# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_suman _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H36 Br N3 O4' _chemical_formula_sum 'C25 H36 Br N3 O4' _chemical_formula_weight 522.48 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' 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.4792(19) _cell_length_b 16.843(2) _cell_length_c 11.8341(17) _cell_angle_alpha 90.00 _cell_angle_beta 107.838(2) _cell_angle_gamma 90.00 _cell_volume 2557.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4563 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 24.95 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.468 _exptl_crystal_size_mid 0.365 _exptl_crystal_size_min 0.245 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.642 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.492 _exptl_absorpt_correction_T_max 0.669 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 17222 _diffrn_reflns_av_R_equivalents 0.0526 _diffrn_reflns_av_sigmaI/netI 0.0455 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 24.99 _reflns_number_total 4450 _reflns_number_gt 3257 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0370P)^2^+3.5441P] 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 4450 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0516 _refine_ls_R_factor_gt 0.0364 _refine_ls_wR_factor_ref 0.0914 _refine_ls_wR_factor_gt 0.0846 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _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 Br1 Br 0.33948(3) 0.809238(18) 0.57665(3) 0.01889(12) Uani 1 1 d . . . O1 O 0.02375(16) 1.12084(13) 0.88123(19) 0.0214(5) Uani 1 1 d . . . O2 O -0.03550(18) 1.05223(14) 0.7060(2) 0.0286(6) Uani 1 1 d . . . O3 O 0.41541(16) 0.80370(12) 0.90733(19) 0.0178(5) Uani 1 1 d . . . O4 O 0.68603(16) 0.92039(12) 0.95304(19) 0.0194(5) Uani 1 1 d . . . N1 N 0.1335(2) 1.04308(15) 0.8283(2) 0.0211(7) Uani 1 1 d . . . H1 H 0.1750 1.0613 0.8936 0.025 Uiso 1 1 calc R . . N2 N 0.51237(19) 0.89925(14) 0.8506(2) 0.0123(6) Uani 1 1 d . . . N3 N 0.6211(2) 0.79716(15) 0.9597(2) 0.0193(6) Uani 1 1 d . . . H3 H 0.5670 0.7672 0.9356 0.023 Uiso 1 1 calc R . . C1 C -0.1449(3) 1.0741(2) 0.8915(4) 0.0405(10) Uani 1 1 d . . . H1A H -0.1666 1.0467 0.8168 0.061 Uiso 1 1 calc R . . H1B H -0.2052 1.0904 0.9125 0.061 Uiso 1 1 calc R . . H1C H -0.1030 1.0394 0.9517 0.061 Uiso 1 1 calc R . . C2 C -0.0818(2) 1.1465(2) 0.8812(3) 0.0229(8) Uani 1 1 d . . . C3 C 0.0331(3) 1.07032(19) 0.7956(3) 0.0206(8) Uani 1 1 d . . . C4 C 0.1760(2) 0.98834(18) 0.7659(3) 0.0181(7) Uani 1 1 d . . . C5 C 0.2694(2) 0.95369(18) 0.8292(3) 0.0188(8) Uani 1 1 d . . . H5 H 0.2990 0.9657 0.9092 0.023 Uiso 1 1 calc R . . C6 C 0.3199(2) 0.90041(17) 0.7735(3) 0.0145(7) Uani 1 1 d . . . C7 C 0.4206(2) 0.86238(18) 0.8487(3) 0.0148(7) Uani 1 1 d . . . C8 C 0.6132(2) 0.87307(18) 0.9262(3) 0.0145(7) Uani 1 1 d . . . C9 C 0.7188(2) 0.76297(18) 1.0364(3) 0.0172(7) Uani 1 1 d . . . H9 H 0.7770 0.7923 1.0230 0.021 Uiso 1 1 calc R . . C10 C 0.7272(3) 0.7697(2) 1.1673(3) 0.0236(8) Uani 1 1 d . . . H10A H 0.6684 0.7430 1.1816 0.028 Uiso 1 1 calc R . . H10B H 0.7247 0.8253 1.1881 0.028 Uiso 