#------------------------------------------------------------------------------ #$Date: 2020-02-18 01:58:29 +0200 (Tue, 18 Feb 2020) $ #$Revision: 248240 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/73/1557327.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1557327 loop_ _publ_author_name 'Smellie, Iain A.' 'Abdelhamid, Yusra' 'Carpenter-Warren, Cameron L.' 'Cordes, David B.' 'Elliott, Clement' 'Lamorte, Sarah' 'Patterson, Iain L. J.' 'Sanders, William' 'Sandison, Iain P.' 'Slawin, Alexandra M. Z.' 'Stewart, Dominic M.' 'Walters, Samuel N.' _publ_section_title ; A Simplified Extractive Metallurgy Exercise to Demonstrate Selective Extraction of Copper ; _journal_name_full 'Journal of Chemical Education' _journal_paper_doi 10.1021/acs.jchemed.9b00996 _journal_year 2020 _chemical_formula_moiety 'C16 H16 Cu N2 O6' _chemical_formula_sum 'C16 H16 Cu N2 O6' _chemical_formula_weight 395.85 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2019-08-07 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 94.790(8) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 8.4484(7) _cell_length_b 4.8581(4) _cell_length_c 18.7404(15) _cell_measurement_reflns_used 613 _cell_measurement_temperature 173 _cell_measurement_theta_max 25.4 _cell_measurement_theta_min 2.2 _cell_volume 766.48(11) _computing_cell_refinement 'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)' _computing_data_collection 'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)' _computing_data_reduction 'CrystalClear-SM Expert 2.1 b45 (Rigaku, 2015)' _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009), enCIFer (Allen et al., 2004)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 173 _diffrn_detector CCD _diffrn_detector_area_resol_mean 13.6612 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; scan: Number of images: 180 Slice: -120.0000 - 60.0000 Image width: 1.0000 Exp time: 30.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 0.0000 XTD: 51.8800 2theta: -29.5400 scan: Number of images: 180 Slice: -120.0000 - 60.0000 Image width: 1.0000 Exp time: 30.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 120.0000 XTD: 51.8800 2theta: -29.5400 scan: Number of images: 180 Slice: -120.0000 - 60.0000 Image width: 1.0000 Exp time: 30.0000 Rotation axis: Omega Omega: 0.0000 Chi: 54.0000 Phi: 240.0000 XTD: 51.8800 2theta: -29.5400 ; _diffrn_measurement_device ; SCXMini: Fixed Chi 2 circle ; _diffrn_measurement_device_type 'Rigaku Mercury2 (2x2 bin mode)' _diffrn_measurement_method 'profile data from \w-scans' _diffrn_measurement_specimen_support Loop _diffrn_orient_matrix_type d*Trek _diffrn_orient_matrix_UB_11 0.060207 _diffrn_orient_matrix_UB_12 0.102374 _diffrn_orient_matrix_UB_13 0.001886 _diffrn_orient_matrix_UB_21 -0.112902 _diffrn_orient_matrix_UB_22 0.063450 _diffrn_orient_matrix_UB_23 0.159994 _diffrn_orient_matrix_UB_31 0.037752 _diffrn_orient_matrix_UB_32 -0.017634 _diffrn_orient_matrix_UB_33 0.033633 _diffrn_radiation_monochromator 'Graphite Monochromator' _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71075 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_unetI/netI 0.0368 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 6266 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.343 _diffrn_reflns_theta_min 2.181 _diffrn_source 'Sealed Tube' _diffrn_source_current 20.0 _diffrn_source_power 1.0 _diffrn_source_type 'Rigaku SCXMini' _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 1.463 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.786 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'REQAB (Rigaku, 1997)' _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 406 _exptl_crystal_preparation Loop _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.340 _refine_diff_density_min -0.258 _refine_diff_density_rms 0.068 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 