# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 182 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Yan, Bin' 'Cramen, Jordan' 'McDonald, Robert' 'Frank, Natia' _publ_contact_author_name 'Frank, Natia' _publ_contact_author_email nlfrank@uvic.ca _publ_section_title ; Ferromagnetic Spin-Delocalized Electron Donors for Multifunctional Materials: p-Conjugated Benzotriazinyl Radicals ; # Attachment '- 1a.cif' data_vic0710 _database_code_depnum_ccdc_archive 'CCDC 799186' #TrackingRef '- 1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H16 N3' _chemical_formula_sum 'C21 H16 N3' _chemical_formula_weight 310.37 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'I 2/a' _symmetry_space_group_name_Hall '-I 2ya' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y, -z' 'x+1/2, y+1/2, z+1/2' '-x+1, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y, z' '-x+1/2, -y+1/2, -z+1/2' 'x, -y+1/2, z+1/2' _cell_length_a 26.247(6) _cell_length_b 4.9783(11) _cell_length_c 26.853(6) _cell_angle_alpha 90.00 _cell_angle_beta 113.635(4) _cell_angle_gamma 90.00 _cell_volume 3214.5(13) _cell_formula_units_Z 8 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 2537 _cell_measurement_theta_min 2.80 _cell_measurement_theta_max 25.59 _exptl_crystal_description plate _exptl_crystal_colour black _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.283 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1304 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9408 _exptl_absorpt_correction_T_max 0.9938 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 11233 _diffrn_reflns_av_R_equivalents 0.0771 _diffrn_reflns_av_sigmaI/netI 0.0657 _diffrn_reflns_limit_h_min -32 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.66 _diffrn_reflns_theta_max 25.83 _reflns_number_total 3087 _reflns_number_gt 1805 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1017P)^2^+0.4133P] 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_number_reflns 3087 _refine_ls_number_parameters 288 _refine_ls_number_restraints 13 _refine_ls_R_factor_all 0.1073 _refine_ls_R_factor_gt 0.0594 _refine_ls_wR_factor_ref 0.1883 _refine_ls_wR_factor_gt 0.1563 _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_restrained_S_all 1.024 _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 N1 N 0.30821(7) 0.3413(4) 0.14735(7) 0.0477(5) Uani 1 1 d D . . N2 N 0.31184(7) 0.1519(4) 0.18526(7) 0.0453(5) Uani 1 1 d . A . N3 N 0.40849(7) 0.2564(4) 0.23316(7) 0.0465(5) Uani 1 1 d . A . C1 C 0.36189(9) 0.1208(4) 0.22568(8) 0.0414(5) Uani 1 1 d . . . C2 C 0.40437(9) 0.4433(4) 0.19449(9) 0.0434(6) Uani 1 1 d . . . C3 C 0.45130(10) 0.5939(5) 0.19906(10) 0.0514(6) Uani 1 1 d . A . H3 H 0.4857 0.5640 0.2290 0.062 Uiso 1 1 calc R . . C4 C 0.44822(10) 0.7833(5) 0.16096(10) 0.0557(7) Uani 1 1 d . . . H4 H 0.4803 0.8844 0.1649 0.067 Uiso 1 1 calc R A . C5 C 0.39806(10) 0.8289(5) 0.11626(10) 0.0543(6) Uani 1 1 d . A . H5 H 0.3964 0.9589 0.0897 0.065 Uiso 1 1 calc R . . C6 C 0.35097(10) 0.6854(5) 0.11057(10) 0.0515(6) Uani 1 1 d . . . H6 H 0.3169 0.7173 0.0803 0.062 Uiso 1 1 calc R A . C7 C 0.35373(9) 0.4936(4) 0.14941(9) 0.0445(6) Uani 1 1 d . A . C11A C 0.2559(4) 0.347(4) 0.0995(4) 0.035(3) Uani 0.50 1 d PD A 1 C12A C 0.2108(2) 0.4377(10) 0.1102(2) 0.0449(11) Uani 0.50 1 d P A 1 H12A H 0.2153 0.4824 0.1461 0.054 Uiso 0.50 1 calc PR A 1 C13A C 0.1590(2) 0.4602(13) 0.0667(3) 0.0504(13) Uani 0.50 1 d P A 1 H13A H 0.1278 0.5226 0.0729 0.060 Uiso 0.50 1 calc PR A 1 C14A C 0.1528(6) 0.391(2) 0.0142(5) 0.053(3) Uani 0.50 1 d P A 1 H14A H 0.1173 0.3981 -0.0151 0.064 Uiso 0.50 1 calc PR A 1 C15A C 0.1988(2) 0.3138(10) 0.0054(2) 0.0590(13) Uani 0.50 1 d P A 1 H15A H 0.1948 0.2720 -0.0305 0.071 Uiso 0.50 1 calc PR A 1 C16A C 0.25068(19) 0.2953(9) 0.04773(18) 0.0493(12) Uani 0.50 1 d P A 1 H16A H 0.2823 0.2470 0.0409 0.059 Uiso 0.50 1 calc PR A 1 C11B C 0.2508(4) 0.389(4) 0.1099(5) 0.042(3) Uani 0.50 1 d PD A 2 C12B C 0.2261(2) 0.6274(11) 0.0996(2) 0.0516(12) Uani 0.50 1 d P A 2 H12B H 0.2447 0.7800 0.1200 0.062 Uiso 0.50 1 calc PR A 2 C13B C 0.1731(2) 0.6543(13) 0.0592(2) 0.0609(14) Uani 0.50 1 d P A 2 H13B H 0.1560 0.8263 0.0522 0.073 Uiso 0.50 1 calc PR A 2 C14B C 0.1456(6) 0.445(3) 0.0300(5) 0.056(3) Uani 0.50 1 d P A 2 H14B H 0.1100 0.4695 0.0015 0.067 Uiso 0.50 1 calc PR A 2 C15B C 0.1694(2) 0.1860(11) 0.0412(2) 0.0575(13) Uani 0.50 1 d P A 2 H15B H 0.1492 0.0347 0.0216 0.069 Uiso 0.50 1 calc PR A 2 C16B C 0.2226(2) 0.1546(10) 0.08142(19) 0.0500(12) Uani 0.50 1 d P A 2 H16B H 0.2398 -0.0172 0.0897 0.060 Uiso 0.50 1 calc PR A 2 C21 C 0.36492(9) -0.0853(5) 0.26678(9) 0.0449(6) Uani 1 1 d . A . C22 C 0.41301(11) -0.1098(5) 0.31426(10) 0.0559(7) Uani 1 1 d . . . H22 H 0.4434 0.0077 0.3199 0.067 Uiso 1 1 calc R A . C23 C 0.41778(12) -0.3008(6) 0.35345(10) 0.0645(8) Uani 