1 1 calc R . . C11 C 0.8287(3) 0.7328(2) 1.2455(3) 0.0262(8) Uani 1 1 d . . . H11A H 0.8875 0.7628 1.2371 0.031 Uiso 1 1 calc R . . H11B H 0.8305 0.7354 1.3280 0.031 Uiso 1 1 calc R . . C12 C 0.8382(3) 0.6462(2) 1.2113(3) 0.0295(9) Uani 1 1 d . . . H12A H 0.9054 0.6255 1.2581 0.035 Uiso 1 1 calc R . . H12B H 0.7845 0.6149 1.2291 0.035 Uiso 1 1 calc R . . C13 C -0.0580(3) 1.1969(3) 0.9921(3) 0.0422(11) Uani 1 1 d . . . H13A H -0.0201 1.1659 1.0596 0.063 Uiso 1 1 calc R . . H13B H -0.1220 1.2151 1.0029 0.063 Uiso 1 1 calc R . . H13C H -0.0167 1.2418 0.9843 0.063 Uiso 1 1 calc R . . C14 C -0.1328(3) 1.1965(2) 0.7723(3) 0.0307(9) Uani 1 1 d . . . H14A H -0.0862 1.2384 0.7665 0.046 Uiso 1 1 calc R . . H14B H -0.1962 1.2190 0.7790 0.046 Uiso 1 1 calc R . . H14C H -0.1481 1.1638 0.7026 0.046 Uiso 1 1 calc R . . C15 C 0.5091(2) 0.97412(17) 0.7807(3) 0.0135(7) Uani 1 1 d . . . H15 H 0.4394 0.9759 0.7226 0.016 Uiso 1 1 calc R . . C16 C 0.5853(3) 0.97417(19) 0.7088(3) 0.0196(7) Uani 1 1 d . . . H16A H 0.5747 0.9272 0.6590 0.024 Uiso 1 1 calc R . . H16B H 0.6563 0.9736 0.7616 0.024 Uiso 1 1 calc R . . C17 C 0.5667(3) 1.0492(2) 0.6313(3) 0.0291(9) Uani 1 1 d . . . H17A H 0.6177 1.0514 0.5887 0.035 Uiso 1 1 calc R . . H17B H 0.4981 1.0465 0.5733 0.035 Uiso 1 1 calc R . . C18 C 0.5746(3) 1.1242(2) 0.7049(3) 0.0304(9) Uani 1 1 d . . . H18A H 0.6453 1.1298 0.7575 0.037 Uiso 1 1 calc R . . H18B H 0.5593 1.1700 0.6526 0.037 Uiso 1 1 calc R . . C19 C 0.4997(3) 1.12236(18) 0.7778(3) 0.0209(8) Uani 1 1 d . . . H19A H 0.4287 1.1222 0.7251 0.025 Uiso 1 1 calc R . . H19B H 0.5092 1.1697 0.8267 0.025 Uiso 1 1 calc R . . C20 C 0.5179(3) 1.04904(18) 0.8567(3) 0.0187(7) Uani 1 1 d . . . H20A H 0.4667 1.0472 0.8991 0.022 Uiso 1 1 calc R . . H20B H 0.5866 1.0516 0.9147 0.022 Uiso 1 1 calc R . . C21 C 0.7268(3) 0.67617(19) 1.0020(3) 0.0243(8) Uani 1 1 d . . . H21A H 0.6675 0.6468 1.0104 0.029 Uiso 1 1 calc R . . H21B H 0.7249 0.6733 0.9195 0.029 Uiso 1 1 calc R . . C22 C 0.8275(3) 0.6385(2) 1.0801(3) 0.0294(9) Uani 1 1 d . . . H22A H 0.8285 0.5827 1.0599 0.035 Uiso 1 1 calc R . . H22B H 0.8865 0.6639 1.0644 0.035 Uiso 1 1 calc R . . C23 C 0.2737(2) 0.88091(18) 0.6554(3) 0.0170(7) Uani 1 1 d . . . C24 C 0.1785(3) 0.91484(19) 0.5922(3) 0.0218(8) Uani 1 1 d . . . H24 H 0.1476 0.9015 0.5129 0.026 Uiso 1 1 calc R . . C25 C 0.1297(3) 0.96818(19) 0.6465(3) 0.0210(8) Uani 1 1 d . . . H25 H 0.0663 0.9906 0.6037 0.025 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 Br1 0.02095(19) 0.01719(18) 0.01872(18) -0.00220(14) 0.00636(13) 0.00078(15) O1 0.0137(12) 0.0224(12) 0.0256(13) -0.0069(10) 0.0025(10) 0.0042(10) O2 0.0202(13) 0.0317(14) 0.0255(13) -0.0107(11) -0.0054(11) 0.0049(11) O3 0.0167(12) 0.0125(11) 0.0241(12) 0.0045(10) 0.0062(10) 0.0000(10) O4 0.0129(12) 0.0157(11) 0.0248(13) 0.0000(10) -0.0013(10) -0.0024(10) N1 0.0152(15) 0.0230(15) 0.0204(15) -0.0073(12) -0.0015(12) 0.0030(12) N2 0.0124(14) 0.0100(13) 0.0132(13) 0.0018(10) 0.0019(11) 0.0005(11) N3 0.0130(14) 0.0134(15) 0.0252(15) 0.0055(11) -0.0034(12) -0.0016(11) C1 0.025(2) 0.043(2) 0.057(3) 0.011(2) 0.016(2) 0.0017(19) C2 0.0107(17) 0.0266(19) 