# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1350 _publ_requested_journal CrystEngComm loop_ _publ_author_name 'Hor, Andy' 'New, Siu Yee' _publ_contact_author_name A.Hor _publ_contact_author_address ; 3 Science Drive 3 Singapore 117543 ; _publ_contact_author_email andyhor@nus.edu.sg # Attachment '- 1.cif' data_8450 _database_code_depnum_ccdc_archive 'CCDC 786079' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C38 H52 Cu2 N8 O14' _chemical_formula_weight 971.96 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.7518(9) _cell_length_b 16.3475(12) _cell_length_c 23.4131(18) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4498.0(6) _cell_formula_units_Z 4 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 3592 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 19.87 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.02 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.435 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2024 _exptl_absorpt_coefficient_mu 1.017 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.7109 _exptl_absorpt_correction_T_max 0.9799 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 31714 _diffrn_reflns_av_R_equivalents 0.0824 _diffrn_reflns_av_sigmaI/netI 0.1017 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_theta_min 1.52 _diffrn_reflns_theta_max 27.64 _reflns_number_total 10372 _reflns_number_gt 7342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0773P)^2^+0.3788P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.025(19) _refine_ls_number_reflns 10372 _refine_ls_number_parameters 579 _refine_ls_number_restraints 54 _refine_ls_R_factor_all 0.1135 _refine_ls_R_factor_gt 0.0782 _refine_ls_wR_factor_ref 0.1750 _refine_ls_wR_factor_gt 0.1590 _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.79331(6) 0.87363(4) 0.85436(3) 0.03332(18) Uani 1 1 d . . . C1 C 1.0349(4) 0.7757(3) 0.8674(2) 0.0276(12) Uani 1 1 d D . . C2 C 0.9795(5) 0.8039(3) 0.9169(2) 0.0340(13) Uani 1 1 d D . . C3 C 1.0296(5) 0.7866(4) 0.9713(3) 0.0417(15) Uani 1 1 d D . . H3 H 0.9934 0.8061 1.0044 0.050 Uiso 1 1 calc R . . C4 C 1.1254(5) 0.7439(4) 0.9768(3) 0.0409(15) Uani 1 1 d D . . H4 H 1.1549 0.7340 1.0135 0.049 Uiso 1 1 calc R . . C5 C 1.2818(6) 0.6653(4) 0.9344(3) 0.0465(16) Uani 1 1 d D . . H5 H 1.3076 0.6526 0.9714 0.056 Uiso 1 1 calc R . . C6 C 1.3400(6) 0.6375(5) 0.8892(3) 0.0533(19) Uani 1 1 d D . . H6 H 1.4068 0.6066 0.8943 0.064 Uiso 1 1 calc R . . C7 C 1.2998(6) 0.6551(4) 0.8341(3) 0.0504(17) Uani 1 1 d D . . H7 H 1.3406 0.6364 0.8022 0.060 Uiso 1 1 calc R . . C8 C 1.2010(6) 0.6996(4) 0.8262(3) 0.0445(15) Uani 1 1 d D . . H8 H 1.1745 0.7100 0.7890 0.053 Uiso 1 1 calc R . . C9 C 1.1408(5) 0.7291(3) 0.8730(2) 0.0341(13) Uani 1 1 d D . . C10 C 1.1840(5) 0.7127(3) 0.9280(3) 0.0374(14) Uani 1 1 d D . . O1 O 0.8829(4) 0.8448(3) 0.91732(17) 0.0424(11) Uani 1 1 d . . . C11 C 0.9914(5) 0.7918(3) 0.8122(2) 0.0295(12) Uani 1 1 d . . . H11 H 1.0356 0.7741 0.7811 0.035 Uiso 1 1 calc R . . N1 N 0.8971(4) 0.8285(3) 0.80034(19) 0.0302(10) Uani 1 1 d . . . C12 C 0.8615(4) 0.8389(3) 0.7404(2) 0.0298(12) Uani 1 1 d . . . H12 H 0.9266 0.8593 0.7177 0.036 Uiso 1 1 calc R . . C13 C 0.7661(5) 0.9021(3) 0.7393(2) 0.0309(12) Uani 1 1 d . . . O2 O 0.7194(4) 0.9215(2) 0.78743(16) 0.0377(9) Uani 1 1 d . . . O3 O 0.7343(4) 0.9303(3) 0.69367(18) 0.0440(11) Uani 1 1 d . . . C14 C 0.8179(5) 0.7597(3) 0.7141(2) 0.0338(13) Uani 1 1 d . . . H14A H 0.7888 0.7713 0.6757 0.041 Uiso 1 1 calc R . . H14B H 0.8816 0.7214 0.7102 0.041 Uiso 1 1 calc R . . C15 C 0.7252(5) 0.7195(4) 0.7486(3) 0.0397(14) Uani 1 1 d . . . H15A H 0.6625 0.7585 0.7532 0.048 Uiso 1 1 calc R . . H15B H 0.7551 0.7073 0.7868 0.048 Uiso 1 1 calc R . . C16 C 0.6780(5) 0.6409(3) 0.7231(2) 0.0345(13) Uani 1 1 d . . . H16A H 0.6276 0.6539 0.6910 0.041 Uiso 1 1 calc R . . H16B H 0.7405 0.6070 0.7087 0.041 Uiso 1 1 calc R . . C17 C 0.5277(5) 0.5457(3) 0.7585(2) 0.0325(13) Uani 1 1 d D . . N2 N 0.6149(4) 0.5965(3) 0.7667(2) 0.0385(12) Uani 1 1 d D . . H2 H 0.6364 0.6039 0.8019 0.046 Uiso 1 1 calc R . . N3 N 0.4917(4) 0.5019(3) 0.8020(2) 0.0380(12) Uani 1 1 d D . . H3A H 0.5246 0.5064 0.8351 0.046 Uiso 1 1 calc R . . H3B H 0.4349 0.4683 0.7976 0.046 Uiso 1 1 calc R . . N4 N 0.4770(4) 0.5368(3) 0.7079(2) 0.0429(12) Uani 1 1 d D . . H4A H 0.4210 0.5024 0.7041 0.051 Uiso 1 1 calc R . . H4B H 0.4999 0.5654 0.6787 0.051 Uiso 1 1 calc R . . C18 C 0.5711(6) 0.8907(4) 0.9057(2) 0.0392(14) Uani 1 1 d D . . C19 C 0.5388(6) 0.8166(4) 0.8710(3) 0.0512(18) Uani 1 1 d D . . H19A H 0.4691 0.7933 0.8860 0.077 Uiso 1 1 calc R . . H19B H 0.5993 0.7764 0.8730 0.077 Uiso 1 1 calc R . . H19C H 0.5271 0.8326 0.8315 0.077 Uiso 1 1 calc R . . O4 O 0.6741(3) 0.9147(3) 0.90315(18) 0.0422(10) Uani 1 1 d D . . O5 O 0.4992(4) 0.9245(3) 0.93572(19) 0.0496(12) Uani 1 1 d D . . Cu2 Cu 0.41980(7) 0.96585(5) 0.52721(4) 0.0470(2) Uani 1 1 d . . . C21 C 0.3720(5) 1.0103(4) 0.3925(3) 0.0408(15) Uani 1 1 d D . . C22 C 0.4635(5) 0.9602(4) 0.4064(3) 0.0515(18) Uani 1 1 d D . . C23 C 0.5352(7) 0.9307(5) 0.3618(4) 0.078(3) Uani 1 1 d D . . H23 H 0.5956 0.8953 0.3708 0.093 Uiso 1 1 calc R . . C24 C 0.5178(8) 0.9529(6) 0.3066(4) 0.078(3) Uani 1 1 d D . . H24 H 0.5697 0.9355 0.2785 0.093 Uiso 1 1 calc R . . C25 C 0.3999(9) 1.0219(7) 0.2329(4) 0.090(4) Uani 1 1 d D . . H25 H 0.4504 1.0028 0.2048 0.108 Uiso 1 1 calc R . . C26 C 0.3125(10) 1.0654(7) 0.2169(4) 0.095(4) Uani 1 1 d D . . H26 H 0.2988 1.0751 0.1779 0.114 Uiso 1 1 calc R . . C27 C 0.2385(8) 1.0978(6) 0.2589(3) 0.079(3) Uani 1 1 d D . . H27 H 0.1773 1.1315 0.2481 0.095 Uiso 1 1 calc R . . C28 C 0.2567(8) 1.0798(5) 0.3157(3) 0.063(2) Uani 1 1 d D . . H28 H 0.2054 1.0995 0.3432 0.075 Uiso 1 1 calc R . . C29 C 0.3501(6) 1.0327(4) 0.3332(3) 0.0474(17) Uani 1 1 d D . . C30 C 0.4217(8) 1.0025(5) 0.2898(3) 0.063(2) Uani 1 1 d D . . O6 O 0.4873(4) 0.9317(3) 0.4573(2) 0.0561(13) Uani 1 1 d . . . C31 C 0.3004(6) 1.0471(4) 0.4364(2) 0.0392(14) Uani 1 1 d . . . H31 H 0.2428 1.0833 0.4246 0.047 Uiso 1 1 calc R . . N5 N 0.3109(4) 1.0330(3) 0.4901(2) 0.0367(11) Uani 1 1 d . . . C32 C 0.2389(5) 1.0741(4) 0.5313(2) 0.0365(13) Uani 1 1 d . . . H32 H 0.2114 1.1269 0.5159 0.044 Uiso 1 1 calc R . . C33 C 0.3088(5) 1.0879(4) 0.5853(2) 0.0377(14) Uani 1 1 d . . . O7 O 0.3901(4) 1.0363(3) 0.59285(18) 0.0504(12) Uani 1 1 d . . . O8 O 0.2832(4) 1.1402(3) 0.62056(18) 0.0555(12) Uani 1 1 d . . . C34 C 0.1370(5) 1.0179(4) 0.5472(2) 0.0346(13) Uani 1 1 d . . . H34A H 0.1019 0.9973 0.5121 0.042 Uiso 1 1 calc R . . H34B H 0.1652 0.9708 0.5689 0.042 Uiso 1 1 calc R . . C35 C 0.0484(5) 1.0620(4) 0.5821(3) 0.0397(15) Uani 1 1 d . . . H35A H 0.0273 1.1129 0.5627 0.048 Uiso 1 1 calc R . . H35B H 0.0805 1.0763 0.6194 0.048 Uiso 1 1 calc R . . C36 C -0.0572(5) 1.0099(4) 0.5907(3) 0.0429(15) Uani 1 1 d . . . H36A H -0.0354 0.9558 0.6050 0.051 Uiso 1 1 calc R . . H36B H -0.1072 1.0357 0.6189 0.051 Uiso 1 1 calc R . . C37 C -0.2173(5) 0.9630(4) 0.5302(3) 0.0450(15) Uani 1 1 d D . . N6 N -0.1172(4) 1.0015(3) 0.5363(2) 0.0420(13) Uani 1 1 d D . . H6A H -0.0861 1.0227 0.5060 0.050 Uiso 1 1 calc R . . N7 N -0.2667(4) 0.9635(4) 0.4792(2) 0.0543(15) Uani 1 1 d D . . H7A H -0.3302 0.9372 0.4739 0.065 Uiso 1 1 calc R . . H7B H -0.2356 0.9900 0.4511 0.065 Uiso 1 1 calc R . . N8 N -0.2623(5) 0.9236(4) 0.5730(2) 0.0514(15) Uani 1 1 d D . . H8A H -0.3258 0.8970 0.5685 0.062 Uiso 1 1 calc R . . H8B H -0.2288 0.9239 0.6062 0.062 Uiso 1 1 calc R . . C38 C 0.4312(10) 0.8411(5) 0.5983(4) 0.072(2) Uani 1 1 d D . . C39 C 0.4802(11) 0.7828(6) 0.6420(5) 0.121(4) Uani 1 1 d D . . H39A H 0.4592 0.8008 0.6801 0.181 Uiso 1 1 calc R . . H39B H 0.5625 0.7820 0.6386 0.181 Uiso 1 1 calc R . . H39C H 0.4504 0.7283 0.6354 0.181 Uiso 1 1 calc R . . O9 O 0.5025(4) 0.8864(4) 0.5724(2) 0.0680(15) Uani 1 1 d D . . O10 O 0.3287(6) 0.8450(4) 0.5891(3) 0.097(2) Uani 1 1 d D . . O1W O 0.4513(8) 0.0870(4) 0.9052(2) 0.104(3) Uani 1 1 d U . . O2W O 0.6154(17) 0.7291(9) 0.3482(8) 0.306(10) Uani 1 1 d U . . O3W O 0.4682(14) 0.7595(7) 0.4490(6) 0.132(5) Uani 0.60 1 d PU A 1 O4W O 0.695(3) 0.6912(10) 0.5371(16) 0.30(2) Uani 0.60 1 d PU B 1 O3W' O 0.425(3) 0.6831(14) 0.5164(10) 0.190(14) Uani 0.40 1 d PU C 2 O4W' O 0.678(6) 0.734(3) 0.489(3) 0.42(4) Uani 0.40 1 d PU D 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0328(3) 0.0398(4) 0.0274(3) -0.0037(3) -0.0011(3) 0.0081(3) C1 0.024(3) 0.022(3) 0.036(3) 0.001(2) -0.003(2) -0.002(2) C2 0.036(3) 0.034(3) 0.032(3) 0.001(2) -0.006(3) -0.010(3) C3 0.046(4) 0.051(4) 0.028(3) 0.002(3) -0.003(3) 0.000(3) C4 0.044(4) 0.050(4) 0.029(3) 0.010(3) -0.009(3) -0.002(3) C5 0.043(4) 0.045(4) 0.051(4) 0.009(3) -0.017(3) 0.002(3) C6 0.036(3) 0.060(5) 0.064(5) 0.010(4) -0.007(3) 0.020(3) C7 0.043(4) 0.054(4) 0.054(4) -0.005(3) 0.005(3) 0.018(3) C8 0.044(4) 0.051(4) 0.038(3) -0.002(3) -0.001(3) 0.015(3) C9 0.037(3) 0.030(3) 0.035(3) -0.001(2) -0.005(3) 0.003(3) C10 0.034(3) 0.026(3) 0.052(4) 0.004(3) -0.011(3) -0.007(2) O1 0.039(2) 0.057(3) 0.031(2) -0.0074(19) -0.0024(18) 0.011(2) C11 0.026(3) 0.033(3) 0.030(3) -0.002(2) 0.001(2) 0.002(2) N1 0.029(2) 0.031(3) 0.031(2) -0.002(2) -0.001(2) 0.002(2) C12 0.023(3) 0.039(3) 0.027(3) 0.002(2) -0.003(2) 0.001(2) C13 0.033(3) 0.024(3) 0.036(3) 0.004(2) 0.002(2) -0.002(2) O2 0.037(2) 0.040(2) 0.036(2) -0.0001(18) -0.0005(19) 0.014(2) O3 0.048(3) 0.050(3) 0.035(2) 0.0127(19) -0.005(2) 0.013(2) C14 0.038(3) 0.030(3) 0.033(3) -0.006(2) -0.009(2) 0.005(3) C15 0.040(3) 0.045(4) 0.034(3) -0.009(3) -0.002(3) 0.000(3) C16 0.040(3) 0.029(3) 0.034(3) 0.000(2) -0.001(2) 0.002(2) C17 0.038(3) 0.028(3) 0.032(3) -0.008(2) -0.007(2) 0.005(3) N2 0.048(3) 0.034(3) 0.034(3) -0.003(2) -0.007(2) -0.008(2) N3 0.039(3) 0.038(3) 0.037(3) -0.003(2) -0.007(2) -0.009(2) N4 0.048(3) 0.047(3) 0.034(3) -0.003(2) -0.006(2) -0.012(3) C18 0.046(4) 0.043(4) 0.028(3) 0.008(3) 0.001(3) 0.011(3) C19 0.056(4) 0.046(4) 0.052(4) 0.000(3) 0.015(3) -0.001(3) O4 0.027(2) 0.059(3) 0.041(2) -0.015(2) 0.0033(18) 0.008(2) O5 0.050(3) 0.058(3) 0.041(3) -0.005(2) 0.015(2) 0.012(2) Cu2 0.0371(4) 0.0576(5) 0.0465(5) -0.0028(4) -0.0070(4) 0.0076(4) C21 0.037(3) 0.047(4) 0.039(3) -0.009(3) 0.004(3) -0.015(3) C22 0.038(4) 0.058(4) 0.058(5) -0.021(4) 0.012(3) -0.010(4) C23 0.061(5) 0.095(6) 0.077(7) -0.034(5) 0.016(5) -0.010(5) C24 0.077(6) 0.099(7) 0.057(5) -0.036(5) 0.033(5) -0.032(6) C25 0.086(7) 0.136(10) 0.049(5) -0.048(6) 0.025(5) -0.071(7) C26 0.116(9) 0.133(10) 0.035(5) -0.006(5) -0.006(5) -0.078(8) C27 0.096(7) 0.094(7) 0.047(5) 0.004(4) -0.015(5) -0.040(5) C28 0.087(6) 0.063(5) 0.038(4) -0.002(3) -0.005(4) -0.033(5) C29 0.067(4) 0.042(4) 0.033(3) -0.011(3) 0.010(3) -0.027(4) C30 0.074(5) 0.074(5) 0.040(4) -0.026(4) 0.009(4) -0.036(5) O6 0.046(3) 0.065(3) 0.058(3) -0.005(2) 0.002(2) 0.011(2) C31 0.046(3) 0.035(3) 0.037(3) -0.009(2) 0.000(3) -0.010(3) N5 0.039(3) 0.040(3) 0.032(3) -0.001(2) -0.006(2) 0.006(2) C32 0.038(3) 0.043(3) 0.028(3) -0.004(3) 0.001(2) 0.001(3) C33 0.036(3) 0.046(4) 0.031(3) 0.002(3) -0.002(3) -0.014(3) O7 0.051(3) 0.061(3) 0.039(2) -0.006(2) -0.019(2) 0.002(3) O8 0.066(3) 0.061(3) 0.040(2) -0.012(2) -0.009(2) -0.009(3) C34 0.035(3) 0.042(4) 0.026(3) -0.003(2) -0.007(2) 0.005(3) C35 0.044(3) 0.042(4) 0.034(3) 0.003(3) -0.001(3) 0.006(3) C36 0.041(3) 0.054(4) 0.034(3) 0.003(3) -0.007(3) 0.000(3) C37 0.040(3) 0.059(4) 0.035(3) -0.004(3) -0.005(3) 0.010(4) N6 0.038(3) 0.064(3) 0.024(3) 0.006(2) -0.001(2) -0.002(3) N7 0.043(3) 0.082(4) 0.037(3) 0.012(3) -0.009(2) -0.022(3) N8 0.048(3) 0.070(4) 0.036(3) 0.009(3) 0.000(3) -0.012(3) C38 0.093(7) 0.052(5) 0.072(6) 0.010(4) 0.002(5) 0.016(5) C39 0.181(12) 0.084(7) 0.098(8) 0.022(6) -0.014(9) 0.065(8) O9 0.052(3) 0.076(4) 0.076(4) 0.008(3) -0.010(3) 0.022(3) O10 0.087(5) 0.064(4) 0.139(7) 0.016(4) 0.005(5) 0.001(4) O1W 0.191(8) 0.074(4) 0.048(3) 0.011(3) 0.025(4) 0.035(5) O2W 0.39(2) 0.227(14) 0.299(18) -0.088(14) -0.084(19) 0.166(16) O3W 0.198(15) 0.064(7) 0.134(12) -0.022(7) 0.031(11) 0.025(9) O4W 0.34(3) 0.077(11) 0.49(5) -0.017(18) 0.30(4) -0.023(17) O3W' 0.31(4) 0.126(18) 0.14(2) -0.018(15) -0.13(2) -0.02(2) O4W' 0.53(8) 0.31(5) 0.41(7) -0.30(5) -0.25(7) 0.22(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.872(4) . ? Cu1 N1 1.906(5) . ? Cu1 O4 1.928(4) . ? Cu1 O2 1.955(4) . ? C1 C2 1.407(8) . ? C1 C11 1.414(7) . ? C1 C9 1.465(8) . ? C2 O1 1.317(7) . ? C2 C3 1.433(8) . ? C3 C4 1.331(9) . ? C4 C10 1.429(9) . ? C5 C6 1.340(10) . ? C5 C10 1.394(9) . ? C6 C7 1.403(9) . ? C7 C8 1.383(9) . ? C8 C9 1.392(8) . ? C9 C10 1.409(8) . ? C11 N1 1.291(7) . ? N1 C12 1.475(7) . ? C12 C14 1.522(8) . ? C12 C13 1.525(8) . ? C13 O3 1.222(7) . ? C13 O2 1.294(7) . ? C14 C15 1.507(8) . ? C15 C16 1.522(8) . ? C16 N2 1.457(7) . ? C17 N3 1.315(8) . ? C17 N2 1.333(7) . ? C17 N4 1.334(7) . ? C18 O5 1.230(7) . ? C18 O4 1.274(8) . ? C18 C19 1.507(9) . ? Cu2 N5 1.897(5) . ? Cu2 O6 1.902(5) . ? Cu2 O9 1.936(5) . ? Cu2 O7 1.952(5) . ? Cu2 O10 2.674(7) . ? C21 C22 1.390(10) . ? C21 C31 1.458(8) . ? C21 C29 1.460(9) . ? C22 O6 1.311(9) . ? C22 C23 1.425(10) . ? C23 C24 1.358(13) . ? C24 C30 1.445(13) . ? C25 C26 1.304(15) . ? C25 C30 1.394(12) . ? C26 C27 1.416(14) . ? C27 C28 1.378(10) . ? C28 C29 1.402(11) . ? C29 C30 1.408(10) . ? C31 N5 1.285(7) . ? N5 C32 1.449(7) . ? C32 C33 1.524(8) . ? C32 C34 1.554(8) . ? C33 O8 1.225(7) . ? C33 O7 1.287(8) . ? C34 C35 1.507(8) . ? C35 C36 1.518(9) . ? C36 N6 1.463(7) . ? C37 N8 1.304(8) . ? C37 N7 1.327(7) . ? C37 N6 1.341(8) . ? C38 O10 1.226(11) . ? C38 O9 1.273(11) . ? C38 C39 1.512(12) . ? 