# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_C551_Comp.1 _database_code_depnum_ccdc_archive 'CCDC 881136' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C15 H21 Cu N3 O5, 3(H2 O)' _chemical_formula_sum 'C15 H27 Cu N3 O8' _chemical_formula_weight 440.94 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y+1/2, z' 3 'x+1/2, -y, -z+1/2' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y-1/2, -z' 7 '-x-1/2, y, z-1/2' 8 'x, -y-1/2, z-1/2' _symmetry_cell_setting Orthorhombic _symmetry_Int_Tables_number 56 _symmetry_space_group_name_H-M 'P c c n' _symmetry_space_group_name_Hall '-P 2ab 2ac' _cell_length_a 34.292(18) _cell_length_b 9.563(5) _cell_length_c 11.407(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3741(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 1987 _cell_measurement_temperature 110(2) _cell_measurement_theta_max 27.15 _cell_measurement_theta_min 2.8425 _exptl_absorpt_coefficient_mu 1.216 _exptl_absorpt_correction_T_max 0.9530 _exptl_absorpt_correction_T_min 0.7672 _exptl_absorpt_correction_type Empirical _exptl_absorpt_process_details SADABS _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.566 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1848 _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0564 _diffrn_reflns_av_sigmaI/netI 0.0488 _diffrn_reflns_limit_h_max 42 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 18037 _diffrn_reflns_theta_full 26.02 _diffrn_reflns_theta_max 26.02 _diffrn_reflns_theta_min 1.19 _diffrn_ambient_temperature 110(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker CCD SMART1000 ' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 3022 _reflns_number_total 3676 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'SMART Software (Bruker, 1997)' _computing_data_collection 'SMART Software (Bruker, 1997)' _computing_data_reduction 'SAINT Software (Bruker, 1997)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _refine_diff_density_max 0.557 _refine_diff_density_min -1.364 _refine_diff_density_rms 0.132 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.307 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 244 _refine_ls_number_reflns 3676 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0920 _refine_ls_R_factor_gt 0.0748 _refine_ls_restrained_S_all 1.307 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0426P)^2^+32.3480P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1688 _refine_ls_wR_factor_ref 0.1842 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.09556(2) 0.07666(8) 0.31250(6) 0.0115(2) Uani 1 1 d . . . O1 O 0.10790(12) 0.3107(5) 0.2832(4) 0.0149(10) Uani 1 1 d . . . H1a H 0.1158 0.3732 0.3455 0.022 Uiso 1 1 d R . . H1b H 0.1178 0.3401 0.2212 0.022 Uiso 1 1 d R . . O11 O 0.09201(12) 0.0604(5) 0.1445(4) 0.0137(9) Uani 1 1 d . . . O12 O 0.13167(13) 0.0579(5) -0.0096(4) 0.0183(10) Uani 1 1 d . . . O21 O 0.10783(11) 0.1069(4) 0.4749(4) 0.0115(9) Uani 1 1 d . . . O22 O 0.15826(12) 0.1292(5) 0.5934(4) 0.0145(9) Uani 1 1 d . . . N3 N 0.03881(14) 0.0719(6) 0.3398(4) 0.0107(10) Uani 1 1 d . . . N9 N 0.03599(15) 0.2638(6) 0.4750(4) 0.0132(11) Uani 1 1 d . . . H9 H 0.0613 0.2780 0.4915 0.016 Uiso 1 1 d R . . N10 N 0.15057(14) 0.0010(5) 0.2981(4) 0.0096(10) Uani 1 1 d . . . C2 C 0.01654(17) -0.0248(7) 0.2865(5) 0.0127(13) Uani 1 1 d . . . H2 H 0.0290 -0.0920 0.2379 0.015 Uiso 1 1 d R . . C1 C -0.02387(19) -0.0316(7) 0.2989(6) 0.0185(14) Uani 1 1 d . . . H1 H -0.0381 -0.1028 0.2597 0.022 Uiso 1 1 d R . . C6 C -0.04316(17) 0.0642(7) 0.3675(5) 0.0146(13) Uani 1 1 d . . . H6 H -0.0707 0.0618 0.3755 0.018 Uiso 1 1 d R . . C5 C -0.02087(18) 0.1648(6) 0.4249(5) 0.0128(13) Uani 1 1 d . . . C4 C 0.01999(17) 0.1608(6) 0.4093(5) 0.0102(12) Uani 1 1 d . . . C8 C 0.00663(19) 0.3327(7) 0.5324(6) 0.0173(14) Uani 1 1 d . . . H8 H 0.0103 0.4084 0.5851 0.021 Uiso 1 1 d R . . C7 C -0.02832(18) 0.2776(7) 0.5032(5) 0.0157(14) Uani 1 1 d . . . H7 H -0.0531 0.3083 0.5298 0.019 Uiso 1 1 d R . . C11 C 0.16113(18) 0.0459(7) 0.1770(5) 0.0153(13) Uani 1 1 d . . . H11a H 0.1802 -0.0209 0.1437 0.018 Uiso 1 1 d R . . H11b H 0.1737 0.1390 0.1804 0.018 Uiso 1 1 d R . . C12 C 0.12570(18) 0.0535(6) 0.0973(5) 0.0124(13) Uani 1 1 d . . . C21 C 0.17115(17) 0.0798(6) 0.3919(5) 0.0100(12) Uani 1 1 d . . . H21a H 0.1806 0.1700 0.3601 0.012 Uiso 1 1 d R . . H21b H 0.1941 0.0255 0.4186 0.012 Uiso 1 1 d R . . C22 C 0.14425(18) 0.1070(6) 0.4952(5) 0.0119(13) Uani 1 1 d . . . C31 C 0.15395(18) -0.1559(7) 0.3164(5) 0.0139(13) Uani 1 1 d . . . C32 C 0.1448(2) -0.1931(7) 0.4424(5) 0.0172(14) Uani 1 1 d . . . H32a H 0.1638 -0.1486 0.4944 0.026 Uiso 1 1 d R . . H32b H 0.1460 -0.2948 0.4523 0.026 Uiso 1 1 d R . . H32c H 0.1185 -0.1600 0.4621 0.026 Uiso 1 1 d R . . C33 C 0.19495(19) -0.2079(7) 0.2867(6) 0.0197(15) Uani 1 1 d . . . H33a H 0.1979 -0.3049 0.3129 0.030 Uiso 1 1 d R . . H33b H 0.2143 -0.1491 0.3263 0.030 Uiso 1 1 d R . . H33c H 0.1990 -0.2029 0.2017 0.030 Uiso 1 1 d R . . C34 C 0.1244(2) -0.2291(7) 0.2376(6) 0.0193(14) Uani 1 1 d . . . H34a H 0.0980 -0.1990 0.2589 0.029 Uiso 1 1 d R . . H34b H 0.1267 -0.3305 0.2477 0.029 Uiso 1 1 d R . . H34c H 0.1296 -0.2047 0.1556 0.029 Uiso 1 1 d R . . O2 O 0.23041(13) 0.3751(5) 0.1919(4) 0.0256(11) Uani 1 1 d . . . H H 0.2086 0.3739 0.1588 0.038 Uiso 1 1 d R . . Ha H 0.2283 0.4208 0.2601 0.038 Uiso 1 1 d R . . O3 O 0.24649(16) 0.6072(6) 0.0445(5) 0.0333(13) Uani 1 1 d . . . Hb H 0.2427 0.5553 0.1114 0.050 Uiso 1 1 d R . . Hc H 0.2656 0.5740 0.0033 0.050 Uiso 1 1 d R . . O4 O 0.20881(16) 0.4413(7) 0.4138(5) 0.0410(15) Uani 1 1 d . . . Hd H 0.1831 0.4409 0.4373 0.062 Uiso 1 1 d R . . He H 0.2150 0.3564 0.3828 0.062 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 Cu1 0.0093(4) 0.0170(4) 0.0081(4) -0.0013(3) -0.0005(3) 0.0011(3) O1 0.019(2) 0.016(2) 0.010(2) 0.0003(18) 0.0005(17) -0.0030(18) O11 0.012(2) 0.021(2) 0.009(2) -0.0021(18) -0.0021(17) -0.0013(19) O12 0.022(2) 0.021(3) 0.012(2) 0.0033(19) 0.0021(19) 0.005(2) O21 0.007(2) 0.016(2) 0.011(2) -0.0005(17) -0.0001(16) -0.0009(16) O22 0.015(2) 0.019(2) 0.009(2) -0.0049(18) -0.0041(18) 0.0020(18) N3 0.013(2) 0.016(3) 0.003(2) 0.002(2) 0.0015(19) -0.001(2) N9 0.013(2) 0.015(3) 0.012(3) -0.001(2) -0.002(2) 0.002(2) N10 0.011(2) 0.014(3) 0.004(2) 0.001(2) -0.0026(19) 0.0002(19) C2 0.015(3) 0.015(3) 0.008(3) -0.001(2) -0.004(2) -0.001(2) C1 0.020(3) 0.020(3) 0.015(3) -0.003(3) 0.003(3) -0.004(3) C6 0.011(3) 0.020(3) 0.013(3) 0.006(3) -0.001(2) -0.002(3) C5 0.015(3) 0.012(3) 0.012(3) 0.006(2) -0.001(2) 0.001(2) C4 0.012(3) 0.010(3) 0.009(3) 0.001(2) 0.001(2) 0.001(2) C8 0.024(4) 0.013(3) 0.015(3) 0.000(3) -0.002(3) 0.004(3) C7 0.012(3) 0.023(4) 0.012(3) 0.001(3) 0.003(2) 0.004(3) C11 0.019(3) 0.016(3) 0.011(3) 0.003(3) 0.007(3) -0.001(2) C12 0.021(3) 0.009(3) 0.007(3) 0.000(2) -0.001(2) -0.001(2) C21 0.010(3) 0.013(3) 0.008(3) -0.002(2) -0.003(2) 0.001(2) C22 0.012(3) 0.009(3) 0.015(3) 0.002(2) 0.002(2) 0.000(2) C31 0.016(3) 0.017(3) 0.009(3) -0.004(3) -0.002(3) 0.002(2) C32 0.025(4) 0.016(3) 0.011(3) 0.003(3) 0.000(3) 0.002(3) C33 0.022(3) 0.017(3) 0.019(4) -0.001(3) 0.002(3) 0.006(3) C34 0.030(4) 0.015(3) 0.014(3) -0.003(3) 0.003(3) 0.000(3) O2 0.017(2) 0.038(3) 0.021(3) -0.003(2) -0.003(2) 0.000(2) O3 0.029(3) 0.038(3) 0.033(3) 0.009(2) -0.003(2) -0.003(3) O4 0.032(3) 0.064(4) 0.027(3) -0.007(3) 0.007(2) 0.010(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 2.302(5) . y Cu1 O11 1.926(4) . y Cu1 O21 1.922(4) . y Cu1 N3 1.972(5) . y Cu1 N10 2.027(5) . y O1 H1a 0.9673 . ? O1 H1b 0.8325 . ? O11 C12 1.276(7) . ? O12 C12 1.237(7) . ? O21 C22 1.270(7) . ? O22 C22 1.238(7) . ? N3 C2 1.344(8) . ? N3 C4 1.329(8) . ? N9 H9 0.8989 . ? N9 C4 1.355(8) . ? N9 C8 1.369(8) . ? N10 C11 1.491(7) . ? N10 C21 1.487(7) . ? N10 C31 1.520(8) . ? C2 H2 0.9500 . ? C2 C1 1.395(9) . ? C1 H1 0.9500 . ? C1 C6 1.375(9) . ? C6 H6 0.9500 . ? C6 C5 1.393(9) . ? C5 C4 1.413(8) . ? C5 C7 1.423(9) . ? C8 H8 0.9500 . ? C8 C7 1.351(9) . ? C7 H7 0.9500 . ? C11 H11a 0.9900 . ? C11 H11b 0.9900 . ? C11 C12 1.520(9) . ? C21 H21a 0.9900 . ? C21 H21b 0.9900 . ? C21 C22 1.519(8) . ? C31 C32 1.514(9) . ? C31 C33 1.529(8) . ? C31 C34 1.524(9) . ? C32 H32a 0.9800 . ? C32 H32b 0.9800 . ? C32 H32c 0.9800 . ? C33 H33a 0.9800 . ? C33 H33b 0.9800 . ? C33 H33c 0.9800 . ? C34 H34a 0.9800 . ? C34 H34b 0.9800 . ? C34 H34c 0.9800 . ? O2 H 0.8370 . ? O2 Ha 0.8949 . ? O3 Hb 0.9193 . ? O3 Hc 0.8669 . ? O4 Hd 0.9228 . ? O4 He 0.9098 . ? 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 O11 Cu1 O1 86.87(17) . . y O11 Cu1 N3 95.34(18) . . y O11 Cu1 N10 87.10(19) . . y O21 Cu1 O1 87.33(17) . . y O21 Cu1 O11 170.06(18) . . y O21 Cu1 N3 93.84(18) . . y O21 Cu1 N10 85.89(18) . . y N3 Cu1 O1 103.12(19) . . y N3 Cu1 N10 157.4(2) . . y N10 Cu1 O1 99.44(18) . . y Cu1 O1 H1a 123.0 . . ? Cu1 O1 H1b 121.7 . . ? H1a O1 H1b 107.6 . . ? C12 O11 Cu1 111.5(4) . . ? C22 O21 Cu1 113.0(4) . . ? C2 N3 Cu1 120.3(4) . . ? C4 N3 Cu1 124.0(4) . . ? C4 N3 C2 115.7(5) . . ? C4 N9 H9 128.1 . . ? C4 N9 C8 108.5(5) . . ? C8 N9 H9 122.6 . . ? C11 N10 Cu1 101.5(4) . . ? C11 N10 C31 113.1(5) . . ? C21 N10 Cu1 101.7(3) . . ? C21 N10 C11 113.9(5) . . ? C21 N10 C31 111.4(5) . . ? C31 N10 Cu1 114.4(4) . . ? N3 C2 H2 118.3 . . ? N3 C2 C1 123.4(6) . . ? C1 C2 H2 118.3 . . ? C2 C1 H1 119.9 . . ? C6 C1 C2 120.3(6) . . ? C6 C1 H1 119.9 . . ? C1 C6 H6 121.2 . . ? C1 C6 C5 117.7(6) . . ? C5 C6 H6 121.2 . . ? C6 C5 C4 117.8(6) . . ? C6 C5 C7 136.1(6) . . ? C4 C5 C7 106.1(5) . . ? N3 C4 N9 126.8(5) . . ? N3 C4 C5 125.0(6) . . ? N9 C4 C5 108.2(5) . . ? N9 C8 H8 124.9 . . ? C7 C8 N9 110.3(6) . . ? C7 C8 H8 124.8 . . ? C5 C7 H7 126.5 . . ? C8 C7 C5 106.9(6) . . ? C8 C7 H7 126.6 . . ? N10 C11 H11a 109.2 . . ? N10 C11 H11b 109.2 . . ? N10 C11 C12 111.9(5) . . ? H11a C11 H11b 107.9 . . ? C12 C11 H11a 109.2 . . ? C12 C11 H11b 109.2 . . ? O11 C12 C11 118.3(5) . . ? O12 C12 O11 124.4(6) . . ? O12 C12 C11 117.3(6) . . ? N10 C21 H21a 109.5 . . ? N10 C21 H21b 109.5 . . ? N10 C21 C22 110.9(5) . . ? H21a C21 H21b 108.0 . . ? C22 C21 H21a 109.5 . . ? C22 C21 H21b 109.5 . . ? O21 C22 C21 117.2(5) . . ? O22 C22 O21 123.1(6) . . ? O22 C22 C21 119.7(5) . . ? N10 C31 C33 111.1(5) . . ? N10 C31 C34 108.8(5) . . ? C32 C31 N10 110.3(5) . . ? C32 C31 C33 109.0(5) . . ? C32 C31 C34 108.3(5) . . ? C34 C31 C33 109.3(5) . . ? C31 C32 H32a 109.5 . . ? C31 C32 H32b 109.5 . . ? C31 C32 H32c 109.5 . . ? H32a C32 H32b 109.5 . . ? H32a C32 H32c 109.5 . . ? H32b C32 H32c 109.5 . . ? C31 C33 H33a 109.5 . . ? C31 C33 H33b 109.5 . . ? C31 C33 H33c 109.5 . . ? H33a C33 H33b 109.5 . . ? H33a C33 H33c 109.5 . . ? H33b C33 H33c 109.5 . . ? C31 C34 H34a 109.5 . . ? C31 C34 H34b 109.5 . . ? C31 C34 H34c 109.5 . . ? H34a C34 H34b 109.5 . . ? H34a C34 H34c 109.5 . . ? H34b C34 H34c 109.5 . . ? H O2 Ha 109.1 . . ? Hb O3 Hc 111.0 . . ? Hd O4 He 109.4 . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O1 H1a O12 0.97 1.86 2.799(6) 162.5 8_566 O1 H1b O22 0.83 2.03 2.828(6) 159.2 8_565 N9 H9 O11 0.90 2.56 3.202(7) 129.1 8_566 N9 H9 O21 0.90 2.29 2.884(7) 123.2 . O2 H O22 0.84 1.88 2.718(6) 176.5 8_565 O2 Ha O4 0.89 1.89 2.712(7) 152.4 . O3 Hb O2 0.92 2.00 2.839(7) 151.3 . O3 Hc O4 0.87 1.85 2.663(8) 155.4 7_655 O4 Hd O12 0.92 1.86 2.786(7) 177.8 8_566 O4 He O2 0.91 2.25 2.712(7) 111.2 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cu1 O11 C12 O12 -171.8(5) . . . . ? Cu1 O11 C12 C11 5.3(7) . . . . ? Cu1 O21 C22 O22 177.6(5) . . . . ? Cu1 O21 C22 C21 -1.7(7) . . . . ? Cu1 N3 C2 C1 -177.9(5) . . . . ? Cu1 N3 C4 N9 -2.6(9) . . . . ? Cu1 N3 C4 C5 176.0(5) . . . . ? Cu1 N10 C11 C12 -30.1(5) . . . . ? Cu1 N10 C21 C22 33.6(5) . . . . ? Cu1 N10 C31 C32 -67.3(5) . . . . ? Cu1 N10 C31 C33 171.7(4) . . . . ? Cu1 N10 C31 C34 51.3(6) . . . . ? O1 Cu1 O11 C12 80.3(4) . . . . ? O1 Cu1 O21 C22 -81.5(4) . . . . ? O1 Cu1 N3 C2 134.8(4) . . . . ? O1 Cu1 N3 C4 -44.8(5) . . . . ? O1 Cu1 N10 C11 -59.4(4) . . . . ? O1 Cu1 N10 C21 58.2(3) . . . . ? O1 Cu1 N10 C31 178.4(4) . . . . ? O11 Cu1 O21 C22 -27.1(13) . . . . ? O11 Cu1 N3 C2 46.8(5) . . . . ? O11 Cu1 N3 C4 -132.9(5) . . . . ? O11 Cu1 N10 C11 26.9(4) . . . . ? O11 Cu1 N10 C21 144.6(4) . . . . ? O11 Cu1 N10 C31 -95.2(4) . . . . ? O21 Cu1 O11 C12 25.8(13) . . . . ? O21 Cu1 N3 C2 -137.0(4) . . . . ? O21 Cu1 N3 C4 43.3(5) . . . . ? O21 Cu1 N10 C11 -146.0(4) . . . . ? O21 Cu1 N10 C21 -28.4(3) . . . . ? O21 Cu1 N10 C31 91.8(4) . . . . ? N3 Cu1 O11 C12 -176.8(4) . . . . ? N3 Cu1 O21 C22 175.6(4) . . . . ? N3 Cu1 N10 C11 123.8(5) . . . . ? N3 Cu1 N10 C21 -118.5(5) . . . . ? N3 Cu1 N10 C31 1.7(7) . . . . ? N3 C2 C1 C6 0.6(10) . . . . ? N9 C8 C7 C5 1.4(7) . . . . ? N10 Cu1 O11 C12 -19.4(4) . . . . ? N10 Cu1 O21 C22 18.2(4) . . . . ? N10 Cu1 N3 C2 -48.5(7) . . . . ? N10 Cu1 N3 C4 131.9(6) . . . . ? N10 C11 C12 O11 18.9(8) . . . . ? N10 C11 C12 O12 -163.8(5) . . . . ? N10 C21 C22 O21 -23.8(7) . . . . ? N10 C21 C22 O22 156.9(5) . . . . ? C2 N3 C4 N9 177.7(6) . . . . ? C2 N3 C4 C5 -3.7(9) . . . . ? C2 C1 C6 C5 -1.2(9) . . . . ? C1 C6 C5 C4 -0.5(9) . . . . ? C1 C6 C5 C7 -178.5(7) . . . . ? C6 C5 C4 N3 3.1(9) . . . . ? C6 C5 C4 N9 -178.1(5) . . . . ? C6 C5 C7 C8 177.0(7) . . . . ? C4 N3 C2 C1 1.8(9) . . . . ? C4 N9 C8 C7 -1.1(7) . . . . ? C4 C5 C7 C8 -1.2(7) . . . . ? C8 N9 C4 N3 179.1(6) . . . . ? C8 N9 C4 C5 0.3(7) . . . . ? C7 C5 C4 N3 -178.3(6) . . . . ? C7 C5 C4 N9 0.5(7) . . . . ? C11 N10 C21 C22 141.9(5) . . . . ? C11 N10 C31 C32 177.2(5) . . . . ? C11 N10 C31 C33 56.2(6) . . . . ? C11 N10 C31 C34 -64.2(6) . . . . ? C21 N10 C11 C12 -138.5(5) . . . . ? C21 N10 C31 C32 47.3(6) . . . . ? C21 N10 C31 C33 -73.7(6) . . . . ? C21 N10 C31 C34 165.9(5) . . . . ? C31 N10 C11 C12 92.9(6) . . . . ? C31 N10 C21 C22 -88.6(6) . . . . ? data_C554_Comp.2 _database_code_depnum_ccdc_archive 'CCDC 881137' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C36 H32 Cu2 F2 N6 O8, 2(H2 O)' _chemical_formula_sum 'C36 H36 Cu2 F2 N6 O10' _chemical_formula_weight 877.79 _chemical_melting_point ? 