# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Dalton Trans.' _journal_coden_cambridge 0222 _publ_contact_author_name 'Frederic-Georges Fontaine' _publ_contact_author_address ; D\'epartement de Chimie Pavillon Alexandre-Vachon, Local 2257 Universit\'e Laval Qu\'ebec, Canada G1K 7P4 ; _publ_contact_author_phone '418 656-5140' _publ_contact_author_fax 418-656-7916 _publ_contact_author_email frederic.fontaine@chm.ulaval.ca _publ_requested_category FM _publ_requested_coeditor_name ? _publ_contact_letter ; Please consider this CIF submission for publication in Acta Crystallographica Section C. All authors have seen and approved of this submission. The CIF has passed the Chester CHECKCIF routines and gives a satisfactory PRINTCIF file. When I hear back from you by e-mail with your reference number I will fax and air-mail a formal Letter of Submission and a signed Copyright Transfer Form. I will then ftp the Artwork and Structure Factor Listing to you (as Postscript and ASCII files respectively). ; #============================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) #============================================================================== _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #============================================================================== # 3. TITLE AND AUTHOR LIST #============================================================================== _publ_section_title ; Title ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address G.Murtaza ; D\'epartement de Chimie Pavillon Alexandre-Vachon, Local 2257 Universit\'e Laval Qu\'ebec, Canada G1K 7P4 ; A.Badshah '' M.Said '' H.Khan '' A.Khan '' S.Khan '' S.Siddiq '' M.Choudhary '' "Fr\'ed\'eric-Georges Fontaine" '' J.Boudreau '' #============================================================================== # 4. TEXT #============================================================================== _publ_section_abstract ; See Text ; _publ_section_comment ; See Text ; _publ_section_exptl_prep ; See text ; _publ_section_exptl_refinement ; The structure was solved by direct method with ShelxS-97. All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters while hydrogen atoms were placed in idealized position. ; _publ_section_references ; Bruker (2005a). XPREP. Version 2005/2. Bruker AXS Inc., Madison, WI, USA. Bruker (2005b). APEX 2. Version 1.0.18. Bruker AXS Inc., Madison, WI, USA. Bruker (2003). SAINT. Version 7.23A. Bruker AXS Inc., Madison, WI, USA. Bruker (2001). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, WI, USA. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Flack, H. D. and Schwarzenbach, D. (1988). Acta Cryst. A44, 499-506. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of G\"ottingen, Germany. Sheldrick, G. M. (2004). SADABS. Version 2004/1. Bruker AXS Inc., Madison, WI, USA. Sheldrick, G. M. (2002). TWINABS. Version 1.05. Bruker AXS Inc., Madison, WI, USA. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. University of Utrecht, Utrecht, The Netherlands. ; _publ_section_figure_captions ; See text ; _publ_section_table_legends ; See text ; _publ_section_acknowledgements ; See text ; data_bad005 _database_code_depnum_ccdc_archive 'CCDC 816341' #TrackingRef '- Compound_1a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C34 H34 Cl2 Cu N6 O2' _chemical_formula_weight 693.11 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 19.020(8) _cell_length_b 14.289(6) _cell_length_c 18.525(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.193(6) _cell_angle_gamma 90.00 _cell_volume 5005(4) _cell_formula_units_Z 6 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 8414 _cell_measurement_theta_min 2.16 _cell_measurement_theta_max 23.49 _exptl_crystal_description Block _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.380 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2154 _exptl_absorpt_coefficient_mu 0.855 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8342 _exptl_absorpt_correction_T_max 0.9194 _exptl_absorpt_process_details 'XPREP (Bruker, 2005a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 60387 _diffrn_reflns_av_R_equivalents 0.1093 _diffrn_reflns_av_sigmaI/netI 0.0939 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.79 _diffrn_reflns_theta_max 28.28 _reflns_number_total 12034 _reflns_number_gt 7243 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2005b)' _computing_cell_refinement 'APEX 2 (Bruker, 2005b)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0730P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 12034 _refine_ls_number_parameters 680 _refine_ls_number_restraints 72 _refine_ls_R_factor_all 0.1047 _refine_ls_R_factor_gt 0.0587 _refine_ls_wR_factor_ref 0.1673 _refine_ls_wR_factor_gt 0.1428 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _refine_ls_shift/su_max 0.005 _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 0.00904(17) 0.3866(2) 0.31574(16) 0.0344(7) Uani 1 1 d . . . C2 C -0.05458(18) 0.3798(2) 0.27230(18) 0.0423(8) Uani 1 1 d . . . H2 H -0.0551 0.3848 0.2211 0.051 Uiso 1 1 calc R . . C3 C -0.11696(19) 0.3658(3) 0.3016(2) 0.0496(9) Uani 1 1 d . . . H3 H -0.1602 0.3622 0.2709 0.060 Uiso 1 1 calc R . . C4 C -0.1166(2) 0.3571(3) 0.3760(2) 0.0523(9) Uani 1 1 d . . . H4 H -0.1595 0.3460 0.3966 0.063 Uiso 1 1 calc R . . C5 C -0.0540(2) 0.3646(3) 0.42003(19) 0.0506(9) Uani 1 1 d . . . H5 H -0.0538 0.3595 0.4712 0.061 Uiso 1 1 calc R . . C6 C 0.00857(19) 0.3793(2) 0.39075(17) 0.0413(8) Uani 1 1 d . . . H6 H 0.0516 0.3845 0.4217 0.050 Uiso 1 1 calc R . . C7 C 0.07581(17) 0.4029(2) 0.28272(16) 0.0349(7) Uani 1 1 d . . . C8 C 0.19435(17) 0.4500(2) 0.30599(17) 0.0377(7) Uani 1 1 d . . . Cl1A Cl 0.23791(12) 0.66020(14) 0.24120(12) 0.0793(6) Uani 0.60 1 d P A 1 C9 C 0.2799(7) 0.4822(7) 0.2236(7) 0.034(2) Uani 0.60 1 d PU A 1 C10 C 0.3009(4) 0.5769(7) 0.2248(5) 0.044(2) Uani 0.60 1 d PU A 1 C11 C 0.3674(6) 0.6116(9) 0.2133(6) 0.056(3) Uani 0.60 1 d PU A 1 H11 H 0.3799 0.6759 0.2172 0.068 Uiso 0.60 1 calc PR A 1 C12 C 0.4132(5) 0.5416(9) 0.1955(5) 0.060(2) Uani 0.60 1 d PU A 1 H12 H 0.4591 0.5589 0.1846 0.071 Uiso 0.60 1 calc PR A 1 C13 C 0.3941(4) 0.4432(7) 0.1929(5) 0.057(2) Uani 0.60 1 d PU A 1 H13 H 0.4281 0.3982 0.1818 0.068 Uiso 0.60 1 calc PR A 1 C14 C 0.3289(6) 0.4138(7) 0.2059(6) 0.049(2) Uani 0.60 1 d PU A 1 H14 H 0.3166 0.3494 0.2033 0.058 Uiso 0.60 1 calc PR A 1 Cl1B Cl 0.3025(2) 0.3384(3) 0.18308(17) 0.0948(12) Uani 0.40 1 d P A 2 C9B C 0.2693(10) 0.5122(11) 0.2295(11) 0.036(4) Uani 0.40 1 d PU A 2 C10B C 0.3210(10) 0.4559(13) 0.2018(9) 0.058(4) Uani 0.40 1 d PU A 2 C11B C 0.3909(10) 0.4964(15) 0.1882(10) 0.079(5) Uani 0.40 1 d PU A 2 H11B H 0.4296 0.4640 0.1715 0.094 Uiso 0.40 1 calc PR A 2 C12B C 0.3879(12) 0.5849(15) 0.2041(11) 0.068(6) Uani 0.40 1 d PU A 2 H12B H 0.4297 0.6159 0.1933 0.082 Uiso 0.40 1 calc PR A 2 C13B C 0.3427(9) 0.6471(13) 0.2315(9) 0.091(5) Uani 0.40 1 d PU A 2 H13B H 0.3527 0.7112 0.2416 0.109 Uiso 0.40 1 calc PR A 2 C14B C 0.2804(8) 0.6021(11) 0.2423(8) 0.058(4) Uani 0.40 1 d PU A 2 H14B H 0.2436 0.6378 0.2597 0.069 Uiso 0.40 1 calc PR A 2 C15 C 0.23875(18) 0.4540(3) 0.43798(17) 0.0451(8) Uani 1 1 d . A . H15 H 0.2138 0.3935 0.4446 0.054 Uiso 1 1 calc R . . C16 C 0.3119(2) 0.4477(3) 0.4786(2) 0.0654(12) Uani 1 1 d . . . H16A H 0.3385 0.3975 0.4578 0.098 Uiso 1 1 calc R . . H16B H 0.3081 0.4343 0.5299 0.098 Uiso 1 1 calc R . . H16C H 0.3367 0.5073 0.4744 0.098 Uiso 1 1 calc R . . C17 C 0.1962(2) 0.5317(3) 0.4676(2) 0.0719(13) Uani 1 1 d . . . H17A H 0.2231 0.5902 0.4684 0.108 Uiso 1 1 calc R . . H17B H 0.1865 0.5159 0.5170 0.108 Uiso 1 1 calc R . . H17C H 0.1515 0.5393 0.4366 0.108 Uiso 1 1 calc R . . C21 C 0.21790(17) 0.5939(2) -0.00931(18) 0.0388(7) Uani 1 1 d . . . C22 C 0.21106(19) 0.6092(3) -0.08275(19) 0.0486(9) Uani 1 1 d . . . H22 H 0.1771 0.5745 -0.1132 0.058 Uiso 1 1 calc R . . C23 C 0.2529(2) 0.6743(3) -0.1132(2) 0.0578(10) Uani 1 1 d . . . H23 H 0.2470 0.6843 -0.1642 0.069 Uiso 1 1 calc R . . C24 C 0.3020(2) 0.7239(3) -0.0712(2) 0.0606(11) Uani 1 1 d . . . H24 H 0.3305 0.7689 -0.0923 0.073 Uiso 1 1 calc R . . C25 C 0.3103(3) 0.7086(4) 0.0016(3) 0.0854(16) Uani 1 1 d . . . H25 H 0.3451 0.7427 0.0313 0.102 Uiso 1 1 calc R . . C26 C 0.2686(2) 0.6440(3) 0.0331(2) 0.0740(14) Uani 1 1 d . . . H26 H 0.2750 0.6343 0.0841 0.089 Uiso 1 1 calc R . . C27 C 0.17488(16) 0.5220(2) 0.02440(17) 0.0355(7) Uani 1 1 d . A . C28 C 0.08362(16) 0.4117(2) 0.00170(17) 0.0340(7) Uani 1 1 d . A . C29 C 0.04620(18) 0.2960(2) 0.08183(16) 0.0365(7) Uani 1 1 d . A . C30 C 0.08031(19) 0.2121(2) 0.09869(19) 0.0461(8) Uani 1 1 d . . . C31 C 0.0430(2) 0.1340(3) 0.1190(2) 0.0531(10) Uani 1 1 d . . . H31 H 0.0669 0.0765 0.1297 0.064 Uiso 1 1 calc R . . C32 C -0.0279(2) 0.1406(3) 0.12355(19) 0.0513(10) Uani 1 1 d . . . H32 H -0.0531 0.0882 0.1390 0.062 Uiso 1 1 calc R . . C33 C -0.06295(19) 0.2227(3) 0.10576(18) 0.0484(9) Uani 1 1 d . . . H33 H -0.1126 0.2264 0.1078 0.058 Uiso 1 1 calc R . . C34 C -0.02628(18) 0.3007(2) 0.08477(18) 0.0410(8) Uani 1 1 d . . . H34 H -0.0510 0.3573 0.0724 0.049 Uiso 1 1 calc R . . C35 C 0.03330(18) 0.4071(2) -0.12826(17) 0.0405(8) Uani 1 1 d . A . H35 H 0.0338 0.4770 -0.1275 0.049 Uiso 1 1 calc R . . C36 C 0.0929(2) 0.3734(3) -0.1695(2) 0.0594(11) Uani 1 1 d . . . H36A H 0.1381 0.3956 -0.1451 0.089 Uiso 1 1 calc R . . H36B H 0.0863 0.3979 -0.2191 0.089 Uiso 1 1 calc R . . H36C H 0.0929 0.3048 -0.1708 0.089 Uiso 1 1 calc R . . C37 C -0.03769(18) 0.3747(3) -0.16440(19) 0.0483(9) Uani 1 1 d . . . H37A H -0.0381 0.3062 -0.1677 0.072 Uiso 1 1 calc R . . H37B H -0.0458 0.4015 -0.2133 0.072 Uiso 1 1 calc R . . H37C H -0.0751 0.3954 -0.1356 0.072 Uiso 1 1 calc R . . C41 C 0.61877(17) 0.4434(2) 0.19869(17) 0.0399(8) Uani 1 1 d . . . C42 C 0.66994(19) 0.5111(3) 0.1968(2) 0.0501(9) Uani 1 1 d . . . H42 H 0.6722 0.5470 0.1539 0.060 Uiso 1 1 calc R . . C43 C 0.7181(2) 0.5273(3) 0.2569(2) 0.0579(10) Uani 1 1 d . . . H43 H 0.7538 0.5736 0.2549 0.070 Uiso 1 1 calc R . . C44 C 0.7145(2) 0.4769(3) 0.3191(2) 0.0638(12) Uani 1 1 d . . . H44 H 0.7476 0.4877 0.3604 0.077 Uiso 1 1 calc R . . C45 C 0.6630(3) 0.4111(3) 0.3213(2) 0.0746(13) Uani 1 1 d . . . H45 H 0.6599 0.3770 0.3649 0.090 Uiso 1 1 calc R . . C46 C 0.6146(2) 0.3929(3) 0.2608(2) 0.0569(10) Uani 1 1 d . . . H46 H 0.5794 0.3461 0.2628 0.068 Uiso 1 1 calc R . . C47 C 0.56882(17) 0.4256(2) 0.13162(18) 0.0393(8) Uani 1 1 d . . . C48 C 0.48844(17) 0.3201(2) 0.07257(18) 0.0403(8) Uani 1 1 d . . . C49 C 0.40283(18) 0.3407(2) -0.02617(18) 0.0437(8) Uani 1 1 d . . . C50 C 0.41154(19) 0.2872(3) -0.0872(2) 0.0487(9) Uani 1 1 d . . . C51 C 0.3530(2) 0.2542(3) -0.1325(2) 0.0593(11) Uani 1 1 d . . . H51 H 0.3596 0.2180 -0.1742 0.071 Uiso 1 1 calc R . . C52 C 0.2866(2) 0.2745(3) -0.1163(2) 0.0595(11) Uani 1 1 d . . . H52 H 0.2468 0.2526 -0.1471 0.071 Uiso 1 1 calc R . . C53 C 0.2765(2) 0.3258(3) -0.0563(2) 0.0621(11) Uani 1 1 d . . . H53 H 0.2297 0.3380 -0.0454 0.075 Uiso 1 1 calc R . . C54 C 0.33350(18) 0.3606(3) -0.0106(2) 0.0527(10) Uani 1 1 d . . . H54 H 0.3257 0.3974 0.0305 0.063 Uiso 1 1 calc R . . C55 C 0.4895(2) 0.1623(3) 0.1322(2) 0.0519(9) Uani 1 1 d . . . H55 H 0.5351 