# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Javier Adrio' _publ_contact_author_email javier.adrio@uam.es loop_ _publ_author_name 'Maria Gonzalez Esguevillas' 'Javier Adrio' 'Juan C. Carretero' data_datos_0m _database_code_depnum_ccdc_archive 'CCDC 846895' #TrackingRef 'web_deposit_cif_file_0_JavierAdrio_1317643518.datos_0m.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H18 Br N3 O3' _chemical_formula_weight 380.24 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 P2(1)2(1)2(1) 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' _cell_length_a 6.7021(7) _cell_length_b 10.2790(10) _cell_length_c 22.975(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1582.8(3) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9451 _cell_measurement_theta_min 2.66 _cell_measurement_theta_max 28.57 _exptl_crystal_description prismatic _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.596 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 776 _exptl_absorpt_coefficient_mu 2.616 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5075 _exptl_absorpt_correction_T_max 0.8180 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 49056 _diffrn_reflns_av_R_equivalents 0.0456 _diffrn_reflns_av_sigmaI/netI 0.0273 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -29 _diffrn_reflns_limit_l_max 29 _diffrn_reflns_theta_min 1.77 _diffrn_reflns_theta_max 27.52 _reflns_number_total 3615 _reflns_number_gt 3403 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _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 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.1532P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.013(7) _refine_ls_number_reflns 3615 _refine_ls_number_parameters 215 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0239 _refine_ls_R_factor_gt 0.0204 _refine_ls_wR_factor_ref 0.0745 _refine_ls_wR_factor_gt 0.0573 _refine_ls_goodness_of_fit_ref 1.178 _refine_ls_restrained_S_all 1.178 _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 Br1 Br 1.43008(4) 0.67691(3) 0.967734(10) 0.02130(9) Uani 1 1 d . . . C1 C 1.2035(4) 0.6080(3) 0.92791(10) 0.0157(5) Uani 1 1 d . . . C2 C 1.1054(4) 0.5020(3) 0.95191(11) 0.0188(5) Uani 1 1 d . . . H2 H 1.1543 0.4620 0.9863 0.023 Uiso 1 1 calc R . . C3 C 0.9346(4) 0.4552(2) 0.92478(10) 0.0181(5) Uani 1 1 d . . . H3 H 0.8677 0.3819 0.9407 0.022 Uiso 1 1 calc R . . C4 C 0.8596(3) 0.5136(2) 0.87473(10) 0.0127(5) Uani 1 1 d . . . C5 C 0.9633(3) 0.6184(3) 0.85069(10) 0.0153(5) Uani 1 1 d . . . H5 H 0.9158 0.6577 0.8159 0.018 Uiso 1 1 calc R . . C6 C 1.1371(4) 0.6664(3) 0.87727(10) 0.0162(5) Uani 1 1 d . . . H6 H 1.2076 0.7376 0.8608 0.019 Uiso 1 1 calc R . . C7 C 0.6627(3) 0.4675(2) 