# 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_Compound_1 # data_c515 CCDC 938967 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H22 Br2 N2 Zn' _chemical_formula_weight 587.65 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' Zn Zn 0.2839 1.4301 '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)/n 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 9.4853(5) _cell_length_b 12.9621(6) _cell_length_c 19.1602(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.9170(10) _cell_angle_gamma 90.00 _cell_volume 2355.4(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 5534 _cell_measurement_theta_min 2.38 _cell_measurement_theta_max 27.43 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.657 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 4.451 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2690 _exptl_absorpt_correction_T_max 0.4851 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16391 _diffrn_reflns_av_R_equivalents 0.0337 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.90 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5394 _reflns_number_gt 4658 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The restraints/contraints used in .ins file SADI 0.01 C8 C11A C9A C12A C10A C13A C2A C5A C1A C4A SADI 0.01 C8 C11 C9 C12 C10 C13 C2 C5 C1 C4 SADI 0.01 C8A C9A C9A C10A C10A C11A C11A C12A C12A C13A C13A C8A SADI 0.01 C1A C2A C2A C3A C3A C4A C4A C5A SADI 0.01 C8 C9 C9 C10 C10 C11 C11 C12 C12 C13 C13 C8 SADI 0.01 C1 C2 C2 C3 C3 C4 C4 C5 SADI 0.01 N1 C1 N1 C5 N1A C1A N1A C5A N2 C14 N2 C18 DFIX 1.30 C6 C7 DFIX 1.50 C3 C6 C7 C8 SADI 0.01 C7 C13 C7 C9 SADI 0.01 C6 C4 C6 C2 ISOR 0.01 0.02 C2A DFIX 1.30 C6A C7A DFIX 1.50 C3A C6A C7A C8A SADI 0.01 C7A C13A C7A C9A SADI 0.01 C6A C4A C6A C2A SIMU 0.01 0.02 N1 > C13A DELU 0.01 0.02 N1 > C13A ; _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^)+(0.0395P)^2^+0.0000P] 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 5394 _refine_ls_number_parameters 407 _refine_ls_number_restraints 579 _refine_ls_R_factor_all 0.0367 _refine_ls_R_factor_gt 0.0293 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0703 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.010 _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 Zn1 Zn 0.43504(3) 0.62244(2) 0.209491(13) 0.01475(7) Uani 1 1 d . . . Br1 Br 0.23089(2) 0.594849(18) 0.138704(12) 0.02014(7) Uani 1 1 d . A . Br2 Br 0.48757(3) 0.795558(18) 0.234553(12) 0.02213(7) Uani 1 1 d . A . N2 N 0.4096(2) 0.54705(14) 0.30236(9) 0.0158(4) Uani 1 1 d D A . N1 N 0.5920(14) 0.541(2) 0.1652(8) 0.0141(17) Uani 0.619(5) 1 d PDU A 1 C1 C 0.7263(9) 0.5350(11) 0.1903(4) 0.0157(12) Uani 0.619(5) 1 d PDU A 1 H1 H 0.7463 0.5643 0.2348 0.019 Uiso 0.619(5) 1 calc PR A 1 C2 C 0.8365(6) 0.4884(5) 0.1551(2) 0.0129(10) Uani 0.619(5) 1 d PDU A 1 H2 H 0.9278 0.4841 0.1761 0.015 Uiso 0.619(5) 1 calc PR A 1 C3 C 0.8107(5) 0.4481(4) 0.0886(2) 0.0120(9) Uani 0.619(5) 1 d PDU A 1 C4 C 0.6742(5) 0.4569(6) 0.0603(3) 0.0155(11) Uani 0.619(5) 1 d PDU A 1 H4 H 0.6536 0.4325 0.0145 0.019 Uiso 0.619(5) 1 calc PR A 1 C5 C 0.5687(7) 0.5020(10) 0.1003(5) 0.0175(13) Uani 0.619(5) 1 d PDU A 1 H5 H 0.4759 0.5053 0.0811 0.021 Uiso 0.619(5) 1 calc PR A 1 C6 C 0.9212(4) 0.3996(3) 0.0474(2) 0.0161(8) Uani 0.619(5) 1 d PDU A 1 H6 H 0.8993 0.3867 -0.0004 0.019 Uiso 0.619(5) 1 calc PR A 1 C7 C 1.0488(4) 0.3718(3) 0.06969(19) 0.0155(8) Uani 0.619(5) 1 d PDU A 1 H7 H 1.0701 0.3836 0.1176 0.019 Uiso 0.619(5) 1 calc PR A 1 C8 C 1.1613(5) 0.3243(4) 0.0280(2) 0.0132(10) Uani 0.619(5) 1 d PDU A 1 C9 C 1.2927(5) 0.3079(5) 0.0591(3) 0.0167(10) Uani 0.619(5) 1 d PDU A 1 H9 H 1.3086 0.3267 0.1065 0.020 Uiso 0.619(5) 1 calc PR A 1 C10 C 1.4004(7) 0.2640(9) 0.0213(4) 0.0219(12) Uani 0.619(5) 1 d PDU A 1 H10 H 1.4896 0.2518 0.0430 0.026 Uiso 0.619(5) 1 calc PR A 1 C11 C 1.3783(10) 0.2378(16) -0.0485(5) 0.0217(15) Uani 0.619(5) 1 d PDU A 1 H11 H 1.4532 0.2099 -0.0749 0.026 Uiso 0.619(5) 1 calc PR A 1 C12 C 1.2464(8) 0.2526(9) -0.0794(4) 0.0224(13) Uani 0.619(5) 1 d PDU A 1 H12 H 1.2300 0.2328 -0.1266 0.027 Uiso 0.619(5) 1 calc PR A 1 C13 C 1.1385(7) 0.2963(6) -0.0412(3) 0.0181(12) Uani 0.619(5) 1 d PDU A 1 H13 H 1.0486 0.3070 -0.0626 0.022 Uiso 0.619(5) 1 calc PR A 1 N1A N 0.598(2) 0.545(4) 0.1618(13) 0.015(2) Uani 0.381(5) 1 d PDU A 2 C1A C 0.7140(15) 0.5404(18) 0.2035(7) 0.0156(18) Uani 0.381(5) 1 d PDU A 2 H1A H 0.7115 0.5671 0.2496 0.019 Uiso 0.381(5) 1 calc PR A 2 C2A C 0.8356(11) 0.4967(9) 0.1791(4) 0.0130(16) Uani 0.381(5) 1 d PDU A 2 H2A H 0.9180 0.4960 0.2079 0.016 Uiso 0.381(5) 1 calc PR A 2 C3A C 0.8395(8) 0.4539(7) 0.1132(4) 0.0110(14) Uani 0.381(5) 1 d PDU A 2 C4A C 0.7183(8) 0.4569(8) 0.0729(4) 0.0114(16) Uani 0.381(5) 1 d PDU A 2 H4A H 0.7175 0.4263 0.0278 0.014 Uiso 0.381(5) 1 calc PR A 2 C5A C 0.5984(11) 0.5038(16) 0.0969(8) 0.0168(19) Uani 0.381(5) 1 d PDU A 2 H5A H 0.5162 0.5071 0.0680 0.020 Uiso 0.381(5) 1 calc PR A 2 C6A C 0.9712(7) 0.4045(5) 0.0884(3) 0.0162(13) Uani 0.381(5) 1 d PDU A 2 H6A H 1.0476 0.4013 0.1211 0.019 Uiso 0.381(5) 1 calc PR A 2 C7A C 0.9936(6) 0.3653(5) 0.0273(3) 0.0151(13) Uani 0.381(5) 1 d PDU A 2 H7A H 0.9173 0.3662 -0.0054 0.018 Uiso 0.381(5) 1 calc PR A 2 C8A C 1.1266(8) 0.3196(7) 0.0043(4) 0.0145(15) Uani 0.381(5) 1 d PDU A 2 C9A C 1.2452(8) 0.3146(8) 0.0476(4) 0.0151(16) Uani 0.381(5) 1 d PDU A 2 H9A H 1.2396 0.3410 0.0937 0.018 Uiso 0.381(5) 1 calc PR A 2 C10A C 1.3706(11) 0.2727(15) 0.0261(6) 0.0211(18) Uani 0.381(5) 1 d PDU A 2 H10A H 1.4499 0.2710 0.0571 0.025 Uiso 0.381(5) 1 calc PR A 2 C11A C 1.3808(16) 0.233(3) -0.0409(8) 0.023(2) Uani 0.381(5) 1 d PDU A 2 H11A H 1.4667 0.2035 -0.0560 0.027 Uiso 0.381(5) 1 calc PR A 2 C12A C 1.2643(13) 0.2372(15) -0.0856(6) 0.0202(19) Uani 0.381(5) 1 d PDU A 2 H12A H 1.2702 0.2113 -0.1319 0.024 Uiso 0.381(5) 1 calc PR A 2 C13A C 1.1397(11) 0.2792(10) -0.0623(4) 0.0165(17) Uani 0.381(5) 1 d PDU A 2 H13A H 1.0601 0.2805 -0.0930 0.020 Uiso 0.381(5) 1 calc PR A 2 C14 C 0.4068(2) 0.59871(18) 0.36325(11) 0.0188(5) Uani 1 1 d D . . H14 H 0.4316 0.6697 0.3636 0.023 Uiso 1 1 calc R A . C15 C 0.3694(2) 0.55271(18) 0.42519(12) 0.0194(5) Uani 1 1 d . A . H15 H 0.3685 0.5920 0.4671 0.023 Uiso 1 1 calc R . . C16 C 0.3329(2) 0.44870(18) 0.42623(12) 0.0178(5) Uani 1 1 d . . . C17 C 0.3408(3) 0.39441(18) 0.36344(12) 0.0219(5) Uani 1 1 d . A . H17 H 0.3209 0.3226 0.3621 0.026 Uiso 1 1 calc R . . C18 C 0.3778(3) 0.44611(18) 0.30317(12) 0.0215(5) Uani 1 1 d D . . H18 H 0.3808 0.4086 0.2606 0.026 Uiso 1 1 calc R A . C19 C 0.2818(2) 0.39750(18) 0.48920(12) 0.0187(5) Uani 1 1 d . A . H19 H 0.2960 0.3252 0.4937 0.022 Uiso 1 1 calc R . . C20 C 0.2166(3) 0.44661(18) 0.54041(12) 0.0208(5) Uani 1 1 d . . . H20 H 0.2093 0.5194 0.5363 0.025 Uiso 1 1 calc R A . C21 C 0.1550(2) 0.39986(17) 0.60270(12) 0.0177(5) Uani 1 1 d . A . C22 C 0.0413(3) 0.44844(19) 0.63403(12) 0.0222(5) Uani 1 1 d . . . H22 H 0.0095 0.5132 0.6167 0.027 Uiso 1 1 calc R A . C23 C -0.0261(3) 0.40380(19) 0.69006(13) 0.0244(5) Uani 1 1 d . A . H23 H -0.1042 0.4375 0.7105 0.029 Uiso 1 1 calc R . . C24 C 0.0201(3) 0.31034(19) 0.71617(13) 0.0238(5) Uani 1 1 d . . . H24 H -0.0271 0.2792 0.7541 0.029 Uiso 1 1 calc R A . C25 C 0.1357(3) 0.26168(19) 0.68698(12) 0.0212(5) Uani 1 1 d . A . H25 H 0.1687 0.1981 0.7057 0.025 Uiso 1 1 calc R . . C26 C 0.2032(2) 0.30583(17) 0.63046(12) 0.0192(5) Uani 1 1 d . . . H26 H 0.2821 0.2723 0.6106 0.023 Uiso 1 1 calc R A . 