# Electronic Supplementary Material (ESI) for RSC Advances # 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_sa _database_code_depnum_ccdc_archive 'CCDC 917035' #TrackingRef 'catalyst 1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H32 Br2 N4' _chemical_formula_weight 560.38 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 Orthorhombic _symmetry_space_group_name_H-M Pna2(1) 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' _cell_length_a 18.050(4) _cell_length_b 6.7540(14) _cell_length_c 21.429(4) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2612.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 8031 _cell_measurement_theta_min 3.0 _cell_measurement_theta_max 27.4 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.18 _exptl_crystal_size_min 0.16 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 3.123 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5466 _exptl_absorpt_correction_T_max 0.6349 _exptl_absorpt_process_details PROCESS-AUTO _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 RAXIS-RAPID _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22541 _diffrn_reflns_av_R_equivalents 0.0760 _diffrn_reflns_av_sigmaI/netI 0.0732 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5850 _reflns_number_gt 3248 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _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^)+(0.0827P)^2^+0.1449P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.514(18) _refine_ls_number_reflns 5850 _refine_ls_number_parameters 295 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1203 _refine_ls_R_factor_gt 0.0553 _refine_ls_wR_factor_ref 0.1715 _refine_ls_wR_factor_gt 0.1322 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _refine_ls_shift/su_max 0.002 _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 0.48792(4) 0.42524(10) 0.33605(4) 0.0595(2) Uani 1 1 d . . . Br2 Br 0.76506(5) 0.90803(11) 0.45923(4) 0.0668(3) Uani 1 1 d . . . N1 N 0.5209(3) -0.2660(8) 0.5026(3) 0.0459(17) Uani 1 1 d . . . N2 N 0.4588(4) -0.1172(8) 0.4306(3) 0.0484(15) Uani 1 1 d . . . N3 N 0.2947(4) 0.1269(9) 0.3580(3) 0.0506(15) Uani 1 1 d . . . N4 N 0.2335(4) 0.2685(8) 0.2846(4) 0.0488(17) Uani 1 1 d . . . C1 C 0.4589(4) -0.2726(9) 0.4700(4) 0.0442(18) Uani 1 1 d . . . H1 H 0.4218 -0.3677 0.4736 0.053 Uiso 1 1 calc R . . C2 C 0.5607(5) -0.1017(9) 0.4838(4) 0.054(2) Uani 1 1 d . . . H2 H 0.6068 -0.0635 0.4989 0.065 Uiso 1 1 calc R . . C3 C 0.5216(4) -0.0078(13) 0.4403(4) 0.056(2) Uani 1 1 d . . . H3 H 0.5344 0.1095 0.4203 0.067 Uiso 1 1 calc R . . C4 C 0.4011(5) -0.0762(11) 0.3826(4) 0.056(2) Uani 1 1 d . . . H4A H 0.3731 -0.1958 0.3739 0.067 Uiso 1 1 calc R . . H4B H 0.4243 -0.0330 0.3441 0.067 Uiso 1 1 calc R . . C5 C 0.3499(4) 0.0832(10) 0.4066(4) 0.0515(19) Uani 1 1 d . . . H5A H 0.3253 0.0385 0.4443 0.062 Uiso 1 1 calc R . . H5B H 0.3780 0.2016 0.4164 0.062 Uiso 1 1 calc R . . C6 C 0.2948(5) 0.2814(11) 0.3208(5) 0.060(3) Uani 1 1 d . . . H6 H 0.3304 0.3809 0.3195 0.072 Uiso 1 1 calc R . . C7 C 0.2315(4) 0.0143(12) 0.3479(4) 0.057(2) Uani 1 1 d . . . H7 H 0.2181 -0.1014 0.3686 0.069 Uiso 1 1 calc R . . C8 C 0.1929(5) 0.1067(10) 0.3018(4) 0.057(2) Uani 1 1 d . . . H8 H 0.1477 0.0672 0.2851 0.068 Uiso 1 1 calc R . . C9 C 0.5401(4) -0.4003(10) 0.5533(3) 0.0429(16) Uani 1 1 d . . . C10 C 0.5900(4) -0.5519(10) 0.5423(3) 0.0444(16) Uani 1 1 d . . . C11 C 0.6078(4) -0.6756(11) 0.5928(4) 0.0541(19) Uani 1 1 d . . . H11 H 0.6411 -0.7792 0.5870 0.065 Uiso 1 1 calc R . . C12 C 0.5765(5) -0.6455(11) 0.6512(4) 0.055(2) Uani 1 1 d . . . C13 C 0.5288(5) -0.4889(12) 0.6605(4) 0.056(2) Uani 1 1 d . . . H13 H 0.5095 -0.4668 0.7001 0.068 Uiso 1 1 calc R . . C14 C 0.5085(5) -0.3613(11) 0.6112(4) 0.0542(19) Uani 1 1 d . . . C15 C 0.6286(5) -0.5757(10) 0.4799(4) 0.061(2) Uani 1 1 d . . . H15A H 0.5928 -0.5656 0.4469 0.091 Uiso 1 1 calc R . . H15B H 0.6522 -0.7029 0.4781 0.091 Uiso 1 1 calc R . . H15C H 0.6652 -0.4736 0.4751 0.091 Uiso 1 1 calc R . . C16 C 0.5969(7) -0.7756(15) 0.7061(5) 0.091(4) Uani 1 1 d . . . H16A H 0.5715 -0.7301 0.7427 0.137 Uiso 1 1 calc R . . H16B H 0.6494 -0.7695 0.7129 0.137 Uiso 1 1 calc R . . H16C H 0.5827 -0.9098 0.6974 0.137 Uiso 1 1 calc R . . C17 C 0.4586(6) -0.1912(14) 0.6237(5) 0.075(3) Uani 1 1 d . . . H17A H 0.4756 -0.0775 0.6009 0.112 Uiso 1 1 calc R . . H17B H 0.4588 -0.1621 0.6675 0.112 Uiso 1 1 calc R . . H17C H 0.4092 -0.2239 0.6107 0.112 Uiso 1 1 calc R . . C18 C 0.2132(4) 0.4077(10) 0.2346(4) 0.0475(19) Uani 1 1 d . . . C19 C 0.1607(4) 0.5556(10) 0.2483(3) 0.0451(17) Uani 1 1 d . . . C20 C 