# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _journal_volume ? _journal_page_first ? _journal_year ? _publ_contact_author_name 'Dr Hegen Zheng' _publ_contact_author_email zhenghg@nju.edu.cn _publ_section_title ; Synthesis and properties of five unexpected copper complexes with ring-cleavage of 3,6-di-2-pyridyl-1,2,4,5-tetrazine by one pot in situ hydrothermal reaction ; loop_ _publ_author_name 'Jiehu Cui' 'Liangfang Huang' 'Zhenzhong Lu' 'Yizhi Li' 'Zijian Guo' ; Hegen Zheng ; # Attachment '- 1.cif' data_aa _database_code_depnum_ccdc_archive 'CCDC 831075' #TrackingRef '- 1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 Cu4 N8 O17 S2' _chemical_formula_sum 'C24 H26 Cu4 N8 O17 S2' _chemical_formula_weight 1016.87 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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.8549(10) _cell_length_b 12.9803(13) _cell_length_c 13.1435(13) _cell_angle_alpha 88.025(2) _cell_angle_beta 78.041(2) _cell_angle_gamma 85.364(2) _cell_volume 1639.2(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 5049 _cell_measurement_theta_min 2.251 _cell_measurement_theta_max 28.2225 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.060 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1020.0 _exptl_absorpt_coefficient_mu 2.780 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.439 _exptl_absorpt_correction_T_max 0.558 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 8189 _diffrn_reflns_av_R_equivalents 0.0642 _diffrn_reflns_av_sigmaI/netI 0.0520 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.25 _diffrn_reflns_theta_max 25.00 _reflns_number_total 5787 _reflns_number_gt 4938 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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. TITL aa in P-1 CELL 0.71073 9.8549 12.9803 13.1435 88.025 78.041 85.364 ZERR 2.00 0.0010 0.0013 0.0013 0.002 0.002 0.002 LATT 1 SFAC C H N O Cu S UNIT 48 44 16 34 8 4 OMIT 0.00 50.00 L.S. 10 ACTA BOND $H FMAP 2 PLAN 10 ISOR 0.01 N5 N16 WGHT 0.064800 0.000000 FVAR 0.13093 C1 1 0.51750 1.15413 0.17599 11.00000 0.05516 0.02217 = 0.03137 0.00974 -0.01054 -0.00267 AFIX 43 H1 2 0.52988 1.17999 0.10809 11.00000 -1.20000 AFIX 0 C2 1 0.48382 1.22112 0.25596 11.00000 0.06902 0.01925 = 0.03773 0.00535 -0.01024 -0.00023 AFIX 43 H2 2 0.47140 1.29180 0.24309 11.00000 -1.20000 AFIX 0 C3 1 0.46834 1.18292 0.35630 11.00000 0.06495 0.02288 = 0.03312 -0.00630 -0.00634 -0.00213 AFIX 43 H3 2 0.44738 1.22793 0.41187 11.00000 -1.20000 AFIX 0 C4 1 0.48395 1.07788 0.37431 11.00000 0.04704 0.02778 = 0.02360 0.00371 -0.00596 0.00253 AFIX 43 H4 2 0.47370 1.05092 0.44172 11.00000 -1.20000 AFIX 0 C5 1 0.51495 1.01415 0.29039 11.00000 0.02592 0.02094 = 0.02378 0.00585 -0.00515 -0.00191 C6 1 0.53309 0.89799 0.30131 11.00000 0.02847 0.02055 = 0.02267 0.00423 -0.00447 -0.00110 C7 1 0.61340 0.73582 0.09162 11.00000 0.02065 0.02070 = 0.02710 0.00231 -0.00588 -0.00107 C8 1 0.64018 0.62734 0.05620 11.00000 0.02464 0.02112 = 0.02818 0.00542 -0.00640 -0.00145 C9 1 0.66808 0.60257 -0.04668 11.00000 0.03395 0.02813 = 0.02628 -0.00076 -0.00296 0.00225 AFIX 43 H9 2 0.67275 0.65396 -0.09810 11.00000 -1.20000 AFIX 0 C10 1 0.68905 0.49993 -0.07231 11.00000 0.04284 0.04258 = 0.02809 -0.01093 -0.00613 0.00316 AFIX 43 H10 2 0.70743 0.48083 -0.14165 11.00000 -1.20000 AFIX 0 C11 1 0.68271 0.42646 0.00465 11.00000 0.04274 0.02367 = 0.05083 -0.00816 -0.01116 -0.00024 AFIX 43 H11 2 0.69565 0.35672 -0.01164 11.00000 -1.20000 AFIX 0 C12 1 0.65718 0.45606 0.10602 11.00000 0.03808 0.01948 = 0.04202 0.00335 -0.01258 -0.00207 AFIX 43 H12 2 0.65565 0.40559 0.15813 11.00000 -1.20000 AFIX 0 C13 1 -0.03003 0.82619 -0.16322 11.00000 0.05428 0.02638 = 0.02481 0.00363 -0.01122 -0.00320 AFIX 43 H13 2 -0.04625 0.89326 -0.18752 11.00000 -1.20000 AFIX 0 C14 1 0.01100 0.74896 -0.23393 11.00000 0.06413 0.03906 = 0.02848 0.00258 -0.01008 -0.00827 AFIX 43 H14 2 0.02370 0.76327 -0.30496 11.00000 -1.20000 AFIX 0 C15 1 0.03321 0.64868 -0.19703 11.00000 0.06136 0.02406 = 0.03163 -0.00740 -0.00696 -0.00339 AFIX 43 H15 2 0.06093 0.59461 -0.24318 11.00000 -1.20000 AFIX 0 C16 1 0.01395 0.63049 -0.09256 11.00000 0.04173 0.02103 = 0.03579 0.00108 -0.01052 -0.00266 AFIX 43 H16 2 0.02659 0.56367 -0.06649 11.00000 -1.20000 AFIX 0 C17 1 -0.02460 0.71246 -0.02577 11.00000 0.02563 0.02068 = 0.02924 0.00344 -0.00932 -0.00354 C18 1 -0.04507 0.69897 0.09028 11.00000 0.03105 0.02067 = 0.02834 0.00368 -0.01005 -0.00294 C19 1 -0.13183 0.90286 0.25942 11.00000 0.01944 0.01987 = 0.02747 0.00524 -0.00306 -0.00187 C20 1 -0.14798 0.93637 0.36784 11.00000 0.02239 0.02507 = 0.02769 0.00247 -0.00411 -0.00277 C21 1 -0.18610 1.03723 0.39664 11.00000 0.03271 0.02558 = 0.03558 -0.00112 -0.00425 -0.00231 AFIX 43 H21 2 -0.20375 1.08732 0.34777 11.00000 -1.20000 AFIX 0 C22 1 -0.19747 1.06235 0.49764 11.00000 0.03552 0.03899 = 0.04320 -0.01322 -0.00416 -0.00273 AFIX 43 H22 2 -0.22382 1.12994 0.51883 11.00000 -1.20000 AFIX 0 C23 1 -0.16985 0.98734 0.56826 11.00000 0.03752 0.04958 = 0.03165 -0.01110 -0.00110 -0.00290 AFIX 43 H23 2 -0.17594 1.00380 0.63745 11.00000 -1.20000 AFIX 0 C24 1 -0.13295 0.88728 0.53547 11.00000 0.03747 0.04138 = 0.02589 0.00256 -0.00630 -0.00127 AFIX 43 H24 2 -0.11668 0.83611 0.58372 11.00000 -1.20000 AFIX 0 CU1 5 0.57561 0.94156 0.08919 11.00000 0.03124 0.01746 = 0.01923 0.00737 -0.00519 -0.00298 CU2 5 -0.09519 0.90893 0.05276 11.00000 0.02913 0.01513 = 0.02313 0.00588 -0.00616 -0.00217 CU3 5 0.60640 0.61550 0.27319 11.00000 0.03353 0.01737 = 0.02149 0.00623 -0.00499 -0.00262 CU4 5 -0.05249 0.72648 0.37081 11.00000 0.03289 0.02179 = 0.02277 0.00598 -0.00615 -0.00122 N1 3 0.53345 1.05139 0.19222 11.00000 0.03417 0.01855 = 0.02310 0.00336 -0.00801 -0.00289 N2 3 0.55840 0.85482 0.21152 11.00000 0.03141 0.01191 = 0.02387 0.00648 -0.00696 -0.00457 N3 3 0.58302 0.74856 0.19279 11.00000 0.02671 0.01631 = 0.01976 0.00391 -0.00375 -0.00323 O3 4 0.62419 0.80730 0.02275 11.00000 0.03857 0.02170 = 0.02203 0.00732 -0.00334 0.00034 N5 3 0.63415 0.55623 0.13273 11.00000 0.02880 0.01965 = 0.02556 0.00091 -0.00512 -0.00226 N6 3 -0.04748 0.80916 -0.06177 11.00000 0.03361 0.01804 = 0.02782 0.00269 -0.00925 -0.00251 N7 3 -0.07488 0.78778 0.13558 11.00000 0.02794 0.01576 = 0.02402 0.00310 -0.00651 -0.00234 N8 3 -0.09516 0.80257 0.24246 11.00000 0.02542 0.01998 = 0.02229 0.00244 -0.00410 -0.00301 N9 3 -0.11994 0.86194 0.43529 11.00000 0.02955 0.03186 = 0.02344 0.00156 -0.00607 -0.00026 O4 4 -0.15041 0.97059 0.19030 11.00000 0.03423 0.01687 = 0.02472 0.00368 -0.00345 0.00172 O1 4 0.52347 0.85917 0.39046 11.00000 0.07797 0.02299 = 0.01895 0.00618 -0.00286 0.00533 O2 4 -0.03278 0.60955 0.12813 11.00000 0.10425 0.01598 = 0.03383 0.00710 -0.02214 0.00264 O5 4 0.64836 0.47692 0.33478 11.00000 0.03296 0.02710 = 0.02571 0.00740 -0.00362 0.00298 AFIX 3 H5A 2 0.73591 0.46586 0.32822 11.00000 -1.50000 H5B 2 0.60991 0.47588 0.39894 11.00000 -1.50000 AFIX 0 O6 4 0.64062 0.67968 0.39427 11.00000 0.05179 0.02589 = 0.02761 0.00212 -0.01198 -0.00137 AFIX 3 H6B 2 0.58707 0.73443 0.40697 11.00000 -1.50000 H6C 2 0.62512 0.63814 0.44607 11.00000 -1.50000 AFIX 0 O7 4 -0.03139 0.58858 0.31749 11.00000 0.04595 0.02518 = 0.02996 0.00628 -0.01015 -0.00597 AFIX 3 H7B 2 0.00218 0.59039 0.25250 11.00000 -1.50000 H7C 2 0.02325 0.55096 0.34798 11.00000 -1.50000 AFIX 0 O8 4 -0.01857 0.66724 0.50863 11.00000 0.03259 0.03145 = 0.02973 0.00954 -0.00427 -0.00119 AFIX 3 H8A 2 -0.09389 0.64676 0.54452 11.00000 -1.50000 H8B 2 0.04228 0.61644 0.49738 11.00000 -1.50000 AFIX 0 O9 4 0.17585 0.75976 0.32540 11.00000 0.03178 0.03438 = 0.04064 0.01900 -0.00137 -0.00124 AFIX 3 H9A 2 0.19127 0.78786 0.26513 11.00000 -1.50000 H9C 2 0.22646 0.70347 0.32479 11.00000 -1.50000 AFIX 0 O10 4 0.36672 0.97635 0.03773 11.00000 0.02731 0.02957 = 0.02377 0.01447 -0.00550 -0.01157 O11 4 0.12983 0.96563 0.02507 11.00000 0.02604 0.02089 = 0.03539 0.01149 -0.01214 -0.00539 O12 4 0.19757 0.93614 0.18865 11.00000 0.04194 0.06790 = 0.02281 0.01224 -0.00227 -0.00986 O13 4 0.26838 0.81240 0.05503 11.00000 0.04441 0.01331 = 0.08816 0.00784 -0.01581 -0.00076 O16 4 0.23288 0.56718 0.49780 11.00000 0.03384 0.04764 = 0.03115 0.00641 -0.00763 0.00455 O15 4 0.18490 0.46478 0.36309 11.00000 0.04363 0.03965 = 0.04298 0.01146 -0.01912 -0.01144 O17 4 0.39699 0.42749 0.42647 11.00000 0.03705 0.02573 = 0.03520 0.01430 -0.00555 0.00002 O14 4 0.36864 0.58119 0.32259 11.00000 0.02997 0.02979 = 0.03824 0.01903 -0.00014 -0.00146 S1 6 0.24014 0.91977 0.07901 11.00000 0.02187 0.01736 = 0.02395 0.01055 -0.00549 -0.00400 S2 6 0.29588 0.51077 0.40203 11.00000 0.02829 0.02559 = 0.02561 0.01223 -0.00563 -0.00357 HKLF 4 END ; _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^)+(0.0648P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5682 _refine_ls_number_parameters 496 _refine_ls_number_restraints 6 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0415 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.1072 _refine_ls_goodness_of_fit_ref 1.069 _refine_ls_restrained_S_all 1.068 _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 C1 C 0.5175(5) 1.1541(3) 0.1760(3) 0.0364(10) Uani 1 1 d . . . H1 H 0.5301 1.1800 0.1080 0.044 Uiso 1 1 calc R . . C2 C 0.4836(5) 1.2213(3) 0.2560(4) 0.0426(12) Uani 1 1 d . . . H2 H 0.4713 1.2920 0.2431 0.051 Uiso 1 1 calc R . . C3 C 0.4676(5) 1.1832(3) 0.3565(3) 0.0409(11) Uani 1 1 d . . . H3 H 0.4462 1.2281 0.4122 0.049 Uiso 1 1 calc R . . C4 C 0.4837(5) 1.0779(3) 0.3742(3) 0.0335(10) Uani 1 1 d . . . H4 H 0.4735 1.0508 0.4415 0.040 Uiso 1 1 calc R . . C5 C 0.5149(4) 1.0142(3) 0.2904(3) 0.0239(8) Uani 1 1 d . . . C6 C 0.5328(4) 0.8979(3) 0.3015(3) 0.0247(8) Uani 1 1 d . . . C7 C 0.6133(4) 0.7358(3) 0.0917(3) 0.0227(8) Uani 1 1 d . . . C8 C 0.6399(4) 0.6273(3) 0.0564(3) 0.0248(8) Uani 1 1 d . . . C9 C 0.6678(4) 0.6025(3) -0.0468(3) 0.0301(9) Uani 1 1 d . . . H9 H 0.6724 0.6539 -0.0981 0.036 Uiso 1 1 calc R . . C10 C 0.6889(5) 0.4999(3) -0.0726(3) 0.0382(10) Uani 1 1 d . . . H10 H 0.7070 0.4807 -0.1419 0.046 Uiso 1 1 calc R . . C11 C 0.6828(5) 0.4265(3) 0.0047(4) 0.0390(11) Uani 1 1 d . . . H11 H 0.6960 0.3567 -0.0115 0.047 Uiso 1 1 calc R . . C12 C 0.6572(5) 0.4561(3) 0.1059(3) 0.0326(9) Uani 1 1 d . . . H12 H 0.6557 0.4056 0.1580 0.039 Uiso 1 1 calc R . . C13 C -0.0297(5) 0.8264(3) -0.1635(3) 0.0351(10) Uani 1 1 d . . . H13 H -0.0457 0.8935 -0.1878 0.042 Uiso 1 1 calc R . . C14 C 0.0112(5) 0.7489(3) -0.2339(4) 0.0435(11) Uani 1 1 d . . . H14 H 0.0238 0.7631 -0.3050 0.052 Uiso 1 1 calc R . . C15 C 0.0333(5) 0.6487(3) -0.1970(3) 0.0392(11) Uani 1 1 d . . . H15 H 0.0610 0.5947 -0.2432 0.047 Uiso 1 1 calc R . . C16 C 0.0141(5) 0.6303(3) -0.0924(3) 0.0327(9) Uani 1 1 d . . . H16 H 0.0268 0.5635 -0.0664 0.039 Uiso 1 1 calc R . . C17 C -0.0244(4) 0.7124(3) -0.0258(3) 0.0245(8) Uani 1 1 d . . . C18 C -0.0453(4) 0.6988(3) 0.0903(3) 0.0262(9) Uani 1 1 d . . . C19 C -0.1320(4) 0.9027(3) 0.2594(3) 0.0225(8) Uani 1 1 d . . . C20 C -0.1479(4) 0.9361(3) 0.3679(3) 0.0251(8) Uani 1 1 d . . . C21 C -0.1862(4) 1.0372(3) 0.3966(3) 0.0314(9) Uani 1 1 d . . . H21 H -0.2038 1.0873 0.3477 0.038 Uiso 1 1 calc R . . C22 C -0.1977(5) 1.0624(3) 0.4979(4) 0.0401(11) Uani 1 1 d . . . H22 H -0.2240 1.1300 0.5191 0.048 Uiso 1 1 calc R . . C23 C -0.1703(5) 0.9872(4) 0.5685(4) 0.0401(11) Uani 1 1 d . . . H23 H -0.1769 1.0035 0.6378 0.048 Uiso 1 1 calc R . . C24 C -0.1330(5) 0.8874(3) 0.5354(3) 0.0347(10) Uani 1 1 d . . . H24 H -0.1164 0.8363 0.5836 0.042 Uiso 1 1 calc R . . Cu1 Cu 0.57559(5) 0.94154(3) 0.08919(3) 0.02290(14) Uani 1 1 d . . . Cu2 Cu -0.09520(5) 0.90894(3) 0.05277(3) 0.02267(14) Uani 1 1 d . . . Cu3 Cu 0.60640(5) 0.61550(3) 0.27320(3) 0.02450(14) Uani 1 1 d . . . Cu4 Cu -0.05250(5) 0.72648(3) 0.37077(4) 0.02614(14) Uani 1 1 d . . . N1 N 0.5332(3) 1.0515(2) 0.1922(2) 0.0249(7) Uani 1 1 d . . . N2 N 0.5583(3) 0.8548(2) 0.2114(2) 0.0225(7) Uani 1 1 d . . . N3 N 0.5829(3) 0.7484(2) 0.1927(2) 0.0213(7) Uani 1 1 d . . . O3 O 0.6239(3) 0.80734(19) 0.0227(2) 0.0283(6) Uani 1 1 d . . . N5 N 0.6340(3) 0.5562(2) 0.1326(2) 0.0247(7) Uani 1 1 d U . . N6 N -0.0472(3) 0.8090(2) -0.0617(2) 0.0261(7) Uani 1 1 d . . . N7 N -0.0750(3) 0.7878(2) 0.1356(2) 0.0226(7) Uani 1 1 d . . . N8 N -0.0953(3) 0.8025(2) 0.2425(2) 0.0227(7) Uani 1 1 d . . . N9 N -0.1199(3) 0.8620(2) 0.4353(2) 0.0283(7) Uani 1 1 d . . . O4 O -0.1504(3) 0.97051(18) 0.1904(2) 0.0262(6) Uani 1 1 d . . . O1 O 0.5231(4) 0.8591(2) 0.3905(2) 0.0415(8) Uani 1 1 d . . . O2 O -0.0328(4) 0.6097(2) 0.1280(2) 0.0503(9) Uani 1 1 d . . . O5 O 0.6483(3) 0.47699(19) 0.3348(2) 0.0296(6) Uani 1 1 d . . . H5A H 0.7359 0.4659 0.3283 0.044 Uiso 1 1 d R . . H5B H 0.6099 0.4760 0.3990 0.044 Uiso 1 1 d R . . O6 O 0.6423(3) 0.6803(2) 0.3933(2) 0.0355(7) Uani 1 1 d . . . H6B H 0.5888 0.7351 0.4060 0.053 Uiso 1 1 d R . . H6C H 0.6268 0.6388 0.4451 0.053 Uiso 1 1 d R . . O7 O -0.0337(3) 0.58880(19) 0.3173(2) 0.0337(7) Uani 1 1 d . . . H7B H -0.0001 0.5906 0.2523 0.051 Uiso 1 1 d R . . H7C H 0.0210 0.5512 0.3478 0.051 Uiso 1 1 d R . . O8 O -0.0188(3) 0.6673(2) 0.5084(2) 0.0321(6) Uani 1 1 d . . . H8A H -0.0941 0.6468 0.5443 0.048 Uiso 1 1 d R . . H8B H 0.0421 0.6165 0.4971 0.048 Uiso 1 1 d R . . O9 O 0.1754(3) 0.7599(2) 0.3253(2) 0.0370(7) Uani 1 1 d . . . H9A H 0.1909 0.7880 0.2651 0.056 Uiso 1 1 d R . . H9C H 0.2261 0.7037 0.3247 0.056 Uiso 1 1 d R . . O10 O 0.3669(3) 0.97643(19) 0.0377(2) 0.0268(6) Uani 1 1 d . . . O11 O 0.1298(3) 0.96558(19) 0.0250(2) 0.0266(6) Uani 1 1 d . . . O12 O 0.1972(3) 0.9362(3) 0.1886(2) 0.0451(8) Uani 1 1 d . . . O13 O 0.2682(3) 0.8125(2) 0.0548(3) 0.0490(9) Uani 1 1 d . . . O16 O 0.2330(3) 0.5672(2) 0.4977(2) 0.0382(7) Uani 1 1 d . . . O15 O 0.1854(3) 0.4648(2) 0.3631(2) 0.0405(7) Uani 1 1 d . . . O17 O 0.3971(3) 0.4275(2) 0.4264(2) 0.0339(7) Uani 1 1 d . . . O14 O 0.3684(3) 0.5810(2) 0.3229(2) 