# Electronic Supplementary Material (ESI) for Chemical Science. # This journal is © The Royal Society of Chemistry 2021 ####################################################################### # # This file contains crystal structure data downloaded from the # Cambridge Structural Database (CSD) hosted by the Cambridge # Crystallographic Data Centre (CCDC). # # Full information about CCDC data access policies and citation # guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 # # Audit and citation data items may have been added by the CCDC. # Please retain this information to preserve the provenance of # this file and to allow appropriate attribution of the data. # ####################################################################### data_db-3-281 _database_code_depnum_ccdc_archive 'CCDC 2033833' loop_ _audit_author_name _audit_author_address 'Benjamin S. Gelfand' ;University of Calgary Canada ; _audit_update_record ; 2020-09-24 deposited with the CCDC. 2021-02-02 downloaded from the CCDC. ; _audit_creation_date 2019-11-06 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _shelx_SHELXL_version_number 2018/3 _chemical_name_common ? _chemical_name_systematic ? _chemical_formula_moiety 'C15 H15 N3 O4, 0.377(C4 H8 O2), 0.123(C6 H14)' _chemical_formula_sum 'C17.24 H19.73 N3 O4.75' _chemical_formula_weight 345.09 _chemical_melting_point ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _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. ; _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.2814(2) _cell_length_b 10.1224(2) _cell_length_c 12.1780(3) _cell_angle_alpha 92.523(2) _cell_angle_beta 106.963(2) _cell_angle_gamma 100.062(2) _cell_volume 841.02(4) _cell_formula_units_Z 2 _cell_measurement_reflns_used 9480 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 68.208 _cell_measurement_theta_min 3.814 _shelx_estimated_absorpt_T_max 0.846 _shelx_estimated_absorpt_T_min 0.763 _exptl_absorpt_coefficient_mu 0.839 _exptl_absorpt_correction_T_max 0.7531 _exptl_absorpt_correction_T_min 0.6985 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0679 before and 0.0366 after correction. The Ratio of minimum to maximum transmission is 0.9275. The \l/2 correction factor is Not present.' _exptl_absorpt_special_details ? _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.363 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_F_000 364.5 _exptl_crystal_size_max 0.341 _exptl_crystal_size_mid 0.263 _exptl_crystal_size_min 0.206 _exptl_transmission_factor_max ? _exptl_transmission_factor_min ? _diffrn_reflns_av_R_equivalents 0.0315 _diffrn_reflns_av_unetI/netI 0.0109 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 3077 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 67.679 _diffrn_reflns_theta_max 68.282 _diffrn_reflns_theta_min 3.814 _diffrn_ambient_temperature 173.0 _diffrn_detector_area_resol_mean ? _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_source ? _diffrn_standards_number 0 _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_full . _reflns_Friedel_fraction_max . _reflns_number_gt 2989 _reflns_number_total 3077 _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _reflns_threshold_expression 'I > 2\s(I)' _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_collection ? _computing_data_reduction 'SAINT v8.37A (Bruker, 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)' _refine_diff_density_max 0.309 _refine_diff_density_min -0.332 _refine_diff_density_rms 0.075 _refine_ls_extinction_coef . _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 323 _refine_ls_number_reflns 3077 _refine_ls_number_restraints 286 _refine_ls_R_factor_all 0.0490 _refine_ls_R_factor_gt 0.0482 _refine_ls_restrained_S_all 1.031 _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^)+(0.0836P)^2^+0.4639P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1237 _refine_ls_wR_factor_ref 0.1247 _refine_special_details ? _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. Restrained distances C6T-C2S 1.51 with sigma of 0.02 O1S-C2S 1.2 with sigma of 0.02 O2S-C2S 1.35 with sigma of 0.02 O2S-C3S 1.45 with sigma of 0.02 C4S-C3S 1.52 with sigma of 0.02 C1T-C2T = C2T-C3T = C3T-C4T = C4T-C5T = C5T-C6T 1.53 with sigma of 0.02 C1T-C5T = C3T-C6T -2.75 with sigma of 0.02 C1T-C3T = C2T-C4T = C3T-C5T = C4T-C6T 2.54 with sigma of 0.04 O1S-C6T 2.25 with sigma of 0.04 C6T-O2S 2.52 with sigma of 0.04 O2S-O1S 2.25 with sigma of 0.04 C2S-C3S 2.37 with sigma of 0.04 O2S-C4S 2.46 with sigma of 0.04 3. Restrained planarity