# Supplementary Material (ESI) for ChemComm # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 182/1619 data_s92 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H28 Br N3 O' _chemical_formula_weight 382.34 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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 13.352(3) _cell_length_b 14.822(3) _cell_length_c 18.105(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3583.0(13) _cell_formula_units_Z 8 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 24587 _cell_measurement_theta_min 2.25 _cell_measurement_theta_max 27.49 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.05 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.418 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1600 _exptl_absorpt_coefficient_mu 2.303 _exptl_absorpt_correction_type multi-scans _exptl_absorpt_correction_T_min 0.463 _exptl_absorpt_correction_T_max 0.918 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Phi and Omega scans' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24587 _diffrn_reflns_av_R_equivalents 0.0807 _diffrn_reflns_av_sigmaI/netI 0.0445 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 27.49 _reflns_number_total 4107 _reflns_number_gt 3164 _reflns_threshold_expression >2sigma(I) loop_ _computing_data_collection 'DENZO (Otwinowski and Minor, 1997)' 'COLLECT (Hooft, 1998)' _computing_cell_refinement 'DENZO and COLLECT' _computing_data_reduction 'DENZO and COLLECT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'CAMERON (Watkin and Pearce, 1995)' _computing_publication_material ? _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 w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment riding _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4107 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0410 _refine_ls_wR_factor_ref 0.1283 _refine_ls_wR_factor_gt 0.1123 _refine_ls_goodness_of_fit_ref 0.908 _refine_ls_restrained_S_all 0.908 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.67084(2) 0.113390(16) 0.347826(14) 0.02808(13) Uani 1 d . . . O1 O 0.36868(14) -0.53120(12) 0.43143(10) 0.0311(4) Uani 1 d . . . N1 N 0.43509(16) -0.10510(12) 0.38478(12) 0.0243(4) Uani 1 d . . . N2 N 0.62289(15) -0.17004(12) 0.29788(12) 0.0253(4) Uani 1 d . . . N3 N 0.51107(16) -0.09036(13) 0.22322(12) 0.0273(5) Uani 1 d . . . C1 C 0.5158(2) -0.10415(16) 0.44100(15) 0.0294(6) Uani 1 d . . . H1A H 0.4856 -0.1069 0.4897 0.035 Uiso 1 calc R . . H1B H 0.5517 -0.0474 0.4374 0.035 Uiso 1 calc R . . C2 C 0.59106(19) -0.18186(17) 0.43352(14) 0.0308(6) Uani 1 d . . . H2A H 0.6260 -0.1888 0.4801 0.037 Uiso 1 calc R . . H2B H 0.5543 -0.2372 0.4244 0.037 Uiso 1 calc R . . C3 C 0.66866(18) -0.16966(19) 0.37211(16) 0.0293(6) Uani 1 