#------------------------------------------------------------------------------ #$Date: 2020-04-04 06:55:26 +0300 (Sat, 04 Apr 2020) $ #$Revision: 250043 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/51/75/4517519.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_4517519 loop_ _publ_author_name 'Zhu, Cuiju' 'Kuniyil, Rositha' 'Jei, Becky B.' 'Ackermann, Lutz' _publ_section_title ; Domino C--H Activation/Directing Group Migration/Alkyne Annulation: Unique Selectivity by d6-Cobalt(III) Catalysts ; _journal_issue 7 _journal_name_full 'ACS Catalysis' _journal_page_first 4444 _journal_paper_doi 10.1021/acscatal.9b05413 _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C21 H18 N2 O' _chemical_formula_sum 'C21 H18 N2 O' _chemical_formula_weight 314.37 _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 _audit_creation_date 2019-01-18 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 97.3950(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 10.2077(4) _cell_length_b 19.7705(7) _cell_length_c 8.1575(3) _cell_measurement_reflns_used 5173 _cell_measurement_temperature 99.93 _cell_measurement_theta_max 29.611 _cell_measurement_theta_min 2.518 _cell_volume 1632.58(11) _computing_cell_refinement 'SAINT V8.38A (?, 2016)' _computing_data_reduction 'SAINT V8.38A (?, 2016)' _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, 2015)' _diffrn_ambient_temperature 99.93 _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.0160 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 4532 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.663 _diffrn_reflns_theta_min 2.880 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_T_max 0.825235 _exptl_absorpt_correction_T_min 0.768980 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. Final HKLF 4 output contains 58044 reflections, Rint = 0.0290 (47689 with I > 3sig(I), Rint = 0.0281) ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.279 _exptl_crystal_description block _exptl_crystal_F_000 664 _exptl_crystal_recrystallization_method 'The material was recrystallised from Ethylacetate by slow evaporation' _exptl_crystal_size_max 0.475 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.242 _refine_diff_density_max 0.353 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 220 _refine_ls_number_reflns 4532 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.071 _refine_ls_R_factor_all 0.0380 _refine_ls_R_factor_gt 0.0364 _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^)+(0.0488P)^2^+0.3803P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0939 _refine_ls_wR_factor_ref 0.0953 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4338 _reflns_number_total 4532 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file cs9b05413_si_002.cif _cod_data_source_block 0536_cg_0m_4 _cod_depositor_comments 'Adding full bibliography for 4517519--4517521.cif.' _cod_database_code 4517519 _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. ; _shelx_estimated_absorpt_t_max 0.981 _shelx_estimated_absorpt_t_min 0.963 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.6496(12) 0.3504(12) 2. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 3.a Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C4(H4), C8(H8), C9(H9), C10(H10), C11(H11), C12(H12), C18(H18), C19(H19), C20(H20), C21(H21) 3.b Idealised Me refined as rotating group: C15(H15A,H15B,H15C), C16(H16A,H16B,H16C) ; _shelx_res_file ; TITL 0536_cg_0m_4_a.res in P2(1)/c 0536_cg_0m_4.res created by SHELXL-2018/3 at 12:52:10 on 18-Jan-2019 REM Old TITL 0536_CG_0m_4 in P2/c REM SHELXT solution in P2(1)/c REM R1 0.113, Rweak 0.006, Alpha 0.034, Orientation as input REM Formula found by SHELXT: C21 N2 O CELL 0.71073 10.2077 19.7705 8.1575 90 97.395 90 ZERR 4 0.0004 0.0007 0.0003 0 0.001 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 84 72 8 4 L.S. 4 0 0 PLAN 5 SIZE 0.242 0.36 0.475 TEMP -173.22 BOND $H list 4 fmap 2 53 ACTA OMIT 2 5 0 OMIT 1 1 1 OMIT 10 9 6 OMIT -2 3 1 REM REM REM WGHT 0.048800 0.380300 BASF 0.35041 FVAR 1.90853 O1 4 0.212965 0.705420 0.523259 11.00000 0.01584 0.02722 = 0.02308 0.00031 0.00402 0.00622 N1 3 0.397035 0.648634 0.464325 11.00000 0.01191 0.01515 = 0.01229 -0.00016 0.00067 0.00052 N2 3 0.730140 0.663948 0.852548 11.00000 0.01694 0.01998 = 0.01495 -0.00078 0.00108 -0.00379 C1 1 0.265913 0.669056 0.427281 11.00000 0.01256 0.01873 = 0.01755 0.00343 0.00182 0.00110 C2 1 0.202095 0.644047 0.270956 11.00000 0.01452 0.02497 = 0.01940 0.00354 -0.00297 0.00044 AFIX 43 H2 2 0.113108 0.656648 0.235748 11.00000 -1.20000 AFIX 0 C3 1 0.264913 0.603066 0.172284 