#------------------------------------------------------------------------------ #$Date: 2019-11-11 20:29:42 +0200 (Mon, 11 Nov 2019) $ #$Revision: 227274 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035862.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_4035862 loop_ _publ_author_name 'Bookser, Brett C.' 'Weinhouse, Michael I.' 'Burns, Aaron C.' 'Valiere, Andrew N.' 'Valdez, Lino J.' 'Stanczak, Pawel' 'Na, Jim' 'Rheingold, Arnold L.' 'Moore, Curtis E.' 'Dyck, Brian' _publ_section_title ; Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds. ; _journal_issue 12 _journal_name_full 'The Journal of organic chemistry' _journal_page_first 6334 _journal_page_last 6353 _journal_paper_doi 10.1021/acs.joc.8b00540 _journal_volume 83 _journal_year 2018 _chemical_formula_moiety 'C6 H5 Cl N4' _chemical_formula_sum 'C6 H5 Cl N4' _chemical_formula_weight 168.59 _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' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _atom_sites_solution_secondary difmap _audit_creation_date 2016-08-25 _audit_creation_method ; Olex2 1.2 (compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155) ; _cell_angle_alpha 90 _cell_angle_beta 95.259(9) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.176(3) _cell_length_b 12.399(4) _cell_length_c 7.156(2) _cell_measurement_reflns_used 1260 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 67.42 _cell_measurement_theta_min 5.45 _cell_volume 722.4(4) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection 'APEX2 v2013.10-0 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2008)' _diffrn_ambient_temperature 100.0 _diffrn_detector_area_resol_mean 7.9 _diffrn_detector_type 'CCD Area Detector' _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.965 _diffrn_measurement_device 'Kappa Four-Circle Diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0528 _diffrn_reflns_av_unetI/netI 0.0511 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.965 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -6 _diffrn_reflns_number 4602 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.965 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 69.621 _diffrn_reflns_theta_min 5.433 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 4.139 _exptl_absorpt_correction_T_max 0.3200 _exptl_absorpt_correction_T_min 0.1397 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.1261 before and 0.0757 after correction. The Ratio of minimum to maximum transmission is 0.4366. The \l/2 correction factor is 0.00150. ; _exptl_crystal_colour colorless _exptl_crystal_colour_primary colorless _exptl_crystal_density_diffrn 1.550 _exptl_crystal_description plate _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.14 _refine_diff_density_max 0.410 _refine_diff_density_min -0.528 _refine_diff_density_rms 0.092 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.126 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 101 _refine_ls_number_reflns 1310 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.126 _refine_ls_R_factor_all 0.0657 _refine_ls_R_factor_gt 0.0545 _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^)+(0.0787P)^2^+1.1127P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1417 _refine_ls_wR_factor_ref 0.1640 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1098 _reflns_number_total 1310 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jo8b00540_si_004.cif _cod_data_source_block dart168 _cod_database_code 4035862 _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_estimated_absorpt_t_max 0.595 _shelx_estimated_absorpt_t_min 0.370 _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) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C2(H2) 2.b Idealised Me refined as rotating group: C6(H6A,H6B,H6C) ; _shelx_res_file ; dart168.res created by SHELXL-2014/7 TITL dart168 in P2(1)/c CELL 1.54178 8.1759 12.3987 7.1563 90 95.259 90 ZERR 4 0.0025 0.0038 0.0023 0 0.009 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N UNIT 24 20 4 16 L.S. 6 PLAN -2 0 0 SIZE 0.14 0.2 0.3 TEMP -173.15 HTAB WPDB BOND $H CONF MORE -1 fmap 2 acta OMIT 2 10 6 REM REM REM WGHT 0.078700 1.112700 FVAR 0.37399 CL1 3 0.446263 0.152392 0.090651 