#------------------------------------------------------------------------------ #$Date: 2019-10-29 02:26:27 +0200 (Tue, 29 Oct 2019) $ #$Revision: 220329 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/24/1552497.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_1552497 loop_ _publ_author_name 'Gu, Han' 'Ghosh, Saptarshi' 'Staples, Richard J.' 'Bane, Susan L.' _publ_section_title ; \b-Hydroxy-Stabilized Boron-Nitrogen Heterocycles Enable Rapid and Efficient C-Terminal Protein Modification. ; _journal_issue 10 _journal_name_full 'Bioconjugate chemistry' _journal_page_first 2604 _journal_page_last 2613 _journal_paper_doi 10.1021/acs.bioconjchem.9b00534 _journal_volume 30 _journal_year 2019 _chemical_absolute_configuration unk _chemical_formula_moiety 'C16 H16 B N3 O3' _chemical_formula_sum 'C16 H16 B N3 O3' _chemical_formula_weight 309.13 _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' _symmetry_space_group_name_Hall 'P 2yb' _symmetry_space_group_name_H-M 'P 1 21 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2018-11-05 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 91.886(2) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.95450(10) _cell_length_b 4.96270(10) _cell_length_c 25.4669(7) _cell_measurement_reflns_used 3090 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 69.93 _cell_measurement_theta_min 5.21 _cell_volume 752.15(3) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection 'COSMO (BRUKER, V1.61, 2009)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 173(2) _diffrn_detector_area_resol_mean 8.36 _diffrn_measured_fraction_theta_full 0.990 _diffrn_measured_fraction_theta_max 0.983 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0558 _diffrn_reflns_av_unetI/netI 0.0518 _diffrn_reflns_Laue_measured_fraction_full 0.990 _diffrn_reflns_Laue_measured_fraction_max 0.983 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_number 7362 _diffrn_reflns_point_group_measured_fraction_full 0.964 _diffrn_reflns_point_group_measured_fraction_max 0.954 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 70.003 _diffrn_reflns_theta_min 5.213 _diffrn_source 'sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.777 _exptl_absorpt_correction_T_max 0.7533 _exptl_absorpt_correction_T_min 0.6101 _exptl_absorpt_correction_type multi-scan _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.365 _exptl_crystal_description plate _exptl_crystal_F_000 324 _exptl_crystal_recrystallization_method 'used as received' _exptl_crystal_size_max 0.224 _exptl_crystal_size_mid 0.119 _exptl_crystal_size_min 0.022 _refine_diff_density_max 0.188 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.048 _refine_ls_abs_structure_details ; Refined as an inversion twin. ; _refine_ls_abs_structure_Flack 0.2(4) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 225 _refine_ls_number_reflns 2719 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.040 _refine_ls_R_factor_all 0.0569 _refine_ls_R_factor_gt 0.0433 _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^)+(0.0542P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0952 _refine_ls_wR_factor_ref 0.1021 _reflns_Friedel_coverage 0.725 _reflns_Friedel_fraction_full 0.931 _reflns_Friedel_fraction_max 0.917 _reflns_number_gt 2265 _reflns_number_total 2719 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file bc9b00534_si_002.cif _cod_data_source_block jh1018b _cod_database_code 1552497 _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 0.983 _shelx_estimated_absorpt_t_min 0.845 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.8 0.2 2. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups 3.a Ternary CH refined with riding coordinates: C9(H9) 3.b Secondary CH2 refined with riding coordinates: C10(H10A,H10B) 3.c Aromatic/amide H refined with riding coordinates: C1(H1A), C4(H4), C5(H5), C6(H6), C7(H7), C12(H12), C13(H13), C15(H15), C16(H16) ; _shelx_res_file ; TITL jh1018b_a.res in P2(1) jh1018b.res created by SHELXL-2018/3 at 09:51:52 on 05-Nov-2018 REM Old TITL JH1018B in P2(1) REM SHELXT solution in P2(1): R1 0.104, Rweak 0.023, Alpha 0.002 REM 0.327 for 3 systematic absences, Orientation as input REM Flack x = 0.209 ( 0.289 ) from 787 Parsons' quotients REM Formula found by SHELXT: C16 B N3 O3 CELL 1.54178 5.9545 4.9627 25.4669 90 91.886 90 ZERR 2 0.0001 0.0001 0.0007 0 0.002 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H B N O UNIT 32 32 2 6 6 EQIV $1 2-X,-0.5+Y,1-Z EQIV $2 +X,1+Y,+Z EQIV $3 1+X,+Y,+Z L.S. 15 PLAN 5 SIZE 0.022 0.119 