0.0347(7) Uani 1 1 d . . . S1 S 0.24009(9) 0.91978(6) 0.07900(7) 0.0212(2) Uani 1 1 d . . . S2 S 0.29587(10) 0.51082(7) 0.40203(8) 0.0268(2) 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 0.055(3) 0.023(2) 0.031(2) 0.0092(18) -0.010(2) -0.0027(19) C2 0.070(3) 0.018(2) 0.038(3) 0.0057(18) -0.010(2) -0.001(2) C3 0.066(3) 0.023(2) 0.032(2) -0.0061(18) -0.008(2) -0.002(2) C4 0.048(3) 0.028(2) 0.023(2) 0.0036(17) -0.0062(19) 0.0020(19) C5 0.026(2) 0.0210(18) 0.025(2) 0.0057(15) -0.0049(16) -0.0019(15) C6 0.029(2) 0.0211(18) 0.023(2) 0.0048(16) -0.0040(16) -0.0019(16) C7 0.0207(19) 0.0206(18) 0.027(2) 0.0021(16) -0.0065(16) -0.0007(15) C8 0.024(2) 0.0212(18) 0.029(2) 0.0054(16) -0.0064(17) -0.0013(15) C9 0.034(2) 0.028(2) 0.026(2) -0.0007(17) -0.0036(18) 0.0021(17) C10 0.043(3) 0.043(3) 0.028(2) -0.0107(19) -0.006(2) 0.002(2) C11 0.043(3) 0.024(2) 0.051(3) -0.008(2) -0.011(2) -0.0002(18) C12 0.039(2) 0.0199(19) 0.041(2) 0.0035(17) -0.012(2) -0.0025(17) C13 0.055(3) 0.027(2) 0.024(2) 0.0036(17) -0.011(2) -0.0037(19) C14 0.063(3) 0.040(2) 0.028(2) 0.0027(19) -0.010(2) -0.008(2) C15 0.061(3) 0.024(2) 0.032(2) -0.0076(18) -0.006(2) -0.004(2) C16 0.042(2) 0.0211(19) 0.036(2) 0.0012(17) -0.010(2) -0.0026(17) C17 0.025(2) 0.0214(18) 0.029(2) 0.0031(16) -0.0091(17) -0.0032(15) C18 0.030(2) 0.0204(19) 0.030(2) 0.0035(16) -0.0105(18) -0.0034(16) C19 0.0197(19) 0.0196(18) 0.027(2) 0.0052(15) -0.0042(16) -0.0014(14) C20 0.022(2) 0.0250(19) 0.027(2) 0.0023(16) -0.0035(16) -0.0023(15) C21 0.033(2) 0.025(2) 0.035(2) -0.0006(17) -0.0039(19) -0.0026(17) C22 0.036(3) 0.039(2) 0.044(3) -0.014(2) -0.004(2) -0.003(2) C23 0.038(3) 0.050(3) 0.030(2) -0.010(2) -0.002(2) -0.003(2) C24 0.037(2) 0.041(2) 0.025(2) 0.0025(18) -0.0068(19) -0.0011(19) Cu1 0.0313(3) 0.0176(2) 0.0194(2) 0.00739(18) -0.0051(2) -0.00304(19) Cu2 0.0293(3) 0.0153(2) 0.0234(3) 0.00588(18) -0.0061(2) -0.00226(18) Cu3 0.0337(3) 0.0175(2) 0.0216(3) 0.00627(18) -0.0050(2) -0.00267(19) Cu4 0.0331(3) 0.0219(2) 0.0230(3) 0.00602(19) -0.0062(2) -0.0012(2) N1 0.0340(19) 0.0181(15) 0.0232(17) 0.0036(13) -0.0078(14) -0.0025(13) N2 0.0319(18) 0.0116(14) 0.0244(17) 0.0059(12) -0.0071(14) -0.0044(12) N3 0.0266(17) 0.0169(14) 0.0201(16) 0.0037(12) -0.0037(13) -0.0033(12) O3 0.0384(16) 0.0217(13) 0.0223(14) 0.0075(11) -0.0028(12) 0.0003(12) N5 0.0287(17) 0.0200(15) 0.0251(17) 0.0011(13) -0.0049(14) -0.0024(13) N6 0.0331(19) 0.0183(15) 0.0280(18) 0.0026(13) -0.0087(15) -0.0029(13) N7 0.0270(17) 0.0164(15) 0.0246(17) 0.0029(13) -0.0062(14) -0.0025(12) N8 0.0249(17) 0.0208(15) 0.0217(16) 0.0024(13) -0.0031(13) -0.0037(13) N9 0.0294(18) 0.0315(18) 0.0237(18) 0.0017(14) -0.0058(15) -0.0003(14) O4 0.0344(15) 0.0171(12) 0.0249(14) 0.0037(11) -0.0031(12) 0.0014(11) O1 0.077(2) 0.0231(14) 0.0187(14) 0.0058(12) -0.0028(15) 0.0059(15) O2 0.103(3) 0.0162(14) 0.0344(17) 0.0075(13) -0.0234(19) 0.0017(16) O5 0.0339(16) 0.0269(14) 0.0258(14) 0.0077(11) -0.0043(12) 0.0028(12) O6 0.060(2) 0.0229(14) 0.0244(15) 0.0048(11) -0.0117(14) -0.0003(13) O7 0.0496(19) 0.0239(14) 0.0289(15) 0.0070(12) -0.0132(14) -0.0011(13) O8 0.0326(16) 0.0322(15) 0.0294(15) 0.0103(12) -0.0040(13) -0.0014(12) O9 0.0320(16) 0.0339(15) 0.0410(17) 0.0187(13) -0.0011(14) -0.0019(13) O10 0.0276(15) 0.0290(14) 0.0244(14) 0.0150(11) -0.0057(12) -0.0112(11) O11 0.0254(14) 0.0212(13) 0.0353(16) 0.0109(11) -0.0115(12) -0.0056(11) O12 0.0417(19) 0.069(2) 0.0228(15) 0.0122(15) -0.0024(14) -0.0104(16) O13 0.0443(19) 0.0136(14) 0.089(3) 0.0074(15) -0.0153(19) -0.0008(13) O16 0.0340(17) 0.0480(18) 0.0317(16) 0.0063(14) -0.0082(14) 0.0039(14) O15 0.0432(18) 0.0400(16) 0.0431(18) 0.0111(14) -0.0187(15) -0.0110(14) O17 0.0378(17) 0.0258(14) 0.0358(16) 0.0151(12) -0.0058(14) -0.0003(12) O14 0.0305(16) 0.0301(15) 0.0391(17) 0.0198(13) -0.0002(13) -0.0019(12) S1 0.0220(5) 0.0175(4) 0.0242(5) 0.0106(4) -0.0054(4) -0.0040(4) S2 0.0282(5) 0.0258(5) 0.0257(5) 0.0121(4) -0.0055(4) -0.0035(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.343(5) . ? C1 C2 1.360(6) . ? C1 H1 0.9300 . ? C2 C3 1.377(6) . ? C2 H2 0.9300 . ? C3 C4 1.380(5) . ? C3 H3 0.9300 . ? C4 C5 1.368(5) . ? C4 H4 0.9300 . ? C5 N1 1.344(5) . ? C5 C6 1.512(5) . ? C6 O1 1.246(5) . ? C6 N2 1.295(5) . ? C7 O3 1.270(4) . ? C7 N3 1.311(5) . ? C7 C8 1.485(5) . ? C8 N5 1.334(5) . ? C8 C9 1.371(6) . ? C9 C10 1.375(6) . ? C9 H9 0.9300 . ? C10 C11 1.364(6) . ? C10 H10 0.9300 . ? C11 C12 1.364(6) . ? C11 H11 0.9300 . ? C12 N5 1.347(5) . ? C12 H12 0.9300 . ? C13 N6 1.327(5) . ? C13 C14 1.370(6) . ? C13 H13 0.9300 . ? C14 C15 1.388(6) . ? C14 H14 0.9300 . ? C15 C16 1.364(6) . ? C15 H15 0.9300 . ? C16 C17 1.382(5) . ? C16 H16 0.9300 . ? C17 N6 1.342(5) . ? C17 C18 1.503(5) . ? C18 O2 1.249(4) . ? C18 N7 1.302(5) . ? C19 O4 1.271(4) . ? C19 N8 1.335(5) . ? C19 C20 1.478(5) . ? C20 N9 1.336(5) . ? C20 C21 1.379(5) . ? C21 C22 1.362(6) . ? C21 H21 0.9300 . ? C22 C23 1.372(7) . ? C22 H22 0.9300 . ? C23 C24 1.378(6) . ? C23 H23 0.9300 . ? C24 N9 1.345(5) . ? C24 H24 0.9300 . ? Cu1 N2 1.916(3) . ? Cu1 O10 1.955(2) 2_675 ? Cu1 O3 1.955(3) . ? Cu1 N1 1.962(3) . ? Cu1 O10 2.301(3) . ? Cu2 N7 1.903(3) . ? Cu2 O11 1.938(2) 2_575 ? Cu2 O4 1.956(3) . ? Cu2 N6 1.977(3) . ? Cu2 O11 2.345(3) . ? Cu3 O6 1.922(3) . ? Cu3 N5 1.984(3) . ? Cu3 O5 1.994(3) . ? Cu3 N3 2.015(3) . ? Cu3 O14 2.375(3) . ? Cu4 O7 1.924(3) . ? Cu4 N9 1.984(3) . ? Cu4 O8 2.021(3) . ? Cu4 N8 2.026(3) . ? Cu4 O9 2.275(3) . ? N2 N3 1.404(4) . ? N7 N8 1.395(4) . ? O5 H5A 0.8500 . ? O5 H5B 0.8500 . ? O6 H6B 0.8500 . ? O6 H6C 0.8500 . ? O7 H7B 0.8499 . ? O7 H7C 0.8500 . ? O8 H8A 0.8499 . ? O8 H8B 0.8499 . ? O9 H9A 0.8502 . ? O9 H9C 0.8500 . ? O10 S1 1.496(3) . ? O10 Cu1 1.955(2) 2_675 ? O11 S1 1.491(3) . ? O11 Cu2 1.938(2) 2_575 ? O12 S1 1.433(3) . ? O13 S1 1.432(3) . ? O16 S2 1.472(3) . ? O15 S2 1.470(3) . ? O17 S2 1.484(3) . ? O14 S2 1.468(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 121.9(4) . . ? N1 C1 H1 119.1 . . ? C2 C1 H1 119.1 . . ? C1 C2 C3 119.1(4) . . ? C1 C2 H2 120.5 . . ? C3 C2 H2 120.5 . . ? C2 C3 C4 119.6(4) . . ? C2 C3 H3 120.2 . . ? C4 C3 H3 120.2 . . ? C5 C4 C3 118.6(4) . . ? C5 C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? N1 C5 C4 121.9(3) . . ? N1 C5 C6 115.5(3) . . ? C4 C5 C6 122.6(3) . . ? O1 C6 N2 130.7(3) . . ? O1 C6 C5 118.4(3) . . ? N2 C6 C5 111.0(3) . . ? O3 C7 N3 126.2(3) . . ? O3 C7 C8 117.8(3) . . ? N3 C7 C8 116.0(3) . . ? N5 C8 C9 122.8(3) . . ? N5 C8 C7 114.9(3) . . ? C9 C8 C7 122.3(3) . . ? C8 C9 C10 118.5(4) . . ? C8 C9 H9 120.7 . . ? C10 C9 H9 120.7 . . ? C11 C10 C9 119.2(4) . . ? C11 C10 H10 120.4 . . ? C9 C10 H10 120.4 . . ? C10 C11 C12 119.6(4) . . ? C10 C11 H11 120.2 . . ? C12 C11 H11 120.2 . . ? N5 C12 C11 122.0(4) . . ? N5 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? N6 C13 C14 122.2(4) . . ? N6 C13 H13 118.9 . . ? C14 C13 H13 118.9 . . ? C13 C14 C15 118.6(4) . . ? C13 C14 H14 120.7 . . ? C15 C14 H14 120.7 . . ? C16 C15 C14 119.4(4) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C17 119.0(4) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? N6 C17 C16 121.4(4) . . ? N6 C17 C18 116.3(3) . . ? C16 C17 C18 122.2(3) . . ? O2 C18 N7 130.5(4) . . ? O2 C18 C17 118.9(3) . . ? N7 C18 C17 110.6(3) . . ? O4 C19 N8 125.7(3) . . ? O4 C19 C20 118.5(3) . . ? N8 C19 C20 115.8(3) . . ? N9 C20 C21 122.6(4) . . ? N9 C20 C19 115.3(3) . . ? C21 C20 C19 122.1(4) . . ? C22 C21 C20 118.8(4) . . ? C22 C21 H21 120.6 . . ? C20 C21 H21 120.6 . . ? C21 C22 C23 119.5(4) . . ? C21 C22 H22 120.3 . . ? C23 C22 H22 120.3 . . ? C22 C23 C24 119.2(4) . . ? C22 C23 H23 120.4 . . ? C24 C23 H23 120.4 . . ? N9 C24 C23 121.8(4) . . ? N9 C24 H24 119.1 . . ? C23 C24 H24 119.1 . . ? N2 Cu1 O10 168.54(13) . 