11.00000 0.03868 0.02957 = 0.03586 -0.00034 0.00562 0.00919 N4 4 -0.050792 0.330323 0.261651 11.00000 0.02735 0.02174 = 0.02815 0.00105 0.00281 -0.00137 N1 4 0.409853 0.362852 0.089479 11.00000 0.03098 0.03029 = 0.02876 0.00095 0.00162 -0.00183 N3 4 -0.058985 0.220997 0.268367 11.00000 0.03148 0.02134 = 0.03570 0.00311 0.00281 -0.00332 N2 4 0.079203 0.179908 0.218041 11.00000 0.03415 0.02043 = 0.03268 0.00246 0.00407 -0.00093 C1 1 0.325188 0.456152 0.116236 11.00000 0.03586 0.02161 = 0.03682 0.00060 0.00446 -0.00580 AFIX 43 H1 2 0.378354 0.522286 0.092907 11.00000 -1.20000 AFIX 0 C2 1 0.168852 0.461934 0.174356 11.00000 0.03502 0.01962 = 0.03090 -0.00104 0.00000 -0.00139 AFIX 43 H2 2 0.114753 0.528563 0.191245 11.00000 -1.20000 AFIX 0 C3 1 0.095941 0.361841 0.206589 11.00000 0.02790 0.02216 = 0.02162 -0.00057 0.00231 -0.00037 C6 1 -0.188029 0.395422 0.316202 11.00000 0.03347 0.02917 = 0.03979 -0.00043 0.00966 0.00320 AFIX 137 H6A 2 -0.167178 0.471690 0.291369 11.00000 -1.50000 H6B 2 -0.199161 0.385389 0.450279 11.00000 -1.50000 H6C 2 -0.289618 0.372765 0.243476 11.00000 -1.50000 AFIX 0 C5 1 0.337945 0.270928 0.121547 11.00000 0.02960 0.02617 = 0.02256 -0.00050 0.00066 0.00059 C4 1 0.178601 0.265080 0.178135 11.00000 0.03299 0.01785 = 0.02718 0.00092 0.00158 -0.00150 HKLF 4 REM dart168 in P2(1)/c REM R1 = 0.0545 for 1098 Fo > 4sig(Fo) and 0.0657 for all 1310 data REM 101 parameters refined using 0 restraints END WGHT 0.0784 1.1189 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+1, -z HTAB C1 N1_$1 EQIV $2 -x, y+1/2, -z+1/2 HTAB C2 N3_$2 HTAB C2 N2_$2 HTAB C6 N2_$2 EQIV $3 x-1, y, z HTAB C6 N1_$3 REM Highest difference peak 0.410, deepest hole -0.528, 1-sigma level 0.092 Q1 1 0.4833 0.1563 0.2819 11.00000 0.05 0.41 Q2 1 0.4568 0.2415 0.0677 11.00000 0.05 0.37 ; _shelx_res_checksum 64479 _shelx_hkl_file ; 0 0 1 0.08 0.07 0 0 1 0.03 0.07 0 0 -1 0.00 0.07 0 0 3 0.00 0.28 0 0 4 47.97 3.01 0 0 5 -1.50 1.10 0 0 5 0.28 1.17 0 0 5 -0.24 0.43 0 0 6 121.86 7.76 0 0 6 122.27 7.76 0 0 7 0.18 1.28 0 0 7 2.03 1.43 0 -1 0 0.11 0.06 0 1 1 5.33 0.36 0 1 -1 5.04 0.43 0 1 1 5.64 0.43 0 1 1 6.21 0.36 0 -1 1 5.55 0.44 0 -1 1 5.15 0.40 0 -1 -1 6.30 0.39 0 1 -2 1000.00 56.81 0 1 3 25.63 1.60 0 -1 3 22.00 1.53 0 1 4 39.12 2.47 0 -1 4 36.51 2.41 0 1 5 1.25 1.45 0 1 5 1.83 0.63 0 -1 5 3.10 0.66 0 -1 5 2.89 1.29 0 -1 5 3.05 1.31 0 1 6 10.42 1.82 0 1 6 10.31 1.96 0 -1 6 9.76 1.67 0 -1 6 10.36 1.81 0 -1 7 8.41 1.57 0 -1 7 6.05 1.58 0 -1 8 22.81 2.00 0 2 1 152.09 9.24 0 -2 1 159.06 9.29 0 -2 -1 175.63 9.30 0 -2 1 163.47 9.34 0 2 2 113.03 7.00 0 2 2 135.18 7.15 0 -2 -2 120.33 7.05 0 -2 2 124.87 7.15 0 -2 2 122.62 7.09 0 2 3 98.75 5.67 0 -2 3 92.37 5.59 0 2 4 19.76 1.47 0 -2 4 17.19 1.33 0 2 5 12.42 2.01 0 2 5 10.45 1.21 0 -2 5 11.99 1.94 0 -2 5 12.50 1.86 0 -2 5 11.43 1.10 0 2 6 40.63 3.33 0 -2 6 35.23 3.17 0 -2 6 35.44 3.15 0 -2 7 16.58 2.29 0 -2 7 19.74 2.29 0 -2 8 0.24 0.98 0 -3 0 -0.23 0.16 0 -3 0 -0.26 0.20 0 -3 -1 231.23 13.21 0 -3 1 235.85 13.27 0 -3 1 225.74 13.18 0 3 2 5.98 0.41 0 -3 2 6.46 0.54 0 -3 2 6.21 0.62 0 -3 -2 6.93 0.51 0 -3 3 30.90 1.97 0 -3 4 28.04 1.89 0 3 5 24.45 2.53 0 -3 5 25.84 2.41 0 -3 5 22.35 2.34 0 -3 5 22.66 1.71 0 -3 5 21.78 2.27 0 3 6 0.55 1.55 0 -3 6 0.65 1.48 0 -3 6 0.50 1.14 0 -3 7 11.96 1.92 0 -3 7 13.94 1.99 0 -3 8 8.09 1.38 0 -4 0 199.41 11.51 0 -4 -1 186.11 10.23 0 -4 -1 167.72 10.21 0 -4 1 182.73 10.28 0 -4 1 172.06 10.15 0 4 2 33.48 1.98 0 -4 2 32.96 2.20 0 -4 -2 33.86 2.08 0 -4 2 34.48 2.08 0 -4 3 27.78 1.80 0 -4 4 2.78 0.54 0 4 5 -0.40 1.54 0 4 5 0.45 0.75 0 -4 5 -1.36 1.20 0 -4 5 -0.37 1.22 0 -4 5 0.27 1.36 0 -4 5 0.16 1.31 0 -4 5 0.16 0.45 0 -4 6 62.87 4.66 0 -4 6 64.53 4.62 0 -4 6 71.19 4.75 0 -4 7 3.45 1.33 0 -4 7 1.70 1.21 0 -4 8 3.93 0.99 0 -5 0 -0.26 0.26 0 -5 1 9.63 0.87 0 -5 1 8.73 0.70 0 -5 -1 9.04 0.80 0 -5 2 51.03 3.26 0 -5 -2 50.37 3.12 0 -5 2 52.00 3.10 0 5 3 19.30 1.40 0 -5 3 21.13 1.44 0 -5 4 102.21 6.26 0 -5 4 108.74 6.83 0 5 5 0.94 0.77 0 -5 5 2.41 1.36 0 -5 5 -2.33 1.16 0 -5 5 2.90 1.45 0 5 6 4.57 1.10 0 -5 6 6.91 1.87 0 -5 6 6.19 1.50 0 -5 6 2.61 1.60 0 -5 7 5.07 1.29 0 -5 8 33.82 2.40 0 -6 0 261.76 15.18 0 6 1 3.32 0.48 0 -6 -1 4.10 0.62 0 -6 1 2.78 0.42 0 -6 1 3.47 0.60 0 6 2 0.57 