0.224 TEMP -100(2) HTAB O3 O3_$1 HTAB N3 O1_$2 HTAB N3 O2_$3 BOND $H CONF fmap 2 53 acta TWIN -1 0 0 0 -1 0 0 0 -1 2 REM REM REM WGHT 0.054200 BASF 0.18188 FVAR 0.48002 O1 5 0.481034 0.038023 0.217908 11.00000 0.01585 0.02123 = 0.03680 0.00043 0.00215 -0.00125 H1 2 0.599177 0.044779 0.211762 11.00000 0.02996 O2 5 -0.129209 0.346285 0.287409 11.00000 0.01440 0.03459 = 0.03567 0.00128 0.00131 -0.00138 O3 5 0.956939 0.871850 0.477866 11.00000 0.03037 0.02945 = 0.03973 -0.00204 -0.01438 -0.00002 H3 2 0.993625 0.734582 0.493333 11.00000 0.05472 N1 4 0.113075 0.256261 0.220421 11.00000 0.01410 0.02580 = 0.03128 -0.00066 -0.00282 -0.00194 N2 4 -0.050443 0.146016 0.186319 11.00000 0.01726 0.03612 = 0.03590 -0.00814 -0.00607 -0.00593 N3 4 0.430238 0.499154 0.253003 11.00000 0.01186 0.01737 = 0.03103 0.00222 -0.00051 0.00042 H3A 2 0.569191 0.465879 0.262961 11.00000 0.01855 H3B 2 0.421460 0.670051 0.243190 11.00000 0.00860 C1 1 -0.002782 0.169652 0.137336 11.00000 0.02628 0.04357 = 0.03613 -0.01001 -0.00863 -0.00267 AFIX 43 H1A 2 -0.102251 0.083314 0.112735 11.00000 -1.20000 AFIX 0 C2 1 0.186817 0.314177 0.115538 11.00000 0.02643 0.03198 = 0.03327 -0.00606 -0.00074 0.00053 C3 1 0.368469 0.397109 0.148313 11.00000 0.02207 0.02148 = 0.03422 -0.00285 0.00223 0.00385 C4 1 0.534299 0.552908 0.126495 11.00000 0.02952 0.02868 = 0.03425 -0.00056 0.00409 -0.00173 AFIX 43 H4 2 0.659116 0.610007 0.147875 11.00000 -1.20000 AFIX 0 C5 1 0.521293 0.627254 0.073819 11.00000 0.04769 0.03772 = 0.03712 0.00209 0.01028 -0.00693 AFIX 43 H5 2 0.636127 0.735806 0.059737 11.00000 -1.20000 AFIX 0 C6 1 0.342213 0.544176 0.041780 11.00000 0.06366 0.04723 = 0.02716 0.00202 0.00223 -0.00148 AFIX 43 H6 2 0.334888 0.594971 0.005798 11.00000 -1.20000 AFIX 0 C7 1 0.174637 0.387935 0.062021 11.00000 0.04306 0.05016 = 0.03203 -0.00765 -0.00510 0.00102 AFIX 43 H7 2 0.051708 0.330232 0.040102 11.00000 -1.20000 AFIX 0 C8 1 0.056379 0.346311 0.267677 11.00000 0.01585 0.01773 = 0.03066 0.00567 -0.00294 0.00204 C9 1 0.269734 0.450509 0.296106 11.00000 0.01433 0.01933 = 0.03084 0.00208 -0.00179 0.00254 AFIX 13 H9 2 0.331867 0.301063 0.318560 11.00000 -1.20000 AFIX 0 C10 1 0.229689 0.689062 0.331264 11.00000 0.01971 0.02283 = 0.03172 -0.00144 -0.00203 0.00136 AFIX 23 H10A 2 0.090967 0.657904 0.350774 11.00000 -1.20000 H10B 2 0.206013 0.851685 0.309257 11.00000 -1.20000 AFIX 0 C11 1 0.423718 0.739828 0.370316 11.00000 0.01644 0.02410 = 0.02977 -0.00495 0.00155 0.00553 C12 1 0.433905 0.602793 0.417981 11.00000 0.02600 0.02748 = 0.02922 0.00164 0.00249 -0.00551 AFIX 43 H12 2 0.317188 0.480550 0.426035 11.00000 -1.20000 AFIX 0 C13 1 0.610886 0.640856 0.454002 11.00000 0.03400 0.02745 = 0.02701 0.00075 0.00047 -0.00107 AFIX 43 H13 2 0.616716 0.543187 0.486101 11.00000 -1.20000 AFIX 0 C14 1 0.778487 0.822119 0.442736 11.00000 0.02250 0.02390 = 0.03045 -0.00497 -0.00502 0.00413 C15 1 0.773626 0.959798 0.395788 11.00000 0.01876 0.02221 = 0.03745 0.00021 0.00127 0.00108 AFIX 43 H15 2 0.889776 1.083684 0.388196 11.00000 -1.20000 AFIX 0 C16 1 0.597163 0.916225 0.359467 11.00000 0.02060 0.02042 = 0.02882 -0.00014 0.00069 0.00308 AFIX 43 H16 2 0.595520 1.008624 0.326786 11.00000 -1.20000 AFIX 0 B1 3 0.363108 0.285538 0.207295 11.00000 0.01514 0.01749 = 0.03365 -0.00002 -0.00031 -0.00284 HKLF 4 REM jh1018b_a.res in P2(1) REM wR2 = 0.1021, GooF = S = 1.040, Restrained GooF = 1.040 for all data REM R1 = 0.0433 for 2265 Fo > 4sig(Fo) and 0.0569 for all 2719 data REM 225 parameters refined using 1 restraints END WGHT 0.0542 0.0000 REM Highest difference peak 0.188, deepest hole -0.255, 1-sigma level 0.048 Q1 1 0.3669 0.3608 0.1794 11.00000 0.05 0.19 Q2 1 -0.1665 0.7557 0.2809 11.00000 0.05 0.18 Q3 1 0.2160 0.8333 0.2017 11.00000 0.05 0.17 Q4 1 0.6349 0.8036 0.4600 11.00000 0.05 0.15 Q5 1 0.5068 0.3985 0.1380 11.00000 0.05 0.15 ; _shelx_res_checksum 64380 _shelx_hkl_file ; -1 0 0 130.40 2.34 -2 0 0 264.64 4.81 2 0 0 256.52 5.18 -3 0 0 20.30 1.04 3 0 0 19.95 1.31 4 0 0 0.44 0.85 -4 0 0 0.71 0.63 5 0 0 27.23 2.88 5 0 0 30.17 2.46 5 0 0 28.45 1.89 5 0 0 26.99 2.35 5 0 0 28.38 2.80 -5 0 0 29.68 2.06 5 0 0 26.71 3.20 6 0 0 12.50 1.28 6 0 0 15.76 2.44 6 0 0 15.54 1.93 6 0 0 16.91 2.30 7 0 0 2.65 1.11 7 0 0 -0.04 1.20 0 -1 0 -0.08 0.33 -1 -1 0 800.72 14.15 1 1 0 817.77 15.05 1 1 0 799.80 14.15 2 -1 0 7.53 0.76 -2 -1 0 8.38 0.82 2 1 0 9.55 0.87 -3 -1 0 8.65 1.01 3 -1 0 7.16 1.03 3 1 0 7.15 1.05 -4 -1 0 5.09 1.05 4 -1 0 6.88 1.23 4 1 0 4.40 1.14 4 1 0 3.51 1.16 -4 1 0 5.18 0.72 5 -1 0 18.25 2.82 5 -1 0 20.67 