1400 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0317 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0440P)^2^+0.6392P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0790 _refine_ls_wR_factor_ref 0.0843 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1119 _reflns_number_total 1400 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ed9b00996_si_004.cif _cod_data_source_block 3 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. data item '_exptl_absorpt_correction_type' value 'Multi-scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_formula_sum 'C16 H16 Cu1 N2 O6' _cod_database_code 1557327 _shelx_shelxl_version_number 2018/3 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H,H) groups 2. Restrained distances O2-H2 0.98 with sigma of 0.01 3.a Aromatic/amide H refined with riding coordinates: C5(H5), C7(H7), C3(H3), C4(H4) 3.b Idealised Me refined as rotating group: C8(H8A,H8B,H8C) ; _shelx_res_file ; TITL swdc1_a.res in P2(1)/n swdc1.res created by SHELXL-2018/3 at 13:49:50 on 07-Aug-2019 REM Old TITL SWDC1 REM SHELXT solution in P2(1)/n REM R1 0.082, Rweak 0.001, Alpha 0.012, Orientation as input REM Formula found by SHELXT: C16 Cu N4 O3 CELL 0.71075 8.4484 4.8581 18.7404 90 94.79 90 ZERR 2 0.0007 0.0004 0.0015 0 0.008 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H Cu N O UNIT 32 32 2 4 12 EQIV $1 1-X,2-Y,1-Z DFIX 0.98 0.01 O2 H2 L.S. 20 PLAN 20 HTAB O2 O1_$1 BOND $H list 4 fmap 2 53 acta REM REM REM WGHT 0.044000 0.639200 FVAR 0.83568 CU1 3 0.500000 1.000000 0.500000 10.50000 0.02008 0.02060 = 0.02685 0.00243 0.00270 -0.00087 O1 5 0.489192 0.717257 0.568430 11.00000 0.02301 0.02418 = 0.03211 0.00692 0.00375 0.00146 O2 5 0.800104 1.106667 0.444571 11.00000 0.02178 0.03466 = 0.03501 0.01084 0.00459 -0.00241 O3 5 0.411109 0.362841 0.663131 11.00000 0.02850 0.02781 = 0.03529 0.00928 0.00673 -0.00114 N1 4 0.724095 0.940227 0.492282 11.00000 0.02128 0.02783 = 0.02231 0.00096 0.00264 -0.00515 C2 1 0.765282 0.580410 0.580364 11.00000 0.02434 0.02091 = 0.02576 -0.00436 0.00026 -0.00022 C1 1 0.606057 0.561464 0.597768 11.00000 0.02507 0.02000 = 0.02454 -0.00490 0.00002 -0.00016 C5 1 0.683998 0.194939 0.682380 11.00000 0.03682 0.02037 = 0.02753 0.00144 0.00005 -0.00055 AFIX 43 H5 2 0.657328 0.065642 0.715955 11.00000 -1.20000 AFIX 0 C6 1 0.568356 0.364998 0.649508 11.00000 0.02839 0.01898 = 0.02517 -0.00275 0.00229 -0.00198 C7 1 0.816362 0.770068 0.527992 11.00000 0.01876 0.02627 = 0.02990 -0.00373 0.00318 -0.00038 AFIX 43 H7 2 0.923203 0.769518 0.519407 11.00000 -1.20000 AFIX 0 C3 1 0.881458 0.405588 0.615368 11.00000 0.02415 0.02617 = 0.02848 -0.00374 -0.00102 0.00340 AFIX 43 H3 2 0.986543 0.418770 0.604412 11.00000 -1.20000 AFIX 0 C4 1 0.841183 0.218476 0.664859 11.00000 0.03413 0.02267 = 0.03062 -0.00059 -0.00347 0.00569 AFIX 43 H4 2 0.918985 0.105173 0.687239 11.00000 -1.20000 AFIX 0 C8 1 0.362421 0.151286 0.709632 11.00000 0.03895 0.02818 = 0.03335 0.00513 0.00820 -0.00488 AFIX 137 H8A 2 0.391966 -0.025080 0.691831 11.00000 -1.50000 H8B 2 0.249271 0.158479 0.711442 11.00000 -1.50000 H8C 2 0.413339 0.178429 0.756841 11.00000 -1.50000 AFIX 0 H2 2 0.715766 1.229498 0.427136 11.00000 -1.50000 HKLF 4 REM swdc1_a.res in P2(1)/n REM wR2 = 0.0843, GooF = S = 1.011, Restrained GooF = 1.011 for all data REM R1 = 0.0317 for 1119 Fo > 4sig(Fo) and 0.0438 for all 1400 data REM 119 parameters refined using 1 restraints END WGHT 0.0438 0.6435 REM Highest difference peak 0.340, deepest hole -0.258, 1-sigma level 0.068 Q1 1 0.6786 0.5452 0.5805 11.00000 0.05 0.34 Q2 1 0.7886 0.4416 0.5785 11.00000 0.05 0.32 Q3 1 0.5880 0.4095 0.6042 11.00000 0.05 0.29 Q4 1 0.8154 0.4989 0.5984 11.00000 0.05 0.29 Q5 1 0.5533 0.6178 0.5806 11.00000 0.05 0.28 Q6 1 0.6051 0.2155 0.6436 11.00000 0.05 0.27 Q7 1 0.4980 0.3554 0.6578 11.00000 0.05 0.27 Q8 1 0.7467 1.1559 0.4327 11.00000 