#------------------------------------------------------------------------------ #$Date: 2021-11-05 03:51:41 +0200 (Fri, 05 Nov 2021) $ #$Revision: 270320 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158390.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_7158390 loop_ _publ_author_name 'Goryaeva, Marina V.' 'Kushch, Svetlana O.' 'Burgart, Yanina V.' 'Ezhikova, Marina A.' 'Kodess, Mikhail I.' 'Slepukhin, Pavel A.' 'Triandafilova, Galina A.' 'Krasnykh, Olga P.' 'Yakovleva, Ekaterina I.' 'Zarubaev, Vladimir V.' 'Sinegubova, Ekaterina O.' 'Esaulkova, Iana L.' 'Shtro, Anna A.' 'Galochkina, Anastasia V.' 'Nikolaeva, Yulia V.' 'Saloutin, Victor I.' _publ_section_title ; New heteroanalogs of tricyclic ascidian alkaloids: synthesis and biological activity ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB01843D _journal_year 2021 _chemical_formula_moiety 'C11 H14 F3 N O3' _chemical_formula_sum 'C11 H14 F3 N O3' _chemical_formula_weight 265.23 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2021-03-17 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-09-04 deposited with the CCDC. 2021-10-28 downloaded from the CCDC. ; _cell_angle_alpha 93.198(7) _cell_angle_beta 100.084(8) _cell_angle_gamma 92.872(8) _cell_formula_units_Z 2 _cell_length_a 5.4368(6) _cell_length_b 8.6060(7) _cell_length_c 12.6785(11) _cell_measurement_reflns_used 1085 _cell_measurement_temperature 295(2) _cell_measurement_theta_max 28.4020 _cell_measurement_theta_min 4.1820 _cell_volume 582.06(10) _computing_cell_refinement 'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)' _computing_data_collection 'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)' _computing_data_reduction 'CrysAlisPro 1.171.39.38a (Rigaku OD, 2017)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 295(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.5253 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.987 _diffrn_measured_fraction_theta_max 0.857 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -18.00 23.00 1.00 12.00 -- -24.08 101.00-113.00 41 2 \w -65.00 -38.00 1.00 12.00 -- -24.08 101.00-113.00 27 3 \w -23.00 65.00 1.00 12.00 -- 22.52-101.00 142.00 88 4 \w 35.00 81.00 1.00 12.00 -- 22.52 178.00 -90.00 46 5 \w -93.00 -7.00 1.00 12.00 -- -24.08 -57.00-120.00 86 6 \w -90.00 2.00 1.00 12.00 -- -24.08 -77.00 0.00 92 7 \w 9.00 33.00 1.00 12.00 -- -24.08 57.00 30.00 24 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0466616000 _diffrn_orient_matrix_UB_12 -0.0211029000 _diffrn_orient_matrix_UB_13 0.0527331000 _diffrn_orient_matrix_UB_21 0.0552466000 _diffrn_orient_matrix_UB_22 0.0765442000 _diffrn_orient_matrix_UB_23 0.0135303000 _diffrn_orient_matrix_UB_31 -0.1113319000 _diffrn_orient_matrix_UB_32 0.0231331000 _diffrn_orient_matrix_UB_33 0.0167021000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0405 _diffrn_reflns_av_unetI/netI 0.0719 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.857 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 5258 _diffrn_reflns_point_group_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.857 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 30.865 _diffrn_reflns_theta_min 3.814 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.140 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.82866 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.38a (Rigaku Oxford Diffraction, 2017) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.513 _exptl_crystal_description block _exptl_crystal_F_000 276 _exptl_crystal_size_max 0.43 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.263 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.056 _refine_ls_extinction_coef 0.032(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.011 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 188 _refine_ls_number_reflns 3141 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.011 _refine_ls_R_factor_all 0.1090 _refine_ls_R_factor_gt 0.0564 _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^)+(0.0548P)^2^+0.1499P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1207 _refine_ls_wR_factor_ref 0.1697 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1715 _reflns_number_total 3141 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01843d2.cif _cod_data_source_block exp_936 _cod_database_code 7158390 _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 0.990 _shelx_estimated_absorpt_t_min 0.942 _reflns_odcompleteness_completeness 98.30 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 28.22 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H,H) groups 2.a Secondary CH2 refined with riding coordinates: C11(H11A,H11B), C6(H6A,H6B), C8(H8A,H8B), C7(H7A,H7B) ; _shelx_res_file ; TITL exp_936_a.res in P-1 exp_936.res created by SHELXL-2018/3 at 15:23:09 on 17-Mar-2021 REM Old TITL exp_936 in P-1 REM SHELXT solution in P-1: R1 0.220, Rweak 0.009, Alpha 0.034 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C11 N O6 CELL 0.71073 5.4368 8.606 12.6785 93.198 100.084 92.872 ZERR 2 0.0006 0.0007 0.0011 0.007 0.008 0.008 LATT 1 SFAC C H F N O UNIT 22 28 6 2 6 L.S. 10 PLAN 5 SIZE 0.43 0.21 0.07 TEMP 22(2) CONF list 4 fmap 2 53 MORE -1 BOND $H ACTA 52 HTAB OMIT 2 10 6 OMIT -5 -3 12 OMIT 0 -2 2 REM REM REM WGHT 0.054800 0.149900 EXTI 0.032031 FVAR 1.38196 O15 5 0.828528 0.472132 0.662825 11.00000 0.04055 0.04118 = 0.04325 -0.00542 0.01138 0.00120 F1 3 0.524745 0.239441 0.709774 11.00000 0.09378 0.03308 = 0.06139 -0.00284 0.01436 -0.01652 F2 3 0.397871 0.372054 0.835143 11.00000 0.09512 0.05694 = 0.06994 0.00853 0.04269 -0.01471 F3 3 0.783485 0.316965 0.852515 11.00000 0.10070 0.04397 = 0.07070 0.01854 -0.01393 0.00064 O4 5 1.048618 0.842330 0.759114 11.00000 0.04030 0.03956 = 0.06841 0.01173 0.00481 -0.00343 O14 5 0.395099 0.719921 0.509918 11.00000 0.07599 0.04779 = 0.03535 -0.00011 -0.00839 0.00169 N1 4 0.663029 0.808766 0.658283 11.00000 0.04783 0.03207 = 0.03433 0.00479 0.00555 -0.00288 C10 1 0.654440 0.508915 0.730228 11.00000 0.04067 0.03199 = 0.03574 -0.00120 0.01003 -0.00121 C12 1 0.488976 0.704393 0.604405 11.00000 0.04345 0.03498 = 0.03502 -0.00377 0.00477 0.00499 C5 1 0.796837 0.798885 0.768303 11.00000 0.03561 0.03182 = 0.03965 0.00056 0.00028 -0.00319 C9 1 0.785716 0.634944 0.814209 11.00000 0.04741 0.03271 = 0.03374 0.00151 0.00285 0.00095 C11 1 0.417910 0.568627 0.665227 11.00000 0.03896 0.03780 = 0.04291 0.00015 0.00560 -0.00363 AFIX 23 H11A 2 0.331198 0.485896 0.615341 11.00000 -1.20000 H11B 2 0.306279 0.601144 0.713031 11.00000 -1.20000 AFIX 0 C13 1 0.590189 0.359726 0.782332 11.00000 0.06383 0.03351 = 0.04391 0.00060 0.00790 -0.00670 C6 1 0.703094 0.908296 0.849832 11.00000 0.05780 0.04026 = 0.04295 -0.00348 0.00066 0.00573 AFIX 23 H6A 2 0.789637 1.010568 0.855450 11.00000 -1.20000 H6B 2 0.524612 0.919326 0.829734 11.00000 -1.20000 AFIX 0 C2 1 0.798509 0.920299 0.603086 11.00000 0.07089 0.03824 = 0.05192 0.00944 0.01287 -0.00776 C8 1 0.679673 0.660479 0.918069 11.00000 0.09251 0.04442 = 0.03688 -0.00190 0.01699 -0.00710 AFIX 23 H8A 2 0.498676 0.644832 0.904318 11.00000 -1.20000 H8B 2 0.748930 0.590457 0.971384 11.00000 -1.20000 AFIX 0 C7 1 0.762079 0.829544 0.954613 11.00000 0.09216 0.04683 = 0.03880 -0.00586 0.00885 0.00297 AFIX 23 H7A 2 0.667247 0.870116 1.006997 11.00000 -1.20000 H7B 2 0.939274 0.841302 0.984666 11.00000 -1.20000 AFIX 0 C3 1 1.034306 0.963362 0.685283 11.00000 0.05320 0.03846 = 0.07992 0.01674 0.01618 -0.00620 H9 2 0.959554 0.606476 0.832103 11.00000 0.03623 H2A 2 0.832862 0.867467 0.539544 11.00000 0.05942 H3A 2 1.022072 1.068721 0.719156 11.00000 0.07595 H3B 2 1.186592 0.962964 0.651979 11.00000 0.07932 H2B 2 0.698327 1.008531 0.586119 11.00000 0.06841 H15 2 0.750382 0.413104 0.605217 11.00000 0.09998 HKLF 4 REM exp_936_a.res in P-1 REM wR2 = 0.1697, GooF = S = 1.011, Restrained GooF = 1.011 for all data REM R1 = 0.0564 for 1715 Fo > 4sig(Fo) and 0.1090 for all 3141 data REM 188 parameters refined using 0 restraints END WGHT 0.0528 0.1386 REM Instructions for potential hydrogen bonds EQIV $1 x-1, y, z HTAB C11 O4_$1 HTAB C6 O4_$1 EQIV $2 -x+1, -y+1, -z+1 HTAB O15 O14_$2 REM Highest difference peak 0.263, deepest hole -0.251, 1-sigma level 0.056 Q1 1 0.7444 0.6128 0.7451 11.00000 0.05 0.26 Q2 1 0.6824 0.8222 0.7192 11.00000 0.05 0.23 Q3 1 0.7459 0.2971 0.7785 11.00000 0.05 0.23 Q4 1 1.0152 0.8048 0.7018 11.00000 0.05 0.21 Q5 1 0.7239 0.8407 0.6442 11.00000 0.05 0.21 ; _shelx_res_checksum 17033 _shelx_hkl_file ; 0 0 3 3.51 1.58 0 0 3 3.44 