Supplementary Material (ESI) for Analyst This journal is (C) The Royal Society of Chemistry 2009 data_global _journal_name_full 'The Analyst' _journal_coden_Cambridge 0091 _publ_contact_author_name 'Bo Tang' _publ_contact_author_email TANGB@SDNU.EDU.CN _publ_section_title ; Cu2+ Selective Naked-eye and Fluorescent Probe: Its Crystal Structure and Application in Bioimaging ; loop_ _publ_author_name 'Bo Tang' 'Ping Li' 'Jian-Ping Ma' 'Lili Tong' 'Yanlong Xing' 'Fabiao Yu' ; Wenshen Zhang ; # Attachment 'the_cif_document_of_compound_2.cif' data_70917dm _database_code_depnum_ccdc_archive 'CCDC 675992' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H38 N6 O3' _chemical_formula_weight 614.73 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' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.023(3) _cell_length_b 12.111(3) _cell_length_c 15.207(4) _cell_angle_alpha 102.210(4) _cell_angle_beta 96.443(4) _cell_angle_gamma 113.896(4) _cell_volume 1608.5(7) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1563 _cell_measurement_theta_min 2.239 _cell_measurement_theta_max 24.974 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 652 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(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 8183 _diffrn_reflns_av_R_equivalents 0.0195 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 25.01 _reflns_number_total 5583 _reflns_number_gt 3749 _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^)+(0.0948P)^2^+0.2474P] 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 5583 _refine_ls_number_parameters 422 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0999 _refine_ls_R_factor_gt 0.0666 _refine_ls_wR_factor_ref 0.1924 _refine_ls_wR_factor_gt 0.1713 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C1 C 0.5910(3) 1.0566(2) 0.15423(17) 0.0345(6) Uani 1 1 d . . . C2 C 0.4691(3) 0.9654(2) 0.17247(17) 0.0332(6) Uani 1 1 d . . . C3 C 0.3986(3) 1.0076(3) 0.23634(17) 0.0379(6) Uani 1 1 d . . . H3 H 0.3148 0.9481 0.2489 0.046 Uiso 1 1 calc R . . C4 C 0.4461(3) 1.1326(3) 0.28190(18) 0.0396(7) Uani 1 1 d . . . C5 C 0.3669(4) 1.1708(3) 0.3517(2) 0.0545(8) Uani 1 1 d . . . H5A H 0.2834 1.0974 0.3552 0.082 Uiso 1 1 calc R . . H5B H 0.3319 1.2274 0.3335 0.082 Uiso 1 1 calc R . . H5C H 0.4348 1.2122 0.4109 0.082 Uiso 1 1 calc R . . C6 C 0.5726(3) 1.2240(3) 0.26213(18) 0.0407(7) Uani 1 1 d . . . C7 C 0.6421(3) 1.1831(3) 0.19726(18) 0.0407(7) Uani 1 1 d . . . H7 H 0.7242 1.2417 0.1827 0.049 Uiso 1 1 calc R . . C8 C 0.7547(4) 1.4497(3) 0.2989(2) 0.0650(9) Uani 1 1 d . . . H8A H 0.7471 1.5281 0.3183 0.078 Uiso 1 1 calc R . . H8B H 0.7602 1.4354 0.2345 0.078 Uiso 1 1 calc R . . C9 C 0.8951(5) 1.4630(4) 0.3540(3) 0.1002(14) Uani 1 1 d . . . H9A H 0.8922 1.4796 0.4182 0.150 Uiso 1 1 calc R . . H9B H 0.9789 1.5316 0.3451 0.150 Uiso 1 1 calc R . . H9C H 0.9051 1.3866 0.3344 0.150 Uiso 1 1 calc R . . C10 C 0.6207(3) 0.9054(2) 0.04187(18) 0.0364(6) Uani 1 1 d . . . C11 C 0.7033(3) 0.8867(3) -0.02244(18) 0.0412(7) Uani 1 1 d . . . H11 H 0.7837 0.9554 -0.0293 0.049 Uiso 1 1 calc R . . C12 C 0.6668(3) 0.7670(3) -0.07612(18) 0.0401(7) Uani 1 1 d . . . C13 C 0.8837(3) 0.8458(3) -0.1479(2) 0.0605(9) Uani 1 1 d . . . H13A H 0.9508 0.8933 -0.0879 0.073 Uiso 1 1 calc R . . H13B H 0.8564 0.9028 -0.1732 0.073 Uiso 1 1 calc R . . C14 C 0.9622(4) 0.7927(4) -0.2108(2) 0.0827(12) Uani 1 1 d . . . H14A H 0.9928 0.7391 -0.1844 0.124 Uiso 1 1 calc R . . H14B H 1.0487 0.8604 -0.2183 0.124 Uiso 1 1 calc R . . H14C H 0.8953 0.7449 -0.2699 0.124 Uiso 1 1 calc R . . C15 C 0.5425(3) 0.6638(3) -0.06619(18) 0.0409(7) Uani 1 1 d . . . C16 C 0.5025(4) 0.5323(3) -0.1221(2) 0.0618(9) Uani 1 1 d . . . H16A H 0.4207 0.4735 -0.1036 0.093 Uiso 1 1 calc R . . H16B H 0.5874 0.5149 -0.1121 0.093 Uiso 1 1 calc R . . H16C H 0.4738 0.5243 -0.1864 0.093 Uiso 1 1 calc R . . C17 C 0.4648(3) 0.6882(3) -0.00202(18) 0.0402(7) Uani 1 1 d . . . H17 H 0.3830 0.6204 0.0046 0.048 Uiso 1 1 calc R . . C18 C 0.4998(3) 0.8074(2) 0.05377(17) 0.0341(6) Uani 1 1 d . . . C19 C 0.4178(3) 0.8269(2) 0.12891(17) 0.0336(6) Uani 1 1 d . . . C20 C 0.2496(3) 0.7534(2) 0.09964(17) 0.0358(6) Uani 1 1 d . . . C21 C 0.1511(3) 0.7670(3) 0.0368(2) 0.0480(7) Uani 1 1 d . . . H21 H 0.1857 0.8238 0.0024 0.058 Uiso 1 1 calc R . . C22 C -0.0003(3) 0.6943(3) 0.0263(2) 0.0611(9) Uani 1 1 d . . . H22 H -0.0684 0.7031 -0.0152 0.073 Uiso 1 1 calc R . . C23 C -0.0525(3) 0.6085(3) 0.0762(2) 0.0664(10) Uani 1 1 d . . . H23 H -0.1550 0.5611 0.0684 0.080 Uiso 1 1 calc R . . C24 C 0.0444(3) 0.5930(3) 0.1366(2) 0.0564(8) Uani 1 1 d . . . H24 H 0.0095 0.5343 0.1695 0.068 Uiso 1 1 calc R . . C25 C 0.1960(3) 0.6659(3) 0.14813(18) 0.0408(7) Uani 1 1 d . . . C26 C 0.3221(3) 0.6703(3) 0.21022(19) 0.0433(7) Uani 1 1 d . . . C27 C 0.6381(3) 0.8107(3) 0.3199(2) 0.0476(7) Uani 1 1 d . . . C28 C 0.5564(4) 0.8318(4) 0.3941(2) 0.0723(11) Uani 1 1 d . . . H28A H 0.4887 0.8636 0.3735 0.109 Uiso 1 1 calc R . . H28B H 0.6273 0.8917 0.4490 0.109 Uiso 1 1 calc R . . H28C H 0.5011 0.7536 0.4071 0.109 Uiso 1 1 calc R . . C29 C 0.7897(3) 0.8202(3) 0.3490(2) 