#------------------------------------------------------------------------------ #$Date: 2015-10-29 12:03:11 +0200 (Thu, 29 Oct 2015) $ #$Revision: 169849 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/24/12/2241260.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2241260 loop_ _publ_author_name 'Liu, Chen' 'Abboud, Khalil A.' _publ_section_title ; Crystal structures of \m-oxalato-bis[azido(histamine)copper(II)] and \m-oxalato-bis[(dicyanamido)(histamine)copper(II)] ; _journal_coeditor_code ZL2645 _journal_issue 11 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first 1379 _journal_page_last 1383 _journal_paper_doi 10.1107/S2056989015019908 _journal_volume 71 _journal_year 2015 _chemical_formula_iupac '[Cu2 (C2 O4) (C2 N3)2 (C5 H9 N3)2]' _chemical_formula_moiety 'C16 H18 Cu2 N12 O4' _chemical_formula_sum 'C16 H18 Cu2 N12 O4' _chemical_formula_weight 569.50 _chemical_name_systematic \m-Oxalato-\k^4^O^1^,O^2^:O^1'^,O^2'^-bis[[4-(2-aminoethyl)-1H-imidazole-\k^2^N^3^,N^4^](dicyanamido-\kN^1^)copper(II)] _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014/6 _cell_angle_alpha 90 _cell_angle_beta 90.1120(10) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 9.6816(7) _cell_length_b 14.7236(11) _cell_length_c 7.4604(6) _cell_measurement_reflns_used 87 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 28.0 _cell_measurement_theta_min 2.0 _cell_volume 1063.46(14) _computing_cell_refinement ; SMART and SAINT (Bruker, 1998) ; _computing_data_collection ; SMART (Bruker, 1998) ; _computing_data_reduction ; SAINT (Bruker, 1998) ; _computing_molecular_graphics ; SHELXTL-Plus (Sheldrick, 2008) ; _computing_publication_material ; publCIF (Westrip, 2010) ; _computing_structure_refinement ; SHELXL2014 (Sheldrick, 2015) ; _computing_structure_solution ; SHELXS97 (Sheldrick, 2015) ; _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measurement_device_type 'Bruker SMART CCD area-detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0611 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 6331 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_min 2.104 _exptl_absorpt_coefficient_mu 2.054 _exptl_absorpt_correction_T_max 0.5034 _exptl_absorpt_correction_T_min 0.3399 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; (SADABS; Bruker, 1998) ; _exptl_crystal_colour blue _exptl_crystal_density_diffrn 1.778 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 576 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.18 _refine_diff_density_max 0.336 _refine_diff_density_min -0.424 _refine_ls_extinction_coef 0.022(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method ; SHELXL2014 (Sheldrick, 2015) ; _refine_ls_goodness_of_fit_ref 1.146 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 198 _refine_ls_number_reflns 2374 _refine_ls_number_restraints 55 _refine_ls_restrained_S_all 1.136 _refine_ls_R_factor_all 0.0364 _refine_ls_R_factor_gt 0.0338 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0382P)^2^+1.0333P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0944 _refine_ls_wR_factor_ref 0.0956 _reflns_number_gt 2172 _reflns_number_total 2374 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file zl2645sup1.cif _cod_data_source_block II _cod_database_code 2241260 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_hkl_file ; 0 0 -1 1.05 0.26 0 0 1 2.43 0.30 0 0 2 1160.20 5.65 0 0 3 1.07 0.73 0 0 4 1580.06 8.56 0 0 5 0.37 1.21 0 0 6 255.87 4.31 0 0 7 -1.84 1.54 0 0 8 32.87 2.27 0 0 9 0.75 1.77 0 -1 0 0.07 0.07 0 -1 1 515.85 2.94 0 1 -1 511.03 2.89 0 1 1 499.27 2.88 0 -1 2 2801.62 14.34 0 1 -2 2517.66 12.09 0 1 2 2794.41 14.30 0 -1 3 725.80 5.12 0 1 -3 652.85 4.69 0 1 3 784.53 5.33 0 -1 4 26.03 1.39 0 1 4 27.77 1.45 0 -1 5 440.92 5.03 0 1 5 476.47 5.22 0 -1 6 131.10 3.22 0 1 6 123.13 3.07 0 -1 7 901.97 8.52 0 1 7 976.01 8.88 0 -1 8 72.82 2.98 0 1 8 71.17 2.94 0 -1 9 156.52 4.41 0 1 9 125.19 4.02 0 -2 0 2026.91 12.29 0 -2 1 2954.98 14.51 0 2 -1 2980.82 14.66 0 -2 2 881.63 4.65 0 2 -2 806.71 4.36 0 2 2 525.41 3.51 0 -2 3 877.64 5.52 0 2 -3 788.61 5.13 0 2 3 882.66 5.54 0 -2 4 1406.70 8.19 0 2 -4 1417.66 8.04 0 2 4 1619.11 8.81 0 -2 5 120.73 2.79 0 2 5 127.03 2.90 0 -2 6 189.59 3.76 0 2 6 158.16 3.45 0 -2 7 4.63 1.49 0 2 7 