# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2003 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Alan Cowley' _publ_contact_author_name 'Dr Alan Cowley' _publ_contact_author_address ; Chemistry & Biochemistry The University of Texas at Austin 1 University Station A5300 Austin TX 78712-0165 UNITED STATES OF AMERICA ; _publ_contact_author_email COWLEY@MAIL.UTEXAS.EDU _publ_requested_journal 'Chemical Communications' _publ_section_title ; An unprecedented mode of ligation for a bridged amido-cyclopentadienide (constrained geometry) ligand; pi-olefinic interactions with gallium and indium ; data_shelx _database_code_CSD 211521 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C60 H60 Br7.50 N7.50' _chemical_formula_weight 1485.48 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 28.819(5) _cell_length_b 10.496(5) _cell_length_c 19.591(5) _cell_angle_alpha 90.000(5) _cell_angle_beta 119.054(5) _cell_angle_gamma 90.000(5) _cell_volume 5180(3) _cell_formula_units_Z 4 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used all _cell_measurement_theta_min 3.12 _cell_measurement_theta_max 60.52 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.3 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.905 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2940 _exptl_absorpt_coefficient_mu 5.859 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23863 _diffrn_reflns_av_R_equivalents 0.0924 _diffrn_reflns_av_sigmaI/netI 0.0726 _diffrn_reflns_limit_h_min -38 _diffrn_reflns_limit_h_max 33 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 30.52 _reflns_number_total 6955 _reflns_number_gt 4922 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect Software' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXL-97 (Sheldrick, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0575P)^2^+2.8028P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.00030(9) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6955 _refine_ls_number_parameters 358 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0836 _refine_ls_R_factor_gt 0.0509 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1089 _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_restrained_S_all 1.053 _refine_ls_shift/su_max 0.054 _refine_ls_shift/su_mean 0.005 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 Br2 Br 0.024874(15) 0.69074(4) -0.06741(2) 0.03484(13) Uani 1 1 d . . . Br1 Br -0.021610(13) -0.04052(4) 0.13489(2) 0.03387(13) Uani 1 1 d . . . Br3 Br 0.254558(14) 0.26792(4) 0.33260(2) 0.03125(12) Uani 1 1 d . . . N3 N 0.17779(10) 0.1512(3) 0.13662(17) 0.0212(6) Uani 1 1 d . . . N2 N 0.23264(11) 0.2774(3) 0.11961(17) 0.0217(6) Uani 1 1 d . . . N1 N 0.25724(10) 0.1673(3) 0.15697(16) 0.0203(6) Uani 1 1 d . . . C21 C 0.11723(14) 0.1546(4) 0.1901(2) 0.0257(8) Uani 1 1 d . . . C1 C 0.22460(13) 0.0930(3) 0.1673(2) 0.0218(7) Uani 1 1 d . . . C20 C 0.13145(12) 0.1017(3) 0.1386(2) 0.0204(7) Uani 1 1 d . . . C12 C 0.12555(14) 0.5884(4) 0.0397(2) 0.0239(7) Uani 1 1 d . . . C30 C 0.31415(12) 0.1447(3) 0.18025(19) 0.0196(7) Uani 1 1 d . . . C32 C 0.39656(13) 0.0363(4) 0.2780(2) 0.0266(8) Uani 1 1 d . . . C25 C 0.10280(14) 0.0043(4) 0.0884(2) 0.0269(8) Uani 1 1 d . . . C36 C 0.40057(15) -0.0303(4) 0.2117(2) 0.0303(8) Uani 1 1 d . . . C10 C 0.14352(12) 0.3655(3) 0.06869(19) 0.0190(6) Uani 1 1 d . . . C14 C 0.05430(14) 0.4347(3) -0.0182(2) 0.0248(7) Uiso 1 1 d . . . C35 C 0.34309(13) 0.2732(4) 0.1986(2) 0.0247(7) Uani 1 1 d . . . C15 C 0.08993(14) 0.3371(3) 0.0208(2) 0.0248(7) Uani 1 1 d . . . C39 C 0.40526(15) 0.1812(4) 0.1568(2) 0.0310(8) Uani 1 1 d . . . C13 C 0.07304(13) 0.5588(3) -0.0087(2) 0.0232(7) Uiso 1 1 d . . . C2 C 0.18379(12) 0.2664(3) 0.10768(19) 0.0195(6) Uani 1 1 d . . . C38 C 0.31720(14) 0.0791(4) 0.1131(2) 0.0257(8) Uani 1 1 d . . . C22 C 0.07161(13) 0.1115(4) 0.1905(2) 0.0272(8) Uani 1 1 d . . . C11 C 0.16108(13) 0.4909(3) 0.0778(2) 0.0231(7) Uani 1 1 d . . . C23 C 0.04200(13) 0.0163(3) 0.1389(2) 0.0249(7) Uani 1 1 d . . . C37 C 0.37598(14) 0.0545(4) 0.1390(2) 0.0302(8) Uani 1 1 d . . . C31 C 0.33803(13) 0.0603(4) 0.2532(2) 0.0239(7) Uani 1 1 d . . . C33 C 0.42609(14) 0.1640(4) 0.2965(2) 0.0308(8) Uani 1 1 d . . . C34 C 0.40164(14) 0.2478(4) 0.2237(2) 0.0278(8) Uani 1 1 d . . . C24 C 0.05735(15) -0.0386(4) 0.0884(2) 0.0281(8) Uani 1 1 d . . . H4 H 0.1975(15) 0.509(3) 0.114(2) 0.021(9) Uiso 1 1 d . . . H5 H 0.0767(13) 0.250(3) 0.006(2) 0.014(8) Uiso 1 1 d . . . H2 H 0.0398(14) -0.099(4) 0.055(2) 0.018(9) Uiso 1 1 d . . . H1 H 0.1137(15) -0.035(4) 0.056(2) 0.024(10) Uiso 1 1 d . . . H3 H 0.2304(14) 0.022(4) 0.184(2) 0.015(9) Uiso 1 1 d . . . H6 H 0.1333(16) 0.665(4) 0.039(2) 0.033(11) Uiso 1 1 d . . . H20 H 0.4224(13) 0.324(3) 0.2375(19) 0.012(8) Uiso 1 1 d . . . H21 H 0.3258(16) 0.322(4) 0.153(3) 0.033(11) Uiso 1 1 d . . . H24 H 0.2991(14) 0.132(4) 0.062(2) 0.020(9) Uiso 1 1 d . . . H23 H 0.3007(14) 0.007(4) 0.105(2) 0.017(9) Uiso 1 1 d . . . H16 H 0.3346(14) 0.103(4) 0.292(2) 0.025(10) Uiso 1 1 d . . . H13 H 0.4620(17) 0.154(4) 0.314(2) 0.032(10) Uiso 1 1 d . . . H22 H 0.3389(13) 0.313(3) 0.241(2) 0.014(8) Uiso 1 1 d . . . H15 H 0.3164(14) -0.017(4) 0.238(2) 0.016(8) Uiso 1 1 d . . . H26 H 0.3912(14) 0.236(3) 0.110(2) 0.017(9) Uiso 1 1 d . . . H30 H 0.4372(19) -0.047(4) 0.231(3) 0.042(12) Uiso 1 1 d . . . H25 H 0.443(2) 0.159(5) 0.178(3) 0.053(13) Uiso 1 1 d . . . H12 H 0.4294(14) 0.211(3) 0.352(2) 0.023(9) Uiso 1 1 d . . . H10 H 0.1341(15) 0.212(4) 0.219(2) 0.020(10) Uiso 1 1 d . . . H14 