# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_coden_Cambridge 182 _publ_contact_author_name 'Professor Daniel L. Reger' _publ_contact_author_address ; Department of Chemistry and Biochemistry University of South Carolina Columbia, South Carolina 29208 USA ; _publ_contact_author_phone '1 803 777 2587' _publ_contact_author_fax '1 803 777 9521' _publ_contact_author_email reger@mail.chem.sc.edu _publ_requested_journal ' Chemical Communications ' loop_ _publ_author_name _publ_author_address 'Reger, Daniel L.' ; Department of Chemistry and Biochemistry University of South Carolina Columbia, South Carolina, 29208 USA ; 'Elgin, J. Derek' ; Department of Chemistry and Biochemistry University of South Carolina Columbia, South Carolina, 29208 USA ; 'Semeniuc, Radu F.' ; Department of Chemistry and Biochemistry University of South Carolina Columbia, South Carolina, 29208 USA ; 'Pellechia, Perry J.' ; Department of Chemistry and Biochemistry University of South Carolina Columbia, South Carolina, 29208 USA ; 'Smith, Mark D.' ; Department of Chemistry and Biochemistry University of South Carolina Columbia, South Carolina, 29208 USA ; _publ_section_title ; Directional Control of pi Stacked Building Blocks for Crystal Engineering: the 1,8-Naphthalimide Synthon ; data_compound_1 _database_code_depnum_ccdc_archive 'CCDC 268888' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H15 Br N5 O5 Re, C2 D6 O S' _chemical_formula_sum 'C25 H15 Br D6 N5 O6 Re S' _chemical_formula_weight 791.67 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' D D 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 '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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6135(5) _cell_length_b 10.6869(6) _cell_length_c 15.7050(10) _cell_angle_alpha 73.9250(10) _cell_angle_beta 75.0370(10) _cell_angle_gamma 83.6960(10) _cell_volume 1340.90(14) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 5467 _cell_measurement_theta_min 2.450 _cell_measurement_theta_max 26.381 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.961 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 760 _exptl_absorpt_coefficient_mu 6.149 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5837 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details 'SADABS (Bruker, 2001)' _exptl_special_details ; Crystallized from d6-dmso ; _diffrn_ambient_temperature 150(1) _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 13416 _diffrn_reflns_av_R_equivalents 0.0234 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.39 _diffrn_reflns_theta_max 26.39 _reflns_number_total 5462 _reflns_number_gt 5173 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.628 (Bruker, 2001)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _refine_special_details ; Solvent D atoms included in refinement for correct FW, d(calc). 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^)+(0.0302P)^2^+0.5399P] 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 5462 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0236 _refine_ls_R_factor_gt 0.0220 _refine_ls_wR_factor_ref 0.0559 _refine_ls_wR_factor_gt 0.0551 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.004 _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 Re1 Re 0.606100(12) 0.575103(10) 0.716210(7) 0.02157(5) Uani 1 1 d . . . Br1 Br 0.55289(4) 0.65574(3) 0.55186(2) 0.02839(8) Uani 1 1 d . . . C1 C 0.9020(3) 0.3260(3) 0.70150(19) 0.0214(6) Uani 1 1 d . . . H1 H 0.9847 0.2618 0.67895 0.026 Uiso 1 1 calc R . . C2 C 0.8942(4) 0.3028(3) 0.8037(2) 0.0250(6) Uani 1 1 d . . . H2A H 0.9768 0.3533 0.8116 0.030 Uiso 1 1 calc R . . H2B H 0.7873 0.3323 0.8352 0.030 Uiso 1 1 calc R . . C11 C 1.1026(3) 0.4810(3) 0.5919(2) 0.0268(6) Uani 1 1 d . . . H11 H 1.1893 0.4196 0.5818 0.032 Uiso 1 1 calc R . . C12 C 1.1044(4) 0.6119(3) 0.5536(2) 0.0326(7) Uani 1 1 d . . . H12 H 1.1919 0.6599 0.5122 0.039 Uiso 1 1 calc R . . C13 C 0.9522(4) 0.6606(3) 0.5876(2) 0.0285(7) Uani 1 1 d . . . H13 H 0.9178 0.7497 0.5715 0.034 Uiso 1 1 calc R . . C21 C 0.7171(3) 0.1880(3) 0.6711(2) 0.0243(6) Uani 1 1 d . . . H21 H 0.7909 0.1179 0.6606 0.029 Uiso 1 1 calc R . . C22 C 0.5564(4) 0.1947(3) 0.6741(2) 0.0287(7) Uani 1 1 d . . . H22 H 0.4963 0.1314 0.6659 0.034 Uiso 1 1 calc R . . C23 C 0.5000(3) 0.3142(3) 0.6917(2) 0.0278(7) Uani 1 1 d . . . H23 H 0.3915 0.3461 0.6969 0.033 Uiso 1 1 calc R . . C31 C 1.0825(3) 0.1185(3) 0.8313(2) 