O1S, O2S, C6T, C2S with sigma of 0.1 4. Uiso/Uaniso restraints and constraints C2T \\sim C3T \\sim C4T \\sim C1T \\sim C5T \\sim C6T \\sim C4S \\sim O1S \\sim C2S \\sim O2S \\sim C1SA \\sim C3S: within 2.6A with sigma of 0.03 and sigma for terminal atoms of 0.06 5. Rigid body (RIGU) restrains C5T, C3T, C2T, C4T, C1T, C6T with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004 6. Others Sof(C3T)=Sof(H3TA)=Sof(H3TB)=Sof(C6T)=Sof(H6TA)=Sof(H6TB)=Sof(H6TC)=Sof(C1T)= Sof(H1TA)=Sof(H1TB)=Sof(H1TC)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=Sof(C4T)=Sof(H4TA)= Sof(H4TB)=Sof(C5T)=Sof(H5TA)=Sof(H5TB)=0.5*(1-FVAR(2)) Sof(O1S)=Sof(O2S)=Sof(C2S)=Sof(C3S)=Sof(H3SA)=Sof(H3SB)=Sof(C4S)=Sof(H4SA)= Sof(H4SB)=Sof(H4SC)=Sof(C1SA)=Sof(H1SA)=Sof(H1SB)=Sof(H1SC)=0.5*FVAR(2) Sof(C15)=Sof(H15A)=Sof(H15B)=FVAR(2) 7.a Ternary CH refined with riding coordinates: C11(H11) 7.b Secondary CH2 refined with riding coordinates: C14(H14A,H14B), C15(H15A,H15B), C3T(H3TA,H3TB), C2T(H2TA,H2TB), C3S(H3SA, H3SB), C4T(H4TA,H4TB), C5T(H5TA,H5TB) 7.c Aromatic/amide H refined with riding coordinates: N3(H3), C4(H4), C5(H5), C6(H6) 7.d Idealised Me refined as rotating group: C1(H1A,H1B,H1C), C6T(H6TA,H6TB,H6TC), C1T(H1TA,H1TB,H1TC), C4S(H4SA,H4SB, H4SC), C1SA(H1SA,H1SB,H1SC) ; _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _atom_sites_solution_secondary ? loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O 0.33820(19) 0.42088(12) 0.77534(10) 0.0340(3) Uani 1 1 d . . . . . O2 O 0.05758(19) 0.15674(12) 0.43537(10) 0.0330(3) Uani 1 1 d . . . . . O3 O 0.51537(17) 0.17136(12) 0.73062(11) 0.0304(3) Uani 1 1 d . . . . . O4 O 0.26038(19) -0.01730(17) 0.99452(12) 0.0469(4) Uani 1 1 d . . . . . N1 N 0.4170(2) 0.71237(15) 0.67328(16) 0.0378(4) Uani 1 1 d . . . . . N2 N 0.18079(19) 0.26484(13) 0.61954(11) 0.0220(3) Uani 1 1 d . . . . . N3 N 0.38090(19) 0.08175(14) 0.86191(11) 0.0245(3) Uani 1 1 d . . . . . H3 H 0.499028 0.078265 0.906314 0.029 Uiso 1 1 calc R . . . . C1 C 0.5130(3) 0.8477(2) 0.6611(3) 0.0563(7) Uani 1 1 d . . . . . H1A H 0.608297 0.841261 0.619507 0.084 Uiso 1 1 calc GR . . . . H1B H 0.580452 0.896083 0.737728 0.084 Uiso 1 1 calc GR . . . . H1C H 0.414665 0.896490 0.617901 0.084 Uiso 1 1 calc GR . . . . C2 C 0.3188(3) 0.7137(2) 0.7615(2) 0.0417(5) Uani 1 1 d . . . . . H2A H 0.221(4) 0.777(3) 0.745(2) 0.063 Uiso 1 1 d R . . . . H2B H 0.414(4) 0.749(3) 0.835(3) 0.063 Uiso 1 1 d R . . . . H2C H 0.250(4) 0.625(3) 0.769(2) 0.063 Uiso 1 1 d R . . . . C3 C 0.3370(2) 0.62201(16) 0.57530(16) 0.0273(4) Uani 1 1 d . . . . . C4 C 0.3314(2) 0.66254(17) 0.46491(18) 0.0332(4) Uani 1 1 d . . . . . H4 H 0.381859 0.754264 0.459336 0.040 Uiso 1 1 calc R . . . . C5 C 0.2568(3) 0.57612(19) 0.36529(17) 0.0338(4) Uani 1 1 d . . . . . H5 H 0.257697 0.609538 0.293735 0.041 Uiso 1 1 calc R . . . . C6 C 0.1794(2) 0.43993(18) 0.36712(15) 0.0278(4) Uani 1 1 d . . . . . H6 H 0.125778 0.379613 0.298642 0.033 Uiso 1 1 calc R . . . . C7 C 0.1858(2) 0.39869(15) 0.47384(14) 0.0213(3) Uani 1 1 d . . . . . C8 C 0.2630(2) 0.48365(15) 0.57662(14) 0.0215(3) Uani 1 1 d . . . . . C9 C 0.2692(2) 0.39663(15) 0.67174(14) 0.0228(3) Uani 1 1 d . . . . . C10 C 0.1298(2) 0.25864(15) 0.50098(13) 0.0213(3) Uani 1 1 d . . . . . C11 C 0.1655(2) 0.14848(15) 0.68419(13) 0.0216(3) Uani 1 1 d . . . . . H11 H 0.115987 0.066676 0.626928 0.026 Uiso 1 1 calc R . . . . C12 C 0.3700(2) 0.13822(15) 0.75943(13) 0.0211(3) Uani 1 1 d . . . . . C13 C 0.2275(2) 0.03024(17) 0.90243(14) 0.0268(4) Uani 1 1 d . . . . . C14 C 0.0253(2) 0.03221(18) 0.82674(14) 0.0277(4) Uani 1 1 d . . . . . H14A H -0.060725 0.038829 0.875629 0.033 Uiso 1 1 calc R . . . . H14B H -0.026684 -0.053731 0.776256 0.033 Uiso 1 1 calc R . . . . C15 C 0.0193(2) 0.14933(18) 0.75183(14) 0.0272(6) Uani 0.998(8) 1 d . . P . . H15A H -0.114250 0.141029 0.697653 0.033 Uiso 0.998(8) 1 calc R . P . . H15B H 0.052040 0.235696 0.801217 0.033 Uiso 0.998(8) 1 calc R . P . . O1S O 0.0391(13) 0.6921(8) 0.9190(7) 0.108(3) Uani 0.377(4) 1 d D U P A -1 O2S O 0.0090(13) 0.5114(10) 1.0245(4) 0.0648(19) Uani 0.377(4) 1 d D U P A -1 C3T C 0.127(4) 0.564(3) 1.005(3) 0.100(7) Uani 0.123(4) 1 d D U P A -2 H3TA H 0.064198 0.608237 1.054723 0.120 Uiso 0.123(4) 1 calc R . P A -2 H3TB H 0.218167 0.634072 0.981890 0.120 Uiso 0.123(4) 1 calc R . P A -2 C6T C -0.257(5) 0.559(5) 0.989(4) 0.113(11) Uani 0.123(4) 1 d D U P A -2 H6TA H -0.342174 0.592137 0.922287 0.170 Uiso 0.123(4) 1 calc GR . P A -2 H6TB H -0.137292 0.627808 1.022773 0.170 Uiso 0.123(4) 1 calc GR . P A -2 H6TC H -0.325016 0.541000 1.046721 0.170 Uiso 0.123(4) 1 calc GR . P A -2 C1T C 0.110(5) 0.316(3) 1.058(3) 0.083(8) Uani 0.123(4) 1 d D U P A -2 H1TA H -0.027479 0.318499 1.018567 0.124 Uiso 0.123(4) 1 calc GR . P A -2 H1TB H 0.122364 0.287449 1.135184 0.124 Uiso 0.123(4) 1 calc GR . P A -2 H1TC H 0.153429 0.251200 1.013430 0.124 Uiso 0.123(4) 1 calc GR . P A -2 C2S C -0.0476(13) 0.6174(10) 0.9653(6) 0.067(2) Uani 0.377(4) 1 d D U P A -1 C2T C 0.235(6) 0.454(4) 1.067(3) 0.102(8) Uani 0.123(4) 1 d D U P A -2 H2TA H 0.343049 0.445561 1.035506 0.122 Uiso 0.123(4) 1 calc R . P A -2 H2TB H 0.294175 0.486901 1.150262 0.122 Uiso 0.123(4) 1 calc R . P A -2 C3S C 0.2035(17) 0.4944(14) 1.0142(10) 0.086(3) Uani 0.377(4) 1 d D U P A -1 H3SA H 0.310435 0.563774 1.065969 0.103 Uiso 0.377(4) 1 calc R . P A -1 H3SB H 0.206905 0.500478 0.933917 0.103 Uiso 0.377(4) 1 calc R . P A -1 C4T C -0.025(4) 0.478(4) 0.900(3) 0.107(6) Uani 0.123(4) 1 d D U P A -2 H4TA H 0.025522 0.402249 0.873600 0.128 Uiso 0.123(4) 1 calc R . P A -2 H4TB H -0.065701 0.533388 0.834950 0.128 Uiso 0.123(4) 1 calc R . P A -2 C4S C 0.221(4) 0.354(2) 1.0506(19) 0.105(8) Uani 0.377(4) 1 d D U P A -1 H4SA H 0.097371 0.290691 1.013250 0.158 Uiso 0.377(4) 1 calc GR . P A -1 H4SB H 0.250894 0.355964 1.134563 0.158 Uiso 0.377(4) 1 calc GR . P A -1 H4SC H 0.326613 0.324032 1.027272 0.158 Uiso 0.377(4) 1 calc GR . P A -1 C5T C -0.201(4) 0.427(4) 0.950(3) 0.116(8) Uani 0.123(4) 1 d D U P A -2 H5TA H -0.312900 0.370313 0.889262 0.139 Uiso 0.123(4) 1 calc R . P A -2 H5TB H -0.158905 0.373484 1.015465 0.139 Uiso 0.123(4) 1 calc R . P A -2 C1SA C -0.241(3) 0.623(2) 0.9551(15) 0.079(5) Uani 0.377(4) 1 d . U P A -1 H1SA H -0.261511 0.715129 0.944020 0.118 Uiso 0.377(4) 1 calc GR . P A -1 H1SB H -0.270313 0.595818 1.025431 0.118 Uiso 0.377(4) 1 calc GR . P A -1 H1SC H -0.327930 0.561509 0.888665 0.118 Uiso 0.377(4) 1 calc GR . P A -1 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 0.0442(7) 0.0302(6) 0.0225(6) 0.0003(5) 0.0032(5) 0.0061(5) O2 0.0482(8) 0.0238(6) 0.0227(6) 0.0021(5) 0.0095(5) -0.0017(5) O3 0.0297(6) 0.0321(6) 0.0378(7) 0.0178(5) 0.0195(5) 0.0087(5) O4 0.0348(7) 0.0864(11) 0.0377(7) 0.0427(8) 0.0227(6) 0.0306(7) N1 0.0275(8) 0.0221(7) 0.0617(11) -0.0054(7) 0.0135(7) 0.0018(6) N2 0.0290(7) 0.0175(6) 0.0191(6) 0.0067(5) 0.0063(5) 0.0041(5) N3 0.0215(7) 0.0335(7) 0.0238(7) 0.0140(6) 0.0097(5) 0.0113(6) C1 0.0442(12) 0.0272(10) 0.099(2) -0.0098(11) 0.0334(12) -0.0060(9) C2 0.0383(10) 0.0335(10) 0.0492(12) -0.0091(9) 0.0101(9) 0.0054(8) C3 0.0166(7) 0.0208(8) 0.0469(10) 0.0074(7) 0.0104(7) 0.0076(6) C4 0.0243(8) 0.0236(8) 0.0576(12) 0.0200(8) 0.0172(8) 0.0076(6) C5 0.0268(8) 0.0385(10) 0.0439(10) 0.0267(8) 0.0162(8) 0.0115(7) C6 0.0239(8) 0.0340(9) 0.0283(8) 0.0146(7) 0.0094(6) 0.0077(7) C7 0.0167(7) 0.0222(8) 0.0270(8) 0.0100(6) 0.0070(6) 0.0066(6) C8 0.0164(7) 0.0202(8) 0.0294(8) 0.0071(6) 0.0068(6) 0.0071(6) C9 0.0229(7) 0.0210(8) 0.0246(8) 0.0033(6) 0.0056(6) 0.0071(6) C10 0.0226(7) 0.0218(8) 0.0205(7) 0.0065(6) 0.0071(6) 0.0049(6) C11 0.0277(8) 0.0195(7) 0.0189(7) 0.0078(6) 0.0080(6) 0.0045(6) C12 0.0265(8) 0.0173(7) 0.0235(8) 0.0072(6) 0.0119(6) 0.0064(6) C13 0.0278(8) 0.0354(9) 0.0256(8) 0.0147(7) 0.0151(7) 0.0135(7) C14 0.0233(8) 0.0374(9) 0.0267(8) 0.0147(7) 0.0118(7) 0.0075(7) C15 0.0243(9) 0.0353(10) 0.0261(9) 0.0141(7) 0.0093(7) 0.0112(7) O1S 0.126(7) 0.104(5) 0.102(5) 0.017(4) 0.041(5) 0.028(5) O2S 0.066(3) 0.096(5) 0.031(5) -0.006(4) 0.016(4) 0.015(3) C3T 0.092(12) 0.132(12) 0.077(12) 0.018(11) 0.011(11) 0.047(10) C6T 0.09(2) 0.16(2) 0.07(2) 0.00(2) 0.006(17) 0.02(2) C1T 0.10(2) 0.124(15) 0.054(14) 0.015(13) 0.056(15) 0.056(15) C2S 0.068(5) 0.106(7) 0.030(3) -0.002(4) 0.012(3) 0.031(5) C2T 0.104(14) 0.128(14) 0.071(14) 0.014(13) 0.012(13) 0.045(12) C3S 0.091(6) 0.135(9) 0.053(5) 0.006(5) 0.028(4) 0.071(6) C4T 0.099(11) 0.137(13) 0.074(11) 0.021(11) 0.003(10) 0.031(11) C4S 0.139(16) 0.142(16) 0.065(10) 0.006(9) 0.040(10) 0.094(13) C5T 0.115(13) 0.148(15) 0.069(14) 0.002(13) 0.009(12) 0.022(13) C1SA 0.083(9) 0.087(8) 0.040(7) 0.005(6) -0.016(6) 0.009(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C9 1.210(2) . ? O2 C10 1.213(2) . ? O3 C12 1.2079(19) . ? O4 C13 1.216(2) . ? N1 C1 1.459(3) . ? N1 C2 1.455(3) . ? N1 C3 1.383(2) . ? N2 C9 1.409(2) . ? N2 C10 1.3775(19) . ? N2 C11 1.4514(18) . ? N3 C12 1.3826(19) . ? N3 C13 1.380(2) . ? C3 C4 1.414(3) . ? C3 C8 1.413(2) . ? C4 C5 1.374(3) . ? C5 C6 1.399(2) . ? C6 C7 1.373(2) . ? C7 C8 1.396(2) . ? C7 C10 1.484(2) . ? C8 C9 1.481(2) . ? C11 C12 1.528(2) . ? C11 C15 1.525(2) . ? C13 C14 1.496(2) . ? C14 C15 1.526(2) . ? O1S C2S 1.169(11) . ? O2S C2S 1.375(12) . ? O2S C3S 1.495(12) . ? C3T C2T 1.57(2) . ? C3T C4T 1.54(2) . ? C6T C5T 1.56(2) . ? C1T C2T 1.51(2) . ? C2S C1SA 1.39(2) . ? C3S C4S 1.526(18) . ? C4T C5T 1.59(2) . ? 