2_675 ? N2 Cu1 O3 81.02(11) . . ? O10 Cu1 O3 95.48(11) 2_675 . ? N2 Cu1 N1 82.42(12) . . ? O10 Cu1 N1 100.13(12) 2_675 . ? O3 Cu1 N1 163.11(12) . . ? N2 Cu1 O10 112.32(11) . . ? O10 Cu1 O10 78.85(11) 2_675 . ? O3 Cu1 O10 96.86(11) . . ? N1 Cu1 O10 92.47(12) . . ? N7 Cu2 O11 175.61(12) . 2_575 ? N7 Cu2 O4 81.19(12) . . ? O11 Cu2 O4 95.98(11) 2_575 . ? N7 Cu2 N6 82.47(13) . . ? O11 Cu2 N6 100.09(12) 2_575 . ? O4 Cu2 N6 163.16(12) . . ? N7 Cu2 O11 100.98(11) . . ? O11 Cu2 O11 82.47(11) 2_575 . ? O4 Cu2 O11 93.23(11) . . ? N6 Cu2 O11 93.82(12) . . ? O6 Cu3 N5 161.34(13) . . ? O6 Cu3 O5 89.86(11) . . ? N5 Cu3 O5 91.23(12) . . ? O6 Cu3 N3 95.30(12) . . ? N5 Cu3 N3 81.90(12) . . ? O5 Cu3 N3 171.92(12) . . ? O6 Cu3 O14 103.59(12) . . ? N5 Cu3 O14 95.07(12) . . ? O5 Cu3 O14 86.36(10) . . ? N3 Cu3 O14 98.42(11) . . ? O7 Cu4 N9 166.21(13) . . ? O7 Cu4 O8 89.51(11) . . ? N9 Cu4 O8 90.78(12) . . ? O7 Cu4 N8 97.45(12) . . ? N9 Cu4 N8 82.00(12) . . ? O8 Cu4 N8 172.78(12) . . ? O7 Cu4 O9 97.64(12) . . ? N9 Cu4 O9 96.15(12) . . ? O8 Cu4 O9 89.39(11) . . ? N8 Cu4 O9 91.57(11) . . ? C5 N1 C1 119.1(3) . . ? C5 N1 Cu1 112.4(2) . . ? C1 N1 Cu1 128.5(3) . . ? C6 N2 N3 126.2(3) . . ? C6 N2 Cu1 118.6(2) . . ? N3 N2 Cu1 115.1(2) . . ? C7 N3 N2 108.0(3) . . ? C7 N3 Cu3 112.8(2) . . ? N2 N3 Cu3 138.7(2) . . ? C7 O3 Cu1 109.6(2) . . ? C8 N5 C12 117.9(3) . . ? C8 N5 Cu3 113.7(2) . . ? C12 N5 Cu3 128.3(3) . . ? C13 N6 C17 119.3(3) . . ? C13 N6 Cu2 129.1(3) . . ? C17 N6 Cu2 111.5(3) . . ? C18 N7 N8 125.1(3) . . ? C18 N7 Cu2 119.0(3) . . ? N8 N7 Cu2 115.9(2) . . ? C19 N8 N7 107.4(3) . . ? C19 N8 Cu4 112.3(2) . . ? N7 N8 Cu4 139.0(2) . . ? C20 N9 C24 118.1(3) . . ? C20 N9 Cu4 114.1(3) . . ? C24 N9 Cu4 127.7(3) . . ? C19 O4 Cu2 109.4(2) . . ? Cu3 O5 H5A 109.1 . . ? Cu3 O5 H5B 109.3 . . ? H5A O5 H5B 109.5 . . ? Cu3 O6 H6B 109.4 . . ? Cu3 O6 H6C 109.0 . . ? H6B O6 H6C 109.5 . . ? Cu4 O7 H7B 109.4 . . ? Cu4 O7 H7C 108.9 . . ? H7B O7 H7C 109.5 . . ? Cu4 O8 H8A 109.6 . . ? Cu4 O8 H8B 109.1 . . ? H8A O8 H8B 109.5 . . ? Cu4 O9 H9A 109.2 . . ? Cu4 O9 H9C 109.4 . . ? H9A O9 H9C 109.5 . . ? S1 O10 Cu1 132.61(16) . 2_675 ? S1 O10 Cu1 123.83(14) . . ? Cu1 O10 Cu1 101.15(11) 2_675 . ? S1 O11 Cu2 137.32(16) . 2_575 ? S1 O11 Cu2 123.72(14) . . ? Cu2 O11 Cu2 97.53(11) 2_575 . ? S2 O14 Cu3 131.80(17) . . ? O13 S1 O12 112.4(2) . . ? O13 S1 O11 109.42(18) . . ? O12 S1 O11 109.50(18) . . ? O13 S1 O10 109.79(17) . . ? O12 S1 O10 109.14(17) . . ? O11 S1 O10 106.45(15) . . ? O14 S2 O16 110.42(17) . . ? O14 S2 O15 110.08(18) . . ? O16 S2 O15 108.78(19) . . ? O14 S2 O17 109.09(17) . . ? O16 S2 O17 109.10(17) . . ? O15 S2 O17 109.34(17) . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.998 _refine_diff_density_min -0.778 _refine_diff_density_rms 0.129 # Attachment '- 2.cif' data_pbca _database_code_depnum_ccdc_archive 'CCDC 831076' #TrackingRef '- 2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ' C12 H14 Cu2 N4 O9 S ' _chemical_formula_sum ' C12 H14 Cu2 N4 O9 S ' _chemical_formula_weight 517.44 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' S S 0.1246 0.1234 '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 Pbca _symmetry_space_group_name_Hall '-P 2ac 2ab ' 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' '-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 11.3702(14) _cell_length_b 17.100(2) _cell_length_c 17.374(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3378.0(7) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4912 _cell_measurement_theta_min 2.3445 _cell_measurement_theta_max 26.756 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 2.035 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2080.0 _exptl_absorpt_coefficient_mu 2.702 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.449 _exptl_absorpt_correction_T_max 0.567 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 15739 _diffrn_reflns_av_R_equivalents 0.0514 _diffrn_reflns_av_sigmaI/netI 0.0354 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 2.34 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2969 _reflns_number_gt 2470 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0599P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2969 _refine_ls_number_parameters 253 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0363 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0956 _refine_ls_goodness_of_fit_ref 1.028 _refine_ls_restrained_S_all 1.028 _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 C1 C 0.6029(3) 0.1324(2) 0.3434(2) 0.0288(8) Uani 1 1 d . . . C2 C 0.5629(4) 0.1737(2) 0.2807(2) 0.0366(10) Uani 1 1 d . . . H2 H 0.4927 0.2015 0.2831 0.044 Uiso 1 1 calc R . . C3 C 0.6295(4) 0.1731(2) 0.2142(2) 0.0434(11) Uani 1 1 d . . . H3 H 0.6043 0.2000 0.1707 0.052 Uiso 1 1 calc R . . C4 C 0.7325(4) 0.1325(3) 0.2130(2) 0.0458(11) Uani 1 1 d . . . H4A H 0.7785 0.1317 0.1687 0.055 Uiso 1 1 calc R . . C5 C 0.7679(4) 0.0925(2) 0.2778(2) 0.0421(11) Uani 1 1 d . . . H5A H 0.8383 0.0649 0.2766 0.051 Uiso 1 1 calc R . . C6 C 0.5385(3) 0.13098(19) 0.4170(2) 0.0263(8) Uani 1 1 d . . . C7 C 0.5402(3) 0.0667(2) 0.6059(2) 0.0276(8) Uani 1 1 d . . . C8 C 0.4514(3) 0.0921(2) 0.6646(2) 0.0297(9) Uani 1 1 d . . . C9 C 0.4578(4) 0.0718(3) 0.7402(2) 0.0455(11) Uani 1 1 d . . . H9 H 0.5191 0.0403 0.7574 0.055 Uiso 1 1 calc R . . C10 C 0.3740(4) 0.0977(3) 0.7911(3) 0.0514(12) Uani 1 1 d . . . H10 H 0.3776 0.0836 0.8427 0.062 Uiso 1 1 calc R . . C11 C 0.2853(4) 0.1444(3) 0.7645(3) 0.0499(12) Uani 1 1 d . . . H11 H 0.2284 0.1635 0.7981 0.060 Uiso 1 1 calc R . . C12 C 0.2813(4) 0.1629(2) 0.6877(3) 0.0416(11) Uani 1 1 d . . . H12 H 0.2198 0.1936 0.6695 0.050 Uiso 1 1 calc R . . Cu1 Cu 0.73860(4) 0.03746(2) 0.44099(3) 0.02635(16) Uani 1 1 d . . . Cu2 Cu 0.38654(4) 0.16688(3) 0.52814(3) 0.03054(16) Uani 1 1 d . . . N1 N 0.7042(3) 0.09232(17) 0.34258(17) 0.0313(7) Uani 1 1 d . . . N2 N 0.5884(3) 0.09041(17) 0.47330(16) 0.0245(7) Uani 1 1 d . . . N3 N 0.5196(3) 0.09844(17) 0.53940(16) 0.0258(7) Uani 1 1 d . . . N4 N 0.3629(3) 0.13806(17) 0.63835(18) 0.0307(7) Uani 1 1 d . . . O1 O 0.5370(2) 0.41732(14) 0.56476(15) 0.0325(6) Uani 1 1 d . . . O2 O 0.5514(3) 