0.0302(19) -0.0053(15) 0.0045(15) 0.0040(15) C3 0.0179(18) 0.0172(17) 0.0256(19) -0.0004(15) 0.0052(16) 0.0028(15) C4 0.0170(18) 0.0147(16) 0.0222(17) -0.0010(14) 0.0054(14) -0.0003(14) C5 0.0110(17) 0.0150(17) 0.0250(18) 0.0056(14) -0.0027(14) -0.0037(14) C6 0.0128(17) 0.0108(16) 0.0197(17) 0.0023(13) 0.0045(14) -0.0027(13) C7 0.0179(17) 0.0119(16) 0.0150(16) -0.0044(13) 0.0057(14) 0.0008(13) C8 0.0166(17) 0.0170(17) 0.0098(15) -0.0018(13) 0.0037(13) 0.0022(15) C9 0.0111(16) 0.0168(17) 0.0202(17) 0.0057(13) -0.0004(14) 0.0007(13) C10 0.0194(19) 0.0260(19) 0.0240(18) 0.0020(15) 0.0047(15) 0.0049(15) C11 0.027(2) 0.033(2) 0.0166(17) 0.0047(15) 0.0034(15) 0.0059(17) C12 0.021(2) 0.029(2) 0.031(2) 0.0120(16) -0.0030(16) 0.0033(16) C13 0.026(2) 0.065(3) 0.031(2) -0.015(2) 0.0025(18) 0.016(2) C14 0.0218(19) 0.037(2) 0.033(2) -0.0007(17) 0.0080(16) 0.0111(17) C15 0.0131(16) 0.0110(15) 0.0140(16) 0.0030(12) 0.0008(13) -0.0015(13) C16 0.0232(19) 0.0154(17) 0.0223(18) 0.0013(14) 0.0100(15) 0.0005(15) C17 0.034(2) 0.026(2) 0.035(2) 0.0118(17) 0.0211(18) 0.0020(17) C18 0.032(2) 0.0161(18) 0.045(2) 0.0099(16) 0.0139(19) 0.0013(16) C19 0.0220(19) 0.0096(16) 0.0280(19) 0.0002(14) 0.0029(15) 0.0005(14) C20 0.0196(18) 0.0137(16) 0.0181(17) -0.0013(13) -0.0011(14) -0.0001(14) C21 0.0230(19) 0.0180(18) 0.0252(18) 0.0001(14) -0.0024(15) 0.0031(15) C22 0.028(2) 0.0183(18) 0.036(2) -0.0030(16) 0.0007(17) 0.0043(16) C23 0.0165(17) 0.0120(16) 0.0234(18) 0.0012(13) 0.0073(14) -0.0018(14) C24 0.0222(19) 0.0220(18) 0.0177(17) 0.0012(14) 0.0011(15) -0.0002(15) C25 0.0158(17) 0.0233(18) 0.0200(18) -0.0008(14) -0.0003(15) 0.0040(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 Br1 C23 1.902(3) . ? O1 C3 1.358(4) . ? O1 C2 1.486(4) . ? O2 C3 1.213(4) . ? O3 C7 1.222(4) . ? O4 C8 1.228(4) . ? N1 C3 1.368(4) . ? N1 C4 1.407(4) . ? N1 H1 0.8600 . ? N2 C7 1.378(4) . ? N2 C8 1.449(4) . ? N2 C15 1.501(4) . ? N3 C8 1.333(4) . ? N3 C9 1.469(4) . ? N3 H3 0.8600 . ? C1 C2 1.512(5) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C13 1.514(5) . ? C2 C14 1.516(5) . ? C4 C5 1.382(4) . ? C4 C25 1.401(4) . ? C5 C6 1.407(5) . ? C5 H5 0.9300 . ? C6 C23 1.384(4) . ? C6 C7 1.517(4) . ? C9 C10 1.522(5) . ? C9 C21 1.530(4) . ? C9 H9 0.9800 . ? C10 C11 1.530(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.529(5) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C22 1.521(5) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.521(4) . ? C15 C20 1.533(4) . ? C15 H15 0.9800 . ? C16 C17 1.536(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.519(5) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.515(5) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.523(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.527(5) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.394(4) . ? C24 C25 1.382(5) . ? C24 H24 0.9300 . ? C25 H25 0.9300 . ? 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 C3 O1 C2 119.3(2) . . ? C3 N1 C4 126.7(3) . . ? C3 N1 H1 116.7 . . ? C4 N1 H1 116.7 . . ? C7 N2 C8 122.8(3) . . ? C7 N2 C15 119.6(2) . . ? C8 N2 C15 117.4(2) . . ? C8 N3 C9 122.3(3) . . ? C8 N3 H3 118.9 . . ? C9 N3 H3 118.9 . . ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? O1 C2 C1 109.1(3) . . ? O1 C2 C13 102.3(3) . . ? C1 C2 C13 110.9(3) . . ? O1 C2 C14 110.3(3) . . ? C1 C2 C14 113.4(3) . . ? C13 C2 C14 110.2(3) . . ? O2 C3 O1 126.1(3) . . ? O2 C3 N1 125.9(3) . . ? O1 C3 N1 108.0(3) . . ? C5 C4 C25 119.6(3) . . ? C5 C4 N1 116.2(3) . . ? C25 C4 N1 124.1(3) . . ? C4 C5 C6 120.5(3) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C23 C6 C5 119.4(3) . . ? C23 C6 C7 122.5(3) . . ? C5 C6 C7 118.0(3) . . ? O3 C7 N2 124.2(3) . . ? O3 C7 C6 118.6(3) . . ? N2 C7 C6 117.2(3) . . ? O4 C8 N3 124.2(3) . . ? O4 C8 N2 119.1(3) . . ? N3 C8 N2 116.7(3) . . ? N3 C9 C10 111.8(3) . . ? N3 C9 C21 109.5(2) . . ? C10 C9 C21 110.7(3) . . ? N3 C9 H9 108.3 . . ? C10 C9 H9 108.3 . . ? C21 C9 H9 108.3 . . ? C9 C10 C11 111.1(3) . . ? C9 C10 H10A 109.4 . . ? C11 C10 H10A 109.4 . . ? C9 C10 H10B 109.4 . . ? C11 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? C12 C11 C10 111.1(3) . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C22 C12 C11 111.3(3) . . ? C22 C12 H12A 109.4 . . ? C11 C12 H12A 109.4 . . ? C22 C12 H12B 109.4 . . ? C11 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C2 C13 H13A 109.5 . . ? C2 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C2 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C2 C14 H14A 109.5 . . ? C2 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C2 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? N2 C15 C16 113.4(3) . . ? N2 C15 C20 112.6(2) . . ? C16 C15 C20 112.6(3) . . ? N2 C15 H15 105.8 . . ? C16 C15 H15 105.8 . . ? C20 C15 H15 105.8 . . ? C15 C16 C17 108.6(3) . . ? C15 C16 H16A 110.0 . . ? C17 C16 H16A 110.0 . . ? C15 C16 H16B 110.0 . . ? C17 C16 H16B 110.0 . . ? H16A C16 H16B 108.3 . . ? C18 C17 C16 111.9(3) . . ? C18 C17 H17A 109.2 . . ? C16 C17 H17A 109.2 . . ? C18 C17 H17B 109.2 . . ? C16 C17 H17B 109.2 . . ? H17A C17 H17B 107.9 . . ? C19 C18 C17 111.5(3) . . ? C19 C18 H18A 109.3 . . ? C17 C18 H18A 109.3 . . ? C19 C18 H18B 109.3 . . ? C17 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C18 C19 C20 110.9(3) . . ? C18 C19 H19A 109.5 . . ? C20 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C20 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? C19 C20 C15 109.8(3) . . ? C19 C20 H20A 109.7 . . ? C15 C20 H20A 109.7 . . ? C19 C20 H20B 109.7 . . ? C15 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C22 C21 C9 111.0(3) . . ? C22 C21 H21A 109.4 . . ? C9 C21 H21A 109.4 . . ? C22 C21 H21B 109.4 . . ? C9 C21 H21B 109.4 . . ? H21A C21 H21B 108.0 . . ? C12 C22 C21 111.8(3) . . ? C12 C22 H22A 109.3 . . ? C21 C22 H22A 109.3 . . ? C12 C22 H22B 109.3 . . ? C21 C22 H22B 109.3 . . ? H22A C22 H22B 107.9 . . ? C6 C23 C24 120.0(3) . . ? C6 C23 Br1 120.8(2) . . ? C24 C23 Br1 119.2(2) . . ? C25 C24 C23 120.5(3) . . ? C25 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C24 C25 C4 119.9(3) . . ? C24 C25 H25 120.1 . . ? C4 C25 H25 120.1 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.517 _refine_diff_density_min -0.502 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 942337' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_dh _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H36 Br N3 O4' _chemical_formula_sum 'C25 H36 Br N3 O4' _chemical_formula_weight 522.48 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' 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 Monoclinic _symmetry_space_group_name_H-M 'P2(1)/c ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 13.649(13) _cell_length_b 16.921(16) _cell_length_c 12.008(12) _cell_angle_alpha 90.00 _cell_angle_beta 108.526(15) _cell_angle_gamma 90.00 _cell_volume 2629(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 2.88 _cell_measurement_theta_max 18.02 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.481 _exptl_crystal_size_mid 0.393 _exptl_crystal_size_min 0.256 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1096 _exptl_absorpt_coefficient_mu 1.597 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.476 _exptl_absorpt_correction_T_max 0.664 _exptl_absorpt_process_details '(SADABS; Bruker, 2008)' _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 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 19475 _diffrn_reflns_av_R_equivalents 0.0901 _diffrn_reflns_av_sigmaI/netI 0.1239 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 24.94 _reflns_number_total 4442 _reflns_number_gt 2200 _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, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0417P)^2^+1.1983P] 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 4442 _refine_ls_number_parameters 301 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1519 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.0924 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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 Br1 Br 0.66380(4) 0.18808(3) 0.42481(4) 0.0555(2) Uani 1 1 d . . . O1 O 0.9737(2) -0.1147(2) 0.1192(3) 0.0569(10) Uani 1 1 d . . . O2 O 1.0318(3) -0.0504(2) 0.2945(3) 0.0781(13) Uani 1 1 d . . . O3 O 0.5855(2) 0.1966(2) 0.1001(3) 0.0522(9) Uani 1 1 d . . . O4 O 0.3175(3) 0.0791(2) 0.0457(3) 0.0486(10) Uani 1 1 d . . . N1 N 0.4891(3) 0.1000(2) 0.1493(3) 0.0320(10) Uani 1 1 d . . . C26 C 0.7298(3) 0.0483(3) 0.1748(4) 0.0397(13) Uani 1 1 d . . . H2 H 0.6989 0.0366 0.0957 0.048 Uiso 1 1 calc R . . N3 N 0.8645(3) -0.0396(2) 0.1727(3) 0.0491(12) Uani 1 1 d . . . H3 H 0.8227 -0.0568 0.1075 0.059 Uiso 1 1 calc R . . C1 C 0.1682(5) 0.3538(4) -0.2024(6) 0.094(2) Uani 1 1 d . . . H1A H 0.2229 0.3850 -0.2158 0.113 Uiso 1 1 calc R . . H1B H 0.1026 0.3760 -0.2495 0.113 Uiso 1 1 calc R . . C2 C 0.1762(5) 0.2687(5) -0.2408(5) 0.093(2) Uani 1 1 d . . . H2A H 0.1745 0.2679 -0.3222 0.112 Uiso 1 1 calc R . . H2B H 0.1179 0.2383 -0.2346 0.112 Uiso 1 1 calc R . . C3 C 0.2768(4) 0.2317(4) -0.1633(4) 0.0767(19) Uani 1 1 d . . . H3A H 0.2795 0.1768 -0.1854 0.092 Uiso 1 1 calc R . . H3B H 0.3349 0.2590 -0.1759 0.092 Uiso 1 1 calc R . . C4 C 0.2853(4) 0.2364(3) -0.0355(4) 0.0488(14) Uani 1 1 d . . . H4 H 0.2276 0.2065 -0.0244 0.059 Uiso 1 1 calc R . . N2 N 0.3819(3) 0.2007(2) 0.0395(3) 0.0547(12) Uani 1 1 d . . . H5 H 0.4361 0.2299 0.0634 0.066 Uiso 1 1 calc R . . C6 C 0.3893(4) 0.1254(3) 0.0721(4) 