#------------------------------------------------------------------------------ #$Date: 2019-11-26 03:52:37 +0200 (Tue, 26 Nov 2019) $ #$Revision: 242551 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/13/26/4132604.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_4132604 loop_ _publ_author_name 'Kapoor, Mohit' 'Liu, Daniel' 'Young, Michael C.' _publ_section_title ; Carbon Dioxide-Mediated C(sp3)-H Arylation of Amine Substrates. ; _journal_issue 22 _journal_name_full 'Journal of the American Chemical Society' _journal_page_first 6818 _journal_page_last 6822 _journal_paper_doi 10.1021/jacs.8b05061 _journal_volume 140 _journal_year 2018 _chemical_absolute_configuration syn _chemical_formula_moiety 'C13 H17.50 N0.50 O2' _chemical_formula_sum 'C13 H17.5 N0.5 O2' _chemical_formula_weight 212.77 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens mixed _audit_creation_method SHELXL-2016/6 _cell_angle_alpha 90 _cell_angle_beta 102.884(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.9712(10) _cell_length_b 7.0406(5) _cell_length_c 13.2586(9) _cell_measurement_reflns_used 3450 _cell_measurement_temperature 100 _cell_measurement_theta_max 46.10 _cell_measurement_theta_min 3.42 _cell_volume 1180.36(15) _computing_structure_refinement 'SHELXL-2016/6 (Sheldrick, 2016)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100 _diffrn_measured_fraction_theta_full 0.964 _diffrn_measured_fraction_theta_max 0.964 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0214 _diffrn_reflns_av_unetI/netI 0.0309 _diffrn_reflns_Laue_measured_fraction_full 0.964 _diffrn_reflns_Laue_measured_fraction_max 0.964 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 3450 _diffrn_reflns_point_group_measured_fraction_full 0.871 _diffrn_reflns_point_group_measured_fraction_max 0.871 _diffrn_reflns_theta_full 46.099 _diffrn_reflns_theta_max 46.099 _diffrn_reflns_theta_min 3.419 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.635 _exptl_absorpt_correction_T_max 0.7465 _exptl_absorpt_correction_T_min 0.6849 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details sadabs _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.197 _exptl_crystal_description Block _exptl_crystal_F_000 460 _exptl_crystal_size_max 0.070 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.011 _exptl_transmission_factor_max 0.7507 _exptl_transmission_factor_min 0.6531 _refine_diff_density_max 0.256 _refine_diff_density_min -0.145 _refine_diff_density_rms 0.035 _refine_ls_abs_structure_details ; Flack x determined using 607 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.3(2) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.089 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 290 _refine_ls_number_reflns 1759 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.088 _refine_ls_R_factor_all 0.0429 _refine_ls_R_factor_gt 0.0400 _refine_ls_shift/su_max 6.295 _refine_ls_shift/su_mean 0.022 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1204 _refine_ls_wR_factor_ref 0.1233 _reflns_Friedel_coverage 0.620 _reflns_Friedel_fraction_full 0.753 _reflns_Friedel_fraction_max 0.753 _reflns_number_gt 1652 _reflns_number_total 1759 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file ja8b05061_si_002.cif _cod_data_source_block cu_MK_002_182_0m_a_a _cod_original_sg_symbol_H-M 'P 21' _cod_original_formula_sum 'C13 H17.50 N0.50 O2' _cod_database_code 4132604 _shelx_shelxl_version_number 2016/6 _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. ; _exptl_absorpt_special_details SADABS;Sheldrick1996;Blessing,ActaC.1995,A51,33 _shelx_res_file ; TITL cu_MK_002_182_0m_a_a.res in P2(1) cu_MK_002_182_0m_a_a.res created by SHELXL-2016/6 at 16:25:37 on 27-Mar-2018 REM Old TITL cu_MK_002_182_0m_a.res in P2(1) REM SHELXT solution in P2(1) REM R1 0.121, Rweak 0.033, Alpha 0.003, Orientation as input REM Flack x = 0.430 ( 0.187 ) from Parsons' quotients REM Formula found by SHELXT: C26 N O4 CELL 1.54178 12.9712 7.0406 13.2586 90.000 102.884 90.000 ZERR 4.000 0.0010 0.0005 0.0009 0.000 0.005 0.000 LATT -1 SYMM -X, 1/2+Y, -Z SFAC C H N O UNIT 52 70 2 8 TEMP 100 L.S. 500 BOND $H ACTA LIST 6 FMAP 2 PLAN 20 WGHT 0.100000 FVAR 0.67043 O1 4 0.507856 0.470646 0.095589 11.00000 0.05915 0.04263 = 0.06044 0.00675 0.03636 0.00040 O2 4 0.587126 0.743884 0.130547 11.00000 0.07421 0.04920 = 0.05192 -0.00933 0.02726 -0.00271 H2 2 0.751072 0.752549 0.231451 10.50000 -0.00100 O3 4 0.714108 1.021836 0.173751 11.00000 0.06162 0.10873 = 0.05521 0.01744 0.02205 0.00528 O4 4 0.821137 0.845208 0.284267 11.00000 0.07534 0.09792 = 0.12874 -0.00475 0.03337 -0.00326 N1 3 