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 Cu1 N1 93.73(19) . . ? O1 Cu1 O4 91.70(18) . . ? N1 Cu1 O4 173.19(19) . . ? O1 Cu1 O2 169.1(2) . . ? N1 Cu1 O2 84.69(18) . . ? O4 Cu1 O2 90.73(18) . . ? C2 C1 C11 121.6(5) . . ? C2 C1 C9 119.2(5) . . ? C11 C1 C9 119.1(5) . . ? O1 C2 C1 124.9(5) . . ? O1 C2 C3 116.6(5) . . ? C1 C2 C3 118.6(5) . . ? C4 C3 C2 122.5(6) . . ? C3 C4 C10 121.2(6) . . ? C6 C5 C10 121.6(6) . . ? C5 C6 C7 119.0(6) . . ? C8 C7 C6 121.0(6) . . ? C7 C8 C9 120.2(6) . . ? C8 C9 C10 118.1(5) . . ? C8 C9 C1 122.7(5) . . ? C10 C9 C1 119.2(5) . . ? C5 C10 C9 120.1(6) . . ? C5 C10 C4 120.6(6) . . ? C9 C10 C4 119.2(5) . . ? C2 O1 Cu1 127.3(4) . . ? N1 C11 C1 126.4(5) . . ? C11 N1 C12 120.1(5) . . ? C11 N1 Cu1 126.0(4) . . ? C12 N1 Cu1 113.9(3) . . ? N1 C12 C14 112.5(5) . . ? N1 C12 C13 107.6(4) . . ? C14 C12 C13 108.8(4) . . ? O3 C13 O2 122.7(5) . . ? O3 C13 C12 119.7(5) . . ? O2 C13 C12 117.6(5) . . ? C13 O2 Cu1 114.4(4) . . ? C15 C14 C12 113.4(5) . . ? C14 C15 C16 114.9(5) . . ? N2 C16 C15 109.3(5) . . ? N3 C17 N2 118.4(5) . . ? N3 C17 N4 118.9(5) . . ? N2 C17 N4 122.7(6) . . ? C17 N2 C16 126.9(5) . . ? O5 C18 O4 122.8(6) . . ? O5 C18 C19 119.7(6) . . ? O4 C18 C19 117.5(6) . . ? C18 O4 Cu1 127.7(4) . . ? N5 Cu2 O6 93.3(2) . . ? N5 Cu2 O9 167.7(2) . . ? O6 Cu2 O9 93.6(2) . . ? N5 Cu2 O7 84.18(19) . . ? O6 Cu2 O7 157.7(2) . . ? O9 Cu2 O7 93.2(2) . . ? N5 Cu2 O10 114.0(2) . . ? O6 Cu2 O10 114.6(2) . . ? O9 Cu2 O10 53.8(2) . . ? O7 Cu2 O10 86.4(2) . . ? C22 C21 C31 121.7(6) . . ? C22 C21 C29 120.4(6) . . ? C31 C21 C29 117.7(6) . . ? O6 C22 C21 126.0(6) . . ? O6 C22 C23 114.8(7) . . ? C21 C22 C23 119.0(8) . . ? C24 C23 C22 121.2(9) . . ? C23 C24 C30 121.7(7) . . ? C26 C25 C30 122.9(9) . . ? C25 C26 C27 119.2(9) . . ? C28 C27 C26 119.6(10) . . ? C27 C28 C29 121.4(9) . . ? C28 C29 C30 116.8(7) . . ? C28 C29 C21 123.6(6) . . ? C30 C29 C21 119.5(7) . . ? C25 C30 C29 119.9(9) . . ? C25 C30 C24 122.1(8) . . ? C29 C30 C24 117.9(7) . . ? C22 O6 Cu2 126.1(4) . . ? N5 C31 C21 124.1(6) . . ? C31 N5 C32 120.9(5) . . ? C31 N5 Cu2 128.1(4) . . ? C32 N5 Cu2 110.9(4) . . ? N5 C32 C33 107.9(5) . . ? N5 C32 C34 109.6(5) . . ? C33 C32 C34 107.7(5) . . ? O8 C33 O7 123.2(6) . . ? O8 C33 C32 122.0(6) . . ? O7 C33 C32 114.6(5) . . ? C33 O7 Cu2 114.3(4) . . ? C35 C34 C32 112.3(5) . . ? C34 C35 C36 111.7(5) . . ? N6 C36 C35 109.4(5) . . ? N8 C37 N7 121.2(6) . . ? N8 C37 N6 120.3(6) . . ? N7 C37 N6 118.5(6) . . ? C37 N6 C36 124.1(5) . . ? O10 C38 O9 122.2(8) . . ? O10 C38 C39 121.7(10) . . ? O9 C38 C39 116.1(10) . . ? C38 O9 Cu2 108.7(5) . . ? C38 O10 Cu2 74.9(5) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.64 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.644 _refine_diff_density_min -0.400 _refine_diff_density_rms 0.094 # Attachment '- 2.cif' data_9089-new _database_code_depnum_ccdc_archive 'CCDC 786080' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C13 H22 Cl Cu N5 O10' _chemical_formula_weight 507.35 _chemical_absolute_configuration syn 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 Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 8.2119(8) _cell_length_b 8.7239(9) _cell_length_c 14.2024(14) _cell_angle_alpha 90.923(2) _cell_angle_beta 96.679(2) _cell_angle_gamma 99.903(2) _cell_volume 994.82(17) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 6144 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 27.51 _exptl_crystal_description 'Thin Plate' _exptl_crystal_colour Green _exptl_crystal_size_max 0.44 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.694 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 522 _exptl_absorpt_coefficient_mu 1.296 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5995 _exptl_absorpt_correction_T_max 0.8814 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12676 _diffrn_reflns_av_R_equivalents 0.0270 _diffrn_reflns_av_sigmaI/netI 0.0662 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 27.49 _reflns_number_total 9021 _reflns_number_gt 8342 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0259P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.023(8) _refine_ls_number_reflns 9021 _refine_ls_number_parameters 577 _refine_ls_number_restraints 126 _refine_ls_R_factor_all 0.0415 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_ref 0.0846 _refine_ls_wR_factor_gt 0.0832 _refine_ls_goodness_of_fit_ref 1.010 _refine_ls_restrained_S_all 1.006 _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 Cu1 Cu 0.14843(4) 0.45599(4) 0.11457(2) 0.02118(10) Uani 1 1 d . . . Cl1 Cl 0.29062(11) 0.23746(10) 0.07159(7) 0.0328(2) Uani 1 1 d . . . O1 O 0.0685(3) 0.3604(3) 0.22515(16) 0.0267(5) Uani 1 1 d D . . C1 C 0.1872(4) 0.5698(4) 0.3383(2) 0.0195(6) Uani 1 1 d D . . C2 C 0.0856(4) 0.4217(4) 0.3098(2) 0.0195(7) Uani 1 1 d D . . C3 C -0.0003(4) 0.3402(4) 0.3798(2) 0.0261(7) Uani 1 1 d D . . H3 H -0.0654 0.2418 0.3634 0.031 Uiso 1 1 calc R . . C4 C 0.0078(4) 0.3985(4) 0.4692(2) 0.0276(7) Uani 1 1 d D . . H4 H -0.0539 0.3431 0.5133 0.033 Uiso 1 1 calc R . . C5 C 0.1096(4) 0.5434(4) 0.4955(2) 0.0226(7) Uani 1 1 d D . . C6 C 0.1983(4) 0.6269(4) 0.4319(2) 0.0233(7) Uani 1 1 d D . . H6 H 0.2667 0.7227 0.4511 0.028 Uiso 1 1 calc R . . C7 C 0.2774(4) 0.6693(4) 0.2742(2) 0.0224(7) Uani 1 1 d D . . H7 H 0.3428 0.7633 0.2993 0.027 Uiso 1 1 calc R . . N1 N 0.2743(3) 0.6383(3) 0.18598(17) 0.0182(5) Uani 1 1 d . . . C8 C 0.3689(4) 0.7524(4) 0.1275(2) 0.0194(6) Uani 1 1 d . . . H8 H 0.3335 0.8539 0.1366 0.023 Uiso 1 1 calc R . . C9 C 0.3205(4) 0.7003(4) 0.0243(2) 0.0193(6) Uani 1 1 d . . . O2 O 0.2163(3) 0.5738(3) 0.00530(15) 0.0236(5) Uani 1 1 d . . . O3 O 0.3802(3) 0.7824(3) -0.03812(16) 0.0318(6) Uani 1 1 d . . . C10 C 0.5557(4) 0.7742(4) 0.1579(2) 0.0217(6) Uani 1 1 d . . . H10A H 0.6134 0.8438 0.1142 0.026 Uiso 1 1 calc R . . H10B H 0.5803 0.8247 0.2213 0.026 Uiso 1 1 calc R . . C11 C 0.6229(4) 0.6241(4) 0.1598(3) 0.0278(7) Uani 1 1 d . . . H11A H 0.5880 0.5674 0.0987 0.033 Uiso 1 1 calc R . . H11B H 0.5760 0.5591 0.2091 0.033 Uiso 1 1 calc R . . C12 C 0.8131(4) 0.6527(4) 0.1794(3) 0.0279(7) Uani 1 1 d . . . H12A H 0.8491 0.7183 0.2372 0.033 Uiso 1 1 calc R . . H12B H 0.8515 0.5532 0.1895 0.033 Uiso 1 1 calc R . . C13 C 0.9733(4) 0.8725(4) 0.0983(2) 0.0286(7) Uani 1 1 d D . . N2 N 0.8872(4) 0.7288(3) 0.0999(2) 0.0275(7) Uani 1 1 d D . . H2 H 0.8734 0.6735 0.0472 0.033 Uiso 1 1 calc R . . N3 N 1.0056(4) 0.9682(4) 0.1736(2) 0.0394(8) Uani 1 1 d D . . H3A H 1.0648 1.0605 0.1704 0.047 Uiso 1 1 calc R . . H3B H 0.9679 0.9392 0.2264 0.047 Uiso 1 1 calc R . . N4 N 1.0311(4) 0.9176(4) 0.0186(2) 0.0428(8) Uani 1 1 d D . . H4A H 1.0901 1.0100 0.0159 0.051 Uiso 1 1 calc R . . H4B H 1.0102 0.8550 -0.0313 0.051 Uiso 1 1 calc R . . N5 N 0.1197(4) 0.6063(4) 0.5913(2) 0.0287(7) Uani 1 1 d D . . O4 O 0.0270(3) 0.5337(3) 0.64551(17) 0.0364(6) Uani 1 1 d D . . O5 O 0.2164(4) 0.7275(4) 0.61578(19) 0.0445(7) Uani 1 1 d D . . O1W O -0.0649(3) 0.3592(3) 0.03223(17) 0.0229(5) Uani 1 1 d D . . H1WA H -0.099(4) 0.417(4) -0.008(2) 0.027 Uiso 1 1 d D . . H1WB H -0.142(3) 0.313(4) 0.057(2) 0.027 Uiso 1 1 d D . . O6W O 0.1834(4) 0.8747(3) -0.1890(2) 0.0453(7) Uani 1 1 d DU . . H6WA H 0.243(5) 0.820(5) -0.156(2) 0.054 Uiso 1 1 d D . . H6WB H 0.175(6) 0.830(5) -0.2440(16) 0.054 Uiso 1 1 d D . . Cu2 Cu 0.42404(4) 0.33534(4) 0.78240(3) 0.02195(10) Uani 1 1 d . . . O6 O 0.2839(3) 0.2381(3) 0.67288(16) 0.0275(5) Uani 1 1 d D . . C21 C 0.4718(4) 0.3289(4) 0.5593(2) 0.0207(7) Uani 1 1 d D . . C22 C 0.3324(4) 0.2266(4) 0.5890(2) 0.0197(6) Uani 1 1 d D . . C23 C 0.2443(4) 0.1088(4) 0.5242(2) 0.0266(7) Uani 1 1 d D . . H23 H 0.1514 0.0420 0.5421 0.032 Uiso 1 1 calc R . . C24 C 0.2900(4) 0.0889(4) 0.4362(2) 0.0263(7) Uani 1 1 d D . . H24 H 0.2302 0.0088 0.3943 0.032 Uiso 1 1 calc R . . C25 C 0.4272(4) 0.1893(4) 0.4092(2) 0.0263(8) Uani 