0.0366(13) Uani 1 1 d . . . C7 C 0.5802(4) 0.1373(3) 0.1549(4) 0.0361(13) Uani 1 1 d . . . C8 C 0.6808(3) 0.0997(3) 0.2292(4) 0.0345(12) Uani 1 1 d . . . C9 C 0.8239(4) 0.0136(3) 0.2351(4) 0.0416(13) Uani 1 1 d . . . C10 C 0.9647(4) -0.0674(3) 0.2045(5) 0.0547(15) Uani 1 1 d . . . C11 C 1.0777(4) -0.1412(4) 0.1202(5) 0.0598(17) Uani 1 1 d . . . C12 C 1.1408(5) -0.0688(4) 0.1163(6) 0.101(2) Uani 1 1 d . . . H12A H 1.0977 -0.0303 0.0648 0.151 Uiso 1 1 calc R . . H12B H 1.1967 -0.0830 0.0879 0.151 Uiso 1 1 calc R . . H12C H 1.1681 -0.0469 0.1938 0.151 Uiso 1 1 calc R . . C13 C 1.0523(5) -0.1868(4) 0.0065(6) 0.115(3) Uani 1 1 d . . . H13A H 1.0123 -0.2327 0.0110 0.172 Uiso 1 1 calc R . . H13B H 1.1152 -0.2029 -0.0067 0.172 Uiso 1 1 calc R . . H13C H 1.0133 -0.1538 -0.0572 0.172 Uiso 1 1 calc R . . C14 C 1.1274(4) -0.1936(4) 0.2238(5) 0.0812(19) Uani 1 1 d . . . H14A H 1.1421 -0.1633 0.2949 0.122 Uiso 1 1 calc R . . H14B H 1.1906 -0.2147 0.2172 0.122 Uiso 1 1 calc R . . H14C H 1.0814 -0.2361 0.2255 0.122 Uiso 1 1 calc R . . C15 C 0.7278(4) 0.1177(3) 0.3465(4) 0.0367(12) Uani 1 1 d . . . C16 C 0.8225(4) 0.0843(3) 0.4066(4) 0.0540(15) Uani 1 1 d . . . H16 H 0.8543 0.0973 0.4851 0.065 Uiso 1 1 calc R . . C17 C 0.8699(4) 0.0325(3) 0.3532(4) 0.0566(16) Uani 1 1 d . . . H17 H 0.9329 0.0100 0.3955 0.068 Uiso 1 1 calc R . . C18 C 0.1761(5) 0.3580(4) -0.0780(6) 0.093(2) Uani 1 1 d . . . H18A H 0.1176 0.3310 -0.0660 0.112 Uiso 1 1 calc R . . H18B H 0.1737 0.4129 -0.0557 0.112 Uiso 1 1 calc R . . C19 C 0.2765(4) 0.3204(3) 0.0006(5) 0.0778(19) Uani 1 1 d . . . H19A H 0.3351 0.3506 -0.0051 0.093 Uiso 1 1 calc R . . H19B H 0.2775 0.3217 0.0817 0.093 Uiso 1 1 calc R . . C20 C 0.4920(3) 0.0253(3) 0.2167(4) 0.0326(12) Uani 1 1 d . . . H20 H 0.5616 0.0229 0.2739 0.039 Uiso 1 1 calc R . . C21 C 0.4191(4) 0.0259(3) 0.2885(4) 0.0480(14) Uani 1 1 d . . . H21A H 0.3482 0.0273 0.2368 0.058 Uiso 1 1 calc R . . H21B H 0.4313 0.0725 0.3380 0.058 Uiso 1 1 calc R . . C22 C 0.4365(5) -0.0480(4) 0.3642(5) 0.0719(18) Uani 1 1 d . . . H22A H 0.5047 -0.0457 0.4222 0.086 Uiso 1 1 calc R . . H22B H 0.3862 -0.0495 0.4059 0.086 Uiso 1 1 calc R . . C23 C 0.4274(5) -0.1224(3) 0.2926(5) 0.0734(19) Uani 1 1 d . . . H23A H 0.4432 -0.1677 0.3448 0.088 Uiso 1 1 calc R . . H23B H 0.3568 -0.1279 0.2410 0.088 Uiso 1 1 calc R . . C24 C 0.4991(4) -0.1217(3) 0.2202(5) 0.0590(16) Uani 1 1 d . . . H24A H 0.4876 -0.1685 0.1713 0.071 Uiso 1 1 calc R . . H24B H 0.5701 -0.1225 0.2717 0.071 Uiso 1 1 calc R . . C25 C 0.4812(4) -0.0486(3) 0.1436(4) 0.0444(14) Uani 1 1 d . . . H25A H 0.5308 -0.0474 0.1010 0.053 Uiso 1 1 calc R . . H25B H 0.4125 -0.0506 0.0866 0.053 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 Br1 0.0569(4) 0.0581(4) 0.0503(3) -0.0086(3) 0.0156(3) 0.0048(3) O1 0.030(2) 0.073(3) 0.060(2) -0.021(2) 0.0041(18) 0.009(2) O2 0.039(2) 0.109(4) 0.066(3) -0.032(2) -0.012(2) 0.019(2) O3 0.044(2) 0.039(2) 0.071(2) 0.015(2) 0.0154(18) -0.0022(19) O4 0.035(2) 0.042(2) 0.054(2) 0.0019(17) -0.0063(17) -0.0015(19) N1 0.029(3) 0.030(3) 0.034(2) 0.0051(18) 0.0053(19) 0.000(2) C26 0.026(3) 0.042(3) 0.041(3) -0.002(3) -0.003(3) 