0.05 0.27 Q9 1 0.6525 0.8816 0.4814 11.00000 0.05 0.26 Q10 1 0.7910 0.9169 0.4445 11.00000 0.05 0.26 Q11 1 0.7689 0.9066 0.5185 11.00000 0.05 0.26 Q12 1 0.5004 0.7503 0.5400 11.00000 0.05 0.25 Q13 1 0.6198 0.2530 0.6562 11.00000 0.05 0.25 Q14 1 0.5196 0.9988 0.5580 11.00000 0.05 0.24 Q15 1 0.4178 0.9977 0.4426 11.00000 0.05 0.23 Q16 1 0.3983 0.2664 0.6827 11.00000 0.05 0.23 Q17 1 0.9127 0.3940 0.5893 11.00000 0.05 0.23 Q18 1 0.3990 0.8758 0.5402 11.00000 0.05 0.22 Q19 1 0.3624 0.3987 0.6476 11.00000 0.05 0.21 Q20 1 0.7833 0.5966 0.5474 11.00000 0.05 0.21 ; _shelx_res_checksum 47383 _shelx_hkl_file ; 0 0 2 6491.52 193.73 -1 0 0 0.75 4.89 -1 0 0 1.85 12.17 1 0 0 3.10 5.56 -1 0 -1 2914.35 88.55 -1 0 2 0.57 7.13 1 0 -2 -2.30 7.64 -1 0 2 2.83 9.27 0 0 -3 3.38 8.13 0 0 3 2.57 7.52 0 0 -3 5.14 6.15 0 0 -3 6.36 6.99 1 0 2 6.11 7.23 -1 0 -2 0.14 6.81 1 0 2 -0.02 6.44 1 0 -3 1132.25 38.31 -1 0 3 1161.40 38.09 -1 0 3 1143.34 38.35 1 0 -3 1085.95 36.13 0 -1 0 -0.55 6.48 0 -1 0 -4.87 7.26 0 1 0 -1.39 5.75 0 1 0 -1.77 7.56 -1 0 -3 357.09 17.38 1 0 3 329.91 15.26 -1 0 -3 362.31 18.48 0 -1 1 1327.96 42.94 0 1 1 1166.96 39.09 0 -1 -1 1184.47 39.86 0 1 1 1344.65 43.63 0 1 -1 1261.44 41.66 0 -1 -1 1278.07 40.66 0 1 -1 1303.71 42.35 0 0 4 292.55 15.98 0 0 -4 293.20 16.32 0 0 -4 289.96 15.33 0 -1 -2 613.08 25.98 0 -1 2 633.69 22.76 0 1 -2 640.43 24.44 0 1 2 686.02 25.74 0 1 -2 663.62 25.35 0 -1 -2 650.11 24.21 -1 0 4 0.71 6.62 -1 0 4 -1.87 6.89 1 0 -4 1.96 6.01 1 0 -4 -2.75 8.11 2 0 0 112.50 9.72 -2 0 0 121.44 10.68 2 0 0 119.53 11.90 1 1 0 568.35 21.95 1 1 0 534.17 21.72 1 -1 0 477.43 19.48 -1 -1 0 537.82 21.99 1 -1 0 517.99 20.03 -1 1 0 554.14 22.34 -2 0 1 0.29 8.07 2 0 -1 5.09 7.05 1 1 -1 312.64 15.86 1 -1 -1 295.42 14.31 -1 1 1 314.15 15.71 1 -1 -1 280.16 13.37 -1 -1 1 320.65 16.30 1 1 -1 340.77 16.59 1 -1 1 121.10 9.56 -1 -1 -1 115.82 9.17 1 1 1 116.47 10.50 -1 1 -1 120.53 11.07 -1 -1 -1 110.60 10.11 -1 1 -1 121.81 13.25 2 0 1 3.18 5.79 -2 0 -1 7.89 5.65 2 0 1 -3.67 7.56 -2 0 -1 6.99 8.17 2 0 -2 82.42 10.23 -2 0 2 75.47 10.27 -2 0 2 86.08 10.33 -1 0 -4 -3.32 8.03 -1 0 -4 -2.02 6.83 1 0 4 4.59 7.56 1 -1 -2 7.38 7.91 1 1 -2 6.81 8.89 1 1 -2 12.39 6.99 -1 1 2 13.25 8.23 -1 1 2 6.15 8.46 -1 -1 2 0.65 8.89 0 -1 -3 7523.05 214.46 0 -1 -3 7403.75 210.73 0 1 3 7338.27 217.96 0 1 -3 7116.74 201.76 1 1 2 5591.24 161.12 -1 1 -2 5333.48 152.73 -1 -1 -2 5023.14 150.14 -1 1 -2 5419.30 157.13 -1 1 -2 5274.16 152.28 -1 -1 -2 5194.80 149.81 0 0 -5 1.39 8.95 0 0 -5 8.46 8.52 0 0 5 -16.06 9.19 -2 0 -2 1444.82 47.75 2 0 2 1394.91 44.35 2 0 2 1224.84 39.23 -2 0 3 -1.32 8.54 -2 0 3 1.18 7.87 2 0 -3 -2.98 7.99 -1 1 3 4.63 5.85 -1 -1 3 0.92 7.64 -1 1 3 5.48 8.66 1 1 -3 7.48 6.81 1 1 -3 7.03 7.58 1 -1 -3 1.16 6.42 1 0 -5 302.48 15.73 -1 0 5 309.53 14.80 -1 0 5 269.05 14.69 1 0 -5 301.95 14.29 -1 -1 -3 3216.71 94.56 -1 -1 -3 3082.02 93.54 -1 1 -3 3228.24 95.56 1 1 3 3409.76 102.08 -1 1 -3 3139.33 94.15 -1 1 -3 3131.54 92.95 -2 0 -3 -2.18 7.46 2 0 3 -0.41 8.25 -2 0 -3 5.87 8.58 -1 0 -5 5581.14 161.98 1 0 5 5427.09 156.94 -1 0 -5 5618.88 160.55 2 0 -4 797.01 29.02 -2 0 4 813.15 28.88 -2 0 4 908.22 31.67 -1 -1 4 290.90 14.08 -1 1 4 287.84 13.12 -1 1 4 307.98 15.73 1 1 -4 313.58 14.75 1 1 -4 310.73 16.53 1 -1 -4 283.30 14.69 -2 1 0 718.40 26.31 -2 -1 0 787.55 28.67 -2 1 0 755.74 28.27 2 1 0 776.04 27.45 2 1 0 665.07 25.74 2 -1 0 768.60 26.92 -2 -1 1 35.83 10.21 2 1 -1 43.12 8.19 -2 1 1 44.37 7.70 2 1 -1 41.92 8.62 -2 1 1 54.19 11.07 2 -1 -1 48.93 8.72 0 0 6 3325.68 107.52 0 0 -6 3348.52 98.49 0 0 -6 3551.40 104.43 2 1 1 22.62 7.91 -2 1 -1 25.58 7.15 -2 -1 -1 22.13 10.58 -2 1 -1 24.94 8.31 2 -1 1 23.01 7.13 -2 1 2 308.06 14.57 -2 1 2 304.15 15.33 2 1 -2 330.37 15.33 2 1 -2 306.73 16.53 2 -1 -2 309.63 14.90 -2 -1 2 322.00 17.34 -1 -1 -4 9257.04 270.52 -1 1 -4 9380.95 268.67 -1 -1 -4 9374.85 264.67 1 1 4 9999.00 273.76 -2 0 -4 461.64 20.91 -2 