# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_tianli0327 _audit_creation_date 2013-03-29 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:20:19, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C30 H24 Br N3 O3' _chemical_formula_sum 'C30 H24 Br N3 O3' _chemical_formula_weight 554.43 _chemical_absolute_configuration ad _chemical_melting_point ? 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' _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_H-M_alt 'P 21 21 21' _space_group_name_Hall 'P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' _cell_length_a 11.4213(5) _cell_length_b 13.1929(4) _cell_length_c 17.2730(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2602.68(16) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2016 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 20.3190 _cell_measurement_theta_min 3.7340 _exptl_absorpt_coefficient_mu 1.616 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.93834 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1136 _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.11 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_unetI/netI 0.0829 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 9098 _diffrn_reflns_theta_full 25.50 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 2.96 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean 16.0733 _diffrn_measured_fraction_theta_full 0.9970 _diffrn_measured_fraction_theta_max 0.8791 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -4.00 22.40 1.2000 25.0000 omega____ theta____ kappa____ phi______ frames - -19.2137 -99.0000 -120.0000 22 #__ type_ start__ end____ width___ exp.time_ 2 omega 24.00 84.00 1.2000 25.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 57.0000 -90.0000 50 #__ type_ start__ end____ width___ exp.time_ 3 omega 24.00 48.00 1.2000 25.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 -57.0000 -30.0000 20 #__ type_ start__ end____ width___ exp.time_ 4 omega -2.00 89.20 1.2000 25.0000 omega____ theta____ kappa____ phi______ frames - 22.6512 57.0000 30.0000 76 ; _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0102751000 _diffrn_orient_matrix_UB_12 -0.0023609000 _diffrn_orient_matrix_UB_13 -0.0404571000 _diffrn_orient_matrix_UB_21 0.0604670000 _diffrn_orient_matrix_UB_22 -0.0086097000 _diffrn_orient_matrix_UB_23 -0.0065707000 _diffrn_orient_matrix_UB_31 -0.0093614000 _diffrn_orient_matrix_UB_32 -0.0530335000 _diffrn_orient_matrix_UB_33 0.0029279000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3382 _reflns_number_total 5296 _reflns_odcompleteness_completeness 99.70 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.36.24 (release 03-12-2012 CrysAlis171 .NET) (compiled Dec 3 2012,18:21:49) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.327 _refine_diff_density_min -0.372 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(8) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 338 _refine_ls_number_reflns 5296 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1025 _refine_ls_R_factor_gt 0.0530 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0177P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.0883 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H29 of C29, H14 of C14, H21 of C21, H12 of C12, H15 of C15, H13 of C13, H20 of C20, H30 of C30, H16 of C16, H17 of C17, H24 of C24, H23 of C23, H26 of C26, H22 of C22, H18 of C18, H27 of C27, H11 of C11, {H9A,H9B} of C9, H5 of C5, H4 of C4, H3 of C3, H2A of C2 2.a Ternary CH refined with riding coordinates: C16(H16), C17(H17), C18(H18) 2.b Secondary CH2 refined with riding coordinates: C9(H9A,H9B) 2.c Aromatic/amide H refined with riding coordinates: C2(H2A), C3(H3), C4(H4), C5(H5), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15), C20(H20), C21(H21), C22(H22), C23(H23), C24(H24), C26(H26), C27(H27), C29(H29), C30(H30) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 0.72502(5) 0.70611(4) 0.43046(3) 0.0808(2) Uani 1 1 d . . . O1 O 1.2219(3) 0.4473(3) 0.63268(19) 0.0857(11) Uani 1 1 d . . . O2 O 0.8902(2) 0.26472(18) 0.70265(17) 0.0510(8) Uani 1 1 d . . . O3 O 1.2959(3) 0.5640(2) 0.7021(2) 0.0774(10) Uani 1 1 d . . . N1 N 0.7345(3) 0.3679(2) 0.73251(17) 0.0377(8) Uani 1 1 d . . . N2 N 1.0091(3) 0.4080(3) 0.8077(2) 0.0428(9) Uani 1 1 d . . . H2 H 0.986(3) 0.404(3) 0.8477(18) 0.024(12) Uiso 1 1 d . . . N3 N 1.2148(3) 0.5121(3) 0.6820(2) 0.0498(9) Uani 1 1 d . . . C1 C 0.8257(3) 0.5100(3) 0.7777(2) 0.0342(9) Uani 1 1 d . . . C2 C 0.8306(4) 0.6039(3) 0.8128(2) 0.0478(11) Uani 1 1 d . . . H2A H 0.9018 0.6367 0.8204 0.057 Uiso 1 1 calc R . . C3 C 0.7263(5) 0.6481(3) 0.8365(2) 0.0585(12) Uani 1 1 d . . . H3 H 0.7283 0.7108 0.8612 0.070 Uiso 1 1 calc R . . C4 C 0.6212(4) 0.6020(3) 0.8245(3) 0.0608(14) Uani 1 1 d . . . H4 H 0.5528 0.6336 0.8409 0.073 Uiso 1 1 calc R . . C5 C 0.6150(4) 0.5087(3) 0.7881(3) 0.0519(12) Uani 1 1 d . . . H5 H 0.5436 