1 1 d D A . C24 C 0.37293(14) -0.4709(6) 0.34450(11) 0.0683(8) Uani 1 1 d . . . H24 H 0.3755 -0.6045 0.3707 0.082 Uiso 1 1 calc R A . C25 C 0.32453(12) -0.4480(5) 0.29788(11) 0.0614(7) Uani 1 1 d . A . H25 H 0.2939 -0.5634 0.2925 0.074 Uiso 1 1 calc R . . C26 C 0.32070(10) -0.2571(5) 0.25906(10) 0.0519(6) Uani 1 1 d . . . H26 H 0.2876 -0.2435 0.2269 0.062 Uiso 1 1 calc R A . C27 C 0.46994(19) -0.3209(7) 0.40370(13) 0.1164(15) Uani 1 1 d D . . H27A H 0.4939 -0.1722 0.4075 0.140 Uiso 0.60 1 calc PRD A 1 H27B H 0.4764 -0.4981 0.4180 0.140 Uiso 0.40 1 calc PRD A 2 C28A C 0.4891(3) -0.4747(15) 0.4400(2) 0.134(3) Uani 0.60 1 d PD A 1 H28A H 0.5243(4) -0.449(8) 0.4691(9) 0.161 Uiso 0.60 1 d PD B 1 H28B H 0.4677(14) -0.630(4) 0.4393(17) 0.161 Uiso 0.60 1 d PD C 1 C28B C 0.5048(3) -0.171(2) 0.4297(4) 0.140(4) Uiso 0.40 1 d PD A 2 H28C H 0.5365(10) -0.214(12) 0.4617(6) 0.168 Uiso 0.40 1 d PD D 2 H28D H 0.499(2) 0.007(5) 0.416(2) 0.168 Uiso 0.40 1 d PD E 2 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 0.0438(11) 0.0424(11) 0.0481(11) 0.0063(9) 0.0093(9) 0.0040(9) N2 0.0464(11) 0.0417(11) 0.0442(11) 0.0030(9) 0.0145(9) 0.0059(9) N3 0.0436(11) 0.0438(11) 0.0476(11) -0.0015(9) 0.0137(9) 0.0029(9) C1 0.0415(12) 0.0396(12) 0.0401(13) -0.0036(10) 0.0132(10) 0.0079(10) C2 0.0445(13) 0.0395(12) 0.0441(13) -0.0038(10) 0.0155(11) 0.0053(10) C3 0.0443(13) 0.0497(14) 0.0547(15) -0.0047(12) 0.0141(12) 0.0001(11) C4 0.0544(15) 0.0463(14) 0.0668(16) -0.0046(13) 0.0249(13) -0.0044(12) C5 0.0590(15) 0.0461(14) 0.0590(15) 0.0012(12) 0.0252(13) -0.0013(12) C6 0.0513(14) 0.0448(14) 0.0499(14) 0.0011(11) 0.0114(11) 0.0033(11) C7 0.0445(13) 0.0351(12) 0.0488(14) -0.0049(10) 0.0133(11) 0.0015(10) C11A 0.039(4) 0.025(5) 0.038(5) 0.000(4) 0.013(3) 0.007(3) C12A 0.049(3) 0.043(3) 0.045(3) 0.003(2) 0.021(3) 0.006(2) C13A 0.040(3) 0.049(4) 0.058(4) 0.002(3) 0.015(3) 0.004(2) C14A 0.054(6) 0.039(5) 0.052(7) -0.001(4) 0.006(4) 0.001(4) C15A 0.069(4) 0.060(3) 0.043(3) 0.003(2) 0.018(3) -0.001(3) C16A 0.047(3) 0.055(3) 0.046(3) 0.001(2) 0.018(2) 0.006(2) C11B 0.051(5) 0.039(7) 0.035(4) -0.011(3) 0.017(4) 0.003(3) C12B 0.053(3) 0.044(3) 0.050(3) 0.000(2) 0.013(2) 0.002(3) C13B 0.057(3) 0.055(4) 0.062(4) 0.008(3) 0.015(3) 0.007(3) C14B 0.050(4) 0.057(6) 0.048(7) -0.001(5) 0.005(5) 0.008(4) C15B 0.053(3) 0.062(3) 0.050(3) -0.001(3) 0.012(2) -0.017(3) C16B 0.051(3) 0.043(3) 0.055(3) 0.007(2) 0.020(2) -0.001(2) C21 0.0471(13) 0.0439(13) 0.0440(13) -0.0014(11) 0.0185(11) 0.0091(11) C22 0.0563(15) 0.0574(16) 0.0501(15) 0.0002(13) 0.0172(12) 0.0094(12) C23 0.0763(19) 0.0661(18) 0.0459(15) 0.0067(14) 0.0190(14) 0.0206(16) C24 0.094(2) 0.0608(18) 0.0611(18) 0.0195(14) 0.0422(17) 0.0264(16) C25 0.0730(18) 0.0531(16) 0.0702(18) 0.0074(14) 0.0412(16) 0.0094(14) C26 0.0537(14) 0.0506(15) 0.0530(14) 0.0026(12) 0.0232(12) 0.0102(12) C27 0.163(4) 0.108(3) 0.057(2) 0.027(2) 0.021(2) 0.050(3) C28A 0.119(5) 0.178(7) 0.070(4) 0.053(5) 0.000(4) -0.020(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 N2 1.363(2) . ? N1 C7 1.397(3) . ? N1 C11A 1.457(5) . ? N1 C11B 1.457(5) . ? N2 C1 1.336(3) . ? N3 C1 1.340(3) . ? N3 C2 1.366(3) . ? C1 C21 1.486(3) . ? C2 C3 1.405(3) . ? C2 C7 1.416(3) . ? C3 C4 1.370(3) . ? C4 C5 1.399(3) . ? C5 C6 1.382(3) . ? C6 C7 1.394(3) . ? C11A C16A 1.365(14) . ? C11A C12A 1.402(12) . ? C12A C13A 1.397(8) . ? C13A C14A 1.396(12) . ? C14A C15A 1.375(12) . ? C15A C16A 1.383(7) . ? C11B C12B 1.328(18) . ? C11B C16B 1.427(18) . ? C12B C13B 1.384(7) . ? C13B C14B 1.331(14) . ? C14B C15B 1.409(14) . ? C15B C16B 1.391(7) . ? C21 C26 1.389(3) . ? C21 C22 1.394(3) . ? C22 C23 1.386(4) . ? C23 C24 1.391(4) . ? C23 C27 1.491(5) . ? C24 C25 1.385(4) . ? C25 C26 1.384(3) . ? C27 C28B 1.169(6) . ? C27 C28A 1.181(5) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N2 N1 C7 122.90(18) . . ? N2 N1 C11A 115.7(9) . . ? C7 N1 C11A 120.8(9) . . ? N2 N1 C11B 111.8(10) . . ? C7 N1 C11B 124.8(10) . . ? C1 N2 N1 116.02(18) . . ? C1 N3 C2 116.10(19) . . ? N2 C1 N3 127.2(2) . . ? N2 C1 C21 115.2(2) . . ? N3 C1 C21 117.57(19) . . ? N3 C2 C3 119.9(2) . . ? N3 C2 C7 122.1(2) . . ? C3 C2 C7 118.0(2) . . ? C4 C3 C2 121.0(2) . . ? C3 C4 C5 120.4(2) . . ? C6 C5 C4 120.2(2) . . ? C5 C6 C7 119.7(2) . . ? C6 C7 N1 123.7(2) . . ? C6 C7 C2 120.7(2) . . ? N1 C7 C2 115.6(2) . . ? C16A C11A C12A 121.5(4) . . ? C16A C11A N1 124.7(9) . . ? C12A C11A N1 113.6(9) . . ? C13A C12A C11A 118.2(6) . . ? C14A C13A C12A 120.3(7) . . ? C15A C14A C13A 119.2(11) . . ? C14A C15A C16A 121.4(7) . . ? C11A C16A C15A 119.2(5) . . ? C12B C11B C16B 121.0(4) . . ? C12B C11B N1 124.9(13) . . ? C16B C11B N1 114.0(12) . . ? C11B C12B C13B 120.2(6) . . ? C14B C13B C12B 121.5(8) . . ? C13B C14B C15B 120.1(11) . . ? C16B C15B C14B 119.3(7) . . ? C15B C16B C11B 117.9(6) . . ? C26 C21 C22 