1.43 0 0 -3 6.61 2.06 0 0 4 135.73 9.89 0 0 -4 121.88 9.18 0 0 5 70.41 8.03 0 0 -5 76.87 8.64 0 0 6 1278.74 38.05 0 0 -6 1301.02 37.34 0 0 -7 28.26 6.01 0 0 7 29.93 6.21 0 0 8 2.01 1.29 0 0 -8 -1.81 2.78 0 0 9 151.54 16.50 0 0 -9 163.40 16.53 0 0 10 40.77 8.89 0 0 -10 33.06 8.29 0 0 11 119.32 15.63 0 0 -11 148.24 18.01 0 0 12 129.20 17.37 0 0 -12 124.07 17.06 0 0 13 -2.01 1.78 0 0 -13 5.19 4.13 0 0 -14 -1.12 5.02 0 0 -15 12.38 6.90 0 0 -16 46.64 12.94 0 0 -17 -15.49 7.78 0 1 -17 2.60 4.61 0 1 -16 0.37 2.77 0 1 -15 40.92 11.34 0 1 -14 44.26 11.73 0 1 -13 283.15 27.76 0 1 -12 102.02 16.03 0 1 -11 127.61 17.07 0 1 -10 2.17 2.50 0 -1 10 4.15 2.07 0 1 -9 31.90 7.13 0 -1 9 35.94 7.87 0 1 -8 286.54 20.73 0 -1 8 254.59 19.22 0 -1 7 -1.87 1.57 0 1 -7 -3.87 4.47 0 1 -6 165.66 5.44 0 1 -6 193.52 14.92 0 -1 6 188.83 14.09 0 -1 5 1077.64 30.18 0 1 -5 1112.51 32.49 0 1 -5 1017.91 15.99 0 -1 4 407.15 16.72 0 1 -4 435.51 17.89 0 1 -4 448.23 10.93 0 1 -3 1741.22 30.32 0 1 -3 1758.16 33.97 0 1 -2 30.69 3.32 0 -1 2 33.51 4.20 0 -1 -2 2145.13 29.64 0 1 2 1988.48 29.42 0 1 3 264.03 12.86 0 -1 -3 273.90 12.31 0 1 4 15.03 1.94 0 -1 -4 12.50 2.76 0 1 5 340.98 9.14 0 -1 -5 315.88 16.92 0 1 6 2612.20 21.73 0 -1 -6 2633.46 53.79 0 1 6 2587.99 56.97 0 1 7 217.08 17.66 0 -1 -7 206.28 16.20 0 -1 -8 763.39 33.91 0 1 8 758.28 35.75 0 -1 -9 31.70 7.71 0 1 9 31.23 7.43 0 1 10 1.34 1.89 0 -1 -10 -3.16 3.08 0 1 11 22.07 7.49 0 -1 -11 26.72 8.61 0 1 12 4.95 5.00 0 -1 -12 1.80 2.03 0 -1 -13 19.47 7.46 0 1 13 16.51 6.44 0 1 14 6.81 3.14 0 -1 -14 17.71 7.24 0 -1 -15 5.04 4.76 0 1 15 19.21 8.18 0 -1 -16 -1.77 2.61 0 -1 -17 0.01 3.49 0 2 -17 73.56 17.96 0 2 -16 2.51 1.75 0 2 -15 62.56 13.97 0 2 -14 -0.92 4.19 0 2 -13 40.65 10.41 0 2 -12 51.41 10.93 0 2 -11 12.19 4.09 0 2 -10 41.83 9.47 0 -2 9 892.51 18.34 0 2 -9 853.80 39.92 0 2 -8 -2.36 4.12 0 2 -8 0.83 0.73 0 2 -7 91.33 11.22 0 2 -7 89.13 6.77 0 2 -6 158.20 9.49 0 2 -6 194.34 15.81 0 2 -5 124.32 11.59 0 2 -5 105.47 7.93 0 2 -4 2764.18 50.69 0 2 -3 598.19 21.12 0 2 -2 31.27 4.42 0 -2 1 3155.92 40.50 0 2 -1 3029.53 32.85 0 2 0 1293.76 20.68 0 -2 0 1360.55 21.11 0 -2 0 1402.59 19.51 0 2 0 1385.12 20.23 0 2 1 4952.27 43.86 0 -2 -1 5174.38 43.63 0 -2 -2 1102.76 24.13 0 2 2 1039.74 23.64 0 2 3 1872.10 36.44 0 2 4 4.64 2.18 0 2 4 6.66 1.98 0 2 5 326.41 13.75 0 -2 -5 326.57 17.98 0 2 6 0.14 0.61 0 -2 -6 2.47 2.09 0 -2 -7 9.39 3.21 0 2 7 8.02 2.10 0 2 8 249.73 10.17 0 2 8 250.22 20.99 0 -2 -8 223.04 18.75 0 -2 -8 193.10 8.58 0 2 9 63.30 4.10 0 -2 -9 48.33 8.86 0 2 9 50.24 10.24 0 -2 -9 43.89 3.18 0 -2 -10 322.89 25.54 0 2 10 314.29 26.03 0 -2 -11 208.00 21.36 0 2 11 198.72 21.77 0 -2 -12 137.27 18.01 0 2 12 141.03 19.14 0 -2 -13 0.02 2.04 0 2 13 0.51 2.83 0 2 14 37.43 10.77 0 -2 -14 34.90 9.89 0 -2 -15 15.14 7.08 0 2 15 10.03 4.28 0 -2 -16 -5.25 5.45 0 2 16 -6.19 4.27 0 -2 -17 3.48 4.35 0 3 -16 22.89 8.74 0 3 -15 8.08 5.02 0 3 -14 4.53 4.02 0 3 -13 47.49 11.47 0 3 -12 -2.77 3.72 0 3 -11 -0.39 3.18 0 3 -10 207.01 21.46 0 3 -9 490.34 19.27 0 3 -9 541.36 33.23 0 3 -8 85.75 8.34 0 3 -8 82.32 11.74 0 3 -7 160.18 16.27 0 3 -7 153.33 11.51 0 3 -6 1.87 1.25 0 3 -6 -3.70 4.64 0 3 -5 14.38 5.93 0 3 -5 3.00 2.37 0 3 -4 280.24 17.42 0 3 -3 4877.57 67.81 0 3 -1 1769.44 30.95 0 3 -1 1775.69 30.01 0 3 0 41.92 4.22 0 -3 0 48.91 4.90 0 -3 0 48.36 4.49 0 3 0 41.42 4.53 0 -3 -1 62.76 5.86 0 3 1 63.49 5.73 0 3 2 398.32 16.75 0 3 3 2929.52 48.40 0 3 4 1895.81 43.15 0 3 5 144.06 12.83 0 3 5 161.47 11.73 0 -3 -6 734.30 30.69 0 3 6 768.65 25.49 0 -3 -7 18.08 5.08 0 3 7 24.46 4.49 0 -3 -8 438.36 26.60 0 3 8 434.27 18.72 0 3 9 38.34 9.40 0 3 9 48.38 5.79 0 -3 -9 36.06 8.09 0 3 10 341.50 28.30 0 -3 -10 382.58 27.70 0 -3 -11 -3.26 3.45 0 3 11 0.72 2.00 0 -3 -12 -0.95 2.39 0 3 12 -0.59 2.18 0 3 13 117.18 18.47 0 -3 -13 113.36 17.46 0 -3 -14 -7.94 6.25 0 3 14 0.68 3.06 0 3 15 1.93 2.90 0 -3 -15 -2.41 4.70 0 -3 -16 -2.50 4.20 0 -3 -17 -1.82 4.75 0 4 -16 5.24 4.98 0 4 -15 -5.60 4.76 0 4 -14 -6.08 4.73 0 4 -13 3.71 3.48 0 4 -12 19.00 6.67 0 4 -11 97.77 15.29 0 4 -10 34.98 5.91 0 4 -10 31.19 8.35 0 4 -9 239.25 16.49 0 4 -9 275.97 24.65 0 4 -8 102.10 10.99 0 4 -8 116.40 15.34 0 4 -7 -2.21 1.90 0 4 -7 0.89 2.43 0 4 -6 33.45 7.64 0 4 -6 20.32 4.79 0 4 -5 1378.08 40.77 0 4 -5 1462.50 45.43 0 