0.84950(10) 0.0121(4) Uani 1 1 d . . . H7 H 0.5550 0.4982 0.8763 0.014 Uiso 1 1 calc R . . C8 C 0.6367(3) 0.3170(3) 0.84255(9) 0.0128(4) Uani 1 1 d . . . H8 H 0.7649 0.2742 0.8312 0.015 Uiso 1 1 calc R . . C9 C 0.5421(4) 0.2506(2) 0.89480(10) 0.0150(5) Uani 1 1 d . . . C10 C 0.2954(4) 0.2518(2) 0.82453(11) 0.0145(5) Uani 1 1 d . . . C11 C 0.4794(3) 0.3046(2) 0.79441(9) 0.0116(4) Uani 1 1 d . . . H11 H 0.5257 0.2437 0.7633 0.014 Uiso 1 1 calc R . . C12 C 0.4514(3) 0.4454(2) 0.76964(10) 0.0125(4) Uani 1 1 d . . . H12 H 0.3221 0.4832 0.7833 0.015 Uiso 1 1 calc R . . C13 C 0.2097(4) 0.1570(3) 0.92181(11) 0.0216(6) Uani 1 1 d . . . H13A H 0.0717 0.1725 0.9096 0.032 Uiso 1 1 calc R . . H13B H 0.2303 0.1931 0.9608 0.032 Uiso 1 1 calc R . . H13C H 0.2360 0.0633 0.9224 0.032 Uiso 1 1 calc R . . C14 C 0.4596(3) 0.4443(2) 0.70340(10) 0.0134(5) Uani 1 1 d . . . C15 C 0.0891(4) 0.4582(3) 0.70119(11) 0.0178(5) Uani 1 1 d . . . H15A H 0.0737 0.3905 0.7309 0.027 Uiso 1 1 calc R . . H15B H -0.0145 0.4479 0.6714 0.027 Uiso 1 1 calc R . . H15C H 0.0762 0.5440 0.7194 0.027 Uiso 1 1 calc R . . C16 C 0.2880(4) 0.4324(3) 0.61103(10) 0.0196(5) Uani 1 1 d . . . H16A H 0.4257 0.4351 0.5968 0.029 Uiso 1 1 calc R . . H16B H 0.2114 0.5034 0.5934 0.029 Uiso 1 1 calc R . . H16C H 0.2273 0.3489 0.6005 0.029 Uiso 1 1 calc R . . N1 N 0.6201(3) 0.5220(2) 0.79211(9) 0.0130(4) Uani 1 1 d . . . N2 N 0.3455(3) 0.2199(2) 0.88101(9) 0.0150(4) Uani 1 1 d . . . N3 N 0.2872(3) 0.4467(2) 0.67394(9) 0.0147(4) Uani 1 1 d . . . O1 O 0.6162(3) 0.22683(19) 0.94153(8) 0.0246(4) Uani 1 1 d . . . O2 O 0.1289(3) 0.23870(18) 0.80415(8) 0.0196(4) Uani 1 1 d . . . O3 O 0.6252(2) 0.43771(18) 0.67989(8) 0.0177(4) Uani 1 1 d . . . H1 H 0.728(5) 0.506(3) 0.7686(13) 0.025(8) 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 Br1 0.01820(12) 0.02763(15) 0.01808(12) -0.00467(10) -0.00151(10) -0.00937(10) C1 0.0140(11) 0.0166(13) 0.0165(11) -0.0063(9) 0.0000(9) -0.0025(9) C2 0.0224(13) 0.0178(13) 0.0163(12) 0.0011(9) -0.0031(9) -0.0039(10) C3 0.0213(12) 0.0156(13) 0.0174(11) 0.0018(9) 0.0001(11) -0.0068(11) C4 0.0120(10) 0.0115(12) 0.0147(11) -0.0033(9) 0.0011(9) -0.0009(9) C5 0.0145(13) 0.0154(12) 0.0160(11) 0.0014(9) -0.0009(9) -0.0009(9) C6 0.0161(11) 0.0140(12) 0.0186(11) -0.0002(10) 0.0013(9) -0.0033(9) C7 0.0123(10) 0.0114(12) 0.0125(11) 0.0002(8) 0.0004(9) -0.0021(9) C8 0.0134(10) 0.0117(11) 0.0134(10) -0.0001(9) -0.0001(8) -0.0030(9) C9 0.0204(13) 0.0077(12) 0.0170(12) -0.0001(8) -0.0025(10) -0.0042(9) C10 0.0161(11) 0.0099(13) 0.0175(11) -0.0009(9) 0.0006(10) -0.0010(9) C11 0.0131(10) 0.0101(12) 0.0116(10) -0.0006(8) 0.0004(8) -0.0006(8) C12 0.0107(10) 0.0133(12) 0.0134(10) 0.0009(8) 