H 0.4100(16) -0.015(4) 0.327(3) 0.036(11) Uiso 1 1 d . . . H31 H 0.3790(15) 0.020(4) 0.101(2) 0.027(10) Uiso 1 1 d . . . H11 H 0.0146(16) 0.410(4) -0.053(2) 0.034(10) Uiso 1 1 d . . . H40 H 0.0584(15) 0.153(4) 0.228(2) 0.035(11) Uiso 1 1 d . . . H42 H 0.3830(15) -0.107(4) 0.205(2) 0.023(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br2 0.0323(2) 0.0312(2) 0.0382(2) 0.00941(17) 0.01495(18) 0.01173(15) Br1 0.02034(18) 0.0411(2) 0.0420(2) 0.00904(17) 0.01657(17) -0.00469(15) Br3 0.0315(2) 0.0259(2) 0.0351(2) 0.00078(16) 0.01515(17) 0.00413(14) N3 0.0163(13) 0.0212(14) 0.0280(16) 0.0020(12) 0.0123(12) -0.0004(11) N2 0.0197(13) 0.0209(14) 0.0249(15) 0.0027(12) 0.0113(12) 0.0007(11) N1 0.0175(13) 0.0224(15) 0.0237(15) 0.0023(12) 0.0121(12) 0.0016(11) C21 0.0207(17) 0.0256(19) 0.030(2) -0.0035(16) 0.0118(16) -0.0040(14) C1 0.0214(17) 0.0174(18) 0.0291(19) 0.0046(15) 0.0143(15) -0.0002(13) C20 0.0146(15) 0.0212(17) 0.0264(18) 0.0037(14) 0.0108(14) -0.0001(12) C12 0.0286(18) 0.0207(18) 0.0243(19) -0.0011(15) 0.0142(16) 0.0000(14) C30 0.0138(14) 0.0260(18) 0.0204(17) 0.0007(14) 0.0094(13) 0.0003(12) C32 0.0189(16) 0.034(2) 0.0257(19) 0.0069(16) 0.0103(15) 0.0029(14) C25 0.0279(18) 0.0267(19) 0.031(2) -0.0032(16) 0.0186(17) -0.0006(14) C36 0.0215(18) 0.028(2) 0.045(2) 0.0008(17) 0.0185(17) 0.0024(15) C10 0.0182(15) 0.0210(16) 0.0221(17) -0.0023(14) 0.0131(13) -0.0001(12) C35 0.0200(16) 0.0252(18) 0.029(2) 0.0012(16) 0.0121(15) -0.0025(14) C15 0.0247(17) 0.0233(19) 0.0264(19) -0.0012(15) 0.0125(15) -0.0003(14) C39 0.0219(18) 0.043(2) 0.035(2) 0.0051(18) 0.0190(17) 0.0016(16) C2 0.0193(15) 0.0195(16) 0.0213(17) 0.0002(13) 0.0111(13) -0.0014(12) C38 0.0201(17) 0.030(2) 0.029(2) -0.0035(17) 0.0142(16) -0.0028(15) C22 0.0222(17) 0.033(2) 0.030(2) 0.0029(16) 0.0150(16) 0.0010(14) C11 0.0191(16) 0.0282(18) 0.0228(18) -0.0031(15) 0.0108(15) -0.0023(13) C23 0.0164(15) 0.0285(19) 0.0306(19) 0.0091(15) 0.0120(15) -0.0023(13) C37 0.0242(18) 0.043(2) 0.029(2) -0.0085(18) 0.0171(16) 0.0012(16) C31 0.0194(16) 0.031(2) 0.0246(19) 0.0044(16) 0.0133(15) 0.0017(14) C33 0.0196(18) 0.042(2) 0.028(2) -0.0002(17) 0.0095(16) -0.0033(15) C34 0.0203(17) 0.030(2) 0.034(2) -0.0024(16) 0.0136(16) -0.0088(14) C24 0.0273(18) 0.0236(19) 0.033(2) -0.0012(17) 0.0147(17) -0.0057(15) _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 Br2 C13 1.901(3) . ? Br1 C23 1.893(3) . ? N3 C1 1.329(4) . ? N3 C2 1.381(4) . ? N3 C20 1.451(4) . ? N2 C2 1.315(4) . ? N2 N1 1.367(4) . ? N1 C1 1.312(4) . ? N1 C30 1.493(4) . ? C21 C20 1.376(5) . ? C21 C22 1.394(5) . ? C20 C25 1.380(5) . ? C12 C13 1.375(5) . ? C12 C11 1.382(5) . ? C30 C38 1.525(5) . ? C30 C31 1.531(5) . ? C30 C35 1.534(5) . ? C32 C36 1.527(5) . ? C32 C33 1.534(5) . ? C32 C31 1.533(5) . ? C25 