0.0254(6) Uani 1 1 d . . . C32 C 1.1147(3) -0.0189(3) 0.8763(2) 0.0243(6) Uani 1 1 d . . . C33 C 0.9836(4) -0.1010(3) 0.92219(19) 0.0251(6) Uani 1 1 d . . . C34 C 0.8235(4) -0.0520(3) 0.9284(2) 0.0267(6) Uani 1 1 d . . . C35 C 0.7881(3) 0.0866(3) 0.8888(2) 0.0262(6) Uani 1 1 d . . . C36 C 1.2700(4) -0.0672(3) 0.8729(2) 0.0322(7) Uani 1 1 d . . . H36 H 1.3572 -0.0114 0.8424 0.039 Uiso 1 1 calc R . . C37 C 1.3002(4) -0.1989(4) 0.9142(2) 0.0376(8) Uani 1 1 d . . . H37 H 1.4079 -0.2320 0.9113 0.045 Uiso 1 1 calc R . . C38 C 1.1764(5) -0.2796(3) 0.9582(2) 0.0384(8) Uani 1 1 d . . . H38 H 1.1990 -0.3684 0.9859 0.046 Uiso 1 1 calc R . . C39 C 1.0148(4) -0.2338(3) 0.9637(2) 0.0332(7) Uani 1 1 d . . . C40 C 0.8827(5) -0.3137(3) 1.0101(2) 0.0440(9) Uani 1 1 d . . . H40 H 0.9016 -0.4032 1.0380 0.053 Uiso 1 1 calc R . . C41 C 0.7284(5) -0.2646(4) 1.0156(3) 0.0501(10) Uani 1 1 d . . . H41 H 0.6410 -0.3197 1.0474 0.060 Uiso 1 1 calc R . . C42 C 0.6986(4) -0.1339(4) 0.9748(2) 0.0390(8) Uani 1 1 d . . . H42 H 0.5908 -0.1006 0.9790 0.047 Uiso 1 1 calc R . . C51 C 0.3795(4) 0.5681(3) 0.7691(2) 0.0289(7) Uani 1 1 d . . . C52 C 0.6034(4) 0.7536(3) 0.7185(2) 0.0299(7) Uani 1 1 d . . . C53 C 0.6355(4) 0.5323(3) 0.8383(2) 0.0313(7) Uani 1 1 d . . . N1 N 0.9224(3) 0.1634(2) 0.84327(16) 0.0222(5) Uani 1 1 d . . . N11 N 0.8599(3) 0.5654(2) 0.64614(17) 0.0226(5) Uani 1 1 d . . . N12 N 0.9545(3) 0.4546(2) 0.64696(16) 0.0214(5) Uani 1 1 d . . . N21 N 0.6174(3) 0.3787(2) 0.70042(17) 0.0224(5) Uani 1 1 d . . . N22 N 0.7515(3) 0.2990(2) 0.68583(16) 0.0209(5) Uani 1 1 d . . . O1 O 1.1883(2) 0.1928(2) 0.78557(17) 0.0357(5) Uani 1 1 d . . . O2 O 0.6538(2) 0.1362(2) 0.89314(16) 0.0348(5) Uani 1 1 d . . . O51 O 0.2433(3) 0.5584(2) 0.80027(18) 0.0420(6) Uani 1 1 d . . . O52 O 0.6045(3) 0.8603(2) 0.7203(2) 0.0505(7) Uani 1 1 d . . . O53 O 0.6458(3) 0.5150(3) 0.90965(18) 0.0474(7) Uani 1 1 d . . . S1 S 0.77544(10) -0.01039(9) 0.38283(7) 0.03655(19) Uani 1 1 d . . . O61 O 0.9278(3) -0.0932(3) 0.3774(2) 0.0514(7) Uani 1 1 d . . . C61 C 0.8312(5) 0.1510(4) 0.3225(3) 0.0480(10) Uani 1 1 d . . . D61A H 0.9268 0.1705 0.3386 0.072 Uiso 1 1 calc R . . D61B H 0.7425 0.2123 0.3389 0.072 Uiso 1 1 calc R . . D61C H 0.8550 0.1593 0.2568 0.072 Uiso 1 1 calc R . . C62 C 0.7234(5) 0.0158(4) 0.4936(3) 0.0504(10) Uani 1 1 d . . . D62A H 0.6821 -0.0643 0.5385 0.076 Uiso 1 1 calc R . . D62B H 0.6406 0.0862 0.4961 0.076 Uiso 1 1 calc R . . D62C H 0.8189 0.0400 0.5074 0.076 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 Re1 0.02135(7) 0.01800(7) 0.02294(7) -0.00544(5) -0.00199(5) 0.00182(4) Br1 0.02603(15) 0.03084(16) 0.02613(15) -0.00643(12) -0.00597(12) 0.00490(12) C1 0.0189(12) 0.0190(13) 0.0255(14) -0.0061(11) -0.0047(11) 0.0022(10) C2 0.0265(14) 0.0227(15) 0.0267(15) -0.0075(12) -0.0076(12) 0.0018(12) C11 0.0180(13) 0.0364(17) 0.0276(15) -0.0127(13) -0.0024(11) -0.0033(12) C12 0.0269(15) 0.0399(19) 0.0283(16) -0.0034(14) -0.0035(13) -0.0121(14) C13 0.0287(15) 0.0242(15) 0.0310(16) -0.0020(13) -0.0068(13) -0.0085(12) C21 0.0288(14) 0.0190(14) 0.0248(15) -0.0074(11) -0.0033(12) -0.0020(12) C22 0.0298(15) 0.0236(15) 0.0334(17) -0.0080(13) -0.0050(13) -0.0089(12) C23 0.0217(14) 0.0272(16) 0.0342(17) -0.0064(13) -0.0071(12) -0.0031(12) C31 0.0235(14) 0.0279(16) 0.0245(15) -0.0075(12) -0.0047(12) 0.0000(12) C32 0.0264(14) 0.0259(15) 0.0231(14) -0.0098(12) -0.0080(12) 0.0025(12) C33 0.0330(15) 0.0261(15) 0.0168(13) -0.0077(11) -0.0051(11) -0.0007(12) C34 0.0285(15) 0.0289(16) 0.0208(14) -0.0069(12) -0.0007(12) -0.0045(12) C35 0.0231(14) 0.0336(17) 0.0205(14) -0.0070(12) -0.0020(11) -0.0032(12) C36 0.0300(15) 0.0405(19) 0.0281(16) -0.0126(14) -0.0094(13) 0.0062(14) C37 0.0418(18) 0.043(2) 0.0324(17) -0.0165(15) -0.0191(15) 0.0208(16) C38 0.058(2) 0.0313(18) 0.0268(17) -0.0087(14) -0.0170(16) 0.0133(16) C39 0.051(2) 0.0261(16) 0.0209(15) -0.0069(12) -0.0070(14) 0.0023(14) C40 0.070(3) 0.0268(17) 0.0301(18) -0.0026(14) -0.0058(17) -0.0080(17) C41 0.061(3) 0.044(2) 0.039(2) -0.0083(17) 0.0047(18) -0.021(2) C42 0.0383(18) 0.044(2) 0.0327(18) -0.0125(15) 0.0038(14) -0.0145(16) C51 0.0308(16) 0.0219(15) 0.0290(16) -0.0055(12) -0.0022(13) 0.0045(12) C52 0.0356(16) 0.0250(17) 0.0272(16) -0.0093(13) -0.0025(13) 0.0011(13) C53 0.0293(15) 0.0217(15) 0.039(2) -0.0085(14) -0.0039(14) 0.0077(12) N1 0.0206(11) 0.0220(12) 0.0227(12) -0.0056(10) -0.0041(9) 0.0009(10) N11 0.0216(11) 0.0179(12) 