0 -4 432.54 19.79 2 0 4 409.20 18.61 -1 0 6 0.51 7.91 -1 0 6 -7.66 6.15 1 0 -6 -1.41 7.97 -2 1 -2 283.32 14.96 -2 -1 -2 282.56 13.35 2 1 2 301.97 15.61 2 -1 2 281.46 13.39 -2 1 -2 277.35 15.02 -2 -1 -2 281.12 15.00 2 0 -5 -1.55 7.74 -2 0 5 5.14 6.77 -2 0 5 13.72 7.87 2 1 -3 2203.59 66.91 2 -1 -3 2114.72 64.58 2 1 -3 2141.13 66.52 -2 1 3 2134.44 65.83 -2 1 3 2164.20 66.78 -2 -1 3 2207.14 67.05 1 -1 -5 62.26 9.56 -1 1 5 53.09 9.52 -1 1 5 68.60 7.89 1 1 -5 63.20 9.78 1 1 -5 60.87 7.72 -1 -1 5 54.33 7.74 -1 0 -6 -2.12 8.29 -1 0 -6 6.20 7.72 1 0 6 -2.79 5.60 -3 0 1 5264.48 158.47 3 0 -1 5244.77 150.65 3 0 -1 5345.63 154.72 -3 0 0 1.77 7.99 3 0 0 -10.76 9.76 -2 -1 -3 605.56 24.31 2 1 3 622.48 23.95 -2 1 -3 571.41 23.15 -2 1 -3 609.54 24.17 -2 -1 -3 617.99 22.72 3 0 -2 0.33 6.79 -3 0 2 2.98 8.21 3 0 -2 -7.97 7.13 3 0 1 6291.75 180.32 -3 0 -1 6322.57 182.76 -1 1 -5 679.66 25.43 -1 -1 -5 668.00 24.44 -1 1 -5 674.16 26.17 1 1 5 717.53 26.94 -1 1 -5 635.36 23.95 -1 -1 -5 680.01 26.68 2 -1 -4 48.73 7.91 2 1 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2 1 -21 47.00 19.89 -2 1 21 65.40 17.28 -2 -1 21 50.13 16.10 7 2 -14 6.28 16.85 -7 -2 14 23.93 12.31 -7 2 14 23.99 13.12 7 -2 -14 22.99 17.02 -5 -4 11 206.47 20.97 5 4 -11 153.23 18.12 5 -4 -11 199.23 20.18 -5 4 11 161.14 16.18 8 -1 -13 337.63 26.41 -8 -1 13 354.26 24.62 -8 1 13 352.22 28.88 8 1 -13 342.97 30.30 -9 2 4 -19.52 16.81 -9 2 4 -12.43 15.59 9 2 -4 -10.82 13.88 -9 -2 4 5.18 19.12 1 4 -15 258.62 21.93 -1 -4 15 289.37 24.09 1 -4 -15 256.85 21.95 -1 4 15 237.14 24.50 -6 0 18 69.92 16.87 6 0 -18 36.79 14.53 -3 -4 14 -4.24 14.47 -3 4 14 -10.21 18.22 3 -4 -14 -5.01 11.70 3 4 -14 8.64 14.39 0 4 -15 120.65 17.02 0 -4 -15 154.03 19.83 0 -4 15 122.60 17.14 0 4 15 101.45 17.73 4 5 3 54.15 15.39 -4 -5 -3 44.86 14.18 -4 5 -3 60.43 21.05 4 -5 3 83.48 16.59 -8 2 -8 143.57 19.10 8 -2 8 130.80 18.40 -8 -2 -8 133.63 19.52 8 2 8 154.70 20.89 -3 0 21 100.43 17.04 3 0 -21 125.50 15.79 9 -2 1 38.52 11.58 9 2 1 26.29 16.83 -9 2 -1 34.77 13.31 -9 -2 -1 52.48 15.63 -8 2 11 10.17 14.41 -8 2 11 -3.18 13.84 -8 -2 11 5.60 15.20 8 -2 -11 16.22 13.63 8 2 -11 20.56 18.22 -2 4 -14 312.89 24.25 2 -4 14 291.08 22.58 2 4 14 274.53 25.35 -2 -4 -14 201.62 21.58 -2 -4 -14 243.66 22.03 -6 4 -6 351.41 29.00 6 4 6 282.60 28.02 6 -4 6 386.07 30.57 -6 -4 -6 296.36 28.47 -2 -3 18 25.72 14.88 2 3 -18 37.48 15.20 2 -3 -18 27.08 18.65 -2 3 18 8.07 15.08 6 -2 14 250.14 24.90 -6 -2 -14 308.41 30.98 -6 2 -14 251.65 28.65 6 2 14 222.87 25.74 2 -5 -9 118.45 21.30 2 5 -9 140.95 18.69 -2 5 9 125.36 22.46 2 5 -9 121.14 17.61 -5 -1 19 3.55 13.49 -5 1 19 -0.51 10.60 5 1 -19 8.60 14.84 5 -1 -19 3.67 11.60 4 -1 -20 165.48 20.99 4 1 -20 160.37 22.23 -4 1 20 197.09 22.60 -4 -1 20 237.14 24.41 -2 -2 20 186.25 22.34 2 -2 -20 176.55 22.58 -2 2 20 140.62 17.36 2 2 -20 112.09 19.52 -3 4 -13 91.97 16.83 -3 -4 -13 70.11 17.91 3 -4 13 94.77 18.12 3 4 13 111.72 22.27 9 -1 -9 -2.47 15.39 -9 -1 9 -4.85 12.59 9 -1 -9 2.18 13.70 -9 1 9 8.82 12.66 4 -4 -13 2.75 10.96 -4 -4 13 21.91 17.57 -4 4 13 44.47 19.46 4 4 -13 -6.62 14.67 -9 0 10 5.95 16.85 9 0 -10 5.07 16.55 -4 5 5 332.56 29.43 4 5 -5 328.58 31.18 4 -5 -5 292.39 26.25 -4 -5 5 333.51 29.43 8 3 3 225.81 23.05 -8 3 -3 243.15 24.84 -8 -3 -3 272.23 30.43 -9 2 5 451.98 37.01 -9 2 5 424.35 37.19 -9 -2 5 389.60 32.18 9 -2 -5 359.99 31.89 9 2 -5 434.84 35.32 8 3 -6 1.32 12.49 -8 3 6 12.98 16.75 -8 -3 6 2.34 15.26 8 -3 -6 5.01 15.41 -3 0 -20 22.40 15.75 -7 3 11 -2.57 11.09 -7 -3 11 -6.89 17.49 7 3 -11 -0.08 17.95 7 -3 -11 3.42 12.31 5 -2 16 -15.35 16.20 5 2 16 1.94 15.45 -5 2 -16 -5.12 10.84 -5 -2 -16 -20.11 19.81 4 0 19 -2.00 13.31 -4 0 -19 16.73 15.94 9 -2 2 38.62 11.80 -9 2 -2 25.60 14.61 -9 -2 -2 12.02 18.89 9 2 2 5.34 15.08 1 -1 21 -2.98 10.25 -1 1 -21 29.77 15.43 1 1 21 9.68 12.80 -1 -1 -21 38.80 16.12 -8 0 -11 -7.46 22.23 8 0 11 -3.10 18.02 1 3 18 228.72 27.19 1 -3 18 306.14 26.60 1 3 18 233.12 24.76 -1 3 -18 295.95 26.51 -1 -3 -18 276.43 24.78 -6 0 -16 565.15 30.79 6 0 16 558.71 48.83 3 -5 -8 388.40 32.38 3 5 -8 256.72 26.45 -3 5 8 323.85 30.85 -9 -1 -6 250.41 27.27 9 1 6 264.08 29.73 9 -1 6 224.60 25.47 -9 1 -6 281.06 28.37 -8 0 14 480.08 39.64 8 0 -14 479.31 38.90 0 -5 -10 18.77 10.82 0 5 -10 18.46 14.63 0 5 10 13.14 14.51 0 -5 10 -10.27 14.65 2 4 -15 -14.84 11.74 -2 4 15 -8.54 18.79 -2 -4 15 -16.18 13.49 2 -4 -15 -12.11 13.17 -4 5 -4 8.89 12.41 -4 -5 -4 14.63 13.06 4 -5 4 -4.91 15.55 4 5 4 11.53 16.30 7 1 -16 141.74 22.32 -7 1 16 87.06 14.57 7 -1 -16 111.46 21.93 -7 -1 16 94.07 15.77 3 5 7 16.10 15.59 -3 -5 -7 -5.09 13.59 3 -5 7 -11.23 15.41 -3 5 -7 4.38 14.69 1 5 -10 28.94 16.71 -1 5 10 58.14 15.59 1 -5 -10 55.76 16.77 4 -2 -19 -6.97 13.04 4 2 -19 10.94 18.16 -4 2 19 0.55 14.14 -4 -2 19 -8.78 14.98 9 0 7 217.49 25.54 -9 0 -7 213.74 23.56 -1 2 -20 -3.61 11.41 1 -2 20 6.15 12.37 -1 -2 -20 -15.53 12.72 1 2 20 -10.35 9.05 -1 -4 -15 274.23 24.68 1 -4 15 340.44 29.80 1 4 15 307.10 27.27 -1 4 -15 354.08 29.94 5 -2 -18 23.88 17.47 5 2 -18 15.81 18.00 -5 2 18 19.28 15.69 -5 -2 18 14.94 11.51 -7 0 -14 5.50 19.10 7 0 14 -7.28 13.33 -9 -2 6 -6.11 18.38 -9 2 6 -2.22 18.18 9 -2 -6 0.02 14.55 9 2 -6 5.09 13.39 -9 2 6 -6.70 11.82 6 -4 -9 118.16 20.03 -6 -4 9 117.77 18.81 -6 4 9 160.73 20.89 6 4 -9 99.21 19.73 6 -3 -14 14.33 11.84 -6 -3 14 -10.94 18.04 6 3 -14 21.09 16.69 -6 3 14 20.36 11.29 4 -5 -6 22.05 14.57 -4 5 6 -9.33 14.18 4 5 -6 -12.78 13.04 -4 -5 6 1.06 11.70 -7 -2 -12 63.03 20.01 7 2 12 39.27 17.69 -7 2 -12 63.63 19.42 7 -2 12 49.56 16.71 4 -3 -17 185.03 22.85 4 3 -17 195.81 22.91 -4 -3 17 200.35 23.29 -8 -3 -4 8.72 19.89 8 3 4 2.71 15.04 -8 3 -4 -1.47 11.07 -6 1 18 -11.43 11.17 -6 -1 18 -3.18 11.82 6 1 -18 16.06 18.04 6 -1 -18 2.98 11.76 -7 -4 1 141.99 18.44 -7 4 1 186.98 22.93 7 -4 -1 187.84 20.24 7 4 -1 176.98 19.58 -8 3 7 163.10 20.89 8 -3 -7 167.58 21.07 -8 -3 7 173.88 22.40 -2 0 -21 -4.85 16.51 2 0 21 2.20 12.86 -7 4 2 27.08 15.86 -7 -4 2 19.63 13.27 7 4 -2 11.60 16.81 7 -4 -2 14.73 14.18 9 2 3 109.19 20.42 -9 -2 -3 84.03 24.46 -9 2 -3 88.08 18.02 9 -2 3 79.01 12.55 3 -1 -21 11.86 21.79 3 1 -21 -5.46 15.47 -3 1 21 -6.05 13.86 -3 -1 21 11.94 16.85 2 5 9 258.68 27.45 -2 -5 -9 262.96 24.29 2 -5 9 303.76 27.61 -2 5 -9 297.40 28.63 -4 4 -12 50.68 18.00 4 4 12 54.19 14.20 4 -4 12 42.78 12.23 -4 -4 -12 51.54 15.49 -7 -4 0 9.42 13.55 -7 4 0 24.19 15.84 7 4 0 -16.22 15.86 7 -4 0 -4.46 12.09 5 -3 14 66.80 14.49 -5 3 -14 110.25 16.96 -5 -3 -14 146.47 23.33 5 3 14 89.73 19.08 5 -3 14 93.05 15.12 5 -4 10 -0.98 16.94 5 4 10 -8.36 15.81 -5 4 -10 5.97 14.55 -5 -4 -10 5.22 16.81 -1 5 -10 233.51 23.56 -1 -5 -10 200.54 20.24 1 -5 10 228.56 22.74 1 5 10 212.19 25.68 -6 4 -7 -8.50 10.76 6 4 7 -5.60 14.88 6 -4 7 1.47 12.21 -6 -4 -7 9.40 18.85 -7 -3 -9 0.96 18.28 7 3 9 -1.06 15.90 -7 3 -9 14.18 15.77 -7 4 3 155.05 18.61 7 4 -3 162.18 20.16 7 -4 -3 159.80 18.42 -7 -4 3 134.69 17.63 -9 1 10 208.14 23.91 9 1 -10 151.93 21.50 9 -1 -10 171.49 23.13 -9 -1 10 177.30 19.12 5 0 18 -1.37 13.63 -5 0 -18 -8.25 12.98 4 -5 5 64.87 16.55 4 5 5 55.55 13.88 -4 5 -5 71.33 13.88 -1 0 22 -1.63 14.16 1 0 -22 -0.26 20.22 6 -3 12 -2.85 11.01 -6 -3 -12 10.35 19.99 6 3 12 6.24 14.98 -6 3 -12 4.34 18.83 -7 -4 -1 147.10 19.42 -7 4 -1 166.36 18.73 7 -4 1 173.84 20.11 7 4 1 157.64 19.03 3 2 -20 -2.61 11.80 -3 2 20 -3.34 15.77 -3 -2 20 2.04 15.55 3 -2 -20 5.60 15.92 -5 -4 12 44.92 17.71 5 -4 -12 49.64 15.73 5 4 -12 35.75 20.34 -5 4 12 23.54 15.73 3 -3 -18 87.57 24.80 3 3 -18 74.96 19.99 -3 -3 18 119.91 18.50 3 -1 20 114.53 14.00 -3 -1 -20 78.85 15.96 -8 2 -9 -8.05 13.82 8 2 9 -7.76 12.51 8 -2 9 -25.76 14.78 2 5 -10 33.20 18.55 2 -5 -10 19.65 19.18 -2 5 10 2.22 18.02 5 3 -16 108.15 18.63 5 -3 -16 120.30 19.32 -5 -3 16 154.91 20.73 8 2 -12 100.00 20.99 8 -2 -12 118.71 19.93 -8 2 12 126.35 20.20 -8 -2 