0.34774(16) 0.44584(17) 0.0441(7) Uani 1 1 d . . . O3 O 0.4892(3) 0.28061(14) 0.55909(17) 0.0479(8) Uani 1 1 d . . . O4 O 0.2509(2) 0.23462(16) 0.5106(2) 0.0529(9) Uani 1 1 d . . . H4B H 0.2091 0.2363 0.5512 0.063 Uiso 1 1 d R . . H4C H 0.2093 0.2157 0.4745 0.063 Uiso 1 1 d R . . O5 O 0.8755(2) -0.01399(14) 0.39161(14) 0.0328(6) Uani 1 1 d . . . H5B H 0.9275 -0.0227 0.4257 0.049 Uiso 1 1 d R . . H5C H 0.8538 -0.0571 0.3717 0.049 Uiso 1 1 d R . . O6 O 0.7422(2) -0.03971(14) 0.52241(15) 0.0298(6) Uani 1 1 d . . . H6A H 0.8028 -0.0683 0.5173 0.045 Uiso 1 1 d R . . H6B H 0.7446 -0.0167 0.5658 0.045 Uiso 1 1 d R . . O7 O 0.3607(2) 0.37479(15) 0.50073(16) 0.0327(6) Uani 1 1 d . . . O8 O 0.4428(2) 0.16882(14) 0.42211(15) 0.0304(6) Uani 1 1 d . . . O9 O 0.6201(2) 0.02059(17) 0.62692(15) 0.0427(7) Uani 1 1 d . . . S1 S 0.48399(8) 0.35429(5) 0.51761(5) 0.0274(2) 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 0.025(2) 0.0309(19) 0.031(2) -0.0022(16) -0.0036(16) -0.0014(16) C2 0.032(2) 0.045(2) 0.033(2) 0.0018(18) -0.0076(19) -0.0002(18) C3 0.050(3) 0.051(3) 0.029(2) 0.0053(19) -0.008(2) -0.004(2) C4 0.050(3) 0.057(3) 0.030(2) 0.002(2) 0.008(2) 0.000(2) C5 0.039(3) 0.052(3) 0.036(2) 0.002(2) 0.0074(19) 0.007(2) C6 0.022(2) 0.0242(18) 0.033(2) -0.0027(16) -0.0053(16) -0.0054(16) C7 0.024(2) 0.0297(19) 0.029(2) -0.0014(16) -0.0050(16) 0.0001(16) C8 0.029(2) 0.030(2) 0.030(2) -0.0036(16) -0.0018(17) -0.0018(17) C9 0.039(3) 0.063(3) 0.034(2) 0.006(2) -0.002(2) 0.013(2) C10 0.051(3) 0.073(3) 0.031(2) 0.002(2) 0.005(2) 0.006(3) C11 0.049(3) 0.055(3) 0.045(3) -0.002(2) 0.019(2) 0.006(2) C12 0.037(3) 0.044(2) 0.044(3) 0.004(2) 0.010(2) 0.0094(19) Cu1 0.0207(3) 0.0293(3) 0.0290(3) 0.00061(19) 0.00007(19) 0.00088(18) Cu2 0.0237(3) 0.0316(3) 0.0363(3) 0.0058(2) 0.0023(2) 0.00481(19) N1 0.0282(18) 0.0381(18) 0.0276(17) 0.0026(14) 0.0013(14) 0.0012(14) N2 0.0182(15) 0.0284(16) 0.0269(17) 0.0024(13) -0.0005(13) -0.0021(12) N3 0.0202(16) 0.0302(16) 0.0271(17) 0.0033(13) 0.0000(13) 0.0004(13) N4 0.0268(18) 0.0306(17) 0.0347(18) 0.0004(14) 0.0049(14) 0.0009(14) O1 0.0226(14) 0.0311(14) 0.0438(16) -0.0073(12) -0.0050(12) -0.0030(11) O2 0.0344(17) 0.0439(16) 0.0540(19) -0.0142(14) 0.0140(14) -0.0088(14) O3 0.054(2) 0.0297(15) 0.060(2) 0.0059(14) -0.0299(16) -0.0048(14) O4 0.0226(16) 0.0447(18) 0.091(3) 0.0100(18) -0.0046(15) -0.0011(13) O5 0.0293(15) 0.0384(14) 0.0306(15) -0.0087(12) -0.0027(11) 0.0035(12) O6 0.0251(15) 0.0301(14) 0.0341(15) 0.0026(11) 0.0010(11) 0.0045(11) O7 0.0177(13) 0.0340(14) 0.0465(16) -0.0065(12) -0.0054(11) 0.0044(11) O8 0.0255(15) 0.0345(14) 0.0311(15) 0.0022(11) -0.0023(11) 0.0053(12) O9 0.0374(17) 0.0602(18) 0.0304(15) 0.0053(13) -0.0022(13) 0.0206(14) S1 0.0173(5) 0.0257(5) 0.0393(6) -0.0017(4) -0.0025(4) -0.0004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.341(5) . ? C1 C2 1.376(5) . ? C1 C6 1.473(5) . ? C2 C3 1.382(6) . ? C2 H2 0.9300 . ? C3 C4 1.361(6) . ? C3 H3 0.9300 . ? C4 C5 1.378(6) . ? C4 H4A 0.9300 . ? C5 N1 1.337(5) . ? C5 H5A 0.9300 . ? C6 O8 1.269(4) . ? C6 N2 1.327(4) . ? C7 O9 1.257(4) . ? C7 N3 1.298(4) . ? C7 C8 1.500(5) . ? C8 N4 1.356(5) . ? C8 C9 1.360(5) . ? C9 C10 1.373(6) . ? C9 H9 0.9300 . ? C10 C11 1.368(6) . ? C10 H10 0.9300 . ? C11 C12 1.372(6) . ? C11 H11 0.9300 . ? C12 N4 1.333(5) . ? C12 H12 0.9300 . ? Cu1 O6 1.935(2) . ? Cu1 O5 1.983(2) . ? Cu1 N1 1.989(3) . ? Cu1 N2 2.013(3) . ? Cu1 O7 2.281(3) 4_556 ? Cu2 N3 1.923(3) . ? Cu2 O8 1.950(3) . ? Cu2 O4 1.953(3) . ? Cu2 N4 1.995(3) . ? Cu2 O3 2.331(3) . ? N2 N3 1.397(4) . ? O1 S1 1.482(3) . ? O2 S1 1.468(3) . ? O3 S1 1.453(3) . ? O4 H4B 0.8499 . ? O4 H4C 0.8500 . ? O5 H5B 0.8500 . ? O5 H5C 0.8500 . ? O6 H6A 0.8501 . ? O6 H6B 0.8499 . ? O7 S1 1.475(3) . ? O7 Cu1 2.281(3) 4_456 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 122.5(4) . . ? N1 C1 C6 115.4(3) . . ? C2 C1 C6 122.1(3) . . ? C1 C2 C3 118.5(4) . . ? C1 C2 H2 120.7 . . ? C3 C2 H2 120.7 . . ? C4 C3 C2 119.2(4) . . ? C4 C3 H3 120.4 . . ? C2 C3 H3 120.4 . . ? C3 C4 C5 119.4(4) . . ? C3 C4 H4A 120.3 . . ? C5 C4 H4A 120.3 . . ? N1 C5 C4 122.1(4) . . ? N1 C5 H5A 119.0 . . ? C4 C5 H5A 119.0 . . ? O8 C6 N2 125.6(3) . . ? O8 C6 C1 118.6(3) . . ? N2 C6 C1 115.8(3) . . ? O9 C7 N3 130.7(4) . . ? O9 C7 C8 118.1(3) . . ? N3 C7 C8 111.2(3) . . ? N4 C8 C9 120.8(4) . . ? N4 C8 C7 116.0(3) . . ? C9 C8 C7 123.1(4) . . ? C8 C9 C10 120.2(4) . . ? C8 C9 H9 119.9 . . ? C10 C9 H9 119.9 . . ? C11 C10 C9 118.9(4) . . ? C11 C10 H10 120.6 . . ? C9 C10 H10 120.6 . . ? C10 C11 C12 119.1(4) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? N4 C12 C11 122.0(4) . . ? N4 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? O6 Cu1 O5 89.83(11) . . ? O6 Cu1 N1 162.61(12) . . ? O5 Cu1 N1 89.51(12) . . ? O6 Cu1 N2 96.95(11) . . ? O5 Cu1 N2 170.44(11) . . ? N1 Cu1 N2 82.00(12) . . ? O6 Cu1 O7 96.38(11) . 4_556 ? O5 Cu1 O7 90.37(10) . 4_556 ? N1 Cu1 O7 101.00(11) . 4_556 ? N2 Cu1 O7 95.54(10) . 4_556 ? N3 Cu2 O8 81.27(11) . . ? N3 Cu2 O4 176.79(14) . . ? O8 Cu2 O4 95.87(13) . . ? N3 Cu2 N4 81.84(12) . . ? O8 Cu2 N4 162.69(11) . . ? O4 Cu2 N4 100.91(14) . . ? N3 Cu2 O3 95.18(11) . . ? O8 Cu2 O3 92.26(11) . . ? O4 Cu2 O3 86.37(11) . . ? N4 Cu2 O3 92.99(12) . . ? C5 N1 C1 118.2(3) . . ? C5 N1 Cu1 128.2(3) . . ? C1 N1 Cu1 113.6(2) . . ? C6 N2 N3 108.4(3) . . ? C6 N2 Cu1 113.1(2) . . ? N3 N2 Cu1 138.5(2) . . ? C7 N3 N2 126.1(3) . . ? C7 N3 Cu2 119.2(2) . . ? N2 N3 Cu2 114.7(2) . . ? C12 N4 C8 119.0(3) . . ? C12 N4 Cu2 129.3(3) . . ? C8 N4 Cu2 111.5(2) . . ? S1 O3 Cu2 126.05(16) . . ? Cu2 O4 H4B 109.4 . . ? Cu2 O4 H4C 109.2 . . ? H4B O4 H4C 108.2 . . ? Cu1 O5 H5B 108.8 . . ? Cu1 O5 H5C 109.4 . . ? H5B O5 H5C 109.5 . . ? Cu1 O6 H6A 109.4 . . ? Cu1 O6 H6B 109.5 . . ? H6A O6 H6B 109.5 . . ? S1 O7 Cu1 130.29(16) . 4_456 ? C6 O8 Cu2 109.8(2) . . ? O3 S1 O2 109.50(18) . . ? O3 S1 O7 110.11(18) . . ? O2 S1 O7 110.23(18) . . ? O3 S1 O1 109.86(16) . . ? O2 S1 O1 108.20(16) . . ? O7 S1 O1 108.90(15) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.538 _refine_diff_density_min -0.634 _refine_diff_density_rms 0.102 # Attachment '- 3.cif' data_cui _database_code_depnum_ccdc_archive 'CCDC 831077' #TrackingRef '- 3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C14 H8 Cu2 N6 O' _chemical_formula_sum 'C14 H8 Cu2 N6 O' _chemical_formula_weight 403.34 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 monoclinic _symmetry_space_group_name_H-M 'C2/c ' _symmetry_space_group_name_Hall -C2yc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' _cell_length_a 9.763(2) _cell_length_b 15.902(4) _cell_length_c 9.503(2) _cell_angle_alpha 90.00 _cell_angle_beta 109.733(4) _cell_angle_gamma 90.00 _cell_volume 1388.7(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1233 _cell_measurement_theta_min 2.56 _cell_measurement_theta_max 26.6665 _exptl_crystal_description block _exptl_crystal_colour red _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.929 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 3.