0.456228 0.091572 0.094122 11.00000 0.04875 0.02482 = 0.03446 -0.00146 0.02817 0.00460 AFIX 137 H1A 2 0.483585 0.056565 0.041101 11.00000 -1.50000 H1B 2 0.483564 0.020286 0.149007 11.00000 -1.50000 H1C 2 0.471393 0.213091 0.108953 11.00000 -1.50000 AFIX 0 C1 1 0.338596 0.065934 0.066010 11.00000 0.03334 0.02316 = 0.02675 -0.00002 0.01300 -0.00066 AFIX 13 H1 2 0.313342 0.133301 0.000472 11.00000 -1.20000 AFIX 0 C2 1 0.304793 -0.144891 0.045660 11.00000 0.04151 0.02764 = 0.03273 0.00079 0.01259 -0.00213 AFIX 23 H2A 2 0.282167 -0.171202 -0.027771 11.00000 -1.20000 H2B 2 0.361484 -0.231146 0.076232 11.00000 -1.20000 AFIX 0 C3 1 0.212214 -0.157483 0.100042 11.00000 0.03508 0.01801 = 0.03454 -0.00243 0.00583 -0.00171 AFIX 13 H3 2 0.161351 -0.258063 0.072893 11.00000 -1.20000 AFIX 0 C4 1 0.258428 -0.172042 0.216568 11.00000 0.03180 0.02424 = 0.04053 0.00335 0.01484 0.00452 AFIX 23 H4A 2 0.315730 -0.263527 0.231496 11.00000 -1.20000 H4B 2 0.204616 -0.208424 0.253259 11.00000 -1.20000 AFIX 0 C5 1 0.298973 0.030412 0.246103 11.00000 0.03264 0.02363 = 0.03584 -0.00624 0.02359 -0.00424 AFIX 13 H5 2 0.251133 0.083025 0.286669 11.00000 -1.20000 AFIX 0 C6 1 0.272590 0.139356 0.140326 11.00000 0.04501 0.00380 = 0.03532 -0.00149 0.01736 -0.00135 C7 1 0.164253 0.043010 0.088236 11.00000 0.03645 0.01757 = 0.03748 0.00132 0.01139 -0.00179 C8 1 0.118505 0.100570 -0.024346 11.00000 0.04631 0.03606 = 0.05295 0.00181 0.00907 0.00667 AFIX 137 H8A 2 0.168459 0.070734 -0.065621 11.00000 -1.50000 H8B 2 0.104497 0.234580 -0.027716 11.00000 -1.50000 H8C 2 0.053908 0.032447 -0.050212 11.00000 -1.50000 AFIX 0 C9 1 0.075722 0.075126 0.146327 11.00000 0.02816 0.02597 = 0.06526 -0.00512 0.01147 0.00090 AFIX 137 H9A 2 0.014658 0.002337 0.114108 11.00000 -1.50000 H9B 2 0.057644 0.207512 0.144198 11.00000 -1.50000 H9C 2 0.099510 0.035609 0.216996 11.00000 -1.50000 AFIX 0 C10 1 0.272629 0.352902 0.149533 11.00000 0.03848 0.03330 = 0.04433 -0.00424 0.02117 0.00356 AFIX 137 H10A 2 0.250605 0.408105 0.081942 11.00000 -1.50000 H10B 2 0.342634 0.395989 0.180984 11.00000 -1.50000 H10C 2 0.224674 0.390517 0.191531 11.00000 -1.50000 AFIX 0 C11 1 0.409153 0.053930 0.313050 11.00000 0.03436 0.02945 = 0.02654 -0.00174 0.01699 0.00392 C12 1 0.488669 -0.078214 0.318760 11.00000 0.03314 0.03490 = 0.03181 -0.00128 0.01785 -0.00883 AFIX 43 H12 2 0.473916 -0.191515 0.282341 11.00000 -1.20000 AFIX 0 C13 1 0.589986 -0.047095 0.377220 11.00000 0.03942 0.04843 = 0.03177 0.00460 0.02215 0.00329 AFIX 43 H13 2 0.642277 -0.137270 0.376790 11.00000 -1.20000 AFIX 0 C14 1 0.615164 0.117975 0.437068 11.00000 0.03767 0.05192 = 0.02567 -0.00909 0.01713 -0.01549 C15 1 0.533311 0.246947 0.434948 11.00000 0.05152 0.04100 = 0.02918 -0.01433 0.01641 -0.00489 AFIX 43 H15 2 0.546429 0.357341 0.474239 11.00000 -1.20000 AFIX 0 C16 1 0.433083 0.214147 0.375671 11.00000 0.03681 0.03664 = 0.03839 -0.00232 0.02418 -0.00190 AFIX 43 H16 2 0.379856 0.301681 0.377572 11.00000 -1.20000 AFIX 0 C17 1 0.724928 0.153869 0.494858 11.00000 0.05199 0.06989 = 0.02867 -0.01177 0.02462 -0.01534 C18 1 0.794312 0.009579 0.534866 11.00000 0.04287 0.08013 = 0.04191 -0.00805 0.01876 -0.01060 AFIX 43 H18 2 0.770420 -0.115346 0.529275 11.00000 -1.20000 AFIX 0 C19 1 0.898450 0.046410 0.583036 11.00000 0.03765 0.13355 = 0.05725 -0.02179 0.01676 -0.00119 AFIX 43 H19 2 0.943799 -0.052885 0.609343 11.00000 -1.20000 AFIX 0 C20 1 0.934931 0.232946 0.591885 11.00000 0.04250 0.12129 = 0.05828 -0.03355 0.02161 -0.02586 AFIX 43 H20 2 1.004923 0.258962 0.623691 11.00000 -1.20000 AFIX 0 C21 1 0.867662 0.376704 0.553776 11.00000 0.05527 0.10580 = 0.04745 -0.03233 0.02215 -0.02431 AFIX 43 H21 2 0.891933 0.501389 0.559779 11.00000 -1.20000 AFIX 0 C22 1 0.764124 0.339958 0.506440 11.00000 0.04543 0.08679 = 0.03569 -0.01273 0.02133 -0.01765 AFIX 43 H22 2 0.719171 0.440598 0.481597 11.00000 -1.20000 AFIX 0 C23 1 0.635715 0.494408 0.250767 11.00000 0.07550 0.05614 = 0.07321 0.00141 0.01929 -0.00246 AFIX 137 H23A 2 0.647993 0.360310 0.247542 11.00000 -1.50000 H23B 2 0.602210 0.520825 0.306899 11.00000 -1.50000 H23C 2 0.701948 0.560731 0.261697 11.00000 -1.50000 AFIX 0 C24 1 0.567800 0.556820 0.154429 11.00000 0.02483 0.03691 = 0.00657 -0.00406 0.00685 0.01049 C25 1 0.868267 1.168932 0.279286 11.00000 0.05225 0.07736 = 0.07419 -0.01702 0.02294 -0.02613 AFIX 137 H25A 2 0.863213 1.256965 0.223101 11.00000 -1.50000 H25B 2 0.940214 1.127457 0.302011 11.00000 -1.50000 H25C 2 0.845913 1.230021 0.335531 11.00000 -1.50000 AFIX 0 C26 1 0.799098 1.001763 0.243901 11.00000 0.08935 0.08676 = 0.05261 0.03131 0.04617 0.03863 HKLF 4 REM cu_MK_002_182_0m_a_a.res