0.4771 0.7790 0.062 Uiso 1 1 calc R . . C6 C 0.7184(4) 0.4649(3) 0.76601(19) 0.0381(9) Uani 1 1 d . . . C7 C 0.8506(3) 0.3451(3) 0.7261(2) 0.0360(10) Uani 1 1 d . . . C8 C 0.9207(3) 0.4381(2) 0.7514(2) 0.0339(9) Uani 1 1 d . . . C9 C 0.6405(3) 0.2959(3) 0.7154(2) 0.0463(10) Uani 1 1 d . . . H9A H 0.5760 0.3081 0.7508 0.056 Uiso 1 1 calc R . . H9B H 0.6690 0.2277 0.7246 0.056 Uiso 1 1 calc R . . C10 C 0.5961(3) 0.3028(3) 0.6340(2) 0.0413(10) Uani 1 1 d . . . C11 C 0.6469(4) 0.2476(3) 0.5758(3) 0.0661(13) Uani 1 1 d . . . H11 H 0.7137 0.2097 0.5863 0.079 Uiso 1 1 calc R . . C12 C 0.6008(6) 0.2471(4) 0.5018(3) 0.0863(18) Uani 1 1 d . . . H12 H 0.6367 0.2088 0.4634 0.104 Uiso 1 1 calc R . . C13 C 0.5049(5) 0.3013(5) 0.4849(3) 0.0826(16) Uani 1 1 d . . . H13 H 0.4731 0.3002 0.4353 0.099 Uiso 1 1 calc R . . C14 C 0.4553(5) 0.3579(4) 0.5419(3) 0.0866(18) Uani 1 1 d . . . H14 H 0.3897 0.3969 0.5305 0.104 Uiso 1 1 calc R . . C15 C 0.4990(4) 0.3590(4) 0.6154(3) 0.0680(14) Uani 1 1 d . . . H15 H 0.4626 0.3981 0.6532 0.082 Uiso 1 1 calc R . . C16 C 0.9985(3) 0.4751(3) 0.6839(2) 0.0358(9) Uani 1 1 d . . . H16 H 1.0300 0.4143 0.6588 0.043 Uiso 1 1 calc R . . C17 C 1.1011(3) 0.5266(3) 0.7246(2) 0.0377(10) Uani 1 1 d . . . H17 H 1.0848 0.5994 0.7282 0.045 Uiso 1 1 calc R . . C18 C 1.1051(3) 0.4817(3) 0.8081(2) 0.0410(10) Uani 1 1 d . . . H18 H 1.0849 0.5359 0.8446 0.049 Uiso 1 1 calc R . . C19 C 1.2161(4) 0.4325(3) 0.8357(2) 0.0404(9) Uani 1 1 d . . . C20 C 1.2778(5) 0.4722(3) 0.8975(2) 0.0668(13) Uani 1 1 d . . . H20 H 1.2531 0.5323 0.9203 0.080 Uiso 1 1 calc R . . C21 C 1.3773(5) 0.4226(5) 0.9259(3) 0.0811(16) Uani 1 1 d . . . H21 H 1.4186 0.4498 0.9674 0.097 Uiso 1 1 calc R . . C22 C 1.4132(4) 0.3357(5) 0.8931(3) 0.0770(17) Uani 1 1 d . . . H22 H 1.4798 0.3034 0.9118 0.092 Uiso 1 1 calc R . . C23 C 1.3532(4) 0.2944(4) 0.8331(3) 0.0621(13) Uani 1 1 d . . . H23 H 1.3784 0.2339 0.8110 0.074 Uiso 1 1 calc R . . C24 C 1.2545(4) 0.3425(3) 0.8049(2) 0.0501(11) Uani 1 1 d . . . H24 H 1.2133 0.3133 0.7642 0.060 Uiso 1 1 calc R . . C25 C 0.9354(3) 0.5345(3) 0.6218(2) 0.0346(9) Uani 1 1 d . . . C26 C 0.9331(3) 0.6392(3) 0.6181(2) 0.0421(10) Uani 1 1 d . . . H26 H 0.9739 0.6767 0.6549 0.051 Uiso 1 1 calc R . . C27 C 0.8715(3) 0.6893(3) 0.5611(2) 0.0488(10) Uani 1 1 d . . . H27 H 0.8721 0.7597 0.5591 0.059 Uiso 1 1 calc R . . C28 C 0.8098(4) 0.6353(3) 0.5078(2) 0.0468(11) Uani 1 1 d . . . C29 C 0.8086(4) 0.5317(3) 0.5100(2) 