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 Zn1 0.01472(14) 0.01555(14) 0.01404(13) -0.00208(10) 0.00171(10) 0.00108(10) Br1 0.01544(12) 0.02415(14) 0.02075(12) -0.00232(9) -0.00280(9) 0.00151(9) Br2 0.02955(14) 0.01616(13) 0.02073(13) -0.00257(9) 0.00209(10) -0.00258(9) N2 0.0156(10) 0.0170(10) 0.0148(9) -0.0009(8) 0.0009(7) 0.0019(7) N1 0.015(2) 0.015(3) 0.013(2) 0.000(3) 0.003(2) 0.001(2) C1 0.018(2) 0.017(2) 0.012(3) 0.000(2) 0.005(2) -0.002(2) C2 0.0130(17) 0.016(2) 0.010(3) 0.000(2) 0.004(2) 0.0014(15) C3 0.017(2) 0.0107(17) 0.009(2) 0.0027(18) -0.0025(18) -0.0016(17) C4 0.009(3) 0.023(2) 0.014(2) -0.0016(18) -0.0027(19) 0.004(2) C5 0.016(3) 0.022(2) 0.016(2) -0.0022(18) 0.012(2) 0.004(3) C6 0.0172(19) 0.0170(18) 0.0141(18) -0.0017(14) 0.0015(15) -0.0012(14) C7 0.0166(19) 0.0179(18) 0.0120(17) -0.0022(14) 0.0002(15) -0.0025(14) C8 0.013(2) 0.0105(17) 0.016(2) 0.0031(19) 0.0006(17) 0.0008(18) C9 0.014(3) 0.019(2) 0.018(2) 0.0031(18) -0.0002(19) 0.003(2) C10 0.016(3) 0.021(3) 0.028(2) 0.0048(19) 0.005(2) 0.006(2) C11 0.021(2) 0.019(3) 0.026(3) 0.000(3) 0.013(2) 0.004(2) C12 0.027(3) 0.017(3) 0.023(2) 0.002(2) 0.003(2) 0.004(2) C13 0.0161(19) 0.017(3) 0.021(3) 0.000(2) 0.003(2) 0.0045(17) N1A 0.014(3) 0.016(4) 0.016(3) 0.005(3) 0.005(3) 0.003(3) C1A 0.012(3) 0.016(3) 0.018(4) 0.003(4) 0.006(3) 0.003(3) C2A 0.018(3) 0.014(3) 0.008(4) -0.003(3) 0.008(3) -0.001(2) C3A 0.011(3) 0.015(3) 0.008(3) 0.002(3) -0.001(3) 0.000(2) C4A 0.009(4) 0.018(3) 0.007(3) 0.001(2) -0.004(3) -0.002(3) C5A 0.012(4) 0.020(3) 0.018(3) 0.003(3) -0.001(3) 0.000(4) C6A 0.014(3) 0.020(3) 0.015(3) 0.002(2) -0.001(2) -0.003(2) C7A 0.012(3) 0.016(3) 0.018(3) -0.001(2) -0.001(2) 0.003(2) C8A 0.009(3) 0.016(3) 0.018(4) 0.003(3) 0.000(3) 0.002(2) C9A 0.010(4) 0.019(3) 0.016(3) 0.002(3) -0.002(3) 0.005(3) C10A 0.013(4) 0.023(4) 0.027(3) -0.002(3) -0.006(3) 0.003(3) C11A 0.018(3) 0.018(4) 0.033(4) 0.005(4) 0.002(3) 0.005(3) C12A 0.020(3) 0.019(4) 0.022(3) -0.001(3) 0.012(3) 0.005(3) C13A 0.020(3) 0.015(4) 0.015(4) -0.002(3) 0.005(3) 0.000(3) C14 0.0194(12) 0.0178(12) 0.0191(11) -0.0032(9) 0.0025(9) -0.0032(9) C15 0.0214(12) 0.0205(12) 0.0165(11) -0.0033(9) 0.0027(9) -0.0026(9) C16 0.0146(11) 0.0182(12) 0.0205(11) 0.0005(9) 0.0004(9) 0.0014(9) C17 0.0295(14) 0.0134(12) 0.0227(12) -0.0005(9) 0.0021(10) 0.0009(10) C18 0.0278(14) 0.0181(12) 0.0186(11) -0.0047(10) 0.0042(10) 0.0017(10) C19 0.0181(12) 0.0159(12) 0.0223(12) 0.0030(9) 0.0011(9) 0.0003(9) C20 0.0207(12) 0.0159(12) 0.0257(12) 0.0035(10) 0.0021(10) 0.0002(9) C21 0.0168(11) 0.0172(12) 0.0193(11) 0.0002(9) 0.0026(9) -0.0014(9) C22 0.0200(12) 0.0199(13) 0.0267(12) 0.0026(10) 0.0036(10) 0.0042(9) C23 0.0202(13) 0.0261(14) 0.0272(13) -0.0006(11) 0.0079(10) 0.0039(10) C24 0.0253(13) 0.0217(13) 0.0244(12) 0.0029(10) 0.0050(10) -0.0041(10) C25 0.0251(13) 0.0159(12) 0.0226(12) 0.0022(10) 0.0001(10) 0.0003(10) C26 0.0192(12) 0.0157(12) 0.0228(12) -0.0026(9) 0.0032(9) 0.0009(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 Zn1 N1 2.021(12) . ? Zn1 N2 2.0478(18) . ? Zn1 N1A 2.06(2) . ? Zn1 Br2 2.3465(4) . ? Zn1 Br1 2.3735(3) . ? N2 C18 1.343(3) . ? N2 C14 1.346(3) . ? N1 C1 1.356(6) . ? N1 C5 1.359(5) . ? C1 C2 1.391(6) . ? C2 C3 1.396(5) . ? C3 C4 1.399(5) . ? C3 C6 1.465(6) . ? C4 C5 1.398(6) . ? C6 C7 1.327(6) . ? C7 C8 1.477(5) . ? C8 C13 1.388(5) . ? C8 C9 1.390(4) . ? C9 C10 1.385(5) . ? C10 C11 1.393(6) . ? C11 C12 1.389(6) . ? C12 C13 1.388(6) . ? N1A C1A 1.354(7) . ? N1A C5A 1.355(7) . ? C1A C2A 1.373(8) . ? C2A C3A 1.380(6) . ? C3A C4A 1.376(6) . ? C3A C6A 1.489(10) . ? C4A C5A 1.375(8) . ? C6A C7A 1.296(9) . ? C7A C8A 1.468(9) . ? C8A C13A 1.387(6) . ? C8A C9A 1.388(6) . ? C9A C10A 1.376(7) . ? C10A C11A 1.388(7) . ? C11A C12A 1.389(7) . ? C12A C13A 1.383(7) . ? C14 C15 1.380(3) . ? C15 C16 1.392(3) . ? C16 C17 1.397(3) . ? C16 C19 1.466(3) . ? C17 C18 1.385(3) . ? C19 C20 1.330(3) . ? C20 C21 1.468(3) . ? C21 C22 1.393(3) . ? C21 C26 1.404(3) . ? C22 C23 1.385(3) . ? C23 C24 1.380(3) . ? C24 C25 1.390(3) . ? C25 C26 1.390(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N2 102.4(8) . . ? N1 Zn1 N1A 2(2) . . ? N2 Zn1 N1A 104.6(13) . . ? N1 Zn1 Br2 115.3(8) . . ? N2 Zn1 Br2 107.83(5) . . ? N1A Zn1 Br2 113.4(14) . . ? N1 Zn1 Br1 106.4(3) . . ? N2 Zn1 Br1 108.56(5) . . ? N1A Zn1 Br1 106.4(4) . . ? Br2 Zn1 Br1 115.446(14) . . ? C18 N2 C14 117.86(19) . . ? C18 N2 Zn1 120.31(14) . . ? C14 N2 Zn1 121.33(15) . . ? C1 N1 C5 116.1(9) . . ? C1 N1 Zn1 125.2(7) . . ? C5 N1 Zn1 118.0(7) . . ? N1 C1 C2 124.3(7) . . ? C1 C2 C3 118.9(5) . . ? C2 C3 C4 118.1(5) . . ? C2 C3 C6 122.4(4) . . ? C4 C3 C6 119.5(4) . . ? C5 C4 C3 119.2(5) . . ? N1 C5 C4 123.5(7) . . ? C7 C6 C3 126.9(4) . . ? C6 C7 C8 127.0(4) . . ? C13 C8 C9 119.6(4) . . ? C13 C8 C7 121.6(4) . . ? C9 C8 C7 118.8(4) . . ? C10 C9 C8 120.1(5) . . ? C9 C10 C11 120.2(5) . . ? C12 C11 C10 119.8(5) . . ? C13 C12 C11 119.9(5) . . ? C12 C13 C8 120.4(5) . . ? C1A N1A C5A 120.5(16) . . ? C1A N1A Zn1 111.7(10) . . ? C5A N1A Zn1 127.9(10) . . ? N1A C1A C2A 120.0(12) . . ? C1A C2A C3A 120.8(8) . . ? C4A C3A C2A 117.9(8) . . ? C4A C3A C6A 122.0(6) . . ? C2A C3A C6A 120.0(6) . . ? C5A C4A C3A 120.8(8) . . ? N1A C5A C4A 119.9(12) . . ? C7A C6A C3A 127.4(6) . . ? C6A C7A C8A 125.7(6) . . ? C13A C8A C9A 116.6(8) . . ? C13A C8A C7A 121.2(6) . . ? C9A C8A C7A 122.1(6) . . ? C10A C9A C8A 122.4(8) . . ? C9A C10A C11A 119.7(8) . . ? C10A C11A C12A 119.4(8) . . ? C13A C12A C11A 119.4(8) . . ? C12A C13A C8A 122.4(8) . . ? N2 C14 C15 122.6(2) . . ? C14 C15 C16 119.9(2) . . ? C15 C16 C17 117.3(2) . . ? C15 C16 C19 122.4(2) . . ? C17 C16 C19 120.2(2) . . ? C18 C17 C16 119.5(2) . . ? N2 C18 C17 122.8(2) . . ? C20 C19 C16 123.6(2) . . ? C19 C20 C21 126.7(2) . . ? C22 C21 C26 118.6(2) . . ? C22 C21 C20 119.0(2) . . ? C26 C21 C20 122.3(2) . . ? C23 C22 C21 121.0(2) . . ? C24 C23 C22 120.0(2) . . ? C23 C24 C25 120.1(2) . . ? C26 C25 C24 120.2(2) . . ? C25 C26 C21 120.1(2) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.705 _refine_diff_density_min -0.321 _refine_diff_density_rms 0.093 _database_code_depnum_ccdc_archive 'CCDC 938967' ####################################################################### # # 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_compound_2 # data_c554 CCDC 938968 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H44 Br4 N4 Zn2' _chemical_formula_weight 1175.29 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' Zn Zn 0.2839 1.4301 '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)/n 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 9.5694(12) _cell_length_b 13.0123(16) _cell_length_c 19.216(2) _cell_angle_alpha 90.00 _cell_angle_beta 91.437(3) _cell_angle_gamma 90.00 _cell_volume 2392.0(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2850 _cell_measurement_theta_min 2.35 _cell_measurement_theta_max 25.53 _exptl_crystal_description Block _exptl_crystal_colour Light_Yellow _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.19 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.632 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1168 _exptl_absorpt_coefficient_mu 4.383 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3158 _exptl_absorpt_correction_T_max 0.5629 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13276 _diffrn_reflns_av_R_equivalents 0.0581 _diffrn_reflns_av_sigmaI/netI 0.0611 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 25.00 _reflns_number_total 4200 _reflns_number_gt 3252 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. the contraints/restraints used in .ins file ISOR 0.01 0.01 N2 SADI 0.01 ZN1 N2 ZN1 N2X SADI C19 C20 C19X C20X DFIX 1.52 0.01 C19 C16 C19X C16X C20 C21 C20X C21X EADP C14X C15X C16X C17X C18X C19X C20X EADP C21X C22X C26X EADP C23X C24X C25X ; _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^)+(0.0954P)^2^+11.9522P] 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 4200 _refine_ls_number_parameters 272 _refine_ls_number_restraints 12 _refine_ls_R_factor_all 0.0840 _refine_ls_R_factor_gt 0.0641 _refine_ls_wR_factor_ref 0.1879 _refine_ls_wR_factor_gt 0.1776 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _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 Zn1 Zn 0.55429(9) 0.63913(6) 0.21595(4) 0.0235(3) Uani 1 1 d D . . Br1 Br 0.74996(8) 0.61947(6) 0.14386(4) 0.0301(3) Uani 1 1 d . A . Br2 Br 0.49284(9) 0.80718(6) 0.24574(5) 0.0378(3) Uani 1 1 d . A . N1 N 0.5935(6) 0.5570(5) 0.3038(3) 0.0241(14) Uani 1 1 d . A . C1 C 0.5811(8) 0.5970(6) 0.3684(4) 0.0291(18) Uani 1 1 d . . . H1 H 0.5449 0.6646 0.3727 0.035 Uiso 1 1 calc R A . C2 C 0.6183(8) 0.5448(6) 0.4274(4) 0.0323(19) Uani 1 1 d . A . H2 H 0.6086 0.5763 0.4716 0.039 Uiso 1 1 calc R . . C3 C 0.6707(8) 0.4446(6) 0.4231(4) 0.0280(17) Uani 1 1 d . . . C4 C 0.6790(10) 0.4031(6) 0.3559(5) 0.036(2) Uani 1 1 d . A . H4 H 0.7121 0.3349 0.3498 0.043 Uiso 1 1 calc