in P2(1) REM R1 = 0.0400 for 1652 Fo > 4sig(Fo) and 0.0429 for all 1759 data REM 290 parameters refined using 1 restraints END WGHT 0.0536 0.7060 REM Highest difference peak 0.256, deepest hole -0.145, 1-sigma level 0.035 Q1 1 0.7461 0.8144 0.2155 11.00000 0.05 0.22 Q2 1 0.6807 1.1779 0.1800 11.00000 0.05 0.21 Q3 1 0.6443 0.9429 0.1341 11.00000 0.05 0.17 Q4 1 0.9366 -0.0910 0.6407 11.00000 0.05 0.13 Q5 1 0.6442 0.6262 0.1789 11.00000 0.05 0.12 Q6 1 0.7429 0.5340 0.2249 11.00000 0.05 0.11 Q7 1 0.7616 1.1774 0.2414 11.00000 0.05 0.10 Q8 1 0.1234 0.3808 0.0004 11.00000 0.05 0.10 Q9 1 0.7015 0.8370 0.1049 11.00000 0.05 0.10 Q10 1 0.2999 -0.1612 -0.0742 11.00000 0.05 0.10 Q11 1 0.6763 0.3290 0.1998 11.00000 0.05 0.10 Q12 1 0.9813 0.0857 0.6620 11.00000 0.05 0.10 Q13 1 0.5989 0.2160 0.4937 11.00000 0.05 0.10 Q14 1 0.4627 0.5468 0.3330 11.00000 0.05 0.10 Q15 1 0.0911 0.3154 0.1966 11.00000 0.05 0.10 Q16 1 0.9211 0.0792 0.5794 11.00000 0.05 0.10 Q17 1 0.5145 0.3216 0.0032 11.00000 0.05 0.10 Q18 1 0.9570 1.5309 0.2335 11.00000 0.05 0.10 Q19 1 0.7670 1.0074 0.1310 11.00000 0.05 0.09 Q20 1 -0.0656 0.1996 0.1078 11.00000 0.05 0.09 ; _shelx_res_checksum 22484 _shelx_hkl_file ; 1 0 0 1792.82 37.10 -1 0 0 1856.11 37.20 2 0 0 690.23 14.70 -2 0 0 685.23 14.00 2 0 0 675.53 14.00 3 0 0 658.43 14.30 -3 0 0 614.34 13.30 3 0 0 642.74 13.30 4 0 0 58.99 2.00 4 0 0 58.09 2.90 4 0 0 57.79 3.30 5 0 0 237.88 6.50 5 0 0 238.48 7.50 5 0 0 240.18 7.20 6 0 0 239.08 7.80 6 0 0 249.48 7.00 7 0 0 84.79 2.90 7 0 0 93.09 5.00 8 0 0 3.60 1.10 8 0 0 2.60 2.00 9 0 0 57.49 4.70 9 0 0 55.59 2.80 10 0 0 40.20 2.80 11 0 0 -1.60 1.30 0 -1 0 0.40 0.50 1 -1 0 302.57 7.10 1 -1 0 310.77 6.80 2 -1 0 625.94 13.90 2 -1 0 625.54 13.20 2 1 0 611.64 13.60 2 1 0 635.84 13.30 3 -1 0 842.42 17.60 3 -1 0 831.42 18.60 3 1 0 850.21 18.30 3 1 0 823.82 17.60 4 -1 0 178.98 5.80 4 -1 0 177.18 4.60 4 1 0 184.98 5.60 4 1 0 186.08 4.70 4 1 0 174.68 5.00 5 -1 0 27.20 1.80 5 -1 0 26.00 2.70 5 -1 0 27.60 2.70 5 1 0 25.60 2.20 5 1 0 26.20 2.60 6 -1 0 244.98 8.10 6 -1 0 250.47 8.40 6 1 0 245.58 7.30 6 1 0 259.97 8.10 7 -1 0 78.99 4.60 7 -1 0 74.19 5.00 7 -1 0 74.19 2.70 7 1 0 72.59 3.70 7 1 0 75.59 4.30 8 -1 0 82.99 5.40 8 -1 0 80.39 3.10 8 1 0 84.19 4.50 8 1 0 76.09 3.00 8 1 0 81.09 5.10 9 -1 0 95.99 6.20 9 -1 0 93.99 3.50 9 1 0 97.59 5.20 9 1 0 95.59 3.60 9 1 0 92.39 5.90 10 -1 0 8.10 1.70 10 1 0 7.00 1.60 11 -1 0 62.69 3.30 11 1 0 62.09 3.30 0 -2 0 981.00 20.90 0 2 0 983.90 21.20 1 -2 0 98.29 3.70 1 -2 0 101.49 3.30 1 2 0 100.99 3.50 2 -2 0 374.06 9.70 2 -2 0 391.26 9.60 2 -2 0 386.16 9.00 2 2 0 375.56 9.20 3 -2 0 103.69 4.20 3 -2 0 109.79 3.50 3 -2 0 107.89 4.50 3 2 0 98.69 3.90 3 2 0 105.89 3.60 3 2 0 106.19 3.70 4 -2 0 488.25 12.10 4 -2 0 457.45 12.10 4 -2 0 455.45 10.60 4 2 0 449.36 11.00 4 2 0 435.26 11.30 4 2 0 446.16 10.70 5 -2 0 91.89 4.70 5 -2 0 88.49 3.10 5 -2 0 87.29 4.80 5 2 0 89.59 3.80 5 2 0 93.99 4.30 6 -2 0 199.68 5.30 6 -2 0 188.68 7.60 6 -2 0 193.18 7.30 6 2 0 189.38 6.30 6 2 0 189.08 6.80 7 -2 0 123.19 6.30 7 -2 0 124.09 3.90 7 -2 0 128.69 6.70 7 2 0 134.49 5.40 7 2 0 133.19 5.90 8 -2 0 18.40 1.70 8 -2 0 24.90 3.60 -8 -2 0 25.10 2.90 8 -2 0 21.30 3.80 8 2 0 21.30 2.80 9 -2 0 7.40 3.10 9 -2 0 6.10 1.50 9 -2 0 6.60 2.60 -9 -2 0 7.80 1.90 9 2 0 6.60 2.30 9 2 0 7.10 0.90 9 2 0 9.60 1.70 -10 -2 0 62.99 4.10 10 -2 0 57.19 3.20 10 2 0 65.89 3.20 10 2 0 61.49 4.90 11 -2 0 13.90 1.80 -11 -2 0 16.90 2.50 11 2 0 14.60 1.90 0 3 0 0.10 1.20 -1 3 0 311.97 8.70 1 3 0 304.17 8.40 2 -3 0 23.20 2.00 2 -3 0 25.90 2.80 2 3 0 20.00 2.10 2 3 0 22.70 2.00 3 -3 0 282.27 7.80 3 -3 0 285.97 8.70 3 -3 0 272.97 8.70 3 3 0 281.67 7.80 3 3 0 278.17 7.90 3 3 0 280.37 8.00 4 -3 0 10.00 2.30 4 -3 0 11.90 2.30 4 -3 0 9.60 1.70 4 3 0 11.60 1.80 4 3 0 10.50 1.70 5 -3 0 161.48 6.60 5 -3 0 144.49 6.60 5 3 0 148.49 5.50 -6 -3 0 17.60 2.40 6 -3 0 19.00 3.20 6 -3 0 15.20 3.00 6 3 0 18.20 2.40 -7 -3 0 61.69 3.40 7 -3 0 60.99 5.30 7 -3 0 65.09 5.10 7 3 0 65.79 4.10 -8 -3 0 36.60 3.10 8 -3 0 31.90 4.10 8 -3 0 30.50 4.50 8 3 0 33.50 3.70 -9 -3 0 16.40 2.30 9 -3 0 7.60 3.20 9 3 0 15.60 3.10 -10 -3 0 36.90 3.60 10 3 0 47.40 3.00 10 3 0 38.50 1.80 0 -4 0 497.65 11.40 0 -4 0 462.35 10.90 1 -4 0 87.39 3.40 -1 -4 0 89.29 3.20 -1 -4 0 93.99 3.50 -1 4 0 90.99 4.80 -2 -4 0 387.86 9.20 -2 -4 0 384.86 9.40 2 -4 0 374.56 9.30 2 -4 0 390.26 11.50 2 4 0 380.26 10.20 -2 4 0 375.06 11.30 3 -4 0 11.60 2.50 3 -4 0 12.10 1.60 -3 -4 0 14.90 1.80 -3 4 0 10.40 2.20 3 4 0 7.80 1.70 4 -4 0 21.80 3.30 -4 -4 0 21.80 2.10 4 4 0 21.70 2.70 5 -4 0 34.20 3.90 5 -4 0 42.10 4.30 5 4 0 46.00 3.60 6 -4 0 19.10 3.50 6 -4 0 22.00 