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.413 _exptl_absorpt_correction_T_max 0.524 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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_reflns_number 3416 _diffrn_reflns_av_R_equivalents 0.0481 _diffrn_reflns_av_sigmaI/netI 0.0483 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 25.00 _reflns_number_total 1227 _reflns_number_gt 931 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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. TITL cui in C2/c CELL 0.71073 9.7630 15.9025 9.5027 90.000 109.733 90.000 ZERR 4.00 0.0023 0.0037 0.0022 0.000 0.004 0.000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H N O Cu UNIT 56 32 24 4 8 OMIT 0.00 50.00 L.S. 21 ACTA BOND FMAP 2 PLAN 20 delu 0.003 N3 C7 Cu1 N2 Cu1 N3 WGHT 0.042600 0.000000 FVAR 0.151490 MOLE 1 C1 1 1.001597 0.798437 0.921595 11.000000 0.033910 0.038670 = 0.028590 0.000700 0.012950 -0.007970 AFIX 43 H1 2 1.075267 0.838510 0.949470 11.000000 -1.200000 AFIX 0 C2 1 1.040835 0.715166 0.935862 11.000000 0.035450 0.044160 = 0.027300 0.004430 0.012900 0.004970 AFIX 43 H2 2 1.138402 0.699827 0.973778 11.000000 -1.200000 AFIX 0 C3 1 0.934601 0.655051 0.893599 11.000000 0.044970 0.032400 = 0.035690 0.005900 0.018980 0.006800 AFIX 43 H3 2 0.958580 0.598237 0.901252 11.000000 -1.200000 AFIX 0 C4 1 0.791279 0.680385 0.839433 11.000000 0.037450 0.028370 = 0.031950 0.000790 0.013610 -0.003560 AFIX 43 H4 2 0.716442 0.641110 0.808970 11.000000 -1.200000 AFIX 0 C5 1 0.761782 0.764423 0.831559 11.000000 0.035450 0.029170 = 0.019600 0.001020 0.012960 -0.000270 C6 1 0.614779 0.797230 0.784422 11.000000 0.035510 0.025440 = 0.020750 -0.000620 0.011050 -0.003070 C7 1 0.794982 0.996083 0.515740 11.000000 0.048300 0.021220 = 0.024230 0.001850 0.015850 0.007840 Cu1 5 0.788310 0.958732 0.829263 11.000000 0.078390 0.035500 = 0.030480 -0.000280 0.026780 0.000290 N1 3 0.864882 0.825232 0.870427 11.000000 0.034000 0.032040 = 0.024590 0.001180 0.011670 -0.001850 AFIX 2 N2 3 0.576153 0.875188 0.772568 11.000000 0.045690 0.039410 = 0.031640 -0.001240 0.006440 0.003600 AFIX 0 N3 3 0.794368 0.979423 0.631828 11.000000 0.065090 0.032510 = 0.038960 0.002490 0.024390 0.008020 O1 4 0.500000 0.744146 0.750000 10.500000 0.031780 0.025930 = 0.030240 0.000000 0.013190 0.000000 HKLF 4 END ; _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^)+(0.0357P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1227 _refine_ls_number_parameters 99 _refine_ls_number_restraints 5 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_ref 0.0807 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.018 _refine_ls_restrained_S_all 1.040 _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 1.0015(4) 0.7985(2) 0.9215(4) 0.0331(9) Uani 1 1 d . . . H1 H 1.0752 0.8385 0.9494 0.040 Uiso 1 1 calc R . . C2 C 1.0408(4) 0.7152(2) 0.9358(4) 0.0350(9) Uani 1 1 d . . . H2 H 1.1383 0.6998 0.9738 0.042 Uiso 1 1 calc R . . C3 C 0.9346(4) 0.6551(2) 0.8936(4) 0.0363(9) Uani 1 1 d . . . H3 H 0.9586 0.5983 0.9013 0.044 Uiso 1 1 calc R . . C4 C 0.7912(4) 0.6804(2) 0.8394(4) 0.0319(8) Uani 1 1 d . . . H4 H 0.7164 0.6412 0.8089 0.038 Uiso 1 1 calc R . . C5 C 0.7618(4) 0.7644(2) 0.8316(3) 0.0269(8) Uani 1 1 d . . . C6 C 0.6148(4) 0.7972(2) 0.7844(3) 0.0267(8) Uani 1 1 d . . . C7 C 0.7950(4) 0.9961(2) 0.5156(4) 0.0301(8) Uani 1 1 d U . . Cu1 Cu 0.78832(6) 0.95874(3) 0.82925(5) 0.0460(2) Uani 1 1 d U . . N1 N 0.8648(3) 0.82524(17) 0.8704(3) 0.0296(7) Uani 1 1 d . . . N2 N 0.5762(3) 0.87519(19) 0.7726(3) 0.041 Uani 1 1 d U . . N3 N 0.7944(4) 0.97944(19) 0.6318(3) 0.0439(8) Uani 1 1 d U . . O1 O 0.5000 0.7441(2) 0.7500 0.0284(8) Uani 1 2 d S . . 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 0.034(2) 0.038(2) 0.0288(19) 0.0008(17) 0.0132(17) -0.0080(17) C2 0.035(2) 0.044(2) 0.0272(19) 0.0042(17) 0.0128(17) 0.0050(19) C3 0.045(3) 0.032(2) 0.036(2) 0.0059(17) 0.0190(18) 0.0065(18) C4 0.037(2) 0.028(2) 0.0319(19) 0.0008(16) 0.0134(17) -0.0035(17) C5 0.035(2) 0.029(2) 0.0193(16) 0.0010(15) 0.0127(15) -0.0002(16) C6 0.035(2) 0.026(2) 0.0205(17) -0.0007(14) 0.0111(15) -0.0030(16) C7 0.048(2) 0.0211(19) 0.0240(15) 0.0017(14) 0.0158(17) 0.0080(17) Cu1 0.0784(4) 0.0355(3) 0.0305(3) -0.0003(2) 0.0268(3) 0.0002(3) N1 0.0337(18) 0.0321(18) 0.0245(15) 0.0013(13) 0.0116(13) -0.0019(14) N2 0.046 0.039 0.032 -0.001 0.006 0.004 N3 0.065(2) 0.0326(19) 0.0391(16) 0.0024(14) 0.0245(17) 0.0080(15) O1 0.031(2) 0.0256(19) 0.0301(18) 0.000 0.0130(15) 0.000 _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 N1 1.327(4) . ? C1 C2 1.373(5) . ? C2 C3 1.367(5) . ? C3 C4 1.379(5) . ? C4 C5 1.363(5) . ? C5 N1 1.353(4) . ? C5 C6 1.449(5) . ? C6 N2 1.289(4) . ? C6 O1 1.353(4) . ? C7 N3 1.137(4) . ? C7 Cu1 1.892(3) 6_575 ? Cu1 C7 1.892(3) 6_576 ? Cu1 N3 1.926(3) . ? Cu1 N1 2.241(3) . ? Cu1 N2 2.365(3) . ? N2 N2 1.402(6) 2_656 ? O1 C6 1.353(4) 2_656 ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 124.0(3) . . ? C3 C2 C1 119.1(3) . . ? C2 C3 C4 118.6(4) . . ? C5 C4 C3 118.4(3) . . ? N1 C5 C4 124.2(3) . . ? N1 C5 C6 113.2(3) . . ? C4 C5 C6 122.6(3) . . ? N2 C6 O1 112.6(3) . . ? N2 C6 C5 127.1(3) . . ? O1 C6 C5 120.2(3) . . ? N3 C7 Cu1 170.9(3) . 6_575 ? C7 Cu1 N3 147.65(15) 6_576 . ? C7 Cu1 N1 106.99(12) 6_576 . ? N3 Cu1 N1 102.35(11) . . ? C7 Cu1 N2 100.20(13) 6_576 . ? N3 Cu1 N2 100.77(12) . . ? N1 Cu1 N2 73.86(10) . . ? C1 N1 C5 115.7(3) . . ? C1 N1 Cu1 127.1(2) . . ? C5 N1 Cu1 117.2(2) . . ? C6 N2 N2 106.0(2) . 2_656 ? C6 N2 Cu1 108.2(2) . . ? N2 N2 Cu1 145.78(7) 2_656 . ? C7 N3 Cu1 176.1(3) . . ? C6 O1 C6 102.7(4) . 2_656 ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 1.052 _refine_diff_density_min -0.370 _refine_diff_density_rms 0.075 # Attachment '- 4.cif' data_qq _database_code_depnum_ccdc_archive 'CCDC 831078' #TrackingRef '- 4.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H14 Cu2 N4 O7 ' _chemical_formula_sum 'C20 H14 Cu2 N4 O7 ' _chemical_formula_weight 549.45 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 Triclinic _symmetry_space_group_name_H-M P-1 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2659(14) _cell_length_b 9.9624(19) _cell_length_c 13.716(3) _cell_angle_alpha 94.208(4) _cell_angle_beta 98.334(3) _cell_angle_gamma 103.150(4) _cell_volume 950.7(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1088 _cell_measurement_theta_min 2.729 _cell_measurement_theta_max 24.973 _exptl_crystal_description block _exptl_crystal_colour 'dark green' _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.919 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 552.0 _exptl_absorpt_coefficient_mu 2.294 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.494 _exptl_absorpt_correction_T_max 0.618 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 4757 _diffrn_reflns_av_R_equivalents 0.0415 _diffrn_reflns_av_sigmaI/netI 0.0947 