0.0508(8) Uani 1 1 d . . . C30 C 0.8836(4) 0.8208(4) 0.2863(2) 0.0728(11) Uani 1 1 d . . . H30 H 0.8493 0.8174 0.2260 0.087 Uiso 1 1 calc R . . C31 C 1.0597(4) 0.8291(4) 0.3979(2) 0.0654(9) Uani 1 1 d . . . C32 C 1.1967(4) 0.8284(4) 0.4261(3) 0.0897(13) Uani 1 1 d . . . H32 H 1.2560 0.8242 0.3839 0.108 Uiso 1 1 calc R . . C33 C 1.2442(5) 0.8339(5) 0.5155(3) 0.0930(14) Uani 1 1 d . . . H33 H 1.3351 0.8324 0.5336 0.112 Uiso 1 1 calc R . . C34 C 1.1565(4) 0.8417(4) 0.5796(3) 0.0884(13) Uani 1 1 d . . . H34 H 1.1901 0.8469 0.6406 0.106 Uiso 1 1 calc R . . C35 C 1.0221(4) 0.8417(4) 0.5533(3) 0.0803(12) Uani 1 1 d . . . H35 H 0.9645 0.8473 0.5963 0.096 Uiso 1 1 calc R . . C36 C 0.9705(3) 0.8332(3) 0.4616(2) 0.0563(8) Uani 1 1 d . . . C37 C 0.3217(6) 0.4788(5) 0.4333(3) 0.1214(18) Uani 1 1 d . . . H37A H 0.3452 0.4400 0.4778 0.182 Uiso 1 1 calc R . . H37B H 0.2166 0.4350 0.4057 0.182 Uiso 1 1 calc R . . H37C H 0.3474 0.5651 0.4635 0.182 Uiso 1 1 calc R . . N1 N 0.8329(3) 0.8284(3) 0.43577(17) 0.0583(7) Uani 1 1 d . . . N2 N 1.0149(3) 0.8257(4) 0.3083(2) 0.0843(10) Uani 1 1 d . . . N3 N 0.5929(2) 0.7885(2) 0.23365(15) 0.0423(6) Uani 1 1 d . . . N4 N 0.4470(2) 0.7673(2) 0.20232(14) 0.0369(5) Uani 1 1 d . . . N5 N 0.6216(3) 1.3491(2) 0.30717(18) 0.0577(7) Uani 1 1 d . . . H5 H 0.5689 1.3686 0.3428 0.069 Uiso 1 1 calc R . . N6 N 0.7517(3) 0.7467(3) -0.13741(16) 0.0519(7) Uani 1 1 d . . . H6 H 0.7243 0.6712 -0.1709 0.062 Uiso 1 1 calc R . . O1 O 0.6703(2) 1.02971(17) 0.09181(13) 0.0455(5) Uani 1 1 d . . . O2 O 0.3189(2) 0.5999(2) 0.25829(15) 0.0636(6) Uani 1 1 d . . . O3 O 0.4055(4) 0.4734(3) 0.3629(2) 0.1152(11) Uani 1 1 d . . . H3A H 0.3885 0.5095 0.3263 0.173 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 C1 0.0298(14) 0.0414(16) 0.0332(14) 0.0106(12) 0.0080(11) 0.0162(12) C2 0.0284(13) 0.0409(15) 0.0331(14) 0.0148(12) 0.0073(11) 0.0156(12) C3 0.0363(15) 0.0455(17) 0.0370(15) 0.0167(13) 0.0124(12) 0.0194(13) C4 0.0414(16) 0.0489(18) 0.0350(15) 0.0134(13) 0.0081(12) 0.0255(14) C5 0.061(2) 0.062(2) 0.0493(18) 0.0149(16) 0.0210(15) 0.0334(17) C6 0.0410(16) 0.0455(17) 0.0368(15) 0.0102(13) 0.0035(12) 0.0222(14) C7 0.0357(15) 0.0412(17) 0.0420(16) 0.0127(13) 0.0086(12) 0.0134(13) C8 0.069(2) 0.046(2) 0.069(2) 0.0096(17) 0.0138(18) 0.0180(17) C9 0.077(3) 0.088(3) 0.108(3) 0.020(3) 0.003(3) 0.017(2) C10 0.0339(15) 0.0392(16) 0.0387(15) 0.0132(13) 0.0093(12) 0.0172(12) C11 0.0356(15) 0.0493(18) 0.0428(16) 0.0170(14) 0.0152(12) 0.0191(13) C12 0.0379(15) 0.0599(19) 0.0329(14) 0.0154(14) 0.0110(12) 0.0297(14) C13 0.0439(18) 0.093(3) 0.0469(18) 0.0146(18) 0.0168(14) 0.0332(18) C14 0.059(2) 0.136(4) 0.060(2) 0.019(2) 0.0296(18) 0.051(2) C15 0.0443(16) 0.0480(17) 0.0370(15) 0.0121(13) 0.0079(12) 0.0270(14) C16 0.075(2) 0.059(2) 0.060(2) 0.0109(17) 0.0260(17) 0.0374(19) C17 0.0397(16) 0.0402(16) 0.0415(16) 0.0144(13) 0.0106(12) 0.0167(13) C18 0.0312(14) 0.0427(16) 0.0330(14) 0.0144(12) 0.0075(11) 0.0190(12) C19 0.0349(14) 0.0402(15) 0.0333(14) 0.0173(12) 0.0108(11) 0.0197(12) C20 0.0348(15) 0.0375(15) 0.0364(15) 0.0094(12) 0.0120(12) 0.0167(12) C21 0.0417(17) 0.0517(18) 0.0501(18) 0.0149(15) 0.0062(14) 0.0210(14) C22 0.0392(18) 0.071(2) 0.064(2) 0.0117(19) 0.0017(15) 0.0217(16) C23 0.0321(17) 0.072(2) 0.072(2) 0.007(2) 0.0086(16) 0.0080(16) C24 0.0458(19) 0.053(2) 0.062(2) 0.0196(17) 0.0237(16) 0.0097(15) C25 0.0398(16) 0.0442(17) 0.0395(15) 0.0129(13) 0.0160(12) 0.0173(13) C26 0.0558(18) 0.0448(17) 0.0397(16) 0.0188(14) 0.0228(14) 0.0257(15) C27 0.0485(18) 0.059(2) 0.0454(18) 0.0176(15) 0.0147(14) 0.0306(15) C28 0.064(2) 0.113(3) 0.050(2) 0.017(2) 0.0184(17) 0.049(2) C29 0.0496(18) 0.065(2) 0.0465(18) 0.0201(16) 0.0135(14) 0.0310(16) C30 0.060(2) 0.121(3) 0.053(2) 0.027(2) 0.0170(17) 0.053(2) C31 0.056(2) 0.090(3) 0.059(2) 0.022(2) 0.0107(17) 0.040(2) C32 0.059(2) 0.139(4) 0.087(3) 0.030(3) 0.014(2) 0.061(3) C33 0.064(3) 0.131(4) 0.101(3) 0.041(3) 0.004(2) 0.059(3) C34 0.067(3) 0.127(4) 0.081(3) 0.050(3) 0.005(2) 0.044(3) C35 0.068(2) 0.125(4) 0.066(2) 0.047(2) 0.0121(19) 0.051(2) C36 0.0479(19) 0.073(2) 0.056(2) 0.0270(17) 0.0107(15) 0.0309(17) C37 0.155(5) 0.122(4) 0.101(4) 0.035(3) 0.038(4) 0.071(4) N1 0.0556(17) 0.085(2) 0.0466(15) 0.0266(14) 0.0114(12) 0.0387(15) N2 0.062(2) 0.148(3) 0.061(2) 0.032(2) 0.0213(15) 0.062(2) N3 0.0410(14) 0.0555(15) 0.0406(14) 0.0205(12) 0.0116(11) 0.0270(12) N4 0.0354(12) 0.0473(14) 0.0398(13) 0.0220(11) 0.0131(10) 0.0235(11) N5 0.0608(17) 0.0442(16) 0.0616(17) 0.0030(13) 0.0206(13) 0.0210(13) N6 0.0481(15) 0.0646(17) 0.0482(15) 0.0102(13) 0.0196(12) 0.0306(13) O1 0.0400(11) 0.0413(12) 0.0525(12) 0.0104(10) 0.0241(9) 0.0132(9) O2 0.0750(16) 0.0667(15) 0.0684(15) 0.0459(13) 0.0296(12) 0.0333(12) O3 0.167(3) 0.127(3) 0.110(3) 0.060(2) 0.046(2) 0.105(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 C1 O1 1.374(3) . ? C1 C2 1.378(3) . ? C1 C7 1.379(4) . ? C2 C3 1.393(3) . ? C2 C19 1.508(4) . ? C3 C4 1.377(4) . ? C3 H3 0.9300 . ? C4 C6 1.419(4) . ? C4 C5 1.500(4) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N5 1.374(4) . ? C6 C7 1.390(4) . ? C7 H7 0.9300 . ? C8 N5 1.437(4) . ? C8 C9 1.484(5) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C18 1.373(3) . ? C10 O1 1.384(3) . ? C10 C11 1.390(4) . ? C11 C12 1.380(4) . ? C11 H11 0.9300 . ? C12 N6 1.380(3) . ? C12 C15 1.414(4) . ? C13 N6 1.434(4) . ? C13 C14 1.506(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 C17 1.372(4) . ? C15 C16 1.501(4) . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 C18 1.390(4) . ? C17 H17 0.9300 . ? C18 C19 1.514(3) . ? C19 C20 1.510(3) . ? C19 N4 1.513(3) . ? C20 C21 1.380(4) . ? C20 C25 1.383(3) . ? C21 C22 1.381(4) . ? C21 H21 0.9300 . ? C22 C23 1.383(5) . ? C22 H22 0.9300 . ? C23 C24 1.357(4) . ? C23 H23 0.9300 . ? C24 C25 1.381(4) . ? C24 H24 0.9300 . ? C25 C26 1.466(4) . ? C26 O2 1.229(3) . ? C26 N4 1.366(3) . ? C27 N3 1.272(3) . ? C27 C29 1.484(4) . ? C27 C28 1.504(4) . ? C28 H28A 0.9600 . ? C28 H28B 0.9600 . ? C28 H28C 0.9600 . ? C29 N1 1.311(4) . ? C29 C30 1.412(4) . ? C30 N2 1.295(4) . ? C30 H30 0.9300 . ? C31 N2 1.372(4) . ? C31 C32 1.396(5) . ? C31 C36 1.396(4) . ? C32 C33 1.367(5) . ? C32 H32 0.9300 . ? C33 C34 1.398(6) . ? C33 H33 0.9300 . ? C34 C35 1.361(5) . ? C34 H34 0.9300 . ? C35 C36 1.399(4) . ? C35 H35 0.9300 . ? C36 N1 1.366(4) . ? C37 O3 1.439(5) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? N3 N4 1.385(3) . ? N5 H5 0.8600 . ? N6 H6 0.8600 . ? O3 H3A 0.8200 . ? 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 O1 C1 C2 123.2(2) . . ? O1 C1 C7 114.6(2) . . ? C2 C1 C7 122.1(2) . . ? C1 C2 C3 116.5(2) . . ? C1 C2 C19 122.1(2) . . ? C3 C2 C19 121.3(2) . . ? C4 C3 C2 123.6(2) . . ? C4 C3 H3 118.2 . . ? C2 C3 H3 118.2 . . ? C3 C4 C6 118.5(2) . . ? C3 C4 C5 120.6(3) . . ? C6 C4 C5 120.8(3) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N5 C6 C7 122.5(3) . . ? N5 C6 C4 119.2(2) . . ? C7 C6 C4 118.3(3) . . ? C1 C7 C6 120.9(3) . . ? C1 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? N5 C8 C9 114.1(3) . . ? N5 C8 H8A 108.7 . . ? C9 C8 H8A 108.7 . . ? N5 C8 H8B 108.7 . . ? C9 C8 H8B 108.7 . . ? H8A C8 H8B 107.6 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C18 C10 O1 123.4(2) . . ? C18 C10 C11 122.0(3) . . ? O1 C10 C11 114.6(2) . . ? C12 C11 C10 120.5(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? N6 C12 C11 121.0(3) . . ? N6 C12 C15 119.8(3) . . ? C11 C12 C15 119.1(2) . . ? N6 C13 C14 110.6(3) . . ? N6 C13 H13A 109.5 . . ? C14 C13 H13A 109.5 . . ? N6 C13 H13B 109.5 . . ? C14 C13 H13B 109.5 . . ? H13A C13 H13B 108.1 . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C17 C15 C12 117.7(3) . . ? C17 C15 C16 122.0(3) . . ? C12 C15 C16 120.3(3) . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C15 C17 C18 124.5(3) . . ? C15 C17 H17 117.8 . . ? C18 C17 H17 117.8 . . ? C10 C18 C17 116.2(2) . . ? C10 C18 C19 121.8(2) . . ? C17 C18 C19 121.8(2) . . ? C2 C19 C20 113.0(2) . . ? C2 C19 N4 109.2(2) . . ? C20 C19 N4 99.28(18) . . ? C2 C19 C18 110.4(2) . . ? C20 C19 C18 114.4(2) . . ? N4 C19 C18 109.9(2) . . ? C21 C20 C25 120.0(2) . . ? C21 C20 C19 128.8(2) . . ? C25 C20 C19 111.2(2) . . ? C20 C21 C22 118.3(3) . . ? C20 C21 H21 120.9 . . ? C22 C21 H21 120.9 . . ? C21 C22 C23 121.2(3) . . ? C21 C22 H22 119.4 . . ? C23 C22 H22 119.4 . . ? C24 C23 C22 120.6(3) . . ? C24 C23 H23 119.7 . . ? C22 C23 H23 119.7 . . ? C23 C24 C25 118.6(3) . . ? C23 C24 H24 120.7 . . ? C25 C24 H24 120.7 . . ? C24 C25 C20 121.3(3) . . ? C24 C25 C26 129.3(3) . . ? C20 C25 C26 109.3(2) . . ? O2 C26 N4 126.1(3) . . ? O2 C26 C25 127.8(3) . . ? N4 C26 C25 106.1(2) . . ? N3 C27 C29 115.4(3) . . ? N3 C27 C28 126.9(3) . . ? C29 C27 C28 117.7(3) . . ? C27 C28 H28A 109.5 . . ? C27 C28 H28B 109.5 . . ? H28A C28 H28B 109.5 . . ? C27 C28 H28C 109.5 . . ? H28A C28 H28C 109.5 . . ? H28B C28 H28C 109.5 . . ? N1 C29 C30 121.3(3) . . ? N1 C29 C27 117.0(3) . . ? C30 C29 C27 121.6(3) . . ? N2 C30 C29 123.6(3) . . ? N2 C30 H30 118.2 . . ? C29 C30 H30 118.2 . . ? N2 C31 C32 119.6(3) . . ? N2 C31 C36 121.2(3) . . ? C32 C31 C36 119.2(3) . . ? C33 C32 C31 120.4(4) . . ? C33 C32 H32 119.8 . . ? C31 C32 H32 119.8 . . ? C32 C33 C34 120.1(4) . . ? C32 C33 H33 119.9 . . ? C34 C33 H33 119.9 . . ? C35 C34 C33 120.4(4) . . ? C35 C34 H34 119.8 . . ? C33 C34 H34 119.8 . . ? C34 C35 C36 120.1(4) . . ? C34 C35 H35 119.9 . . ? C36 C35 H35 119.9 . . ? N1 C36 C31 121.0(3) . . ? N1 C36 C35 119.2(3) . . ? C31 C36 C35 119.7(3) . . ? O3 C37 H37A 109.5 . . ? O3 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O3 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C29 N1 C36 116.8(3) . . ? C30 N2 C31 116.0(3) . . ? C27 N3 N4 117.5(2) . . ? C26 N4 N3 125.2(2) . . ? C26 N4 C19 113.9(2) . . ? N3 N4 C19 118.06(19) . . ? C6 N5 C8 124.6(3) . . ? C6 N5 H5 117.7 . . ? C8 N5 H5 117.7 . . ? C12 N6 C13 123.0(3) . . ? C12 N6 H6 118.5 . . ? C13 N6 H6 118.5 . . ? C1 O1 C10 118.1(2) . . ? C37 O3 H3A 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 -178.8(2) . . . . ? C7 C1 C2 C3 0.6(4) . . . . ? O1 C1 C2 C19 3.6(4) . . . . ? C7 C1 C2 C19 -177.0(2) . . . . ? C1 C2 C3 C4 -1.4(4) . . . . ? C19 C2 C3 C4 176.2(2) . . . . ? C2 C3 C4 C6 0.9(4) . . . . ? C2 C3 C4 C5 -178.4(2) . . . . ? C3 C4 C6 N5 -179.9(2) . . . . ? C5 C4 C6 N5 -0.6(4) . . . . ? C3 C4 C6 C7 0.3(4) . . . . ? C5 C4 C6 C7 179.6(2) . . . . ? O1 C1 C7 C6 -180.0(2) . . . . ? C2 C1 C7 C6 0.6(4) . . . . ? N5 C6 C7 C1 179.2(2) . . . . ? C4 C6 C7 C1 -1.0(4) . . . . ? C18 C10 C11 C12 -0.9(4) . . . . ? O1 C10 C11 C12 179.3(2) . . . . ? C10 C11 C12 N6 -177.3(2) . . . . ? C10 C11 C12 C15 1.2(4) . . . . ? N6 C12 C15 C17 177.7(2) . . . . ? C11 C12 C15 C17 -0.8(4) . . . . ? N6 C12 C15 C16 0.0(4) . . . . ? C11 C12 C15 C16 -178.6(2) . . . . ? C12 C15 C17 C18 0.0(4) . . . . ? C16 C15 C17 C18 177.7(3) . . . . ? O1 C10 C18 C17 179.9(2) . . . . ? C11 C10 C18 C17 0.1(4) . . . . ? O1 C10 C18 C19 -5.1(4) . . . . ? C11 C10 C18 C19 175.1(2) . . . . ? C15 C17 C18 C10 0.3(4) . . . . ? C15 C17 C18 C19 -174.7(2) . . . . ? C1 C2 C19 C20 -139.3(2) . . . . ? C3 C2 C19 C20 43.2(3) . . . . ? C1 C2 C19 N4 111.2(2) . . . . ? C3 C2 C19 N4 -66.3(3) . . . . ? C1 C2 C19 C18 -9.7(3) . . . . ? C3 C2 C19 C18 172.8(2) . . . . ? C10 C18 C19 C2 10.4(3) . . . . ? C17 C18 C19 C2 -174.9(2) . . . . ? C10 C18 C19 C20 139.3(2) . . . . ? C17 C18 C19 C20 -46.1(3) . . . . ? C10 C18 C19 N4 -110.1(3) . . . . ? C17 C18 C19 N4 64.6(3) . . . . ? C2 C19 C20 C21 60.8(3) . . . . ? N4 C19 C20 C21 176.4(3) . . . . ? C18 C19 C20 C21 -66.7(4) . . . . ? C2 C19 C20 C25 -116.6(2) . . . . ? N4 C19 C20 C25 -1.0(3) . . . . ? C18 C19 C20 C25 115.9(2) . . . . ? C25 C20 C21 C22 1.8(4) . . . . ? C19 C20 C21 C22 -175.3(3) . . . . ? C20 C21 C22 C23 -0.9(5) . . . . ? C21 C22 C23 C24 -0.6(5) . . . . ? C22 C23 C24 C25 1.0(5) . . . . ? C23 C24 C25 C20 -0.1(5) . . . . ? C23 C24 C25 C26 177.9(3) . . . . ? C21 C20 C25 C24 -1.4(4) . . . . ? C19 C20 C25 C24 176.2(3) . . . . ? C21 C20 C25 C26 -179.7(2) . . . . ? C19 C20 C25 C26 -2.1(3) . . . . ? C24 C25 C26 O2 8.3(5) . . . . ? C20 C25 C26 O2 -173.6(3) . . . . ? C24 C25 C26 N4 -173.5(3) . . . . ? C20 C25 C26 N4 4.6(3) . . . . ? N3 C27 C29 N1 -172.3(3) . . . . ? C28 C27 C29 N1 9.5(4) . . . . ? N3 C27 C29 C30 7.9(5) . . . . ? C28 C27 C29 C30 -170.3(3) . . . . ? N1 C29 C30 N2 2.0(6) . . . . ? C27 C29 C30 N2 -178.2(4) . . . . ? N2 C31 C32 C33 179.0(4) . . . . ? C36 C31 C32 C33 -1.2(7) . . . . ? C31 C32 C33 C34 -0.7(7) . . . . ? C32 C33 C34 C35 1.2(7) . . . . ? C33 C34 C35 C36 0.3(7) . . . . ? N2 C31 C36 N1 2.8(6) . . . . ? C32 C31 C36 N1 -177.1(3) . . . . ? N2 C31 C36 C35 -177.5(4) . . . . ? C32 C31 C36 C35 2.6(6) . . . . ? C34 C35 C36 N1 177.5(4) . . . . ? C34 C35 C36 C31 -2.3(6) . . . . ? C30 C29 N1 C36 -2.2(5) . . . . ? C27 C29 N1 C36 178.0(3) . . . . ? C31 C36 N1 C29 -0.1(5) . . . . ? C35 C36 N1 C29 -179.9(3) . . . . ? C29 C30 N2 C31 0.6(6) . . . . ? C32 C31 N2 C30 177.0(4) . . . . ? C36 C31 N2 C30 -2.9(6) . . . . ? C29 C27 N3 N4 174.2(2) . . . . ? C28 C27 N3 N4 -7.8(5) . . . . ? O2 C26 N4 N3 12.5(4) . . . . ? C25 C26 N4 N3 -165.8(2) . . . . ? O2 C26 N4 C19 172.7(3) . . . . ? C25 C26 N4 C19 -5.5(3) . . . . ? C27 N3 N4 C26 -62.3(4) . . . . ? C27 N3 N4 C19 138.2(3) . . . . ? C2 C19 N4 C26 122.6(2) . . . . ? C20 C19 N4 C26 4.2(3) . . . . ? C18 C19 N4 C26 -116.2(2) . . . . ? C2 C19 N4 N3 -75.6(3) . . . . ? C20 C19 N4 N3 165.9(2) . . . . ? C18 C19 N4 N3 45.6(3) . . . . ? C7 C6 N5 C8 -5.4(4) . . . . ? C4 C6 N5 C8 174.8(3) . . . . ? C9 C8 N5 C6 -78.5(4) . . . . ? C11 C12 N6 C13 1.7(4) . . . . ? C15 C12 N6 C13 -176.7(3) . . . . ? C14 C13 N6 C12 173.0(3) . . . . ? C2 C1 O1 C10 3.1(3) . . . . ? C7 C1 O1 C10 -176.4(2) . . . . ? C18 C10 O1 C1 -2.3(4) . . . . ? C11 C10 O1 C1 177.5(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3A O2 0.82 1.92 2.726(3) 166.9 . N5 H5 O3 0.86 2.45 3.192(4) 144.4 1_565 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.365 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.045 # Attachment 'the_cif_document_of_compound_3.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 675993' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C37 H39 Br3 Cl Cu Hg N6 O3' _chemical_formula_weight 1155.05 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Hg Hg -2.3894 9.2266 '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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5212(16) _cell_length_b 11.861(2) _cell_length_c 17.621(3) _cell_angle_alpha 92.939(3) _cell_angle_beta 94.128(3) _cell_angle_gamma 102.065(2) _cell_volume 1936.5(6) _cell_formula_units_Z 2 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 1953 _cell_measurement_theta_min 2.173 _cell_measurement_theta_max 21.703 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.981 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1116 _exptl_absorpt_coefficient_mu 7.717 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.2941 _exptl_absorpt_correction_T_max 0.4578 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 10218 _diffrn_reflns_av_R_equivalents 0.0356 _diffrn_reflns_av_sigmaI/netI 0.0868 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.76 _diffrn_reflns_theta_max 25.50 _reflns_number_total 7079 _reflns_number_gt 4968 _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 ADP of atom C34 was restrained to be isotropic within a standard deviation of 0.01 ?2 