118.6(2) . . ? C26 C21 C1 121.5(2) . . ? C22 C21 C1 120.0(2) . . ? C23 C22 C21 121.9(3) . . ? C22 C23 C24 118.3(2) . . ? C22 C23 C27 120.3(3) . . ? C24 C23 C27 121.5(3) . . ? C25 C24 C23 120.8(3) . . ? C26 C25 C24 120.0(3) . . ? C25 C26 C21 120.4(2) . . ? C28B C27 C23 135.4(6) . . ? C28A C27 C23 136.2(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 C7 N1 N2 C1 0.9(3) . . . . ? C11A N1 N2 C1 171.5(6) . . . . ? C11B N1 N2 C1 -171.3(6) . . . . ? N1 N2 C1 N3 0.6(3) . . . . ? N1 N2 C1 C21 179.63(17) . . . . ? C2 N3 C1 N2 -1.3(3) . . . . ? C2 N3 C1 C21 179.63(17) . . . . ? C1 N3 C2 C3 -179.8(2) . . . . ? C1 N3 C2 C7 0.7(3) . . . . ? N3 C2 C3 C4 -179.7(2) . . . . ? C7 C2 C3 C4 -0.2(3) . . . . ? C2 C3 C4 C5 -0.5(4) . . . . ? C3 C4 C5 C6 0.9(4) . . . . ? C4 C5 C6 C7 -0.4(4) . . . . ? C5 C6 C7 N1 179.3(2) . . . . ? C5 C6 C7 C2 -0.3(3) . . . . ? N2 N1 C7 C6 179.0(2) . . . . ? C11A N1 C7 C6 8.9(7) . . . . ? C11B N1 C7 C6 -9.8(7) . . . . ? N2 N1 C7 C2 -1.4(3) . . . . ? C11A N1 C7 C2 -171.5(6) . . . . ? C11B N1 C7 C2 169.8(6) . . . . ? N3 C2 C7 C6 -179.8(2) . . . . ? C3 C2 C7 C6 0.6(3) . . . . ? N3 C2 C7 N1 0.5(3) . . . . ? C3 C2 C7 N1 -179.0(2) . . . . ? N2 N1 C11A C16A -116.5(16) . . . . ? C7 N1 C11A C16A 54.3(19) . . . . ? N2 N1 C11A C12A 69.2(15) . . . . ? C7 N1 C11A C12A -120.0(12) . . . . ? C16A C11A C12A C13A 3(2) . . . . ? N1 C11A C12A C13A 177.8(9) . . . . ? C11A C12A C13A C14A 0.6(15) . . . . ? C12A C13A C14A C15A -3.1(15) . . . . ? C13A C14A C15A C16A 1.8(14) . . . . ? C12A C11A C16A C15A -5(2) . . . . ? N1 C11A C16A C15A -178.5(12) . . . . ? C14A C15A C16A C11A 2.0(14) . . . . ? N2 N1 C11B C12B 125.6(16) . . . . ? C7 N1 C11B C12B -46.4(17) . . . . ? N2 N1 C11B C16B -57.9(13) . . . . ? C7 N1 C11B C16B 130.1(12) . . . . ? C16B C11B C12B C13B -3(2) . . . . ? N1 C11B C12B C13B 173.4(11) . . . . ? C11B C12B C13B C14B 0.3(14) . . . . ? C12B C13B C14B C15B 2.5(14) . . . . ? C13B C14B C15B C16B -2.9(14) . . . . ? C14B C15B C16B C11B 0.5(12) . . . . ? C12B C11B C16B C15B 2(2) . . . . ? N1 C11B C16B C15B -174.3(9) . . . . ? N2 C1 C21 C26 8.6(3) . . . . ? N3 C1 C21 C26 -172.2(2) . . . . ? N2 C1 C21 C22 -171.6(2) . . . . ? N3 C1 C21 C22 7.6(3) . . . . ? C26 C21 C22 C23 0.4(4) . . . . ? C1 C21 C22 C23 -179.4(2) . . . . ? C21 C22 C23 C24 0.0(4) . . . . ? C21 C22 C23 C27 179.9(2) . . . . ? C22 C23 C24 C25 -0.7(4) . . . . ? C27 C23 C24 C25 179.3(3) . . . . ? C23 C24 C25 C26 1.1(4) . . . . ? C24 C25 C26 C21 -0.8(4) . . . . ? C22 C21 C26 C25 0.1(3) . . . . ? C1 C21 C26 C25 179.9(2) . . . . ? C22 C23 C27 C28B 28.8(11) . . . . ? C24 C23 C27 C28B -151.2(9) . . . . ? C22 C23 C27 C28A -168.8(6) . . . . ? C24 C23 C27 C28A 11.2(8) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.83 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.312 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.045 # Attachment '- 1b.cif' data_vic0626 _database_code_depnum_ccdc_archive 'CCDC 799187' #TrackingRef '- 1b.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic '1-(4-bromophenyl)-3-(3-vinylphenyl)-1,2,4-benzotriazin-4(1H)-yl radical' _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H15 Br N3' _chemical_formula_sum 'C21 H15 Br N3' _chemical_formula_weight 389.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 16.5376(18) _cell_length_b 13.7569(15) _cell_length_c 22.820(3) _cell_angle_alpha 90.00 _cell_angle_beta 93.7888(18) _cell_angle_gamma 90.00 _cell_volume 5180.3(10) _cell_formula_units_Z 12 _cell_measurement_temperature 193(2) _cell_measurement_reflns_used 4213 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 24.24 _exptl_crystal_description prism _exptl_crystal_colour brown _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.497 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2364 _exptl_absorpt_coefficient_mu 2.388 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3755 _exptl_absorpt_correction_T_max 0.5649 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1996)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 193(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 PLATFORM diffractometer/SMART 1000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 35190 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.00 _reflns_number_total 9135 _reflns_number_gt 6107 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART (Bruker, 1997)' _computing_cell_refinement 'Bruker SAINT (Bruker, 1997)' _computing_data_reduction 'Bruker SAINT (Bruker, 1997)' _computing_structure_solution 'DIRDIF-96 (Beurskens et al., 1996)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL (Bruker, 1997)' _computing_publication_material 'Bruker SHELXTL (Bruker, 1997)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+3.3754P] 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 9135 _refine_ls_number_parameters 