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.11 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3345 _reflns_number_gt 2270 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0002P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3282 _refine_ls_number_parameters 298 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0660 _refine_ls_R_factor_gt 0.0442 _refine_ls_wR_factor_ref 0.0725 _refine_ls_wR_factor_gt 0.0692 _refine_ls_goodness_of_fit_ref 0.949 _refine_ls_restrained_S_all 0.949 _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 0.7562(7) 0.5449(5) 0.8969(3) 0.0270(13) Uani 1 1 d . . . C2 C 0.8341(6) 0.5982(5) 0.8081(3) 0.0242(12) Uani 1 1 d . . . C3 C 0.8385(7) 0.7288(6) 0.7835(4) 0.0393(15) Uani 1 1 d . . . H3 H 0.7955 0.7909 0.8232 0.047 Uiso 1 1 calc R . . C4 C 0.9086(7) 0.7678(6) 0.6978(4) 0.0512(17) Uani 1 1 d . . . H4 H 0.9154 0.8571 0.6805 0.061 Uiso 1 1 calc R . . C5 C 0.9668(8) 0.6749(7) 0.6399(4) 0.0502(18) Uani 1 1 d . . . H5 H 1.0097 0.6984 0.5813 0.060 Uiso 1 1 calc R . . C6 C 0.9615(7) 0.5462(6) 0.6691(4) 0.0415(16) Uani 1 1 d . . . H6 H 1.0034 0.4829 0.6298 0.050 Uiso 1 1 calc R . . C7 C 0.7781(6) 0.2286(5) 0.9769(3) 0.0258(12) Uani 1 1 d . . . C8 C 0.7263(7) 0.1371(5) 1.0541(3) 0.0236(12) Uani 1 1 d . . . C9 C 0.7564(7) 0.0062(5) 1.0533(4) 0.0385(14) Uani 1 1 d . . . H9 H 0.8130 -0.0285 1.0036 0.046 Uiso 1 1 calc R . . C10 C 0.7016(8) -0.0736(6) 1.1272(4) 0.0481(16) Uani 1 1 d . . . H10 H 0.7244 -0.1616 1.1288 0.058 Uiso 1 1 calc R . . C11 C 0.6128(7) -0.0218(6) 1.1986(4) 0.0424(15) Uani 1 1 d . . . H11 H 0.5684 -0.0752 1.2470 0.051 Uiso 1 1 calc R . . C12 C 0.5923(7) 0.1123(6) 1.1955(4) 0.0326(13) Uani 1 1 d . . . H12 H 0.5362 0.1495 1.2445 0.039 Uiso 1 1 calc R . . C13 C 0.8455(8) 0.1457(5) 0.6473(4) 0.0302(13) Uani 1 1 d . . . C14 C 0.9272(7) 0.0728(5) 0.5701(3) 0.0233(12) Uani 1 1 d . . . C15 C 1.1212(7) 0.0929(5) 0.5726(3) 0.0265(12) Uani 1 1 d . . . H15 H 1.2046 0.1561 0.6218 0.032 Uiso 1 1 calc R . . C16 C 0.8034(7) -0.0210(5) 0.4967(3) 0.0282(13) Uani 1 1 d . . . H16 H 0.6715 -0.0359 0.4935 0.034 Uiso 1 1 calc R . . C17 C 0.5786(6) 0.5172(6) 1.2996(3) 0.0247(12) Uani 1 1 d . . . C18 C 0.5395(6) 0.5070(5) 1.4046(3) 0.0236(12) Uani 1 1 d . . . C19 C 0.4833(6) 0.6144(5) 1.4511(3) 0.0259(12) Uani 1 1 d . . . H19 H 0.4721 0.6918 1.4188 0.031 Uiso 1 1 calc R . . C20 C 0.5567(6) 0.3942(5) 1.4529(3) 0.0292(13) Uani 1 1 d . . . H20 H 0.5957 0.3222 1.4213 0.035 Uiso 1 1 calc R . . Cu1 Cu 0.65929(8) 0.39037(6) 1.11988(4) 0.02459(18) Uani 1 1 d . . . Cu2 Cu 0.89301(8) 0.32960(7) 0.81323(4) 0.03034(19) Uani 1 1 d . . . N1 N 0.8002(5) 0.4270(4) 0.9139(3) 0.0234(10) Uani 1 1 d . . . N2 N 0.7394(5) 0.3503(4) 0.9896(3) 0.0211(10) Uani 1 1 d . . . N3 N 0.8983(5) 0.5078(4) 0.7518(3) 0.0287(11) Uani 1 1 d . . . N5 N 0.6485(5) 0.1907(4) 1.1261(3) 0.0240(10) Uani 1 1 d . . . O1 O 0.6624(4) 0.6149(3) 0.9424(2) 0.0292(9) Uani 1 1 d . . . O2 O 0.8503(4) 0.1841(3) 0.9053(2) 0.0341(9) Uani 1 1 d . . . O3 O 0.9735(5) 0.2323(4) 0.7104(2) 0.0430(11) Uani 1 1 d . . . O4 O 0.6762(5) 0.1202(4) 0.6488(3) 0.0504(11) Uani 1 1 d . . . O5 O 0.5740(5) 0.6268(3) 1.2627(2) 0.0319(9) Uani 1 1 d . . . O6 O 0.6141(4) 0.4123(3) 1.2563(2) 0.0268(8) Uani 1 1 d . . . O7 O 0.7586(4) 0.5896(3) 1.1243(2) 0.0258(8) Uani 1 1 d . . . H7A H 0.7383 0.6303 1.1770 0.039 Uiso 1 1 d R . . H7C H 0.7018 0.6179 1.0741 0.039 Uiso 1 1 d 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 0.022(3) 0.035(4) 0.019(3) 0.001(3) 0.000(2) 0.001(3) C2 0.026(3) 0.031(3) 0.016(3) 0.005(2) 0.004(2) 0.007(3) C3 0.039(4) 0.045(4) 0.034(3) 0.011(3) 0.006(3) 0.008(3) C4 0.052(4) 0.052(5) 0.053(4) 0.037(4) 0.015(3) 0.004(3) C5 0.042(4) 0.083(6) 0.033(3) 0.028(4) 0.018(3) 0.015(4) C6 0.034(3) 0.069(5) 0.021(3) 0.010(3) 0.009(3) 0.007(3) C7 0.025(3) 0.030(3) 0.023(3) -0.001(3) 0.007(2) 0.007(3) C8 0.026(3) 0.021(3) 0.025(3) 0.000(2) 0.010(2) 0.008(2) C9 0.054(4) 0.029(4) 0.037(3) 0.000(3) 0.019(3) 0.012(3) C10 0.069(4) 0.027(4) 0.054(4) 0.009(3) 0.019(3) 0.018(3) C11 0.057(4) 0.029(4) 0.040(4) 0.015(3) 0.007(3) 0.006(3) C12 0.033(3) 0.042(4) 0.025(3) 0.010(3) 0.013(2) 0.007(3) C13 0.045(4) 0.026(3) 0.022(3) 0.008(3) 0.018(3) 0.006(3) C14 0.037(3) 0.021(3) 0.016(3) 0.007(2) 0.010(2) 0.011(2) C15 0.037(3) 0.022(3) 0.017(3) -0.001(2) 0.006(2) 0.003(2) C16 0.030(3) 0.032(3) 0.023(3) 0.000(3) 0.011(2) 0.006(3) C17 0.022(3) 0.032(4) 0.017(3) -0.001(3) 0.004(2) 0.002(3) C18 0.027(3) 0.029(3) 0.013(2) -0.001(2) 0.006(2) 0.002(2) C19 0.034(3) 0.027(3) 0.015(3) 0.001(2) 0.009(2) 0.003(2) C20 0.040(3) 0.030(3) 0.020(3) -0.004(3) 0.014(2) 0.012(3) Cu1 0.0362(4) 0.0256(4) 0.0150(3) 0.0025(3) 0.0104(3) 0.0096(3) Cu2 0.0393(4) 0.0337(4) 0.0190(3) -0.0030(3) 0.0137(3) 0.0074(3) N1 0.033(3) 0.027(3) 0.014(2) 0.008(2) 0.0128(19) 0.008(2) N2 0.033(3) 0.020(3) 0.015(2) -0.0004(19) 0.0097(18) 0.014(2) N3 0.024(2) 0.043(3) 0.020(2) 0.009(2) 0.0085(19) 0.005(2) N5 0.028(2) 0.020(3) 0.026(2) 0.003(2) 0.0092(19) 0.0067(19) O1 0.042(2) 0.034(2) 0.0178(18) 0.0022(16) 0.0101(16) 0.0177(18) O2 0.051(2) 0.027(2) 0.031(2) 0.0023(17) 0.0250(18) 0.0119(18) O3 0.046(2) 0.047(3) 0.031(2) -0.017(2) 0.0193(18) 0.001(2) O4 0.039(2) 0.065(3) 0.047(2) -0.013(2) 0.020(2) 0.011(2) O5 0.050(2) 0.033(2) 0.0173(18) 0.0030(17) 0.0166(16) 0.0121(19) O6 0.042(2) 0.031(2) 0.0119(17) 0.0006(16) 0.0125(15) 0.0151(17) O7 0.042(2) 0.024(2) 0.0132(17) 0.0005(15) 0.0112(15) 0.0100(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 O1 1.272(5) . ? C1 N1 1.314(6) . ? C1 C2 1.498(6) . ? C2 N3 1.349(5) . ? C2 C3 1.362(7) . ? C3 C4 1.394(7) . ? C3 H3 0.9300 . ? C4 C5 1.354(7) . ? C4 H4 0.9300 . ? C5 C6 1.365(7) . ? C5 H5 0.9300 . ? C6 N3 1.333(6) . ? C6 H6 0.9300 . ? C7 O2 1.277(5) . ? C7 N2 1.311(6) . ? C7 C8 1.481(6) . ? C8 N5 1.343(5) . ? C8 C9 1.370(6) . ? C9 C10 1.382(7) . ? C9 H9 0.9300 . ? C10 C11 1.379(7) . ? C10 H10 0.9300 . ? C11 C12 1.381(7) . ? C11 H11 0.9300 . ? C12 N5 1.326(6) . ? C12 H12 0.9300 . ? C13 O4 1.202(5) . ? C13 O3 1.284(5) . ? C13 C14 1.506(6) . ? C14 C15 1.373(6) . ? C14 C16 1.383(6) . ? C15 C16 1.395(5) 2_756 ? C15 H15 0.9300 . ? C16 C15 1.395(5) 2_756 ? C16 H16 0.9300 . ? C17 O5 1.243(6) . ? C17 O6 1.259(5) . ? C17 C18 1.514(6) . ? C18 C20 1.367(6) . ? C18 C19 1.375(6) . ? C19 C20 1.393(5) 2_668 ? C19 H19 0.9300 . ? C20 C19 1.393(5) 2_668 ? C20 H20 0.9300 . ? Cu1 O7 1.945(3) . ? Cu1 O6 1.951(3) . ? Cu1 N5 1.982(4) . ? Cu1 N2 1.998(3) . ? Cu1 O1 2.357(3) 2_667 ? Cu2 O3 1.889(3) . ? Cu2 N1 1.916(4) . ? Cu2 O2 1.992(3) . ? Cu2 N3 2.016(4) . ? N1 N2 1.397(5) . ? O1 Cu1 2.357(3) 2_667 ? O7 H7A 0.8500 . ? O7 H7C 0.8499 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 N1 130.7(5) . . ? O1 C1 C2 118.8(5) . . ? N1 C1 C2 110.6(4) . . ? N3 C2 C3 121.2(5) . . ? N3 C2 C1 115.8(5) . . ? C3 C2 C1 123.0(5) . . ? C2 C3 C4 118.8(5) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 119.6(6) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C4 C5 C6 118.9(5) . . ? C4 C5 H5 120.6 . . ? C6 C5 H5 120.6 . . ? N3 C6 C5 122.4(6) . . ? N3 C6 H6 118.8 . . ? C5 C6 H6 118.8 . . ? O2 C7 N2 126.2(5) . . ? O2 C7 C8 119.4(4) . . ? N2 C7 C8 114.4(4) . . ? N5 C8 C9 121.6(5) . . ? N5 C8 C7 115.8(4) . . ? C9 C8 C7 122.6(4) . . ? C8 C9 C10 119.2(5) . . ? C8 C9 H9 120.4 . . ? C10 C9 H9 120.4 . . ? C9 C10 C11 119.6(5) . . ? C9 C10 H10 120.2 . . ? C11 C10 H10 120.2 . . ? C12 C11 C10 117.6(5) . . ? C12 C11 H11 121.2 . . ? C10 C11 H11 121.2 . . ? N5 C12 C11 123.2(5) . . ? N5 C12 H12 118.4 . . ? C11 C12 H12 118.4 . . ? O4 C13 O3 125.0(5) . . ? O4 C13 C14 121.5(5) . . ? O3 C13 C14 113.5(4) . . ? C15 C14 C16 119.1(4) . . ? C15 C14 C13 121.8(4) . . ? C16 C14 C13 119.1(4) . . ? C14 C15 C16 121.7(4) . 