2.04 5 -1 0 22.11 2.75 5 -1 0 22.89 2.66 5 1 0 19.92 2.97 5 1 0 16.55 2.32 5 1 0 22.88 2.23 5 1 0 22.14 2.91 5 1 0 21.59 2.00 6 -1 0 55.09 3.54 6 -1 0 52.83 2.85 6 -1 0 56.47 3.22 6 1 0 49.76 2.78 6 1 0 52.41 2.51 6 1 0 51.98 3.07 6 1 0 54.67 3.35 7 -1 0 0.08 1.08 7 1 0 1.31 1.24 0 -2 0 28.90 1.49 0 -2 0 29.26 1.32 0 2 0 30.15 1.23 1 -2 0 552.29 10.22 -1 -2 0 549.09 10.90 -1 -2 0 541.75 11.58 1 -2 0 558.96 11.84 -1 2 0 584.81 10.57 1 2 0 556.62 11.02 2 -2 0 137.99 3.90 3 -2 0 2.81 1.00 -4 -2 0 41.93 3.64 4 -2 0 46.13 2.59 4 -2 0 37.07 3.04 4 -2 0 38.09 3.16 4 2 0 44.64 3.60 4 2 0 45.91 3.02 5 -2 0 1.74 1.12 5 -2 0 4.87 1.79 -5 -2 0 2.68 1.66 5 -2 0 2.59 1.69 5 -2 0 3.32 1.43 5 2 0 3.27 2.00 5 2 0 5.53 1.48 5 2 0 4.20 1.47 6 -2 0 0.22 1.72 6 2 0 0.74 1.16 0 -3 0 0.00 0.76 0 -3 0 0.21 0.64 0 3 0 1.38 0.70 1 -3 0 19.76 1.73 -1 -3 0 22.40 1.70 1 -3 0 22.73 1.09 -1 -3 0 23.64 1.79 -1 3 0 19.68 1.37 1 3 0 21.43 1.64 1 3 0 19.33 1.49 2 -3 0 50.41 2.57 -2 -3 0 50.87 2.90 -2 3 0 47.93 1.80 3 -3 0 0.05 1.37 3 -3 0 0.92 1.26 3 -3 0 2.26 1.36 -3 -3 0 -0.68 1.75 3 3 0 3.66 1.99 -4 -3 0 12.00 2.13 4 -3 0 15.34 2.58 4 -3 0 14.49 2.12 4 3 0 14.67 2.51 -5 -3 0 31.77 3.01 5 -3 0 32.50 2.68 5 3 0 30.86 2.60 5 3 0 28.31 2.91 -6 -3 0 28.15 2.56 6 3 0 34.14 2.03 0 -4 0 21.93 2.65 0 -4 0 20.23 1.62 0 -4 0 20.17 2.62 0 -4 0 23.49 1.71 0 -4 0 25.71 2.35 0 4 0 22.96 2.19 -1 -4 0 24.56 2.73 1 -4 0 30.58 2.41 -1 -4 0 30.77 2.95 1 -4 0 30.90 3.24 1 -4 0 34.49 3.02 -1 -4 0 32.93 2.00 -1 -4 0 32.75 2.36 -1 -4 0 31.51 2.42 2 -4 0 13.91 2.04 -2 -4 0 20.01 2.96 -2 -4 0 12.64 1.82 -2 -4 0 14.90 2.10 2 -4 0 17.16 2.60 -2 -4 0 13.39 1.96 2 4 0 15.47 2.52 -3 -4 0 18.95 2.66 3 -4 0 20.75 3.02 -3 -4 0 23.23 2.67 -3 -4 0 29.73 3.30 3 4 0 18.32 2.62 4 -4 0 0.22 1.59 4 4 0 0.80 1.51 5 4 0 6.30 1.49 0 -5 0 -0.20 1.55 0 -5 0 0.23 1.46 1 -5 0 12.74 2.09 -1 -5 0 14.08 1.24 -1 -5 0 6.61 1.91 2 -5 0 1.71 1.96 2 -5 0 0.63 1.42 -2 -5 0 3.52 1.11 2 5 0 0.23 1.56 -3 -5 0 7.55 1.31 3 -5 0 2.79 1.45 3 5 0 2.65 1.43 0 6 0 3.57 1.56 7 0 -1 2.55 1.28 7 0 -1 2.85 1.36 6 0 -1 44.45 2.99 6 0 -1 45.09 1.81 6 0 -1 43.96 3.24 6 0 -1 43.07 2.61 5 0 -1 3.52 1.39 5 0 -1 4.72 1.71 5 0 -1 5.50 1.98 5 0 -1 5.92 1.10 -5 0 1 5.32 1.24 -4 0 1 13.00 1.16 4 0 -1 13.43 1.52 -3 0 1 0.79 0.45 3 0 -1 0.30 0.58 2 0 -1 28.79 1.23 -2 0 1 30.56 0.90 -1 0 1 183.86 3.46 -1 0 -1 294.40 5.19 2 0 1 147.97 3.30 -2 0 -1 146.51 2.94 -3 0 -1 20.60 1.05 3 0 1 19.09 1.32 4 0 1 4.39 1.11 -4 0 -1 4.09 0.78 5 0 1 37.75 3.17 5 0 1 36.40 2.44 5 0 1 35.80 3.07 5 0 1 37.22 2.37 5 0 1 35.50 2.13 -5 0 -1 35.83 2.26 5 0 1 37.09 2.76 6 0 1 67.59 4.03 6 0 1 69.09 2.48 6 0 1 68.76 3.38 6 0 1 69.13 3.90 6 0 1 67.29 3.49 7 0 1 0.18 1.12 7 0 1 1.59 1.01 7 -1 -1 8.64 1.44 7 1 -1 9.46 1.46 7 1 -1 7.95 1.58 6 -1 -1 45.83 3.32 6 -1 -1 40.79 2.62 6 -1 -1 47.02 2.99 6 1 -1 42.78 3.20 6 1 -1 45.13 3.44 6 1 -1 47.58 2.35 6 1 -1 46.55 2.84 5 -1 -1 47.50 3.33 5 -1 -1 44.54 3.22 -5 -1 1 44.88 3.60 5 -1 -1 48.38 2.90 5 -1 -1 45.29 2.90 5 1 -1 48.32 3.27 5 1 -1 47.68 3.06 5 1 -1 47.63 2.59 5 1 -1 46.44 2.83 -4 -1 1 49.60 2.13 4 -1 -1 52.63 2.51 4 1 -1 46.52 2.45 4 1 -1 50.54 2.44 -4 1 1 48.34 1.66 3 -1 -1 0.19 0.65 -3 -1 1 0.18 0.55 3 1 -1 0.71 0.66 -2 -1 1 35.99 1.35 2 -1 -1 35.18 1.38 2 1 -1 37.00 1.44 -1 -1 1 318.14 5.85 1 1 -1 315.40 6.20 1 1 -1 310.38 5.83 1 1 -1 311.92 6.23 0 -1 1 448.78 8.33 0 -1 -1 450.29 8.29 0 1 -1 454.29 8.45 -1 -1 -1 556.49 10.45 -1 -1 -1 550.43 9.93 1 1 1 564.66 9.96 -2 -1 -1 42.90 1.45 2 -1 1 39.37 1.48 2 1 1 43.38 1.55 -3 -1 -1 8.31 1.04 3 -1 1 7.83 1.06 -3 1 -1 8.68 0.66 3 1 1 8.54 1.09 4 -1 1 123.00 3.84 4 -1 1 119.68 4.03 -4 -1 -1 120.63 3.56 4 1 1 118.69 4.00 4 1 1 121.43 3.82 -4 1 -1 120.65 3.03 5 -1 1 76.62 4.28 5 -1 1 75.53 3.85 5 -1 1 77.96 3.56 5 -1 1 83.03 4.38 5 1 1 77.06 3.91 5 1 1 69.60 3.92 5 1 1 75.77 3.31 5 1 1 81.33 3.54 5 1 1 76.24 3.43 5 1 1 75.57 4.03 6 -1 1 2.82 1.72 6 -1 1 2.63 1.59 6 -1 1 0.31 1.09 6 -1 1 1.07 1.39 6 1 1 1.87 1.91 6 1 1 2.92 1.05 6 1 1 0.42 1.25 6 1 1 0.26 1.43 6 1 1 0.75 1.75 7 -1 1 7.80 1.43 7 1 1 6.62 1.16 6 -2 -1 18.06 2.22 -6 -2 1 18.86 2.91 6 2 -1 16.11 1.65 6 2 -1 17.48 2.10 5 -2 -1 10.89 2.05 5 -2 -1 10.07 2.00 5 -2 -1 9.34 1.58 -5 -2 1 11.17 2.01 5 2 -1 11.79 2.04 5 2 -1 11.73 2.01 5 2 -1 11.29 2.02 4 -2 -1 0.31 1.27 4 -2 -1 2.51 1.13 -4 -2 1 1.05 1.77 4 2 -1 1.71 1.45 3 -2 -1 4.21 1.11 2 -2 -1 50.70 2.14 1 -2 -1 101.47 3.08 -1 -2 1 99.54 2.84 -1 -2 1 101.45 2.88 1 2 -1 99.59 2.74 0 -2 -1 63.62 2.29 0 -2 1 65.29 1.95 0 -2 -1 66.92 1.91 0 -2 1 67.64 2.25 0 2 1 67.46 1.94 0 