12 96.11 20.05 -8 2 12 86.67 17.75 -4 1 -19 160.59 26.33 -4 -1 -19 103.20 15.75 4 1 19 84.72 17.81 9 0 -11 48.14 13.65 -9 0 11 51.25 18.59 7 -4 -4 35.03 11.94 7 4 -4 31.98 12.86 -7 4 4 38.21 13.86 -7 -4 4 27.39 15.98 -8 1 -11 15.63 23.38 -8 -1 -11 18.57 20.26 8 1 11 21.81 18.06 8 -1 11 14.78 12.84 -9 2 7 323.00 30.59 9 -2 -7 282.63 26.41 -9 -2 7 292.86 29.14 -9 2 7 318.66 30.83 -6 1 -16 10.35 13.63 -6 -1 -16 14.39 15.41 6 -1 16 10.39 18.04 6 1 16 47.26 15.77 0 0 -22 9.31 19.46 0 0 22 11.19 11.05 8 1 -14 -20.05 20.20 8 -1 -14 25.82 14.57 -8 1 14 12.43 18.16 -8 -1 14 -2.77 17.30 -3 5 9 8.66 16.39 3 -5 -9 -5.77 14.75 3 5 -9 -12.25 20.99 -3 3 -17 13.74 16.36 3 3 17 3.48 14.20 3 -3 17 21.36 13.02 -3 -3 -17 6.18 18.71 -3 2 -19 65.68 16.67 3 2 19 26.21 11.13 3 -2 19 59.35 12.80 -3 -2 -19 62.61 15.75 9 1 7 15.10 17.61 -9 1 -7 10.21 18.91 -9 -1 -7 35.91 20.11 9 -1 7 35.73 12.00 5 0 -20 -2.47 13.02 -5 0 20 -7.68 13.63 7 0 -17 80.38 17.42 -7 0 17 79.40 13.96 -7 2 15 36.42 16.47 7 2 -15 48.85 19.40 7 -2 -15 42.88 14.18 -7 -2 15 77.42 19.83 -3 5 -8 449.29 38.40 3 -5 8 484.24 38.25 -3 -5 -8 393.57 32.97 3 5 8 404.94 32.85 -7 -4 -2 4.95 19.69 -7 4 -2 -8.97 14.78 7 4 2 22.32 14.53 7 -4 2 9.03 13.96 -4 5 7 166.42 23.17 4 5 -7 107.01 19.63 -4 -5 7 109.34 14.71 4 -5 -7 161.90 18.97 7 -3 -12 134.57 17.28 7 3 -12 108.15 20.36 -7 3 12 98.62 15.88 -7 -3 12 98.03 14.04 -9 2 -4 2.00 16.06 -9 -2 -4 10.29 21.85 9 2 4 -13.47 23.64 9 -2 4 8.62 10.50 2 0 -22 211.54 19.40 -2 0 22 268.32 18.44 6 -2 -17 -1.57 11.74 6 2 -17 -15.33 23.52 -6 -2 17 16.87 17.02 -6 2 17 9.54 11.78 -8 -3 -5 168.85 22.85 8 3 5 150.93 16.16 -8 3 -5 206.41 17.65 7 -1 14 14.37 19.38 7 1 14 59.59 18.87 -7 -1 -14 33.69 15.33 -7 1 -14 24.99 16.02 8 -3 -8 30.69 15.77 -8 3 8 22.32 11.90 -8 -3 8 16.02 17.83 -4 2 -18 33.40 18.02 -4 -2 -18 62.73 23.50 4 2 18 27.39 14.55 -4 0 21 -5.99 20.95 4 0 -21 8.68 14.29 -10 0 2 152.40 20.62 10 0 -2 175.63 17.83 3 4 -15 99.58 18.20 -3 4 15 101.80 17.32 3 -4 -15 106.71 15.18 -3 -4 15 127.72 15.00 9 0 8 -2.53 15.10 -9 0 -8 -1.90 17.08 -10 0 1 2.85 14.49 10 0 -1 5.83 21.34 -7 -4 5 139.70 19.71 -7 4 5 150.36 17.53 7 4 -5 145.21 17.18 7 -4 -5 131.65 13.82 10 0 -3 0.45 16.26 -10 0 3 -3.38 18.97 -2 3 -18 7.01 20.05 2 3 18 5.56 17.73 2 -3 18 9.62 13.19 -2 -3 -18 3.14 18.71 -4 -4 14 138.52 16.36 -4 4 14 174.10 20.79 4 4 -14 181.85 16.24 4 -4 -14 182.87 16.32 0 -5 11 323.43 16.18 0 5 11 316.60 18.57 0 -5 -11 292.04 17.67 -2 1 -21 53.31 15.59 2 1 21 81.36 16.39 2 -1 21 72.90 10.74 1 -5 -11 56.88 17.75 1 5 -11 65.24 17.67 -1 5 11 59.18 20.11 -6 -4 10 5.48 15.28 6 -4 -10 -1.20 11.80 6 4 -10 3.10 21.26 -6 4 10 29.69 18.67 -1 4 16 12.39 18.63 -1 -4 16 3.24 16.24 1 -4 -16 2.85 13.55 1 4 -16 3.75 17.59 4 -3 16 14.63 12.33 4 3 16 39.50 16.85 -4 3 -16 52.07 17.26 4 -3 16 4.85 13.08 -4 -3 -16 14.33 18.44 -5 5 1 52.74 14.73 5 5 -1 67.78 12.98 5 -5 -1 116.78 14.20 -5 -5 1 75.06 16.96 1 -3 -19 6.50 13.00 1 3 -19 -7.19 19.91 -1 3 19 22.99 15.33 -1 -3 19 9.54 17.28 -10 0 0 506.58 23.82 10 0 0 480.90 26.51 2 -4 15 65.34 14.47 2 4 15 29.45 20.56 -2 4 -15 46.22 20.77 -2 -4 -15 47.53 15.04 -3 -4 -14 9.01 19.79 3 4 14 0.20 14.10 0 -4 -16 161.57 19.18 0 4 -16 141.25 19.61 0 -4 16 155.82 15.12 0 4 16 151.38 22.60 5 -5 0 83.82 12.86 5 5 0 77.16 15.53 -5 5 0 78.99 13.02 5 5 -2 52.97 19.44 5 -5 -2 66.01 15.75 -5 -5 2 57.57 14.65 -5 5 2 64.01 17.12 -4 5 -6 17.79 19.12 4 -5 6 20.11 16.94 4 5 6 1.41 18.04 -10 0 4 54.03 17.26 10 0 -4 101.00 18.81 2 -2 20 39.48 12.55 -2 -2 -20 38.97 20.26 -2 2 -20 34.50 14.82 0 -3 -19 135.71 18.57 0 3 -19 165.24 17.02 0 3 19 160.37 15.51 0 -3 19 189.06 18.30 -7 -4 -3 33.30 22.66 -7 4 -3 12.70 15.55 7 4 3 16.45 11.70 7 -4 3 15.81 14.90 8 0 12 121.81 19.67 -8 0 -12 74.39 19.95 -6 2 -15 -6.93 16.57 -6 -2 -15 2.06 18.32 6 2 15 -3.24 13.00 6 -2 15 9.97 15.51 -9 2 8 9.40 18.95 -9 2 8 -2.02 17.08 9 -2 -8 32.55 12.51 -9 -2 8 26.60 17.16 5 -1 18 110.82 17.10 5 1 18 77.08 18.18 -5 -1 -18 130.25 20.83 -5 1 -18 115.72 16.61 5 -5 1 -7.89 15.79 -5 5 -1 -2.30 16.36 5 5 1 21.68 12.78 6 4 8 102.82 19.81 -6 -4 -8 136.38 19.01 -6 4 -8 104.06 18.20 6 -4 8 95.62 15.67 -8 0 15 -6.64 16.87 8 0 -15 9.21 14.39 -1 1 22 18.57 11.33 1 1 -22 21.81 15.14 1 -1 -22 18.36 14.65 -1 -1 22 26.62 14.78 5 -5 -3 3.91 17.77 5 5 -3 16.02 18.16 -5 5 3 -4.63 18.46 -5 -5 3 -12.06 12.37 -6 0 19 12.11 11.76 6 0 -19 3.59 13.45 2 5 10 -33.69 15.94 2 -5 10 9.29 15.57 -2 -5 -10 -20.11 13.17 -2 5 -10 10.54 16.69 10 0 1 -10.15 14.75 -10 0 -1 6.52 18.65 -1 0 -22 -14.53 15.18 1 0 22 14.20 12.06 -1 2 21 85.29 17.26 -1 -2 21 166.32 17.02 1 2 -21 124.83 17.91 1 -2 -21 146.71 19.63 9 -1 -11 8.95 18.61 -9 1 11 11.21 18.87 -9 -1 11 1.37 12.53 9 1 -11 9.35 17.75 -7 -4 6 -1.30 21.91 7 -4 -6 17.63 20.30 7 4 -6 -2.79 17.16 -7 4 6 26.68 18.65 10 0 -5 -9.90 16.34 -10 0 5 3.65 18.12 0 1 -22 -5.67 17.53 0 -1 -22 16.26 19.54 0 1 22 -0.20 10.21 0 -1 22 -2.51 11.88 -9 2 -5 65.07 15.49 -9 -2 -5 88.41 20.79 9 2 5 101.23 14.14 9 -2 5 68.54 14.94 1 -5 11 -4.93 10.17 -1 5 -11 -27.10 16.32 1 5 11 22.30 19.01 -1 -5 -11 -22.17 14.35 2 3 -19 76.08 16.98 2 -3 -19 54.88 16.73 -2 -3 19 111.99 19.16 7 3 10 80.13 14.43 -7 -3 -10 88.79 19.79 0 2 -21 30.41 21.62 0 2 21 14.67 19.91 0 -2 21 15.33 12.51 0 -2 -21 -7.30 15.77 5 -5 2 102.39 17.81 5 5 2 67.40 11.84 -5 5 -2 94.48 18.04 -2 4 16 191.81 18.28 -2 -4 16 229.01 17.83 2 -4 -16 215.33 15.77 2 4 -16 211.68 20.58 4 -5 -8 14.02 16.10 -4 5 8 -0.90 14.80 -5 -1 20 174.94 14.06 5 -1 -20 194.42 20.50 5 1 -20 202.17 18.67 -5 1 20 267.03 19.91 7 -1 -17 10.39 14.69 7 1 -17 4.81 16.22 -7 -1 17 17.40 13.25 -7 1 17 24.58 19.40 -5 -4 -11 34.14 19.48 5 -4 11 33.57 12.80 5 4 11 36.72 11.78 -5 4 -11 67.93 19.73 -5 -5 4 232.31 17.04 5 5 -4 220.65 19.56 5 -5 -4 251.77 15.06 -5 5 4 266.22 16.75 -8 -3 -6 62.83 20.50 -8 3 -6 15.71 17.06 8 3 6 22.80 17.47 -6 -3 15 237.65 17.79 6 -3 -15 249.83 14.65 6 3 -15 306.63 25.66 -2 5 11 64.73 16.02 2 5 -11 44.86 13.70 2 -5 -11 48.63 18.40 -2 1 22 4.06 13.33 -2 -1 22 16.34 12.45 2 -1 -22 2.53 16.94 2 1 -22 26.86 21.13 -8 -3 9 71.65 18.48 8 -3 -9 63.34 17.24 -8 3 9 70.92 18.55 -9 0 12 8.99 18.59 9 0 -12 -16.92 17.67 3 5 -10 295.63 19.30 -3 5 10 271.91 22.38 3 -5 -10 277.53 16.71 -5 2 -17 38.93 15.00 -5 -2 -17 58.86 16.83 5 2 17 49.24 13.59 5 -2 17 73.96 15.75 7 -2 13 254.99 21.58 -7 2 -13 312.66 22.17 -7 -2 -13 276.74 21.42 7 2 13 215.07 20.60 -1 4 -16 78.93 17.61 -1 -4 -16 65.26 15.84 1 4 16 73.57 21.66 1 -4 16 97.35 16.14 4 -1 -21 225.15 17.53 4 1 -21 180.81 19.67 -4 1 21 227.87 20.73 -4 -1 21 208.83 20.14 10 -1 -2 5.14 15.22 -10 1 2 17.49 17.34 -10 -1 2 -14.53 14.88 10 1 -2 19.24 20.60 -4 -4 -13 -8.36 12.76 -4 4 -13 1.10 15.63 4 4 13 -2.00 18.04 4 -4 13 -15.49 18.34 -10 0 -2 601.40 26.84 10 0 2 555.26 31.96 8 2 10 243.48 19.38 -8 2 -10 245.15 23.62 -8 -2 -10 209.20 19.44 8 -2 10 211.56 16.08 3 0 -22 -4.77 17.02 -3 0 22 -1.53 19.58 7 -4 4 -7.99 14.41 7 4 4 6.26 21.56 -7 4 -4 -5.03 13.49 -7 -4 -4 4.12 21.60 6 0 17 14.10 17.71 -6 0 -17 2.85 15.73 -9 -1 -8 237.44 21.89 9 -1 8 202.96 16.32 -9 1 -8 208.69 18.14 9 1 8 203.06 21.05 10 -1 -1 161.53 17.95 -10 1 1 146.29 24.05 -10 -1 1 138.11 20.64 10 1 -1 157.88 21.50 2 2 -21 6.87 15.69 -2 2 21 37.74 18.44 -2 -2 21 13.63 13.10 2 -2 -21 15.94 14.73 5 4 -13 351.94 24.84 -5 4 13 292.14 19.30 -5 -4 13 353.73 22.97 5 -4 -13 373.42 19.93 8 2 -13 27.76 15.98 -8 -2 13 6.85 12.96 -8 2 13 -3.79 17.10 8 -2 -13 0.00 18.53 3 5 9 7.70 14.23 3 -5 9 11.72 13.31 -3 5 -9 20.44 13.55 -10 1 3 398.52 25.78 -10 -1 3 374.44 21.64 10 1 -3 385.77 21.77 10 -1 -3 364.63 22.60 7 0 15 242.13 20.73 -7 0 -15 195.85 17.67 -10 0 6 66.91 18.71 10 0 -6 81.70 17.97 1 -3 19 -0.06 12.70 1 3 19 34.50 15.28 1 3 19 11.15 16.51 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 99903 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cu1 