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 C2 N1 C1 111.74(16) . . ? C3 N1 C1 118.01(19) . . ? C3 N1 C2 120.23(15) . . ? C9 N2 C11 123.37(13) . . ? C10 N2 C9 111.79(13) . . ? C10 N2 C11 124.53(13) . . ? C13 N3 C12 127.34(13) . . ? N1 C3 C4 121.18(16) . . ? N1 C3 C8 123.90(16) . . ? C8 C3 C4 114.86(16) . . ? C5 C4 C3 123.39(15) . . ? C4 C5 C6 121.34(16) . . ? C7 C6 C5 115.96(16) . . ? C6 C7 C8 124.00(15) . . ? C6 C7 C10 126.83(15) . . ? C8 C7 C10 108.98(13) . . ? C3 C8 C9 132.38(15) . . ? C7 C8 C3 120.41(15) . . ? C7 C8 C9 106.75(13) . . ? O1 C9 N2 121.75(15) . . ? O1 C9 C8 131.76(15) . . ? N2 C9 C8 106.44(13) . . ? O2 C10 N2 125.28(14) . . ? O2 C10 C7 128.86(14) . . ? N2 C10 C7 105.85(13) . . ? N2 C11 C12 108.98(12) . . ? N2 C11 C15 112.62(13) . . ? C15 C11 C12 113.33(12) . . ? O3 C12 N3 120.55(14) . . ? O3 C12 C11 123.04(14) . . ? N3 C12 C11 116.33(13) . . ? O4 C13 N3 119.72(15) . . ? O4 C13 C14 123.18(15) . . ? N3 C13 C14 117.06(14) . . ? C13 C14 C15 112.65(14) . . ? C11 C15 C14 109.83(13) . . ? C2S O2S C3S 109.1(8) . . ? C4T C3T C2T 101(2) . . ? O1S C2S O2S 128.9(9) . . ? O1S C2S C1SA 119.6(13) . . ? O2S C2S C1SA 111.3(12) . . ? C1T C2T C3T 116(2) . . ? O2S C3S C4S 103.8(12) . . ? C3T C4T C5T 102(2) . . ? C6T C5T C4T 104(2) . . ? _shelx_res_file ; TITL 1_a.res in P-1 db-3-281.res created by SHELXL-2018/3 at 10:23:39 on 06-Nov-2019 REM Old TITL 1 in P-1 REM SHELXT solution in P-1: R1 0.178, Rweak 0.010, Alpha 0.083 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C32 N5 O8 CELL 1.54178 7.2814 10.1224 12.178 92.523 106.963 100.062 ZERR 2 0.0002 0.0002 0.0003 0.002 0.002 0.002 LATT 1 SFAC C H N O UNIT 34.49 39.47 6 9.51 DFIX 1.51 C6T C2S DFIX 1.2 O1S C2S DFIX 1.35 O2S C2S DFIX 1.45 O2S C3S DFIX 1.52 C4S C3S DFIX 1.53 C1T C2T C2T C3T C3T C4T C4T C5T C5T C6T DFIX -2.75 C1T C5T C3T C6T DANG 2.54 C1T C3T C2T C4T C3T C5T C4T C6T DANG 2.25 O1S C6T DANG 2.52 C6T O2S DANG 2.25 O2S O1S DANG 2.37 C2S C3S DANG 2.46 O2S C4S FLAT O1S O2S C6T C2S SIMU 0.03 0.06 2.6 C2T C3T C4T C1T C5T C6T C4S O1S C2S O2S C1SA C3S RIGU C5T C3T C2T C4T C1T C6T L.S. 50 0 561 PLAN 20 SIZE 0.206 0.263 0.341 TEMP -100.15 BOND list 4 fmap 2 53 acta OMIT -1 -2 5 REM REM REM WGHT 0.083600 0.463900 FVAR 0.66397 0.75372 0.99765 O1 4 0.338198 0.420879 0.775335 11.00000 0.04425 0.03017 = 0.02246 0.00034 0.00319 0.00608 O2 4 0.057584 0.156738 0.435367 11.00000 0.04820 0.02380 = 0.02267 0.00207 0.00950 -0.00169 O3 4 0.515366 0.171358 0.730623 11.00000 0.02965 0.03211 = 0.03780 0.01777 0.01950 0.00871 O4 4 0.260376 -0.017299 0.994522 11.00000 0.03482 0.08639 = 0.03770 0.04274 0.02275 0.03065 N1 3 0.417001 0.712372 0.673281 11.00000 0.02750 0.02209 = 0.06172 -0.00543 0.01351 0.00178 N2 3 0.180790 0.264845 0.619541 11.00000 0.02900 0.01754 = 0.01910 0.00673 0.00633 0.00411 N3 3 0.380900 0.081752 0.861908 11.00000 0.02147 0.03351 = 0.02376 0.01395 0.00968 0.01129 AFIX 43 H3 2 0.499028 0.078265 0.906314 11.00000 -1.20000 AFIX 0 C1 1 0.512986 0.847662 0.661104 11.00000 0.04419 0.02723 = 0.09863 -0.00977 0.03341 -0.00598 AFIX 137 H1A 2 0.608297 0.841261 0.619507 11.00000 -1.50000 H1B 2 0.580452 0.896083 0.737728 11.00000 -1.50000 H1C 2 0.414665 0.896490 0.617901 11.00000 -1.50000 AFIX 0 C2 1 0.318779 0.713671 0.761539 11.00000 0.03834 0.03351 = 0.04921 -0.00912 0.01007 0.00544 H2A 2 0.220970 0.777236 0.745375 11.00000 -1.50000 H2B 2 0.413854 0.748847 0.834521 11.00000 -1.50000 H2C 2 0.250137 0.624550 0.768754 11.00000 -1.50000 C3 1 0.336982 0.622007 0.575301 11.00000 0.01661 0.02076 = 0.04694 0.00742 0.01036 0.00755 C4 1 0.331401 0.662543 0.464911 11.00000 0.02425 0.02357 = 0.05763 0.02005 0.01725 0.00758 AFIX 43 H4 2 0.381859 0.754264 0.459336 11.00000 -1.20000 AFIX 0 C5 1 0.256768 0.576120 0.365295 11.00000 0.02676 0.03846 = 0.04385 0.02669 0.01625 0.01153 AFIX 43 H5 2 0.257697 0.609538 0.293735 11.00000 -1.20000 AFIX 0 C6 1 0.179448 0.439929 0.367117 11.00000 0.02393 0.03401 = 0.02831 0.01461 0.00936 0.00771 AFIX 43 H6 2 0.125778 0.379613 0.298642 11.00000 -1.20000 AFIX 0 C7 1 0.185807 0.398692 0.473840 11.00000 0.01673 0.02224 = 0.02698 0.01002 0.00704 0.00658 C8 1 0.263004 0.483648 0.576616 11.00000 0.01642 0.02023 = 0.02945 0.00710 0.00676 0.00715 C9 1 