0.1840 0.1588 0.062 Uiso 1 1 calc R . . C56 C 0.5014(3) 0.0692(4) 0.0972(3) 0.107(2) Uani 1 1 d . . . H56A H 0.4583 0.0503 0.0670 0.160 Uiso 1 1 calc R . . H56B H 0.5133 0.0220 0.1350 0.160 Uiso 1 1 calc R . . H56C H 0.5404 0.0747 0.0669 0.160 Uiso 1 1 calc R . . C57 C 0.4361(3) 0.1553(4) 0.1842(3) 0.0964(18) Uani 1 1 d . . . H57A H 0.4299 0.2167 0.2062 0.145 Uiso 1 1 calc R . . H57B H 0.4520 0.1100 0.2222 0.145 Uiso 1 1 calc R . . H57C H 0.3910 0.1346 0.1586 0.145 Uiso 1 1 calc R . . Cl21 Cl 0.17096(6) 0.20334(8) 0.09548(8) 0.0825(4) Uani 1 1 d . . . Cl61 Cl 0.49574(6) 0.25983(10) -0.10723(6) 0.0793(4) Uani 1 1 d . . . Cu1 Cu 0.141579(19) 0.43157(3) 0.152773(19) 0.03392(12) Uani 1 1 d . A . Cu2 Cu 0.5000 0.5000 0.0000 0.04205(17) Uani 1 2 d S . . N1 N 0.13157(14) 0.42517(19) 0.32832(14) 0.0403(6) Uani 1 1 d . . . N2 N 0.20732(14) 0.4615(2) 0.23741(14) 0.0430(7) Uani 1 1 d . . . N3 N 0.24595(14) 0.4654(2) 0.36058(14) 0.0450(7) Uani 1 1 d . . . H1 H 0.2873 0.4837 0.3487 0.054 Uiso 1 1 calc R A . N21 N 0.12212(14) 0.48568(18) -0.01820(14) 0.0364(6) Uani 1 1 d . . . N22 N 0.08676(14) 0.37720(18) 0.06888(13) 0.0349(6) Uani 1 1 d . . . N23 N 0.04192(15) 0.37296(19) -0.05338(13) 0.0413(7) Uani 1 1 d . . . H21 H 0.0178 0.3228 -0.0436 0.050 Uiso 1 1 calc R A . N41 N 0.53797(14) 0.3437(2) 0.12813(14) 0.0418(7) Uani 1 1 d . . . N42 N 0.46112(14) 0.37658(19) 0.01976(15) 0.0431(7) Uani 1 1 d . . . N43 N 0.46604(16) 0.2311(2) 0.07623(16) 0.0534(8) Uani 1 1 d . . . H41 H 0.4340 0.2123 0.0414 0.064 Uiso 1 1 calc R . . O1 O 0.07210(12) 0.39406(17) 0.21431(11) 0.0430(6) Uani 1 1 d . . . O21 O 0.19408(12) 0.50330(18) 0.09060(12) 0.0501(6) Uani 1 1 d . . . O41 O 0.56229(14) 0.49293(18) 0.08663(14) 0.0583(7) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0477(18) 0.0300(16) 0.0258(15) -0.0002(13) 0.0054(14) 0.0004(13) C2 0.052(2) 0.047(2) 0.0277(17) -0.0001(15) 0.0016(15) 0.0001(16) C3 0.0433(19) 0.060(2) 0.046(2) -0.0014(18) 0.0061(17) 0.0004(17) C4 0.050(2) 0.060(2) 0.050(2) -0.0014(19) 0.0213(19) 0.0031(18) C5 0.067(2) 0.056(2) 0.0298(18) 0.0007(17) 0.0132(18) 0.0000(19) C6 0.054(2) 0.0416(19) 0.0277(17) -0.0002(15) 0.0020(15) 0.0010(16) C7 0.0478(18) 0.0345(17) 0.0222(15) 0.0003(13) 0.0025(14) 0.0019(14) C8 0.0426(18) 0.0435(19) 0.0255(16) -0.0033(14) -0.0035(14) -0.0027(14) Cl1A 0.0967(14) 0.0488(10) 0.0915(15) -0.0170(10) 0.0059(12) 0.0017(10) C9 0.039(5) 0.042(5) 0.022(4) -0.005(4) 0.001(3) 0.003(4) C10 0.037(4) 0.050(5) 0.045(4) -0.006(3) 0.003(3) -0.002(3) C11 0.053(6) 0.063(6) 0.051(5) -0.005(4) -0.001(4) 0.006(5) C12 0.047(4) 0.082(6) 0.049(4) 0.001(5) 0.001(4) -0.015(4) C13 0.045(4) 0.074(5) 0.053(4) 0.000(4) 0.007(3) 0.004(4) C14 0.046(4) 0.062(5) 0.038(4) 0.013(5) 0.006(3) 0.003(4) Cl1B 0.112(3) 0.114(3) 0.0575(18) -0.0074(18) 0.0050(18) 0.060(2) C9B 0.041(7) 0.045(8) 0.021(5) 0.000(6) 0.000(5) -0.002(6) C10B 0.052(7) 0.087(9) 0.035(6) -0.001(7) -0.001(5) -0.007(7) C11B 0.079(8) 0.094(9) 0.066(8) -0.002(8) 0.019(6) -0.007(8) C12B 0.073(10) 0.072(10) 0.061(8) 0.004(7) 0.010(7) 0.007(7) C13B 0.092(8) 0.100(9) 0.077(8) 0.011(7) -0.006(7) -0.036(7) C14B 0.050(7) 0.062(8) 0.059(7) 0.004(6) -0.005(5) -0.006(6) C15 0.0470(19) 0.062(2) 0.0241(16) -0.0035(16) -0.0046(15) 0.0080(17) C16 0.060(2) 0.098(4) 0.034(2) -0.011(2) -0.0142(18) 0.016(2) C17 0.073(3) 0.090(3) 0.047(2) -0.024(2) -0.015(2) 0.029(3) C21 0.0437(18) 0.0402(18) 0.0326(17) 0.0067(14) 0.0045(15) -0.0023(14) C22 0.055(2) 0.053(2) 0.0373(19) 0.0055(17) 0.0024(17) -0.0070(17) C23 0.067(2) 0.065(3) 0.042(2) 0.0150(19) 0.0114(19) -0.012(2) C24 0.064(2) 0.059(3) 0.061(3) 0.013(2) 0.017(2) -0.014(2) C25 0.083(3) 0.098(4) 0.071(3) 0.005(3) -0.006(3) -0.054(3) C26 0.087(3) 0.088(3) 0.044(2) 0.007(2) -0.008(2) -0.047(3) C27 0.0408(17) 0.0370(17) 0.0279(16) 0.0015(14) 0.0004(14) -0.0009(14) C28 0.0410(17) 0.0337(17) 0.0265(16) -0.0020(13) -0.0001(13) -0.0031(13) C29 0.056(2) 0.0338(17) 0.0188(14) -0.0041(13) -0.0015(14) -0.0071(15) C30 0.058(2) 0.042(2) 0.0370(19) 0.0027(16) -0.0020(16) 0.0005(16) C31 0.079(3) 0.034(2) 0.042(2) 0.0060(16) -0.010(2) -0.0046(18) C32 0.075(3) 0.044(2) 0.0332(19) 0.0046(16) -0.0014(18) -0.0222(19) C33 0.053(2) 0.054(2) 0.039(2) -0.0052(17) 0.0066(17) -0.0160(18) C34 0.0485(19) 0.0395(19) 0.0342(18) -0.0026(15) 0.0013(15) -0.0062(15) C35 0.053(2) 0.0435(19) 0.0233(15) 0.0033(14) -0.0049(15) -0.0069(15) C36 0.064(2) 0.080(3) 0.034(2) -0.002(2) 0.0051(18) -0.009(2) C37 0.053(2) 0.048(2) 0.040(2) 0.0024(17) -0.0110(17) -0.0025(16) C41 0.0447(18) 0.044(2) 0.0292(17) -0.0019(15) -0.0062(14) 0.0012(15) C42 0.054(2) 0.055(2) 0.0373(19) -0.0019(17) -0.0136(17) -0.0058(17) C43 0.049(2) 0.070(3) 0.052(2) -0.013(2) -0.0099(18) -0.0048(19) C44 0.064(3) 0.076(3) 0.045(2) -0.012(2) -0.026(2) 0.011(2) C45 0.099(3) 0.083(3) 0.036(2) 0.013(2) -0.018(2) 0.004(3) C46 0.071(3) 0.056(2) 0.039(2) 0.0086(18) -0.0126(19) -0.005(2) C47 0.0435(18) 0.0402(19) 0.0317(17) 0.0032(15) -0.0070(14) -0.0020(15) C48 0.0435(18) 0.0418(19) 0.0348(18) 0.0017(15) 0.0001(15) -0.0067(15) C49 0.050(2) 0.0424(19) 0.0358(18) 0.0091(15) -0.0085(16) -0.0116(15) C50 0.053(2) 0.049(2) 0.043(2) 0.0050(17) -0.0021(17) -0.0082(17) C51 0.079(3) 0.052(2) 0.044(2) -0.0030(18) -0.010(2) -0.015(2) C52 0.058(2) 0.056(2) 0.060(3) 0.005(2) -0.017(2) -0.0162(19) C53 0.050(2) 0.068(3) 0.066(3) 0.010(2) -0.006(2) -0.004(2) C54 0.046(2) 0.058(2) 0.051(2) 0.0069(19) -0.0119(17) -0.0058(17) C55 0.055(2) 0.045(2) 0.051(2) 0.0131(18) -0.0138(18) -0.0075(17) C56 0.134(5) 0.077(4) 0.101(4) -0.002(3) -0.023(4) 0.040(3) C57 0.103(4) 0.102(4) 0.086(4) 0.046(3) 0.022(3) 0.017(3) Cl21 0.0622(6) 0.0619(7) 0.1227(11) 0.0122(7) 0.0059(7) 0.0123(5) Cl61 0.0647(7) 0.1117(10) 0.0627(7) -0.0129(7) 0.0126(6) 0.0021(6) Cu1 0.0407(2) 0.0389(2) 0.02131(19) -0.00022(16) -0.00085(16) -0.00508(17) Cu2 0.0490(3) 0.0419(3) 0.0314(3) 0.0079(3) -0.0131(3) -0.0108(3) N1 0.0453(16) 0.0506(17) 0.0240(13) -0.0006(12) -0.0013(12) -0.0035(13) N2 0.0426(15) 0.0597(18) 0.0257(14) -0.0010(13) -0.0004(12) -0.0112(14) N3 0.0406(15) 0.0671(19) 0.0257(14) -0.0021(14) -0.0037(12) -0.0064(14) N21 0.0433(15) 0.0404(16) 0.0245(13) 0.0019(11) -0.0010(12) -0.0069(12) N22 0.0467(15) 0.0349(14) 0.0226(13) 0.0024(11) 0.0017(11) -0.0071(12) N23 0.0586(17) 0.0409(16) 0.0222(13) 0.0029(12) -0.0055(12) -0.0166(13) N41 0.0449(15) 0.0450(17) 0.0331(15) 0.0046(13) -0.0068(13) -0.0070(13) N42 0.0470(16) 0.0454(16) 0.0332(15) 0.0078(13) -0.0117(13) -0.0103(13) N43 0.0613(19) 0.0487(18) 0.0442(17) 0.0130(14) -0.0211(15) -0.0194(15) O1 0.0472(13) 0.0580(15) 0.0237(11) -0.0043(11) 0.0031(10) -0.0114(11) O21 0.0514(14) 0.0678(17) 0.0288(12) 0.0106(12) -0.0058(11) -0.0217(12) O41 0.0713(17) 0.0522(16) 0.0436(15) 0.0162(12) -0.0290(13) -0.0214(13) _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 C2 1.383(4) . ? C1 C6 1.394(4) . ? C1 C7 1.486(4) . ? C2 C3 1.371(5) . ? C2 H2 0.9500 . ? C3 C4 1.383(5) . ? C3 H3 0.9500 . ? C4 C5 1.373(5) . ? C4 H4 0.9500 . ? C5 C6 1.376(5) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.268(3) . ? C7 N1 1.321(4) . ? C8 N2 1.330(4) . ? C8 N3 1.349(4) . ? C8 N1 1.353(4) . ? Cl1A C10 1.740(8) . ? C9 C10 1.410(15) . ? C9 C14 1.414(13) . ? C9 N2 1.461(13) . ? C10 C11 1.395(14) . ? C11 C12 1.390(15) . ? C11 H11 0.9500 . ? C12 C13 1.452(14) . ? C12 H12 0.9500 . ? C13 C14 1.355(14) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? Cl1B C10B 1.742(18) . ? C9B C14B 1.32(2) . ? C9B N2 1.40(2) . ? C9B C10B 1.41(2) . ? C10B C11B 1.50(3) . ? C11B C12B 1.30(3) . ? C11B H11B 0.9500 . ? C12B C13B 1.37(2) . ? C12B H12B 0.9500 . ? C13B C14B 1.38(2) . ? C13B H13B 0.9500 . ? C14B H14B 0.9500 . ? C15 N3 1.464(4) . ? C15 C17 1.511(5) . ? C15 C16 1.512(5) . ? C15 H15 1.0000 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C21 C22 1.370(5) . ? C21 C26 1.378(5) . ? C21 C27 1.492(4) . ? C22 C23 1.383(5) . ? C22 H22 0.9500 . ? C23 C24 1.350(5) . ? C23 H23 0.9500 . ? C24 C25 1.359(6) . ? C24 H24 0.9500 . ? C25 C26 1.386(6) . ? C25 H25 0.9500 . ? C26 H26 0.9500 . ? C27 O21 1.270(4) . ? C27 N21 1.315(4) . ? C28 N22 1.334(4) . ? C28 N23 1.343(4) . ? C28 N21 1.359(4) . ? C29 C30 1.383(5) . ? C29 C34 1.387(5) . ? C29 N22 1.428(4) . ? C30 C31 1.396(5) . ? C30 Cl21 1.736(4) . ? C31 C32 1.363(5) . ? C31 H31 0.9500 . ? C32 C33 1.372(5) . ? C32 H32 0.9500 . ? C33 C34 1.392(5) . ? C33 H33 0.9500 . ? C34 H34 0.9500 . ? C35 N23 1.463(4) . ? C35 C36 1.512(5) . ? C35 C37 1.513(4) . ? C35 H35 1.0000 . ? C36 H36A 0.9800 . ? C36 H36B 0.9800 . ? C36 H36C 0.9800 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 0.9800 . ? C41 C46 1.369(5) . ? C41 C42 1.376(5) . ? C41 C47 1.502(4) . ? C42 C43 1.382(5) . ? C42 H42 0.9500 . ? C43 C44 1.367(6) . ? C43 H43 0.9500 . ? C44 C45 1.362(6) . ? C44 H44 0.9500 . ? C45 C46 1.395(5) . ? C45 H45 0.9500 . ? C46 H46 0.9500 . ? C47 O41 1.270(4) . ? C47 N41 1.307(4) . ? C48 N42 1.330(4) . ? C48 N43 1.346(4) . ? C48 N41 1.361(4) . ? C49 C50 1.390(5) . ? C49 C54 1.409(5) . ? C49 N42 1.419(4) . ? C50 C51 1.402(5) . ? C50 Cl61 1.727(4) . ? C51 C52 1.361(6) . ? C51 H51 0.9500 . ? C52 C53 1.361(6) . ? C52 H52 0.9500 . ? C53 C54 1.393(5) . ? C53 H53 0.9500 . ? C54 H54 0.9500 . ? C55 N43 1.463(4) . ? C55 C57 1.475(6) . ? C55 C56 1.509(6) . ? C55 H55 1.0000 . ? C56 H56A 0.9800 . ? C56 H56B 0.9800 . ? C56 H56C 0.9800 . ? C57 H57A 0.9800 . ? C57 H57B 0.9800 . ? C57 H57C 0.9800 . ? Cu1 O21 1.903(2) . ? Cu1 O1 1.913(2) . ? Cu1 N22 1.938(3) . ? Cu1 N2 1.945(3) . ? Cu2 O41 1.892(2) 3_665 ? Cu2 O41 1.892(2) . ? Cu2 N42 1.962(3) 3_665 ? Cu2 N42 1.962(3) . ? N3 H1 0.8800 . ? N23 H21 0.8800 . ? N43 H41 0.8800 . ? 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 C2 C1 C6 118.4(3) . . ? C2 C1 C7 120.3(3) . . ? C6 C1 C7 121.3(3) . . ? C3 C2 C1 121.3(3) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 119.8(3) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 119.7(3) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 120.2(3) . . ? C5 C6 H6 119.9 . . ? C1 C6 H6 119.9 . . ? O1 C7 N1 128.1(3) . . ? O1 C7 C1 116.0(3) . . ? N1 C7 C1 115.9(3) . . ? N2 C8 N3 120.1(3) . . ? N2 C8 N1 125.8(3) . . ? N3 C8 N1 114.1(3) . . ? C10 C9 C14 118.3(11) . . ? C10 C9 N2 117.7(8) . . ? C14 C9 N2 124.0(9) . . ? C11 C10 C9 126.8(9) . . ? C11 C10 Cl1A 115.9(8) . . ? C9 C10 Cl1A 117.3(7) . . ? C12 C11 C10 112.5(10) . . ? C12 C11 H11 123.8 . . ? C10 C11 H11 123.8 . . ? C11 C12 C13 122.9(9) . . ? C11 C12 H12 118.5 . . ? C13 C12 H12 118.5 . . ? C14 C13 C12 121.7(9) . . ? C14 C13 H13 119.2 . . ? C12 C13 H13 119.2 . . ? C13 C14 C9 117.7(10) . . ? C13 C14 H14 121.1 . . ? C9 C14 H14 121.1 . . ? C14B C9B N2 127.1(14) . . ? C14B C9B C10B 121.1(18) . . ? N2 C9B C10B 111.7(13) . . ? C9B C10B C11B 120.6(17) . . ? C9B C10B Cl1B 119.2(14) . . ? C11B C10B Cl1B 120.2(16) . . ? C12B C11B C10B 106.0(18) . . ? C12B C11B H11B 127.0 . . ? C10B C11B H11B 127.0 . . ? C11B C12B C13B 139(2) . . ? C11B C12B H12B 110.4 . . ? C13B C12B H12B 110.4 . . ? C12B C13B C14B 109.5(19) . . ? C12B C13B H13B 125.3 . . ? C14B C13B H13B 125.3 . . ? C9B C14B C13B 123.4(17) . . ? C9B C14B H14B 118.3 . . ? C13B C14B H14B 118.3 . . ? N3 C15 C17 112.6(3) . . ? N3 C15 C16 108.4(3) . . ? C17 C15 C16 111.3(3) . . ? N3 C15 H15 108.1 . . ? C17 C15 H15 108.1 . . ? C16 C15 H15 108.1 . . ? 