4 -4 152.10 14.15 0 4 -2 430.42 18.55 0 4 -1 3820.06 49.89 0 4 -1 3812.68 51.41 0 4 0 54.22 5.90 0 4 0 57.12 5.70 0 4 1 745.70 22.47 0 -4 -1 446.29 15.47 0 4 2 327.61 16.29 0 -4 -2 113.14 8.33 0 4 3 252.72 15.43 0 4 4 219.98 16.04 0 4 4 207.60 15.16 0 4 5 704.03 28.86 0 4 5 640.90 28.82 0 4 6 49.99 8.67 0 4 6 55.54 7.97 0 -4 -7 76.35 10.87 0 4 7 78.51 9.55 0 -4 -8 -0.13 2.75 0 4 8 1.02 0.82 0 -4 -9 124.30 15.46 0 4 9 134.87 11.98 0 -4 -10 251.29 23.43 0 4 10 252.50 25.05 0 -4 -11 84.82 14.00 0 4 11 71.22 13.40 0 4 12 4.28 3.95 0 -4 -12 -1.52 3.75 0 4 13 66.26 14.12 0 -4 -13 60.56 12.92 0 4 14 -6.32 5.06 0 -4 -14 3.62 3.91 0 -4 -15 -2.35 4.09 0 4 15 -11.68 6.56 0 -4 -16 2.81 4.30 0 5 -15 -2.39 3.49 0 5 -14 5.53 1.68 0 5 -13 -4.06 4.49 0 5 -12 75.52 14.58 0 5 -11 4.43 4.57 0 5 -10 2.30 1.67 0 5 -10 4.69 4.84 0 5 -9 328.56 22.11 0 5 -9 313.31 26.41 0 5 -8 69.66 12.19 0 5 -8 54.79 9.25 0 5 -7 43.02 7.96 0 5 -7 51.79 10.30 0 5 -6 6.81 4.66 0 5 -6 -0.09 0.99 0 5 -5 178.45 17.92 0 5 -5 147.62 14.97 0 5 -4 64.82 8.59 0 5 -4 47.12 8.30 0 5 -3 472.51 22.56 0 5 -2 223.51 14.07 0 5 -2 223.79 14.20 0 5 -1 16.63 3.67 0 5 -1 16.55 3.63 0 5 0 16.78 3.53 0 5 1 271.31 15.01 0 5 2 442.71 20.79 0 5 3 25.89 5.84 0 5 3 23.97 5.00 0 5 4 924.81 33.66 0 5 4 937.91 37.64 0 5 5 330.37 22.22 0 5 5 335.30 21.65 0 5 6 6.84 2.86 0 5 6 7.88 3.62 0 5 7 72.20 10.49 0 5 8 169.06 16.03 0 -5 -8 171.29 18.34 0 5 9 62.13 9.49 0 -5 -9 48.96 9.95 0 -5 -10 50.52 10.89 0 5 11 2.98 3.08 0 -5 -11 2.40 3.55 0 -5 -12 2.70 3.08 0 5 12 3.75 2.91 0 -5 -13 4.10 3.86 0 5 13 3.35 2.88 0 5 14 7.14 4.95 0 -5 -14 0.93 1.54 0 -5 -15 9.87 7.02 0 6 -14 -2.75 3.51 0 6 -13 1.12 2.30 0 6 -12 22.15 7.54 0 6 -11 22.23 8.03 0 6 -10 4.83 2.65 0 6 -10 11.71 5.97 0 6 -9 17.96 6.83 0 6 -9 27.57 7.08 0 6 -8 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2.11 -5 -1 -4 1.38 1.75 -5 -1 -5 3.91 2.32 5 1 5 12.31 6.07 -5 -1 -5 11.45 4.71 -5 -1 -6 28.81 8.08 5 1 6 28.99 9.14 -5 -1 -6 47.64 10.99 -5 -1 -7 1.36 1.92 5 1 7 2.77 4.06 -5 -1 -7 1.61 2.93 5 1 8 14.70 6.92 5 1 9 -3.38 3.51 5 1 10 0.01 2.36 5 2 -14 3.73 5.80 5 2 -13 2.78 4.01 5 2 -12 -3.87 3.64 5 2 -11 -2.41 2.86 5 2 -10 5.21 4.89 5 2 -9 13.19 6.12 5 2 -8 2.66 1.94 5 2 -7 76.85 15.05 5 2 -7 57.31 10.08 5 2 -6 107.69 17.36 5 2 -6 112.07 13.26 5 2 -5 2.00 2.10 5 2 -4 157.26 20.51 5 2 -3 300.43 28.31 5 2 -2 13.09 6.53 5 2 -1 68.15 12.96 5 2 0 27.89 7.97 5 2 1 12.39 5.76 5 2 2 55.92 11.67 5 2 3 47.12 10.63 5 2 4 1.78 2.92 5 2 5 15.49 6.67 5 2 6 10.06 4.81 -5 -2 -7 21.92 7.83 5 2 7 32.60 10.66 5 2 8 0.00 2.27 5 2 9 4.18 4.66 5 2 10 0.01 3.83 5 3 -14 35.64 11.65 5 3 -13 4.13 6.53 5 3 -12 0.78 1.25 5 3 -11 0.00 2.47 5 3 -10 2.09 3.04 5 3 -9 2.35 2.60 5 3 -8 28.44 9.82 5 3 -8 33.73 8.24 5 3 -7 -2.31 4.35 5 3 -6 71.23 14.59 5 3 -5 4.10 3.10 5 3 -4 19.88 8.14 5 3 -3 73.55 14.43 5 3 -2 117.27 18.24 5 3 -1 86.16 15.40 5 3 0 1.45 3.27 5 3 1 28.33 8.30 5 3 2 29.92 9.69 5 3 3 22.85 8.06 5 3 4 1.79 2.98 5 3 5 13.86 7.29 5 3 6 4.01 2.99 5 3 7 1.25 2.77 5 3 8 5.44 6.40 5 3 9 1.83 2.93 5 4 -14 3.28 6.60 5 4 -13 -7.38 5.19 5 4 -12 0.05 1.00 5 4 -11 -0.69 1.86 5 4 -10 4.06 4.46 5 4 -9 15.70 6.98 5 4 -8 -2.04 3.43 5 4 -7 1.12 2.60 5 4 -6 -0.70 2.14 -5 -4 6 1.04 3.28 -5 -4 5 12.39 5.06 5 4 -5 9.25 4.32 5 4 -4 1.03 2.56 -5 -4 4 -1.51 3.81 5 4 -3 5.85 3.79 -5 -4 3 12.34 5.96 5 4 -2 24.75 8.54 -5 -4 2 28.74 9.45 5 4 -1 46.67 11.98 -5 -4 1 42.06 10.60 5 4 0 21.45 7.57 -5 -4 0 10.66 5.08 -5 -4 -1 51.77 12.05 5 4 1 49.36 12.15 5 4 2 60.67 13.41 5 4 3 -2.87 3.57 5 4 4 4.06 3.54 5 4 5 36.12 11.67 5 4 6 5.94 3.23 5 4 7 13.34 8.39 5 4 8 -3.12 3.83 5 5 -14 -8.37 5.84 5 5 -13 -5.94 4.76 5 5 -11 -6.04 5.33 5 5 -10 2.97 3.24 5 5 -9 28.23 10.14 -5 -5 9 13.81 6.49 5 5 -8 -5.35 5.77 -5 -5 8 0.02 1.61 5 5 -7 14.21 7.67 -5 -5 7 1.51 2.32 5 5 -6 -4.61 5.14 -5 -5 6 -2.49 3.60 -5 -5 5 17.23 6.42 5 5 -5 18.31 8.33 -5 -5 4 5.96 4.73 5 5 -4 -2.47 2.93 5 5 -3 4.26 4.31 -5 -5 3 -0.97 4.41 5 5 -2 8.98 4.93 -5 -5 2 23.99 8.09 -5 -5 1 56.09 12.60 5 5 -1 64.58 13.87 -5 -5 0 6.18 5.07 5 5 0 9.05 5.43 5 5 1 5.55 5.58 -5 -5 -1 0.00 2.95 -5 -5 -2 9.09 6.45 5 5 2 9.22 4.91 5 5 3 2.04 2.81 -5 -5 -3 -0.42 2.64 -5 -5 -4 0.59 1.76 5 5 4 -3.10 3.45 5 5 5 17.32 9.62 5 5 6 -5.11 6.67 -5 -6 11 7.54 5.74 -5 -6 10 -2.85 3.24 5 6 -10 