0.0578(12) Uani 1 1 d . . . H29 H 0.7652 0.4952 0.4740 0.069 Uiso 1 1 calc R . . C30 C 0.8728(4) 0.4816(3) 0.5664(2) 0.0493(11) Uani 1 1 d . . . H30 H 0.8738 0.4111 0.5669 0.059 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 0.0996(4) 0.0899(3) 0.0528(3) -0.0047(3) -0.0245(3) 0.0273(3) O1 0.050(2) 0.124(3) 0.083(2) -0.039(2) 0.018(2) -0.003(2) O2 0.0397(17) 0.0339(14) 0.079(2) -0.0047(15) 0.0089(16) 0.0022(13) O3 0.040(2) 0.076(2) 0.116(3) -0.012(2) 0.012(2) -0.0250(18) N1 0.031(2) 0.0338(16) 0.0484(18) 0.0005(15) 0.0005(17) -0.0026(16) N2 0.030(2) 0.055(2) 0.044(2) 0.010(2) 0.0015(19) -0.0002(18) N3 0.035(2) 0.056(2) 0.058(2) 0.005(2) 0.001(2) -0.005(2) C1 0.035(2) 0.034(2) 0.034(2) -0.0001(19) 0.0053(18) 0.0076(18) C2 0.050(3) 0.046(2) 0.047(3) -0.002(2) 0.004(2) 0.000(2) C3 0.070(4) 0.046(2) 0.060(3) -0.007(2) 0.010(3) 0.022(3) C4 0.052(3) 0.057(3) 0.073(4) 0.004(3) 0.016(3) 0.023(3) C5 0.035(3) 0.054(3) 0.067(3) 0.008(3) 0.006(2) 0.006(2) C6 0.037(2) 0.039(2) 0.038(2) 0.0084(19) 0.007(2) 0.001(2) C7 0.031(2) 0.037(2) 0.040(2) 0.011(2) 0.0052(19) 0.0021(19) C8 0.028(2) 0.0329(19) 0.041(2) 0.0036(19) 0.0057(19) -0.0019(18) C9 0.034(2) 0.041(2) 0.064(3) 0.013(3) 0.005(2) -0.004(2) C10 0.031(2) 0.038(2) 0.055(3) 0.006(2) 0.003(2) -0.007(2) C11 0.059(3) 0.058(3) 0.081(4) -0.015(3) 0.002(3) 0.008(2) C12 0.094(5) 0.100(4) 0.065(4) -0.030(3) 0.016(3) -0.004(4) C13 0.069(4) 0.122(5) 0.057(3) 0.016(4) 0.001(3) -0.023(4) C14 0.073(4) 0.119(4) 0.068(4) 0.005(4) -0.015(3) 0.027(4) C15 0.055(3) 0.090(4) 0.059(3) 0.004(3) 0.003(3) 0.017(3) C16 0.034(2) 0.0280(18) 0.045(2) -0.003(2) 0.0061(19) -0.0013(18) C17 0.030(2) 0.032(2) 0.051(2) -0.004(2) 0.003(2) -0.0010(19) C18 0.037(3) 0.041(2) 0.045(2) -0.009(2) 0.004(2) 0.002(2) C19 0.036(2) 0.045(2) 0.039(2) 0.0000(19) -0.001(2) -0.003(2) C20 0.060(3) 0.081(3) 0.059(3) -0.020(3) -0.010(3) -0.007(3) C21 0.057(4) 0.129(5) 0.057(3) -0.013(4) -0.024(3) -0.021(3) C22 0.039(3) 0.133(5) 0.059(3) 0.023(4) -0.007(3) 0.005(3) C23 0.047(3) 0.072(3) 0.067(3) 0.015(3) 0.001(2) 0.008(3) C24 0.043(3) 0.055(2) 0.052(2) -0.001(2) -0.012(2) 0.005(2) C25 0.030(2) 0.037(2) 0.036(2) -0.005(2) 0.0052(19) -0.0019(19) C26 0.048(3) 0.039(2) 0.039(2) -0.006(2) -0.012(2) -0.001(2) C27 0.061(3) 0.042(2) 0.043(2) -0.002(2) 0.003(2) 0.004(2) C28 0.048(3) 0.055(3) 0.037(2) -0.003(2) 0.000(2) 0.006(2) C29 0.063(3) 0.064(3) 0.047(3) -0.010(2) -0.007(2) 0.002(3) C30 0.057(3) 0.042(2) 