R . . C5 C 0.6399(9) 0.4602(6) 0.3001(4) 0.035(2) Uani 1 1 d . . . H5 H 0.6458 0.4298 0.2553 0.042 Uiso 1 1 calc R A . C6 C 0.7253(9) 0.3883(6) 0.4838(4) 0.0323(19) Uani 1 1 d . A . H6 H 0.7216 0.3154 0.4827 0.039 Uiso 1 1 calc R . . C7 C 0.7793(9) 0.4327(6) 0.5398(5) 0.035(2) Uani 1 1 d . . . H7 H 0.7777 0.5057 0.5405 0.042 Uiso 1 1 calc R A . C8 C 0.8414(9) 0.3823(6) 0.6011(4) 0.0308(18) Uani 1 1 d . A . C9 C 0.9488(9) 0.4332(7) 0.6375(5) 0.037(2) Uani 1 1 d . . . H9 H 0.9755 0.5004 0.6239 0.045 Uiso 1 1 calc R A . C10 C 1.0170(9) 0.3860(7) 0.6937(5) 0.038(2) Uani 1 1 d . A . H10 H 1.0906 0.4204 0.7182 0.046 Uiso 1 1 calc R . . C11 C 0.9766(9) 0.2882(7) 0.7135(5) 0.037(2) Uani 1 1 d . . . H11 H 1.0241 0.2548 0.7512 0.044 Uiso 1 1 calc R A . C12 C 0.8700(9) 0.2403(7) 0.6797(5) 0.0345(19) Uani 1 1 d . A . H12 H 0.8416 0.1741 0.6946 0.041 Uiso 1 1 calc R . . C13 C 0.8019(9) 0.2856(6) 0.6240(5) 0.036(2) Uani 1 1 d . . . H13 H 0.7271 0.2504 0.6009 0.043 Uiso 1 1 calc R A . N2 N 0.3959(7) 0.5590(6) 0.1705(4) 0.023(3) Uani 0.594(15) 1 d PGDU A 1 C14 C 0.2680(9) 0.5625(7) 0.2031(4) 0.034(4) Uani 0.594(15) 1 d PG A 1 H14 H 0.2630 0.5873 0.2495 0.040 Uiso 0.594(15) 1 calc PR A 1 C15 C 0.1474(7) 0.5297(7) 0.1679(5) 0.032(3) Uani 0.594(15) 1 d PG A 1 H15 H 0.0600 0.5321 0.1903 0.038 Uiso 0.594(15) 1 calc PR A 1 C16 C 0.1547(7) 0.4934(7) 0.1001(5) 0.025(3) Uani 0.594(15) 1 d PGD A 1 C17 C 0.2826(9) 0.4899(7) 0.0674(3) 0.030(3) Uani 0.594(15) 1 d PG A 1 H17 H 0.2876 0.4651 0.0211 0.036 Uiso 0.594(15) 1 calc PR A 1 C18 C 0.4032(7) 0.5227(7) 0.1026(4) 0.025(3) Uani 0.594(15) 1 d PG A 1 H18 H 0.4906 0.5203 0.0803 0.030 Uiso 0.594(15) 1 calc PR A 1 C19 C 0.0200(11) 0.4893(10) 0.0568(6) 0.028(4) Uani 0.594(15) 1 d PD . 1 H19 H -0.0616 0.4822 0.0879 0.033 Uiso 0.594(15) 1 calc PR A 1 C20 C -0.0049(11) 0.5853(8) 0.0042(6) 0.023(3) Uani 0.594(15) 1 d PD . 1 H20 H -0.0975 0.6177 0.0132 0.027 Uiso 0.594(15) 1 calc PR A 1 C21 C 0.1088(9) 0.6680(7) 0.0054(5) 0.028(3) Uani 0.594(15) 1 d PGD A 1 C22 C 0.1268(9) 0.7250(7) 0.0662(6) 0.035(4) Uani 0.594(15) 1 d PG A 1 H22 H 0.0575 0.7232 0.1007 0.042 Uiso 0.594(15) 1 calc PR A 1 C23 C 0.2461(12) 0.7845(5) 0.0764(6) 0.048(5) Uani 0.594(15) 1 d PG A 1 H23 H 0.2585 0.8235 0.1179 0.058 Uiso 0.594(15) 1 calc PR A 1 C24 C 0.3475(10) 0.7870(6) 0.0258(7) 0.053(7) Uani 0.594(15) 1 d PG A 1 H24 H 0.4291 0.8277 0.0328 0.063 Uiso 0.594(15) 1 calc PR A 1 C25 C 0.3295(11) 0.7300(8) -0.0349(6) 0.056(6) Uani 0.594(15) 1 d PG A 1 H25 H 0.3987 0.7318 -0.0694 0.067 Uiso 0.594(15) 1 calc PR A 1 C26 C 0.2101(12) 0.6705(7) -0.0451(4) 0.038(4) Uani 0.594(15) 1 d PG A 1 H26 H 0.1978 0.6316 -0.0866 0.045 Uiso 0.594(15) 1 calc PR A 1 N2X N 0.4112(11) 0.5471(7) 0.1650(5) 0.019 Uiso 0.406(15) 1 d PGD A 2 C14X C 0.2733(13) 0.5494(8) 0.1860(4) 0.019(3) Uiso 0.406(15) 1 d PG A 2 H14X H 0.2516 0.5765 0.2303 0.023 Uiso 0.406(15) 1 calc PR A 2 C15X C 0.1673(10) 0.5121(8) 0.1421(5) 0.019(3) Uiso 0.406(15) 1 d PG A 2 H15X H 0.0730 0.5137 0.1565 0.023 Uiso 0.406(15) 1 calc PR A 2 C16X C 0.1991(12) 0.4725(6) 0.0773(5) 0.019(3) Uiso 0.406(15) 1 d PGD A 2 C17X C 0.3370(12) 0.4701(6) 0.0562(5) 0.019(3) Uiso 0.406(15) 1 d PG A 2 H17X H 0.3588 0.4430 0.0119 0.023 Uiso 0.406(15) 1 calc PR A 2 C18X C 0.4431(10) 0.5074(7) 0.1001(6) 0.019(3) Uiso 0.406(15) 1 d PG A 2 H18X H 0.5373 0.5058 0.0857 0.023 Uiso 0.406(15) 1 calc PR A 2 C19X C 0.0917(16) 0.4518(12) 0.0183(7) 0.019(3) Uiso 0.406(15) 1 d PD . 2 H19X H 0.1181 0.3893 -0.0087 0.023 Uiso 0.406(15) 1 calc PR A 2 C20X C 0.0662(17) 0.5488(10) -0.0332(9) 0.019(3) Uiso 0.406(15) 1 d PD . 2 H20X H 0.0816 0.5277 -0.0825 0.023 Uiso 0.406(15) 1 calc PR A 2 C21X C 0.1485(15) 0.6461(10) -0.0164(9) 0.022(4) Uiso 0.406(15) 1 d PGD A 2 C22X C 0.1384(14) 0.7010(12) 0.0453(9) 0.022(4) Uiso 0.406(15) 1 d PG A 2 H22X H 0.0605 0.6909 0.0742 0.027 Uiso 0.406(15) 1 calc PR A 2 C23X C 0.2423(17) 0.7708(12) 0.0647(8) 0.027(4) Uiso 0.406(15) 1 d PG A 2 H23X H 0.2354 0.8083 0.1069 0.033 Uiso 0.406(15) 1 calc PR A 2 C24X C 0.3563(15) 0.7856(11) 0.0224(9) 0.027(4) Uiso 0.406(15) 1 d PG A 2 H24X H 0.4272 0.8332 0.0357 0.033 Uiso 0.406(15) 1 calc PR A 2 C25X C 0.3664(14) 0.7307(14) -0.0393(8) 0.027(4) Uiso 0.406(15) 1 d PG A 2 H25X H 0.4443 0.7408 -0.0682 0.033 Uiso 0.406(15) 1 calc PR A 2 C26X C 0.2625(18) 0.6609(12) -0.0587(7) 0.022(4) Uiso 0.406(15) 1 d PG A 2 H26X H 0.2694 0.6234 -0.1008 0.027 Uiso 0.406(15) 1 calc PR A 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 Zn1 0.0214(5) 0.0252(5) 0.0238(5) -0.0018(4) 0.0026(4) -0.0015(3) Br1 0.0244(4) 0.0346(5) 0.0317(5) -0.0038(3) 0.0079(3) -0.0012(3) Br2 0.0433(5) 0.0262(5) 0.0444(6) -0.0034(4) 0.0109(4) 0.0032(3) N1 0.025(3) 0.026(3) 0.022(3) -0.002(3) 0.006(3) -0.003(3) C1 0.029(4) 0.025(4) 0.034(5) -0.007(3) -0.003(3) 0.006(3) C2 0.033(4) 0.038(5) 0.025(4) -0.008(4) -0.003(4) 0.011(4) C3 0.031(4) 0.027(4) 0.025(4) -0.003(3) -0.003(3) 0.000(3) C4 0.047(5) 0.023(4) 0.037(5) -0.004(4) 0.004(4) -0.002(4) C5 0.047(5) 0.033(5) 0.024(4) -0.003(4) -0.003(4) 0.000(4) C6 0.039(5) 0.026(4) 0.032(5) 0.000(4) 0.002(4) 0.001(4) C7 0.034(5) 0.027(4) 0.042(5) -0.001(4) -0.005(4) 0.002(4) C8 0.032(4) 0.030(4) 0.029(5) -0.001(3) 0.001(4) 0.007(3) C9 0.040(5) 0.028(4) 0.044(5) 0.001(4) -0.004(4) -0.004(4) C10 0.035(5) 0.045(5) 0.034(5) 0.000(4) -0.011(4) 0.001(4) C11 0.041(5) 0.037(5) 0.032(5) 0.006(4) -0.001(4) 0.006(4) C12 0.040(5) 0.028(4) 0.035(5) 0.005(4) 0.002(4) -0.001(4) C13 0.038(5) 0.029(4) 0.040(5) -0.002(4) -0.005(4) 0.003(4) N2 0.026(5) 0.019(5) 0.023(5) -0.003(4) 0.001(4) 0.004(4) C14 0.027(7) 0.032(8) 0.042(9) 0.011(7) 0.004(7) -0.004(6) C15 0.041(9) 0.023(7) 0.032(8) 0.002(6) 0.009(7) -0.004(6) C16 0.011(6) 0.019(6) 0.045(9) 0.002(6) 0.011(6) 0.002(5) C17 0.024(8) 0.039(8) 0.028(7) -0.004(6) 0.004(6) 0.003(6) C18 0.007(6) 0.030(7) 0.038(8) -0.006(6) 0.004(5) 0.002(5) C19 0.031(8) 0.029(7) 0.023(7) 0.000(6) 0.004(6) 0.002(6) C20 0.026(7) 0.019(6) 0.024(7) 0.001(5) 0.003(5) 0.003(5) C21 0.024(7) 0.039(8) 0.021(8) 0.005(6) 0.006(6) -0.005(6) C22 0.041(9) 0.021(7) 0.043(10) -0.003(7) 0.002(7) 0.006(6) C23 0.073(13) 0.019(8) 0.051(11) -0.011(7) -0.008(9) -0.006(8) C24 0.032(9) 0.035(9) 0.090(16) -0.007(9) -0.001(9) -0.021(7) C25 0.030(9) 0.031(9) 0.108(18) 0.009(10) 0.031(10) 0.002(8) C26 0.041(10) 0.036(9) 0.037(9) -0.014(7) 0.003(8) 0.011(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.021(5) . ? Zn1 N1 2.026(6) . ? Zn1 N2X 2.050(7) . ? Zn1 Br2 2.3392(12) . ? Zn1 Br1 2.3709(11) . ? N1 C5 1.338(10) . ? N1 C1 1.354(10) . ? C1 C2 1.362(12) . ? C2 C3 1.400(11) . ? C3 C4 1.403(12) . ? C3 C6 1.463(11) . ? C4 C5 1.351(12) . ? C6 C7 1.316(12) . ? C7 C8 1.460(12) . ? C8 C13 1.389(12) . ? C8 C9 1.396(12) . ? C9 C10 1.390(12) . ? C10 C11 1.387(12) . ? C11 C12 1.348(13) . ? C12 C13 1.372(12) . ? N2 C14 1.3900 . ? N2 C18 1.3900 . ? C14 C15 1.3900 . ? C15 C16 1.3900 . ? C16 C17 1.3900 . ? C16 C19 1.517(8) . ? C17 C18 1.3900 . ? C19 C20 1.526(17) 3_565 ? C19 C20 1.620(14) . ? C20 C19 1.526(17) 3_565 ? C20 C21 1.530(8) . ? C21 C22 1.3900 . ? C21 C26 1.3900 . ? C22 C23 1.3900 . ? C23 C24 1.3900 . ? C24 C25 1.3900 . ? C25 C26 1.3900 . ? N2X C14X 1.3900 . ? N2X C18X 1.3900 . ? C14X C15X 1.3900 . ? C15X C16X 1.3900 . ? C16X C17X 1.3900 . ? C16X C19X 1.534(9) . ? C17X C18X 1.3900 . ? C19X C20X 1.55(2) 3_565 ? C19X C20X 1.618(17) . ? C20X C21X 1.522(9) . ? C20X C19X 1.55(2) 3_565 ? C21X C22X 1.3900 . ? C21X C26X 1.3900 . ? C22X C23X 1.3900 . ? C23X C24X 1.3900 . ? C24X C25X 1.3900 . ? C25X C26X 1.3900 . ? 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 Zn1 N1 102.1(3) . . ? N2 Zn1 N2X 6.7(5) . . ? N1 Zn1 N2X 101.4(3) . . ? N2 Zn1 Br2 113.4(3) . . ? N1 Zn1 Br2 109.38(18) . . ? N2X Zn1 Br2 119.6(3) . . ? N2 Zn1 Br1 106.7(3) . . ? N1 Zn1 Br1 107.32(18) . . ? N2X Zn1 Br1 100.7(4) . . ? Br2 Zn1 Br1 116.80(4) . . ? C5 N1 C1 116.6(7) . . ? C5 N1 Zn1 120.4(5) . . ? C1 N1 Zn1 122.8(5) . . ? N1 C1 C2 123.0(7) . . ? C1 C2 C3 120.1(7) . . ? C2 C3 C4 116.3(7) . . ? C2 C3 C6 122.7(7) . . ? C4 C3 C6 120.9(7) . . ? C5 C4 C3 119.8(8) . . ? N1 C5 C4 124.1(8) . . ? C7 C6 C3 123.9(8) . . ? C6 C7 C8 127.3(8) . . ? C13 C8 C9 118.2(8) . . ? C13 C8 C7 123.6(8) . . ? C9 C8 C7 118.1(8) . . ? C10 C9 C8 120.4(8) . . ? C11 C10 C9 119.4(8) . . ? C12 C11 C10 120.3(8) . . ? C11 C12 C13 121.1(8) . . ? C12 C13 C8 120.6(8) . . ? C14 N2 C18 120.0 . . ? C14 N2 Zn1 116.6(5) . . ? C18 N2 Zn1 121.7(5) . . ? C15 C14 N2 120.0 . . ? C14 C15 C16 120.0 . . ? C15 C16 C17 120.0 . . ? C15 C16 C19 117.7(8) . . ? C17 C16 C19 119.8(8) . . ? C18 C17 C16 120.0 . . ? C17 C18 N2 120.0 . . ? C16 C19 C20 120.4(10) . 