0.0005(9) -0.0001(9) C13 0.0257(13) 0.0208(15) 0.0182(12) 0.0037(10) 0.0034(10) -0.0081(11) C14 0.0136(12) 0.0107(12) 0.0159(11) 0.0017(9) 0.0009(9) 0.0004(9) C15 0.0101(11) 0.0206(13) 0.0227(12) 0.0011(10) 0.0007(10) 0.0019(10) C16 0.0190(12) 0.0260(14) 0.0138(12) 0.0006(10) -0.0039(10) -0.0002(10) N1 0.0115(9) 0.0136(10) 0.0141(10) 0.0020(8) -0.0005(7) -0.0012(7) N2 0.0171(10) 0.0140(11) 0.0139(10) -0.0003(8) 0.0019(8) -0.0039(8) N3 0.0103(9) 0.0207(12) 0.0130(10) 0.0017(8) 0.0008(8) 0.0011(8) O1 0.0322(11) 0.0232(10) 0.0185(9) 0.0082(7) -0.0088(8) -0.0122(8) O2 0.0155(9) 0.0215(10) 0.0217(9) 0.0039(7) -0.0033(7) -0.0059(7) O3 0.0102(8) 0.0265(10) 0.0165(9) 0.0016(7) 0.0027(6) -0.0001(7) _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 Br1 C1 1.909(2) . ? C1 C6 1.382(3) . ? C1 C2 1.387(4) . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . ? C4 C5 1.396(3) . ? C4 C7 1.517(3) . ? C5 C6 1.405(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 N1 1.461(3) . ? C7 C8 1.565(3) . ? C7 H7 1.0000 . ? C8 C9 1.519(3) . ? C8 C11 1.533(3) . ? C8 H8 1.0000 . ? C9 O1 1.208(3) . ? C9 N2 1.392(3) . ? C10 O2 1.218(3) . ? C10 N2 1.380(3) . ? C10 C11 1.514(3) . ? C11 C12 1.567(3) . ? C11 H11 1.0000 . ? C12 N1 1.471(3) . ? C12 C14 1.523(3) . ? C12 H12 1.0000 . ? C13 N2 1.457(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C14 O3 1.236(3) . ? C14 N3 1.339(3) . ? C15 N3 1.473(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 N3 1.453(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? N1 H1 0.92(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 C6 C1 C2 121.5(2) . . ? C6 C1 Br1 119.90(19) . . ? C2 C1 Br1 118.53(18) . . ? C1 C2 C3 119.0(2) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 121.3(2) . . ? C2 C3 H3 119.4 . . ? C4 C3 H3 119.4 . . ? C3 C4 C5 118.7(2) . . ? C3 C4 C7 119.7(2) . . ? C5 C4 C7 121.5(2) . . ? C4 C5 C6 120.8(2) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 118.7(2) . . ? C1 C6 H6 120.6 . . ? C5 C6 H6 120.6 . . ? N1 C7 C4 113.26(19) . . ? N1 C7 C8 105.39(18) . . ? C4 C7 C8 116.41(19) . . ? N1 C7 H7 107.1 . . ? C4 C7 H7 107.1 . . ? C8 C7 H7 107.1 . . ? C9 C8 C11 104.21(18) . . ? C9 C8 C7 114.20(19) . . ? C11 C8 C7 103.46(19) . . ? C9 C8 H8 111.5 . . ? C11 C8 H8 111.5 . . ? C7 C8 H8 111.5 . . ? O1 C9 N2 123.1(2) . . ? O1 C9 C8 128.4(2) . . ? N2 C9 C8 108.5(2) . . ? O2 C10 N2 123.9(2) . . ? O2 C10 C11 127.6(2) . . ? N2 C10 C11 108.5(2) . . ? C10 C11 C8 105.08(18) . . ? C10 C11 C12 113.54(19) . . ? C8 C11 C12 105.49(19) . . ? C10 C11 H11 110.8 . . ? C8 C11 H11 110.8 . . ? C12 C11 H11 110.8 . . ? N1 C12 C14 109.11(19) . . ? N1 C12 C11 105.96(18) . . ? C14 C12 C11 110.57(19) . . ? N1 C12 H12 110.4 . . ? C14 C12 H12 110.4 . . ? C11 C12 H12 110.4 . . ? N2 C13 H13A 109.5 . . ? N2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? N2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O3 C14 N3 123.7(2) . . ? O3 C14 C12 118.0(2) . . ? N3 C14 C12 118.3(2) . . ? N3 C15 H15A 109.5 . . ? N3 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? N3 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? N3 C16 H16A 109.5 . . ? N3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? N3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C7 N1 C12 105.17(18) . . ? C7 N1 H1 107.8(19) . . ? C12 N1 H1 107(2) . . ? C10 N2 C9 113.0(2) . . ? C10 N2 C13 124.0(2) . . ? C9 N2 C13 123.0(2) . . ? C14 N3 C16 119.8(2) . . ? C14 N3 C15 124.4(2) . . ? C16 N3 C15 115.75(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -1.1(4) . . . . ? Br1 C1 C2 C3 176.9(2) . . . . ? C1 C2 C3 C4 -0.8(4) . . . . ? C2 C3 C4 C5 2.2(4) . . . . ? C2 C3 C4 C7 -174.5(2) . . . . ? C3 C4 C5 C6 -1.7(4) . . . . ? C7 C4 C5 C6 174.9(2) . . . . ? C2 C1 C6 C5 1.6(4) . . . . ? Br1 C1 C6 C5 -176.37(18) . . . . ? C4 C5 C6 C1 -0.2(4) . . . . ? C3 C4 C7 N1 -170.2(2) . . . . ? C5 C4 C7 N1 13.2(3) . . . . ? C3 C4 C7 C8 -47.8(3) . . . . ? C5 C4 C7 C8 135.6(2) . . . . ? N1 C7 C8 C9 -142.22(19) . . . . ? C4 C7 C8 C9 91.3(2) . . . . ? N1 C7 C8 C11 -29.6(2) . . . . ? C4 C7 C8 C11 -156.06(19) . . . . ? C11 C8 C9 O1 173.4(2) . . . . ? C7 C8 C9 O1 -74.5(3) . . . . ? C11 C8 C9 N2 -7.2(3) . . . . ? C7 C8 C9 N2 104.9(2) . . . . ? O2 C10 C11 C8 172.2(2) . . . . ? N2 C10 C11 C8 -7.4(3) . . . . ? O2 C10 C11 C12 57.4(3) . . . . ? N2 C10 C11 C12 -122.2(2) . . . . ? C9 C8 C11 C10 8.6(2) . . . . ? C7 C8 C11 C10 -111.06(19) . . . . ? C9 C8 C11 C12 128.89(19) . . . . ? C7 C8 C11 C12 9.2(2) . . . . ? C10 C11 C12 N1 128.4(2) . . . . ? C8 C11 C12 N1 13.8(2) . . . . ? C10 C11 C12 C14 -113.5(2) . . . . ? C8 C11 C12 C14 131.94(19) . . . . ? N1 C12 C14 O3 37.6(3) . . . . ? C11 C12 C14 O3 -78.5(3) . . . . ? N1 C12 C14 N3 -144.2(2) . . . . ? C11 C12 C14 N3 99.6(2) . . . . ? C4 C7 N1 C12 167.68(18) . . . . ? C8 C7 N1 C12 39.3(2) . . . . ? C14 C12 N1 C7 -152.14(19) . . . . ? C11 C12 N1 C7 -33.1(2) . . . . ? O2 C10 N2 C9 -176.6(2) . . . . ? C11 C10 N2 C9 3.1(3) . . . . ? O2 C10 N2 C13 5.1(4) . . . . ? C11 C10 N2 C13 -175.2(2) . . . . ? O1 C9 N2 C10 -177.8(2) . . . . ? C8 C9 N2 C10 2.8(3) . . . . ? O1 C9 N2 C13 0.5(4) . . . . ? C8 C9 N2 C13 -179.0(2) . . . . ? O3 C14 N3 C16 4.3(4) . . . . ? C12 C14 N3 C16 -173.7(2) . . . . ? O3 C14 N3 C15 -178.2(2) . . . . ? C12 C14 N3 C15 3.8(4) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.52 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.292 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.088