#------------------------------------------------------------------------------ #$Date: 2021-07-31 04:52:40 +0300 (Sat, 31 Jul 2021) $ #$Revision: 267842 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564279.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_1564279 loop_ _publ_author_name 'Eagling, Louise' 'Leonard, Daniel J.' 'Schwarz, Maria' 'Urruzuno, I\~naki' 'Boden, Grace' 'Wailes, J. Steven' 'Ward, John W.' 'Clayden, Jonathan' _publ_section_title ; ‘Reverse biomimetic’ synthesis of l-arogenate and its stabilized analogues from l-tyrosine ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D1SC03554A _journal_year 2021 _chemical_absolute_configuration syn _chemical_formula_moiety 'C17 H24 N2 O3' _chemical_formula_sum 'C17 H24 N2 O3' _chemical_formula_weight 304.38 _space_group_crystal_system monoclinic _space_group_IT_number 4 _space_group_name_Hall 'P 2yb' _space_group_name_H-M_alt 'P 1 21 1' _atom_sites_solution_hydrogens geom _audit_creation_date 2018-06-07 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2021-03-12 deposited with the CCDC. 2021-07-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 95.471(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.7444(2) _cell_length_b 12.0901(5) _cell_length_c 12.1546(6) _cell_measurement_reflns_used 1785 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.81 _cell_measurement_theta_min 2.38 _cell_volume 840.30(6) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_collection 'Bruker Apex suite' _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 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'Bruker area detector' _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'Bruker Apex II kappa CCD area detector' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0355 _diffrn_reflns_av_unetI/netI 0.0476 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6822 _diffrn_reflns_point_group_measured_fraction_full 0.850 _diffrn_reflns_point_group_measured_fraction_max 0.827 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.082 _diffrn_reflns_theta_min 2.381 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.083 _exptl_absorpt_correction_T_max 0.7455 _exptl_absorpt_correction_T_min 0.6244 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0549 before and 0.0433 after correction. The Ratio of minimum to maximum transmission is 0.8376. The \l/2 correction factor is Not present.' _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.203 _exptl_crystal_description block _exptl_crystal_F_000 328 _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.24 _exptl_crystal_size_min 0.2 _refine_diff_density_max 0.213 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 205 _refine_ls_number_reflns 3061 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.020 _refine_ls_R_factor_all 0.0544 _refine_ls_R_factor_gt 0.0417 _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^)+(0.0369P)^2^+0.2057P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0841 _refine_ls_wR_factor_ref 0.0903 _reflns_Friedel_coverage 0.579 _reflns_Friedel_fraction_full 0.684 _reflns_Friedel_fraction_max 0.638 _reflns_number_gt 2596 _reflns_number_total 3061 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03554a2.cif _cod_data_source_block le166_4 _cod_database_code 1564279 _shelx_shelxl_version_number 2017/1 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups, All O(H) groups 2.a Ternary CH refined with riding coordinates: C1(H1), C3(H3), C8(H8) 2.b Secondary CH2 refined with riding coordinates: C4(H4A,H4B) 2.c Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C10(H10) 2.d Idealised Me refined as rotating group: C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C15(H15A,H15B,H15C), C16(H16A,H16B, H16C), C17(H17A,H17B,H17C) 2.e Idealised tetrahedral OH refined as rotating group: O2(H2) ; _shelx_res_file ; TITL testm1_a.res in P2(1) le166_4.res created by SHELXL-2017/1 at 14:37:40 on 07-Jun-2018 REM Old TITL REM SHELXT solution in P2(1) REM R1 0.092, Rweak 0.025, Alpha 0.006, Orientation as input REM Flack x = 0.302 ( 0.769 ) from Parsons' quotients REM Formula found by SHELXT: C17 N2 O3 CELL 0.71073 5.7444 12.0901 12.1546 90 95.471 90 ZERR 2 0.0002 0.0005 0.0006 0 0.003 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 34 48 4 6 L.S. 4 PLAN 5 TEMP -173.13 BOND $H CONF list 4 fmap 2 acta REM REM REM WGHT 0.036900 0.205700 FVAR 1.00645 O1 4 -0.000982 0.241173 0.075170 11.00000 0.03451 0.02168 = 0.02383 -0.00307 -0.00345 -0.00769 O2 4 0.295951 0.882482 0.055856 11.00000 0.03575 0.01767 = 0.03100 0.00652 -0.00108 0.00151 AFIX 147 H2 2 0.208777 0.843457 0.012086 11.00000 -1.50000 AFIX 0 O3 4 0.662950 0.501551 0.304982 11.00000 0.01707 0.01902 = 0.02141 -0.00105 0.00124 -0.00019 N1 3 0.279970 0.230446 0.221843 11.00000 0.02680 0.01283 = 0.02025 -0.00053 0.00071 -0.00061 N2 3 0.312362 0.410102 0.272696 11.00000 0.01553 0.01348 = 0.01755 -0.00078 0.00057 0.00213 C1 1 0.386811 0.299838 0.312583 11.00000 0.01764 0.01224 = 0.01932 0.00094 -0.00066 0.00148 AFIX 13 H1 2 0.560956 0.294291 0.315307 11.00000 -1.20000 AFIX 0 C2 1 0.121369 0.283695 0.152622 11.00000 0.02162 0.01739 = 0.02138 -0.00083 0.00641 -0.00511 C3 1 0.121603 0.404141 0.183660 11.00000 0.01300 0.01798 = 0.01778 -0.00069 -0.00074 -0.00001 AFIX 13 H3 2 -0.030967 0.426736 0.210128 11.00000 -1.20000 AFIX 0 C4 1 0.198187 0.485034 0.096443 11.00000 0.01956 0.01736 = 0.01805 0.00177 -0.00047 0.00012 AFIX 23 H4A 2 0.061451 0.521351 0.055769 11.00000 -1.20000 H4B 2 0.290162 0.446790 0.043014 11.00000 -1.20000 AFIX 0 C5 1 0.351176 0.570158 0.166848 11.00000 0.01741 0.01447 = 0.01853 0.00068 0.00188 0.00180 C6 1 0.534462 0.623490 0.105087 11.00000 0.01851 0.02151 = 0.02089 0.00276 0.00419 0.00478 AFIX 43 H6 2 0.637796 0.577222 0.069401 11.00000 -1.20000 AFIX 0 C7 1 0.559570 0.731516 0.097768 11.00000 0.01697 0.02278 = 0.02439 0.00503 0.00246 -0.00182 AFIX 43 H7 2 0.686663 0.758434 0.060869 11.00000 -1.20000 AFIX 0 C8 1 0.402409 0.814377 0.143366 11.00000 0.02098 0.01656 = 0.02209 0.00196 -0.00234 -0.00062 AFIX 13 H8 2 0.501431 0.863311 0.195045 11.00000 -1.20000 AFIX 0 C9 1 