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _cell_length_a 37.308(8) _cell_length_b 8.0550(16) _cell_length_c 25.933(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.42(3) _cell_angle_gamma 90.00 _cell_volume 7255(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used ? _cell_measurement_temperature 100(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 1.251 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.607 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 3600 _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_max 47 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 7667 _diffrn_reflns_theta_full 28.14 _diffrn_reflns_theta_max 28.14 _diffrn_reflns_theta_min 2.43 _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9.6 _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measurement_device_type 'Single-axis HUBER diffractometer' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_radiation_detector 'ADSC Q210r CCD (binned mode)' _diffrn_radiation_monochromator 'Si 111' _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.7380 _diffrn_source synchrotron _diffrn_source_type 'ESRF-CRG BM16' _reflns_number_gt 6108 _reflns_number_total 7667 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_collection 'MxCube (ESRF, 2006)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.057 _refine_diff_density_min -1.306 _refine_diff_density_rms 0.094 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.023 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 505 _refine_ls_number_reflns 7667 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0564 _refine_ls_R_factor_gt 0.0432 _refine_ls_restrained_S_all 1.023 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0657P)^2^+13.6398P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1133 _refine_ls_wR_factor_ref 0.1209 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.609909(9) 0.49700(4) 0.753185(12) 0.01535(10) Uani 1 1 d . . . Cu2 Cu 0.612736(9) 0.99224(4) 0.869901(12) 0.01462(10) Uani 1 1 d . . . N10 N 0.56445(6) 0.5856(3) 0.68970(8) 0.0183(5) Uani 1 1 d . . . C11 C 0.54374(7) 0.6868(3) 0.71754(10) 0.0211(6) Uani 1 1 d . . . H11a H 0.5262 0.6152 0.7286 0.025 Uiso 1 1 calc R . . H11b H 0.5281 0.7726 0.6918 0.025 Uiso 1 1 calc R . . C12 C 0.57296(7) 0.7697(3) 0.76884(10) 0.0188(5) Uani 1 1 d . . . O2 O 0.50324(7) 0.8703(5) 0.03557(10) 0.0755(11) Uani 1 1 d . . . O11 O 0.60622(5) 0.7034(2) 0.78902(7) 0.0197(4) Uani 1 1 d . . . O12 O 0.56315(6) 0.8930(2) 0.78884(7) 0.0244(4) Uani 1 1 d . . . C21 C 0.54394(8) 0.4345(3) 0.66119(11) 0.0214(6) Uani 1 1 d . . . H21a H 0.5309 0.4580 0.6212 0.026 Uiso 1 1 calc R . . H21b H 0.5240 0.4040 0.6763 0.026 Uiso 1 1 calc R . . C22 C 0.57167(8) 0.2891(3) 0.66873(10) 0.0205(6) Uani 1 1 d . . . O21 O 0.60477(5) 0.3011(2) 0.70793(7) 0.0197(4) Uani 1 1 d . . . O22 O 0.56057(6) 0.1650(3) 0.63920(8) 0.0295(5) Uani 1 1 d . . . C31 C 0.57571(9) 0.6971(3) 0.65174(11) 0.0243(6) Uani 1 1 d . . . H31a H 0.5523 0.7268 0.6198 0.029 Uiso 1 1 calc R . . H31b H 0.5866 0.8010 0.6718 0.029 Uiso 1 1 calc R . . C32 C 0.60440(8) 0.6226(3) 0.63056(10) 0.0223(6) Uani 1 1 d . . . C33 C 0.59279(8) 0.5498(4) 0.57825(11) 0.0232(6) Uani 1 1 d . . . H33 H 0.5661 0.5421 0.5565 0.028 Uiso 1 1 calc R . . C34 C 0.61958(9) 0.4884(4) 0.55748(12) 0.0270(7) Uani 1 1 d . . . H34 H 0.6117 0.4377 0.5220 0.032 Uiso 1 1 calc R . . C35 C 0.65790(9) 0.5034(4) 0.58994(12) 0.0312(7) Uani 1 1 d . . . F35 F 0.68456(5) 0.4483(3) 0.56942(7) 0.0476(5) Uani 1 1 d . . . C36 C 0.67079(9) 0.5716(5) 0.64188(12) 0.0364(8) Uani 1 1 d . . . H36 H 0.6975 0.5778 0.6634 0.044 Uiso 1 1 calc R . . C37 C 0.64364(9) 0.6311(4) 0.66211(11) 0.0303(7) Uani 1 1 d . . . H37 H 0.6519 0.6785 0.6981 0.036 Uiso 1 1 calc R . . C5 C 0.70717(8) 0.3821(3) 0.89969(10) 0.0205(5) Uani 1 1 d . . . C3 C 0.73287(8) 0.3076(3) 0.87925(11) 0.0232(6) Uani 1 1 d . . . H3 H 0.7559 0.2568 0.9033 0.028 Uiso 1 1 calc R . . C4 C 0.72371(8) 0.3103(3) 0.82260(11) 0.0229(6) Uani 1 1 d . . . H4 H 0.7414 0.2661 0.8075 0.027 Uiso 1 1 calc R . . C7 C 0.68910(8) 0.3766(3) 0.78757(11) 0.0210(6) Uani 1 1 d . . . H7 H 0.6835 0.3728 0.7488 0.025 Uiso 1 1 calc R . . N3 N 0.66309(6) 0.4460(3) 0.80569(8) 0.0163(4) Uani 1 1 d . . . C8 C 0.67306(7) 0.4516(3) 0.86089(10) 0.0161(5) Uani 1 1 d . . . N9 N 0.65209(7) 0.5192(3) 0.88860(9) 0.0185(5) Uani 1 1 d . . . H9 H 0.6316 0.5883 0.8758 0.022 Uiso 1 1 d R . . C9 C 0.67207(9) 0.4964(3) 0.94427(11) 0.0235(6) Uani 1 1 d . . . H9a H 0.6637 0.5343 0.9727 0.028 Uiso 1 1 calc R . . C15 C 0.70537(9) 0.4126(4) 0.95322(11) 0.0267(6) Uani 1 1 d . . . H15 H 0.7238 0.3804 0.9880 0.032 Uiso 1 1 calc R . . N10A N 0.56973(6) 1.0815(3) 0.89125(9) 0.0177(5) Uani 1 1 d . . . C21A C 0.54936(7) 0.9304(3) 0.89857(11) 0.0202(5) Uani 1 1 d . . . H21c H 0.5278 0.9055 0.8635 0.024 Uiso 1 1 calc R . . H21d H 0.5384 0.9513 0.9274 0.024 Uiso 1 1 calc R . . C22A C 0.57625(8) 0.7812(3) 0.91532(10) 0.0202(5) Uani 1 1 d . . . O21A O 0.60877(5) 0.7934(2) 0.90921(7) 0.0178(4) Uani 1 1 d . . . O22A O 0.56543(6) 0.6543(2) 0.93219(8) 0.0289(5) Uani 1 1 d . . . C11A C 0.54777(7) 1.1897(3) 0.84419(11) 0.0212(6) Uani 1 1 d . . . H11c H 0.5345 1.2777 0.8571 0.025 Uiso 1 1 calc R . . H11d H 0.5280 1.1234 0.8156 0.025 Uiso 1 1 calc R . . C12A C 0.57509(8) 0.2687(3) 0.81919(10) 0.0206(5) Uani 1 1 d . . . O12A O 0.56429(6) 0.3915(2) 0.78911(8) 0.0249(4) Uani 1 1 d . . . O11A O 0.60794(5) 1.1996(2) 0.83050(7) 0.0186(4) Uani 1 1 d . . . C31A C 0.58389(8) 1.1866(3) 0.94236(11) 0.0226(6) Uani 1 1 d . . . H31c H 0.5615 1.2265 0.9506 0.027 Uiso 1 1 calc R . . H31d H 0.5972 1.2851 0.9350 0.027 Uiso 1 1 calc R . . C32A C 0.61103(8) 1.0979(3) 0.99257(11) 0.0210(6) Uani 1 1 d . . . C37A C 0.65018(8) 1.0858(4) 1.00205(12) 0.0261(6) Uani 1 1 d . . . H37A H 0.6599 1.1338 0.9763 0.031 Uiso 1 1 calc R . . C36A C 0.67515(9) 1.0051(4) 1.04819(13) 0.0281(7) Uani 1 1 d . . . H36A H 0.7018 0.9961 1.0545 0.034 Uiso 1 1 calc R . . C35A C 0.66002(8) 0.9378(4) 1.08483(11) 0.0278(6) Uani 1 1 d . . . F35A F 0.68469(5) 0.8615(3) 1.13113(7) 0.0407(5) Uani 1 1 d . . . C34A C 0.62191(8) 0.9468(4) 1.07740(11) 0.0253(6) Uani 1 1 d . . . H34A H 0.6126 0.8990 1.1036 0.030 Uiso 1 1 calc R . . C33A C 0.59722(8) 1.0273(4) 1.03079(11) 0.0224(6) Uani 1 1 d . . . H33A H 0.5706 1.0345 1.0248 0.027 Uiso 1 1 calc R . . C5A C 0.70613(8) 0.8929(3) 0.81578(11) 0.0213(6) Uani 1 1 d . . . C6A C 0.73370(8) 0.8194(4) 0.86158(12) 0.0259(6) Uani 1 1 d . . . H6A H 0.7568 0.7758 0.8595 0.031 Uiso 1 1 calc R . . O1 O 0.50524(8) 0.3771(5) 0.46847(10) 0.0719(10) Uani 1 1 d . . . C1A C 0.72666(8) 0.8114(4) 0.91007(12) 0.0260(6) Uani 1 1 d . . . H1A H 0.7454 0.7650 0.9424 0.031 Uiso 1 1 calc R . . C2A C 0.69217(7) 0.8709(3) 0.91191(11) 0.0206(5) Uani 1 1 d . . . H2A H 0.6879 0.8614 0.9457 0.025 Uiso 1 1 calc R . . N3A N 0.66449(6) 0.9414(3) 0.86838(8) 0.0153(4) Uani 1 1 d . . . C4A C 0.67242(7) 0.9546(3) 0.82200(10) 0.0161(5) Uani 1 1 d . . . N9A N 0.64966(7) 1.0241(3) 0.77364(9) 0.0191(5) Uani 1 1 d . . . H9Aa H 0.6285 1.0885 0.7693 0.023 Uiso 1 1 d R . . C8A C 0.66840(9) 1.0107(3) 0.73645(12) 0.0249(6) Uani 1 1 d . . . H8A H 0.6588 1.0521 0.6996 0.030 Uiso 1 1 calc R . . C7A C 0.70233(9) 0.9307(4) 0.76002(12) 0.0278(6) Uani 1 1 d . . . H7A H 0.7202 0.9045 0.7429 0.033 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.01948(18) 0.0146(2) 0.01055(16) -0.00017(11) 0.00374(13) 0.00008(11) Cu2 0.01793(17) 0.01370(19) 0.01539(17) 0.00229(11) 0.00982(13) 0.00146(11) N10 0.0255(11) 0.0158(12) 0.0112(10) 0.0003(8) 0.0038(8) -0.0020(9) C11 0.0250(14) 0.0213(15) 0.0192(13) -0.0022(11) 0.0112(11) -0.0029(11) C11 0.0223(13) 0.0214(15) 0.0164(12) -0.0002(10) 0.0034(10) 0.0043(11) C12 0.0265(14) 0.0169(14) 0.0128(11) 0.0027(10) 0.0068(10) 0.0002(10) C12 0.0291(15) 0.0252(15) 0.0125(12) 0.0031(11) 0.0041(11) -0.0028(12) O2 0.0386(15) 0.162(3) 0.0280(13) 0.0181(17) 0.0152(11) 0.0387(18) O11 0.0233(9) 0.0205(10) 0.0136(8) -0.0026(7) 0.0046(7) -0.0014(7) O12 0.0326(11) 0.0206(11) 0.0187(9) -0.0015(8) 0.0078(8) 0.0048(8) C21 0.0236(13) 0.0195(15) 0.0151(12) -0.0001(10) 0.0001(10) -0.0034(11) C21 0.0195(13) 0.0193(15) 0.0266(14) 0.0009(11) 0.0035(11) -0.0009(11) C22 0.0343(16) 0.0260(17) 0.0143(12) 0.0038(11) 0.0026(11) -0.0002(12) C22 0.0317(14) 0.0162(14) 0.0156(12) 0.0001(10) 0.0110(11) -0.0035(11) O21 0.0245(9) 0.0186(10) 0.0147(8) 0.0001(7) 0.0054(7) 0.0001(7) O22 0.0379(12) 0.0219(11) 0.0257(10) -0.0090(8) 0.0082(9) -0.0055(9) C31 0.0410(16) 0.0153(14) 0.0153(12) 0.0050(10) 0.0090(11) -0.0002(12) C32 0.0363(15) 0.0157(14) 0.0130(12) 0.0047(10) 0.0067(11) -0.0054(11) C34 0.0344(16) 0.0320(18) 0.0137(13) 0.0035(11) 0.0078(11) -0.0011(12) C35 0.0343(17) 0.044(2) 0.0192(14) 0.0129(12) 0.0145(13) -0.0001(13) F35 0.0344(10) 0.0894(16) 0.0233(9) 0.0185(10) 0.0159(8) 0.0098(10) C36 0.0277(15) 0.060(2) 0.0187(14) 0.0116(14) 0.0049(12) -0.0148(15) C37 0.0398(17) 0.0349(18) 0.0131(12) 0.0019(11) 0.0059(12) -0.0166(13) C5 0.0251(14) 0.0160(14) 0.0176(12) 0.0016(10) 0.0046(10) -0.0018(10) C4 0.0210(13) 0.0219(15) 0.0287(14) -0.0018(11) 0.0125(11) -0.0007(11) N3 0.0194(11) 0.0159(11) 0.0141(10) 0.0002(8) 0.0065(8) -0.0003(8) C8 0.0210(13) 0.0132(13) 0.0134(11) -0.0005(9) 0.0055(10) -0.0017(10) N9 0.0254(12) 0.0162(12) 0.0145(10) -0.0008(8) 0.0079(9) 0.0031(9) C9 0.0374(16) 0.0213(16) 0.0121(12) 0.0005(10) 0.0095(11) -0.0012(11) N10A 0.0218(11) 0.0171(12) 0.0176(10) 0.0029(9) 0.0113(9) 0.0024(9) C21A 0.0222(13) 0.0206(15) 0.0216(13) 0.0027(11) 0.0125(11) -0.0016(11) C22A 0.0265(14) 0.0210(15) 0.0150(12) -0.0006(10) 0.0100(10) -0.0017(11) O21A 0.0234(9) 0.0165(10) 0.0161(8) 0.0016(7) 0.0102(7) 0.0019(7) O22A 0.0367(12) 0.0217(11) 0.0344(11) 0.0099(9) 0.0202(9) -0.0024(8) C11A 0.0217(13) 0.0208(15) 0.0240(13) 0.0067(11) 0.0120(11) 0.0069(11) C12A 0.0280(14) 0.0185(15) 0.0169(12) 0.0008(10) 0.0102(10) 0.0002(11) O12A 0.0312(11) 0.0213(11) 0.0253(10) 0.0088(8) 0.0141(8) 0.0055(8) O11A 0.0224(9) 0.0179(10) 0.0192(9) 0.0026(7) 0.0117(7) 0.0011(7) C31A 0.0358(15) 0.0154(14) 0.0237(14) -0.0026(11) 0.0193(12) 0.0020(11) C32A 0.0300(14) 0.0170(14) 0.0194(12) -0.0073(10) 0.0131(11) -0.0024(11) C37A 0.0317(15) 0.0264(17) 0.0263(14) -0.0116(12) 0.0177(12) -0.0087(12) C36A 0.0212(14) 0.0373(19) 0.0269(15) -0.0140(12) 0.0100(12) -0.0044(12) C35A 0.0283(15) 0.0368(18) 0.0168(13) -0.0087(12) 0.0063(11) 0.0056(13) F35A 0.0335(10) 0.0679(14) 0.0174(8) -0.0034(8) 0.0054(7) 0.0191(9) C34A 0.0302(15) 0.0325(16) 0.0158(13) -0.0033(12) 0.0116(11) 0.0022(12) C33A 0.0230(14) 0.0271(16) 0.0205(13) -0.0045(11) 0.0121(11) 0.0016(11) C5A 0.0245(13) 0.0190(14) 0.0261(14) -0.0052(11) 0.0159(11) -0.0032(11) C6A 0.0195(13) 0.0241(16) 0.0362(16) -0.0047(12) 0.0128(12) 0.0018(11) O1 0.0381(14) 0.148(3) 0.0286(13) 0.0024(17) 0.0113(11) 0.0299(17) C1A 0.0213(13) 0.0257(16) 0.0285(15) 0.0004(12) 0.0061(11) 0.0026(11) C2A 0.0231(13) 0.0199(15) 0.0183(13) -0.0002(10) 0.0069(10) -0.0010(10) N3A 0.0176(10) 0.0151(11) 0.0151(10) 0.0002(8) 0.0084(8) -0.0001(8) C4A 0.0216(13) 0.0133(13) 0.0169(12) -0.0013(10) 0.0114(10) -0.0020(10) N9A 0.0244(12) 0.0192(12) 0.0175(11) 0.0020(9) 0.0122(9) 0.0019(9) C8A 0.0372(17) 0.0246(16) 0.0196(13) -0.0038(11) 0.0186(12) -0.0055(12) C7A 0.0360(16) 0.0296(17) 0.0278(15) -0.0074(12) 0.0235(13) -0.0030(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 Cu1 N10 2.014(2) . ? Cu1 O11 1.9338(19) . ? Cu1 O21 1.9342(18) . ? Cu1 N3 1.997(2) . ? Cu1 O12A 2.376(2) . ? Cu2 O12 2.375(2) . ? Cu2 N10A 2.011(2) . ? Cu2 O21A 1.9327(18) . ? Cu2 O11A 1.9323(18) . ? Cu2 N3A 1.988(2) . ? N10 C11 1.480(3) . ? N10 C21 1.484(3) . ? N10 C31 1.502(3) . ? C11 H11a 0.9900 . ? C11 H11b 0.9900 . ? C11 C12 1.531(4) . ? C11 H7 0.9500 . ? C11 N3 1.345(3) . ? C12 O11 1.275(3) . ? C12 O12 1.236(3) . ? C12 H33 0.9500 . ? C12 C34 1.388(4) . ? C21 H21a 0.9900 . ? C21 H21b 0.9900 . ? C21 C22 1.527(4) . ? C21 H3 0.9500 . ? C21 C4 1.382(4) . ? C22 O21 1.285(3) . ? C22 O22 1.235(3) . ? C22 H15 0.9500 . ? C31 H31a 0.9900 . ? C31 H31b 0.9900 . ? C31 C32 1.496(4) . ? C32 C12 1.393(4) . ? C32 C37 1.394(4) . ? C34 H34 0.9500 . ? C34 C35 1.374(4) . ? C35 F35 1.362(4) . ? C35 C36 1.369(4) . ? C36 H36 0.9500 . ? C36 C37 1.386(5) . ? C37 H37 0.9500 . ? C5 C21 1.390(4) . ? C5 C22 1.435(4) . ? C5 C8 1.417(4) . ? C4 C11 1.386(4) . ? C4 H4 0.9500 . ? N3 C8 1.342(3) . ? C8 N9 1.355(3) . ? N9 H9 0.9056 . ? N9 C9 1.374(3) . ? C9 C22 1.358(4) . ? C9 H9a 0.9500 . ? N10A C21A 1.483(3) . ? N10A C11A 1.480(3) . ? N10A C31A 1.497(3) . ? C21A H21c 0.9900 . ? C21A H21d 0.9900 . ? C21A C22A 1.524(4) . ? C22A O21A 1.283(3) . ? C22A O22A 1.236(3) . ? C11A H11c 0.9900 . ? C11A H11d 0.9900 . ? C11A C12A 1.532(4) 1_565 ? C12A C11A 1.532(4) 1_545 ? C12A O12A 1.233(3) . ? C12A O11A 1.279(3) 1_545 ? O11A C12A 1.279(3) 1_565 ? C31A H31c 0.9900 . ? C31A H31d 0.9900 . ? C31A C32A 1.506(4) . ? C32A C37A 1.393(4) . ? C32A C33A 1.394(4) . ? C37A H37A 0.9500 . ? C37A C36A 1.381(4) . ? C36A H36A 0.9500 . ? C36A C35A 1.381(4) . ? C35A F35A 1.364(3) . ? C35A C34A 1.365(4) . ? C34A H34A 0.9500 . ? C34A C33A 1.384(4) . ? C33A H33A 0.9500 . ? C5A C6A 1.388(4) . ? C5A C4A 1.415(4) . ? C5A C7A 1.433(4) . ? C6A H6A 0.9500 . ? C6A C1A 1.377(4) . ? C1A H1A 0.9500 . ? C1A C2A 1.390(4) . ? C2A H2A 0.9500 . ? C2A N3A 1.346(3) . ? N3A C4A 1.343(3) . ? C4A N9A 1.352(3) . ? N9A H9Aa 0.9177 . ? N9A C8A 1.387(3) . ? C8A H8A 0.9500 . ? C8A C7A 1.351(4) . ? C7A H7A 0.9500 . ? 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 N10 Cu1 O12A 86.40(8) . . ? O11 Cu1 N10 84.35(8) . . ? O11 Cu1 O21 169.87(7) . . ? O11 Cu1 N3 94.40(8) . . ? O11 Cu1 O12A 86.10(7) . . ? O21 Cu1 N10 85.76(8) . . ? O21 Cu1 N3 95.70(8) . . ? O21 Cu1 O12A 91.14(7) . . ? N3 Cu1 N10 163.91(9) . . ? N3 Cu1 O12A 109.56(8) . . ? N10A Cu2 O12 85.53(8) . . ? O21A Cu2 O12 90.17(7) . . ? O21A Cu2 N10A 85.90(8) . . ? O21A Cu2 N3A 95.85(8) . . ? O11A Cu2 O12 86.06(7) . . ? O11A Cu2 N10A 84.69(8) . . ? O11A Cu2 O21A 170.11(7) . . ? O11A Cu2 N3A 94.04(8) . . ? N3A Cu2 O12 111.18(8) . . ? N3A Cu2 N10A 163.15(9) . . ? C11 N10 Cu1 103.31(15) . . ? C11 N10 C21 115.4(2) . . ? C11 N10 C31 108.1(2) . . ? C21 N10 Cu1 104.09(16) . . ? C21 N10 C31 112.4(2) . . ? C31 N10 Cu1 113.21(17) . . ? N10 C11 H11a 109.8 . . ? N10 C11 H11b 109.8 . . ? N10 C11 C12 109.3(2) . . ? H11a C11 H11b 108.3 . . ? C12 C11 H11a 109.8 . . ? C12 C11 H11b 109.8 . . ? C4 C11 H7 118.3 . . ? N3 C11 C4 123.3(2) . . ? N3 C11 H7 118.3 . . ? O11 C12 C11 116.8(2) . . ? O12 C12 C11 119.3(2) . . ? O12 C12 O11 123.9(2) . . ? C32 C12 H33 119.5 . . ? C34 C12 C32 121.1(3) . . ? C34 C12 H33 119.5 . . ? C12 O11 Cu1 113.12(16) . . ? C12 O12 Cu2 112.80(16) . . ? N10 C21 H21a 109.4 . . ? N10 C21 H21b 109.4 . . ? N10 C21 C22 111.3(2) . . ? H21a C21 H21b 108.0 . . ? C22 C21 H21a 109.4 . . ? C22 C21 H21b 109.4 . . ? C5 C21 H3 121.2 . . ? C4 C21 C5 117.5(2) . . ? C4 C21 H3 121.2 . . ? O21 C22 C21 117.0(2) . . ? O22 C22 C21 118.9(2) . . ? O22 C22 O21 124.0(3) . . ? C5 C22 H15 126.8 . . ? C9 C22 C5 106.4(2) . . ? C9 C22 H15 126.8 . . ? C22 O21 Cu1 113.26(16) . . ? N10 C31 H31a 108.7 . . ? N10 C31 H31b 108.7 . . ? H31a C31 H31b 107.6 . . ? C32 C31 N10 114.2(2) . . ? C32 C31 H31a 108.7 . . ? C32 C31 H31b 108.7 . . ? C12 C32 C31 121.1(3) . . ? C12 C32 C37 118.6(3) . . ? C37 C32 C31 120.2(2) . . ? C12 C34 H34 121.1 . . ? C35 C34 C12 117.8(3) . . ? C35 C34 H34 121.1 . . ? F35 C35 C34 118.5(3) . . ? F35 C35 C36 118.1(3) . . ? C36 C35 C34 123.5(3) . . ? C35 C36 H36 121.0 . . ? C35 C36 C37 117.9(3) . . ? C37 C36 H36 121.0 . . ? C32 C37 H37 119.4 . . ? C36 C37 C32 121.1(3) . . ? C36 C37 H37 119.4 . . ? C21 C5 C22 136.5(3) . . ? C21 C5 C8 117.7(2) . . ? C8 C5 C22 105.8(2) . . ? C11 C4 H4 119.6 . . ? C21 C4 C11 120.8(2) . . ? C21 C4 H4 119.6 . . ? C11 N3 Cu1 120.76(17) . . ? C8 N3 Cu1 122.67(17) . . ? C8 N3 C11 115.6(2) . . ? N3 C8 C5 124.8(2) . . ? N3 C8 N9 126.2(2) . . ? N9 C8 C5 108.9(2) . . ? C8 N9 H9 128.9 . . ? C8 N9 C9 107.9(2) . . ? C9 N9 H9 121.9 . . ? C22 C9 N9 111.0(3) . . ? C22 C9 H9a 124.5 . . ? N9 C9 H9a 124.5 . . ? C21A N10A Cu2 103.86(16) . . ? C21A N10A C31A 112.5(2) . . ? C11A N10A Cu2 103.93(15) . . ? C11A N10A C21A 115.7(2) . . ? C11A N10A C31A 107.9(2) . . ? C31A N10A Cu2 112.76(16) . . ? N10A C21A H21c 109.3 . . ? N10A C21A H21d 109.3 . . ? N10A C21A C22A 111.7(2) . . ? H21c C21A H21d 108.0 . . ? C22A C21A H21c 109.3 . . ? C22A C21A H21d 109.3 . . ? O21A C22A C21A 117.2(2) . . ? O22A C22A C21A 119.1(2) . . ? O22A C22A O21A 123.6(3) . . ? C22A O21A Cu2 112.77(16) . . ? N10A C11A H11c 109.7 . . ? N10A C11A H11d 109.7 . . ? N10A C11A C12A 109.9(2) . 