C24 1.385(5) . ? C36 C37 1.531(6) . ? C10 C11 1.390(5) . ? C10 C15 1.395(5) . ? C10 C2 1.467(5) . ? C14 C15 1.388(5) . ? C14 C13 1.388(5) . ? C35 C34 1.535(5) . ? C39 C37 1.523(6) . ? C39 C34 1.533(5) . ? C38 C37 1.536(5) . ? C22 C23 1.382(5) . ? C23 C24 1.389(5) . ? C33 C34 1.525(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 C1 N3 C2 106.6(3) . . ? C1 N3 C20 124.6(3) . . ? C2 N3 C20 128.7(3) . . ? C2 N2 N1 104.7(3) . . ? C1 N1 N2 111.2(3) . . ? C1 N1 C30 128.5(3) . . ? N2 N1 C30 120.4(2) . . ? C20 C21 C22 119.4(3) . . ? N1 C1 N3 107.6(3) . . ? C21 C20 C25 122.2(3) . . ? C21 C20 N3 118.7(3) . . ? C25 C20 N3 119.1(3) . . ? C13 C12 C11 118.9(3) . . ? N1 C30 C38 108.9(3) . . ? N1 C30 C31 107.8(2) . . ? C38 C30 C31 110.9(3) . . ? N1 C30 C35 108.8(3) . . ? C38 C30 C35 110.3(3) . . ? C31 C30 C35 110.1(3) . . ? C36 C32 C33 109.8(3) . . ? C36 C32 C31 109.4(3) . . ? C33 C32 C31 109.3(3) . . ? C20 C25 C24 118.6(3) . . ? C32 C36 C37 109.5(3) . . ? C11 C10 C15 120.3(3) . . ? C11 C10 C2 117.3(3) . . ? C15 C10 C2 122.4(3) . . ? C15 C14 C13 118.9(3) . . ? C30 C35 C34 108.1(3) . . ? C14 C15 C10 119.6(3) . . ? C37 C39 C34 109.5(3) . . ? C12 C13 C14 122.0(3) . . ? C12 C13 Br2 119.2(3) . . ? C14 C13 Br2 118.7(3) . . ? N2 C2 N3 109.9(3) . . ? N2 C2 C10 122.6(3) . . ? N3 C2 C10 127.5(3) . . ? C30 C38 C37 107.9(3) . . ? C23 C22 C21 118.6(3) . . ? C12 C11 C10 120.2(3) . . ? C22 C23 C24 121.6(3) . . ? C22 C23 Br1 119.9(3) . . ? C24 C23 Br1 118.5(3) . . ? C39 C37 C36 109.9(3) . . ? C39 C37 C38 109.2(3) . . ? C36 C37 C38 110.1(3) . . ? C30 C31 C32 108.5(3) . . ? C34 C33 C32 109.4(3) . . ? C33 C34 C39 110.2(3) . . ? C33 C34 C35 109.6(3) . . ? C39 C34 C35 109.1(3) . . ? C23 C24 C25 119.6(3) . . ? _diffrn_measured_fraction_theta_max 0.880 _diffrn_reflns_theta_full 30.52 _diffrn_measured_fraction_theta_full 0.880 _refine_diff_density_max 1.111 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.134 data_shelx_2 _database_code_CSD 211522 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H23 Br2 N3' _chemical_formula_sum 'C24 H23 Br2 N3' _chemical_formula_weight 513.27 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.489(5) _cell_length_b 12.008(5) _cell_length_c 12.485(5) _cell_angle_alpha 80.890(5) _cell_angle_beta 75.043(5) _cell_angle_gamma 79.011(5) _cell_volume 1057.7(9) _cell_formula_units_Z 2 _cell_measurement_temperature 153(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.612 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 3.848 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 153(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Kappa CCD' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 8038 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0565 