3.70 6 4 0 27.00 3.30 7 -4 0 8.10 3.00 7 4 0 12.40 2.70 8 -4 0 65.19 6.50 8 4 0 76.19 5.30 0 -5 0 -0.20 1.10 1 -5 0 176.88 5.60 -1 -5 0 162.78 5.50 -1 -5 0 168.48 5.20 -2 -5 0 101.09 3.80 -2 -5 0 96.89 4.00 2 -5 0 101.39 4.00 -3 -5 0 61.99 3.10 3 -5 0 63.69 3.30 -3 -5 0 62.69 3.10 3 5 0 61.79 4.10 -4 -5 0 17.20 1.90 -4 -5 0 17.80 2.10 4 5 0 22.40 3.00 -5 -5 0 1.50 1.40 5 5 0 -0.20 1.60 -6 -5 0 29.10 2.70 6 5 0 26.80 3.40 -7 -5 0 15.00 2.00 0 -6 0 58.99 3.50 1 -6 0 31.50 2.90 -1 -6 0 29.60 2.80 -2 -6 0 300.17 8.60 2 -6 0 287.87 8.50 -3 -6 0 10.40 2.00 3 -6 0 8.60 2.00 -3 -6 0 11.00 2.00 -4 -6 0 62.89 3.50 -4 -6 0 59.19 3.50 11 0 -1 -1.60 1.30 10 0 -1 18.60 1.90 9 0 -1 1.40 1.20 9 0 -1 1.90 2.10 8 0 -1 113.59 5.80 8 0 -1 117.29 3.70 7 0 -1 21.30 2.80 6 0 -1 50.79 2.20 6 0 -1 42.70 3.20 5 0 -1 19.60 2.20 5 0 -1 16.50 1.70 4 0 -1 1033.00 22.30 -4 0 1 994.40 20.40 4 0 -1 1000.20 20.40 4 0 -1 1000.70 21.50 3 0 -1 34.10 2.10 3 0 -1 34.60 0.90 2 0 -1 7.10 1.10 -1 0 1 1.90 0.20 1 0 -1 1.80 0.20 0 0 1 111.99 2.50 0 0 -1 105.59 2.50 -1 0 -1 433.86 9.30 1 0 1 448.66 9.30 2 0 1 247.68 5.60 2 0 1 234.08 5.90 3 0 1 321.27 8.00 3 0 1 316.17 7.30 4 0 1 168.48 5.40 4 0 1 168.58 4.60 4 0 1 178.38 5.70 5 0 1 1224.78 27.70 5 0 1 1246.88 26.50 5 0 1 1234.28 26.20 5 0 1 1261.17 27.50 6 0 1 448.66 12.10 6 0 1 452.35 11.00 6 0 1 437.96 12.40 7 0 1 28.20 2.00 7 0 1 30.80 3.30 7 0 1 33.00 2.60 8 0 1 1.10 1.10 8 0 1 1.20 1.90 9 0 1 1.10 1.40 9 0 1 2.00 2.20 10 0 1 6.40 1.70 11 0 1 9.60 1.80 11 -1 -1 14.50 1.90 11 1 -1 15.60 1.90 10 -1 -1 42.40 2.70 10 1 -1 42.90 2.70 9 -1 -1 45.70 2.50 9 -1 -1 42.50 4.30 9 1 -1 42.50 4.40 9 1 -1 43.70 2.50 8 -1 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1.60 9 0 -8 0.30 1.40 8 0 -8 17.00 1.90 7 0 -8 5.80 1.40 6 0 -8 141.29 4.80 -5 0 8 142.79 4.80 5 0 -8 138.59 4.60 -4 0 8 679.83 15.70 4 0 -8 696.13 15.60 3 0 -8 3.30 1.10 -3 0 8 5.00 1.50 3 0 -8 5.00 1.30 2 0 -8 67.59 3.00 -2 0 8 70.09 3.10 -1 0 8 143.69 4.70 1 0 -8 134.89 4.50 0 0 8 19.70 2.00 0 0 -8 20.40 1.90 1 0 8 130.69 4.50 -1 0 -8 128.79 4.40 -2 0 -8 27.10 2.50 2 0 8 25.60 2.40 -3 0 -8 12.90 2.00 -4 0 -8 100.49 4.30 -5 0 -8 8.50 2.10 -6 0 -8 69.89 4.10 -7 0 -8 14.60 2.50 10 -1 -8 84.59 4.20 9 -1 -8 55.49 3.50 8 -1 -8 21.80 2.30 7 -1 -8 23.80 2.30 7 1 -8 22.30 3.70 6 -1 -8 61.99 3.00 6 -1 -8 58.19 3.00 6 1 -8 62.89 5.00 -5 -1 8 53.79 3.00 5 -1 -8 55.89 2.80 5 -1 -8 54.09 2.90 5 1 -8 49.90 4.30 5 1 -8 51.99 1.80 -5 1 8 52.19 3.00 4 -1 -8 98.79 3.70 4 -1 -8 105.69 4.00 -4 -1 8 103.19 4.00 -4 1 8 107.69 4.10 3 -1 -8 205.68 5.90 -3 -1 8 189.48 5.80 3 -1 -8 201.18 5.50 -3 1 8 185.98 5.80 3 1 -8 181.38 5.40 -2 -1 8 11.50 1.70 2 -1 -8 10.40 1.30 2 -1 -8 12.50 1.60 2 1 -8 10.80 1.40 1 -1 -8 13.30 1.60 -1 -1 8 12.50 1.90 1 -1 -8 9.90 1.50 1 1 -8 11.10 1.50 0 -1 -8 25.90 2.20 0 -1 8 19.30 2.00 0 1 -8 18.40 1.80 1 -1 8 43.00 2.80 -1 -1 -8 44.10 2.60 1 1 8 47.70 2.90 -1 1 -8 43.00 2.60 -2 -1 -8 197.18 5.90 2 -1 8 183.58 5.80 -2 1 -8 191.28 5.90 -2 1 -8 188.48 5.10 2 1 8 183.38 5.80 -3 -1 -8 99.89 4.10 -3 1 -8 106.19 4.30 -4 -1 -8 72.69 3.90 -4 1 -8 79.29 3.90 -5 -1 -8 6.40 1.80 -5 1 -8 10.10 2.20 -6 -1 -8 45.80 3.70 -6 1 -8 43.30 3.70 -7 -1 -8 28.00 3.00 -7 1 -8 25.70 2.90 9 -2 -8 15.60 2.40 8 -2 -8 34.80 2.90 7 -2 -8 71.49 3.70 7 -2 -8 67.79 3.60 7 2 -8 70.49 2.20 6 -2 -8 193.18 6.00 6 -2 -8 191.28 6.10 6 2 -8 183.48 8.50 6 2 -8 196.08 4.80 -5 -2 8 110.19 4.40 5 -2 -8 105.19 4.30 5 -2 -8 109.09 4.20 5 2 -8 116.99 6.50 5 2 -8 114.99 3.30 4 -2 -8 73.39 3.30 4 -2 -8 79.19 3.50 -4 -2 8 75.39 3.60 4 2 -8 80.79 5.30 4 2 -8 77.29 2.70 3 -2 -8 117.49 4.10 3 -2 -8 122.69 4.30 -3 -2 8 121.39 4.50 3 2 -8 112.19 3.50 3 2 -8 111.89 6.10 2 -2 -8 28.40 2.20 2 -2 -8 27.00 2.30 -2 -2 8 26.60 2.30 2 2 -8 26.90 3.60 -1 -2 8 15.80 2.10 1 -2 -8 12.80 1.70 1 -2 -8 12.10 1.50 1 2 -8 11.90 2.50 0 -2 8 29.70 2.50 0 -2 -8 30.80 2.20 0 -2 -8 32.00 2.20 0 2 -8 23.80 3.50 1 -2 8 44.90 2.80 -1 -2 -8 47.00 2.80 -2 -2 -8 21.20 2.20 2 -2 8 18.40 2.30 -3 -2 -8 3.50 1.30 -4 -2 -8 9.10 1.30 -4 -2 -8 8.70 1.90 -5 -2 -8 73.39 3.30 -5 -2 -8 72.79 3.90 -5 2 -8 73.59 4.10 -6 -2 -8 14.30 1.70 -6 -2 -8 14.30 2.20 -6 2 -8 14.40 2.30 8 -3 -8 8.30 2.00 8 3 -8 8.00 1.00 7 -3 -8 48.50 3.30 7 -3 -8 48.40 3.20 7 3 -8 51.79 2.20 6 -3 -8 16.40 2.20 -6 -3 8 19.30 2.70 6 -3 -8 19.90 2.40 6 3 -8 16.70 1.50 -5 -3 8 6.50 1.90 5 -3 -8 4.20 1.50 5 -3 -8 6.20 1.50 5 3 -8 6.00 1.20 4 -3 -8 36.00 2.70 -4 -3 8 38.00 2.90 4 -3 -8 35.30 2.70 4 3 -8 32.90 2.00 4 3 -8 23.70 3.70 3 -3 -8 66.39 3.40 3 -3 -8 72.19 3.50 -3 -3 8 71.49 3.60 3 3 -8 75.39 5.60 3 3 -8 71.69 2.80 2 -3 -8 69.79 3.30 2 -3 -8 66.19 3.30 -2 -3 8 