0.1428(5) 0.6831(12) 0.2002(4) 0.057(2) Uani 1 1 d . . . H20 H 0.1104 0.7871 0.2083 0.068 Uiso 1 1 calc R . . C21 C 0.1710(5) 0.6622(12) 0.1404(4) 0.057(2) Uani 1 1 d . . . C22 C 0.2205(5) 0.5107(13) 0.1287(4) 0.059(2) Uani 1 1 d . . . H22 H 0.2397 0.4955 0.0887 0.070 Uiso 1 1 calc R . . C23 C 0.2421(5) 0.3801(11) 0.1756(4) 0.0539(19) Uani 1 1 d . . . C24 C 0.1250(5) 0.5714(11) 0.3106(4) 0.059(2) Uani 1 1 d . . . H24A H 0.1009 0.6975 0.3142 0.089 Uiso 1 1 calc R . . H24B H 0.1620 0.5593 0.3426 0.089 Uiso 1 1 calc R . . H24C H 0.0891 0.4676 0.3153 0.089 Uiso 1 1 calc R . . C25 C 0.1468(6) 0.7968(15) 0.0872(6) 0.085(3) Uani 1 1 d . . . H25A H 0.1008 0.7495 0.0703 0.128 Uiso 1 1 calc R . . H25B H 0.1840 0.7966 0.0552 0.128 Uiso 1 1 calc R . . H25C H 0.1402 0.9290 0.1027 0.128 Uiso 1 1 calc R . . C26 C 0.2955(6) 0.2131(15) 0.1612(5) 0.083(3) Uani 1 1 d . . . H26A H 0.3363 0.2178 0.1899 0.124 Uiso 1 1 calc R . . H26B H 0.3137 0.2273 0.1193 0.124 Uiso 1 1 calc R . . H26C H 0.2704 0.0885 0.1653 0.124 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 0.0523(5) 0.0630(4) 0.0631(5) 0.0087(4) -0.0038(4) 0.0002(3) Br2 0.0485(5) 0.0696(5) 0.0823(6) -0.0207(5) -0.0073(4) 0.0003(4) N1 0.035(4) 0.049(3) 0.054(4) 0.007(3) -0.006(3) 0.001(3) N2 0.043(4) 0.048(3) 0.054(4) 0.007(3) -0.006(3) 0.006(3) N3 0.038(4) 0.057(3) 0.057(4) 0.000(3) -0.009(3) 0.001(3) N4 0.040(4) 0.050(3) 0.057(4) 0.011(3) -0.011(3) -0.005(3) C1 0.043(4) 0.043(3) 0.047(5) 0.006(4) -0.006(4) 0.001(3) C2 0.050(5) 0.056(4) 0.056(5) 0.010(4) -0.015(4) -0.015(4) C3 0.045(5) 0.059(4) 0.063(5) 0.009(4) -0.005(4) -0.005(4) C4 0.055(5) 0.064(5) 0.050(5) -0.002(4) -0.009(4) 0.006(4) C5 0.046(5) 0.056(4) 0.052(5) 0.003(3) -0.010(4) 0.013(3) C6 0.043(5) 0.040(3) 0.097(8) 0.017(4) -0.015(5) -0.007(3) C7 0.042(5) 0.059(4) 0.071(5) 0.020(4) -0.009(4) -0.012(3) C8 0.040(5) 0.060(5) 0.071(5) 0.015(4) -0.015(4) -0.012(3) C9 0.032(4) 0.050(4) 0.046(4) 0.005(3) -0.004(3) 0.000(3) C10 0.042(4) 0.048(4) 0.043(4) -0.002(3) -0.007(3) 0.003(3) C11 0.054(5) 0.045(4) 0.063(5) 0.004(4) -0.008(4) 0.010(4) C12 0.062(5) 0.049(4) 0.055(5) 0.008(4) -0.004(4) 0.008(4) C13 0.062(6) 0.055(4) 0.053(5) 0.005(4) 0.004(4) 0.006(4) C14 0.051(5) 0.053(4) 0.059(5) 0.008(4) -0.006(4) 0.010(4) C15 0.065(6) 0.063(5) 0.055(5) 0.000(4) 0.002(4) 0.012(4) C16 0.135(11) 0.083(6) 0.056(6) 0.026(5) 0.000(7) 0.044(6) C17 0.078(7) 0.076(6) 0.070(6) 0.008(5) 0.022(5) 0.027(5) C18 0.041(4) 0.051(4) 0.051(5) 0.016(3) -0.015(3) -0.006(3) C19 0.039(4) 0.046(4) 0.050(4) 0.006(3) -0.006(3) -0.001(3) C20 0.054(6) 0.054(4) 0.061(5) 0.003(4) -0.008(4) 0.003(4) C21 0.043(5) 0.059(5) 0.068(6) 0.020(4) -0.001(4) -0.003(4) C22 0.055(6) 0.075(5) 0.045(4) 0.017(4) 0.001(4) -0.013(4) C23 0.041(4) 0.060(4) 0.061(5) 0.003(4) 0.010(4) -0.004(4) C24 0.057(5) 0.058(4) 0.062(5) 0.002(4) 0.001(4) -0.004(3) C25 0.090(8) 0.085(6) 0.081(7) 0.040(6) -0.002(7) 0.012(6) C26 0.064(7) 0.078(6) 0.107(8) 0.017(6) 0.018(6) 0.024(5) _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 N1 C1 1.320(10) . ? N1 C2 1.382(9) . ? N1 C9 1.457(9) . ? N2 C1 1.348(9) . ? N2 C3 1.369(10) . ? N2 C4 1.490(10) . ? N3 C6 1.313(10) . ? N3 C7 1.388(10) . ? N3 C5 1.472(9) . ? N4 C6 1.354(11) . ? N4 C8 1.366(9) . ? N4 C18 1.472(9) . ? C1 H1 0.9300 . ? C2 C3 1.331(10) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.510(8) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6 0.9300 . ? C7 C8 1.361(11) . ? C7 H7 0.9300 . ? C8 H8 0.9300 . ? C9 C10 1.384(10) . ? C9 C14 1.389(11) . ? C10 C11 1.404(11) . ? C10 C15 1.517(11) . ? C11 C12 1.388(11) . ? C11 H11 0.9300 . ? C12 C13 1.378(11) . ? C12 C16 1.514(12) . ? C13 C14 1.411(11) . ? C13 H13 0.9300 . ? C14 C17 1.485(11) . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C23 1.379(11) . ? C18 C19 1.408(10) . ? C19 C20 1.381(10) . ? C19 C24 1.487(11) . ? C20 C21 1.388(12) . ? C20 H20 0.9300 . ? C21 C22 1.381(13) . ? C21 C25 1.521(12) . ? C22 C23 1.394(11) . ? C22 H22 0.9300 . ? C23 C26 1.516(12) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? 