#------------------------------------------------------------------------------ #$Date: 2019-10-28 02:15:44 +0200 (Mon, 28 Oct 2019) $ #$Revision: 219588 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/24/1552484.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_1552484 loop_ _publ_author_name 'Wang, Guotong' 'Cui, Pengcheng' 'Bai, Hongjin' 'Wei, Sanyue' 'Li, Shengkun' _publ_section_title ; Late-Stage C-H Functionalization of Nicotinamides for the Expedient Discovery of Novel Antifungal Leads. ; _journal_name_full 'Journal of agricultural and food chemistry' _journal_paper_doi 10.1021/acs.jafc.9b05349 _journal_year 2019 _chemical_formula_moiety 'C17 H17 N3 O3' _chemical_formula_sum 'C17 H17 N3 O3' _chemical_formula_weight 311.33 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -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 88.093(9) _cell_angle_beta 83.682(9) _cell_angle_gamma 89.913(9) _cell_formula_units_Z 2 _cell_length_a 7.7965(9) _cell_length_b 8.6490(9) _cell_length_c 10.9982(11) _cell_measurement_reflns_used 2882 _cell_measurement_temperature 99.99(10) _cell_measurement_theta_max 28.9580 _cell_measurement_theta_min 2.6360 _cell_volume 736.72(14) _computing_cell_refinement 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2684 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _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 -60.00 40.00 1.00 1.00 -- 11.74 -57.00 -90.00 100 2 \w -21.00 88.00 1.00 1.00 -- 11.74 77.00-180.00 109 3 \w -16.00 85.00 1.00 1.00 -- 11.74 57.00 60.00 101 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0448665000 _diffrn_orient_matrix_UB_12 0.0531381000 _diffrn_orient_matrix_UB_13 0.0396587000 _diffrn_orient_matrix_UB_21 0.0198069000 _diffrn_orient_matrix_UB_22 -0.0456254000 _diffrn_orient_matrix_UB_23 0.0513827000 _diffrn_orient_matrix_UB_31 0.0772852000 _diffrn_orient_matrix_UB_32 0.0427513000 _diffrn_orient_matrix_UB_33 0.0013927000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0205 _diffrn_reflns_av_unetI/netI 0.0349 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 5288 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.996 _diffrn_reflns_theta_max 24.996 _diffrn_reflns_theta_min 2.356 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.89627 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015) 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 1.403 _exptl_crystal_description block _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.169 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.053 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 209 _refine_ls_number_reflns 2589 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0441 _refine_ls_R_factor_gt 0.0386 _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^)+(0.0376P)^2^+0.2875P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0863 _refine_ls_wR_factor_ref 0.0906 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2276 _reflns_number_total 2589 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL b26-2_a.res in P-1 b26-2.res created by SHELXL-2018/3 at 17:24:14 on 18-Jan-2019 REM Old TITL b26-2 in P-1 REM SHELXT solution in P-1: R1 0.115, Rweak 0.007, Alpha 0.028 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N3 O3 CELL 0.71073 7.7965 8.649 10.9982 88.093 83.682 89.913 ZERR 2 0.0009 0.0009 0.0011 0.009 0.009 0.009 LATT 1 SFAC C H N O UNIT 34 34 6 6 L.S. 20 PLAN 20 BOND $H list 4 fmap 2 acta OMIT -3 