9.04 6.90 5 6 -9 -3.64 4.98 -5 -6 9 -11.92 7.24 5 6 -8 -0.19 2.07 -5 -6 8 10.37 6.46 5 6 -7 -1.08 5.08 -5 -6 7 6.57 5.84 5 6 -6 88.11 18.18 -5 -6 6 68.39 15.07 5 6 -5 15.66 7.48 -5 -6 5 17.60 7.85 5 6 -4 4.85 5.16 -5 -6 4 3.14 4.23 5 6 -3 25.60 9.37 -5 -6 3 20.72 8.18 5 6 -2 13.93 7.31 -5 -6 2 6.07 4.63 5 6 -1 3.59 2.52 -5 -6 1 0.23 1.30 5 6 0 13.48 7.81 -5 -6 0 4.20 5.01 5 6 1 8.92 5.47 -5 -6 -1 8.66 5.98 5 6 2 31.31 10.41 -5 -6 -2 10.50 6.53 -5 -6 -3 -5.20 4.27 5 6 3 4.50 3.67 5 6 4 7.37 6.26 -5 -6 -4 0.86 2.77 5 6 5 -6.76 5.58 -5 -6 -5 0.03 2.13 -5 -7 11 1.63 4.56 -5 -7 10 0.01 1.68 -5 -7 9 7.82 6.24 5 7 -8 0.56 2.98 -5 -7 8 8.49 6.50 5 7 -7 7.35 3.51 -5 -7 7 1.63 2.77 -5 -7 6 2.83 4.15 5 7 -6 -7.42 5.74 -5 -7 5 71.14 16.41 5 7 -5 99.48 19.95 -5 -7 4 1.02 2.34 5 7 -4 -0.81 2.24 -5 -7 3 8.35 6.71 5 7 -3 21.97 9.14 -5 -7 2 1.66 2.09 5 7 -2 0.10 2.90 -5 -7 1 0.37 3.75 5 7 -1 5.18 4.30 -5 -7 0 -3.79 4.01 5 7 0 6.91 6.50 -5 -7 -1 0.01 1.95 5 7 1 1.60 2.35 5 7 2 0.17 2.83 -5 -7 -2 2.14 3.56 5 7 3 13.58 8.25 -5 -7 -3 -3.67 3.86 -5 -7 -4 -3.23 3.56 -5 -7 -5 8.84 8.54 5 8 -5 0.83 1.63 5 8 -4 9.84 7.41 5 8 -3 2.37 5.34 5 8 -2 2.35 1.63 5 8 -1 1.65 3.03 -6 6 10 12.03 7.93 -6 6 9 0.87 3.71 -6 6 8 8.93 6.69 -6 6 7 0.67 1.80 -6 6 6 -1.72 2.96 -6 6 5 3.22 4.11 -6 6 4 0.64 2.56 -6 6 3 -2.12 4.73 -6 6 2 -3.02 4.56 -6 6 1 1.91 2.04 -6 6 0 36.12 12.00 -6 6 -1 -3.89 4.01 -6 6 -2 35.53 11.70 -6 6 -3 1.75 1.69 -6 6 -4 8.18 6.51 -6 6 -5 -0.20 1.43 -6 6 -6 6.25 6.32 -6 5 10 0.93 3.15 6 -5 -10 4.54 6.22 -6 5 9 -1.33 3.17 6 -5 -9 0.48 2.78 -6 5 8 1.13 2.62 6 -5 -8 11.07 7.40 -6 5 7 4.18 4.44 -6 5 6 12.44 7.90 -6 5 5 14.67 7.15 -6 5 4 3.49 1.66 -6 5 3 3.20 3.37 -6 5 2 -5.07 5.20 -6 5 1 11.49 6.97 -6 5 0 15.88 8.06 -6 5 -1 8.26 5.61 -6 5 -2 9.03 6.19 -6 5 -3 -5.42 4.58 -6 5 -4 2.96 4.26 -6 5 -4 13.69 7.53 -6 5 -5 -4.23 4.14 -6 5 -5 -3.01 3.63 -6 5 -6 -0.01 2.27 6 -4 -11 0.01 3.67 6 -4 -10 -12.33 6.71 -6 4 9 -0.48 1.45 6 -4 -9 -3.34 3.47 -6 4 8 -0.78 1.87 6 -4 -8 3.79 4.19 -6 4 7 9.87 6.03 6 -4 -7 3.19 4.32 -6 4 6 5.82 4.29 -6 4 5 25.43 9.35 -6 4 4 -5.22 5.34 -6 4 3 1.18 2.45 -6 4 2 1.39 2.33 -6 4 1 19.40 8.05 -6 4 0 9.81 6.61 -6 4 -1 -5.77 3.93 -6 4 -2 25.55 9.30 -6 4 -3 45.13 12.97 -6 4 -4 3.02 3.42 -6 4 -4 3.92 4.56 -6 4 -5 -0.02 0.91 -6 4 -6 0.47 2.43 6 -3 -12 -5.26 4.66 6 -3 -11 -3.90 3.84 6 -3 -10 9.57 7.21 6 -3 -9 9.18 6.71 6 -3 -8 3.01 4.03 6 -3 -7 -3.44 3.18 -6 3 7 -8.97 5.48 6 -3 -6 -4.86 3.63 -6 3 6 3.38 3.88 -6 3 5 -7.86 5.90 6 -3 -5 -3.70 3.10 -6 3 5 -1.65 2.94 -6 3 4 1.40 1.69 -6 3 4 -3.43 4.75 -6 3 3 -0.09 1.30 -6 3 3 3.12 4.40 -6 3 2 23.91 8.94 -6 3 2 12.59 5.61 -6 3 1 9.44 4.99 -6 3 1 22.42 8.13 -6 3 0 33.62 10.65 -6 3 0 29.81 9.37 -6 3 -1 4.70 3.92 -6 3 -1 9.43 5.39 -6 3 -2 53.87 12.90 -6 3 -4 3.97 4.00 -6 3 -5 19.90 8.52 -6 3 -6 10.47 7.29 -6 3 -7 -2.00 2.87 6 -2 -12 5.47 4.62 6 -2 -11 -2.77 3.32 6 -2 -10 9.59 6.87 -6 2 10 17.00 7.86 -6 2 9 -6.06 4.44 6 -2 -9 -5.04 4.00 -6 2 8 23.34 8.73 6 -2 -8 5.87 4.79 -6 2 7 27.25 9.23 6 -2 -7 7.39 4.79 -6 2 6 1.13 1.18 6 -2 -6 6.20 3.96 -6 2 5 9.31 5.71 6 -2 -5 4.29 3.98 -6 2 4 2.38 2.95 -6 2 3 2.71 2.52 -6 2 2 31.51 10.02 -6 2 1 4.83 2.69 -6 2 0 2.53 3.79 -6 2 -1 2.58 3.45 -6 2 -2 -1.84 2.75 -6 2 -3 0.65 1.76 -6 2 -4 9.69 5.38 -6 2 -4 6.69 4.94 -6 2 -5 50.39 13.37 -6 2 -5 30.75 10.50 -6 2 -6 4.21 4.13 -6 2 -6 -2.54 2.84 -6 2 -7 0.01 2.06 -6 2 -8 -4.43 4.16 6 -1 -13 0.01 3.98 6 -1 -12 0.17 2.75 -6 1 11 -5.24 4.14 6 -1 -11 -5.15 4.23 -6 1 10 6.60 5.50 6 -1 -10 9.69 7.12 6 -1 -9 -5.31 5.11 -6 1 9 1.60 3.21 6 -1 -9 2.50 3.45 6 -1 -8 4.74 3.69 -6 1 8 9.91 5.52 6 -1 -8 17.50 7.20 6 -1 -7 -0.89 1.65 -6 1 7 -7.99 4.95 6 -1 -7 -7.03 4.76 6 -1 -6 5.46 3.65 -6 1 6 -1.52 3.51 6 -1 -5 25.59 8.14 -6 1 5 41.16 10.69 6 -1 -4 2.44 2.73 -6 1 4 -0.87 3.27 6 -1 -3 -0.52 1.78 -6 1 3 -6.88 5.34 6 -1 -2 2.77 3.42 -6 1 2 2.40 4.02 6 -1 -1 28.48 7.91 -6 1 1 49.96 11.72 6 -1 0 -2.04 2.56 -6 1 0 -0.86 3.49 6 -1 1 27.35 7.72 -6 1 -1 29.26 8.54 6 -1 2 -0.27 1.57 -6 1 -2 5.15 4.62 6 -1 3 1.31 1.53 -6 1 -3 3.10 3.21 -6 1 -4 1.17 1.76 -6 1 -4 1.53 1.53 6 -1 5 -0.79 2.31 -6 1 -5 0.48 1.88 -6 1 -6 -2.27 2.82 -6 1 -6 6.49 5.10 -6 1 -7 -2.98 3.30 -6 1 -8 -5.20 4.37 -6 1 -9 0.02 3.02 6 0 -13 10.64 9.07 6 0 -12 0.01 3.51 -6 0 11 3.49 3.25 6 0 -11 -0.50 1.51 -6 0 