066(9) 0.6751(4) 0.7944(8) 0.0201(19) Uani 1 1 d U . . H18A H 0.8158 0.6757 0.7896 0.024 Uiso 1 1 calc R . . H18B H 0.9320 0.7131 0.7812 0.024 Uiso 1 1 calc R . . C19 C 0.9824(10) 0.6567(5) 0.9091(9) 0.030(2) Uani 1 1 d U . . H19A H 0.9537 0.6200 0.9242 0.045 Uiso 1 1 calc R . . H19B H 0.9702 0.6831 0.9637 0.045 Uiso 1 1 calc R . . H19C H 1.0722 0.6550 0.9135 0.045 Uiso 1 1 calc R . . C20 C 1.0134(9) 0.6564(4) 0.6466(8) 0.0205(19) Uani 1 1 d U . . H20A H 1.0460 0.6236 0.6169 0.025 Uiso 1 1 calc R . . H20B H 1.0862 0.6758 0.6974 0.025 Uiso 1 1 calc R . . C21 C 0.9483(10) 0.6950(4) 0.5514(8) 0.024(2) Uani 1 1 d U . . H21A H 0.8818 0.6747 0.4969 0.036 Uiso 1 1 calc R . . H21B H 1.0104 0.7088 0.5163 0.036 Uiso 1 1 calc R . . H21C H 0.9108 0.7262 0.5798 0.036 Uiso 1 1 calc R . . C22 C 0.5833(14) 0.2048(5) 0.3470(9) 0.040(3) Uani 1 1 d U . . C23 C 0.7080(12) 0.2307(5) 0.3651(9) 0.038(3) Uani 1 1 d U . . H23A H 0.7730 0.2019 0.3780 0.057 Uiso 1 1 calc R . . H23B H 0.7253 0.2551 0.4295 0.057 Uiso 1 1 calc R . . H23C H 0.7086 0.2523 0.2998 0.057 Uiso 1 1 calc R . . N1 N 0.6222(6) 0.4113(3) 0.4813(6) 0.0129(14) Uani 1 1 d U . . N2 N 0.6836(7) 0.4052(3) 0.3164(6) 0.0144(15) Uani 1 1 d U . . N3 N 0.5089(7) 0.3521(3) 0.3359(6) 0.0145(15) Uani 1 1 d U . . N4 N 0.5768(7) 0.3437(3) 0.1800(6) 0.0199(16) Uani 1 1 d U . . N5 N 0.5203(7) 0.4280(3) 0.6655(6) 0.0169(15) Uani 1 1 d U . . N6 N 0.3123(6) 0.3924(3) 0.6498(6) 0.0138(15) Uani 1 1 d U . . N7 N 0.4031(7) 0.4623(3) 0.7853(6) 0.0146(15) Uani 1 1 d U . . N8 N 0.2108(7) 0.4216(3) 0.7774(6) 0.0141(14) Uani 1 1 d U . . N9 N 0.7291(7) 0.4958(3) 0.6396(6) 0.0135(15) Uani 1 1 d U . . N10 N 0.7807(7) 0.5784(3) 0.7443(6) 0.0163(15) Uani 1 1 d U . . N11 N 0.8741(6) 0.5609(3) 0.5998(6) 0.0128(14) Uani 1 1 d U . . N12 N 0.9259(7) 0.6382(3) 0.7086(6) 0.0176(15) Uani 1 1 d U . . N13 N 0.4963(12) 0.1841(5) 0.3334(10) 0.054(3) Uani 1 1 d U . . Cu1 Cu 0.70644(12) 0.40879(6) 0.64793(11) 0.0173(3) Uani 1 1 d . . . Se1 Se 0.83281(9) 0.47406(4) 0.46124(8) 0.0163(2) Uani 1 1 d . . . Se2 Se 0.40913(8) 0.34749(4) 0.50101(8) 0.0151(2) Uani 1 1 d . . . Se3 Se 0.61274(9) 0.52057(4) 0.80824(8) 0.0155(2) Uani 1 1 d . . . Br1 Br 0.82997(9) 0.40871(4) 0.83736(8) 0.0231(2) Uani 1 1 d . . . Br2 Br 0.77175(11) 0.31596(5) 0.61778(9) 0.0310(3) 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 0.014(3) 0.013(3) 0.012(3) 0.000(3) -0.004(3) 0.000(3) C2 0.013(3) 0.013(3) 0.017(3) 0.000(3) 0.000(3) 0.002(3) C3 0.011(3) 0.013(3) 0.016(3) 0.000(3) 0.004(3) 0.003(3) C4 0.015(4) 0.020(4) 0.021(4) -0.005(3) 0.011(3) -0.002(3) C5 0.025(5) 0.029(5) 0.016(4) 0.002(4) 0.006(4) 0.000(4) C6 0.021(4) 0.020(4) 0.020(4) -0.001(3) 