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 N1 C2 108.3(6) . . ? C1 N1 C9 125.1(6) . . ? C2 N1 C9 126.5(7) . . ? C1 N2 C3 108.9(6) . . ? C1 N2 C4 125.4(6) . . ? C3 N2 C4 125.7(6) . . ? C6 N3 C7 110.0(7) . . ? C6 N3 C5 126.0(7) . . ? C7 N3 C5 123.8(6) . . ? C6 N4 C8 109.6(7) . . ? C6 N4 C18 125.4(6) . . ? C8 N4 C18 125.0(7) . . ? N1 C1 N2 107.9(6) . . ? N1 C1 H1 126.1 . . ? N2 C1 H1 126.1 . . ? C3 C2 N1 108.2(7) . . ? C3 C2 H2 125.9 . . ? N1 C2 H2 125.9 . . ? C2 C3 N2 106.8(7) . . ? C2 C3 H3 126.6 . . ? N2 C3 H3 126.6 . . ? N2 C4 C5 108.9(5) . . ? N2 C4 H4A 109.9 . . ? C5 C4 H4A 109.9 . . ? N2 C4 H4B 109.9 . . ? C5 C4 H4B 109.9 . . ? H4A C4 H4B 108.3 . . ? N3 C5 C4 108.4(6) . . ? N3 C5 H5A 110.0 . . ? C4 C5 H5A 110.0 . . ? N3 C5 H5B 110.0 . . ? C4 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? N3 C6 N4 107.2(7) . . ? N3 C6 H6 126.4 . . ? N4 C6 H6 126.4 . . ? C8 C7 N3 106.4(7) . . ? C8 C7 H7 126.8 . . ? N3 C7 H7 126.8 . . ? C7 C8 N4 106.8(7) . . ? C7 C8 H8 126.6 . . ? N4 C8 H8 126.6 . . ? C10 C9 C14 124.0(7) . . ? C10 C9 N1 119.3(6) . . ? C14 C9 N1 116.7(6) . . ? C9 C10 C11 117.3(7) . . ? C9 C10 C15 121.8(6) . . ? C11 C10 C15 120.7(6) . . ? C12 C11 C10 120.9(7) . . ? C12 C11 H11 119.5 . . ? C10 C11 H11 119.5 . . ? C13 C12 C11 119.8(7) . . ? C13 C12 C16 119.0(8) . . ? C11 C12 C16 121.1(8) . . ? C12 C13 C14 121.5(8) . . ? C12 C13 H13 119.3 . . ? C14 C13 H13 119.3 . . ? C9 C14 C13 116.5(7) . . ? C9 C14 C17 123.8(7) . . ? C13 C14 C17 119.7(8) . . ? C10 C15 H15A 109.5 . . ? C10 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C10 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C12 C16 H16A 109.5 . . ? C12 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C12 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C14 C17 H17A 109.5 . . ? C14 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C14 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C23 C18 C19 122.8(7) . . ? C23 C18 N4 119.1(7) . . ? C19 C18 N4 117.9(7) . . ? C20 C19 C18 116.4(7) . . ? C20 C19 C24 121.5(7) . . ? C18 C19 C24 122.0(7) . . ? C19 C20 C21 122.7(8) . . ? C19 C20 H20 118.7 . . ? C21 C20 H20 118.7 . . ? C22 C21 C20 118.7(7) . . ? C22 C21 C25 119.5(9) . . ? C20 C21 C25 121.7(8) . . ? C21 C22 C23 121.3(8) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C18 C23 C22 118.0(7) . . ? C18 C23 C26 121.9(8) . . ? C22 C23 C26 120.1(8) . . ? C19 C24 H24A 109.5 . . ? C19 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C19 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C21 C25 H25A 109.5 . . ? C21 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C21 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C23 C26 H26A 109.5 . . ? C23 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C23 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 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 C2 N1 C1 N2 0.5(9) . . . . ? C9 N1 C1 N2 175.7(6) . . . . ? C3 N2 C1 N1 -1.8(9) . . . . ? C4 N2 C1 N1 176.0(7) . . . . ? C1 N1 C2 C3 1.0(10) . . . . ? C9 N1 C2 C3 -174.1(7) . . . . ? N1 C2 C3 N2 -2.0(9) . . . . ? C1 N2 C3 C2 2.4(9) . . . . ? C4 N2 C3 C2 -175.4(7) . . . . ? C1 N2 C4 C5 101.6(8) . . . . ? C3 N2 C4 C5 -81.1(9) . . . . ? C6 N3 C5 C4 -103.0(9) . . . . ? C7 N3 C5 C4 81.5(9) . . . . ? N2 C4 C5 N3 178.2(7) . . . . ? C7 N3 C6 N4 -2.1(10) . . . . ? C5 N3 C6 N4 -178.1(7) . . . . ? C8 N4 C6 N3 2.6(11) . . . . ? C18 N4 C6 N3 -177.6(7) . . . . ? C6 N3 C7 C8 0.7(10) . . . . ? C5 N3 C7 C8 176.9(7) . . . . ? N3 C7 C8 N4 0.9(10) . . . . ? C6 N4 C8 C7 -2.2(10) . . . . ? C18 N4 C8 C7 178.1(7) . . . . ? C1 N1 C9 C10 102.6(9) . . . . ? C2 N1 C9 C10 -83.0(9) . . . . ? C1 N1 C9 C14 -80.0(10) . . . . ? C2 N1 C9 C14 94.3(9) . . . . ? C14 C9 C10 C11 1.7(11) . . . . ? N1 C9 C10 C11 178.9(6) . . . . ? C14 C9 C10 C15 -173.8(7) . . . . ? N1 C9 C10 C15 3.4(10) . . . . ? C9 C10 C11 C12 -0.2(11) . . . . ? C15 C10 C11 C12 175.4(8) . . . . ? C10 C11 C12 C13 -1.8(13) . . . . ? C10 C11 C12 C16 -178.6(9) . . . . ? C11 C12 C13 C14 2.4(13) . . . . ? C16 C12 C13 C14 179.3(9) . . . . ? C10 C9 C14 C13 -1.2(12) . . . . ? N1 C9 C14 C13 -178.4(7) . . . . ? C10 C9 C14 C17 176.1(8) . . . . ? N1 C9 C14 C17 -1.2(12) . . . . ? C12 C13 C14 C9 -1.0(12) . . . . ? C12 C13 C14 C17 -178.3(9) . . . . ? C6 N4 C18 C23 85.3(11) . . . . ? C8 N4 C18 C23 -94.9(10) . . . . ? C6 N4 C18 C19 -99.1(10) . . . . ? C8 N4 C18 C19 80.6(10) . . . . ? C23 C18 C19 C20 -4.3(11) . . . . ? N4 C18 C19 C20 -179.7(6) . . . . ? C23 C18 C19 C24 174.2(7) . . . . ? N4 C18 C19 C24 -1.2(10) . . . . ? C18 C19 C20 C21 3.6(11) . . . . ? C24 C19 C20 C21 -174.9(8) . . . . ? C19 C20 C21 C22 -1.6(13) . . . . ? C19 C20 C21 C25 176.2(8) . . . . ? C20 C21 C22 C23 0.0(13) . . . . ? C25 C21 C22 C23 -177.8(8) . . . . ? C19 C18 C23 C22 2.9(12) . . . . ? N4 C18 C23 C22 178.3(7) . . . . ? C19 C18 C23 C26 -176.8(8) . . . . ? N4 C18 C23 C26 -1.4(12) . . . . ? C21 C22 C23 C18 -0.7(12) . . . . ? C21 C22 C23 C26 179.0(9) . . . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.240 _refine_diff_density_min -0.988 _refine_diff_density_rms 0.103 data_sa2 _database_code_depnum_ccdc_archive 'CCDC 917036' #TrackingRef 'catalyst 1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H36 Br2 N4 O' _chemical_formula_weight 592.42 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 6.8588(14) _cell_length_b 18.823(4) _cell_length_c 22.137(4) _cell_angle_alpha 90.00 _cell_angle_beta 93.85(3) _cell_angle_gamma 90.00 _cell_volume 2851.5(10) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 13348 _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 27.5 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 2.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5461 _exptl_absorpt_correction_T_max 0.6263 _exptl_absorpt_process_details PROCESS-AUTO _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 RAXIS-RAPID _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 26197 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 3.17 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6459 _reflns_number_gt 3862 _reflns_threshold_expression >2sigma(I) _computing_data_collection PROCESS-AUTO _computing_cell_refinement PROCESS-AUTO _computing_data_reduction PROCESS-AUTO _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^)+(0.0413P)^2^+1.7287P] 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 0.0013(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6459 _refine_ls_number_parameters 320 _refine_ls_number_restraints 3 _refine_ls_R_factor_all 0.0905 _refine_ls_R_factor_gt 0.0401 _refine_ls_wR_factor_ref 0.1154 _refine_ls_wR_factor_gt 0.0851 _refine_ls_goodness_of_fit_ref 1.066 _refine_ls_restrained_S_all 1.066 _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 N1 N -0.1842(4) 0.33454(13) 0.50291(12) 0.0400(6) Uani 1 1 d . . . N2 N -0.0511(4) 0.37012(14) 0.42295(12) 0.0413(6) Uani 1 1 d . . . N3 N -0.1987(4) 0.11406(13) 0.62150(12) 0.0391(6) Uani 1 1 d . . . N4 N -0.0556(4) 0.01249(13) 0.63746(12) 0.0394(6) Uani 1 1 d . . . C1 C -0.0235(5) 0.33233(17) 0.47326(15) 0.0440(8) Uani 1 1 d . . . H1 H 0.0905 0.3082 0.4857 0.053 Uiso 1 1 calc R . . C2 C -0.3191(5) 0.3757(2) 0.47087(18) 0.0553(10) Uani 1 1 d . . . H2 H -0.4449 0.3859 0.4815 0.066 Uiso 1 1 calc R . . C3 C -0.2366(5) 0.3983(2) 0.42153(18) 0.0621(11) Uani 1 1 d . . . H3 H -0.2939 0.4278 0.3916 0.075 Uiso 1 1 calc R . . C4 C -0.2078(5) 0.30191(17) 0.56267(16) 0.0468(8) Uani 1 1 d . . . H4A H -0.3286 0.3184 0.5783 0.056 Uiso 1 1 calc R . . H4B H -0.1007 0.3165 0.5908 0.056 Uiso 1 1 calc R . . C5 C -0.2114(4) 0.22157(16) 0.55807(15) 0.0406(8) Uani 1 1 d . . . H5A H -0.0916 0.2047 0.5421 0.049 Uiso 1 1 calc R . . H5B H -0.3205 0.2065 0.5309 0.049 Uiso 1 1 calc R . . C6 C -0.2316(5) 0.19108(17) 0.62087(16) 0.0457(8) Uani 1 1 d . . . H6A H -0.1378 0.2137 0.6494 0.055 Uiso 1 1 calc R . . H6B H -0.3615 0.2011 0.6335 0.055 Uiso 1 1 calc R . . C7 C -0.0405(5) 0.08246(16) 0.64668(15) 0.0412(8) Uani 1 1 d . . . H7 H 0.0640 0.1053 0.6674 0.049 Uiso 1 1 calc R . . C8 C -0.3185(5) 0.06324(18) 0.59447(15) 0.0456(8) Uani 1 1 d . . . H8 H -0.4381 0.0710 0.5732 0.055 Uiso 1 1 calc R . . C9 C -0.2309(5) 0.00019(18) 0.60439(15) 0.0447(8) Uani 1 1 d . . . H9 H -0.2792 -0.0438 0.5914 0.054 Uiso 1 1 calc R . . C10 C 0.0880(4) 0.37964(16) 0.37700(15) 0.0390(7) Uani 1 1 d . . . C11 C 0.2088(4) 0.43870(16) 0.38114(15) 0.0388(7) Uani 1 1 d . . . C12 C 0.3363(4) 0.44757(17) 0.33536(16) 0.0446(8) Uani 1 1 d . . . H12 H 0.4202 0.4864 0.3369 0.053 Uiso 1 1 calc R . . C13 C 0.3417(5) 0.40013(17) 0.28746(16) 0.0433(8) Uani 1 1 d . . . C14 C 0.2166(5) 0.34232(17) 0.28549(15) 0.0453(8) Uani 1 1 d . . . H14 H 0.2191 0.3106 0.2533 0.054 Uiso 1 1 calc R . . C15 C 0.0873(5) 0.33026(17) 0.33016(15) 0.0440(8) Uani 1 1 d . . . C16 C 0.2033(6) 0.49194(19) 0.43152(18) 0.0564(9) Uani 1 1 d . . . H16A H 0.0813 0.5171 0.4280 0.085 Uiso 1 1 calc R . . H16B H 0.3090 0.5250 0.4290 0.085 Uiso 1 1 calc R . . H16C H 0.2161 0.4678 0.4698 0.085 Uiso 1 1 calc R . . C17 C 0.4809(6) 0.4114(2) 0.23823(19) 0.0670(11) Uani 1 1 d . . . H17A H 0.6113 0.3997 0.2534 0.101 Uiso 1 1 calc R . . H17B H 0.4763 0.4603 0.2257 0.101 Uiso 1 1 calc R . . H17C H 0.4434 0.3815 0.2043 0.101 Uiso 1 1 calc R . . C18 C -0.0420(6) 0.2658(2) 0.3280(2) 0.0718(12) Uani 1 1 d . . . H18A H 0.0021 0.2334 0.3596 0.108 Uiso 1 1 calc R . . H18B H -0.0367 0.2429 0.2894 0.108 Uiso 1 1 calc R . . H18C H -0.1740 0.2799 0.3337 0.108 Uiso 1 1 calc R . . C19 C 0.0866(4) -0.03862(15) 0.66155(15) 0.0385(7) Uani 1 1 d . . . C20 C 0.2212(5) -0.06571(16) 0.62313(15) 0.0424(8) Uani 1 1 d . . . C21 C 0.3613(5) -0.11245(18) 0.64864(18) 0.0515(9) Uani 1 1 d . . . H21 H 0.4525 -0.1318 0.6241 0.062 Uiso 1 1 calc R . . C22 C 0.3693(5) -0.13090(18) 