68.39 3.70 2 3 -8 70.39 5.50 1 -3 -8 42.10 2.70 1 -3 -8 35.60 2.50 -1 -3 8 37.60 3.00 1 3 -8 43.90 4.80 0 -3 -8 38.60 2.70 0 -3 8 39.30 3.00 0 -3 -8 39.00 2.70 0 3 -8 38.40 4.50 -1 -3 -8 31.90 2.60 -1 -3 -8 33.40 2.70 1 -3 8 31.40 4.40 1 -3 8 31.80 2.80 -1 3 -8 29.90 4.40 2 -3 8 14.40 4.00 2 -3 8 10.80 2.10 -3 -3 -8 14.10 2.30 3 -3 8 16.10 4.00 4 -3 8 254.57 11.30 7 -4 -8 60.39 3.50 7 4 -8 59.99 2.60 -6 -4 8 27.60 2.90 6 -4 -8 24.00 2.40 6 -4 -8 30.20 2.80 6 4 -8 28.80 2.10 5 -4 -8 76.09 4.00 5 -4 -8 76.49 3.90 -5 -4 8 74.39 4.00 5 4 -8 77.79 3.10 4 -4 -8 272.67 7.90 -4 -4 8 269.87 8.20 4 4 -8 260.87 6.90 -3 -4 8 47.30 3.40 3 -4 -8 48.40 3.20 2 -4 -8 50.89 3.10 -2 -4 8 46.00 3.40 1 -4 -8 48.00 3.20 -1 -4 8 46.70 3.50 0 -4 -8 46.50 3.00 0 -4 8 49.20 3.40 1 -4 8 70.79 6.70 -1 -4 -8 69.99 3.60 1 -4 8 67.39 3.70 -2 -4 -8 5.60 1.60 2 -4 8 3.10 3.10 2 -4 8 4.50 1.80 2 -5 -8 36.70 2.90 -2 -5 8 43.20 3.20 -1 -5 8 16.40 2.40 1 -5 -8 19.40 2.40 9 0 -9 1.30 1.90 8 0 -9 106.39 4.40 7 0 -9 33.30 2.60 6 0 -9 1.40 1.20 -5 0 9 35.80 2.70 5 0 -9 35.30 2.50 4 0 -9 159.58 5.20 -4 0 9 156.78 5.40 -3 0 9 870.41 19.70 3 0 -9 861.91 19.40 2 0 -9 94.19 3.80 -2 0 9 94.49 4.00 1 0 -9 45.90 2.70 -1 0 9 44.40 2.90 0 0 -9 5.70 1.50 0 0 9 5.70 1.60 1 0 9 1.40 1.50 -1 0 -9 0.20 1.20 -2 0 -9 41.50 2.90 2 0 9 36.50 2.90 -3 0 -9 9.70 2.00 -4 0 -9 29.80 2.80 -5 0 -9 1.20 1.70 -6 0 -9 19.30 2.60 9 -1 -9 20.80 2.40 8 -1 -9 52.69 3.40 7 -1 -9 1.10 1.40 6 -1 -9 49.10 3.00 5 -1 -9 126.29 4.70 -5 -1 9 133.59 4.90 5 -1 -9 127.09 4.60 -5 1 9 127.69 4.90 5 1 -9 128.69 3.20 4 -1 -9 27.90 2.30 4 -1 -9 24.20 2.40 -4 -1 9 21.60 2.40 4 1 -9 25.50 1.40 -4 1 9 26.10 2.70 3 -1 -9 37.20 2.70 -3 -1 9 33.70 2.60 3 -1 -9 35.20 2.50 3 1 -9 38.00 1.70 -3 1 9 38.40 2.90 2 -1 -9 46.80 2.90 2 -1 -9 49.90 2.80 -2 -1 9 51.79 3.00 2 1 -9 56.09 2.90 2 1 -9 55.99 2.10 -2 1 9 55.59 3.20 1 -1 -9 64.79 3.20 -1 -1 9 63.59 3.40 1 1 -9 61.59 3.00 1 1 -9 59.69 2.40 -1 1 9 59.89 3.30 0 -1 9 29.20 2.70 0 -1 -9 23.60 2.20 0 1 -9 27.30 1.80 0 1 9 24.70 2.40 0 1 -9 26.20 2.40 -1 -1 -9 62.99 3.30 1 -1 9 64.09 3.50 -1 1 -9 67.59 3.50 -1 1 -9 65.29 2.70 1 1 9 65.99 3.50 -2 -1 -9 12.30 1.90 2 -1 9 10.40 1.90 2 1 9 12.60 2.20 -2 1 -9 11.80 1.90 -3 -1 -9 3.90 1.60 -3 1 -9 2.60 1.60 -4 -1 -9 56.39 3.50 -4 1 -9 54.69 3.60 -5 -1 -9 17.60 2.40 -5 1 -9 21.80 2.70 9 -2 -9 18.20 2.30 8 -2 -9 16.30 2.30 7 -2 -9 18.10 2.40 6 -2 -9 41.00 3.00 6 -2 -9 45.10 3.10 -6 -2 9 44.30 3.20 6 2 -9 43.60 1.80 5 -2 -9 37.70 2.90 5 -2 -9 40.00 2.90 -5 -2 9 43.30 3.10 5 2 -9 40.30 1.90 5 2 -9 37.50 4.80 -5 2 9 40.50 3.20 -4 -2 9 77.79 3.90 4 -2 -9 70.99 3.60 4 -2 -9 69.79 3.50 4 2 -9 72.89 8.70 4 2 -9 77.49 2.70 -3 -2 9 102.49 4.30 3 -2 -9 97.49 4.00 3 -2 -9 102.09 4.20 3 2 -9 99.69 3.20 -2 -2 9 11.70 2.00 2 -2 -9 15.10 1.90 2 -2 -9 14.80 2.00 2 2 -9 12.50 1.40 1 -2 -9 12.20 1.80 -1 -2 9 19.10 2.30 1 -2 -9 13.90 1.80 1 2 -9 15.70 1.50 0 -2 -9 6.30 1.60 0 -2 9 8.00 1.90 0 2 -9 9.00 1.30 1 -2 9 26.60 2.70 -1 -2 -9 19.50 2.10 -1 2 -9 23.30 1.90 2 -2 9 3.40 1.80 -2 -2 -9 4.10 1.70 2 2 9 5.30 2.10 -3 -2 -9 33.40 3.00 -4 -2 -9 39.10 3.20 -5 -2 -9 5.00 1.80 8 -3 -9 9.00 2.00 8 3 -9 9.70 1.30 7 -3 -9 38.20 3.00 7 -3 -9 39.90 3.20 7 3 -9 36.50 1.90 6 -3 -9 24.00 2.70 6 -3 -9 24.50 2.60 -6 -3 9 24.30 2.80 6 3 -9 20.10 1.60 5 -3 -9 62.39 3.60 -5 -3 9 57.39 3.70 5 -3 -9 57.39 3.50 5 3 -9 58.99 2.60 4 -3 -9 24.90 2.50 -4 -3 9 20.20 2.60 4 -3 -9 29.30 2.80 4 3 -9 19.30 1.60 3 -3 -9 71.69 3.70 -3 -3 9 72.59 3.90 3 -3 -9 69.29 3.50 3 3 -9 67.89 2.80 -2 -3 9 71.49 3.80 2 -3 -9 61.99 3.50 2 -3 -9 63.99 3.50 2 3 -9 64.09 2.80 1 -3 -9 35.60 2.80 -1 -3 9 31.50 2.90 1 -3 -9 31.00 2.70 0 -3 -9 16.90 2.10 0 -3 -9 17.20 2.00 0 -3 9 23.90 2.70 1 -3 9 3.30 3.20 1 -3 9 3.10 1.80 -1 -3 -9 3.70 1.60 2 -3 9 11.10 2.20 -2 -3 -9 10.60 1.90 2 -3 9 14.40 5.70 -3 -3 -9 5.60 1.70 5 -4 -9 21.50 2.60 -5 -4 9 17.00 2.40 5 -4 -9 16.70 2.20 5 4 -9 20.60 1.70 -4 -4 9 12.40 2.10 4 -4 -9 13.00 2.60 4 -4 -9 16.90 2.20 4 4 -9 19.30 1.70 3 -4 -9 23.20 2.40 -3 -4 9 30.60 3.10 3 4 -9 27.70 2.00 2 -4 -9 2.00 1.40 -2 -4 9 -0.30 1.60 1 -4 -9 16.20 2.10 -1 -4 9 13.10 2.20 0 -4 9 2.00 1.60 0 -4 -9 0.40 1.40 -1 -4 -9 10.90 1.90 1 -4 9 16.60 2.40 7 0 -10 84.29 4.00 -6 0 10 53.79 4.90 6 0 -10 37.70 2.90 -5 0 10 12.80 2.20 5 0 -10 14.40 2.00 4 0 -10 259.37 7.60 -4 0 10 259.67 7.70 -3 0 10 192.38 6.40 3 0 -10 188.98 6.10 2 0 -10 48.60 3.10 -2 0 10 50.19 3.40 1 0 -10 9.00 1.80 -1 0 10 6.90 2.10 0 0 -10 7.60 1.70 0 0 10 10.20 2.10 1 0 10 1.20 1.50 -1 0 -10 0.00 1.40 2 0 10 5.80 1.80 -2 0 -10 5.20 1.70 -3 0 -10 20.80 2.40 -4 0 -10 0.70 1.60 8 -1 -10 30.50 2.90 7 -1 -10 127.69 5.10 -6 -1 10 58.49 3.80 6 -1 -10 60.89 3.60 5 -1 -10 125.99 4.90 -5 -1 10 118.99 4.90 -5 1 10 125.19 5.10 4 -1 -10 323.87 9.00 4 -1 -10 350.26 9.50 -4 -1 10 356.96 9.60 -4 1 10 346.77 9.50 3 -1 -10 29.10 2.70 -3 -1 10 30.70 3.00 -3 1 10 31.70 3.10 -2 -1 10 -0.30 1.70 2 -1 -10 -0.20 1.30 -2 1 10 0.40 1.80 -1 -1 10 33.80 3.10 1 -1 -10 32.80 2.70 1 1 -10 32.70 2.80 -1 1 10 31.90 3.10 0 -1 -10 39.70 2.90 0 -1 10 40.70 3.20 0 1 10 35.20 3.10 0 1 -10 38.30 2.80 -1 -1 -10 38.10 3.00 1 -1 10 40.90 3.10 -1 1 -10 35.90 2.90 1 1 10 34.50 3.00 2 -1 10 13.10 2.30 -2 -1 -10 13.20 2.00 -2 1 -10 13.90 2.20 2 1 10 11.80 2.20 -3 -1 -10 35.80 3.20 -3 1 -10 31.70 2.90 -4 -1 -10 10.50 2.10 -4 1 -10 14.90 2.20 8 -2 -10 82.59 4.30 7 -2 -10 34.90 3.10 6 -2 -10 7.90 1.90 -6 -2 10 9.70 2.20 6 -2 -10 6.10 1.90 6 2 -10 7.70 0.80 5 -2 -10 33.40 3.00 5 -2 -10 27.00 2.60 -5 -2 10 32.00 3.10 5 2 -10 30.70 1.70 -5 2 10 32.00 3.10 4 -2 -10 12.70 1.80 -4 -2 10 14.10 2.30 4 -2 -10 10.10 1.90 -4 2 10 15.10 2.50 4 2 -10 13.30 1.30 3 -2 -10 20.20 2.30 3 -2 -10 17.80 2.30 -3 -2 10 17.80 2.60 -3 2 10 18.80 2.90 3 2 -10 16.70 1.50 2 -2 -10 7.90 1.90 2 -2 -10 6.70 1.70 -2 -2 10 9.90 2.30 -2 2 10 9.20 2.40 2 2 -10 6.20 1.20 1 -2 -10 5.40 1.70 -1 -2 10 9.00 2.20 1 2 -10 6.10 1.30 -1 2 10 7.70 2.30 0 -2 10 11.10 2.20 0 -2 -10 10.20 1.80 0 2 10 16.40 2.70 0 2 -10 12.50 1.50 -1 -2 -10 20.90 2.30 1 -2 10 29.40 3.00 -1 2 -10 22.50 1.90 1 2 10 31.70 3.10 -2 -2 -10 142.39 5.20 2 -2 10 125.49 5.20 2 2 10 129.49 5.20 -3 -2 -10 86.89 4.30 -6 -3 10 152.38 5.70 6 -3 -10 161.58 5.90 6 -3 -10 154.78 5.70 6 3 -10 161.98 4.20 5 -3 -10 193.68 6.50 -5 -3 10 184.78 6.50 5 -3 -10 191.78 6.30 -5 3 10 178.68 6.60 5 3 -10 183.58 5.00 4 -3 -10 0.10 1.50 4 -3 -10 1.10 1.40 -4 -3 10 0.90 1.60 4 3 -10 1.90 1.10 3 -3 -10 16.10 2.10 -3 -3 10 24.70 2.90 3 -3 -10 21.60 2.60 3 3 -10 17.50 1.60 2 -3 -10 0.90 1.50 -2 -3 10 0.00 1.50 2 -3 -10 0.70 1.50 2 3 -10 2.10 1.10 1 -3 -10 3.20 1.60 -1 -3 10 1.90 1.70 1 -3 -10 3.00 1.60 1 3 -10 2.60 1.10 0 -3 -10 -0.80 1.40 0 -3 10 0.20 1.60 0 3 -10 2.30 1.10 -1 -3 -10 3.40 1.50 1 -3 10 3.50 1.70 -2 -3 -10 17.20 2.20 2 3 10 26.30 2.80 -6 0 11 304.27 8.80 5 0 -11 126.89 5.10 -5 0 11 132.99 5.30 -4 0 11 213.48 7.10 4 0 -11 215.38 6.90 -3 0 11 89.69 4.40 3 0 -11 87.39 4.10 -2 0 11 -0.90 1.80 2 0 -11 1.80 1.50 1 0 -11 -0.40 1.50 -1 0 11 1.50 1.90 0 0 11 11.70 2.20 0 0 -11 9.10 1.90 -1 0 -11 1.80 1.50 1 0 11 0.20 1.60 -2 0 -11 33.70 3.10 2 0 11 38.30 3.20 -3 0 -11 35.90 3.20 7 -1 -11 1.80 1.50 -6 -1 11 19.90 2.60 6 -1 -11 27.50 2.70 -6 1 11 22.50 3.00 -5 -1 11 66.49 3.90 5 -1 -11 72.89 3.90 -5 1 11 65.69 4.00 4 -1 -11 30.80 3.00 -4 -1 11 20.60 2.60 -4 1 11 28.40 3.20 3 -1 -11 6.30 1.80 -3 -1 11 8.10 2.20 -3 1 11 4.50 2.10 -2 -1 11 8.40 2.20 2 -1 -11 13.10 2.20 -2 1 11 14.60 2.60 -1 -1 11 0.30 1.60 1 -1 -11 1.90 1.60 -1 1 11 0.00 1.90 0 -1 -11 22.50 2.40 0 -1 11 23.60 2.70 0 1 11 22.20 2.70 0 1 -11 23.40 3.30 -1 -1 -11 41.30 3.20 1 -1 11 36.50 3.10 1 1 11 40.20 3.30 -1 1 -11 36.50 3.10 -2 -1 -11 63.39 3.70 -2 1 -11 58.49 3.60 2 1 11 53.99 3.60 6 -2 -11 36.20 3.20 -6 -2 11 28.40 2.90 5 -2 -11 3.80 1.70 -5 -2 11 4.80 1.80 5 -2 -11 4.70 1.90 -5 2 11 1.30 1.90 4 -2 -11 6.10 1.90 4 -2 -11 4.70 1.80 -4 -2 11 4.70 1.80 -4 2 11 9.00 2.40 4 2 -11 7.60 1.10 3 -2 -11 14.80 2.30 -3 -2 11 11.20 2.30 3 2 -11 12.70 1.40 -3 2 11 12.50 2.30 2 -2 -11 31.80 2.90 -2 -2 11 18.10 2.50 -2 2 11 32.20 3.30 2 2 -11 27.10 2.00 1 -2 -11 14.10 2.30 -1 -2 11 13.30 2.30 1 2 -11 11.30 1.50 -1 2 11 17.40 2.60 0 -2 -11 20.40 2.50 0 -2 11 17.60 2.60 0 2 11 16.70 2.60 1 -2 11 2.20 1.60 -1 -2 -11 1.00 1.60 1 2 11 4.60 1.90 3 -3 -11 31.30 2.90 -3 -3 11 19.20 2.50 3 -3 -11 29.40 2.70 -3 3 11 21.60 2.70 3 3 -11 27.00 1.90 2 -3 -11 60.69 5.50 -2 -3 11 51.59 3.50 2 -3 -11 49.90 3.40 2 3 -11 47.00 2.50 -2 3 11 52.89 3.80 5 0 -12 55.29 3.60 -5 0 12 46.70 3.50 -4 0 12 3.60 1.90 4 0 -12 1.70 1.60 3 0 -12 1.40 1.60 -3 0 12 2.10 1.80 2 0 -12 1.30 1.50 -2 0 12 2.90 1.80 -1 0 12 47.20 3.40 1 0 -12 43.30 3.30 0 0 12 19.30 2.60 0 0 -12 25.00 2.70 4 -1 -12 22.70 2.50 -4 -1 12 13.80 2.20 -4 1 12 30.50 3.20 -3 -1 12 23.00 2.70 3 -1 -12 32.90 3.10 -3 1 12 26.90 2.90 -2 -1 12 19.50 2.80 2 -1 -12 10.90 2.10 -2 1 12 17.10 2.60 -1 -1 12 4.30 1.80 1 -1 -12 5.60 1.90 -1 1 12 2.60 1.70 0 0 0 0.00 0.00 _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' ; _shelx_hkl_checksum 96765 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' 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 O1 O 0.5079(4) 0.4706(7) 0.0956(4) 0.0505(14) Uani 1 1 d . . . O2 O 0.5871(4) 0.7439(8) 0.1305(3) 0.0564(14) Uani 1 1 d . . . H2 H 0.751(7) 