50 REM REM REM WGHT 0.037600 0.287500 FVAR 0.86614 O2 4 0.769403 0.093374 0.739572 11.00000 0.02496 0.01346 = 0.01805 0.00064 0.00296 0.00224 O3 4 0.685162 0.707632 0.409919 11.00000 0.02940 0.01376 = 0.01451 0.00182 -0.00131 0.00630 O1 4 0.432862 0.154489 0.891915 11.00000 0.01506 0.02582 = 0.01653 -0.00383 0.00067 -0.00510 N2 3 0.761993 0.346029 0.669154 11.00000 0.01922 0.01155 = 0.01173 -0.00165 -0.00067 0.00159 AFIX 43 H2 2 0.732900 0.437220 0.692508 11.00000 -1.20000 AFIX 0 N1 3 0.767735 0.441809 1.052318 11.00000 0.01900 0.01969 = 0.01292 -0.00042 -0.00377 -0.00015 N3 3 0.634388 0.630251 0.609604 11.00000 0.01665 0.01254 = 0.01572 -0.00126 -0.00067 0.00070 C13 1 0.699723 0.599613 0.501259 11.00000 0.01339 0.01251 = 0.01433 0.00204 -0.00432 -0.00325 C7 1 0.822007 0.333959 0.543734 11.00000 0.01173 0.01544 = 0.01203 -0.00054 -0.00210 -0.00302 C6 1 0.744467 0.231368 0.757636 11.00000 0.00972 0.01547 = 0.01444 0.00048 -0.00142 -0.00056 C5 1 0.693833 0.290176 0.883971 11.00000 0.01581 0.01257 = 0.01250 0.00297 -0.00251 0.00327 C12 1 0.793475 0.458452 0.461676 11.00000 0.01051 0.01396 = 0.01378 -0.00140 -0.00303 -0.00155 C1 1 0.536229 0.245244 0.950358 11.00000 0.01631 0.01454 = 0.01399 0.00209 -0.00459 0.00082 C8 1 0.914983 0.205426 0.499209 11.00000 0.01555 0.01452 = 0.01622 0.00252 -0.00176 0.00048 AFIX 43 H8 2 0.935207 0.123261 0.552438 11.00000 -1.20000 AFIX 0 C9 1 0.977498 0.199417 0.375942 11.00000 0.01521 0.01610 = 0.01707 -0.00314 -0.00024 0.00179 AFIX 43 H9 2 1.038551 0.112978 0.347525 11.00000 -1.20000 AFIX 0 C2 1 0.498036 0.300552 1.067896 11.00000 0.01505 0.02069 = 0.01387 0.00252 0.00001 0.00109 AFIX 43 H2A 2 0.395566 0.273131 1.115076 11.00000 -1.20000 AFIX 0 C3 1 0.615969 0.397217 1.112903 11.00000 0.01899 0.02085 = 0.01199 0.00016 -0.00257 0.00420 AFIX 43 H3 2 0.587883 0.434047 1.191060 11.00000 -1.20000 AFIX 0 C4 1 0.802233 0.386829 0.938917 11.00000 0.01514 0.01425 = 0.01422 0.00283 -0.00036 0.00153 AFIX 43 H4 2 0.906170 0.415775 0.894318 11.00000 -1.20000 AFIX 0 C11 1 0.859414 0.449383 0.338415 11.00000 0.01471 0.01506 = 0.01407 0.00317 -0.00347 -0.00258 AFIX 43 H11 2 0.842139 0.531550 0.284433 11.00000 -1.20000 AFIX 0 C10 1 0.949712 0.320902 0.295110 11.00000 0.01585 0.01926 = 0.01249 -0.00161 0.00054 -0.00110 AFIX 43 H10 2 0.991239 0.316163 0.212749 11.00000 -1.20000 AFIX 0 C15 1 0.600398 0.840194 0.467955 11.00000 0.02025 0.01163 = 0.02069 -0.00152 -0.00124 0.00324 AFIX 23 H15A 2 0.496019 0.866569 0.431436 11.00000 -1.20000 H15B 2 0.676485 0.929436 0.460674 11.00000 -1.20000 AFIX 0 C14 1 0.558036 0.786836 0.602830 11.00000 0.01911 0.01342 = 0.01864 -0.00255 -0.00224 0.00128 AFIX 23 H14A 2 0.609100 0.855965 0.656539 11.00000 -1.20000 H14B 2 0.434271 0.783028 0.625487 11.00000 -1.20000 AFIX 0 C16 1 0.259670 0.124024 0.949686 11.00000 0.01514 0.02440 = 0.02032 0.00116 0.00176 -0.00376 AFIX 23 H16A 2 0.199612 0.220122 0.968271 11.00000 -1.20000 H16B 2 0.262756 0.063091 1.025066 11.00000 -1.20000 AFIX 0 C17 1 0.170958 0.035421 0.858182 11.00000 0.02068 0.03749 = 0.02503 -0.00185 -0.00111 -0.00843 AFIX 137 H17A 2 0.172503 0.095942 0.783297 11.00000 -1.50000 H17B 2 0.053666 0.014406 0.890737 11.00000 -1.50000 H17C 2 0.230361 -0.060358 0.842394 11.00000 -1.50000 AFIX 0 HKLF 4 REM b26-2_a.res in P-1 REM wR2 = 0.0906, GooF = S = 1.027, Restrained GooF = 1.027 for all data REM R1 = 0.0386 for 2276 Fo > 4sig(Fo) and 0.0441 for all 2589 data REM 209 parameters