10 0.07 2.19 6 0 -10 -2.73 3.74 6 0 -9 0.00 2.16 -6 0 9 0.24 2.52 6 0 -8 0.36 1.65 -6 0 8 0.21 3.46 6 0 -7 1.54 1.68 -6 0 7 -3.65 3.37 6 0 -6 7.44 4.16 -6 0 6 9.67 5.14 6 0 -5 0.72 1.36 -6 0 5 1.04 2.03 6 0 -4 32.49 9.24 -6 0 4 27.86 8.41 6 0 -3 47.79 10.77 -6 0 3 45.60 10.80 6 0 -2 5.28 3.56 -6 0 2 7.35 5.17 6 0 -1 11.54 5.85 -6 0 1 8.64 4.95 6 0 0 12.73 5.92 -6 0 0 15.77 5.81 6 0 1 3.23 3.20 -6 0 -1 10.13 3.49 6 0 2 3.14 2.69 -6 0 -2 -2.83 2.86 6 0 3 4.85 3.99 -6 0 -3 2.85 2.79 6 0 4 -0.74 2.50 -6 0 -4 -3.86 3.39 6 0 5 1.64 3.31 -6 0 -5 1.01 2.93 -6 0 -5 1.06 1.65 6 0 6 5.51 4.95 -6 0 -6 13.12 6.20 6 0 7 9.51 6.40 6 0 8 0.01 1.28 6 0 9 -3.58 3.69 6 1 -13 3.18 4.27 6 1 -12 4.84 4.09 -6 -1 11 12.10 6.52 6 1 -11 0.00 3.27 6 1 -10 3.20 4.37 -6 -1 10 4.33 3.91 6 1 -9 -2.35 3.05 -6 -1 9 -1.99 2.40 6 1 -8 -0.24 1.72 -6 -1 8 4.37 3.97 6 1 -7 2.39 4.06 -6 -1 7 13.63 6.66 6 1 -6 21.76 8.24 6 1 -5 2.29 1.43 6 1 -4 14.30 6.82 6 1 -3 3.65 2.54 6 1 -2 1.28 2.15 6 1 -1 8.96 4.80 6 1 0 1.69 1.31 -6 -1 -1 1.00 2.67 6 1 1 9.36 5.02 -6 -1 -2 9.77 5.21 6 1 2 9.68 5.34 -6 -1 -3 6.44 4.14 6 1 3 12.09 6.00 -6 -1 -4 0.07 1.10 6 1 4 0.61 3.94 -6 -1 -5 1.83 1.56 6 1 5 -2.64 3.09 -6 -1 -6 5.49 4.40 6 1 6 0.50 1.64 6 1 7 -3.91 3.89 6 1 8 0.01 3.81 6 2 -11 -2.11 3.11 -6 -2 11 -3.84 3.37 6 2 -10 4.80 5.04 6 2 -9 -6.18 4.90 6 2 -8 8.33 5.92 6 2 -7 7.55 5.24 6 2 -6 -2.57 3.24 6 2 -5 10.59 6.60 6 2 -4 28.53 9.29 6 2 -3 1.14 3.02 6 2 -2 45.55 11.98 6 2 -1 1.16 2.13 6 2 0 -0.35 2.62 6 2 1 2.03 2.43 6 2 2 -3.56 3.52 6 2 3 -1.11 2.16 6 2 4 -6.59 4.92 -6 -2 -5 -0.51 1.32 6 2 5 1.61 3.80 -6 -2 -6 -2.82 2.84 6 2 6 7.67 6.16 6 2 7 -3.58 3.88 6 3 -11 -4.92 4.79 6 3 -10 -3.79 4.42 6 3 -9 5.73 5.70 6 3 -8 13.21 7.53 6 3 -7 11.85 6.97 6 3 -6 20.44 8.43 6 3 -5 8.73 5.15 6 3 -4 22.60 9.14 6 3 -3 -0.14 2.38 6 3 -2 41.55 12.06 6 3 -1 -2.10 2.85 6 3 0 7.44 5.67 6 3 1 10.63 6.70 6 3 2 8.73 5.78 6 3 3 0.01 3.08 6 3 4 10.15 6.47 6 3 5 -7.99 5.78 6 3 6 -0.01 2.72 6 4 -10 -9.42 6.55 6 4 -9 0.01 2.37 6 4 -8 8.29 6.31 6 4 -7 -2.20 3.21 6 4 -6 18.19 8.34 6 4 -5 17.08 8.47 6 4 -4 1.19 3.62 6 4 -3 7.08 5.02 6 4 -2 60.72 15.08 6 4 -1 11.91 5.63 6 4 0 55.05 14.27 6 4 1 10.95 6.59 6 4 2 17.81 8.97 6 4 3 -2.18 4.73 6 4 4 0.44 1.97 6 5 -8 21.24 10.66 6 5 -7 10.05 6.42 6 5 -6 60.25 16.01 6 5 -5 3.19 3.34 6 5 -4 21.97 9.24 6 5 -3 14.72 7.91 6 5 -2 50.47 13.72 6 5 -1 5.19 2.90 6 5 0 20.03 8.68 6 5 1 18.84 8.32 6 5 2 -3.35 5.11 -6 -6 5 92.22 19.17 6 6 -4 4.25 4.71 -6 -6 4 -1.36 3.13 6 6 -3 36.17 12.51 -6 -6 3 28.37 10.67 -6 -6 2 2.36 3.53 6 6 -2 3.17 4.01 -6 -6 1 0.82 2.71 -7 3 6 18.15 8.88 -7 3 5 18.74 9.38 -7 3 4 -11.53 6.72 -7 3 3 9.08 6.97 -7 3 2 0.13 4.07 -7 3 1 0.01 3.40 -7 3 0 1.88 2.28 -7 3 -1 6.54 5.01 -7 2 9 5.91 5.65 -7 2 8 1.64 2.43 -7 2 7 4.00 4.08 -7 2 6 13.68 7.46 -7 2 5 9.68 7.05 -7 2 4 5.09 5.96 -7 2 3 1.36 1.34 -7 2 2 14.56 8.56 -7 2 1 -6.50 5.07 -7 2 0 12.36 6.97 -7 2 -1 0.03 2.85 -7 2 -2 0.27 2.93 -7 2 -3 2.58 3.35 -7 2 -4 16.12 9.15 -7 1 10 0.04 1.33 -7 1 9 2.85 2.70 -7 1 8 2.87 2.98 -7 1 7 5.89 4.70 -7 1 6 9.51 6.38 -7 1 5 0.85 3.74 -7 1 4 31.93 10.79 -7 1 3 10.37 5.93 -7 1 2 -2.34 3.14 -7 1 1 -0.01 3.67 -7 1 0 -7.42 5.27 -7 1 -1 -4.22 3.98 -7 1 -2 -4.32 4.03 -7 1 -3 14.00 8.27 -7 1 -4 12.05 8.04 7 0 -11 3.09 6.51 7 0 -10 -10.93 6.50 -7 0 10 0.69 2.09 7 0 -9 2.97 4.77 -7 0 9 6.20 5.62 7 0 -8 1.88 4.38 -7 0 8 2.88 4.49 7 0 -7 -3.64 3.61 -7 0 7 2.81 4.15 7 0 -6 1.18 3.06 -7 0 6 8.10 5.97 7 0 -5 10.32 6.79 -7 0 5 34.28 10.79 7 0 -4 3.79 4.48 -7 0 4 -8.87 5.67 7 0 -3 2.26 3.40 -7 0 3 0.10 1.18 7 0 -2 1.09 2.72 -7 0 2 0.00 1.39 7 0 -1 1.32 1.89 -7 0 1 7.56 5.47 7 0 0 6.94 5.45 -7 0 0 14.09 7.38 -7 0 -1 0.23 0.71 -7 0 -2 6.61 5.53 -7 0 -3 3.90 5.15 -7 0 -4 3.00 4.45 7 1 -10 -7.02 5.44 7 1 -9 13.97 7.52 -7 -1 9 32.64 11.54 7 1 -8 0.79 2.07 -7 -1 8 3.56 4.89 7 1 -7 5.81 6.89 -7 -1 7 16.29 7.16 7 1 -6 1.26 3.59 -7 -1 6 7.73 4.92 7 1 -5 -1.38 2.42 -7 -1 5 -5.45 4.39 7 1 -4 5.41 5.45 -7 -1 4 -13.57 6.78 7 1 -3 4.61 4.79 -7 -1 3 0.00 2.24 -7 -1 2 0.00 1.04 7 1 -2 -0.03 1.06 -7 -1 1 30.52 10.32 7 1 -1 5.09 4.95 -7 -1 0 0.00 1.99 7 1 0 -6.47 4.67 -7 -1 -1 28.32 10.22 7 1 1 18.45 9.57 -7 -1 -2 7.78 5.44 7 1 2 0.02 1.62 -7 -1 -3 12.03 7.55 7 1 3 6.31 4.94 7 1 4 0.81 4.35 7 2 -8 -0.86 2.18 7 2 -7 6.00 6.72 -7 -2 7 6.18 