11.00000 0.01958 0.02343 = 0.01593 0.00080 -0.00372 -0.00335 AFIX 43 H3 2 0.219100 0.587851 0.070192 11.00000 -1.20000 AFIX 0 C4 1 0.397631 0.582634 0.219093 11.00000 0.01869 0.01742 = 0.01405 -0.00112 0.00055 -0.00118 AFIX 43 H4 2 0.440990 0.553049 0.151738 11.00000 -1.20000 AFIX 0 C5 1 0.460736 0.607193 0.364991 11.00000 0.01437 0.01290 = 0.01275 0.00087 0.00197 -0.00044 C6 1 0.596823 0.598985 0.443105 11.00000 0.01294 0.01237 = 0.01291 0.00094 0.00179 0.00023 C7 1 0.694907 0.558385 0.367740 11.00000 0.01397 0.01218 = 0.01544 -0.00221 0.00192 -0.00049 C8 1 0.767962 0.508439 0.460126 11.00000 0.01587 0.01365 = 0.01598 -0.00073 0.00146 -0.00063 AFIX 43 H8 2 0.752650 0.499819 0.570641 11.00000 -1.20000 AFIX 0 C9 1 0.862877 0.471302 0.391308 11.00000 0.01560 0.01362 = 0.02330 -0.00172 0.00030 0.00180 AFIX 43 H9 2 0.912039 0.437411 0.454846 11.00000 -1.20000 AFIX 0 C10 1 0.885992 0.483634 0.229891 11.00000 0.02001 0.01771 = 0.02507 -0.00404 0.00731 0.00318 AFIX 43 H10 2 0.951528 0.458578 0.183341 11.00000 -1.20000 AFIX 0 C11 1 0.812952 0.532733 0.136747 11.00000 0.02678 0.02134 = 0.01793 -0.00123 0.00869 0.00402 AFIX 43 H11 2 0.828463 0.541083 0.026187 11.00000 -1.20000 AFIX 0 C12 1 0.717136 0.569766 0.204580 11.00000 0.02059 0.01688 = 0.01696 0.00030 0.00477 0.00323 AFIX 43 H12 2 0.666741 0.602862 0.139741 11.00000 -1.20000 AFIX 0 C13 1 0.613109 0.634548 0.586332 11.00000 0.01180 0.01279 = 0.01211 0.00150 0.00141 0.00009 C14 1 0.483133 0.666491 0.619746 11.00000 0.01208 0.01439 = 0.01122 -0.00069 0.00135 0.00046 C15 1 0.427421 0.633446 0.766780 11.00000 0.01499 0.02021 = 0.01344 0.00085 0.00318 -0.00192 AFIX 137 H15A 2 0.342165 0.654080 0.780224 11.00000 -1.50000 H15B 2 0.489239 0.640324 0.867675 11.00000 -1.50000 H15C 2 0.415352 0.584872 0.746149 11.00000 -1.50000 AFIX 0 C16 1 0.496568 0.743359 0.638580 11.00000 0.01895 0.01309 = 0.01758 -0.00083 0.00333 0.00137 AFIX 137 H16A 2 0.534815 0.761979 0.544027 11.00000 -1.50000 H16B 2 0.554268 0.753936 0.740870 11.00000 -1.50000 H16C 2 0.409215 0.763337 0.642891 11.00000 -1.50000 AFIX 0 C17 1 0.737952 0.650731 0.691678 11.00000 0.01283 0.01164 = 0.01481 0.00035 0.00088 -0.00030 C18 1 0.856189 0.658029 0.623578 11.00000 0.01454 0.01605 = 0.01868 -0.00175 0.00348 -0.00013 AFIX 43 H18 2 0.859550 0.647815 0.510400 11.00000 -1.20000 AFIX 0 C19 1 0.968626 0.680357 0.723071 11.00000 0.01315 0.01630 = 0.02753 -0.00055 0.00241 -0.00076 AFIX 43 H19 2 1.049646 0.685791 0.678844 11.00000 -1.20000 AFIX 0 C20 1 0.960661 0.694568 0.887837 11.00000 0.01576 0.01808 = 0.02341 0.00097 -0.00395 -0.00311 AFIX 43 H20 2 1.035465 0.710340 0.958915 11.00000 -1.20000 AFIX 0 C21 1 0.839960 0.685038 0.945777 11.00000 0.02091 0.02299 = 0.01547 -0.00056 -0.00121 -0.00610 AFIX 43 H21 2 0.835016 0.694097 1.059185 11.00000 -1.20000 AFIX 0 HKLF 5 REM 0536_cg_0m_4_a.res in P2(1)/c REM wR2 = 0.095329, GooF = S = 1.07148, Restrained GooF = 1.07148 for all data REM R1 = 0.036450 for 4338 Fo > 4sig(Fo) and 0.037970 for all 4532 data REM 220 parameters refined using 0 restraints END WGHT 0.0488 0.3803 REM Highest difference peak 0.353, deepest hole -0.210, 1-sigma level 0.041 Q1 1 0.7954 0.6557 0.6605 11.00000 0.05 0.35 Q2 1 0.6753 0.6407 0.6374 11.00000 0.05 0.35 Q3 1 0.5294 0.5997 0.3988 11.00000 0.05 0.35 Q4 1 0.5501 0.6539 0.6082 11.00000 0.05 0.31 Q5 1 0.2375 0.6578 0.3437 11.00000 0.05 0.31 ; _shelx_res_checksum 64244 _shelx_hkl_file ; 5 0 0 2938.50 34.7938 -2 5 0 0 2938.50 34.7938 1 6 0 0 4240.80 49.3178 -2 6 0 0 4240.80 49.3178 1 7 0 0 3069.55 37.4120 -2 7 0 0 3069.55 37.4120 1 8 0 0 2650.70 33.6035 -2 8 0 0 2650.70 33.6035 1 9 0 0 5017.74 59.6509 -2 9 0 0 5017.74 59.6509 1 10 0 0 539.140 11.1253 -2 10 0 0 539.140 11.1253 1 11 0 0 1122.36 21.6583 -2 11 0 0 1122.36 21.6583 1 12 0 0 463.310 12.8452 -2 12 0 0 463.310 12.8452 1 13 0 0 503.555 24.3389 -2 13 0 0 503.555 24.3389 1 14 0 0 223.301 11.9170 -2 14 0 0 223.301 11.9170 1 3 1 0 5.38470 0.39617 -2 3 1 0 5.38470 0.39617 1 5 1 0 2511.32 20.3028 -2 5 1 0 2511.32 20.3028 1 6 1 0 261.796 4.70865 -2 6 1 0 261.796 4.70865 1 7 1 0 420.605 6.70283 -2 7 1 0 420.605 6.70283 1 8 1 0 6752.27 63.1137 -2 8 1 0 6752.27 63.1137 1 9 1 0 1052.60 11.8233 -2 9 1 0 1052.60 11.8233 1 10 1 0 21.9159 1.77114 -2 10 1 0 21.9159 1.77114 1 11 1 0 298.143 8.30736 -2 11 1 0 298.143 8.30736 1 12 1 0 61.2500 3.79886 -2 12 1 0 61.2500 3.79886 1 13 1 0 12.8536 3.14751 -2 13 1 0 12.8536 3.14751 1 14 1 0 507.520 14.8200 -2 14 1 0 507.520 14.8200 1 1 2 0 431.192 3.87999 -2 1 2 0 431.192 3.87999 1 3 2 0 300.872 3.12135 -2 3 2 0 300.872 3.12135 1 5 2 0 607.748 5.89945 -2 5 2 0 