676 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0425 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1014 _refine_ls_goodness_of_fit_ref 1.005 _refine_ls_restrained_S_all 1.005 _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 Br1A Br 0.85634(3) -0.13312(4) 0.14844(3) 0.07196(18) Uani 1 1 d . . . N1A N 0.50387(17) -0.0485(2) 0.18826(12) 0.0345(7) Uani 1 1 d . . . N2A N 0.46898(17) 0.0121(2) 0.14630(12) 0.0347(7) Uani 1 1 d . . . N3A N 0.34400(17) 0.0056(2) 0.19367(12) 0.0358(7) Uani 1 1 d . . . C1A C 0.3913(2) 0.0344(2) 0.15202(15) 0.0333(8) Uani 1 1 d . . . C2A C 0.3792(2) -0.0585(2) 0.23380(15) 0.0338(8) Uani 1 1 d . . . C3A C 0.3323(2) -0.0962(3) 0.27773(16) 0.0409(9) Uani 1 1 d . . . H3A H 0.2782 -0.0744 0.2805 0.049 Uiso 1 1 calc R . . C4A C 0.3644(2) -0.1642(3) 0.31653(17) 0.0432(9) Uani 1 1 d . . . H4A H 0.3323 -0.1894 0.3460 0.052 Uiso 1 1 calc R . . C5A C 0.4433(2) -0.1963(3) 0.31320(17) 0.0461(10) Uani 1 1 d . . . H5A H 0.4643 -0.2445 0.3399 0.055 Uiso 1 1 calc R . . C6A C 0.4916(2) -0.1594(3) 0.27167(16) 0.0405(9) Uani 1 1 d . . . H6A H 0.5459 -0.1813 0.2699 0.049 Uiso 1 1 calc R . . C7A C 0.4601(2) -0.0895(2) 0.23213(15) 0.0335(8) Uani 1 1 d . . . C11A C 0.5868(2) -0.0700(2) 0.18034(15) 0.0327(8) Uani 1 1 d . . . C12A C 0.6096(2) -0.0928(2) 0.12452(16) 0.0373(9) Uani 1 1 d . . . H12A H 0.5699 -0.0955 0.0925 0.045 Uiso 1 1 calc R . . C13A C 0.6898(2) -0.1116(3) 0.11527(17) 0.0416(9) Uani 1 1 d . . . H13A H 0.7053 -0.1278 0.0771 0.050 Uiso 1 1 calc R . . C14A C 0.7464(2) -0.1067(3) 0.16136(18) 0.0420(9) Uani 1 1 d . . . C15A C 0.7260(2) -0.0819(3) 0.21704(17) 0.0451(10) Uani 1 1 d . . . H15A H 0.7664 -0.0774 0.2485 0.054 Uiso 1 1 calc R . . C16A C 0.6456(2) -0.0637(3) 0.22614(16) 0.0416(9) Uani 1 1 d . . . H16A H 0.6306 -0.0466 0.2643 0.050 Uiso 1 1 calc R . . C21A C 0.3547(2) 0.1014(2) 0.10629(15) 0.0348(8) Uani 1 1 d . . . C22A C 0.2715(2) 0.1144(3) 0.10188(16) 0.0391(9) Uani 1 1 d . . . H22A H 0.2393 0.0804 0.1282 0.047 Uiso 1 1 calc R . . C23A C 0.2335(2) 0.1757(3) 0.06004(16) 0.0421(9) Uani 1 1 d . . . C24A C 0.2821(3) 0.2258(3) 0.02275(16) 0.0477(10) Uani 1 1 d . . . H24A H 0.2578 0.2688 -0.0058 0.057 Uiso 1 1 calc R . . C25A C 0.3648(3) 0.2138(3) 0.02681(17) 0.0496(10) Uani 1 1 d . . . H25A H 0.3971 0.2490 0.0012 0.059 Uiso 1 1 calc R . . C26A C 0.4017(2) 0.1508(3) 0.06795(16) 0.0421(9) Uani 1 1 d . . . H26A H 0.4587 0.1417 0.0698 0.051 Uiso 1 1 calc R . . C27A C 0.1436(3) 0.1837(3) 0.05612(19) 0.0560(11) Uani 1 1 d . . . H27A H 0.1165 0.1431 0.0823 0.067 Uiso 1 1 calc R . . C28A C 0.0992(4) 0.2356(5) 0.0237(3) 0.0999(19) Uani 1 1 d . . . H28A H 0.1221 0.2780 -0.0036 0.120 Uiso 1 1 calc R . . H28B H 0.0421 0.2332 0.0260 0.120 Uiso 1 1 calc R . . Br1B Br -0.35746(2) 0.70859(4) 0.37702(2) 0.05793(15) Uani 1 1 d . . . N1B N -0.00829(17) 0.8047(2) 0.33416(12) 0.0345(7) Uani 1 1 d . . . N2B N 0.02533(17) 0.8720(2) 0.37307(12) 0.0361(7) Uani 1 1 d . . . N3B N 0.15451(17) 0.8481(2) 0.33323(13) 0.0369(7) Uani 1 1 d . . . C1B C 0.1045(2) 0.8886(2) 0.36992(15) 0.0349(8) Uani 1 1 d . . . C2B C 0.1184(2) 0.7873(2) 0.29167(15) 0.0345(8) Uani 1 1 d . . . C3B C 0.1652(2) 0.7472(3) 0.24814(16) 0.0410(9) Uani 1 1 d . . . H3B H 0.2216 0.7609 0.2488 0.049 Uiso 1 1 calc R . . C4B C 0.1302(2) 0.6888(3) 0.20501(16) 0.0431(9) Uani 1 1 d . . . H4B H 0.1627 0.6615 0.1764 0.052 Uiso 1 1 calc R . . C5B C 0.0483(2) 0.6693(3) 0.20265(17) 0.0464(10) Uani 1 1 d . . . H5B H 0.0248 0.6292 0.1722 0.056 Uiso 1 1 calc R . . C6B C 0.0000(2) 0.7077(3) 0.24425(16) 0.0428(9) Uani 1 1 d . . . H6B H -0.0567 0.6953 0.2419 0.051 Uiso 1 1 calc R . . C7B C 0.0352(2) 0.7645(2) 0.28966(15) 0.0338(8) Uani 1 1 d . . . C11B C -0.0906(2) 0.7825(2) 0.34265(15) 0.0333(8) Uani 1 1 d . . . C12B C -0.1444(2) 0.8563(3) 0.35338(15) 0.0369(8) Uani 1 1 d . . . H12B H -0.1267 0.9220 0.3540 0.044 Uiso 1 1 calc R . . C13B C -0.2236(2) 0.8347(3) 0.36320(15) 0.0394(9) Uani 1 1 d . . . H13B H -0.2607 0.8854 0.3704 0.047 Uiso 1 1 calc R . . C14B C -0.2489(2) 0.7393(3) 0.36262(14) 0.0363(8) Uani 1 1 d . . . C15B C -0.1955(2) 0.6648(3) 0.35295(16) 0.0402(9) Uani 1 1 d . . . H15B H -0.2132 0.5991 0.3530 0.048 Uiso 1 1 calc R . . C16B C -0.1163(2) 0.6870(3) 0.34327(16) 0.0397(9) Uani 1 1 d . . . H16B H -0.0790 0.6362 0.3369 0.048 Uiso 1 1 calc R . . C21B C 0.1393(2) 0.9620(3) 0.41268(15) 0.0361(8) Uani 1 1 d . . . C22B C 0.2215(2) 0.9828(3) 0.41524(16) 0.0441(9) Uani 1 1 d . . . H22B H 0.2556 0.9480 0.3907 0.053 Uiso 1 1 calc R . . C23B C 0.2553(3) 1.0536(3) 0.45304(18) 0.0500(11) Uani 1 1 d . . . C24B C 0.2037(3) 1.1041(3) 0.48828(17) 0.0500(11) Uani 1 1 d . . . H24B H 0.2250 1.1543 0.5134 0.060 Uiso 1 1 calc R . . C25B C 0.1231(3) 1.0824(3) 0.48715(17) 0.0486(10) Uani 1 1 d . . . H25B H 0.0892 1.1165 0.5122 0.058 Uiso 1 1 calc