1 1 d D . . C26 C 0.5151(4) 0.3085(4) 0.4685(2) 0.0262(7) Uani 1 1 d D . . H26 H 0.6046 0.3764 0.4478 0.031 Uiso 1 1 calc R . . C27 C 0.5788(4) 0.4485(4) 0.6200(2) 0.0219(6) Uani 1 1 d D . . H27 H 0.6626 0.5148 0.5932 0.026 Uiso 1 1 calc R . . N6 N 0.5665(3) 0.4696(3) 0.70758(19) 0.0195(5) Uani 1 1 d . . . C28 C 0.6880(4) 0.5848(3) 0.7665(2) 0.0195(6) Uani 1 1 d . . . H28 H 0.7959 0.5992 0.7401 0.023 Uiso 1 1 calc R . . C29 C 0.7094(4) 0.5219(4) 0.8651(2) 0.0224(7) Uani 1 1 d . . . O7 O 0.5964(3) 0.4137(3) 0.88707(16) 0.0282(6) Uani 1 1 d . . . O8 O 0.8347(3) 0.5804(3) 0.91993(16) 0.0299(5) Uani 1 1 d . . . C30 C 0.6290(4) 0.7407(4) 0.7716(2) 0.0211(6) Uani 1 1 d . . . H30A H 0.5148 0.7229 0.7881 0.025 Uiso 1 1 calc R . . H30B H 0.6995 0.8064 0.8225 0.025 Uiso 1 1 calc R . . C31 C 0.6333(4) 0.8264(4) 0.6798(2) 0.0246(7) Uani 1 1 d . . . H31A H 0.5558 0.7644 0.6301 0.030 Uiso 1 1 calc R . . H31B H 0.7454 0.8369 0.6607 0.030 Uiso 1 1 calc R . . C32 C 0.5873(4) 0.9870(4) 0.6877(2) 0.0263(7) Uani 1 1 d . . . H32A H 0.5980 1.0379 0.6272 0.032 Uiso 1 1 calc R . . H32B H 0.4704 0.9755 0.6990 0.032 Uiso 1 1 calc R . . C33 C 0.8500(4) 1.1467(4) 0.7599(2) 0.0254(7) Uani 1 1 d D . . N7 N 0.6900(4) 1.0864(3) 0.7633(2) 0.0247(6) Uani 1 1 d D . . H7A H 0.6447 1.1076 0.8132 0.030 Uiso 1 1 calc R . . N8 N 0.9193(4) 1.1470(4) 0.6811(2) 0.0336(7) Uani 1 1 d D . . H8A H 1.0232 1.1895 0.6809 0.040 Uiso 1 1 calc R . . H8B H 0.8614 1.1046 0.6292 0.040 Uiso 1 1 calc R . . N9 N 0.9387(4) 1.2115(4) 0.8392(2) 0.0375(7) Uani 1 1 d D . . H9A H 1.0425 1.2540 0.8389 0.045 Uiso 1 1 calc R . . H9B H 0.8929 1.2114 0.8915 0.045 Uiso 1 1 calc R . . N10 N 0.4847(4) 0.1625(4) 0.3187(2) 0.0348(8) Uani 1 1 d D . . O9 O 0.4127(4) 0.0506(3) 0.26896(19) 0.0438(7) Uani 1 1 d D . . O10 O 0.6049(4) 0.2544(4) 0.2963(2) 0.0575(9) Uani 1 1 d D . . O2W O 0.2268(3) 0.4732(3) 0.82031(18) 0.0325(6) Uani 1 1 d D . . H2WA H 0.234(5) 0.506(5) 0.8751(14) 0.039 Uiso 1 1 d D . . H2WB H 0.151(4) 0.509(5) 0.790(2) 0.039 Uiso 1 1 d D . . O3W O 0.3238(4) 0.1697(3) 0.85965(19) 0.0422(7) Uani 1 1 d D . . H3WA H 0.336(6) 0.179(5) 0.9180(13) 0.051 Uiso 1 1 d D . . H3WB H 0.282(6) 0.083(3) 0.843(3) 0.051 Uiso 1 1 d D . . Cl2 Cl 0.78743(14) 0.88273(13) 0.44028(7) 0.0364(2) Uani 1 1 d DU . . O11 O 0.6282(5) 0.7971(6) 0.4120(3) 0.1129(19) Uani 1 1 d DU . . O12 O 0.8814(5) 0.8044(5) 0.5060(3) 0.0881(13) Uani 1 1 d DU . . O13 O 0.7723(5) 1.0250(4) 0.4871(2) 0.0692(10) Uani 1 1 d DU . . O14 O 0.8740(5) 0.9226(4) 0.3606(2) 0.0812(13) Uani 1 1 d DU . . O4W O 0.6535(4) 0.0134(3) -0.04620(19) 0.0393(6) Uani 1 1 d DU . . H4WA H 0.679(5) 0.058(5) 0.0081(18) 0.047 Uiso 1 1 d D . . H4WB H 0.564(4) 0.045(5) -0.064(3) 0.047 Uiso 1 1 d D . . O5W O 0.6691(3) 0.2231(3) 0.10876(18) 0.0367(6) Uani 1 1 d DU . . H5WA H 0.574(3) 0.242(5) 0.094(3) 0.044 Uiso 1 1 d D . . H5WB H 0.681(5) 0.216(5) 0.1664(13) 0.044 Uiso 1 1 d 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 Cu1 0.0240(2) 0.0206(2) 0.01542(19) -0.00037(15) 0.00507(16) -0.00745(15) Cl1 0.0317(5) 0.0306(5) 0.0382(5) 0.0006(4) 0.0112(4) 0.0071(4) O1 0.0336(14) 0.0234(12) 0.0192(12) -0.0009(9) 0.0086(10) -0.0090(10) C1 0.0177(15) 0.0255(17) 0.0149(15) 0.0044(12) 0.0063(12) -0.0001(13) C2 0.0194(15) 0.0228(16) 0.0163(16) 0.0045(13) 0.0024(12) 0.0032(13) C3 0.0289(18) 0.0256(17) 0.0213(16) 0.0028(13) 0.0016(13) -0.0018(14) C4 0.0277(17) 0.0300(18) 0.0249(17) 0.0111(14) 0.0080(14) -0.0001(14) C5 0.0225(16) 0.0300(18) 0.0153(15) 0.0033(13) 0.0039(12) 0.0035(14) C6 0.0222(16) 0.0251(17) 0.0213(16) 0.0014(13) 0.0041(13) -0.0010(13) C7 0.0189(15) 0.0225(16) 0.0228(16) 0.0008(13) 0.0016(12) -0.0042(12) N1 0.0150(12) 0.0228(13) 0.0141(12) 0.0015(10) 0.0030(10) -0.0055(10) C8 0.0150(14) 0.0204(15) 0.0214(15) 0.0055(12) 0.0045(12) -0.0028(12) C9 0.0184(15) 0.0187(15) 0.0203(15) -0.0010(12) 0.0049(12) 0.0002(12) O2 0.0274(12) 0.0232(12) 0.0153(11) -0.0013(9) 0.0035(9) -0.0100(10) O3 0.0401(14) 0.0306(13) 0.0186(11) 0.0030(10) 0.0087(10) -0.0145(11) C10 0.0198(15) 0.0230(16) 0.0196(15) -0.0010(12) 0.0046(12) -0.0055(12) C11 0.0218(17) 0.0250(17) 0.035(2) 0.0011(15) 0.0042(15) -0.0010(13) C12 0.0216(17) 0.0278(18) 0.0331(19) -0.0008(15) 0.0016(15) 0.0026(14) C13 0.0171(16) 0.041(2) 0.0278(18) 0.0015(15) 0.0026(13) 0.0048(15) N2 0.0225(15) 0.0336(17) 0.0248(15) -0.0091(13) 0.0060(12) -0.0005(12) N3 0.0410(19) 0.0347(18) 0.0354(18) -0.0058(14) 0.0104(15) -0.0170(14) N4 0.0335(18) 0.055(2) 0.0364(19) 0.0029(16) 0.0103(15) -0.0058(16) N5 0.0311(16) 0.0411(18) 0.0147(14) 0.0019(13) 0.0063(12) 0.0061(14) O4 0.0429(16) 0.0459(16) 0.0208(13) 0.0051(11) 0.0125(11) 0.0022(12) O5 0.0505(18) 0.0518(18) 0.0233(14) -0.0110(13) 0.0062(13) -0.0132(15) O1W 0.0189(12) 0.0251(12) 0.0213(12) 0.0040(9) 0.0032(9) -0.0065(10) O6W 0.065(2) 0.0290(15) 0.0371(16) -0.0008(12) 0.0027(15) -0.0025(13) Cu2 0.0237(2) 0.0214(2) 0.01756(19) 0.00025(15) 0.00381(16) -0.00590(16) O6 0.0214(12) 0.0337(13) 0.0229(12) -0.0053(10) 0.0057(9) -0.0091(10) C21 0.0200(15) 0.0226(16) 0.0173(16) -0.0012(13) -0.0010(12) 0.0004(13) C22 0.0168(15) 0.0214(16) 0.0196(16) -0.0008(13) -0.0005(12) 0.0014(12) C23 0.0202(16) 0.0272(17) 0.0281(18) -0.0039(14) 0.0010(13) -0.0055(13) C24 0.0261(17) 0.0269(17) 0.0234(17) -0.0078(14) -0.0026(14) 0.0021(14) C25 0.0286(18) 0.0294(19) 0.0197(17) -0.0038(14) 0.0008(14) 0.0036(15) C26 0.0260(17) 0.0265(17) 0.0243(17) -0.0012(14) 0.0034(14) -0.0009(14) C27 0.0241(16) 0.0187(15) 0.0212(16) 0.0018(12) 0.0039(13) -0.0017(13) N6 0.0190(13) 0.0185(13) 0.0197(14) -0.0009(10) 0.0024(11) -0.0007(10) C28 0.0208(15) 0.0197(15) 0.0153(14) -0.0021(12) -0.0002(12) -0.0018(12) C29 0.0256(17) 0.0221(16) 0.0187(15) 0.0001(12) 0.0000(13) 0.0036(13) O7 0.0307(14) 0.0276(13) 0.0210(12) 0.0060(10) 0.0000(10) -0.0076(10) O8 0.0313(13) 0.0295(13) 0.0231(12) 0.0012(10) -0.0053(10) -0.0055(10) C30 0.0251(16) 0.0178(15) 0.0189(15) -0.0028(12) 0.0036(12) -0.0008(12) C31 0.0290(17) 0.0202(16) 0.0221(17) -0.0005(13) 0.0036(14) -0.0034(13) C32 0.0263(17) 0.0232(16) 0.0292(18) 0.0073(14) 0.0070(14) 0.0011(13) C33 0.0305(18) 0.0159(15) 0.0301(18) 0.0025(13) 0.0107(15) 0.0001(13) N7 0.0285(15) 0.0176(13) 0.0286(16) -0.0002(11) 0.0145(13) -0.0019(11) N8 0.0284(16) 0.0399(17) 0.0276(16) -0.0042(14) 0.0115(13) -0.0130(13) N9 0.0329(17) 0.0418(18) 0.0328(17) -0.0091(14) 0.0099(14) -0.0105(14) N10 0.0409(19) 0.0386(19) 0.0225(16) -0.0082(14) -0.0008(14) 0.0040(15) O9 0.069(2) 0.0331(15) 0.0260(14) -0.0109(12) 0.0089(14) -0.0006(14) O10 0.056(2) 0.077(2) 0.0291(15) -0.0186(15) 0.0186(14) -0.0254(17) O2W 0.0337(14) 0.0409(15) 0.0227(13) -0.0053(11) 0.0017(11) 0.0079(12) O3W 0.065(2) 0.0284(15) 0.0232(14) -0.0004(11) 0.0061(14) -0.0209(14) Cl2 0.0337(4) 0.0461(5) 0.0252(4) -0.0055(4) 0.0072(3) -0.0069(4) O11 0.061(2) 0.163(5) 0.079(3) -0.005(3) -0.009(2) -0.068(3) O12 0.080(3) 0.113(4) 0.086(3) 0.018(3) 0.015(2) 0.055(3) O13 0.099(3) 0.065(2) 0.049(2) 0.0022(17) 0.0295(19) 0.016(2) O14 0.111(3) 0.077(3) 0.045(2) -0.0255(17) 0.050(2) -0.037(2) O4W 0.0433(16) 0.0421(16) 0.0272(14) -0.0031(12) 0.0135(12) -0.0133(13) O5W 0.0265(13) 0.0525(17) 0.0280(13) -0.0046(13) 