4.46 7 2 -6 -11.29 6.71 7 2 -5 -2.67 3.29 7 2 -4 3.60 5.42 7 2 -3 0.68 1.88 7 2 -2 0.84 4.36 7 2 -1 -0.01 2.49 7 2 0 2.13 3.73 -7 -2 -1 -5.39 4.34 7 2 1 -8.78 5.74 7 2 2 4.47 6.12 7 2 3 -12.87 7.27 7 3 -6 9.58 7.61 7 3 -5 -17.59 8.51 7 3 -4 -0.37 6.46 7 3 -3 -4.86 4.35 7 3 -2 -0.83 2.08 7 3 -1 2.90 4.68 7 3 0 5.33 6.48 0 0 0 0.00 0.00 TITL exp_936 in P-1 REM P-1 (#2 in standard setting) CELL 0.71073 5.436793 8.606014 12.678544 93.1982 100.0843 92.8718 ZERR 3.00 0.000572 0.000747 0.001095 0.0071 0.0080 0.0078 LATT 1 SFAC C H N O UNIT 33.00 30.00 3.00 3.00 TREF HKLF 4 END _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' ; _shelx_hkl_checksum 39558 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.134 _oxdiff_exptl_absorpt_empirical_full_min 0.857 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 _atom_site_disorder_assembly _atom_site_disorder_group O15 O 0.8285(3) 0.47213(19) 0.66283(14) 0.0415(4) Uani 1 1 d . . . . . F1 F 0.5247(3) 0.23944(17) 0.70977(13) 0.0636(5) Uani 1 1 d . . . . . F2 F 0.3979(3) 0.3721(2) 0.83514(13) 0.0711(5) Uani 1 1 d . . . . . F3 F 0.7835(3) 0.31696(19) 0.85252(14) 0.0749(6) Uani 1 1 d . . . . . O4 O 1.0486(3) 0.8423(2) 0.75911(15) 0.0499(5) Uani 1 1 d . . . . . O14 O 0.3951(4) 0.7199(2) 0.50992(14) 0.0554(5) Uani 1 1 d . . . . . N1 N 0.6630(4) 0.8088(2) 0.65828(15) 0.0384(5) Uani 1 1 d . . . . . C10 C 0.6544(4) 0.5089(3) 0.73023(17) 0.0360(5) Uani 1 1 d . . . . . C12 C 0.4890(4) 0.7044(3) 0.60440(18) 0.0382(5) Uani 1 1 d . . . . . C5 C 0.7968(4) 0.7989(3) 0.76830(18) 0.0367(5) Uani 1 1 d . . . . . C9 C 0.7857(5) 0.6349(3) 0.81421(18) 0.0386(5) Uani 1 1 d . . . . . C11 C 0.4179(4) 0.5686(3) 0.66523(19) 0.0404(6) Uani 1 1 d . . . . . H11A H 0.331198 0.485896 0.615341 0.048 Uiso 1 1 calc R U . . . H11B H 0.306279 0.601144 0.713031 0.048 Uiso 1 1 calc R U . . . C13 C 0.5902(5) 0.3597(3) 0.7823(2) 0.0477(6) Uani 1 1 d . . . . . C6 C 0.7031(5) 0.9083(3) 0.84983(19) 0.0482(6) Uani 1 1 d . . . . . H6A H 0.789637 1.010568 0.855450 0.058 Uiso 1 1 calc R U . . . H6B H 0.524612 0.919326 0.829734 0.058 Uiso 1 1 calc R U . . . C2 C 0.7985(6) 0.9203(3) 0.6031(2) 0.0536(7) Uani 1 1 d . . . . . C8 C 0.6797(6) 0.6605(3) 0.9181(2) 0.0578(8) Uani 1 1 d . . . . . H8A H 0.498676 0.644832 0.904318 0.069 Uiso 1 1 calc R U . . . H8B H 0.748930 0.590457 0.971384 0.069 Uiso 1 1 calc R U . . . C7 C 0.7621(6) 0.8295(3) 0.9546(2) 0.0600(8) Uani 1 1 d . . . . . H7A H 0.667247 0.870116 1.006997 0.072 Uiso 1 1 calc R U . . . H7B H 0.939274 0.841302 0.984666 0.072 Uiso 1 1 calc R U . . . C3 C 1.0343(6) 0.9634(3) 0.6853(3) 0.0565(8) Uani 1 1 d . . . . . H9 H 0.960(4) 0.606(3) 0.8321(18) 0.036(6) Uiso 1 1 d . . . . . H2A H 0.833(5) 0.867(3) 0.540(2) 0.059(8) Uiso 1 1 d . . . . . H3A H 1.022(6) 1.069(4) 0.719(2) 0.076(10) Uiso 1 1 d . . . . . H3B H 1.187(6) 0.963(4) 0.652(2) 0.079(10) Uiso 1 1 d . . . . . H2B H 0.698(5) 1.009(4) 0.586(2) 0.068(9) Uiso 1 1 d . . . . . H15 H 0.750(7) 0.413(4) 0.605(3) 0.100(13) Uiso 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 O15 0.0405(9) 0.0412(10) 0.0432(10) -0.0054(8) 0.0114(7) 0.0012(7) F1 0.0938(13) 0.0331(8) 0.0614(10) -0.0028(7) 0.0144(9) -0.0165(8) F2 0.0951(13) 0.0569(11) 0.0699(12) 0.0085(9) 0.0427(10) -0.0147(9) F3 0.1007(14) 0.0440(9) 0.0707(12) 0.0185(8) -0.0139(10) 0.0006(9) O4 0.0403(9) 0.0396(10) 0.0684(12) 0.0117(8) 0.0048(8) -0.0034(7) O14 0.0760(13) 0.0478(11) 0.0354(10) -0.0001(8) -0.0084(9) 0.0017(9) N1 0.0478(11) 0.0321(10) 0.0343(10) 0.0048(8) 0.0055(8) -0.0029(8) C10 0.0407(12) 0.0320(11) 0.0357(12) -0.0012(9) 0.0100(9) -0.0012(9) C12 0.0434(12) 0.0350(12) 0.0350(12) -0.0038(9) 0.0048(10) 0.0050(10) C5 0.0356(11) 0.0318(11) 0.0397(13) 0.0006(9) 0.0003(9) -0.0032(9) C9 0.0474(14) 0.0327(12) 0.0337(12) 0.0015(9) 0.0028(10) 0.0009(10) C11 0.0390(12) 0.0378(13) 0.0429(13) 0.0001(10) 0.0056(10) -0.0036(10) C13 0.0638(17) 0.0335(13) 0.0439(14) 0.0006(10) 0.0079(12) -0.0067(11) C6 0.0578(16) 0.0403(14) 0.0429(14) -0.0035(11) 0.0007(11) 0.0057(12) C2 0.0709(19) 0.0382(15) 0.0519(18) 0.0094(12) 0.0129(14) -0.0078(14) C8 0.093(2) 0.0444(15) 0.0369(14) -0.0019(11) 0.0170(13) -0.0071(14) C7 0.092(2) 0.0468(16) 0.0388(15) -0.0059(12) 0.0088(14) 0.0030(15) C3 0.0532(17) 0.0385(15) 0.080(2) 0.0167(14) 