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 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C22 C21 C26 118.0(3) . . ? C22 C21 C27 121.9(3) . . ? C26 C21 C27 120.1(3) . . ? C21 C22 C23 121.0(4) . . ? C21 C22 H22 119.5 . . ? C23 C22 H22 119.5 . . ? C24 C23 C22 120.8(4) . . ? C24 C23 H23 119.6 . . ? C22 C23 H23 119.6 . . ? C23 C24 C25 119.0(4) . . ? C23 C24 H24 120.5 . . ? C25 C24 H24 120.5 . . ? C24 C25 C26 121.1(4) . . ? C24 C25 H25 119.5 . . ? C26 C25 H25 119.5 . . ? C21 C26 C25 120.2(4) . . ? C21 C26 H26 119.9 . . ? C25 C26 H26 119.9 . . ? O21 C27 N21 128.2(3) . . ? O21 C27 C21 115.8(3) . . ? N21 C27 C21 116.0(3) . . ? N22 C28 N23 121.3(3) . . ? N22 C28 N21 124.7(3) . . ? N23 C28 N21 114.0(3) . . ? C30 C29 C34 118.5(3) . . ? C30 C29 N22 119.6(3) . . ? C34 C29 N22 121.6(3) . . ? C29 C30 C31 120.9(3) . . ? C29 C30 Cl21 119.9(3) . . ? C31 C30 Cl21 119.2(3) . . ? C32 C31 C30 119.8(3) . . ? C32 C31 H31 120.1 . . ? C30 C31 H31 120.1 . . ? C31 C32 C33 120.1(3) . . ? C31 C32 H32 119.9 . . ? C33 C32 H32 119.9 . . ? C32 C33 C34 120.5(3) . . ? C32 C33 H33 119.8 . . ? C34 C33 H33 119.8 . . ? C29 C34 C33 120.1(3) . . ? C29 C34 H34 119.9 . . ? C33 C34 H34 119.9 . . ? N23 C35 C36 111.1(3) . . ? N23 C35 C37 108.7(3) . . ? C36 C35 C37 111.2(3) . . ? N23 C35 H35 108.6 . . ? C36 C35 H35 108.6 . . ? C37 C35 H35 108.6 . . ? 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 . . ? C35 C37 H37A 109.5 . . ? C35 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? C35 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 109.5 . . ? C46 C41 C42 119.8(3) . . ? C46 C41 C47 121.2(3) . . ? C42 C41 C47 119.0(3) . . ? C41 C42 C43 120.5(4) . . ? C41 C42 H42 119.8 . . ? C43 C42 H42 119.8 . . ? C44 C43 C42 120.0(4) . . ? C44 C43 H43 120.0 . . ? C42 C43 H43 120.0 . . ? C45 C44 C43 119.5(4) . . ? C45 C44 H44 120.3 . . ? C43 C44 H44 120.3 . . ? C44 C45 C46 121.2(4) . . ? C44 C45 H45 119.4 . . ? C46 C45 H45 119.4 . . ? C41 C46 C45 119.0(4) . . ? C41 C46 H46 120.5 . . ? C45 C46 H46 120.5 . . ? O41 C47 N41 129.3(3) . . ? O41 C47 C41 115.0(3) . . ? N41 C47 C41 115.7(3) . . ? N42 C48 N43 120.6(3) . . ? N42 C48 N41 126.2(3) . . ? N43 C48 N41 113.1(3) . . ? C50 C49 C54 118.3(3) . . ? C50 C49 N42 122.2(3) . . ? C54 C49 N42 119.5(3) . . ? C49 C50 C51 121.0(4) . . ? C49 C50 Cl61 119.6(3) . . ? C51 C50 Cl61 119.4(3) . . ? C52 C51 C50 119.5(4) . . ? C52 C51 H51 120.3 . . ? C50 C51 H51 120.3 . . ? C51 C52 C53 120.7(4) . . ? C51 C52 H52 119.6 . . ? C53 C52 H52 119.6 . . ? C52 C53 C54 121.3(4) . . ? C52 C53 H53 119.3 . . ? C54 C53 H53 119.3 . . ? C53 C54 C49 119.1(4) . . ? C53 C54 H54 120.4 . . ? C49 C54 H54 120.4 . . ? N43 C55 C57 109.3(3) . . ? N43 C55 C56 109.6(4) . . ? C57 C55 C56 111.5(4) . . ? N43 C55 H55 108.8 . . ? C57 C55 H55 108.8 . . ? C56 C55 H55 108.8 . . ? C55 C56 H56A 109.5 . . ? C55 C56 H56B 109.5 . . ? H56A C56 H56B 109.5 . . ? C55 C56 H56C 109.5 . . ? H56A C56 H56C 109.5 . . ? H56B C56 H56C 109.5 . . ? C55 C57 H57A 109.5 . . ? C55 C57 H57B 109.5 . . ? H57A C57 H57B 109.5 . . ? C55 C57 H57C 109.5 . . ? H57A C57 H57C 109.5 . . ? H57B C57 H57C 109.5 . . ? O21 Cu1 O1 162.36(11) . . ? O21 Cu1 N22 90.15(10) . . ? O1 Cu1 N22 91.09(10) . . ? O21 Cu1 N2 92.05(11) . . ? O1 Cu1 N2 90.38(11) . . ? N22 Cu1 N2 167.99(12) . . ? O41 Cu2 O41 180.00(17) 3_665 . ? O41 Cu2 N42 90.45(10) 3_665 3_665 ? O41 Cu2 N42 89.55(10) . 3_665 ? O41 Cu2 N42 89.55(10) 3_665 . ? O41 Cu2 N42 90.45(10) . . ? N42 Cu2 N42 180.00(16) 3_665 . ? C7 N1 C8 122.8(3) . . ? C8 N2 C9B 114.0(8) . . ? C8 N2 C9 117.9(6) . . ? C9B N2 C9 19.6(7) . . ? C8 N2 Cu1 125.0(2) . . ? C9B N2 Cu1 120.2(8) . . ? C9 N2 Cu1 116.2(5) . . ? C8 N3 C15 125.4(3) . . ? C8 N3 H1 117.3 . . ? C15 N3 H1 117.3 . . ? C27 N21 C28 122.9(3) . . ? C28 N22 C29 119.1(2) . . ? C28 N22 Cu1 124.5(2) . . ? C29 N22 Cu1 116.40(19) . . ? C28 N23 C35 125.4(3) . . ? C28 N23 H21 117.3 . . ? C35 N23 H21 117.3 . . ? C47 N41 C48 122.0(3) . . ? C48 N42 C49 116.1(3) . . ? C48 N42 Cu2 123.9(2) . . ? C49 N42 Cu2 119.9(2) . . ? C48 N43 C55 126.6(3) . . ? C48 N43 H41 116.7 . . ? C55 N43 H41 116.7 . . ? C7 O1 Cu1 126.9(2) . . ? C27 O21 Cu1 125.6(2) . . ? C47 O41 Cu2 127.2(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 C6 C1 C2 C3 -0.2(5) . . . . ? C7 C1 C2 C3 -179.2(3) . . . . ? C1 C2 C3 C4 -0.9(5) . . . . ? C2 C3 C4 C5 1.4(6) . . . . ? C3 C4 C5 C6 -0.9(6) . . . . ? C4 C5 C6 C1 -0.2(5) . . . . ? C2 C1 C6 C5 0.7(5) . . . . ? C7 C1 C6 C5 179.7(3) . . . . ? C2 C1 C7 O1 -11.5(4) . . . . ? C6 C1 C7 O1 169.5(3) . . . . ? C2 C1 C7 N1 168.3(3) . . . . ? C6 C1 C7 N1 -10.7(4) . . . . ? C14 C9 C10 C11 -3.2(18) . . . . ? N2 C9 C10 C11 179.8(9) . . . . ? C14 C9 C10 Cl1A 176.1(9) . . . . ? N2 C9 C10 Cl1A -0.9(13) . . . . ? C9 C10 C11 C12 3.6(16) . . . . ? Cl1A C10 C11 C12 -175.8(8) . . . . ? C10 C11 C12 C13 -2.7(15) . . . . ? C11 C12 C13 C14 1.8(15) . . . . ? C12 C13 C14 C9 -1.1(15) . . . . ? C10 C9 C14 C13 1.7(17) . . . . ? N2 C9 C14 C13 178.5(9) . . . . ? C14B C9B C10B C11B 2(3) . . . . ? N2 C9B C10B C11B 179.2(14) . . . . ? C14B C9B C10B Cl1B -177.8(14) . . . . ? N2 C9B C10B Cl1B 0(2) . . . . ? C9B C10B C11B C12B -2(2) . . . . ? Cl1B C10B C11B C12B 177.2(14) . . . . ? C10B C11B C12B C13B 4(4) . . . . ? C11B C12B C13B C14B -4(4) . . . . ? N2 C9B C14B C13B -178.5(15) . . . . ? C10B C9B C14B C13B -2(3) . . . . ? C12B C13B C14B C9B 2(2) . . . . ? C26 C21 C22 C23 -1.2(6) . . . . ? C27 C21 C22 C23 -178.1(3) . . . . ? C21 C22 C23 C24 0.6(6) . . . . ? C22 C23 C24 C25 0.4(7) . . . . ? C23 C24 C25 C26 -0.7(8) . . . . ? C22 C21 C26 C25 0.9(7) . . . . ? C27 C21 C26 C25 177.8(4) . . . . ? C24 C25 C26 C21 0.1(8) . . . . ? C22 C21 C27 O21 168.5(3) . . . . ? C26 C21 C27 O21 -8.3(5) . . . . ? C22 C21 C27 N21 -11.2(5) . . . . ? C26 C21 C27 N21 172.0(4) . . . . ? C34 C29 C30 C31 -0.7(5) . . . . ? N22 C29 C30 C31 173.3(3) . . . . ? C34 C29 C30 Cl21 179.9(2) . . . . ? N22 C29 C30 Cl21 -6.1(4) . . . . ? C29 C30 C31 C32 -1.0(5) . . . . ? Cl21 C30 C31 C32 178.4(3) . . . . ? C30 C31 C32 C33 2.2(6) . . . . ? C31 C32 C33 C34 -1.6(5) . . . . ? C30 C29 C34 C33 1.3(5) . . . . ? N22 C29 C34 C33 -172.6(3) . . . . ? C32 C33 C34 C29 -0.1(5) . . . . ? C46 C41 C42 C43 1.2(6) . . . . ? C47 C41 C42 C43 -178.0(3) . . . . ? C41 C42 C43 C44 -1.0(6) . . . . ? C42 C43 C44 C45 -0.2(7) . . . . ? C43 C44 C45 C46 1.2(7) . . . . ? C42 C41 C46 C45 -0.2(6) . . . . ? C47 C41 C46 C45 179.0(4) . . . . ? C44 C45 C46 C41 -1.0(7) . . . . ? C46 C41 C47 O41 158.7(4) . . . . ? C42 C41 C47 O41 -22.1(5) . . . . ? C46 C41 C47 N41 -20.8(5) . . . . ? C42 C41 C47 N41 158.5(3) . . . . ? C54 C49 C50 C51 0.4(5) . . . . ? N42 C49 C50 C51 -178.7(3) . . . . ? C54 C49 C50 Cl61 -179.0(3) . . . . ? N42 C49 C50 Cl61 1.9(5) . . . . ? C49 C50 C51 C52 -0.4(6) . . . . ? Cl61 C50 C51 C52 179.0(3) . . . . ? C50 C51 C52 C53 -0.4(6) . . . . ? C51 C52 C53 C54 1.3(6) . . . . ? C52 C53 C54 C49 -1.2(6) . . . . ? C50 C49 C54 C53 0.4(5) . . . . ? N42 C49 C54 C53 179.5(3) . . . . ? O1 C7 N1 C8 5.7(5) . . . . ? C1 C7 N1 C8 -174.1(3) . . . . ? N2 C8 N1 C7 4.7(5) . . . . ? N3 C8 N1 C7 -176.6(3) . . . . ? N3 C8 N2 C9B -15.8(8) . . . . ? N1 C8 N2 C9B 162.8(7) . . . . ? N3 C8 N2 C9 5.6(6) . . . . ? N1 C8 N2 C9 -175.8(5) . . . . ? N3 C8 N2 Cu1 174.2(2) . . . . ? N1 C8 N2 Cu1 -7.2(5) . . . . ? C14B C9B N2 C8 -70(2) . . . . ? C10B C9B N2 C8 113.3(14) . . . . ? C14B C9B N2 C9 -176(5) . . . . ? C10B C9B N2 C9 7(3) . . . . ? C14B C9B N2 Cu1 101.0(19) . . . . ? C10B C9B N2 Cu1 -76.2(16) . . . . ? C10 C9 N2 C8 -87.7(10) . . . . ? C14 C9 N2 C8 95.5(12) . . . . ? C10 C9 N2 C9B -4(3) . . . . ? C14 C9 N2 C9B 179(5) . . . . ? C10 C9 N2 Cu1 102.7(9) . . . . ? C14 C9 N2 Cu1 -74.1(12) . . . . ? O21 Cu1 N2 C8 164.1(3) . . . . ? O1 Cu1 N2 C8 1.6(3) . . . . ? N22 Cu1 N2 C8 -95.5(6) . . . . ? O21 Cu1 N2 C9B -5.4(7) . . . . ? O1 Cu1 N2 C9B -167.9(7) . . . . ? N22 Cu1 N2 C9B 95.1(9) . . . . ? O21 Cu1 N2 C9 -27.1(5) . . . . ? O1 Cu1 N2 C9 170.3(5) . . . . ? N22 Cu1 N2 C9 73.3(7) . . . . ? N2 C8 N3 C15 -179.1(3) . . . . ? N1 C8 N3 C15 2.2(5) . . . . ? C17 C15 N3 C8 -74.2(5) . . . . ? C16 C15 N3 C8 162.3(4) . . . . ? O21 C27 N21 C28 -7.9(5) . . . . ? C21 C27 N21 C28 171.8(3) . . . . ? N22 C28 N21 C27 11.1(5) . . . . ? N23 C28 N21 C27 -167.3(3) . . . . ? N23 C28 N22 C29 1.5(5) . . . . ? N21 C28 N22 C29 -176.7(3) . . . . ? N23 C28 N22 Cu1 -176.8(2) . . . . ? N21 C28 N22 Cu1 4.9(5) . . . . ? C30 C29 N22 C28 110.3(3) . . . . ? C34 C29 N22 C28 -75.9(4) . . . . ? C30 C29 N22 Cu1 -71.1(3) . . . . ? C34 C29 N22 Cu1 102.6(3) . . . . ? O21 Cu1 N22 C28 -16.3(3) . . . . ? O1 Cu1 N22 C28 146.1(3) . . . . ? N2 Cu1 N22 C28 -116.9(5) . . . . ? O21 Cu1 N22 C29 165.3(2) . . . . ? O1 Cu1 N22 C29 -32.3(2) . . . . ? N2 Cu1 N22 C29 64.7(6) . . . . ? N22 C28 N23 C35 178.2(3) . . . . ? N21 C28 N23 C35 -3.4(5) . . . . ? C36 C35 N23 C28 81.9(4) . . . . ? C37 C35 N23 C28 -155.5(3) . . . . ? O41 C47 N41 C48 -3.2(6) . . . . ? C41 C47 N41 C48 176.1(3) . . . . ? N42 C48 N41 C47 -5.9(5) . . . . ? N43 C48 N41 C47 176.2(3) . . . . ? N43 C48 N42 C49 6.8(5) . . . . ? N41 C48 N42 C49 -171.0(3) . . . . ? N43 C48 N42 Cu2 -169.7(3) . . . . ? N41 C48 N42 Cu2 12.5(5) . . . . ? C50 C49 N42 C48 -86.9(4) . . . . ? C54 C49 N42 C48 94.1(4) . . . . ? C50 C49 N42 Cu2 89.7(4) . . . . ? C54 C49 N42 Cu2 -89.3(3) . . . . ? O41 Cu2 N42 C48 171.1(3) 3_665 . . . ? O41 Cu2 N42 C48 -8.9(3) . . . . ? N42 Cu2 N42 C48 5(100) 3_665 . . . ? O41 Cu2 N42 C49 -5.3(3) 3_665 . . . ? O41 Cu2 N42 C49 174.7(3) . . . . ? N42 Cu2 N42 C49 -172(100) 3_665 . . . ? N42 C48 N43 C55 -177.9(3) . . . . ? N41 C48 N43 C55 0.2(5) . . . . ? C57 C55 N43 C48 101.0(5) . . . . ? C56 C55 N43 C48 -136.6(4) . . . . ? N1 C7 O1 Cu1 -12.1(5) . . . . ? C1 C7 O1 Cu1 167.7(2) . . . . ? O21 Cu1 O1 C7 -90.7(4) . . . . ? N22 Cu1 O1 C7 175.4(3) . . . . ? N2 Cu1 O1 C7 7.3(3) . . . . ? N21 C27 O21 Cu1 -11.5(5) . . . . ? C21 C27 O21 Cu1 168.8(2) . . . . ? O1 Cu1 O21 C27 -74.5(4) . . . . ? N22 Cu1 O21 C27 19.6(3) . . . . ? N2 Cu1 O21 C27 -172.2(3) . . . . ? N41 C47 O41 Cu2 4.1(6) . . . . ? C41 C47 O41 Cu2 -175.3(2) . . . . ? O41 Cu2 O41 C47 86(100) 3_665 . . . ? N42 Cu2 O41 C47 -178.4(3) 3_665 . . . ? N42 Cu2 O41 C47 1.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 28.28 _diffrn_measured_fraction_theta_full 0.969 _refine_diff_density_max 1.105 _refine_diff_density_min -0.846 _refine_diff_density_rms 0.078 #============================================================================== # 4. TEXT #============================================================================== _publ_section_abstract ; See Text ; _publ_section_comment ; See Text ; _publ_section_exptl_prep ; See text ; _publ_section_exptl_refinement ; The structure was solved by direct method with ShelxS-97. All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters while hydrogen atoms were placed in idealized position. ; _publ_section_references ; Bruker (2005a). XPREP. Version 2005/2. Bruker AXS Inc., Madison, WI, USA. Bruker (2005b). APEX 2. Version 1.0.18. Bruker AXS Inc., Madison, WI, USA. Bruker (2003). SAINT. Version 7.23A. Bruker AXS Inc., Madison, WI, USA. Bruker (2001). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, WI, USA. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Flack, H. D. and Schwarzenbach, D. (1988). Acta Cryst. A44, 499-506. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of G\"ottingen, Germany. Sheldrick, G. M. (2004). SADABS. Version 2004/1. Bruker AXS Inc., Madison, WI, USA. Sheldrick, G. M. (2002). TWINABS. Version 1.05. Bruker AXS Inc., Madison, WI, USA. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. University of Utrecht, Utrecht, The Netherlands. ; _publ_section_figure_captions ; See text ; _publ_section_table_legends ; See text ; _publ_section_acknowledgements ; See text ; data_bad003 _database_code_depnum_ccdc_archive 'CCDC 816342' #TrackingRef '- Compound_4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Cl N3 O' _chemical_formula_weight 329.82 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' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.0536(15) _cell_length_b 14.736(2) _cell_length_c 12.5743(19) _cell_angle_alpha 90.00 _cell_angle_beta 113.060(2) _cell_angle_gamma 90.00 _cell_volume 1714.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 3680 _cell_measurement_theta_min 2.20 _cell_measurement_theta_max 24.31 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.17 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.278 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.231 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9618 _exptl_absorpt_correction_T_max 0.9728 _exptl_absorpt_process_details 'XPREP (Bruker, 2005a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 20438 _diffrn_reflns_av_R_equivalents 0.0561 _diffrn_reflns_av_sigmaI/netI 0.0514 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.20 _diffrn_reflns_theta_max 28.22 _reflns_number_total 4170 _reflns_number_gt 2621 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2005b)' _computing_cell_refinement 'APEX 2 (Bruker, 2005b)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0326P)^2^+0.6539P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4170 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0933 _refine_ls_R_factor_gt 0.0439 _refine_ls_wR_factor_ref 0.1005 _refine_ls_wR_factor_gt 0.0831 _refine_ls_goodness_of_fit_ref 1.001 _refine_ls_restrained_S_all 1.001 _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 0.31560(19) 0.36486(12) 0.66870(15) 0.0284(4) Uani 1 1 d . . . C2 C 0.1742(2) 0.39042(13) 0.60261(17) 0.0358(5) Uani 1 1 d . . . H2 H 0.1392 0.3885 0.5207 0.043 Uiso 1 1 calc R . . C3 C 0.0840(2) 0.41863(15) 0.6556(2) 0.0449(5) Uani 1 1 d . . . H3 H -0.0133 0.4349 0.6101 0.054 Uiso 1 1 calc R . . C4 C 0.1354(3) 0.42309(14) 0.7742(2) 0.0449(5) Uani 1 1 d . . . H4 H 0.0734 0.4424 0.8106 0.054 Uiso 1 1 calc R . . C5 C 0.2761(3) 0.39966(14) 0.84036(18) 0.0448(5) Uani 1 1 d . . . H5 H 0.3118 0.4040 0.9222 0.054 Uiso 1 1 calc R . . C6 C 0.3651(2) 0.36988(13) 0.78764(16) 0.0362(5) Uani 1 1 d . . . H6 H 0.4617 0.3526 0.8336 0.043 Uiso 1 1 calc R . . C7 C 0.4132(2) 0.32797(12) 0.61497(16) 0.0296(4) Uani 1 1 d . . . O1 O 0.51234(14) 0.27588(9) 0.67380(11) 0.0395(3) Uani 1 1 d . . . N1 N 0.37868(16) 0.35448(10) 0.50466(12) 0.0288(3) Uani 1 1 d . . . C8 C 0.46379(19) 0.33327(12) 0.44929(15) 0.0284(4) Uani 1 1 d . . . N2 N 0.59376(16) 0.29230(11) 0.50263(14) 0.0316(4) Uani 1 1 d . . . H52 H 0.606(2) 0.2721(14) 0.5666(18) 0.042(6) Uiso 1 1 d . . . C9 C 0.70090(18) 0.27838(12) 0.45814(15) 0.0284(4) Uani 1 1 d . . . C10 C 0.77184(19) 0.19559(13) 0.47587(15) 0.0310(4) Uani 1 1 d . . . Cl1 Cl 0.72784(6) 0.11094(3) 0.55175(5) 0.04267(15) Uani 1 1 d . . . C11 C 0.8783(2) 0.17932(14) 0.43433(18) 0.0398(5) Uani 1 1 d . . . H11 H 0.9268 0.1225 0.4480 0.048 Uiso 1 1 calc R . . C12 C 0.9136(2) 0.24558(15) 0.37326(19) 0.0447(5) Uani 1 1 d . . . H12 H 0.9841 0.2340 0.3420 0.054 Uiso 1 1 calc R . . C13 C 0.8469(2) 0.32860(15) 0.35744(18) 0.0407(5) Uani 1 1 d . . . H13 H 0.8729 0.3748 0.3165 0.049 Uiso 1 1 calc R . . C14 C 0.7424(2) 0.34563(14) 0.40048(17) 0.0347(5) Uani 1 1 d . . . H14 H 0.6987 0.4039 0.3905 0.042 Uiso 1 1 calc R . . N3 N 0.42119(17) 0.35405(11) 0.33767(13) 0.0307(4) Uani 1 1 d . . . H53 H 0.463(2) 0.3284(13) 0.3006(16) 0.029(5) Uiso 1 1 d . . . C15 C 0.29277(19) 0.40759(12) 0.26626(16) 0.0309(4) Uani 1 1 d . . . C16 C 0.1546(2) 0.35781(15) 0.25264(18) 0.0421(5) Uani 1 1 d . . . H16A H 0.1543 0.2977 0.2191 0.063 Uiso 1 1 calc R . . H16B H 0.0709 0.3926 0.2016 0.063 Uiso 1 1 calc R . . H16C H 0.1496 0.3509 0.3285 0.063 Uiso 1 1 calc R . . C17 C 0.2986(2) 0.50077(14) 0.31906(19) 0.0471(6) Uani 1 1 d . . . H17A H 0.2919 0.4946 0.3944 0.071 Uiso 1 1 calc R . . H17B H 0.2177 0.5376 0.2678 0.071 Uiso 1 1 calc R . . H17C H 0.3901 0.5304 0.3291 0.071 Uiso 1 1 calc R . . C18 C 0.3018(2) 0.41628(17) 0.14868(18) 0.0502(6) Uani 1 1 d . . . H18A H 0.3929 0.4459 0.1577 0.075 Uiso 1 1 calc R . . H18B H 0.2205 0.4527 0.0974 0.075 Uiso 1 1 calc R . . H18C H 0.2980 0.3558 0.1152 0.075 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 0.0314(10) 0.0275(10) 0.0271(10) 0.0008(8) 0.0123(8) -0.0012(8) C2 0.0339(11) 0.0424(11) 0.0299(10) -0.0039(9) 0.0111(9) 0.0008(9) C3 0.0368(12) 0.0483(13) 0.0521(14) -0.0045(11) 0.0202(11) 0.0050(10) C4 0.0547(14) 0.0395(12) 0.0541(14) -0.0080(10) 0.0358(12) 0.0005(11) C5 0.0659(15) 0.0420(12) 0.0320(11) -0.0027(9) 0.0253(11) 0.0026(11) C6 0.0425(12) 0.0338(11) 0.0302(11) 0.0001(8) 0.0120(9) 0.0019(9) C7 0.0279(10) 0.0318(10) 0.0277(10) -0.0001(8) 0.0095(8) -0.0015(8) O1 0.0380(8) 0.0498(9) 0.0317(8) 0.0113(6) 0.0149(6) 0.0133(7) N1 0.0272(8) 0.0346(8) 0.0249(8) 0.0021(7) 0.0106(7) 0.0033(7) C8 0.0278(10) 0.0273(10) 0.0286(10) 0.0008(8) 0.0095(8) -0.0009(8) N2 0.0288(9) 0.0398(10) 0.0270(9) 0.0066(8) 0.0119(7) 0.0065(7) C9 0.0236(9) 0.0360(11) 0.0228(9) -0.0028(8) 0.0059(8) -0.0022(8) C10 0.0291(10) 0.0343(11) 0.0269(10) -0.0018(8) 0.0081(8) -0.0023(8) Cl1 0.0479(3) 0.0369(3) 0.0431(3) 0.0080(2) 0.0177(2) 0.0039(2) C11 0.0348(11) 0.0393(12) 0.0454(12) -0.0062(10) 0.0157(10) 0.0044(9) C12 0.0357(12) 0.0554(14) 0.0502(14) -0.0060(11) 0.0247(11) -0.0033(10) C13 0.0321(11) 0.0489(13) 0.0418(12) 0.0020(10) 0.0153(10) -0.0089(10) C14 0.0274(10) 0.0364(11) 0.0363(11) 0.0019(9) 0.0081(9) -0.0029(8) N3 0.0278(9) 0.0403(9) 0.0249(8) 0.0029(7) 0.0114(7) 0.0056(7) C15 0.0287(10) 0.0346(11) 0.0275(10) 0.0061(8) 0.0090(8) 0.0028(8) C16 0.0295(11) 0.0526(13) 0.0369(12) 0.0024(10) 0.0052(9) -0.0008(10) C17 0.0523(14) 0.0355(12) 0.0475(13) 0.0040(10) 0.0133(11) 0.0027(10) C18 0.0531(14) 0.0651(15) 0.0336(12) 0.0165(11) 0.0182(11) 0.0136(12) _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 C6 1.381(3) . ? C1 C2 1.389(3) . ? C1 C7 1.494(2) . ? C2 C3 1.383(3) . ? C2 H2 0.9500 . ? C3 C4 1.376(3) . ? C3 H3 0.9500 . ? C4 C5 1.375(3) . ? C4 H4 0.9500 . ? C5 C6 1.378(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.246(2) . ? C7 N1 1.349(2) . ? N1 C8 1.335(2) . ? C8 N3 1.333(2) . ? C8 N2 1.355(2) . ? N2 C9 1.410(2) . ? N2 H52 0.82(2) . ? C9 C14 1.385(3) . ? C9 C10 1.386(3) . ? C10 C11 1.383(3) . ? C10 Cl1 1.7299(19) . ? C11 C12 1.372(3) . ? C11 H11 0.9500 . ? C12 C13 1.372(3) . ? C12 H12 0.9500 . ? C13 C14 1.380(3) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? N3 C15 1.479(2) . ? N3 H53 0.833(18) . ? C15 C17 1.516(3) . ? C15 C16 1.520(3) . ? C15 C18 1.522(3) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C6 C1 C2 118.94(17) . . ? C6 C1 C7 119.14(17) . . ? C2 C1 C7 121.85(16) . . ? C3 C2 C1 120.28(18) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C4 C3 C2 119.9(2) . . ? C4 C3 H3 120.1 . . ? C2 C3 H3 120.1 . . ? C5 C4 C3 120.28(19) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C4 C5 C6 119.83(19) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C5 C6 C1 120.77(19) . . ? C5 C6 H6 119.6 . . ? C1 C6 H6 119.6 . . ? O1 C7 N1 127.75(17) . . ? O1 C7 C1 118.04(16) . . ? N1 C7 C1 114.18(16) . . ? C8 N1 C7 120.63(16) . . ? N3 C8 N1 119.23(16) . . ? N3 C8 N2 118.27(16) . . ? N1 C8 N2 122.50(16) . . ? C8 N2 C9 127.38(16) . . ? C8 N2 H52 113.0(15) . . ? C9 N2 H52 119.5(15) . . ? C14 C9 C10 118.17(17) . . ? C14 C9 N2 122.50(17) . . ? C10 C9 N2 119.29(16) . . ? C11 C10 C9 121.14(18) . . ? C11 C10 Cl1 119.09(15) . . ? C9 C10 Cl1 119.77(14) . . ? C12 C11 C10 119.75(19) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 119.78(19) . . ? C13 C12 H12 120.1 . . ? C11 C12 H12 120.1 . . ? C12 C13 C14 120.62(19) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C13 C14 C9 120.45(19) . . ? C13 C14 H14 119.8 . . ? C9 C14 H14 119.8 . . ? C8 N3 C15 127.30(16) . . ? C8 N3 H53 117.4(13) . . ? C15 N3 H53 114.6(13) . . ? N3 C15 C17 110.02(16) . . ? N3 C15 C16 110.65(15) . . ? C17 C15 C16 111.31(17) . . ? N3 C15 C18 105.33(15) . . ? C17 C15 C18 110.02(17) . . ? C16 C15 C18 109.33(17) . . ? 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 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C6 C1 C2 C3 -1.3(3) . . . . ? C7 C1 C2 C3 175.71(18) . . . . ? C1 C2 C3 C4 1.3(3) . . . . ? C2 C3 C4 C5 0.0(3) . . . . ? C3 C4 C5 C6 -1.3(3) . . . . ? C4 C5 C6 C1 1.2(3) . . . . ? C2 C1 C6 C5 0.0(3) . . . . ? C7 C1 C6 C5 -177.05(18) . . . . ? C6 C1 C7 O1 24.0(3) . . . . ? C2 C1 C7 O1 -152.99(18) . . . . ? C6 C1 C7 N1 -157.66(17) . . . . ? C2 C1 C7 N1 25.3(3) . . . . ? O1 C7 N1 C8 -7.8(3) . . . . ? C1 C7 N1 C8 174.07(16) . . . . ? C7 N1 C8 N3 174.66(17) . . . . ? C7 N1 C8 N2 -6.3(3) . . . . ? N3 C8 N2 C9 8.8(3) . . . . ? N1 C8 N2 C9 -170.27(17) . . . . ? C8 N2 C9 C14 45.0(3) . . . . ? C8 N2 C9 C10 -137.44(19) . . . . ? C14 C9 C10 C11 -1.9(3) . . . . ? N2 C9 C10 C11 -179.57(17) . . . . ? C14 C9 C10 Cl1 177.81(14) . . . . ? N2 C9 C10 Cl1 0.1(2) . . . . ? C9 C10 C11 C12 -0.8(3) . . . . ? Cl1 C10 C11 C12 179.52(16) . . . . ? C10 C11 C12 C13 2.4(3) . . . . ? C11 C12 C13 C14 -1.3(3) . . . . ? C12 C13 C14 C9 -1.5(3) . . . . ? C10 C9 C14 C13 3.0(3) . . . . ? N2 C9 C14 C13 -179.39(17) . . . . ? N1 C8 N3 C15 6.5(3) . . . . ? N2 C8 N3 C15 -172.52(17) . . . . ? C8 N3 C15 C17 57.5(2) . . . . ? C8 N3 C15 C16 -65.9(2) . . . . ? C8 N3 C15 C18 176.01(19) . . . . ? 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 N2 H52 O1 0.82(2) 1.92(2) 2.596(2) 139(2) . N3 H53 O1 0.833(18) 2.401(19) 3.199(2) 160.6(17) 4_565 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 28.22 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.220 _refine_diff_density_min -0.279 _refine_diff_density_rms 0.044 #============================================================================== # 4. TEXT #============================================================================== _publ_section_abstract ; See Text ; _publ_section_comment ; See Text ; _publ_section_exptl_prep ; See text ; _publ_section_exptl_refinement ; The structure was solved by direct method with ShelxS-97. All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters while hydrogen atoms were placed in idealized position. ; _publ_section_references ; Bruker (2005a). XPREP. Version 2005/2. Bruker AXS Inc., Madison, WI, USA. Bruker (2005b). APEX 2. Version 1.0.18. Bruker AXS Inc., Madison, WI, USA. Bruker (2003). SAINT. Version 7.23A. Bruker AXS Inc., Madison, WI, USA. Bruker (2001). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, WI, USA. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Flack, H. D. and Schwarzenbach, D. (1988). Acta Cryst. A44, 499-506. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of G\"ottingen, Germany. Sheldrick, G. M. (2004). SADABS. Version 2004/1. Bruker AXS Inc., Madison, WI, USA. Sheldrick, G. M. (2002). TWINABS. Version 1.05. Bruker AXS Inc., Madison, WI, USA. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. University of Utrecht, Utrecht, The Netherlands. ; _publ_section_figure_captions ; See text ; _publ_section_table_legends ; See text ; _publ_section_acknowledgements ; See text ; data_bad004 _database_code_depnum_ccdc_archive 'CCDC 816343' #TrackingRef '- Compound_4a.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C36 H38 Cl2 Cu N6 O2' _chemical_formula_weight 721.16 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' _symmetry_cell_setting Rhombohedral _symmetry_space_group_name_H-M R-3 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' '-x+2/3, -y+1/3, -z+1/3' 'y+2/3, -x+y+1/3, -z+1/3' 'x-y+2/3, x+1/3, -z+1/3' '-x+1/3, -y+2/3, -z+2/3' 'y+1/3, -x+y+2/3, -z+2/3' 'x-y+1/3, x+2/3, -z+2/3' _cell_length_a 40.2231(18) _cell_length_b 40.2231(18) _cell_length_c 11.5607(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 16198.2(19) _cell_formula_units_Z 18 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5075 _cell_measurement_theta_min 2.34 _cell_measurement_theta_max 22.43 _exptl_crystal_description Block _exptl_crystal_colour blue _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.331 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 6750 _exptl_absorpt_coefficient_mu 0.795 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.8445 _exptl_absorpt_correction_T_max 0.9106 _exptl_absorpt_process_details 'XPREP (Bruker, 2005a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 67939 _diffrn_reflns_av_R_equivalents 0.0688 _diffrn_reflns_av_sigmaI/netI 0.0465 _diffrn_reflns_limit_h_min -53 _diffrn_reflns_limit_h_max 53 _diffrn_reflns_limit_k_min -53 _diffrn_reflns_limit_k_max 53 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.75 _diffrn_reflns_theta_max 28.26 _reflns_number_total 8841 _reflns_number_gt 6097 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2005b)' _computing_cell_refinement 'APEX 2 (Bruker, 2005b)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0497P)^2^+17.0489P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 8841 _refine_ls_number_parameters 565 _refine_ls_number_restraints 169 _refine_ls_R_factor_all 0.0749 _refine_ls_R_factor_gt 0.0433 _refine_ls_wR_factor_ref 0.1155 _refine_ls_wR_factor_gt 0.1015 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.030 _refine_ls_shift/su_mean 0.001 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 0.91925(7) 0.03872(7) 0.2344(2) 0.0378(6) Uani 1 1 d . . . C2 C 0.93741(7) 0.02750(7) 0.3148(3) 0.0462(6) Uani 1 1 d . . . H2 H 0.9241 0.0137 0.3821 0.055 Uiso 1 1 calc R . . C3 C 0.97515(8) 0.03661(8) 0.2962(3) 0.0610(9) Uani 1 1 d . . . H3 H 0.9879 0.0296 0.3519 0.073 Uiso 1 1 calc R . . C4 C 0.99412(9) 0.05576(10) 0.1976(4) 0.0693(10) Uani 1 1 d . . . H4 H 1.0198 0.0616 0.1850 0.083 Uiso 1 1 calc R . . C5 C 0.97628(9) 0.06654(11) 0.1176(3) 0.0717(10) Uani 1 1 d . . . H5 H 0.9895 0.0798 0.0495 0.086 Uiso 1 1 calc R . . C6 C 0.93882(8) 0.05810(9) 0.1362(3) 0.0546(7) Uani 1 1 d . . . H6 H 0.9265 0.0657 0.0807 0.066 Uiso 1 1 calc R . . C7 C 0.87906(6) 0.03094(7) 0.2535(2) 0.0341(5) Uani 1 1 d . A . C8 C 0.82301(7) -0.00335(7) 0.3615(2) 0.0387(5) Uani 1 1 d . A . C9 C 0.76299(18) -0.00578(18) 0.3460(5) 0.0334(12) Uani 0.80 1 d PDU A 1 C10 C 0.75398(14) 0.00551(15) 0.4497(4) 0.0384(11) Uani 0.80 1 d PDU A 1 C11 C 0.71506(15) -0.01034(16) 0.4839(5) 0.0436(12) Uani 0.80 1 d PDU A 1 H11 H 0.7088 -0.0029 0.5549 0.052 Uiso 0.80 1 calc PR A 1 C12 C 0.68689(14) -0.03624(15) 0.4142(5) 0.0462(11) Uani 0.80 1 d PDU A 1 H12 H 0.6608 -0.0470 0.4367 0.055 Uiso 0.80 1 calc PR A 1 C13 C 0.69587(14) -0.04716(15) 0.3104(5) 0.0453(11) Uani 0.80 1 d PDU A 1 H13 H 0.6756 -0.0648 0.2619 0.054 Uiso 0.80 1 calc PR A 1 C14 C 0.73302(15) -0.03335(16) 0.2756(5) 0.0366(12) Uani 0.80 1 d PDU A 1 H14 H 0.7386 -0.0421 0.2058 0.044 Uiso 0.80 1 calc PR A 1 Cl1 Cl 0.79162(3) 0.04052(3) 0.53623(8) 0.0571(2) Uani 0.80 1 d PD A 1 C9B C 0.7679(7) 0.0007(6) 0.3686(18) 0.028(6) Uani 0.20 1 d PDU A 2 C10B C 0.7371(6) -0.0271(5) 0.3037(13) 0.020(4) Uani 0.20 1 d PDU A 2 C11B C 0.6982(6) -0.0423(6) 0.3471(15) 0.040(6) Uani 0.20 1 d PDU A 2 H11B H 0.6766 -0.0609 0.3050 0.048 Uiso 0.20 1 calc PR A 2 C12B C 0.6943(6) -0.0289(6) 0.4486(14) 0.035(5) Uani 0.20 1 d PDU A 2 H12B H 0.6693 -0.0387 0.4796 0.041 Uiso 0.20 1 calc PR A 2 C13B C 0.7248(5) -0.0017(6) 0.5100(17) 0.036(5) Uani 0.20 1 d PDU A 2 H13B H 0.7201 0.0064 0.5822 0.043 Uiso 0.20 1 calc PR A 2 C14B C 0.7620(6) 0.0144(6) 0.4721(18) 0.048(7) Uani 0.20 1 d PDU A 2 H14B H 0.7828 0.0340 0.5148 0.058 Uiso 0.20 1 calc PR A 2 Cl1B Cl 0.74822(17) -0.04127(17) 0.1694(7) 0.111(2) Uani 0.20 1 d PD A 2 C15 C 0.82441(8) -0.04608(8) 0.5227(2) 0.0479(7) Uani 1 1 d . A . C16 C 0.85500(10) -0.01364(9) 0.5946(3) 0.0619(8) Uani 1 1 d . . . H16A H 0.8764 0.0037 0.5445 0.093 Uiso 1 1 calc R . . H16B H 0.8644 -0.0243 0.6542 0.093 Uiso 1 1 calc R . . H16C H 0.8440 0.0006 0.6315 0.093 Uiso 1 1 calc R . . C17 C 0.84029(9) -0.06821(8) 0.4584(3) 0.0553(7) Uani 1 1 d . . . H17A H 0.8204 -0.0872 0.4072 0.083 Uiso 1 1 calc R . . H17B H 0.8481 -0.0814 0.5143 0.083 Uiso 1 1 calc R . . H17C H 0.8626 -0.0503 0.4123 0.083 Uiso 1 1 calc R . . C18 C 0.79154(10) -0.07397(12) 0.6006(3) 0.0872(13) Uani 1 1 d . . . H18A H 0.7797 -0.0605 0.6378 0.131 Uiso 1 1 calc R . . H18B H 0.8015 -0.0840 0.6600 0.131 Uiso 1 1 calc R . . H18C H 0.7723 -0.0953 0.5540 0.131 Uiso 1 1 calc R . . C51 C 0.73195(6) 0.07474(6) 0.18269(19) 0.0295(5) Uani 1 1 d . . . C52 C 0.71307(7) 0.05545(8) 0.2821(2) 0.0437(6) Uani 1 1 d . . . H52 H 0.7234 0.0431 0.3276 0.052 Uiso 1 1 calc R . . C53 C 0.67937(8) 0.05394(8) 0.3162(3) 0.0504(7) Uani 1 1 d . . . H53 H 0.6668 0.0407 0.3850 0.061 Uiso 1 1 calc R . . C54 C 0.66418(7) 0.07159(8) 0.2504(2) 0.0459(6) Uani 1 1 d . . . H54 H 0.6412 0.0708 0.2741 0.055 Uiso 1 1 calc R . . C55 C 0.68237(8) 0.09039(8) 0.1502(2) 0.0472(6) Uani 1 1 d . . . H55 H 0.6716 0.1021 0.1038 0.057 Uiso 1 1 calc R . . C56 C 0.71639(7) 0.09233(7) 0.1169(2) 0.0396(6) Uani 1 1 d . . . H56 H 0.7291 0.1058 0.0485 0.048 Uiso 1 1 calc R . . C57 C 0.76893(6) 0.07659(6) 0.14924(19) 0.0287(5) Uani 1 1 d . A . C58 C 0.82297(6) 0.10703(7) 0.03064(19) 0.0329(5) Uani 1 1 d . A . C59 C 0.87866(9) 0.10325(10) 0.0234(3) 0.0330(7) Uani 0.80 1 d PDU A 1 C60 C 0.91012(12) 0.13337(13) 0.0746(4) 0.0514(11) Uani 0.80 1 d PDU A 1 H60 H 0.9065 0.1443 0.1428 0.062 Uiso 0.80 1 calc PR A 1 C61 C 0.94680(11) 0.14839(12) 0.0313(4) 0.0665(11) Uani 0.80 1 d PDU A 1 H61 H 0.9679 0.1696 0.0679 0.080 Uiso 0.80 1 calc PR A 1 C62 C 0.95197(15) 0.13232(16) -0.0638(5) 0.0673(14) Uani 0.80 1 d PDU A 1 H62 H 0.9772 0.1423 -0.0936 0.081 Uiso 0.80 1 calc PR A 1 C63 C 0.92220(13) 0.10215(17) -0.1192(4) 0.0626(12) Uani 0.80 1 d PDU A 1 H63 H 0.9265 0.0914 -0.1869 0.075 Uiso 0.80 1 calc PR A 1 C64 C 0.88507(10) 0.08741(11) -0.0735(3) 0.0457(8) Uani 0.80 1 d PDU A 1 Cl2 Cl 0.84673(4) 0.04958(4) -0.14138(12) 0.0924(5) Uani 0.80 1 d P A 1 C59B C 0.8708(4) 0.0867(3) -0.0134(12) 0.035(3) Uani 0.20 1 d PDU A 2 C60B C 0.8641(4) 0.0574(4) -0.0898(10) 0.037(3) Uani 0.20 1 d PDU A 2 H60B H 0.8393 0.0355 -0.0969 0.044 Uiso 0.20 1 calc PR A 2 C61B C 0.8946(4) 0.0610(4) -0.1554(12) 0.059(4) Uani 0.20 1 d PDU A 2 H61B H 0.8905 0.0414 -0.2091 0.071 Uiso 0.20 1 calc PR A 2 C62B C 0.9286(5) 0.0907(5) -0.1446(17) 0.064(5) Uani 0.20 1 d PDU A 2 H62B H 0.9489 0.0915 -0.1888 0.076 Uiso 0.20 1 calc PR A 2 C63B C 0.9365(6) 0.1199(7) -0.0754(19) 0.067(7) Uani 0.20 1 d PDU A 2 H63B H 0.9614 0.1421 -0.0751 0.080 Uiso 0.20 1 calc PR A 2 C64B C 0.9067(4) 0.1177(4) 0.0002(13) 0.048(3) Uani 0.20 1 d PDU A 2 Cl2B Cl 0.91511(15) 0.15249(16) 0.0949(5) 0.0706(14) Uani 0.20 1 d P A 2 C65 C 0.82840(7) 0.16208(7) -0.0931(2) 0.0402(6) Uani 1 1 d . A . C66 C 0.82277(9) 0.18391(8) 0.0052(2) 0.0505(7) Uani 1 1 d . . . H66A H 0.8002 0.1662 0.0507 0.076 Uiso 1 1 calc R . . H66B H 0.8190 0.2043 -0.0267 0.076 Uiso 1 1 calc R . . H66C H 0.8455 0.1952 0.0551 0.076 Uiso 1 1 calc R . . C67 C 0.79246(8) 0.14078(8) -0.1665(2) 0.0522(7) Uani 1 1 d . . . H67A H 0.7971 0.1270 -0.2287 0.078 Uiso 1 1 calc R . . H67B H 0.7859 0.1592 -0.2000 0.078 Uiso 1 1 calc R . . H67C H 0.7712 0.1224 -0.1181 0.078 Uiso 1 1 calc R . . C68 C 0.86239(9) 0.19044(10) -0.1679(3) 0.0674(9) Uani 1 1 d . . . H68A H 0.8854 0.2037 -0.1196 0.101 Uiso 1 1 calc R . . H68B H 0.8566 0.2093 -0.2020 0.101 Uiso 1 1 calc R . . H68C H 0.8668 0.1764 -0.2296 0.101 Uiso 1 1 calc R . . Cu1 Cu 0.822049(7) 0.050390(8) 0.19174(2) 0.02962(9) Uani 1 1 d . A . N1 N 0.86006(6) 0.00745(6) 0.33776(18) 0.0385(5) Uani 1 1 d . . . N2 N 0.80289(5) 0.01092(6) 0.31186(18) 0.0374(5) Uani 1 1 d . . . N3 N 0.80628(7) -0.03159(7) 0.4407(2) 0.0505(6) Uani 1 1 d . . . N51 N 0.78795(5) 0.10050(5) 0.06559(16) 0.0316(4) Uani 1 1 d . . . N52 N 0.84057(5) 0.08844(6) 0.06754(17) 0.0369(5) Uani 1 1 d . . . N53 N 0.84006(7) 0.13514(7) -0.0490(2) 0.0457(6) Uani 1 1 d . . . O1 O 0.86811(5) 0.04811(5) 0.18399(15) 0.0436(4) Uani 1 1 d . . . O51 O 0.77761(5) 0.05532(5) 0.20742(15) 0.0390(4) Uani 1 1 d . . . H1 H 0.7838(8) -0.0375(8) 0.462(2) 0.047(8) Uiso 1 1 d . . . H51 H 0.8605(9) 0.1388(9) -0.067(3) 0.057(9) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0317(12) 0.0332(12) 0.0509(15) -0.0091(11) -0.0004(11) 0.0178(10) C2 0.0397(14) 0.0362(13) 0.0705(19) -0.0034(13) -0.0017(13) 0.0249(12) C3 0.0422(16) 0.0496(17) 0.102(3) -0.0016(17) -0.0034(17) 0.0309(14) C4 0.0380(16) 0.065(2) 0.115(3) 0.001(2) 0.0105(18) 0.0339(16) C5 0.0440(17) 0.089(3) 0.086(2) 0.008(2) 0.0202(17) 0.0361(18) C6 0.0400(15) 0.073(2) 0.0555(18) 0.0020(15) 0.0055(13) 0.0317(15) C7 0.0312(12) 0.0349(12) 0.0370(13) -0.0077(10) -0.0040(10) 0.0172(10) C8 0.0363(13) 0.0414(14) 0.0398(14) 0.0065(11) 0.0013(11) 0.0205(11) C9 0.036(3) 0.033(2) 0.035(2) 0.0070(19) 0.003(2) 0.020(2) C10 0.043(2) 0.035(2) 0.036(2) 0.0059(18) 0.0035(18) 0.0188(18) C11 0.044(3) 0.044(3) 0.045(3) 0.012(2) 0.011(2) 0.024(2) C12 0.039(2) 0.047(2) 0.054(3) 0.014(2) 0.009(2) 0.0220(19) C13 0.038(2) 0.040(2) 0.056(3) 0.002(2) -0.001(2) 0.0180(16) C14 0.031(2) 0.038(2) 0.038(2) 0.0023(19) -0.0029(18) 0.0152(17) Cl1 0.0700(6) 0.0547(5) 0.0456(5) -0.0080(4) 0.0012(4) 0.0303(5) C9B 0.028(7) 0.029(7) 0.030(7) 0.010(4) -0.003(4) 0.015(5) C10B 0.017(5) 0.020(5) 0.021(6) -0.001(4) 0.000(4) 0.008(4) C11B 0.039(7) 0.040(7) 0.035(7) 0.003(4) -0.003(4) 0.015(4) C12B 0.036(7) 0.034(6) 0.029(6) -0.002(4) 0.002(4) 0.014(4) C13B 0.033(6) 0.034(6) 0.033(6) 0.005(4) -0.004(4) 0.011(4) C14B 0.051(8) 0.049(8) 0.048(8) 0.002(4) 0.003(4) 0.026(5) Cl1B 0.080(4) 0.083(4) 0.157(6) -0.019(4) -0.021(4) 0.031(3) C15 0.0465(15) 0.0570(17) 0.0490(16) 0.0187(13) 0.0028(12) 0.0325(14) C16 0.085(2) 0.073(2) 0.0505(18) -0.0008(15) -0.0099(16) 0.057(2) C17 0.0637(19) 0.0477(16) 0.0596(19) 0.0045(14) -0.0077(15) 0.0316(15) C18 0.068(2) 0.118(3) 0.087(3) 0.065(2) 