2_756 ? C14 C15 H15 119.1 . . ? C16 C15 H15 119.1 2_756 . ? C15 C16 C14 119.2(4) 2_756 . ? C15 C16 H16 120.4 2_756 . ? C14 C16 H16 120.4 . . ? O5 C17 O6 124.9(4) . . ? O5 C17 C18 118.4(4) . . ? O6 C17 C18 116.7(5) . . ? C20 C18 C19 120.0(4) . . ? C20 C18 C17 121.7(5) . . ? C19 C18 C17 118.3(5) . . ? C18 C19 C20 119.2(5) . 2_668 ? C18 C19 H19 120.4 . . ? C20 C19 H19 120.4 2_668 . ? C18 C20 C19 120.9(5) . 2_668 ? C18 C20 H20 119.6 . . ? C19 C20 H20 119.6 2_668 . ? O7 Cu1 O6 90.65(13) . . ? O7 Cu1 N5 161.29(14) . . ? O6 Cu1 N5 91.43(15) . . ? O7 Cu1 N2 93.45(14) . . ? O6 Cu1 N2 169.99(15) . . ? N5 Cu1 N2 81.80(15) . . ? O7 Cu1 O1 96.81(12) . 2_667 ? O6 Cu1 O1 91.45(12) . 2_667 ? N5 Cu1 O1 101.73(13) . 2_667 ? N2 Cu1 O1 97.11(13) . 2_667 ? O3 Cu2 N1 177.41(16) . . ? O3 Cu2 O2 100.15(15) . . ? N1 Cu2 O2 80.43(15) . . ? O3 Cu2 N3 98.07(16) . . ? N1 Cu2 N3 81.27(16) . . ? O2 Cu2 N3 161.64(14) . . ? C1 N1 N2 123.2(4) . . ? C1 N1 Cu2 119.1(3) . . ? N2 N1 Cu2 115.8(3) . . ? C7 N2 N1 108.4(4) . . ? C7 N2 Cu1 114.0(3) . . ? N1 N2 Cu1 136.3(3) . . ? C6 N3 C2 119.1(5) . . ? C6 N3 Cu2 129.2(4) . . ? C2 N3 Cu2 111.7(3) . . ? C12 N5 C8 118.9(4) . . ? C12 N5 Cu1 128.3(3) . . ? C8 N5 Cu1 112.6(3) . . ? C1 O1 Cu1 121.3(3) . 2_667 ? C7 O2 Cu2 108.9(3) . . ? C13 O3 Cu2 118.4(3) . . ? C17 O6 Cu1 126.5(3) . . ? Cu1 O7 H7A 109.8 . . ? Cu1 O7 H7C 108.9 . . ? H7A O7 H7C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.543 _refine_diff_density_min -0.613 _refine_diff_density_rms 0.092 # Attachment '- 5.cif' data_eeew _database_code_depnum_ccdc_archive 'CCDC 831079' #TrackingRef '- 5.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H8 Cu N2 O4' _chemical_formula_sum 'C12 H8 Cu N2 O4' _chemical_formula_weight 307.74 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 monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_space_group_name_Hall '-P 2ybc' 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 3.7781(17) _cell_length_b 12.032(5) _cell_length_c 11.896(5) _cell_angle_alpha 90.00 _cell_angle_beta 91.585(9) _cell_angle_gamma 90.00 _cell_volume 540.6(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 756 _cell_measurement_theta_min 2.408 _cell_measurement_theta_max 23.8945 _exptl_crystal_description block _exptl_crystal_colour blue _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.891 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 310 _exptl_absorpt_coefficient_mu 2.032 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.549 _exptl_absorpt_correction_T_max 0.653 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 2597 _diffrn_reflns_av_R_equivalents 0.0836 _diffrn_reflns_av_sigmaI/netI 0.0709 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.41 _diffrn_reflns_theta_max 24.99 _reflns_number_total 956 _reflns_number_gt 694 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SMART (Bruker, 2000)' _computing_data_reduction 'SMART (Bruker, 2000)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics SHELXTL _computing_publication_material 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^)+(0.0123P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 951 _refine_ls_number_parameters 88 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0538 _refine_ls_R_factor_gt 0.0386 _refine_ls_wR_factor_ref 0.0756 _refine_ls_wR_factor_gt 0.0734 _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 O1 O 0.1924(7) 0.51158(18) 0.36892(19) 0.0480(7) Uani 1 1 d . . . C1 C 0.6403(10) 0.2572(3) 0.5232(3) 0.0369(9) Uani 1 1 d . . . H1 H 0.7462 0.2713 0.5932 0.044 Uiso 1 1 calc R . . C2 C 0.6341(10) 0.1505(3) 0.4821(3) 0.0401(10) Uani 1 1 d . . . H2 H 0.7339 0.0928 0.5243 0.048 Uiso 1 1 calc R . . C3 C 0.4804(9) 0.1297(3) 0.3791(3) 0.0424(10) Uani 1 1 d . . . H3 H 0.4787 0.0581 0.3496 0.051 Uiso 1 1 calc R . . C4 C 0.3296(9) 0.2153(3) 0.3201(3) 0.0368(9) Uani 1 1 d . . . H4 H 0.2219 0.2025 0.2500 0.044 Uiso 1 1 calc R . . C5 C 0.3374(9) 0.3210(3) 0.3645(3) 0.0320(8) Uani 1 1 d . . . C6 C 0.1643(10) 0.4206(3) 0.3095(3) 0.0379(9) Uani 1 1 d . . . Cu1 Cu 0.5000 0.5000 0.5000 0.0422(2) Uani 1 2 d S . . N1 N 0.4970(7) 0.3411(2) 0.4643(2) 0.0330(7) Uani 1 1 d . . . O2 O 0.0078(7) 0.41255(19) 0.22040(19) 0.0503(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 O1 0.0703(19) 0.0295(14) 0.0427(14) -0.0037(11) -0.0234(14) 0.0024(14) C1 0.044(2) 0.037(2) 0.0287(19) 0.0035(16) -0.0079(16) 0.000(2) C2 0.050(2) 0.032(2) 0.039(2) 0.0081(16) 0.002(2) 0.0010(19) C3 0.054(3) 0.033(2) 0.041(2) -0.0088(18) 0.004(2) -0.002(2) C4 0.047(2) 0.039(2) 0.0247(18) -0.0030(16) -0.0046(17) -0.005(2) C5 0.033(2) 0.039(2) 0.0237(18) -0.0007(16) -0.0008(16) -0.0110(17) C6 0.043(2) 0.036(2) 0.035(2) 0.0085(17) -0.0030(18) -0.0070(19) Cu1 0.0601(5) 0.0293(4) 0.0361(4) -0.0023(3) -0.0188(3) -0.0004(4) N1 0.0407(19) 0.0288(16) 0.0292(16) 0.0001(12) -0.0030(15) -0.0023(14) O2 0.0695(19) 0.0489(16) 0.0310(14) -0.0010(12) -0.0246(13) -0.0020(15) _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 C6 1.305(4) . ? O1 Cu1 1.924(2) . ? C1 N1 1.335(4) . ? C1 C2 1.374(5) . ? C1 H1 0.9300 . ? C2 C3 1.365(5) . ? C2 H2 0.9300 . ? C3 C4 1.363(5) . ? C3 H3 0.9300 . ? C4 C5 1.377(4) . ? C4 H4 0.9300 . ? C5 N1 1.339(4) . ? C5 C6 1.506(4) . ? C6 O2 1.204(4) . ? Cu1 O1 1.924(2) 3_666 ? Cu1 N1 1.958(3) . ? Cu1 N1 1.958(3) 3_666 ? 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 O1 Cu1 114.6(2) . . ? N1 C1 C2 121.2(3) . . ? N1 C1 H1 119.4 . . ? C2 C1 H1 119.4 . . ? C3 C2 C1 119.6(3) . . ? C3 C2 H2 120.2 . . ? C1 C2 H2 120.2 . . ? C4 C3 C2 119.0(3) . . ? C4 C3 H3 120.5 . . ? C2 C3 H3 120.5 . . ? C3 C4 C5 119.8(3) . . ? C3 C4 H4 120.1 . . ? C5 C4 H4 120.1 . . ? N1 C5 C4 120.8(3) . . ? N1 C5 C6 114.9(3) . . ? C4 C5 C6 124.3(3) . . ? O2 C6 O1 125.1(3) . . ? O2 C6 C5 121.0(3) . . ? O1 C6 C5 113.9(3) . . ? O1 Cu1 O1 179.999(1) . 3_666 ? O1 Cu1 N1 83.98(10) . . ? O1 Cu1 N1 96.02(10) 3_666 . ? O1 Cu1 N1 96.02(10) . 3_666 ? O1 Cu1 N1 83.98(10) 3_666 3_666 ? N1 Cu1 N1 180.00(15) . 3_666 ? C1 N1 C5 119.6(3) . . ? C1 N1 Cu1 128.7(2) . . ? C5 N1 Cu1 111.6(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.521 _refine_diff_density_min -0.241 _refine_diff_density_rms 0.073