0.0092(11) -0.0054(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 Cu1 O1 1.920(2) . ? Cu1 N1 1.941(2) . ? Cu1 O2 1.957(2) . ? Cu1 O1W 2.033(2) . ? Cu1 Cl1 2.5028(9) . ? O1 C2 1.290(4) . ? C1 C6 1.399(4) . ? C1 C2 1.437(4) . ? C1 C7 1.447(4) . ? C2 C3 1.416(4) . ? C3 C4 1.350(5) . ? C4 C5 1.409(5) . ? C5 C6 1.367(4) . ? C5 N5 1.447(4) . ? C7 N1 1.273(4) . ? N1 C8 1.481(4) . ? C8 C9 1.515(4) . ? C8 C10 1.522(4) . ? C9 O3 1.240(4) . ? C9 O2 1.278(4) . ? C10 C11 1.505(5) . ? C11 C12 1.531(5) . ? C12 N2 1.460(4) . ? C13 N4 1.318(4) . ? C13 N3 1.319(4) . ? C13 N2 1.331(4) . ? N5 O5 1.226(4) . ? N5 O4 1.248(4) . ? Cu2 O6 1.915(2) . ? Cu2 N6 1.931(3) . ? Cu2 O3W 1.955(3) . ? Cu2 O7 1.956(2) . ? Cu2 O2W 2.283(3) . ? O6 C22 1.307(4) . ? C21 C26 1.394(5) . ? C21 C22 1.435(4) . ? C21 C27 1.443(4) . ? C22 C23 1.409(4) . ? C23 C24 1.362(5) . ? C24 C25 1.399(5) . ? C25 C26 1.372(5) . ? C25 N10 1.449(4) . ? C27 N6 1.273(4) . ? N6 C28 1.462(4) . ? C28 C29 1.515(4) . ? C28 C30 1.524(4) . ? C29 O8 1.244(4) . ? C29 O7 1.274(4) . ? C30 C31 1.514(4) . ? C31 C32 1.518(4) . ? C32 N7 1.457(4) . ? C33 N8 1.312(4) . ? C33 N9 1.329(4) . ? C33 N7 1.335(4) . ? N10 O9 1.218(4) . ? N10 O10 1.236(4) . ? Cl2 O11 1.401(3) . ? Cl2 O12 1.403(4) . ? Cl2 O14 1.422(3) . ? Cl2 O13 1.429(4) . ? 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 Cu1 N1 93.42(10) . . ? O1 Cu1 O2 173.17(10) . . ? N1 Cu1 O2 83.26(10) . . ? O1 Cu1 O1W 91.36(10) . . ? N1 Cu1 O1W 147.32(10) . . ? O2 Cu1 O1W 88.28(9) . . ? O1 Cu1 Cl1 94.80(7) . . ? N1 Cu1 Cl1 120.18(8) . . ? O2 Cu1 Cl1 92.02(7) . . ? O1W Cu1 Cl1 91.53(7) . . ? C2 O1 Cu1 127.2(2) . . ? C6 C1 C2 119.9(3) . . ? C6 C1 C7 116.6(3) . . ? C2 C1 C7 123.5(3) . . ? O1 C2 C3 119.0(3) . . ? O1 C2 C1 124.0(3) . . ? C3 C2 C1 117.0(3) . . ? C4 C3 C2 122.5(3) . . ? C3 C4 C5 119.3(3) . . ? C6 C5 C4 121.3(3) . . ? C6 C5 N5 119.1(3) . . ? C4 C5 N5 119.6(3) . . ? C5 C6 C1 120.0(3) . . ? N1 C7 C1 124.6(3) . . ? C7 N1 C8 119.2(3) . . ? C7 N1 Cu1 126.8(2) . . ? C8 N1 Cu1 113.96(18) . . ? N1 C8 C9 108.1(2) . . ? N1 C8 C10 111.8(2) . . ? C9 C8 C10 113.2(2) . . ? O3 C9 O2 122.8(3) . . ? O3 C9 C8 119.3(3) . . ? O2 C9 C8 117.9(3) . . ? C9 O2 Cu1 116.0(2) . . ? C11 C10 C8 113.5(3) . . ? C10 C11 C12 111.8(3) . . ? N2 C12 C11 110.6(3) . . ? N4 C13 N3 119.5(3) . . ? N4 C13 N2 117.9(3) . . ? N3 C13 N2 122.5(3) . . ? C13 N2 C12 127.9(3) . . ? O5 N5 O4 122.9(3) . . ? O5 N5 C5 119.5(3) . . ? O4 N5 C5 117.6(3) . . ? O6 Cu2 N6 93.10(10) . . ? O6 Cu2 O3W 89.43(11) . . ? N6 Cu2 O3W 165.94(13) . . ? O6 Cu2 O7 169.76(10) . . ? N6 Cu2 O7 83.74(11) . . ? O3W Cu2 O7 91.35(11) . . ? O6 Cu2 O2W 92.31(10) . . ? N6 Cu2 O2W 106.30(11) . . ? O3W Cu2 O2W 87.40(12) . . ? O7 Cu2 O2W 97.93(10) . . ? C22 O6 Cu2 124.36(19) . . ? C26 C21 C22 119.3(3) . . ? C26 C21 C27 116.6(3) . . ? C22 C21 C27 124.0(3) . . ? O6 C22 C23 118.9(3) . . ? O6 C22 C21 123.0(3) . . ? C23 C22 C21 118.1(3) . . ? C24 C23 C22 121.9(3) . . ? C23 C24 C25 119.0(3) . . ? C26 C25 C24 121.6(3) . . ? C26 C25 N10 118.7(3) . . ? C24 C25 N10 119.6(3) . . ? C25 C26 C21 120.1(3) . . ? N6 C27 C21 123.9(3) . . ? C27 N6 C28 120.8(3) . . ? C27 N6 Cu2 126.0(2) . . ? C28 N6 Cu2 112.12(19) . . ? N6 C28 C29 107.4(2) . . ? N6 C28 C30 111.4(3) . . ? C29 C28 C30 109.4(2) . . ? O8 C29 O7 124.2(3) . . ? O8 C29 C28 118.0(3) . . ? O7 C29 C28 117.8(3) . . ? C29 O7 Cu2 114.4(2) . . ? C31 C30 C28 113.3(3) . . ? C30 C31 C32 113.0(3) . . ? N7 C32 C31 113.4(3) . . ? N8 C33 N9 119.9(3) . . ? N8 C33 N7 122.2(3) . . ? N9 C33 N7 117.9(3) . . ? C33 N7 C32 123.5(3) . . ? O9 N10 O10 123.6(3) . . ? O9 N10 C25 118.4(3) . . ? O10 N10 C25 118.1(3) . . ? O11 Cl2 O12 112.2(3) . . ? O11 Cl2 O14 111.0(3) . . ? O12 Cl2 O14 110.6(3) . . ? O11 Cl2 O13 109.2(3) . . ? O12 Cl2 O13 106.2(2) . . ? O14 Cl2 O13 107.3(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N2 H2 O8 0.87 1.94 2.800(4) 170.8 1_554 N3 H3A Cl1 0.87 2.74 3.479(3) 144.1 1_665 N3 H3B O14 0.87 2.13 2.989(4) 167.0 . N4 H4A Cl1 0.87 2.41 3.226(4) 156.9 1_665 N4 H4B O8 0.87 2.61 3.306(4) 137.5 1_554 O1W H1WA O8 0.822(17) 1.889(19) 2.700(3) 168(4) 1_454 O1W H1WB O5W 0.804(17) 1.857(19) 2.658(3) 174(3) 1_455 O6W H6WA O3 0.848(19) 1.97(2) 2.748(4) 151(4) . O6W H6WB O5 0.856(18) 2.26(2) 3.096(4) 167(4) 1_554 N7 H7A O4W 0.87 2.17 2.828(4) 132.2 1_566 N8 H8A O6 0.87 2.13 2.980(4) 166.3 1_665 N8 H8B O13 0.87 2.13 2.979(5) 166.0 . N9 H9A O2W 0.87 2.26 3.031(4) 147.0 1_665 N9 H9B O1W 0.87 2.32 3.015(4) 137.1 1_666 O2W H2WA O2 0.818(18) 1.96(2) 2.772(3) 171(4) 1_556 O2W H2WB O4 0.827(18) 2.21(2) 2.920(4) 144(3) . O3W H3WA Cl1 0.824(18) 2.32(2) 3.110(3) 161(4) 1_556 O3W H3WB O6W 0.796(18) 1.882(19) 2.677(4) 177(4) 1_546 O4W H4WA O5W 0.846(18) 2.03(3) 2.816(4) 154(4) . O4W H4WB O3W 0.844(18) 2.55(2) 3.385(5) 169(4) 1_554 O5W H5WA Cl1 0.828(18) 2.31(2) 3.116(3) 165(4) . O5W H5WB O10 0.818(18) 2.05(3) 2.793(4) 150(3) . _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.723 _refine_diff_density_min -0.490 _refine_diff_density_rms 0.074 # Attachment '- 3.cif' data_9059a _database_code_depnum_ccdc_archive 'CCDC 786081' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H32 Cu N4 O10' _chemical_formula_weight 504.00 _chemical_absolute_configuration syn 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' Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M C222(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x, y, -z+1/2' 'x, -y, -z' 'x+1/2, y+1/2, z' '-x+1/2, -y+1/2, z+1/2' '-x+1/2, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 11.7263(10) _cell_length_b 19.1424(10) _cell_length_c 21.0208(14) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4718.5(6) _cell_formula_units_Z 8 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used 4173 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 25.53 _exptl_crystal_description Rod _exptl_crystal_colour Green _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.419 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2120 _exptl_absorpt_coefficient_mu 0.981 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.5074 _exptl_absorpt_correction_T_max 0.9083 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16649 _diffrn_reflns_av_R_equivalents 0.0548 _diffrn_reflns_av_sigmaI/netI 0.0693 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.94 _diffrn_reflns_theta_max 27.50 _reflns_number_total 5400 _reflns_number_gt 4795 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0409P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.032(13) _refine_ls_number_reflns 5400 _refine_ls_number_parameters 312 _refine_ls_number_restraints 60 _refine_ls_R_factor_all 0.0530 _refine_ls_R_factor_gt 0.0461 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.1010 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.19050(3) 0.288254(18) 0.328552(18) 0.02904(11) Uani 1 1 d . . . O1 O 0.1441(2) 0.31468(11) 0.24634(11) 0.0363(5) Uani 1 1 d D . . C1 C 0.1227(3) 0.19866(17) 0.20331(15) 0.0300(7) Uani 1 1 d D . . C2 C 0.1162(3) 0.27271(17) 0.20024(16) 0.0336(8) Uani 1 1 d D . . C3 C 0.0762(3) 0.3015(2) 0.14264(17) 0.0412(9) Uani 1 1 d D . . H3 H 0.0672 0.3502 0.1396 0.049 