and the rigid bond of Hg1 and Br2 was restrained within a standard deviation of 0.05 ?. In total seven restraintswere used. ; _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^)+(0.1027P)^2^+15.6734P] 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 7079 _refine_ls_number_parameters 475 _refine_ls_number_restraints 7 _refine_ls_R_factor_all 0.0993 _refine_ls_R_factor_gt 0.0671 _refine_ls_wR_factor_ref 0.1984 _refine_ls_wR_factor_gt 0.1769 _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_restrained_S_all 1.031 _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 Cu1 Cu 0.51284(15) 0.78700(12) 0.50941(8) 0.0221(3) Uani 1 1 d . . . Hg1 Hg 0.38811(6) 0.38634(4) 0.92738(3) 0.0349(2) Uani 1 1 d U . . Br1 Br 0.65106(14) 0.41697(11) 0.99183(9) 0.0360(3) Uani 1 1 d . . . Br2 Br 0.3620(2) 0.42954(19) 0.79123(13) 0.0757(6) Uani 1 1 d U . . Br3 Br 0.20774(16) 0.20850(13) 0.95005(10) 0.0467(4) Uani 1 1 d . . . C1 C 0.8778(17) 0.3471(13) 0.8339(10) 0.050(4) Uani 1 1 d . . . H1A H 0.8136 0.3879 0.8080 0.074 Uiso 1 1 calc R . . H1B H 0.8239 0.2911 0.8642 0.074 Uiso 1 1 calc R . . H1C H 0.9243 0.3085 0.7971 0.074 Uiso 1 1 calc R . . C2 C 0.9875(13) 0.4296(11) 0.8838(8) 0.033(3) Uani 1 1 d . . . H2A H 0.9406 0.4593 0.9252 0.039 Uiso 1 1 calc R . . H2B H 1.0564 0.3883 0.9061 0.039 Uiso 1 1 calc R . . C3 C 1.0189(12) 0.6229(10) 0.8313(6) 0.019(2) Uani 1 1 d . . . C4 C 1.1027(12) 0.7099(10) 0.7913(6) 0.020(2) Uani 1 1 d . . . C5 C 1.2514(12) 0.6971(10) 0.7724(7) 0.024(3) Uani 1 1 d . . . H5A H 1.3032 0.7687 0.7559 0.036 Uiso 1 1 calc R . . H5B H 1.2427 0.6373 0.7325 0.036 Uiso 1 1 calc R . . H5C H 1.3025 0.6771 0.8170 0.036 Uiso 1 1 calc R . . C6 C 1.0508(12) 0.8021(10) 0.7701(7) 0.022(3) Uani 1 1 d . . . H6A H 1.1038 0.8543 0.7398 0.026 Uiso 1 1 calc R . . C7 C 0.9152(12) 0.8218(9) 0.7931(6) 0.018(2) Uani 1 1 d . . . C8 C 0.8410(12) 0.7389(10) 0.8374(7) 0.021(3) Uani 1 1 d . . . C9 C 0.8858(12) 0.6385(10) 0.8561(7) 0.020(2) Uani 1 1 d . . . H9 H 0.8304 0.5838 0.8839 0.024 Uiso 1 1 calc R . . C10 C 0.8510(12) 0.9122(9) 0.7695(7) 0.020(2) Uani 1 1 d . . . C11 C 0.9218(11) 0.9948(9) 0.7147(7) 0.020(2) Uani 1 1 d . . . C12 C 1.0402(12) 1.0781(10) 0.7426(7) 0.024(3) Uani 1 1 d . . . H12 H 1.0724 1.0823 0.7940 0.029 Uiso 1 1 calc R . . C13 C 1.1125(12) 1.1564(10) 0.6945(8) 0.029(3) Uani 1 1 d . . . H13 H 1.1928 1.2120 0.7138 0.035 Uiso 1 1 calc R . . C14 C 1.0662(13) 1.1516(11) 0.6206(8) 0.031(3) Uani 1 1 d . . . H14 H 1.1158 1.2034 0.5889 0.037 Uiso 1 1 calc R . . C15 C 0.9438(13) 1.0693(10) 0.5901(8) 0.025(3) Uani 1 1 d . . . H15 H 0.9107 1.0674 0.5390 0.031 Uiso 1 1 calc R . . C16 C 0.8728(11) 0.9901(9) 0.6387(6) 0.016(2) Uani 1 1 d . . . C17 C 0.7446(12) 0.9027(9) 0.6033(7) 0.021(3) Uani 1 1 d . . . C18 C 0.6250(13) 0.5787(11) 0.6815(7) 0.027(3) Uani 1 1 d . . . H18A H 0.7243 0.6181 0.6895 0.040 Uiso 1 1 calc R . . H18B H 0.6192 0.4985 0.6674 0.040 Uiso 1 1 calc R . . H18C H 0.5788 0.5858 0.7276 0.040 Uiso 1 1 calc R . . C19 C 0.5527(13) 0.6304(10) 0.6202(7) 0.024(3) Uani 1 1 d . . . C20 C 0.4267(12) 0.5679(10) 0.5722(7) 0.022(3) Uani 1 1 d . . . C21 C 0.3602(13) 0.4509(10) 0.5815(7) 0.025(3) Uani 1 1 d . . . H21 H 0.3973 0.4132 0.6207 0.030 Uiso 1 1 calc R . . C22 C 0.1931(13) 0.4537(11) 0.4837(8) 0.030(3) Uani 1 1 d . . . C23 C 0.0660(15) 0.3959(13) 0.4352(9) 0.043(4) Uani 1 1 d . . . H23 H 0.0256 0.3183 0.4396 0.052 Uiso 1 1 calc R . . C24 C 0.0073(15) 0.4573(14) 0.3832(8) 0.041(4) Uani 1 1 d . . . H24 H -0.0737 0.4209 0.3516 0.049 Uiso 1 1 calc R . . C25 C 0.0656(15) 0.5722(13) 0.3764(8) 0.039(3) Uani 1 1 d . . . H25 H 0.0196 0.6120 0.3418 0.047 Uiso 1 1 calc R . . C26 C 0.1857(13) 0.6294(11) 0.4173(8) 0.031(3) Uani 1 1 d . . . H26 H 0.2247 0.7060 0.4091 0.037 Uiso 1 1 calc R . . C27 C 0.2521(12) 0.5717(9) 0.4729(7) 0.022(3) Uani 1 1 d . . . C28 C 0.7244(11) 0.9271(9) 0.8013(6) 0.016(2) Uani 1 1 d . . . C29 C 0.6606(12) 0.8449(9) 0.8510(7) 0.019(2) Uani 1 1 d . . . C30 C 0.5425(12) 0.8554(10) 0.8875(7) 0.022(3) Uani 1 1 d . . . H30 H 0.5037 0.7992 0.9195 0.026 Uiso 1 1 calc R . . C31 C 0.4795(11) 0.9498(9) 0.8772(6) 0.015(2) Uani 1 1 d . . . C32 C 0.5408(12) 1.0348(10) 0.8267(7) 0.022(3) Uani 1 1 d . . . C33 C 0.6564(12) 1.0194(10) 0.7903(7) 0.023(3) Uani 1 1 d . . . H33 H 0.6926 1.0731 0.7560 0.028 Uiso 1 1 calc R . . C34 C 0.4760(14) 1.1388(11) 0.8148(8) 0.031(3) Uani 1 1 d U . . H34A H 0.5253 1.1840 0.7772 0.047 Uiso 1 1 calc R . . H34B H 0.4857 1.1850 0.8621 0.047 Uiso 1 1 calc R . . H34C H 0.3758 1.1139 0.7976 0.047 Uiso 1 1 calc R . . C35 C 0.2951(12) 0.8796(10) 0.9654(7) 0.025(3) Uani 1 1 d . . . H35A H 0.3619 0.8798 1.0097 0.030 Uiso 1 1 calc R . . H35B H 0.2733 0.8026 0.9402 0.030 Uiso 1 1 calc R . . C36 C 0.1581(14) 0.9087(12) 0.9909(8) 0.036(3) Uani 1 1 d . . . H36A H 0.1812 0.9787 1.0233 0.053 Uiso 1 1 calc R . . H36B H 0.1088 0.8469 1.0186 0.053 Uiso 1 1 calc R . . H36C H 0.0971 0.9188 0.9471 0.053 Uiso 1 1 calc R . . C37 C 0.2965(18) 0.8969(14) 0.6061(9) 0.047(4) Uani 1 1 d . . . H37A H 0.2639 0.8230 0.6260 0.071 Uiso 1 1 calc R . . H37B H 0.2189 0.9372 0.6029 0.071 Uiso 1 1 