4.30 1.44 0 -2 8 8.60 1.77 0 2 8 9.05 1.60 0 -2 9 11.25 2.07 0 2 9 11.98 2.07 0 -3 1 1243.37 5.11 0 3 -1 1103.74 4.68 0 3 1 1055.59 4.52 0 -3 2 144.47 1.84 0 3 -2 139.04 1.80 0 3 2 146.49 1.88 0 -3 3 18.35 1.02 0 3 -3 17.52 0.97 0 3 3 16.56 1.00 0 -3 4 1130.85 7.25 0 3 -4 1062.53 6.92 0 3 4 1099.80 7.15 0 -3 5 414.72 5.06 0 3 -5 277.58 4.02 0 3 5 389.83 4.87 0 -3 6 948.26 8.26 0 3 6 871.68 7.85 0 -3 7 155.57 3.73 0 3 7 124.88 3.36 0 -3 8 437.04 6.59 0 -3 9 18.32 2.27 0 3 9 22.20 2.17 0 -4 0 780.34 3.81 0 -4 -1 1307.71 5.34 0 -4 1 1347.87 5.47 0 4 -1 1382.42 5.49 0 -4 2 86.26 1.49 0 4 2 119.76 1.75 0 -4 3 1189.90 6.49 0 4 -3 1068.31 6.08 0 4 3 1010.79 5.98 0 -4 4 139.96 2.65 0 4 -4 121.49 2.44 0 4 4 126.56 2.51 0 -4 5 202.54 3.59 0 4 -5 180.96 3.36 0 4 5 188.65 3.44 0 -4 6 63.57 2.45 0 4 6 68.79 2.61 0 -4 7 2.91 1.43 0 4 7 3.15 1.44 0 -4 8 13.05 1.95 0 4 8 11.94 1.91 0 -4 9 13.21 2.16 0 4 9 14.54 2.18 0 -5 -1 26.91 0.83 0 -5 1 21.21 0.77 0 5 -1 20.28 0.78 0 -5 2 238.73 2.56 0 5 -2 256.18 2.62 0 5 2 236.41 2.55 0 -5 3 69.60 1.72 0 5 -3 79.48 1.76 0 5 3 66.30 1.70 0 -5 4 898.18 6.51 0 5 -4 893.07 6.43 0 5 4 999.19 6.86 0 -5 5 108.36 2.74 0 5 -5 105.46 2.68 0 5 5 120.21 2.82 0 -5 6 263.01 4.55 0 5 -6 216.17 4.09 0 5 6 217.84 4.18 0 -5 7 73.50 2.88 0 5 7 63.10 2.70 0 5 8 306.75 5.66 0 -5 9 3.42 1.97 0 5 9 3.82 1.92 0 -6 0 936.21 4.77 0 -6 -1 400.62 3.12 0 -6 1 553.53 3.73 0 6 -1 569.22 3.65 0 -6 2 289.93 2.93 0 6 -2 230.03 1.75 0 6 2 287.03 2.87 0 6 2 212.07 2.55 0 -6 3 1322.29 7.15 0 6 -3 1251.75 6.90 0 6 3 1286.75 7.07 0 -6 4 151.23 2.82 0 6 -4 133.41 2.65 0 6 4 151.76 2.84 0 -6 5 0.64 1.13 0 6 -5 0.16 1.14 0 6 5 0.69 1.23 0 -6 6 19.20 1.75 0 6 -6 14.46 1.57 0 6 6 15.63 1.51 0 -6 7 119.41 3.58 0 6 7 88.78 3.14 0 -6 8 4.59 1.81 0 6 8 4.43 1.77 0 6 9 1.18 1.93 0 -7 0 0.25 0.57 0 -7 -1 4.25 0.64 0 -7 1 4.47 0.69 0 7 -1 6.51 0.66 0 -7 2 126.47 2.09 0 7 -2 127.06 2.08 0 7 -2 130.91 1.27 0 7 2 121.19 2.02 0 7 2 123.34 2.10 0 -7 3 1102.50 6.72 0 7 -3 954.45 6.18 0 7 3 1033.62 6.51 0 -7 4 221.21 3.43 0 7 -4 227.99 3.45 0 7 4 232.77 3.53 0 -7 5 664.38 6.46 0 7 -5 389.97 4.97 0 7 5 661.79 6.42 0 -7 6 -0.20 1.74 0 7 -6 0.26 0.96 0 7 6 -0.42 1.81 0 -7 7 61.39 2.77 0 7 -7 48.61 2.49 0 7 7 55.82 2.69 0 -7 8 8.14 1.96 0 7 8 6.12 1.67 0 -8 0 42.52 1.27 0 -8 -1 0.72 0.62 0 -8 1 0.54 0.69 0 8 -1 0.81 0.65 0 -8 2 552.54 4.50 0 8 -2 528.38 4.31 0 8 -2 633.00 3.37 0 8 2 484.94 4.12 0 8 2 564.06 4.57 0 -8 3 180.52 2.87 0 8 -3 170.99 2.78 0 8 3 187.38 2.95 0 -8 4 326.04 4.22 0 8 -4 253.52 3.72 0 8 4 261.23 3.82 0 -8 5 34.61 1.89 0 8 -5 35.36 1.84 0 8 5 32.19 1.75 0 -8 6 1.01 1.29 0 8 -6 1.92 1.32 0 8 6 2.82 1.34 0 -8 7 122.48 3.66 0 8 -7 123.11 3.64 0 8 7 136.64 3.86 0 -8 8 1.25 1.86 0 8 8 1.01 1.80 0 -9 0 0.15 0.66 0 -9 -1 22.66 1.11 0 -9 1 24.55 1.17 0 9 -1 23.03 1.07 0 -9 2 55.70 1.68 0 9 -2 53.90 1.64 0 9 2 52.25 1.60 0 9 2 52.10 1.67 0 -9 3 14.23 1.16 0 9 -3 15.35 1.19 0 9 3 15.14 1.29 0 -9 4 111.90 2.65 0 9 -4 66.43 2.13 0 9 4 101.36 2.55 0 -9 5 200.20 3.79 0 9 -5 143.71 3.25 0 9 5 154.79 3.39 0 -9 6 118.46 3.30 0 9 -6 78.40 2.77 0 9 6 107.52 3.18 0 -9 7 157.00 4.14 0 9 -7 95.27 3.33 0 9 7 153.98 4.11 0 -9 8 13.09 2.25 0 9 8 13.96 2.26 0 -10 0 48.49 1.53 0 -10 -1 127.13 2.33 0 -10 1 142.25 2.52 0 10 -1 129.58 2.26 0 -10 2 254.80 3.43 0 10 -2 181.50 2.84 0 10 2 185.62 2.90 0 -10 3 110.36 2.52 0 10 -3 75.18 2.11 0 10 3 95.84 2.40 0 -10 4 16.94 1.39 0 10 -4 17.95 1.44 0 10 4 21.16 1.52 0 -10 5 174.38 3.63 0 10 -5 149.70 3.39 0 10 5 134.11 3.25 0 -10 6 2.65 1.42 0 10 -6 1.64 1.42 0 10 6 1.24 1.45 0 -10 7 1.01 1.63 0 10 -7 1.96 1.61 0 10 7 0.72 1.68 0 -10 8 3.87 2.04 0 10 -8 2.23 1.94 0 10 8 2.58 2.05 0 -11 0 0.18 1.15 0 11 0 -0.14 0.60 0 -11 -1 9.92 1.02 0 -11 1 19.70 1.26 0 11 -1 8.54 1.03 0 -11 2 52.84 1.84 0 11 -2 50.64 1.75 0 11 2 50.69 1.78 0 11 2 57.81 1.96 0 -11 3 8.40 1.21 0 11 -3 5.55 1.14 0 11 3 6.79 1.25 0 -11 4 75.85 2.40 0 11 -4 64.12 2.24 0 11 4 74.03 2.48 0 -11 5 7.29 1.41 0 11 -5 3.48 1.31 0 11 5 5.10 1.39 0 -11 6 73.63 2.86 0 11 -6 76.58 2.90 0 11 6 66.95 2.80 0 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0.20 1.60 0 17 3 22.07 2.14 0 17 4 2.51 2.06 -1 0 0 590.92 3.47 -1 0 0 625.72 5.99 -1 0 -1 0.88 0.26 -1 0 -1 0.45 0.21 -1 0 1 1.36 0.25 -1 0 1 1.30 0.25 