0.70892(19) 0.0537(9) Uani 1 1 d . . . C23 C 0.2296(6) -0.10394(17) 0.74456(17) 0.0526(9) Uani 1 1 d . . . H23 H 0.2328 -0.1171 0.7851 0.063 Uiso 1 1 calc R . . C24 C 0.0838(5) -0.05769(17) 0.72199(15) 0.0436(8) Uani 1 1 d . . . C25 C 0.2164(6) -0.0465(2) 0.55703(17) 0.0600(10) Uani 1 1 d . . . H25A H 0.1021 -0.0667 0.5363 0.090 Uiso 1 1 calc R . . H25B H 0.3311 -0.0647 0.5399 0.090 Uiso 1 1 calc R . . H25C H 0.2128 0.0043 0.5528 0.090 Uiso 1 1 calc R . . C26 C 0.5242(7) -0.1813(2) 0.7354(2) 0.0817(14) Uani 1 1 d . . . H26A H 0.4633 -0.2240 0.7485 0.123 Uiso 1 1 calc R . . H26B H 0.5943 -0.1591 0.7694 0.123 Uiso 1 1 calc R . . H26C H 0.6134 -0.1926 0.7052 0.123 Uiso 1 1 calc R . . C27 C -0.0708(5) -0.0303(2) 0.76130(17) 0.0588(10) Uani 1 1 d . . . H27A H -0.0525 0.0198 0.7679 0.088 Uiso 1 1 calc R . . H27B H -0.0607 -0.0546 0.7995 0.088 Uiso 1 1 calc R . . H27C H -0.1977 -0.0385 0.7416 0.088 Uiso 1 1 calc R . . Br1 Br 0.28027(6) 0.16124(2) 0.49048(2) 0.07097(17) Uani 1 1 d . . . Br2 Br 0.30549(5) 0.39064(2) 0.595725(19) 0.05937(15) Uani 1 1 d . . . O1 O 0.2590(5) 0.21761(16) 0.63206(13) 0.0724(8) Uani 1 1 d D . . H1B H 0.265(8) 0.2625(13) 0.628(2) 0.109 Uiso 1 1 d D . . H1A H 0.269(7) 0.199(2) 0.5956(15) 0.109 Uiso 1 1 d 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 N1 0.0397(14) 0.0374(14) 0.0439(17) 0.0072(12) 0.0098(12) 0.0027(12) N2 0.0407(14) 0.0417(14) 0.0421(17) 0.0075(12) 0.0078(12) 0.0022(12) N3 0.0394(14) 0.0373(14) 0.0411(16) 0.0048(12) 0.0062(11) 0.0009(12) N4 0.0392(14) 0.0366(14) 0.0423(17) 0.0031(12) 0.0016(12) -0.0033(12) C1 0.0382(17) 0.049(2) 0.045(2) 0.0092(16) 0.0077(15) 0.0021(15) C2 0.0390(18) 0.066(2) 0.062(3) 0.014(2) 0.0115(17) 0.0154(18) C3 0.047(2) 0.087(3) 0.053(2) 0.024(2) 0.0082(17) 0.025(2) C4 0.0497(19) 0.0429(18) 0.049(2) 0.0112(16) 0.0155(16) 0.0045(16) C5 0.0367(16) 0.0387(17) 0.047(2) 0.0057(15) 0.0084(14) -0.0001(14) C6 0.0477(19) 0.0389(18) 0.052(2) 0.0049(15) 0.0124(16) 0.0065(15) C7 0.0398(17) 0.0359(16) 0.048(2) 0.0016(14) -0.0009(15) -0.0035(15) C8 0.0371(17) 0.051(2) 0.048(2) 0.0004(16) 0.0017(15) 0.0018(16) C9 0.0430(18) 0.0450(19) 0.045(2) -0.0028(15) -0.0009(15) -0.0048(16) C10 0.0388(16) 0.0398(17) 0.0387(19) 0.0073(14) 0.0058(14) 0.0001(14) C11 0.0399(16) 0.0372(17) 0.0393(19) 0.0019(14) 0.0019(14) -0.0008(14) C12 0.0368(17) 0.0420(18) 0.055(2) 0.0057(16) 0.0008(15) -0.0012(15) C13 0.0403(17) 0.0464(19) 0.044(2) 0.0047(16) 0.0098(14) 0.0053(15) C14 0.056(2) 0.0395(18) 0.041(2) -0.0033(15) 0.0071(16) 0.0053(16) C15 0.0500(19) 0.0387(18) 0.044(2) 0.0017(15) 0.0050(16) -0.0031(15) C16 0.063(2) 0.049(2) 0.058(2) -0.0067(18) 0.0059(18) -0.0014(18) C17 0.060(2) 0.081(3) 0.063(3) 0.002(2) 0.024(2) -0.003(2) C18 0.081(3) 0.052(2) 0.083(3) -0.011(2) 0.015(2) -0.024(2) C19 0.0415(17) 0.0300(15) 0.043(2) 0.0021(13) -0.0017(14) 0.0008(14) C20 0.0425(17) 0.0379(17) 0.047(2) -0.0013(15) 0.0036(15) -0.0022(15) C21 0.0432(19) 0.045(2) 0.066(3) -0.0066(18) 0.0048(17) -0.0020(16) C22 0.057(2) 0.0346(17) 0.067(3) -0.0008(17) -0.0107(19) 0.0028(17) C23 0.068(2) 0.0394(18) 0.048(2) 0.0064(16) -0.0101(18) -0.0012(18) C24 0.0533(19) 0.0391(17) 0.039(2) 0.0005(14) 0.0060(15) -0.0063(16) C25 0.063(2) 0.068(2) 0.050(2) 0.0002(19) 0.0127(18) 0.000(2) C26 0.077(3) 0.057(3) 0.107(4) 0.005(2) -0.025(3) 0.018(2) C27 0.065(2) 0.064(2) 0.048(2) 0.0021(18) 0.0094(19) -0.004(2) Br1 0.0523(2) 0.0707(3) 0.0892(4) -0.0282(2) 0.0002(2) 0.0092(2) Br2 0.0560(2) 0.0605(2) 0.0627(3) -0.00382(19) 0.01265(18) -0.00018(18) O1 0.0772(19) 0.0736(19) 0.065(2) 0.0107(15) -0.0026(16) -0.0066(17) _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 N1 C1 1.321(4) . ? N1 C2 1.367(4) . ? N1 C4 1.477(4) . ? N2 C1 1.324(4) . ? N2 C3 1.378(4) . ? N2 C10 1.452(4) . ? N3 C7 1.327(4) . ? N3 C8 1.372(4) . ? N3 C6 1.467(4) . ? N4 C7 1.336(4) . ? N4 C9 1.385(4) . ? N4 C19 1.446(4) . ? C1 H1 0.9300 . ? C2 C3 1.333(5) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.516(4) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.519(5) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 H7 0.9300 . ? C8 C9 1.341(5) . ? C8 H8 0.9300 . ? C9 H9 0.9300 . ? C10 C11 1.386(4) . ? C10 C15 1.392(4) . ? C11 C12 1.392(4) . ? C11 C16 1.502(5) . ? C12 C13 1.389(5) . ? C12 H12 0.9300 . ? C13 C14 1.385(5) . ? C13 C17 1.511(5) . ? C14 C15 1.390(5) . ? C14 H14 0.9300 . ? C15 C18 1.502(5) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 C24 1.387(4) . ? C19 C20 1.393(4) . ? C20 C21 1.394(5) . ? C20 C25 1.506(5) . ? C21 C22 1.376(5) . ? C21 H21 0.9300 . ? C22 C23 1.378(5) . ? C22 C26 1.513(5) . ? C23 C24 1.393(5) . ? C23 H23 0.9300 . ? C24 C27 1.507(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? O1 H1B 0.85(2) . ? O1 H1A 0.89(2) . ? 