0.36 0 -6 2 0.35 0.30 0 -6 -2 0.40 0.31 0 -6 2 0.53 0.41 0 6 3 128.29 7.66 0 -6 3 133.25 7.68 0 6 -4 -0.07 1.06 0 6 4 -0.08 0.64 0 -6 4 -1.06 1.21 0 -6 4 0.84 0.82 0 -6 4 0.25 1.05 0 -6 4 0.21 0.46 0 6 5 27.99 2.21 0 -6 5 33.04 2.93 0 -6 5 27.43 2.65 0 -6 5 31.88 2.89 0 -6 6 100.94 6.38 0 -6 6 101.37 6.46 0 -6 6 95.05 6.45 0 -6 7 2.21 1.11 0 7 0 -0.08 0.29 0 -7 0 0.01 0.31 0 7 1 79.83 4.73 0 7 -1 79.18 4.70 0 -7 1 79.99 4.69 0 -7 1 78.85 4.93 0 -7 -1 75.44 4.85 0 7 2 51.61 3.15 0 -7 2 52.02 3.13 0 -7 2 46.85 3.46 0 7 3 12.44 1.12 0 7 -3 14.45 1.83 0 7 3 12.71 1.31 0 7 3 13.64 1.12 0 -7 3 11.63 1.78 0 -7 3 13.81 1.14 0 -7 3 13.49 1.42 0 7 4 0.82 0.89 0 7 4 0.48 0.45 0 7 -4 0.73 1.00 0 -7 4 0.37 0.99 0 -7 4 0.67 0.93 0 -7 4 0.58 0.51 0 -7 4 -0.36 1.18 0 7 5 33.15 2.59 0 -7 5 35.17 3.10 0 -7 5 33.24 2.88 0 -7 5 39.52 3.35 0 7 6 0.46 0.71 0 -7 6 0.55 1.21 0 -7 6 3.63 1.63 0 -7 6 0.17 1.06 0 -7 7 1.17 0.82 0 8 0 23.32 1.66 0 8 -1 1.06 0.39 0 8 1 1.00 0.43 0 -8 1 0.43 0.35 0 8 -2 10.97 1.48 0 8 2 8.70 0.91 0 8 2 8.00 1.06 0 8 2 9.27 0.95 0 -8 2 8.95 0.90 0 -8 2 9.09 1.26 0 8 3 130.36 7.91 0 8 3 143.68 7.98 0 8 -3 138.37 8.25 0 8 3 126.93 8.02 0 -8 3 134.88 7.94 0 -8 3 124.41 8.19 0 -8 3 142.44 8.13 0 8 4 18.99 1.62 0 8 4 16.43 1.42 0 8 -4 15.36 2.00 0 8 4 18.58 1.74 0 -8 4 18.75 2.01 0 -8 4 18.52 2.30 0 8 5 3.64 1.01 0 -8 5 4.00 1.38 0 -8 5 7.67 1.85 0 -8 5 4.02 1.48 0 8 6 -0.26 0.62 0 -8 6 -0.33 0.95 0 -8 6 0.20 1.07 0 -8 7 0.13 0.54 0 9 0 0.45 0.81 0 9 0 0.35 0.89 0 9 0 0.89 0.48 0 9 0 0.12 0.45 0 -9 0 0.29 0.62 0 9 1 35.77 2.49 0 9 -1 32.92 2.79 0 9 -1 34.77 2.45 0 9 -1 44.55 2.62 0 9 1 42.50 2.74 0 9 -1 39.63 2.81 0 9 1 39.89 2.56 0 -9 1 36.61 2.68 0 9 -2 172.82 11.40 0 9 2 181.04 11.25 0 9 2 197.51 11.23 0 9 2 188.35 11.15 0 -9 2 221.37 11.82 0 -9 2 189.69 11.34 0 9 3 8.57 1.24 0 9 -3 7.16 1.39 0 9 3 5.41 0.87 0 9 3 6.74 0.91 0 -9 3 9.24 1.58 0 -9 3 7.29 1.34 0 9 4 4.14 0.79 0 9 4 3.79 1.04 0 9 -4 4.91 1.26 0 9 4 4.91 0.80 0 -9 4 7.13 1.77 0 -9 4 5.90 1.31 0 9 5 5.33 0.99 0 9 -5 5.54 1.14 0 -9 5 4.66 1.52 0 -9 5 4.95 1.27 0 9 6 0.68 0.63 0 -9 6 1.08 0.79 0 10 0 199.76 12.62 0 10 0 215.71 12.48 0 10 0 214.77 12.43 0 10 0 219.90 12.36 0 -10 0 213.36 12.58 0 10 -1 33.70 2.79 0 10 -1 33.03 2.26 0 10 1 34.33 2.50 0 10 1 34.69 2.41 0 10 1 33.56 2.35 0 -10 1 35.04 2.63 0 10 2 11.23 1.21 0 10 2 11.84 1.46 0 10 2 8.54 1.11 0 10 -2 12.40 1.81 0 -10 2 12.10 1.48 0 10 3 24.11 1.88 0 10 3 25.84 2.16 0 10 3 23.88 1.84 0 10 -3 26.44 2.45 0 -10 3 25.31 2.33 0 10 4 51.95 3.19 0 10 -4 50.76 3.61 0 10 4 49.64 3.36 0 10 4 47.20 3.17 0 -10 4 50.46 3.56 0 10 5 17.14 1.52 0 10 -5 15.43 1.65 0 -10 5 15.61 1.81 0 10 6 26.26 1.81 0 11 0 -0.06 0.49 0 11 0 0.07 1.16 0 11 0 0.73 1.21 0 11 0 0.17 0.55 0 -11 0 -0.23 0.89 0 11 1 21.14 1.72 0 11 -1 22.46 2.34 0 11 1 22.91 1.98 0 11 -1 23.94 1.72 0 11 1 24.24 1.83 0 -11 1 23.15 2.13 0 -11 -1 22.32 2.08 0 11 -2 52.91 3.89 0 11 2 53.71 3.57 0 11 2 58.24 3.53 0 11 2 49.59 3.40 0 -11 2 54.50 3.73 0 11 -3 79.81 5.32 0 11 3 82.47 5.01 0 11 3 82.39 4.96 0 11 3 79.57 5.11 0 -11 3 82.95 5.21 0 11 4 8.42 1.13 0 11 4 8.03 0.98 0 11 4 7.38 0.88 0 11 -4 7.90 1.22 0 -11 4 8.54 1.28 0 11 -5 14.30 1.35 0 11 5 17.74 1.43 0 -11 5 16.17 1.46 0 12 0 0.04 0.54 0 12 0 0.05 1.10 0 12 0 0.06 0.53 0 -12 0 -0.65 0.93 0 12 -1 -0.25 1.11 0 12 1 0.62 1.11 0 12 1 0.07 0.57 0 12 1 0.48 0.58 0 12 -1 -0.23 0.90 0 -12 -1 -0.26 0.88 0 -12 1 -0.27 0.82 0 12 2 0.72 0.83 0 12 2 0.13 0.53 0 12 2 0.32 0.60 0 12 -2 -0.54 0.95 0 -12 2 0.01 0.95 0 -12 -2 -0.33 0.79 0 12 3 8.97 1.26 0 12 3 8.70 0.98 0 12 -3 9.36 1.38 0 12 3 10.02 1.05 0 -12 -3 8.38 1.04 0 -12 3 6.09 1.14 0 12 -4 1.98 0.76 0 12 4 0.31 0.61 0 12 4 1.64 0.54 0 -12 4 0.44 0.81 0 -12 -4 1.61 0.81 0 12 5 5.34 1.01 0 13 0 -0.12 1.02 0 13 0 -0.20 0.47 0 -13 0 -0.01 0.75 0 13 1 16.37 1.35 0 13 1 16.12 1.38 0 13 -1 16.82 1.78 0 13 1 11.80 1.55 0 -13 -1 18.05 1.69 0 -13 1 16.23 1.65 0 13 2 10.81 1.29 0 13 -2 10.44 1.52 0 13 2 10.51 1.08 0 13 2 9.52 1.07 0 -13 2 9.75 1.33 0 -13 -2 10.82 1.28 0 13 3 1.59 0.59 0 13 3 1.44 0.82 0 13 -3 1.71 0.82 0 -13 -3 1.14 0.44 0 -13 3 2.07 0.78 0 13 -4 0.59 0.57 0 13 4 1.11 0.63 0 -13 4 1.18 0.70 0 14 0 -0.01 0.39 0 -14 0 1.60 0.61 0 -14 0 1.48 0.72 0 14 