3_565 ? C16 C19 C20 115.1(9) . . ? C20 C19 C20 90.1(8) 3_565 . ? C19 C20 C21 120.9(10) 3_565 . ? C19 C20 C19 89.9(8) 3_565 . ? C21 C20 C19 116.0(8) . . ? C22 C21 C26 120.0 . . ? C22 C21 C20 117.5(8) . . ? C26 C21 C20 120.9(8) . . ? C21 C22 C23 120.0 . . ? C24 C23 C22 120.0 . . ? C25 C24 C23 120.0 . . ? C24 C25 C26 120.0 . . ? C25 C26 C21 120.0 . . ? C14X N2X C18X 120.0 . . ? C14X N2X Zn1 118.4(6) . . ? C18X N2X Zn1 119.1(6) . . ? N2X C14X C15X 120.0 . . ? C16X C15X C14X 120.0 . . ? C17X C16X C15X 120.0 . . ? C17X C16X C19X 113.9(10) . . ? C15X C16X C19X 124.7(10) . . ? C16X C17X C18X 120.0 . . ? C17X C18X N2X 120.0 . . ? C16X C19X C20X 120.3(13) . 3_565 ? C16X C19X C20X 113.8(11) . . ? C20X C19X C20X 89.1(11) 3_565 . ? C21X C20X C19X 117.9(14) . 3_565 ? C21X C20X C19X 116.7(12) . . ? C19X C20X C19X 90.9(11) 3_565 . ? C22X C21X C26X 120.0 . . ? C22X C21X C20X 124.2(13) . . ? C26X C21X C20X 113.6(13) . . ? C23X C22X C21X 120.0 . . ? C24X C23X C22X 120.0 . . ? C23X C24X C25X 120.0 . . ? C24X C25X C26X 120.0 . . ? C25X C26X C21X 120.0 . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 2.109 _refine_diff_density_min -0.566 _refine_diff_density_rms 0.197 _database_code_depnum_ccdc_archive 'CCDC 938968' ####################################################################### # # 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_compound_6' # data_d014 CCDC 938969 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 Br2 F2 N2 Zn' _chemical_formula_weight 623.63 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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)/n 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 11.015(3) _cell_length_b 12.395(4) _cell_length_c 18.034(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.529(8) _cell_angle_gamma 90.00 _cell_volume 2462.2(13) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 878 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 23.14 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.682 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 4.275 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.3083 _exptl_absorpt_correction_T_max 0.4028 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14949 _diffrn_reflns_av_R_equivalents 0.0584 _diffrn_reflns_av_sigmaI/netI 0.0672 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 1.99 _diffrn_reflns_theta_max 26.00 _reflns_number_total 4815 _reflns_number_gt 3836 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1694P)^2^+187.3621P] 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 SHELXL _refine_ls_extinction_coef 0.0025(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4815 _refine_ls_number_parameters 299 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1613 _refine_ls_R_factor_gt 0.1462 _refine_ls_wR_factor_ref 0.4281 _refine_ls_wR_factor_gt 0.4208 _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_restrained_S_all 1.076 _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 Zn1 Zn 0.7272(2) 0.93023(17) 0.14663(12) 0.0308(7) Uani 1 1 d . . . Br1 Br 0.92497(19) 0.97685(19) 0.18839(15) 0.0480(8) Uani 1 1 d . . . Br2 Br 0.6683(2) 0.75008(16) 0.13866(12) 0.0404(7) Uani 1 1 d . . . N1 N 0.6072(14) 1.0121(14) 0.2076(9) 0.033(4) Uani 1 1 d . . . C1 C 0.514(2) 0.9716(17) 0.2408(16) 0.050(6) Uani 1 1 d . . . H1 H 0.5019 0.8957 0.2386 0.060 Uiso 1 1 calc R . . C2 C 0.430(2) 1.0330(18) 0.2793(12) 0.044(5) Uani 1 1 d . . . H2 H 0.3581 1.0003 0.2979 0.053 Uiso 1 1 calc R . . C3 C 0.4509(19) 1.1433(17) 0.2906(11) 0.037(4) Uani 1 1 d . . . C4 C 0.5508(19) 1.1879(18) 0.2557(13) 0.042(5) Uani 1 1 d . . . H4 H 0.5666 1.2631 0.2584 0.050 Uiso 1 1 calc R . . C5 C 0.626(2) 1.120(2) 0.2170(14) 0.048(6) Uani 1 1 d . . . H5 H 0.6967 1.1510 0.1954 0.058 Uiso 1 1 calc R . . N2 N 0.7080(16) 1.0164(13) 0.0491(10) 0.037(4) Uani 1 1 d . . . C6 C 0.6124(19) 1.0756(17) 0.0326(12) 0.038(5) Uani 1 1 d . . . H6 H 0.5446 1.0725 0.0648 0.045 Uiso 1 1 calc R . . C7 C 0.605(2) 1.1418(16) -0.0284(11) 0.036(4) Uani 1 1 d . . . H7 H 0.5351 1.1856 -0.0361 0.043 Uiso 1 1 calc R . . C8 C 0.6982(19) 1.1446(15) -0.0784(13) 0.038(5) Uani 1 1 d . . . C9 C 0.794(2) 1.0781(17) -0.0649(11) 0.038(5) Uani 1 1 d . . . H9 H 0.8568 1.0724 -0.1001 0.046 Uiso 1 1 calc R . . C10 C 0.799(2) 1.0170(17) 0.0015(11) 0.040(5) Uani 1 1 d . . . H10 H 0.8701 0.9756 0.0121 0.048 Uiso 1 1 calc R . . F1 F 0.0659(18) 1.098(2) 0.4585(11) 0.092(6) Uani 1 1 d . . . F2 F 0.397(4) 1.393(5) 0.172(2) 0.29(4) Uani 1 1 d . . . C11 C 0.370(2) 1.2135(17) 0.3331(13) 0.041(5) Uani 1 1 d . . . H11 H 0.4205 1.2506 0.3717 0.049 Uiso 1 1 calc R . . C12 C 0.2577(19) 1.1698(16) 0.3712(12) 0.037(5) Uani 1 1 d . . . H12 H 0.2198 1.1138 0.3385 0.045 Uiso 1 1 calc R . . C13 C 0.1913(18) 1.2823(16) 0.3559(12) 0.034(4) Uani 1 1 d . . . H13 H 0.1069 1.2738 0.3358 0.041 Uiso 1 1 calc R . . C14 C 0.288(2) 1.3029(17) 0.2940(13) 0.044(6) Uani 1 1 d . . . H14 H 0.3249 1.3762 0.2989 0.053 Uiso 1 1 calc R . . C15 C 0.2663(19) 1.125(2) 0.4498(11) 0.042(5) Uani 1 1 d . . . C16 C 0.165(2) 1.0988(17) 0.4867(11) 0.036(4) Uani 1 1 d . . . C17 C 0.171(3) 1.058(2) 0.5608(17) 0.063(8) Uani 1 1 d . . . H17 H 0.0994 1.0331 0.5845 0.076 Uiso 1 1 calc R . . C18 C 0.276(3) 1.055(3) 0.5954(19) 0.078(10) Uani 1 1 d . . . H18 H 0.2787 1.0320 0.6455 0.093 Uiso 1 1 calc R . . C19 C 0.379(3) 1.085(3) 0.5620(16) 0.072(8) Uani 1 1 d . . . H19 H 0.4549 1.0799 0.5873 0.086 Uiso 1 1 calc R . . C20 C 0.373(3) 1.124(3) 0.4907(16) 0.066(7) Uani 1 1 d . . . H20 H 0.4451 1.1502 0.4685 0.079 Uiso 1 1 calc R . . C21 C 0.249(2) 1.2807(16) 0.2157(12) 0.039(5) Uani 1 1 d . . . C22 C 0.316(2) 1.327(2) 0.1583(16) 0.054(6) Uani 1 1 d . . . C23 C 0.283(3) 1.314(2) 0.0816(16) 0.060(7) Uani 1 1 d . . . H23 H 0.3267 1.3488 0.0436 0.072 Uiso 1 1 calc R . . C24 C 0.196(4) 1.256(3) 0.0669(14) 0.076(10) Uani 1 1 d . . . H24 H 0.1761 1.2444 0.0162 0.092 Uiso 1 1 calc R . . C25 C 0.124(3) 1.206(2) 0.1217(13) 0.061(7) Uani 1 1 d . . . H25 H 0.0572 1.1627 0.1072 0.073 Uiso 1 1 calc R . . C26 C 0.150(2) 1.2200(16) 0.1961(12) 0.042(5) Uani 1 1 d . . . H26 H 0.1009 1.1879 0.2328 0.051 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 Zn1 0.0383(13) 0.0251(11) 0.0292(12) 0.0044(9) 0.0118(9) 0.0077(9) Br1 0.0346(11) 0.0398(13) 0.0698(16) 0.0118(11) 0.0097(10) 0.0066(9) Br2 0.0524(13) 0.0259(10) 0.0429(12) 0.0019(8) 0.0003(9) 0.0045(8) N1 0.033(8) 0.034(9) 0.032(8) 0.013(7) 0.012(7) 0.005(7) C1 0.044(12) 0.023(10) 0.085(18) 0.004(11) 0.028(12) 0.006(9) C2 0.051(13) 0.041(12) 0.042(12) -0.004(10) 0.032(10) -0.004(10) C3 0.041(11) 0.032(10) 0.036(10) -0.005(8) 0.004(8) -0.008(8) C4 0.040(11) 0.035(11) 0.049(12) -0.021(10) 0.001(9) -0.002(9) C5 0.042(12) 0.047(13) 0.057(14) -0.028(11) 0.019(10) -0.010(10) N2 0.046(10) 0.023(8) 0.043(10) 0.003(7) 0.015(8) 0.009(7) C6 0.039(11) 0.036(11) 0.038(11) 0.016(9) 0.002(9) -0.006(9) C7 0.055(12) 0.024(9) 0.030(10) 0.003(8) 0.009(9) 0.000(8) C8 0.048(11) 0.016(8) 0.052(12) 0.012(8) 0.012(10) 0.001(8) C9 0.055(12) 0.034(11) 0.027(10) 0.014(8) 0.009(9) 0.012(9) C10 0.060(13) 0.034(11) 0.026(10) 0.013(8) 0.007(9) 0.022(10) F1 0.078(12) 0.119(17) 0.078(13) -0.008(12) 0.017(10) -0.018(12) F2 0.23(4) 0.48(8) 0.18(3) -0.20(5) 0.13(3) -0.22(5) C11 0.043(11) 0.029(10) 0.052(13) -0.007(9) -0.002(10) -0.008(9) C12 0.041(11) 0.027(10) 0.044(11) 0.001(9) 0.012(9) 0.008(8) C13 0.036(10) 0.026(9) 0.041(11) -0.002(8) 0.004(8) -0.011(8) C14 0.048(12) 0.033(11) 0.050(13) -0.030(10) 0.023(10) -0.014(9) C15 0.042(11) 0.063(15) 0.022(9) 0.010(9) -0.004(8) -0.002(10) C16 0.042(11) 0.034(11) 0.033(10) 0.002(8) 0.000(9) -0.007(9) C17 0.08(2) 0.041(14) 0.065(17) -0.002(12) 0.033(16) 0.002(13) C18 0.10(2) 0.07(2) 0.067(19) 0.042(16) 