0.048(3) -0.008(2) 0.000(2) -0.001(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C28 1.896(4) . ? O1 N3 1.209(4) . ? O2 C7 1.222(4) . ? O3 N3 1.204(4) . ? N1 C6 1.416(4) . ? N1 C7 1.363(4) . ? N1 C9 1.463(4) . ? N2 H2 0.74(3) . ? N2 C8 1.457(5) . ? N2 C18 1.465(5) . ? N3 C17 1.505(5) . ? C1 C2 1.380(5) . ? C1 C6 1.378(5) . ? C1 C8 1.512(5) . ? C2 H2A 0.9300 . ? C2 C3 1.388(5) . ? C3 H3 0.9300 . ? C3 C4 1.362(6) . ? C4 H4 0.9300 . ? C4 C5 1.384(6) . ? C5 H5 0.9300 . ? C5 C6 1.369(5) . ? C7 C8 1.529(5) . ? C8 C16 1.545(5) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9 C10 1.497(5) . ? C10 C11 1.370(5) . ? C10 C15 1.373(6) . ? C11 H11 0.9300 . ? C11 C12 1.382(7) . ? C12 H12 0.9300 . ? C12 C13 1.340(6) . ? C13 H13 0.9300 . ? C13 C14 1.359(6) . ? C14 H14 0.9300 . ? C14 C15 1.365(6) . ? C15 H15 0.9300 . ? C16 H16 0.9800 . ? C16 C17 1.527(5) . ? C16 C25 1.510(5) . ? C17 H17 0.9800 . ? C17 C18 1.560(5) . ? C18 H18 0.9800 . ? C18 C19 1.502(5) . ? C19 C20 1.381(5) . ? C19 C24 1.373(5) . ? C20 H20 0.9300 . ? C20 C21 1.400(6) . ? C21 H21 0.9300 . ? C21 C22 1.343(6) . ? C22 H22 0.9300 . ? C22 C23 1.356(6) . ? C23 H23 0.9300 . ? C23 C24 1.383(5) . ? C24 H24 0.9300 . ? C25 C26 1.384(4) . ? C25 C30 1.384(5) . ? C26 H26 0.9300 . ? C26 C27 1.379(5) . ? C27 H27 0.9300 . ? C27 C28 1.360(5) . ? C28 C29 1.368(5) . ? C29 H29 0.9300 . ? C29 C30 1.387(5) . ? C30 H30 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 N1 C9 125.0(3) . . ? C7 N1 C6 111.0(3) . . ? C7 N1 C9 123.6(3) . . ? C8 N2 H2 113(3) . . ? C8 N2 C18 109.9(3) . . ? C18 N2 H2 108(3) . . ? O1 N3 C17 119.5(4) . . ? O3 N3 O1 123.7(4) . . ? O3 N3 C17 116.8(4) . . ? C2 C1 C8 131.8(4) . . ? C6 C1 C2 119.3(4) . . ? C6 C1 C8 108.9(3) . . ? C1 C2 H2A 120.9 . . ? C1 C2 C3 118.1(4) . . ? C3 C2 H2A 120.9 . . ? C2 C3 H3 119.2 . . ? C4 C3 C2 121.6(4) . . ? C4 C3 H3 119.2 . . ? C3 C4 H4 119.6 . . ? C3 C4 C5 120.7(4) . . ? C5 C4 H4 119.6 . . ? C4 C5 H5 121.3 . . ? C6 C5 C4 117.3(4) . . ? C6 C5 H5 121.3 . . ? C1 C6 N1 109.6(3) . . ? C5 C6 N1 127.5(4) . . ? C5 C6 C1 122.9(3) . . ? O2 C7 N1 125.3(4) . . ? O2 C7 C8 126.6(4) . . ? N1 C7 C8 108.0(3) . . ? N2 C8 C1 117.9(3) . . ? N2 C8 C7 109.6(3) . . ? N2 C8 C16 101.1(3) . . ? C1 C8 C7 102.3(3) . . ? C1 C8 C16 116.2(3) . . ? C7 C8 C16 109.8(3) . . ? N1 C9 H9A 108.9 . . ? N1 C9 H9B 108.9 . . ? N1 C9 C10 113.5(3) . . ? H9A C9 H9B 107.7 . . ? C10 C9 H9A 108.9 . . ? C10 C9 H9B 108.9 . . ? C11 C10 C9 120.9(4) . . ? C11 C10 C15 