1 0.74 0.48 0 14 -1 0.57 0.80 0 -14 -1 0.71 0.66 0 -14 1 0.34 0.61 0 14 -2 13.50 1.29 0 14 2 14.51 1.10 0 -14 2 14.42 1.30 0 -14 -2 12.02 1.11 0 14 -3 12.25 1.36 -1 0 7 -0.08 1.24 -1 0 7 2.08 1.49 -1 0 6 82.43 5.63 -1 0 6 88.62 5.73 -1 0 5 -0.54 1.01 -1 0 5 -0.42 0.47 -1 0 4 300.59 17.28 -1 0 3 0.05 0.24 -1 0 2 3.83 0.34 -1 0 2 3.26 0.31 -1 0 2 3.41 0.31 -1 0 2 4.49 0.41 -1 0 1 -0.12 0.10 1 0 -1 0.02 0.12 -1 0 1 -0.03 0.10 -1 0 1 -0.08 0.09 -1 0 0 32.67 1.79 -1 0 0 28.09 1.86 -1 0 -1 -0.12 0.19 1 0 1 -0.01 0.11 1 0 1 0.18 0.24 1 0 3 -0.76 0.31 1 0 4 886.29 50.51 1 0 5 -0.22 1.19 1 0 5 -0.22 1.00 1 0 5 0.21 0.48 1 0 5 0.53 1.05 1 0 5 0.37 1.18 1 0 6 34.80 3.37 1 0 6 45.36 3.46 1 0 7 0.06 1.33 1 0 8 8.06 1.38 -1 -1 8 10.37 1.28 -1 1 7 2.79 1.51 -1 -1 7 2.14 1.28 -1 -1 7 4.03 1.48 -1 1 6 28.78 2.97 -1 -1 6 31.02 2.97 -1 -1 6 32.90 2.80 -1 1 5 19.75 1.59 -1 1 5 20.98 2.05 -1 -1 5 19.04 1.97 -1 -1 5 18.30 1.50 -1 -1 5 18.22 2.00 -1 1 4 14.80 1.28 -1 -1 4 17.94 1.25 -1 1 3 8.98 0.75 -1 1 3 7.49 0.56 -1 -1 3 8.44 0.71 -1 1 2 424.40 22.01 -1 1 2 393.23 21.95 -1 -1 2 358.14 22.00 -1 -1 2 369.49 21.99 -1 1 1 58.56 3.38 -1 1 1 57.25 3.37 -1 1 1 63.56 3.37 1 1 -1 59.75 3.43 1 -1 -1 62.35 3.41 -1 -1 1 58.96 3.37 -1 -1 1 49.18 3.40 -1 1 0 489.33 27.14 -1 1 0 463.39 27.06 -1 1 -1 1.41 0.27 1 1 1 2.36 0.33 1 -1 1 1.85 0.29 1 -1 1 1.75 0.22 -1 -1 -1 1.41 0.28 1 1 2 255.98 14.61 1 1 2 248.77 14.61 -1 1 -2 242.45 14.66 1 -1 2 262.12 14.58 -1 -1 -2 259.87 14.65 1 -1 2 260.34 14.64 1 1 3 22.62 1.59 1 -1 3 24.05 1.57 1 1 4 391.74 23.00 1 -1 4 409.48 22.97 1 1 5 1.01 0.85 1 1 5 1.37 1.44 1 1 5 -0.69 0.92 1 1 5 2.30 1.38 1 1 5 1.86 0.61 1 -1 5 1.66 1.41 1 -1 5 1.31 0.98 1 -1 5 2.18 0.59 1 -1 5 3.20 1.37 1 1 6 11.76 1.91 1 1 6 10.17 1.47 1 -1 6 10.42 1.93 1 1 7 2.65 1.61 1 -1 7 3.15 1.53 1 -1 8 13.73 1.55 -1 -2 8 -0.52 0.86 -1 -2 8 0.38 0.91 -1 2 7 5.85 1.65 -1 -2 7 7.61 1.64 -1 -2 7 6.07 1.54 -1 2 6 0.33 1.41 -1 -2 6 -0.61 1.14 -1 -2 6 0.58 1.42 -1 2 5 1.68 1.22 -1 2 5 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307.68 17.18 -2 2 1 291.06 17.04 2 -2 -1 298.72 17.15 2 2 0 369.49 19.97 -2 2 0 331.90 19.79 2 -2 0 343.15 19.94 2 2 1 50.43 2.95 2 -2 1 43.98 2.75 2 -2 1 46.44 2.92 2 2 2 18.07 1.28 2 -2 2 15.84 1.27 2 -2 2 15.87 1.11 2 -2 3 168.52 9.77 2 2 4 35.10 2.46 2 -2 4 39.18 2.45 2 2 5 4.72 1.15 2 2 5 6.02 1.79 2 -2 5 4.89 0.83 2 -2 5 7.42 1.71 2 -2 5 3.50 1.01 2 2 6 58.44 4.55 2 2 6 55.00 3.90 2 -2 6 55.81 3.79 2 -2 6 60.09 4.42 2 -2 6 64.76 4.10 2 2 7 0.43 0.74 2 2 7 -0.39 1.62 2 -2 7 1.33 1.46 2 -2 8 1.67 0.74 -2 -3 8 8.27 1.33 -2 -3 8 8.53 1.23 -2 3 7 1.75 1.52 -2 -3 7 1.87 1.20 -2 -3 7 2.00 1.43 -2 3 6 -0.92 1.59 -2 -3 6 1.49 1.55 -2 -3 6 1.10 1.44 -2 -3 6 0.02 1.27 -2 3 5 25.90 2.61 -2 -3 5 24.01 2.38 -2 -3 5 28.09 2.64 -2 -3 5 28.70 2.41 -2 -3 5 26.95 1.93 -2 -3 4 28.09 1.92 -2 3 3 59.91 3.55 -2 -3 3 61.29 3.67 2 3 -2 145.36 8.16 -2 3 2 138.72 7.96 -2 -3 2 137.84 8.03 2 -3 -2 131.97 8.01 -2 3 1 79.02 4.78 2 3 -1 81.91 4.95 2 -3 -1 87.33 4.90 -2 3 0 25.58 1.58 2 3 0 26.46 1.77 2 -3 0 26.92 1.73 2 3 1 23.24 1.58 2 -3 1 21.85 1.38 2 -3 1 22.97 1.57 2 -3 2 13.51 0.97 2 -3 2 14.46 1.16 2 -3 3 49.86 3.06 2 3 4 3.10 0.70 2 -3 4 4.17 0.65 2 3 5 15.63 3.03 2 3 5 17.98 1.78 2 -3 5 18.96 2.19 2 -3 5 21.29 1.96 2 -3 5 17.93 1.65 2 3 6 2.05 1.09 2 -3 6 4.27 1.47 2 -3 6 1.57 1.14 2 3 7 20.03 1.69 2 -3 7 20.06 2.25 2 -3 7 21.69 1.70 2 -3 8 0.32 0.81 -2 -4 8 0.42 1.18 -2 -4 8 1.35 0.79 -2 -4 7 4.84 1.40 -2 -4 7 6.55 1.45 -2 -4 7 4.78 1.27 -2 4 6 11.00 2.21 -2 -4 6 13.36 2.12 -2 -4 6 14.21 2.00 -2 -4 6 11.05 1.84 -2 -4 5 14.12 2.10 -2 -4 5 12.09 1.76 -2 -4 5 8.83 1.09 -2 -4 5 10.29 1.91 -2 -4 4 125.94 8.84 -2 -4 4 162.88 8.52 -2 4 3 53.56 3.18 -2 4 3 50.34 3.30 -2 -4 3 58.08 3.35 -2 4 2 8.46 0.67 2 -4 -2 8.92 0.72 -2 -4 2 8.49 0.78 2 4 -1 11.12 1.03 -2 4 1 11.22 0.82 2 -4 -1 13.39 0.95 2 4 0 280.44 16.40 -2 4 0 279.46 16.19 2 -4 0 292.31 16.37 2 4 1 0.04 0.26 2 -4 1 0.17 0.25 2 -4 1 0.10 0.14 2 -4 2 70.93 4.40 2 -4 2 71.57 4.19 2 -4 3 3.46 0.50 2 4 4 2.66 0.70 2 -4 4 0.91 1.02 2 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1.03 1.00 2 -5 6 1.87 1.29 2 -5 6 2.44 1.09 2 5 7 0.40 0.64 2 -5 7 0.79 0.62 2 -5 7 0.97 1.10 -2 -6 7 4.18 1.34 -2 -6 7 4.99 1.17 -2 -6 6 15.31 2.14 -2 -6 6 11.25 2.02 2 6 -5 0.30 0.99 -2 -6 5 0.30 1.47 -2 -6 5 -0.67 1.29 -2 6 4 58.33 3.63 -2 -6 4 59.80 3.71 -2 -6 4 55.85 4.02 -2 -6 4 62.91 4.31 -2 -6 4 54.27 4.29 -2 6 3 0.22 0.47 -2 -6 3 0.38 0.47 -2 6 2 57.39 3.41 -2 6 2 58.07 3.57 -2 -6 2 58.28 3.56 -2 -6 2 53.58 3.75 2 -6 -2 58.70 3.54 -2 6 1 5.32 0.70 -2 6 1 5.69 0.57 2 -6 -1 5.08 0.66 2 6 0 369.51 21.28 2 6 0 342.83 21.47 -2 6 0 382.64 21.36 -2 6 0 389.40 21.20 2 -6 0 374.64 21.43 2 6 1 104.80 5.55 -2 6 -1 82.12 5.60 2 6 2 8.79 0.75 2 -6 2 6.91 0.90 2 6 3 40.87 2.71 2 6 3 51.36 3.21 2 -6 3 42.10 2.99 2 -6 3 41.06 2.87 2 6 4 1.73 1.07 2 -6 4 1.63 0.64 2 -6 4 3.31 1.37 2 -6 4 4.35 1.14 2 6 5 2.87 1.13 2 -6 5 4.15 1.51 2 -6 5 3.47 1.31 2 6 6 30.19 2.41 2 -6 6 29.09 2.69 2 -6 6 32.79 2.47 2 6 7 1.35 0.63 2 -6 7 1.31 0.47 2 -6 7 2.60 0.98 -2 -7 7 -0.67 0.93 -2 -7 7 1.01 0.91 -2 -7 6 8.93 1.70 -2 -7 6 6.30 1.40 2 7 -5 6.74 1.38 -2 -7 5 9.24 2.03 -2 -7 5 6.92 1.69 -2 7 4 2.41 0.67 2 7 -4 3.36 1.11 -2 -7 4 2.61 1.38 -2 -7 4 2.04 1.47 -2 -7 4 2.49 1.49 -2 7 3 23.86 1.70 -2 7 3 20.71 1.72 -2 7 3 21.53 1.60 2 7 -3 22.03 2.07 -2 -7 3 21.60 2.21 -2 -7 3 23.41 2.29 -2 -7 3 20.47 2.10 -2 -7 3 25.47 1.77 -2 7 2 14.12 1.21 -2 7 2 13.10 1.02 -2 -7 2 13.65 1.21 -2 7 1 3.11 0.45 -2 7 1 3.45 0.67 -2 7 0 1.98 0.53 2 7 0 2.12 0.42 -2 7 0 2.37 0.36 2 7 1 27.11 1.80 -2 7 -1 26.23 1.85 2 7 2 1.81 0.42 2 -7 2 1.32 0.41 2 7 3 37.22 2.76 2 7 3 37.41 2.43 -2 7 -3 36.41 2.70 2 -7 3 37.63 2.71 2 7 4 11.45 1.26 2 7 4 11.22 1.49 2 -7 4 10.81 1.49 2 7 5 15.14 1.85 2 -7 5 17.53 2.26 2 -7 5 18.14 1.96 2 7 6 2.68 0.93 2 -7 6 2.30 1.26 2 -7 6 4.63 0.98 2 7 7 11.02 0.98 2 -7 7 12.51 1.62 -2 -8 6 0.06 1.11 -2 -8 6 1.07 1.45 2 8 -5 8.34 1.39 -2 -8 5 9.02 1.78 -2 -8 5 14.65 2.33 -2 8 4 40.58 2.66 2 8 -4 32.05 2.85 -2 8 4 32.95 2.39 -2 -8 4 32.77 3.04 -2 -8 4 36.43 3.12 -2 8 3 67.34 4.10 -2 8 3 67.60 4.19 -2 8 3 74.27 4.26 2 8 -3 66.45 4.53 -2 -8 3 68.95 4.75 -2 -8 3 67.72 4.75 -2 -8 3 61.83 4.57 -2 -8 3 62.20 4.33 2 8 -2 4.95 1.25 -2 8 2 3.88 0.66 -2 8 2 5.18 0.92 -2 8 2 4.64 0.79 -2 -8 2 4.68 0.79 -2 -8 2 4.92 1.35 -2 -8 2 3.64 0.96 -2 8 1 7.17 0.82 -2 8 1 11.45 1.36 -2 8 1 6.75 0.74 -2 8 1 8.14 1.02 2 8 0 3.31 0.52 -2 8 0 3.56 1.43 -2 8 0 4.20 0.72 -2 8 0 3.63 0.47 -2 8 0 4.99 0.71 -2 8 -1 29.79 2.22 2 8 1 36.39 2.21 -2 8 -1 33.45 2.55 -2 8 -1 31.19 2.42 2 -8 1 33.79 2.43 2 8 2 36.43 2.71 2 8 2 39.72 2.47 2 8 2 36.26 2.50 -2 8 -2 37.67 2.83 2 -8 2 39.86 2.74 2 -8 2 34.59 2.40 2 8 3 116.90 6.99 2 8 3 113.78 7.20 2 8 3 116.18 7.03 -2 8 -3 121.49 7.25 2 -8 3 120.58 7.22 2 8 4 0.61 0.65 2 8 4 -0.02 1.05 2 -8 4 0.39 1.01 2 8 5 1.05 0.99 2 -8 5 3.49 1.18 2 8 6 3.46 0.78 2 -8 6 4.19 0.88 -2 -9 6 28.73 2.29 2 9 -5 1.07 1.02 -2 -9 5 0.72 1.17 -2 -9 5 3.67 1.71 -2 9 4 1.81 0.87 -2 9 4 0.35 0.64 2 9 -4 2.37 1.20 -2 9 4 1.58 0.65 -2 -9 4 3.98 1.80 -2 -9 4 0.45 1.42 -2 9 3 106.38 6.46 2 9 -3 110.33 6.86 -2 9 3 106.49 6.33 -2 9 3 103.43 6.44 -2 -9 3 119.87 6.70 -2 -9 3 103.51 6.82 -2 -9 3 94.58 6.83 -2 9 2 52.71 3.36 2 9 -2 46.21 3.57 -2 9 2 49.75 3.14 -2 9 2 52.72 3.30 -2 -9 2 48.99 3.43 -2 -9 2 46.63 3.68 -2 9 1 57.08 3.57 -2 9 1 55.63 3.48 -2 9 1 53.20 3.39 -2 9 1 52.03 3.30 2 9 -1 52.52 3.85 -2 9 1 55.15 3.71 2 9 -1 48.51 3.48 2 -9 -1 60.16 3.61 -2 -9 1 52.77 3.69 -2 -9 1 53.85 3.52 -2 9 0 18.41 2.00 2 9 0 20.03 1.46 -2 9 0 19.15 1.36 -2 9 0 18.57 1.43 -2 9 0 19.96 1.58 -2 9 0 18.43 1.69 2 9 0 18.42 1.46 2 -9 0 19.52 1.64 -2 9 -1 11.86 1.11 -2 9 -1 11.74 1.01 2 9 1 12.64 1.15 -2 9 -1 11.46 1.58 2 9 1 12.11 1.21 2 9 1 10.54 1.46 2 -9 1 11.76 1.30 2 -9 1 13.04 1.11 -2 9 -2 10.24 1.54 2 9 2 9.03 1.12 2 9 2 10.82 1.53 2 9 2 10.42 1.05 2 -9 2 9.29 1.08 2 -9 2 10.22 1.41 2 9 3 20.49 2.09 2 9 3 21.06 1.77 -2 9 -3 22.10 2.13 2 -9 3 21.72 2.06 -2 9 -4 82.31 5.19 2 9 4 78.58 5.26 2 9 4 82.16 5.00 2 -9 4 83.33 5.32 2 9 5 13.52 1.49 2 -9 5 13.03 1.55 2 10 -5 21.01 2.03 -2 -10 5 23.54 2.35 -2 10 4 64.71 3.89 2 10 -4 62.53 4.26 -2 10 4 61.95 3.75 -2 10 4 58.56 3.83 -2 -10 4 56.58 4.34 2 10 -3 26.58 2.64 -2 10 3 24.64 1.86 -2 10 3 25.56 2.01 -2 10 3 24.88 1.98 -2 -10 3 25.15 2.34 -2 10 2 10.56 1.34 -2 10 2 12.53 1.53 2 10 -2 16.27 2.06 -2 10 2 12.31 1.27 -2 -10 2 12.01 1.73 -2 -10 2 11.22 