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.40 _diffrn_reflns_theta_max 30.50 _reflns_number_total 5309 _reflns_number_gt 4122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0512P)^2^+2.9822P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.0125(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 5309 _refine_ls_number_parameters 355 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0722 _refine_ls_R_factor_gt 0.0499 _refine_ls_wR_factor_ref 0.1319 _refine_ls_wR_factor_gt 0.1167 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 Br23 Br 0.22194(6) 0.69958(3) 0.66556(3) 0.03025(14) Uani 1 1 d . . . Br13 Br 0.15732(7) -0.06805(4) 0.84071(3) 0.03679(15) Uani 1 1 d . . . C10 C 0.2384(6) 0.1494(3) 0.4944(3) 0.0252(8) Uani 1 1 d . . . N1 N 0.3001(5) 0.2615(3) 0.2139(3) 0.0246(7) Uani 1 1 d . . . N2 N 0.2624(5) 0.2161(3) 0.3866(3) 0.0250(7) Uani 1 1 d . . . C20 C 0.2536(6) 0.4158(3) 0.4416(3) 0.0238(8) Uani 1 1 d . . . N3 N 0.2876(5) 0.3631(3) 0.2571(3) 0.0252(7) Uani 1 1 d . . . C30 C 0.3232(6) 0.2703(3) 0.0916(3) 0.0235(7) Uani 1 1 d . . . C22 C 0.1542(6) 0.4873(3) 0.6215(3) 0.0245(8) Uani 1 1 d . . . C13 C 0.1907(6) 0.0214(3) 0.6992(3) 0.0268(8) Uani 1 1 d . . . C14 C 0.3614(6) 0.0586(3) 0.6520(3) 0.0276(8) Uani 1 1 d . . . C11 C 0.0694(7) 0.1113(4) 0.5423(4) 0.0320(9) Uani 1 1 d . . . C1 C 0.2830(6) 0.1684(3) 0.2893(3) 0.0260(8) Uani 1 1 d . . . C15 C 0.3851(6) 0.1234(3) 0.5479(3) 0.0284(8) Uani 1 1 d . . . C38 C 0.3606(7) 0.1505(3) 0.0542(4) 0.0290(9) Uani 1 1 d . . . C35 C 0.1439(6) 0.3374(3) 0.0611(3) 0.0268(8) Uani 1 1 d . . . C2 C 0.2668(5) 0.3322(3) 0.3636(3) 0.0238(7) Uani 1 1 d . . . C33 C 0.3325(7) 0.4121(4) -0.1235(4) 0.0323(9) Uani 1 1 d . . . C36 C 0.2055(7) 0.2296(4) -0.1042(4) 0.0319(9) Uani 1 1 d . . . C31 C 0.4882(6) 0.3330(4) 0.0340(3) 0.0278(8) Uani 1 1 d . . . C25 C 0.3279(6) 0.5156(3) 0.3960(3) 0.0274(8) Uani 1 1 d . . . C37 C 0.3849(7) 0.1629(4) -0.0737(4) 0.0321(9) Uani 1 1 d . . . C21 C 0.1659(6) 0.4024(3) 0.5548(3) 0.0246(8) Uani 1 1 d . . . C39 C 0.5505(7) 0.2257(4) -0.1321(4) 0.0369(10) Uani 1 1 d . . . C24 C 0.3181(6) 0.6010(3) 0.4619(3) 0.0259(8) Uani 1 1 d . . . C12 C 0.0444(7) 0.0461(4) 0.6460(4) 0.0329(9) Uani 1 1 d . . . C34 C 0.1675(6) 0.3489(4) -0.0664(3) 0.0281(8) Uani 1 1 d . . . C23 C 0.2321(6) 0.5850(3) 0.5742(3) 0.0254(8) Uani 1 1 d . . . C32 C 0.5112(7) 0.3452(4) -0.0932(3) 0.0334(9) Uani 1 1 d . . . H39A H 0.679(8) 0.188(4) -0.118(4) 0.040(14) Uiso 1 1 d . . . H31A H 0.604(7) 0.290(4) 0.049(4) 0.038(13) Uiso 1 1 d . . . H31B H 0.459(6) 0.407(4) 0.054(4) 0.023(11) Uiso 1 1 d . . . H21 H 0.106(6) 0.334(4) 0.591(4) 0.025(11) Uiso 1 1 d . . . H35B H 0.109(6) 0.417(4) 0.085(4) 0.023(11) Uiso 1 1 d . . . H15 H 0.501(7) 0.152(4) 0.512(4) 0.030(12) Uiso 1 1 d . . . H14 H 0.462(6) 0.036(4) 0.688(4) 0.024(11) Uiso 1 1 d . . . H38A H 0.474(7) 0.104(4) 0.077(4) 0.033(13) Uiso 1 1 d . . . H11 H -0.035(7) 0.135(4) 0.499(4) 0.033(12) Uiso 1 1 d . . . H37 H 0.416(7) 0.079(4) -0.094(4) 0.038(13) Uiso 1 1 d . . . H36A H 0.097(8) 0.185(5) -0.062(4) 0.042(14) Uiso 1 1 d . . . H35A H 0.030(8) 0.299(5) 0.101(4) 0.042(14) Uiso 1 1 d . . . H12 H -0.068(7) 0.017(4) 0.680(4) 0.029(12) Uiso 1 1 d . . . H23 H 0.370(6) 0.671(4) 0.433(4) 0.024(11) Uiso 1 1 d . . . H24 H 0.399(7) 0.523(4) 0.316(5) 0.044(14) Uiso 1 1 d . . . H36B H 0.213(7) 0.234(4) -0.181(4) 0.036(13) Uiso 1 1 d . . . H34 H 0.046(7) 0.392(4) -0.084(4) 0.037(14) Uiso 1 1 d . . . H38B H 0.258(8) 0.108(5) 0.097(4) 0.042(14) Uiso 1 1 d . . . H22 H 0.092(7) 0.481(4) 0.697(4) 0.036(13) Uiso 1 1 d . . . H33B H 0.302(7) 0.493(4) -0.102(4) 0.035(13) Uiso 1 1 d . . . H32 H 0.618(8) 0.386(5) -0.129(5) 0.047(15) Uiso 1 1 d . . . H33A H 0.345(8) 0.419(5) -0.196(5) 0.047(15) Uiso 1 1 d . . . H39B H 0.580(7) 0.228(4) -0.217(5) 0.045(15) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br23 0.0378(3) 0.0295(2) 0.0252(2) -0.00814(15) -0.00615(16) -0.00687(17) Br13 0.0556(3) 0.0347(2) 0.0248(2) 0.01035(16) -0.01606(19) -0.0208(2) C10 0.038(2) 0.0187(17) 0.0202(17) 0.0012(13) -0.0086(15) -0.0069(15) N1 0.0370(19) 0.0195(15) 0.0192(15) -0.0008(12) -0.0089(13) -0.0070(13) N2 0.0366(19) 0.0207(15) 0.0198(15) 0.0019(12) -0.0103(13) -0.0083(14) C20 0.028(2) 0.0251(18) 0.0185(17) 0.0000(14) -0.0074(14) -0.0030(15) N3 0.0364(19) 0.0192(15) 0.0210(15) -0.0030(12) -0.0071(13) -0.0055(14) C30 0.034(2) 0.0194(17) 0.0186(17) -0.0012(13) -0.0074(15) -0.0063(15) C22 0.027(2) 0.0260(19) 0.0197(17) -0.0022(14) -0.0056(15) -0.0032(15) C13 0.043(2) 0.0177(17) 0.0214(18) 0.0034(13) -0.0111(16) -0.0088(16) C14 0.035(2) 0.0260(19) 0.0223(18) 0.0005(15) -0.0086(16) -0.0072(17) C11 0.041(2) 0.032(2) 0.027(2) 0.0090(16) -0.0141(18) -0.0158(18) C1 0.033(2) 0.0219(18) 0.0233(18) -0.0013(14) -0.0082(15) -0.0049(16) C15 0.036(2) 0.0262(19) 0.0237(19) -0.0028(15) -0.0076(16) -0.0069(17) C38 0.041(2) 0.0167(17) 0.029(2) -0.0013(15) -0.0116(18) -0.0015(17) C35 0.035(2) 0.0234(19) 0.0212(18) -0.0030(15) -0.0055(16) -0.0041(17) C2 0.0258(19) 0.0240(18) 0.0220(18) -0.0007(14) -0.0084(14) -0.0025(15) C33 0.048(3) 0.031(2) 0.0198(19) 0.0045(16) -0.0125(18) -0.0116(19) C36 0.047(3) 0.029(2) 0.024(2) -0.0046(16) -0.0147(18) -0.0080(19) C31 0.037(2) 0.025(2) 0.0233(19) -0.0003(15) -0.0083(16) -0.0100(17) C25 0.033(2) 0.0273(19) 0.0218(19) -0.0038(15) -0.0050(16) -0.0061(17) C37 0.045(3) 0.024(2) 0.028(2) -0.0078(16) -0.0093(18) -0.0025(18) C21 0.029(2) 0.0243(18) 0.0198(17) -0.0012(14) -0.0062(15) -0.0040(16) C39 0.041(3) 0.041(3) 0.025(2) -0.0086(18) -0.0037(18) 