calc R . . H37C H 0.3752 0.9413 0.6393 0.071 Uiso 1 1 calc R . . Cl1 Cl 0.5019(4) 0.8068(3) 0.38488(18) 0.0370(8) Uani 1 1 d . . . N1 N 0.7130(10) 0.8064(8) 0.6384(5) 0.020(2) Uani 1 1 d . . . H1 H 0.7594 0.7912 0.6790 0.024 Uiso 1 1 calc R . . N2 N 0.5957(10) 0.7350(8) 0.6008(6) 0.022(2) Uani 1 1 d . . . N3 N 0.3744(10) 0.6253(8) 0.5172(6) 0.022(2) Uani 1 1 d . . . N4 N 0.2485(11) 0.3938(9) 0.5371(6) 0.029(2) Uani 1 1 d . . . N5 N 1.0655(11) 0.5269(9) 0.8461(6) 0.029(2) Uani 1 1 d . . . H5 H 1.1489 0.5222 0.8321 0.035 Uiso 1 1 calc R . . N6 N 0.3634(10) 0.9625(8) 0.9130(6) 0.022(2) Uani 1 1 d . . . H6 H 0.3273 1.0219 0.9048 0.027 Uiso 1 1 calc R . . O1 O 0.7139(8) 0.7491(7) 0.8631(4) 0.0208(17) Uani 1 1 d . . . O2 O 0.6775(8) 0.9213(7) 0.5415(5) 0.0247(19) Uani 1 1 d . . . O3 O 0.3426(9) 0.8811(7) 0.5331(5) 0.030(2) Uani 1 1 d . . . H3 H 0.2988 0.9120 0.4926 0.036 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 Cu1 0.0243(7) 0.0173(7) 0.0221(8) 0.0049(6) 0.0005(6) -0.0017(6) Hg1 0.0346(3) 0.0289(3) 0.0389(3) 0.0028(2) 0.0041(2) 0.0010(2) Br1 0.0282(7) 0.0294(7) 0.0514(9) -0.0016(6) 0.0063(6) 0.0084(5) Br2 0.0847(14) 0.0736(14) 0.0735(14) 0.0117(11) 0.0175(11) 0.0221(11) Br3 0.0452(9) 0.0414(9) 0.0534(10) 0.0064(7) 0.0070(7) 0.0072(7) C1 0.058(10) 0.030(8) 0.064(11) 0.011(8) 0.027(9) 0.009(7) C2 0.027(7) 0.033(7) 0.047(9) 0.026(7) 0.011(6) 0.019(6) C3 0.021(6) 0.018(6) 0.017(6) 0.004(5) -0.002(5) 0.007(5) C4 0.022(6) 0.020(6) 0.018(6) 0.003(5) 0.003(5) 0.004(5) C5 0.014(6) 0.025(6) 0.037(7) 0.012(6) 0.008(5) 0.008(5) C6 0.013(5) 0.030(7) 0.021(6) 0.007(5) 0.007(5) -0.001(5) C7 0.021(6) 0.016(6) 0.018(6) 0.001(5) -0.004(5) 0.008(5) C8 0.014(5) 0.029(7) 0.018(6) -0.003(5) -0.003(5) 0.002(5) C9 0.017(6) 0.024(6) 0.020(6) 0.003(5) 0.001(5) 0.005(5) C10 0.020(6) 0.015(6) 0.023(6) -0.003(5) 0.002(5) -0.002(5) C11 0.016(6) 0.014(5) 0.031(7) 0.003(5) 0.009(5) 0.005(4) C12 0.026(6) 0.018(6) 0.027(7) 0.013(5) -0.002(5) 0.000(5) C13 0.019(6) 0.014(6) 0.046(8) -0.009(6) -0.006(6) -0.011(5) C14 0.027(7) 0.024(7) 0.040(8) 0.012(6) 0.012(6) -0.002(5) C15 0.025(6) 0.018(6) 0.033(7) 0.009(5) 0.004(5) 0.000(5) C16 0.019(6) 0.008(5) 0.020(6) 0.002(4) 0.008(5) 0.003(4) C17 0.021(6) 0.013(6) 0.025(7) 0.002(5) 0.005(5) -0.003(5) C18 0.027(6) 0.027(7) 0.024(7) 0.009(5) 0.002(5) -0.001(5) C19 0.025(6) 0.028(7) 0.020(6) 0.003(5) 0.007(5) 0.001(5) C20 0.018(6) 0.023(6) 0.022(6) 0.004(5) 0.010(5) -0.004(5) C21 0.036(7) 0.015(6) 0.025(7) 0.001(5) 0.009(6) 0.007(5) C22 0.020(6) 0.030(7) 0.034(8) -0.007(6) 0.008(6) -0.008(5) C23 0.036(8) 0.045(9) 0.039(9) -0.008(7) 0.016(7) -0.014(7) C24 0.030(7) 0.068(11) 0.022(7) -0.023(7) -0.004(6) 0.010(7) C25 0.040(8) 0.041(8) 0.033(8) 0.000(7) -0.003(7) 0.005(7) C26 0.023(6) 0.031(7) 0.037(8) 0.000(6) 0.009(6) 0.002(5) C27 0.020(6) 0.014(6) 0.031(7) 0.002(5) 0.008(5) -0.001(5) C28 0.018(5) 0.016(5) 0.013(6) -0.004(4) 0.001(5) 0.003(4) C29 0.019(6) 0.012(5) 0.022(6) -0.005(5) 0.001(5) -0.002(4) C30 0.023(6) 0.022(6) 0.021(6) 0.010(5) -0.002(5) 0.007(5) C31 0.018(6) 0.018(6) 0.008(5) -0.006(4) 0.002(4) 0.000(4) C32 0.023(6) 0.024(6) 0.017(6) 0.000(5) -0.001(5) 0.005(5) C33 0.026(6) 0.029(7) 0.013(6) 0.005(5) 0.006(5) 0.002(5) C34 0.032(6) 0.032(6) 0.035(6) 0.014(5) 0.011(5) 0.012(5) C35 0.021(6) 0.024(6) 0.030(7) 0.006(5) 0.011(5) 0.001(5) C36 0.028(7) 0.041(8) 0.039(8) 0.001(7) 0.019(6) 0.004(6) C37 0.060(10) 0.044(9) 0.043(9) 0.006(7) 0.010(8) 0.020(8) Cl1 0.0389(18) 0.046(2) 0.0224(16) 0.0073(15) 0.0031(14) -0.0007(15) N1 0.022(5) 0.015(5) 0.019(5) 0.000(4) -0.002(4) -0.003(4) N2 0.018(5) 0.015(5) 0.029(6) 0.004(4) 0.003(4) -0.005(4) N3 0.022(5) 0.020(5) 0.022(5) -0.003(4) 0.002(4) -0.002(4) N4 0.031(6) 0.022(5) 0.031(6) -0.001(5) 0.003(5) -0.003(5) N5 0.023(5) 0.028(6) 0.040(7) 0.016(5) 0.005(5) 0.007(4) N6 0.019(5) 0.020(5) 0.029(6) 0.006(4) 0.005(4) 0.005(4) O1 0.019(4) 0.023(4) 0.024(4) 0.007(3) 0.004(3) 0.008(3) O2 0.020(4) 0.020(4) 0.029(5) 0.009(4) 0.004(4) -0.007(3) O3 0.034(5) 0.025(5) 0.033(5) 0.009(4) 0.005(4) 0.011(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 Cu1 N2 1.928(10) . ? Cu1 O2 2.013(8) . ? Cu1 N3 2.105(9) . ? Cu1 O3 2.203(8) . ? Cu1 Cl1 2.216(3) . ? Hg1 Br2 2.485(2) . ? Hg1 Br3 2.4959(16) . ? Hg1 Br1 2.6188(15) . ? Hg1 Br1 2.7764(15) 2_667 ? Br1 Hg1 2.7764(15) 2_667 ? C1 C2 1.47(2) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N5 1.455(15) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 N5 1.337(15) . ? C3 C9 1.414(16) . ? C3 C4 1.418(16) . ? C4 C6 1.350(16) . ? C4 C5 1.514(15) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C7 1.441(15) . ? C6 H6A 0.9300 . ? C7 C8 1.394(16) . ? C7 C10 1.408(15) . ? C8 O1 1.349(13) . ? C8 C9 1.393(16) . ? C9 H9 0.9300 . ? C10 C28 1.405(15) . ? C10 C11 1.504(16) . ? C11 C12 1.376(16) . ? C11 C16 1.382(16) . ? C12 C13 1.398(17) . ? C12 H12 0.9300 . ? C13 C14 1.339(19) . ? C13 H13 0.9300 . ? C14 C15 1.407(17) . ? C14 H14 0.9300 . ? C15 C16 1.404(15) . ? C15 H15 0.9300 . ? C16 C17 1.499(15) . ? C17 O2 1.275(14) . ? C17 N1 1.316(14) . ? C18 C19 1.467(17) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N2 