607.748 5.89945 1 6 2 0 974.923 9.37761 -2 6 2 0 974.923 9.37761 1 7 2 0 1380.99 13.5443 -2 7 2 0 1380.99 13.5443 1 8 2 0 76.3851 2.36416 -2 8 2 0 76.3851 2.36416 1 9 2 0 1141.04 13.4527 -2 9 2 0 1141.04 13.4527 1 10 2 0 164.664 4.34352 -2 10 2 0 164.664 4.34352 1 11 2 0 28.0626 2.45477 -2 11 2 0 28.0626 2.45477 1 12 2 0 67.2425 4.33826 -2 12 2 0 67.2425 4.33826 1 13 2 0 492.841 10.7672 -2 13 2 0 492.841 10.7672 1 14 2 0 77.9948 6.17785 -2 14 2 0 77.9948 6.17785 1 0 3 0 0.70036 0.32940 -2 0 3 0 0.70036 0.32940 1 1 3 0 1497.15 11.1710 -2 1 3 0 1497.15 11.1710 1 2 3 0 617.294 4.69755 -2 2 3 0 617.294 4.69755 1 4 3 0 1742.81 13.0580 -2 4 3 0 1742.81 13.0580 1 5 3 0 1007.59 8.90762 -2 5 3 0 1007.59 8.90762 1 6 3 0 333.535 4.62831 -2 6 3 0 333.535 4.62831 1 7 3 0 14.8993 1.15393 -2 7 3 0 14.8993 1.15393 1 8 3 0 3.37308 1.03100 -2 8 3 0 3.37308 1.03100 1 9 3 0 982.877 11.2675 -2 9 3 0 982.877 11.2675 1 10 3 0 70.3080 3.13755 -2 10 3 0 70.3080 3.13755 1 11 3 0 283.799 6.06912 -2 11 3 0 283.799 6.06912 1 12 3 0 188.646 6.18418 -2 12 3 0 188.646 6.18418 1 13 3 0 31.6150 3.25999 -2 13 3 0 31.6150 3.25999 1 2 4 0 72.9550 0.96233 -2 2 4 0 72.9550 0.96233 1 4 4 0 435.927 4.20861 -2 4 4 0 435.927 4.20861 1 5 4 0 2706.64 19.7461 -2 5 4 0 2706.64 19.7461 1 6 4 0 5453.05 38.1606 -2 6 4 0 5453.05 38.1606 1 7 4 0 3456.16 27.9835 -2 7 4 0 3456.16 27.9835 1 8 4 0 52.8743 1.96853 -2 8 4 0 52.8743 1.96853 1 9 4 0 2749.77 23.6041 -2 9 4 0 2749.77 23.6041 1 10 4 0 2.86575 1.51895 -2 10 4 0 2.86575 1.51895 1 11 4 0 632.058 9.64850 -2 11 4 0 632.058 9.64850 1 12 4 0 16.3411 2.66101 -2 12 4 0 16.3411 2.66101 1 13 4 0 -4.0818 2.91516 -2 13 4 0 -4.0818 2.91516 1 0 5 0 6.18931 0.38710 -2 0 5 0 6.18931 0.38710 1 1 5 0 126.281 1.37895 -2 1 5 0 126.281 1.37895 1 2 5 0 1069.13 26.2300 -2 2 5 0 1069.13 26.2300 1 3 5 0 2097.93 14.2414 -2 3 5 0 2097.93 14.2414 1 4 5 0 1702.82 13.4530 -2 4 5 0 1702.82 13.4530 1 5 5 0 1430.85 11.8312 -2 5 5 0 1430.85 11.8312 1 6 5 0 29.8972 1.12924 -2 6 5 0 29.8972 1.12924 1 7 5 0 1640.14 15.6610 -2 7 5 0 1640.14 15.6610 1 8 5 0 1187.09 11.7254 -2 8 5 0 1187.09 11.7254 1 9 5 0 3951.87 32.2148 -2 9 5 0 3951.87 32.2148 1 10 5 0 91.5133 3.25724 -2 10 5 0 91.5133 3.25724 1 11 5 0 305.925 6.70418 -2 11 5 0 305.925 6.70418 1 12 5 0 18.0254 2.66816 -2 12 5 0 18.0254 2.66816 1 13 5 0 8.36911 3.18955 -2 13 5 0 8.36911 3.18955 1 3 6 0 3785.08 23.8563 -2 3 6 0 3785.08 23.8563 1 4 6 0 243.519 3.52510 -2 4 6 0 243.519 3.52510 1 5 6 0 430.172 4.44316 -2 5 6 0 430.172 4.44316 1 6 6 0 62.3370 1.54846 -2 6 6 0 62.3370 1.54846 1 7 6 0 132.010 2.99306 -2 7 6 0 132.010 2.99306 1 8 6 0 1577.52 14.6389 -2 8 6 0 1577.52 14.6389 1 9 6 0 13.0013 1.48833 -2 9 6 0 13.0013 1.48833 1 10 6 0 1394.03 14.9181 -2 10 6 0 1394.03 14.9181 1 11 6 0 11.3347 2.27434 -2 11 6 0 11.3347 2.27434 1 12 6 0 56.4133 4.04362 -2 12 6 0 56.4133 4.04362 1 13 6 0 384.163 10.4187 -2 13 6 0 384.163 10.4187 1 0 7 0 14.7095 0.61463 -2 0 7 0 14.7095 0.61463 1 1 7 0 5991.78 144.026 -2 1 7 0 5991.78 144.026 1 2 7 0 764.950 5.90274 -2 2 7 0 764.950 5.90274 1 3 7 0 2808.05 17.9592 -2 3 7 0 2808.05 17.9592 1 4 7 0 43.1861 1.08367 -2 4 7 0 43.1861 1.08367 1 5 7 0 1991.23 16.7242 -2 5 7 0 1991.23 16.7242 1 6 7 0 1.90225 0.59207 -2 6 7 0 1.90225 0.59207 1 7 7 0 3148.18 23.3434 -2 7 7 0 3148.18 23.3434 1 8 7 0 1369.89 12.4246 -2 8 7 0 1369.89 12.4246 1 9 7 0 260.763 5.07790 -2 9 7 0 260.763 5.07790 1 10 7 0 64.5871 2.89231 -2 10 7 0 64.5871 2.89231 1 11 7 0 297.167 8.25936 -2 11 7 0 297.167 8.25936 1 12 7 0 489.069 10.0556 -2 12 7 0 489.069 10.0556 1 13 7 0 2.89594 2.66955 -2 13 7 0 2.89594 2.66955 1 0 8 0 573.916 8.12400 -2 0 8 0 573.916 8.12400 1 2 8 0 2118.35 13.9012 -2 2 8 0 2118.35 13.9012 1 3 8 0 4514.04 32.1413 -2 3 8 0 4514.04 32.1413 1 4 8 0 1507.48 10.9710 -2 4 8 0 1507.48 10.9710 1 5 8 0 440.917 4.79937 -2 5 8 0 440.917 4.79937 1 6 8 0 1692.50 14.0801 -2 6 8 0 1692.50 14.0801 1 7 8 0 716.051 7.05219 -2 7 8 0 716.051 7.05219 1 8 8 0 1209.75 12.7610 -2 8 8 0 1209.75 12.7610 1 9 8 0 1033.14 11.5264 -2 9 8 0 1033.14 11.5264 1 10 8 0 100.184 3.30115 -2 10 8 0 100.184 3.30115 1 11 8 0 5.09640 1.48825 -2 11 8 0 5.09640 1.48825 1 12 8 0 249.615 7.54271 -2 12 8 0 249.615 7.54271 1 13 8 0 28.3688 4.13229 -2 13 8 0 28.3688 4.13229 1 0 9 0 7.50684 0.52391 -2 0 9 0 7.50684 0.52391 1 1 9 0 69.1247 1.26209 -2 1 9 0 69.1247 1.26209 1 2 9 0 837.974 6.62953 -2 2 9 0 837.974 6.62953 1 3 9 0 8066.68 58.9435 -2 3 9 0 8066.68 58.9435 1 4 9 0 626.208 4.98515 -2 4 9 0 626.208 4.98515 1 5 9 0 180.108 2.57504 -2 5 9 0 180.108 2.57504 1 6 9 0 484.466 5.42148 -2 6 9 0 484.466 5.42148 