0.007(3) -0.005(3) C7 0.021(5) 0.037(6) 0.027(5) 0.008(5) -0.008(4) -0.003(4) C8 0.017(3) 0.014(3) 0.011(3) 0.004(3) 0.004(3) -0.004(3) C9 0.013(3) 0.011(3) 0.010(3) -0.001(3) 0.001(3) 0.000(3) C10 0.014(3) 0.016(3) 0.013(3) -0.001(3) 0.007(3) 0.002(3) C11 0.004(3) 0.024(4) 0.023(4) -0.001(3) 0.000(3) 0.003(3) C12 0.016(4) 0.021(5) 0.047(6) 0.010(4) -0.002(4) -0.002(4) C13 0.010(3) 0.018(4) 0.018(4) 0.001(3) 0.006(3) -0.001(3) C14 0.030(5) 0.025(5) 0.025(5) -0.009(4) 0.013(4) -0.003(4) C15 0.013(3) 0.012(3) 0.014(3) 0.001(3) 0.003(3) 0.002(3) C16 0.016(3) 0.014(3) 0.014(3) 0.007(3) 0.004(3) -0.003(3) C17 0.013(3) 0.014(3) 0.018(3) -0.003(3) 0.009(3) 0.002(3) C18 0.024(4) 0.013(4) 0.029(4) -0.002(3) 0.018(3) 0.002(3) C19 0.030(5) 0.026(5) 0.036(5) -0.007(4) 0.014(4) 0.006(4) C20 0.019(4) 0.019(4) 0.025(4) 0.000(3) 0.008(3) -0.005(3) C21 0.037(5) 0.019(5) 0.016(4) 0.004(4) 0.008(4) -0.001(4) C22 0.077(7) 0.026(5) 0.015(5) 0.002(4) 0.010(5) -0.009(5) C23 0.068(7) 0.028(6) 0.018(5) 0.002(4) 0.013(5) 0.009(5) N1 0.011(3) 0.012(3) 0.018(3) -0.002(2) 0.007(2) -0.007(3) N2 0.016(3) 0.013(3) 0.013(3) -0.006(3) 0.003(2) 0.004(3) N3 0.015(3) 0.012(3) 0.017(3) 0.003(3) 0.005(3) 0.000(3) N4 0.017(3) 0.020(3) 0.018(3) -0.002(3) -0.001(3) 0.000(3) N5 0.015(3) 0.020(3) 0.017(3) -0.004(3) 0.005(3) -0.006(3) N6 0.009(3) 0.018(3) 0.015(3) 0.003(3) 0.003(2) 0.000(3) N7 0.015(3) 0.015(3) 0.014(3) -0.001(3) 0.004(3) 0.000(3) N8 0.009(3) 0.018(3) 0.016(3) 0.002(3) 0.004(2) 0.002(2) N9 0.018(3) 0.011(3) 0.012(3) -0.003(2) 0.006(2) -0.008(3) N10 0.019(3) 0.015(3) 0.015(3) -0.001(3) 0.004(3) 0.007(3) N11 0.009(3) 0.016(3) 0.017(3) -0.001(3) 0.008(2) 0.002(3) N12 0.021(3) 0.014(3) 0.020(3) 0.000(3) 0.009(3) -0.003(3) N13 0.067(7) 0.044(6) 0.043(6) 0.013(5) 0.003(5) -0.018(6) Cu1 0.0165(6) 0.0178(7) 0.0175(6) -0.0005(5) 0.0049(5) -0.0004(5) Se1 0.0158(4) 0.0183(5) 0.0165(4) -0.0031(4) 0.0072(3) -0.0044(4) Se2 0.0133(4) 0.0148(4) 0.0178(5) -0.0029(4) 0.0056(3) -0.0032(4) Se3 0.0167(4) 0.0149(4) 0.0164(5) -0.0037(4) 0.0070(3) -0.0024(4) Br1 0.0217(5) 0.0255(5) 0.0222(5) 0.0027(4) 0.0067(4) 0.0038(4) Br2 0.0343(6) 0.0251(5) 0.0281(6) -0.0028(4) 0.0005(4) 0.0092(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 C1 N2 1.310(12) . ? C1 N1 1.334(12) . ? C1 Se1 1.920(9) . ? C2 N4 1.316(12) . ? C2 N3 1.359(12) . ? C2 N2 1.388(11) . ? C3 N3 1.295(12) . ? C3 N1 1.360(11) . ? C3 Se2 1.908(9) . ? C4 N4 1.474(12) . ? C4 C5 1.523(13) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 N4 1.464(12) . ? C6 C7 1.512(13) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 N6 1.315(12) . ? C8 N5 1.347(11) . ? C8 Se2 1.915(9) . ? C9 N8 1.347(12) . ? C9 N7 