1_565 ? H11c C11A H11d 108.2 . . ? C12A C11A H11c 109.7 1_565 . ? C12A C11A H11d 109.7 1_565 . ? O12A C12A C11A 119.1(2) . 1_545 ? O12A C12A O11A 124.0(2) . 1_545 ? O11A C12A C11A 116.9(2) 1_545 1_545 ? C12A O12A Cu1 114.81(17) . . ? C12A O11A Cu2 113.16(16) 1_565 . ? N10A C31A H31c 108.8 . . ? N10A C31A H31d 108.8 . . ? N10A C31A C32A 113.9(2) . . ? H31c C31A H31d 107.7 . . ? C32A C31A H31c 108.8 . . ? C32A C31A H31d 108.8 . . ? C37A C32A C31A 121.1(2) . . ? C37A C32A C33A 118.8(3) . . ? C33A C32A C31A 120.1(2) . . ? C32A C37A H37A 119.4 . . ? C36A C37A C32A 121.2(3) . . ? C36A C37A H37A 119.4 . . ? C37A C36A H36A 121.1 . . ? C35A C36A C37A 117.7(3) . . ? C35A C36A H36A 121.1 . . ? F35A C35A C36A 117.9(3) . . ? F35A C35A C34A 118.8(3) . . ? C34A C35A C36A 123.3(3) . . ? C35A C34A H34A 120.8 . . ? C35A C34A C33A 118.3(3) . . ? C33A C34A H34A 120.8 . . ? C32A C33A H33A 119.6 . . ? C34A C33A C32A 120.7(3) . . ? C34A C33A H33A 119.6 . . ? C6A C5A C4A 117.6(2) . . ? C6A C5A C7A 136.3(3) . . ? C4A C5A C7A 106.0(2) . . ? C5A C6A H6A 120.9 . . ? C1A C6A C5A 118.2(2) . . ? C1A C6A H6A 120.9 . . ? C6A C1A H1A 119.9 . . ? C6A C1A C2A 120.2(3) . . ? C2A C1A H1A 119.9 . . ? C1A C2A H2A 118.2 . . ? N3A C2A C1A 123.6(2) . . ? N3A C2A H2A 118.2 . . ? C2A N3A Cu2 121.55(17) . . ? C4A N3A Cu2 122.31(17) . . ? C4A N3A C2A 115.6(2) . . ? N3A C4A C5A 124.7(2) . . ? N3A C4A N9A 126.4(2) . . ? N9A C4A C5A 108.8(2) . . ? C4A N9A H9Aa 124.7 . . ? C4A N9A C8A 107.9(2) . . ? C8A N9A H9Aa 126.0 . . ? N9A C8A H8A 124.8 . . ? C7A C8A N9A 110.4(3) . . ? C7A C8A H8A 124.8 . . ? C5A C7A H7A 126.6 . . ? C8A C7A C5A 106.8(2) . . ? C8A C7A H7A 126.6 . . ? 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 N9 H9 O11 0.91 2.30 2.928(3) 126.7 . N9 H9 O21A 0.91 2.18 2.900(3) 136.2 . N9A H9Aa O21 0.92 2.28 2.933(3) 127.4 1_565 N9A H9Aa O11A 0.92 2.19 2.876(3) 130.9 . data_C482_Comp.3 _database_code_depnum_ccdc_archive 'CCDC 881138' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H15 Cl Cu N4 O4, 2(H2 O)' _chemical_formula_sum 'C17 H19 Cl Cu N4 O6' _chemical_formula_weight 474.35 _chemical_melting_point ? 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' 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' 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _symmetry_cell_setting Monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _cell_length_a 13.418(4) _cell_length_b 7.707(2) _cell_length_c 19.083(5) _cell_angle_alpha 90.00 _cell_angle_beta 106.648(13) _cell_angle_gamma 90.00 _cell_volume 1890.7(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 1874 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 19.612 _cell_measurement_theta_min 2.335 _exptl_absorpt_coefficient_mu 1.341 _exptl_absorpt_correction_T_max 0.9867 _exptl_absorpt_correction_T_min 0.6585 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 972 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.01 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0981 _diffrn_reflns_av_sigmaI/netI 0.1382 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 20471 _diffrn_reflns_theta_full 27.26 _diffrn_reflns_theta_max 27.26 _diffrn_reflns_theta_min 1.58 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker X8 KappaAPEXII' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _reflns_number_gt 4310 _reflns_number_total 4314 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'APEX2 Software (Bruker, 2005)' _computing_data_collection 'APEX2 Software (Bruker, 2005)' _computing_data_reduction 'APEX2 Software (Bruker, 2005)' _computing_molecular_graphics 'PLATON (Spek, 2004)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.536 _refine_diff_density_min -1.771 _refine_diff_density_rms 0.149 _refine_ls_extinction_coef 0.0021(13) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 263 _refine_ls_number_reflns 4314 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0896 _refine_ls_R_factor_gt 0.0722 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0121P)^2^+0.0347P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1945 _refine_ls_wR_factor_ref 0.2107 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.02567(5) 0.19919(7) 0.14603(3) 0.0255(3) Uani 1 1 d . . . Cl1 Cl 0.33535(12) 0.38694(16) -0.07407(8) 0.0358(4) Uani 1 1 d . . . O11 O 0.0867(3) 0.4251(4) 0.1378(2) 0.0276(8) Uani 1 1 d . . . O12 O 0.2201(3) 0.5903(4) 0.1937(2) 0.0305(8) Uani 1 1 d . . . O21 O -0.0070(3) -0.0414(4) 0.1638(2) 0.0275(8) Uani 1 1 d . . . O22 O 0.0317(3) -0.2275(4) 0.2575(2) 0.0271(8) Uani 1 1 d . . . N10 N 0.1624(3) 0.1448(5) 0.2165(2) 0.0220(8) Uani 1 1 d . . . N3 N -0.3601(4) 0.2303(5) -0.0426(3) 0.0284(9) Uani 1 1 d . . . N7 N -0.0941(3) 0.2399(5) 0.0618(2) 0.0205(8) Uani 1 1 d . . . N9 N -0.1883(4) 0.3034(5) -0.0520(3) 0.0294(10) Uani 1 1 d . . . H9A H -0.2036 0.3379 -0.0978 0.035 Uiso 1 1 calc R . . C1 C -0.3536(4) 0.1360(7) 0.0798(3) 0.0304(11) Uani 1 1 d . . . H1 H -0.3919 0.0995 0.1120 0.036 Uiso 1 1 calc R . . C2 C -0.4066(5) 0.1721(7) 0.0062(4) 0.0332(12) Uani 1 1 d . . . H2 H -0.4797 0.1542 -0.0097 0.040 Uiso 1 1 calc R . . C4 C -0.2567(4) 0.2471(6) -0.0152(3) 0.0248(9) Uani 1 1 d . . . C5 C -0.1969(4) 0.2110(6) 0.0559(3) 0.0271(10) Uani 1 1 d . . . C6 C -0.2484(4) 0.1525(6) 0.1055(3) 0.0261(10) Uani 1 1 d . . . H6 H -0.2118 0.1256 0.1547 0.031 Uiso 1 1 calc R . . C8 C -0.0944(4) 0.2950(6) -0.0043(3) 0.0256(10) Uani 1 1 d . . . H8 H -0.0328 0.3257 -0.0164 0.031 Uiso 1 1 calc R . . C11 C 0.2030(4) 0.3132(6) 0.2474(3) 0.0236(10) Uani 1 1 d . . . H11A H 0.2799 0.3097 0.2644 0.028 Uiso 1 1 calc R . . H11B H 0.1771 0.3405 0.2898 0.028 Uiso 1 1 calc R . . C12 C 0.1675(4) 0.4498(7) 0.1894(3) 0.0276(10) Uani 1 1 d . . . C21 C 0.1366(4) 0.0224(6) 0.2678(3) 0.0265(10) Uani 1 1 d . . . H21A H 0.1155 0.0870 0.3061 0.032 Uiso 1 1 calc R . . H21B H 0.1984 -0.0488 0.2919 0.032 Uiso 1 1 calc R . . C22 C 0.0483(4) -0.0940(6) 0.2260(3) 0.0258(10) Uani 1 1 d . . . C31 C 0.2355(5) 0.0564(6) 0.1821(3) 0.0330(12) Uani 1 1 d . . . H31A H 0.2070 -0.0595 0.1649 0.040 Uiso 1 1 calc R . . H31B H 0.3026 0.0386 0.2200 0.040 Uiso 1 1 calc R . . C32 C 0.2560(4) 0.1530(6) 0.1183(3) 0.0289(11) Uani 1 1 d . . . C33 C 0.3461(4) 0.2482(7) 0.1281(3) 0.0296(11) Uani 1 1 d . . . H33 H 0.3924 0.2610 0.1759 0.035 Uiso 1 1 calc R . . C34 C 0.3702(5) 0.3253(6) 0.0693(3) 0.0300(11) Uani 1 1 d . . . H34 H 0.4322 0.3910 0.0759 0.036 Uiso 1 1 calc R . . C35 C 0.3012(5) 0.3030(6) 0.0012(3) 0.0291(11) Uani 1 1 d . . . C36 C 0.2084(5) 0.2141(6) -0.0105(3) 0.0300(11) Uani 1 1 d . . . H36 H 0.1608 0.2043 -0.0580 0.036 Uiso 1 1 calc R . . C37 C 0.1877(5) 0.1403(7) 0.0498(3) 0.0314(11) Uani 1 1 d . . . H37 H 0.1244 0.0789 0.0435 0.038 Uiso 1 1 calc R . . O1 O 0.4846(4) 0.2480(7) 0.3177(3) 0.0422(10) Uani 1 1 d . . . H1A H 0.5420 0.2467 0.3515 0.063 Uiso 1 1 d R . . H1B H 0.4722 0.3512 0.3013 0.063 Uiso 1 1 d R . . O2 O 0.4269(4) 0.5747(7) 0.2714(3) 0.0520(12) Uani 1 1 d . . . H2A H 0.4597 0.6499 0.2538 0.078 Uiso 1 1 d R . . H2B H 0.3783 0.5307 0.2366 0.078 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 Cu1 0.0321(5) 0.0144(4) 0.0295(5) 0.00001(19) 0.0082(3) -0.00014(19) Cl1 0.0439(9) 0.0261(6) 0.0380(7) 0.0023(5) 0.0124(6) 0.0021(5) O11 0.0324(19) 0.0213(16) 0.0280(17) 0.0015(13) 0.0068(15) -0.0010(14) O12 0.036(2) 0.0190(15) 0.036(2) -0.0016(14) 0.0095(17) -0.0030(14) O21 0.036(2) 0.0157(14) 0.0298(18) 0.0007(13) 0.0074(15) 0.0019(13) O22 0.033(2) 0.0174(15) 0.0312(19) -0.0013(13) 0.0090(16) -0.0003(13) N10 0.025(2) 0.0175(17) 0.0235(19) 0.0016(15) 0.0069(16) -0.0015(15) N3 0.036(3) 0.0179(17) 0.032(2) -0.0013(15) 0.011(2) -0.0006(16) N7 0.026(2) 0.0131(15) 0.0215(18) -0.0017(14) 0.0051(15) 0.0019(14) N9 0.035(3) 0.023(2) 0.030(2) -0.0018(15) 0.008(2) 0.0013(16) C1 0.034(3) 0.026(2) 0.031(3) 0.0011(19) 0.009(2) 0.002(2) C2 0.037(3) 0.021(2) 0.042(3) -0.004(2) 0.012(3) -0.001(2) C4 0.026(2) 0.021(2) 0.027(2) -0.0011(18) 0.0071(19) -0.0005(18) C5 0.031(3) 0.022(2) 0.027(2) 0.0012(16) 0.007(2) 0.0009(17) C6 0.030(3) 0.021(2) 0.026(2) 0.0024(17) 0.0072(19) -0.0008(18) C8 0.027(2) 0.023(2) 0.027(2) -0.0032(16) 0.007(2) -0.0011(17) C11 0.025(2) 0.021(2) 0.024(2) 0.0004(17) 0.0055(19) -0.0010(17) C12 0.029(2) 0.027(2) 0.028(2) -0.0015(19) 0.0083(19) 0.0013(19) C21 0.031(3) 0.0174(19) 0.031(2) 0.0021(17) 0.008(2) 0.0023(17) C22 0.033(3) 0.0156(19) 0.028(2) -0.0025(16) 0.007(2) -0.0013(17) C31 0.042(3) 0.019(2) 0.040(3) 0.005(2) 0.015(3) 0.003(2) C32 0.033(3) 0.021(2) 0.033(3) -0.0033(19) 0.011(2) 0.0010(19) C33 0.029(3) 0.025(2) 0.034(3) -0.001(2) 0.007(2) 0.004(2) C34 0.037(3) 0.020(2) 0.035(3) -0.0013(19) 0.013(2) 0.0022(19) C35 0.037(3) 0.018(2) 0.030(3) 0.0037(16) 0.007(2) 0.0058(18) C36 0.031(3) 0.025(2) 0.033(3) -0.0027(18) 0.007(2) 0.0010(18) C37 0.033(3) 0.028(2) 0.033(3) -0.002(2) 0.008(2) 0.001(2) O1 0.041(2) 0.044(2) 0.042(2) 0.000(2) 0.0120(19) 0.000(2) O2 0.051(3) 0.054(3) 0.051(3) 0.000(2) 0.015(2) 0.000(2) _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 Cu1 5.7130(14) 2_545 y Cu1 Cu1 5.7130(14) 2 y Cu1 O11 1.950(4) . y Cu1 O21 1.957(3) . y Cu1 O22 2.262(4) 2 y Cu1 N10 1.984(4) . y Cu1 N7 1.946(4) . y Cl1 C35 1.752(6) . ? O11 C12 1.252(7) . ? O12 C12 1.283(6) . ? O21 C22 1.273(6) . ? O22 Cu1 2.262(4) 2_545 ? O22 C22 1.242(6) . ? N10 C11 1.465(6) . ? N10 C21 1.471(6) . ? N10 C31 1.491(7) . ? N3 C2 1.339(8) . ? N3 C4 1.341(7) . ? N7 C5 1.371(7) . ? N7 C8 1.330(7) . ? N9 H9A 0.8800 . ? N9 C4 1.376(7) . ? N9 C8 1.327(7) . ? C1 H1 0.9500 . ? C1 C2 1.407(8) . ? C1 C6 1.361(8) . ? C2 H2 0.9500 . ? C4 C5 1.393(7) . ? C5 C6 1.397(7) . ? C6 H6 0.9500 . ? C8 H8 0.9500 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C11 C12 1.503(7) . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C21 C22 1.518(7) . ? C31 H31A 0.9900 . ? C31 H31B 0.9900 . ? C31 C32 1.518(8) . ? C32 C33 1.381(8) . ? C32 C37 1.368(8) . ? C33 H33 0.9500 . ? C33 C34 1.386(8) . ? C34 H34 0.9500 . ? C34 C35 1.374(8) . ? C35 C36 1.382(8) . ? C36 H36 0.9500 . ? C36 C37 1.380(8) . ? C37 H37 0.9500 . ? O1 H1A 0.8507 . ? O1 H1B 0.8542 . ? O2 H2A 0.8525 . ? O2 H2B 0.8558 . ? 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 Cu1 Cu1 Cu1 84.83(3) 2 2_545 ? O11 Cu1 Cu1 65.86(11) . 2 ? O11 Cu1 Cu1 142.72(11) . 2_545 ? O11 Cu1 O21 168.57(17) . . ? O11 Cu1 O22 95.27(14) . 2 ? O11 Cu1 N10 85.13(16) . . ? O11 Cu1 N7 93.19(16) . . ? O21 Cu1 Cu1 116.17(12) . 2 ? O21 Cu1 Cu1 33.17(11) . 2_545 ? O21 Cu1 O22 87.14(15) . 2 ? O21 Cu1 N10 83.78(16) . . ? O22 Cu1 Cu1 29.43(9) 2 2 ? O22 Cu1 Cu1 57.73(9) 2 2_545 ? N10 Cu1 Cu1 70.05(12) . 2_545 ? N10 Cu1 Cu1 86.79(12) . 2 ? N10 Cu1 O22 88.03(16) . 2 ? N7 Cu1 Cu1 116.59(13) . 2_545 ? N7 Cu1 Cu1 103.29(12) . 2 ? N7 Cu1 O21 97.08(16) . . ? N7 Cu1 O22 103.85(16) . 2 ? N7 Cu1 N10 168.11(18) . . ? C12 O11 Cu1 111.1(3) . . ? C22 O21 Cu1 111.4(3) . . ? C22 O22 Cu1 138.6(3) . 2_545 ? C11 N10 Cu1 104.5(3) . . ? C11 N10 C31 111.5(4) . . ? C21 N10 Cu1 103.8(3) . . ? C21 N10 C11 115.5(4) . . ? C21 N10 C31 108.0(4) . . ? C31 N10 Cu1 113.3(3) . . ? C2 N3 C4 113.4(5) . . ? C5 N7 Cu1 128.0(4) . . ? C8 N7 Cu1 127.8(4) . . ? C8 N7 C5 104.2(4) . . ? C4 N9 H9A 127.0 . . ? C8 N9 H9A 127.0 . . ? C8 N9 C4 106.0(5) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C6 C1 C2 121.1(5) . . ? N3 C2 C1 123.9(6) . . ? N3 C2 H2 118.1 . . ? C1 C2 H2 118.0 . . ? N3 C4 N9 126.8(5) . . ? N3 C4 C5 127.1(5) . . ? N9 C4 C5 106.1(5) . . ? N7 C5 C4 109.4(5) . . ? N7 C5 C6 132.8(5) . . ? C4 C5 C6 117.8(5) . . ? C1 C6 C5 116.7(5) . . ? C1 C6 H6 121.6 . . ? C5 C6 H6 121.7 . . ? N7 C8 H8 122.9 . . ? N9 C8 N7 114.2(5) . . ? N9 C8 H8 122.9 . . ? N10 C11 H11A 110.0 . . ? N10 C11 H11B 109.9 . . ? N10 C11 C12 108.8(4) . . ? H11A C11 H11B 108.3 . . ? C12 C11 H11A 109.9 . . ? C12 C11 H11B 109.9 . . ? O11 C12 O12 121.0(5) . . ? O11 C12 C11 119.5(5) . . ? O12 C12 C11 119.4(5) . . ? N10 C21 H21A 109.9 . . ? N10 C21 H21B 109.9 . . ? N10 C21 C22 109.0(4) . . ? H21A C21 H21B 108.3 . . ? C22 C21 H21A 109.9 . . ? C22 C21 H21B 109.8 . . ? O21 C22 C21 117.4(4) . . ? O22 C22 O21 125.2(5) . . ? O22 C22 C21 117.1(5) . . ? N10 C31 H31A 108.7 . . ? N10 C31 H31B 108.5 . . ? N10 C31 C32 114.9(4) . . ? H31A C31 H31B 107.5 . . ? C32 C31 H31A 108.6 . . ? C32 C31 H31B 108.4 . . ? C33 C32 C31 120.4(5) . . ? C37 C32 C31 120.4(5) . . ? C37 C32 C33 119.2(5) . . ? C32 C33 H33 119.5 . . ? C34 C33 C32 121.1(5) . . ? C34 C33 H33 119.4 . . ? C33 C34 H34 121.3 . . ? C35 C34 C33 117.4(5) . . ? C35 C34 H34 121.3 . . ? C34 C35 Cl1 117.8(5) . . ? C34 C35 C36 123.2(5) . . ? C36 C35 Cl1 119.1(4) . . ? C35 C36 H36 121.5 . . ? C37 C36 C35 117.1(5) . . ? C37 C36 H36 121.4 . . ? C32 C37 C36 121.9(5) . . ? C32 C37 H37 119.1 . . ? C36 C37 H37 119.0 . . ? H1A O1 H1B 109.2 . . ? H2A O2 H2B 109.3 . . ? 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 N9 H9A O12 0.88 1.86 2.740(7) 173.6 3_565 O1 H1A N3 0.85 2.08 2.879(7) 156.6 4_666 O1 H1B O2 0.85 1.86 2.708(8) 170.9 . O2 H2A O1 0.85 1.89 2.691(8) 155.7 2_655 O2 H2B O12 0.86 2.10 2.748(7) 132.7 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cu1 Cu1 O11 C12 31.5(5) 2_545 . . . ? Cu1 Cu1 O11 C12 72.8(3) 2 . . . ? Cu1 Cu1 O21 C22 -58.3(4) 2 . . . ? Cu1 Cu1 O21 C22 -37.5(3) 2_545 . . . ? Cu1 Cu1 N10 C11 -38.3(3) 2 . . . ? Cu1 Cu1 N10 C11 -124.0(3) 2_545 . . . ? Cu1 Cu1 N10 C21 -2.5(3) 2_545 . . . ? Cu1 Cu1 N10 C21 83.2(3) 2 . . . ? Cu1 Cu1 N10 C31 -159.9(3) 2 . . . ? Cu1 Cu1 N10 C31 114.5(3) 2_545 . . . ? Cu1 Cu1 N7 C5 -67.5(4) 2 . . . ? Cu1 Cu1 N7 C5 23.4(4) 2_545 . . . ? Cu1 Cu1 N7 C8 115.8(4) 2 . . . ? Cu1 Cu1 N7 C8 -153.4(3) 2_545 . . . ? Cu1 O11 C12 O12 179.3(4) . . . . ? Cu1 O11 C12 C11 -1.0(6) . . . . ? Cu1 O21 C22 O22 165.9(4) . . . . ? Cu1 O21 C22 C21 -9.0(6) . . . . ? Cu1 O22 C22 O21 -107.5(6) 2_545 . . . ? Cu1 O22 C22 C21 67.5(7) 2_545 . . . ? Cu1 N10 C11 C12 -33.5(5) . . . . ? Cu1 N10 C21 C22 36.3(4) . . . . ? Cu1 N10 C31 C32 55.7(5) . . . . ? Cu1 N7 C5 C4 -176.2(3) . . . . ? Cu1 N7 C5 C6 2.5(8) . . . . ? Cu1 N7 C8 N9 177.2(3) . . . . ? Cl1 C35 C36 C37 175.8(4) . . . . ? O11 Cu1 O21 C22 39.2(10) . . . . ? O11 Cu1 N10 C11 27.7(3) . . . . ? O11 Cu1 N10 C21 149.2(3) . . . . ? O11 Cu1 N10 C31 -93.8(3) . . . . ? O11 Cu1 N7 C5 -133.4(4) . . . . ? O11 Cu1 N7 C8 49.8(4) . . . . ? O21 Cu1 O11 C12 -30.0(10) . . . . ? O21 Cu1 N10 C11 -155.1(3) . . . . ? O21 Cu1 N10 C21 -33.6(3) . . . . ? O21 Cu1 N10 C31 83.4(3) . . . . ? O21 Cu1 N7 C5 51.6(4) . . . . ? O21 Cu1 N7 C8 -125.1(4) . . . . ? O22 Cu1 O11 C12 71.7(4) 2 . . . ? O22 Cu1 O21 C22 -63.3(4) 2 . . . ? O22 Cu1 N10 C11 -67.7(3) 2 . . . ? O22 Cu1 N10 C21 53.8(3) 2 . . . ? O22 Cu1 N10 C31 170.7(3) 2 . . . ? O22 Cu1 N7 C5 -37.2(4) 2 . . . ? O22 Cu1 N7 C8 146.1(4) 2 . . . ? N10 Cu1 O11 C12 -15.9(4) . . . . ? N10 Cu1 O21 C22 25.0(4) . . . . ? N10 Cu1 N7 C5 145.1(7) . . . . ? N10 Cu1 N7 C8 -31.7(10) . . . . ? N10 C11 C12 O11 24.8(7) . . . . ? N10 C11 C12 O12 -155.5(5) . . . . ? N10 C21 C22 O21 -19.6(6) . . . . ? N10 C21 C22 O22 165.0(4) . . . . ? N10 C31 C32 C33 100.8(6) . . . . ? N10 C31 C32 C37 -82.3(6) . . . . ? N3 C4 C5 N7 178.2(5) . . . . ? N3 C4 C5 C6 -0.7(8) . . . . ? N7 Cu1 O11 C12 175.9(4) . . . . ? N7 Cu1 O21 C22 -166.9(4) . . . . ? N7 Cu1 N10 C11 110.1(8) . . . . ? N7 Cu1 N10 C21 -128.4(7) . . . . ? N7 Cu1 N10 C31 -11.5(9) . . . . ? N7 C5 C6 C1 -178.8(5) . . . . ? N9 C4 C5 N7 -1.7(5) . . . . ? N9 C4 C5 C6 179.4(4) . . . . ? C2 N3 C4 N9 179.9(5) . . . . ? C2 N3 C4 C5 0.0(7) . . . . ? C2 C1 C6 C5 1.6(7) . . . . ? C4 N3 C2 C1 1.6(7) . . . . ? C4 N9 C8 N7 -0.8(5) . . . . ? C4 C5 C6 C1 -0.2(7) . . . . ? C5 N7 C8 N9 -0.2(5) . . . . ? C6 C1 C2 N3 -2.6(8) . . . . ? C8 N7 C5 C4 1.2(5) . . . . ? C8 N7 C5 C6 179.9(5) . . . . ? C8 N9 C4 N3 -178.4(5) . . . . ? C8 N9 C4 C5 1.5(5) . . . . ? C11 N10 C21 C22 150.1(4) . . . . ? C11 N10 C31 C32 -61.9(6) . . . . ? C21 N10 C11 C12 -146.9(4) . . . . ? C21 N10 C31 C32 170.2(5) . . . . ? C31 N10 C11 C12 89.3(5) . . . . ? C31 N10 C21 C22 -84.3(5) . . . . ? C31 C32 C33 C34 174.6(5) . . . . ? C31 C32 C37 C36 -174.3(5) . . . . ? C32 C33 C34 C35 -0.1(8) . . . . ? C33 C32 C37 C36 2.6(8) . . . . ? C33 C34 C35 Cl1 -175.6(4) . . . . ? C33 C34 C35 C36 2.6(8) . . . . ? C34 C35 C36 C37 -2.4(8) . . . . ? C35 C36 C37 C32 -0.3(8) . . . . ? C37 C32 C33 C34 -2.4(8) . . . . ? data_C555_Comp.4 _database_code_depnum_ccdc_archive 'CCDC 881139' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety '2(C16 H19 Cu N5 O8), H2 O' _chemical_formula_sum 'C32 H40 Cu2 N10 O17' _chemical_formula_weight 963.82 _chemical_melting_point ? 