0.004(18) 0.013(17) C19 0.09(2) 0.08(2) 0.048(15) 0.018(15) -0.007(15) -0.018(17) C20 0.067(17) 0.08(2) 0.055(16) 0.009(14) -0.009(13) -0.001(15) C21 0.057(13) 0.025(10) 0.035(11) 0.000(8) 0.017(9) 0.009(9) C22 0.053(14) 0.039(13) 0.069(17) -0.017(12) 0.016(12) -0.019(11) C23 0.09(2) 0.031(12) 0.058(16) 0.007(11) 0.030(15) -0.004(13) C24 0.11(3) 0.09(2) 0.023(12) -0.006(13) 0.010(14) 0.01(2) C25 0.086(19) 0.066(17) 0.031(12) 0.000(11) 0.009(12) -0.028(15) C26 0.065(14) 0.023(9) 0.038(11) -0.008(8) 0.004(10) -0.004(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 Zn1 N1 2.004(16) . ? Zn1 N2 2.067(18) . ? Zn1 Br2 2.329(3) . ? Zn1 Br1 2.369(3) . ? N1 C1 1.30(3) . ? N1 C5 1.37(3) . ? C1 C2 1.39(3) . ? C2 C3 1.40(3) . ? C3 C4 1.39(3) . ? C3 C11 1.47(3) . ? C4 C5 1.37(3) . ? N2 C6 1.32(3) . ? N2 C10 1.33(3) . ? C6 C7 1.38(3) . ? C7 C8 1.37(3) . ? C8 C9 1.36(3) . ? C8 C13 1.49(3) 4_685 ? C9 C10 1.42(3) . ? F1 C16 1.21(3) . ? F2 C22 1.23(4) . ? C11 C12 1.52(3) . ? C11 C14 1.59(3) . ? C12 C15 1.52(3) . ? C12 C13 1.60(3) . ? C13 C8 1.49(3) 4_586 ? C13 C14 1.57(3) . ? C14 C21 1.50(3) . ? C15 C16 1.34(3) . ? C15 C20 1.38(3) . ? C16 C17 1.43(4) . ? C17 C18 1.31(5) . ? C18 C19 1.35(5) . ? C19 C20 1.37(4) . ? C21 C26 1.36(3) . ? C21 C22 1.40(3) . ? C22 C23 1.44(4) . ? C23 C24 1.22(4) . ? C24 C25 1.42(4) . ? C25 C26 1.38(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 Zn1 N2 98.2(6) . . ? N1 Zn1 Br2 109.5(5) . . ? N2 Zn1 Br2 114.6(5) . . ? N1 Zn1 Br1 108.1(5) . . ? N2 Zn1 Br1 103.4(5) . . ? Br2 Zn1 Br1 120.54(12) . . ? C1 N1 C5 116.4(18) . . ? C1 N1 Zn1 126.0(15) . . ? C5 N1 Zn1 117.5(13) . . ? N1 C1 C2 124(2) . . ? C1 C2 C3 120(2) . . ? C4 C3 C2 117.0(19) . . ? C4 C3 C11 119.3(19) . . ? C2 C3 C11 123.6(18) . . ? C5 C4 C3 118(2) . . ? N1 C5 C4 124(2) . . ? C6 N2 C10 117.4(18) . . ? C6 N2 Zn1 123.8(14) . . ? C10 N2 Zn1 118.7(13) . . ? N2 C6 C7 124(2) . . ? C8 C7 C6 120(2) . . ? C9 C8 C7 116.7(19) . . ? C9 C8 C13 123.1(18) . 4_685 ? C7 C8 C13 120.2(18) . 4_685 ? C8 C9 C10 120.5(19) . . ? N2 C10 C9 121.3(19) . . ? C3 C11 C12 121.7(18) . . ? C3 C11 C14 121.9(19) . . ? C12 C11 C14 89.2(16) . . ? C11 C12 C15 120.4(19) . . ? C11 C12 C13 89.1(15) . . ? C15 C12 C13 120.2(18) . . ? C8 C13 C14 115.8(16) 4_586 . ? C8 C13 C12 111.9(18) 4_586 . ? C14 C13 C12 87.3(15) . . ? C21 C14 C13 116.8(18) . . ? C21 C14 C11 116.5(16) . . ? C13 C14 C11 87.6(17) . . ? C16 C15 C20 116(2) . . ? C16 C15 C12 120.4(19) . . ? C20 C15 C12 123(2) . . ? F1 C16 C15 123(2) . . ? F1 C16 C17 115(2) . . ? C15 C16 C17 122(2) . . ? C18 C17 C16 119(3) . . ? C17 C18 C19 122(3) . . ? C18 C19 C20 119(3) . . ? C19 C20 C15 123(3) . . ? C26 C21 C22 117(2) . . ? C26 C21 C14 124.4(19) . . ? C22 C21 C14 118(2) . . ? F2 C22 C21 120(3) . . ? F2 C22 C23 117(3) . . ? C21 C22 C23 122(2) . . ? C24 C23 C22 118(2) . . ? C23 C24 C25 123(3) . . ? C26 C25 C24 121(3) . . ? C21 C26 C25 119(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 2.070 _refine_diff_density_min -1.522 _refine_diff_density_rms 0.309 #===#END _database_code_depnum_ccdc_archive 'CCDC 938969' ####################################################################### # # 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_Compound_4 # data_d087 CCDC 938970 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C26 H20 Br2 F2 N2 Zn' _chemical_formula_weight 623.63 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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)/n 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 9.6230(9) _cell_length_b 13.0226(11) _cell_length_c 19.0893(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.861(2) _cell_angle_gamma 90.00 _cell_volume 2391.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4990 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 27.17 _exptl_crystal_description Block _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.33 _exptl_crystal_size_min 0.23 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.732 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 4.400 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2720 _exptl_absorpt_correction_T_max 0.4310 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16474 _diffrn_reflns_av_R_equivalents 0.0364 _diffrn_reflns_av_sigmaI/netI 0.0427 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.89 _diffrn_reflns_theta_max 27.47 _reflns_number_total 5449 _reflns_number_gt 4553 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ISOR 0.001 0.002 F2 F2A EADP F1 F1A ISOR 0.005 0.008 F1 F1A N2 N2A EADP F2 F2A EADP C18 C18A SIZE 0.40 0.33 0.23 DELU 0.005 N2 > C26A SIMU 0.005 0.008 N2 > C26A SADI 0.01 C19A C15A C19A C17A SADI 0.01 C20A C22A C20A C26A SADI 0.01 C19 C15 C19 C17 SADI 0.01 C20 C22 C20 C26 DFIX 1.50 C16A C19A C20A C21A DFIX 1.50 C16 C19 C20 C21 DFIX 1.30 C19A C20A DFIX 1.30 C19 C20 SADI 0.01 N2 C14 N2 C18 N2A C14A N2A C18A SADI 0.01 C14A C15A C15A C16A C16A C17A C17A C18A SADI 0.01 C14 C15 C15 C16 C16 C17 C17 C18 DFIX 1.5 0.01 C21A C22A C22A C23A C23A C24A C24A C25A C25A C26A C26A C21A DFIX 1.5 0.01 C21 C22 C22 C23 C23 C24 C24 C25 C25 C26 C26 C21 SADI 0.01 C21A C24A C22A C25A C23A C26A C14A C17A C18A C15A SADI 0.01 C21 C24 C22 C25 C23 C26 C14 C17 C18 C15 DFIX 1.5 0.01 C8 C9 C9 C10 C10 C11 C11 C12 C12 C13 C13 C8 SADI 0.01 C9 F1 C13 F1A C22 F2 C26A F2A SIMU 0.01 0.02 F1 F1A F2 F2A DELU 0.005 F1 F1A F2 F2A ; _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^)+(0.0679P)^2^+3.5379P] 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 5449 _refine_ls_number_parameters 426 _refine_ls_number_restraints 597 _refine_ls_R_factor_all 0.0552 _refine_ls_R_factor_gt 0.0441 _refine_ls_wR_factor_ref 0.1269 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.104 _refine_ls_restrained_S_all 1.223 _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 Zn1 Zn 0.56382(5) -0.12471(4) 0.20748(3) 0.01987(15) Uani 1 1 d . . . Br1 Br 0.76248(5) -0.09993(4) 0.13701(2) 0.02651(14) Uani 1 1 d . B . Br2 Br 0.50820(5) -0.29537(3) 0.23542(2) 0.02673(14) Uani 1 1 d . B . F1 F 1.0178(3) -0.0173(2) 0.60312(16) 0.0297(8) Uani 0.905(6) 1 d PDU A 3 F1A F 0.686(2) 0.241(2) 0.5972(13) 0.0297(8) Uani 0.095(6) 1 d PDU A 4 N1 N 0.5937(4) -0.0473(3) 0.29995(19) 0.0194(7) Uani 1 1 d . B . C1 C 0.5954(5) -0.0968(3) 0.3617(2) 0.0233(9) Uani 1 1 d . . . H1 H 0.5719 -0.1677 0.3624 0.028 Uiso 1 1 calc R B . C2 C 0.6297(5) -0.0495(3) 0.4240(2) 0.0231(9) Uani 1 1 d . B . H2 H 0.6302 -0.0875 0.4665 0.028 Uiso 1 1 calc R . . C3 C 0.6637(4) 0.0551(3) 0.4243(2) 0.0204(9) Uani 1 1 d . . . C4 C 0.6572(5) 0.1067(4) 0.3603(3) 0.0255(10) Uani 1 1 d . B . H4 H 0.6752 0.1784 0.3583 0.031 Uiso 1 1 calc R . . C5 C 0.6244(5) 0.0535(4) 0.3000(2) 0.0257(10) Uani 1 1 d . . . H5 H 0.6234 0.0893 0.2567 0.031 Uiso 1 1 calc R B . C6 C 0.7119(5) 0.1078(3) 0.4878(2) 0.0220(9) Uani 1 1 d . B . H6 H 0.6931 0.1790 0.4927 0.026 Uiso 1 1 calc R . . C7 C 0.7812(4) 0.0596(3) 0.5390(2) 0.0202(9) Uani 1 1 d . . . H7 H 0.7934 -0.0124 0.5340 0.024 Uiso 1 1 calc R B . C8 C 0.8401(4) 0.1067(3) 0.6019(2) 0.0194(9) Uani 1 1 d D A . C9 C 0.9604(5) 0.0644(3) 0.6331(2) 0.0238(9) Uani 1 1 d D . . H9A H 0.9988 0.0045 0.6126 0.029 Uiso 0.095(6) 1 calc PR A 4 C10 C 1.0272(5) 0.1050(4) 0.6927(2) 0.0285(10) Uani 1 1 d D A . H10 H 1.1078 0.0735 0.7123 0.034 Uiso 1 1 calc R . . C11 C 0.9701(5) 0.1943(4) 0.7223(2) 0.0273(10) Uani 1 1 d D . . H11 H 1.0125 0.2238 0.7628 0.033 Uiso 1 1 calc R A . C12 C 0.8509(5) 0.2404(4) 0.6924(2) 0.0256(10) Uani 1 1 d D A . H12 H 0.8143 0.3014 0.7122 0.031 Uiso 1 1 calc R . . C13 C 0.7862(5) 0.1961(3) 0.6334(2) 0.0214(9) Uani 1 1 d D . . H13 H 0.7045 0.2268 0.6143 0.026 Uiso 0.905(6) 1 calc PR A 3 F2 F -0.3104(5) 0.1666(4) 0.1284(3) 0.0429(10) Uani 0.652(4) 1 d PDU B 1 N2 N 0.4048(13) -0.047(2) 0.1630(8) 0.0182(10) Uani 0.652(4) 1 d PDU B 1 C14 C 0.2742(9) -0.0383(9) 0.1885(4) 0.0181(11) Uani 0.652(4) 1 d PDU B 1 H14 H 0.2575 -0.0662 0.2336 0.022 Uiso 0.652(4) 1 calc PR B 1 C15 C 0.1626(7) 0.0081(6) 0.1532(3) 0.0177(11) Uani 0.652(4) 1 d PDU B 1 H15 H 0.0738 0.0120 0.1740 0.021 Uiso 0.652(4) 1 calc PR B 1 C16 C 0.1845(7) 0.0491(6) 0.0862(3) 0.0178(11) Uani 0.652(4) 1 d PDU B 1 C17 C 0.3192(6) 0.0426(7) 