0.0281(13) -0.0049(10) -0.0071(10) 0.0003(9) N12 0.0180(11) 0.0220(12) 0.0243(12) -0.0078(10) -0.0027(9) -0.0014(9) N21 0.0181(11) 0.0211(12) 0.0261(13) -0.0054(10) -0.0031(9) -0.0005(9) N22 0.0188(11) 0.0182(11) 0.0250(12) -0.0067(10) -0.0032(9) 0.0000(9) O1 0.0231(10) 0.0324(12) 0.0457(14) -0.0020(11) -0.0050(10) -0.0056(9) O2 0.0204(10) 0.0435(14) 0.0338(12) -0.0048(10) -0.0021(9) 0.0023(9) O51 0.0281(12) 0.0386(14) 0.0463(15) -0.0051(11) 0.0055(11) 0.0030(10) O52 0.0676(18) 0.0228(13) 0.0541(17) -0.0142(11) 0.0016(14) -0.0012(12) O53 0.0640(17) 0.0449(15) 0.0334(14) -0.0127(12) -0.0181(13) 0.0198(13) S1 0.0303(4) 0.0325(4) 0.0508(5) -0.0210(4) -0.0084(4) 0.0051(3) O61 0.0351(13) 0.0376(14) 0.084(2) -0.0309(15) -0.0080(13) 0.0135(11) C61 0.068(3) 0.037(2) 0.036(2) -0.0100(16) -0.0102(18) 0.0040(19) C62 0.062(3) 0.041(2) 0.038(2) -0.0076(17) -0.0043(18) 0.0123(19) _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 Re1 C51 1.914(3) . ? Re1 C52 1.915(3) . ? Re1 C53 1.920(4) . ? Re1 N21 2.170(2) . ? Re1 N11 2.185(2) . ? Re1 Br1 2.6282(4) . ? C1 H1 1.0000 . ? C1 N22 1.453(4) . ? C1 N12 1.454(3) . ? C1 C2 1.539(4) . ? C2 H2B 0.9900 . ? C2 H2A 0.9900 . ? C2 N1 1.467(4) . ? C11 H11 0.9500 . ? C11 N12 1.353(3) . ? C11 C12 1.361(5) . ? C12 H12 0.9500 . ? C12 C13 1.384(5) . ? C13 H13 0.9500 . ? C13 N11 1.339(4) . ? C21 H21 0.9500 . ? C21 N22 1.346(4) . ? C21 C22 1.368(4) . ? C22 H22 0.9500 . ? C22 C23 1.390(4) . ? C23 H23 0.9500 . ? C23 N21 1.339(4) . ? C31 O1 1.217(4) . ? C31 N1 1.392(4) . ? C31 C32 1.474(4) . ? C32 C36 1.373(4) . ? C32 C33 1.418(4) . ? C33 C34 1.409(4) . ? C33 C39 1.416(4) . ? C34 C42 1.379(4) . ? C34 C35 1.471(4) . ? C35 O2 1.212(4) . ? C35 N1 1.407(4) . ? C36 H36 0.9500 . ? C36 C37 1.404(5) . ? C37 H37 0.9500 . ? C37 C38 1.360(5) . ? C38 H38 0.9500 . ? C38 C39 1.413(5) . ? C39 C40 1.414(5) . ? C40 H40 0.9500 . ? C40 C41 1.365(6) . ? C41 H41 0.9500 . ? C41 C42 1.392(6) . ? C42 H42 0.9500 . ? C51 O51 1.153(4) . ? C52 O52 1.150(4) . ? C53 O53 1.110(4) . ? N11 N12 1.360(3) . ? N21 N22 1.367(3) . ? S1 O61 1.497(2) . ? S1 C61 1.773(4) . ? S1 C62 1.773(4) . ? C61 D61B 0.9800 . ? C61 D61A 0.9800 . ? C61 D61C 0.9800 . ? C62 D62C 0.9800 . ? C62 D62B 0.9800 . ? C62 D62A 0.9800 . ? 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 C51 Re1 C52 90.95(13) . . ? C51 Re1 C53 87.31(14) . . ? C52 Re1 C53 86.22(14) . . ? C51 Re1 N21 91.67(11) . . ? C52 Re1 N21 174.84(11) . . ? C53 Re1 N21 98.35(11) . . ? C51 Re1 N11 172.51(12) . . ? C52 Re1 N11 95.29(11) . . ? C53 Re1 N11 97.21(11) . . ? N21 Re1 N11 81.79(9) . . ? C51 Re1 Br1 90.48(10) . . ? C52 Re1 Br1 88.62(10) . . ? C53 Re1 Br1 174.34(9) . . ? N21 Re1 Br1 86.91(7) . . ? N11 Re1 Br1 85.55(7) . . ? H1 C1 N22 106.61 . . ? H1 C1 N12 106.61 . . ? N22 C1 N12 110.8(2) . . ? H1 C1 C2 106.61 . . ? N22 C1 C2 112.2(2) . . ? N12 C1 C2 113.6(2) . . ? H2B C2 H2A 108.3 . . ? H2B C2 N1 109.86 . . ? H2A C2 N1 109.86 . . ? H2B C2 C1 109.86 . . ? H2A C2 C1 109.86 . . ? N1 C2 C1 109.1(2) . . ? H11 C11 N12 126.38 . . ? H11 C11 C12 126.38 . . ? N12 C11 C12 107.2(3) . . ? H12 C12 C11 127.10 . . ? H12 C12 C13 127.10 . . ? C11 C12 C13 105.8(3) . . ? H13 C13 N11 124.49 . . ? H13 C13 C12 124.49 . . ? N11 C13 C12 111.0(3) . . ? H21 C21 N22 126.29 . . ? H21 C21 C22 126.29 . . ? N22 C21 C22 107.4(3) . . ? H22 C22 C21 127.44 . . ? H22 C22 C23 127.44 . . ? C21 C22 C23 105.1(3) . . ? H23 C23 N21 124.15 . . ? H23 C23 C22 124.15 . . ? N21 C23 C22 111.7(3) . . ? O1 C31 N1 119.6(3) . . ? O1 C31 C32 123.2(3) . . ? N1 C31 C32 117.2(2) . . ? C36 C32 C33 120.5(3) . . ? C36 C32 C31 120.3(3) . . ? C33 C32 C31 119.2(3) . . ? C34 C33 C39 119.7(3) . . ? C34 C33 C32 121.1(3) . . ? C39 C33 C32 119.2(3) . . ? C42 C34 C33 119.7(3) . . ? C42 C34 C35 119.6(3) . . ? C33 C34 C35 120.7(3) . . ? O2 C35 N1 119.7(3) . . ? O2 C35 C34 124.4(3) . . ? N1 C35 C34 115.9(2) . . ? H36 C36 C32 119.96 . . ? H36 C36 C37 120.0 . . ? C32 C36 C37 120.1(3) . . ? H37 C37 C38 119.76 . . ? H37 C37 C36 119.8 . . ? C38 C37 C36 120.5(3) . . ? H38 C38 C37 119.38 . . ? H38 C38 C39 119.4 . . ? C37 C38 C39 121.2(3) . . ? C38 C39 C40 123.0(3) . . ? C38 C39 C33 118.5(3) . . ? C40 C39 C33 118.4(3) . . ? H40 C40 C41 119.5 . . ? H40 C40 C39 119.5 . . ? C41 C40 C39 121.1(3) . . ? H41 C41 C40 119.9 . . ? H41 C41 C42 119.9 . . ? C40 C41 C42 120.2(3) . . ? H42 C42 C34 119.5 . . ? H42 C42 C41 119.5 . . ? C34 C42 C41 120.9(4) . . ? O51 C51 Re1 176.9(3) . . ? O52 C52 Re1 