1.352(11) . ? C9 N6 1.378(11) . ? C10 N7 1.313(12) . ? C10 N5 1.354(12) . ? C10 Se3 1.922(9) . ? C11 N8 1.459(11) . ? C11 C12 1.508(14) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? C13 N8 1.454(12) . ? C13 C14 1.497(13) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 N10 1.296(12) . ? C15 N9 1.334(11) . ? C15 Se3 1.917(9) . ? C16 N12 1.334(12) . ? C16 N11 1.340(12) . ? C16 N10 1.361(12) . ? C17 N11 1.323(11) . ? C17 N9 1.365(12) . ? C17 Se1 1.904(9) . ? C18 N12 1.468(12) . ? C18 C19 1.517(14) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? C20 N12 1.481(12) . ? C20 C21 1.528(13) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 N13 1.053(17) . ? C22 C23 1.471(19) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N1 Cu1 2.044(7) . ? N5 Cu1 2.186(8) . ? N9 Cu1 2.126(7) . ? Cu1 Br1 2.3887(17) . ? Cu1 Br2 2.4230(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 N2 C1 N1 128.6(8) . . ? N2 C1 Se1 109.6(7) . . ? N1 C1 Se1 121.6(6) . . ? N4 C2 N3 120.2(8) . . ? N4 C2 N2 118.6(8) . . ? N3 C2 N2 121.2(8) . . ? N3 C3 N1 127.2(8) . . ? N3 C3 Se2 109.4(6) . . ? N1 C3 Se2 123.4(7) . . ? N4 C4 C5 113.5(8) . . ? N4 C4 H4A 108.9 . . ? C5 C4 H4A 108.9 . . ? N4 C4 H4B 108.9 . . ? C5 C4 H4B 108.9 . . ? H4A C4 H4B 107.7 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C6 C7 113.6(8) . . ? N4 C6 H6A 108.8 . . ? C7 C6 H6A 108.8 . . ? N4 C6 H6B 108.8 . . ? C7 C6 H6B 108.8 . . ? H6A C6 H6B 107.7 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N6 C8 N5 129.7(9) . . ? N6 C8 Se2 109.3(6) . . ? N5 C8 Se2 121.0(7) . . ? N8 C9 N7 118.5(8) . . ? N8 C9 N6 117.6(7) . . ? N7 C9 N6 123.8(8) . . ? N7 C10 N5 129.5(8) . . ? N7 C10 Se3 109.0(6) . . ? N5 C10 Se3 121.5(6) . . ? N8 C11 C12 112.8(7) . . ? N8 C11 H11A 109.0 . . ? C12 C11 H11A 109.0 . . ? N8 C11 H11B 109.0 . . ? C12 C11 H11B 109.0 . . ? H11A C11 H11B 107.8 . . ? 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 . . ? N8 C13 C14 112.7(7) . . ? N8 C13 H13A 109.1 . . ? C14 C13 H13A 109.1 . . ? N8 C13 H13B 109.1 . . ? C14 C13 H13B 109.1 . . ? H13A C13 H13B 107.8 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N10 C15 N9 128.9(9) . . ? N10 C15 Se3 108.8(6) . . ? N9 C15 Se3 122.3(6) . . ? N12 C16 N11 118.2(8) . . ? N12 C16 N10 117.5(8) . . ? N11 C16 N10 124.3(8) . . ? N11 C17 N9 126.7(8) . . ? N11 C17 Se1 111.6(6) . . ? N9 C17 Se1 121.6(6) . . ? N12 C18 C19 111.8(8) . . ? N12 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? N12 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? N12 C20 C21 111.7(8) . . ? N12 C20 H20A 109.3 . . ? C21 C20 H20A 109.3 . . ? N12 C20 H20B 109.3 . . ? C21 C20 H20B 109.3 . . ? H20A C20 H20B 108.0 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N13 C22 C23 176.8(15) . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C1 N1 C3 111.5(7) . . ? C1 N1 Cu1 119.1(5) . . ? C3 N1 Cu1 120.3(6) . . ? C1 N2 C2 114.7(8) . . ? C3 N3 C2 116.7(8) . . ? C2 N4 C6 120.9(8) . . ? C2 N4 C4 119.7(8) . . ? C6 N4 C4 119.5(8) . . ? C8 N5 C10 109.3(8) . . ? C8 N5 Cu1 123.2(6) . . ? C10 N5 Cu1 125.1(6) . . ? C8 N6 C9 113.2(7) . . ? C10 N7 C9 113.8(8) . . ? C9 N8 C13 121.7(7) . . ? C9 N8 C11 120.2(8) . . ? C13 N8 C11 118.1(7) . . ? C15 N9 C17 111.3(7) . . ? C15 N9 Cu1 125.2(6) . . ? C17 N9 Cu1 117.2(6) . . ? C15 N10 C16 114.2(8) . . ? C17 N11 C16 114.5(8) . . ? C16 N12 C18 120.2(8) . . ? C16 N12 C20 121.6(8) . . ? C18 N12 C20 118.1(7) . . ? N1 Cu1 N9 86.8(3) . . ? N1 Cu1 N5 86.5(3) . . ? N9 Cu1 N5 85.6(3) . . ? N1 Cu1 Br1 172.5(2) . . ? N9 Cu1 Br1 90.5(2) . . ? N5 Cu1 Br1 100.2(2) . . ? N1 Cu1 Br2 86.1(2) . . ? N9 Cu1 Br2 149.8(2) . . ? N5 Cu1 Br2 123.1(2) . . ? Br1 Cu1 Br2 92.75(6) . . ? C17 Se1 C1 105.6(4) . . ? C3 Se2 C8 105.9(4) . . ? C15 Se3 C10 107.5(4) . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 2.315 _refine_diff_density_min -1.217 _refine_diff_density_rms 0.234 # Attachment '- 4c.cif' data_wim143 _database_code_depnum_ccdc_archive 'CCDC 816095' #TrackingRef '- 4c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H30 Br Cu N12 Se3' _chemical_formula_sum 'C21 H30 Br Cu N12 Se3' _chemical_formula_weight 830.90 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting rhombohedral _symmetry_space_group_name_H-M 'R -3 c' _symmetry_space_group_name_Hall '-R 3 2"c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, -z+1/2' 'x-y, -y, -z+1/2' '-x, -x+y, -z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'y+2/3, x+1/3, -z+5/6' 'x-y+2/3, -y+1/3, -z+5/6' '-x+2/3, -x+y+1/3, -z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' 'y+1/3, x+2/3, -z+7/6' 'x-y+1/3, -y+2/3, -z+7/6' '-x+1/3, -x+y+2/3, -z+7/6' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-y, -x, z-1/2' '-x+y, y, z-1/2' 'x, x-y, z-1/2' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-y+2/3, -x+1/3, z-1/6' '-x+y+2/3, y+1/3, z-1/6' 'x+2/3, x-y+1/3, z-1/6' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' '-y+1/3, -x+2/3, z+1/6' '-x+y+1/3, y+2/3, z+1/6' 'x+1/3, x-y+2/3, z+1/6' _cell_length_a 16.8242(2) _cell_length_b 16.8242(2) _cell_length_c 72.520(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 17777.0(6) _cell_formula_units_Z 24 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description plate _exptl_crystal_colour yellow _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.863 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 9744 _exptl_absorpt_coefficient_mu 