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 N1 C2 108.5(3) . . ? C1 N1 C4 125.3(3) . . ? C2 N1 C4 126.1(3) . . ? C1 N2 C3 107.8(3) . . ? C1 N2 C10 126.3(3) . . ? C3 N2 C10 125.9(3) . . ? C7 N3 C8 108.6(3) . . ? C7 N3 C6 124.6(3) . . ? C8 N3 C6 126.7(3) . . ? C7 N4 C9 107.5(3) . . ? C7 N4 C19 123.8(3) . . ? C9 N4 C19 128.6(3) . . ? N1 C1 N2 108.9(3) . . ? N1 C1 H1 125.5 . . ? N2 C1 H1 125.5 . . ? C3 C2 N1 107.3(3) . . ? C3 C2 H2 126.4 . . ? N1 C2 H2 126.4 . . ? C2 C3 N2 107.5(3) . . ? C2 C3 H3 126.3 . . ? N2 C3 H3 126.3 . . ? N1 C4 C5 110.9(3) . . ? N1 C4 H4A 109.5 . . ? C5 C4 H4A 109.5 . . ? N1 C4 H4B 109.5 . . ? C5 C4 H4B 109.5 . . ? H4A C4 H4B 108.0 . . ? C4 C5 C6 108.5(3) . . ? C4 C5 H5A 110.0 . . ? C6 C5 H5A 110.0 . . ? C4 C5 H5B 110.0 . . ? C6 C5 H5B 110.0 . . ? H5A C5 H5B 108.4 . . ? N3 C6 C5 111.0(3) . . ? N3 C6 H6A 109.4 . . ? C5 C6 H6A 109.4 . . ? N3 C6 H6B 109.4 . . ? C5 C6 H6B 109.4 . . ? H6A C6 H6B 108.0 . . ? N3 C7 N4 109.0(3) . . ? N3 C7 H7 125.5 . . ? N4 C7 H7 125.5 . . ? C9 C8 N3 107.3(3) . . ? C9 C8 H8 126.4 . . ? N3 C8 H8 126.4 . . ? C8 C9 N4 107.6(3) . . ? C8 C9 H9 126.2 . . ? N4 C9 H9 126.2 . . ? C11 C10 C15 123.8(3) . . ? C11 C10 N2 118.1(3) . . ? C15 C10 N2 118.0(3) . . ? C10 C11 C12 116.7(3) . . ? C10 C11 C16 122.7(3) . . ? C12 C11 C16 120.6(3) . . ? C13 C12 C11 122.0(3) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C14 C13 C12 118.7(3) . . ? C14 C13 C17 120.5(3) . . ? C12 C13 C17 120.7(3) . . ? C13 C14 C15 122.0(3) . . ? C13 C14 H14 119.0 . . ? C15 C14 H14 119.0 . . ? C14 C15 C10 116.8(3) . . ? C14 C15 C18 120.9(3) . . ? C10 C15 C18 122.4(3) . . ? C11 C16 H16A 109.5 . . ? C11 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C11 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C24 C19 C20 123.2(3) . . ? C24 C19 N4 118.4(3) . . ? C20 C19 N4 118.5(3) . . ? C19 C20 C21 116.8(3) . . ? C19 C20 C25 122.2(3) . . ? C21 C20 C25 121.0(3) . . ? C22 C21 C20 122.2(3) . . ? C22 C21 H21 118.9 . . ? C20 C21 H21 118.9 . . ? C21 C22 C23 118.6(3) . . ? C21 C22 C26 121.0(4) . . ? C23 C22 C26 120.4(4) . . ? C22 C23 C24 122.3(3) . . ? C22 C23 H23 118.8 . . ? C24 C23 H23 118.8 . . ? C19 C24 C23 116.9(3) . . ? C19 C24 C27 121.6(3) . . ? C23 C24 C27 121.5(3) . . ? C20 C25 H25A 109.5 . . ? C20 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C20 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C22 C26 H26A 109.5 . . ? C22 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C22 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C24 C27 H27A 109.5 . . ? C24 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C24 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? H1B O1 H1A 107(3) . . ? 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 C2 N1 C1 N2 -0.6(4) . . . . ? C4 N1 C1 N2 -176.7(3) . . . . ? C3 N2 C1 N1 1.1(4) . . . . ? C10 N2 C1 N1 -178.3(3) . . . . ? C1 N1 C2 C3 -0.2(4) . . . . ? C4 N1 C2 C3 176.0(3) . . . . ? N1 C2 C3 N2 0.8(5) . . . . ? C1 N2 C3 C2 -1.2(5) . . . . ? C10 N2 C3 C2 178.2(3) . . . . ? C1 N1 C4 C5 -70.0(4) . . . . ? C2 N1 C4 C5 114.4(4) . . . . ? N1 C4 C5 C6 178.9(3) . . . . ? C7 N3 C6 C5 107.2(4) . . . . ? C8 N3 C6 C5 -69.6(4) . . . . ? C4 C5 C6 N3 -169.2(3) . . . . ? C8 N3 C7 N4 -0.8(4) . . . . ? C6 N3 C7 N4 -178.2(3) . . . . ? C9 N4 C7 N3 0.6(4) . . . . ? C19 N4 C7 N3 -176.7(3) . . . . ? C7 N3 C8 C9 0.7(4) . . . . ? C6 N3 C8 C9 178.0(3) . . . . ? N3 C8 C9 N4 -0.4(4) . . . . ? C7 N4 C9 C8 -0.2(4) . . . . ? C19 N4 C9 C8 176.9(3) . . . . ? C1 N2 C10 C11 -93.7(4) . . . . ? C3 N2 C10 C11 87.1(4) . . . . ? C1 N2 C10 C15 88.6(4) . . . . ? C3 N2 C10 C15 -90.6(4) . . . . ? C15 C10 C11 C12 -0.4(5) . . . . ? N2 C10 C11 C12 -178.0(3) . . . . ? C15 C10 C11 C16 178.7(3) . . . . ? N2 C10 C11 C16 1.1(5) . . . . ? C10 C11 C12 C13 0.6(5) . . . . ? C16 C11 C12 C13 -178.5(3) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? C11 C12 C13 C17 179.6(3) . . . . ? C12 C13 C14 C15 -0.5(5) . . . . ? C17 C13 C14 C15 179.8(3) . . . . ? C13 C14 C15 C10 0.6(5) . . . . ? C13 C14 C15 C18 -177.9(3) . . . . ? C11 C10 C15 C14 -0.1(5) . . . . ? N2 C10 C15 C14 177.5(3) . . . . ? C11 C10 C15 C18 178.3(3) . . . . ? N2 C10 C15 C18 -4.1(5) . . . . ? C7 N4 C19 C24 78.1(4) . . . . ? C9 N4 C19 C24 -98.6(4) . . . . ? C7 N4 C19 C20 -101.2(4) . . . . ? C9 N4 C19 C20 82.2(4) . . . . ? C24 C19 C20 C21 -2.0(5) . . . . ? N4 C19 C20 C21 177.3(3) . . . . ? C24 C19 C20 C25 177.5(3) . . . . ? N4 C19 C20 C25 -3.3(5) . . . . ? C19 C20 C21 C22 -0.6(5) . . . . ? C25 C20 C21 C22 179.9(3) . . . . ? C20 C21 C22 C23 2.2(5) . . . . ? C20 C21 C22 C26 -179.4(3) . . . . ? C21 C22 C23 C24 -1.3(5) . . . . ? C26 C22 C23 C24 -179.7(3) . . . . ? C20 C19 C24 C23 2.8(5) . . . . ? N4 C19 C24 C23 -176.5(3) . . . . ? C20 C19 C24 C27 -176.6(3) . . . . ? N4 C19 C24 C27 4.1(4) . . . . ? C22 C23 C24 C19 -1.0(5) . . . . ? C22 C23 C24 C27 178.