refined using 0 restraints END WGHT 0.0417 0.2201 REM Highest difference peak 0.169, deepest hole -0.259, 1-sigma level 0.053 Q1 1 0.7776 0.2746 0.9256 11.00000 0.05 0.17 Q2 1 0.6553 0.5783 0.6692 11.00000 0.05 0.17 Q3 1 0.7150 0.3862 0.8849 11.00000 0.05 0.16 Q4 1 0.7130 0.2762 0.8254 11.00000 0.05 0.15 Q5 1 0.8664 0.4269 0.5060 11.00000 0.05 0.15 Q6 1 0.6533 0.4092 0.6937 11.00000 0.05 0.15 Q7 1 0.7852 0.6278 0.6606 11.00000 0.05 0.14 Q8 1 0.3751 0.8312 0.5006 11.00000 0.05 0.14 Q9 1 1.0257 0.3150 0.1875 11.00000 0.05 0.14 Q10 1 0.9630 0.1362 0.5715 11.00000 0.05 0.14 Q11 1 0.6164 0.3030 0.5101 11.00000 0.05 0.14 Q12 1 0.9411 0.2985 0.5305 11.00000 0.05 0.14 Q13 1 0.7867 0.9355 0.4576 11.00000 0.05 0.13 Q14 1 0.1488 0.1147 0.6389 11.00000 0.05 0.13 Q15 1 0.7545 0.3805 0.4932 11.00000 0.05 0.13 Q16 1 0.7742 0.4180 0.3874 11.00000 0.05 0.13 Q17 1 0.7306 0.9036 0.4044 11.00000 0.05 0.13 Q18 1 0.5895 0.5996 1.1717 11.00000 0.05 0.13 Q19 1 0.6027 0.2910 0.8998 11.00000 0.05 0.13 Q20 1 0.8694 0.4681 0.4160 11.00000 0.05 0.13 REM The information below was added by Olex2. REM REM R1 = 0.0386 for 2276 Fo > 4sig(Fo) and 0.0441 for all 6240 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.17, deepest hole -0.26 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0441 REM R1_gt = 0.0386 REM wR_ref = 0.0906 REM GOOF = 1.027 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 6240 REM Reflections_gt = 2276 REM Parameters = n/a REM Hole = -0.26 REM Peak = 0.17 REM Flack = n/a ; _cod_data_source_file jf9b05349_si_005.cif _cod_data_source_block b26-2 _cod_database_code 1552484 _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. ; _reflns_odcompleteness_completeness 99.83 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 26.32 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C15(H15A,H15B), C14(H14A,H14B), C16(H16A,H16B) 2.b Aromatic/amide H refined with riding coordinates: N2(H2), C8(H8), C9(H9), C2(H2A), C3(H3), C4(H4), C11(H11), C10(H10) 2.c Idealised Me refined as rotating group: C17(H17A,H17B,H17C) ; _olex2_date_sample_data_collection 2019-01-17 _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 1.283 _oxdiff_exptl_absorpt_empirical_full_min 0.776 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 O2 O 0.76940(13) 0.09337(12) 0.73957(10) 0.0192(3) Uani 1 1 d . O3 O 0.68516(14) 0.70763(12) 0.40992(9) 0.0194(3) Uani 1 1 d . O1 O 0.43286(13) 0.15449(12) 0.89191(10) 0.0192(3) Uani 1 1 d . N2 N 0.76199(15) 0.34603(14) 0.66915(11) 0.0142(3) Uani 1 1 d . H2 H 0.732900 0.437220 0.692508 0.017 Uiso 1 1 calc R N1 N 0.76773(16) 0.44181(15) 1.05232(11) 0.0171(3) Uani 1 1 d . N3 N 0.63439(15) 0.63025(14) 0.60960(11) 0.0150(3) Uani 1 1 d . C13 C 0.69972(18) 0.59961(16) 0.50126(13) 0.0133(3) Uani 1 1 d . C7 C 0.82201(18) 0.33396(17) 0.54373(13) 0.0130(3) Uani 1 1 d . C6 C 0.74447(17) 0.23137(17) 0.75764(13) 0.0132(3) Uani 1 1 d . C5 C 0.69383(18) 0.29018(17) 0.88397(13) 0.0136(3) Uani 1 1 d . C12 C 0.79347(17) 0.45845(17) 0.46168(13) 0.0126(3) Uani 1 1 d . C1 C 0.53623(18) 0.24524(17) 0.95036(14) 0.0148(3) Uani 1 1 d . C8 C 0.91498(18) 0.20543(18) 0.49921(14) 0.0155(3) Uani 1 1 d . H8 H 0.935207 0.123261 0.552438 0.019 Uiso 1 1 calc R C9 C 0.97750(18) 0.19942(18) 0.37594(14) 0.0162(3) Uani 1 1 d . H9 H 1.038551 0.112978 0.347525 0.019 Uiso 1 1 calc R C2 C 0.49804(19) 0.30055(18) 1.06790(14) 0.0167(3) Uani 1 1 d . H2A H 0.395566 0.273131 1.115076 0.020 Uiso 1 1 calc R C3 