7.122 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.350 _exptl_absorpt_correction_T_max 0.700 _exptl_absorpt_process_details 'Bruker SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator 'crossed G\"obel mirrors' _diffrn_measurement_device_type 'SMART 6000' _diffrn_measurement_method '\w and \f scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 48298 _diffrn_reflns_av_R_equivalents 0.0735 _diffrn_reflns_av_sigmaI/netI 0.0271 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -89 _diffrn_reflns_limit_l_max 84 _diffrn_reflns_theta_min 3.27 _diffrn_reflns_theta_max 71.38 _reflns_number_total 3837 _reflns_number_gt 3309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material Platon _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^)+(0.0690P)^2^+174.3209P] 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 3837 _refine_ls_number_parameters 233 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0636 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1447 _refine_ls_wR_factor_gt 0.1384 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.069 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4997(3) 0.1830(4) 0.10895(6) 0.0378(10) Uani 1 1 d . . . C2 C 0.3713(4) 0.1849(4) 0.10170(7) 0.0418(11) Uani 1 1 d . . . C3 C 0.6844(3) 0.1847(4) 0.10887(7) 0.0378(10) Uani 1 1 d . . . C4 C 0.2299(4) 0.0418(4) 0.09376(9) 0.0534(14) Uani 1 1 d . . . H4A H 0.1672 0.0198 0.0977 0.064 Uiso 1 1 calc R . . H4B H 0.2555 0.0132 0.1015 0.064 Uiso 1 1 calc R . . C5 C 0.2299(5) 0.0141(5) 0.07402(10) 0.0628(16) Uani 1 1 d . . . H5A H 0.2083 0.0454 0.0662 0.094 Uiso 1 1 calc R . . H5B H 0.1902 -0.0510 0.0728 0.094 Uiso 1 1 calc R . . H5C H 0.2911 0.0302 0.0705 0.094 Uiso 1 1 calc R . . C6 C 0.2402(5) 0.1962(5) 0.09061(10) 0.0628(17) Uani 1 1 d . . . H6A H 0.1919 0.1613 0.0818 0.075 Uiso 1 1 calc R . . H6B H 0.2856 0.2524 0.0847 0.075 Uiso 1 1 calc R . . C7 C 0.2008(6) 0.2193(7) 0.10675(13) 0.093(3) Uani 1 1 d . . . H7A H 0.1569 0.1638 0.1128 0.139 Uiso 1 1 calc R . . H7B H 0.1710 0.2521 0.1026 0.139 Uiso 1 1 calc R . . H7C H 0.2490 0.2569 0.1152 0.139 Uiso 1 1 calc R . . C8 C 0.9360(4) 1.1163(4) 0.02626(7) 0.0416(11) Uani 1 1 d . . . C9 C 0.7333(4) 0.7538(4) 0.01909(8) 0.0491(13) Uani 1 1 d . . . C10 C 0.8166(4) 0.9042(4) 0.02628(7) 0.0397(11) Uani 1 1 d . . . C11 C 0.6447(5) 0.5894(4) 0.01245(10) 0.0638(17) Uani 1 1 d . . . H11A H 0.5861 0.5440 0.0176 0.077 Uiso 1 1 calc R . . H11B H 0.6927 0.5872 0.0195 0.077 Uiso 1 1 calc R . . C12 C 0.6497(6) 0.5651(5) -0.00728(11) 0.076(2) Uani 1 1 d . . . H12A H 0.6054 0.5716 -0.0145 0.114 Uiso 1 1 calc R . . H12B H 0.6369 0.5028 -0.0080 0.114 Uiso 1 1 calc R . . H12C H 0.7101 0.6054 -0.0120 0.114 Uiso 1 1 calc R . . C13 C 0.5734(5) 0.6899(5) 0.00982(11) 0.0679(18) Uani 1 1 d . . . H13A H 0.5934 0.7492 0.0042 0.082 Uiso 1 1 calc R . . H13B H 0.5356 0.6428 0.0010 0.082 Uiso 1 1 calc R . . C14 C 0.5191(6) 0.6806(7) 0.02615(12) 0.093(3) Uani 1 1 d . . . H14A H 0.4964 0.6206 0.0314 0.140 Uiso 1 1 calc R . . H14B H 0.4684 0.6886 0.0228 0.140 Uiso 1 1 calc R . . H14C H 0.5567 0.7263 0.0350 0.140 Uiso 1 1 calc R . . N1 N 0.4128(3) 0.1350(3) 0.10426(6) 0.0422(10) Uani 1 1 d . . . N2 N 0.7221(3) 0.1363(3) 0.10382(6) 0.0437(10) Uani 1 1 d . . . N3 N 0.5489(3) 0.2734(3) 0.11212(6) 0.0414(10) Uani 1 1 d . . . N4 N 0.2837(3) 0.1421(3) 0.09619(7) 0.0504(11) Uani 1 1 d . . . N5 N 0.9358(3) 1.1914(3) 0.02125(6) 0.0456(10) Uani 1 1 d . . . N6 N 0.7366(3) 0.8357(3) 0.02132(7) 0.0464(10) Uani 1 1 d . . . N7 N 1.0084(3) 1.1062(3) 0.02973(6) 0.0413(9) Uani 1 1 d . . . N8 N 0.6549(3) 0.6816(4) 0.01438(8) 0.0556(12) Uani 1 1 d . . . Cu1 Cu 0.6667 0.3333 0.128202(17) 0.0417(3) Uani 1 3 d S . . Cu2 Cu 1.0000 1.0000 0.045686(18) 0.0435(3) Uani 1 3 d S . . Se1 Se 0.55421(4) 0.10669(4) 0.111693(9) 0.04596(19) Uani 1 1 d . . . Se2 Se 0.81186(4) 1.01566(4) 0.028992(10) 0.0503(2) Uani 1 1 d . . . Br1 Br 0.6667 0.3333 0.159305(19) 0.1222(8) Uani 1 3 d S . . Br2 Br 1.0000 1.0000 0.077360(13) 0.0451(3) Uani 1 3 d S . . 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 0.039(3) 0.043(3) 0.029(2) 0.0018(19) 0.0027(19) 0.019(2) C2 0.035(3) 0.045(3) 0.040(2) 0.000(2) -0.001(2) 0.016(2) C3 0.038(3) 0.043(3) 0.033(2) 0.002(2) -0.0005(19) 0.021(2) C4 0.034(3) 0.044(3) 0.071(4) 0.003(3) -0.004(3) 0.011(2) C5 0.054(4) 0.055(4) 0.074(4) -0.003(3) 0.000(3) 0.024(3) C6 0.049(3) 0.059(4) 0.078(4) -0.001(3) -0.010(3) 0.025(3) C7 0.081(6) 0.116(8) 0.102(7) -0.011(6) 0.001(5) 0.065(6) C8 0.049(3) 0.045(3) 0.033(2) -0.002(2) 0.001(2) 0.025(2) C9 0.048(3) 0.043(3) 0.049(3) 0.002(2) -0.003(2) 0.017(3) C10 0.042(3) 0.040(3) 0.035(2) 0.000(2) 0.001(2) 0.019(2) C11 0.047(3) 0.043(3) 0.082(5) 0.004(3) -0.006(3) 0.007(3) C12 0.076(5) 0.066(4) 0.083(5) -0.012(4) -0.001(4) 0.032(4) C13 0.048(3) 0.055(4) 0.091(5) -0.015(4) -0.011(3) 0.018(3) C14 0.084(6) 0.107(7) 0.082(6) -0.012(5) -0.010(5) 0.042(5) N1 0.036(2) 0.041(2) 0.045(2) 0.0025(18) 0.0018(18) 0.0153(19) N2 0.044(2) 0.041(2) 0.048(2) -0.0015(19) 0.0005(19) 0.023(2) N3 0.038(2) 0.041(2) 0.043(2) -0.0033(18) -0.0057(18) 0.0176(19) N4 0.036(2) 0.045(3) 0.063(3) -0.001(2) -0.005(2) 0.015(2) N5 0.053(3) 0.044(2) 0.043(2) 0.0021(19) 0.005(2) 0.027(2) N6 0.042(2) 0.043(2) 0.050(3) 0.000(2) -0.005(2) 0.018(2) N7 0.041(2) 0.039(2) 0.042(2) 0.0049(18) 0.0005(18) 0.0191(19) N8 0.046(3) 