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1B Br2 0.85(2) 2.54(3) 3.375(3) 168(4) . O1 H1A Br1 0.89(2) 2.44(3) 3.321(3) 173(4) . _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.544 _refine_diff_density_min -0.594 _refine_diff_density_rms 0.085 data_sa-sr _database_code_depnum_ccdc_archive 'CCDC 917037' #TrackingRef 'catalyst 1c.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C28 H36 Br2 N4' _chemical_formula_sum 'C28 H36 Br2 N4' _chemical_formula_weight 588.43 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 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 14.276(3) _cell_length_b 9.1205(18) _cell_length_c 13.007(3) _cell_angle_alpha 90.00 _cell_angle_beta 113.75(3) _cell_angle_gamma 90.00 _cell_volume 1550.2(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min 3.1 _cell_measurement_theta_max 25.0 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.261 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 604 _exptl_absorpt_coefficient_mu 2.635 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7093 _exptl_absorpt_correction_T_max 0.7786 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Rigaku RAXIS-RAPID' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11289 _diffrn_reflns_av_R_equivalents 0.1139 _diffrn_reflns_av_sigmaI/netI 0.1123 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 3.12 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2708 _reflns_number_gt 1673 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROCESS-AUTO ' _computing_cell_refinement 'PROCESS-AUTO ' _computing_data_reduction 'CrystalStructure ' _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^)+(0.1464P)^2^+12.7781P] 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 0.012(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2708 _refine_ls_number_parameters 158 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1437 _refine_ls_R_factor_gt 0.1107 _refine_ls_wR_factor_ref 0.3575 _refine_ls_wR_factor_gt 0.3370 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 0.31048(11) 0.16365(13) 0.14693(13) 0.0739(7) Uani 1 1 d . . . N1 N 0.3719(8) 0.5966(11) 0.1347(9) 0.063(3) Uani 1 1 d . . . N2 N 0.2306(7) 0.6499(9) 0.1504(8) 0.051(2) Uani 1 1 d . . . C1 C 0.2862(8) 0.5399(11) 0.1330(8) 0.045(2) Uani 1 1 d . . . H1 H 0.2673 0.4416 0.1218 0.054 Uiso 1 1 calc R . . C2 C 0.3741(12) 0.7420(15) 0.1574(15) 0.087(5) Uani 1 1 d . . . H2 H 0.4282 0.8052 0.1673 0.105 Uiso 1 1 calc R . . C3 C 0.2844(12) 0.7803(15) 0.1631(12) 0.073(4) Uani 1 1 d . . . H3 H 0.2635 0.8737 0.1732 0.088 Uiso 1 1 calc R . . C4 C 0.4534(9) 0.5141(15) 0.1197(10) 0.062(3) Uani 1 1 d . . . H4A H 0.4433 0.4103 0.1277 0.075 Uiso 1 1 calc R . . H4B H 0.5187 0.5417 0.1783 0.075 Uiso 1 1 calc R . . C5 C 0.4569(10) 0.5405(15) 0.0068(12) 0.068(3) Uani 1 1 d . . . H5A H 0.3925 0.5096 -0.0518 0.082 Uiso 1 1 calc R . . H5B H 0.4647 0.6447 -0.0024 0.082 Uiso 1 1 calc R . . C6 C 0.1302(8) 0.6290(11) 0.1544(9) 0.047(2) Uani 1 1 d . . . C7 C 0.1277(9) 0.5430(13) 0.2410(9) 0.058(3) Uani 1 1 d . . . C8 C 0.0324(11) 0.5195(16) 0.2430(11) 0.070(4) Uani 1 1 d . . . H8 H 0.0278 0.4611 0.2995 0.083 Uiso 1 1 calc R . . C9 C -0.0541(10) 0.5790(16) 0.1654(12) 0.066(3) Uani 1 1 d . . . C10 C -0.0468(11) 0.6604(16) 0.0808(16) 0.083(5) Uani 1 1 d . . . H10 H -0.1069 0.6972 0.0260 0.100 Uiso 1 1 calc R . . C11 C 0.0443(9) 0.6918(12) 0.0715(9) 0.052(3) Uani 1 1 d . . . C12 C 0.2199(13) 0.4808(19) 0.3325(12) 0.093(5) Uani 1 1 d . . . H12A H 0.2005 0.4354 0.3876 0.139 Uiso 1 1 calc R . . H12B H 0.2682 0.5578 0.3671 0.139 Uiso 1 1 calc R . . H12C H 0.2506 0.4089 0.3018 0.139 Uiso 1 1 calc R . . C13 C -0.1614(13) 0.545(3) 0.1641(16) 0.120(7) Uani 1 1 d . . . H13A H -0.2096 0.6175 0.1198 0.179 Uiso 1 1 calc R . . H13B H -0.1575 0.5469 0.2395 0.179 Uiso 1 1 calc R . . H13C H -0.1834 0.4497 0.1321 0.179 Uiso 1 1 calc R . . C14 C 0.0518(13) 0.7868(17) -0.0219(12) 0.086(5) Uani 1 1 d . . . H14A H 0.0870 0.8763 0.0098 0.129 Uiso 1 1 calc R . . H14B H -0.0158 0.8091 -0.0762 0.129 Uiso 1 1 calc R . . H14C H 0.0888 0.7347 -0.0577 0.129 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 0.0815(12) 0.0452(8) 0.0929(12) 0.0016(6) 