0.0585(4) 0.0192(11) Uani 0.652(4) 1 d PDU B 1 H17 H 0.3381 0.0686 0.0132 0.023 Uiso 0.652(4) 1 calc PR B 1 C18 C 0.4247(7) -0.0030(10) 0.0993(5) 0.0201(9) Uani 0.652(4) 1 d PDU B 1 H18 H 0.5161 -0.0035 0.0811 0.024 Uiso 0.652(4) 1 calc PR B 1 C19 C 0.0736(6) 0.1000(5) 0.0467(3) 0.0166(10) Uani 0.652(4) 1 d PDU B 1 H19 H 0.0916 0.1164 -0.0008 0.020 Uiso 0.652(4) 1 calc PR B 1 C20 C -0.0533(6) 0.1263(5) 0.0715(3) 0.0176(10) Uani 0.652(4) 1 d PDU B 1 H20 H -0.0702 0.1113 0.1193 0.021 Uiso 0.652(4) 1 calc PR B 1 C21 C -0.1664(7) 0.1753(6) 0.0319(3) 0.0197(10) Uani 0.652(4) 1 d PDU B 1 C22 C -0.2959(7) 0.1919(6) 0.0624(3) 0.0221(12) Uani 0.652(4) 1 d PDU B 1 C23 C -0.4064(7) 0.2335(7) 0.0253(3) 0.0225(12) Uani 0.652(4) 1 d PDU B 1 H23 H -0.4947 0.2399 0.0465 0.027 Uiso 0.652(4) 1 calc PR B 1 C24 C -0.3880(8) 0.2660(8) -0.0435(4) 0.0245(12) Uani 0.652(4) 1 d PDU B 1 H24 H -0.4629 0.2972 -0.0686 0.029 Uiso 0.652(4) 1 calc PR B 1 C25 C -0.2602(7) 0.2529(7) -0.0756(4) 0.0244(12) Uani 0.652(4) 1 d PDU B 1 H25 H -0.2474 0.2754 -0.1224 0.029 Uiso 0.652(4) 1 calc PR B 1 C26 C -0.1504(7) 0.2061(6) -0.0384(3) 0.0207(11) Uani 0.652(4) 1 d PDU B 1 H26 H -0.0642 0.1952 -0.0608 0.025 Uiso 0.652(4) 1 calc PR B 1 F2A F -0.0543(9) 0.2213(7) -0.0926(5) 0.0429(10) Uani 0.348(4) 1 d PDU B 2 N2A N 0.401(3) -0.042(4) 0.1578(14) 0.0188(13) Uani 0.348(4) 1 d PDU B 2 C14A C 0.2896(17) -0.0467(19) 0.2007(8) 0.0205(14) Uani 0.348(4) 1 d PDU B 2 H14A H 0.2963 -0.0774 0.2458 0.025 Uiso 0.348(4) 1 calc PR B 2 C15A C 0.1640(14) -0.0039(13) 0.1760(6) 0.0210(15) Uani 0.348(4) 1 d PDU B 2 H15A H 0.0826 -0.0063 0.2035 0.025 Uiso 0.348(4) 1 calc PR B 2 C16A C 0.1619(13) 0.0427(12) 0.1093(6) 0.0195(13) Uani 0.348(4) 1 d PDU B 2 C17A C 0.2787(12) 0.0428(14) 0.0662(7) 0.0196(14) Uani 0.348(4) 1 d PDU B 2 H17A H 0.2751 0.0735 0.0211 0.024 Uiso 0.348(4) 1 calc PR B 2 C18A C 0.4015(13) -0.0038(19) 0.0916(9) 0.0201(9) Uani 0.348(4) 1 d PDU B 2 H18A H 0.4819 -0.0081 0.0635 0.024 Uiso 0.348(4) 1 calc PR B 2 C19A C 0.0310(13) 0.0952(10) 0.0858(6) 0.0234(13) Uani 0.348(4) 1 d PDU B 2 H19A H -0.0379 0.0985 0.1209 0.028 Uiso 0.348(4) 1 calc PR B 2 C20A C -0.0051(13) 0.1352(10) 0.0294(6) 0.0241(13) Uani 0.348(4) 1 d PDU B 2 H20A H 0.0636 0.1397 -0.0057 0.029 Uiso 0.348(4) 1 calc PR B 2 C21A C -0.1410(12) 0.1758(13) 0.0117(6) 0.0227(13) Uani 0.348(4) 1 d PDU B 2 C22A C -0.2535(12) 0.1756(12) 0.0590(7) 0.0239(15) Uani 0.348(4) 1 d PDU B 2 H22A H -0.2418 0.1407 0.1024 0.029 Uiso 0.348(4) 1 calc PR B 2 C23A C -0.3836(13) 0.2253(14) 0.0447(7) 0.0242(14) Uani 0.348(4) 1 d PDU B 2 H23A H -0.4533 0.2307 0.0793 0.029 Uiso 0.348(4) 1 calc PR B 2 C24A C -0.4032(14) 0.2664(15) -0.0242(7) 0.0245(15) Uani 0.348(4) 1 d PDU B 2 H24A H -0.4925 0.2916 -0.0373 0.029 Uiso 0.348(4) 1 calc PR B 2 C25A C -0.2945(13) 0.2712(13) -0.0742(7) 0.0247(15) Uani 0.348(4) 1 d PDU B 2 H25A H -0.3073 0.3039 -0.1183 0.030 Uiso 0.348(4) 1 calc PR B 2 C26A C -0.1663(11) 0.2246(14) -0.0547(6) 0.0244(14) Uani 0.348(4) 1 d PDU B 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 Zn1 0.0225(3) 0.0199(3) 0.0170(3) 0.00155(19) -0.0053(2) 0.00389(19) Br1 0.0243(2) 0.0305(3) 0.0246(3) 0.00472(19) -0.00105(18) 0.00335(18) Br2 0.0375(3) 0.0194(2) 0.0231(2) 0.00126(17) -0.00345(19) -0.00005(18) F1 0.0310(16) 0.0276(15) 0.0304(16) -0.0077(13) -0.0058(13) 0.0125(13) F1A 0.0310(16) 0.0276(15) 0.0304(16) -0.0077(13) -0.0058(13) 0.0125(13) N1 0.0213(18) 0.0194(18) 0.0175(18) 0.0016(14) -0.0044(14) 0.0054(14) C1 0.026(2) 0.021(2) 0.023(2) 0.0019(18) -0.0053(18) -0.0005(18) C2 0.027(2) 0.021(2) 0.021(2) 0.0039(18) -0.0036(18) -0.0043(18) C3 0.0153(19) 0.024(2) 0.022(2) 0.0006(18) -0.0029(16) 0.0051(17) C4 0.029(2) 0.021(2) 0.026(2) 0.0032(18) -0.0062(19) 0.0036(18) C5 0.032(3) 0.024(2) 0.021(2) 0.0059(18) -0.0060(19) 0.0038(19) C6 0.025(2) 0.018(2) 0.023(2) -0.0017(17) -0.0021(18) 0.0014(17) C7 0.020(2) 0.020(2) 0.020(2) -0.0027(17) -0.0008(17) -0.0003(17) C8 0.021(2) 0.019(2) 0.018(2) 0.0009(16) -0.0008(17) -0.0006(16) C9 0.027(2) 0.022(2) 0.022(2) -0.0010(18) -0.0015(18) 0.0049(18) C10 0.026(2) 0.034(3) 0.025(2) 0.000(2) -0.0062(19) -0.002(2) C11 0.034(3) 0.027(2) 0.021(2) -0.0016(19) -0.0042(19) -0.004(2) C12 0.029(2) 0.024(2) 0.024(2) -0.0025(19) 0.0002(19) -0.0001(19) C13 0.023(2) 0.019(2) 0.021(2) 0.0007(17) -0.0020(17) 0.0017(17) F2 0.0395(15) 0.0449(15) 0.0443(15) -0.0026(13) 0.0042(12) 0.0016(13) N2 0.0213(18) 0.019(2) 0.014(2) -0.0001(19) -0.0053(18) 0.0035(17) C14 0.022(2) 0.019(2) 0.013(2) 0.004(2) -0.007(2) 0.001(2) C15 0.020(2) 0.020(2) 0.013(3) 0.005(2) -0.004(2) 0.0008(18) C16 0.020(2) 0.021(2) 0.013(2) 0.003(2) -0.0022(19) 0.0005(19) C17 0.018(2) 0.022(2) 0.017(2) 0.000(2) -0.003(2) 0.004(2) C18 0.0224(19) 0.0228(16) 0.0148(18) 0.0010(16) -0.0077(17) 0.0030(18) C19 0.019(2) 0.019(2) 0.013(2) 0.0022(19) -0.0009(19) 0.0007(18) C20 0.020(2) 0.017(2) 0.016(2) -0.0013(19) -0.0009(19) -0.0005(18) C21 0.019(2) 0.019(2) 0.020(2) -0.005(2) -0.0026(19) 0.0018(19) C22 0.021(2) 0.022(3) 0.024(2) -0.005(2) -0.004(2) 0.004(2) C23 0.024(2) 0.022(2) 0.021(3) -0.004(2) -0.008(2) 0.005(2) C24 0.026(2) 0.023(2) 0.025(3) -0.001(2) -0.005(2) 0.004(2) C25 0.024(2) 0.023(3) 0.026(2) -0.001(2) -0.007(2) 0.002(2) C26 0.020(2) 0.021(3) 0.022(2) -0.002(2) -0.006(2) -0.0024(19) F2A 0.0395(15) 0.0449(15) 0.0443(15) -0.0026(13) 0.0042(12) 0.0016(13) N2A 0.022(2) 0.020(2) 0.015(2) 0.000(2) -0.005(2) 0.003(2) C14A 0.022(3) 0.022(3) 0.017(3) 0.001(3) -0.006(2) 0.002(2) C15A 0.023(3) 0.023(3) 0.017(3) 0.003(3) -0.006(3) 0.000(3) C16A 0.021(2) 0.022(2) 0.016(3) 0.001(3) -0.003(2) 0.000(2) C17A 0.021(3) 0.022(3) 0.016(3) 0.001(2) -0.004(2) 0.002(3) C18A 0.0224(19) 0.0228(16) 0.0148(18) 0.0010(16) -0.0077(17) 0.0030(18) C19A 0.024(3) 0.024(3) 0.022(3) 0.000(3) -0.003(2) 0.002(2) C20A 0.024(3) 0.024(3) 0.024(3) -0.001(3) -0.002(2) 0.001(2) C21A 0.021(2) 0.021(2) 0.025(3) -0.004(2) -0.005(2) 0.000(2) C22A 0.023(3) 0.023(3) 0.025(3) -0.006(3) -0.004(3) 0.003(3) C23A 0.025(3) 0.023(3) 0.024(3) -0.003(3) -0.004(3) 0.004(3) C24A 0.025(3) 0.023(3) 0.026(3) -0.003(3) -0.002(2) 0.004(2) C25A 0.025(3) 0.023(3) 0.026(3) -0.002(3) -0.004(3) 0.002(3) C26A 0.023(3) 0.023(3) 0.027(3) -0.002(3) -0.006(2) 0.000(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Zn1 N2 2.015(12) . ? Zn1 N1 2.049(4) . ? Zn1 N2A 2.11(2) . ? Zn1 Br2 2.3491(7) . ? Zn1 Br1 2.3761(7) . ? F1 C9 1.332(5) . ? F1A C13 1.315(10) . ? N1 C1 1.344(6) . ? N1 C5 1.346(6) . ? C1 C2 1.374(6) . ? C2 C3 1.401(6) . ? C3 C4 1.395(6) . ? C3 C6 1.462(6) . ? C4 C5 1.376(7) . ? C6 C7 1.332(6) . ? C7 C8 1.455(6) . ? C8 C9 1.407(5) . ? C8 C13 1.413(5) . ? C9 C10 1.401(6) . ? C10 C11 1.409(6) . ? C11 C12 1.407(6) . ? C12 C13 1.403(6) . ? F2 C22 1.310(7) . ? N2 C18 1.357(7) . ? N2 C14 1.359(7) . ? C14 C15 1.397(7) . ? C15 C16 1.403(6) . ? C16 C17 1.409(7) . ? C16 C19 1.458(9) . ? C17 C18 1.402(7) . ? C19 C20 1.360(8) . ? C20 C21 1.462(8) . ? C21 C22 1.400(7) . ? C21 C26 1.410(7) . ? C22 C23 1.380(7) . ? C23 C24 1.395(8) . ? C24 C25 1.393(8) . ? C25 C26 1.404(7) . ? F2A C26A 1.308(9) . ? N2A C18A 1.360(8) . ? N2A C14A 1.360(9) . ? C14A C15A 1.406(10) . ? C15A C16A 1.410(9) . ? C16A C17A 1.403(9) . ? C16A C19A 1.496(15) . ? C17A C18A 1.408(10) . ? C19A C20A 1.242(14) . ? C20A C21A 1.446(14) . ? C21A C22A 1.419(10) . ? C21A C26A 1.436(10) . ? C22A C23A 1.432(10) . ? C23A C24A 1.431(10) . ? C24A C25A 1.428(10) . ? C25A C26A 1.419(10) . ? 