1 0 1 2.49 0.31 -1 0 -2 190.33 1.99 -1 0 -2 203.96 1.84 -1 0 2 639.37 3.48 -1 0 2 668.06 4.04 1 0 2 235.76 2.39 -1 0 3 0.59 0.68 1 0 3 0.53 0.66 -1 0 4 1881.95 9.37 1 0 4 1507.86 8.42 -1 0 5 -0.09 1.35 1 0 5 -0.56 1.30 -1 0 6 1005.42 8.26 1 0 6 123.21 3.14 -1 0 7 -0.67 1.82 1 0 7 -0.04 1.61 -1 0 8 558.52 7.25 1 0 8 249.26 4.96 -1 0 9 -1.33 2.39 1 0 9 0.30 1.75 -1 -1 0 328.82 2.12 -1 -1 0 425.03 2.55 -1 1 0 403.89 2.46 -1 -1 -1 3110.54 17.55 -1 -1 -1 3006.88 16.38 -1 -1 1 2153.93 12.34 -1 -1 1 2037.06 10.99 -1 1 -1 3140.71 16.07 -1 1 -1 3145.78 17.37 -1 1 1 2307.53 12.02 -1 1 1 2403.46 12.98 1 -1 1 3518.11 18.63 1 1 1 3316.45 15.88 -1 -1 -2 310.62 2.49 -1 -1 2 332.96 2.22 -1 1 -2 258.95 2.33 -1 1 -2 274.35 1.98 -1 1 2 385.76 3.07 1 -1 2 352.21 2.97 1 1 2 323.67 2.75 -1 -1 3 1283.61 5.54 -1 -1 3 1276.14 6.69 -1 1 -3 3426.69 16.39 1 -1 3 3976.52 20.48 1 1 3 3968.28 19.00 -1 -1 4 14.27 0.92 -1 -1 4 14.68 1.20 -1 1 -4 732.14 5.66 -1 1 4 11.20 1.06 1 -1 4 776.23 6.00 1 1 4 793.06 6.17 -1 -1 5 26.53 1.18 -1 -1 5 25.40 1.59 -1 1 5 22.25 1.52 1 -1 5 335.76 4.42 1 1 5 348.76 4.59 -1 -1 6 0.85 1.32 -1 1 6 0.61 1.28 1 -1 6 46.57 2.08 1 1 6 46.43 2.05 -1 -1 7 89.51 3.01 -1 1 7 88.68 2.92 1 -1 7 145.11 3.62 1 1 7 138.69 3.56 -1 -1 8 18.09 2.01 -1 1 8 16.80 1.96 1 -1 8 3.84 1.64 1 1 8 3.57 1.61 -1 -1 9 74.34 3.18 -1 1 9 84.82 3.44 1 -1 9 32.61 2.56 1 1 9 28.25 2.47 -1 -2 0 442.37 2.58 -1 -2 0 519.23 2.82 -1 2 0 482.64 2.73 1 -2 0 565.51 4.57 -1 -2 -1 32.15 0.78 -1 -2 1 235.58 1.71 -1 -2 1 178.59 1.63 -1 2 -1 31.04 0.71 -1 2 -1 31.71 0.54 -1 2 1 184.21 1.57 1 -2 1 31.86 0.65 1 2 -1 169.27 1.54 1 2 1 33.41 0.73 1 2 1 33.21 0.74 -1 -2 2 1017.47 4.97 -1 -2 2 936.35 4.81 -1 2 -2 19.55 0.78 -1 2 -2 15.22 0.45 -1 2 2 939.47 4.91 1 -2 2 20.59 0.82 1 2 -2 924.45 4.92 1 2 2 20.25 0.79 -1 -2 3 2118.67 7.82 -1 -2 3 2468.77 9.52 -1 2 -3 725.21 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1.83 -7 -3 7 27.68 2.24 -7 3 -7 0.65 1.63 7 3 7 1.49 1.85 -7 -3 8 12.38 2.30 7 3 8 12.10 2.45 -7 -4 0 3.19 1.15 -7 -4 0 5.19 1.02 -7 4 0 4.45 1.23 -7 -4 -1 231.15 3.77 -7 -4 -1 233.41 3.19 -7 -4 1 65.25 2.12 -7 -4 1 51.90 1.65 -7 4 -1 239.96 3.36 -7 4 -1 240.79 3.65 -7 4 1 48.70 2.01 -7 -4 -2 137.55 3.01 -7 -4 2 2.24 1.04 -7 -4 2 2.73 1.07 -7 4 -2 145.95 2.75 -7 4 -2 145.97 2.89 -7 4 2 1.29 1.17 7 4 2 141.12 2.65 7 4 2 145.98 2.78 -7 -4 -3 442.93 5.40 -7 -4 3 16.74 1.46 -7 -4 3 16.81 1.35 -7 4 -3 452.13 4.93 -7 4 -3 440.13 4.83 -7 4 3 17.48 1.47 7 4 3 475.68 5.19 -7 -4 -4 83.46 2.62 -7 -4 4 76.55 2.37 -7 4 -4 93.52 2.62 -7 4 -4 95.14 2.45 -7 4 4 92.00 2.86 7 4 4 100.00 2.82 -7 -4 -5 254.65 4.53 -7 -4 5 88.66 2.75 -7 4 -5 245.73 4.25 -7 4 5 77.77 2.83 7 4 5 280.30 4.76 -7 -4 -6 4.23 1.41 -7 -4 6 16.94 1.80 -7 4 -6 2.45 1.56 -7 4 6 16.31 1.89 7 4 6 2.56 1.62 -7 -4 7 217.02 4.75 -7 4 -7 200.28 4.62 -7 4 7 206.92 4.78 7 4 7 218.08 5.09 -7 -4 8 10.44 2.26 -7 -5 0 401.60 4.90 -7 -5 0 434.11 4.45 -7 5 0 533.08 5.50 -7 -5 -1 212.42 3.69 -7 -5 -1 228.10 3.31 -7 -5 1 43.81 1.84 -7 -5 1 52.50 1.73 -7 5 -1 244.70 3.55 -7 5 -1 218.95 3.53 -7 5 1 59.58 2.21 -7 -5 -2 83.96 2.48 -7 -5 2 161.73 3.17 -7 -5 2 177.62 3.10 -7 5 -2 83.02 2.27 -7 5 -2 83.57 2.27 -7 5 2 171.37 3.47 7 5 2 86.79 2.30 7 5 2 88.38 2.42 -7 -5 -3 24.67 1.73 -7 -5 3 17.24 1.45 -7 -5 3 15.04 1.42 -7 5 -3 26.86 1.67 -7 5 -3 29.27 1.62 -7 5 3 15.65 1.59 7 5 3 27.76 1.81 -7 -5 -4 183.81 3.81 -7 -5 4 282.21 4.31 -7 5 -4 182.50 3.54 -7 5 -4 213.66 3.48 -7 5 4 335.37 5.15 7 5 4 203.57 3.87 -7 -5 -5 3.75 1.39 -7 -5 5 219.61 4.12 -7 5 -5 4.75 1.40 -7 5 5 224.40 4.52 7 5 5 3.93 1.60 -7 -5 -6 20.32 1.91 -7 -5 6 64.59 2.69 -7 5 -6 19.50 1.94 -7 5 6 74.87 3.06 7 5 6 19.54 2.06 -7 -5 7 0.67 1.73 -7 5 -7 14.69 2.09 -7 5 7 2.02 1.84 7 5 7 17.71 2.31 -7 -6 0 23.96 1.49 -7 -6 0 25.45 1.51 -7 6 0 23.20 1.59 -7 -6 -1 180.32 3.46 -7 -6 -1 178.36 3.11 -7 -6 1 3.80 1.12 -7 -6 1 3.83 0.98 -7 6 -1 186.24 3.27 -7 6 -1 196.30 3.41 -7 6 1 5.86 1.28 -7 -6 -2 298.37 4.56 -7 -6 2 2.67 1.07 -7 -6 2 3.01 1.15 -7 6 -2 316.77 4.27 -7 6 -2 321.01 4.17 -7 6 2 2.99 1.26 7 6 2 305.97 4.13 7 6 2 333.00 4.44 -7 -6 -3 39.28 2.06 -7 -6 3 90.83 2.59 -7 -6 3 94.46 2.57 -7 6 -3 30.33 1.73 -7 6 -3 31.46 1.67 -7 6 3 100.68 2.97 7 6 3 35.34 1.90 -7 -6 -4 286.69 4.83 -7 -6 4 2.24 1.26 -7 6 -4 287.11 4.48 -7 6 4 2.62 1.20 7 6 4 305.10 4.80 -7 -6 -5 262.29 4.86 -7 6 -5 255.06 4.55 -7 6 5 84.04 3.09 7 6 5 282.93 5.01 -7 -6 6 147.90 3.85 -7 6 -6 189.37 4.30 -7 6 6 137.48 4.01 7 6 6 201.42 4.62 -7 -6 7 91.43 3.54 -7 6 -7 48.83 2.79 -7 6 7 81.21 3.58 7 6 7 63.15 3.34 -7 -7 0 12.85 1.39 -7 -7 0 12.78 1.30 -7 7 0 14.21 1.48 -7 -7 -1 122.77 3.01 -7 -7 -1 131.97 2.85 -7 -7 1 337.38 4.61 -7 -7 1 344.51 4.40 -7 7 -1 124.83 2.86 -7 7 -1 119.81 2.82 -7 7 1 391.83 5.07 -7 -7 -2 1.45 1.20 -7 -7 2 140.01 3.06 -7 -7 2 158.27 3.23 -7 7 -2 2.17 1.16 -7 7 -2 0.44 1.06 -7 7 2 164.46 3.54 7 7 2 0.58 1.15 7 7 2 1.64 1.30 -7 -7 -3 22.19 1.71 -7 -7 3 435.43 5.33 -7 7 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0.78 1.42 -7 -12 -1 9.92 1.74 -7 -12 -1 10.37 1.58 -7 -12 1 5.81 1.34 -7 12 -1 11.11 1.71 -7 12 1 6.84 1.56 -7 -12 -2 30.34 2.24 -7 12 -2 30.88 1.98 -7 12 2 20.84 2.00 7 12 2 29.58 2.11 7 12 2 30.78 2.33 -7 -12 3 24.82 2.09 -7 12 -3 88.40 3.15 -7 12 3 31.14 2.33 7 12 3 89.42 3.15 7 12 3 94.29 3.32 -7 -12 4 27.84 2.31 -7 12 -4 0.21 1.28 -7 12 4 22.08 2.26 7 12 4 2.12 1.88 -7 -13 0 83.94 2.99 -7 13 0 85.26 2.96 -7 -13 -1 29.62 2.26 -7 -13 -1 37.88 2.27 -7 -13 1 103.41 3.28 -7 13 -1 40.51 2.34 -7 13 1 107.21 3.35 -7 -13 2 177.50 4.21 -7 13 -2 82.17 3.04 -7 13 2 190.32 4.48 7 13 2 88.42 3.15 7 13 2 91.51 3.40 -7 -13 3 14.50 1.93 -7 13 -3 101.94 3.44 -7 13 3 25.33 2.32 7 13 3 105.66 3.52 7 13 3 109.04 3.68 -7 -13 4 46.36 2.83 -7 13 -4 1.39 1.70 7 13 4 -0.02 2.71 -7 -14 0 4.65 1.43 -7 14 0 7.33 1.69 -7 -14 -1 55.60 2.59 -7 -14 1 23.19 1.96 -7 14 -1 49.65 2.48 -7 14 1 27.89 2.23 -7 -14 2 8.47 1.81 -7 14 -2 6.38 1.73 -7 14 2 10.51 2.00 7 14 2 7.06 1.80 7 14 2 9.08 2.12 -7 -14 3 8.92 1.93 -7 14 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3 473.09 6.64 -10 -1 -4 22.41 2.07 -10 -1 4 64.90 2.93 -10 1 -4 25.03 2.06 -10 1 4 69.19 3.04 -10 -1 -5 17.46 2.15 -10 -1 5 291.52 5.68 -10 1 -5 17.14 2.16 -10 1 5 248.93 5.34 -10 -1 -6 2.83 2.04 -10 -2 0 71.46 2.72 -10 2 0 81.51 2.86 -10 -2 -1 257.11 4.70 -10 -2 1 23.80 1.93 -10 2 -1 240.06 4.51 -10 2 1 19.11 1.86 -10 -2 -2 97.90 3.08 -10 -2 2 130.23 3.56 -10 2 -2 106.77 3.14 -10 2 2 145.62 3.82 -10 -2 -3 272.01 5.06 -10 -2 3 10.17 1.75 -10 2 -3 248.07 4.63 -10 2 3 9.27 1.81 -10 -2 -4 273.01 5.21 -10 -2 4 12.06 2.04 -10 2 -4 287.35 5.09 -10 2 4 10.35 1.97 -10 -2 -5 179.17 4.45 -10 2 -5 182.95 4.30 -10 2 5 2.06 1.92 -10 -2 -6 69.84 3.25 -10 2 6 6.16 2.19 -10 -3 0 291.77 5.05 -10 3 0 301.62 5.10 -10 -3 -1 0.98 1.34 -10 -3 1 1.21 1.31 -10 3 -1 0.98 1.32 -10 3 1 0.46 1.37 -10 -3 -2 7.69 1.58 -10 -3 2 260.07 4.83 -10 3 -2 8.20 1.51 -10 3 2 319.45 5.47 -10 -3 -3 7.25 1.65 -10 -3 3 80.51 3.00 -10 3 -3 6.96 1.51 -10 3 3 67.05 2.93 -10 -3 -4 23.70 2.13 -10 -3 4 274.19 5.21 -10 3 -4 22.57 2.17 -10 3 4 274.08 5.47 -10 -3 -5 45.10 2.71 -10 3 5 49.48 2.89 -10 -4 0 11.15 1.63 -10 4 0 11.63 1.54 -10 -4 -1 320.62 5.41 -10 -4 1 88.47 3.01 -10 4 -1 299.53 5.03 -10 4 1 91.66 3.14 -10 -4 -2 22.32 1.98 -10 -4 2 27.63 2.05 -10 4 -2 22.13 1.88 -10 4 2 33.18 2.25 -10 -4 -3 300.92 5.43 -10 -4 3 8.87 1.75 -10 4 -3 293.60 4.97 -10 4 3 10.29 1.88 -10 -4 -4 21.12 2.13 -10 4 -4 20.95 1.96 -10 4 4 9.37 1.93 -10 -4 -5 145.18 4.20 -10 4 5 52.47 2.99 -10 -5 0 174.27 4.10 -10 5 0 166.30 3.96 -10 -5 -1 90.44 3.16 -10 -5 1 87.97 3.06 -10 5 -1 86.24 2.94 -10 5 1 117.46 3.42 -10 -5 -2 27.98 2.14 -10 -5 2 54.95 2.55 -10 5 -2 32.46 2.10 -10 5 2 64.24 2.86 -10 -5 -3 2.76 1.60 -10 -5 3 29.73 2.17 -10 5 -3 5.10 1.48 -10 5 3 35.27 2.41 -10 -5 -4 4.32 1.71 -10 5 4 207.66 4.95 -10 5 5 52.65 3.07 -10 -6 0 9.17 1.74 -10 6 0 7.67 1.64 -10 -6 -1 121.35 3.65 -10 -6 1 46.92 2.49 -10 6 -1 139.45 3.48 -10 6 -1 138.67 3.69 -10 6 1 55.66 2.66 -10 -6 -2 68.55 2.97 -10 -6 2 3.77 1.56 -10 6 -2 67.35 2.69 -10 6 2 3.99 1.68 -10 -6 -3 48.93 2.69 -10 6 -3 48.58 2.39 -10 6 3 -0.42 2.14 -10 -6 -4 60.02 2.97 -10 6 4 59.83 3.05 -10 -7 0 2.87 1.58 -10 7 0 3.94 1.69 -10 -7 -1 46.18 2.59 -10 -7 1 169.16 4.21 -10 7 -1 55.50 2.53 -10 7 -1 51.87 2.53 -10 7 1 187.50 4.46 -10 -7 -2 1.49 1.60 -10 -7 2 35.31 2.33 -10 7 -2 1.80 1.54 -10 7 -2 1.99 1.51 -10 7 2 33.44 2.41 -10 -7 -3 2.62 1.70 -10 7 -3 3.02 1.70 -10 7 -3 1.97 1.51 -10 7 3 120.29 3.79 -10 -7 -4 7.11 1.94 -10 7 4 34.93 2.65 -10 -8 0 118.33 3.25 -10 8 0 128.33 3.72 -10 -8 -1 -0.18 2.50 -10 -8 -1 0.72 1.48 -10 -8 1 2.39 1.78 -10 -8 1 0.58 1.41 -10 8 -1 2.19 1.60 -10 8 -1 0.57 1.58 -10 8 1 1.04 1.56 -10 -8 -2 57.26 2.91 -10 -8 2 9.15 1.65 -10 8 -2 55.66 2.64 -10 8 -2 59.78 2.65 -10 8 2 10.94 1.92 -10 -8 -3 42.87 2.70 -10 -8 3 73.19 2.91 -10 8 -3 36.31 2.46 -10 8 -4 120.10 3.71 -10 -9 0 5.48 1.81 -10 -9 0 7.86 1.66 -10 9 0 9.06 1.93 -10 -9 -1 8.85 1.92 -10 -9 -1 7.96 1.93 -10 -9 1 14.56 2.06 -10 -9 1 14.52 1.96 -10 9 -1 8.29 1.83 -10 9 -1 10.70 1.93 -10 9 1 16.07 2.06 -10 -9 -2 23.96 2.33 -10 -9 2 8.28 1.86 -10 9 -2 28.46 2.28 -10 9 -2 29.62 2.33 -10 9 2 5.91 1.89 -10 -9 3 101.76 3.48 -10 9 -3 15.39 2.03 -10 9 3 93.58 3.67 -10 -9 4 36.68 2.73 -10 9 -4 4.39 1.87 -10 -10 0 65.01 3.12 -10 -10 0 70.79 2.90 -10 10 0 72.13 2.94 -10 10 0 76.17 3.28 -10 -10 -1 -3.63 2.53 -10 -10 -1 0.09 2.61 -10 -10 1 15.63 1.98 -10 10 -1 0.12 1.30 -10 10 -1 -0.14 2.54 -10 10 1 15.83 2.22 -10 -10 -2 34.88 2.66 -10 -10 2 18.74 2.11 -10 10 -2 37.20 2.51 -10 10 2 16.69 2.25 10 10 2 37.75 2.62 10 10 2 38.13 2.80 -10 -10 3 1.16 1.96 -10 10 -3 104.40 3.63 10 10 3 110.51 4.02 -10 -11 0 27.53 2.55 -10 -11 0 30.56 2.35 -10 11 0 26.96 2.30 -10 11 0 30.74 2.67 -10 -11 -1 23.94 2.59 -10 -11 -1 22.50 2.42 -10 -11 1 28.32 2.34 -10 11 -1 23.35 2.31 -10 11 -1 27.26 2.60 -10 11 1 31.16 2.63 -10 -11 2 105.94 3.70 10 11 2 30.97 2.62 10 11 2 27.43 2.79 -10 -12 0 1.30 1.79 -10 12 0 0.62 2.43 -11 0 0 416.51 6.28 -11 0 -1 0.38 1.43 -11 0 1 1.33 1.29 -11 0 -2 197.74 4.47 -11 0 2 372.76 6.11 -11 0 -3 -2.57 2.26 -11 0 3 0.22 1.88 -11 0 -4 227.63 4.99 -11 0 4 183.60 4.73 -11 0 -5 0.05 2.89 -11 0 5 1.95 2.06 -11 -1 0 3.12 1.34 -11 1 0 2.68 1.50 -11 -1 -1 89.77 3.18 -11 -1 1 9.42 1.55 -11 1 -1 92.96 3.19 -11 1 1 15.65 1.91 -11 -1 -2 5.92 1.64 -11 -1 2 1.20 1.57 -11 1 -2 4.94 1.60 -11 1 2 1.76 1.71 -11 -1 -3 56.52 2.80 -11 -1 3 32.42 2.44 -11 1 -3 51.88 2.67 -11 1 3 44.71 2.67 -11 -1 -4 82.82 3.36 -11 -1 4 18.57 2.47 -11 1 -4 91.88 3.39 -11 1 4 20.43 2.34 -11 -2 0 218.88 4.64 -11 2 0 273.43 5.16 -11 -2 -1 94.43 3.29 -11 -2 1 140.92 3.88 -11 2 -1 103.85 3.34 -11 2 1 184.90 4.40 -11 -2 -2 23.64 1.98 -11 -2 2 234.55 4.93 -11 2 -2 21.52 1.98 -11 2 2 175.38 4.42 -11 -2 -3 9.36 1.80 -11 -2 3 74.52 3.16 -11 2 -3 6.93 1.71 -11 2 3 83.60 3.34 -11 -2 -4 87.35 3.46 -11 -2 4 168.20 4.49 -11 2 -4 80.41 3.22 -11 2 4 196.03 4.93 -11 -3 0 44.70 2.52 -11 3 0 49.01 2.57 -11 -3 -1 1.82 1.55 -11 -3 1 0.89 1.52 -11 3 -1 2.04 1.53 -11 3 1 0.81 1.59 -11 -3 -2 147.77 4.08 -11 -3 2 6.88 1.74 -11 3 -2 142.58 3.83 -11 3 2 7.13 1.77 -11 -3 -3 12.16 1.98 -11 -3 3 28.54 2.31 -11 3 -3 12.59 1.87 -11 3 3 26.96 2.41 -11 -3 -4 117.77 3.94 -11 -3 4 130.06 4.01 -11 3 -4 111.36 3.63 -11 3 4 126.11 4.20 -11 -4 0 4.49 1.62 -11 4 0 4.70 1.69 -11 -4 -1 251.57 5.18 -11 -4 1 249.25 5.09 -11 4 -1 239.39 4.85 -11 4 1 270.97 5.30 -11 -4 -2 2.50 1.64 -11 -4 2 0.07 2.36 -11 4 -2 0.76 1.51 -11 4 2 0.47 1.66 -11 -4 -3 62.82 3.05 -11 -4 3 177.25 4.45 -11 4 -3 61.07 2.79 -11 4 3 163.87 4.51 -11 4 -4 4.44 1.83 -11 -5 0 5.26 1.73 -11 5 0 4.91 1.76 -11 -5 -1 7.61 1.80 -11 -5 1 4.64 1.69 -11 5 -1 8.44 1.80 -11 5 1 5.17 1.78 -11 -5 -2 106.13 3.68 -11 -5 2 1.06 1.62 -11 5 -2 115.83 3.64 -11 5 2 0.43 1.45 -11 -5 -3 31.04 2.52 -11 -5 3 11.28 2.00 -11 5 -3 30.45 2.28 -11 5 3 10.59 2.09 -11 -6 0 185.45 4.62 -11 6 0 188.36 4.53 -11 -6 -1 156.98 4.34 -11 -6 1 28.48 2.33 -11 6 -1 165.99 4.18 -11 6 1 43.98 2.67 -11 -6 -2 22.82 2.33 -11 -6 2 81.18 3.29 -11 6 -2 24.66 2.20 -11 6 2 90.63 3.54 -11 6 -3 16.59 2.04 -11 -7 0 3.74 1.79 -11 7 0 4.28 1.82 -11 -7 -1 42.45 2.76 -11 -7 1 17.57 2.21 -11 7 -1 43.83 2.59 -11 7 1 19.43 2.22 -11 -7 -2 6.36 1.97 -11 -7 2 1.17 1.85 -11 7 -2 10.39 2.06 -11 7 2 0.69 1.86 -11 8 0 125.16 3.70 -11 8 0 127.55 3.97 -11 -8 -1 11.46 2.18 -11 -8 1 8.51 2.04 -11 8 -1 17.34 2.18 -11 8 1 12.21 2.15 -11 8 -2 30.67 2.40 -11 -9 0 9.04 2.14 -11 9 0 9.94 2.03 -11 9 0 12.85 2.23 -11 -9 1 9.49 2.19 -11 9 -1 56.42 3.01 -11 9 -1 68.60 3.29 -11 9 -2 17.84 2.36 -12 0 0 11.44 1.94 -12 0 -1 1.06 1.64 -12 0 1 0.73 1.47 -12 0 -2 25.49 2.33 -12 0 2 15.91 2.16 -12 -1 0 21.58 2.05 -12 1 0 31.68 2.43 -12 -1 -1 184.85 4.66 -12 -1 1 162.12 4.41 -12 1 -1 162.78 4.36 -12 1 1 163.11 4.43 -12 -1 2 10.69 