0.021(2) 0.056(2) C51 0.0266(11) 0.0271(11) 0.0329(12) -0.0005(9) 0.0019(9) 0.0119(9) C52 0.0412(14) 0.0510(15) 0.0466(15) 0.0156(12) 0.0128(12) 0.0289(13) C53 0.0452(15) 0.0574(17) 0.0526(16) 0.0148(14) 0.0191(13) 0.0286(14) C54 0.0353(13) 0.0517(16) 0.0539(16) -0.0031(13) 0.0071(12) 0.0243(12) C55 0.0422(14) 0.0558(16) 0.0537(16) 0.0042(13) -0.0020(12) 0.0319(13) C56 0.0358(13) 0.0462(14) 0.0384(14) 0.0069(11) 0.0036(11) 0.0217(11) C57 0.0288(11) 0.0261(11) 0.0290(11) -0.0026(9) 0.0004(9) 0.0121(9) C58 0.0307(12) 0.0377(12) 0.0257(11) 0.0032(9) 0.0032(9) 0.0137(10) C59 0.0294(16) 0.0388(17) 0.0298(16) 0.0052(14) 0.0074(13) 0.0163(14) C60 0.040(2) 0.050(2) 0.056(3) -0.006(2) 0.0034(17) 0.016(2) C61 0.0373(18) 0.066(2) 0.080(3) -0.004(2) 0.0056(18) 0.0143(17) C62 0.043(2) 0.081(3) 0.070(3) 0.013(2) 0.017(2) 0.024(2) C63 0.065(3) 0.080(3) 0.048(2) 0.002(2) 0.019(2) 0.040(2) C64 0.0399(17) 0.059(2) 0.0331(17) -0.0044(15) 0.0048(14) 0.0213(16) Cl2 0.0635(7) 0.1109(10) 0.0856(9) -0.0612(8) -0.0095(6) 0.0307(7) C59B 0.037(5) 0.033(5) 0.031(5) 0.000(4) 0.000(4) 0.015(4) C60B 0.037(5) 0.035(5) 0.040(5) 0.008(4) 0.005(4) 0.019(4) C61B 0.062(5) 0.064(6) 0.056(6) 0.002(4) 0.010(4) 0.035(4) C62B 0.071(7) 0.066(7) 0.060(7) 0.002(4) 0.001(4) 0.039(5) C63B 0.064(8) 0.068(8) 0.062(8) 0.003(5) 0.001(5) 0.028(5) C64B 0.050(5) 0.047(5) 0.049(5) 0.001(4) 0.007(4) 0.027(4) Cl2B 0.050(2) 0.072(3) 0.067(3) -0.022(3) -0.001(2) 0.014(3) C65 0.0427(14) 0.0389(13) 0.0342(13) 0.0109(11) 0.0034(11) 0.0169(11) C66 0.0607(18) 0.0421(15) 0.0418(15) -0.0038(12) -0.0101(13) 0.0204(14) C67 0.0649(18) 0.0605(18) 0.0312(13) -0.0002(12) -0.0095(13) 0.0314(15) C68 0.065(2) 0.068(2) 0.064(2) 0.0379(17) 0.0202(16) 0.0288(17) Cu1 0.02649(15) 0.03333(16) 0.02909(15) 0.00407(11) 0.00345(11) 0.01500(12) N1 0.0318(10) 0.0417(11) 0.0437(12) 0.0059(9) 0.0005(9) 0.0197(9) N2 0.0301(10) 0.0438(11) 0.0410(11) 0.0129(9) 0.0065(9) 0.0204(9) N3 0.0372(12) 0.0626(15) 0.0579(15) 0.0292(12) 0.0100(11) 0.0297(12) N51 0.0294(10) 0.0350(10) 0.0286(10) 0.0049(8) 0.0031(8) 0.0148(8) N52 0.0282(10) 0.0477(12) 0.0345(11) 0.0102(9) 0.0089(8) 0.0188(9) N53 0.0378(12) 0.0554(14) 0.0450(13) 0.0244(11) 0.0174(10) 0.0241(11) O1 0.0336(9) 0.0579(11) 0.0443(10) 0.0159(8) 0.0087(8) 0.0266(9) O51 0.0355(9) 0.0435(9) 0.0444(10) 0.0193(8) 0.0154(7) 0.0244(8) _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 C6 1.380(4) . ? C1 C2 1.390(4) . ? C1 C7 1.501(3) . ? C2 C3 1.389(4) . ? C2 H2 0.9500 . ? C3 C4 1.373(5) . ? C3 H3 0.9500 . ? C4 C5 1.367(5) . ? C4 H4 0.9500 . ? C5 C6 1.386(4) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.273(3) . ? C7 N1 1.305(3) . ? C8 N2 1.333(3) . ? C8 N3 1.348(3) . ? C8 N1 1.356(3) . ? C9 C10 1.393(7) . ? C9 C14 1.417(7) . ? C9 N2 1.451(6) . ? C10 C11 1.419(6) . ? C10 Cl1 1.773(6) . ? C11 C12 1.356(7) . ? C11 H11 0.9500 . ? C12 C13 1.387(7) . ? C12 H12 0.9500 . ? C13 C14 1.368(6) . ? C13 H13 0.9500 . ? C14 H14 0.9500 . ? C9B C14B 1.386(19) . ? C9B C10B 1.402(17) . ? C9B N2 1.41(3) . ? C10B C11B 1.454(18) . ? C10B Cl1B 1.786(15) . ? C11B C12B 1.334(18) . ? C11B H11B 0.9500 . ? C12B C13B 1.364(15) . ? C12B H12B 0.9500 . ? C13B C14B 1.372(18) . ? C13B H13B 0.9500 . ? C14B H14B 0.9500 . ? C15 N3 1.482(3) . ? C15 C16 1.517(4) . ? C15 C17 1.524(4) . ? C15 C18 1.528(4) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C51 C52 1.382(3) . ? C51 C56 1.384(3) . ? C51 C57 1.502(3) . ? C52 C53 1.384(3) . ? C52 H52 0.9500 . ? C53 C54 1.375(4) . ? C53 H53 0.9500 . ? C54 C55 1.377(4) . ? C54 H54 0.9500 . ? C55 C56 1.386(3) . ? C55 H55 0.9500 . ? C56 H56 0.9500 . ? C57 O51 1.267(3) . ? C57 N51 1.308(3) . ? C58 N52 1.331(3) . ? C58 N53 1.350(3) . ? C58 N51 1.359(3) . ? C59 C60 1.373(5) . ? C59 C64 1.376(4) . ? C59 N52 1.432(3) . ? C60 C61 1.379(6) . ? C60 H60 0.9500 . ? C61 C62 1.344(6) . ? C61 H61 0.9500 . ? C62 C63 1.365(7) . ? C62 H62 0.9500 . ? C63 C64 1.405(5) . ? C63 H63 0.9500 . ? C64 Cl2 1.721(4) . ? C59B C64B 1.362(14) . ? C59B C60B 1.387(15) . ? C59B N52 1.564(15) . ? C60B C61B 1.386(14) . ? C60B H60B 0.9500 . ? C61B C62B 1.296(16) . ? C61B H61B 0.9500 . ? C62B C63B 1.323(17) . ? C62B H62B 0.9500 . ? C63B C64B 1.451(17) . ? C63B H63B 0.9500 . ? C64B Cl2B 1.674(14) . ? C65 N53 1.471(3) . ? C65 C67 1.518(4) . ? C65 C66 1.521(4) . ? C65 C68 1.535(4) . ? C66 H66A 0.9800 . ? C66 H66B 0.9800 . ? C66 H66C 0.9800 . ? C67 H67A 0.9800 . ? C67 H67B 0.9800 . ? C67 H67C 0.9800 . ? C68 H68A 0.9800 . ? C68 H68B 0.9800 . ? C68 H68C 0.9800 . ? Cu1 O1 1.9022(16) . ? Cu1 O51 1.9031(15) . ? Cu1 N52 1.9543(19) . ? Cu1 N2 1.9543(19) . ? N3 H1 0.85(3) . ? N53 H51 0.79(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 C6 C1 C2 119.3(2) . . ? C6 C1 C7 119.3(2) . . ? C2 C1 C7 121.3(2) . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 120.3(3) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 120.4(3) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 119.8(3) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 120.6(3) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O1 C7 N1 128.9(2) . . ? O1 C7 C1 115.0(2) . . ? N1 C7 C1 116.1(2) . . ? N2 C8 N3 120.0(2) . . ? N2 C8 N1 125.6(2) . . ? N3 C8 N1 114.4(2) . . ? C10 C9 C14 119.4(5) . . ? C10 C9 N2 119.4(5) . . ? C14 C9 N2 121.2(5) . . ? C9 C10 C11 120.1(5) . . ? C9 C10 Cl1 119.1(4) . . ? C11 C10 Cl1 120.8(4) . . ? C12 C11 C10 119.4(5) . . ? C12 C11 H11 120.3 . . ? C10 C11 H11 120.3 . . ? C11 C12 C13 120.5(5) . . ? C11 C12 H12 119.7 . . ? C13 C12 H12 119.7 . . ? C14 C13 C12 122.0(5) . . ? C14 C13 H13 119.0 . . ? C12 C13 H13 119.0 . . ? C13 C14 C9 118.6(5) . . ? C13 C14 H14 120.7 . . ? C9 C14 H14 120.7 . . ? C14B C9B C10B 121(2) . . ? C14B C9B N2 128.9(18) . . ? C10B C9B N2 109.7(16) . . ? C9B C10B C11B 119.2(17) . . ? C9B C10B Cl1B 117.2(14) . . ? C11B C10B Cl1B 123.6(13) . . ? C12B C11B C10B 116.9(17) . . ? C12B C11B H11B 121.5 . . ? C10B C11B H11B 121.5 . . ? C11B C12B C13B 123(2) . . ? C11B C12B H12B 118.6 . . ? C13B C12B H12B 118.6 . . ? C12B C13B C14B 123(2) . . ? C12B C13B H13B 118.5 . . ? C14B C13B H13B 118.5 . . ? C13B C14B C9B 117(2) . . ? C13B C14B H14B 121.6 . . ? C9B C14B H14B 121.6 . . ? N3 C15 C16 111.0(2) . . ? N3 C15 C17 110.5(2) . . ? C16 C15 C17 111.9(2) . . ? N3 C15 C18 104.5(2) . . ? C16 C15 C18 109.9(3) . . ? C17 C15 C18 108.7(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 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C15 C18 H18A 109.5 . . ? C15 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C15 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C52 C51 C56 118.8(2) . . ? C52 C51 C57 119.6(2) . . ? C56 C51 C57 121.5(2) . . ? C51 C52 C53 120.9(2) . . ? C51 C52 H52 119.6 . . ? C53 C52 H52 119.6 . . ? C54 C53 C52 119.9(2) . . ? C54 C53 H53 120.0 . . ? C52 C53 H53 120.0 . . ? C53 C54 C55 119.8(2) . . ? C53 C54 H54 120.1 . . ? C55 C54 H54 120.1 . . ? C54 C55 C56 120.2(2) . . ? C54 C55 H55 119.9 . . ? C56 C55 H55 119.9 . . ? C51 C56 C55 120.3(2) . . ? C51 C56 H56 119.9 . . ? C55 C56 H56 119.9 . . ? O51 C57 N51 129.2(2) . . ? O51 C57 C51 115.49(19) . . ? N51 C57 C51 115.31(19) . . ? N52 C58 N53 119.9(2) . . ? N52 C58 N51 126.0(2) . . ? N53 C58 N51 114.2(2) . . ? C60 C59 C64 117.2(3) . . ? C60 C59 N52 122.4(3) . . ? C64 C59 N52 120.4(3) . . ? C59 C60 C61 122.8(4) . . ? C59 C60 H60 118.6 . . ? C61 C60 H60 118.6 . . ? C62 C61 C60 118.4(4) . . ? C62 C61 H61 120.8 . . ? C60 C61 H61 120.8 . . ? C61 C62 C63 122.3(5) . . ? C61 C62 H62 118.9 . . ? C63 C62 H62 118.9 . . ? C62 C63 C64 118.3(5) . . ? C62 C63 H63 120.9 . . ? C64 C63 H63 120.9 . . ? C59 C64 C63 121.1(4) . . ? C59 C64 Cl2 119.2(3) . . ? C63 C64 Cl2 119.7(3) . . ? C64B C59B C60B 121.1(14) . . ? C64B C59B N52 112.5(11) . . ? C60B C59B N52 126.4(10) . . ? C61B C60B C59B 118.3(14) . . ? C61B C60B H60B 120.8 . . ? C59B C60B H60B 120.8 . . ? C62B C61B C60B 120.9(17) . . ? C62B C61B H61B 119.5 . . ? C60B C61B H61B 119.5 . . ? C61B C62B C63B 123(2) . . ? C61B C62B H62B 118.3 . . ? C63B C62B H62B 118.3 . . ? C62B C63B C64B 119(2) . . ? C62B C63B H63B 120.5 . . ? C64B C63B H63B 120.5 . . ? C59B C64B C63B 116.9(15) . . ? C59B C64B Cl2B 121.3(11) . . ? C63B C64B Cl2B 121.7(13) . . ? N53 C65 C67 110.0(2) . . ? N53 C65 C66 111.1(2) . . ? C67 C65 C66 111.6(2) . . ? N53 C65 C68 104.4(2) . . ? C67 C65 C68 110.4(2) . . ? C66 C65 C68 109.0(2) . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C65 C67 H67A 109.5 . . ? C65 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? C65 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? C65 C68 H68A 109.5 . . ? C65 C68 H68B 109.5 . . ? H68A C68 H68B 109.5 . . ? C65 C68 H68C 109.5 . . ? H68A C68 H68C 109.5 . . ? H68B C68 H68C 109.5 . . ? O1 Cu1 O51 176.07(8) . . ? O1 Cu1 N52 90.23(7) . . ? O51 Cu1 N52 89.91(7) . . ? O1 Cu1 N2 89.56(7) . . ? O51 Cu1 N2 90.43(7) . . ? N52 Cu1 N2 177.99(9) . . ? C7 N1 C8 122.3(2) . . ? C8 N2 C9B 113.9(10) . . ? C8 N2 C9 116.9(3) . . ? C9B N2 C9 14.1(9) . . ? C8 N2 Cu1 125.29(16) . . ? C9B N2 Cu1 119.8(10) . . ? C9 N2 Cu1 117.7(3) . . ? C8 N3 C15 129.0(2) . . ? C8 N3 H1 116.3(19) . . ? C15 N3 H1 111.9(19) . . ? C57 N51 C58 122.05(19) . . ? C58 N52 C59 114.3(2) . . ? C58 N52 C59B 118.5(5) . . ? C59 N52 C59B 27.2(4) . . ? C58 N52 Cu1 125.02(15) . . ? C59 N52 Cu1 119.82(17) . . ? C59B N52 Cu1 113.9(5) . . ? C58 N53 C65 129.6(2) . . ? C58 N53 H51 113(2) . . ? C65 N53 H51 117(2) . . ? C7 O1 Cu1 127.29(15) . . ? C57 O51 Cu1 127.60(14) . . ? 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 C6 C1 C2 C3 1.3(4) . . . . ? C7 C1 C2 C3 -177.4(2) . . . . ? C1 C2 C3 C4 -1.6(4) . . . . ? C2 C3 C4 C5 0.9(5) . . . . ? C3 C4 C5 C6 0.1(5) . . . . ? C2 C1 C6 C5 -0.3(4) . . . . ? C7 C1 C6 C5 178.4(3) . . . . ? C4 C5 C6 C1 -0.4(5) . . . . ? C6 C1 C7 O1 -9.9(3) . . . . ? C2 C1 C7 O1 168.7(2) . . . . ? C6 C1 C7 N1 169.6(2) . . . . ? C2 C1 C7 N1 -11.8(3) . . . . ? C14 C9 C10 C11 -0.4(7) . . . . ? N2 C9 C10 C11 179.5(5) . . . . ? C14 C9 C10 Cl1 -179.1(4) . . . . ? N2 C9 C10 Cl1 0.8(6) . . . . ? C9 C10 C11 C12 -0.5(7) . . . . ? Cl1 C10 C11 C12 178.1(4) . . . . ? C10 C11 C12 C13 -0.1(8) . . . . ? C11 C12 C13 C14 1.9(8) . . . . ? C12 C13 C14 C9 -2.8(6) . . . . ? C10 C9 C14 C13 2.1(6) . . . . ? N2 C9 C14 C13 -177.9(5) . . . . ? C14B C9B C10B C11B -1.0(18) . . . . ? N2 C9B C10B C11B 179.0(18) . . . . ? C14B C9B C10B Cl1B 177.9(19) . . . . ? N2 C9B C10B Cl1B -2.1(18) . . . . ? C9B C10B C11B C12B -0.9(18) . . . . ? Cl1B C10B C11B C12B -179.7(19) . . . . ? C10B C11B C12B C13B 1(3) . . . . ? C11B C12B C13B C14B 1(4) . . . . ? C12B C13B C14B C9B -2(3) . . . . ? C10B C9B C14B C13B 3(3) . . . . ? N2 C9B C14B C13B -177(2) . . . . ? C56 C51 C52 C53 -0.6(4) . . . . ? C57 C51 C52 C53 178.7(2) . . . . ? C51 C52 C53 C54 0.4(4) . . . . ? C52 C53 C54 C55 0.6(4) . . . . ? C53 C54 C55 C56 -1.5(4) . . . . ? C52 C51 C56 C55 -0.3(4) . . . . ? C57 C51 C56 C55 -179.5(2) . . . . ? C54 C55 C56 C51 1.3(4) . . . . ? C52 C51 C57 O51 9.6(3) . . . . ? C56 C51 C57 O51 -171.1(2) . . . . ? C52 C51 C57 N51 -169.1(2) . . . . ? C56 C51 C57 N51 10.1(3) . . . . ? C64 C59 C60 C61 1.6(6) . . . . ? N52 C59 C60 C61 -178.5(4) . . . . ? C59 C60 C61 C62 -1.3(7) . . . . ? C60 C61 C62 C63 0.8(8) . . . . ? C61 C62 C63 C64 -0.7(8) . . . . ? C60 C59 C64 C63 -1.4(6) . . . . ? N52 C59 C64 C63 178.7(3) . . . . ? C60 C59 C64 Cl2 180.0(3) . . . . ? N52 C59 C64 Cl2 0.1(4) . . . . ? C62 C63 C64 C59 1.0(7) . . . . ? C62 C63 C64 Cl2 179.6(4) . . . . ? C64B C59B C60B C61B -2.3(14) . . . . ? N52 C59B C60B C61B 179.6(11) . . . . ? C59B C60B C61B C62B 1.0(16) . . . . ? C60B C61B C62B C63B -3(3) . . . . ? C61B C62B C63B C64B 5(3) . . . . ? C60B C59B C64B C63B 5(2) . . . . ? N52 C59B C64B C63B -176.8(14) . . . . ? C60B C59B C64B Cl2B -178.3(10) . . . . ? N52 C59B C64B Cl2B 0.1(16) . . . . ? C62B C63B C64B C59B -6(3) . . . . ? C62B C63B C64B Cl2B 176.9(16) . . . . ? O1 C7 N1 C8 2.2(4) . . . . ? C1 C7 N1 C8 -177.2(2) . . . . ? N2 C8 N1 C7 -7.0(4) . . . . ? N3 C8 N1 C7 171.5(2) . . . . ? N3 C8 N2 C9B 14.3(9) . . . . ? N1 C8 N2 C9B -167.4(9) . . . . ? N3 C8 N2 C9 -1.0(5) . . . . ? N1 C8 N2 C9 177.4(4) . . . . ? N3 C8 N2 Cu1 -177.6(2) . . . . ? N1 C8 N2 Cu1 0.8(4) . . . . ? C14B C9B N2 C8 74(2) . . . . ? C10B C9B N2 C8 -105.8(12) . . . . ? C14B C9B N2 Cu1 -95(2) . . . . ? C10B C9B N2 Cu1 85.3(14) . . . . ? C10 C9 N2 C8 79.6(5) . . . . ? C14 C9 N2 C8 -100.4(5) . . . . ? C10 C9 N2 Cu1 -103.5(4) . . . . ? C14 C9 N2 Cu1 76.5(5) . . . . ? O1 Cu1 N2 C8 6.3(2) . . . . ? O51 Cu1 N2 C8 -169.8(2) . . . . ? N52 Cu1 N2 C8 90(2) . . . . ? O1 Cu1 N2 C9B 173.8(9) . . . . ? O51 Cu1 N2 C9B -2.3(9) . . . . ? N52 Cu1 N2 C9B -102(2) . . . . ? O1 Cu1 N2 C9 -170.3(3) . . . . ? O51 Cu1 N2 C9 13.6(3) . . . . ? N52 Cu1 N2 C9 -86(2) . . . . ? N2 C8 N3 C15 -166.3(3) . . . . ? N1 C8 N3 C15 15.1(4) . . . . ? C16 C15 N3 C8 53.9(4) . . . . ? C17 C15 N3 C8 -70.9(4) . . . . ? C18 C15 N3 C8 172.4(3) . . . . ? O51 C57 N51 C58 -2.6(4) . . . . ? C51 C57 N51 C58 175.9(2) . . . . ? N52 C58 N51 C57 6.1(4) . . . . ? N53 C58 N51 C57 -174.1(2) . . . . ? N53 C58 N52 C59 5.1(3) . . . . ? N51 C58 N52 C59 -175.1(2) . . . . ? N53 C58 N52 C59B -25.0(6) . . . . ? N51 C58 N52 C59B 154.8(5) . . . . ? N53 C58 N52 Cu1 174.27(18) . . . . ? N51 C58 N52 Cu1 -5.9(3) . . . . ? C60 C59 N52 C58 85.3(4) . . . . ? C64 C59 N52 C58 -94.8(3) . . . . ? C60 C59 N52 C59B -169.2(12) . . . . ? C64 C59 N52 C59B 10.7(11) . . . . ? C60 C59 N52 Cu1 -84.5(4) . . . . ? C64 C59 N52 Cu1 95.4(3) . . . . ? C64B C59B N52 C58 87.0(10) . . . . ? C60B C59B N52 C58 -94.7(10) . . . . ? C64B C59B N52 C59 -1.0(7) . . . . ? C60B C59B N52 C59 177.3(19) . . . . ? C64B C59B N52 Cu1 -110.1(9) . . . . ? C60B C59B N52 Cu1 68.1(11) . . . . ? O1 Cu1 N52 C58 -173.7(2) . . . . ? O51 Cu1 N52 C58 2.3(2) . . . . ? N2 Cu1 N52 C58 102(2) . . . . ? O1 Cu1 N52 C59 -5.1(2) . . . . ? O51 Cu1 N52 C59 171.0(2) . . . . ? N2 Cu1 N52 C59 -89(2) . . . . ? O1 Cu1 N52 C59B 24.7(5) . . . . ? O51 Cu1 N52 C59B -159.2(5) . . . . ? N2 Cu1 N52 C59B -59(2) . . . . ? N52 C58 N53 C65 -172.8(2) . . . . ? N51 C58 N53 C65 7.4(4) . . . . ? C67 C65 N53 C58 -69.6(3) . . . . ? C66 C65 N53 C58 54.6(4) . . . . ? C68 C65 N53 C58 172.0(3) . . . . ? N1 C7 O1 Cu1 8.6(4) . . . . ? C1 C7 O1 Cu1 -171.96(15) . . . . ? O51 Cu1 O1 C7 79.2(11) . . . . ? N52 Cu1 O1 C7 171.3(2) . . . . ? N2 Cu1 O1 C7 -10.7(2) . . . . ? N51 C57 O51 Cu1 -0.7(4) . . . . ? C51 C57 O51 Cu1 -179.20(14) . . . . ? O1 Cu1 O51 C57 92.8(10) . . . . ? N52 Cu1 O51 C57 0.7(2) . . . . ? N2 Cu1 O51 C57 -177.3(2) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.908 _refine_diff_density_min -0.411 _refine_diff_density_rms 0.057 #============================================================================== # 4. TEXT #============================================================================== _publ_section_abstract ; See Text ; _publ_section_comment ; See Text ; _publ_section_exptl_prep ; See text ; _publ_section_exptl_refinement ; The structure was solved by direct method with ShelxS-97. All non-H atoms were refined by full-matrix least-squares with anisotropic displacement parameters while hydrogen atoms were placed in idealized position. ; _publ_section_references ; Bruker (2005a). XPREP. Version 2005/2. Bruker AXS Inc., Madison, WI, USA. Bruker (2005b). APEX 2. Version 1.0.18. Bruker AXS Inc., Madison, WI, USA. Bruker (2003). SAINT. Version 7.23A. Bruker AXS Inc., Madison, WI, USA. Bruker (2001). SHELXTL. Version 6.12. Bruker AXS Inc., Madison, WI, USA. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Flack, H. D. and Schwarzenbach, D. (1988). Acta Cryst. A44, 499-506. Sheldrick, G. M. (1997). SHELXS97 and SHELXL97. University of G\"ottingen, Germany. Sheldrick, G. M. (2004). SADABS. Version 2004/1. Bruker AXS Inc., Madison, WI, USA. Sheldrick, G. M. (2002). TWINABS. Version 1.05. Bruker AXS Inc., Madison, WI, USA. Spek, A. L. (1990). Acta Cryst. A46, C-34. Spek, A. L. (2005). PLATON, A Multipurpose Crystallographic Tool. University of Utrecht, Utrecht, The Netherlands. ; _publ_section_figure_captions ; See text ; _publ_section_table_legends ; See text ; _publ_section_acknowledgements ; See text ; data_bad002 _database_code_depnum_ccdc_archive 'CCDC 816344' #TrackingRef '- compound_1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H18 Cl N3 O' _chemical_formula_weight 315.79 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' _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 13.5978(19) _cell_length_b 11.6143(16) _cell_length_c 20.150(3) _cell_angle_alpha 90.00 _cell_angle_beta 98.910(2) _cell_angle_gamma 90.00 _cell_volume 3143.8(8) _cell_formula_units_Z 8 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2668 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 20.37 _exptl_crystal_description Block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.334 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1328 _exptl_absorpt_coefficient_mu 0.248 _exptl_absorpt_correction_type integration _exptl_absorpt_correction_T_min 0.9428 _exptl_absorpt_correction_T_max 0.9901 _exptl_absorpt_process_details 'XPREP (Bruker, 2005a)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker Smart APEX II CCD' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 28021 _diffrn_reflns_av_R_equivalents 0.0805 _diffrn_reflns_av_sigmaI/netI 0.0584 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.69 _diffrn_reflns_theta_max 24.00 _reflns_number_total 4938 _reflns_number_gt 2967 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX 2 (Bruker, 2005b)' _computing_cell_refinement 'APEX 2 (Bruker, 2005b)' _computing_data_reduction 'SAINT (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'SHELXTL (Bruker, 2001)' _computing_publication_material 'SHELXTL (Bruker, 2001)' _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^)+(0.0620P)^2^+0.4651P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4938 _refine_ls_number_parameters 417 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1000 _refine_ls_R_factor_gt 0.0495 _refine_ls_wR_factor_ref 0.1339 _refine_ls_wR_factor_gt 0.1075 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 Cl1 Cl 0.76485(7) 0.46569(8) 0.07431(4) 0.0546(3) Uani 1 1 d . . . Cl2 Cl 0.89329(7) 0.02267(8) 0.91763(4) 0.0557(3) Uani 1 1 d . . . C7 C 0.8253(2) 0.1944(3) 0.70446(17) 0.0337(8) Uani 1 1 d . . . C8 C 0.8021(2) -0.0046(3) 0.70663(16) 0.0341(8) Uani 1 1 d . . . C9 C 0.8895(2) -0.1109(3) 0.80752(17) 0.0365(8) Uani 1 1 d . . . C2 C 0.8802(2) 0.3957(3) 0.68583(17) 0.0406(8) Uani 1 1 d . . . H2 H 0.8920 0.4055 0.7322 0.049 Uiso 1 1 calc R . . C1 C 0.8437(2) 0.2910(3) 0.65863(16) 0.0328(8) Uani 1 1 d . . . C10 C 0.9183(2) -0.1027(3) 0.87625(17) 0.0394(8) Uani 1 1 d . . . C6 C 0.8266(2) 0.2792(3) 0.58934(17) 0.0415(8) Uani 1 1 d . . . H6 H 0.8032 0.2094 0.5705 0.050 Uiso 1 1 calc R . . C3 C 0.8989(2) 0.4849(3) 0.64453(19) 0.0476(9) Uani 1 1 d . . . H3 H 0.9236 0.5543 0.6632 0.057 Uiso 1 1 calc R . . C14 C 0.9133(2) -0.2132(3) 0.77681(17) 0.0438(9) Uani 1 1 d . . . H14 H 0.8960 -0.2218 0.7306 0.053 Uiso 1 1 calc R . . C15 C 0.7224(2) -0.1018(3) 0.60358(15) 0.0398(8) Uani 1 1 d . . . H15 H 0.7559 -0.0429 0.5804 0.048 Uiso 1 1 calc R . . C12 C 0.9897(3) -0.2903(3) 0.8826(2) 0.0556(10) Uani 1 1 d . . . H12 H 1.0226 -0.3501 0.9076 0.067 Uiso 1 1 calc R . . C13 C 0.9621(3) -0.3009(3) 0.8142(2) 0.0531(10) Uani 1 1 d . . . H13 H 0.9766 -0.3685 0.7930 0.064 Uiso 1 1 calc R . . C11 C 0.9679(2) -0.1899(3) 0.91344(18) 0.0501(10) Uani 1 1 d . . . H11 H 0.9868 -0.1810 0.9595 0.060 Uiso 1 1 calc R . . C4 C 0.8815(3) 0.4720(3) 0.57623(19) 0.0495(9) Uani 1 1 d . . . H4 H 0.8949 0.5323 0.5486 0.059 Uiso 1 1 calc R . . C17 C 0.7453(3) -0.2176(3) 0.57682(18) 0.0625(11) Uani 1 1 d . . . H17A H 0.8161 -0.2273 0.5812 0.094 Uiso 1 1 calc R . . H17B H 0.7166 -0.2229 0.5303 0.094 Uiso 1 1 calc R . . H17C H 0.7179 -0.2767 0.6018 0.094 Uiso 1 1 calc R . . C5 C 0.8436(3) 0.3687(3) 0.54803(18) 0.0494(9) Uani 1 1 d . . . H5 H 0.8298 0.3604 0.5016 0.059 Uiso 1 1 calc R . . C16 C 0.6128(3) -0.0769(4) 0.5919(2) 0.0804(14) Uani 1 1 d . . . H16A H 0.5787 -0.1342 0.6141 0.121 Uiso 1 1 calc R . . H16B H 0.5885 -0.0784 0.5446 0.121 Uiso 1 1 calc R . . H16C H 0.6011 -0.0023 0.6096 0.121 Uiso 1 1 calc R . . O1 O 0.83289(16) 0.21270(17) 0.76624(11) 0.0428(6) Uani 1 1 d . . . N1 N 0.80112(18) 0.0940(2) 0.67282(12) 0.0342(6) Uani 1 1 d . . . N2 N 0.8454(2) -0.0156(2) 0.77193(14) 0.0378(7) Uani 1 1 d . . . N3 N 0.7623(2) -0.0974(3) 0.67460(14) 0.0421(7) Uani 1 1 d . . . C57 C 0.8480(2) 0.2927(2) 0.28601(16) 0.0322(7) Uani 1 1 d . . . C59 C 0.8523(2) 0.5970(3) 0.17774(15) 0.0339(8) Uani 1 1 d . . . C58 C 0.8395(2) 0.4930(3) 0.28519(16) 0.0328(8) Uani 1 1 d . . . C52 C 0.9411(2) 0.2038(3) 0.39134(16) 0.0423(8) Uani 1 1 d . . . H52 H 0.9373 0.2735 0.4135 0.051 Uiso 1 1 calc R . . C51 C 0.8980(2) 0.1937(3) 0.32495(15) 0.0329(8) Uani 1 1 d . . . C65 C 0.8318(2) 0.5925(3) 0.39232(15) 0.0360(8) Uani 1 1 d . . . H65 H 0.8717 0.5275 0.4125 0.043 Uiso 1 1 calc R . . C67 C 0.8819(3) 0.7036(3) 0.41812(17) 0.0474(9) Uani 1 1 d . . . H67A H 0.9487 0.7050 0.4082 0.071 Uiso 1 1 calc R . . H67B H 0.8834 0.7085 0.4658 0.071 Uiso 1 1 calc R . . H67C H 0.8454 0.7677 0.3967 0.071 Uiso 1 1 calc R . . C64 C 0.9009(2) 0.6968(3) 0.20268(17) 0.0415(8) Uani 1 1 d . . . H64 H 0.9237 0.7035 0.2485 0.050 Uiso 1 1 calc R . . C56 C 0.9044(2) 0.0877(3) 0.29344(16) 0.0387(8) Uani 1 1 d . . . H56 H 0.8749 0.0784 0.2489 0.046 Uiso 1 1 calc R . . C60 C 0.8232(2) 0.5895(3) 0.10884(16) 0.0381(8) Uani 1 1 d . . . C61 C 0.8399(3) 0.6781(3) 0.06649(17) 0.0478(9) Uani 1 1 d . . . H61 H 0.8205 0.6705 0.0204 0.057 Uiso 1 1 calc R . . C62 C 0.8850(3) 0.7775(3) 0.09219(19) 0.0506(9) Uani 1 1 d . . . H62 H 0.8948 0.8383 0.0639 0.061 Uiso 1 1 calc R . . C54 C 0.9965(3) 0.0083(3) 0.39323(19) 0.0491(9) Uani 1 1 d . . . H54 H 1.0297 -0.0534 0.4161 0.059 Uiso 1 1 calc R . . C63 C 0.9155(3) 0.7860(3) 0.16005(19) 0.0491(9) Uani 1 1 d . . . H63 H 0.9466 0.8531 0.1777 0.059 Uiso 1 1 calc R . . C55 C 0.9538(3) -0.0035(3) 0.32741(18) 0.0451(9) Uani 1 1 d . . . H55 H 0.9582 -0.0734 0.3055 0.054 Uiso 1 1 calc R . . C53 C 0.9902(3) 0.1115(3) 0.42535(18) 0.0516(10) Uani 1 1 d . . . H53 H 1.0188 0.1196 0.4701 0.062 Uiso 1 1 calc R . . C66 C 0.7275(3) 0.5828(3) 0.41023(18) 0.0548(10) Uani 1 1 d . . . H66A H 0.6885 0.6477 0.3922 0.082 Uiso 1 1 calc R . . H66B H 0.7314 0.5815 0.4582 0.082 Uiso 1 1 calc R . . H66C H 0.6969 0.5131 0.3916 0.082 Uiso 1 1 calc