2 -1 68.79 1.95 1 -2 1 52.66 2.05 1 -2 1 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5 59.37 3.34 5 -1 5 68.85 3.39 5 -1 5 55.44 3.70 5 -1 5 70.87 4.13 5 1 5 64.26 4.15 5 1 5 63.69 3.18 5 1 5 66.35 4.01 5 1 5 62.20 3.33 5 1 5 63.75 3.30 5 1 5 65.21 3.49 6 -1 5 24.35 2.42 6 -1 5 23.03 2.64 6 -1 5 28.18 2.78 6 -1 5 22.97 2.06 6 1 5 25.63 2.72 6 1 5 24.17 2.06 6 1 5 23.66 2.65 6 -2 -5 3.25 1.89 6 2 -5 1.29 1.29 6 2 -5 1.73 1.16 -5 -2 5 24.76 2.80 5 -2 -5 22.18 3.00 5 2 -5 20.97 2.44 5 2 -5 18.00 2.11 5 2 -5 21.81 2.37 4 2 -5 5.27 1.78 4 2 -5 7.08 2.00 4 2 -5 7.44 1.39 3 2 -5 4.12 1.53 2 -2 -5 78.22 2.83 2 2 -5 79.40 2.95 1 -2 -5 185.00 4.77 -1 -2 5 183.45 4.45 0 -2 5 165.10 4.33 0 -2 -5 164.28 3.70 0 -2 -5 157.16 4.34 0 2 -5 166.97 3.90 1 -2 5 133.69 3.86 -1 -2 -5 134.54 3.72 -1 -2 -5 134.92 3.50 -1 2 -5 134.57 3.31 1 2 5 136.86 3.25 2 -2 5 53.08 2.28 -2 -2 -5 53.91 2.38 2 2 5 56.12 1.98 3 -2 5 21.07 1.89 3 2 5 21.35 1.77 -3 2 -5 20.51 2.12 4 -2 5 104.58 4.28 -4 -2 -5 99.31 4.72 4 -2 5 101.00 4.69 4 -2 5 100.28 4.52 4 -2 5 103.90 4.71 4 -2 5 111.44 4.09 4 2 5 102.29 4.70 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10.74 1.91 3 2 -8 8.95 1.72 3 2 -8 8.91 1.96 2 -2 -8 28.68 1.89 2 2 -8 27.48 2.28 -1 -2 8 18.06 1.57 1 -2 -8 17.15 1.55 1 2 -8 14.45 1.60 0 -2 -8 41.07 1.68 0 -2 -8 41.60 2.21 0 2 8 42.14 1.51 0 2 -8 37.88 2.12 -1 -2 -8 150.20 4.01 -1 -2 -8 154.10 4.38 1 2 8 152.63 3.74 -1 2 -8 146.25 4.54 -2 -2 -8 27.74 2.05 2 2 8 34.79 1.85 -2 2 -8 33.28 2.36 -3 2 -8 33.36 2.65 3 2 8 29.92 2.11 4 -2 8 17.95 2.56 4 -2 8 19.74 2.59 4 -2 8 17.88 2.52 4 2 8 17.19 2.79 4 2 8 17.91 2.09 4 2 8 17.36 2.17 5 -2 8 20.28 2.55 5 -2 8 22.04 2.77 5 2 8 20.51 2.70 5 2 8 19.68 1.72 6 -2 8 27.73 2.43 6 2 8 24.51 1.98 6 2 8 26.62 2.24 6 3 -8 1.19 1.04 6 3 -8 1.92 0.73 -5 -3 8 2.50 1.51 5 3 -8 2.55 1.41 5 3 -8 3.39 1.26 5 3 -8 3.79 1.69 -4 -3 8 29.04 3.47 4 3 -8 25.61 3.02 4 3 -8 26.78 2.47 4 3 -8 31.53 2.71 4 3 -8 22.73 2.80 3 -3 -8 2.46 1.53 3 -3 -8 5.80 2.23 -3 -3 8 8.35 2.21 3 3 -8 4.85 2.15 3 3 -8 5.98 1.72 3 3 -8 3.37 1.81 2 -3 -8 23.18 2.24 2 -3 -8 19.33 2.81 2 3 -8 19.01 3.11 1 -3 -8 63.79 3.02 -1 -3 8 67.40 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14.33 2.43 6 1 -9 9.30 1.15 6 1 -9 12.26 1.91 5 -1 -9 20.32 2.30 5 -1 -9 24.10 2.64 5 1 -9 26.38 2.52 5 1 -9 20.41 1.82 5 1 -9 21.10 2.68 5 1 -9 20.97 2.88 5 1 -9 19.74 2.42 4 -1 -9 38.26 2.27 -4 -1 9 37.23 2.22 4 -1 -9 41.02 2.92 4 -1 -9 34.78 3.39 4 1 -9 33.49 3.42 4 1 -9 35.00 3.39 4 1 -9 36.22 1.94 4 1 -9 38.96 2.45 -4 1 9 38.99 1.66 4 1 -9 39.82 3.14 3 -1 -9 50.12 2.34 -3 -1 9 48.73 2.01 3 1 -9 46.26 2.28 -3 1 9 48.04 1.42 3 1 -9 51.45 2.33 3 1 -9 52.52 2.31 -2 -1 9 16.31 1.21 2 -1 -9 14.40 1.48 2 -1 -9 15.27 1.38 2 1 -9 17.25 1.56 2 1 -9 17.07 1.40 -1 -1 9 42.55 1.60 1 -1 -9 42.57 1.50 1 -1 -9 41.82 1.97 1 1 -9 37.03 1.98 1 1 -9 39.35 2.07 -1 1 9 39.87 1.28 0 -1 -9 82.22 2.36 0 -1 -9 80.29 2.80 0 1 -9 81.81 2.84 0 1 9 81.16 2.15 0 1 -9 86.59 2.77 -1 -1 -9 155.78 4.24 -1 -1 -9 155.12 3.99 1 1 9 156.67 3.64 -1 1 -9 148.84 4.30 2 -1 9 19.39 1.34 -2 -1 -9 21.04 1.69 -2 1 -9 15.39 1.86 3 -1 9 13.01 1.56 3 -1 9 21.78 1.98 3 1 9 20.20 1.77 4 -1 9 8.74 2.18 4 -1 9 3.45 1.56 4 -1 9 4.98 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-23 38.33 3.49 2 1 23 35.56 3.09 3 -1 23 6.71 1.02 3 -1 23 9.68 1.77 3 -1 23 8.02 1.61 -3 -1 -23 6.46 1.37 3 1 23 12.72 2.01 3 1 23 8.75 1.85 -4 -1 -23 3.99 1.11 4 -1 23 4.67 1.38 4 1 23 4.04 0.67 4 1 23 3.84 1.05 4 1 23 5.34 1.42 4 -2 -23 9.85 1.69 4 2 -23 10.71 1.29 3 -2 -23 24.87 2.74 -3 -2 23 23.22 2.46 3 2 -23 19.23 2.19 3 2 -23 20.83 1.55 3 2 -23 19.20 2.31 2 -2 -23 2.70 1.67 -2 -2 23 4.06 1.90 2 -2 -23 4.26 0.93 2 2 -23 4.32 1.51 2 2 -23 5.98 1.11 2 2 -23 5.91 1.81 -1 -2 23 17.15 2.58 1 -2 -23 11.60 2.40 1 -2 -23 15.83 2.82 1 -2 -23 15.32 2.00 1 2 -23 12.99 2.25 1 2 -23 16.84 2.23 1 2 -23 14.90 2.57 0 -2 -23 12.39 2.00 0 -2 23 15.00 2.45 0 -2 23 11.04 1.95 0 -2 -23 15.13 1.40 0 -2 -23 11.99 2.05 0 -2 -23 14.25 2.51 0 2 -23 12.34 2.04 0 2 -23 16.22 2.40 1 -2 23 16.02 2.35 1 -2 23 17.74 2.49 -1 -2 -23 15.47 1.94 -1 -2 -23 16.38 2.43 1 2 23 16.23 2.68 -2 -2 -23 1.50 0.81 2 -2 23 1.05 0.86 2 -2 23 1.15 1.40 -2 -2 -23 0.10 1.39 2 2 23 2.00 1.69 3 -2 23 -0.85 0.78 -3 -2 -23 -0.77 0.90 -3 -2 -23 -0.10 1.08 3 -2 23 -1.29 1.28 3 2 23 1.58 1.43 3 2 23 -0.98 1.33 -4 -2 -23 2.08 1.11 -4 -2 -23 2.49 0.64 4 2 23 2.39 0.96 4 2 23 2.58 0.60 4 2 23 1.80 1.04 -3 -3 23 2.59 1.38 -3 -3 23 2.73 1.27 3 -3 -23 2.52 1.50 3 3 -23 0.38 1.23 2 -3 -23 -0.83 1.34 -2 -3 23 2.87 1.37 -2 -3 23 -0.19 1.45 2 3 -23 0.91 0.78 2 3 -23 1.12 1.22 2 3 -23 0.82 1.11 -1 -3 23 0.98 1.19 -1 -3 23 1.70 1.34 1 -3 -23 1.41 1.53 1 -3 -23 0.87 0.66 1 -3 -23 0.02 1.48 1 3 -23 -1.03 1.04 1 3 -23 1.04 1.31 0 -3 -23 4.85 1.16 0 -3 23 4.23 1.26 0 -3 -23 6.94 1.92 0 -3 -23 3.30 1.58 0 -3 23 3.24 1.47 0 -3 23 4.58 1.38 0 3 -23 5.17 1.55 -1 -3 -23 15.61 2.49 1 -3 23 8.32 1.46 -1 -3 -23 11.32 1.66 1 3 23 10.34 1.92 -2 -3 -23 7.14 0.96 2 -3 23 6.14 0.76 -2 -3 -23 4.48 1.28 2 3 23 7.55 1.70 -3 -3 -23 8.65 0.85 3 3 23 12.32 1.94 1 -4 -23 11.06 1.66 0 -4 -23 14.24 1.92 0 -4 23 12.26 0.79 0 4 -23 10.70 1.61 -4 0 24 1.31 1.53 4 0 -24 3.02 1.38 3 0 -24 0.75 1.78 3 0 -24 0.66 1.14 2 0 -24 -1.37 1.26 2 0 -24 1.19 0.75 1 0 -24 21.78 2.70 1 0 -24 24.06 2.30 1 0 -24 24.15 1.42 1 0 -24 26.63 3.03 0 0 -24 5.84 1.76 0 0 -24 2.85 2.06 0 0 -24 4.70 1.16 -1 0 -24 100.68 4.76 -1 0 -24 96.05 3.88 -1 0 -24 90.97 4.59 2 0 24 0.44 2.03 2 0 24 1.31 2.14 -2 0 -24 0.00 1.31 3 0 24 7.99 1.56 -3 0 -24 14.99 2.49 3 0 24 20.91 2.71 3 0 24 10.75 1.81 -4 0 -24 1.28 1.08 4 0 24 1.53 0.80 4 0 24 1.34 1.19 -4 -1 24 -0.62 1.37 4 -1 -24 -0.31 1.20 4 1 -24 -1.35 1.56 4 1 -24 -0.98 0.73 -3 -1 24 6.82 1.67 3 -1 -24 6.56 0.97 3 -1 -24 7.99 1.82 3 1 -24 7.63 1.45 -2 -1 24 11.15 2.01 2 -1 -24 15.16 1.94 2 -1 -24 13.88 2.14 2 1 -24 13.92 1.89 2 1 -24 16.41 2.79 2 1 -24 13.21 1.83 -1 -1 24 5.95 1.77 1 -1 -24 6.73 1.60 1 -1 -24 6.50 1.85 1 -1 -24 10.35 1.33 1 1 -24 4.62 1.25 1 1 -24 8.33 2.36 1 1 -24 6.22 1.57 0 -1 -24 16.57 2.59 0 -1 24 13.93 2.17 0 -1 -24 11.43 2.13 0 -1 -24 13.03 1.93 0 1 -24 18.91 2.78 0 1 -24 19.17 2.34 0 1 -24 10.32 2.36 -1 -1 -24 11.65 1.87 1 -1 24 12.92 2.33 -1 -1 -24 12.78 1.60 -1 -1 -24 15.58 2.54 -1 1 -24 19.41 2.84 -1 1 -24 12.74 2.55 -2 -1 -24 22.57 2.21 2 -1 24 20.69 2.37 2 -1 24 17.18 2.13 -2 -1 -24 19.90 2.58 2 1 24 23.01 2.80 3 -1 24 -0.07 0.66 -3 -1 -24 1.14 1.24 3 -1 24 -0.76 1.17 3 -1 24 2.03 1.68 3 1 24 1.80 1.45 3 1 24 1.06 1.53 -4 -1 -24 3.98 0.91 4 -1 24 9.44 1.45 4 1 24 7.62 1.15 4 1 24 7.69 1.51 4 -2 -24 -0.89 1.25 4 2 -24 1.01 0.80 -3 -2 24 0.33 1.20 3 -2 -24 0.87 1.42 3 2 -24 -0.32 1.24 3 2 -24 0.40 0.77 3 2 -24 0.20 1.19 2 -2 -24 2.08 1.56 -2 -2 24 3.31 1.49 2 -2 -24 1.05 0.74 2 2 -24 1.67 1.06 2 2 -24 1.92 1.45 2 2 -24 1.44 0.81 1 -2 -24 12.24 1.75 -1 -2 24 7.59 1.68 1 -2 -24 9.64 1.89 1 2 -24 7.07 1.44 1 2 -24 4.31 2.06 1 2 -24 8.88 1.93 0 -2 -24 23.49 2.88 0 -2 24 26.94 2.71 0 -2 -24 31.29 2.45 0 -2 24 26.94 2.94 0 2 -24 26.60 2.42 1 -2 24 5.40 1.65 -1 -2 -24 4.30 1.66 -1 -2 -24 3.49 1.15 1 -2 24 4.79 1.49 1 2 24 5.41 2.21 2 -2 24 18.25 1.36 2 -2 24 13.66 1.68 -2 -2 -24 20.51 2.03 -2 -2 -24 16.61 1.17 2 2 24 23.17 3.05 -3 -2 -24 0.35 0.94 3 -2 24 -0.06 1.46 -3 -2 -24 0.06 0.63 3 2 24 0.03 1.28 3 2 24 -1.26 1.37 3 -3 -24 5.19 1.18 3 3 -24 3.56 0.98 -2 -3 24 1.44 1.13 2 -3 -24 1.98 1.36 -2 -3 24 1.38 1.38 2 3 -24 -0.96 1.03 2 3 -24 0.74 0.60 -1 -3 24 2.20 1.18 1 -3 -24 4.33 1.72 -1 -3 24 2.38 1.22 1 3 -24 1.98 1.24 1 3 -24 2.27 1.01 0 -3 24 6.51 1.12 0 -3 24 4.33 1.35 0 -3 -24 5.74 1.79 0 -3 -24 4.53 1.05 0 -3 24 3.06 1.25 0 3 -24 5.51 1.36 0 3 -24 3.98 1.40 1 -3 24 16.59 1.59 -1 -3 -24 15.56 1.63 1 3 24 16.05 2.63 -2 -3 -24 2.89 1.23 2 3 24 2.19 1.66 4 0 -25 0.07 1.44 -4 0 25 1.65 1.11 3 0 -25 0.27 1.73 3 0 -25 -0.85 0.97 2 0 -25 25.19 2.27 1 0 -25 0.18 1.97 1 0 -25 1.24 1.25 1 0 -25 0.69 1.46 0 0 -25 2.11 1.63 0 0 -25 0.28 0.89 0 0 -25 1.48 1.50 -1 0 -25 1.98 1.27 -1 0 -25 -2.07 2.17 -1 0 -25 -0.40 1.42 2 0 25 -1.60 1.48 -2 0 -25 -0.36 1.07 2 0 25 -0.41 1.59 3 0 25 -1.61 0.86 3 0 25 0.71 1.32 3 0 25 1.73 1.57 -3 0 -25 1.32 1.42 4 0 25 0.75 0.60 -4 0 -25 -1.08 0.85 4 0 25 0.08 1.05 4 -1 -25 4.53 1.23 -3 -1 25 -0.19 1.25 3 -1 -25 1.31 1.39 3 1 -25 -0.04 1.22 -2 -1 25 -1.70 1.17 2 -1 -25 1.15 1.12 2 -1 -25 2.56 1.94 2 1 -25 2.60 1.14 2 1 -25 0.19 1.42 1 -1 -25 -0.24 1.50 -1 -1 25 2.32 1.52 1 1 -25 0.83 0.97 1 1 -25 2.04 1.56 0 -1 -25 10.22 2.04 0 -1 -25 15.00 1.76 0 -1 25 13.27 2.42 0 1 -25 12.76 1.81 0 1 -25 12.64 2.58 0 1 -25 12.64 2.05 -1 -1 -25 1.26 0.86 1 -1 25 0.62 1.73 -1 -1 -25 -0.02 1.19 -1 1 -25 0.73 1.24 -2 -1 -25 0.58 1.39 2 -1 25 -0.16 1.85 2 -1 25 -0.70 1.23 -2 -1 -25 1.30 1.08 -2 1 -25 -0.57 1.32 2 1 25 -2.53 1.56 3 -1 25 0.48 0.86 -3 -1 -25 0.95 1.39 -3 -1 -25 0.46 0.98 3 -1 25 -0.59 1.29 3 1 25 2.36 1.36 3 1 25 -0.24 1.72 3 1 25 0.46 1.21 -3 -2 25 3.36 1.51 3 -2 -25 1.05 1.60 3 2 -25 -0.13 1.29 3 2 -25 1.02 1.20 2 -2 -25 5.09 1.90 -2 -2 25 2.31 1.38 2 2 -25 2.21 1.34 2 2 -25 2.09 1.22 1 -2 -25 7.33 1.76 