2.03 -12 1 -2 7.83 1.91 -12 1 2 8.86 2.00 -12 -2 0 2.97 1.78 -12 2 0 6.03 1.84 -12 -2 -1 2.72 1.74 -12 -2 1 7.67 1.92 -12 2 -1 1.99 1.68 -12 2 1 4.82 1.81 -12 -2 2 25.13 2.38 -12 2 -2 11.00 1.97 -12 -3 0 153.20 4.26 -12 3 0 136.64 4.07 -12 -3 -1 6.29 1.92 -12 -3 1 15.04 2.10 -12 3 -1 5.20 1.83 -12 -3 2 79.48 3.40 -12 3 -2 66.71 3.08 -12 -4 0 0.59 1.51 -12 4 0 1.45 1.74 -12 -4 1 2.04 1.82 -12 4 -1 23.19 2.30 -12 -4 2 7.04 2.17 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 27818 _shelx_res_file ; ZL2645_IIb.res created by SHELXL-2014/7 TITL cl39 in P2(1)/c CELL 0.71073 9.6816 14.7236 7.4604 90.000 90.112 90.000 ZERR 2.00 0.0007 0.0011 0.0006 0.000 0.001 0.000 LATT 1 SYMM -X, 0.5+Y, 0.5-Z SFAC C H N O CU UNIT 32 36 24 8 4 LIST 6 ! automatically inserted. Change 6 to 4 for CHECKCIF!! OMIT -3.00 55.00 TEMP -100 L.S. 8 acta BOND $H FMAP 2 PLAN 10 htab EQIV $1 -x+1, -y+1, -z+1 HTAB N1 O1_$1 EQIV $2 x, -y+3/2, z+1/2 HTAB N1 N4_$2 HTAB N1 O1_$1 HTAB N1 N4_$2 EQIV $3 x-1, -y+3/2, z-1/2 HTAB N3 N6_$3 sump 1 0 1.0 2 1.0 3 1.0 4 RIGU C4 C2" C3" N1 C2' C3' C2 C3 SADI 0.005 C4 C3 C4 C3' C4 C3" SADI 0.005 C3 C2 C3' C2' C3" C2" SADI 0.005 N1 C2 N1 C2' N1 C2" WGHT 0.038200 1.033300 EXTI 0.021660 FVAR 0.53189 0.51618 0.24335 0.24047 CU1 5 0.313339 0.564299 0.217220 11.00000 0.01728 0.04471 = 0.01783 -0.00297 0.00023 0.00787 O1 4 0.506719 0.513952 0.232151 11.00000 0.01778 0.04991 = 0.01874 -0.00111 0.00041 0.00681 O2 4 0.329803 0.532317 -0.042105 11.00000 0.01724 0.05046 = 0.02039 -0.00148 0.00078 0.00754 N1 3 0.319881 0.589731 0.478148 11.00000 0.02230 0.03814 = 0.02182 -0.00244 -0.00129 0.00564 AFIX 23 PART 1 H1A 2 0.370191 0.544659 0.530268 21.00000 -1.20000 H1B 2 0.368250 0.642173 0.493322 21.00000 -1.20000 AFIX 23 PART 2 H1C 2 0.310176 0.535918 0.536779 31.00000 -1.20000 H1D 2 0.405708 0.611197 0.504407 31.00000 -1.20000 PART 3 AFIX 23 H1E 2 0.386231 0.554727 0.530203 41.00000 -1.20000 H1F 2 0.342628 0.649007 0.496139 41.00000 -1.20000 AFIX 0 PART 0 N2 3 0.121309 0.605451 0.189496 11.00000 0.01895 0.02929 = 0.02220 -0.00108 0.00091 0.00400 N3 3 -0.083879 0.629439 0.076423 11.00000 0.02187 0.04574 = 0.02893 0.00063 -0.00158 0.00708 H3 2 -0.145306 0.634048 -0.015107 11.00000 0.07303 N4 3 0.422361 0.708252 0.146511 11.00000 0.05005 0.05433 = 0.05036 0.00719 0.00017 -0.02251 N5 3 0.645817 0.776079 0.067525 11.00000 0.03447 0.05259 = 0.03561 -0.01244 0.00263 -0.01182 N6 3 0.763028 0.896496 0.237333 11.00000 0.03569 0.03593 = 0.03650 0.00088 -0.00279 -0.00358 C1 1 0.551345 0.494551 0.079672 11.00000 0.01825 0.03332 = 0.01931 0.00102 -0.00043 0.00093 PART 1 C2 1 0.188535 0.598748 0.582149 21.00000 0.02886 0.03047 = 0.02073 -0.00166 0.00728 0.00512 AFIX 23 H2A 2 0.209928 0.615464 0.707704 21.00000 -1.20000 H2B 2 0.139199 0.539855 0.583023 21.00000 -1.20000 AFIX 0 C3 1 0.097001 0.671176 0.498172 21.00000 0.03066 0.02787 = 0.02689 -0.00424 0.00081 0.00993 AFIX 23 H3A 2 0.021342 0.686744 0.581796 21.00000 -1.20000 H3B 2 0.151991 0.726775 0.476484 21.00000 -1.20000 AFIX 0 PART 2 C2' 1 0.216853 0.654811 0.554746 31.00000 0.02826 0.03905 = 0.02490 -0.00770 -0.00107 0.00649 AFIX 23 H2'A 2 0.227160 0.715317 0.498461 31.00000 -1.20000 H2'B 2 0.231086 0.661274 0.685571 31.00000 -1.20000 AFIX 0 C3' 1 0.073839 0.616474 0.516305 31.00000 0.02462 0.05184 = 0.02209 -0.01327 0.00469 0.00480 AFIX 23 H3'A 2 0.005307 0.644173 0.598054 31.00000 -1.20000 H3'B 2 0.073577 0.549967 0.535827 31.00000 -1.20000 AFIX 0 PART 3 C2" 1 0.183210 0.570368 0.563967 41.00000 0.03071 0.04444 = 0.01153 -0.00656 -0.00012 0.01094 AFIX 23 H2"A 2 0.194893 0.566874 0.695648 41.00000 -1.20000 H2"B 2 0.148028 0.511008 0.521444 41.00000 -1.20000 AFIX 0 C3" 1 0.079496 0.644486 0.518083 41.00000 0.03271 0.04077 = 0.02698 -0.01805 -0.00376 0.00785 AFIX 23 H3"A 2 0.121313 0.704762 0.540844 41.00000 -1.20000 H3"B 2 -0.002831 0.638361 0.595648 41.00000 -1.20000 AFIX 0 PART 0 C4 1 0.036229 0.637707 0.322052 11.00000 0.02428 0.04754 = 0.02653 -0.00704 0.00119 0.01162 C5 1 -0.092047 0.652256 0.252340 11.00000 0.02175 0.04620 = 0.03153 -0.00032 0.00190 0.01095 AFIX 43 H5A 2 -0.171099 0.673950 0.314251 11.00000 -1.20000 AFIX 0 C6 1 0.044923 0.601256 0.042998 11.00000 0.02442 0.05555 = 0.02357 -0.00322 -0.00208 0.00979 AFIX 