R . . O51 O 0.80201(17) 0.27612(17) 0.22829(11) 0.0422(6) Uani 1 1 d . . . N51 N 0.85786(18) 0.3945(2) 0.31841(12) 0.0337(6) Uani 1 1 d . . . N52 N 0.8372(2) 0.5009(2) 0.21752(14) 0.0370(7) Uani 1 1 d . . . N53 N 0.8279(2) 0.5884(2) 0.31995(14) 0.0359(7) Uani 1 1 d . . . H40 H 0.853(2) 0.047(3) 0.7936(15) 0.034(10) Uiso 1 1 d . . . H90 H 0.823(3) 0.437(3) 0.1953(18) 0.067(13) Uiso 1 1 d . . . H91 H 0.803(2) 0.643(3) 0.2976(15) 0.035(10) Uiso 1 1 d . . . H41 H 0.749(2) -0.154(3) 0.6972(16) 0.049(11) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0621(6) 0.0604(6) 0.0403(5) -0.0086(5) 0.0048(4) -0.0100(5) Cl2 0.0617(6) 0.0596(6) 0.0440(6) -0.0070(5) 0.0021(4) 0.0066(5) C7 0.0266(18) 0.0328(19) 0.041(2) -0.0011(16) 0.0021(15) 0.0023(14) C8 0.0324(18) 0.037(2) 0.035(2) -0.0041(16) 0.0118(15) -0.0017(15) C9 0.0311(19) 0.0321(19) 0.047(2) 0.0055(17) 0.0092(16) 0.0010(15) C2 0.039(2) 0.035(2) 0.047(2) -0.0012(17) 0.0022(16) 0.0042(15) C1 0.0243(17) 0.0309(18) 0.043(2) 0.0009(15) 0.0056(14) 0.0040(14) C10 0.0339(19) 0.041(2) 0.044(2) 0.0040(17) 0.0094(16) -0.0010(15) C6 0.043(2) 0.035(2) 0.045(2) 0.0015(17) 0.0035(17) 0.0011(15) C3 0.043(2) 0.032(2) 0.066(3) -0.0003(18) 0.0041(19) -0.0042(16) C14 0.042(2) 0.045(2) 0.046(2) -0.0008(18) 0.0109(17) 0.0000(17) C15 0.055(2) 0.0340(19) 0.0312(19) -0.0009(16) 0.0083(16) -0.0069(16) C12 0.047(2) 0.048(2) 0.070(3) 0.014(2) 0.004(2) 0.0053(18) C13 0.048(2) 0.042(2) 0.071(3) 0.005(2) 0.014(2) 0.0088(18) C11 0.041(2) 0.058(3) 0.050(2) 0.012(2) 0.0026(17) -0.0010(18) C4 0.048(2) 0.041(2) 0.061(3) 0.010(2) 0.0100(19) -0.0001(17) C17 0.095(3) 0.044(2) 0.052(2) -0.0082(19) 0.021(2) -0.002(2) C5 0.054(2) 0.049(2) 0.044(2) 0.0053(18) 0.0053(18) 0.0024(18) C16 0.059(3) 0.116(4) 0.062(3) -0.011(3) -0.005(2) 0.024(3) O1 0.0567(16) 0.0344(13) 0.0369(14) -0.0054(11) 0.0065(11) 0.0014(11) N1 0.0347(16) 0.0310(16) 0.0372(16) 0.0003(13) 0.0062(12) -0.0004(12) N2 0.0452(18) 0.0309(17) 0.0374(18) -0.0043(15) 0.0064(14) 0.0003(14) N3 0.059(2) 0.0318(17) 0.0356(18) 0.0016(15) 0.0075(14) -0.0063(15) C57 0.0325(19) 0.0295(18) 0.036(2) -0.0008(15) 0.0091(15) -0.0049(14) C59 0.0305(18) 0.0354(19) 0.037(2) 0.0038(16) 0.0076(15) 0.0059(15) C58 0.0289(18) 0.034(2) 0.035(2) -0.0041(15) 0.0014(14) -0.0013(14) C52 0.052(2) 0.0326(19) 0.043(2) 0.0009(16) 0.0098(17) 0.0023(16) C51 0.0304(18) 0.0299(18) 0.040(2) 0.0005(15) 0.0108(15) -0.0038(14) C65 0.045(2) 0.0292(18) 0.033(2) 0.0001(15) 0.0032(15) 0.0034(15) C67 0.057(2) 0.040(2) 0.043(2) -0.0045(17) 0.0013(17) -0.0014(17) C64 0.042(2) 0.039(2) 0.044(2) 0.0002(17) 0.0091(16) -0.0010(16) C56 0.037(2) 0.0360(19) 0.043(2) -0.0031(17) 0.0084(16) -0.0022(15) C60 0.0341(19) 0.043(2) 0.037(2) -0.0004(17) 0.0056(15) 0.0028(15) C61 0.043(2) 0.063(3) 0.038(2) 0.0056(19) 0.0070(17) 0.0097(19) C62 0.058(2) 0.045(2) 0.051(3) 0.0127(19) 0.0148(19) 0.0033(19) C54 0.047(2) 0.036(2) 0.064(3) 0.0087(19) 0.0091(19) 0.0039(16) C63 0.051(2) 0.041(2) 0.058(3) 0.0007(19) 0.0152(19) -0.0054(17) C55 0.049(2) 0.030(2) 0.057(2) -0.0028(17) 0.0135(19) 0.0023(16) C53 0.061(3) 0.046(2) 0.047(2) 0.0043(19) 0.0029(19) 0.0007(19) C66 0.058(3) 0.056(2) 0.053(2) 0.0003(19) 0.0175(19) -0.0085(19) O51 0.0499(15) 0.0336(13) 0.0407(15) -0.0031(11) -0.0003(12) -0.0047(11) N51 0.0374(16) 0.0235(14) 0.0409(16) -0.0007(13) 0.0080(12) -0.0004(11) N52 0.0468(18) 0.0317(17) 0.0328(17) -0.0008(13) 0.0072(13) -0.0013(13) N53 0.0455(18) 0.0273(16) 0.0344(17) 0.0036(14) 0.0046(13) 0.0084(13) _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 Cl1 C60 1.735(3) . ? Cl2 C10 1.738(3) . ? C7 O1 1.251(4) . ? C7 N1 1.345(4) . ? C7 C1 1.498(4) . ? C8 N3 1.328(4) . ? C8 N1 1.332(4) . ? C8 N2 1.362(4) . ? C9 C10 1.383(4) . ? C9 C14 1.400(4) . ? C9 N2 1.402(4) . ? C2 C3 1.376(4) . ? C2 C1 1.394(4) . ? C2 H2 0.9300 . ? C1 C6 1.386(4) . ? C10 C11 1.373(4) . ? C6 C5 1.374(4) . ? C6 H6 0.9300 . ? C3 C4 1.368(5) . ? C3 H3 0.9300 . ? C14 C13 1.375(5) . ? C14 H14 0.9300 . ? C15 N3 1.451(4) . ? C15 C16 1.499(5) . ? C15 C17 1.500(4) . ? C15 H15 0.9800 . ? C12 C11 1.375(5) . ? C12 C13 1.377(5) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C11 H11 0.9300 . ? C4 C5 1.391(5) . ? C4 H4 0.9300 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C5 H5 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? N2 H40 0.85(3) . ? N3 H41 0.84(3) . ? C57 O51 1.247(3) . ? C57 N51 1.347(4) . ? C57 C51 1.496(4) . ? C59 C60 1.386(4) . ? C59 C64 1.389(4) . ? C59 N52 1.408(4) . ? C58 N51 1.330(4) . ? C58 N53 1.333(4) . ? C58 N52 1.362(4) . ? C52 C51 1.380(4) . ? C52 C53 1.386(4) . ? C52 H52 0.9300 . ? C51 C56 1.394(4) . ? C65 N53 1.452(4) . ? C65 C67 1.513(4) . ? C65 C66 1.520(4) . ? C65 H65 0.9800 . ? C67 H67A 0.9600 . ? C67 H67B 0.9600 . ? C67 H67C 0.9600 . ? C64 C63 1.380(4) . ? C64 H64 0.9300 . ? C56 C55 1.379(4) . ? C56 H56 0.9300 . ? C60 C61 1.378(4) . ? C61 C62 1.370(5) . ? C61 H61 0.9300 . ? C62 C63 1.370(5) . ? C62 H62 0.9300 . ? C54 C55 1.370(5) . ? C54 C53 1.372(4) . ? C54 H54 0.9300 . ? C63 H63 0.9300 . ? C55 H55 0.9300 . ? C53 H53 0.9300 . ? C66 H66A 0.9600 . ? C66 H66B 0.9600 . ? C66 H66C 0.9600 . ? N52 H90 0.88(4) . ? N53 H91 0.82(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 O1 C7 N1 126.5(3) . . ? O1 C7 C1 119.4(3) . . ? N1 C7 C1 114.1(3) . . ? N3 C8 N1 118.6(3) . . ? N3 C8 N2 118.4(3) . . ? N1 C8 N2 122.9(3) . . ? C10 C9 C14 116.8(3) . . ? C10 C9 N2 119.4(3) . . ? C14 C9 N2 123.6(3) . . ? C3 C2 C1 120.4(3) . . ? C3 C2 H2 119.8 . . ? C1 C2 H2 119.8 . . ? C6 C1 C2 118.5(3) . . ? C6 C1 C7 121.9(3) . . ? C2 C1 C7 119.6(3) . . ? C11 C10 C9 122.4(3) . . ? C11 C10 Cl2 118.2(3) . . ? C9 C10 Cl2 119.5(2) . . ? C5 C6 C1 121.2(3) . . ? C5 C6 H6 119.4 . . ? C1 C6 H6 119.4 . . ? C4 C3 C2 120.4(3) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C13 C14 C9 120.7(3) . . ? C13 C14 H14 119.6 . . ? C9 C14 H14 119.6 . . ? N3 C15 C16 111.1(3) . . ? N3 C15 C17 108.6(3) . . ? C16 C15 C17 111.9(3) . . ? N3 C15 H15 108.4 . . ? C16 C15 H15 108.4 . . ? C17 C15 H15 108.4 . . ? C11 C12 C13 118.9(3) . . ? C11 C12 H12 120.5 . . ? C13 C12 H12 120.5 . . ? C14 C13 C12 121.1(4) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C10 C11 C12 120.1(3) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C3 C4 C5 120.0(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C6 C5 C4 119.4(3) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? 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 . . ? C8 N1 C7 121.4(3) . . ? C8 N2 C9 130.9(3) . . ? C8 N2 H40 115(2) . . ? C9 N2 H40 114(2) . . ? C8 N3 C15 124.7(3) . . ? C8 N3 H41 119(2) . . ? C15 N3 H41 116(2) . . ? O51 C57 N51 125.9(3) . . ? O51 C57 C51 119.4(3) . . ? N51 C57 C51 114.7(3) . . ? C60 C59 C64 117.5(3) . . ? C60 C59 N52 118.4(3) . . ? C64 C59 N52 124.0(3) . . ? N51 C58 N53 118.6(3) . . ? N51 C58 N52 122.4(3) . . ? N53 C58 N52 118.9(3) . . ? C51 C52 C53 120.8(3) . . ? C51 C52 H52 119.6 . . ? C53 C52 H52 119.6 . . ? C52 C51 C56 118.0(3) . . ? C52 C51 C57 122.2(3) . . ? C56 C51 C57 119.7(3) . . ? N53 C65 C67 108.5(3) . . ? N53 C65 C66 110.3(3) . . ? C67 C65 C66 111.6(3) . . ? N53 C65 H65 108.8 . . ? C67 C65 H65 108.8 . . ? C66 C65 H65 108.8 . . ? C65 C67 H67A 109.5 . . ? C65 C67 H67B 109.5 . . ? H67A C67 H67B 109.5 . . ? C65 C67 H67C 109.5 . . ? H67A C67 H67C 109.5 . . ? H67B C67 H67C 109.5 . . ? C63 C64 C59 120.5(3) . . ? C63 C64 H64 119.7 . . ? C59 C64 H64 119.7 . . ? C55 C56 C51 120.8(3) . . ? C55 C56 H56 119.6 . . ? C51 C56 H56 119.6 . . ? C61 C60 C59 121.6(3) . . ? C61 C60 Cl1 118.7(3) . . ? C59 C60 Cl1 119.7(3) . . ? C62 C61 C60 120.1(3) . . ? C62 C61 H61 119.9 . . ? C60 C61 H61 119.9 . . ? C63 C62 C61 119.1(3) . . ? C63 C62 H62 120.4 . . ? C61 C62 H62 120.4 . . ? C55 C54 C53 119.8(3) . . ? C55 C54 H54 120.1 . . ? C53 C54 H54 120.1 . . ? C62 C63 C64 121.1(3) . . ? C62 C63 H63 119.5 . . ? C64 C63 H63 119.5 . . ? C54 C55 C56 120.3(3) . . ? C54 C55 H55 119.8 . . ? C56 C55 H55 119.8 . . ? C54 C53 C52 120.2(3) . . ? C54 C53 H53 119.9 . . ? C52 C53 H53 119.9 . . ? C65 C66 H66A 109.5 . . ? C65 C66 H66B 109.5 . . ? H66A C66 H66B 109.5 . . ? C65 C66 H66C 109.5 . . ? H66A C66 H66C 109.5 . . ? H66B C66 H66C 109.5 . . ? C58 N51 C57 121.0(3) . . ? C58 N52 C59 129.8(3) . . ? C58 N52 H90 115(2) . . ? C59 N52 H90 115(2) . . ? C58 N53 C65 124.5(3) . . ? C58 N53 H91 115(2) . . ? C65 N53 H91 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 C3 C2 C1 C6 -0.2(5) . . . . ? C3 C2 C1 C7 179.1(3) . . . . ? O1 C7 C1 C6 -173.2(3) . . . . ? N1 C7 C1 C6 6.4(4) . . . . ? O1 C7 C1 C2 7.5(4) . . . . ? N1 C7 C1 C2 -172.8(3) . . . . ? C14 C9 C10 C11 0.0(5) . . . . ? N2 C9 C10 C11 -175.5(3) . . . . ? C14 C9 C10 Cl2 178.9(2) . . . . ? N2 C9 C10 Cl2 3.4(4) . . . . ? C2 C1 C6 C5 -1.0(5) . . . . ? C7 C1 C6 C5 179.8(3) . . . . ? C1 C2 C3 C4 0.3(5) . . . . ? C10 C9 C14 C13 0.7(5) . . . . ? N2 C9 C14 C13 176.0(3) . . . . ? C9 C14 C13 C12 -0.7(5) . . . . ? C11 C12 C13 C14 -0.1(5) . . . . ? C9 C10 C11 C12 -0.7(5) . . . . ? Cl2 C10 C11 C12 -179.6(3) . . . . ? C13 C12 C11 C10 0.8(5) . . . . ? C2 C3 C4 C5 0.7(5) . . . . ? C1 C6 C5 C4 2.0(5) . . . . ? C3 C4 C5 C6 -1.8(5) . . . . ? N3 C8 N1 C7 169.2(3) . . . . ? N2 C8 N1 C7 -13.3(4) . . . . ? O1 C7 N1 C8 -14.1(5) . . . . ? C1 C7 N1 C8 166.3(3) . . . . ? N3 C8 N2 C9 26.6(5) . . . . ? N1 C8 N2 C9 -150.9(3) . . . . ? C10 C9 N2 C8 -172.6(3) . . . . ? C14 C9 N2 C8 12.3(5) . . . . ? N1 C8 N3 C15 3.8(5) . . . . ? N2 C8 N3 C15 -173.8(3) . . . . ? C16 C15 N3 C8 -92.7(4) . . . . ? C17 C15 N3 C8 143.9(3) . . . . ? C53 C52 C51 C56 0.6(5) . . . . ? C53 C52 C51 C57 -177.6(3) . . . . ? O51 C57 C51 C52 -173.2(3) . . . . ? N51 C57 C51 C52 6.9(4) . . . . ? O51 C57 C51 C56 8.6(4) . . . . ? N51 C57 C51 C56 -171.3(3) . . . . ? C60 C59 C64 C63 2.4(5) . . . . ? N52 C59 C64 C63 178.0(3) . . . . ? C52 C51 C56 C55 -1.1(5) . . . . ? C57 C51 C56 C55 177.2(3) . . . . ? C64 C59 C60 C61 -1.1(5) . . . . ? N52 C59 C60 C61 -177.0(3) . . . . ? C64 C59 C60 Cl1 178.5(2) . . . . ? N52 C59 C60 Cl1 2.6(4) . . . . ? C59 C60 C61 C62 -1.0(5) . . . . ? Cl1 C60 C61 C62 179.4(3) . . . . ? C60 C61 C62 C63 1.8(5) . . . . ? C61 C62 C63 C64 -0.4(5) . . . . ? C59 C64 C63 C62 -1.7(5) . . . . ? C53 C54 C55 C56 -0.2(5) . . . . ? C51 C56 C55 C54 0.9(5) . . . . ? C55 C54 C53 C52 -0.3(5) . . . . ? C51 C52 C53 C54 0.0(5) . . . . ? N53 C58 N51 C57 164.8(3) . . . . ? N52 C58 N51 C57 -18.6(4) . . . . ? O51 C57 N51 C58 -16.8(5) . . . . ? C51 C57 N51 C58 163.2(3) . . . . ? N51 C58 N52 C59 -156.2(3) . . . . ? N53 C58 N52 C59 20.4(5) . . . . ? C60 C59 N52 C58 -165.0(3) . . . . ? C64 C59 N52 C58 19.5(5) . . . . ? N51 C58 N53 C65 -1.4(4) . . . . ? N52 C58 N53 C65 -178.1(3) . . . . ? C67 C65 N53 C58 143.2(3) . . . . ? C66 C65 N53 C58 -94.3(4) . . . . ? 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 N2 H40 O1 0.85(3) 2.01(3) 2.658(3) 133(3) . N2 H40 Cl2 0.85(3) 2.49(3) 2.941(3) 114(2) . N52 H90 O51 0.88(4) 2.01(4) 2.669(3) 131(3) . N52 H90 Cl1 0.88(4) 2.47(3) 2.930(3) 113(3) . N53 H91 O51 0.82(3) 2.12(3) 2.879(4) 155(3) 2_655 N3 H41 O1 0.84(3) 2.11(3) 2.905(4) 160(3) 2_646 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.00 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.392 _refine_diff_density_min -0.274 _refine_diff_density_rms 0.052