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 Zn1 N1 102.2(7) . . ? N2 Zn1 N2A 1.9(7) . . ? N1 Zn1 N2A 103.3(13) . . ? N2 Zn1 Br2 113.5(7) . . ? N1 Zn1 Br2 107.41(10) . . ? N2A Zn1 Br2 114.4(13) . . ? N2 Zn1 Br1 107.8(3) . . ? N1 Zn1 Br1 108.50(11) . . ? N2A Zn1 Br1 105.9(5) . . ? Br2 Zn1 Br1 116.43(3) . . ? C1 N1 C5 117.8(4) . . ? C1 N1 Zn1 121.3(3) . . ? C5 N1 Zn1 120.6(3) . . ? N1 C1 C2 122.9(4) . . ? C1 C2 C3 119.5(4) . . ? C4 C3 C2 117.2(4) . . ? C4 C3 C6 120.6(4) . . ? C2 C3 C6 122.1(4) . . ? C5 C4 C3 119.8(4) . . ? N1 C5 C4 122.7(4) . . ? C7 C6 C3 122.4(4) . . ? C6 C7 C8 126.2(4) . . ? C9 C8 C13 116.6(4) . . ? C9 C8 C7 119.4(4) . . ? C13 C8 C7 123.9(4) . . ? F1 C9 C10 117.5(4) . . ? F1 C9 C8 118.3(4) . . ? C10 C9 C8 124.1(4) . . ? C9 C10 C11 117.4(4) . . ? C12 C11 C10 120.7(4) . . ? C13 C12 C11 119.9(4) . . ? F1A C13 C12 123.5(13) . . ? F1A C13 C8 114.4(13) . . ? C12 C13 C8 121.3(4) . . ? C18 N2 C14 115.6(10) . . ? C18 N2 Zn1 118.2(7) . . ? C14 N2 Zn1 126.1(7) . . ? N2 C14 C15 124.7(8) . . ? C14 C15 C16 118.7(6) . . ? C15 C16 C17 118.0(6) . . ? C15 C16 C19 121.7(5) . . ? C17 C16 C19 120.2(5) . . ? C18 C17 C16 118.7(6) . . ? N2 C18 C17 124.2(8) . . ? C20 C19 C16 126.1(6) . . ? C19 C20 C21 126.5(6) . . ? C22 C21 C26 117.6(6) . . ? C22 C21 C20 120.8(5) . . ? C26 C21 C20 121.6(5) . . ? F2 C22 C23 120.0(6) . . ? F2 C22 C21 118.0(5) . . ? C23 C22 C21 122.0(6) . . ? C22 C23 C24 119.7(6) . . ? C25 C24 C23 120.2(6) . . ? C24 C25 C26 119.5(6) . . ? C25 C26 C21 120.9(6) . . ? C18A N2A C14A 126.0(19) . . ? C18A N2A Zn1 126.3(13) . . ? C14A N2A Zn1 107.2(12) . . ? N2A C14A C15A 117.6(16) . . ? C14A C15A C16A 118.3(11) . . ? C17A C16A C15A 121.9(11) . . ? C17A C16A C19A 120.2(8) . . ? C15A C16A C19A 117.9(8) . . ? C16A C17A C18A 118.3(11) . . ? N2A C18A C17A 117.7(16) . . ? C20A C19A C16A 132.4(11) . . ? C19A C20A C21A 126.6(11) . . ? C22A C21A C26A 116.2(10) . . ? C22A C21A C20A 123.1(8) . . ? C26A C21A C20A 120.6(8) . . ? C21A C22A C23A 123.5(10) . . ? C22A C23A C24A 116.5(10) . . ? C25A C24A C23A 122.9(10) . . ? C26A C25A C24A 116.7(10) . . ? F2A C26A C25A 126.1(10) . . ? F2A C26A C21A 110.1(9) . . ? C25A C26A C21A 123.8(10) . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 27.47 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 1.928 _refine_diff_density_min -0.901 _refine_diff_density_rms 0.158 _database_code_depnum_ccdc_archive 'CCDC 938970' ####################################################################### # # 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_compound_5 # data_c786 CCDC 938971 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C52 H40 Br4 F4 N4 Zn2' _chemical_formula_weight 1247.26 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Zn Zn 0.2839 1.4301 '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)/n 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 9.6691(15) _cell_length_b 13.252(2) _cell_length_c 19.137(3) _cell_angle_alpha 90.00 _cell_angle_beta 92.175(4) _cell_angle_gamma 90.00 _cell_volume 2450.4(7) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 643 _cell_measurement_theta_min 2.63 _cell_measurement_theta_max 19.63 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas 'Not measured' _exptl_crystal_density_diffrn 1.690 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1232 _exptl_absorpt_coefficient_mu 4.295 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2656 _exptl_absorpt_correction_T_max 0.5119 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16947 _diffrn_reflns_av_R_equivalents 0.1052 _diffrn_reflns_av_sigmaI/netI 0.1315 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.87 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5626 _reflns_number_gt 2829 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. the constraints/restraints used in .ins file is shown below DFIX 1.45 0.01 C21 C22 C22 C23 C23 C24 C24 C25 C25 C26 C26 C21 SADI 0.05 F1A C8A F1A C12A SADI 0.05 C9 F1 C13A F1A C22 F2 C26 F2A DELU 0.01 0.02 F1 F1A F2 F2A SIMU 0.01 0.02 F1 F1A F2 F2A DELU 0.01 0.02 N1 > C13A SIMU 0.01 0.02 N1 > C13A SADI 0.01 C6A C4A C6A C2A SADI 0.01 C7A C13A C7A C9A SADI 0.01 C6 C4 C6 C2 SADI 0.01 C7 C13 C7 C9 SADI 0.01 C3 C6 C7 C8 C3A C6A C7A C8A SADI 0.01 C6 C7 C6A C7A SADI 0.01 N1 C1 N1 C5 N1A C1A N1A C5A N2 C14 N2 C18 SADI 0.01 C1 C2 C2 C3 C3 C4 C4 C5 SADI 0.01 C8 C9 C9 C10 C10 C11 C11 C12 C12 C13 C13 C8 SADI 0.01 C1A C2A C2A C3A C3A C4A C4A C5A SADI 0.01 C8A C9A C9A C10A C10A C11A C11A C12A C12A C13A C13A C8A SADI 0.01 C8 C11 C9 C12 C10 C13 C2 C5 C1 C4 SADI 0.01 C8A C11A C9A C12A C10A C13A C2A C5A C1A C4A ; _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^)+(0.0943P)^2^+0.0000P] 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 5626 _refine_ls_number_parameters 396 _refine_ls_number_restraints 554 _refine_ls_R_factor_all 0.1483 _refine_ls_R_factor_gt 0.0632 _refine_ls_wR_factor_ref 0.1857 _refine_ls_wR_factor_gt 0.1478 _refine_ls_goodness_of_fit_ref 0.943 _refine_ls_restrained_S_all 0.925 _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 Zn1 Zn 0.55567(8) 0.35400(7) 0.71352(4) 0.0304(2) Uani 1 1 d . . . Br1 Br 0.48117(9) 0.19210(6) 0.74270(5) 0.0472(3) Uani 1 1 d . B . Br2 Br 0.75063(8) 0.36529(7) 0.64216(4) 0.0407(2) Uani 1 1 d . B . F2 F 0.6926(6) 0.7570(5) 1.0878(3) 0.043(2) Uani 0.723(11) 1 d PD A 1 F2A F 1.0015(19) 0.4880(13) 1.1105(9) 0.062(7) Uani 0.277(11) 1 d PD A 2 F1 F -0.2820(8) 0.6126(6) 0.6187(5) 0.072(3) Uani 0.674(6) 1 d PD B 3 N1 N 0.4052(8) 0.4458(11) 0.6658(5) 0.0305(18) Uani 0.674(6) 1 d PGDU B 3 C1 C 0.4416(5) 0.4873(11) 0.6023(5) 0.031(2) Uani 0.674(6) 1 d PGDU B 3 H1 H 0.5358 0.4883 0.5900 0.037 Uiso 0.674(6) 1 calc PR B 3 C2 C 0.3401(5) 0.5272(8) 0.5570(3) 0.0250(19) Uani 0.674(6) 1 d PGDU B 3 H2 H 0.3650 0.5556 0.5136 0.030 Uiso 0.674(6) 1 calc PR B 3 C3 C 0.2022(5) 0.5256(6) 0.5750(3) 0.0213(18) Uani 0.674(6) 1 d PGDU B 3 C4 C 0.1658(6) 0.4841(7) 0.6385(3) 0.025(2) Uani 0.674(6) 1 d PGDU B 3 H4 H 0.0716 0.4831 0.6508 0.030 Uiso 0.674(6) 1 calc PR B 3 C5 C 0.2673(8) 0.4442(9) 0.6838(4) 0.0290(19) Uani 0.674(6) 1 d PGDU B 3 H5 H 0.2424 0.4158 0.7272 0.035 Uiso 0.674(6) 1 calc PR B 3 C6 C 0.0899(8) 0.5457(7) 0.5179(4) 0.0198(17) Uani 0.674(6) 1 d PDU . 3 H6 H 0.1132 0.6078 0.4910 0.024 Uiso 0.674(6) 1 calc PR B 3 C7 C -0.0636(8) 0.5462(6) 0.5343(4) 0.0190(17) Uani 0.674(6) 1 d PDU . 3 H7 H -0.0750 0.5231 0.5835 0.023 Uiso 0.674(6) 1 calc PR B 3 C8 C -0.1494(7) 0.6424(6) 0.5207(4) 0.0307(19) Uani 0.674(6) 1 d PGDU B 3 C9 C -0.2638(8) 0.6606(7) 0.5608(4) 0.036(2) Uani 0.674(6) 1 d PGDU B 3 C10 C -0.3606(8) 0.7330(8) 0.5396(5) 0.046(2) Uani 0.674(6) 1 d PGDU B 3 H10 H -0.4388 0.7454 0.5670 0.056 Uiso 0.674(6) 1 calc PR B 3 C11 C -0.3430(10) 0.7872(8) 0.4784(5) 0.049(2) Uani 0.674(6) 1 d PGDU B 3 H11 H -0.4092 0.8367 0.4640 0.059 Uiso 0.674(6) 1 calc PR B 3 C12 C -0.2287(10) 0.7691(8) 0.4384(5) 0.043(2) Uani 0.674(6) 1 d PGDU B 3 H12 H -0.2167 0.8062 0.3966 0.052 Uiso 0.674(6) 1 calc PR B 3 C13 C -0.1319(8) 0.6967(7) 0.4596(4) 0.036(2) Uani 0.674(6) 1 d PGDU B 3 H13 H -0.0537 0.6843 0.4322 0.043 Uiso 0.674(6) 1 calc PR B 3 F1A F -0.0488(12) 0.7120(11) 0.4057(7) 0.048(3) Uani 0.326(6) 1 d PDU B 4 N1A N 0.4143(15) 0.442(2) 0.6610(11) 0.030(2) Uani 0.326(6) 1 d PGDU B 4 C1A C 0.4130(11) 0.485(2) 0.5947(10) 0.030(2) Uani 0.326(6) 1 d PGDU B 4 H1A H 0.4969 0.4919 0.5709 0.036 Uiso 0.326(6) 1 calc PR B 4 C2A C 0.2889(13) 0.5173(17) 0.5633(7) 0.026(3) Uani 0.326(6) 1 d PGDU B 4 H2A H 0.2880 0.5467 0.5181 0.031 Uiso 0.326(6) 1 calc PR B 4 C3A C 0.1662(11) 0.5068(14) 0.5982(6) 0.026(3) Uani 0.326(6) 1 d PGDU B 4 C4A C 0.1675(14) 0.4637(15) 0.6644(6) 0.029(3) Uani 0.326(6) 1 d PGDU B 4 H4A H 0.0836 0.4566 0.6882 0.034 Uiso 0.326(6) 1 calc PR B 4 C5A C 0.2916(18) 0.431(2) 0.6958(8) 0.031(3) Uani 0.326(6) 1 d PGDU B 4 H5A H 0.2925 0.4017 0.7411 0.037 Uiso 0.326(6) 1 calc PR B 4 C6A C 0.0286(15) 0.5073(14) 0.5559(8) 0.030(3) Uani 0.326(6) 1 d PDU . 4 H6A H -0.0486 0.5070 0.5892 0.036 Uiso 0.326(6) 1 calc PR B 4 C7A C -0.0038(19) 0.5845(13) 0.4997(9) 0.032(2) Uani 0.326(6) 1 d PDU . 