1 7 9 0 862.862 8.97644 -2 7 9 0 862.862 8.97644 1 8 9 0 1194.78 11.1864 -2 8 9 0 1194.78 11.1864 1 9 9 0 34.8042 2.08526 -2 9 9 0 34.8042 2.08526 1 10 9 0 1044.33 12.7663 -2 10 9 0 1044.33 12.7663 1 11 9 0 61.8474 2.82884 -2 11 9 0 61.8474 2.82884 1 12 9 0 24.4002 2.72655 -2 12 9 0 24.4002 2.72655 1 13 9 0 17.6043 5.08467 -2 13 9 0 17.6043 5.08467 1 0 10 0 2173.44 32.8033 -2 0 10 0 2173.44 32.8033 1 1 10 0 4670.75 37.6024 -2 1 10 0 4670.75 37.6024 1 2 10 0 316.416 3.07302 -2 2 10 0 316.416 3.07302 1 3 10 0 100.126 1.43543 -2 3 10 0 100.126 1.43543 1 4 10 0 116.539 1.63788 -2 4 10 0 116.539 1.63788 1 5 10 0 2229.18 16.6920 -2 5 10 0 2229.18 16.6920 1 6 10 0 385.676 4.42818 -2 6 10 0 385.676 4.42818 1 7 10 0 615.898 8.01755 -2 7 10 0 615.898 8.01755 1 8 10 0 199.966 4.14755 -2 8 10 0 199.966 4.14755 1 9 10 0 1506.52 16.2485 -2 9 10 0 1506.52 16.2485 1 10 10 0 527.752 8.04545 -2 10 10 0 527.752 8.04545 1 11 10 0 36.0736 2.31696 -2 11 10 0 36.0736 2.31696 1 12 10 0 196.666 5.08374 -2 12 10 0 196.666 5.08374 1 13 10 0 76.1823 7.22890 -2 13 10 0 76.1823 7.22890 1 0 11 0 67.8431 3.04047 -2 0 11 0 67.8431 3.04047 1 1 11 0 4936.29 45.4876 -2 1 11 0 4936.29 45.4876 1 2 11 0 2066.72 15.0244 -2 2 11 0 2066.72 15.0244 1 3 11 0 3545.79 21.8422 -2 3 11 0 3545.79 21.8422 1 4 11 0 1038.54 8.03786 -2 4 11 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655.162 24.2058 -2 5 8 4 655.162 24.2058 1 -7 8 4 -3.3569 4.07963 -2 6 8 4 -3.3569 4.07963 1 -8 8 4 1005.96 33.9772 -2 7 8 4 1005.96 33.9772 1 8 8 4 8.85287 1.04892 1 -10 8 4 314.501 18.7703 -2 9 8 4 314.501 18.7703 1 -11 8 4 196.030 16.8301 -2 10 8 4 196.030 16.8301 1 11 8 4 6.65525 2.06334 1 -12 9 4 552.319 10.5184 1 -11 9 4 30.8488 2.28285 1 -10 9 4 119.351 3.77641 1 -9 9 4 10.5728 1.17235 1 -8 9 4 71.2652 2.85021 1 -7 9 4 642.689 7.77656 1 -6 9 4 15.4397 1.23474 1 -5 9 4 151.121 2.74016 1 -4 9 4 129.230 2.42280 1 -3 9 4 6.55903 0.69722 1 -2 9 4 486.839 5.00209 1 -1 9 4 169.352 2.56630 1 0 9 4 1417.46 10.4263 1 1 9 4 523.183 4.93248 1 2 9 4 38.9464 1.33830 1 3 9 4 351.001 4.36856 1 4 9 4 1684.37 12.3065 1 5 9 4 13.2355 1.01008 1 -7 9 4 365.618 14.9575 -2 6 9 4 365.618 14.9575 1 7 9 4 319.003 4.79931 1 8 9 4 34.0037 1.78793 1 -10 9 4 905.186 33.6702 -2 9 9 4 905.186 33.6702 1 -11 9 4 58.9157 11.8071 -2 10 9 4 58.9157 11.8071 1 -12 9 4 316.643 15.2538 -2 11 9 4 316.643 15.2538 1 -12 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-2 -7 8 9 19.4532 3.63017 1 3 8 9 24.2194 3.64291 -2 -6 8 9 24.2194 3.64291 1 2 8 9 526.729 9.80519 -2 -5 8 9 526.729 9.80519 1 1 8 9 195.175 5.75755 -2 -4 8 9 195.175 5.75755 1 0 8 9 113.180 4.76482 -2 -3 8 9 113.180 4.76482 1 -1 8 9 186.165 4.79883 -2 -2 8 9 186.165 4.79883 1 -2 8 9 240.792 5.56953 -2 -1 8 9 240.792 5.56953 1 -3 8 9 226.450 5.24515 -2 0 8 9 226.450 5.24515 1 -4 8 9 197.590 6.68065 -2 1 8 9 197.590 6.68065 1 -5 8 9 608.688 11.1343 -2 2 8 9 608.688 11.1343 1 -6 8 9 49.8092 4.75799 -2 3 8 9 49.8092 4.75799 1 -7 8 9 14.4822 4.40604 -2 4 8 9 14.4822 4.40604 1 -8 8 9 1208.29 24.9829 -2 5 8 9 1208.29 24.9829 1 6 8 9 189.863 11.0335 1 5 9 9 10.1789 4.69314 -2 -8 9 9 10.1789 4.69314 1 4 9 9 406.979 10.1003 -2 -7 9 9 406.979 10.1003 1 3 9 9 115.950 5.50036 -2 -6 9 9 115.950 5.50036 1 2 9 9 154.001 5.18127 -2 -5 9 9 154.001 5.18127 1 1 9 9 65.9431 3.53302 -2 -4 9 9 65.9431 3.53302 1 0 9 9 326.017 6.87694 -2 -3 9 9 326.017 6.87694 1 -1 9 9 54.2537 3.07212 -2 -2 9 9 54.2537 3.07212 1 -2 9 9 68.4021 3.10841 -2 -1 9 9 68.4021 3.10841 1 -3 9 9 472.152 7.64296 -2 0 9 9 472.152 7.64296 1 -4 9 9 123.793 5.68956 -2 1 9 9 123.793 5.68956 1 -5 9 9 265.189 7.88399 -2 2 9 9 265.189 7.88399 1 -6 9 9 201.784 8.86431 -2 3 9 9 201.784 8.86431 1 -7 9 9 288.320 8.19324 -2 4 9 9 288.320 8.19324 1 -8 9 9 0.22618 5.19418 -2 5 9 9 0.22618 5.19418 1 5 10 9 551.001 16.3681 -2 -8 10 9 551.001 16.3681 1 4 10 9 49.5733 4.99501 -2 -7 10 9 49.5733 4.99501 1 3 10 9 29.7412 4.36528 -2 -6 10 9 29.7412 4.36528 1 2 10 9 275.493 7.34136 -2 -5 10 9 275.493 7.34136 1 1 10 9 249.232 5.97249 -2 -4 10 9 249.232 5.97249 1 0 10 9 374.986 7.39801 -2 -3 10 9 374.986 7.39801 1 -1 10 9 93.3858 3.79730 -2 -2 10 9 93.3858 3.79730 1 -2 10 9 163.431 4.44665 -2 -1 10 9 163.431 4.44665 1 -3 10 9 625.597 8.64272 -2 0 10 9 625.597 8.64272 1 -4 10 9 437.686 10.1581 -2 1 10 9 437.686 10.1581 1 -5 10 9 524.272 14.2323 -2 2 10 9 524.272 14.2323 1 -6 10 9 28.7867 4.07708 -2 3 10 9 28.7867 4.07708 1 -7 10 9 91.2198 6.08733 -2 4 10 9 91.2198 6.08733 1 -8 10 9 353.057 19.7860 -2 5 10 9 353.057 19.7860 1 4 11 9 30.6377 5.40772 -2 -7 11 9 30.6377 5.40772 1 3 11 9 237.146 7.85723 -2 -6 