0.269199 0.396635 0.671741 11.00000 0.02286 0.02100 = 0.02461 0.00332 0.00562 0.00706 C10 1 0.129850 0.258640 0.500984 11.00000 0.02263 0.02181 = 0.02047 0.00647 0.00710 0.00490 C11 1 0.165507 0.148478 0.684187 11.00000 0.02766 0.01946 = 0.01888 0.00783 0.00801 0.00454 AFIX 13 H11 2 0.115987 0.066676 0.626928 11.00000 -1.20000 AFIX 0 C12 1 0.369987 0.138223 0.759425 11.00000 0.02651 0.01731 = 0.02353 0.00720 0.01190 0.00644 C13 1 0.227467 0.030239 0.902427 11.00000 0.02776 0.03541 = 0.02561 0.01475 0.01509 0.01346 C14 1 0.025307 0.032209 0.826743 11.00000 0.02329 0.03745 = 0.02672 0.01471 0.01177 0.00747 AFIX 23 H14A 2 -0.060725 0.038829 0.875629 11.00000 -1.20000 H14B 2 -0.026684 -0.053731 0.776256 11.00000 -1.20000 AFIX 0 C15 1 0.019296 0.149330 0.751826 31.00000 0.02432 0.03533 = 0.02606 0.01410 0.00933 0.01118 AFIX 23 H15A 2 -0.114250 0.141029 0.697653 31.00000 -1.20000 H15B 2 0.052040 0.235696 0.801217 31.00000 -1.20000 AFIX 0 PART -1 O1S 4 0.039094 0.692104 0.919005 20.50000 0.12608 0.10361 = 0.10205 0.01702 0.04130 0.02832 O2S 4 0.008989 0.511376 1.024460 20.50000 0.06601 0.09647 = 0.03133 -0.00631 0.01643 0.01461 PART 0 PART -2 C3T 1 0.127404 0.564417 1.005310 -20.50000 0.09161 0.13209 = 0.07659 0.01839 0.01119 0.04681 AFIX 23 H3TA 2 0.064198 0.608237 1.054723 -20.50000 -1.20000 H3TB 2 0.218167 0.634072 0.981890 -20.50000 -1.20000 AFIX 0 C6T 1 -0.256541 0.559269 0.989011 -20.50000 0.09500 0.15511 = 0.07254 -0.00450 0.00572 0.01811 AFIX 137 H6TA 2 -0.342174 0.592137 0.922287 -20.50000 -1.50000 H6TB 2 -0.137292 0.627808 1.022773 -20.50000 -1.50000 H6TC 2 -0.325016 0.541000 1.046721 -20.50000 -1.50000 AFIX 0 C1T 1 0.109762 0.315653 1.057800 -20.50000 0.10430 0.12449 = 0.05355 0.01517 0.05555 0.05626 AFIX 137 H1TA 2 -0.027479 0.318499 1.018567 -20.50000 -1.50000 H1TB 2 0.122364 0.287449 1.135184 -20.50000 -1.50000 H1TC 2 0.153429 0.251200 1.013430 -20.50000 -1.50000 AFIX 0 PART 0 PART -1 C2S 1 -0.047590 0.617436 0.965323 20.50000 0.06775 0.10650 = 0.02977 -0.00194 0.01170 0.03062 PART 0 PART -2 C2T 1 0.234803 0.454342 1.067403 -20.50000 0.10445 0.12825 = 0.07109 0.01431 0.01205 0.04508 AFIX 23 H2TA 2 0.343049 0.445561 1.035506 -20.50000 -1.20000 H2TB 2 0.294175 0.486901 1.150262 -20.50000 -1.20000 AFIX 0 PART 0 PART -1 C3S 1 0.203463 0.494423 1.014233 20.50000 0.09132 0.13486 = 0.05299 0.00552 0.02763 0.07059 AFIX 23 H3SA 2 0.310435 0.563774 1.065969 20.50000 -1.20000 H3SB 2 0.206905 0.500478 0.933917 20.50000 -1.20000 AFIX 0 PART 0 PART -2 C4T 1 -0.025324 0.478408 0.899791 -20.50000 0.09908 0.13693 = 0.07359 0.02123 0.00308 0.03095 AFIX 23 H4TA 2 0.025522 0.402249 0.873600 -20.50000 -1.20000 H4TB 2 -0.065701 0.533388 0.834950 -20.50000 -1.20000 AFIX 0 PART 0 PART -1 C4S 1 0.221169 0.353691 1.050580 20.50000 0.13926 0.14161 = 0.06481 0.00649 0.03982 0.09405 AFIX 137 H4SA 2 0.097371 0.290691 1.013250 20.50000 -1.50000 H4SB 2 0.250894 0.355964 1.134563 20.50000 -1.50000 H4SC 2 0.326613 0.324032 1.027272 20.50000 -1.50000 AFIX 0 PART 0 PART -2 C5T 1 -0.200934 0.426646 0.949534 -20.50000 0.11538 0.14845 = 0.06891 0.00154 0.00850 0.02225 AFIX 23 H5TA 2 -0.312900 0.370313 0.889262 -20.50000 -1.20000 H5TB 2 -0.158905 0.373484 1.015465 -20.50000 -1.20000 AFIX 0 PART 0 PART -1 C1SA 1 -0.241074 0.622873 0.955108 20.50000 0.08348 0.08740 = 0.04006 0.00522 -0.01565 0.00856 AFIX 137 H1SA 2 -0.261511 0.715129 0.944020 20.50000 -1.50000 H1SB 2 -0.270313 0.595818 1.025431 20.50000 -1.50000 H1SC 2 -0.327930 0.561509 0.888665 20.50000 -1.50000 AFIX 0 HKLF 4 REM 1_a.res in P-1 REM wR2 = 0.1247, GooF = S = 1.068, Restrained GooF = 1.031 for all data REM R1 = 0.0482 for 2989 Fo > 4sig(Fo) and 0.0490 for all 3077 data REM 323 parameters refined using 286 restraints END WGHT 0.0836 0.4639 REM Highest difference peak 0.309, deepest hole -0.332, 1-sigma level 0.075 Q1 1 0.0228 0.4391 0.8726 11.00000 0.05 0.31 Q2 1 0.0617 0.5394 0.9409 11.00000 0.05 0.30 Q3 1 0.2732 0.6509 1.0176 11.00000 0.05 0.26 Q4 1 0.0973 0.1498 0.7157 11.00000 0.05 0.23 Q5 1 0.2604 0.1414 0.7196 11.00000 0.05 0.23 Q6 1 -0.1117 0.3614 0.9964 11.00000 0.05 0.19 Q7 1 0.3317 0.5395 0.5834 11.00000 0.05 0.19 Q8 1 -0.0605 0.5707 1.0244 11.00000 0.05 0.19 Q9 1 0.6661 0.8350 0.6531 11.00000 0.05 0.18 Q10 1 -0.2374 0.8601 0.8771 11.00000 0.05 0.18 Q11 1 0.5490 0.6734 0.7256 11.00000 0.05 0.17 Q12 1 0.0355 0.0976 0.7966 11.00000 0.05 0.17 Q13 1 0.6079 0.7142 0.4588 11.00000 0.05 0.17 Q14 1 -0.0769 -0.0213 0.8412 11.00000 0.05 0.17 Q15 1 0.7761 0.8968 0.8096 11.00000 0.05 0.16 Q16 1 0.2540 