1.294(15) . ? C19 C20 1.457(16) . ? C20 N3 1.338(15) . ? C20 C21 1.423(16) . ? C21 N4 1.314(16) . ? C21 H21 0.9300 . ? C22 N4 1.350(17) . ? C22 C27 1.422(16) . ? C22 C23 1.452(18) . ? C23 C24 1.36(2) . ? C23 H23 0.9300 . ? C24 C25 1.37(2) . ? C24 H24 0.9300 . ? C25 C26 1.339(18) . ? C25 H25 0.9300 . ? C26 C27 1.410(18) . ? C26 H26 0.9300 . ? C27 N3 1.371(15) . ? C28 C33 1.399(16) . ? C28 C29 1.415(16) . ? C29 O1 1.358(13) . ? C29 C30 1.360(16) . ? C30 C31 1.390(16) . ? C30 H30 0.9300 . ? C31 N6 1.342(14) . ? C31 C32 1.439(16) . ? C32 C33 1.353(16) . ? C32 C34 1.507(16) . ? C33 H33 0.9300 . ? C34 H34A 0.9600 . ? C34 H34B 0.9600 . ? C34 H34C 0.9600 . ? C35 N6 1.468(14) . ? C35 C36 1.510(16) . ? C35 H35A 0.9700 . ? C35 H35B 0.9700 . ? C36 H36A 0.9600 . ? C36 H36B 0.9600 . ? C36 H36C 0.9600 . ? C37 O3 1.405(17) . ? C37 H37A 0.9600 . ? C37 H37B 0.9600 . ? C37 H37C 0.9600 . ? N1 N2 1.359(13) . ? N1 H1 0.8600 . ? N5 H5 0.8600 . ? N6 H6 0.8600 . ? O3 H3 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 N2 Cu1 O2 78.4(4) . . ? N2 Cu1 N3 78.4(4) . . ? O2 Cu1 N3 156.8(4) . . ? N2 Cu1 O3 112.2(4) . . ? O2 Cu1 O3 95.2(3) . . ? N3 Cu1 O3 92.5(3) . . ? N2 Cu1 Cl1 151.8(3) . . ? O2 Cu1 Cl1 98.4(3) . . ? N3 Cu1 Cl1 102.6(3) . . ? O3 Cu1 Cl1 96.0(3) . . ? Br2 Hg1 Br3 109.77(7) . . ? Br2 Hg1 Br1 116.88(6) . . ? Br3 Hg1 Br1 119.25(5) . . ? Br2 Hg1 Br1 104.75(6) . 2_667 ? Br3 Hg1 Br1 113.35(5) . 2_667 ? Br1 Hg1 Br1 90.40(4) . 2_667 ? Hg1 Br1 Hg1 89.60(4) . 2_667 ? C2 C1 H1A 109.5 . . ? C2 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C2 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? N5 C2 C1 114.8(12) . . ? N5 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? N5 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.5 . . ? N5 C3 C9 120.0(11) . . ? N5 C3 C4 120.4(10) . . ? C9 C3 C4 119.6(10) . . ? C6 C4 C3 120.8(10) . . ? C6 C4 C5 120.6(10) . . ? C3 C4 C5 118.7(10) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 C7 121.7(11) . . ? C4 C6 H6A 119.2 . . ? C7 C6 H6A 119.2 . . ? C8 C7 C10 119.4(10) . . ? C8 C7 C6 115.8(10) . . ? C10 C7 C6 124.6(11) . . ? O1 C8 C9 114.6(10) . . ? O1 C8 C7 121.0(10) . . ? C9 C8 C7 124.3(10) . . ? C8 C9 C3 117.4(11) . . ? C8 C9 H9 121.3 . . ? C3 C9 H9 121.3 . . ? C28 C10 C7 118.6(10) . . ? C28 C10 C11 121.0(10) . . ? C7 C10 C11 120.2(10) . . ? C12 C11 C16 119.5(11) . . ? C12 C11 C10 117.7(11) . . ? C16 C11 C10 122.8(10) . . ? C11 C12 C13 120.6(11) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 120.2(11) . . ? C14 C13 H13 119.9 . . ? C12 C13 H13 119.9 . . ? C13 C14 C15 121.0(12) . . ? C13 C14 H14 119.5 . . ? C15 C14 H14 119.5 . . ? C16 C15 C14 118.5(12) . . ? C16 C15 H15 120.7 . . ? C14 C15 H15 120.7 . . ? C11 C16 C15 120.2(10) . . ? C11 C16 C17 123.2(10) . . ? C15 C16 C17 116.6(10) . . ? O2 C17 N1 124.0(10) . . ? O2 C17 C16 120.6(10) . . ? N1 C17 C16 115.4(10) . . ? C19 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C19 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N2 C19 C20 112.2(10) . . ? N2 C19 C18 124.2(11) . . ? C20 C19 C18 123.6(11) . . ? N3 C20 C21 120.1(11) . . ? N3 C20 C19 117.0(10) . . ? C21 C20 C19 122.9(11) . . ? N4 C21 C20 122.8(11) . . ? N4 C21 H21 118.6 . . ? C20 C21 H21 118.6 . . ? N4 C22 C27 123.3(11) . . ? N4 C22 C23 118.8(12) . . ? C27 C22 C23 118.0(13) . . ? C24 C23 C22 118.8(14) . . ? C24 C23 H23 120.6 . . ? C22 C23 H23 120.6 . . ? C23 C24 C25 121.1(13) . . ? C23 C24 H24 119.4 . . ? C25 C24 H24 119.4 . . ? C26 C25 C24 123.1(14) . . ? C26 C25 H25 118.5 . . ? C24 C25 H25 118.5 . . ? C25 C26 C27 119.0(13) . . ? C25 C26 H26 120.5 . . ? C27 C26 H26 120.5 . . ? N3 C27 C26 122.1(10) . . ? N3 C27 C22 118.0(11) . . ? C26 C27 C22 120.0(11) . . ? C33 C28 C10 125.6(11) . . ? C33 C28 C29 115.9(10) . . ? C10 C28 C29 118.5(10) . . ? O1 C29 C30 116.5(10) . . ? O1 C29 C28 120.8(10) . . ? C30 C29 C28 122.6(10) . . ? C29 C30 C31 120.3(11) . . ? C29 C30 H30 119.9 . . ? C31 C30 H30 119.9 . . ? N6 C31 C30 121.4(10) . . ? N6 C31 C32 119.9(10) . . ? C30 C31 C32 118.7(10) . . ? C33 C32 C31 118.9(11) . . ? C33 C32 C34 121.0(11) . . ? C31 C32 C34 120.1(10) . . ? C32 C33 C28 123.5(11) . . ? C32 C33 H33 118.3 . . ? C28 C33 H33 118.3 . . ? C32 C34 H34A 109.5 . . ? C32 C34 H34B 109.5 . . ? H34A C34 H34B 109.5 . . ? C32 C34 H34C 109.5 . . ? H34A C34 H34C 109.5 . . ? H34B C34 H34C 109.5 . . ? N6 C35 C36 111.7(10) . . ? N6 C35 H35A 109.3 . . ? C36 C35 H35A 109.3 . . ? N6 C35 H35B 109.3 . . ? C36 C35 H35B 109.3 . . ? H35A C35 H35B 107.9 . . ? C35 C36 H36A 109.5 . . ? C35 C36 H36B 109.5 . . ? H36A C36 H36B 109.5 . . ? C35 C36 H36C 109.5 . . ? H36A C36 H36C 109.5 . . ? H36B C36 H36C 109.5 . . ? O3 C37 H37A 109.5 . . ? O3 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O3 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C17 N1 N2 109.5(9) . . ? C17 N1 H1 125.2 . . ? N2 N1 H1 125.2 . . ? C19 N2 N1 120.8(10) . . ? C19 N2 Cu1 121.0(8) . . ? N1 N2 Cu1 117.6(7) . . ? C20 N3 C27 119.0(10) . . ? C20 N3 Cu1 110.4(7) . . ? C27 N3 Cu1 130.4(8) . . ? C21 N4 C22 116.6(10) . . ? C3 N5 C2 125.7(10) . . ? C3 N5 H5 117.2 . . ? C2 N5 H5 117.2 . . ? C31 N6 C35 123.0(10) . . ? C31 N6 H6 118.5 . . ? C35 N6 H6 118.5 . . ? C8 O1 C29 120.5(9) . . ? C17 O2 Cu1 110.4(7) . . ? C37 O3 Cu1 123.5(8) . . ? C37 O3 H3 118.2 . . ? Cu1 O3 H3 118.2 . . ? 