178.7(3) . . ? O53 C53 Re1 175.1(3) . . ? C31 N1 C35 125.6(2) . . ? C31 N1 C2 116.1(2) . . ? C35 N1 C2 118.2(2) . . ? C13 N11 N12 104.8(2) . . ? C13 N11 Re1 129.2(2) . . ? N12 N11 Re1 125.67(17) . . ? C11 N12 N11 111.1(2) . . ? C11 N12 C1 125.2(2) . . ? N11 N12 C1 123.8(2) . . ? C23 N21 N22 104.2(2) . . ? C23 N21 Re1 128.2(2) . . ? N22 N21 Re1 127.19(18) . . ? C21 N22 N21 111.6(2) . . ? C21 N22 C1 126.2(2) . . ? N21 N22 C1 121.3(2) . . ? O61 S1 C61 106.49(18) . . ? O61 S1 C62 106.07(19) . . ? C61 S1 C62 96.71(19) . . ? D61B C61 D61A 109.5 . . ? D61B C61 D61C 109.5 . . ? D61A C61 D61C 109.5 . . ? D61B C61 S1 109.47 . . ? D61A C61 S1 109.47 . . ? D61C C61 S1 109.47 . . ? D62C C62 D62B 109.5 . . ? D62C C62 D62A 109.5 . . ? D62B C62 D62A 109.5 . . ? D62C C62 S1 109.47 . . ? D62B C62 S1 109.47 . . ? D62A C62 S1 109.47 . . ? 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 N22 C1 C2 N1 82.1(3) . . . . ? N12 C1 C2 N1 -151.4(2) . . . . ? N12 C11 C12 C13 -0.5(4) . . . . ? C11 C12 C13 N11 1.3(4) . . . . ? N22 C21 C22 C23 -0.4(3) . . . . ? C21 C22 C23 N21 -0.7(4) . . . . ? O1 C31 C32 C36 4.2(5) . . . . ? N1 C31 C32 C36 -175.4(3) . . . . ? O1 C31 C32 C33 -175.0(3) . . . . ? N1 C31 C32 C33 5.5(4) . . . . ? C36 C32 C33 C34 178.3(3) . . . . ? C31 C32 C33 C34 -2.6(4) . . . . ? C36 C32 C33 C39 -0.6(5) . . . . ? C31 C32 C33 C39 178.6(3) . . . . ? C39 C33 C34 C42 -0.1(5) . . . . ? C32 C33 C34 C42 -178.9(3) . . . . ? C39 C33 C34 C35 177.8(3) . . . . ? C32 C33 C34 C35 -1.1(5) . . . . ? C42 C34 C35 O2 -0.5(5) . . . . ? C33 C34 C35 O2 -178.4(3) . . . . ? C42 C34 C35 N1 179.5(3) . . . . ? C33 C34 C35 N1 1.7(4) . . . . ? C33 C32 C36 C37 0.5(5) . . . . ? C31 C32 C36 C37 -178.6(3) . . . . ? C32 C36 C37 C38 -0.3(5) . . . . ? C36 C37 C38 C39 0.1(5) . . . . ? C37 C38 C39 C40 -178.9(3) . . . . ? C37 C38 C39 C33 -0.1(5) . . . . ? C34 C33 C39 C38 -178.5(3) . . . . ? C32 C33 C39 C38 0.4(5) . . . . ? C34 C33 C39 C40 0.3(5) . . . . ? C32 C33 C39 C40 179.2(3) . . . . ? C38 C39 C40 C41 178.3(4) . . . . ? C33 C39 C40 C41 -0.4(5) . . . . ? C39 C40 C41 C42 0.3(6) . . . . ? C33 C34 C42 C41 0.0(5) . . . . ? C35 C34 C42 C41 -177.9(3) . . . . ? C40 C41 C42 C34 -0.1(6) . . . . ? O1 C31 N1 C35 175.3(3) . . . . ? C32 C31 N1 C35 -5.1(4) . . . . ? O1 C31 N1 C2 -4.1(4) . . . . ? C32 C31 N1 C2 175.5(3) . . . . ? O2 C35 N1 C31 -178.4(3) . . . . ? C34 C35 N1 C31 1.6(4) . . . . ? O2 C35 N1 C2 1.0(4) . . . . ? C34 C35 N1 C2 -179.0(3) . . . . ? C1 C2 N1 C31 82.3(3) . . . . ? C1 C2 N1 C35 -97.1(3) . . . . ? C12 C13 N11 N12 -1.6(4) . . . . ? C12 C13 N11 Re1 -175.8(2) . . . . ? C52 Re1 N11 C13 -28.4(3) . . . . ? C53 Re1 N11 C13 -115.3(3) . . . . ? N21 Re1 N11 C13 147.3(3) . . . . ? Br1 Re1 N11 C13 59.8(3) . . . . ? C52 Re1 N11 N12 158.5(2) . . . . ? C53 Re1 N11 N12 71.6(2) . . . . ? N21 Re1 N11 N12 -25.8(2) . . . . ? Br1 Re1 N11 N12 -113.4(2) . . . . ? C12 C11 N12 N11 -0.5(4) . . . . ? C12 C11 N12 C1 -179.6(3) . . . . ? C13 N11 N12 C11 1.3(3) . . . . ? Re1 N11 N12 C11 175.8(2) . . . . ? C13 N11 N12 C1 -179.6(3) . . . . ? Re1 N11 N12 C1 -5.1(4) . . . . ? N22 C1 N12 C11 -128.9(3) . . . . ? C2 C1 N12 C11 103.8(3) . . . . ? N22 C1 N12 N11 52.2(4) . . . . ? C2 C1 N12 N11 -75.1(3) . . . . ? C22 C23 N21 N22 1.4(3) . . . . ? C22 C23 N21 Re1 174.1(2) . . . . ? C51 Re1 N21 C23 26.0(3) . . . . ? C53 Re1 N21 C23 113.5(3) . . . . ? N11 Re1 N21 C23 -150.3(3) . . . . ? Br1 Re1 N21 C23 -64.4(2) . . . . ? C51 Re1 N21 N22 -162.8(2) . . . . ? C53 Re1 N21 N22 -75.3(2) . . . . ? N11 Re1 N21 N22 20.9(2) . . . . ? Br1 Re1 N21 N22 106.8(2) . . . . ? C22 C21 N22 N21 1.3(3) . . . . ? C22 C21 N22 C1 170.6(3) . . . . ? C23 N21 N22 C21 -1.6(3) . . . . ? Re1 N21 N22 C21 -174.47(19) . . . . ? C23 N21 N22 C1 -171.5(2) . . . . ? Re1 N21 N22 C1 15.6(3) . . . . ? N12 C1 N22 C21 134.2(3) . . . . ? C2 C1 N22 C21 -97.7(3) . . . . ? N12 C1 N22 N21 -57.4(3) . . . . ? C2 C1 N22 N21 70.