117.2(4) . . ? C15 C10 C9 121.8(4) . . ? C10 C11 H11 119.3 . . ? C10 C11 C12 121.4(4) . . ? C12 C11 H11 119.3 . . ? C11 C12 H12 119.7 . . ? C13 C12 C11 120.7(5) . . ? C13 C12 H12 119.7 . . ? C12 C13 H13 120.8 . . ? C12 C13 C14 118.4(5) . . ? C14 C13 H13 120.8 . . ? C13 C14 H14 119.1 . . ? C13 C14 C15 121.9(5) . . ? C15 C14 H14 119.1 . . ? C10 C15 H15 119.8 . . ? C14 C15 C10 120.5(5) . . ? C14 C15 H15 119.8 . . ? C8 C16 H16 106.6 . . ? C17 C16 C8 103.5(3) . . ? C17 C16 H16 106.6 . . ? C25 C16 C8 115.2(3) . . ? C25 C16 H16 106.6 . . ? C25 C16 C17 117.6(3) . . ? N3 C17 C16 112.3(3) . . ? N3 C17 H17 108.6 . . ? N3 C17 C18 112.3(3) . . ? C16 C17 H17 108.6 . . ? C16 C17 C18 106.2(3) . . ? C18 C17 H17 108.6 . . ? N2 C18 C17 103.1(3) . . ? N2 C18 H18 108.1 . . ? N2 C18 C19 110.3(3) . . ? C17 C18 H18 108.1 . . ? C19 C18 C17 118.8(3) . . ? C19 C18 H18 108.1 . . ? C20 C19 C18 120.8(4) . . ? C24 C19 C18 121.4(4) . . ? C24 C19 C20 117.6(4) . . ? C19 C20 H20 119.7 . . ? C19 C20 C21 120.6(4) . . ? C21 C20 H20 119.7 . . ? C20 C21 H21 120.1 . . ? C22 C21 C20 119.8(5) . . ? C22 C21 H21 120.1 . . ? C21 C22 H22 119.6 . . ? C21 C22 C23 120.8(5) . . ? C23 C22 H22 119.6 . . ? C22 C23 H23 120.1 . . ? C22 C23 C24 119.8(5) . . ? C24 C23 H23 120.1 . . ? C19 C24 C23 121.4(4) . . ? C19 C24 H24 119.3 . . ? C23 C24 H24 119.3 . . ? C26 C25 C16 124.0(3) . . ? C30 C25 C16 118.4(3) . . ? C30 C25 C26 117.5(4) . . ? C25 C26 H26 119.3 . . ? C27 C26 C25 121.4(4) . . ? C27 C26 H26 119.3 . . ? C26 C27 H27 120.1 . . ? C28 C27 C26 119.8(4) . . ? C28 C27 H27 120.1 . . ? C27 C28 Br1 118.9(3) . . ? C27 C28 C29 120.6(4) . . ? C29 C28 Br1 120.4(3) . . ? C28 C29 H29 120.3 . . ? C28 C29 C30 119.4(4) . . ? C30 C29 H29 120.3 . . ? C25 C30 C29 121.3(4) . . ? C25 C30 H30 119.4 . . ? C29 C30 H30 119.4 . . ? 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 Br1 C28 C29 C30 179.0(3) . . . . ? O1 N3 C17 C16 -15.7(5) . . . . ? O1 N3 C17 C18 103.9(4) . . . . ? O2 C7 C8 N2 -51.3(5) . . . . ? O2 C7 C8 C1 -177.2(4) . . . . ? O2 C7 C8 C16 58.9(5) . . . . ? O3 N3 C17 C16 167.5(3) . . . . ? O3 N3 C17 C18 -72.8(4) . . . . ? N1 C7 C8 N2 129.9(3) . . . . ? N1 C7 C8 C1 4.1(4) . . . . ? N1 C7 C8 C16 -119.9(3) . . . . ? N1 C9 C10 C11 88.4(5) . . . . ? N1 C9 C10 C15 -95.9(5) . . . . ? N2 C8 C16 C17 -36.9(3) . . . . ? N2 C8 C16 C25 -166.6(3) . . . . ? N2 C18 C19 C20 -124.8(4) . . . . ? N2 C18 C19 C24 49.9(5) . . . . ? N3 C17 C18 N2 -121.7(3) . . . . ? N3 C17 C18 C19 