0.753(13) 0.231(6) 0.00(2) Uiso 0.5 1 d . . P O3 O 0.7141(4) 1.0218(9) 0.1738(4) 0.0738(17) Uani 1 1 d . . . O4 O 0.8211(5) 0.8452(12) 0.2843(6) 0.099(2) Uani 1 1 d . . . N1 N 0.4562(4) 0.0916(7) 0.0941(4) 0.0331(14) Uani 1 1 d . . . H1A H 0.483585 0.056565 0.041101 0.050 Uiso 1 1 calc R U . H1B H 0.483564 0.020286 0.149007 0.050 Uiso 1 1 calc R U . H1C H 0.471393 0.213091 0.108953 0.050 Uiso 1 1 calc R U . C1 C 0.3386(5) 0.0659(8) 0.0660(4) 0.0268(16) Uani 1 1 d . . . H1 H 0.313342 0.133301 0.000472 0.032 Uiso 1 1 calc R U . C2 C 0.3048(5) -0.1449(9) 0.0457(5) 0.0333(17) Uani 1 1 d . . . H2A H 0.282167 -0.171202 -0.027771 0.040 Uiso 1 1 calc R U . H2B H 0.361484 -0.231146 0.076232 0.040 Uiso 1 1 calc R U . C3 C 0.2122(4) -0.1575(8) 0.1000(4) 0.0295(17) Uani 1 1 d . . . H3 H 0.161351 -0.258063 0.072893 0.035 Uiso 1 1 calc R U . C4 C 0.2584(5) -0.1720(8) 0.2166(4) 0.0311(17) Uani 1 1 d . . . H4A H 0.315730 -0.263527 0.231496 0.037 Uiso 1 1 calc R U . H4B H 0.204616 -0.208424 0.253259 0.037 Uiso 1 1 calc R U . C5 C 0.2990(4) 0.0304(8) 0.2461(5) 0.0282(16) Uani 1 1 d . . . H5 H 0.251133 0.083025 0.286669 0.034 Uiso 1 1 calc R U . C6 C 0.2726(4) 0.1394(8) 0.1403(4) 0.0267(16) Uani 1 1 d . . . C7 C 0.1643(5) 0.0430(8) 0.0882(4) 0.0300(16) Uani 1 1 d . . . C8 C 0.1185(5) 0.1006(10) -0.0243(5) 0.0454(19) Uani 1 1 d . . . H8A H 0.168459 0.070734 -0.065621 0.068 Uiso 1 1 calc R U . H8B H 0.104497 0.234580 -0.027716 0.068 Uiso 1 1 calc R U . H8C H 0.053908 0.032447 -0.050212 0.068 Uiso 1 1 calc R U . C9 C 0.0757(4) 0.0751(9) 0.1463(5) 0.0396(18) Uani 1 1 d . . . H9A H 0.014658 0.002337 0.114108 0.059 Uiso 1 1 calc R U . H9B H 0.057644 0.207512 0.144198 0.059 Uiso 1 1 calc R U . H9C H 0.099510 0.035609 0.216996 0.059 Uiso 1 1 calc R U . C10 C 0.2726(5) 0.3529(9) 0.1495(5) 0.0368(17) Uani 1 1 d . . . H10A H 0.250605 0.408105 0.081942 0.055 Uiso 1 1 calc R U . H10B H 0.342634 0.395989 0.180984 0.055 Uiso 1 1 calc R U . H10C H 0.224674 0.390517 0.191531 0.055 Uiso 1 1 calc R U . C11 C 0.4092(5) 0.0539(9) 0.3130(4) 0.0285(17) Uani 1 1 d . . . C12 C 0.4887(5) -0.0782(10) 0.3188(4) 0.0316(17) Uani 1 1 d . . . H12 H 0.473916 -0.191515 0.282341 0.038 Uiso 1 1 calc R U . C13 C 0.5900(5) -0.0471(11) 0.3772(5) 0.0377(18) Uani 1 1 d . . . H13 H 0.642277 -0.137270 0.376790 0.045 Uiso 1 1 calc R U . C14 C 0.6152(5) 0.1180(10) 0.4371(4) 0.0368(19) Uani 1 1 d . . . C15 C 0.5333(5) 0.2469(11) 0.4349(4) 0.0394(18) Uani 1 1 d . . . H15 H 0.546429 0.357341 0.474239 0.047 Uiso 1 1 calc R U . C16 C 0.4331(5) 0.2141(9) 0.3757(5) 0.0348(17) Uani 1 1 d . . . H16 H 0.379856 0.301681 0.377572 0.042 Uiso 1 1 calc R U . C17 C 0.7249(6) 0.1539(14) 0.4949(5) 0.048(2) Uani 1 1 d . . . C18 C 0.7943(6) 0.0096(14) 0.5349(5) 0.054(2) Uani 1 1 d . . . H18 H 0.770420 -0.115346 0.529275 0.064 Uiso 1 1 calc R U . C19 C 0.8985(6) 0.0464(18) 0.5830(6) 0.075(3) Uani 1 1 d . . . H19 H 0.943799 -0.052885 0.609343 0.090 Uiso 1 1 calc R U . C20 C 0.9349(7) 0.2329(19) 0.5919(6) 0.072(3) Uani 1 1 d . . . H20 H 1.004923 0.258962 0.623691 0.087 Uiso 1 1 calc R U . C21 C 0.8677(7) 0.3767(16) 0.5538(6) 0.068(3) Uani 1 1 d . . . H21 H 0.891933 0.501389 0.559779 0.081 Uiso 1 1 calc R U . C22 C 0.7641(6) 0.3400(13) 0.5064(5) 0.054(2) Uani 1 1 d . . . H22 H 0.719171 0.440598 0.481597 0.065 Uiso 1 1 calc R U . C23 C 0.6357(6) 0.4944(12) 0.2508(6) 0.068(2) Uani 1 1 d . . . H23A H 0.647993 0.360310 0.247542 0.102 Uiso 1 1 calc R U . H23B H 0.602210 0.520825 0.306899 0.102 Uiso 1 1 calc R U . H23C H 0.701948 0.560731 0.261697 0.102 Uiso 1 1 calc R U . C24 C 0.5678(5) 0.5568(11) 0.1544(4) 0.0222(16) Uani 1 1 d . . . C25 C 0.8683(6) 1.1689(13) 0.2793(6) 0.067(2) Uani 1 1 d . . . H25A H 0.863213 1.256965 0.223101 0.100 Uiso 1 1 calc R U . H25B H 0.940214 1.127457 0.302011 0.100 Uiso 1 1 calc R U . H25C H 0.845913 1.230021 0.335531 0.100 Uiso 1 1 calc R U . C26 C 0.7991(8) 1.0018(17) 0.2439(7) 0.071(3) 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 O1 0.059(3) 0.043(3) 0.060(3) 0.007(3) 0.036(3) 0.000(3) O2 0.074(4) 0.049(4) 0.052(3) -0.009(3) 0.027(3) -0.003(3) O3 0.062(3) 0.109(5) 0.055(3) 0.017(3) 0.022(3) 0.005(4) O4 0.075(5) 0.098(6) 0.129(6) -0.005(5) 0.033(4) -0.003(5) N1 0.049(4) 0.025(3) 0.034(3) -0.001(2) 0.028(2) 0.005(3) C1 0.033(4) 0.023(4) 0.027(4) 0.000(3) 0.013(3) -0.001(3) C2 0.042(4) 0.028(4) 0.033(4) 0.001(3) 0.013(3) -0.002(3) C3 0.035(4) 0.018(4) 0.035(4) -0.002(3) 0.006(3) -0.002(3) C4 0.032(4) 0.024(4) 0.041(4) 0.003(3) 0.015(3) 0.005(3) C5 0.033(4) 0.024(4) 0.036(4) -0.006(3) 0.024(3) -0.004(3) C6 0.045(4) 0.004(4) 0.035(4) -0.001(3) 0.017(3) -0.001(3) C7 