0.0162(15) -0.0062(12) 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' F F 0.0171 0.0103 '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 C10 O15 H15 109(2) . . ? C5 O4 C3 106.19(18) . . ? C12 N1 C5 125.99(19) . . ? C12 N1 C2 121.7(2) . . ? C2 N1 C5 109.71(19) . . ? O15 C10 C9 106.51(18) . . ? O15 C10 C11 110.70(18) . . ? O15 C10 C13 107.31(19) . . ? C11 C10 C9 110.60(18) . . ? C13 C10 C9 111.40(18) . . ? C13 C10 C11 110.22(19) . . ? O14 C12 N1 121.0(2) . . ? O14 C12 C11 122.8(2) . . ? N1 C12 C11 116.26(19) . . ? O4 C5 N1 102.28(18) . . ? O4 C5 C9 109.50(18) . . ? O4 C5 C6 111.35(19) . . ? N1 C5 C9 115.76(18) . . ? N1 C5 C6 113.10(18) . . ? C6 C5 C9 104.97(19) . . ? C10 C9 C5 112.48(18) . . ? C10 C9 C8 117.9(2) . . ? C10 C9 H9 105.6(13) . . ? C5 C9 H9 105.9(14) . . ? C8 C9 C5 105.0(2) . . ? C8 C9 H9 109.3(13) . . ? C10 C11 H11A 109.8 . . ? C10 C11 H11B 109.8 . . ? C12 C11 C10 109.32(18) . . ? C12 C11 H11A 109.8 . . ? C12 C11 H11B 109.8 . . ? H11A C11 H11B 108.3 . . ? F1 C13 F2 105.8(2) . . ? F1 C13 C10 111.9(2) . . ? F2 C13 C10 113.3(2) . . ? F3 C13 F1 106.5(2) . . ? F3 C13 F2 106.8(2) . . ? F3 C13 C10 112.0(2) . . ? C5 C6 H6A 110.9 . . ? C5 C6 H6B 110.9 . . ? H6A C6 H6B 108.9 . . ? C7 C6 C5 104.20(19) . . ? C7 C6 H6A 110.9 . . ? C7 C6 H6B 110.9 . . ? N1 C2 C3 102.4(2) . . ? N1 C2 H2A 107.7(18) . . ? N1 C2 H2B 109.7(18) . . ? C3 C2 H2A 112.4(17) . . ? C3 C2 H2B 112.9(18) . . ? H2A C2 H2B 111(2) . . ? C9 C8 H8A 111.1 . . ? C9 C8 H8B 111.1 . . ? H8A C8 H8B 109.1 . . ? C7 C8 C9 103.3(2) . . ? C7 C8 H8A 111.1 . . ? C7 C8 H8B 111.1 . . ? C6 C7 C8 101.4(2) . . ? C6 C7 H7A 111.5 . . ? C6 C7 H7B 111.5 . . ? C8 C7 H7A 111.5 . . ? C8 C7 H7B 111.5 . . ? H7A C7 H7B 109.3 . . ? O4 C3 C2 105.2(2) . . ? O4 C3 H3A 113.7(18) . . ? O4 C3 H3B 107.9(19) . . ? C2 C3 H3A 109.2(17) . . ? C2 C3 H3B 111.7(18) . . ? H3A C3 H3B 109(3) . . ? 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 O15 C10 1.418(3) . ? O15 H15 0.89(4) . ? F1 C13 1.337(3) . ? F2 C13 1.342(3) . ? F3 C13 1.334(3) . ? O4 C5 1.427(3) . ? O4 C3 1.435(3) . ? O14 C12 1.235(3) . ? N1 C12 1.338(3) . ? N1 C5 1.465(3) . ? N1 C2 1.462(3) . ? C10 C9 1.532(3) . ? C10 C11 1.529(3) . ? C10 C13 1.529(3) . ? C12 C11 1.506(3) . ? C5 C9 1.558(3) . ? C5 C6 1.529(3) . ? C9 C8 1.537(3) . ? C9 H9 0.98(2) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C6 C7 1.517(4) . ? C2 C3 1.519(4) . ? C2 H2A 0.95(3) . ? C2 H2B 0.97(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 C7 1.523(4) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C3 H3A 0.99(3) . ? C3 H3B 0.99(3) . ? 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O15 C10 C9 C5 76.9(2) . . . . ? O15 C10 C9 C8 -160.7(2) . . . . ? O15 C10 C11 C12 -54.9(2) . . . . ? O15 C10 C13 F1 -50.7(3) . . . . ? O15 C10 C13 F2 -170.17(18) . . . . ? O15 C10 C13 F3 68.9(3) . . . . ? O4 C5 C9 C10 -109.5(2) . . . . ? O4 C5 C9 C8 121.0(2) . . . . ? O4 C5 C6 C7 -92.3(2) . . . . ? O14 C12 C11 C10 136.8(2) . . . . ? N1 C12 C11 C10 -42.7(3) . . . . ? N1 C5 C9 C10 5.4(3) . . . . ? N1 C5 C9 C8 -124.1(2) . . . . ? N1 C5 C6 C7 153.2(2) . . . . ? N1 C2 C3 O4 17.8(3) . . . . ? C10 C9 C8 C7 -154.3(2) . . . . ? C12 N1 C5 O4 135.7(2) . . . . ? C12 N1 C5 C9 16.8(3) . . . . ? C12 N1 C5 C6 -104.4(3) . . . . ? C12 N1 C2 C3 -157.6(2) . . . . ? C5 O4 C3 C2 -35.4(3) . . . . ? C5 N1 C12 O14 -176.6(2) . . . . ? C5 N1 C12 C11 2.9(3) . . . . ? C5 N1 C2 C3 5.2(3) . . . . ? C5 C9 C8 C7 -28.1(3) . . . . ? C5 C6 C7 C8 -43.7(3) . . . . ? C9 C10 C11 C12 62.9(2) . . . . ? C9 C10 C13 F1 -166.9(2) . . . . ? C9 C10 C13 F2 73.6(3) . . . . ? C9 C10 C13 F3 -47.4(3) . . . . ? C9 C5 C6 C7 26.1(2) . . . . ? C9 C8 C7 C6 44.3(3) . . . . ? C11 C10 C9 C5 -43.5(3) . . . . ? C11 C10 C9 C8 79.0(3) . . . . ? C11 C10 C13 F1 70.0(3) . . . . ? C11 C10 C13 F2 -49.6(3) . . . . ? C11 C10 C13 F3 -170.5(2) . . . . ? C13 C10 C9 C5 -166.4(2) . . . . ? C13 C10 C9 C8 -44.0(3) . . . . ? C13 C10 C11 C12 -173.49(19) . . . . ? C6 C5 C9 C10 130.9(2) . . . . ? C6 C5 C9 C8 1.4(2) . . . . ? C2 N1 C12 O14 -16.7(4) . . . . ? C2 N1 C12 C11 162.9(2) . . . . ? C2 N1 C5 O4 -26.2(3) . . . . ? C2 N1 C5 C9 -145.2(2) . . . . ? C2 N1 C5 C6 93.7(3) . . . . ? C3 O4 C5 N1 37.7(2) . . . . ? C3 O4 C5 C9 161.0(2) . . . . ? C3 O4 C5 C6 -83.4(2) . . . . ?