Uiso 1 1 calc R . . C4 C 0.0497(3) 0.2606(2) 0.09057(18) 0.0430(9) Uani 1 1 d D . . H4 H 0.0257 0.2823 0.0527 0.052 Uiso 1 1 calc R . . C5 C 0.0578(3) 0.1882(2) 0.09269(17) 0.0418(9) Uani 1 1 d D . . C6 C 0.0928(3) 0.1588(2) 0.14898(17) 0.0372(8) Uani 1 1 d D . . H6 H 0.0973 0.1099 0.1516 0.045 Uiso 1 1 calc R . . C7 C 0.1624(3) 0.16194(16) 0.25849(16) 0.0292(7) Uani 1 1 d D . . H7 H 0.1642 0.1129 0.2563 0.035 Uiso 1 1 calc R . . N1 N 0.1958(2) 0.19013(12) 0.31052(11) 0.0253(5) Uani 1 1 d . . . C8 C 0.2392(3) 0.14798(16) 0.36368(14) 0.0270(6) Uani 1 1 d . . . H8 H 0.1875 0.1079 0.3711 0.032 Uiso 1 1 calc R . . C9 C 0.2427(3) 0.19405(16) 0.42318(14) 0.0286(7) Uani 1 1 d . . . O2 O 0.2257(2) 0.25907(11) 0.41472(10) 0.0325(5) Uani 1 1 d . . . O3 O 0.2650(2) 0.16844(12) 0.47547(10) 0.0381(6) Uani 1 1 d . . . C10 C 0.3605(3) 0.12086(16) 0.34956(15) 0.0266(7) Uani 1 1 d . . . H10A H 0.3867 0.0929 0.3858 0.032 Uiso 1 1 calc R . . H10B H 0.3575 0.0901 0.3123 0.032 Uiso 1 1 calc R . . C11 C 0.4466(3) 0.17888(16) 0.33710(14) 0.0270(6) Uani 1 1 d . . . H11A H 0.4440 0.2126 0.3721 0.032 Uiso 1 1 calc R . . H11B H 0.4260 0.2034 0.2978 0.032 Uiso 1 1 calc R . . C12 C 0.5679(3) 0.14989(16) 0.33093(15) 0.0299(6) Uani 1 1 d . . . H12A H 0.5681 0.1120 0.2996 0.036 Uiso 1 1 calc R . . H12B H 0.6184 0.1869 0.3153 0.036 Uiso 1 1 calc R . . C13 C 0.6504(3) 0.16412(16) 0.43734(14) 0.0267(6) Uani 1 1 d D . . N2 N 0.6116(2) 0.12369(13) 0.39085(13) 0.0282(6) Uani 1 1 d D . . H2 H 0.6124 0.0787 0.3967 0.034 Uiso 1 1 calc R . . N3 N 0.6638(2) 0.23210(14) 0.42964(13) 0.0334(6) Uani 1 1 d D . . H3A H 0.6896 0.2575 0.4608 0.040 Uiso 1 1 calc R . . H3B H 0.6467 0.2515 0.3934 0.040 Uiso 1 1 calc R . . N4 N 0.6764(3) 0.13513(15) 0.49248(13) 0.0392(7) Uani 1 1 d D . . H4A H 0.7023 0.1608 0.5235 0.047 Uiso 1 1 calc R . . H4B H 0.6678 0.0904 0.4978 0.047 Uiso 1 1 calc R . . C14 C 0.0305(3) 0.1435(3) 0.03474(19) 0.0569(12) Uani 1 1 d D . . H14A H 0.0521 0.0955 0.0431 0.085 Uiso 1 1 calc R . . H14B H 0.0727 0.1608 -0.0017 0.085 Uiso 1 1 calc R . . H14C H -0.0506 0.1458 0.0259 0.085 Uiso 1 1 calc R . . C15 C 0.3196(4) 0.39768(17) 0.34475(18) 0.0441(9) Uani 1 1 d D . . O4 O 0.2146(2) 0.38616(11) 0.35543(12) 0.0374(6) Uani 1 1 d D . . O5 O 0.3813(2) 0.35370(13) 0.31726(13) 0.0470(6) Uani 1 1 d D . . C16 C 0.3667(5) 0.4652(3) 0.3667(4) 0.094(2) Uani 1 1 d D . . H16A H 0.4491 0.4643 0.3632 0.141 Uiso 1 1 calc R . . H16B H 0.3452 0.4729 0.4107 0.141 Uiso 1 1 calc R . . H16C H 0.3365 0.5027 0.3405 0.141 Uiso 1 1 calc R . . O1W O 0.2211(4) -0.03459(17) 0.35187(17) 0.0736(10) Uani 1 1 d DU . . H1WA H 0.205(5) -0.0777(13) 0.348(3) 0.110 Uiso 1 1 d D . . H1WB H 0.191(6) -0.025(3) 0.3877(18) 0.110 Uiso 1 1 d D . . O2W O 0.3559(3) -0.05463(13) 0.45943(14) 0.0496(7) Uani 1 1 d DU . . H2WA H 0.375(4) -0.0934(15) 0.474(2) 0.074 Uiso 1 1 d D . . H2WB H 0.310(4) -0.063(2) 0.4306(18) 0.074 Uiso 1 1 d D . . O3W O 0.5800(2) -0.01888(13) 0.42300(14) 0.0443(6) Uani 1 1 d DU . . H3WA H 0.609(3) -0.0502(18) 0.401(2) 0.066 Uiso 1 1 d D . . H3WB H 0.5107(17) -0.029(2) 0.426(2) 0.066 Uiso 1 1 d D . . O4W O 0.3831(5) -0.0311(2) 0.2556(2) 0.1122(17) Uani 1 1 d DU . . H4WA H 0.374(6) -0.053(4) 0.223(2) 0.168 Uiso 1 1 d D . . H4WB H 0.321(4) -0.030(5) 0.275(3) 0.168 Uiso 1 1 d D . . O5W O 0.6149(2) 0.33192(14) 0.32354(14) 0.0446(6) Uani 1 1 d DU . . H5WA H 0.5442(17) 0.341(2) 0.321(2) 0.067 Uiso 1 1 d D . . H5WB H 0.636(4) 0.337(2) 0.2849(11) 0.067 Uiso 1 1 d 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 Cu1 0.0365(2) 0.02237(17) 0.02829(18) -0.00085(15) 0.00178(17) 0.00293(16) O1 0.0477(14) 0.0292(11) 0.0322(12) 0.0024(9) -0.0035(11) 0.0055(10) C1 0.0276(16) 0.0345(18) 0.0281(16) -0.0004(13) 0.0011(13) 0.0043(13) C2 0.0270(16) 0.041(2) 0.0329(17) 0.0022(14) 0.0035(14) 0.0049(14) C3 0.0363(18) 0.051(2) 0.0366(19) 0.0119(17) 0.0010(15) 0.0054(17) C4 0.0337(19) 0.064(2) 0.0312(19) 0.0092(17) 0.0014(15) 0.0107(18) C5 0.0270(18) 0.070(3) 0.0288(18) -0.0064(17) -0.0011(14) 0.0094(17) C6 0.0309(18) 0.046(2) 0.0352(18) -0.0068(15) -0.0018(14) 0.0075(15) C7 0.0266(17) 0.0253(14) 0.0356(17) -0.0027(12) 0.0017(13) 0.0018(12) N1 0.0250(12) 0.0253(11) 0.0257(12) 0.0001(9) 0.0008(11) 0.0013(11) C8 0.0316(16) 0.0248(15) 0.0245(15) 0.0017(12) 0.0011(13) -0.0034(13) C9 0.0255(15) 0.0323(17) 0.0278(16) -0.0014(12) 0.0058(13) 0.0002(13) O2 0.0402(14) 0.0305(11) 0.0268(11) -0.0009(9) -0.0002(10) 0.0054(10) O3 0.0481(15) 0.0402(13) 0.0260(12) 0.0035(10) 0.0006(10) 0.0097(11) C10 0.0297(16) 0.0245(15) 0.0256(15) -0.0006(11) -0.0005(13) -0.0001(12) C11 0.0299(16) 0.0298(14) 0.0212(16) -0.0036(12) -0.0003(12) -0.0011(12) C12 0.0291(15) 0.0377(16) 0.0228(14) -0.0056(14) 0.0007(14) 0.0000(13) C13 0.0216(15) 0.0340(16) 0.0244(15) 0.0003(12) 0.0018(12) 0.0021(12) N2 0.0292(14) 0.0235(12) 0.0318(14) -0.0025(10) -0.0028(11) -0.0003(11) N3 0.0394(17) 0.0355(15) 0.0253(13) -0.0030(10) -0.0001(11) -0.0066(12) N4 0.0467(18) 0.0384(15) 0.0326(15) -0.0004(12) -0.0046(14) -0.0056(15) C14 0.042(2) 0.093(3) 0.036(2) -0.021(2) -0.0075(17) 0.013(2) C15 0.058(3) 0.0265(16) 0.047(2) 0.0019(14) 0.0035(19) -0.0046(18) O4 0.0442(15) 0.0265(11) 0.0415(13) -0.0042(9) 0.0045(11) 0.0027(10) O5 0.0435(15) 0.0409(13) 0.0565(17) -0.0050(12) 0.0069(13) -0.0021(12) C16 0.080(4) 0.051(3) 0.152(6) -0.038(3) 0.028(4) -0.026(3) O1W 0.091(3) 0.0527(18) 0.077(2) 0.0001(16) -0.012(2) -0.0178(18) O2W 0.0629(19) 0.0378(14) 0.0481(17) -0.0005(12) 0.0093(14) -0.0094(13) O3W 0.0524(16) 0.0287(12) 0.0518(17) -0.0071(11) 0.0076(14) 0.0008(12) O4W 0.159(4) 0.080(3) 0.097(4) -0.045(2) 0.033(3) -0.047(3) O5W 0.0414(14) 0.0492(14) 0.0431(14) 0.0062(13) 0.0035(13) -0.0035(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 Cu1 O1 1.881(2) . ? Cu1 N1 1.917(2) . ? Cu1 O2 1.940(2) . ? Cu1 O4 1.978(2) . ? O1 C2 1.301(4) . ? C1 C6 1.417(5) . ? C1 C2 1.421(5) . ? C1 C7 1.434(4) . ? C2 C3 1.411(5) . ? C3 C4 1.381(5) . ? C4 C5 1.389(6) . ? C5 C6 1.373(5) . ? C5 C14 1.523(5) . ? C7 N1 1.281(4) . ? N1 C8 1.469(4) . ? C8 C9 1.531(4) . ? C8 C10 1.543(5) . ? C9 O3 1.232(4) . ? C9 O2 1.273(4) . ? C10 C11 1.524(4) . ? C11 C12 1.532(4) . ? C12 N2 1.449(4) . ? C13 N3 1.321(4) . ? C13 N4 1.321(4) . ? C13 N2 1.327(4) . ? C15 O5 1.252(4) . ? C15 O4 1.271(5) . ? C15 C16 1.479(6) . ? 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 Cu1 N1 95.24(10) . . ? O1 Cu1 O2 175.39(10) . . ? N1 Cu1 O2 84.00(10) . . ? O1 Cu1 O4 92.80(10) . . ? N1 Cu1 O4 168.61(11) . . ? O2 Cu1 O4 88.62(10) . . ? C2 O1 Cu1 126.2(2) . . ? C6 C1 C2 119.1(3) . . ? C6 C1 C7 117.9(3) . . ? C2 C1 C7 122.9(3) . . ? O1 C2 C3 118.8(3) . . ? O1 C2 C1 124.6(3) . . ? C3 C2 C1 116.5(3) . . ? C4 C3 C2 122.2(4) . . ? C3 C4 C5 121.7(4) . . ? C6 C5 C4 117.2(4) . . ? C6 C5 C14 121.4(4) . . ? C4 C5 C14 121.4(4) . . ? C5 C6 C1 123.2(3) . . ? N1 C7 C1 125.7(3) . . ? C7 N1 C8 121.6(2) . . ? C7 N1 Cu1 124.9(2) . . ? C8 N1 Cu1 113.51(19) . . ? N1 C8 C9 108.3(2) . . ? N1 C8 C10 110.9(3) . . ? C9 C8 C10 109.0(3) . . ? O3 C9 O2 123.2(3) . . ? O3 C9 C8 120.4(3) . . ? O2 C9 C8 116.4(3) . . ? C9 O2 Cu1 116.4(2) . . ? C11 C10 C8 113.5(2) . . ? C10 C11 C12 111.5(3) . . ? N2 C12 C11 112.3(3) . . ? N3 C13 N4 119.6(3) . . ? N3 C13 N2 121.7(3) . . ? N4 C13 N2 118.7(3) . . ? C13 N2 C12 124.0(3) . . ? O5 C15 O4 121.7(3) . . ? O5 C15 C16 121.0(4) . . ? O4 C15 C16 117.3(4) . . ? C15 O4 Cu1 104.6(2) . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.530 _refine_diff_density_min -0.271 _refine_diff_density_rms 0.069 # Attachment '- RNap.cif' data_8181 _database_code_depnum_ccdc_archive 'CCDC 786082' #TrackingRef '- RNap.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H22 N4 O4' _chemical_formula_weight 346.39 _chemical_absolute_configuration syn loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' _cell_length_a 6.9339(5) _cell_length_b 8.4735(6) _cell_length_c 15.3249(10) _cell_angle_alpha 75.124(2) _cell_angle_beta 82.496(2) _cell_angle_gamma 80.882(2) _cell_volume 855.41(10) _cell_formula_units_Z 2 _cell_measurement_temperature 223(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Plate _exptl_crystal_colour Yellow _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.345 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 368 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9620 _exptl_absorpt_correction_T_max 0.9903 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2001)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 223(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 ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11184 _diffrn_reflns_av_R_equivalents 0.0304 _diffrn_reflns_av_sigmaI/netI 0.0736 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 1.38 _diffrn_reflns_theta_max 27.53 _reflns_number_total 7760 _reflns_number_gt 6085 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0722P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.1(13) _refine_ls_number_reflns 7760 _refine_ls_number_parameters 465 _refine_ls_number_restraints 28 _refine_ls_R_factor_all 0.0806 _refine_ls_R_factor_gt 0.0617 _refine_ls_wR_factor_ref 0.1532 _refine_ls_wR_factor_gt 0.1327 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.056 _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 O1 O 1.1909(4) 0.5327(3) 0.00001(16) 0.0346(6) Uani 1 1 d D . . C1 C 1.0703(5) 0.7571(4) -0.1170(2) 0.0229(6) Uani 1 1 d D . . C2 C 1.2209(5) 0.6357(4) -0.0761(2) 0.0248(7) Uani 1 1 d D . . C3 C 1.4165(5) 0.6332(5) -0.1224(2) 0.0332(8) Uani 1 1 d D . . H3 H 1.5189 0.5569 -0.0957 0.040 Uiso 1 1 calc R . . C4 C 1.4544(6) 0.7374(5) -0.2027(2) 0.0381(9) Uani 1 1 d D . . H4 H 1.5841 0.7340 -0.2300 0.046 Uiso 1 1 calc R . . C5 C 1.3452(8) 0.9527(5) -0.3370(3) 0.0605(14) Uani 1 1 d D . . H5 H 1.4735 0.9438 -0.3656 0.073 Uiso 1 1 calc R . . C6 C 1.2033(9) 1.0590(6) -0.3810(3) 0.0746(18) Uani 1 1 d D . . H6 H 1.2328 1.1244 -0.4394 0.089 Uiso 1 1 calc R . . C7 C 1.0135(8) 1.0711(5) -0.3395(3) 0.0651(15) Uani 1 1 d D . . H7 H 0.9145 1.1448 -0.3704 0.078 Uiso 1 1 calc R . . C8 C 0.9674(7) 0.9776(5) -0.2540(2) 0.0471(11) Uani 1 1 d D . . H8 H 0.8377 0.9885 -0.2270 0.057 Uiso 1 1 calc R . . C9 C 1.1121(5) 0.8659(4) -0.2066(2) 0.0324(8) Uani 1 1 d D . . C10 C 1.3056(6) 0.8537(5) -0.2484(3) 0.0410(10) Uani 1 1 d D . . C11 C 0.8829(5) 0.7700(4) -0.07018(19) 0.0235(6) Uani 1 1 d D . . H11 H 0.7857 0.8515 -0.0976 0.028 Uiso 1 1 calc R . . N1 N 0.8351(4) 0.6758(3) 0.00916(16) 0.0206(5) Uani 1 1 d D . . H1N H 0.912(3) 0.607(2) 0.0292(7) 0.025 Uiso 1 1 calc RD . . C12 C 0.6464(4) 0.6922(4) 0.0622(2) 0.0173(6) Uani 1 1 d . . . H12 H 0.5431 0.6734 0.0285 0.021 Uiso 1 1 calc R . . C13 C 0.5944(5) 0.8638(4) 0.0827(2) 0.0209(7) Uani 1 1 d . . . O2 O 0.4187(3) 0.9231(3) 0.08114(17) 0.0291(6) Uani 1 1 d . . . O3 O 0.7301(3) 0.9270(3) 0.10180(16) 0.0281(5) Uani 1 1 d . . . C14 C 0.6534(5) 0.5626(4) 0.1530(2) 0.0197(7) Uani 1 1 d . . . H14A H 0.7502 0.5868 0.1874 0.024 Uiso 1 1 calc R . . H14B H 0.5252 0.5738 0.1878 0.024 Uiso 1 1 calc R . . C15 C 0.7047(5) 0.3845(4) 0.1458(2) 0.0202(7) Uani 1 1 d . . . H15A H 0.6094 0.3571 0.1119 0.024 Uiso 1 1 calc R . . H15B H 0.8353 0.3688 0.1136 0.024 Uiso 1 1 calc R . . C16 C 0.7009(5) 0.2734(4) 0.2412(2) 0.0196(7) Uani 1 1 d . . . H16A H 0.7924 0.3053 0.2752 0.024 Uiso 1 1 calc R . . H16B H 0.5690 0.2889 0.2722 0.024 Uiso 1 1 calc R . . C17 C 0.7757(4) -0.0167(4) 0.3171(2) 0.0207(7) Uani 1 1 d D . . N2 N 0.7541(4) 0.1004(3) 0.24085(18) 0.0215(6) Uani 1 1 d D . . H2 H 0.7723 0.0725 0.1893 0.026 Uiso 1 1 calc R . . N3 N 0.8294(4) -0.1724(3) 0.3111(2) 0.0268(7) Uani 1 1 d D . . H3A H 0.8437 -0.2509 0.3601 0.032 Uiso 1 1 calc R . . H3B H 0.8501 -0.1954 0.2582 0.032 Uiso 1 1 calc R . . N4 N 0.7442(4) 0.0188(3) 0.39718(19) 0.0251(6) Uani 1 1 d D . . H4A H 0.7086 0.1202 0.4009 0.030 Uiso 1 1 calc R . . H4B H 0.7591 -0.0593 0.4463 0.030 Uiso 1 1 calc R . . O4 O 0.7812(4) 0.7180(3) 0.52601(16) 0.0320(6) Uani 1 1 d D . . C21 C 0.6699(5) 0.5043(4) 0.6460(2) 0.0228(6) Uani 1 1 d D . . C22 C 0.8023(5) 0.6207(4) 0.6040(2) 0.0266(8) Uani 1 1 d D . . C23 C 0.9682(5) 0.6234(4) 0.6510(2) 0.0305(7) Uani 1 1 d D . . H23 H 1.0603 0.6958 0.6234 0.037 Uiso 1 1 calc R . . C24 C 0.9935(5) 0.5243(4) 0.7335(2) 0.0350(8) Uani 1 1 d D . . H24 H 1.1044 0.5281 0.7619 0.042 Uiso 1 1 calc R . . C25 C 0.8815(7) 0.3197(5) 0.8692(3) 0.0490(11) Uani 1 1 d D . . H25 H 0.9914 0.3269 0.8973 0.059 Uiso 1 1 calc R . . C26 C 0.7473(8) 0.2193(5) 0.9153(3) 0.0559(13) Uani 1 1 d D . . H26 H 0.7632 0.1599 0.9754 0.067 Uiso 1 1 calc R . . C27 C 0.5866(8) 0.2045(5) 0.8735(3) 0.0515(11) Uani 1 1 d D . . H27 H 0.4954 0.1339 0.9053 0.062 Uiso 1 1 calc R . . C28 C 0.5605(6) 0.2928(4) 0.7857(2) 0.0365(8) Uani 1 1 d D . . H28 H 0.4523 0.2808 0.7580 0.044 Uiso 1 1 calc R . . C29 C 0.6943(5) 0.4010(4) 0.7371(2) 0.0278(8) Uani 1 1 d D . . C30 C 0.8574(5) 0.4131(4) 0.7796(2) 0.0333(8) Uani 1 1 d D . . C31 C 0.5178(5) 0.4888(3) 0.5981(2) 0.0224(6) Uani 1 1 d D . . H31 H 0.4367 0.4073 0.6257 0.027 Uiso 1 1 calc R . . N5 N 0.4811(4) 0.5795(3) 0.51792(16) 0.0219(5) Uani 1 1 d D . . H5N H 0.535(2) 0.654(3) 0.4989(7) 0.026 Uiso 1 1 calc RD . . C32 C 0.3434(5) 0.5479(4) 0.4625(2) 0.0209(7) Uani 1 1 d . . . H32 H 0.2104 0.5538 0.4950 0.025 Uiso 1 1 calc R . . C33 C 0.3994(5) 0.3767(4) 0.4417(2) 0.0199(7) Uani 1 1 d . . . O5 O 0.5709(3) 0.3064(3) 0.45137(17) 0.0307(6) Uani 1 1 d . . . O6 O 0.2675(4) 0.3232(3) 0.41382(17) 0.0302(6) Uani 1 1 d . . . C34 C 0.3421(5) 0.6784(4) 0.3725(2) 0.0204(7) Uani 1 1 d . . . H34A H 0.2530 0.6523 0.3351 0.024 Uiso 1 1 calc R . . H34B H 0.4741 0.6703 0.3407 0.024 Uiso 1 1 calc R . . C35 C 0.2809(5) 0.8567(4) 0.3794(2) 0.0214(7) Uani 1 1 d . . . H35A H 0.1475 0.8692 0.4093 0.026 Uiso 1 1 calc R . . H35B H 0.3698 0.8871 0.4152 0.026 Uiso 1 1 calc R . . C36 C 0.2892(5) 0.9667(4) 0.2846(2) 0.0199(7) Uani 1 1 d . . . H36A H 0.4228 0.9511 0.2553 0.024 Uiso 1 1 calc R . . H36B H 0.2012 0.9336 0.2494 0.024 Uiso 1 1 calc R . . C37 C 0.2235(4) 1.2583(4) 0.2067(2) 0.0196(7) Uani 1 1 d D . . N6 N 0.2336(4) 1.1411(3) 0.28314(19) 0.0234(6) Uani 1 1 d D . . H6A H 0.2060 1.1694 0.3345 0.028 Uiso 1 1 calc R . . N7 N 0.1718(4) 1.4138(3) 0.2118(2) 0.0272(7) Uani 1 1 d D . . H7A H 0.1629 1.4920 0.1625 0.033 Uiso 1 1 calc R . . H7B H 0.1468 1.4373 