0.4403 0.5236 11.00000 0.05 0.16 Q17 1 0.6277 0.7140 0.5744 11.00000 0.05 0.16 Q18 1 -0.2250 0.2786 0.9187 11.00000 0.05 0.15 Q19 1 0.0423 0.6448 0.3008 11.00000 0.05 0.15 Q20 1 0.1721 0.3350 0.4818 11.00000 0.05 0.15 ; _shelx_res_checksum 54748 _shelx_hkl_file ; 1 0 0 14.15 0.27 2 0 0 466.16 3.43 3 0 0 103.15 0.73 4 0 0 106.45 0.99 5 0 0 19.52 0.39 6 0 0 49.54 0.37 7 0 0 2.03 0.08 8 0 0 9.60 0.19 -8 1 0 80.44 0.67 -7 1 0 1.02 0.06 -6 1 0 17.32 0.36 -5 1 0 0.05 0.10 -4 1 0 6.25 0.17 -3 1 0 0.28 0.05 -2 1 0 3791.81 45.57 -1 1 0 435.48 5.03 0 1 0 141.13 9.16 1 1 0 511.08 8.94 2 1 0 11.56 0.18 3 1 0 51.77 0.45 4 1 0 42.51 0.49 5 1 0 33.01 0.45 6 1 0 52.21 0.37 7 1 0 7.70 0.11 8 1 0 0.47 0.05 -8 2 0 19.40 0.24 -7 2 0 0.12 0.03 -6 2 0 0.23 0.09 -5 2 0 4.78 0.22 -4 2 0 687.15 5.05 -3 2 0 980.25 6.74 -2 2 0 1225.74 8.59 -1 2 0 368.18 4.30 0 2 0 52.35 0.66 1 2 0 1.72 0.09 2 2 0 67.99 0.57 3 2 0 24.38 0.30 4 2 0 16.56 0.28 5 2 0 18.17 0.25 6 2 0 100.23 0.68 7 2 0 0.53 0.04 -8 3 0 0.31 0.05 -7 3 0 14.06 0.19 -6 3 0 11.15 0.22 -5 3 0 1.53 0.16 -4 3 0 17.56 0.35 -3 3 0 361.22 2.37 -2 3 0 1541.74 12.46 -1 3 0 499.95 3.68 0 3 0 14.06 0.16 1 3 0 468.97 3.11 2 3 0 65.16 0.55 3 3 0 14.47 0.23 4 3 0 12.46 0.23 5 3 0 0.69 0.05 6 3 0 57.43 0.40 7 3 0 0.05 0.03 -8 4 0 1.06 0.07 -7 4 0 0.24 0.05 -6 4 0 58.14 0.56 -5 4 0 31.19 0.60 -4 4 0 0.29 0.07 -3 4 0 81.28 0.87 -2 4 0 6.38 0.14 -1 4 0 32.96 0.28 0 4 0 210.35 1.36 1 4 0 649.10 4.47 2 4 0 101.75 0.90 3 4 0 15.14 0.24 4 4 0 48.51 0.50 5 4 0 0.35 0.03 6 4 0 27.14 0.23 7 4 0 72.37 0.60 -8 5 0 11.37 0.19 -7 5 0 1.55 0.09 -6 5 0 0.46 0.06 -5 5 0 153.98 2.00 -4 5 0 92.20 1.16 -3 5 0 42.13 0.65 -2 5 0 117.61 1.16 -1 5 0 111.26 0.83 0 5 0 65.32 0.55 1 5 0 14.50 0.24 2 5 0 57.32 0.57 3 5 0 2.19 0.11 4 5 0 87.58 0.85 5 5 0 7.51 0.12 6 5 0 8.29 0.13 -7 6 0 10.22 0.14 -6 6 0 0.35 0.05 -5 6 0 4.85 0.19 -4 6 0 147.65 1.64 -3 6 0 3.07 0.19 -2 6 0 178.52 1.83 -1 6 0 5.47 0.20 0 6 0 6.11 0.17 1 6 0 26.46 0.34 2 6 0 187.93 1.49 3 6 0 4.91 0.13 4 6 0 76.54 0.51 5 6 0 62.57 0.47 6 6 0 1.12 0.06 -7 7 0 3.38 0.10 -6 7 0 38.36 0.31 -5 7 0 32.21 0.35 -4 7 0 17.18 0.36 -3 7 0 14.37 0.31 -2 7 0 1.82 0.18 -1 7 0 16.48 0.39 0 7 0 467.95 4.11 1 7 0 34.69 0.39 2 7 0 0.33 0.05 3 7 0 9.84 0.14 4 7 0 5.59 0.10 5 7 0 3.13 0.08 -7 8 0 66.59 0.88 -6 8 0 22.28 0.23 -5 8 0 5.77 0.11 -4 8 0 1.29 0.07 -3 8 0 0.98 0.12 -2 8 0 10.67 0.27 -1 8 0 125.53 1.44 0 8 0 16.40 0.29 1 8 0 6.43 0.20 2 8 0 108.48 0.79 3 8 0 1.62 0.07 4 8 0 3.59 0.09 5 8 0 3.04 0.09 -6 9 0 1.36 0.06 -5 9 0 22.22 0.21 -4 9 0 30.81 0.38 -3 9 0 13.00 0.20 -2 9 0 13.58 0.19 -1 9 0 17.21 0.21 0 9 0 192.56 1.40 1 9 0 15.37 0.18 2 9 0 47.09 0.38 3 9 0 0.53 0.04 4 9 0 0.60 0.04 -6 10 0 13.34 0.24 -5 10 0 13.36 0.20 -4 10 0 3.95 0.13 -3 10 0 40.38 0.43 -2 10 0 89.21 0.87 -1 10 0 25.55 0.30 0 10 0 25.53 0.26 1 10 0 15.45 0.19 2 10 0 0.16 0.04 3 10 0 0.51 0.04 -5 11 0 16.11 0.33 -4 11 0 6.03 0.12 -3 11 0 98.30 0.99 -2 11 0 1.17 0.08 -1 11 0 18.60 0.26 0 11 0 5.35 0.13 1 11 0 0.36 0.04 2 11 0 3.83 0.09 -3 12 0 2.48 0.08 -2 12 0 5.01 0.14 -1 12 0 9.50 0.16 0 -12 1 2.94 0.10 1 -12 1 2.23 0.10 2 -12 1 -0.03 0.04 -2 -11 1 18.17 0.24 -1 -11 1 3.32 0.11 0 -11 1 14.17 0.22 1 -11 1 25.90 0.32 2 -11 1 7.31 0.19 3 -11 1 41.55 0.44 4 -11 1 17.80 0.24 -3 -10 1 17.18 0.23 -2 -10 1 13.55 0.21 -1 -10 1 3.82 0.12 0 -10 1 0.04 0.04 1 -10 1 40.42 0.42 2 -10 1 12.18 0.22 3 -10 1 107.50 1.01 4 -10 1 1.09 0.07 5 -10 1 3.79 0.10 -4 -9 1 0.08 0.03 -3 -9 1 4.03 0.12 -2 -9 1 0.20 0.04 -1 -9 1 29.83 0.30 0 -9 1 15.76 0.21 1 -9 1 178.04 1.38 2 -9 1 2.96 0.10 3 -9 1 0.14 0.06 4 -9 1 0.67 0.07 5 -9 1 28.52 0.23 6 -9 1 0.20 0.03 -5 -8 1 14.51 0.19 -4 -8 1 2.41 0.08 -3 -8 1 28.00 0.33 -2 -8 1 17.71 0.21 -1 -8 1 14.94 0.31 0 -8 1 99.01 1.33 1 -8 1 26.71 0.46 2 -8 1 6.90 0.22 3 -8 1 11.78 0.30 4 -8 1 6.55 0.14 5 -8 1 12.28 0.16 6 -8 1 39.17 0.37 7 -8 1 3.03 0.08 -5 -7 1 12.29 0.16 -4 -7 1 1.03 0.06 -3 -7 1 24.79 0.26 -2 -7 1 68.76 0.90 -1 -7 1 96.41 1.12 0 -7 1 64.85 0.95 1 -7 1 19.08 0.44 2 -7 1 75.49 1.10 3 -7 1 101.18 1.21 4 -7 1 42.04 0.65 5 -7 1 131.86 0.98 6 -7 1 1.69 0.08 7 -7 1 35.57 0.35 -6 -6 1 0.22 0.04 -5 -6 1 17.82 0.22 -4 -6 1 7.76 0.13 -3 -6 1 6.52 0.18 -2 -6 1 398.78 3.41 -1 -6 1 50.26 0.59 0 -6 1 0.43 0.07 1 -6 1 158.37 1.50 2 -6 1 3.39 0.17 3 -6 1 154.79 1.87 4 -6 1 0.18 0.07 5 -6 1 28.40 0.33 6 -6 1 23.66 0.23 7 -6 1 10.08 0.15 -6 -5 1 9.50 0.16 -5 -5 1 25.46 0.31 -4 -5 1 36.03 0.56 -3 -5 1 9.50 0.20 -2 -5 1 3.64 0.12 -1 -5 1 58.01 0.60 0 -5 1 5.10 0.14 1 -5 1 310.83 2.44 2 -5 1 1.54 0.10 