d . . . H3A H 0.7036 -0.1130 0.3795 0.035 Uiso 1 calc R . . H3B H 0.7176 -0.2179 0.3751 0.035 Uiso 1 calc R . . C4 C 0.57668(19) -0.09623(15) 0.27662(15) 0.0254(5) Uani 1 d . . . H4 H 0.5920 -0.0434 0.3018 0.030 Uiso 1 calc R . . C5 C 0.59504(19) -0.25640(17) 0.26436(16) 0.0302(6) Uani 1 d . . . H5A H 0.5402 -0.2833 0.2917 0.036 Uiso 1 calc R . . H5B H 0.6515 -0.2975 0.2661 0.036 Uiso 1 calc R . . C6 C 0.5639(2) -0.24111(18) 0.18521(15) 0.0355(6) Uani 1 d . . . H6A H 0.5397 -0.2972 0.1642 0.043 Uiso 1 calc R . . H6B H 0.6212 -0.2213 0.1566 0.043 Uiso 1 calc R . . C7 C 0.4821(2) -0.17047(18) 0.18139(16) 0.0343(6) Uani 1 d . . . H7A H 0.4701 -0.1541 0.1303 0.041 Uiso 1 calc R . . H7B H 0.4205 -0.1950 0.2015 0.041 Uiso 1 calc R . . C8 C 0.4464(2) -0.00998(17) 0.22207(16) 0.0334(6) Uani 1 d . . . H8A H 0.4148 -0.0053 0.1740 0.040 Uiso 1 calc R . . H8B H 0.4875 0.0433 0.2291 0.040 Uiso 1 calc R . . C9 C 0.3654(2) -0.01216(18) 0.28153(16) 0.0332(6) Uani 1 d . . . H9A H 0.3245 -0.0656 0.2743 0.040 Uiso 1 calc R . . H9B H 0.3224 0.0401 0.2754 0.040 Uiso 1 calc R . . C10 C 0.4060(2) -0.01266(16) 0.36036(15) 0.0304(6) Uani 1 d . . . H10A H 0.4640 0.0267 0.3631 0.036 Uiso 1 calc R . . H10B H 0.3554 0.0109 0.3935 0.036 Uiso 1 calc R . . C11 C 0.34433(19) -0.15006(18) 0.41322(16) 0.0307(6) Uani 1 d . . . H11A H 0.2889 -0.1357 0.3807 0.037 Uiso 1 calc R . . H11B H 0.3289 -0.1251 0.4614 0.037 Uiso 1 calc R . . C12 C 0.35103(18) -0.25109(16) 0.42029(15) 0.0262(5) Uani 1 d . . . C13 C 0.34661(18) -0.30605(19) 0.35759(13) 0.0260(5) Uani 1 d . . . H13 H 0.3403 -0.2794 0.3113 0.031 Uiso 1 calc R . . C14 C 0.3513(2) -0.39854(18) 0.36255(15) 0.0266(5) Uani 1 d . . . H14 H 0.3483 -0.4338 0.3201 0.032 Uiso 1 calc R . . C15 C 0.36052(18) -0.43884(16) 0.43158(14) 0.0243(5) Uani 1 d . . . C16 C 0.3616(2) -0.38622(16) 0.49476(15) 0.0275(6) Uani 1 d . . . H16 H 0.3652 -0.4131 0.5411 0.033 Uiso 1 calc R . . C17 C 0.35717(17) -0.29253(17) 0.48840(14) 0.0277(5) Uani 1 d . . . H17 H 0.3584 -0.2573 0.5309 0.033 Uiso 1 calc R . . C18 C 0.3715(2) -0.57556(18) 0.50154(16) 0.0357(6) Uani 1 d . . . H18A H 0.4297 -0.5563 0.5284 0.054 Uiso 1 calc R . . H18B H 0.3742 -0.6397 0.4942 0.054 Uiso 1 calc R . . H18C H 0.3124 -0.5605 0.5291 0.054 Uiso 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 Br1 0.02780(19) 0.02232(18) 0.03412(19) -0.00293(9) -0.00053(10) -0.00498(9) O1 0.0320(10) 0.0214(9) 0.0397(10) 0.0013(7) 0.0033(8) -0.0027(8) N1 0.0178(10) 0.0192(10) 0.0360(12) 0.0025(8) 0.0008(9) 0.0018(8) N2 0.0191(10) 0.0178(10) 0.0389(12) -0.0022(8) -0.0028(9) -0.0007(8) N3 0.0246(11) 0.0222(10) 0.0350(12) 0.0025(9) -0.0033(9) -0.0015(9) C1 0.0263(13) 0.0267(12) 0.0350(14) -0.0025(10) -0.0004(11) -0.0010(11) C2 0.0288(13) 0.0276(13) 