0.036(4) 0.018(4) 0.037(4) 0.001(3) 0.011(3) -0.002(3) C8 0.046(4) 0.036(5) 0.053(4) 0.002(3) 0.009(3) 0.007(4) C9 0.028(4) 0.026(4) 0.065(4) -0.005(3) 0.011(3) 0.001(3) C10 0.038(4) 0.033(5) 0.044(4) -0.004(3) 0.021(3) 0.004(3) C11 0.034(4) 0.029(4) 0.027(4) -0.002(4) 0.017(3) 0.004(4) C12 0.033(4) 0.035(4) 0.032(4) -0.001(3) 0.018(4) -0.009(4) C13 0.039(5) 0.048(5) 0.032(4) 0.005(4) 0.022(3) 0.003(4) C14 0.038(5) 0.052(5) 0.026(4) -0.009(4) 0.017(3) -0.015(4) C15 0.052(5) 0.041(5) 0.029(4) -0.014(3) 0.016(4) -0.005(4) C16 0.037(5) 0.037(5) 0.038(4) -0.002(4) 0.024(4) -0.002(3) C17 0.052(5) 0.070(6) 0.029(4) -0.012(4) 0.025(4) -0.015(6) C18 0.043(5) 0.080(7) 0.042(4) -0.008(4) 0.019(4) -0.011(5) C19 0.038(5) 0.134(10) 0.057(5) -0.022(6) 0.017(4) -0.001(6) C20 0.043(5) 0.121(9) 0.058(5) -0.034(6) 0.022(4) -0.026(7) C21 0.055(6) 0.106(8) 0.047(5) -0.032(5) 0.022(4) -0.024(6) C22 0.045(6) 0.087(8) 0.036(4) -0.013(4) 0.021(4) -0.018(5) C23 0.075(5) 0.056(6) 0.073(6) 0.001(5) 0.019(5) -0.002(5) C24 0.025(4) 0.037(5) 0.007(3) -0.004(4) 0.007(3) 0.010(4) C25 0.052(5) 0.077(7) 0.074(5) -0.017(5) 0.023(4) -0.026(5) C26 0.089(8) 0.087(8) 0.053(6) 0.031(6) 0.046(6) 0.039(7) 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' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C26 O4 H2 99(4) C1 N1 H1A 109.5 C1 N1 H1B 109.5 H1A N1 H1B 109.5 C1 N1 H1C 109.5 H1A N1 H1C 109.5 H1B N1 H1C 109.5 N1 C1 C6 118.9(5) N1 C1 C2 113.0(5) C6 C1 C2 104.9(5) N1 C1 H1 106.4 C6 C1 H1 106.4 C2 C1 H1 106.4 C3 C2 C1 101.2(5) C3 C2 H2A 111.5 C1 C2 H2A 111.5 C3 C2 H2B 111.5 C1 C2 H2B 111.5 H2A C2 H2B 109.4 C4 C3 C2 107.9(5) C4 C3 C7 102.9(5) C2 C3 C7 103.9(5) C4 C3 H3 113.7 C2 C3 H3 113.7 C7 C3 H3 113.7 C3 C4 C5 103.3(5) C3 C4 H4A 111.1 C5 C4 H4A 111.1 C3 C4 H4B 111.1 C5 C4 H4B 111.1 H4A C4 H4B 109.1 C11 C5 C4 118.3(5) C11 C5 C6 117.4(5) C4 C5 C6 103.4(4) C11 C5 H5 105.5 C4 C5 H5 105.5 C6 C5 H5 105.5 C10 C6 C1 113.5(5) C10 C6 C5 114.8(5) C1 C6 C5 111.6(5) C10 C6 C7 116.7(5) C1 C6 C7 98.3(4) C5 C6 C7 100.2(4) C8 C7 C9 106.2(5) C8 C7 C3 113.7(5) C9 C7 C3 114.5(5) C8 C7 C6 115.3(5) C9 C7 C6 114.3(5) C3 C7 C6 92.8(4) C7 C8 H8A 109.5 C7 C8 H8B 109.5 H8A C8 H8B 109.5 C7 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C7 C9 H9A 109.5 C7 C9 H9B 109.5 H9A C9 H9B 109.5 C7 C9 H9C 109.5 H9A C9 H9C 109.5 H9B C9 H9C 109.5 C6 C10 H10A 109.5 C6 C10 H10B 109.5 H10A C10 H10B 109.5 C6 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 C12 C11 C16 116.7(5) C12 C11 C5 123.7(6) C16 C11 C5 119.6(5) C11 C12 C13 121.9(6) C11 C12 H12 119.0 C13 C12 H12 119.0 C12 C13 C14 121.3(6) C12 C13 H13 119.4 C14 C13 H13 119.4 C15 C14 C13 116.6(5) C15 C14 C17 122.7(7) C13 C14 C17 120.6(7) C16 C15 C14 121.3(6) C16 C15 H15 119.4 C14 C15 H15 119.4 C15 C16 C11 122.1(6) C15 C16 H16 119.0 C11 C16 H16 119.0 C18 C17 C22 117.1(7) C18 C17 C14 122.8(8) C22 C17 C14 120.0(8) C17 C18 C19 121.6(9) C17 C18 H18 119.2 C19 C18 H18 119.2 C18 C19 C20 119.6(10) C18 C19 H19 120.2 C20 C19 H19 120.2 C21 C20 C19 119.6(9) C21 C20 H20 120.2 C19 C20 H20 120.2 C20 C21 C22 120.7(9) C20 C21 H21 119.6 C22 C21 H21 119.6 C21 C22 C17 121.3(8) C21 C22 H22 119.3 C17 C22 H22 119.3 C24 C23 H23A 109.5 C24 C23 H23B 109.5 H23A C23 H23B 109.5 C24 C23 H23C 109.5 H23A C23 H23C 109.5 H23B C23 H23C 109.5 O1 C24 O2 118.4(6) O1 C24 C23 128.8(7) O2 C24 C23 112.5(7) C26 C25 H25A 109.5 C26 C25 H25B 109.5 H25A C25 H25B 109.5 C26 C25 H25C 109.5 H25A C25 H25C 109.5 H25B C25 H25C 109.5 O4 C26 O3 119.5(11) O4 C26 C25 120.3(10) O3 C26 C25 120.1(9) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C24 1.145(7) O2 C24 1.390(9) O3 C26 1.282(10) O4 C26 1.231(10) O4 H2 1.21(9) N1 C1 1.499(7) N1 H1A 0.8900 N1 H1B 0.8900 N1 H1C 0.8900 C1 C6 1.532(8) C1 C2 1.554(9) C1 H1 0.9800 C2 C3 1.535(9) C2 H2A 0.9700 C2 H2B 0.9700 C3 C4 1.531(8) C3 C7 1.536(8) C3 H3 0.9800 C4 C5 1.539(8) C4 H4A 0.9700 C4 H4B 0.9700 C5 C11 1.514(8) C5 C6 1.568(9) C5 H5 0.9800 C6 C10 1.508(8) C6 C7 1.575(8) C7 C8 1.533(9) C7 C9 1.535(8) C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 C9 H9A 0.9600 C9 H9B 0.9600 C9 H9C 0.9600 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 C12 1.379(8) C11 C16 1.394(8) C12 C13 1.386(8) C12 H12 0.9300 C13 C14 1.404(9) C13 H13 0.9300 C14 C15 1.393(9) C14 C17 1.480(9) C15 C16 1.380(8) C15 H15 0.9300 C16 H16 0.9300 C17 C18 1.382(11) C17 C22 1.401(11) C18 C19 1.384(10) C18 H18 0.9300 C19 C20 1.392(13) C19 H19 0.9300 C20 C21 1.358(13) C20 H20 0.9300 C21 C22 1.374(10) C21 H21 0.9300 C22 H22 0.9300 C23 C24 1.449(9) C23 H23A 0.9600 C23 H23B 0.9600 C23 H23C 0.9600 C25 C26 1.491(14) C25 H25A 0.9600 C25 H25B 0.9600 C25 H25C 0.9600