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 Br2 Hg1 Br1 Hg1 106.79(7) . . . 2_667 ? Br3 Hg1 Br1 Hg1 -117.27(6) . . . 2_667 ? Br1 Hg1 Br1 Hg1 0.0 2_667 . . 2_667 ? N5 C3 C4 C6 173.9(11) . . . . ? C9 C3 C4 C6 -6.5(17) . . . . ? N5 C3 C4 C5 -5.7(17) . . . . ? C9 C3 C4 C5 173.8(11) . . . . ? C3 C4 C6 C7 6.0(18) . . . . ? C5 C4 C6 C7 -174.4(11) . . . . ? C4 C6 C7 C8 -1.0(17) . . . . ? C4 C6 C7 C10 -176.2(11) . . . . ? C10 C7 C8 O1 -5.4(16) . . . . ? C6 C7 C8 O1 179.1(10) . . . . ? C10 C7 C8 C9 171.9(11) . . . . ? C6 C7 C8 C9 -3.6(17) . . . . ? O1 C8 C9 C3 -179.6(10) . . . . ? C7 C8 C9 C3 3.0(17) . . . . ? N5 C3 C9 C8 -178.4(11) . . . . ? C4 C3 C9 C8 2.1(16) . . . . ? C8 C7 C10 C28 10.2(16) . . . . ? C6 C7 C10 C28 -174.8(11) . . . . ? C8 C7 C10 C11 -173.2(10) . . . . ? C6 C7 C10 C11 1.8(17) . . . . ? C28 C10 C11 C12 100.7(13) . . . . ? C7 C10 C11 C12 -75.8(14) . . . . ? C28 C10 C11 C16 -79.2(14) . . . . ? C7 C10 C11 C16 104.3(13) . . . . ? C16 C11 C12 C13 -1.1(17) . . . . ? C10 C11 C12 C13 179.0(10) . . . . ? C11 C12 C13 C14 0.5(19) . . . . ? C12 C13 C14 C15 0.8(19) . . . . ? C13 C14 C15 C16 -1.5(19) . . . . ? C12 C11 C16 C15 0.4(16) . . . . ? C10 C11 C16 C15 -179.7(10) . . . . ? C12 C11 C16 C17 -179.8(10) . . . . ? C10 C11 C16 C17 0.1(16) . . . . ? C14 C15 C16 C11 0.9(17) . . . . ? C14 C15 C16 C17 -178.9(10) . . . . ? C11 C16 C17 O2 158.8(11) . . . . ? C15 C16 C17 O2 -21.4(16) . . . . ? C11 C16 C17 N1 -24.3(16) . . . . ? C15 C16 C17 N1 155.5(10) . . . . ? N2 C19 C20 N3 -0.5(15) . . . . ? C18 C19 C20 N3 -178.3(11) . . . . ? N2 C19 C20 C21 179.2(11) . . . . ? C18 C19 C20 C21 1.4(18) . . . . ? N3 C20 C21 N4 1.2(18) . . . . ? C19 C20 C21 N4 -178.4(11) . . . . ? N4 C22 C23 C24 177.9(12) . . . . ? C27 C22 C23 C24 -1.6(19) . . . . ? C22 C23 C24 C25 0(2) . . . . ? C23 C24 C25 C26 3(2) . . . . ? C24 C25 C26 C27 -3(2) . . . . ? C25 C26 C27 N3 -179.4(12) . . . . ? C25 C26 C27 C22 1.3(19) . . . . ? N4 C22 C27 N3 2.4(18) . . . . ? C23 C22 C27 N3 -178.1(11) . . . . ? N4 C22 C27 C26 -178.3(12) . . . . ? C23 C22 C27 C26 1.2(18) . . . . ? C7 C10 C28 C33 172.8(11) . . . . ? C11 C10 C28 C33 -3.8(18) . . . . ? C7 C10 C28 C29 -5.1(16) . . . . ? C11 C10 C28 C29 178.3(10) . . . . ? C33 C28 C29 O1 177.0(10) . . . . ? C10 C28 C29 O1 -4.9(16) . . . . ? C33 C28 C29 C30 -1.6(16) . . . . ? C10 C28 C29 C30 176.5(11) . . . . ? O1 C29 C30 C31 -178.9(10) . . . . ? C28 C29 C30 C31 -0.2(17) . . . . ? C29 C30 C31 N6 -179.6(11) . . . . ? C29 C30 C31 C32 0.7(16) . . . . ? N6 C31 C32 C33 -178.9(11) . . . . ? C30 C31 C32 C33 0.7(16) . . . . ? N6 C31 C32 C34 0.9(16) . . . . ? C30 C31 C32 C34 -179.4(11) . . . . ? C31 C32 C33 C28 -2.8(18) . . . . ? C34 C32 C33 C28 177.4(11) . . . . ? C10 C28 C33 C32 -174.8(11) . . . . ? C29 C28 C33 C32 3.1(17) . . . . ? O2 C17 N1 N2 -3.0(16) . . . . ? C16 C17 N1 N2 -179.9(9) . . . . ? C20 C19 N2 N1 -179.2(10) . . . . ? C18 C19 N2 N1 -1.4(18) . . . . ? C20 C19 N2 Cu1 -8.0(14) . . . . ? C18 C19 N2 Cu1 169.8(9) . . . . ? C17 N1 N2 C19 173.1(11) . . . . ? C17 N1 N2 Cu1 1.6(12) . . . . ? O2 Cu1 N2 C19 -171.7(10) . . . . ? N3 Cu1 N2 C19 9.4(9) . . . . ? O3 Cu1 N2 C19 97.3(9) . . . . ? Cl1 Cu1 N2 C19 -85.6(11) . . . . ? O2 Cu1 N2 N1 -0.2(8) . . . . ? N3 Cu1 N2 N1 -179.1(9) . . . . ? O3 Cu1 N2 N1 -91.2(8) . . . . ? Cl1 Cu1 N2 N1 85.9(10) . . . . ? C21 C20 N3 C27 3.3(16) . . . . ? C19 C20 N3 C27 -177.0(10) . . . . ? C21 C20 N3 Cu1 -172.4(8) . . . . ? C19 C20 N3 Cu1 7.3(13) . . . . ? C26 C27 N3 C20 175.8(11) . . . . ? C22 C27 N3 C20 -4.9(16) . . . . ? C26 C27 N3 Cu1 -9.5(17) . . . . ? C22 C27 N3 Cu1 169.7(8) . . . . ? N2 Cu1 N3 C20 -8.6(8) . . . . ? O2 Cu1 N3 C20 -11.4(14) . . . . ? O3 Cu1 N3 C20 -120.7(8) . . . . ? Cl1 Cu1 N3 C20 142.6(7) . . . . ? N2 Cu1 N3 C27 176.4(11) . . . . ? O2 Cu1 N3 C27 173.6(9) . . . . ? O3 Cu1 N3 C27 64.3(10) . . . . ? Cl1 Cu1 N3 C27 -32.4(10) . . . . ? C20 C21 N4 C22 -3.7(17) . . . . ? C27 C22 N4 C21 1.9(18) . . . . ? C23 C22 N4 C21 -177.5(12) . . . . ? C9 C3 N5 C2 3.0(19) . . . . ? C4 C3 N5 C2 -177.4(12) . . . . ? C1 C2 N5 C3 81.7(17) . . . . ? C30 C31 N6 C35 0.5(17) . . . . ? C32 C31 N6 C35 -179.9(10) . . . . ? C36 C35 N6 C31 -174.1(11) . . . . ? C9 C8 O1 C29 177.7(10) . . . . ? C7 C8 O1 C29 -4.8(16) . . . . ? C30 C29 O1 C8 -171.3(10) . . . . ? C28 C29 O1 C8 10.1(15) . . . . ? N1 C17 O2 Cu1 2.9(14) . . . . ? C16 C17 O2 Cu1 179.5(8) . . . . ? N2 Cu1 O2 C17 -1.3(8) . . . . ? N3 Cu1 O2 C17 1.5(14) . . . . ? O3 Cu1 O2 C17 110.3(8) . . . . ? Cl1 Cu1 O2 C17 -152.8(7) . . . . ? N2 Cu1 O3 C37 -2.4(11) . . . . ? O2 Cu1 O3 C37 -82.0(10) . . . . ? N3 Cu1 O3 C37 76.1(11) . . . . ? Cl1 Cu1 O3 C37 179.0(10) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O3 H3 O2 0.93 2.07 2.780(11) 132.2 2_676 N5 H5 Br2 0.86 2.63 3.446(11) 159.5 1_655 N6 H6 Br3 0.86 2.80 3.590(10) 153.7 1_565 _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 2.137 _refine_diff_density_min -3.039 _refine_diff_density_rms 0.233