R . . C26B C 0.0898(2) 1.0106(3) 0.44964(16) 0.0405(9) Uani 1 1 d . . . H26B H 0.0338 0.9952 0.4495 0.049 Uiso 1 1 calc R . . C27B C 0.3418(3) 1.0782(5) 0.4575(2) 0.0786(16) Uani 1 1 d . . . H27B H 0.3559 1.1350 0.4796 0.094 Uiso 1 1 calc R . . C28B C 0.3965(5) 1.0372(6) 0.4376(3) 0.119(2) Uani 1 1 d . . . H28C H 0.3869 0.9798 0.4151 0.143 Uiso 1 1 calc R . . H28D H 0.4500 1.0616 0.4441 0.143 Uiso 1 1 calc R . . Br1C Br -0.35732(2) 0.07608(3) 0.38185(2) 0.05377(14) Uani 1 1 d . . . N1C N -0.00768(17) 0.1627(2) 0.33273(12) 0.0358(7) Uani 1 1 d . . . N2C N 0.03074(17) 0.2235(2) 0.37296(12) 0.0363(7) Uani 1 1 d . . . N3C N 0.15530(18) 0.1990(2) 0.32724(13) 0.0385(7) Uani 1 1 d . . . C1C C 0.1098(2) 0.2384(2) 0.36745(15) 0.0355(8) Uani 1 1 d . . . C2C C 0.1170(2) 0.1325(2) 0.28992(15) 0.0346(8) Uani 1 1 d . . . C3C C 0.1621(2) 0.0829(3) 0.24947(16) 0.0407(9) Uani 1 1 d . . . H3C H 0.2178 0.0977 0.2469 0.049 Uiso 1 1 calc R . . C4C C 0.1261(2) 0.0126(3) 0.21336(16) 0.0428(9) Uani 1 1 d . . . H4C H 0.1572 -0.0212 0.1863 0.051 Uiso 1 1 calc R . . C5C C 0.0450(2) -0.0088(3) 0.21648(17) 0.0448(9) Uani 1 1 d . . . H5C H 0.0208 -0.0575 0.1915 0.054 Uiso 1 1 calc R . . C6C C -0.0018(2) 0.0393(3) 0.25533(16) 0.0410(9) Uani 1 1 d . . . H6C H -0.0576 0.0240 0.2571 0.049 Uiso 1 1 calc R . . C7C C 0.0341(2) 0.1111(2) 0.29212(15) 0.0341(8) Uani 1 1 d . . . C11C C -0.0908(2) 0.1452(2) 0.34352(15) 0.0343(8) Uani 1 1 d . . . C12C C -0.1101(2) 0.1199(2) 0.39967(15) 0.0349(8) Uani 1 1 d . . . H12C H -0.0686 0.1160 0.4304 0.042 Uiso 1 1 calc R . . C13C C -0.1895(2) 0.1003(2) 0.41098(16) 0.0366(8) Uani 1 1 d . . . H13C H -0.2028 0.0823 0.4494 0.044 Uiso 1 1 calc R . . C14C C -0.2490(2) 0.1071(2) 0.36608(16) 0.0374(8) Uani 1 1 d . . . C15C C -0.2309(2) 0.1350(3) 0.31007(16) 0.0406(9) Uani 1 1 d . . . H15C H -0.2727 0.1414 0.2797 0.049 Uiso 1 1 calc R . . C16C C -0.1518(2) 0.1535(3) 0.29894(16) 0.0392(9) Uani 1 1 d . . . H16C H -0.1387 0.1719 0.2606 0.047 Uiso 1 1 calc R . . C21C C 0.1501(2) 0.3035(2) 0.41216(16) 0.0368(8) Uani 1 1 d . . . C22C C 0.2322(2) 0.3226(3) 0.41111(16) 0.0411(9) Uani 1 1 d . . . H22C H 0.2615 0.2962 0.3804 0.049 Uiso 1 1 calc R . . C23C C 0.2728(2) 0.3800(3) 0.45427(18) 0.0479(10) Uani 1 1 d . . . C24C C 0.2280(3) 0.4189(3) 0.49859(18) 0.0511(10) Uani 1 1 d . . . H24C H 0.2543 0.4579 0.5285 0.061 Uiso 1 1 calc R . . C25C C 0.1463(3) 0.4013(3) 0.49923(17) 0.0503(10) Uani 1 1 d . . . H25C H 0.1164 0.4293 0.5291 0.060 Uiso 1 1 calc R . . C26C C 0.1072(2) 0.3433(3) 0.45685(16) 0.0430(9) Uani 1 1 d . . . H26C H 0.0509 0.3306 0.4582 0.052 Uiso 1 1 calc R . . C27C C 0.3598(3) 0.3999(4) 0.4557(2) 0.0668(13) Uani 1 1 d . . . H27C H 0.3797 0.4444 0.4851 0.080 Uiso 1 1 calc R . . C28C C 0.4088(4) 0.3682(5) 0.4254(3) 0.108(2) Uani 1 1 d . . . H28E H 0.3931 0.3233 0.3951 0.130 Uiso 1 1 calc R . . H28F H 0.4639 0.3877 0.4313 0.130 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 Br1A 0.0338(2) 0.0787(4) 0.1045(4) -0.0045(3) 0.0129(2) 0.0049(2) N1A 0.0334(17) 0.0369(17) 0.0337(17) 0.0021(13) 0.0048(13) -0.0007(13) N2A 0.0348(16) 0.0351(17) 0.0344(16) 0.0010(13) 0.0038(13) 0.0003(13) N3A 0.0350(16) 0.0374(17) 0.0355(17) 0.0012(14) 0.0067(13) 0.0010(13) C1A 0.038(2) 0.0288(18) 0.033(2) -0.0046(15) 0.0023(16) -0.0023(15) C2A 0.036(2) 0.031(2) 0.035(2) -0.0023(16) 0.0064(16) -0.0021(15) C3A 0.036(2) 0.043(2) 0.045(2) 0.0022(18) 0.0092(17) 0.0025(16) C4A 0.038(2) 0.051(2) 0.042(2) 0.0092(19) 0.0119(17) -0.0001(18) C5A 0.044(2) 0.051(2) 0.044(2) 0.0134(19) 0.0062(18) 0.0030(18) C6A 0.034(2) 0.043(2) 0.045(2) 0.0039(18) 0.0063(17) 0.0023(17) C7A 0.036(2) 0.034(2) 0.0318(19) -0.0014(16) 0.0074(15) -0.0018(15) C11A 0.0331(19) 0.0301(18) 0.035(2) -0.0011(15) 0.0022(16) -0.0039(15) C12A 0.040(2) 0.037(2) 0.036(2) -0.0048(16) 0.0035(16) -0.0051(16) C13A 0.040(2) 0.044(2) 0.042(2) -0.0096(18) 0.0107(18) -0.0038(17) C14A 0.034(2) 0.034(2) 0.058(3) 0.0012(18) 0.0075(18) -0.0019(16) C15A 0.034(2) 0.053(2) 0.047(2) 0.0088(19) -0.0049(18) -0.0043(18) C16A 0.044(2) 0.045(2) 0.036(2) -0.0012(17) 0.0065(17) -0.0009(18) C21A 0.043(2) 0.032(2) 0.0296(19) -0.0042(15) 0.0025(16) 0.0004(16) C22A 0.045(2) 0.039(2) 0.035(2) -0.0026(17) 0.0064(17) 0.0011(17) C23A 0.053(2) 0.039(2) 0.034(2) -0.0083(17) -0.0016(18) 0.0048(18) C24A 0.062(3) 0.045(2) 0.035(2) 0.0017(18) -0.0050(19) 0.005(2) C25A 0.063(3) 0.049(2) 0.037(2) 0.0069(19) 0.004(2) -0.006(2) C26A 0.048(2) 0.043(2) 0.035(2) -0.0010(18) 0.0007(17) -0.0037(18) C27A 0.062(3) 0.056(3) 0.048(3) -0.002(2) -0.012(2) 0.017(2) C28A 0.090(4) 0.125(5) 0.082(4) 0.011(4) -0.004(3) 0.027(4) Br1B 0.0316(2) 0.0833(3) 0.0595(3) 0.0085(2) 0.00782(18) -0.0014(2) N1B 0.0330(16) 0.0336(16) 0.0372(17) -0.0013(14) 0.0030(13) -0.0001(13) N2B 0.0346(17) 0.0359(17) 0.0378(17) -0.0018(14) 0.0028(13) -0.0008(13) N3B 