3 -5 1 21.58 0.47 4 -5 1 63.25 0.89 5 -5 1 18.28 0.46 6 -5 1 5.24 0.10 7 -5 1 14.51 0.21 -7 -4 1 17.84 0.19 -6 -4 1 0.55 0.04 -5 -4 1 91.35 0.65 -4 -4 1 149.45 1.21 -3 -4 1 42.19 0.43 -2 -4 1 47.04 0.44 -1 -4 1 410.52 2.93 0 -4 1 952.18 6.36 1 -4 1 6.59 0.14 2 -4 1 12.20 0.22 3 -4 1 243.45 2.02 4 -4 1 30.12 0.61 5 -4 1 1.49 0.12 6 -4 1 17.96 0.22 7 -4 1 4.64 0.11 8 -4 1 0.40 0.04 -7 -3 1 3.88 0.11 -6 -3 1 0.39 0.04 -5 -3 1 11.15 0.23 -4 -3 1 80.19 0.72 -3 -3 1 650.40 4.17 -2 -3 1 119.93 0.91 -1 -3 1 100.85 0.76 0 -3 1 51.76 0.52 1 -3 1 957.09 8.39 2 -3 1 13.22 0.17 3 -3 1 295.94 1.94 4 -3 1 237.13 1.72 5 -3 1 0.28 0.05 6 -3 1 19.46 0.20 7 -3 1 0.27 0.04 8 -3 1 19.29 0.26 -8 -2 1 0.00 0.03 -7 -2 1 9.65 0.16 -6 -2 1 30.41 0.33 -5 -2 1 43.74 0.47 -4 -2 1 75.09 0.76 -3 -2 1 61.21 0.50 -2 -2 1 107.46 0.83 -1 -2 1 230.96 2.23 0 -2 1 153.31 2.00 1 -2 1 115.83 1.53 2 -2 1 89.37 0.74 3 -2 1 2.11 0.10 4 -2 1 0.26 0.04 5 -2 1 14.87 0.22 6 -2 1 12.55 0.15 7 -2 1 5.82 0.10 8 -2 1 0.97 0.07 -8 -1 1 4.44 0.12 -7 -1 1 9.36 0.14 -6 -1 1 173.67 1.18 -5 -1 1 3.32 0.13 -4 -1 1 9.77 0.19 -3 -1 1 27.81 0.29 -2 -1 1 108.94 0.91 -1 -1 1 408.16 6.47 0 -1 1 121.56 1.51 1 -1 1 179.19 2.29 2 -1 1 1476.64 11.60 3 -1 1 7.76 0.16 4 -1 1 0.21 0.04 5 -1 1 0.33 0.04 6 -1 1 2.17 0.08 7 -1 1 0.04 0.03 8 -1 1 2.88 0.09 -8 0 1 0.02 0.04 -7 0 1 0.56 0.04 -6 0 1 153.43 1.46 -5 0 1 105.79 1.29 -4 0 1 20.05 0.33 -3 0 1 102.04 0.75 -2 0 1 716.09 7.86 -1 0 1 728.90 14.67 0 0 1 479.23 23.14 1 0 1 1326.60 21.40 2 0 1 204.51 1.38 3 0 1 269.19 1.98 4 0 1 201.58 1.55 5 0 1 3.42 0.11 6 0 1 0.07 0.03 7 0 1 0.87 0.04 8 0 1 48.17 0.44 -8 1 1 1.16 0.07 -7 1 1 2.88 0.11 -6 1 1 16.10 0.25 -5 1 1 15.15 0.41 -4 1 1 447.51 3.59 -3 1 1 6.11 0.13 -2 1 1 4712.08 90.16 -1 1 1 322.51 3.68 0 1 1 1285.12 27.60 1 1 1 8.41 0.21 2 1 1 48.03 0.44 3 1 1 5.82 0.12 4 1 1 13.55 0.25 5 1 1 6.32 0.14 6 1 1 48.47 0.33 7 1 1 0.86 0.04 -8 2 1 41.95 0.45 -7 2 1 0.97 0.05 -6 2 1 64.60 0.73 -5 2 1 32.49 0.56 -4 2 1 626.22 5.09 -3 2 1 32.30 0.38 -2 2 1 629.91 5.22 -1 2 1 47.27 0.72 0 2 1 2291.45 26.95 1 2 1 70.90 0.60 2 2 1 2.77 0.09 3 2 1 0.72 0.06 4 2 1 78.52 0.83 5 2 1 148.33 1.21 6 2 1 21.07 0.20 7 2 1 0.53 0.03 -8 3 1 60.71 0.66 -7 3 1 2.23 0.10 -6 3 1 57.75 0.97 -5 3 1 133.04 1.67 -4 3 1 327.46 3.04 -3 3 1 242.00 2.07 -2 3 1 73.58 0.63 -1 3 1 3.20 0.08 0 3 1 1605.62 13.12 1 3 1 21.66 0.21 2 3 1 18.37 0.27 3 3 1 140.69 1.17 4 3 1 18.58 0.31 5 3 1 36.69 0.29 6 3 1 74.79 0.49 7 3 1 16.78 0.17 -8 4 1 3.94 0.12 -7 4 1 14.11 0.21 -6 4 1 63.82 0.61 -5 4 1 11.82 0.31 -4 4 1 54.30 0.70 -3 4 1 63.01 0.72 -2 4 1 72.73 0.65 -1 4 1 518.76 3.15 0 4 1 0.14 0.03 1 4 1 30.84 0.34 2 4 1 43.48 0.52 3 4 1 11.07 0.21 4 4 1 1.63 0.08 5 4 1 55.42 0.42 6 4 1 3.15 0.08 7 4 1 26.04 0.27 -8 5 1 17.61 0.25 -7 5 1 2.53 0.10 -6 5 1 16.74 0.26 -5 5 1 11.30 0.33 -4 5 1 0.04 0.06 -3 5 1 213.18 2.21 -2 5 1 133.69 1.28 -1 5 1 2.90 0.09 0 5 1 1.32 0.06 1 5 1 8.94 0.18 2 5 1 5.67 0.14 3 5 1 32.39 0.37 4 5 1 44.64 0.49 5 5 1 63.73 0.48 6 5 1 49.69 0.38 -8 6 1 29.74 0.56 -7 6 1 61.16 0.42 -6 6 1 7.00 0.17 -5 6 1 0.31 0.08 -4 6 1 131.29 1.32 -3 6 1 14.05 0.33 -2 6 1 109.27 1.24 -1 6 1 180.32 1.23 0 6 1 45.83 0.49 1 6 1 43.18 0.46 2 6 1 0.06 0.03 3 6 1 95.07 0.84 4 6 1 0.20 0.03 5 6 1 10.39 0.13 6 6 1 1.29 0.05 -7 7 1 3.04 0.08 -6 7 1 0.01 0.03 -5 7 1 22.53 0.33 -4 7 1 1.34 0.12 -3 7 1 1.72 0.11 -2 7 1 98.56 1.35 -1 7 1 55.87 0.70 0 7 1 47.68 0.66 1 7 1 0.24 0.05 2 7 1 54.69 0.55 3 7 1 51.33 0.40 4 7 1 44.32 0.36 5 7 1 13.06 0.14 -7 8 1 14.24 0.20 -6 8 1 0.15 0.04 -5 8 1 37.21 0.40 -4 8 1 107.35 0.98 -3 8 1 0.36 0.09 -2 8 1 47.94 0.61 -1 8 1 26.29 0.39 0 8 1 0.39 0.06 1 8 1 127.75 1.40 2 8 1 14.08 0.15 3 8 1 0.26 0.03 4 8 1 7.57 0.11 -6 9 1 12.15 0.14 -5 9 1 9.67 0.14 -4 9 1 0.13 0.05 -3 9 1 52.13 0.52 -2 9 1 4.15 0.10 -1 9 1 86.18 0.72 0 9 1 79.97 0.61 1 9 1 4.18 0.10 2 9 1 2.78 0.09 3 9 1 0.39 0.04 4 9 1 0.18 0.03 -6 10 1 21.44 0.36 -5 10 1 1.89 0.10 -4 10 1 32.07 0.38 -3 10 1 17.83 0.24 -2 10 1 60.67 0.58 -1 10 1 8.22 0.13 0 10 1 48.32 0.42 1 10 1 0.01 0.04 2 10 1 15.46 0.16 3 10 1 29.79 0.27 -5 11 1 4.75 0.16 -4 11 1 21.11 0.32 -3 11 1 7.79 0.17 -2 11 1 7.48 0.15 -1 11 1 10.36 0.17 0 11 1 11.78 0.16 1 11 1 0.08 0.03 -2 12 1 0.72 0.05 -1 12 1 0.04 0.04 0 -12 2 0.39 0.08 1 -12 2 15.01 0.25 2 -12 2 10.27 0.24 -2 -11 2 15.61 0.23 -1 -11 2 0.06 0.04 0 -11 2 1.74 0.10 1 -11 2 7.05 0.15 2 -11 2 6.35 0.16 3 -11 2 7.73 0.15 4 -11 2 3.10 0.13 -3 -10 2 8.53 0.16 -2 -10 2 1.33 0.09 -1 -10 2 15.57 0.26 0 -10 2 0.06 0.04 1 -10 2 94.78 1.11 2 -10 2 57.22 