0.002(3) N3 0.031(3) 0.057(3) 0.050(3) -0.015(2) -0.001(2) 0.012(2) C1 0.082(5) 0.077(6) 0.096(6) 0.050(5) -0.009(4) 0.017(4) C2 0.083(5) 0.119(7) 0.059(4) 0.012(4) -0.003(4) 0.032(5) C3 0.069(4) 0.101(5) 0.055(4) 0.009(3) 0.013(3) 0.034(4) C4 0.036(3) 0.043(4) 0.056(4) 0.017(3) -0.002(3) 0.003(3) N2 0.034(3) 0.038(3) 0.073(3) 0.014(2) -0.010(2) 0.000(2) C6 0.039(4) 0.036(4) 0.031(3) 0.002(3) 0.004(3) 0.005(3) C7 0.037(3) 0.032(4) 0.040(3) -0.005(3) 0.013(3) -0.001(3) C8 0.028(3) 0.027(3) 0.046(3) 0.004(2) 0.009(3) -0.002(2) C9 0.037(3) 0.043(4) 0.042(3) -0.002(3) 0.007(3) 0.000(3) C10 0.040(4) 0.057(4) 0.060(4) -0.004(3) 0.006(3) 0.009(3) C11 0.028(3) 0.082(5) 0.065(4) -0.014(4) 0.009(3) 0.015(3) C12 0.054(4) 0.122(7) 0.129(6) 0.026(5) 0.032(4) 0.001(5) C13 0.072(5) 0.175(8) 0.092(5) -0.050(5) 0.019(4) 0.033(5) C14 0.059(4) 0.084(5) 0.097(5) 0.002(4) 0.018(4) 0.016(4) C15 0.036(3) 0.039(3) 0.033(3) -0.002(2) 0.008(3) 0.001(3) C16 0.044(4) 0.065(4) 0.039(3) -0.007(3) -0.007(3) 0.000(3) C17 0.042(3) 0.069(4) 0.046(4) -0.006(3) -0.004(3) 0.017(3) C18 0.077(5) 0.068(5) 0.101(6) -0.015(4) -0.018(4) 0.032(4) C19 0.074(5) 0.063(5) 0.074(4) -0.007(3) -0.008(3) 0.019(4) C20 0.028(3) 0.034(3) 0.029(3) 0.005(2) 0.000(2) 0.005(2) C21 0.051(4) 0.044(4) 0.048(3) 0.003(3) 0.014(3) 0.000(3) C22 0.083(5) 0.074(5) 0.069(4) 0.023(4) 0.039(3) 0.004(4) C23 0.068(4) 0.048(5) 0.097(5) 0.025(4) 0.016(4) -0.001(4) C24 0.062(4) 0.039(4) 0.068(4) 0.003(3) 0.009(3) 0.006(3) C25 0.054(3) 0.031(3) 0.042(3) -0.002(3) 0.006(3) 0.001(3) _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 C15 1.894(5) . ? O1 C10 1.336(6) . ? O1 C11 1.485(6) . ? O2 C10 1.208(6) . ? O3 C7 1.214(5) . ? O4 C6 1.215(5) . ? N1 C7 1.377(6) . ? N1 C6 1.448(6) . ? N1 C20 1.495(5) . ? C26 C8 1.383(6) . ? C26 C9 1.389(6) . ? C26 H2 0.9300 . ? N3 C10 1.381(6) . ? N3 C9 1.393(6) . ? N3 H3 0.8600 . ? C1 C18 1.465(8) . ? C1 C2 1.526(9) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.527(7) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.504(7) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N2 1.470(6) . ? C4 C19 1.502(7) . ? C4 H4 0.9800 . ? N2 C6 1.327(6) . ? N2 H5 0.8600 . ? C7 C8 1.520(6) . ? C8 C15 1.383(6) . ? C9 C17 1.393(6) . ? C11 C14 1.502(7) . ? C11 C12 1.507(8) . ? C11 C13 1.510(7) . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C16 1.385(6) . ? C16 C17 1.365(7) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 C19 1.532(7) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C25 1.509(6) . ? C20 C21 1.510(6) . ? C20 H20 0.9800 . ? C21 C22 1.519(7) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 C23 1.508(8) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C23 C24 1.501(7) . ? C23 H23A 0.9700 . ? C23 H23B 0.9700 . ? C24 C25 1.514(6) . ? C24 H24A 0.9700 . ? C24 H24B 0.9700 . ? C25 H25A 0.9700 . ? C25 H25B 0.9700 . ? 