0.218888 0.762408 0.208002 11.00000 0.01544 0.01851 = 0.01927 -0.00063 -0.00228 0.00318 C10 1 0.198831 0.653323 0.218304 11.00000 0.01693 0.01652 = 0.02001 0.00045 0.00262 0.00126 AFIX 43 H10 2 0.080807 0.626088 0.260860 11.00000 -1.20000 AFIX 0 C11 1 0.054622 0.840243 0.257199 11.00000 0.02398 0.02155 = 0.03239 -0.00221 0.00216 0.00318 AFIX 137 H11A 2 -0.017582 0.889217 0.199412 11.00000 -1.50000 H11B 2 0.141268 0.884614 0.314874 11.00000 -1.50000 H11C 2 -0.067353 0.797851 0.289516 11.00000 -1.50000 AFIX 0 C12 1 0.466935 0.492783 0.256728 11.00000 0.01691 0.01392 = 0.01647 -0.00286 0.00528 0.00163 C13 1 0.309543 0.274164 0.427593 11.00000 0.01864 0.02145 = 0.02119 0.00580 0.00012 -0.00285 C14 1 0.042694 0.273075 0.424883 11.00000 0.02106 0.03463 = 0.02363 0.00477 0.00231 -0.00257 AFIX 137 H14A 2 -0.021142 0.215526 0.373818 11.00000 -1.50000 H14B 2 -0.019401 0.345273 0.399948 11.00000 -1.50000 H14C 2 -0.002282 0.257728 0.499146 11.00000 -1.50000 AFIX 0 C15 1 0.407866 0.161855 0.469183 11.00000 0.03112 0.02918 = 0.03185 0.01549 0.00055 0.00126 AFIX 137 H15A 2 0.575827 0.158886 0.460997 11.00000 -1.50000 H15B 2 0.328012 0.102320 0.425803 11.00000 -1.50000 H15C 2 0.382431 0.152772 0.547258 11.00000 -1.50000 AFIX 0 C16 1 0.410255 0.364702 0.506119 11.00000 0.02864 0.03688 = 0.01971 0.00098 0.00206 -0.00503 AFIX 137 H16A 2 0.338918 0.435887 0.483912 11.00000 -1.50000 H16B 2 0.579871 0.369075 0.503067 11.00000 -1.50000 H16C 2 0.376518 0.347163 0.581700 11.00000 -1.50000 AFIX 0 C17 1 0.351004 0.116758 0.202648 11.00000 0.06457 0.01446 = 0.03558 -0.00127 -0.00304 0.00758 AFIX 137 H17A 2 0.278730 0.067224 0.253402 11.00000 -1.50000 H17B 2 0.521595 0.110908 0.215430 11.00000 -1.50000 H17C 2 0.300402 0.095771 0.126217 11.00000 -1.50000 AFIX 0 HKLF 4 REM testm1_a.res in P2(1) REM R1 = 0.0417 for 2596 Fo > 4sig(Fo) and 0.0544 for all 3061 data REM 205 parameters refined using 1 restraints END WGHT 0.0369 0.2058 REM Highest difference peak 0.213, deepest hole -0.206, 1-sigma level 0.042 Q1 1 0.3019 0.6170 0.1997 11.00000 0.05 0.21 Q2 1 0.7382 0.0631 0.1601 11.00000 0.05 0.18 Q3 1 0.3890 0.9180 0.1200 11.00000 0.05 0.18 Q4 1 0.4526 0.7663 0.1191 11.00000 0.05 0.18 Q5 1 0.1760 0.2751 0.4226 11.00000 0.05 0.16 ; _shelx_res_checksum 37973 _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 _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O1 O -0.0010(4) 0.24117(17) 0.07517(18) 0.0271(5) Uani 1 1 d . . . . . O2 O 0.2960(4) 0.88248(16) 0.05586(19) 0.0284(5) Uani 1 1 d . . . . . H2 H 0.208777 0.843457 0.012086 0.043 Uiso 1 1 calc GR . . . . O3 O 0.6629(3) 0.50155(16) 0.30498(16) 0.0192(4) Uani 1 1 d . . . . . N1 N 0.2800(4) 0.23045(19) 0.2218(2) 0.0201(5) Uani 1 1 d . . . . . N2 N 0.3124(4) 0.41010(18) 0.27270(18) 0.0156(5) Uani 1 1 d . . . . . C1 C 0.3868(5) 0.2998(2) 0.3126(2) 0.0166(6) Uani 1 1 d . . . . . H1 H 0.560956 0.294291 0.315307 0.020 Uiso 1 1 calc R . . . . C2 C 0.1214(5) 0.2837(2) 0.1526(2) 0.0199(6) Uani 1 1 d . . . . . C3 C 0.1216(5) 0.4041(2) 0.1837(2) 0.0164(6) Uani 1 1 d . . . . . H3 H -0.030967 