C 0.61597(19) 0.39722(18) 1.11290(14) 0.0172(3) Uani 1 1 d . H3 H 0.587883 0.434047 1.191060 0.021 Uiso 1 1 calc R C4 C 0.80223(18) 0.38683(17) 0.93892(14) 0.0147(3) Uani 1 1 d . H4 H 0.906170 0.415775 0.894318 0.018 Uiso 1 1 calc R C11 C 0.85941(18) 0.44938(17) 0.33841(14) 0.0146(3) Uani 1 1 d . H11 H 0.842139 0.531550 0.284433 0.017 Uiso 1 1 calc R C10 C 0.94971(18) 0.32090(18) 0.29511(14) 0.0160(3) Uani 1 1 d . H10 H 0.991239 0.316163 0.212749 0.019 Uiso 1 1 calc R C15 C 0.6004(2) 0.84019(17) 0.46796(14) 0.0176(3) Uani 1 1 d . H15A H 0.496019 0.866569 0.431436 0.021 Uiso 1 1 calc R H15B H 0.676485 0.929436 0.460674 0.021 Uiso 1 1 calc R C14 C 0.5580(2) 0.78684(17) 0.60283(14) 0.0170(3) Uani 1 1 d . H14A H 0.609100 0.855965 0.656539 0.020 Uiso 1 1 calc R H14B H 0.434271 0.783028 0.625487 0.020 Uiso 1 1 calc R C16 C 0.25967(19) 0.12402(19) 0.94969(15) 0.0203(4) Uani 1 1 d . H16A H 0.199612 0.220122 0.968271 0.024 Uiso 1 1 calc R H16B H 0.262756 0.063091 1.025066 0.024 Uiso 1 1 calc R C17 C 0.1710(2) 0.0354(2) 0.85818(16) 0.0278(4) Uani 1 1 d . H17A H 0.172503 0.095942 0.783297 0.042 Uiso 1 1 calc GR H17B H 0.053666 0.014406 0.890737 0.042 Uiso 1 1 calc GR H17C H 0.230361 -0.060358 0.842394 0.042 Uiso 1 1 calc GR 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 O2 0.0250(6) 0.0135(6) 0.0181(6) 0.0006(5) 0.0030(4) 0.0022(4) O3 0.0294(6) 0.0138(6) 0.0145(6) 0.0018(5) -0.0013(5) 0.0063(4) O1 0.0151(6) 0.0258(6) 0.0165(6) -0.0038(5) 0.0007(4) -0.0051(4) N2 0.0192(7) 0.0116(7) 0.0117(7) -0.0016(5) -0.0007(5) 0.0016(5) N1 0.0190(7) 0.0197(7) 0.0129(7) -0.0004(6) -0.0038(5) -0.0002(5) N3 0.0167(7) 0.0125(7) 0.0157(7) -0.0013(5) -0.0007(5) 0.0007(5) C13 0.0134(8) 0.0125(8) 0.0143(8) 0.0020(6) -0.0043(6) -0.0032(6) C7 0.0117(7) 0.0154(8) 0.0120(8) -0.0005(6) -0.0021(6) -0.0030(6) C6 0.0097(7) 0.0155(8) 0.0144(8) 0.0005(6) -0.0014(6) -0.0006(6) C5 0.0158(8) 0.0126(8) 0.0125(8) 0.0030(6) -0.0025(6) 0.0033(6) C12 0.0105(7) 0.0140(8) 0.0138(8) -0.0014(6) -0.0030(6) -0.0015(6) C1 0.0163(8) 0.0145(8) 0.0140(8) 0.0021(6) -0.0046(6) 0.0008(6) C8 0.0156(8) 0.0145(8) 0.0162(8) 0.0025(6) -0.0018(6) 0.0005(6) C9 0.0152(8) 0.0161(8) 0.0171(8) -0.0031(7) -0.0002(6) 0.0018(6) C2 0.0150(8) 0.0207(8) 0.0139(8) 0.0025(7) 0.0000(6) 0.0011(6) C3 0.0190(8) 0.0209(9) 0.0120(8) 0.0002(6) -0.0026(6) 0.0042(6) C4 0.0151(8) 0.0142(8) 0.0142(8) 0.0028(6) -0.0004(6) 0.0015(6) C11 0.0147(8) 0.0151(8) 0.0141(8) 0.0032(6) -0.0035(6) -0.0026(6) C10 0.0159(8) 0.0193(8) 0.0125(8) -0.0016(6) 0.0005(6) -0.0011(6) C15 0.0203(8) 0.0116(8) 0.0207(9) -0.0015(6) -0.0012(6) 0.0032(6) C14 0.0191(8) 0.0134(8) 0.0186(8) -0.0025(6) -0.0022(6) 0.0013(6) C16 0.0151(8) 0.0244(9) 0.0203(9) 0.0012(7) 0.0018(6) -0.0038(6) C17 0.0207(9) 0.0375(11) 0.0250(10) -0.0018(8) -0.0011(7) -0.0084(7) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 C13 O3 C15 106.13(11) C1 O1 C16 117.91(11) C7 N2 H2 115.9 C6 N2 H2 115.9 C6 N2 C7 128.16(12) C3 N1 C4 115.42(13) C13 N3 C14 106.91(12) O3 C13 C12 114.48(12) N3 C13 O3 118.16(13) N3 C13 C12 127.36(13) N2 C7 C12 119.00(13) C8 C7 N2 121.97(13) C8 C7 C12 118.98(13) O2 C6 N2 124.82(14) O2 C6 C5 121.94(13) N2 C6 C5 113.23(12) C1 C5 C6 120.50(13) C4 C5 C6 121.19(13) C4 C5 C1 118.29(13) C7 C12 C13 122.56(13) C11 C12 C13 118.41(13) C11 C12 C7 119.02(13) O1 C1 C5 116.18(13) O1 C1 C2 125.85(13) C2 C1 C5 117.94(14) C7 C8 H8 119.7 C9 C8 C7 120.58(14) C9 C8 H8 119.7 C8 C9 H9 119.7 C10 C9 C8 120.69(14) C10 