1.85 -2 10 1 9.16 1.07 -2 10 1 8.29 1.10 -2 10 1 9.40 1.36 2 10 -1 8.31 1.53 2 10 -1 6.24 1.06 -2 -10 1 9.19 1.39 2 -10 -1 9.49 1.22 -2 10 0 27.78 2.41 -2 10 0 29.15 2.15 2 10 0 28.78 2.06 -2 10 0 29.23 2.02 2 -10 0 28.39 2.24 -2 10 -1 30.23 2.04 2 10 1 29.55 2.08 2 10 1 27.53 2.11 2 10 1 28.81 2.38 -2 10 -1 27.70 2.46 2 -10 1 30.56 2.33 2 -10 1 26.60 2.04 2 10 2 65.66 4.56 -2 10 -2 71.30 4.67 2 10 2 70.76 4.42 2 -10 2 74.87 4.57 2 -10 2 67.50 4.32 2 10 3 1.40 0.72 -2 10 -3 1.07 1.07 2 10 3 1.52 1.12 2 -10 3 1.28 1.10 2 10 4 14.08 1.35 -2 10 -4 12.80 1.52 2 10 4 10.85 1.61 2 -10 4 14.22 1.73 2 10 5 26.45 1.98 2 -10 5 23.55 1.96 2 10 6 1.01 0.64 2 11 -5 19.91 1.74 2 11 -4 4.32 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7.61 0.76 -4 4 3 7.79 1.05 -4 -4 3 6.60 0.93 -4 -4 3 8.23 1.48 -4 4 2 120.03 6.40 -4 4 2 111.94 6.63 4 -4 -2 97.76 6.60 -4 4 1 20.91 1.36 4 4 -1 19.59 1.76 -4 4 1 19.87 1.64 -4 4 0 1.26 0.30 4 4 0 0.36 0.42 -4 4 0 0.41 0.55 4 -4 0 0.72 0.42 -4 4 -1 24.91 1.55 -4 4 -1 24.88 1.89 4 4 1 26.75 2.78 4 -4 1 22.26 1.65 4 4 2 101.31 6.24 -4 4 -2 104.57 5.96 4 -4 2 101.58 6.06 4 4 3 18.72 1.79 4 4 3 20.26 1.81 4 -4 3 18.06 1.76 4 -4 3 18.59 2.21 4 -4 3 18.72 1.48 -4 -4 -3 18.70 2.61 4 4 4 43.42 3.03 4 4 4 42.30 3.06 4 4 4 34.82 3.85 4 -4 4 43.73 3.49 4 -4 4 42.88 2.76 4 -4 4 42.83 3.04 4 4 5 7.70 1.29 4 -4 5 9.22 1.45 4 -4 5 11.27 1.90 4 4 6 8.45 1.22 4 -4 6 7.77 1.50 4 -4 6 10.36 1.24 4 -4 6 9.81 1.09 4 4 7 -0.40 0.39 4 -4 7 -0.14 0.39 4 -4 7 0.42 0.81 -4 -5 7 14.30 1.58 -4 -5 7 12.62 1.47 -4 -5 7 11.57 1.45 -4 -5 6 166.20 10.51 -4 -5 6 173.30 10.47 -4 -5 6 177.72 10.66 -4 -5 5 3.91 1.48 -4 -5 5 3.11 1.76 -4 -5 5 4.45 1.74 -4 -5 5 4.50 1.87 -4 5 4 69.01 4.34 -4 -5 4 70.10 4.89 -4 -5 4 68.28 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-1.27 1.13 -7 4 3 29.28 2.42 -7 4 3 31.93 2.64 -7 -4 3 30.63 2.89 -7 -4 3 31.88 2.84 -7 -4 3 32.46 2.98 -7 4 2 2.42 0.99 -7 -4 2 1.75 1.44 -7 -4 2 1.52 1.28 -7 4 1 15.03 1.76 -7 -4 1 15.55 2.43 -7 4 0 23.72 2.10 7 -4 0 23.47 1.77 -7 -4 0 26.50 2.79 7 4 1 14.89 1.96 -7 4 -1 21.61 1.78 7 -4 1 18.39 1.49 -7 -4 -1 18.97 2.82 7 4 2 18.42 1.79 7 -4 2 22.35 1.67 -7 -4 -2 24.06 2.43 -7 4 -3 1.41 0.76 7 -4 3 1.33 0.56 -7 -4 -3 1.97 1.18 -7 -4 -4 24.59 2.26 7 -4 4 32.61 1.87 7 -4 4 29.20 1.94 -7 4 -5 1.78 0.45 -7 -5 5 -1.22 1.14 -7 -5 5 0.36 0.92 -7 -5 5 -0.36 0.85 -7 5 4 33.31 2.66 -7 5 4 47.01 2.99 -7 -5 4 38.99 3.02 -7 -5 4 36.95 3.10 -7 -5 4 35.87 3.28 -7 -5 4 41.80 3.24 -7 5 3 -0.10 0.96 -7 5 3 0.84 0.87 -7 -5 3 -0.76 1.22 -7 -5 3 0.07 1.14 -7 -5 3 0.28 1.34 -7 5 2 -0.04 0.54 -7 5 2 -0.03 0.93 -7 -5 2 -0.17 1.34 -7 5 1 9.65 1.37 -7 5 1 9.46 1.07 -7 -5 1 8.94 1.88 -7 5 0 20.57 1.83 -7 -5 0 16.11 2.53 7 -5 0 19.94 1.51 -7 5 -1 17.55 1.63 -7 -5 -1 15.71 2.21 7 -5 1 16.34 1.39 -7 -5 -2 85.57 5.82 7 -5 2 81.90 5.02 -7 5 -3 1.03 0.68 7 -5 3 0.18 0.52 -7 -5 -3 0.44 1.01 7 -5 4 17.24 1.17 7 -5 4 16.30 1.22 -7 -6 5 10.86 1.20 -7 -6 5 7.75 1.22 -7 -6 5 11.38 1.21 -7 -6 4 -1.42 0.99 -7 -6 4 -0.73 1.09 -7 -6 4 -0.86 1.01 -7 -6 4 -0.47 0.96 -7 6 3 5.59 1.04 -7 6 3 5.21 1.12 -7 -6 3 6.27 1.39 -7 -6 3 5.47 1.26 -7 6 2 12.01 1.12 -7 6 2 12.17 1.56 -7 -6 2 11.98 1.90 -7 6 1 1.25 0.59 -7 6 1 1.11 0.86 -7 -6 1 1.34 1.21 -7 6 0 11.07 1.47 -7 6 0 10.14 1.07 7 -6 0 9.12 1.03 -7 -6 0 8.97 1.67 7 -6 1 66.18 4.12 -7 -6 -1 69.26 4.95 7 -6 2 10.47 1.01 -7 -6 -2 8.40 1.55 -7 6 -3 14.40 1.76 -7 -6 -3 15.96 1.48 7 -6 3 17.55 1.28 -7 6 -4 29.62 2.34 7 -6 4 38.61 2.11 7 7 -5 0.31 0.71 -7 -7 4 22.42 2.39 -7 -7 4 18.44 1.83 -7 -7 4 19.67 1.96 -7 7 3 10.61 1.30 -7 -7 3 9.86 1.79 -7 -7 3 10.18 1.63 -7 7 2 1.16 0.54 -7 7 2 1.35 0.83 -7 7 2 1.60 0.93 -7 -7 2 1.15 1.33 -7 7 1 65.87 4.22 -7 7 1 63.35 3.91 -7 -7 1 63.65 4.76 -7 7 0 10.90 1.06 -7 7 0 11.14 1.42 7 -7 0 11.50 1.06 -7 -7 0 10.29 1.93 7 -7 1 22.02 1.54 -7 -7 -1 19.62 2.03 7 -7 2 4.97 0.69 7 -7 3 5.97 0.71 7 8 -4 0.45 0.61 -7 -8 4 1.00 1.20 -7 -8 4 0.41 0.76 7 8 -3 1.80 0.69 -7 -8 3 3.31 1.18 -7 -8 3 2.19 0.96 -7 -8 3 2.33 0.80 -7 8 2 -0.21 0.66 -7 8 2 0.79 0.47 -7 8 2 0.04 0.72 -7 -8 2 0.10 0.85 -7 -8 2 0.04 1.03 -7 8 1 2.19 0.52 -7 8 1 2.32 0.73 7 -8 -1 2.53 0.61 -7 -8 1 1.66 1.21 -7 8 0 7.97 0.86 -7 8 0 7.96 1.05 7 -8 0 7.63 0.87 -7 -8 0 8.36 