0.000(2) C24 0.035(2) 0.0249(19) 0.0201(18) -0.0018(14) -0.0061(15) -0.0102(16) C12 0.038(2) 0.035(2) 0.027(2) 0.0098(17) -0.0118(18) -0.0155(19) C34 0.036(2) 0.029(2) 0.0208(18) 0.0009(15) -0.0107(16) -0.0053(17) C23 0.029(2) 0.0248(18) 0.0229(18) -0.0057(14) -0.0064(15) -0.0035(15) C32 0.039(2) 0.041(2) 0.0216(19) 0.0010(17) -0.0054(17) -0.015(2) _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 Br23 C23 1.900(4) . ? Br13 C13 1.900(4) . ? C10 C11 1.383(6) . ? C10 C15 1.390(6) . ? C10 N2 1.440(5) . ? N1 C1 1.346(5) . ? N1 N3 1.388(4) . ? N1 C30 1.481(5) . ? N2 C2 1.384(5) . ? N2 C1 1.384(5) . ? C20 C25 1.394(6) . ? C20 C21 1.395(5) . ? C20 C2 1.478(5) . ? N3 C2 1.300(5) . ? C30 C31 1.529(6) . ? C30 C35 1.533(6) . ? C30 C38 1.535(5) . ? C22 C23 1.388(6) . ? C22 C21 1.392(5) . ? C13 C12 1.385(6) . ? C13 C14 1.388(6) . ? C14 C15 1.393(5) . ? C11 C12 1.391(6) . ? C38 C37 1.545(6) . ? C35 C34 1.542(5) . ? C33 C32 1.528(7) . ? C33 C34 1.531(6) . ? C36 C34 1.531(6) . ? C36 C37 1.533(6) . ? C31 C32 1.539(6) . ? C25 C24 1.394(5) . ? C37 C39 1.535(7) . ? C39 C32 1.538(7) . ? C24 C23 1.384(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 C11 C10 C15 121.1(4) . . ? C11 C10 N2 119.1(4) . . ? C15 C10 N2 119.8(4) . . ? C1 N1 N3 115.6(3) . . ? C1 N1 C30 128.4(3) . . ? N3 N1 C30 115.9(3) . . ? C2 N2 C1 110.6(3) . . ? C2 N2 C10 127.1(3) . . ? C1 N2 C10 122.3(3) . . ? C25 C20 C21 119.1(4) . . ? C25 C20 C2 116.7(3) . . ? C21 C20 C2 124.1(4) . . ? C2 N3 N1 103.5(3) . . ? N1 C30 C31 108.7(3) . . ? N1 C30 C35 109.1(3) . . ? C31 C30 C35 109.7(3) . . ? N1 C30 C38 110.0(3) . . ? C31 C30 C38 109.8(3) . . ? C35 C30 C38 109.5(3) . . ? C23 C22 C21 119.3(4) . . ? C12 C13 C14 122.2(4) . . ? C12 C13 Br13 118.8(3) . . ? C14 C13 Br13 119.0(3) . . ? C13 C14 C15 118.6(4) . . ? C10 C11 C12 119.8(4) . . ? N1 C1 N2 100.3(3) . . ? C10 C15 C14 119.6(4) . . ? C30 C38 C37 108.6(3) . . ? C30 C35 C34 109.6(3) . . ? N3 C2 N2 109.9(3) . . ? N3 C2 C20 121.3(3) . . ? N2 C2 C20 128.8(3) . . ? C32 C33 C34 109.7(3) . . ? C34 C36 C37 109.3(3) . . ? C30 C31 C32 109.3(3) . . ? C24 C25 C20 121.1(4) . . ? C36 C37 C39 109.7(4) . . ? C36 C37 C38 109.6(4) . . ? C39 C37 C38 110.0(4) . . ? C22 C21 C20 120.3(4) . . ? C37 C39 C32 108.9(4) . . ? C23 C24 C25 118.5(4) . . ? C13 C12 C11 118.7(4) . . ? C36 C34 C33 109.8(4) . . ? C36 C34 C35 109.2(3) . . ? C33 C34 C35 109.0(3) . . ? C24 C23 C22 121.6(4) . . ? C24 C23 Br23 118.9(3) . . ? C22 C23 Br23 119.5(3) . . ? C33 C32 C39 109.6(4) . . ? C33 C32 C31 109.8(4) . . ? C39 C32 C31 109.3(4) . . ? _diffrn_measured_fraction_theta_max 0.822 _diffrn_reflns_theta_full 30.50 _diffrn_measured_fraction_theta_full 0.822 _refine_diff_density_max 0.819 _refine_diff_density_min -0.959 _refine_diff_density_rms 0.128