C9 H9 119.7 C1 C2 H2A 120.7 C3 C2 C1 118.60(14) C3 C2 H2A 120.7 N1 C3 C2 125.01(14) N1 C3 H3 117.5 C2 C3 H3 117.5 N1 C4 C5 124.73(13) N1 C4 H4 117.6 C5 C4 H4 117.6 C12 C11 H11 119.2 C10 C11 C12 121.50(14) C10 C11 H11 119.2 C9 C10 H10 120.4 C11 C10 C9 119.22(14) C11 C10 H10 120.4 O3 C15 H15A 110.9 O3 C15 H15B 110.9 O3 C15 C14 104.27(11) H15A C15 H15B 108.9 C14 C15 H15A 110.9 C14 C15 H15B 110.9 N3 C14 C15 104.36(11) N3 C14 H14A 110.9 N3 C14 H14B 110.9 C15 C14 H14A 110.9 C15 C14 H14B 110.9 H14A C14 H14B 108.9 O1 C16 H16A 110.6 O1 C16 H16B 110.6 O1 C16 C17 105.69(12) H16A C16 H16B 108.7 C17 C16 H16A 110.6 C17 C16 H16B 110.6 C16 C17 H17A 109.5 C16 C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17B 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O2 C6 1.2281(18) O3 C13 1.3628(18) O3 C15 1.4534(17) O1 C1 1.3521(18) O1 C16 1.4483(17) N2 H2 0.8600 N2 C7 1.4142(18) N2 C6 1.362(2) N1 C3 1.3430(19) N1 C4 1.3488(19) N3 C13 1.2793(19) N3 C14 1.4814(19) C13 C12 1.475(2) C7 C12 1.415(2) C7 C8 1.399(2) C6 C5 1.507(2) C5 C1 1.407(2) C5 C4 1.388(2) C12 C11 1.401(2) C1 C2 1.394(2) C8 H8 0.9300 C8 C9 1.392(2) C9 H9 0.9300 C9 C10 1.386(2) C2 H2A 0.9300 C2 C3 1.385(2) C3 H3 0.9300 C4 H4 0.9300 C11 H11 0.9300 C11 C10 1.384(2) C10 H10 0.9300 C15 H15A 0.9700 C15 H15B 0.9700 C15 C14 1.539(2) C14 H14A 0.9700 C14 H14B 0.9700 C16 H16A 0.9700 C16 H16B 0.9700 C16 C17 1.511(2) C17 H17A 0.9600 C17 H17B 0.9600 C17 H17C 0.9600 loop_ _refln_index_h _refln_index_k _refln_index_l _refln_F_squared_meas _refln_F_squared_sigma 0 0 -2 2278.11 14.37 0 0 2 2279.42 14.86 0 0 3 27.48 2.03 0 0 -3 25.4 1.92 0 0 3 27.88 1.99 0 0 -3 23.65 1.81 0 0 4 232.05 6.63 0 0 -4 224.95 6.6 0 0 4 218.09 6.58 0 0 -4 222.21 6.42 0 0 5 881.81 14.46 0 0 -5 909.09 14.79 0 0 -5 900.94 14.46 0 0 -6 362.17 10.19 0 0 6 356.99 10.15 0 0 7 172.09 7.68 0 0 -7 178.58 7.83 0 0 -7 173.33 7.71 0 0 -8 43.52 4.15 0 0 8 37.77 3.92 0 0 -8 40.26 4.04 0 0 -9 86.04 6.39 0 0 -10 17.92 3.11 0 0 -11 141.19 9.38 0 0 -12 21.25 3.78 0 0 -13 13.27 3.5 0 0 -13 10.51 3.13 0 0 -14 95.15 9.26 0 1 -13 35.14 5.49 0 1 -13 27.21 4.97 0 1 -12 5.17 2.24 0 1 -12 1.78 0.91 0 1 -11 117.27 9.22 0 1 -11 100.86 8.21 0 1 -10 137.4 8.98 0 1 -10 149.71 9.7 0 1 -9 72.19 6.28 0 1 -9 62.73 5.69 0 1 -8 349.13 11.37 0 1 -8 326.49 12 0 -1 7 50.25 4.2 0 1 -7 49.4 3.98 0 1 -7 47.32 4.28 0 -1 6 91.66 5.25 0 1 -6 82.01 4.67 0 1 -6 87.54 5.3 0 1 -5 275.69 7.72 0 1 -5 275.21 8.57 0 -1 5 290.55 8.41 0 -1 4 47.02 3.03 0 1 -4 48.33 2.89 0 1 -4 51.95 3.34 0 1 -3 496.87 7.82 0 1 -3 499.01 9.51 0 -1 3 507.88 8.91 0 1 -3 504.85 9.37 0 1 -2 1861.68 11.9 0 1 -2 1841.38 15.94 0 1 -1 0.54 0.27 0 1 0 814.21 8.57 0 -1 -1 1041.62 9.63 0 1 1 1027.58 8.41 0 -1 -1 1020.78 8.33 0 -1 -2 18.83 1.47 0 1 2 22.08 1.61 0 1 2 19.79 1.56 0 1 3 69.4 3.43 0 1 3 77.93 3.52 0 -1 -3 71.9 3.26 0 1 4 14.96 1.75 0 1 4 10.31 1.5 0 -1 -4 10.41 1.4 0 -1 -5 1090.05 16.17 0 1 5 1126.22 16.84 0 -1 -6 437.92 11.27 0 1 6 435.62 11.36 0 -1 -7 202.91 8.64 0 -1 -7 195.4 8.22 0 1 7 208.82 8.6 0 1 8 41.74 4.12 0 -1 -8 32.22 3.54 0 -1 -9 30.62 3.78 0 -1 -10 59.7 5.57 0 -1 -11 14.32 3 0 -1 -12 10.79 2.73 0 -1 -13 21.73 4.12 0 -1 -14 51.2 6.8 0 2 -13 2.66 1.52 0 2 -12 2 1.56 0 2 -11 -0.56 0.88 0 2 -10 29.57 4.57 0 2 -9 2.32 1.3 0 2 -9 1.84 0.8 0 2 -8 15.04 2.84 0 2 -8 20.72 3.27 0 2 -8 13.04 2.1 0 2 -7 95.68 6.64 0 -2 7 93.16 5.82 0 2 -6 490.81 10.93 0 -2 6 494.03 12.63 0 2 -6 523.97 14.46 0 2 -5 551.88 10.35 0 -2 5 570.58 12.61 