0.0349(17) 0.0379(17) 0.0382(17) 0.0021(14) 0.0063(14) -0.0028(14) C1B 0.037(2) 0.0341(19) 0.0340(19) 0.0077(16) 0.0028(16) 0.0007(16) C2B 0.035(2) 0.034(2) 0.036(2) 0.0051(16) 0.0046(16) 0.0039(15) C3B 0.032(2) 0.046(2) 0.046(2) 0.0041(19) 0.0088(17) 0.0023(17) C4B 0.043(2) 0.047(2) 0.040(2) -0.0018(18) 0.0089(18) 0.0052(18) C5B 0.043(2) 0.054(2) 0.042(2) -0.0100(19) 0.0036(18) -0.0010(19) C6B 0.037(2) 0.050(2) 0.041(2) -0.0040(19) 0.0012(17) -0.0011(17) C7B 0.0317(19) 0.033(2) 0.037(2) 0.0048(16) 0.0067(16) 0.0043(15) C11B 0.0324(19) 0.035(2) 0.0323(19) 0.0006(15) 0.0023(15) 0.0015(15) C12B 0.036(2) 0.034(2) 0.040(2) 0.0009(16) 0.0035(16) 0.0050(16) C13B 0.038(2) 0.042(2) 0.038(2) 0.0019(17) 0.0041(16) 0.0125(17) C14B 0.0286(19) 0.055(2) 0.0257(18) 0.0006(17) 0.0021(14) 0.0030(17) C15B 0.043(2) 0.038(2) 0.040(2) 0.0011(17) 0.0038(17) -0.0021(17) C16B 0.038(2) 0.033(2) 0.049(2) 0.0004(17) 0.0088(17) 0.0033(16) C21B 0.039(2) 0.0337(19) 0.036(2) 0.0072(16) 0.0003(16) -0.0006(16) C22B 0.045(2) 0.051(2) 0.037(2) 0.0017(18) 0.0032(17) -0.0092(19) C23B 0.056(3) 0.051(3) 0.042(2) 0.014(2) -0.004(2) -0.018(2) C24B 0.071(3) 0.043(2) 0.035(2) 0.0072(18) -0.008(2) -0.011(2) C25B 0.065(3) 0.042(2) 0.039(2) 0.0015(18) 0.000(2) 0.004(2) C26B 0.045(2) 0.040(2) 0.036(2) 0.0034(17) -0.0013(17) 0.0040(17) C27B 0.061(4) 0.108(5) 0.067(4) 0.011(3) 0.006(3) -0.022(3) C28B 0.114(6) 0.135(7) 0.106(6) -0.002(5) -0.004(5) -0.042(5) Br1C 0.0350(2) 0.0624(3) 0.0654(3) -0.0025(2) 0.01426(19) 0.00123(19) N1C 0.0337(16) 0.0397(17) 0.0341(17) -0.0006(14) 0.0040(13) 0.0001(13) N2C 0.0387(18) 0.0368(17) 0.0335(17) 0.0009(13) 0.0027(13) -0.0011(13) N3C 0.0357(17) 0.0409(18) 0.0393(18) 0.0022(15) 0.0044(14) -0.0015(14) C1C 0.038(2) 0.033(2) 0.035(2) 0.0085(16) 0.0016(16) 0.0029(16) C2C 0.038(2) 0.034(2) 0.0325(19) 0.0079(16) 0.0034(16) -0.0026(16) C3C 0.032(2) 0.044(2) 0.046(2) 0.0028(18) 0.0086(17) 0.0002(17) C4C 0.045(2) 0.042(2) 0.043(2) -0.0029(18) 0.0107(18) 0.0020(18) C5C 0.046(2) 0.045(2) 0.044(2) -0.0077(18) 0.0059(18) -0.0042(18) C6C 0.036(2) 0.043(2) 0.045(2) -0.0033(18) 0.0082(17) -0.0065(17) C7C 0.0337(19) 0.0346(19) 0.034(2) 0.0039(16) 0.0042(15) 0.0020(15) C11C 0.035(2) 0.0311(19) 0.037(2) -0.0012(16) 0.0065(16) 0.0006(15) C12C 0.039(2) 0.0334(19) 0.032(2) 0.0017(16) 0.0000(15) 0.0034(16) C13C 0.042(2) 0.035(2) 0.034(2) 0.0014(16) 0.0105(17) 0.0070(16) C14C 0.034(2) 0.033(2) 0.045(2) -0.0042(17) 0.0081(17) 0.0042(15) C15C 0.039(2) 0.042(2) 0.040(2) -0.0049(17) 0.0014(17) 0.0037(17) C16C 0.040(2) 0.045(2) 0.033(2) 0.0004(17) 0.0056(16) 0.0020(17) C21C 0.040(2) 0.032(2) 0.039(2) 0.0069(17) 0.0017(17) 0.0007(16) C22C 0.047(2) 0.036(2) 0.040(2) 0.0048(17) 0.0033(18) -0.0035(17) C23C 0.051(2) 0.041(2) 0.051(3) 0.0109(19) -0.006(2) -0.0102(19) C24C 0.062(3) 0.043(2) 0.046(2) -0.0035(19) -0.008(2) -0.004(2) C25C 0.060(3) 0.052(3) 0.038(2) -0.0015(19) -0.001(2) 0.005(2) C26C 0.044(2) 0.047(2) 0.038(2) 0.0050(18) -0.0026(18) 0.0030(18) C27C 0.060(3) 0.075(4) 0.066(3) 0.006(3) 0.009(3) -0.012(3) C28C 0.108(6) 0.119(6) 0.095(5) 0.008(4) -0.010(4) -0.028(4) _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 Br1A C14A 1.895(4) . ? N1A N2A 1.368(4) . ? N1A C7A 1.392(4) . ? N1A C11A 1.426(4) . ? N2A C1A 1.336(4) . ? N3A C1A 1.331(4) . ? N3A C2A 1.372(4) . ? C1A C21A 1.490(5) . ? C2A C3A 1.406(5) . ? C2A C7A 1.408(5) . ? C3A C4A 1.371(5) . ? C4A C5A 1.384(5) . ? C5A C6A 1.377(5) . ? C6A C7A 1.396(5) . ? C11A C16A 1.383(5) . ? C11A C12A 1.388(5) . ? C12A C13A 1.381(5) . ? C13A C14A 1.364(5) . ? C14A C15A 1.379(5) . ? C15A C16A 1.383(5) . ? C21A C22A 1.385(5) . ? C21A C26A 1.386(5) . ? C22A C23A 1.392(5) . ? C23A C24A 1.392(5) . ? C23A C27A 1.487(6) . ? C24A C25A 1.374(6) . ? C25A C26A 1.389(5) . ? C27A C28A 1.236(6) . ? Br1B C14B 1.895(3) . ? N1B N2B 1.374(4) . ? N1B C7B 1.397(4) . ? N1B C11B 1.420(4) . ? N2B C1B 1.336(4) . ? N3B C1B 1.337(4) . ? N3B C2B 1.372(4) . ? C1B C21B 1.492(5) . ? C2B C7B 1.409(5) . ? C2B C3B 1.411(5) . ? C3B C4B 1.369(5) . ? C4B C5B 1.378(5) . ? C5B C6B 1.385(5) . ? C6B C7B 1.395(5) . ? C11B C16B 1.382(5) . ? C11B C12B 1.383(5) . ? C12B C13B 1.376(5) . ? C13B C14B 1.377(5) . ? C14B C15B 1.380(5) . ? C15B C16B 1.377(5) . ? C21B C26B 1.385(5) . ? C21B C22B 1.387(5) . ? C22B C23B 1.393(5) . ? C23B C24B 1.395(6) . ? C23B C27B 1.468(6) . ? C24B C25B 1.366(6) . ? C25B C26B 1.396(5) . ? C27B C28B 1.181(8) . ? Br1C C14C 1.898(4) . ? N1C N2C 1.367(4) . ? N1C C7C 1.388(4) . ? N1C C11C 1.433(4) . ? N2C C1C 1.337(4) . ? N3C C1C 1.340(4) . ? N3C C2C 1.375(4) . ? C1C C21C 1.482(5) . ? C2C C3C 1.402(5) . ? C2C C7C 1.406(5) . ? C3C C4C 1.379(5) . ? C4C C5C 1.380(5) . ? C5C C6C 1.383(5) . ? C6C C7C 1.402(5) . ? C11C C12C 1.385(5) . ? C11C C16C 1.389(5) . ? C12C C13C 1.381(5) . ? C13C C14C 1.377(5) . ? C14C C15C 1.387(5) . ? C15C C16C 1.372(5) . ? C21C C22C 1.384(5) . ? C21C C26C 1.392(5) . ? C22C C23C 1.399(5) . ? C23C C24C 1.400(6) . ? C23C C27C 1.463(6) . ? C24C C25C 1.373(6) . ? C25C C26C 1.381(5) . ? C27C C28C 1.183(8) . ? 