43 H6A 2 0.076952 0.581028 -0.070472 11.00000 -1.20000 AFIX 0 C7 1 0.527993 0.741429 0.117323 11.00000 0.03460 0.02999 = 0.03145 0.00282 -0.00524 0.00018 C8 1 0.702504 0.840440 0.163171 11.00000 0.02479 0.03393 = 0.02612 0.00383 0.00078 0.00352 HKLF 4 REM cl39 in P2(1)/c REM R1 = 0.0338 for 2172 Fo > 4sig(Fo) and 0.0364 for all 2374 data REM 198 parameters refined using 55 restraints END WGHT 0.0380 1.0333 REM Instructions for potential hydrogen bonds HTAB N1 O1_$1 HTAB N1 N4_$2 HTAB N1 O1_$1 HTAB N1 N4_$2 HTAB N3 N6_$3 EQIV $4 x, y, z+1 HTAB C2 O2_$4 EQIV $5 x-1, -y+3/2, z+1/2 HTAB C3' N6_$5 HTAB C2" O2_$4 HTAB C3" N6_$5 HTAB C5 N5_$5 REM Highest difference peak 0.336, deepest hole -0.424, 1-sigma level 0.091 Q1 1 -0.0184 0.6729 0.2730 11.00000 0.05 0.34 Q2 1 -0.1409 0.5520 0.1370 11.00000 0.05 0.30 Q3 1 0.3027 0.6461 0.1873 11.00000 0.05 0.30 Q4 1 0.1944 0.6325 0.1757 11.00000 0.05 0.30 Q5 1 0.0644 0.6540 0.3889 11.00000 0.05 0.29 Q6 1 0.4837 0.6785 0.1775 11.00000 0.05 0.29 Q7 1 0.2917 0.5620 0.3919 11.00000 0.05 0.28 Q8 1 0.5692 0.8013 0.0932 11.00000 0.05 0.27 Q9 1 0.5918 0.8182 0.0856 11.00000 0.05 0.27 Q10 1 0.6598 0.8391 0.1047 11.00000 0.05 0.26 ; _shelx_res_checksum 80975 _shelxl_version_number 2014/6 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu Cu1 0.31334(3) 0.56430(2) 0.21722(4) 0.02660(15) Uani d 1 . . O O1 0.50672(18) 0.51395(14) 0.2322(2) 0.0288(4) Uani d 1 . . O O2 0.32980(18) 0.53232(14) -0.0421(2) 0.0294(4) Uani d 1 . . N N1 0.3199(2) 0.58973(16) 0.4781(3) 0.0274(4) Uani d 1 . . H H1A 0.3702 0.5447 0.5303 0.033 Uiso calc 0.516(3) A 1 H H1B 0.3682 0.6422 0.4933 0.033 Uiso calc 0.516(3) A 1 H H1C 0.3102 0.5359 0.5368 0.033 Uiso calc 0.243(3) A 2 H H1D 0.4057 0.6112 0.5044 0.033 Uiso calc 0.243(3) A 2 H H1E 0.3862 0.5547 0.5302 0.033 Uiso calc 0.240(3) A 3 H H1F 0.3426 0.6490 0.4961 0.033 Uiso calc 0.240(3) A 3 N N2 0.1213(2) 0.60545(14) 0.1895(3) 0.0235(4) Uani d 1 . . N N3 -0.0839(2) 0.62944(17) 0.0764(3) 0.0322(5) Uani d 1 . . H H3 -0.145(5) 0.634(3) -0.015(7) 0.073(14) Uiso d 1 . . N N4 0.4224(3) 0.7083(2) 0.1465(4) 0.0516(7) Uani d 1 . . N N5 0.6458(3) 0.7761(2) 0.0675(4) 0.0409(6) Uani d 1 . . N N6 0.7630(3) 0.89650(17) 0.2373(3) 0.0360(5) Uani d 1 . . C C1 0.5513(2) 0.49455(17) 0.0797(3) 0.0236(5) Uani d 1 . . C C2 0.1885(7) 0.5987(6) 0.5821(12) 0.0267(19) Uani d 0.516(3) A 1 H H2A 0.2099 0.6155 0.7077 0.032 Uiso calc 0.516(3) A 1 H H2B 0.1392 0.5399 0.5830 0.032 Uiso calc 0.516(3) A 1 C C3 0.0970(10) 0.6712(6) 0.4982(8) 0.0285(19) Uani d 0.516(3) A 1 H H3A 0.0213 0.6867 0.5818 0.034 Uiso calc 0.516(3) A 1 H H3B 0.1520 0.7268 0.4765 0.034 Uiso calc 0.516(3) A 1 C C2' 0.2169(9) 0.6548(8) 0.5547(15) 0.031(2) Uani d 0.243(3) A 2 H H2'A 0.2272 0.7153 0.4985 0.037 Uiso calc 0.243(3) A 2 H H2'B 0.2311 0.6613 0.6856 0.037 Uiso calc 0.243(3) A 2 C C3' 0.0738(14) 0.6165(13) 0.5163(10) 0.033(4) Uani d 0.243(3) A 2 H H3'A 0.0053 0.6442 0.5981 0.039 Uiso calc 0.243(3) A 2 H H3'B 0.0736 0.5500 0.5358 0.039 Uiso calc 0.243(3) A 2 C C2" 0.1832(11) 0.5704(13) 0.564(3) 0.029(4) Uani d 0.240(3) A 3 H H2"A 0.1949 0.5669 0.6956 0.035 Uiso calc 0.240(3) A 3 H H2"B 0.1480 0.5110 0.5214 0.035 Uiso calc 0.240(3) A 3 C C3" 0.079(3) 0.6445(17) 0.5181(13) 0.033(6) Uani d 0.240(3) A 3 H H3"A 0.1213 0.7048 0.5408 0.040 Uiso calc 0.240(3) A 3 H H3"B -0.0028 0.6384 0.5956 0.040 Uiso calc 0.240(3) A 3 C C4 0.0362(3) 0.6377(2) 0.3221(4) 0.0328(6) Uani d 1 . . C C5 -0.0920(3) 0.6523(2) 0.2523(4) 0.0332(6) Uani d 1 . . H H5A -0.1711 0.6739 0.3143 0.040 Uiso calc 1 . . C C6 0.0449(3) 0.6013(2) 0.0430(4) 0.0345(6) Uani d 1 . . H H6A 0.0770 0.5810 -0.0705 0.041 Uiso calc 1 . . C C7 0.5280(3) 0.74143(19) 0.1173(4) 0.0320(6) Uani d 1 . . C C8 0.7025(3) 0.84044(18) 0.1632(3) 0.0283(5) Uani d 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cu1 0.01728(19) 0.0447(2) 0.01783(19) 0.00787(12) 0.00023(11) -0.00297(12) O1 0.0178(8) 0.0499(11) 0.0187(8) 0.0068(7) 0.0004(6) -0.0011(8) O2 0.0172(8) 0.0505(11) 0.0204(8) 0.0075(7) 0.0008(6) -0.0015(8) N1 0.0223(10) 0.0381(12) 0.0218(10) 0.0056(9) -0.0013(8) -0.0024(9) N2 0.0189(9) 0.0293(11) 0.0222(10) 0.0040(8) 0.0009(7) -0.0011(8) N3 0.0219(10) 0.0457(13) 0.0289(11) 0.0071(9) -0.0016(9) 0.0006(10) N4 0.0501(16) 