0 2 -5 555.26 13.71 0 2 -4 1.04 0.45 0 -2 4 0.76 0.55 0 2 -4 0.99 0.66 0 2 -3 119.67 3.47 0 2 -3 116.85 5.42 0 2 -2 1361.5 8.43 0 2 -2 1371.97 17.24 0 2 -1 142.02 5.22 0 2 0 1483.49 7.8 0 2 0 1461.46 16.37 0 -2 0 1477.84 7.39 0 -2 -1 1819 12.6 0 2 1 1797.09 18.1 0 2 1 1823.11 12.87 0 2 2 179.77 4.99 0 -2 -2 166.01 5.85 0 -2 -2 169.17 5.47 0 -2 -2 169.44 4.75 0 2 2 172.52 5.76 0 -2 -3 1.38 0.49 0 2 3 1.96 0.67 0 2 3 1.7 0.63 0 -2 -4 302.01 8.37 0 2 4 301.39 8.57 0 2 4 301.26 8.71 0 2 5 144.51 6.57 0 2 5 134.03 6.3 0 -2 -5 127.61 5.75 0 -2 -6 49.66 3.87 0 2 6 42.7 3.9 0 -2 -7 14.77 2.4 0 2 7 15.94 2.55 0 -2 -7 13.96 2.21 0 -2 -8 16.96 2.65 0 -2 -9 97.32 6.76 0 -2 -10 176.03 9.61 0 -2 -11 88.65 7.21 0 -2 -12 3.01 1.74 0 -2 -13 2.42 1.12 0 3 -13 33.66 5.86 0 3 -12 5.68 2.58 0 3 -11 -0.39 0.86 0 3 -10 165.21 11.25 0 3 -9 5.62 2.06 0 3 -9 6.06 1.6 0 3 -8 119.73 6.18 0 3 -8 118.53 8.44 0 3 -7 141.77 8.68 0 -3 6 1.8 0.98 0 3 -6 2.84 0.85 0 3 -5 0.65 0.43 0 -3 5 0 0.29 0 3 -4 289.22 5.93 0 3 -4 311.01 10.83 0 3 -3 338.04 4.93 0 3 -3 337.14 10.62 0 3 -2 111.37 5.79 0 3 -1 18.01 2.29 0 3 0 14.64 2.06 0 -3 0 10.35 0.8 0 3 1 24.46 1.65 0 3 1 22.31 2.44 0 -3 -1 20.81 2.43 0 3 2 98.23 3.99 0 -3 -2 102.72 5.51 0 -3 -2 102.09 5.12 0 -3 -2 101.32 3.93 0 3 2 112.55 5.58 0 -3 -3 62.72 4.49 0 -3 -3 59.28 3.98 0 -3 -3 65.01 3.62 0 3 3 65.8 3.76 0 3 3 64.85 4.34 0 3 4 69.06 4.27 0 -3 -4 69.27 4.18 0 3 4 59.45 4.43 0 -3 -4 68.3 4.36 0 -3 -4 67.14 4.93 0 -3 -5 1.41 0.68 0 -3 -5 1.86 0.81 0 3 5 0.77 0.6 0 3 6 21.03 2.96 0 -3 -6 21.37 2.7 0 -3 -6 19.67 2.66 0 -3 -7 61.26 4.83 0 -3 -7 65.49 5.16 0 3 7 63.79 5.49 0 -3 -8 18.85 2.89 0 -3 -9 1.15 1.03 0 -3 -10 28.71 4.05 0 -3 -11 47.42 5.4 0 -3 -12 0.47 0.76 0 -3 -13 -0.38 0.81 0 4 -12 -0.12 0.72 0 4 -11 7.5 2.85 0 4 -10 42.83 6.06 0 4 -9 60.94 6.83 0 4 -9 61.65 4.57 0 4 -8 1.53 1.28 0 4 -7 29.19 4.36 0 4 -7 25.4 2.47 0 4 -6 1.2 1.05 0 4 -6 1.32 0.55 0 -4 5 291.24 10.72 0 -4 5 287.75 11.01 0 4 -5 270.45 6.07 0 4 -5 272.41 11.81 0 4 -4 73.84 2.5 0 4 -4 68.99 5.71 0 4 -3 388.73 12.93 0 4 -2 291.81 10.9 0 4 -1 281.74 10.49 0 -4 0 291.09 4.79 0 4 0 314.69 10.81 0 -4 -1 542.26 14.4 0 -4 -1 542.79 8 0 4 1 551.23 14.17 0 -4 -2 582.4 9.9 0 -4 -2 562.08 15 0 -4 -2 590.93 14.23 0 -4 -3 247.68 9.24 0 -4 -3 250.3 7.43 0 -4 -4 104 6.8 0 -4 -4 108.24 5.43 0 -4 -4 99.83 5.95 0 4 5 74.95 5.82 0 -4 -5 67.86 5.67 0 -4 -5 68.61 5.06 0 -4 -5 73 4.86 0 -4 -6 4.84 1.49 0 4 6 4.07 1.32 0 -4 -6 3.88 1.29 0 -4 -6 3.79 1.36 0 -4 -7 4.63 1.37 0 -4 -8 1.83 0.92 0 -4 -9 36.05 4.38 0 -4 -10 1.16 0.56 0 -4 -11 28.13 4.29 0 -4 -12 2.43 1.45 0 -4 -13 26.95 4.53 0 5 -11 46.62 6.94 0 5 -10 25.34 4.96 0 5 -9 14.33 3.73 0 5 -8 12.26 3.17 0 5 -8 8.4 1.44 0 5 -7 5.36 1.02 0 5 -7 6.72 2.41 0 5 -6 19.45 1.7 0 5 -6 22.57 3.9 0 5 -5 12.41 2.8 0 5 -5 11.78 1.08 0 5 -4 1 0.8 0 -5 4 -0.15 0.63 0 5 -3 80.95 6.61 0 -5 3 84.12 6.24 0 5 -2 81.76 6.48 0 -5 2 79.94 5.99 0 5 -1 10.23 2.23 0 -5 1 8.81 2.05 0 -5 0 6.61 0.81 0 5 0 5.61 1.68 0 -5 0 3.42 1.32 0 -5 -1 62.81 5.55 0 5 1 70.82 5.74 0 -5 -1 68.36 3.09 0 5 2 247.62 10.61 0 -5 -2 238.04 10.94 0 -5 -2 241.68 6.67 0 -5 -2 244.17 10.27 0 -5 -3 564.93 11.56 0 -5 -3 548.68 17.03 0 -5 -3 574.21 15.79 0 -5 -4 89.36 5.08 0 -5 -4 91.44 6.3 0 -5 -4 85.38 6.85 0 -5 -5 11.7 2 0 -5 -5 16.09 3.09 0 -5 -5 14.42 2.51 0 -5 -6 227.79 9.57 0 -5 -6 221.52 10.14 0 -5 -7 818.81 20.02 0 -5 -8 719.71 19.37 0 -5 -9 77.67 6.61 0 -5 -10 34.27 4.61 0 -5 -11 17.31 3.47 0 -5 -12 