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M P-1 _cell_length_a 7.270(5) _cell_length_b 8.502(5) _cell_length_c 14.780(5) _cell_angle_alpha 90.628(5) _cell_angle_beta 92.540(5) _cell_angle_gamma 97.828(5) _cell_volume 904.0(9) _cell_formula_units_Z 1 _cell_measurement_reflns_used ? _cell_measurement_temperature 100(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 1.272 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.770 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 496 _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0200 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 2986 _diffrn_reflns_theta_full 26.25 _diffrn_reflns_theta_max 26.25 _diffrn_reflns_theta_min 3.84 _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9.6 _diffrn_measured_fraction_theta_full 0.916 _diffrn_measured_fraction_theta_max 0.916 _diffrn_measurement_device_type 'Single-axis HUBER diffractometer' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_radiation_detector 'ADSC Q210r CCD (binned mode)' _diffrn_radiation_monochromator 'Si 111' _diffrn_radiation_probe x-ray _diffrn_radiation_wavelength 0.7380 _diffrn_source synchrotron _diffrn_source_type 'ESRF-CRG BM16' _reflns_number_gt 2959 _reflns_number_total 2986 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_collection 'MxCube (ESRF, 2006)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.645 _refine_diff_density_min -0.790 _refine_diff_density_rms 0.136 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 280 _refine_ls_number_reflns 2986 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0349 _refine_ls_R_factor_gt 0.0347 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0751P)^2^+1.1179P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1104 _refine_ls_wR_factor_ref 0.1106 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.36520(4) 0.21963(3) 0.215561(18) 0.00927(15) Uani 1 1 d . . . N20 N 0.2809(3) 0.0443(2) 0.33436(13) 0.0083(4) Uani 1 1 d . . . C21 C 0.4037(4) -0.0777(3) 0.32598(17) 0.0106(5) Uani 1 1 d . . . H21a H 0.3279 -0.1785 0.3057 0.013 Uiso 1 1 calc R . . H21b H 0.4605 -0.0952 0.3865 0.013 Uiso 1 1 calc R . . C22 C 0.5581(4) -0.0371(3) 0.26039(16) 0.0113(5) Uani 1 1 d . . . O21 O 0.5686(3) 0.0903(2) 0.21687(12) 0.0131(4) Uani 1 1 d . . . O22 O 0.6704(3) -0.1355(2) 0.25201(12) 0.0151(4) Uani 1 1 d . . . C23 C 0.0845(4) -0.0230(3) 0.32926(16) 0.0101(5) Uani 1 1 d . . . H23a H 0.0567 -0.0793 0.2702 0.012 Uiso 1 1 calc R . . H23b H 0.0089 0.0654 0.3305 0.012 Uiso 1 1 calc R . . C24 C 0.0231(4) -0.1380(3) 0.40432(17) 0.0117(5) Uani 1 1 d . . . O26 O -0.1507(3) -0.2103(2) 0.39457(12) 0.0133(4) Uani 1 1 d . . . H26 H -0.2204 -0.1849 0.3421 0.016 Uiso 1 1 d R . . O25 O 0.1215(3) -0.1648(2) 0.46890(12) 0.0178(4) Uani 1 1 d . . . C19 C 0.3296(4) 0.1510(3) 0.41404(16) 0.0119(5) Uani 1 1 d . . . H19a H 0.3400 0.0867 0.4690 0.014 Uiso 1 1 calc R . . H19b H 0.2296 0.2174 0.4222 0.014 Uiso 1 1 calc R . . C18 C 0.5119(4) 0.2572(3) 0.40236(16) 0.0121(5) Uani 1 1 d . . . H18a H 0.5432 0.3253 0.4571 0.015 Uiso 1 1 calc R . . H18b H 0.6123 0.1908 0.3954 0.015 Uiso 1 1 calc R . . N10 N 0.4998(3) 0.3589(2) 0.32155(14) 0.0099(4) Uani 1 1 d . . . C11 C 0.3866(4) 0.4882(3) 0.33782(18) 0.0140(5) Uani 1 1 d . . . H11a H 0.4602 0.5911 0.3239 0.017 Uiso 1 1 calc R . . H11b H 0.3589 0.4905 0.4028 0.017 Uiso 1 1 calc R . . C12 C 0.2051(4) 0.4697(3) 0.28136(17) 0.0121(5) Uani 1 1 d . . . O11 O 0.1638(3) 0.3482(2) 0.22993(12) 0.0139(4) Uani 1 1 d . . . O12 O 0.1072(3) 0.5780(2) 0.28899(13) 0.0172(4) Uani 1 1 d . . . C14 C 0.6875(4) 0.4243(3) 0.29480(17) 0.0123(5) Uani 1 1 d . . . H14a H 0.7672 0.3387 0.2945 0.015 Uiso 1 1 calc R . . H14b H 0.7433 0.5066 0.3395 0.015 Uiso 1 1 calc R . . C15 C 0.6803(4) 0.4966(3) 0.20127(17) 0.0129(5) Uani 1 1 d . . . O17 O 0.8344(3) 0.5796(2) 0.17629(12) 0.0148(4) Uani 1 1 d . . . H17 H 0.9346 0.5727 0.2167 0.018 Uiso 1 1 d R . . O16 O 0.5405(3) 0.4766(2) 0.15189(13) 0.0183(4) Uani 1 1 d . . . N9 N 0.2899(3) 0.1410(3) 0.09141(14) 0.0134(5) Uani 1 1 d . . . C8 C 0.2900(4) 0.2200(3) 0.01470(18) 0.0159(6) Uani 1 1 d . . . H8 H 0.3172 0.3323 0.0119 0.019 Uiso 1 1 calc R . . N7 N 0.2476(3) 0.1255(3) -0.05865(14) 0.0160(5) Uani 1 1 d . . . H7 H 0.2483 0.1451 -0.1147 0.019 Uiso 1 1 d R . . C5 C 0.2203(4) -0.0298(3) -0.02816(17) 0.0144(5) Uani 1 1 d . . . C6 C 0.1708(4) -0.1777(3) -0.07008(18) 0.0188(6) Uani 1 1 d . . . H6 H 0.1432 -0.1904 -0.1334 0.023 Uiso 1 1 calc R . . C1 C 0.1649(4) -0.3045(3) -0.01239(19) 0.0183(6) Uani 1 1 d . . . H1 H 0.1345 -0.4094 -0.0365 0.022 Uiso 1 1 calc R . . C2 C 0.2025(4) -0.2822(3) 0.08034(19) 0.0160(6) Uani 1 1 d . . . H2 H 0.2006 -0.3741 0.1164 0.019 Uiso 1 1 calc R . . N3 N 0.2411(3) -0.1408(3) 0.12227(15) 0.0141(5) Uani 1 1 d . . . C4 C 0.2498(4) -0.0184(3) 0.06579(17) 0.0114(5) Uani 1 1 d . . . O1 O 0.1037(9) 0.4914(6) 0.4957(4) 0.0498(15) Uani 0.50 1 d P B -1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0110(2) 0.0077(2) 0.0087(2) -0.00061(12) -0.00058(13) 0.00023(13) N20 0.0090(11) 0.0066(9) 0.0089(10) 0.0005(7) 0.0017(8) -0.0011(8) C21 0.0110(14) 0.0092(11) 0.0120(12) 0.0021(9) 0.0005(9) 0.0023(9) C22 0.0104(14) 0.0122(12) 0.0102(11) -0.0034(9) -0.0014(9) -0.0017(10) O21 0.0134(10) 0.0110(9) 0.0140(9) 0.0015(7) 0.0043(7) -0.0028(7) O22 0.0141(10) 0.0176(9) 0.0152(9) -0.0003(7) 0.0011(7) 0.0074(8) C23 0.0071(13) 0.0114(11) 0.0117(12) 0.0036(9) 0.0020(9) 0.0003(9) C24 0.0137(14) 0.0098(11) 0.0123(12) 0.0014(9) 0.0049(10) 0.0023(10) O26 0.0123(10) 0.0144(9) 0.0127(9) 0.0037(7) 0.0041(7) -0.0015(7) O25 0.0170(11) 0.0212(10) 0.0150(10) 0.0083(7) 0.0000(8) 0.0015(8) C19 0.0155(15) 0.0126(12) 0.0074(11) -0.0001(9) 0.0007(9) 0.0014(10) C18 0.0146(14) 0.0113(12) 0.0099(12) -0.0001(9) -0.0032(9) 0.0011(10) N10 0.0100(12) 0.0070(9) 0.0122(10) 0.0012(8) -0.0012(8) -0.0004(8) C11 0.0151(15) 0.0093(11) 0.0174(13) -0.0031(9) -0.0024(10) 0.0026(10) C12 0.0115(14) 0.0105(12) 0.0131(12) 0.0026(9) 0.0017(9) -0.0029(10) O11 0.0140(11) 0.0112(9) 0.0152(9) -0.0017(7) -0.0036(7) -0.0013(7) O12 0.0109(11) 0.0141(9) 0.0267(10) -0.0052(7) -0.0019(8) 0.0039(7) C14 0.0103(14) 0.0088(11) 0.0166(13) 0.0026(9) -0.0023(10) -0.0020(9) C15 0.0134(14) 0.0089(11) 0.0161(13) 0.0010(9) 0.0003(10) 0.0013(10) O17 0.0102(10) 0.0149(9) 0.0189(9) 0.0037(7) 0.0002(7) 0.0004(7) O16 0.0137(11) 0.0226(10) 0.0173(9) 0.0034(8) -0.0037(8) -0.0012(8) N9 0.0166(13) 0.0132(10) 0.0098(10) 0.0023(8) -0.0008(8) -0.0002(9) C8 0.0159(15) 0.0156(12) 0.0154(13) 0.0045(10) -0.0021(10) -0.0005(10) N7 0.0193(13) 0.0200(11) 0.0072(10) 0.0058(8) -0.0008(8) -0.0033(9) C5 0.0096(14) 0.0210(13) 0.0118(12) 0.0009(10) 0.0020(9) -0.0020(10) C6 0.0145(15) 0.0279(15) 0.0123(13) -0.0041(11) 0.0044(10) -0.0039(12) C1 0.0175(15) 0.0156(13) 0.0208(14) -0.0033(10) 0.0063(11) -0.0028(11) C2 0.0150(15) 0.0138(13) 0.0189(13) 0.0022(10) 0.0037(10) 0.0000(10) N3 0.0140(13) 0.0137(11) 0.0141(11) 0.0011(8) 0.0014(8) -0.0004(9) C4 0.0097(14) 0.0138(12) 0.0103(12) 0.0004(9) 0.0000(9) 0.0001(10) O1 0.072(4) 0.032(3) 0.048(3) 0.021(2) 0.025(3) 0.009(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 N20 2.363(2) . ? Cu1 O21 1.959(2) . ? Cu1 N10 2.079(2) . ? Cu1 O11 1.960(2) . ? Cu1 N9 1.974(2) . ? N20 C21 1.465(3) . ? N20 C23 1.463(3) . ? N20 C19 1.479(3) . ? C21 H21a 0.9900 . ? C21 H21b 0.9900 . ? C21 C22 1.522(3) . ? C22 O21 1.261(3) . ? C22 O22 1.255(3) . ? C23 H23a 0.9900 . ? C23 H23b 0.9900 . ? C23 C24 1.528(3) . ? C24 O26 1.329(3) . ? C24 O25 1.210(3) . ? O26 H26 0.9506 . ? C19 H19a 0.9900 . ? C19 H19b 0.9900 . ? C19 C18 1.516(4) . ? C18 H18a 0.9900 . ? C18 H18b 0.9900 . ? C18 N10 1.489(3) . ? N10 C11 1.483(3) . ? N10 C14 1.474(3) . ? C11 H11a 0.9900 . ? C11 H11b 0.9900 . ? C11 C12 1.519(4) . ? C12 O11 1.270(3) . ? C12 O12 1.245(3) . ? C14 H14a 0.9900 . ? C14 H14b 0.9900 . ? C14 C15 1.521(3) . ? C15 O17 1.310(3) . ? C15 O16 1.216(3) . ? O17 H17 0.9297 . ? N9 C8 1.324(3) . ? N9 C4 1.391(3) . ? C8 H8 0.9500 . ? C8 N7 1.342(4) . ? N7 H7 0.8468 . ? N7 C5 1.391(4) . ? C5 C6 1.391(4) . ? C5 C4 1.396(4) . ? C6 H6 0.9500 . ? C6 C1 1.379(4) . ? C1 H1 0.9500 . ? C1 C2 1.391(4) . ? C2 H2 0.9500 . ? C2 N3 1.336(4) . ? N3 C4 1.338(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 O21 Cu1 N20 79.01(8) . . ? O21 Cu1 N10 90.02(9) . . ? O21 Cu1 O11 173.22(7) . . ? O21 Cu1 N9 89.38(9) . . ? N10 Cu1 N20 82.37(8) . . ? O11 Cu1 N20 95.74(8) . . ? O11 Cu1 N10 84.99(9) . . ? O11 Cu1 N9 96.85(9) . . ? N9 Cu1 N20 116.49(9) . . ? N9 Cu1 N10 160.61(9) . . ? C21 N20 Cu1 103.73(14) . . ? C21 N20 C19 113.4(2) . . ? C23 N20 Cu1 113.48(14) . . ? C23 N20 C21 112.20(19) . . ? C23 N20 C19 112.43(19) . . ? C19 N20 Cu1 100.78(14) . . ? N20 C21 H21a 108.7 . . ? N20 C21 H21b 108.7 . . ? N20 C21 C22 114.2(2) . . ? H21a C21 H21b 107.6 . . ? C22 C21 H21a 108.7 . . ? C22 C21 H21b 108.7 . . ? O21 C22 C21 120.1(2) . . ? O22 C22 C21 117.1(2) . . ? O22 C22 O21 122.8(2) . . ? C22 O21 Cu1 120.74(17) . . ? N20 C23 H23a 108.4 . . ? N20 C23 H23b 108.4 . . ? N20 C23 C24 115.5(2) . . ? H23a C23 H23b 107.5 . . ? C24 C23 H23a 108.4 . . ? C24 C23 H23b 108.4 . . ? O26 C24 C23 115.2(2) . . ? O25 C24 C23 124.2(2) . . ? O25 C24 O26 120.5(2) . . ? C24 O26 H26 116.5 . . ? N20 C19 H19a 109.5 . . ? N20 C19 H19b 109.5 . . ? N20 C19 C18 110.9(2) . . ? H19a C19 H19b 108.0 . . ? C18 C19 H19a 109.5 . . ? C18 C19 H19b 109.5 . . ? C19 C18 H18a 109.4 . . ? C19 C18 H18b 109.4 . . ? H18a C18 H18b 108.0 . . ? N10 C18 C19 111.0(2) . . ? N10 C18 H18a 109.4 . . ? N10 C18 H18b 109.4 . . ? C18 N10 Cu1 108.36(15) . . ? C11 N10 Cu1 106.65(16) . . ? C11 N10 C18 111.7(2) . . ? C14 N10 Cu1 109.01(15) . . ? C14 N10 C18 110.3(2) . . ? C14 N10 C11 110.7(2) . . ? N10 C11 H11a 108.9 . . ? N10 C11 H11b 108.9 . . ? N10 C11 C12 113.2(2) . . ? H11a C11 H11b 107.8 . . ? C12 C11 H11a 108.9 . . ? C12 C11 H11b 108.9 . . ? O11 C12 C11 119.0(2) . . ? O12 C12 C11 116.3(2) . . ? O12 C12 O11 124.7(2) . . ? C12 O11 Cu1 114.89(17) . . ? N10 C14 H14a 109.5 . . ? N10 C14 H14b 109.5 . . ? N10 C14 C15 110.9(2) . . ? H14a C14 H14b 108.0 . . ? C15 C14 H14a 109.5 . . ? C15 C14 H14b 109.5 . . ? O17 C15 C14 116.2(2) . . ? O16 C15 C14 122.0(2) . . ? O16 C15 O17 121.9(2) . . ? C15 O17 H17 112.7 . . ? C8 N9 Cu1 129.37(19) . . ? C8 N9 C4 105.2(2) . . ? C4 N9 Cu1 124.87(17) . . ? N9 C8 H8 123.4 . . ? N9 C8 N7 113.2(2) . . ? N7 C8 H8 123.4 . . ? C8 N7 H7 131.6 . . ? C8 N7 C5 106.9(2) . . ? C5 N7 H7 121.1 . . ? N7 C5 C4 105.6(2) . . ? C6 C5 N7 134.4(2) . . ? C6 C5 C4 120.0(2) . . ? C5 C6 H6 122.7 . . ? C1 C6 C5 114.6(2) . . ? C1 C6 H6 122.7 . . ? C6 C1 H1 119.3 . . ? C6 C1 C2 121.4(3) . . ? C2 C1 H1 119.3 . . ? C1 C2 H2 117.7 . . ? N3 C2 C1 124.7(3) . . ? N3 C2 H2 117.7 . . ? C2 N3 C4 113.6(2) . . ? N9 C4 C5 109.1(2) . . ? N3 C4 N9 125.4(2) . . ? N3 C4 C5 125.6(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 O26 H26 O22 0.95 1.61 2.559(3) 177.1 1_455 O17 H17 O12 0.93 1.61 2.535(3) 174.6 1_655 N7 H7 O22 0.85 2.14 2.945(3) 158.0 2_655 data_C607_Comp.5 _database_code_depnum_ccdc_archive 'CCDC 881140' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety ? _chemical_formula_sum 'C14 H17 Cu2 N5 O9' _chemical_formula_weight 526.41 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0039 0.0018 'Henke tables from the CCTBX' H H 0.0000 0.0000 'Henke tables from the CCTBX' N N 0.0072 0.0035 'Henke tables from the CCTBX' O O 0.0126 0.0067 'Henke tables from the CCTBX' Cu Cu 0.3287 1.3789 'Henke tables from the CCTBX' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, z+1/2' 3 '-x, y, z' 4 'x, -y, z+1/2' 5 'x+1/2, y+1/2, z' 6 '-x+1/2, -y+1/2, z+1/2' 7 '-x+1/2, y+1/2, z' 8 'x+1/2, -y+1/2, z+1/2' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Cmc21 _cell_length_a 15.401(3) _cell_length_b 14.480(3) _cell_length_c 8.1120(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1809.0(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used ? _cell_measurement_temperature 100(2) _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 2.415 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour 'pale blue' _exptl_crystal_density_diffrn 1.933 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1064 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.02 _exptl_crystal_size_min 0.02 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0237 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 1048 _diffrn_reflns_theta_full 28.21 _diffrn_reflns_theta_max 28.21 _diffrn_reflns_theta_min 4.60 _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9.6 _diffrn_measured_fraction_theta_full 0.945 _diffrn_measured_fraction_theta_max 0.945 _diffrn_measurement_device_type 'Single-axis HUBER diffractometer' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_radiation_detector 'ADSC Q210r CCD (binned mode)' _diffrn_radiation_monochromator 'Si 111' _diffrn_radiation_source synchrotron _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.73800 _diffrn_source_type 'ESRF-CRG BM16' _reflns_number_gt 1031 _reflns_number_total 1048 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_collection 'MxCube (ESRF, 2006)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.695 _refine_diff_density_min -0.672 _refine_diff_density_rms 0.097 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.09(3) _refine_ls_extinction_coef 0.034(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.042 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 1048 _refine_ls_number_restraints 4 _refine_ls_R_factor_all 0.0466 _refine_ls_R_factor_gt 0.0463 _refine_ls_restrained_S_all 1.130 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1143P)^2^+0.7631P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1290 _refine_ls_wR_factor_ref 0.1298 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.0000 0.1005(6) 0.4499(16) 0.092(3) Uani 1 2 d S . . H1 H 0.0414 0.1374 0.4773 0.111 Uiso 1 1 d R . . Cu1 Cu 0.30729(3) 0.14696(4) 0.93048(15) 0.0479(4) Uani 1 1 d . . . N10 N 0.1857(3) 0.1579(3) 1.0029(10) 0.0491(13) Uani 1 1 d . . . H10 H 0.1804 0.2145 