11 9 237.146 7.85723 1 2 11 9 61.1689 5.99372 -2 -5 11 9 61.1689 5.99372 1 1 11 9 122.579 5.48524 -2 -4 11 9 122.579 5.48524 1 0 11 9 97.4123 4.32971 -2 -3 11 9 97.4123 4.32971 1 -1 11 9 262.204 6.02710 -2 -2 11 9 262.204 6.02710 1 -2 11 9 167.855 4.34840 -2 -1 11 9 167.855 4.34840 1 -3 11 9 76.2256 4.31790 -2 0 11 9 76.2256 4.31790 1 -4 11 9 86.0904 5.13591 -2 1 11 9 86.0904 5.13591 1 -5 11 9 30.6231 4.09202 -2 2 11 9 30.6231 4.09202 1 -6 11 9 123.414 5.83157 -2 3 11 9 123.414 5.83157 1 -7 11 9 72.7707 11.4989 -2 4 11 9 72.7707 11.4989 1 5 11 9 81.5434 7.85898 1 4 12 9 253.959 13.2909 -2 -7 12 9 253.959 13.2909 1 3 12 9 519.423 11.3844 -2 -6 12 9 519.423 11.3844 1 2 12 9 402.483 9.72363 -2 -5 12 9 402.483 9.72363 1 1 12 9 81.1074 4.37337 -2 -4 12 9 81.1074 4.37337 1 0 12 9 79.9153 4.63021 -2 -3 12 9 79.9153 4.63021 1 -1 12 9 82.4647 4.75931 -2 -2 12 9 82.4647 4.75931 1 -2 12 9 90.2232 3.87992 -2 -1 12 9 90.2232 3.87992 1 -3 12 9 68.4473 5.60171 -2 0 12 9 68.4473 5.60171 1 -4 12 9 68.3227 5.07680 -2 1 12 9 68.3227 5.07680 1 -5 12 9 752.305 18.2550 -2 2 12 9 752.305 18.2550 1 -6 12 9 831.932 19.4970 -2 3 12 9 831.932 19.4970 1 -7 12 9 274.627 12.4998 -2 4 12 9 274.627 12.4998 1 3 13 9 -0.7808 6.11166 -2 -6 13 9 -0.7808 6.11166 1 2 13 9 194.446 6.80418 -2 -5 13 9 194.446 6.80418 1 1 13 9 131.690 6.53844 -2 -4 13 9 131.690 6.53844 1 0 13 9 84.5689 3.98699 -2 -3 13 9 84.5689 3.98699 1 -1 13 9 27.3152 2.91165 -2 -2 13 9 27.3152 2.91165 1 -2 13 9 29.4825 2.89129 -2 -1 13 9 29.4825 2.89129 1 -3 13 9 156.711 6.22609 -2 0 13 9 156.711 6.22609 1 -4 13 9 163.520 8.11373 -2 1 13 9 163.520 8.11373 1 -5 13 9 183.049 8.55934 -2 2 13 9 183.049 8.55934 1 -6 13 9 -5.7113 5.54110 -2 3 13 9 -5.7113 5.54110 1 3 14 9 95.5678 13.2241 -2 -6 14 9 95.5678 13.2241 1 2 14 9 518.757 14.7470 -2 -5 14 9 518.757 14.7470 1 1 14 9 108.561 5.42815 -2 -4 14 9 108.561 5.42815 1 0 14 9 118.208 5.63987 -2 -3 14 9 118.208 5.63987 1 -1 14 9 118.698 6.09287 -2 -2 14 9 118.698 6.09287 1 -2 14 9 86.5215 4.50951 -2 -1 14 9 86.5215 4.50951 1 -3 14 9 160.073 10.7860 -2 0 14 9 160.073 10.7860 1 -4 14 9 75.7202 6.42640 -2 1 14 9 75.7202 6.42640 1 -5 14 9 314.938 19.0214 -2 2 14 9 314.938 19.0214 1 2 15 9 249.187 18.9760 -2 -5 15 9 249.187 18.9760 1 1 15 9 339.583 13.6216 -2 -4 15 9 339.583 13.6216 1 0 15 9 455.244 13.1385 -2 -3 15 9 455.244 13.1385 1 -1 15 9 207.942 11.5961 -2 -2 15 9 207.942 11.5961 1 -2 15 9 138.506 6.84193 -2 -1 15 9 138.506 6.84193 1 -3 15 9 531.602 26.2555 -2 0 15 9 531.602 26.2555 1 -4 15 9 250.211 17.3923 -2 1 15 9 250.211 17.3923 1 0 16 9 325.494 13.1117 -2 -3 16 9 325.494 13.1117 1 -1 16 9 84.7424 7.54142 -2 -2 16 9 84.7424 7.54142 1 5 0 10 83.0642 10.8974 -2 -8 0 10 83.0642 10.8974 1 4 0 10 216.099 9.81774 -2 -7 0 10 216.099 9.81774 1 3 0 10 576.046 19.0322 -2 -6 0 10 576.046 19.0322 1 2 0 10 124.405 9.17840 -2 -5 0 10 124.405 9.17840 1 1 0 10 314.643 11.3377 -2 -4 0 10 314.643 11.3377 1 0 0 10 232.232 11.8969 -2 -3 0 10 232.232 11.8969 1 -1 0 10 180.795 8.69308 -2 -2 0 10 180.795 8.69308 1 -2 0 10 231.139 12.1129 -2 -1 0 10 231.139 12.1129 1 -3 0 10 424.041 16.2550 -2 0 0 10 424.041 16.2550 1 -4 0 10 253.640 17.8729 -2 1 0 10 253.640 17.8729 1 -5 0 10 219.644 12.2751 -2 2 0 10 219.644 12.2751 1 -6 0 10 961.333 27.4228 -2 3 0 10 961.333 27.4228 1 -7 0 10 310.153 20.8831 -2 4 0 10 310.153 20.8831 1 5 1 10 285.420 22.3379 -2 -8 1 10 285.420 22.3379 1 4 1 10 102.410 5.37234 -2 -7 1 10 102.410 5.37234 1 3 1 10 665.872 14.7126 -2 -6 1 10 665.872 14.7126 1 2 1 10 88.1812 5.77101 -2 -5 1 10 88.1812 5.77101 1 1 1 10 162.739 7.07731 -2 -4 1 10 162.739 7.07731 1 0 1 10 103.852 5.98734 -2 -3 1 10 103.852 5.98734 1 -1 1 10 51.1790 4.93196 -2 -2 1 10 51.1790 4.93196 1 -2 1 10 55.5571 5.22756 -2 -1 1 10 55.5571 5.22756 1 -3 1 10 60.0692 5.23017 -2 0 1 10 60.0692 5.23017 1 -4 1 10 78.6037 7.90556 -2 1 1 10 78.6037 7.90556 1 -5 1 10 136.086 7.12488 -2 2 1 10 136.086 7.12488 1 -6 1 10 605.123 16.3531 -2 3 1 10 605.123 16.3531 1 -7 1 10 40.4563 5.34359 -2 4 1 10 40.4563 5.34359 1 -8 1 10 420.460 17.3280 -2 5 1 10 420.460 17.3280 1 -8 2 10 308.759 9.10727 1 4 2 10 150.111 6.40409 -2 -7 2 10 150.111 6.40409 1 3 2 10 110.188 6.25989 -2 -6 2 10 110.188 6.25989 1 2 2 10 424.805 11.4605 -2 -5 2 10 424.805 11.4605 1 1 2 10 2.66986 3.86516 -2 -4 2 10 2.66986 3.86516 1 0 2 10 8.74502 4.52225 -2 -3 2 10 8.74502 4.52225 1 -1 2 10 56.6958 5.19551 -2 -2 2 10 56.6958 5.19551 1 -2 2 10 96.3612 5.42271 -2 -1 2 10 96.3612 5.42271 1 -3 2 10 11.6155 4.12029 -2 0 2 10 11.6155 4.12029 1 -4 2 10 -0.3768 7.39753 -2 1 2 10 -0.3768 7.39753 1 -5 2 10 244.327 