1.32 -7 -8 -1 23.04 2.36 7 -8 1 31.25 1.86 7 -8 2 0.26 0.40 7 8 3 0.69 0.39 7 9 -3 1.96 0.72 -7 -9 3 2.09 0.71 -7 9 2 17.03 1.20 -7 -9 2 15.30 1.64 -7 9 1 12.30 0.93 7 -9 -1 8.81 1.01 -7 -9 1 10.45 1.50 -7 -9 1 8.88 1.19 7 -9 0 14.22 1.06 -7 -9 0 12.07 1.48 -7 -9 -1 1.77 0.60 7 -9 1 1.54 0.39 7 9 2 8.45 0.81 -7 -10 2 12.54 1.26 -7 10 1 2.66 0.42 -7 -10 1 1.91 0.67 -7 -10 0 1.72 0.96 -8 0 5 -0.05 0.70 -8 0 4 1.19 1.04 -8 0 3 -0.11 0.65 -8 0 3 -0.69 0.94 -8 0 2 0.75 1.07 -8 0 2 0.72 0.77 -8 0 1 0.87 0.80 -8 0 1 1.05 0.97 -8 0 0 188.12 10.24 -8 0 0 140.77 9.78 8 0 1 -0.15 0.57 -8 0 -1 0.63 0.92 8 0 2 28.01 2.06 -8 0 -2 31.26 2.51 -8 0 -3 0.33 0.81 8 0 3 0.06 0.50 -8 0 -4 2.02 0.66 -8 1 5 0.44 0.52 -8 -1 5 -0.07 0.71 -8 1 4 5.36 1.01 -8 -1 4 6.27 1.04 -8 1 3 1.07 0.71 -8 1 3 1.58 0.88 -8 -1 3 1.22 1.10 -8 -1 3 0.80 1.02 -8 -1 3 1.57 0.66 -8 1 2 51.13 3.39 -8 1 2 50.11 3.48 -8 -1 2 50.25 3.53 -8 -1 2 49.76 3.36 -8 -1 2 47.50 3.56 -8 1 1 10.25 1.51 -8 1 1 7.81 1.16 -8 -1 1 9.78 1.62 -8 1 0 34.05 2.50 -8 1 0 26.26 2.27 -8 -1 0 28.56 2.82 -8 1 -1 1.89 0.73 -8 1 -1 1.66 0.91 8 1 1 1.77 0.83 -8 -1 -1 0.60 1.14 8 -1 1 1.21 0.58 -8 1 -2 5.19 1.00 8 1 2 5.74 0.79 8 -1 2 6.15 0.84 -8 -1 -2 4.15 1.27 8 1 3 3.28 0.61 -8 1 -3 1.57 0.73 -8 -1 -3 3.27 0.92 8 -1 3 2.47 0.52 -8 1 -4 2.62 0.58 -8 -1 -4 4.67 0.81 -8 2 5 16.53 1.54 -8 -2 5 20.78 1.65 -8 2 4 1.72 0.91 -8 -2 4 2.57 0.94 -8 -2 4 1.39 0.85 -8 2 3 21.48 1.70 -8 2 3 18.50 1.94 -8 -2 3 17.25 2.05 -8 -2 3 18.01 2.00 -8 -2 3 21.91 2.19 -8 2 2 0.13 0.92 -8 2 2 -0.32 0.72 -8 -2 2 0.79 1.03 -8 2 1 5.25 0.96 -8 2 1 5.31 1.10 -8 -2 1 2.26 1.12 -8 -2 1 1.98 1.13 -8 -2 0 13.11 1.92 -8 2 -1 10.84 1.21 -8 2 -1 9.32 1.43 -8 -2 -1 9.57 1.69 8 -2 1 8.91 1.01 -8 2 -2 13.67 1.49 8 2 2 13.80 1.27 -8 -2 -2 13.01 1.66 8 -2 2 15.23 1.24 8 2 3 8.33 0.99 8 -2 3 10.84 0.97 -8 -2 -3 10.19 1.46 -8 2 -4 1.28 0.52 -8 -2 -4 0.57 0.47 -8 3 5 2.25 0.67 -8 -3 5 2.02 0.69 -8 -3 5 2.69 0.76 -8 3 4 2.93 0.78 -8 -3 4 2.87 0.91 -8 -3 4 1.84 0.96 -8 -3 4 0.82 0.85 -8 3 3 3.29 0.92 -8 3 3 3.06 0.81 -8 -3 3 3.46 1.24 -8 -3 3 2.61 1.04 -8 3 2 0.80 0.75 -8 3 2 1.88 1.06 -8 -3 2 0.43 1.00 -8 -3 2 0.36 1.01 -8 3 1 32.76 2.52 -8 3 1 39.20 2.70 -8 -3 1 30.06 2.99 -8 3 0 1.93 0.78 -8 -3 0 0.20 1.24 -8 3 -1 17.81 1.46 -8 -3 -1 13.17 2.11 8 -3 1 15.30 1.29 8 3 2 0.09 0.49 -8 3 -2 -0.04 0.65 -8 -3 -2 -0.09 0.80 8 -3 2 0.03 0.46 -8 3 -3 19.97 1.66 -8 -3 -3 22.21 1.81 -8 3 -4 2.06 0.52 -8 -3 -4 0.37 0.47 -8 -4 5 3.05 1.03 -8 4 4 21.87 1.68 -8 -4 4 18.34 1.79 -8 -4 4 19.96 1.84 -8 4 3 6.07 0.88 -8 4 3 4.48 1.03 -8 -4 3 3.65 1.12 -8 -4 3 5.49 1.09 -8 4 2 8.12 1.13 -8 4 2 9.81 1.35 -8 -4 2 6.35 1.29 -8 4 1 2.61 0.77 -8 4 1 4.22 0.98 -8 -4 1 1.71 1.14 -8 4 0 7.63 1.01 -8 -4 0 3.96 1.07 -8 4 -1 24.87 2.21 8 -4 1 23.50 1.65 -8 -4 -1 21.43 2.46 -8 -4 -2 2.02 0.90 8 -4 2 4.25 0.63 -8 -4 -3 4.10 0.93 8 -4 3 3.21 0.49 -8 -5 4 0.98 0.64 -8 -5 4 2.49 0.69 -8 5 3 0.28 0.76 -8 -5 3 0.15 0.89 -8 -5 3 -0.15 0.79 -8 5 2 24.61 1.93 -8 5 2 21.09 1.95 -8 -5 2 27.12 2.21 -8 5 1 -0.23 0.65 -8 -5 1 -0.81 1.01 -8 5 0 4.58 0.79 -8 -5 0 4.42 1.52 8 -5 0 6.45 0.81 -8 -5 -1 4.13 1.09 8 -5 1 5.02 0.65 -8 -5 -2 0.64 0.58 8 -5 2 1.23 0.43 -8 -5 -3 8.17 0.97 -8 -6 4 0.46 0.65 -8 6 3 10.94 1.17 -8 -6 3 11.07 1.30 -8 6 2 9.75 1.21 -8 6 2 9.75 1.34 -8 -6 2 9.01 1.34 -8 6 1 0.27 0.67 -8 6 1 0.23 0.64 -8 -6 1 -0.13 0.95 -8 6 0 7.16 1.12 8 -6 0 6.82 0.79 -8 -6 0 8.56 1.49 -8 -6 -1 6.51 1.03 8 -6 1 5.74 0.73 -8 -6 -2 -0.01 0.69 8 -6 2 0.47 0.37 -8 -7 3 5.88 1.10 -8 -7 3 7.60 1.06 -8 7 2 10.69 1.09 -8 -7 2 10.44 1.37 -8 -7 2 8.64 1.21 -8 -7 1 11.99 1.39 -8 -7 0 4.04 0.90 8 -7 0 4.17 0.58 -8 -7 -1 10.71 1.28 8 -7 1 13.35 1.01 -8 -7 -2 0.29 0.46 -8 -8 2 -0.41 0.70 -8 8 1 3.13 0.61 -8 -8 1 2.70 0.95 -8 -8 1 1.49 0.62 -8 -8 0 0.55 0.44 -9 0 4 9.30 1.06 -9 0 3 0.95 0.74 -9 0 2 6.33 1.01 -9 0 1 0.54 0.72 -9 0 1 0.97 0.79 -9 0 -1 -0.21 0.64 -9 0 -2 58.50 3.76 -9 1 4 8.08 0.93 -9 -1 4 8.87 0.93 -9 1 3 1.90 0.83 -9 -1 3 1.49 0.65 -9 1 2 8.35 1.22 -9 -1 2 12.85 1.27 -9 1 1 6.18 1.04 -9 -1 1 4.23 0.98 -9 1 0 2.00 0.73 -9 -1 0 1.73 0.71 -9 -1 0 2.17 0.89 -9 1 -1 1.10 0.55 -9 -1 -1 0.85 0.76 -9 1 -2 15.30 1.48 -9 -1 -2 18.80 1.51 -9 2 4 1.20 0.51 -9 2 3 20.57 1.55 -9 -2 3 17.19 1.51 -9 2 2 7.79 1.11 -9 -2 2 6.58 0.99 -9 -2 2 6.81 1.03 -9 2 1 1.32 0.73 -9 -2 1 0.31 0.74 -9 -2 1 0.74 0.65 -9 2 0 1.07 0.66 -9 -2 0 -0.10 0.61 -9 -2 -1 9.86 1.36 -9 -2 -2 1.55 0.64 -9 3 3 2.64 0.60 -9 -3 3 2.02 0.87 -9 3 2 3.96 0.75 -9 -3 2 2.27 0.72 -9 3 1 12.43 1.18 -9 -3 1 8.96 1.44 -9 -3 1 11.78 1.24 -9 3 0 0.34 0.58 -9 -3 0 0.07 0.58 -9 3 -1 2.81 0.61 -9 -3 -1 4.07 0.91 -9 -3 -2 -0.08 0.63 -9 4 3 5.18 0.77 -9 4 2 2.39 0.58 -9 -4 2 1.34 0.70 -9 -4 2 2.42 0.70 -9 4 1 0.55 0.52 -9 -4 1 0.62 0.63 -9 -4 1 0.29 0.69 -9 4 0 8.85 0.95 -9 -4 0 5.80 1.14 -9 4 -1 0.40 0.48 -9 -4 -1 0.42 0.64 -9 5 2 4.45 0.74 -9 5 1 0.23 0.50 -9 -5 1 -0.03 0.58 -9 -5 1 0.63 0.54 -9 5 0 1.98 0.52 -9 -5 0 1.09 0.67 -9 -5 -1 0.25 0.49 -9 6 1 0.84 0.53 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 75736 _shelx_shelxl_version_number 2014/7 _olex2_submission_special_instructions 'No special instructions were received' 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_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 Cl1 Cl 0.44626(11) 0.15239(7) 0.09065(13) 0.0346(3) Uani 1 1 d . N4 N -0.0508(3) 0.3303(2) 0.2617(4) 0.0257(7) Uani 1 1 d . N1 N 0.4099(4) 0.3629(2) 0.0895(4) 0.0301(7) Uani 1 1 d . N3 N -0.0590(4) 0.2210(2) 0.2684(4) 0.0295(7) Uani 1 1 d . N2 N 0.0792(4) 0.1799(2) 0.2180(4) 0.0290(7) Uani 1 1 d . C1 C 0.3252(4) 0.4562(3) 0.1162(5) 0.0314(8) Uani 1 1 d . H1 H 0.3784 0.5223 0.0929 0.038 Uiso 1 1 calc R C2 C 0.1689(4) 0.4619(3) 0.1744(5) 0.0287(8) Uani 1 1 d . H2 H 0.1148 0.5286 0.1912 0.034 Uiso 1 1 calc R C3 C 0.0959(4) 0.3618(3) 0.2066(5) 0.0239(7) Uani 1 1 d . C6 C -0.1880(5) 0.3954(3) 0.3162(6) 0.0338(8) Uani 1 1 d . H6A H -0.1672 0.4717 0.2914 0.051 Uiso 1 1 calc GR H6B H -0.1992 0.3854 0.4503 0.051 Uiso 1 1 calc GR H6C H -0.2896 0.3728 0.2435 0.051 Uiso 1 1 calc GR C5 C 0.3379(4) 0.2709(3) 0.1215(5) 0.0262(8) Uani 1 1 d . C4 C 0.1786(4) 0.2651(2) 0.1781(5) 0.0261(8) 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 Cl1 0.0387(6) 0.0296(5) 0.0359(6) -0.0003(3) 0.0056(4) 0.0092(3) N4 0.0274(15) 0.0217(14) 0.0282(16) 0.0010(11) 0.0028(12) -0.0014(11) N1 0.0310(15) 0.0303(16) 0.0288(16) 0.0009(12) 0.0016(12) -0.0018(12) N3 0.0315(16) 0.0213(14) 0.0357(17) 0.0031(12) 0.0028(12) -0.0033(11) N2 0.0342(16) 0.0204(14) 0.0327(17) 0.0025(12) 0.0041(12) -0.0009(11) C1 0.0359(19) 0.0216(17) 0.037(2) 0.0006(15) 0.0045(15) -0.0058(14) C2 0.0350(19) 0.0196(16) 0.0309(19) -0.0010(14) 0.0000(14) -0.0014(13) C3 0.0279(17) 0.0222(16) 0.0216(17) -0.0006(13) 0.0023(13) -0.0004(12) C6 0.0335(19) 0.0292(18) 0.040(2) -0.0004(16) 0.0097(15) 0.0032(15) C5 0.0296(18) 0.0262(17) 0.0226(18) -0.0005(13) 0.0007(13) 0.0006(13) C4 0.0330(18) 0.0179(16) 0.0272(19) 0.0009(13) 0.0016(14) -0.0015(13) 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' Cl Cl 0.3639 0.7018 '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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N3 N4 C6 120.0(3) C3 N4 N3 110.3(3) C3 N4 C6 129.8(3) C5 N1 C1 117.9(3) N2 N3 N4 109.2(3) N3 N2 C4 107.3(3) N1 C1 H1 117.3 N1 C1 C2 125.4(3) C2 C1 H1 117.3 C1 C2 H2 122.5 C1 C2 C3 114.9(3) C3 C2 H2 122.5 N4 C3 C2 134.7(3) N4 C3 C4 104.3(3) C4 C3 C2 121.0(3) N4 C6 H6A 109.5 N4 C6 H6B 109.5 N4 C6 H6C 109.5 H6A C6 H6B 109.5 H6A C6 H6C 109.5 H6B C6 H6C 109.5 N1 C5 Cl1 118.0(3) N1 C5 C4 122.6(3) C4 C5 Cl1 119.4(3) N2 C4 C3 108.9(3) N2 C4 C5 132.9(3) C3 C4 C5 118.1(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Cl1 C5 1.740(3) N4 N3 1.358(4) N4 C3 1.354(4) N4 C6 1.464(5) N1 C1 1.371(5) N1 C5 1.312(5) N3 N2 1.319(4) N2 C4 1.378(4) C1 H1 0.9500 C1 C2 1.382(5) C2 H2 0.9500 C2 C3 1.405(5) C3 C4 1.401(5) C6 H6A 0.9800 C6 H6B 0.9800 C6 H6C 0.9800 C5 C4 1.401(5) 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 Cl1 C5 C4 N2 -0.2(6) Cl1 C5 C4 C3 178.4(3) N4 N3 N2 C4 0.0(4) N4 C3 C4 N2 -0.3(4) N4 C3 C4 C5 -179.2(3) N1 C1 C2 C3 -0.1(6) N1 C5 C4 N2 179.5(3) N1 C5 C4 C3 -2.0(5) N3 N4 C3 C2 179.2(4) N3 N4 C3 C4 0.4(4) N3 N2 C4 C3 0.2(4) N3 N2 C4 C5 178.8(4) C1 N1 C5 Cl1 -179.2(3) C1 N1 C5 C4 1.2(5) C1 C2 C3 N4 -179.5(4) C1 C2 C3 C4 -0.8(5) C2 C3 C4 N2 -179.4(3) C2 C3 C4 C5 1.7(5) C3 N4 N3 N2 -0.3(4) C6 N4 N3 N2 -178.4(3) C6 N4 C3 C2 -2.9(6) C6 N4 C3 C4 178.3(3) C5 N1 C1 C2 -0.1(6)