1.0562 0.059 Uiso 1 1 calc R . . C11 C 0.1288(4) 0.1607(4) 0.8589(10) 0.0512(13) Uani 1 1 d . . . H11a H 0.0797 0.2031 0.8804 0.061 Uiso 1 1 calc R . . H11b H 0.1047 0.0983 0.8382 0.061 Uiso 1 1 calc R . . C12 C 0.1791(4) 0.1936(4) 0.7062(9) 0.0525(13) Uani 1 1 d . . . O11 O 0.2612(2) 0.2014(3) 0.7236(6) 0.0562(10) Uani 1 1 d . . . O12 O 0.1396(3) 0.2120(3) 0.5787(7) 0.0601(11) Uani 1 1 d . . . C21 C 0.1694(4) 0.0850(4) 1.1279(8) 0.0515(12) Uani 1 1 d . . . H21a H 0.1425 0.0306 1.0743 0.062 Uiso 1 1 calc R . . H21b H 0.1285 0.1084 1.2123 0.062 Uiso 1 1 calc R . . C22 C 0.2541(3) 0.0566(3) 1.2098(7) 0.0472(11) Uani 1 1 d . . . O21 O 0.3249(3) 0.0854(3) 1.1412(6) 0.0497(9) Uani 1 1 d . . . O22 O 0.2522(2) 0.0074(3) 1.3310(7) 0.0579(11) Uani 1 1 d . . . N7 N 0.4268(3) 0.1375(3) 0.8431(8) 0.0465(11) Uani 1 1 d . . . C8 C 0.5000 0.1483(4) 0.9340(16) 0.0420(13) Uani 1 2 d S . . H8 H 0.5000 0.1619 1.0485 0.050 Uiso 1 2 calc SR . . C3 C 0.4074(4) 0.1026(4) 0.5430(8) 0.0554(13) Uani 1 1 d D . . H3 H 0.3457 0.1014 0.5425 0.066 Uiso 1 1 calc R A . N1 N 0.4549(4) 0.0873(3) 0.4016(7) 0.0618(15) Uani 0.50 1 d PD A -1 H1a H 0.4247 0.0810 0.3148 0.074 Uiso 0.50 1 d PR A -1 C1 C 0.4549(4) 0.0873(3) 0.4016(7) 0.0618(15) Uani 0.50 1 d PD . -2 H1b H 0.4247 0.0810 0.3148 0.074 Uiso 0.50 1 d PR . -2 C4 C 0.4540(3) 0.1198(3) 0.6858(7) 0.0431(11) Uani 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 0.060(4) 0.090(5) 0.128(9) -0.044(6) 0.000 0.000 Cu1 0.0365(5) 0.0521(5) 0.0552(6) 0.0053(3) -0.0007(3) 0.00143(17) N10 0.035(3) 0.049(2) 0.063(3) -0.001(2) -0.0025(19) -0.0004(14) C11 0.044(3) 0.052(2) 0.058(3) 0.003(2) 0.002(3) 0.002(2) C12 0.045(2) 0.046(2) 0.067(4) 0.007(3) 0.001(2) 0.003(2) O11 0.0409(18) 0.060(2) 0.067(3) 0.015(2) -0.0060(19) 0.0022(15) O12 0.048(2) 0.066(2) 0.066(3) 0.015(2) -0.0100(19) -0.0046(16) C21 0.043(2) 0.056(3) 0.056(3) -0.001(2) 0.001(2) 0.001(2) C22 0.045(2) 0.045(2) 0.051(3) -0.003(2) -0.001(2) -0.0020(18) O21 0.0406(16) 0.0544(19) 0.054(2) 0.0025(18) -0.0045(17) 0.0024(15) O22 0.050(2) 0.0588(19) 0.065(3) 0.006(2) -0.0034(19) -0.0003(16) N7 0.035(2) 0.049(2) 0.056(3) 0.0013(18) -0.003(2) 0.0003(14) C8 0.041(3) 0.050(3) 0.035(3) 0.001(3) 0.000 0.000 C3 0.060(3) 0.045(2) 0.061(3) -0.001(3) -0.011(3) -0.001(2) N1 0.093(4) 0.044(2) 0.048(3) -0.001(2) -0.009(3) -0.004(2) C1 0.093(4) 0.044(2) 0.048(3) -0.001(2) -0.009(3) -0.004(2) C4 0.042(3) 0.039(2) 0.048(3) -0.0028(18) 0.001(2) 0.0020(18) _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 N10 1.969(6) . ? Cu1 O11 1.985(4) . ? Cu1 O12 2.507(4) 6 ? Cu1 O21 1.947(5) . ? Cu1 O22 2.524(5) 4_554 ? Cu1 N7 1.977(5) . ? N10 C11 1.461(10) . ? N10 C21 1.486(9) . ? C11 C12 1.536(10) . ? C12 O11 1.278(6) . ? C12 O12 1.229(9) . ? C21 C22 1.520(8) . ? C22 O21 1.293(7) . ? C22 O22 1.214(8) . ? N7 C8 1.356(9) . ? N7 C4 1.367(8) . ? C8 N7 1.356(9) 3_655 ? C3 N1 1.378(8) . ? C3 C4 1.386(7) . ? C4 C4 1.417(9) 3_655 ? 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 N10 Cu1 O11 83.1(3) . . ? N10 Cu1 O12 95.8(2) . 6 ? N10 Cu1 O22 81.19(19) . 4_554 ? N10 Cu1 N7 176.3(3) . . ? O11 Cu1 O12 101.45(18) . 6 ? O11 Cu1 O22 87.78(18) . 4_554 ? O12 Cu1 O22 169.95(19) 6 4_554 ? O21 Cu1 N10 84.7(3) . . ? O21 Cu1 O11 166.85(17) . . ? O21 Cu1 O12 84.62(18) . 6 ? O21 Cu1 O22 85.54(18) . 4_554 ? O21 Cu1 N7 98.8(2) . . ? N7 Cu1 O11 93.3(2) . . ? N7 Cu1 O12 85.67(18) . 6 ? N7 Cu1 O22 97.89(17) . 4_554 ? C11 N10 Cu1 109.6(5) . . ? C11 N10 C21 117.6(5) . . ? C21 N10 Cu1 107.9(4) . . ? N10 C11 C12 110.5(5) . . ? O11 C12 C11 115.9(6) . . ? O12 C12 C11 119.8(5) . . ? O12 C12 O11 124.3(6) . . ? C12 O11 Cu1 114.3(4) . . ? N10 C21 C22 110.1(5) . . ? O21 C22 C21 116.7(5) . . ? O22 C22 C21 119.4(5) . . ? O22 C22 O21 123.9(5) . . ? C22 O2A Cu1 114.1(4) . . ? C8 N7 Cu1 124.8(6) . . ? C8 N7 C4 105.9(6) . . ? C4 N7 Cu1 129.2(4) . . ? N7 C8 N7 112.5(10) 3_655 . ? N1 C3 C4 116.7(5) . . ? N7 C4 C3 130.9(5) . . ? N7 C4 C4 107.8(3) . 3_655 ? C3 C4 C4 121.2(3) . 3_655 ? 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 O1 H1 O12 0.86 2.03 2.885(7) 170.1 . N1 H1a O21A 0.85 2.09 2.910(8) 163.9 1_554 data_C484_Comp.6 _database_code_depnum_ccdc_archive 'CCDC 881141' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C28 H31 Cu2 N5 O10, 2(H2 O)' _chemical_formula_sum 'C28 H35 Cu2 N5 O12' _chemical_formula_weight 760.69 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y, -z+1/2' 3 'x+1/2, y+1/2, z' 4 '-x+1/2, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x, -y, z-1/2' 7 '-x+1/2, -y+1/2, -z' 8 'x+1/2, -y+1/2, z-1/2' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M C2/c _cell_length_a 17.6777(11) _cell_length_b 10.0875(6) _cell_length_c 20.9883(13) _cell_angle_alpha 90.00 _cell_angle_beta 110.719(2) _cell_angle_gamma 90.00 _cell_volume 3500.7(4) _cell_formula_units_Z 4 _cell_measurement_reflns_used 9878 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 66.23 _cell_measurement_theta_min 5.65 _exptl_absorpt_coefficient_mu 2.056 _exptl_absorpt_correction_T_max 0.8208 _exptl_absorpt_correction_T_min 0.7905 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_process_details 'Bruker SADABS, 2010' _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.443 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'cut block' _exptl_crystal_F_000 1568 _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0530 _diffrn_reflns_av_sigmaI/netI 0.0327 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 19804 _diffrn_reflns_theta_full 66.49 _diffrn_reflns_theta_max 66.49 _diffrn_reflns_theta_min 5.65 _diffrn_ambient_temperature 293(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.949 _diffrn_measured_fraction_theta_max 0.949 _diffrn_measurement_device_type 'Bruker X8 Proteum' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'graded multilayer optics' _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _reflns_number_gt 2740 _reflns_number_total 2912 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics ? _computing_publication_material ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.426 _refine_diff_density_min -0.357 _refine_diff_density_rms 0.066 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 278 _refine_ls_number_reflns 2912 _refine_ls_number_restraints 187 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0471 _refine_ls_restrained_S_all 1.044 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0760P)^2^+9.1228P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1387 _refine_ls_wR_factor_ref 0.1408 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.67665(2) 0.72058(4) 0.80912(2) 0.0315(2) Uani 1 1 d . . . C8 C 0.5000 0.7138(4) 0.7500 0.0344(9) Uani 1 2 d S . . H8 H 0.5000 0.8060 0.7500 0.041 Uiso 1 2 calc SR . . C11 C 0.84574(18) 0.7164(3) 0.85737(17) 0.0348(7) Uani 1 1 d . . . H11a H 0.8950 0.7226 0.8970 0.042 Uiso 1 1 calc R . . H11b H 0.8577 0.7455 0.8179 0.042 Uiso 1 1 calc R . . O21 O 0.63710(12) 0.9042(2) 0.80944(12) 0.0390(5) Uani 1 1 d . . . O11 O 0.73972(12) 0.5551(2) 0.82702(12) 0.0402(5) Uani 1 1 d . . . N10 N 0.78286(14) 0.8020(2) 0.86666(12) 0.0294(5) Uani 1 1 d . A . C5 C 0.54268(16) 0.5129(3) 0.76574(14) 0.0295(6) Uani 1 1 d . . . O12 O 0.86604(13) 0.4831(2) 0.85719(14) 0.0517(6) Uani 1 1 d . . . C12 C 0.81608(17) 0.5733(3) 0.84750(16) 0.0355(7) Uani 1 1 d . . . O22 O 0.68139(13) 1.1113(2) 0.81203(13) 0.0485(6) Uani 1 1 d . . . C21 C 0.77901(17) 0.9382(3) 0.84036(15) 0.0320(6) Uani 1 1 d . . . H21a H 0.7965 0.9391 0.8015 0.038 Uiso 1 1 calc R . . H21b H 0.8149 0.9951 0.8753 0.038 Uiso 1 1 calc R . . C31 C 0.78357(18) 0.7976(3) 0.93860(15) 0.0375(7) Uani 1 1 d DU . . H31c H 0.7776 0.7061 0.9503 0.045 Uiso 0.520(17) 1 calc PR A 2 H31d H 0.7371 0.8462 0.9405 0.045 Uiso 0.520(17) 1 calc PR A 2 H31a H 0.7787 0.7057 0.9503 0.045 Uiso 0.480(17) 1 calc PR A 1 H31b H 0.7360 0.8439 0.9398 0.045 Uiso 0.480(17) 1 calc PR A 1 C22 C 0.69282(18) 0.9898(3) 0.81931(15) 0.0346(6) Uani 1 1 d . . . O1 O 0.69320(15) 0.7501(2) 0.70727(12) 0.0484(6) Uani 1 1 d . . . C32 C 0.859(2) 0.854(6) 0.9915(14) 0.057(4) Uani 0.520(17) 1 d PDU A 2 C37 C 0.8524(10) 0.999(2) 1.0030(8) 0.063(3) Uani 0.520(17) 1 d PDU A 2 H37 H 0.8050 1.0444 0.9789 0.076 Uiso 0.520(17) 1 calc PR A 2 C33 C 0.9276(10) 0.8019(18) 1.0288(8) 0.066(3) Uani 0.520(17) 1 d PDU A 2 H33 H 0.9321 0.7113 1.0229 0.079 Uiso 0.520(17) 1 calc PR A 2 C34 C 0.9934(9) 0.860(2) 1.0750(7) 0.077(3) Uani 0.520(17) 1 d PDU A 2 H34 H 1.0398 0.8116 1.0984 0.092 Uiso 0.520(17) 1 calc PR A 2 C36 C 0.9179(9) 1.0679(17) 1.0504(6) 0.078(3) Uani 0.520(17) 1 d PDU A 2 H36 H 0.9146 1.1582 1.0580 0.094 Uiso 0.520(17) 1 calc PR A 2 C35 C 0.9877(10) 0.996(2) 1.0856(7) 0.079(3) Uani 0.520(17) 1 d PDU A 2 H35 H 1.0316 1.0395 1.1169 0.095 Uiso 0.520(17) 1 calc PR A 2 N9 N 0.56808(13) 0.6427(2) 0.77466(12) 0.0324(5) Uani 1 1 d . . . C1 C 0.5419(2) 0.2825(3) 0.7664(2) 0.0496(8) Uani 0.50 1 d PU . 1 H1 H 0.5687 0.2019 0.7780 0.060 Uiso 1 1 calc R . 1 N1 N 0.5419(2) 0.2825(3) 0.7664(2) 0.0496(8) Uani 0.50 1 d P . 2 C6 C 0.58463(19) 0.3944(3) 0.78177(17) 0.0402(7) Uani 1 1 d U . . H6 H 0.6406 0.3929 0.8025 0.048 Uiso 1 1 calc R . 1 O2 O 1.0264(2) 0.5508(5) 0.8671(3) 0.0773(17) Uani 0.699(9) 1 d PU B 2 O2A O 1.1582(8) 0.5432(16) 0.9947(6) 0.102(5) Uani 0.301(9) 1 d PU B 1 C34A C 0.9912(8) 0.784(2) 1.0723(7) 0.082(3) Uani 0.480(17) 1 d PDU A 1 H34A H 1.0314 0.7215 1.0924 0.099 Uiso 0.480(17) 1 calc PR A 1 C35A C 0.9999(9) 0.916(3) 1.0912(8) 0.079(3) Uani 0.480(17) 1 d PDU A 1 H35A H 1.0484 0.9410 1.1248 0.094 Uiso 0.480(17) 1 calc PR A 1 C33A C 0.9198(10) 0.7502(18) 1.0222(9) 0.065(3) Uani 0.480(17) 1 d PDU A 1 H33A H 0.9102 0.6633 1.0066 0.078 Uiso 0.480(17) 1 calc PR A 1 C36A C 0.9448(11) 1.013(2) 1.0656(8) 0.080(3) Uani 0.480(17) 1 d PDU A 1 H36A H 0.9553 1.1010 1.0793 0.095 Uiso 0.480(17) 1 calc PR A 1 C37A C 0.8700(12) 0.973(3) 1.0167(11) 0.072(4) Uani 0.480(17) 1 d PDU A 1 H37A H 0.8285 1.0351 1.0015 0.086 Uiso 0.480(17) 1 calc PR A 1 C32A C 0.857(2) 0.856(6) 0.9927(15) 0.053(5) Uani 0.480(17) 1 d PD A 1 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0193(3) 0.0258(3) 0.0454(3) -0.00033(16) 0.0068(2) -0.00008(14) C8 0.024(2) 0.025(2) 0.050(2) 0.000 0.0079(18) 0.000 C11 0.0239(14) 0.0352(17) 0.0442(16) 0.0000(12) 0.0105(12) 0.0012(11) O21 0.0245(10) 0.0282(10) 0.0623(13) -0.0024(9) 0.0131(9) -0.0014(8) O11 0.0233(10) 0.0281(10) 0.0631(14) 0.0000(9) 0.0079(9) -0.0007(8) N10 0.0250(11) 0.0266(11) 0.0357(12) 0.0015(9) 0.0099(9) 0.0005(9) C5 0.0227(13) 0.0241(14) 0.0425(15) 0.0013(11) 0.0127(11) 0.0015(11) O12 0.0298(11) 0.0327(12) 0.0844(18) -0.0040(11) 0.0099(11) 0.0068(9) C12 0.0255(14) 0.0306(15) 0.0462(16) 0.0000(12) 0.0074(12) 0.0028(12) O22 0.0381(13) 0.0249(11) 0.0812(18) 0.0031(10) 0.0195(12) 0.0022(9) C21 0.0271(14) 0.0268(14) 0.0414(15) 0.0022(11) 0.0109(12) -0.0009(11) C31 0.0319(15) 0.0437(17) 0.0392(16) 0.0018(12) 0.0154(12) -0.0046(12) C22 0.0294(14) 0.0289(15) 0.0453(16) -0.0009(12) 0.0131(12) 0.0010(12) O1 0.0522(14) 0.0448(12) 0.0511(13) 0.0070(10) 0.0220(11) 0.0124(11) C32 0.052(6) 0.081(7) 0.033(8) -0.006(7) 0.010(5) -0.015(6) C37 0.079(6) 0.079(6) 0.030(5) -0.017(5) 0.018(4) -0.030(4) C33 0.045(4) 0.103(7) 0.041(4) 0.000(5) 0.006(3) -0.019(5) C34 0.054(4) 0.121(8) 0.048(5) -0.006(7) 0.010(3) -0.032(6) C36 0.088(7) 0.097(7) 0.044(5) -0.014(5) 0.016(5) -0.041(5) C35 0.069(6) 0.121(8) 0.047(5) -0.010(6) 0.020(4) -0.045(6) N9 0.0219(11) 0.0245(12) 0.0479(14) 0.0016(10) 0.0088(10) 0.0018(9) C1 0.0455(17) 0.0247(14) 0.093(3) 0.0107(14) 0.0417(18) 0.0086(11) N1 0.0455(17) 0.0247(14) 0.093(3) 0.0107(14) 0.0417(18) 0.0086(11) C6 0.0310(15) 0.0332(15) 0.0609(19) 0.0078(14) 0.0217(14) 0.0071(12) O2 0.050(2) 0.070(3) 0.122(4) 0.000(3) 0.043(3) -0.006(2) O2A 0.079(8) 0.136(12) 0.069(7) 0.018(7) 0.000(6) 0.003(8) C34A 0.049(5) 0.125(8) 0.057(5) 0.005(7) 0.000(4) -0.017(6) C35A 0.060(5) 0.130(9) 0.046(6) -0.005(7) 0.018(4) -0.028(7) C33A 0.038(5) 0.102(8) 0.042(5) 0.012(6) -0.001(4) -0.002(6) C36A 0.073(7) 0.118(7) 0.043(6) -0.006(6) 0.016(5) -0.028(6) C37A 0.068(6) 0.098(9) 0.046(8) -0.004(6) 0.015(4) -0.022(6) C32A 0.030(6) 0.094(10) 0.038(9) 0.001(8) 0.015(5) -0.019(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 O21 1.981(2) . ? Cu1 O11 1.969(2) . ? Cu1 N10 2.013(2) . ? Cu1 O1 2.277(2) . ? Cu1 N9 1.960(2) . ? C8 N9 1.338(3) . ? C8 N9 1.338(3) 2_656 ? C11 N10 1.474(4) . ? C11 C12 1.525(4) . ? O21 C22 1.271(4) . ? O11 C12 1.277(4) . ? N10 C21 1.473(4) . ? N10 C31 1.506(4) . ? C5 C5 1.417(5) 2_656 ? C5 N9 1.375(4) . ? C5 C6 1.384(4) . ? O12 C12 1.233(4) . ? O22 C22 1.243(4) . ? C21 C22 1.520(4) . ? C31 C32 1.52(4) . ? C31 C32A 1.51(4) . ? C32 C37 1.49(6) . ? C32 C33 1.30(5) . ? C37 C36 1.412(16) . ? C33 C34 1.355(17) . ? C34 C35 1.40(2) . ? C36 C35 1.40(2) . ? C1 N1 1.394(7) 2_656 ? C1 C6 1.333(5) . ? C34A C35A 1.39(2) . ? C34A C33A 1.369(16) . ? C35A C36A 1.35(2) . ? C33A C32A 1.51(6) . ? C36A C37A 1.42(2) . ? C37A C32A 1.27(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 O21 Cu1 N10 82.64(9) . . ? O21 Cu1 O1 92.51(9) . . ? O11 Cu1 O21 165.76(9) . . ? O11 Cu1 N10 83.48(9) . . ? O11 Cu1 O1 92.16(9) . . ? N10 Cu1 O1 96.17(9) . . ? N9 Cu1 O21 94.33(9) . . ? N9 Cu1 O11 98.33(9) . . ? N9 Cu1 N10 165.56(10) . . ? N9 Cu1 O1 98.07(10) . . ? N9 C8 N9 115.1(3) 2_656 . ? N10 C11 C12 109.5(2) . . ? C22 O21 Cu1 112.46(18) . . ? C12 O11 Cu1 113.71(18) . . ? C11 N10 Cu1 105.58(17) . . ? C11 N10 C31 112.1(2) . . ? C21 N10 Cu1 104.24(17) . . ? C21 N10 C11 115.7(2) . . ? C21 N10 C31 112.7(2) . . ? C31 N10 Cu1 105.34(17) . . ? N9 C5 C5 107.82(14) . 2_656 ? N9 C5 C6 131.9(3) . . ? C6 C5 C5 120.27(18) . 2_656 ? O11 C12 C11 117.0(2) . . ? O12 C12 C11 118.9(3) . . ? O12 C12 O11 124.0(3) . . ? N10 C21 C22 109.7(2) . . ? N10 C31 C32 114.5(4) . . ? N10 C31 C32A 116.3(4) . . ? C32A C31 C32 2(3) . . ? O21 C22 C21 117.0(3) . . ? O22 C22 O21 124.6(3) . . ? O22 C22 C21 118.4(3) . . ? C37 C32 C31 113(3) . . ? C33 C32 C31 133(4) . . ? C33 C32 C37 114(3) . . ? C36 C37 C32 120.0(19) . . ? C32 C33 C34 130(3) . . ? C33 C34 C35 116.4(15) . . ? C35 C36 C37 118.0(12) . . ? C36 C35 C34 121.6(12) . . ? C8 N9 Cu1 123.9(2) . . ? C8 N9 C5 104.6(2) . . ? C5 N9 Cu1 131.44(18) . . ? C6 C1 N1 122.11(19) . 