0.2645 0.033 Uiso 1 1 calc R . . N8 N 0.2611(4) 1.2232(3) 0.12682(19) 0.0258(6) Uani 1 1 d D . . H8A H 0.2935 1.1214 0.1233 0.031 Uiso 1 1 calc R . . H8B H 0.2536 1.3018 0.0776 0.031 Uiso 1 1 calc R . . O1W O 0.0908(4) 0.7651(3) 0.14456(18) 0.0328(6) Uani 1 1 d D . . H1WA H -0.005(4) 0.838(4) 0.116(2) 0.039 Uiso 1 1 d D . . H1WB H 0.188(4) 0.822(4) 0.114(2) 0.039 Uiso 1 1 d D . . O2W O 0.8988(4) 0.4764(3) 0.38529(19) 0.0375(7) Uani 1 1 d D . . H2WA H 0.982(5) 0.438(5) 0.428(2) 0.045 Uiso 1 1 d D . . H2WB H 0.801(5) 0.426(5) 0.421(2) 0.045 Uiso 1 1 d 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 O1 0.0365(15) 0.0359(15) 0.0203(12) 0.0024(11) 0.0028(10) 0.0085(12) C1 0.0291(17) 0.0221(15) 0.0175(14) -0.0069(12) 0.0035(12) -0.0042(13) C2 0.0345(19) 0.0242(17) 0.0167(16) -0.0088(13) 0.0025(13) -0.0049(14) C3 0.0282(18) 0.042(2) 0.0325(19) -0.0204(16) 0.0037(14) -0.0013(16) C4 0.037(2) 0.043(2) 0.037(2) -0.0202(17) 0.0162(16) -0.0111(17) C5 0.083(4) 0.043(3) 0.042(3) -0.003(2) 0.035(2) -0.013(2) C6 0.120(5) 0.039(3) 0.039(3) 0.014(2) 0.032(3) -0.004(3) C7 0.103(4) 0.041(2) 0.026(2) 0.0109(18) 0.015(2) 0.017(2) C8 0.061(3) 0.033(2) 0.030(2) 0.0027(16) 0.0097(18) 0.0141(19) C9 0.047(2) 0.0188(16) 0.0255(17) -0.0035(13) 0.0094(15) -0.0007(15) C10 0.058(3) 0.032(2) 0.030(2) -0.0104(16) 0.0195(18) -0.0139(18) C11 0.0334(18) 0.0161(15) 0.0186(15) -0.0018(12) -0.0035(12) 0.0009(12) N1 0.0200(13) 0.0201(12) 0.0176(12) -0.0014(10) -0.0008(10) 0.0033(10) C12 0.0177(16) 0.0164(16) 0.0166(15) -0.0025(12) -0.0016(12) -0.0010(13) C13 0.0236(18) 0.0190(16) 0.0176(16) -0.0029(13) 0.0050(13) -0.0034(14) O2 0.0243(13) 0.0236(13) 0.0362(14) -0.0067(10) 0.0018(11) 0.0014(10) O3 0.0302(13) 0.0205(12) 0.0353(13) -0.0095(10) -0.0022(11) -0.0049(10) C14 0.0214(16) 0.0175(16) 0.0184(15) -0.0026(13) 0.0006(12) -0.0023(13) C15 0.0202(16) 0.0177(16) 0.0226(17) -0.0039(13) -0.0004(13) -0.0050(13) C16 0.0185(17) 0.0151(16) 0.0237(17) -0.0037(13) 0.0023(13) -0.0027(13) C17 0.0149(16) 0.0161(16) 0.0297(18) -0.0016(14) -0.0002(13) -0.0061(13) N2 0.0277(15) 0.0156(14) 0.0206(14) -0.0031(11) -0.0014(11) -0.0038(12) N3 0.0339(17) 0.0153(14) 0.0294(16) -0.0025(12) -0.0036(13) -0.0026(13) N4 0.0345(16) 0.0138(14) 0.0238(15) -0.0019(11) -0.0019(12) 0.0017(12) O4 0.0457(16) 0.0277(14) 0.0209(13) 0.0049(10) -0.0084(11) -0.0133(12) C21 0.0311(17) 0.0178(14) 0.0179(14) -0.0051(12) -0.0009(12) 0.0019(12) C22 0.039(2) 0.0198(17) 0.0215(17) -0.0085(14) -0.0035(15) 0.0023(15) C23 0.0306(18) 0.0348(19) 0.0279(17) -0.0108(15) -0.0012(14) -0.0061(15) C24 0.038(2) 0.038(2) 0.0345(19) -0.0161(16) -0.0171(16) 0.0022(16) C25 0.081(3) 0.038(2) 0.0275(19) -0.0051(17) -0.027(2) 0.008(2) C26 0.107(4) 0.036(2) 0.0183(19) 0.0039(17) -0.017(2) 0.003(2) C27 0.090(3) 0.029(2) 0.028(2) 0.0023(16) 0.002(2) -0.006(2) C28 0.058(2) 0.0237(17) 0.0220(17) 0.0010(13) -0.0006(16) -0.0021(16) C29 0.044(2) 0.0205(16) 0.0175(16) -0.0066(13) -0.0053(15) 0.0058(14) C30 0.051(2) 0.0255(18) 0.0207(16) -0.0075(14) -0.0104(15) 0.0121(16) C31 0.0297(17) 0.0151(14) 0.0208(15) -0.0048(12) 0.0012(12) -0.0006(12) N5 0.0292(14) 0.0150(12) 0.0207(13) -0.0022(10) -0.0033(11) -0.0038(10) C32 0.0214(17) 0.0219(17) 0.0193(16) -0.0057(14) 0.0024(13) -0.0050(13) C33 0.0281(19) 0.0147(15) 0.0142(15) 0.0020(12) -0.0006(13) -0.0045(14) O5 0.0291(14) 0.0242(13) 0.0401(14) -0.0127(11) -0.0055(11) 0.0025(11) O6 0.0317(14) 0.0262(13) 0.0362(14) -0.0110(11) -0.0043(11) -0.0076(11) C34 0.0256(17) 0.0197(16) 0.0152(15) -0.0025(13) -0.0030(12) -0.0030(13) C35 0.0237(17) 0.0183(17) 0.0222(16) -0.0033(13) -0.0034(13) -0.0047(13) C36 0.0210(17) 0.0173(16) 0.0217(16) -0.0044(13) -0.0030(13) -0.0032(13) C37 0.0157(16) 0.0203(16) 0.0218(16) -0.0008(13) -0.0045(12) -0.0043(13) N6 0.0319(17) 0.0174(14) 0.0203(15) -0.0022(12) -0.0039(12) -0.0044(12) N7 0.0375(18) 0.0166(14) 0.0249(15) -0.0003(12) -0.0033(13) -0.0028(13) N8 0.0306(16) 0.0200(15) 0.0235(15) -0.0006(12) -0.0028(12) -0.0009(12) O1W 0.0341(15) 0.0276(14) 0.0357(15) -0.0038(12) -0.0060(11) -0.0058(11) O2W 0.0369(16) 0.0319(15) 0.0412(17) 0.0004(13) -0.0074(12) -0.0094(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 O1 C2 1.279(4) . ? C1 C11 1.403(4) . ? C1 C2 1.429(5) . ? C1 C9 1.466(4) . ? C2 C3 1.447(4) . ? C3 C4 1.339(5) . ? C4 C10 1.428(6) . ? C5 C6 1.348(7) . ? C5 C10 1.418(5) . ? C6 C7 1.385(7) . ? C7 C8 1.372(5) . ? C8 C9 1.403(5) . ? C9 C10 1.409(5) . ? C11 N1 1.306(3) . ? N1 C12 1.454(4) . ? C12 C14 1.537(4) . ? C12 C13 1.543(4) . ? C13 O2 1.243(4) . ? C13 O3 1.253(4) . ? C14 C15 1.524(4) . ? C15 C16 1.521(4) . ? C16 N2 1.455(4) . ? C17 N4 1.319(4) . ? C17 N2 1.333(4) . ? C17 N3 1.336(4) . ? O4 C22 1.277(4) . ? C21 C31 1.401(4) . ? C21 C22 1.427(5) . ? C21 C29 1.460(4) . ? C22 C23 1.441(5) . ? C23 C24 1.342(5) . ? C24 C30 1.430(5) . ? C25 C26 1.364(7) . ? C25 C30 1.414(4) . ? C26 C27 1.392(7) . ? C27 C28 1.381(5) . ? C28 C29 1.412(5) . ? C29 C30 1.406(5) . ? C31 N5 1.304(4) . ? N5 C32 1.454(4) . ? C32 C34 1.530(4) . ? C32 C33 1.544(4) . ? C33 O6 1.248(4) . ? C33 O5 1.252(4) . ? C34 C35 1.530(4) . ? C35 C36 1.509(4) . ? C36 N6 1.463(4) . ? C37 N8 1.317(4) . ? C37 N6 1.329(4) . ? C37 N7 1.329(4) . ? 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 C11 C1 C2 118.9(3) . . ? C11 C1 C9 120.9(3) . . ? C2 C1 C9 120.2(3) . . ? O1 C2 C1 123.0(3) . . ? O1 C2 C3 119.1(3) . . ? C1 C2 C3 117.9(3) . . ? C4 C3 C2 121.2(3) . . ? C3 C4 C10 122.6(3) . . ? C6 C5 C10 121.6(4) . . ? C5 C6 C7 119.4(4) . . ? C8 C7 C6 121.3(5) . . ? C7 C8 C9 120.5(4) . . ? C8 C9 C10 118.4(3) . . ? C8 C9 C1 123.1(3) . . ? C10 C9 C1 118.5(3) . . ? C9 C10 C5 118.8(4) . . ? C9 C10 C4 119.5(3) . . ? C5 C10 C4 121.6(4) . . ? N1 C11 C1 124.0(3) . . ? C11 N1 C12 125.5(3) . . ? N1 C12 C14 109.1(2) . . ? N1 C12 C13 112.0(2) . . ? C14 C12 C13 108.1(2) . . ? O2 C13 O3 126.5(3) . . ? O2 C13 C12 115.8(3) . . ? O3 C13 C12 117.6(3) . . ? C15 C14 C12 115.4(3) . . ? C16 C15 C14 108.4(3) . . ? N2 C16 C15 112.2(3) . . ? N4 C17 N2 121.3(3) . . ? N4 C17 N3 120.3(3) . . ? N2 C17 N3 118.5(3) . . ? C17 N2 C16 122.0(3) . . ? C31 C21 C22 119.1(3) . . ? C31 C21 C29 120.4(3) . . ? C22 C21 C29 120.5(3) . . ? O4 C22 C21 122.3(3) . . ? O4 C22 C23 119.6(3) . . ? C21 C22 C23 118.0(3) . . ? C24 C23 C22 121.1(3) . . ? C23 C24 C30 122.1(3) . . ? C26 C25 C30 120.8(4) . . ? C25 C26 C27 120.1(4) . . ? C28 C27 C26 120.4(4) . . ? C27 C28 C29 120.8(4) . . ? C30 C29 C28 118.2(3) . . ? C30 C29 C21 118.1(3) . . ? C28 C29 C21 123.6(3) . . ? C29 C30 C25 119.7(4) . . ? C29 C30 C24 119.9(3) . . ? C25 C30 C24 120.4(3) . . ? N5 C31 C21 124.6(3) . . ? C31 N5 C32 124.5(3) . . ? N5 C32 C34 109.5(2) . . ? N5 C32 C33 111.6(3) . . ? C34 C32 C33 108.4(2) . . ? O6 C33 O5 125.9(3) . . ? O6 C33 C32 115.6(3) . . ? O5 C33 C32 118.4(3) . . ? C32 C34 C35 116.0(3) . . ? C36 C35 C34 108.3(3) . . ? N6 C36 C35 113.0(3) . . ? N8 C37 N6 121.5(3) . . ? N8 C37 N7 119.8(3) . . ? N6 C37 N7 118.7(3) . . ? C37 N6 C36 122.8(3) . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.53 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.270 _refine_diff_density_min -0.235 _refine_diff_density_rms 0.062