1 -2 -25 5.04 1.20 -1 -2 25 7.45 1.57 1 2 -25 7.47 2.02 1 2 -25 6.42 1.28 1 2 -25 6.28 1.60 0 -2 25 10.47 1.80 0 -2 -25 15.86 1.92 0 -2 25 16.17 2.75 0 2 -25 11.29 1.90 0 2 -25 10.87 2.05 -1 -2 -25 5.52 1.60 -1 -2 -25 7.59 1.11 1 -2 25 9.23 1.45 1 -2 25 11.20 2.06 -1 2 -25 4.95 1.48 2 -2 25 17.39 1.58 -2 -2 -25 17.61 1.78 2 2 25 21.45 2.72 -3 -2 -25 5.04 1.08 3 2 25 9.24 1.38 3 2 25 4.98 1.35 2 -3 -25 0.61 1.16 -2 -3 25 0.98 1.04 -2 -3 25 1.81 0.97 2 3 -25 -0.29 1.19 -1 -3 25 0.54 1.01 1 -3 -25 4.98 1.61 -1 -3 25 0.20 1.26 -1 -3 25 -0.01 1.09 1 3 -25 0.56 1.15 1 3 -25 0.94 0.87 0 -3 -25 -0.17 0.72 0 -3 25 0.48 1.28 0 -3 -25 -0.65 1.43 0 -3 25 1.02 1.27 0 -3 25 0.90 0.83 0 3 -25 -0.01 0.99 0 3 -25 0.35 1.18 -1 -3 -25 0.07 0.96 1 -3 25 -0.53 0.82 -1 3 -25 1.31 1.42 -1 3 -25 1.84 1.09 -2 -3 -25 1.08 1.01 -3 0 26 0.18 1.30 3 0 -26 1.77 1.63 3 0 -26 1.57 0.86 2 0 -26 -1.18 1.26 1 0 -26 15.87 1.78 1 0 -26 14.09 2.30 0 0 -26 12.75 1.41 0 0 -26 11.79 1.78 -1 0 -26 7.75 1.73 -1 0 -26 11.67 1.54 -2 0 -26 -2.38 1.47 2 0 26 0.79 1.36 -2 0 -26 -2.00 0.93 -3 0 -26 4.64 1.09 3 0 26 3.95 1.24 3 0 26 4.70 0.88 3 0 26 5.88 1.65 3 -1 -26 1.40 1.30 -3 -1 26 2.99 1.27 3 1 -26 1.11 0.96 2 -1 -26 5.75 1.70 2 -1 -26 4.25 1.28 -2 -1 26 6.22 1.56 2 1 -26 5.72 1.06 2 1 -26 5.71 1.53 1 -1 -26 9.23 1.78 -1 -1 26 6.32 1.58 1 1 -26 7.75 1.27 1 1 -26 11.70 1.98 0 -1 26 7.91 1.91 0 -1 -26 6.75 1.24 0 -1 -26 8.18 2.09 0 1 -26 8.23 1.66 0 1 -26 8.00 1.37 1 -1 26 6.21 1.76 -1 -1 -26 6.61 1.13 -1 -1 -26 5.15 1.43 -1 1 -26 6.76 1.49 -2 -1 -26 3.23 0.88 -2 -1 -26 3.68 1.34 2 -1 26 5.22 1.27 2 -1 26 3.13 1.81 -2 1 -26 3.51 1.29 2 1 26 5.14 1.74 2 1 26 9.16 1.92 3 -1 26 0.32 0.86 -3 -1 -26 1.20 0.76 3 -1 26 0.20 1.18 -3 -1 -26 -0.09 1.34 3 1 26 1.87 1.67 3 1 26 0.13 0.92 3 1 26 0.80 1.15 -3 1 -26 0.09 1.09 3 -2 -26 2.34 1.19 -3 -2 26 2.07 1.12 3 2 -26 2.18 0.87 2 -2 -26 0.17 1.34 -2 -2 26 1.41 1.12 2 2 -26 1.37 1.45 2 2 -26 1.30 0.99 1 -2 -26 3.52 1.79 -1 -2 26 4.08 1.64 1 -2 -26 2.10 1.08 -1 -2 26 2.89 1.58 1 2 -26 2.30 1.51 1 2 -26 2.23 0.86 1 2 -26 1.35 1.60 1 2 -26 4.30 1.45 0 -2 26 11.93 1.97 0 -2 -26 9.90 1.59 0 -2 26 8.14 1.59 0 2 -26 4.19 1.47 0 2 -26 7.89 1.41 0 2 -26 6.31 1.75 1 -2 26 6.55 1.62 -1 -2 -26 17.50 2.16 1 -2 26 10.03 1.67 -1 -2 -26 9.75 1.00 -1 2 -26 11.72 1.98 2 -2 26 8.17 1.29 -2 -2 -26 8.14 1.11 -2 2 -26 4.95 1.35 2 2 26 6.26 1.61 -1 -3 26 8.14 1.33 -1 -3 26 10.39 1.49 -1 -3 26 12.68 1.41 1 -3 -26 12.10 1.73 1 3 -26 7.08 1.29 1 3 -26 9.40 1.13 0 -3 26 13.04 1.51 0 -3 26 15.20 1.03 0 -3 -26 13.46 1.05 0 3 -26 7.74 1.56 -1 -3 -26 2.59 0.86 1 -3 26 1.95 0.70 -1 3 -26 2.29 1.03 -1 3 -26 0.94 1.23 3 0 -27 0.14 0.70 -3 0 27 -0.42 1.19 2 0 -27 2.73 1.29 1 0 -27 1.80 0.88 1 0 -27 -0.19 1.37 0 0 -27 48.04 1.70 0 0 -27 45.15 2.54 -1 0 -27 0.77 0.85 -1 0 -27 0.75 1.17 -2 0 -27 2.38 0.84 2 0 27 2.59 1.30 -2 0 -27 1.88 1.39 3 0 27 0.73 1.18 3 0 27 0.31 0.59 3 0 27 0.65 1.34 -3 0 -27 -0.20 0.84 3 -1 -27 -1.04 1.30 -3 -1 27 -0.74 1.11 3 1 -27 -0.20 0.84 -2 -1 27 7.15 1.49 2 -1 -27 9.11 1.18 2 1 -27 7.92 1.48 1 -1 -27 13.31 1.70 -1 -1 27 15.64 2.58 1 1 -27 13.43 1.80 0 -1 27 8.72 1.76 0 -1 -27 9.23 1.76 0 -1 -27 12.97 1.29 0 1 -27 13.91 1.96 0 1 -27 10.76 1.43 1 -1 27 2.66 1.44 -1 -1 -27 1.56 1.02 -1 1 -27 2.33 1.49 -1 1 -27 0.71 1.15 2 -1 27 3.43 1.32 2 -1 27 2.11 0.92 -2 -1 -27 1.88 1.27 -2 -1 -27 1.53 0.63 2 1 27 0.72 1.46 -2 1 -27 3.73 1.08 -3 -1 -27 1.12 0.54 3 -1 27 1.53 0.71 -3 -1 -27 2.33 0.88 3 1 27 1.44 1.29 -3 1 -27 0.74 0.84 3 1 27 1.27 0.71 -2 -2 27 0.76 1.33 2 -2 -27 -0.15 1.45 -1 -2 27 4.78 1.52 -1 -2 27 4.78 1.36 1 -2 -27 5.02 0.83 1 2 -27 4.40 0.69 1 2 -27 4.13 1.54 1 2 -27 6.13 1.21 1 2 -27 5.58 1.35 0 -2 -27 -0.02 1.08 0 -2 27 0.57 1.12 0 2 -27 0.23 0.94 0 2 -27 0.36 1.39 -1 -2 -27 4.88 1.25 1 -2 27 4.33 1.03 1 -2 27 4.67 1.30 -1 2 -27 6.56 1.14 2 -2 27 2.59 0.91 -2 -2 -27 2.95 0.64 -2 2 -27 2.55 1.02 3 0 -28 1.14 0.49 -3 0 28 1.03 1.14 -2 0 28 0.27 1.32 2 0 -28 1.93 0.88 1 0 -28 -1.25 1.47 -1 0 28 0.19 1.29 0 0 -28 5.72 1.22 -1 0 -28 12.41 1.19 -1 0 -28 14.49 1.97 1 0 28 14.51 2.50 -2 0 -28 3.70 0.92 2 0 28 5.11 1.32 -2 0 -28 5.19 1.28 -3 -1 28 3.94 1.33 3 1 -28 1.49 0.71 -2 -1 28 8.40 1.42 2 -1 -28 8.06 1.00 2 1 -28 6.59 1.31 -1 -1 28 0.20 1.17 1 -1 -28 1.40 1.11 1 1 -28 1.74 1.03 1 1 -28 0.90 0.91 0 -1 -28 -1.02 1.15 0 -1 28 3.67 1.72 0 1 -28 0.53 1.03 0 1 -28 0.09 0.67 1 -1 28 0.82 1.40 -1 -1 -28 1.81 0.93 -1 1 -28 0.33 1.23 -1 1 -28 -0.14 0.89 2 -1 28 24.13 1.71 2 -1 28 20.82 1.38 -2 -1 -28 19.75 1.58 2 1 28 20.11 2.01 -2 1 -28 20.44 1.76 -2 -2 28 4.31 1.08 1 -2 -28 9.65 0.96 -1 -2 28 14.72 2.18 -1 -2 28 12.86 2.01 0 -2 28 3.67 1.25 0 -2 28 4.57 1.44 0 -2 -28 3.48 1.00 0 2 -28 3.54 1.48 0 2 -28 3.01 0.83 1 -2 28 3.87 1.09 -1 -2 -28 2.71 0.97 1 -2 28 2.48 0.68 -1 2 -28 2.82 0.94 -1 2 -28 1.66 1.41 2 0 -29 0.03 0.84 -2 0 29 -0.56 1.14 1 0 -29 0.55 1.03 -1 0 29 -0.69 1.40 0 0 -29 2.83 0.94 1 0 29 1.27 1.40 -1 0 -29 -1.55 0.79 2 0 29 10.33 1.46 2 0 29 7.84 1.48 -2 0 -29 9.53 1.32 -2 0 -29 8.40 0.87 -2 -1 29 1.74 1.01 2 1 -29 1.33 0.86 -1 -1 29 -0.97 1.30 1 -1 -29 0.02 0.95 0 -1 -29 5.08 1.19 0 -1 29 5.01 1.69 0 1 -29 4.34 1.23 1 -1 29 9.04 1.42 -1 -1 -29 7.37 0.92 -1 1 -29 7.47 1.10 -1 1 -29 8.94 1.45 -2 -1 -29 0.19 0.54 2 -1 29 -0.61 0.96 -2 1 -29 0.32 0.71 2 1 29 2.00 1.18 -1 -2 29 7.31 1.43 0 -2 29 2.14 1.50 0 -2 29 5.69 1.02 0 -2 -29 4.18 0.79 0 2 -29 4.74 1.03 2 0 -30 17.83 1.23 -2 0 30 17.04 1.66 1 0 -30 2.98 0.99 -1 0 30 4.25 1.32 0 0 -30 3.56 1.23 0 0 -30 3.34 0.61 1 0 30 0.13 1.05 -1 0 -30 -0.25 0.67 1 -1 -30 2.08 0.72 1 1 -30 1.37 1.04 0 -1 -30 1.30 0.83 0 -1 30 0.81 1.11 0 1 -30 0.64 0.88 1 -1 30 8.15 1.30 -1 1 -30 4.70 1.07 0 0 0 0.00 0.00 ; _shelx_hkl_checksum 15627 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems' _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a nylon loop with paratone oil' _olex2_submission_original_sample_id '2 Tyrosine hydrazide DAB' _olex2_submission_special_instructions 'No special instructions were received' 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 O1 O 0.4810(4) 0.0380(5) 0.21791(10) 0.0246(5) Uani 1 1 d . H1 H 0.599(7) 0.045(9) 0.2118(15) 0.030(12) Uiso 1 1 d . O2 O -0.1292(3) 0.3463(5) 0.28741(9) 0.0282(6) Uani 1 1 d . O3 O 0.9569(4) 0.8718(6) 0.47787(10) 0.0335(6) Uani 1 1 d . H3 H 0.994(9) 0.735(11) 0.493(2) 0.055(15) Uiso 1 1 d . N1 N 0.1131(4) 0.2563(6) 0.22042(11) 0.0238(6) Uani 1 1 d . N2 N -0.0504(4) 0.1460(7) 0.18632(12) 0.0299(7) Uani 1 1 d . N3 N 0.4302(4) 0.4992(6) 0.25300(11) 0.0201(6) Uani 1 1 d . H3A H 0.569(6) 0.466(7) 0.2630(13) 0.019(9) Uiso 1 1 d . H3B H 0.421(5) 0.670(7) 0.2432(12) 0.009(8) Uiso 1 1 d . C1 C -0.0028(6) 0.1697(9) 0.13734(15) 0.0355(9) Uani 1 1 d . H1A H -0.102251 0.083314 0.112735 0.043 Uiso 1 1 calc R C2 C 0.1868(6) 0.3142(8) 0.11554(14) 0.0306(8) Uani 1 1 d . C3 C 0.3685(5) 0.3971(7) 0.14831(13) 0.0259(8) Uani 1 1 d . C4 C 0.5343(6) 0.5529(7) 0.12649(14) 0.0307(8) Uani 1 1 d . H4 H 0.659116 0.610007 0.147875 0.037 Uiso 1 1 calc R C5 C 0.5213(7) 0.6273(9) 0.07382(16) 0.0406(10) Uani 1 1 d . H5 H 0.636127 0.735806 0.059737 0.049 Uiso 1 1 calc R C6 C 0.3422(8) 0.5442(9) 0.04178(15) 0.0460(10) Uani 1 1 d . H6 H 0.334888 0.594971 0.005798 0.055 Uiso 1 1 calc R C7 C 0.1746(7) 0.3879(10) 0.06202(15) 0.0419(10) Uani 1 1 d . H7 H 0.051708 0.330232 0.040102 0.050 Uiso 1 1 calc R C8 C 0.0564(5) 0.3463(7) 0.26768(12) 0.0215(7) Uani 1 1 d . C9 C 0.2697(5) 0.4505(6) 0.29611(13) 0.0216(7) Uani 1 1 d . H9 H 0.331867 0.301063 0.318560 0.026 Uiso 1 1 calc R C10 C 0.2297(5) 0.6891(7) 0.33126(13) 0.0248(7) Uani 1 1 d . H10A H 0.090967 0.657904 0.350774 0.030 Uiso 1 1 calc R H10B H 0.206013 0.851685 0.309257 0.030 Uiso 1 1 calc R C11 C 0.4237(5) 0.7398(7) 0.37032(13) 0.0234(7) Uani 1 1 d . C12 C 0.4339(6) 0.6028(7) 0.41798(13) 0.0275(8) Uani 1 1 d . H12 H 0.317188 0.480550 0.426035 0.033 Uiso 1 1 calc R C13 C 0.6109(6) 0.6409(8) 0.45400(14) 0.0295(8) Uani 1 1 d . H13 H 0.616716 0.543187 0.486101 0.035 Uiso 1 1 calc R C14 C 0.7785(5) 0.8221(7) 0.44274(13) 0.0257(7) Uani 1 1 d . C15 C 0.7736(5) 0.9598(7) 0.39579(14) 0.0261(8) Uani 1 1 d . H15 H 0.889776 1.083684 0.388196 0.031 Uiso 1 1 calc R C16 C 0.5972(5) 0.9162(7) 0.35947(13) 0.0233(7) Uani 1 1 d . H16 H 0.595520 1.008624 0.326786 0.028 Uiso 1 1 calc R B1 B 0.3631(6) 0.2855(8) 0.20730(15) 0.0221(8) Uani 1 1 d . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0158(12) 0.0212(13) 0.0368(13) 0.0004(10) 0.0021(10) -0.0013(11) O2 0.0144(10) 0.0346(14) 0.0357(13) 0.0013(11) 0.0013(9) -0.0014(11) O3 0.0304(13) 0.0294(15) 0.0397(14) -0.0020(12) -0.0144(11) 0.0000(13) N1 0.0141(12) 0.0258(15) 0.0313(15) -0.0007(12) -0.0028(11) -0.0019(12) N2 0.0173(13) 0.0361(17) 0.0359(17) -0.0081(13) -0.0061(12) -0.0059(14) N3 0.0119(13) 0.0174(17) 0.0310(15) 0.0022(11) -0.0005(11) 0.0004(12) C1 0.0263(18) 0.044(2) 0.036(2) -0.0100(17) -0.0086(16) -0.0027(18) C2 0.0264(16) 0.032(2) 0.0333(19) -0.0061(15) -0.0007(14) 0.0005(17) C3 0.0221(16) 0.0215(18) 0.0342(18) -0.0028(14) 0.0022(14) 0.0038(15) C4 0.0295(17) 0.029(2) 0.0342(19) -0.0006(15) 