2_656 ? C1 C6 C5 117.6(3) . . ? C33A C34A C35A 115.9(14) . . ? C36A C35A C34A 126.2(15) . . ? C34A C33A C32A 119(2) . . ? C35A C36A C37A 116.2(17) . . ? C32A C37A C36A 123(3) . . ? C33A C32A C31 110(4) . . ? C37A C32A C31 131(4) . . ? C37A C32A C33A 119(3) . . ? data_C606_Comp.7 _database_code_depnum_ccdc_archive 'CCDC 881142' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C10 H13 Cu N5 O5, 2(H2 O)' _chemical_formula_sum 'C10 H17 Cu N5 O7' _chemical_formula_weight 382.83 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _cell_length_a 6.7944(11) _cell_length_b 7.8048(12) _cell_length_c 14.257(2) _cell_angle_alpha 90.174(8) _cell_angle_beta 92.347(8) _cell_angle_gamma 110.213(7) _cell_volume 708.75(19) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2100 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 65.46 _cell_measurement_theta_min 3.10 _exptl_absorpt_coefficient_mu 2.645 _exptl_absorpt_correction_T_max 0.9016 _exptl_absorpt_correction_T_min 0.7779 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_process_details 'Bruker SADABS, 2010' _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.794 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 394 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0595 _diffrn_reflns_av_sigmaI/netI 0.0495 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 9355 _diffrn_reflns_theta_full 66.49 _diffrn_reflns_theta_max 66.49 _diffrn_reflns_theta_min 3.10 _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.942 _diffrn_measured_fraction_theta_max 0.942 _diffrn_measurement_device_type 'Bruker X8 Proteum' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator 'graded multilayer optics' _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _reflns_number_gt 2037 _reflns_number_total 2344 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ? _computing_publication_material ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.898 _refine_diff_density_min -0.413 _refine_diff_density_rms 0.091 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2344 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0491 _refine_ls_R_factor_gt 0.0428 _refine_ls_restrained_S_all 1.070 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0660P)^2^+0.6844P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1131 _refine_ls_wR_factor_ref 0.1180 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.60030(7) 0.74967(6) 0.72750(3) 0.01764(19) Uani 1 1 d . . . O11 O 0.2949(3) 0.6181(3) 0.71359(15) 0.0215(5) Uani 1 1 d . . . O21 O 0.8978(3) 0.8722(3) 0.77062(15) 0.0234(5) Uani 1 1 d . . . O12 O 0.0306(3) 0.4282(3) 0.79082(17) 0.0276(6) Uani 1 1 d . . . N9 N 0.8803(4) 1.1398(3) 0.62165(18) 0.0166(6) Uani 1 1 d . . . H9 H 0.8915 1.1418 0.6834 0.020 Uiso 1 1 calc R . . N3 N 0.6329(4) 0.8321(3) 0.59715(18) 0.0141(5) Uani 1 1 d . . . N1 N 0.5374(4) 0.7506(3) 0.43594(17) 0.0145(5) Uani 1 1 d . . . N6 N 0.6751(4) 0.9422(4) 0.31354(18) 0.0206(6) Uani 1 1 d . . . H6a H 0.5978 0.8556 0.2743 0.025 Uiso 1 1 calc R . . H6b H 0.7575 1.0468 0.2919 0.025 Uiso 1 1 calc R . . O22 O 1.1124(4) 0.8632(4) 0.89202(18) 0.0358(6) Uani 1 1 d . . . C4 C 0.7609(4) 0.9980(4) 0.5674(2) 0.0137(6) Uani 1 1 d . . . C2 C 0.5265(5) 0.7201(4) 0.5274(2) 0.0145(6) Uani 1 1 d . . . H2 H 0.4317 0.6049 0.5452 0.017 Uiso 1 1 calc R . . C7 C 0.9268(5) 1.2315(4) 0.4723(2) 0.0177(7) Uani 1 1 d . . . H7 H 0.9737 1.3033 0.4186 0.021 Uiso 1 1 calc R . . N10 N 0.5521(5) 0.7242(4) 0.8634(2) 0.0263(7) Uani 1 1 d . . . H10 H 0.5240 0.8207 0.8794 0.032 Uiso 1 1 d R . . C8 C 0.9832(5) 1.2830(4) 0.5636(2) 0.0194(7) Uani 1 1 d . . . H8 H 1.0782 1.3989 0.5845 0.023 Uiso 1 1 calc R . . C12 C 0.2145(5) 0.5365(4) 0.7874(2) 0.0201(7) Uani 1 1 d . . . C5 C 0.7824(4) 1.0473(4) 0.4734(2) 0.0147(6) Uani 1 1 d . . . C6 C 0.6674(5) 0.9148(4) 0.4063(2) 0.0147(6) Uani 1 1 d . . . C11 C 0.3560(5) 0.5716(5) 0.8765(2) 0.0225(7) Uani 1 1 d . . . H11a H 0.2821 0.6003 0.9295 0.027 Uiso 1 1 calc R . . H11b H 0.3882 0.4603 0.8921 0.027 Uiso 1 1 calc R . . C22 C 0.9335(5) 0.8265(5) 0.8545(2) 0.0251(8) Uani 1 1 d . . . C21 C 0.7461(5) 0.7145(5) 0.9083(2) 0.0256(8) Uani 1 1 d . . . H21a H 0.7394 0.5858 0.9098 0.031 Uiso 1 1 calc R . . H21b H 0.7614 0.7614 0.9738 0.031 Uiso 1 1 calc R . . O1 O 0.6713(4) 0.4876(3) 0.71014(17) 0.0278(6) Uani 1 1 d . . . H1a H 0.7917 0.4791 0.7272 0.042 Uiso 1 1 d R . . H1b H 0.6164 0.4097 0.6643 0.042 Uiso 1 1 d R . . O2 O 0.8122(4) 0.1522(4) 0.91607(19) 0.0412(7) Uani 1 1 d . . . H2a H 0.8946 0.2415 0.8891 0.049 Uiso 1 1 d R . . H2b H 0.8420 0.1704 0.9742 0.049 Uiso 1 1 d R . . O3 O 0.4321(5) 0.1952(4) 0.8894(2) 0.0489(8) Uani 1 1 d . . . H3a H 0.3493 0.0856 0.8853 0.059 Uiso 1 1 d R . . H3b H 0.5441 0.1684 0.8879 0.059 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 Cu1 0.0148(3) 0.0197(3) 0.0134(3) 0.00250(18) -0.00077(18) -0.0003(2) O11 0.0177(11) 0.0258(12) 0.0165(12) 0.0068(9) 0.0016(9) 0.0016(9) O21 0.0203(12) 0.0250(12) 0.0165(12) 0.0027(9) -0.0021(9) -0.0024(10) O12 0.0125(12) 0.0352(13) 0.0279(13) 0.0101(10) -0.0022(9) -0.0008(10) N9 0.0156(13) 0.0149(13) 0.0183(14) -0.0004(10) -0.0023(10) 0.0042(11) N3 0.0135(13) 0.0114(12) 0.0170(13) 0.0032(10) -0.0011(10) 0.0042(10) N1 0.0117(12) 0.0147(12) 0.0169(13) 0.0013(10) 0.0003(10) 0.0043(10) N6 0.0186(14) 0.0220(14) 0.0181(14) 0.0051(11) 0.0023(11) 0.0030(11) O22 0.0213(13) 0.0474(16) 0.0258(13) 0.0060(12) -0.0069(11) -0.0036(12) C4 0.0083(14) 0.0128(14) 0.0206(16) 0.0004(12) -0.0012(11) 0.0043(12) C2 0.0100(14) 0.0141(14) 0.0189(16) 0.0031(12) 0.0010(12) 0.0034(12) C7 0.0144(16) 0.0120(15) 0.0266(17) 0.0053(12) 0.0024(13) 0.0042(13) N10 0.0259(16) 0.0283(15) 0.0209(15) 0.0035(12) 0.0016(12) 0.0043(13) C8 0.0136(16) 0.0135(15) 0.0299(18) 0.0004(13) -0.0013(13) 0.0033(12) C12 0.0183(17) 0.0220(16) 0.0212(17) 0.0027(13) -0.0009(13) 0.0088(14) C5 0.0086(14) 0.0158(15) 0.0221(17) 0.0047(12) 0.0032(12) 0.0067(12) C6 0.0099(14) 0.0171(15) 0.0194(16) 0.0026(12) 0.0027(12) 0.0074(12) C11 0.0168(17) 0.0286(18) 0.0195(17) 0.0047(13) 0.0004(13) 0.0047(14) C22 0.0243(19) 0.0234(17) 0.0193(17) -0.0002(13) -0.0022(14) -0.0021(14) C21 0.0232(18) 0.0268(18) 0.0207(17) 0.0044(14) -0.0036(14) 0.0015(15) O1 0.0281(13) 0.0213(12) 0.0322(14) -0.0065(10) -0.0150(11) 0.0081(10) O2 0.0392(16) 0.0418(16) 0.0312(15) 0.0048(12) -0.0063(12) 0.0005(13) O3 0.0356(16) 0.0305(15) 0.077(2) -0.0065(14) 0.0045(15) 0.0070(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 O11 1.973(2) . ? Cu1 O21 1.984(2) . ? Cu1 N3 1.964(3) . ? Cu1 N10 1.978(3) . ? Cu1 O1 2.273(2) . ? O11 C12 1.273(4) . ? O21 C22 1.287(4) . ? O12 C12 1.246(4) . ? N9 H9 0.8800 . ? N9 C4 1.343(4) . ? N9 C8 1.391(4) . ? N3 C4 1.367(4) . ? N3 C2 1.332(4) . ? N1 C2 1.326(4) . ? N1 C6 1.361(4) . ? N6 H6a 0.8800 . ? N6 H6b 0.8800 . ? N6 C6 1.341(4) . ? O22 C22 1.245(4) . ? C4 C5 1.395(4) . ? C2 H2 0.9500 . ? C7 H7 0.9500 . ? C7 C8 1.361(5) . ? C7 C5 1.434(4) . ? N10 H10 0.8702 . ? N10 C11 1.468(4) . ? N10 C21 1.467(4) . ? C8 H8 0.9500 . ? C12 C11 1.526(4) . ? C5 C6 1.403(4) . ? C11 H11a 0.9900 . ? C11 H11b 0.9900 . ? C22 C21 1.512(5) . ? C21 H21a 0.9900 . ? C21 H21b 0.9900 . ? O1 H1a 0.8686 . ? O1 H1b 0.8703 . ? O2 H2a 0.8341 . ? O2 H2b 0.8440 . ? O3 H3a 0.8460 . ? O3 H3b 0.8569 . ? 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 O11 Cu1 O21 167.68(9) . . ? O11 Cu1 N10 83.99(10) . . ? O11 Cu1 O1 92.13(9) . . ? O21 Cu1 O1 88.11(9) . . ? N3 Cu1 O11 95.52(10) . . ? N3 Cu1 O21 96.63(10) . . ? N3 Cu1 N10 165.48(11) . . ? N3 Cu1 O1 98.65(10) . . ? N10 Cu1 O21 83.73(11) . . ? N10 Cu1 O1 95.87(11) . . ? C12 O11 Cu1 113.9(2) . . ? C22 O21 Cu1 111.7(2) . . ? C4 N9 H9 125.8 . . ? C4 N9 C8 108.4(3) . . ? C8 N9 H9 125.8 . . ? C4 N3 Cu1 126.6(2) . . ? C2 N3 Cu1 119.9(2) . . ? C2 N3 C4 113.5(3) . . ? C2 N1 C6 118.8(3) . . ? H6a N6 H6b 120.0 . . ? C6 N6 H6a 120.0 . . ? C6 N6 H6b 120.0 . . ? N9 C4 N3 126.8(3) . . ? N9 C4 C5 109.1(3) . . ? N3 C4 C5 124.1(3) . . ? N3 C2 H2 116.2 . . ? N1 C2 N3 127.6(3) . . ? N1 C2 H2 116.2 . . ? C8 C7 H7 126.8 . . ? C8 C7 C5 106.4(3) . . ? C5 C7 H7 126.8 . . ? Cu1 N10 H10 104.8 . . ? C11 N10 Cu1 108.5(2) . . ? C11 N10 H10 104.4 . . ? C21 N10 Cu1 106.2(2) . . ? C21 N10 H10 114.0 . . ? C21 N10 C11 118.0(3) . . ? N9 C8 H8 125.2 . . ? C7 C8 N9 109.5(3) . . ? C7 C8 H8 125.2 . . ? O11 C12 C11 117.2(3) . . ? O12 C12 O11 124.4(3) . . ? O12 C12 C11 118.4(3) . . ? C4 C5 C7 106.7(3) . . ? C4 C5 C6 116.9(3) . . ? C6 C5 C7 136.4(3) . . ? N1 C6 C5 119.0(3) . . ? N6 C6 N1 117.6(3) . . ? N6 C6 C5 123.4(3) . . ? N10 C11 C12 110.4(3) . . ? N10 C11 H11a 109.6 . . ? N10 C11 H11b 109.6 . . ? C12 C11 H11a 109.6 . . ? C12 C11 H11b 109.6 . . ? H11a C11 H11b 108.1 . . ? O21 C22 C21 117.4(3) . . ? O22 C22 O21 123.8(3) . . ? O22 C22 C21 118.7(3) . . ? N10 C21 C22 110.1(3) . . ? N10 C21 H21a 109.6 . . ? N10 C21 H21b 109.6 . . ? C22 C21 H21a 109.6 . . ? C22 C21 H21b 109.6 . . ? H21a C21 H21b 108.1 . . ? Cu1 O1 H1a 122.6 . . ? Cu1 O1 H1b 122.7 . . ? H1a O1 H1b 108.1 . . ? H2a O2 H2b 106.5 . . ? H3a O3 H3b 94.9 . . ? 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 N9 H9 O21 0.88 2.46 3.011(3) 121.2 . N9 H9 O12 0.88 2.58 3.179(4) 126.4 1_665 N6 H6a O3 0.88 2.35 3.053(4) 136.5 2_666 N6 H6b O21 0.88 2.41 3.057(3) 130.2 2_776 O1 H1a O12 0.87 1.99 2.838(3) 166.7 1_655 O1 H1b N1 0.87 1.91 2.778(3) 172.0 2_666 O2 H2a O12 0.83 2.03 2.839(4) 162.6 1_655 O2 H2b O22 0.84 1.95 2.774(4) 163.7 2_767 O3 H3a O22 0.85 1.92 2.748(4) 164.8 1_445 O3 H3b O2 0.86 1.90 2.729(4) 163.5 . data_C618_Comp.8 _database_code_depnum_ccdc_archive 'CCDC 881143' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_date 2011-04-28 _audit_creation_method ; Olex2 1.1 (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C16 H24 Cu2 N6 O10, 5(H2 O)' _chemical_formula_sum 'C16 H34 Cu2 N6 O15' _chemical_formula_weight 677.57 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0039 0.0018 'Henke tables from the CCTBX' H H 0.0000 0.0000 'Henke tables from the CCTBX' Cu Cu 0.3287 1.3789 'Henke tables from the CCTBX' N N 0.0072 0.0035 'Henke tables from the CCTBX' O O 0.0126 0.0067 'Henke tables from the CCTBX' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M P-1 _cell_length_a 6.9590(14) _cell_length_b 13.536(3) _cell_length_c 14.250(3) _cell_angle_alpha 93.62(3) _cell_angle_beta 102.40(3) _cell_angle_gamma 95.27(3) _cell_volume 1300.7(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used ? _cell_measurement_temperature 100.15 _cell_measurement_theta_max ? _cell_measurement_theta_min ? _exptl_absorpt_coefficient_mu 1.718 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type ? _exptl_absorpt_process_details ? _exptl_crystal_colour ? _exptl_crystal_density_diffrn 1.730 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description ? _exptl_crystal_F_000 700 _exptl_crystal_size_max ? _exptl_crystal_size_mid ? _exptl_crystal_size_min ? _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_unetI/netI 0.0459 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 4376 _diffrn_reflns_theta_full 26.20 _diffrn_reflns_theta_max 26.20 _diffrn_reflns_theta_min 1.57 _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 9.6 _diffrn_measured_fraction_theta_full 0.937 _diffrn_measured_fraction_theta_max 0.937 _diffrn_measurement_device_type 'Single-axis HUBER diffractometer' _diffrn_measurement_method 'CCD rotation images, thick slices' _diffrn_radiation_detector 'ADSC Q210r CCD (binned mode)' _diffrn_radiation_monochromator 'Si 111' _diffrn_radiation_type synchrotron _diffrn_radiation_wavelength 0.73800 _diffrn_source synchrotron _diffrn_source_type 'ESRF-CRG BM16' _reflns_number_gt 3760 _reflns_number_total 4376 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'HKL2000 (Otwinowski & Minor, 1997)' _computing_data_collection 'MxCube (ESRF, 2006)' _computing_data_reduction 'HKL2000 (Otwinowski & Minor, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 1.810 _refine_diff_density_min -1.231 _refine_diff_density_rms 0.150 _refine_ls_extinction_coef 0.0109(19) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 336 _refine_ls_number_reflns 4376 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0723 _refine_ls_R_factor_gt 0.0635 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1036P)^2^+6.2921P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1700 _refine_ls_wR_factor_ref 0.1771 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.18291(9) 0.29204(5) -0.14403(4) 0.0172(2) Uani 1 1 d . B . Cu2 Cu 0.43778(9) 0.19031(5) 0.23330(4) 0.0185(2) Uani 1 1 d . B . O1 O 0.0848(6) 0.3921(3) -0.0375(3) 0.0319(10) Uani 1 1 d . . . H1a H -0.0171 0.3764 -0.0157 0.048 Uiso 1 1 d R . . H1b H 0.1677 0.4303 0.0053 0.048 Uiso 1 1 d R . . O11 O 0.4536(5) 0.3629(3) -0.0987(3) 0.0212(8) Uani 1 1 d . B . O12 O 0.6319(7) 0.5033(4) -0.1163(4) 0.0505(11) Uani 1 1 d . B . O21 O -0.0815(6) 0.2379(3) -0.2188(3) 0.0260(9) Uani 1 1 d . . . O22 O -0.3237(7) 0.2771(4) -0.3344(4) 0.0505(11) Uani 1 1 d . . . O2 O 0.2941(6) 0.3341(3) 0.2197(3) 0.0314(10) Uani 1 1 d . . . H2a H 0.3272 0.3816 0.1883 0.047 Uiso 1 1 d R . . H2b H 0.1795 0.3409 0.2299 0.047 Uiso 1 1 d R . . O31 O 0.2166(5) 0.1201(3) 0.2751(2) 0.0190(8) Uani 1 1 d . B . O32 O 0.1109(6) 0.0917(4) 0.4073(3) 0.0417(9) Uani 1 1 d . C . O41 O 0.6948(5) 0.2544(3) 0.2197(3) 0.0232(9) Uani 1 1 d . B . O42 O 0.9719(6) 0.3372(4) 0.3061(3) 0.0417(9) Uani 1 1 d . C . N10 N 0.1671(8) 0.3838(4) -0.2480(4) 0.0294(12) Uani 1 1 d . . . N30 N 0.5573(7) 0.2140(4) 0.3750(3) 0.0256(11) Uani 1 1 d . . . N1 N 0.2269(6) 0.1765(3) -0.0650(3) 0.0163(9) Uani 1 1 d . . . N3 N 0.3480(6) 0.1373(3) 0.0961(3) 0.0159(9) Uani 1 1 d . . . N6 N 0.0867(7) 0.0547(4) -0.1906(3) 0.0214(10) Uani 1 1 d . . . H6a H 0.0621 0.1020 -0.2297 0.026 Uiso 1 1 calc R B . H6b H 0.0530 -0.0081 -0.2124 0.026 Uiso 1 1 calc R . . C7 C 0.1991(8) -0.0999(4) -0.0386(4) 0.0187(11) Uani 1 1 d . B . H7 H 0.1452 -0.1440 -0.0946 0.022 Uiso 1 1 calc R . . N9 N 0.3362(6) -0.0400(3) 0.1147(3) 0.0182(9) Uani 1 1 d . . . H9 H 0.3880 -0.0383 0.1769 0.022 Uiso 1 1 calc R B . C11 C 0.3058(10) 0.4704(6) -0.2117(5) 0.0416(13) Uani 1 1 d . B . H11a H 0.2387 0.5213 -0.1820 0.050 Uiso 1 1 calc R . . H11b H 0.3535 0.4991 -0.2659 0.050 Uiso 1 1 calc R . . C12 C 0.4798(9) 0.4440(5) -0.1379(5) 0.0346(11) Uani 1 1 d . . . C23 C 0.2359(14) 0.3297(6) -0.3285(5) 0.052(2) Uani 1 1 d . B . H23a H 0.3746 0.3180 -0.3062 0.078 Uiso 1 1 calc R . . H23b H 0.2235 0.3701 -0.3837 0.078 Uiso 1 1 calc R . . H23c H 0.1543 0.2657 -0.3480 0.078 Uiso 1 1 calc R . . C21 C -0.0398(10) 0.3979(6) -0.2785(6) 0.0416(13) Uani 1 1 d . B . H21a H -0.0666 0.4223 -0.3436 0.050 Uiso 1 1 calc R A 1 H21b H -0.0771 0.4471 -0.2330 0.050 Uiso 1 1 calc R A 1 C22 C -0.1580(9) 0.2959(5) -0.2798(5) 0.0346(11) Uani 1 1 d . B 1 C31A C 0.3950(11) 0.2151(7) 0.4195(5) 0.0191(15) Uani 0.659(6) 1 d P C 1 H31a H 0.3421 0.2805 0.4154 0.023 Uiso 0.659(6) 1 calc PR C 1 H31b H 0.4362 0.2030 0.4884 0.023 Uiso 0.659(6) 1 calc PR C 1 C31B C 0.463(2) 0.1420(13) 0.4218(11) 0.0191(15) Uani 0.341(6) 1 d P C 2 H31c H 0.4756 0.1646 0.4905 0.023 Uiso 0.341(6) 1 calc PR C 2 H31d H 0.5200 0.0780 0.4178 0.023 Uiso 0.341(6) 1 calc PR C 2 C32 C 0.2323(9) 0.1299(5) 0.3645(4) 0.0320(11) Uani 1 1 d . . . C43A C 0.6669(14) 0.1206(7) 0.4061(7) 0.0297(19) Uani 0.659(6) 1 d P C 1 H43a H 0.5701 0.0615 0.3968 0.045 Uiso 0.659(6) 1 calc PR C 1 H43b H 0.7351 0.1318 0.4742 0.045 Uiso 0.659(6) 1 calc PR C 1 H43c H 0.7638 0.1104 0.3666 0.045 Uiso 0.659(6) 1 calc PR C 1 C43B C 0.487(3) 0.3207(14) 0.4168(12) 0.0297(19) Uani 0.341(6) 1 d P C 2 H43d H 0.5371 0.3763 0.3849 0.045 Uiso 0.341(6) 1 calc PR C 2 H43e H 0.5397 0.3319 0.4866 0.045 Uiso 0.341(6) 1 calc PR C 2 H43f H 0.3417 0.3160 0.4034 0.045 Uiso 0.341(6) 1 calc PR C 2 C41A C 0.7063(13) 0.2978(7) 0.3859(6) 0.0226(17) Uani 0.659(6) 1 d P C 1 H41a H 0.8065 0.2966 0.4467 0.027 Uiso 0.659(6) 1 calc PR C 1 H41b H 0.6451 0.3609 0.3882 0.027 Uiso 0.659(6) 1 calc PR C 1 C41B C 0.763(2) 0.2365(15) 0.3875(11) 0.0226(17) Uani 0.341(6) 1 d P C 2 H41c H 0.8289 0.1746 0.3927 0.027 Uiso 0.341(6) 1 calc PR C 2 H41d H 0.8168 0.2804 0.4475 0.027 Uiso 0.341(6) 1 calc PR C 2 C42 C 0.8061(9) 0.2906(5) 0.2979(4) 0.0320(11) Uani 1 1 d . . . C2 C 0.3077(7) 0.1998(4) 0.0287(4) 0.0150(10) Uani 1 1 d . B . H2 H 0.3395 0.2687 0.0490 0.018 Uiso 1 1 calc R . . C4 C 