4 H7A H 0.0834 0.6207 0.4886 0.038 Uiso 0.326(6) 1 calc PR B 4 C8A C -0.1219(16) 0.6609(14) 0.5023(8) 0.037(3) Uani 0.326(6) 1 d PGDU B 4 C9A C -0.2145(18) 0.6569(16) 0.5560(8) 0.039(3) Uani 0.326(6) 1 d PGDU B 4 H9A H -0.1960 0.6145 0.5953 0.047 Uiso 0.326(6) 1 calc PR B 4 C10A C -0.3343(18) 0.7150(19) 0.5523(10) 0.044(3) Uani 0.326(6) 1 d PGDU B 4 H10B H -0.3976 0.7123 0.5891 0.053 Uiso 0.326(6) 1 calc PR B 4 C11A C -0.3614(18) 0.7772(19) 0.4949(12) 0.044(3) Uani 0.326(6) 1 d PGDU B 4 H11B H -0.4432 0.8169 0.4924 0.053 Uiso 0.326(6) 1 calc PR B 4 C12A C -0.269(2) 0.7812(17) 0.4412(10) 0.043(3) Uani 0.326(6) 1 d PGDU B 4 H12B H -0.2873 0.8236 0.4019 0.051 Uiso 0.326(6) 1 calc PR B 4 C13A C -0.1490(18) 0.7230(15) 0.4449(9) 0.040(3) Uani 0.326(6) 1 d PGDU B 4 N2 N 0.5974(6) 0.4347(4) 0.8011(3) 0.0349(15) Uani 1 1 d D B . C14 C 0.6500(9) 0.5301(5) 0.7963(4) 0.045(2) Uani 1 1 d D . . H14 H 0.6621 0.5576 0.7511 0.054 Uiso 1 1 calc R B . C15 C 0.6855(9) 0.5873(7) 0.8527(4) 0.048(2) Uani 1 1 d . B . H15 H 0.7197 0.6538 0.8464 0.058 Uiso 1 1 calc R . . C16 C 0.6723(8) 0.5493(6) 0.9200(4) 0.041(2) Uani 1 1 d . . . C17 C 0.6164(8) 0.4518(6) 0.9249(4) 0.041(2) Uani 1 1 d . B . H17 H 0.6032 0.4230 0.9696 0.050 Uiso 1 1 calc R . . C18 C 0.5813(8) 0.3986(6) 0.8668(3) 0.0374(19) Uani 1 1 d D . . H18 H 0.5436 0.3330 0.8720 0.045 Uiso 1 1 calc R B . C19 C 0.7248(8) 0.6064(6) 0.9812(4) 0.041(2) Uani 1 1 d . B . H19 H 0.7206 0.6780 0.9789 0.049 Uiso 1 1 calc R . . C20 C 0.7776(8) 0.5653(6) 1.0393(4) 0.041(2) Uani 1 1 d . . . H20 H 0.7755 0.4937 1.0413 0.049 Uiso 1 1 calc R B . C21 C 0.8370(7) 0.6149(5) 1.0992(4) 0.0338(18) Uani 1 1 d D A . C22 C 0.7956(7) 0.7106(5) 1.1229(4) 0.0353(18) Uani 1 1 d D . . H22A H 0.7212 0.7436 1.0983 0.042 Uiso 0.277(11) 1 calc PR A 2 C23 C 0.8586(7) 0.7596(6) 1.1808(3) 0.0380(19) Uani 1 1 d D A . H23 H 0.8282 0.8247 1.1944 0.046 Uiso 1 1 calc R . . C24 C 0.9675(7) 0.7112(6) 1.2186(4) 0.043(2) Uani 1 1 d D . . H24 H 1.0128 0.7435 1.2575 0.051 Uiso 1 1 calc R A . C25 C 1.0079(8) 0.6139(6) 1.1977(4) 0.044(2) Uani 1 1 d D A . H25 H 1.0791 0.5798 1.2238 0.053 Uiso 1 1 calc R . . C26 C 0.9449(8) 0.5662(6) 1.1387(4) 0.048(2) Uani 1 1 d D . . H26 H 0.9749 0.5009 1.1254 0.058 Uiso 0.723(11) 1 calc PR A 1 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 Zn1 0.0301(5) 0.0328(5) 0.0277(4) 0.0034(4) -0.0058(3) -0.0007(4) Br1 0.0537(6) 0.0337(5) 0.0544(5) 0.0063(4) 0.0055(4) -0.0038(4) Br2 0.0315(4) 0.0541(5) 0.0362(4) 0.0100(4) -0.0019(3) -0.0002(4) F2 0.046(4) 0.040(4) 0.043(4) 0.003(3) -0.016(3) -0.002(3) F2A 0.069(13) 0.058(13) 0.056(12) -0.028(10) -0.033(9) 0.035(10) F1 0.066(6) 0.066(6) 0.084(6) -0.010(5) 0.018(5) -0.003(4) N1 0.030(3) 0.028(4) 0.032(3) -0.008(3) -0.007(3) 0.005(3) C1 0.027(4) 0.032(4) 0.033(4) -0.001(3) -0.017(3) 0.002(4) C2 0.017(4) 0.031(4) 0.026(4) 0.001(3) -0.009(3) -0.004(4) C3 0.021(4) 0.027(4) 0.016(4) -0.001(3) 0.001(3) 0.002(3) C4 0.028(4) 0.027(4) 0.019(4) 0.002(4) -0.007(4) 0.006(4) C5 0.026(4) 0.029(4) 0.031(4) 0.002(3) -0.009(3) 0.010(4) C6 0.021(4) 0.020(4) 0.018(4) 0.000(3) -0.001(3) -0.001(3) C7 0.017(4) 0.024(4) 0.016(4) -0.002(3) 0.003(3) 0.003(3) C8 0.029(4) 0.027(4) 0.035(4) -0.006(3) -0.006(3) 0.005(3) C9 0.026(5) 0.033(4) 0.048(4) -0.007(4) -0.003(4) 0.006(4) C10 0.038(5) 0.034(5) 0.066(5) -0.004(4) -0.002(4) 0.015(4) C11 0.048(5) 0.038(5) 0.062(5) -0.004(4) -0.012(4) 0.017(4) C12 0.047(5) 0.031(5) 0.051(5) -0.002(4) -0.013(4) 0.016(4) C13 0.039(4) 0.028(5) 0.039(4) -0.003(4) -0.014(4) 0.011(4) F1A 0.018(6) 0.063(8) 0.063(8) -0.037(7) 0.002(5) 0.002(6) N1A 0.027(4) 0.029(5) 0.033(4) -0.008(4) -0.008(4) 0.007(4) C1A 0.022(5) 0.032(5) 0.035(4) -0.004(4) -0.011(4) 0.001(5) C2A 0.022(5) 0.030(5) 0.025(5) -0.001(4) -0.007(4) 0.007(5) C3A 0.024(4) 0.025(5) 0.027(5) -0.003(5) -0.008(4) 0.002(5) C4A 0.029(5) 0.030(6) 0.026(5) -0.002(5) -0.016(5) 0.009(5) C5A 0.023(5) 0.034(5) 0.035(5) -0.007(5) -0.013(4) 0.009(5) C6A 0.028(5) 0.032(5) 0.029(5) -0.004(5) -0.007(5) -0.001(5) C7A 0.032(5) 0.029(5) 0.033(5) -0.005(4) -0.006(4) 0.001(4) C8A 0.036(5) 0.032(5) 0.042(5) -0.014(4) -0.008(4) 0.008(4) C9A 0.036(6) 0.034(5) 0.048(5) -0.007(5) -0.007(5) 0.005(5) C10A 0.038(6) 0.038(6) 0.056(6) -0.002(5) -0.007(5) 0.007(5) C11A 0.039(5) 0.035(6) 0.058(6) -0.002(5) -0.005(5) 0.011(5) C12A 0.039(6) 0.034(5) 0.055(6) -0.005(5) -0.005(5) 0.016(5) C13A 0.037(5) 0.033(6) 0.049(5) -0.010(5) -0.006(5) 0.015(5) N2 0.041(4) 0.036(4) 0.028(3) 0.007(3) -0.009(3) 0.001(3) C14 0.066(6) 0.040(5) 0.029(4) 0.006(4) -0.014(4) -0.003(4) C15 0.064(6) 0.040(5) 0.040(5) 0.006(4) -0.010(4) -0.003(4) C16 0.044(5) 0.050(5) 0.029(4) 0.005(4) -0.017(3) -0.008(4) C17 0.041(5) 0.053(6) 0.030(4) 0.010(4) -0.009(3) -0.007(4) C18 0.040(5) 0.040(5) 0.031(4) 0.011(4) -0.007(3) -0.010(4) C19 0.046(5) 0.040(5) 0.035(4) -0.003(4) -0.003(4) -0.005(4) C20 0.044(5) 0.036(5) 0.041(5) 0.005(4) -0.014(4) -0.003(4) C21 0.036(4) 0.034(4) 0.030(4) 0.000(3) -0.007(3) -0.002(3) C22 0.037(4) 0.036(5) 0.033(4) -0.001(3) -0.004(3) -0.004(4) C23 0.039(5) 0.045(5) 0.030(4) -0.005(4) -0.005(3) -0.006(4) C24 0.036(5) 0.056(6) 0.037(4) 0.001(4) -0.007(4) -0.006(4) C25 0.037(5) 0.058(6) 0.037(4) 0.003(4) -0.018(4) -0.002(4) C26 0.044(5) 0.043(5) 0.057(6) 0.000(4) -0.015(4) 0.008(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 Zn1 N2 2.017(6) . ? Zn1 N1A 2.030(14) . ? Zn1 N1 2.081(6) . ? Zn1 Br1 2.3377(12) . ? Zn1 Br2 2.3741(12) . ? F2 C22 1.330(9) . ? F2A C26 1.299(16) . ? F1 C9 1.294(10) . ? N1 C1 1.3900 . ? N1 C5 1.3900 . ? C1 C2 1.3900 . ? C2 C3 1.3900 . ? C3 C4 1.3900 . ? C3 C6 1.535(8) . ? C4 C5 1.3900 . ? C6 C7 1.528(10) . ? C6 C7 1.590(12) 3_566 ? C7 C8 1.538(8) . ? C7 C6 1.590(12) 3_566 ? C8 C9 1.3900 . ? C8 C13 1.3900 . ? C9 C10 1.3900 . ? C10 C11 1.3900 . ? C11 C12 1.3900 . ? C12 C13 1.3900 . ? F1A C13A 1.256(17) . ? N1A C1A 1.3900 . ? N1A C5A 1.3900 . ? C1A C2A 1.3900 . ? C2A C3A 1.3900 . ? C3A C4A 1.3900 . ? C3A C6A 1.531(9) . ? C4A C5A 1.3900 . ? C6A C7A 1.507(12) . ? C6A C7A 1.63(3) 3_566 ? C7A C8A 1.530(9) . ? C7A C6A 1.63(3) 3_566 ? C8A C9A 1.3900 . ? C8A C13A 1.3900 . ? C9A C10A 1.3900 . ? C10A C11A 1.3900 . ? C11A C12A 1.3900 . ? C12A C13A 1.3900 . ? N2 C18 1.359(6) . ? N2 C14 1.367(6) . ? C14 C15 1.353(11) . ? C15 C16 1.394(10) . ? C16 C17 1.405(11) . ? C16 C19 1.469(10) . ? C17 C18 1.349(10) . ? C19 C20 1.324(10) . ? C20 C21 1.423(10) . ? C21 C22 1.410(7) . ? C21 C26 1.421(7) . ? C22 C23 1.405(7) . ? C23 C24 1.409(7) . ? C24 C25 1.410(7) . ? C25 C26 1.411(7) . ? 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 Zn1 N1A 102.6(9) . . ? N2 Zn1 N1 99.8(4) . . ? N1A Zn1 N1 3.7(9) . . ? N2 Zn1 Br1 110.01(15) . . ? N1A Zn1 Br1 115.8(8) . . ? N1 Zn1 Br1 115.1(4) . . ? N2 Zn1 Br2 107.85(17) . . ? N1A Zn1 Br2 102.3(6) . . ? N1 Zn1 Br2 105.5(3) . . ? Br1 Zn1 Br2 116.99(5) . . ? C1 N1 C5 120.0 . . ? C1 N1 Zn1 114.8(5) . . ? C5 N1 Zn1 122.9(5) . . ? N1 C1 C2 120.0 . . ? C1 C2 C3 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 C6 119.7(3) . . ? C2 C3 C6 118.7(3) . . ? C5 C4 C3 120.0 . . ? C4 C5 N1 120.0 . . ? C7 C6 C3 121.4(6) . . ? C7 C6 C7 89.9(6) . 3_566 ? C3 C6 C7 114.0(7) . 3_566 ? C6 C7 C8 119.4(7) . . ? C6 C7 C6 90.1(6) . 3_566 ? C8 C7 C6 117.2(7) . 3_566 ? C9 C8 C13 120.0 . . ? C9 C8 C7 119.1(3) . . ? C13 C8 C7 119.2(3) . . ? F1 C9 C8 121.6(6) . . ? F1 C9 C10 118.4(6) . . ? C8 C9 C10 120.0 . . ? C11 C10 C9 120.0 . . ? C10 C11 C12 120.0 . . ? C11 C12 C13 120.0 . . ? C12 C13 C8 120.0 . . ? C1A N1A C5A 120.0 . . ? C1A N1A Zn1 132.0(10) . . ? C5A N1A Zn1 106.0(10) . . ? C2A C1A N1A 120.0 . . ? C3A C2A C1A 120.0 . . ? C2A C3A C4A 120.0 . . ? C2A C3A C6A 119.1(5) . . ? C4A C3A C6A 117.5(5) . . ? C5A C4A C3A 120.0 . . ? C4A C5A N1A 120.0 . . ? C7A C6A C3A 122.2(13) . . ? C7A C6A C7A 91.1(13) . 3_566 ? C3A C6A C7A 116.5(15) . 3_566 ? C6A C7A C8A 124.2(12) . . ? C6A C7A C6A 88.9(13) . 3_566 ? C8A C7A C6A 115.1(16) . 3_566 ? C9A C8A C13A 120.0 . . ? C9A C8A C7A 120.1(4) . . ? C13A C8A C7A 119.0(4) . . ? C10A C9A C8A 120.0 . . ? C11A C10A C9A 120.0 . . ? C10A C11A C12A 120.0 . . ? C11A C12A C13A 120.0 . . ? F1A C13A C12A 133.9(10) . . ? F1A C13A C8A 106.1(10) . . ? C12A C13A C8A 120.0 . . ? C18 N2 C14 116.4(6) . . ? C18 N2 Zn1 123.7(5) . . ? C14 N2 Zn1 119.8(5) . . ? C15 C14 N2 123.2(7) . . ? C14 C15 C16 120.3(8) . . ? C15 C16 C17 116.3(7) . . ? C15 C16 C19 120.6(8) . . ? C17 C16 C19 122.9(7) . . ? C18 C17 C16 120.7(7) . . ? C17 C18 N2 123.0(7) . . ? C20 C19 C16 124.6(8) . . ? C19 C20 C21 128.1(8) . . ? C22 C21 C26 116.7(6) . . ? C22 C21 C20 124.3(6) . . ? C26 C21 C20 119.0(6) . . ? F2 C22 C23 118.6(6) . . ? F2 C22 C21 118.0(6) . . ? C23 C22 C21 123.4(7) . . ? C22 C23 C24 119.2(7) . . ? C23 C24 C25 118.7(7) . . ? C24 C25 C26 121.5(7) . . ? F2A C26 C25 121.0(9) . . ? F2A C26 C21 116.9(9) . . ? C25 C26 C21 120.5(7) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.074 _refine_diff_density_min -0.630 _refine_diff_density_rms 0.177 _database_code_depnum_ccdc_archive 'CCDC 938971'