0.0041(15) -0.0017(17) C5 0.048(2) 0.038(2) 0.037(2) 0.0021(18) 0.0103(19) -0.007(2) C6 0.064(3) 0.047(2) 0.027(2) 0.0020(18) 0.0022(19) -0.001(3) C7 0.043(2) 0.050(3) 0.032(2) -0.0076(18) -0.0051(17) 0.001(2) C8 0.0158(14) 0.0177(17) 0.0307(17) 0.0057(13) -0.0029(12) 0.0020(14) C9 0.0143(14) 0.0193(17) 0.0308(17) 0.0021(13) -0.0018(13) 0.0025(13) C10 0.0197(16) 0.0228(18) 0.0317(17) -0.0014(14) -0.0020(14) 0.0014(15) C11 0.0164(15) 0.0241(18) 0.0298(17) -0.0049(13) 0.0015(13) 0.0055(14) C12 0.0260(17) 0.027(2) 0.0292(18) 0.0016(14) 0.0025(15) -0.0055(16) C13 0.0340(19) 0.0275(18) 0.0270(18) 0.0007(14) 0.0005(15) -0.0011(17) C14 0.0225(16) 0.0239(19) 0.0305(18) -0.0050(14) -0.0050(13) 0.0041(16) C15 0.0188(15) 0.0222(19) 0.0374(19) 0.0002(14) 0.0013(14) 0.0011(15) C16 0.0206(16) 0.0204(17) 0.0288(17) -0.0001(13) 0.0007(13) 0.0031(14) B1 0.0151(16) 0.0175(19) 0.034(2) 0.0000(14) -0.0003(15) -0.0028(15) 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' B B 0.0090 0.0039 '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 B1 O1 H1 113(4) C14 O3 H3 111(4) N2 N1 B1 124.1(3) C8 N1 N2 120.0(3) C8 N1 B1 115.9(3) C1 N2 N1 113.2(3) H3A N3 H3B 108(3) C9 N3 H3A 112(2) C9 N3 H3B 109(2) C9 N3 B1 105.9(2) B1 N3 H3A 107(2) B1 N3 H3B 114(2) N2 C1 H1A 116.3 N2 C1 C2 127.4(3) C2 C1 H1A 116.3 C3 C2 C1 120.4(3) C3 C2 C7 120.8(4) C7 C2 C1 118.6(3) C2 C3 B1 114.6(3) C4 C3 C2 118.0(3) C4 C3 B1 127.3(3) C3 C4 H4 119.4 C3 C4 C5 121.1(4) C5 C4 H4 119.4 C4 C5 H5 119.8 C6 C5 C4 120.5(4) C6 C5 H5 119.8 C5 C6 H6 120.0 C7 C6 C5 120.1(4) C7 C6 H6 120.0 C2 C7 H7 120.2 C6 C7 C2 119.5(4) C6 C7 H7 120.2 O2 C8 N1 128.7(3) O2 C8 C9 123.4(3) N1 C8 C9 108.0(3) N3 C9 C8 104.3(3) N3 C9 H9 107.8 N3 C9 C10 115.2(3) C8 C9 H9 107.8 C10 C9 C8 113.6(3) C10 C9 H9 107.8 C9 C10 H10A 109.0 C9 C10 H10B 109.0 C9 C10 C11 112.8(3) H10A C10 H10B 107.8 C11 C10 H10A 109.0 C11 C10 H10B 109.0 C12 C11 C10 120.0(3) C16 C11 C10 121.9(3) C16 C11 C12 118.1(3) C11 C12 H12 119.3 C13 C12 C11 121.4(3) C13 C12 H12 119.3 C12 C13 H13 120.3 C14 C13 C12 119.3(3) C14 C13 H13 120.3 C13 C14 O3 121.7(3) C15 C14 O3 117.7(3) C15 C14 C13 120.6(3) C14 C15 H15 120.2 C14 C15 C16 119.6(3) C16 C15 H15 120.2 C11 C16 C15 121.0(3) C11 C16 H16 119.5 C15 C16 H16 119.5 O1 B1 N1 110.4(3) O1 B1 N3 108.5(3) O1 B1 C3 116.6(3) N1 B1 N3 97.1(3) N1 B1 C3 106.5(3) C3 B1 N3 115.9(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 H1 0.73(4) O1 B1 1.436(5) O2 C8 1.229(4) O3 H3 0.81(5) O3 C14 1.388(4) N1 N2 1.395(4) N1 C8 1.337(4) N1 B1 1.543(4) N2 C1 1.294(5) N3 H3A 0.87(4) N3 H3B 0.89(4) N3 C9 1.499(4) N3 B1 1.615(5) C1 H1A 0.9500 C1 C2 1.462(5) C2 C3 1.406(5) C2 C7 1.411(5) C3 C4 1.385(5) C3 B1 1.602(5) C4 H4 0.9500 C4 C5 1.391(5) C5 H5 0.9500 C5 C6 1.384(6) C6 H6 0.9500 C6 C7 1.377(6) C7 H7 0.9500 C8 C9 1.531(4) C9 H9 1.0000 C9 C10 1.508(5) C10 H10A 0.9900 C10 H10B 0.9900 C10 C11 1.520(4) C11 C12 1.391(5) C11 C16 1.389(5) C12 H12 0.9500 C12 C13 1.387(5) C13 H13 0.9500 C13 C14 1.381(5) C14 C15 1.377(5) C15 H15 0.9500 C15 C16 1.394(4) C16 H16 0.9500 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag O3 H3 O3 0.81(5) 1.96(5) 2.766(2) 170(5) 2_746 yes N3 H3A O2 0.87(4) 1.97(4) 2.841(3) 173(3) 1_655 yes N3 H3B O1 0.89(4) 1.97(4) 2.839(4) 166(3) 1_565 yes 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 O2 C8 C9 N3 -161.5(3) O2 C8 C9 C10 -35.2(5) O3 C14 C15 C16 -179.9(3) N1 N2 C1 C2 -5.5(6) N1 C8 C9 N3 19.8(3) N1 C8 C9 C10 146.0(3) N2 N1 C8 O2 0.5(5) N2 N1 C8 C9 179.2(3) N2 N1 B1 O1 -83.6(4) N2 N1 B1 N3 163.6(3) N2 N1 B1 C3 43.8(4) N2 C1 C2 C3 14.0(6) N2 C1 C2 C7 -160.7(4) N3 C9 C10 C11 -76.0(4) C1 C2 C3 C4 -174.6(3) C1 C2 C3 B1 8.0(5) C1 C2 C7 C6 174.4(4) C2 C3 C4 C5 0.5(5) C2 C3 B1 O1 92.6(3) C2 C3 B1 N1 -31.1(4) C2 C3 B1 N3 -137.8(3) C3 C2 C7 C6 -0.3(6) C3 C4 C5 C6 -0.7(6) C4 C3 B1 O1 -84.5(4) C4 C3 B1 N1 151.9(3) C4 C3 B1 N3 45.2(4) C4 C5 C6 C7 0.3(7) C5 C6 C7 C2 0.2(6) C7 C2 C3 C4 0.0(5) C7 C2 C3 B1 -177.3(3) C8 N1 N2 C1 153.2(3) C8 N1 B1 O1 96.9(4) C8 N1 B1 N3 -16.0(4) C8 N1 B1 C3 -135.7(3) C8 C9 C10 C11 163.7(3) C9 N3 B1 O1 -87.3(3) C9 N3 B1 N1 27.0(3) C9 N3 B1 C3 139.3(3) C9 C10 C11 C12 -85.5(4) C9 C10 C11 C16 92.9(4) C10 C11 C12 C13 178.8(3) C10 C11 C16 C15 -179.9(3) C11 C12 C13 C14 1.2(5) C12 C11 C16 C15 -1.5(5) C12 C13 C14 O3 178.7(3) C12 C13 C14 C15 -1.5(5) C13 C14 C15 C16 0.3(5) C14 C15 C16 C11 1.3(5) C16 C11 C12 C13 0.3(5) B1 N1 N2 C1 -26.4(5) B1 N1 C8 O2 -180.0(3) B1 N1 C8 C9 -1.3(4) B1 N3 C9 C8 -29.4(3) B1 N3 C9 C10 -154.7(3) B1 C3 C4 C5 177.5(3) loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.8 2 0.2