0.3061(7) 0.0394(4) 0.0627(4) 0.0156(11) Uani 1 1 d . B . C5 C 0.2216(7) 0.0063(4) -0.0328(4) 0.0164(11) Uani 1 1 d . . . C6 C 0.1748(7) 0.0782(4) -0.0985(4) 0.0161(11) Uani 1 1 d . B . C8 C 0.2704(8) -0.1250(4) 0.0519(4) 0.0196(11) Uani 1 1 d . B . H8 H 0.2748 -0.1913 0.0699 0.023 Uiso 1 1 calc R . . O3 O -0.2219(6) 0.3531(3) 0.0532(3) 0.0293(9) Uani 1 1 d . . . O7 O 0.5367(14) 0.4367(8) 0.5539(8) 0.121(3) Uani 1 1 d . . . O5 O 0.8837(7) 0.9077(3) 0.3982(3) 0.0329(10) Uani 1 1 d . . . O6 O 0.1461(7) 0.4559(4) 0.4707(3) 0.0376(11) Uani 1 1 d . . . O4 O 0.4899(7) 0.9104(4) 0.2980(4) 0.0469(14) 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 Cu1 0.0149(4) 0.0153(4) 0.0178(4) 0.0043(3) -0.0044(2) -0.0008(2) Cu2 0.0134(4) 0.0242(5) 0.0136(4) 0.0018(3) -0.0030(2) -0.0063(3) O1 0.019(2) 0.030(3) 0.043(3) -0.0103(19) 0.0050(18) -0.0029(17) O11 0.0182(19) 0.020(2) 0.0222(19) 0.0068(15) -0.0018(15) -0.0024(15) O12 0.0279(18) 0.055(3) 0.056(2) 0.0286(19) -0.0172(16) -0.0166(16) O21 0.020(2) 0.026(2) 0.026(2) 0.0099(17) -0.0083(16) -0.0036(16) O22 0.0279(18) 0.055(3) 0.056(2) 0.0286(19) -0.0172(16) -0.0166(16) O2 0.036(2) 0.023(2) 0.043(2) 0.0076(19) 0.024(2) 0.0074(19) O31 0.0179(19) 0.020(2) 0.0160(18) 0.0020(14) -0.0012(14) -0.0035(15) O32 0.0227(16) 0.072(3) 0.0241(15) 0.0004(15) 0.0027(12) -0.0230(16) O41 0.0155(18) 0.033(2) 0.0162(18) -0.0023(16) -0.0012(14) -0.0086(16) O42 0.0227(16) 0.072(3) 0.0241(15) 0.0004(15) 0.0027(12) -0.0230(16) N10 0.031(3) 0.023(3) 0.027(3) 0.009(2) -0.009(2) -0.004(2) N30 0.015(2) 0.038(3) 0.017(2) 0.006(2) -0.0056(18) -0.011(2) N1 0.013(2) 0.019(3) 0.014(2) 0.0025(17) -0.0017(16) 0.0004(17) N3 0.012(2) 0.019(3) 0.015(2) 0.0013(17) -0.0003(16) 0.0003(17) N6 0.024(2) 0.018(3) 0.016(2) 0.0010(18) -0.0045(18) -0.0045(19) C7 0.018(3) 0.013(3) 0.024(3) -0.001(2) 0.002(2) 0.001(2) N9 0.016(2) 0.020(3) 0.017(2) 0.0039(18) -0.0001(17) 0.0018(18) C11 0.026(2) 0.039(3) 0.053(3) 0.022(2) -0.008(2) -0.003(2) C12 0.024(2) 0.036(3) 0.039(2) 0.017(2) -0.0037(19) -0.0031(19) C23 0.081(6) 0.044(5) 0.030(4) 0.004(3) 0.010(4) 0.005(4) C21 0.026(2) 0.039(3) 0.053(3) 0.022(2) -0.008(2) -0.003(2) C22 0.024(2) 0.036(3) 0.039(2) 0.017(2) -0.0037(19) -0.0031(19) C31A 0.014(4) 0.025(5) 0.015(3) 0.001(3) -0.001(3) -0.004(3) C31B 0.014(4) 0.025(5) 0.015(3) 0.001(3) -0.001(3) -0.004(3) C32 0.018(2) 0.050(3) 0.022(2) -0.0009(19) -0.0004(16) -0.0142(19) C43A 0.028(4) 0.031(5) 0.027(4) 0.004(3) -0.004(3) 0.009(4) C43B 0.028(4) 0.031(5) 0.027(4) 0.004(3) -0.004(3) 0.009(4) C41A 0.019(4) 0.027(5) 0.017(3) -0.004(4) -0.001(3) -0.009(3) C41B 0.019(4) 0.027(5) 0.017(3) -0.004(4) -0.001(3) -0.009(3) C42 0.018(2) 0.050(3) 0.022(2) -0.0009(19) -0.0004(16) -0.0142(19) C2 0.012(2) 0.013(3) 0.018(2) -0.0021(19) -0.0008(19) -0.0004(19) C4 0.011(2) 0.015(3) 0.018(2) 0.002(2) -0.0015(19) -0.0005(19) C5 0.013(2) 0.015(3) 0.020(3) 0.002(2) 0.001(2) 0.002(2) C6 0.012(2) 0.016(3) 0.018(2) 0.001(2) 0.0008(19) -0.002(2) C8 0.017(3) 0.014(3) 0.027(3) 0.003(2) 0.004(2) 0.004(2) O3 0.024(2) 0.029(3) 0.032(2) 0.0039(18) 0.0009(17) -0.0002(17) O7 0.091(6) 0.128(9) 0.139(8) 0.026(7) 0.012(6) 0.005(6) O5 0.034(2) 0.035(3) 0.023(2) 0.0017(18) -0.0033(17) -0.0058(19) O6 0.033(2) 0.040(3) 0.034(2) -0.001(2) -0.0071(19) 0.004(2) O4 0.036(3) 0.054(4) 0.040(3) 0.024(2) -0.015(2) -0.010(2) _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 2.227(4) . ? Cu1 O11 1.988(4) . ? Cu1 O21 1.967(4) . ? Cu1 N10 1.984(5) . ? Cu1 N1 1.993(4) . ? Cu2 O2 2.268(4) . ? Cu2 O31 1.955(4) . ? Cu2 O41 1.969(4) . ? Cu2 N30 2.005(4) . ? Cu2 N3 1.986(4) . ? O11 C12 1.279(7) . ? O12 C12 1.238(8) . ? O21 C22 1.273(7) . ? O22 C22 1.239(8) . ? O31 C32 1.252(7) . ? O32 C32 1.240(7) . ? O41 C42 1.254(7) . ? O42 C42 1.242(7) . ? N10 C11 1.441(8) . ? N10 C23 1.509(9) . ? N10 C21 1.445(8) . ? N30 C31A 1.410(9) . ? N30 C31B 1.408(16) . ? N30 C43A 1.575(10) . ? N30 C43B 1.682(19) . ? N30 C41A 1.442(10) . ? N30 C41B 1.409(17) . ? N1 C2 1.338(7) . ? N1 C6 1.373(7) . ? N3 C2 1.322(7) . ? N3 C4 1.363(7) . ? N6 C6 1.329(7) . ? C7 C5 1.427(8) . ? C7 C8 1.356(8) . ? N9 C4 1.350(7) . ? N9 C8 1.389(7) . ? C11 C12 1.510(8) . ? C21 C22 1.537(9) . ? C31A C32 1.578(10) . ? C31B C32 1.623(15) . ? C41A C42 1.561(10) . ? C41B C42 1.579(17) . ? C4 C5 1.389(7) . ? C5 C6 1.405(7) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O11 Cu1 O1 88.03(16) . . ? O11 Cu1 N1 96.59(16) . . ? O21 Cu1 O1 97.43(17) . . ? O21 Cu1 O11 165.57(16) . . ? O21 Cu1 N10 82.97(18) . . ? O21 Cu1 N1 95.82(17) . . ? N10 Cu1 O1 97.4(2) . . ? N10 Cu1 O11 83.09(18) . . ? N10 Cu1 N1 164.3(2) . . ? N1 Cu1 O1 98.24(17) . . ? O31 Cu2 O2 93.34(16) . . ? O31 Cu2 O41 167.08(15) . . ? O31 Cu2 N30 84.07(17) . . ? O31 Cu2 N3 94.94(17) . . ? O41 Cu2 O2 93.02(17) . . ? O41 Cu2 N30 84.07(17) . . ? O41 Cu2 N3 95.41(17) . . ? N30 Cu2 O2 96.2(2) . . ? N3 Cu2 O2 97.15(17) . . ? N3 Cu2 N30 166.6(2) . . ? C12 O11 Cu1 113.6(4) . . ? C22 O21 Cu1 112.9(4) . . ? C32 O31 Cu2 113.4(3) . . ? C42 O41 Cu2 113.9(4) . . ? C11 N10 Cu1 107.8(4) . . ? C11 N10 C23 108.3(6) . . ? C11 N10 C21 118.0(6) . . ? C23 N10 Cu1 105.9(4) . . ? C21 N10 Cu1 106.0(4) . . ? C21 N10 C23 110.2(6) . . ? C31A N30 Cu2 105.2(4) . . ? C31A N30 C43A 107.7(6) . . ? C31A N30 C43B 58.0(8) . . ? C31A N30 C41A 122.4(6) . . ? C31B N30 Cu2 107.6(7) . . ? C31B N30 C31A 47.4(8) . . ? C31B N30 C43A 61.7(8) . . ? C31B N30 C43B 102.5(10) . . ? C31B N30 C41A 146.3(8) . . ? C31B N30 C41B 125.8(10) . . ? C43A N30 Cu2 107.3(4) . . ? C43A N30 C43B 143.8(7) . . ? C43B N30 Cu2 108.6(6) . . ? C41A N30 Cu2 106.0(4) . . ? C41A N30 C43A 107.3(6) . . ? C41A N30 C43B 66.7(8) . . ? C41B N30 Cu2 108.3(7) . . ? C41B N30 C31A 145.5(8) . . ? C41B N30 C43A 69.6(9) . . ? C41B N30 C43B 102.9(11) . . ? C41B N30 C41A 39.0(8) . . ? C2 N1 Cu1 115.3(4) . . ? C2 N1 C6 119.3(4) . . ? C6 N1 Cu1 125.4(3) . . ? C2 N3 Cu2 119.4(4) . . ? C2 N3 C4 114.2(4) . . ? C4 N3 Cu2 126.1(3) . . ? C8 C7 C5 106.0(5) . . ? C4 N9 C8 107.4(4) . . ? N10 C11 C12 110.9(5) . . ? O11 C12 C11 116.4(5) . . ? O12 C12 O11 124.8(5) . . ? O12 C12 C11 118.7(6) . . ? N10 C21 C22 106.8(5) . . ? O21 C22 C21 116.4(5) . . ? O22 C22 O21 124.0(6) . . ? O22 C22 C21 119.5(6) . . ? N30 C31A C32 107.2(6) . . ? N30 C31B C32 104.9(10) . . ? O31 C32 C31A 114.6(5) . . ? O31 C32 C31B 111.3(7) . . ? O32 C32 O31 124.8(5) . . ? O32 C32 C31A 119.2(6) . . ? O32 C32 C31B 116.3(7) . . ? C31A C32 C31B 41.4(7) . . ? N30 C41A C42 108.1(6) . . ? N30 C41B C42 108.7(11) . . ? O41 C42 C41A 115.6(5) . . ? O41 C42 C41B 112.9(8) . . ? O42 C42 O41 124.9(6) . . ? O42 C42 C41A 117.9(6) . . ? O42 C42 C41B 117.8(7) . . ? C41A C42 C41B 35.3(7) . . ? N3 C2 N1 127.0(5) . . ? N3 C4 C5 123.9(5) . . ? N9 C4 N3 127.0(5) . . ? N9 C4 C5 109.2(5) . . ? C4 C5 C7 107.1(5) . . ? C4 C5 C6 117.9(5) . . ? C6 C5 C7 135.0(5) . . ? N1 C6 C5 117.6(5) . . ? N6 C6 N1 119.6(5) . . ? N6 C6 C5 122.8(5) . . ? C7 C8 N9 110.3(5) . . ? 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 O1 H1a O3 0.85 1.91 2.751(6) 170.3 . O1 H1b O12 0.85 1.97 2.817(7) 169.7 2_665 O2 H2a O12 0.85 1.95 2.794(6) 172.3 2_665 O2 H2b O42 0.85 1.98 2.781(6) 155.4 1_455 N9 H9 O4 0.88 1.92 2.751(6) 157.3 1_545 data_C616_Comp.9 _database_code_depnum_ccdc_archive 'CCDC 881144' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety ? _chemical_formula_sum 'C17 H17 Cu N5 O4' _chemical_formula_weight 418.90 _chemical_melting_point ? 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' Cu Cu 0.3201 1.2651 '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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _cell_length_a 8.7865(18) _cell_length_b 21.951(5) _cell_length_c 9.1750(19) _cell_angle_alpha 90.00 _cell_angle_beta 107.828(3) _cell_angle_gamma 90.00 _cell_volume 1684.7(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 2412 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.21 _cell_measurement_theta_min 2.61 _exptl_absorpt_coefficient_mu 1.333 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5110 _exptl_absorpt_correction_type MULTI-SCAN _exptl_absorpt_process_details 'Bruker SADABS, 2010' _exptl_crystal_colour 'pale blue' _exptl_crystal_density_diffrn 1.652 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 860 _exptl_crystal_size_max 0.10 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.06 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 3372 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 1.86 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.981 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measurement_device_type 'Bruker SMART APEX' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _reflns_number_gt 2964 _reflns_number_total 3465 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ? _computing_data_collection ? _computing_data_reduction ? _computing_molecular_graphics ? _computing_publication_material ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.786 _refine_diff_density_min -0.405 _refine_diff_density_rms 0.101 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 245 _refine_ls_number_reflns 3465 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0499 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.011 _refine_ls_shift/su_mean 0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0559P)^2^+3.8595P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1262 _refine_ls_wR_factor_ref 0.1342 _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. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 0.93957(7) 0.30344(2) 0.82792(5) 0.01888(19) Uani 1 1 d . . . O11 O 0.9298(4) 0.36041(14) 0.6612(3) 0.0254(7) Uani 1 1 d . . . O22 O 0.7681(3) 0.25978(14) 1.1658(3) 0.0224(7) Uani 1 1 d . . . O21 O 0.9178(3) 0.26227(14) 1.0097(3) 0.0213(7) Uani 1 1 d . . . N10 N 0.7882(4) 0.36368(16) 0.8745(4) 0.0191(8) Uani 1 1 d . . . O12 O 0.7443(4) 0.41657(16) 0.4936(3) 0.0333(8) Uani 1 1 d . . . C4 C 1.1683(5) 0.20010(19) 0.8704(4) 0.0193(9) Uani 1 1 d . . . N6 N 1.5426(4) 0.17852(18) 0.7876(4) 0.0250(9) Uani 1 1 d . . . H6a H 1.6059 0.2008 0.7511 0.030 Uiso 1 1 calc R . . H6b H 1.5686 0.1407 0.8160 0.030 Uiso 1 1 calc R . . N1 N 1.3733(4) 0.26012(18) 0.7550(4) 0.0223(8) Uani 1 1 d . . . N9 N 1.0803(4) 0.16208(17) 0.9280(4) 0.0221(8) Uani 1 1 d . . . H9 H 0.9893 0.1710 0.9444 0.026 Uiso 1 1 calc R . . C31 C 0.8937(5) 0.4118(2) 0.9684(5) 0.0230(9) Uani 1 1 d . . . H31a H 0.9581 0.4297 0.9075 0.028 Uiso 1 1 calc R . . H31b H 0.9687 0.3923 1.0595 0.028 Uiso 1 1 calc R . . C6 C 1.4077(5) 0.2021(2) 0.7999(4) 0.0199(10) Uani 1 1 d . . . C22 C 0.8017(5) 0.2812(2) 1.0537(4) 0.0194(9) Uani 1 1 d . . . C5 C 1.3036(5) 0.1688(2) 0.8596(4) 0.0196(9) Uani 1 1 d . . . C21 C 0.6979(5) 0.3302(2) 0.9601(4) 0.0176(9) Uani 1 1 d . . . H21a H 0.6011 0.3118 0.8878 0.021 Uiso 1 1 calc R . . H21b H 0.6637 0.3585 1.0280 0.021 Uiso 1 1 calc R . . N3 N 1.1355(4) 0.25927(16) 0.8298(4) 0.0197(8) Uani 1 1 d . . . C11 C 0.6921(5) 0.3854(2) 0.7213(4) 0.0218(9) Uani 1 1 d . . . H11a H 0.6476 0.4262 0.7304 0.026 Uiso 1 1 calc R . . H11b H 0.6018 0.3572 0.6775 0.026 Uiso 1 1 calc R . . C2 C 1.2426(5) 0.2850(2) 0.7711(4) 0.0217(9) Uani 1 1 d . . . H2 H 1.2218 0.3259 0.7372 0.026 Uiso 1 1 calc R . . C12 C 0.7965(5) 0.3889(2) 0.6164(5) 0.0252(10) Uani 1 1 d . . . C34 C 0.7020(6) 0.5063(2) 1.2100(5) 0.0301(11) Uani 1 1 d . . . H34 H 0.6830 0.5040 1.3064 0.036 Uiso 1 1 calc R . . C32 C 0.8083(5) 0.4628(2) 1.0217(5) 0.0257(10) Uani 1 1 d . . . C36 C 0.6790(6) 0.5603(2) 0.9824(6) 0.0339(11) Uani 1 1 d . . . H36 H 0.6443 0.5954 0.9205 0.041 Uiso 1 1 calc R . . C35 C 0.6510(6) 0.5559(2) 1.1193(5) 0.0317(11) Uani 1 1 d . . . H35 H 0.5955 0.5876 1.1521 0.038 Uiso 1 1 calc R . . C37 C 0.7577(6) 0.5141(2) 0.9324(5) 0.0294(11) Uani 1 1 d . . . H37 H 0.7772 0.5176 0.8364 0.035 Uiso 1 1 calc R . . C7 C 1.2945(5) 0.1082(2) 0.9152(5) 0.0245(10) Uani 1 1 d . . . H7 H 1.3681 0.0758 0.9219 0.029 Uiso 1 1 calc R . . C33 C 0.7811(5) 0.4592(2) 1.1635(5) 0.0293(11) Uani 1 1 d . . . H33 H 0.8166 0.4247 1.2276 0.035 Uiso 1 1 calc R . . C8 C 1.1584(5) 0.1068(2) 0.9563(5) 0.0282(10) Uani 1 1 d . . . H8 H 1.1220 0.0724 0.9989 0.034 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cu1 0.0190(3) 0.0210(3) 0.0183(3) 0.0004(2) 0.00826(18) 0.0013(2) O11 0.0303(17) 0.0258(17) 0.0260(15) 0.0064(13) 0.0174(13) 0.0051(14) O22 0.0202(15) 0.0294(17) 0.0192(14) 0.0024(13) 0.0086(12) 0.0046(13) O21 0.0213(15) 0.0249(17) 0.0205(13) 0.0003(12) 0.0106(12) 0.0036(13) N10 0.0205(18) 0.0206(19) 0.0169(16) -0.0006(15) 0.0068(15) -0.0020(16) O12 0.0362(19) 0.038(2) 0.0284(16) 0.0077(15) 0.0143(15) 0.0016(16) C4 0.018(2) 0.025(2) 0.0155(18) -0.0014(18) 0.0064(16) 0.0016(19) N6 0.025(2) 0.025(2) 0.0299(19) 0.0014(16) 0.0156(17) 0.0008(17) N1 0.0141(17) 0.035(2) 0.0202(17) -0.0024(16) 0.0084(15) -0.0022(17) N9 0.0198(17) 0.025(2) 0.0255(18) -0.0025(16) 0.0128(15) -0.0010(16) C31 0.020(2) 0.024(2) 0.025(2) -0.0049(18) 0.0059(18) -0.0051(19) C6 0.016(2) 0.030(3) 0.0141(18) -0.0063(18) 0.0045(17) -0.0013(18) C22 0.021(2) 0.022(2) 0.0174(19) -0.0040(17) 0.0097(17) -0.0018(19) C5 0.017(2) 0.028(2) 0.0157(19) -0.0047(18) 0.0067(17) -0.0027(19) C21 0.0138(19) 0.023(2) 0.0198(19) -0.0003(17) 0.0103(17) -0.0016(18) N3 0.0177(18) 0.0218(19) 0.0191(16) -0.0021(15) 0.0047(14) -0.0012(16) C11 0.022(2) 0.022(2) 0.021(2) 0.0026(18) 0.0065(18) 0.0023(19) C2 0.021(2) 0.026(2) 0.0183(19) -0.0024(18) 0.0066(17) -0.0049(19) C12 0.028(2) 0.023(2) 0.026(2) 0.000(2) 0.0094(19) 0.003(2) C34 0.032(3) 0.034(3) 0.026(2) -0.009(2) 0.010(2) 0.003(2) C32 0.025(2) 0.027(3) 0.026(2) -0.003(2) 0.0090(19) -0.003(2) C36 0.030(3) 0.025(3) 0.046(3) 0.005(2) 0.011(2) 0.000(2) C35 0.026(2) 0.031(3) 0.038(3) -0.008(2) 0.010(2) 0.001(2) C37 0.030(2) 0.029(3) 0.031(2) -0.001(2) 0.013(2) -0.005(2) C7 0.026(2) 0.026(2) 0.023(2) 0.0005(19) 0.0100(18) 0.002(2) C33 0.029(2) 0.030(3) 0.026(2) 0.001(2) 0.005(2) 0.000(2) C8 0.032(2) 0.028(3) 0.024(2) -0.0005(19) 0.010(2) -0.002(2) _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 O11 1.957(3) . ? Cu1 O22 2.244(3) 4_565 ? Cu1 O21 1.957(3) . ? Cu1 N10 2.012(3) . ? Cu1 N3 1.971(3) . ? O11 C12 1.280(5) . ? O22 Cu1 2.244(3) 4_566 ? O22 C22 1.246(5) . ? O21 C22 1.276(5) . ? N10 C31 1.493(5) . ? N10 C21 1.473(5) . ? N10 C11 1.480(5) . ? O12 C12 1.237(5) . ? C4 N9 1.350(5) . ? C4 C5 1.403(6) . ? C4 N3 1.358(5) . ? N6 C6 1.329(5) . ? N1 C6 1.344(6) . ? N1 C2 1.320(5) . ? N9 C8 1.378(6) . ? C31 C32 1.509(6) . ? C6 C5 1.407(6) . ? C22 C21 1.499(6) . ? C5 C7 1.436(6) . ? N3 C2 1.343(5) . ? C11 C12 1.521(6) . ? C34 C35 1.360(7) . ? C34 C33 1.385(6) . ? C32 C37 1.384(7) . ? C32 C33 1.395(6) . ? C36 C35 1.355(7) . ? C36 C37 1.384(7) . ? C7 C8 1.360(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 O11 Cu1 O22 91.00(12) . 4_565 ? O11 Cu1 O21 165.63(12) . . ? O11 Cu1 N10 82.67(13) . . ? O11 Cu1 N3 98.65(13) . . ? O21 Cu1 O22 93.34(11) . 4_565 ? O21 Cu1 N10 83.06(12) . . ? O21 Cu1 N3 94.49(13) . . ? N10 Cu1 O22 101.19(12) . 4_565 ? N3 Cu1 O22 96.25(12) . 4_565 ? N3 Cu1 N10 162.50(14) . . ? C12 O11 Cu1 112.4(3) . . ? C22 O22 Cu1 120.0(3) . 