1.44 1.3 0 6 -11 442.26 22.89 0 6 -10 27.84 5.53 0 6 -9 33.61 5.79 0 6 -8 16.63 3.82 0 6 -7 208.66 5.7 0 6 -7 213.63 13.47 0 6 -6 47.23 1.92 0 6 -6 60.56 6.95 0 6 -5 64.61 6.91 0 6 -4 448.59 17.75 0 6 -3 87.37 7.64 0 6 -2 64.53 6.43 0 -6 2 52.57 5.38 0 6 -1 61.37 6.1 0 -6 1 61.21 5.86 0 6 0 12.74 2.82 0 -6 0 9.78 2.45 0 -6 0 5.74 0.85 0 -6 -1 230.39 6.19 0 -6 -1 222.04 11.55 0 6 1 232.25 11.51 0 -6 -2 128.03 8.86 0 -6 -2 142.31 5.47 0 -6 -2 126.22 8.14 0 6 2 140.17 8.85 0 6 3 189.27 10.45 0 -6 -3 180.46 10.64 0 -6 -3 175.56 6.68 0 -6 -3 179.98 9.77 0 -6 -4 10.22 2.4 0 -6 -4 8.11 1.58 0 -6 -5 2.32 0.88 0 -6 -5 2.11 1.11 0 -6 -6 16.91 2.97 0 -6 -7 637.32 18.96 0 -6 -8 161.96 9.76 0 -6 -9 112.54 8.36 0 -6 -10 9.37 2.39 0 -6 -11 50.3 6.06 0 -6 -12 76.93 7.79 0 7 -10 40.89 7.15 0 7 -9 33.78 6.21 0 7 -8 9.14 3.31 0 7 -7 50.39 7.05 0 7 -6 78.95 8.55 0 7 -5 36.81 5.54 0 7 -4 61.33 7.16 0 7 -3 103.8 9.06 0 7 -2 91.68 8.31 0 7 -1 395.08 16.86 0 7 0 11.4 2.99 0 -7 0 6.97 0.93 0 -7 -1 42.54 2.86 0 7 1 45.71 5.62 0 -7 -2 86.35 4.55 0 -7 -2 90.23 7.54 0 7 2 91.04 7.76 0 -7 -3 0.2 0.5 0 7 3 0.45 1.05 0 -7 -3 0.41 1.09 0 -7 -4 323.09 14.19 0 -7 -4 305.52 10.18 0 -7 -5 496.44 17.55 0 -7 -5 480.84 13.71 0 -7 -6 201.31 11.27 0 -7 -7 16.25 3.27 0 -7 -8 122.09 9.05 0 -7 -9 24.16 4.09 0 -7 -10 45.09 5.74 0 -7 -11 52.33 6.4 0 8 -8 2.98 1.94 0 8 -7 -0.07 1.58 0 8 -6 7.45 3.06 0 8 -5 54.1 7.5 0 8 -4 37.93 6.11 0 8 -3 213.17 13.9 0 8 -2 2 1.63 0 8 -1 41.88 5.89 0 8 0 41.74 5.84 0 8 1 94.16 8.73 0 -8 -1 93.94 4.36 0 8 2 9.04 2.86 0 -8 -2 6.85 1.37 0 -8 -2 5.26 2.01 0 8 3 289.37 15.05 0 -8 -3 276.83 9.45 0 -8 -3 291.52 14.65 0 -8 -4 24.03 4.3 0 -8 -4 23.15 2.96 0 -8 -5 0.19 0.85 0 -8 -6 19.98 3.8 0 -8 -7 20.14 3.9 0 -8 -8 12.88 3.1 0 -8 -9 14.51 3.34 0 -8 -10 9.98 2.8 0 9 -7 33.54 6.64 0 9 -6 2.03 2.35 0 9 -5 2.4 2.18 0 9 -4 1.02 1.71 0 9 -3 26.28 5.42 0 9 -2 146.57 12.16 0 9 -1 93.09 9.51 0 9 0 21.62 4.57 0 9 1 3.57 2.05 0 9 2 1 1.47 0 -9 -2 -0.07 1.66 0 -9 -3 199.65 13.08 0 9 3 191.32 13.22 0 -9 -4 274.38 15.19 0 -9 -5 12.85 3.33 0 -9 -6 24.67 4.55 0 -9 -7 10.27 2.89 0 -9 -8 46.22 6.26 0 10 -4 11.21 3.86 0 10 -3 8.15 3.01 0 10 -2 -0.36 1.61 0 10 -1 2.51 1.54 0 10 0 11.9 3.6 0 -10 -1 3.35 1.8 0 10 1 9.78 3.09 0 -10 -2 0.24 1.1 0 10 2 0.5 0.91 0 -10 -3 6.41 2.62 0 -10 -4 20.92 4.5 0 -10 -5 0.56 1 0 -10 -6 17.99 4.15 1 -10 -6 4.07 1.77 1 -10 -5 0.7 1.73 1 -10 -4 1.05 1.38 1 -10 -3 10.18 3.07 -1 10 2 39.13 6.29 1 -10 -2 41.42 6.36 -1 10 1 37.55 6.18 1 -10 -1 38.3 6.19 -1 10 0 -0.72 1.32 -1 10 -1 26.57 5.44 -1 10 -2 9.12 3 -1 10 -3 17.51 4.57 -1 10 -4 18.69 4.84 -1 10 -5 54.27 8.36 1 -9 -8 71.39 7.72 1 -9 -7 36 5.34 1 -9 -6 35.21 5.46 1 -9 -5 229.57 13.62 1 -9 -4 135.39 10.58 1 -9 -3 132.43 10.54 -1 9 2 122.99 10.5 1 -9 -2 110.6 9.71 -1 9 1 27.07 4.93 -1 9 0 171.19 12.55 -1 9 -1 1.1 1.19 -1 9 -2 142.77 11.92 -1 9 -3 9.53 3.24 -1 9 -4 80.83 9.47 -1 9 -5 23.78 5.3 -1 9 -6 13.24 4.08 -1 9 -7 91.81 10.87 1 -8 -10 81.84 8.01 1 -8 -9 17.2 3.67 1 -8 -8 0.19 1.14 1 -8 -7 17.17 3.55 1 -8 -6 41.8 5.51 1 -8 -5 4.32 1.77 1 -8 -4 239.18 13 1 -8 -4 245.09 10.52 1 -8 -3 24.63 3.16 -1 8 3 26.65 4.53 1 -8 -3 24.03 4.22 1 -8 -2 3.59 1.55 -1 8 2 3.47 1.88 1 -8 -2 4.76 1.33 1 -8 -1 18.94 2.34 -1 8 1 16.72 3.64 1 -8 0 86.9 4.06 -1 8 0 88.12 8.44 -1 8 -1 219.15 13.45 -1 8 -2 3.8 1.77 -1 8 -3 26.38 4.8 -1 8 -4 6.17 2.66 -1 8 -5 15.61 3.84 -1 8 -6 46.29 6.99 -1 8 -7 7.41 2.75 -1 8 -8 4.38 2.47 1 -7 -11 12.12 3.04 1 -7 -10 