9.68517 -2 2 2 10 244.327 9.68517 1 -6 2 10 136.566 7.42644 -2 3 2 10 136.566 7.42644 1 -7 2 10 115.805 7.81140 -2 4 2 10 115.805 7.81140 1 -8 2 10 173.871 15.2898 -2 5 2 10 173.871 15.2898 1 -8 3 10 1.32086 1.95032 1 4 3 10 134.516 6.88633 -2 -7 3 10 134.516 6.88633 1 3 3 10 166.660 7.30395 -2 -6 3 10 166.660 7.30395 1 2 3 10 308.566 11.1670 -2 -5 3 10 308.566 11.1670 1 1 3 10 289.632 8.54012 -2 -4 3 10 289.632 8.54012 1 0 3 10 240.194 12.2112 -2 -3 3 10 240.194 12.2112 1 -1 3 10 85.9776 6.72567 -2 -2 3 10 85.9776 6.72567 1 -2 3 10 175.755 6.84362 -2 -1 3 10 175.755 6.84362 1 -3 3 10 459.991 13.9862 -2 0 3 10 459.991 13.9862 1 -4 3 10 195.803 8.85812 -2 1 3 10 195.803 8.85812 1 -5 3 10 180.332 7.48019 -2 2 3 10 180.332 7.48019 1 -6 3 10 157.153 7.56746 -2 3 3 10 157.153 7.56746 1 -7 3 10 279.722 11.6523 -2 4 3 10 279.722 11.6523 1 4 4 10 500.056 18.5952 -2 -7 4 10 500.056 18.5952 1 3 4 10 61.5881 8.68820 -2 -6 4 10 61.5881 8.68820 1 2 4 10 266.002 9.18852 -2 -5 4 10 266.002 9.18852 1 1 4 10 814.321 14.9013 -2 -4 4 10 814.321 14.9013 1 0 4 10 21.9404 5.95437 -2 -3 4 10 21.9404 5.95437 1 -1 4 10 51.8376 10.5492 -2 -2 4 10 51.8376 10.5492 1 -2 4 10 105.299 7.39795 -2 -1 4 10 105.299 7.39795 1 -3 4 10 10.9076 4.90406 -2 0 4 10 10.9076 4.90406 1 -4 4 10 565.730 13.2351 -2 1 4 10 565.730 13.2351 1 -5 4 10 159.813 7.28933 -2 2 4 10 159.813 7.28933 1 -6 4 10 21.5851 5.27550 -2 3 4 10 21.5851 5.27550 1 -7 4 10 277.935 9.10874 -2 4 4 10 277.935 9.10874 1 4 5 10 156.368 8.33877 -2 -7 5 10 156.368 8.33877 1 3 5 10 707.978 32.6109 -2 -6 5 10 707.978 32.6109 1 2 5 10 989.840 28.1124 -2 -5 5 10 989.840 28.1124 1 1 5 10 19.6253 4.80961 -2 -4 5 10 19.6253 4.80961 1 0 5 10 322.453 11.3194 -2 -3 5 10 322.453 11.3194 1 -1 5 10 395.556 15.8261 -2 -2 5 10 395.556 15.8261 1 -2 5 10 672.994 21.1339 -2 -1 5 10 672.994 21.1339 1 -3 5 10 310.933 9.92886 -2 0 5 10 310.933 9.92886 1 -4 5 10 35.2642 4.86964 -2 1 5 10 35.2642 4.86964 1 -5 5 10 576.907 15.0469 -2 2 5 10 576.907 15.0469 1 -6 5 10 449.606 13.1655 -2 3 5 10 449.606 13.1655 1 -7 5 10 299.916 10.4459 -2 4 5 10 299.916 10.4459 1 4 6 10 126.292 7.52545 -2 -7 6 10 126.292 7.52545 1 3 6 10 178.698 13.5633 -2 -6 6 10 178.698 13.5633 1 2 6 10 712.844 15.3682 -2 -5 6 10 712.844 15.3682 1 1 6 10 83.1477 8.62831 -2 -4 6 10 83.1477 8.62831 1 0 6 10 647.733 30.2336 -2 -3 6 10 647.733 30.2336 1 -1 6 10 228.428 18.0948 -2 -2 6 10 228.428 18.0948 1 -2 6 10 151.615 10.0803 -2 -1 6 10 151.615 10.0803 1 -3 6 10 334.377 14.4796 -2 0 6 10 334.377 14.4796 1 -4 6 10 89.9278 7.15064 -2 1 6 10 89.9278 7.15064 1 -5 6 10 938.883 21.2657 -2 2 6 10 938.883 21.2657 1 -6 6 10 311.810 10.5349 -2 3 6 10 311.810 10.5349 1 -7 6 10 85.0200 7.14482 -2 4 6 10 85.0200 7.14482 1 -7 7 10 23.9182 2.86343 1 -6 7 10 367.179 12.7725 1 2 7 10 23.3296 7.65419 -2 -5 7 10 23.3296 7.65419 1 1 7 10 623.020 20.7655 -2 -4 7 10 623.020 20.7655 1 0 7 10 222.995 11.9345 -2 -3 7 10 222.995 11.9345 1 -1 7 10 258.433 18.6121 -2 -2 7 10 258.433 18.6121 1 -2 7 10 254.898 17.9957 -2 -1 7 10 254.898 17.9957 1 -3 7 10 386.819 12.5485 -2 0 7 10 386.819 12.5485 1 -4 7 10 468.575 14.2104 -2 1 7 10 468.575 14.2104 1 -5 7 10 38.0204 6.30314 -2 2 7 10 38.0204 6.30314 1 -6 7 10 599.108 16.5217 -2 3 7 10 599.108 16.5217 1 -6 8 10 258.350 13.0218 1 2 8 10 244.305 19.4526 -2 -5 8 10 244.305 19.4526 1 1 8 10 324.614 11.6876 -2 -4 8 10 324.614 11.6876 1 0 8 10 91.0462 6.99490 -2 -3 8 10 91.0462 6.99490 1 -1 8 10 41.6471 5.75817 -2 -2 8 10 41.6471 5.75817 1 -2 8 10 54.9336 7.49427 -2 -1 8 10 54.9336 7.49427 1 -3 8 10 156.527 6.61990 -2 0 8 10 156.527 6.61990 1 -4 8 10 498.298 11.7547 -2 1 8 10 498.298 11.7547 1 -5 8 10 403.305 11.9230 -2 2 8 10 403.305 11.9230 1 -6 8 10 179.024 11.1498 -2 3 8 10 179.024 11.1498 1 3 9 10 1018.49 40.8026 -2 -6 9 10 1018.49 40.8026 1 2 9 10 991.771 28.1746 -2 -5 9 10 991.771 28.1746 1 1 9 10 28.0220 5.69972 -2 -4 9 10 28.0220 5.69972 1 0 9 10 345.278 12.0070 -2 -3 9 10 345.278 12.0070 1 -1 9 10 300.699 11.2332 -2 -2 9 10 300.699 11.2332 1 -2 9 10 351.686 9.67153 -2 -1 9 10 351.686 9.67153 1 -3 9 10 585.376 11.3204 -2 0 9 10 585.376 11.3204 1 -4 9 10 35.8467 4.64940 -2 1 9 10 35.8467 4.64940 1 -5 9 10 779.575 18.8563 -2 2 9 10 779.575 18.8563 1 2 10 10 132.271 11.0084 -2 -5 10 10 132.271 11.0084 1 1 10 10 254.689 11.3638 -2 -4 10 10 254.689 11.3638 1 0 10 10 57.1417 6.88399 -2 -3 10 10 57.1417 6.88399 1 -1 10 10 343.752 10.8654 -2 -2 10 10 343.752 10.8654 1 -2 10 10 198.798 7.30227 -2 -1 10 10 198.798 7.30227 1 -3 10 10 57.1410 5.45941 -2 0 10 10 57.1410 5.45941 1 -4 10 10 146.539 13.3883 -2 1 10 10 146.539 13.3883 