0.6(5) . . . . ? C1 C2 C3 C4 -1.3(6) . . . . ? C1 C8 C16 C17 92.0(4) . . . . ? C1 C8 C16 C25 -37.7(5) . . . . ? C2 C1 C6 N1 -177.5(3) . . . . ? C2 C1 C6 C5 -0.4(6) . . . . ? C2 C1 C8 N2 53.9(6) . . . . ? C2 C1 C8 C7 174.2(4) . . . . ? C2 C1 C8 C16 -66.2(6) . . . . ? C2 C3 C4 C5 0.1(7) . . . . ? C3 C4 C5 C6 0.9(6) . . . . ? C4 C5 C6 N1 175.8(4) . . . . ? C4 C5 C6 C1 -0.8(6) . . . . ? C6 N1 C7 O2 176.3(4) . . . . ? C6 N1 C7 C8 -4.9(4) . . . . ? C6 N1 C9 C10 94.3(4) . . . . ? C6 C1 C2 C3 1.4(6) . . . . ? C6 C1 C8 N2 -122.2(4) . . . . ? C6 C1 C8 C7 -1.9(4) . . . . ? C6 C1 C8 C16 117.7(3) . . . . ? C7 N1 C6 C1 3.7(4) . . . . ? C7 N1 C6 C5 -173.2(4) . . . . ? C7 N1 C9 C10 -93.4(4) . . . . ? C7 C8 C16 C17 -152.6(3) . . . . ? C7 C8 C16 C25 77.7(4) . . . . ? C8 N2 C18 C17 -26.7(4) . . . . ? C8 N2 C18 C19 -154.5(3) . . . . ? C8 C1 C2 C3 -174.4(4) . . . . ? C8 C1 C6 N1 -0.8(4) . . . . ? C8 C1 C6 C5 176.3(4) . . . . ? C8 C16 C17 N3 144.9(3) . . . . ? C8 C16 C17 C18 21.8(4) . . . . ? C8 C16 C25 C26 97.8(4) . . . . ? C8 C16 C25 C30 -80.2(4) . . . . ? C9 N1 C6 C1 176.8(3) . . . . ? C9 N1 C6 C5 -0.1(6) . . . . ? C9 N1 C7 O2 3.1(6) . . . . ? C9 N1 C7 C8 -178.1(3) . . . . ? C9 C10 C11 C12 174.7(4) . . . . ? C9 C10 C15 C14 -175.1(5) . . . . ? C10 C11 C12 C13 0.3(8) . . . . ? C11 C10 C15 C14 0.8(7) . . . . ? C11 C12 C13 C14 1.0(9) . . . . ? C12 C13 C14 C15 -1.4(9) . . . . ? C13 C14 C15 C10 0.5(9) . . . . ? C15 C10 C11 C12 -1.2(6) . . . . ? C16 C17 C18 N2 1.5(4) . . . . ? C16 C17 C18 C19 123.7(4) . . . . ? C16 C25 C26 C27 -178.4(3) . . . . ? C16 C25 C30 C29 177.0(4) . . . . ? C17 C16 C25 C26 -24.7(5) . . . . ? C17 C16 C25 C30 157.4(3) . . . . ? C17 C18 C19 C20 116.7(4) . . . . ? C17 C18 C19 C24 -68.7(5) . . . . ? C18 N2 C8 C1 -87.3(4) . . . . ? C18 N2 C8 C7 156.3(3) . . . . ? C18 N2 C8 C16 40.5(4) . . . . ? C18 C19 C20 C21 176.1(4) . . . . ? C18 C19 C24 C23 -176.5(4) . . . . ? C19 C20 C21 C22 -0.1(8) . . . . ? C20 C19 C24 C23 -1.7(6) . . . . ? C20 C21 C22 C23 -0.8(8) . . . . ? C21 C22 C23 C24 0.4(7) . . . . ? C22 C23 C24 C19 0.8(6) . . . . ? C24 C19 C20 C21 1.3(6) . . . . ? C25 C16 C17 N3 -86.8(4) . . . . ? C25 C16 C17 C18 150.1(3) . . . . ? C25 C26 C27 C28 1.1(6) . . . . ? C26 C25 C30 C29 -1.0(6) . . . . ? C26 C27 C28 Br1 179.6(3) . . . . ? C26 C27 C28 C29 -0.3(6) . . . . ? C27 C28 C29 C30 -1.1(6) . . . . ? C28 C29 C30 C25 1.8(6) . . . . ? C30 C25 C26 C27 -0.4(6) . . . . ? _database_code_depnum_ccdc_archive 'CCDC 936431'