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 N2A N1A C7A 122.3(3) . . ? N2A N1A C11A 113.7(3) . . ? C7A N1A C11A 123.8(3) . . ? C1A N2A N1A 115.8(3) . . ? C1A N3A C2A 115.2(3) . . ? N3A C1A N2A 128.0(3) . . ? N3A C1A C21A 117.0(3) . . ? N2A C1A C21A 115.0(3) . . ? N3A C2A C3A 118.9(3) . . ? N3A C2A C7A 122.6(3) . . ? C3A C2A C7A 118.5(3) . . ? C4A C3A C2A 120.3(3) . . ? C3A C4A C5A 120.6(3) . . ? C6A C5A C4A 120.8(4) . . ? C5A C6A C7A 119.4(3) . . ? N1A C7A C6A 123.7(3) . . ? N1A C7A C2A 115.9(3) . . ? C6A C7A C2A 120.4(3) . . ? C16A C11A C12A 119.2(3) . . ? C16A C11A N1A 121.7(3) . . ? C12A C11A N1A 119.0(3) . . ? C13A C12A C11A 120.3(3) . . ? C14A C13A C12A 119.4(3) . . ? C13A C14A C15A 121.7(3) . . ? C13A C14A Br1A 119.2(3) . . ? C15A C14A Br1A 119.1(3) . . ? C14A C15A C16A 118.7(3) . . ? C11A C16A C15A 120.7(3) . . ? C22A C21A C26A 119.1(3) . . ? C22A C21A C1A 119.1(3) . . ? C26A C21A C1A 121.8(3) . . ? C21A C22A C23A 121.9(3) . . ? C24A C23A C22A 117.9(4) . . ? C24A C23A C27A 122.8(4) . . ? C22A C23A C27A 119.3(4) . . ? C25A C24A C23A 120.8(4) . . ? C24A C25A C26A 120.7(4) . . ? C21A C26A C25A 119.6(4) . . ? C28A C27A C23A 129.1(5) . . ? N2B N1B C7B 122.1(3) . . ? N2B N1B C11B 114.0(3) . . ? C7B N1B C11B 123.9(3) . . ? C1B N2B N1B 115.9(3) . . ? C1B N3B C2B 115.4(3) . . ? N2B C1B N3B 127.7(3) . . ? N2B C1B C21B 114.7(3) . . ? N3B C1B C21B 117.6(3) . . ? N3B C2B C7B 122.5(3) . . ? N3B C2B C3B 119.4(3) . . ? C7B C2B C3B 118.1(3) . . ? C4B C3B C2B 120.6(3) . . ? C3B C4B C5B 120.7(3) . . ? C4B C5B C6B 120.6(4) . . ? C5B C6B C7B 119.4(4) . . ? C6B C7B N1B 123.6(3) . . ? C6B C7B C2B 120.5(3) . . ? N1B C7B C2B 115.9(3) . . ? C16B C11B C12B 119.6(3) . . ? C16B C11B N1B 120.3(3) . . ? C12B C11B N1B 120.0(3) . . ? C13B C12B C11B 120.1(3) . . ? C12B C13B C14B 119.7(3) . . ? C13B C14B C15B 120.8(3) . . ? C13B C14B Br1B 120.1(3) . . ? C15B C14B Br1B 119.1(3) . . ? C16B C15B C14B 119.1(3) . . ? C15B C16B C11B 120.6(3) . . ? C26B C21B C22B 119.5(3) . . ? C26B C21B C1B 120.5(3) . . ? C22B C21B C1B 120.1(3) . . ? C21B C22B C23B 121.4(4) . . ? C22B C23B C24B 118.0(4) . . ? C22B C23B C27B 123.6(5) . . ? C24B C23B C27B 118.4(4) . . ? C25B C24B C23B 120.9(4) . . ? C24B C25B C26B 120.7(4) . . ? C21B C26B C25B 119.3(4) . . ? C28B C27B C23B 129.1(7) . . ? N2C N1C C7C 122.1(3) . . ? N2C N1C C11C 113.3(3) . . ? C7C N1C C11C 123.7(3) . . ? C1C N2C N1C 116.4(3) . . ? C1C N3C C2C 115.9(3) . . ? N2C C1C N3C 126.8(3) . . ? N2C C1C C21C 115.2(3) . . ? N3C C1C C21C 117.9(3) . . ? N3C C2C C3C 119.2(3) . . ? N3C C2C C7C 121.9(3) . . ? C3C C2C C7C 118.9(3) . . ? C4C C3C C2C 120.5(3) . . ? C3C C4C C5C 120.0(3) . . ? C4C C5C C6C 121.2(4) . . ? C5C C6C C7C 119.2(3) . . ? N1C C7C C6C 123.4(3) . . ? N1C C7C C2C 116.5(3) . . ? C6C C7C C2C 120.1(3) . . ? C12C C11C C16C 119.9(3) . . ? C12C C11C N1C 118.9(3) . . ? C16C C11C N1C 121.2(3) . . ? C13C C12C C11C 120.1(3) . . ? C14C C13C C12C 119.3(3) . . ? C13C C14C C15C 121.1(3) . . ? C13C C14C Br1C 118.8(3) . . ? C15C C14C Br1C 120.1(3) . . ? C16C C15C C14C 119.3(3) . . ? C15C C16C C11C 120.3(3) . . ? C22C C21C C26C 119.0(3) . . ? C22C C21C C1C 120.0(3) . . ? C26C C21C C1C 120.9(3) . . ? C21C C22C C23C 121.4(4) . . ? C22C C23C C24C 118.1(4) . . ? C22C C23C C27C 123.2(4) . . ? C24C C23C C27C 118.6(4) . . ? C25C C24C C23C 120.6(4) . . ? C24C C25C C26C 120.6(4) . . ? C25C C26C C21C 120.2(4) . . ? C28C C27C C23C 129.0(6) . . ? 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 C7A N1A N2A C1A 4.0(5) . . . . ? C11A N1A N2A C1A -179.9(3) . . . . ? C2A N3A C1A N2A -3.2(5) . . . . ? C2A N3A C1A C21A 178.0(3) . . . . ? N1A N2A C1A N3A 0.5(5) . . . . ? N1A N2A C1A C21A 179.3(3) . . . . ? C1A N3A C2A C3A -177.1(3) . . . . ? C1A N3A C2A C7A 1.7(5) . . . . ? N3A C2A C3A C4A 176.5(3) . . . . ? C7A C2A C3A C4A -2.3(5) . . . . ? C2A C3A C4A C5A 0.3(6) . . . . ? C3A C4A C5A C6A 1.3(6) . . . . ? C4A C5A C6A C7A -0.7(6) . . . . ? N2A N1A C7A C6A 172.9(3) . . . . ? C11A N1A C7A C6A -2.9(5) . . . . ? N2A N1A C7A C2A -5.2(5) . . . . ? C11A N1A C7A C2A 179.1(3) . . . . ? C5A C6A C7A N1A -179.4(3) . . . . ? C5A C6A C7A C2A -1.4(6) . . . . ? N3A C2A C7A N1A 2.2(5) . . . . ? C3A C2A C7A N1A -179.0(3) . . . . ? N3A C2A C7A C6A -175.9(3) . . . . ? C3A C2A C7A C6A 2.9(5) . . . . ? N2A N1A C11A C16A 132.1(3) . . . . ? C7A N1A C11A C16A -51.7(5) . . . . ? N2A N1A C11A C12A -44.4(4) . . . . ? C7A N1A C11A C12A 131.7(4) . . . . ? C16A C11A C12A C13A 1.8(5) . . . . ? N1A C11A C12A C13A 178.4(3) . . . . ? C11A C12A C13A C14A -0.6(5) . . . . ? C12A C13A C14A C15A -1.0(6) . . . . ? C12A C13A C14A