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 C10 O1 C11 119.7(4) . . ? C7 N1 C6 123.1(4) . . ? C7 N1 C20 119.6(4) . . ? C6 N1 C20 117.1(4) . . ? C8 C26 C9 121.7(4) . . ? C8 C26 H2 119.1 . . ? C9 C26 H2 119.1 . . ? C10 N3 C9 126.8(4) . . ? C10 N3 H3 116.6 . . ? C9 N3 H3 116.6 . . ? C18 C1 C2 111.4(5) . . ? C18 C1 H1A 109.3 . . ? C2 C1 H1A 109.3 . . ? C18 C1 H1B 109.3 . . ? C2 C1 H1B 109.3 . . ? H1A C1 H1B 108.0 . . ? C1 C2 C3 109.8(5) . . ? C1 C2 H2A 109.7 . . ? C3 C2 H2A 109.7 . . ? C1 C2 H2B 109.7 . . ? C3 C2 H2B 109.7 . . ? H2A C2 H2B 108.2 . . ? C4 C3 C2 111.3(5) . . ? C4 C3 H3A 109.4 . . ? C2 C3 H3A 109.4 . . ? C4 C3 H3B 109.4 . . ? C2 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? N2 C4 C19 110.5(4) . . ? N2 C4 C3 111.5(4) . . ? C19 C4 C3 110.9(5) . . ? N2 C4 H4 107.9 . . ? C19 C4 H4 107.9 . . ? C3 C4 H4 107.9 . . ? C6 N2 C4 123.0(4) . . ? C6 N2 H5 118.5 . . ? C4 N2 H5 118.5 . . ? O4 C6 N2 124.2(4) . . ? O4 C6 N1 119.5(5) . . ? N2 C6 N1 116.2(5) . . ? O3 C7 N1 124.2(4) . . ? O3 C7 C8 117.7(5) . . ? N1 C7 C8 118.0(5) . . ? C26 C8 C15 118.8(4) . . ? C26 C8 C7 118.0(4) . . ? C15 C8 C7 123.1(4) . . ? C26 C9 N3 116.9(4) . . ? C26 C9 C17 118.5(5) . . ? N3 C9 C17 124.6(5) . . ? O2 C10 O1 126.9(5) . . ? O2 C10 N3 124.6(5) . . ? O1 C10 N3 108.5(5) . . ? O1 C11 C14 111.4(5) . . ? O1 C11 C12 107.9(5) . . ? C14 C11 C12 113.1(5) . . ? O1 C11 C13 101.7(4) . . ? C14 C11 C13 111.2(5) . . ? C12 C11 C13 110.9(6) . . ? C11 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C11 C13 H13A 109.5 . . ? C11 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C11 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? 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 . . ? C8 C15 C16 119.7(4) . . ? C8 C15 Br1 120.4(4) . . ? C16 C15 Br1 119.9(4) . . ? C17 C16 C15 121.4(5) . . ? C17 C16 H16 119.3 . . ? C15 C16 H16 119.3 . . ? C16 C17 C9 119.9(5) . . ? C16 C17 H17 120.1 . . ? C9 C17 H17 120.1 . . ? C1 C18 C19 111.7(5) . . ? C1 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? C1 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 107.9 . . ? C4 C19 C18 110.7(4) . . ? C4 C19 H19A 109.5 . . ? C18 C19 H19A 109.5 . . ? C4 C19 H19B 109.5 . . ? C18 C19 H19B 109.5 . . ? H19A C19 H19B 108.1 . . ? N1 C20 C25 113.9(3) . . ? N1 C20 C21 113.3(4) . . ? C25 C20 C21 112.2(4) . . ? N1 C20 H20 105.5 . . ? C25 C20 H20 105.5 . . ? C21 C20 H20 105.5 . . ? C20 C21 C22 109.3(4) . . ? C20 C21 H21A 109.8 . . ? C22 C21 H21A 109.8 . . ? C20 C21 H21B 109.8 . . ? C22 C21 H21B 109.8 . . ? H21A C21 H21B 108.3 . . ? C23 C22 C21 112.1(5) . . ? C23 C22 H22A 109.2 . . ? C21 C22 H22A 109.2 . . ? C23 C22 H22B 109.2 . . ? C21 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C24 C23 C22 111.9(5) . . ? C24 C23 H23A 109.2 . . ? C22 C23 H23A 109.2 . . ? C24 C23 H23B 109.2 . . ? C22 C23 H23B 109.2 . . ? H23A C23 H23B 107.9 . . ? C23 C24 C25 110.5(5) . . ? C23 C24 H24A 109.6 . . ? C25 C24 H24A 109.6 . . ? C23 C24 H24B 109.6 . . ? C25 C24 H24B 109.6 . . ? H24A C24 H24B 108.1 . . ? C20 C25 C24 110.8(4) . . ? C20 C25 H25A 109.5 . . ? C24 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? C24 C25 H25B 109.5 . . ? H25A C25 H25B 108.1 . . ? _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 24.94 _diffrn_measured_fraction_theta_full 0.986 _refine_diff_density_max 0.339 _refine_diff_density_min -0.451 _refine_diff_density_rms 0.069 _database_code_depnum_ccdc_archive 'CCDC 942338'