0.11 1.36 1 -7 -9 11.87 2.85 1 -7 -8 11.97 2.85 1 -7 -7 99.79 7.89 1 -7 -6 93.39 7.54 1 -7 -5 18.91 3.39 1 -7 -4 18.16 3.35 1 -7 -4 13.21 2.31 -1 7 3 11.17 2.83 1 -7 -3 12.79 2.91 1 -7 -3 10.12 1.91 1 -7 -2 -0.41 0.63 -1 7 2 0.45 0.92 1 -7 -2 -1.04 0.86 -1 7 2 0.77 0.57 1 -7 -1 95 5.03 -1 7 1 101.47 8.16 1 -7 0 121.59 5.03 -1 7 0 131.67 9.5 -1 7 -1 777.92 23.43 -1 7 -2 784.62 24.04 -1 7 -3 163.72 11.32 -1 7 -4 2.3 1.7 -1 7 -5 216.64 13.59 -1 7 -6 80.79 8.6 -1 7 -7 23.34 4.65 -1 7 -8 3.41 2.2 -1 7 -9 0.78 1.08 -1 7 -10 11 3.58 1 -6 -12 76.24 7.67 1 -6 -11 27.41 4.45 1 -6 -10 51.33 5.81 1 -6 -9 42.85 5.09 1 -6 -8 0.66 0.51 1 -6 -7 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16.93 4.04 -8 -5 -2 71.48 8.32 -8 -5 -2 66.21 5.43 -8 -5 -3 75.94 5.96 -8 -5 -3 60.4 7.79 -8 -5 -4 211.95 15.23 -8 -5 -4 232.11 10.75 -8 -5 -5 2.35 1.07 -8 -5 -5 2.09 1.83 -8 -5 -6 1.79 1.11 -8 -5 -6 2.89 2.25 -8 -5 -7 10.94 2.74 -8 -5 -7 12.09 3.93 -8 -5 -8 0.53 1.3 -8 -5 -9 192.41 12.02 -8 -6 2 39.77 5.37 -8 -6 1 28.72 4.63 -8 -6 0 9.21 2.64 -8 -6 -1 -0.73 1.54 -8 -6 -2 3.85 1.59 -8 -6 -2 3.19 1.23 -8 -6 -3 24.05 3.69 -8 -6 -3 21.66 4.83 -8 -6 -4 0.34 1.05 -8 -6 -4 0.3 1.21 -8 -6 -5 11.4 2.61 -8 -6 -5 10.22 3.29 -8 -6 -6 4.83 1.99 -8 -6 -6 3.02 1.72 -8 -6 -7 45.05 5.63 -8 -6 -8 37.18 5.47 -8 -7 -2 11.71 3.65 -8 -7 -3 28.64 4.37 -8 -7 -3 18.99 4.49 -8 -7 -4 24.19 4.27 -8 -7 -4 22.43 5.08 -8 -7 -5 1.03 1.01 -8 -7 -5 -0.63 1.82 -8 -7 -6 8.49 2.46 -9 5 -1 2.42 1.55 -9 5 -2 -0.18 0.65 -9 5 -3 6.82 2.81 -9 5 -4 2.45 2.34 -9 4 1 11.57 3.39 -9 4 0 43.73 6.5 -9 4 -1 23.39 4.91 -9 4 -2 47.52 6.97 -9 4 -3 5.88 2.58 -9 4 -4 62.35 8.36 -9 4 -5 162.8 13.6 -9 3 2 90.14 9.17 -9 3 1 9.18 3.11 -9 3 0 26.07 5.1 -9 3 -1 8.38 3.02 -9 3 -2 52.57 7.46 -9 3 -3 64.8 8.44 -9 3 -4 -0.24 1.56 -9 3 -5 348.16 20.19 -9 3 -6 113.09 11.77 -9 2 3 1.35 0.76 -9 2 2 6.58 2.81 -9 2 1 39.05 6.13 -9 2 0 6.59 2.82 -9 2 -1 18.04 4.37 -9 2 -2 -0.39 1.06 -9 2 -3 16.86 4.3 -9 2 -4 266.39 17.45 -9 2 -5 25.56 5.64 -9 2 -6 138.22 13.02 -9 1 3 17.01 4.01 -9 1 2 79.83 8.7 -9 1 1 44 6.5 -9 1 0 14.73 3.81 -9 1 -1 14.68 3.61 -9 1 -2 44.93 6.95 -9 1 -3 13.73 4.01 -9 1 -4 171.31 14.1 -9 1 -5 3.52 1.99 -9 1 -6 1.99 2.13 -9 0 4 42.65 6.36 -9 0 3 7.07 2.85 -9 0 2 13.01 3.6 -9 0 1 0.77 0.6 -9 0 0 3.81 2.05 -9 0 -1 7.18 3.11 -9 0 -2 8.4 3.06 -9 0 -3 54.11 7.74 -9 0 -4 23.23 5.33 -9 0 -5 4.76 2.7 -9 0 -6 0.3 1.45 -9 -1 4 16.32 3.76 -9 -1 3 13.26 3.52 -9 -1 2 48.45 6.7 -9 -1 1 11.48 3.51 -9 -1 0 24.13 4.99 -9 -1 -1 1.57 1.18 -9 -1 -2 48.57 7.27 -9 -1 -3 9.1 3.19 -9 -1 -4 8.22 3.46 -9 -1 -5 13.22 4.19 -9 -1 -6 20 5.15 -9 -2 4 2.08 1.08 -9 -2 3 2.74 1.37 -9 -2 2 -0.73 1.04 -9 -2 1 1.58 1.5 -9 -2 0 9.48 3.15 -9 -2 -1 5.04 2.41 -9 -2 -2 10.76 3.54 -9 -2 -3 20.92 4.75 -9 -2 -4 29.3 5.94 -9 -2 -5 33.12 6.49 -9 -2 -6 17.74 4.8 -9 -3 5 30.21 5.08 -9 -3 4 43.01 6.02 -9 -3 3 -0.82 1.05 -9 -3 2 33.64 5.51 -9 -3 1 8.03 2.81 -9 -3 0 74.27 8.63 -9 -3 -1 11.74 3.72 -9 -3 -2 -0.62 1.23 -9 -3 -3 35.73 6.47 -9 -3 -4 2.37 1.31 -9 -3 -5 5.83 2.73 -9 -4 5 24.4 4.49 -9 -4 4 7.58 2.73 -9 -4 3 -1.12 2.38 -9 -4 2 180.83 12.71 -9 -4 1 93.07 9.43 -9 -4 0 4.52 2.41 -9 -4 -1 4.27 1.31 -9 -4 -2 16.05 4.05 -9 -4 -3 0.29 1.27 -9 -4 -4 33.86 6.32 -9 -4 -5 -1.25 1.54 -9 -5 3 82.81 8.27 -9 -5 2 43.21 6.19 -9 -5 1 53.22 6.94 -9 -5 0 29.94 5.47 -9 -5 -1 0.27 0.89 -9 -5 -2 0.31 1.72 -9 -5 -3 81.06 9.67 -9 -5 -4 -0.27 1 -9 -6 0 3.94 2.11 -9 -6 -1 -0.01 1.65 -9 -6 -2 4.47 1.2 -9 -6 -3 37.55 6.78