0.0543(17) 0.0504(16) -0.0225(14) 0.0002(13) 0.0072(14) N5 0.0345(12) 0.0526(15) 0.0356(13) -0.0118(11) 0.0026(10) -0.0124(11) N6 0.0357(12) 0.0359(13) 0.0365(13) -0.0036(10) -0.0028(10) 0.0009(11) C1 0.0183(10) 0.0333(12) 0.0193(11) 0.0009(9) -0.0004(9) 0.0010(9) C2 0.029(3) 0.030(5) 0.021(3) 0.005(2) 0.007(2) -0.002(3) C3 0.031(3) 0.028(4) 0.027(3) 0.010(3) 0.001(2) -0.004(2) C2' 0.028(4) 0.039(6) 0.025(5) 0.006(4) -0.001(4) -0.008(4) C3' 0.025(5) 0.052(10) 0.022(5) 0.005(5) 0.005(4) -0.013(5) C2" 0.031(5) 0.044(10) 0.012(5) 0.011(5) 0.000(4) -0.007(6) C3" 0.033(8) 0.041(14) 0.027(6) 0.008(7) -0.004(5) -0.018(5) C4 0.0243(12) 0.0475(16) 0.0265(12) 0.0116(11) 0.0012(10) -0.0070(11) C5 0.0218(12) 0.0462(16) 0.0315(13) 0.0110(11) 0.0019(10) -0.0003(12) C6 0.0244(12) 0.0556(17) 0.0236(12) 0.0098(12) -0.0021(10) -0.0032(12) C7 0.0346(14) 0.0300(13) 0.0315(13) 0.0002(11) -0.0052(11) 0.0028(11) C8 0.0248(12) 0.0339(13) 0.0261(12) 0.0035(10) 0.0008(10) 0.0038(10) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle N2 Cu1 N1 . . 94.21(9) N2 Cu1 O2 . . 92.75(8) N1 Cu1 O2 . . 173.01(8) N2 Cu1 O1 . . 175.44(8) N1 Cu1 O1 . . 89.27(8) O2 Cu1 O1 . . 83.74(7) N2 Cu1 N4 . . 96.87(10) N1 Cu1 N4 . . 92.03(10) O2 Cu1 N4 . . 87.70(10) O1 Cu1 N4 . . 85.92(10) C1 O1 Cu1 . . 110.86(15) C1 O2 Cu1 3_665 . 111.54(15) C2 N1 Cu1 . . 120.0(4) C2' N1 Cu1 . . 118.4(4) C2" N1 Cu1 . . 110.9(8) C2 N1 H1A . . 107.3 Cu1 N1 H1A . . 107.3 C2 N1 H1B . . 107.3 Cu1 N1 H1B . . 107.3 H1A N1 H1B . . 106.9 C2' N1 H1C . . 107.7 Cu1 N1 H1C . . 107.7 C2' N1 H1D . . 107.7 Cu1 N1 H1D . . 107.7 H1C N1 H1D . . 107.1 C2" N1 H1E . . 109.5 Cu1 N1 H1E . . 109.5 C2" N1 H1F . . 109.5 Cu1 N1 H1F . . 109.5 H1E N1 H1F . . 108.0 C6 N2 C4 . . 106.1(2) C6 N2 Cu1 . . 126.94(18) C4 N2 Cu1 . . 126.83(17) C6 N3 C5 . . 108.2(2) C6 N3 H3 . . 120(3) C5 N3 H3 . . 132(3) C7 N4 Cu1 . . 142.8(3) C7 N5 C8 . . 119.7(3) O2 C1 O1 3_665 . 126.6(2) O2 C1 C1 3_665 3_665 116.7(3) O1 C1 C1 . 3_665 116.7(3) N1 C2 C3 . . 110.1(7) N1 C2 H2A . . 109.6 C3 C2 H2A . . 109.6 N1 C2 H2B . . 109.6 C3 C2 H2B . . 109.6 H2A C2 H2B . . 108.2 C4 C3 C2 . . 110.7(7) C4 C3 H3A . . 109.5 C2 C3 H3A . . 109.5 C4 C3 H3B . . 109.5 C2 C3 H3B . . 109.5 H3A C3 H3B . . 108.1 N1 C2' C3' . . 107.3(9) N1 C2' H2'A . . 110.3 C3' C2' H2'A . . 110.3 N1 C2' H2'B . . 110.3 C3' C2' H2'B . . 110.3 H2'A C2' H2'B . . 108.5 C2' C3' C4 . . 108.6(8) C2' C3' H3'A . . 110.0 C4 C3' H3'A . . 110.0 C2' C3' H3'B . . 110.0 C4 C3' H3'B . . 110.0 H3'A C3' H3'B . . 108.4 N1 C2" C3" . . 110.5(17) N1 C2" H2"A . . 109.5 C3" C2" H2"A . . 109.5 N1 C2" H2"B . . 109.5 C3" C2" H2"B . . 109.5 H2"A C2" H2"B . . 108.1 C2" C3" C4 . . 110.4(15) C2" C3" H3"A . . 109.6 C4 C3" H3"A . . 109.6 C2" C3" H3"B . . 109.6 C4 C3" H3"B . . 109.6 H3"A C3" H3"B . . 108.1 C5 C4 N2 . . 109.1(2) C5 C4 C3 . . 129.0(4) N2 C4 C3 . . 120.2(4) C5 C4 C3" . . 127.2(10) N2 C4 C3" . . 123.3(10) C5 C4 C3' . . 127.6(6) N2 C4 C3' . . 118.1(7) N3 C5 C4 . . 106.0(2) N3 C5 H5A . . 127.0 C4 C5 H5A . . 127.0 N2 C6 N3 . . 110.6(2) N2 C6 H6A . . 124.7 N3 C6 H6A . . 124.7 N4 C7 N5 . . 174.2(3) N6 C8 N5 . . 173.6(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance Cu1 N2 . 1.966(2) Cu1 N1 . 1.983(2) Cu1 O2 . 1.9978(18) Cu1 O1 . 2.0165(17) Cu1 N4 . 2.426(3) O1 C1 . 1.251(3) O2 C1 3_665 1.249(3) N1 C2 . 1.497(5) N1 C2' . 1.497(6) N1 C2" . 1.498(6) N1 H1A . 0.9100 N1 H1B . 0.9100 N1 H1C . 0.9100 N1 H1D . 0.9100 N1 H1E . 0.9100 N1 H1F . 0.9100 N2 C6 . 1.320(3) N2 C4 . 1.373(3) N3 C6 . 1.338(3) N3 C5 . 1.357(4) N3 H3 . 0.91(5) N4 C7 . 1.154(4) N5 C7 . 1.304(4) N5 C8 . 1.306(4) N6 C8 . 1.153(4) C1 O2 3_665 1.249(3) C1 C1 3_665 1.557(4) C2 C3 . 1.521(7) C2 H2A . 0.9900 C2 H2B . 0.9900 C3 C4 . 1.521(5) C3 H3A . 0.9900 C3 H3B . 0.9900 C2' C3' . 1.522(8) C2' H2'A . 0.9900 C2' H2'B . 0.9900 C3' C4 . 1.526(6) C3' H3'A . 0.9900 C3' H3'B . 0.9900 C2" C3" . 1.521(8) C2" H2"A . 0.9900 C2" H2"B . 0.9900 C3" C4 . 1.524(6) C3" H3"A . 0.9900 C3" H3"B . 0.9900 C4 C5 . 1.362(4) C5 H5A . 0.9500 C6 H6A . 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N1 H1E O1 3_666 0.91 2.29 3.131(3) 154.1 N1 H1F N4 4_576 0.91 2.50 3.377(4) 161.0 N3 H3 N6 4_475 0.91(5) 2.10(5) 2.954(3) 157(4) C2 H2A O2 1_556 0.99 2.52 3.2770(10) 133.1 _cod_database_fobs_code 2241260