Br1A 179.8(3) . . . . ? C13A C14A C15A C16A 1.4(6) . . . . ? Br1A C14A C15A C16A -179.4(3) . . . . ? C12A C11A C16A C15A -1.4(5) . . . . ? N1A C11A C16A C15A -177.9(3) . . . . ? C14A C15A C16A C11A -0.1(6) . . . . ? N3A C1A C21A C22A -13.0(5) . . . . ? N2A C1A C21A C22A 168.0(3) . . . . ? N3A C1A C21A C26A 167.1(3) . . . . ? N2A C1A C21A C26A -11.8(5) . . . . ? C26A C21A C22A C23A 0.0(5) . . . . ? C1A C21A C22A C23A -179.8(3) . . . . ? C21A C22A C23A C24A -1.1(5) . . . . ? C21A C22A C23A C27A 177.7(3) . . . . ? C22A C23A C24A C25A 0.9(6) . . . . ? C27A C23A C24A C25A -178.0(4) . . . . ? C23A C24A C25A C26A 0.5(6) . . . . ? C22A C21A C26A C25A 1.4(5) . . . . ? C1A C21A C26A C25A -178.8(3) . . . . ? C24A C25A C26A C21A -1.6(6) . . . . ? C24A C23A C27A C28A -3.7(7) . . . . ? C22A C23A C27A C28A 177.5(5) . . . . ? C7B N1B N2B C1B -7.1(4) . . . . ? C11B N1B N2B C1B 174.4(3) . . . . ? N1B N2B C1B N3B 0.5(5) . . . . ? N1B N2B C1B C21B 180.0(3) . . . . ? C2B N3B C1B N2B 4.6(5) . . . . ? C2B N3B C1B C21B -174.9(3) . . . . ? C1B N3B C2B C7B -3.4(5) . . . . ? C1B N3B C2B C3B 175.0(3) . . . . ? N3B C2B C3B C4B -177.8(3) . . . . ? C7B C2B C3B C4B 0.6(5) . . . . ? C2B C3B C4B C5B 1.1(6) . . . . ? C3B C4B C5B C6B -0.7(6) . . . . ? C4B C5B C6B C7B -1.6(6) . . . . ? C5B C6B C7B N1B -178.8(3) . . . . ? C5B C6B C7B C2B 3.3(5) . . . . ? N2B N1B C7B C6B -170.0(3) . . . . ? C11B N1B C7B C6B 8.4(5) . . . . ? N2B N1B C7B C2B 7.9(5) . . . . ? C11B N1B C7B C2B -173.7(3) . . . . ? N3B C2B C7B C6B 175.6(3) . . . . ? C3B C2B C7B C6B -2.9(5) . . . . ? N3B C2B C7B N1B -2.5(5) . . . . ? C3B C2B C7B N1B 179.1(3) . . . . ? N2B N1B C11B C16B -133.2(3) . . . . ? C7B N1B C11B C16B 48.3(5) . . . . ? N2B N1B C11B C12B 43.4(4) . . . . ? C7B N1B C11B C12B -135.1(3) . . . . ? C16B C11B C12B C13B -1.6(5) . . . . ? N1B C11B C12B C13B -178.2(3) . . . . ? C11B C12B C13B C14B 0.4(5) . . . . ? C12B C13B C14B C15B 0.7(5) . . . . ? C12B C13B C14B Br1B 179.2(3) . . . . ? C13B C14B C15B C16B -0.6(5) . . . . ? Br1B C14B C15B C16B -179.1(3) . . . . ? C14B C15B C16B C11B -0.6(6) . . . . ? C12B C11B C16B C15B 1.7(5) . . . . ? N1B C11B C16B C15B 178.3(3) . . . . ? N2B C1B C21B C26B -3.2(5) . . . . ? N3B C1B C21B C26B 176.4(3) . . . . ? N2B C1B C21B C22B 177.5(3) . . . . ? N3B C1B C21B C22B -2.9(5) . . . . ? C26B C21B C22B C23B -1.9(6) . . . . ? C1B C21B C22B C23B 177.4(3) . . . . ? C21B C22B C23B C24B -0.5(6) . . . . ? C21B C22B C23B C27B 179.8(4) . . . . ? C22B C23B C24B C25B 2.2(6) . . . . ? C27B C23B C24B C25B -178.1(4) . . . . ? C23B C24B C25B C26B -1.5(6) . . . . ? C22B C21B C26B C25B 2.6(5) . . . . ? C1B C21B C26B C25B -176.8(3) . . . . ? C24B C25B C26B C21B -0.9(6) . . . . ? C22B C23B C27B C28B -10.6(10) . . . . ? C24B C23B C27B C28B 169.7(7) . . . . ? C7C N1C N2C C1C 6.5(5) . . . . ? C11C N1C N2C C1C 176.2(3) . . . . ? N1C N2C C1C N3C -1.0(5) . . . . ? N1C N2C C1C C21C -179.1(3) . . . . ? C2C N3C C1C N2C -3.6(5) . . . . ? C2C N3C C1C C21C 174.5(3) . . . . ? C1C N3C C2C C3C -175.4(3) . . . . ? C1C N3C C2C C7C 2.9(5) . . . . ? N3C C2C C3C C4C 177.0(3) . . . . ? C7C C2C C3C C4C -1.4(5) . . . . ? C2C C3C C4C C5C 0.6(6) . . . . ? C3C C4C C5C C6C 0.2(6) . . . . ? C4C C5C C6C C7C 0.0(6) . . . . ? N2C N1C C7C C6C 171.8(3) . . . . ? C11C N1C C7C C6C 3.2(5) . . . . ? N2C N1C C7C C2C -7.0(5) . . . . ? C11C N1C C7C C2C -175.6(3) . . . . ? C5C C6C C7C N1C -179.5(3) . . . . ? C5C C6C C7C C2C -0.9(5) . . . . ? N3C C2C C7C N1C 2.0(5) . . . . ? C3C C2C C7C N1C -179.7(3) . . . . ? N3C C2C C7C C6C -176.8(3) . . . . ? C3C C2C C7C C6C 1.5(5) . . . . ? N2C N1C C11C C12C -48.5(4) . . . . ? C7C N1C C11C C12C 121.1(4) . . . . ? N2C N1C C11C C16C 131.4(3) . . . . ? C7C N1C C11C C16C -59.1(5) . . . . ? C16C C11C C12C C13C 1.7(5) . . . . ? N1C C11C C12C C13C -178.4(3) . . . . ? C11C C12C C13C C14C -0.6(5) . . . . ? C12C C13C C14C C15C -1.2(5) . . . . ? C12C C13C C14C Br1C 178.1(3) . . . . ? C13C C14C C15C C16C 1.9(5) . . . . ? Br1C C14C C15C C16C -177.4(3) . . . . ? C14C C15C C16C C11C -0.7(5) . . . . ? C12C C11C C16C C15C -1.1(5) . . . . ? N1C C11C C16C C15C 179.1(3) . . . . ? N2C C1C C21C C22C 179.0(3) . . . . ? N3C C1C C21C C22C 0.7(5) . . . . ? N2C C1C C21C C26C 1.3(5) . . . . ? N3C C1C C21C C26C -177.0(3) . . . . ? C26C C21C C22C C23C 0.7(5) . . . . ? C1C C21C C22C C23C -176.9(3) . . . . ? C21C C22C C23C C24C -0.7(6) . . . . ? C21C C22C C23C C27C 178.4(4) . . . . ? C22C C23C C24C C25C -0.3(6) . . . . ? C27C C23C C24C C25C -179.4(4) . . . . ? C23C C24C C25C C26C 1.3(6) . . . . ? C24C C25C C26C C21C -1.3(6) . . . . ? C22C C21C C26C C25C 0.3(5) . . . . ? C1C C21C C26C C25C 177.9(3) . . . . ? C22C C23C C27C C28C -5.3(9) . . . . ? C24C C23C C27C C28C 173.7(6) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 1.125 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.070