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.39 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 1.084 _refine_diff_density_min -0.615 _refine_diff_density_rms 0.102 #===END data_compound_2 _database_code_depnum_ccdc_archive 'CCDC 268889' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H23 Br N5 O5 Re, C3 H6 O' _chemical_formula_sum 'C30 H29 Br N5 O6 Re' _chemical_formula_weight 821.69 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Re Re -1.0185 7.2310 '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' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.8427(5) _cell_length_b 13.4707(8) _cell_length_c 13.9727(8) _cell_angle_alpha 67.1620(10) _cell_angle_beta 89.5790(10) _cell_angle_gamma 82.3020(10) _cell_volume 1518.27(15) _cell_formula_units_Z 2 _cell_measurement_temperature 150(1) _cell_measurement_reflns_used 6322 _cell_measurement_theta_min 2.703 _cell_measurement_theta_max 26.343 _exptl_crystal_description irregular _exptl_crystal_colour yellow _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.797 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 804 _exptl_absorpt_coefficient_mu 5.369 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6739 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details '(SADABS, Bruker, 2001)' _exptl_special_details ; Data crystal cleaved from multi-crystalline mass ; _diffrn_ambient_temperature 150(1) _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 'Bruker SMART APEX CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% none _diffrn_reflns_number 16466 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_sigmaI/netI 0.0321 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 26.38 _reflns_number_total 6199 _reflns_number_gt 5842 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART NT V5.625 (Bruker, 1998)' _computing_cell_refinement 'SAINT+ NT V6.22 (Bruker, 2001)' _computing_data_reduction 'SAINT+ NT V6.22' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL V6.1 (Sheldrick, 2000)' _computing_publication_material 'SHELXTL V6.1' _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^)+(0.0344P)^2^+0.1686P] 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 6199 _refine_ls_number_parameters 394 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0257 _refine_ls_R_factor_gt 0.0239 _refine_ls_wR_factor_ref 0.0612 _refine_ls_wR_factor_gt 0.0605 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 Re1 Re 0.357544(13) 0.396395(8) 0.225537(8) 0.02645(5) Uani 1 1 d . . . Br1 Br 0.54314(4) 0.24789(3) 0.37410(3) 0.04075(9) Uani 1 1 d . . . C1 C 0.3271(3) 0.6225(2) 0.2851(2) 0.0223(6) Uani 1 1 d . . . H1 H 0.3331 0.6780 0.3154 0.027 Uiso 1 1 calc R . . C2 C 0.2184(3) 0.6784(2) 0.1873(2) 0.0251(6) Uani 1 1 d . . . H2A H 0.2711 0.6722 0.1267 0.030 Uiso 1 1 calc R . . H2B H 0.1276 0.6404 0.1971 0.030 Uiso 1 1 calc R . . C11 C 0.2229(4) 0.5271(2) 0.4590(2) 0.0294(6) Uani 1 1 d . . . C12 C 0.1686(4) 0.4298(3) 0.5054(2) 0.0337(7) Uani 1 1 d . . . H12 H 0.1247 0.4039 0.5713 0.040 Uiso 1 1 calc R . . C13 C 0.1896(4) 0.3760(3) 0.4381(2) 0.0320(7) Uani 1 1 d . . . C14 C 0.2314(4) 0.6158(3) 0.4958(3) 0.0401(8) Uani 1 1 d . . . H14A H 0.3381 0.6270 0.4992 0.060 Uiso 1 1 calc R . . H14B H 0.1903 0.5959 0.5651 0.060 Uiso 1 1 calc R . . H14C H 0.1713 0.6830 0.4475 0.060 Uiso 1 1 calc R . . C15 C 0.1517(5) 0.2657(3) 0.4565(3) 0.0443(9) Uani 1 1 d . . . H15A H 0.0696 0.2721 0.4068 0.066 Uiso 1 1 calc R . . H15B H 0.1181 0.2320 0.5275 0.066 Uiso 1 1 calc R . . H15C H 0.2424 0.2204 0.4473 0.066 Uiso 1 1 calc R . . C21 C 0.6056(3) 0.6396(2) 0.2656(2) 0.0288(6) Uani 1 1 d . . . C22 C 0.7255(4) 0.5855(2) 0.2345(3) 0.0325(7) Uani 1 1 d . . . H22 H 0.8281 0.6002 0.2294 0.039 Uiso 1 1 calc R . . C23 C 0.6694(4) 0.5051(2) 0.2120(2) 0.0305(7) Uani 1 1 d . . . C24 C 0.5971(4) 0.7345(3) 0.2960(3) 0.0396(8) Uani 1 1 d . . . H24A H 0.5290 0.7960 0.2460 0.059 Uiso 1 1 calc R . . H24B H 0.6994 0.7548 0.2963 0.059 Uiso 1 1 calc R . . H24C H 0.5573 0.7151 0.3656 0.059 Uiso 1 1 calc R . . C25 C 0.7580(4) 0.4250(3) 0.1766(3) 0.0469(9) Uani 1 1 d . . . H25A H 0.7526 0.3512 0.2274 0.070 Uiso 1 1 calc R . . H25B H 0.8648 0.4377 0.1699 0.070 Uiso 1 1 calc R . . H25C H 0.7150 0.4333 0.1090 0.070 Uiso 1 1 calc R . . C31 C 0.0387(3) 0.8207(2) 0.2130(2) 0.0244(6) Uani 1 1 d . . . C32 C -0.0176(3) 0.9376(2) 0.1826(2) 0.0253(6) Uani 1 1 d . . . C33 C 0.0669(3) 1.0161(2) 0.1143(2) 0.0249(6) Uani 1 1 d . . . C34 C 0.2050(3) 0.9848(2) 0.0755(2) 0.0246(6) Uani 1 1 d . . . C35 C 0.2618(3) 0.8684(2) 0.1037(2) 0.0256(6) Uani 1 1 d . . . C36 C -0.1489(4) 0.9705(3) 0.2213(3) 0.0361(7) Uani 1 1 d . . . H36 H -0.2044 0.9175 0.2680 0.043 Uiso 1 1 calc R . . C37 C -0.2024(4) 1.0812(3) 0.1929(3) 0.0429(8) Uani 1 1 d . . . H37 H -0.2937 1.1028 0.2203 0.051 Uiso 1 1 calc R . . C38 C -0.1239(4) 1.1583(3) 0.1259(3) 0.0367(7) Uani 1 1 d . . . H38 H -0.1624 1.2332 0.1059 0.044 Uiso 1 1 calc R . . C39 C 0.0135(3) 1.1280(2) 0.0862(2) 0.0287(6) Uani 1 1 