0.050(3) 0.064(3) -0.006(2) -0.009(2) 0.019(2) Cu1 0.0470(5) 0.0470(5) 0.0312(6) 0.000 0.000 0.0235(2) Cu2 0.0473(5) 0.0473(5) 0.0358(7) 0.000 0.000 0.0237(2) Se1 0.0397(3) 0.0369(3) 0.0603(4) 0.0003(2) 0.0015(2) 0.0184(2) Se2 0.0406(3) 0.0448(3) 0.0669(4) -0.0026(3) -0.0025(3) 0.0224(3) Br1 0.1663(13) 0.1663(13) 0.0340(6) 0.000 0.000 0.0832(7) Br2 0.0483(4) 0.0483(4) 0.0386(5) 0.000 0.000 0.02415(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.313(7) . ? C1 N3 1.340(7) . ? C1 Se1 1.925(5) . ? C2 N4 1.338(7) . ? C2 N1 1.347(7) . ? C3 N2 1.309(7) . ? C3 Se1 1.920(5) . ? C4 N4 1.473(7) . ? C4 C5 1.506(9) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N4 1.480(8) . ? C6 C7 1.490(11) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 N5 1.315(7) . ? C8 N7 1.336(7) . ? C8 Se2 1.932(6) . ? C9 N8 1.316(8) . ? C9 N6 1.361(8) . ? C10 N6 1.311(7) . ? C10 Se2 1.926(5) . ? C11 N8 1.480(8) . ? C11 C12 1.502(10) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.455(12) . ? C13 N8 1.483(9) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? N3 Cu1 2.075(4) . ? N7 Cu2 2.073(4) . ? Cu1 Br1 2.2555(19) . ? Cu2 Br2 2.2969(16) . ? 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 N3 127.5(5) . . ? N1 C1 Se1 111.8(4) . . ? N3 C1 Se1 120.7(4) . . ? N4 C2 N1 118.7(5) . . ? N2 C3 Se1 110.3(4) . . ? N4 C4 C5 111.9(5) . . ? N4 C4 H4A 109.2 . . ? C5 C4 H4A 109.2 . . ? N4 C4 H4B 109.2 . . ? C5 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N4 C6 C7 111.6(6) . . ? N4 C6 H6A 109.3 . . ? C7 C6 H6A 109.3 . . ? N4 C6 H6B 109.3 . . ? C7 C6 H6B 109.3 . . ? H6A C6 H6B 108.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N5 C8 N7 128.0(5) . . ? N5 C8 Se2 110.4(4) . . ? N7 C8 Se2 121.6(4) . . ? N8 C9 N6 118.7(6) . . ? N6 C10 Se2 111.1(4) . . ? N8 C11 C12 112.5(6) . . ? N8 C11 H11A 109.1 . . ? C12 C11 H11A 109.1 . . ? N8 C11 H11B 109.1 . . ? C12 C11 H11B 109.1 . . ? H11A C11 H11B 107.8 . . ? 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 . . ? C14 C13 N8 111.6(7) . . ? C14 C13 H13A 109.3 . . ? N8 C13 H13A 109.3 . . ? C14 C13 H13B 109.3 . . ? N8 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C1 N1 C2 114.7(5) . . ? C1 N3 Cu1 123.0(4) . . ? C2 N4 C4 122.2(5) . . ? C2 N4 C6 120.0(5) . . ? C4 N4 C6 117.6(5) . . ? C10 N6 C9 115.3(5) . . ? C8 N7 Cu2 122.8(4) . . ? C9 N8 C11 122.0(6) . . ? C9 N8 C13 121.2(6) . . ? C11 N8 C13 116.7(5) . . ? N3 Cu1 Br1 124.20(13) . . ? N7 Cu2 Br2 123.93(13) . . ? C3 Se1 C1 107.1(2) . . ? C10 Se2 C8 106.8(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 71.38 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 1.631 _refine_diff_density_min -1.319 _refine_diff_density_rms 0.132