4_566 ? C22 O21 Cu1 114.6(3) . . ? C31 N10 Cu1 104.7(2) . . ? C21 N10 Cu1 106.5(3) . . ? C21 N10 C31 112.7(3) . . ? C21 N10 C11 115.1(3) . . ? C11 N10 Cu1 103.4(2) . . ? C11 N10 C31 113.1(3) . . ? N9 C4 C5 108.9(4) . . ? N9 C4 N3 126.9(4) . . ? N3 C4 C5 124.2(4) . . ? C2 N1 C6 118.7(4) . . ? C4 N9 C8 107.8(4) . . ? N10 C31 C32 115.4(3) . . ? N6 C6 N1 117.8(4) . . ? N6 C6 C5 122.2(4) . . ? N1 C6 C5 120.0(4) . . ? O22 C22 O21 123.6(4) . . ? O22 C22 C21 119.2(4) . . ? O21 C22 C21 117.2(3) . . ? C4 C5 C6 116.0(4) . . ? C4 C5 C7 106.7(4) . . ? C6 C5 C7 137.2(4) . . ? N10 C21 C22 109.4(3) . . ? C4 N3 Cu1 125.7(3) . . ? C2 N3 Cu1 120.4(3) . . ? C2 N3 C4 113.4(4) . . ? N10 C11 C12 109.8(3) . . ? N1 C2 N3 127.7(4) . . ? O11 C12 C11 116.2(4) . . ? O12 C12 O11 125.4(4) . . ? O12 C12 C11 118.3(4) . . ? C35 C34 C33 120.8(4) . . ? C37 C32 C31 120.8(4) . . ? C37 C32 C33 118.9(4) . . ? C33 C32 C31 120.3(4) . . ? C35 C36 C37 120.4(5) . . ? C36 C35 C34 120.4(5) . . ? C32 C37 C36 120.2(4) . . ? C8 C7 C5 105.6(4) . . ? C34 C33 C32 119.4(4) . . ? C7 C8 N9 110.9(4) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N6 H6a O22 0.88 2.02 2.890(4) 171.9 4_665 N6 H6b O12 0.88 2.25 2.996(4) 142.9 4_666 N9 H9 O11 0.88 2.32 2.882(4) 122.1 4_566 N9 H9 O21 0.88 2.24 2.847(4) 126.0 . data_C613_Comp.10 _database_code_depnum_ccdc_archive 'CCDC 881145' #TrackingRef 'Deazapurine_Dalton.cif' _audit_creation_method SHELXL-97 _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C18 H19 Cu N5 O4' _chemical_formula_sum 'C18 H19 Cu N5 O4' _chemical_formula_weight 432.92 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cu Cu 0.3201 1.2651 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, y+1/2, -z+1/2' 3 '-x, -y, -z' 4 'x, -y-1/2, z-1/2' _symmetry_cell_setting Monoclinic _symmetry_Int_Tables_number 14 _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _cell_length_a 8.8187(3) _cell_length_b 24.1440(10) _cell_length_c 8.9808(3) _cell_angle_alpha 90.00 _cell_angle_beta 110.342(2) _cell_angle_gamma 90.00 _cell_volume 1792.93(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 6924 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.605 _cell_measurement_theta_min 2.463 _exptl_absorpt_coefficient_mu 1.255 _exptl_absorpt_correction_T_max 0.9633 _exptl_absorpt_correction_T_min 0.4371 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details SADABS _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.604 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 892 _exptl_crystal_size_max 0.79 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.03 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0597 _diffrn_reflns_av_sigmaI/netI 0.0449 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 31679 _diffrn_reflns_theta_full 26.37 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 1.69 _diffrn_ambient_temperature 100(2) _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker X8 KappaAPEXII' _diffrn_measurement_method 'omega and phi scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _reflns_number_gt 2941 _reflns_number_total 3659 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'APEX2 sOFTWARE (bRUKER, 2011)' _computing_data_collection 'APEX2 sOFTWARE (bRUKER, 2011)' _computing_data_reduction 'APEX2 sOFTWARE (bRUKER, 2011)' _computing_molecular_graphics 'PLATON (Spek, 2009)' _computing_publication_material 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.779 _refine_diff_density_min -0.571 _refine_diff_density_rms 0.101 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.181 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 253 _refine_ls_number_reflns 3659 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0711 _refine_ls_R_factor_gt 0.0501 _refine_ls_restrained_S_all 1.181 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0225P)^2^+4.4521P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0906 _refine_ls_wR_factor_ref 0.0979 _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. ; _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 1.00342(5) 0.197654(18) 0.67958(5) 0.01001(12) Uani 1 1 d . . . O11 O 1.0264(3) 0.15226(10) 0.8652(3) 0.0135(5) Uani 1 1 d . . . O12 O 1.2127(3) 0.09959(11) 1.0401(3) 0.0193(6) Uani 1 1 d . . . O21 O 1.0218(3) 0.23422(10) 0.4931(3) 0.0128(5) Uani 1 1 d . . . O22 O 1.1799(3) 0.23969(10) 0.3462(3) 0.0128(5) Uani 1 1 d . . . N10 N 1.1562(3) 0.14213(12) 0.6388(3) 0.0115(6) Uani 1 1 d . . . N1 N 0.5765(3) 0.23905(13) 0.7583(3) 0.0144(6) Uani 1 1 d . . . N3 N 0.8051(3) 0.23816(12) 0.6731(3) 0.0115(6) Uani 1 1 d . . . N6 N 0.4234(3) 0.31717(13) 0.7510(3) 0.0166(7) Uani 1 1 d . . . H6a H 0.3600 0.2964 0.7824 0.020 Uiso 1 1 d R . . H6b H 0.3934 0.3491 0.7039 0.020 Uiso 1 1 d R . . N9 N 0.8676(3) 0.32762(12) 0.5855(3) 0.0134(6) Uani 1 1 d . . . H9 H 0.9548 0.3185 0.5646 0.016 Uiso 1 1 d R . . C11 C 1.2547(4) 0.12287(16) 0.8001(4) 0.0152(8) Uani 1 1 d . . . H11a H 1.3506 0.1471 0.8437 0.018 Uiso 1 1 d R . . H11b H 1.2932 0.0847 0.7936 0.018 Uiso 1 1 d R . . C12 C 1.1574(4) 0.12360(15) 0.9113(4) 0.0136(7) Uani 1 1 d . . . C21 C 1.2472(4) 0.17315(15) 0.5555(4) 0.0122(7) Uani 1 1 d . . . H21a H 1.2810 0.1476 0.4866 0.015 Uiso 1 1 d R . . H21b H 1.3458 0.1894 0.6341 0.015 Uiso 1 1 d R . . C22 C 1.1428(4) 0.21891(14) 0.4555(4) 0.0107(7) Uani 1 1 d . . . C31 C 1.0659(4) 0.09571(16) 0.5350(4) 0.0177(8) Uani 1 1 d . . . H31a H 1.1440 0.0665 0.5329 0.021 Uiso 1 1 d R . . H31b H 1.0149 0.1098 0.4253 0.021 Uiso 1 1 d R . . C32 C 0.9371(5) 0.07028(15) 0.5878(4) 0.0163(8) Uani 1 1 d . . . C33 C 0.9688(4) 0.02582(15) 0.6919(4) 0.0184(8) Uani 1 1 d . . . H33 H 1.0730 0.0092 0.7264 0.022 Uiso 1 1 d R . . C34 C 0.8502(5) 0.00507(15) 0.7466(4) 0.0187(8) Uani 1 1 d . . . H34 H 0.8741 -0.0255 0.8176 0.022 Uiso 1 1 d R . . C35 C 0.6974(4) 0.02884(15) 0.6980(4) 0.0175(8) Uani 1 1 d . . . C36 C 0.6639(5) 0.07271(16) 0.5911(4) 0.0206(8) Uani 1 1 d . . . H36 H 0.5591 0.0889 0.5552 0.025 Uiso 1 1 d R . . C37 C 0.7821(5) 0.09309(16) 0.5363(4) 0.0195(8) Uani 1 1 d . . . H37 H 0.7571 0.1230 0.4629 0.023 Uiso 1 1 d R . . C38 C 0.5699(5) 0.00805(17) 0.7621(5) 0.0249(9) Uani 1 1 d . . . H38a H 0.4652 0.0061 0.6755 0.037 Uiso 1 1 d R . . H38b H 0.5622 0.0335 0.8442 0.037 Uiso 1 1 d R . . H38c H 0.6000 -0.0289 0.8080 0.037 Uiso 1 1 d R . . C2 C 0.6997(4) 0.21498(15) 0.7315(4) 0.0124(7) Uani 1 1 d . . . H2 H 0.7150 0.1767 0.7567 0.015 Uiso 1 1 d R . . C4 C 0.7788(4) 0.29282(14) 0.6415(4) 0.0105(7) Uani 1 1 d . . . C5 C 0.6525(4) 0.32309(15) 0.6623(4) 0.0122(7) Uani 1 1 d . . . C6 C 0.5488(4) 0.29358(15) 0.7235(4) 0.0136(7) Uani 1 1 d . . . C7 C 0.6668(4) 0.37873(15) 0.6140(4) 0.0158(8) Uani 1 1 d . . . H7 H 0.5984 0.4091 0.6146 0.019 Uiso 1 1 d R . . C8 C 0.7982(4) 0.37963(16) 0.5667(4) 0.0169(8) Uani 1 1 d . . . H8 H 0.8361 0.4112 0.5270 0.020 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 Cu1 0.0083(2) 0.0176(2) 0.00551(19) 0.00128(18) 0.00412(14) 0.00157(19) O11 0.0151(13) 0.0173(13) 0.0098(12) 0.0032(10) 0.0066(10) 0.0018(10) O12 0.0225(14) 0.0249(15) 0.0108(13) 0.0060(11) 0.0061(11) 0.0011(12) O21 0.0109(12) 0.0226(14) 0.0073(12) 0.0033(10) 0.0063(9) 0.0029(10) O22 0.0123(12) 0.0212(13) 0.0076(12) 0.0027(10) 0.0066(10) 0.0028(10) N10 0.0116(15) 0.0166(15) 0.0071(14) 0.0015(12) 0.0042(11) -0.0005(12) N1 0.0098(15) 0.0249(18) 0.0089(15) -0.0005(13) 0.0039(12) -0.0025(13) N3 0.0077(14) 0.0192(16) 0.0077(14) 0.0002(12) 0.0027(11) 0.0003(12) N6 0.0111(15) 0.0244(18) 0.0181(16) 0.0028(13) 0.0098(13) 0.0014(12) N9 0.0088(15) 0.0210(16) 0.0135(15) -0.0009(13) 0.0076(12) -0.0007(12) C11 0.0107(17) 0.023(2) 0.0133(18) 0.0049(15) 0.0061(14) 0.0039(15) C12 0.0152(18) 0.0184(19) 0.0087(17) -0.0018(14) 0.0062(14) -0.0027(15) C21 0.0096(17) 0.0186(19) 0.0109(17) 0.0040(14) 0.0068(14) 0.0027(14) C22 0.0060(16) 0.0168(18) 0.0073(16) -0.0044(14) -0.0003(13) -0.0010(13) C31 0.025(2) 0.021(2) 0.0109(18) -0.0050(15) 0.0106(15) -0.0039(16) C32 0.023(2) 0.0169(19) 0.0106(18) -0.0050(14) 0.0082(15) -0.0065(15) C33 0.017(2) 0.020(2) 0.020(2) -0.0010(16) 0.0088(16) 0.0002(15) C34 0.025(2) 0.016(2) 0.0183(19) 0.0013(15) 0.0119(16) 0.0010(16) C35 0.019(2) 0.018(2) 0.0173(19) -0.0042(15) 0.0085(15) -0.0040(15) C36 0.0157(19) 0.023(2) 0.021(2) -0.0022(16) 0.0029(16) -0.0028(16) C37 0.025(2) 0.019(2) 0.0108(18) -0.0002(15) 0.0006(15) -0.0043(16) C38 0.023(2) 0.026(2) 0.030(2) 0.0003(18) 0.0139(18) -0.0003(17) C2 0.0107(17) 0.0177(18) 0.0081(16) -0.0004(13) 0.0023(13) -0.0002(14) C4 0.0051(15) 0.0186(19) 0.0059(15) -0.0023(14) -0.0005(12) -0.0001(13) C5 0.0085(16) 0.0211(19) 0.0060(16) -0.0021(14) 0.0013(13) 0.0002(14) C6 0.0088(16) 0.025(2) 0.0060(15) -0.0017(14) 0.0019(12) 0.0013(14) C7 0.0151(18) 0.020(2) 0.0129(18) 0.0008(15) 0.0057(14) 0.0042(15) C8 0.021(2) 0.019(2) 0.0114(18) 0.0000(15) 0.0069(15) 0.0008(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 Cu1 O11 1.946(2) . y Cu1 O21 1.949(2) . y Cu1 O22 2.309(2) 4_566 y Cu1 N10 2.022(3) . y Cu1 N3 1.987(3) . y O11 C12 1.285(4) . ? O12 C12 1.233(4) . ? O21 C22 1.280(4) . ? O22 Cu1 2.309(2) 4_565 ? O22 C22 1.243(4) . ? N10 C11 1.481(4) . ? N10 C21 1.477(4) . ? N10 C31 1.498(4) . ? N1 C2 1.326(4) . ? N1 C6 1.356(5) . ? N3 C2 1.338(4) . ? N3 C4 1.353(4) . ? N6 H6a 0.8683 . ? N6 H6b 0.8755 . ? N6 C6 1.341(4) . ? N9 H9 0.8800 . ? N9 C4 1.359(4) . ? N9 C8 1.381(5) . ? C11 H11a 0.9900 . ? C11 H11b 0.9900 . ? C11 C12 1.526(5) . ? C21 H21a 0.9900 . ? C21 H21b 0.9900 . ? C21 C22 1.517(5) . ? C31 H31a 0.9900 . ? C31 H31b 0.9900 . ? C31 C32 1.506(5) . ? C32 C33 1.386(5) . ? C32 C37 1.395(5) . ? C33 H33 0.9500 . ? C33 C34 1.394(5) . ? C34 H34 0.9500 . ? C34 C35 1.388(5) . ? C35 C36 1.391(5) . ? C35 C38 1.515(5) . ? C36 H36 0.9500 . ? C36 C37 1.388(5) . ? C37 H37 0.9500 . ? C38 H38a 0.9800 . ? C38 H38b 0.9800 . ? C38 H38c 0.9800 . ? C2 H2 0.9500 . ? C4 C5 1.398(5) . ? C5 C6 1.412(5) . ? C5 C7 1.431(5) . ? C7 H7 0.9500 . ? C7 C8 1.366(5) . ? C8 H8 0.9500 . ? 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 O11 Cu1 O21 167.48(10) . . y O11 Cu1 O22 88.16(9) . 4_566 y O11 Cu1 N10 84.50(10) . . y O11 Cu1 N3 97.51(11) . . y O21 Cu1 O22 91.23(9) . 4_566 y O21 Cu1 N10 83.40(10) . . y O21 Cu1 N3 95.01(10) . . y N10 Cu1 O22 102.12(10) . 4_566 y N3 Cu1 O22 94.87(10) . 4_566 y N3 Cu1 N10 162.96(12) . . y C12 O11 Cu1 113.2(2) . . ? C22 O21 Cu1 114.9(2) . . ? C22 O22 Cu1 118.2(2) . 4_565 ? C11 N10 Cu1 103.4(2) . . ? C11 N10 C31 112.2(3) . . ? C21 N10 Cu1 105.6(2) . . ? C21 N10 C11 114.7(3) . . ? C21 N10 C31 109.2(3) . . ? C31 N10 Cu1 111.4(2) . . ? C2 N1 C6 118.5(3) . . ? C2 N3 Cu1 120.5(2) . . ? C2 N3 C4 113.5(3) . . ? C4 N3 Cu1 124.8(2) . . ? H6a N6 H6b 123.1 . . ? C6 N6 H6a 118.7 . . ? C6 N6 H6b 114.6 . . ? C4 N9 H9 125.7 . . ? C4 N9 C8 108.6(3) . . ? C8 N9 H9 125.7 . . ? N10 C11 H11a 109.4 . . ? N10 C11 H11b 109.4 . . ? N10 C11 C12 111.4(3) . . ? H11a C11 H11b 108.0 . . ? C12 C11 H11a 109.4 . . ? C12 C11 H11b 109.4 . . ? O11 C12 C11 116.2(3) . . ? O12 C12 O11 125.0(3) . . ? O12 C12 C11 118.7(3) . . ? N10 C21 H21a 109.6 . . ? N10 C21 H21b 109.6 . . ? N10 C21 C22 110.1(3) . . ? H21a C21 H21b 108.1 . . ? C22 C21 H21a 109.6 . . ? C22 C21 H21b 109.6 . . ? O21 C22 C21 116.4(3) . . ? O22 C22 O21 124.3(3) . . ? O22 C22 C21 119.3(3) . . ? N10 C31 H31a 108.8 . . ? N10 C31 H31b 108.8 . . ? N10 C31 C32 113.9(3) . . ? H31a C31 H31b 107.7 . . ? C32 C31 H31a 108.8 . . ? C32 C31 H31b 108.8 . . ? C33 C32 C31 122.0(3) . . ? C33 C32 C37 118.3(3) . . ? C37 C32 C31 119.6(3) . . ? C32 C33 H33 119.5 . . ? C32 C33 C34 121.0(3) . . ? C34 C33 H33 119.5 . . ? C33 C34 H34 119.8 . . ? C35 C34 C33 120.4(4) . . ? C35 C34 H34 119.8 . . ? C34 C35 C36 118.8(3) . . ? C34 C35 C38 120.7(3) . . ? C36 C35 C38 120.5(3) . . ? C35 C36 H36 119.7 . . ? C37 C36 C35 120.6(4) . . ? C37 C36 H36 119.7 . . ? C32 C37 H37 119.6 . . ? C36 C37 C32 120.8(4) . . ? C36 C37 H37 119.6 . . ? C35 C38 H38a 109.5 . . ? C35 C38 H38b 109.5 . . ? C35 C38 H38c 109.5 . . ? H38a C38 H38b 109.5 . . ? H38a C38 H38c 109.5 . . ? H38b C38 H38c 109.5 . . ? N1 C2 N3 127.8(3) . . ? N1 C2 H2 116.1 . . ? N3 C2 H2 116.1 . . ? N3 C4 N9 127.0(3) . . ? N3 C4 C5 124.7(3) . . ? N9 C4 C5 108.3(3) . . ? C4 C5 C6 116.2(3) . . ? C4 C5 C7 107.0(3) . . ? C6 C5 C7 136.8(3) . . ? N1 C6 C5 119.4(3) . . ? N6 C6 N1 117.6(3) . . ? N6 C6 C5 123.0(3) . . ? C5 C7 H7 126.8 . . ? C8 C7 C5 106.4(3) . . ? C8 C7 H7 126.8 . . ? N9 C8 H8 125.2 . . ? C7 C8 N9 109.6(3) . . ? C7 C8 H8 125.2 . . ? 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 N6 H6a O22 0.87 2.06 2.916(4) 168.8 4_466 N6 H6b O12 0.88 2.15 2.938(4) 150.1 4_465 N9 H9 O11 0.88 2.21 2.835(4) 127.5 4_565 N9 H9 O21 0.88 2.27 2.899(4) 128.0 . loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag Cu1 O11 C12 O12 166.5(3) . . . . ? Cu1 O11 C12 C11 -9.5(4) . . . . ? Cu1 O21 C22 O22 -175.7(3) . . . . ? Cu1 O21 C22 C21 3.0(4) . . . . ? Cu1 O22 C22 O21 -8.0(4) 4_565 . . . ? Cu1 O22 C22 C21 173.5(2) 4_565 . . . ? Cu1 N10 C11 C12 31.5(3) . . . . ? Cu1 N10 C21 C22 -31.1(3) . . . . ? Cu1 N10 C31 C32 -49.0(4) . . . . ? Cu1 N3 C2 N1 168.8(3) . . . . ? Cu1 N3 C4 N9 10.9(5) . . . . ? Cu1 N3 C4 C5 -169.0(2) . . . . ? O11 Cu1 O21 C22 -2.4(6) . . . . ? O11 Cu1 N10 C11 -29.4(2) . . . . ? O11 Cu1 N10 C21 -150.2(2) . . . . ? O11 Cu1 N10 C31 91.3(2) . . . . ? O11 Cu1 N3 C2 -27.5(3) . . . . ? O11 Cu1 N3 C4 139.0(3) . . . . ? O21 Cu1 O11 C12 8.2(6) . . . . ? O21 Cu1 N10 C11 147.4(2) . . . . ? O21 Cu1 N10 C21 26.5(2) . . . . ? O21 Cu1 N10 C31 -91.9(2) . . . . ? O21 Cu1 N3 C2 152.0(2) . . . . ? O21 Cu1 N3 C4 -41.5(3) . . . . ? O22 Cu1 O11 C12 -79.3(2) 4_566 . . . ? O22 Cu1 O21 C22 84.6(2) 4_566 . . . ? O22 Cu1 N10 C11 57.5(2) 4_566 . . . ? O22 Cu1 N10 C21 -63.3(2) 4_566 . . . ? O22 Cu1 N10 C31 178.2(2) 4_566 . . . ? O22 Cu1 N3 C2 -116.3(2) 4_566 . . . ? O22 Cu1 N3 C4 50.2(3) 4_566 . . . ? N10 Cu1 O11 C12 23.1(2) . . . . ? N10 Cu1 O21 C22 -17.4(2) . . . . ? N10 Cu1 N3 C2 68.2(5) . . . . ? N10 Cu1 N3 C4 -125.3(4) . . . . ? N10 C11 C12 O11 -16.5(4) . . . . ? N10 C11 C12 O12 167.2(3) . . . . ? N10 C21 C22 O21 20.2(4) . . . . ? N10 C21 C22 O22 -161.1(3) . . . . ? N10 C31 C32 C33 -90.4(4) . . . . ? N10 C31 C32 C37 87.0(4) . . . . ? N3 Cu1 O11 C12 -173.9(2) . . . . ? N3 Cu1 O21 C22 179.6(2) . . . . ? N3 Cu1 N10 C11 -127.1(4) . . . . ? N3 Cu1 N10 C21 112.1(4) . . . . ? N3 Cu1 N10 C31 -6.4(5) . . . . ? N3 C4 C5 C6 1.2(5) . . . . ? N3 C4 C5 C7 -179.4(3) . . . . ? N9 C4 C5 C6 -178.7(3) . . . . ? N9 C4 C5 C7 0.7(4) . . . . ? C11 N10 C21 C22 -144.3(3) . . . . ? C11 N10 C31 C32 66.4(4) . . . . ? C21 N10 C11 C12 146.0(3) . . . . ? C21 N10 C31 C32 -165.3(3) . . . . ? C31 N10 C11 C12 -88.7(3) . . . . ? C31 N10 C21 C22 88.8(3) . . . . ? C31 C32 C33 C34 176.1(3) . . . . ? C31 C32 C37 C36 -175.9(3) . . . . ? C32 C33 C34 C35 -0.2(6) . . . . ? C33 C32 C37 C36 1.6(5) . . . . ? C33 C34 C35 C36 1.5(6) . . . . ? C33 C34 C35 C38 -177.5(3) . . . . ? C34 C35 C36 C37 -1.2(6) . . . . ? C35 C36 C37 C32 -0.3(6) . . . . ? C37 C32 C33 C34 -1.3(5) . . . . ? C38 C35 C36 C37 177.8(4) . . . . ? C2 N1 C6 N6 179.8(3) . . . . ? C2 N1 C6 C5 -0.9(5) . . . . ? C2 N3 C4 N9 178.3(3) . . . . ? C2 N3 C4 C5 -1.7(5) . . . . ? C4 N3 C2 N1 0.9(5) . . . . ? C4 N9 C8 C7 1.4(4) . . . . ? C4 C5 C6 N1 0.2(5) . . . . ? C4 C5 C6 N6 179.4(3) . . . . ? C4 C5 C7 C8 0.1(4) . . . . ? C5 C7 C8 N9 -0.9(4) . . . . ? C6 N1 C2 N3 0.4(5) . . . . ? C6 C5 C7 C8 179.4(4) . . . . ? C7 C5 C6 N1 -179.0(4) . . . . ? C7 C5 C6 N6 0.2(6) . . . . ? C8 N9 C4 N3 178.8(3) . . . . ? C8 N9 C4 C5 -1.2(4) . . . . ?