d . . . C40 C 0.1034(4) 1.2055(2) 0.0210(2) 0.0341(7) Uani 1 1 d . . . H40 H 0.0694 1.2809 0.0017 0.041 Uiso 1 1 calc R . . C41 C 0.2373(4) 1.1732(2) -0.0141(3) 0.0377(8) Uani 1 1 d . . . H41 H 0.2968 1.2261 -0.0564 0.045 Uiso 1 1 calc R . . C42 C 0.2882(4) 1.0622(2) 0.0118(2) 0.0342(7) Uani 1 1 d . . . H42 H 0.3802 1.0404 -0.0148 0.041 Uiso 1 1 calc R . . C51 C 0.4570(4) 0.3593(3) 0.1186(3) 0.0383(8) Uani 1 1 d . . . C52 C 0.2278(4) 0.2914(3) 0.2346(3) 0.0374(8) Uani 1 1 d . . . C53 C 0.2143(4) 0.4949(2) 0.1197(2) 0.0289(6) Uani 1 1 d . . . N1 N 0.1685(3) 0.79393(18) 0.16552(18) 0.0220(5) Uani 1 1 d . . . N11 N 0.2537(3) 0.43759(19) 0.35085(19) 0.0270(5) Uani 1 1 d . . . N12 N 0.2725(3) 0.53090(19) 0.36573(19) 0.0249(5) Uani 1 1 d . . . N21 N 0.5183(3) 0.50789(19) 0.22801(19) 0.0271(5) Uani 1 1 d . . . N22 N 0.4819(3) 0.59103(18) 0.26202(19) 0.0247(5) Uani 1 1 d . . . O1 O -0.0232(2) 0.74803(16) 0.27510(17) 0.0304(5) Uani 1 1 d . . . O2 O 0.3825(2) 0.83493(17) 0.07689(19) 0.0364(5) Uani 1 1 d . . . O51 O 0.5087(3) 0.3367(3) 0.0531(2) 0.0600(8) Uani 1 1 d . . . O52 O 0.1490(4) 0.2291(2) 0.2366(2) 0.0569(7) Uani 1 1 d . . . O53 O 0.1245(3) 0.54727(19) 0.05608(19) 0.0399(6) Uani 1 1 d . . . C61 C 0.7115(4) 0.0677(3) 0.6336(3) 0.0364(7) Uani 1 1 d . . . C62 C 0.5703(5) 0.0139(4) 0.6528(5) 0.0689(14) Uani 1 1 d . . . H62A H 0.5385 0.0012 0.7234 0.103 Uiso 1 1 calc R . . H62B H 0.5917 -0.0558 0.6450 0.103 Uiso 1 1 calc R . . H62C H 0.4884 0.0610 0.6024 0.103 Uiso 1 1 calc R . . C63 C 0.8292(5) 0.0354(3) 0.5695(3) 0.0558(10) Uani 1 1 d . . . H63A H 0.9132 0.0785 0.5602 0.084 Uiso 1 1 calc R . . H63B H 0.7827 0.0487 0.5014 0.084 Uiso 1 1 calc R . . H63C H 0.8687 -0.0421 0.6050 0.084 Uiso 1 1 calc R . . O61 O 0.7274(3) 0.13622(19) 0.66740(19) 0.0419(6) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Re1 0.03325(8) 0.02041(7) 0.02686(8) -0.01065(5) -0.00151(5) -0.00319(5) Br1 0.0494(2) 0.02440(16) 0.0433(2) -0.00869(14) -0.01388(16) -0.00116(14) C1 0.0240(14) 0.0171(13) 0.0264(14) -0.0085(11) 0.0023(11) -0.0045(11) C2 0.0256(14) 0.0197(13) 0.0301(15) -0.0095(12) -0.0006(12) -0.0038(11) C11 0.0362(17) 0.0296(15) 0.0226(15) -0.0096(13) 0.0030(12) -0.0070(13) C12 0.0395(18) 0.0337(16) 0.0285(16) -0.0113(14) 0.0054(13) -0.0101(14) C13 0.0365(17) 0.0285(16) 0.0302(16) -0.0085(13) 0.0053(13) -0.0112(13) C14 0.060(2) 0.0336(17) 0.0323(18) -0.0161(15) 0.0081(16) -0.0154(16) C15 0.064(2) 0.0326(18) 0.040(2) -0.0125(16) 0.0147(17) -0.0259(17) C21 0.0266(15) 0.0200(13) 0.0370(17) -0.0077(13) 0.0004(13) -0.0046(11) C22 0.0258(15) 0.0281(15) 0.0372(18) -0.0053(14) 0.0033(13) -0.0056(12) C23 0.0309(16) 0.0282(15) 0.0272(16) -0.0065(13) 0.0053(12) -0.0005(12) C24 0.0281(16) 0.0261(16) 0.068(2) -0.0215(17) -0.0065(16) -0.0033(13) C25 0.0369(19) 0.048(2) 0.063(3) -0.031(2) 0.0132(17) -0.0028(16) C31 0.0218(14) 0.0247(14) 0.0269(15) -0.0103(12) 0.0005(11) -0.0035(11) C32 0.0232(14) 0.0237(14) 0.0303(15) -0.0117(12) -0.0009(12) -0.0036(11) C33 0.0255(14) 0.0219(14) 0.0265(15) -0.0084(12) -0.0042(12) -0.0036(11) C34 0.0259(14) 0.0209(13) 0.0237(14) -0.0053(12) 0.0010(11) -0.0025(11) C35 0.0247(14) 0.0238(14) 0.0259(15) -0.0069(12) 0.0026(12) -0.0038(11) C36 0.0291(16) 0.0313(16) 0.050(2) -0.0171(16) 0.0071(14) -0.0061(13) C37 0.0290(17) 0.0387(19) 0.066(3) -0.0273(18) 0.0109(16) -0.0016(14) C38 0.0336(17) 0.0247(15) 0.052(2) -0.0180(15) -0.0043(15) 0.0035(13) C39 0.0297(15) 0.0228(14) 0.0327(16) -0.0102(13) -0.0059(13) -0.0019(12) C40 0.0421(18) 0.0207(14) 0.0338(17) -0.0043(13) -0.0037(14) -0.0044(13) C41 0.0429(19) 0.0237(15) 0.0361(18) 0.0011(14) 0.0054(15) -0.0094(14) C42 0.0334(17) 0.0274(15) 0.0328(17) -0.0018(13) 0.0048(13) -0.0049(13) C51 0.0432(19) 0.0349(18) 0.0412(19) -0.0218(16) -0.0028(15) 0.0021(15) C52 0.052(2) 0.0286(16) 0.0334(18) -0.0126(14) -0.0044(15) -0.0101(15) C53 0.0350(17) 0.0266(15) 0.0309(16) -0.0173(14) 0.0044(14) -0.0054(13) N1 0.0205(11) 0.0184(11) 0.0258(12) -0.0071(10) 0.0022(9) -0.0034(9) N11 0.0357(14) 0.0197(12) 0.0273(13) -0.0088(10) 0.0034(11) -0.0107(10) N12 0.0306(13) 0.0192(11) 0.0258(13) -0.0088(10) 0.0019(10) -0.0068(10) N21 0.0312(13) 0.0205(12) 0.0281(13) -0.0092(10) 0.0022(10) 0.0006(10) N22 0.0241(12) 0.0179(11) 0.0302(13) -0.0073(10) -0.0006(10) -0.0027(9) O1 0.0270(11) 0.0237(10) 0.0394(12) -0.0100(10) 0.0105(9) -0.0081(8) O2 0.0306(12) 0.0268(11) 0.0443(14) -0.0067(10) 0.0146(10) -0.0020(9) O51 0.0634(18) 