0.0328(8) 0.0075(6) N1 0.052(6) 0.058(6) 0.085(7) -0.010(5) 0.035(5) -0.006(5) N2 0.062(6) 0.036(5) 0.063(6) -0.005(4) 0.033(5) -0.006(4) C1 0.050(6) 0.036(5) 0.055(6) -0.010(4) 0.028(5) -0.004(4) C2 0.084(11) 0.058(8) 0.134(14) -0.037(9) 0.059(10) -0.027(7) C3 0.098(11) 0.051(7) 0.095(10) -0.019(7) 0.064(9) -0.014(7) C4 0.057(7) 0.072(8) 0.061(7) -0.013(6) 0.028(6) 0.001(6) C5 0.061(8) 0.070(8) 0.080(8) -0.004(7) 0.035(7) -0.001(6) C6 0.048(6) 0.048(6) 0.051(6) 0.000(5) 0.027(5) 0.005(4) C7 0.061(8) 0.063(7) 0.052(6) 0.008(5) 0.025(6) 0.003(6) C8 0.079(10) 0.076(9) 0.072(8) -0.003(7) 0.049(8) -0.006(7) C9 0.057(8) 0.080(9) 0.075(8) -0.029(7) 0.041(7) -0.011(6) C10 0.045(8) 0.081(10) 0.116(13) -0.018(9) 0.025(8) 0.007(6) C11 0.070(8) 0.050(6) 0.047(6) 0.006(5) 0.035(6) 0.010(5) C12 0.098(12) 0.099(12) 0.077(9) 0.023(9) 0.031(8) 0.019(9) C13 0.076(11) 0.19(2) 0.117(14) -0.038(14) 0.061(10) -0.036(12) C14 0.121(13) 0.079(9) 0.074(9) 0.032(8) 0.056(9) 0.028(9) _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 N1 C1 1.321(13) . ? N1 C2 1.356(17) . ? N1 C4 1.463(15) . ? N2 C1 1.354(13) . ? N2 C3 1.389(15) . ? N2 C6 1.467(14) . ? C1 H1 0.9300 . ? C2 C3 1.36(2) . ? C2 H2 0.9300 . ? C3 H3 0.9300 . ? C4 C5 1.508(17) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C5 1.50(2) 3_665 ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.384(15) . ? C6 C11 1.389(16) . ? C7 C8 1.388(17) . ? C7 C12 1.487(18) . ? C8 C9 1.355(19) . ? C8 H8 0.9300 . ? C9 C10 1.37(2) . ? C9 C13 1.556(18) . ? C10 C11 1.384(19) . ? C10 H10 0.9300 . ? C11 C14 1.530(16) . ? 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 . ? 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 N1 C2 109.1(10) . . ? C1 N1 C4 125.3(10) . . ? C2 N1 C4 125.6(11) . . ? C1 N2 C3 108.7(10) . . ? C1 N2 C6 123.8(8) . . ? C3 N2 C6 127.5(9) . . ? N1 C1 N2 108.0(9) . . ? N1 C1 H1 126.0 . . ? N2 C1 H1 126.0 . . ? N1 C2 C3 108.9(12) . . ? N1 C2 H2 125.6 . . ? C3 C2 H2 125.6 . . ? C2 C3 N2 105.2(11) . . ? C2 C3 H3 127.4 . . ? N2 C3 H3 127.4 . . ? N1 C4 C5 112.9(11) . . ? N1 C4 H4A 109.0 . . ? C5 C4 H4A 109.0 . . ? N1 C4 H4B 109.0 . . ? C5 C4 H4B 109.0 . . ? H4A C4 H4B 107.8 . . ? C5 C5 C4 112.7(14) 3_665 . ? C5 C5 H5A 109.1 3_665 . ? C4 C5 H5A 109.1 . . ? C5 C5 H5B 109.1 3_665 . ? C4 C5 H5B 109.1 . . ? H5A C5 H5B 107.8 . . ? C7 C6 C11 124.1(10) . . ? C7 C6 N2 116.6(10) . . ? C11 C6 N2 119.2(10) . . ? C6 C7 C8 116.8(11) . . ? C6 C7 C12 124.2(12) . . ? C8 C7 C12 119.0(12) . . ? C9 C8 C7 122.0(12) . . ? C9 C8 H8 119.0 . . ? C7 C8 H8 119.0 . . ? C8 C9 C10 118.4(12) . . ? C8 C9 C13 121.8(15) . . ? C10 C9 C13 119.6(15) . . ? C9 C10 C11 124.2(13) . . ? C9 C10 H10 117.9 . . ? C11 C10 H10 117.9 . . ? C10 C11 C6 114.4(11) . . ? C10 C11 C14 123.7(13) . . ? C6 C11 C14 121.9(12) . . ? C7 C12 H12A 109.5 . . ? C7 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C7 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? C9 C13 H13A 109.5 . . ? C9 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C9 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 . . ? 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 C2 N1 C1 N2 2.2(15) . . . . ? C4 N1 C1 N2 179.7(11) . . . . ? C3 N2 C1 N1 0.2(14) . . . . ? C6 N2 C1 N1 -179.9(10) . . . . ? C1 N1 C2 C3 -3.9(18) . . . . ? C4 N1 C2 C3 178.6(13) . . . . ? N1 C2 C3 N2 3.9(18) . . . . ? C1 N2 C3 C2 -2.6(16) . . . . ? C6 N2 C3 C2 177.5(12) . . . . ? C1 N1 C4 C5 106.6(14) . . . . ? C2 N1 C4 C5 -76.3(17) . . . . ? N1 C4 C5 C5 178.0(13) . . . 3_665 ? C1 N2 C6 C7 64.1(14) . . . . ? C3 N2 C6 C7 -116.0(14) . . . . ? C1 N2 C6 C11 -114.2(12) . . . . ? C3 N2 C6 C11 65.7(16) . . . . ? C11 C6 C7 C8 0.1(18) . . . . ? N2 C6 C7 C8 -178.1(10) . . . . ? C11 C6 C7 C12 -177.4(13) . . . . ? N2 C6 C7 C12 4.4(18) . . . . ? C6 C7 C8 C9 -0.8(19) . . . . ? C12 C7 C8 C9 176.8(13) . . . . ? C7 C8 C9 C10 2(2) . . . . ? C7 C8 C9 C13 176.4(14) . . . . ? C8 C9 C10 C11 -3(2) . . . . ? C13 C9 C10 C11 -177.2(14) . . . . ? C9 C10 C11 C6 2.0(19) . . . . ? C9 C10 C11 C14 -178.2(13) . . . . ? C7 C6 C11 C10 -0.6(17) . . . . ? N2 C6 C11 C10 177.6(10) . . . . ? C7 C6 C11 C14 179.6(12) . . . . ? N2 C6 C11 C14 -2.2(16) . . . . ? loop_ _platon_squeeze_void_nr _platon_squeeze_void_average_x _platon_squeeze_void_average_y _platon_squeeze_void_average_z _platon_squeeze_void_volume _platon_squeeze_void_count_electrons _platon_squeeze_void_content 1 0.500 0.000 0.000 99 21 ' ' 2 0.500 0.500 0.500 99 21 ' ' _platon_squeeze_details ; ; _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 1.561 _refine_diff_density_min -0.558 _refine_diff_density_rms 0.144