Cu 0.500000 1.000000 0.500000 0.02247(17) Uani 1 2 d S T P . . O1 O 0.4892(2) 0.7173(4) 0.56843(10) 0.0264(4) Uani 1 1 d . . . . . O2 O 0.8001(2) 1.1067(5) 0.44457(11) 0.0304(5) Uani 1 1 d D . . . . O3 O 0.4111(2) 0.3628(4) 0.66313(11) 0.0303(5) Uani 1 1 d . . . . . N1 N 0.7241(3) 0.9402(5) 0.49228(12) 0.0238(5) Uani 1 1 d . . . . . C2 C 0.7653(3) 0.5804(6) 0.58036(15) 0.0238(6) Uani 1 1 d . . . . . C1 C 0.6061(3) 0.5615(5) 0.59777(14) 0.0233(6) Uani 1 1 d . . . . . C5 C 0.6840(3) 0.1949(6) 0.68238(15) 0.0284(6) Uani 1 1 d . . . . . H5 H 0.657328 0.065642 0.715955 0.034 Uiso 1 1 calc R . . . . C6 C 0.5684(3) 0.3650(6) 0.64951(14) 0.0242(6) Uani 1 1 d . . . . . C7 C 0.8164(3) 0.7701(6) 0.52799(14) 0.0249(6) Uani 1 1 d . . . . . H7 H 0.923203 0.769518 0.519407 0.030 Uiso 1 1 calc R . . . . C3 C 0.8815(3) 0.4056(6) 0.61537(15) 0.0264(6) Uani 1 1 d . . . . . H3 H 0.986543 0.418770 0.604412 0.032 Uiso 1 1 calc R . . . . C4 C 0.8412(3) 0.2185(6) 0.66486(15) 0.0295(7) Uani 1 1 d . . . . . H4 H 0.918985 0.105173 0.687239 0.035 Uiso 1 1 calc R . . . . C8 C 0.3624(4) 0.1513(6) 0.70963(16) 0.0332(7) Uani 1 1 d . . . . . H8A H 0.391966 -0.025080 0.691831 0.050 Uiso 1 1 calc GR . . . . H8B H 0.249271 0.158479 0.711442 0.050 Uiso 1 1 calc GR . . . . H8C H 0.413339 0.178429 0.756841 0.050 Uiso 1 1 calc GR . . . . H2 H 0.716(3) 1.229(6) 0.4271(17) 0.050 Uiso 1 1 d DR . . . . 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 0.0201(3) 0.0206(3) 0.0269(3) 0.0024(2) 0.00270(18) -0.0009(2) O1 0.0230(10) 0.0242(10) 0.0321(11) 0.0069(8) 0.0037(8) 0.0015(8) O2 0.0218(10) 0.0347(11) 0.0350(12) 0.0108(9) 0.0046(9) -0.0024(9) O3 0.0285(11) 0.0278(11) 0.0353(11) 0.0093(9) 0.0067(9) -0.0011(9) N1 0.0213(12) 0.0278(14) 0.0223(11) 0.0010(9) 0.0026(9) -0.0052(9) C2 0.0243(14) 0.0209(14) 0.0258(14) -0.0044(11) 0.0003(12) -0.0002(11) C1 0.0251(14) 0.0200(15) 0.0245(14) -0.0049(10) 0.0000(12) -0.0002(10) C5 0.0368(17) 0.0204(14) 0.0275(15) 0.0014(12) 0.0001(13) -0.0006(12) C6 0.0284(15) 0.0190(14) 0.0252(14) -0.0028(11) 0.0023(11) -0.0020(11) C7 0.0188(13) 0.0263(15) 0.0299(15) -0.0037(12) 0.0032(11) -0.0004(11) C3 0.0241(15) 0.0262(14) 0.0285(15) -0.0037(12) -0.0010(12) 0.0034(12) C4 0.0341(16) 0.0227(15) 0.0306(15) -0.0006(12) -0.0035(13) 0.0057(12) C8 0.0389(17) 0.0282(18) 0.0334(17) 0.0051(13) 0.0082(13) -0.0049(14) 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 Cu1 O1 180.0 3_676 . ? O1 Cu1 N1 92.57(9) . . ? O1 Cu1 N1 92.57(9) 3_676 3_676 ? O1 Cu1 N1 87.43(9) . 3_676 ? O1 Cu1 N1 87.43(9) 3_676 . ? N1 Cu1 N1 180.0 3_676 . ? C1 O1 Cu1 128.36(17) . . ? N1 O2 H2 102(2) . . ? C6 O3 C8 116.8(2) . . ? O2 N1 Cu1 117.73(16) . . ? C7 N1 Cu1 127.8(2) . . ? C7 N1 O2 114.4(2) . . ? C1 C2 C7 123.0(2) . . ? C1 C2 C3 119.3(3) . . ? C3 C2 C7 117.7(2) . . ? O1 C1 C2 123.9(2) . . ? O1 C1 C6 117.8(2) . . ? C2 C1 C6 118.4(2) . . ? C6 C5 H5 120.2 . . ? C6 C5 C4 119.7(3) . . ? C4 C5 H5 120.2 . . ? O3 C6 C1 114.1(2) . . ? O3 C6 C5 124.8(3) . . ? C5 C6 C1 121.1(3) . . ? N1 C7 C2 124.3(3) . . ? N1 C7 H7 117.8 . . ? C2 C7 H7 117.8 . . ? C2 C3 H3 119.6 . . ? C4 C3 C2 120.8(3) . . ? C4 C3 H3 119.6 . . ? C5 C4 H4 119.7 . . ? C3 C4 C5 120.7(3) . . ? C3 C4 H4 119.7 . . ? O3 C8 H8A 109.5 . . ? O3 C8 H8B 109.5 . . ? O3 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cu1 O1 1.8866(18) 3_676 ? Cu1 O1 1.8866(18) . ? Cu1 N1 1.933(2) 3_676 ? Cu1 N1 1.933(2) . ? O1 C1 1.326(3) . ? O2 N1 1.401(3) . ? O2 H2 0.965(10) . ? O3 C6 1.374(3) . ? O3 C8 1.430(3) . ? N1 C7 1.285(3) . ? C2 C1 1.413(4) . ? C2 C7 1.438(4) . ? C2 C3 1.417(4) . ? C1 C6 1.416(4) . ? C5 H5 0.9300 . ? C5 C6 1.384(4) . ? C5 C4 1.399(4) . ? C7 H7 0.9300 . ? C3 H3 0.9300 . ? C3 C4 1.362(4) . ? C4 H4 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? 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 _geom_hbond_publ_flag O2 H2 O1 0.965(10) 1.76(2) 2.582(3) 141(3) 3_676 yes