0.073(2) 0.0592(18) -0.0470(17) 0.0067(15) 0.0024(15) O52 0.081(2) 0.0490(16) 0.0515(16) -0.0238(14) -0.0019(15) -0.0324(15) O53 0.0475(14) 0.0335(12) 0.0369(13) -0.0150(11) -0.0113(11) 0.0052(11) C61 0.0402(18) 0.0253(15) 0.0390(19) -0.0082(14) -0.0014(15) -0.0019(13) C62 0.055(3) 0.052(3) 0.116(4) -0.046(3) 0.018(3) -0.020(2) C63 0.059(3) 0.046(2) 0.063(3) -0.025(2) 0.014(2) -0.0005(19) O61 0.0462(14) 0.0345(12) 0.0470(15) -0.0181(11) -0.0095(11) -0.0047(11) _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 Re1 C53 1.899(3) . ? Re1 C52 1.904(3) . ? Re1 C51 1.923(3) . ? Re1 N11 2.193(3) . ? Re1 N21 2.211(2) . ? Re1 Br1 2.6366(4) . ? C1 N12 1.448(3) . ? C1 N22 1.449(4) . ? C1 C2 1.545(4) . ? C1 H1 1.0000 . ? C2 N1 1.469(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C11 N12 1.356(4) . ? C11 C12 1.369(4) . ? C11 C14 1.482(4) . ? C12 C13 1.392(4) . ? C12 H12 0.9500 . ? C13 N11 1.351(4) . ? C13 C15 1.491(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C21 N22 1.359(4) . ? C21 C22 1.370(4) . ? C21 C24 1.488(4) . ? C22 C23 1.390(4) . ? C22 H22 0.9500 . ? C23 N21 1.351(4) . ? C23 C25 1.485(4) . ? C24 H24A 0.9800 . ? C24 H24B 0.9800 . ? C24 H24C 0.9800 . ? C25 H25A 0.9800 . ? C25 H25B 0.9800 . ? C25 H25C 0.9800 . ? C31 O1 1.220(3) . ? C31 N1 1.397(4) . ? C31 C32 1.478(4) . ? C32 C36 1.369(4) . ? C32 C33 1.416(4) . ? C33 C34 1.412(4) . ? C33 C39 1.415(4) . ? C34 C42 1.376(4) . ? C34 C35 1.476(4) . ? C35 O2 1.215(4) . ? C35 N1 1.404(3) . ? C36 C37 1.400(5) . ? C36 H36 0.9500 . ? C37 C38 1.365(5) . ? C37 H37 0.9500 . ? C38 C39 1.408(4) . ? C38 H38 0.9500 . ? C39 C40 1.423(4) . ? C40 C41 1.360(5) . ? C40 H40 0.9500 . ? C41 C42 1.405(4) . ? C41 H41 0.9500 . ? C42 H42 0.9500 . ? C51 O51 1.145(4) . ? C52 O52 1.153(4) . ? C53 O53 1.137(4) . ? N11 N12 1.382(3) . ? N21 N22 1.378(3) . ? C61 O61 1.211(4) . ? C61 C62 1.497(5) . ? C61 C63 1.498(5) . ? C62 H62A 0.9800 . ? C62 H62B 0.9800 . ? C62 H62C 0.9800 . ? C63 H63A 0.9800 . ? C63 H63B 0.9800 . ? C63 H63C 0.9800 . ? 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 C53 Re1 C52 85.03(14) . . ? C53 Re1 C51 86.92(14) . . ? C52 Re1 C51 86.46(15) . . ? C53 Re1 N11 95.13(11) . . ? C52 Re1 N11 95.07(12) . . ? C51 Re1 N11 177.53(11) . . ? C53 Re1 N21 99.89(11) . . ? C52 Re1 N21 174.96(11) . . ? C51 Re1 N21 94.90(12) . . ? N11 Re1 N21 83.41(9) . . ? C53 Re1 Br1 175.57(9) . . ? C52 Re1 Br1 90.54(10) . . ? C51 Re1 Br1 92.83(10) . . ? N11 Re1 Br1 85.23(7) . . ? N21 Re1 Br1 84.54(6) . . ? N12 C1 N22 110.1(2) . . ? N12 C1 C2 114.1(2) . . ? N22 C1 C2 113.2(2) . . ? N12 C1 H1 106.3 . . ? N22 C1 H1 106.3 . . ? C2 C1 H1 106.3 . . ? N1 C2 C1 112.3(2) . . ? N1 C2 H2A 109.1 . . ? C1 C2 H2A 109.1 . . ? N1 C2 H2B 109.1 . . ? C1 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? N12 C11 C12 106.3(3) . . ? N12 C11 C14 123.1(3) . . ? C12 C11 C14 130.6(3) . . ? C11 C12 C13 107.3(3) . . ? C11 C12 H12 126.4 . . ? C13 C12 H12 126.4 . . ? N11 C13 C12 110.2(3) . . ? N11 C13 C15 123.0(3) . . ? C12 C13 C15 126.8(3) . . ? C11 C14 H14A 109.5 . . ? C11 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N22 C21 C22 106.2(3) . . ? N22 C21 C24 122.7(3) . . ? C22 C21 C24 131.0(3) . . ? C21 C22 C23 107.3(3) . . ? C21 C22 H22 126.4 . . ? C23 C22 H22 126.4 . . ? N21 C23 C22 110.1(3) . . ? N21 C23 C25 123.1(3) . . ? C22 C23 C25 126.7(3) . . ? C21 C24 H24A 109.5 . . ? C21 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C21 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? O1 C31 N1 119.3(3) . . ? O1 C31 C32 123.6(3) . . ? N1 C31 C32 117.0(2) . . ? C36 C32 C33 120.0(3) . . ? C36 C32 C31 120.6(3) . . ? C33 C32 C31 119.4(3) . . ? C34 C33 C39 119.4(3) . . ? C34 C33 C32 121.3(3) . . ? C39 C33 C32 119.3(3) . . ? C42 C34 C33 120.5(3) . . ? C42 C34 C35 119.5(3) . . ? C33 C34 C35 120.0(2) . . ? O2 C35 N1 119.6(3) . . ? O2 C35 C34 123.9(3) . . ? N1 C35 C34 116.5(2) . . ? C32 C36 C37 120.7(3) . . ? C32 C36 H36 119.6 . . ? C37 C36 H36 119.6 . . ? C38 C37 C36 120.3(3) . . ? C38 C37 H37 119.8 . . ? C36 C37 H37 119.8 . . ? C37 C38 C39 120.7(3) . . ? C37 C38 H38 119.6 . . ? C39 C38 H38 119.6 . . ? C38 C39 C33 118.9(3) . . ? C38 C39 C40 122.6(3) . . ? C33 C39 C40 118.4(3) . . ? C41 C40 C39 121.0(3) . . ? C41 C40 H40 119.5 . . ? C39 C40 H40 119.5 . . ? C40 C41 C42 120.4(3) . . ? C40 C41 H41 119.8 . . ? C42 C41 H41 119.8 . . ? C34 C42 C41 120.2(3) . . ? C34 C42 H42 119.9 . . ? C41 C42 H42 119.9 . . ? O51 C51 Re1 176.3(3) . . ? O52 