1 -5 10 10 112.274 12.5120 -2 2 10 10 112.274 12.5120 1 -5 11 10 677.438 22.3668 1 1 11 10 161.754 11.9390 -2 -4 11 10 161.754 11.9390 1 0 11 10 264.252 19.0569 -2 -3 11 10 264.252 19.0569 1 -1 11 10 474.002 12.6813 -2 -2 11 10 474.002 12.6813 1 -2 11 10 273.879 9.01678 -2 -1 11 10 273.879 9.01678 1 -3 11 10 276.473 18.0312 -2 0 11 10 276.473 18.0312 1 -4 11 10 298.646 19.2507 -2 1 11 10 298.646 19.2507 1 -4 12 10 63.3763 11.2354 1 0 12 10 57.2145 8.61346 -2 -3 12 10 57.2145 8.61346 1 -1 12 10 84.3336 9.47174 -2 -2 12 10 84.3336 9.47174 1 -2 12 10 36.2020 6.46887 -2 -1 12 10 36.2020 6.46887 1 -3 12 10 87.7929 9.14747 -2 0 12 10 87.7929 9.14747 1 -5 0 11 -0.8634 3.48472 1 -4 0 11 -1.2526 2.03563 1 -3 0 11 -3.8347 1.98008 1 -2 0 11 3.15703 2.17105 1 -1 0 11 -0.5107 1.85093 1 0 0 11 3.47345 2.11599 1 1 0 11 -2.7688 3.40902 1 -5 1 11 72.3775 5.07552 1 -4 1 11 74.0207 4.24748 1 -3 1 11 606.461 10.7658 1 -2 1 11 29.3928 2.93722 1 -1 1 11 298.002 6.57872 1 0 1 11 4.47054 1.59275 1 1 1 11 32.8104 3.57511 1 -4 2 11 9.69633 2.27295 1 -3 2 11 483.806 9.75616 1 -2 2 11 -0.4763 1.49110 1 -1 2 11 408.357 7.63685 1 0 2 11 59.2205 3.30043 1 1 2 11 35.8261 3.74619 1 -4 3 11 50.5536 3.52934 1 -3 3 11 1.69297 1.71498 1 -2 3 11 325.929 7.03616 1 -1 3 11 53.0476 3.21079 1 0 3 11 3.79031 1.56763 1 1 3 11 59.2870 4.91983 1 -4 4 11 319.623 7.73640 1 -3 4 11 5.12800 1.86850 1 -2 4 11 185.537 5.23970 1 -1 4 11 276.923 6.36743 1 0 4 11 291.471 7.04302 1 1 4 11 224.552 12.8509 1 -3 5 11 47.9879 3.45583 1 -2 5 11 127.101 4.39765 1 -1 5 11 139.367 4.99304 1 0 5 11 71.4210 3.86577 1 -3 6 11 6.13874 2.03285 1 -2 6 11 273.907 7.04749 1 -1 6 11 92.8668 4.63949 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 13220 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 800' _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a MITIGEN holder oil' _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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.21297(7) 0.70542(4) 0.52326(10) 0.02192(16) Uani 1 1 d . . . . . N1 N 0.39703(7) 0.64863(4) 0.46432(10) 0.01319(15) Uani 1 1 d . . . . . N2 N 0.73014(8) 0.66395(4) 0.85255(10) 0.01737(17) Uani 1 1 d . . . . . C1 C 0.26591(9) 0.66906(5) 0.42728(12) 0.01629(18) Uani 1 1 d . . . . . C2 C 0.20209(9) 0.64405(5) 0.27096(13) 0.02008(19) Uani 1 1 d . . . . . H2 H 0.113108 0.656648 0.235748 0.024 Uiso 1 1 calc R . . . . C3 C 0.26491(10) 0.60307(5) 0.17228(13) 0.02017(19) Uani 1 1 d . . . . . H3 H 0.219100 0.587851 0.070192 0.024 Uiso 1 1 calc R . . . . C4 C 0.39763(9) 0.58263(5) 0.21909(12) 0.01686(18) Uani 1 1 d . . . . . H4 H 0.440990 0.553049 0.151738 0.020 Uiso 1 1 calc R . . . . C5 C 0.46074(9) 0.60719(4) 0.36499(11) 0.01332(16) Uani 1 1 d . . . . . C6 C 0.59682(9) 0.59898(4) 0.44310(11) 0.01273(16) Uani 1 1 d . . . . . C7 C 0.69491(9) 0.55839(4) 0.36774(11) 0.01386(17) Uani 1 1 d . . . . . C8 C 0.76796(9) 0.50844(4) 0.46013(12) 0.01522(17) Uani 1 1 d . . . . . H8 H 0.752650 0.499819 0.570641 0.018 Uiso 1 1 calc R . . . . C9 C 0.86288(9) 0.47130(5) 0.39131(13) 0.01770(18) Uani 1 1 d . . . . . H9 H 0.912039 0.437411 0.454846 0.021 Uiso 1 1 calc R . . . . C10 C 0.88599(10) 0.48363(5) 0.22989(14) 0.0205(2) Uani 1 1 d . . . . . H10 H 0.951528 0.458578 0.183341 0.025 Uiso 1 1 calc R . . . . C11 C 0.81295(11) 0.53273(5) 0.13675(13) 0.0215(2) Uani 1 1 d . . . . . H11 H 0.828463 0.541083 0.026187 0.026 Uiso 1 1 calc R . . . . C12 C 0.71714(10) 0.56977(5) 0.20458(12) 0.01794(18) Uani 1 1 d . . . . . H12 H 0.666741 0.602862 0.139741 0.022 Uiso 1 1 calc R . . . . C13 C 0.61311(8) 0.63455(4) 0.58633(11) 0.01224(16) Uani 1 1 d . . . . . C14 C 0.48313(8) 0.66649(4) 0.61975(11) 0.01258(16) Uani 1 1 d . . . . . C15 C 0.42742(9) 0.63345(5) 0.76678(12) 0.01610(17) Uani 1 1 d . . . . . H15A H 0.342165 0.654080 0.780224 0.024 Uiso 1 1 calc GR . . . . H15B H 0.489239 0.640324 0.867675 0.024 Uiso 1 1 calc GR . . . . H15C H 0.415352 0.584872 0.746149 0.024 Uiso 1 1 calc GR . . . . C16 C 0.49657(9) 0.74336(5) 0.63858(12) 0.01645(17) Uani 1 1 d . . . . . H16A H 0.534815 0.761979 0.544027 0.025 Uiso 1 1 calc GR . . . . H16B H 0.554268 0.753936 0.740870 0.025 Uiso 1 1 calc GR . . . . H16C H 0.409215 0.763337 0.642891 0.025 Uiso 1 1 calc GR . . . . C17 C 0.73795(9) 0.65073(4) 0.69168(11) 0.01317(16) Uani 1 1 d . . . . . C18 C 0.85619(9) 0.65803(5) 0.62358(12) 0.01631(18) Uani 1 1 d . . . . . H18 H 0.859550 0.647815 0.510400 0.020 Uiso 1 1 calc R . . . . C19 C 0.96863(9) 0.68036(5) 0.72307(13) 0.01901(19) Uani 1 1 d . . . . . H19 H 1.049646 0.685791 0.678844 0.023 Uiso 1 1 calc R . . . . C20 C 0.96066(10) 0.69457(5) 0.88784(13) 0.01965(19) Uani 1 1 d . . . . . H20 H 1.035465 0.710340 0.958915 0.024 Uiso 1 1 calc R . . . . C21 C 0.83996(10) 0.68504(5) 0.94578(12) 0.0201(2) Uani 1 1 d . . . . . H21 H 0.835016 0.694097 1.059185 0.024 Uiso 1 1 calc R . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0158(3) 0.0272(4) 0.0231(4) 0.0003(3) 0.0040(3) 0.0062(3) N1 0.0119(3) 0.0151(3) 0.0123(3) -0.0002(3) 0.0007(3) 0.0005(3) N2 0.0169(4) 0.0200(4) 0.0149(4) -0.0008(3) 0.0011(3) -0.0038(3) C1 0.0126(4) 0.0187(4) 0.0175(4) 0.0034(3) 0.0018(3) 0.0011(3) C2 0.0145(4) 0.0250(5) 0.0194(5) 0.0035(4) -0.0030(3) 0.0004(3) C3 0.0196(4) 0.0234(4) 0.0159(4) 0.0008(3) -0.0037(4) -0.0033(3) C4 0.0187(4) 0.0174(4) 0.0141(4) -0.0011(3) 0.0005(3) -0.0012(3) C5 0.0144(4) 0.0129(4) 0.0127(4) 0.0009(3) 0.0020(3) -0.0004(3) C6 0.0129(4) 0.0124(4) 0.0129(4) 0.0009(3) 0.0018(3) 0.0002(3) C7 0.0140(4) 0.0122(4) 0.0154(4) -0.0022(3) 0.0019(3) -0.0005(3) C8 0.0159(4) 0.0137(4) 0.0160(4) -0.0007(3) 0.0015(3) -0.0006(3) C9 0.0156(4) 0.0136(4) 0.0233(5) -0.0017(3) 0.0003(4) 0.0018(3) C10 0.0200(4) 0.0177(4) 0.0251(5) -0.0040(4) 0.0073(4) 0.0032(3) C11 0.0268(5) 0.0213(4) 0.0179(4) -0.0012(4) 0.0087(4) 0.0040(4) C12 0.0206(4) 0.0169(4) 0.0170(4) 0.0003(3) 0.0048(4) 0.0032(3) C13 0.0118(4) 0.0128(4) 0.0121(4) 0.0015(3) 0.0014(3) 0.0001(3) C14 0.0121(4) 0.0144(4) 0.0112(4) -0.0007(3) 0.0013(3) 0.0005(3) C15 0.0150(4) 0.0202(4) 0.0134(4) 0.0009(3) 0.0032(3) -0.0019(3) C16 0.0190(4) 0.0131(4) 0.0176(4) -0.0008(3) 0.0033(3) 0.0014(3) C17 0.0128(4) 0.0116(3) 0.0148(4) 0.0004(3) 0.0009(3) -0.0003(3) C18 0.0145(4) 0.0161(4) 0.0187(4) -0.0018(3) 0.0035(3) -0.0001(3) C19 0.0131(4) 0.0163(4) 0.0275(5) -0.0005(4) 0.0024(4) -0.0008(3) C20 0.0158(4) 0.0181(4) 0.0234(5) 0.0010(4) -0.0040(4) -0.0031(3) C21 0.0209(5) 0.0230(4) 0.0155(4) -0.0006(4) -0.0012(4) -0.0061(4) 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' 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 C1 N1 C14 124.13(8) . . ? C5 N1 C1 124.01(8) . . ? C5 N1 C14 111.80(7) . . ? C21 N2 C17 117.57(9) . . ? O1 C1 N1 121.11(9) . . ? O1 C1 C2 125.04(9) . . ? N1 C1 C2 113.84(8) . . ? C1 C2 H2 118.9 . . ? C3 C2 C1 122.27(9) . . ? C3 C2 H2 118.9 . . ? C2 C3 H3 119.4 . . ? C2 C3 C4 121.15(9) . . ? C4 C3 H3 119.4 . . ? C3 C4 H4 121.3 . . ? C5 C4 C3 117.38(9) . . ? C5 C4 H4 121.3 . . ? N1 C5 C6 107.74(7) . . ? C4 C5 N1 121.30(8) . . ? C4 C5 C6 130.93(8) . . ? C5 C6 C7 122.42(8) . . ? C13 C6 C5 108.82(8) . . ? C13 C6 C7 128.75(8) . . ? C8 C7 C6 120.16(8) . . ? C12 C7 C6 120.72(8) . . ? C12 C7 C8 119.12(8) . . ? C7 C8 H8 119.8 . . ? C9 C8 C7 120.43(9) . . ? C9 C8 H8 119.8 . . ? C8 C9 H9 119.9 . . ? C10 C9 C8 120.16(9) . . ? C10 C9 H9 119.9 . . ? C9 C10 H10 120.1 . . ? C9 C10 C11 119.77(9) . . ? C11 C10 H10 120.1 . . ? C10 C11 H11 119.8 . . ? C10 C11 C12 120.34(9) . . ? C12 C11 H11 119.8 . . ? C7 C12 H12 119.9 . . ? C11 C12 C7 120.17(9) . . ? C11 C12 H12 119.9 . . ? C6 C13 C14 110.84(8) . . ? C6 C13 C17 127.92(8) . . ? C17 C13 C14 120.76(8) . . ? N1 C14 C13 100.45(7) . . ? N1 C14 C15 109.05(7) . . ? N1 C14 C16 110.85(7) . . ? C13 C14 C15 112.40(7) . . ? C13 C14 C16 111.10(7) . . ? C16 C14 C15 112.37(7) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N2 C17 C13 116.92(8) . . ? N2 C17 C18 121.84(8) . . ? C18 C17 C13 120.98(8) . . ? C17 C18 H18 120.3 . . ? C19 C18 C17 119.38(9) . . ? C19 C18 H18 120.3 . . ? C18 C19 H19 120.5 . . ? C20 C19 C18 118.93(9) . . ? C20 C19 H19 120.5 . . ? C19 C20 H20 121.0 . . ? C19 C20 C21 117.92(9) . . ? C21 C20 H20 121.0 . . ? N2 C21 C20 124.36(9) . . ? N2 C21 H21 117.8 . . ? C20 C21 H21 117.8 . . ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C1 1.2373(12) . ? N1 C1 1.3934(11) . ? N1 C5 1.3734(11) . ? N1 C14 1.4892(11) . ? N2 C17 1.3504(12) . ? N2 C21 1.3377(12) . ? C1 C2 1.4426(14) . ? C2 H2 0.9500 . ? C2 C3 1.3595(15) . ? C3 H3 0.9500 . ? C3 C4 1.4182(14) . ? C4 H4 0.9500 . ? C4 C5 1.3674(13) . ? C5 C6 1.4609(12) . ? C6 C7 1.4775(12) . ? C6 C13 1.3554(12) . ? C7 C8 1.3980(12) . ? C7 C12 1.3969(13) . ? C8 H8 0.9500 . ? C8 C9 1.3903(13) . ? C9 H9 0.9500 . ? C9 C10 1.3889(15) . ? C10 H10 0.9500 . ? C10 C11 1.3891(15) . ? C11 H11 0.9500 . ? C11 C12 1.3922(13) . ? C12 H12 0.9500 . ? C13 C14 1.5253(12) . ? C13 C17 1.4775(12) . ? C14 C15 1.5377(12) . ? C14 C16 1.5318(12) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 C18 1.3995(12) . ? C18 H18 0.9500 . ? C18 C19 1.3896(13) . ? C19 H19 0.9500 . ? C19 C20 1.3857(15) . ? C20 H20 0.9500 . ? C20 C21 1.3881(14) . ? C21 H21 0.9500 . ? loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.6496(12) 2 0.3504(12)