0.0359(14) 0.0027(10) -0.0067(11) 0.0018(11) C3 0.0190(12) 0.0267(13) 0.0420(14) -0.0016(11) -0.0081(11) 0.0030(10) C4 0.0205(12) 0.0183(11) 0.0374(13) -0.0019(10) 0.0021(10) -0.0032(10) C5 0.0249(13) 0.0192(12) 0.0465(16) -0.0055(10) -0.0021(11) 0.0013(10) C6 0.0312(14) 0.0303(14) 0.0449(16) -0.0095(12) -0.0001(12) -0.0023(12) C7 0.0316(14) 0.0328(14) 0.0384(15) -0.0016(11) -0.0063(12) -0.0052(12) C8 0.0312(14) 0.0258(13) 0.0434(15) 0.0101(11) -0.0030(12) 0.0038(11) C9 0.0228(13) 0.0248(13) 0.0518(16) 0.0096(12) -0.0013(12) 0.0050(11) C10 0.0225(13) 0.0205(12) 0.0482(15) 0.0012(11) 0.0043(11) 0.0048(10) C11 0.0214(12) 0.0263(13) 0.0442(15) 0.0038(12) 0.0054(11) -0.0001(11) C12 0.0158(11) 0.0241(13) 0.0388(13) 0.0033(10) 0.0034(10) 0.0007(10) C13 0.0192(12) 0.0305(14) 0.0284(12) 0.0041(10) 0.0026(9) -0.0007(11) C14 0.0202(12) 0.0321(14) 0.0275(12) -0.0028(10) 0.0013(10) -0.0043(11) C15 0.0154(11) 0.0225(12) 0.0349(13) -0.0013(10) 0.0016(10) -0.0041(10) C16 0.0239(12) 0.0276(14) 0.0311(13) 0.0044(10) 0.0039(11) -0.0047(10) C17 0.0212(11) 0.0309(14) 0.0310(12) -0.0039(11) 0.0034(10) -0.0042(11) C18 0.0303(14) 0.0309(14) 0.0460(16) 0.0108(12) -0.0029(13) -0.0017(12) _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 O1 C15 1.373(3) . ? O1 C18 1.430(3) . ? N1 C11 1.476(3) . ? N1 C1 1.483(3) . ? N1 C10 1.491(3) . ? N2 C4 1.314(3) . ? N2 C5 1.465(3) . ? N2 C3 1.476(3) . ? N3 C4 1.308(3) . ? N3 C7 1.461(3) . ? N3 C8 1.471(3) . ? C1 C2 1.534(4) . ? C2 C3 1.531(4) . ? C5 C6 1.509(4) . ? C6 C7 1.514(4) . ? C8 C9 1.527(4) . ? C9 C10 1.527(4) . ? C11 C12 1.506(4) . ? C12 C17 1.380(4) . ? C12 C13 1.399(4) . ? C13 C14 1.375(4) . ? C14 C15 1.391(4) . ? C15 C16 1.385(4) . ? C16 C17 1.395(3) . ? 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 C15 O1 C18 117.3(2) . . ? C11 N1 C1 111.2(2) . . ? C11 N1 C10 107.75(19) . . ? C1 N1 C10 112.57(19) . . ? C4 N2 C5 119.2(2) . . ? C4 N2 C3 117.3(2) . . ? C5 N2 C3 119.1(2) . . ? C4 N3 C7 120.5(2) . . ? C4 N3 C8 117.2(2) . . ? C7 N3 C8 119.7(2) . . ? N1 C1 C2 114.1(2) . . ? C3 C2 C1 114.8(2) . . ? N2 C3 C2 112.37(19) . . ? N3 C4 N2 125.9(2) . . ? N2 C5 C6 109.4(2) . . ? C5 C6 C7 110.2(2) . . ? N3 C7 C6 110.3(2) . . ? N3 C8 C9 112.9(2) . . ? C8 C9 C10 114.0(2) . . ? N1 C10 C9 112.0(2) . . ? N1 C11 C12 115.5(2) . . ? C17 C12 C13 117.9(2) . . ? C17 C12 C11 121.5(2) . . ? C13 C12 C11 120.5(2) . . ? C14 C13 C12 121.7(2) . . ? C13 C14 C15 119.4(2) . . ? O1 C15 C16 124.2(2) . . ? O1 C15 C14 115.7(2) . . ? C16 C15 C14 120.1(2) . . ? C15 C16 C17 119.5(2) . . ? C12 C17 C16 121.3(2) . . ? _diffrn_measured_fraction_theta_max 0.900 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.900 _refine_diff_density_max 0.731 _refine_diff_density_min -0.939 _refine_diff_density_rms 0.085