C52 Re1 177.7(3) . . ? O53 C53 Re1 174.9(3) . . ? C31 N1 C35 125.0(2) . . ? C31 N1 C2 118.0(2) . . ? C35 N1 C2 116.9(2) . . ? C13 N11 N12 104.6(2) . . ? C13 N11 Re1 130.8(2) . . ? N12 N11 Re1 123.37(18) . . ? C11 N12 N11 111.7(2) . . ? C11 N12 C1 126.3(2) . . ? N11 N12 C1 121.8(2) . . ? C23 N21 N22 104.8(2) . . ? C23 N21 Re1 131.1(2) . . ? N22 N21 Re1 123.61(18) . . ? C21 N22 N21 111.5(2) . . ? C21 N22 C1 126.4(2) . . ? N21 N22 C1 122.0(2) . . ? O61 C61 C62 120.8(3) . . ? O61 C61 C63 121.8(3) . . ? C62 C61 C63 117.4(3) . . ? C61 C62 H62A 109.5 . . ? C61 C62 H62B 109.5 . . ? H62A C62 H62B 109.5 . . ? C61 C62 H62C 109.5 . . ? H62A C62 H62C 109.5 . . ? H62B C62 H62C 109.5 . . ? C61 C63 H63A 109.5 . . ? C61 C63 H63B 109.5 . . ? H63A C63 H63B 109.5 . . ? C61 C63 H63C 109.5 . . ? H63A C63 H63C 109.5 . . ? H63B C63 H63C 109.5 . . ? 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 N12 C1 C2 N1 120.9(2) . . . . ? N22 C1 C2 N1 -112.2(3) . . . . ? N12 C11 C12 C13 0.9(4) . . . . ? C14 C11 C12 C13 -179.0(3) . . . . ? C11 C12 C13 N11 -0.7(4) . . . . ? C11 C12 C13 C15 178.3(3) . . . . ? N22 C21 C22 C23 0.5(3) . . . . ? C24 C21 C22 C23 -178.0(3) . . . . ? C21 C22 C23 N21 0.1(4) . . . . ? C21 C22 C23 C25 -179.2(3) . . . . ? O1 C31 C32 C36 -2.5(4) . . . . ? N1 C31 C32 C36 176.4(3) . . . . ? O1 C31 C32 C33 176.5(3) . . . . ? N1 C31 C32 C33 -4.7(4) . . . . ? C36 C32 C33 C34 178.2(3) . . . . ? C31 C32 C33 C34 -0.8(4) . . . . ? C36 C32 C33 C39 -0.4(4) . . . . ? C31 C32 C33 C39 -179.4(3) . . . . ? C39 C33 C34 C42 0.7(4) . . . . ? C32 C33 C34 C42 -177.9(3) . . . . ? C39 C33 C34 C35 -179.7(3) . . . . ? C32 C33 C34 C35 1.7(4) . . . . ? C42 C34 C35 O2 2.6(5) . . . . ? C33 C34 C35 O2 -176.9(3) . . . . ? C42 C34 C35 N1 -177.5(3) . . . . ? C33 C34 C35 N1 2.9(4) . . . . ? C33 C32 C36 C37 0.9(5) . . . . ? C31 C32 C36 C37 179.9(3) . . . . ? C32 C36 C37 C38 0.0(5) . . . . ? C36 C37 C38 C39 -1.4(5) . . . . ? C37 C38 C39 C33 1.8(5) . . . . ? C37 C38 C39 C40 -176.3(3) . . . . ? C34 C33 C39 C38 -179.6(3) . . . . ? C32 C33 C39 C38 -0.9(4) . . . . ? C34 C33 C39 C40 -1.3(4) . . . . ? C32 C33 C39 C40 177.3(3) . . . . ? C38 C39 C40 C41 178.5(3) . . . . ? C33 C39 C40 C41 0.3(5) . . . . ? C39 C40 C41 C42 1.3(5) . . . . ? C33 C34 C42 C41 0.9(5) . . . . ? C35 C34 C42 C41 -178.7(3) . . . . ? C40 C41 C42 C34 -1.9(5) . . . . ? O1 C31 N1 C35 -171.1(3) . . . . ? C32 C31 N1 C35 10.0(4) . . . . ? O1 C31 N1 C2 4.3(4) . . . . ? C32 C31 N1 C2 -174.6(2) . . . . ? O2 C35 N1 C31 170.8(3) . . . . ? C34 C35 N1 C31 -9.1(4) . . . . ? O2 C35 N1 C2 -4.7(4) . . . . ? C34 C35 N1 C2 175.4(2) . . . . ? C1 C2 N1 C31 -87.8(3) . . . . ? C1 C2 N1 C35 88.0(3) . . . . ? C12 C13 N11 N12 0.2(3) . . . . ? C15 C13 N11 N12 -178.8(3) . . . . ? C12 C13 N11 Re1 167.3(2) . . . . ? C15 C13 N11 Re1 -11.7(5) . . . . ? C53 Re1 N11 C13 117.6(3) . . . . ? C52 Re1 N11 C13 32.2(3) . . . . ? N21 Re1 N11 C13 -143.0(3) . . . . ? Br1 Re1 N11 C13 -57.9(3) . . . . ? C53 Re1 N11 N12 -77.4(2) . . . . ? C52 Re1 N11 N12 -162.8(2) . . . . ? N21 Re1 N11 N12 22.0(2) . . . . ? Br1 Re1 N11 N12 107.1(2) . . . . ? C12 C11 N12 N11 -0.8(3) . . . . ? C14 C11 N12 N11 179.1(3) . . . . ? C12 C11 N12 C1 174.2(3) . . . . ? C14 C11 N12 C1 -5.9(5) . . . . ? C13 N11 N12 C11 0.4(3) . . . . ? Re1 N11 N12 C11 -167.9(2) . . . . ? C13 N11 N12 C1 -174.9(3) . . . . ? Re1 N11 N12 C1 16.8(3) . . . . ? N22 C1 N12 C11 121.6(3) . . . . ? C2 C1 N12 C11 -109.9(3) . . . . ? N22 C1 N12 N11 -63.9(3) . . . . ? C2 C1 N12 N11 64.6(3) . . . . ? C22 C23 N21 N22 -0.6(3) . . . . ? C25 C23 N21 N22 178.7(3) . . . . ? C22 C23 N21 Re1 -172.5(2) . . . . ? C25 C23 N21 Re1 6.8(5) . . . . ? C53 Re1 N21 C23 -121.1(3) . . . . ? C51 Re1 N21 C23 -33.3(3) . . . . ? N11 Re1 N21 C23 144.9(3) . . . . ? Br1 Re1 N21 C23 59.1(3) . . . . ? C53 Re1 N21 N22 68.3(2) . . . . ? C51 Re1 N21 N22 156.1(2) . . . . ? N11 Re1 N21 N22 -25.8(2) . . . . ? Br1 Re1 N21 N22 -111.6(2) . . . . ? C22 C21 N22 N21 -0.9(3) . . . . ? C24 C21 N22 N21 177.7(3) . . . . ? C22 C21 N22 C1 -178.0(3) . . . . ? C24 C21 N22 C1 0.6(5) . . . . ? C23 N21 N22 C21 0.9(3) . . . . ? Re1 N21 N22 C21 173.6(2) . . . . ? C23 N21 N22 C1 178.2(3) . . . . ? Re1 N21 N22 C1 -9.2(3) . . . . ? N12 C1 N22 C21 -124.0(3) . . . . ? C2 C1 N22 C21 107.0(3) . . . . ? N12 C1 N22 N21 59.2(3) . . . . ? C2 C1 N22 N21 -69.9(3) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.219 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.095 #===END