0.66 3 -10 2 0.64 0.06 4 -10 2 33.26 0.42 5 -10 2 0.42 0.04 -4 -9 2 4.14 0.12 -3 -9 2 5.15 0.13 -2 -9 2 2.09 0.11 -1 -9 2 144.22 1.33 0 -9 2 11.29 0.19 1 -9 2 1.60 0.10 2 -9 2 0.41 0.06 3 -9 2 28.81 0.36 4 -9 2 10.01 0.17 5 -9 2 2.28 0.09 6 -9 2 0.54 0.06 -5 -8 2 4.52 0.13 -4 -8 2 1.03 0.06 -3 -8 2 76.04 0.65 -2 -8 2 40.31 0.45 -1 -8 2 36.43 0.91 0 -8 2 10.36 0.27 1 -8 2 130.66 1.68 2 -8 2 24.55 0.48 3 -8 2 2.61 0.18 4 -8 2 7.98 0.12 5 -8 2 9.11 0.13 6 -8 2 0.11 0.03 -6 -7 2 4.09 0.11 -5 -7 2 55.80 0.49 -4 -7 2 71.73 0.66 -3 -7 2 0.13 0.04 -2 -7 2 19.47 0.64 -1 -7 2 0.79 0.16 0 -7 2 322.02 4.27 1 -7 2 4.72 0.23 2 -7 2 5.41 0.26 3 -7 2 61.10 0.83 4 -7 2 7.29 0.23 5 -7 2 6.94 0.11 6 -7 2 30.04 0.25 7 -7 2 1.62 0.07 -6 -6 2 70.74 0.69 -5 -6 2 8.74 0.16 -4 -6 2 4.05 0.11 -3 -6 2 58.30 0.93 -2 -6 2 99.36 1.33 -1 -6 2 0.66 0.10 0 -6 2 1.04 0.11 1 -6 2 141.32 1.48 2 -6 2 0.91 0.10 3 -6 2 254.83 2.81 4 -6 2 9.02 0.26 5 -6 2 7.10 0.12 6 -6 2 17.23 0.17 7 -6 2 24.49 0.27 -7 -5 2 2.71 0.11 -6 -5 2 2.90 0.09 -5 -5 2 1.68 0.07 -4 -5 2 24.24 0.48 -3 -5 2 2.55 0.19 -2 -5 2 55.28 0.77 -1 -5 2 189.34 1.88 0 -5 2 2.70 0.12 1 -5 2 143.15 1.36 2 -5 2 0.77 0.08 3 -5 2 4.75 0.18 4 -5 2 60.28 0.70 5 -5 2 7.30 0.23 6 -5 2 13.51 0.17 7 -5 2 -0.04 0.03 -7 -4 2 0.11 0.03 -6 -4 2 32.35 0.33 -5 -4 2 4.69 0.18 -4 -4 2 6.75 0.20 -3 -4 2 8.44 0.19 -2 -4 2 32.03 0.38 -1 -4 2 80.52 0.71 0 -4 2 149.39 1.05 1 -4 2 50.57 0.43 2 -4 2 45.80 0.42 3 -4 2 84.76 0.73 4 -4 2 15.83 0.28 5 -4 2 72.04 0.84 6 -4 2 10.90 0.15 7 -4 2 1.54 0.07 -7 -3 2 8.04 0.13 -6 -3 2 16.17 0.21 -5 -3 2 139.77 1.35 -4 -3 2 201.50 1.94 -3 -3 2 124.76 1.02 -2 -3 2 433.93 2.98 -1 -3 2 4.42 0.10 0 -3 2 40.41 0.40 1 -3 2 885.18 6.01 2 -3 2 61.59 0.56 3 -3 2 347.99 2.33 4 -3 2 15.43 0.26 5 -3 2 5.61 0.13 6 -3 2 0.27 0.03 7 -3 2 1.00 0.05 -8 -2 2 1.60 0.09 -7 -2 2 1.76 0.08 -6 -2 2 6.56 0.12 -5 -2 2 28.17 0.48 -4 -2 2 18.38 0.30 -3 -2 2 168.28 1.15 -2 -2 2 36.42 0.34 -1 -2 2 418.91 5.11 0 -2 2 12.39 0.24 1 -2 2 0.67 0.05 2 -2 2 154.95 1.05 3 -2 2 112.72 0.92 4 -2 2 2.68 0.11 5 -2 2 2.64 0.12 6 -2 2 17.53 0.17 7 -2 2 9.75 0.12 -8 -1 2 0.28 0.05 -7 -1 2 46.34 0.40 -6 -1 2 22.43 0.40 -5 -1 2 332.98 3.54 -4 -1 2 27.45 0.39 -3 -1 2 84.22 0.67 -2 -1 2 1084.19 8.67 -1 -1 2 117.29 1.67 0 -1 2 581.67 5.97 1 -1 2 233.05 2.76 2 -1 2 789.63 5.30 3 -1 2 0.40 0.05 4 -1 2 9.77 0.20 5 -1 2 10.61 0.23 6 -1 2 36.95 0.30 7 -1 2 1.17 0.05 -8 0 2 0.15 0.05 -7 0 2 0.28 0.04 -6 0 2 161.07 1.82 -5 0 2 13.23 0.40 -4 0 2 11.15 0.24 -3 0 2 150.30 1.07 -2 0 2 557.33 5.93 -1 0 2 825.74 12.14 0 0 2 0.56 0.06 1 0 2 783.55 9.22 2 0 2 501.19 3.04 3 0 2 2.46 0.09 4 0 2 30.09 0.38 5 0 2 1.45 0.09 6 0 2 0.20 0.03 7 0 2 0.25 0.03 -8 1 2 0.04 0.04 -7 1 2 1.56 0.07 -6 1 2 263.20 2.77 -5 1 2 36.06 0.69 -4 1 2 348.37 2.77 -3 1 2 114.70 0.89 -2 1 2 741.08 6.61 -1 1 2 718.07 7.17 0 1 2 354.08 3.44 1 1 2 114.25 0.72 2 1 2 339.90 2.35 3 1 2 81.65 0.70 4 1 2 25.65 0.41 5 1 2 0.99 0.08 6 1 2 1.76 0.06 7 1 2 10.09 0.14 -8 2 2 0.72 0.08 -7 2 2 1.20 0.08 -6 2 2 400.02 5.61 -5 2 2 0.62 0.13 -4 2 2 2190.36 38.42 -3 2 2 82.15 0.65 -2 2 2 287.46 2.04 -1 2 2 939.99 13.63 0 2 2 1067.64 12.09 1 2 2 67.19 0.52 2 2 2 38.24 0.36 3 2 2 7.56 0.17 4 2 2 0.52 0.08 5 2 2 6.35 0.18 6 2 2 0.24 0.04 7 2 2 0.05 0.02 -8 3 2 0.15 0.06 -7 3 2 56.12 0.60 -6 3 2 328.40 4.60 -5 3 2 115.39 1.50 -4 3 2 178.42 1.81 -3 3 2 24.29 0.32 -2 3 2 121.30 0.83 -1 3 2 810.38 5.00 0 3 2 1142.97 10.53 1 3 2 32.03 0.32 2 3 2 76.61 0.62 3 3 2 60.19 0.62 4 3 2 0.19 0.07 5 3 2 0.36 0.04 6 3 2 96.27 0.61 7 3 2 40.87 0.34 -8 4 2 228.66 2.43 -7 4 2 13.39 0.25 -6 4 2 76.11 1.20 -5 4 2 17.58 0.48 -4 4 2 37.67 0.56 -3 4 2 45.20 0.56 -2 4 2 185.20 1.30 -1 4 2 9.89 0.14 0 4 2 322.71 2.01 1 4 2 243.64 1.61 2 4 2 0.62 0.07 3 4 2 18.35 0.30 4 4 2 38.55 0.46 5 4 2 13.01 0.18 6 4 2 29.83 0.28 -8 5 2 12.77 0.27 -7 5 2 0.22 0.07 -6 5 2 1.09 0.07 -5 5 2 7.85 0.23 -4 5 2 2.24 0.16 -3 5 2 12.57 0.29 -2 5 2 199.13 1.35 -1 5 2 0.10 0.03 0 5 2 1.39 0.07 1 5 2 1.65 0.09 2 5 2 3.31 0.11 3 5 2 0.99 0.07 4 5 2 54.60 0.44 5 5 2 180.21 1.19 6 5 2 3.63 0.08 -8 6 2 0.12 0.03 -7 6 2 15.94 0.33 -6 6 2 5.63 0.14 -5 6 2 31.04 0.50 -4 6 2 20.65 0.34 -3 6 2 192.29 1.85 -2 6 2 248.52 1.93 -1 6 2 22.36 0.26 0 6 2 21.60 0.29 1 6 2 27.54 0.37 2 6 2 99.31 0.85 3 6 2 144.94 1.16 4 6 2 33.67 0.32 5 6 2 5.26 0.09 -7 7 2 0.44 0.05 -6 7 2 61.59 0.47 -5 7 2 0.13 0.04 -4 7 2 9.07 0.25 -3 7 2 30.35 0.46 -2 7 2 66.37 0.78 -1 7 2 86.07 0.84 0 7 2 65.99 0.58 1 7 2 194.47 1.55 2 7 2 48.30 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