0.426736 0.210128 0.020 Uiso 1 1 calc R . . . . C4 C 0.1982(5) 0.4850(2) 0.0964(2) 0.0185(6) Uani 1 1 d . . . . . H4A H 0.061451 0.521351 0.055769 0.022 Uiso 1 1 calc R . . . . H4B H 0.290162 0.446790 0.043014 0.022 Uiso 1 1 calc R . . . . C5 C 0.3512(5) 0.5702(2) 0.1668(2) 0.0168(6) Uani 1 1 d . . . . . C6 C 0.5345(5) 0.6235(2) 0.1051(2) 0.0202(6) Uani 1 1 d . . . . . H6 H 0.637796 0.577222 0.069401 0.024 Uiso 1 1 calc R . . . . C7 C 0.5596(5) 0.7315(2) 0.0978(2) 0.0213(6) Uani 1 1 d . . . . . H7 H 0.686663 0.758434 0.060869 0.026 Uiso 1 1 calc R . . . . C8 C 0.4024(5) 0.8144(2) 0.1434(3) 0.0202(6) Uani 1 1 d . . . . . H8 H 0.501431 0.863311 0.195045 0.024 Uiso 1 1 calc R . . . . C9 C 0.2189(5) 0.7624(2) 0.2080(2) 0.0180(6) Uani 1 1 d . . . . . C10 C 0.1988(5) 0.6533(2) 0.2183(2) 0.0178(6) Uani 1 1 d . . . . . H10 H 0.080807 0.626088 0.260860 0.021 Uiso 1 1 calc R . . . . C11 C 0.0546(5) 0.8402(3) 0.2572(3) 0.0260(7) Uani 1 1 d . . . . . H11A H -0.017582 0.889217 0.199412 0.039 Uiso 1 1 calc GR . . . . H11B H 0.141268 0.884614 0.314874 0.039 Uiso 1 1 calc GR . . . . H11C H -0.067353 0.797851 0.289516 0.039 Uiso 1 1 calc GR . . . . C12 C 0.4669(4) 0.4928(2) 0.2567(2) 0.0155(5) Uani 1 1 d . . . . . C13 C 0.3095(5) 0.2742(2) 0.4276(3) 0.0205(6) Uani 1 1 d . . . . . C14 C 0.0427(5) 0.2731(3) 0.4249(3) 0.0264(7) Uani 1 1 d . . . . . H14A H -0.021142 0.215526 0.373818 0.040 Uiso 1 1 calc GR . . . . H14B H -0.019401 0.345273 0.399948 0.040 Uiso 1 1 calc GR . . . . H14C H -0.002282 0.257728 0.499146 0.040 Uiso 1 1 calc GR . . . . C15 C 0.4079(5) 0.1619(3) 0.4692(3) 0.0309(8) Uani 1 1 d . . . . . H15A H 0.575827 0.158886 0.460997 0.046 Uiso 1 1 calc GR . . . . H15B H 0.328012 0.102320 0.425803 0.046 Uiso 1 1 calc GR . . . . H15C H 0.382431 0.152772 0.547258 0.046 Uiso 1 1 calc GR . . . . C16 C 0.4103(5) 0.3647(3) 0.5061(3) 0.0284(7) Uani 1 1 d . . . . . H16A H 0.338918 0.435887 0.483912 0.043 Uiso 1 1 calc GR . . . . H16B H 0.579871 0.369075 0.503067 0.043 Uiso 1 1 calc GR . . . . H16C H 0.376518 0.347163 0.581700 0.043 Uiso 1 1 calc GR . . . . C17 C 0.3510(7) 0.1168(3) 0.2026(3) 0.0387(9) Uani 1 1 d . . . . . H17A H 0.278730 0.067224 0.253402 0.058 Uiso 1 1 calc GR . . . . H17B H 0.521595 0.110908 0.215430 0.058 Uiso 1 1 calc GR . . . . H17C H 0.300402 0.095771 0.126217 0.058 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 O1 0.0345(12) 0.0217(12) 0.0238(12) -0.0031(9) -0.0035(10) -0.0077(9) O2 0.0357(13) 0.0177(12) 0.0310(13) 0.0065(9) -0.0011(10) 0.0015(9) O3 0.0171(10) 0.0190(11) 0.0214(11) -0.0011(9) 0.0012(8) -0.0002(8) N1 0.0268(13) 0.0128(12) 0.0203(13) -0.0005(10) 0.0007(11) -0.0006(10) N2 0.0155(11) 0.0135(12) 0.0176(12) -0.0008(9) 0.0006(9) 0.0021(9) C1 0.0176(14) 0.0122(14) 0.0193(14) 0.0009(11) -0.0007(11) 0.0015(11) C2 0.0216(15) 0.0174(15) 0.0214(16) -0.0008(12) 0.0064(13) -0.0051(11) C3 0.0130(13) 0.0180(15) 0.0178(14) -0.0007(11) -0.0007(11) 0.0000(11) C4 0.0196(14) 0.0174(15) 0.0180(14) 0.0018(12) -0.0005(11) 0.0001(12) C5 0.0174(14) 0.0145(15) 0.0185(15) 0.0007(11) 0.0019(12) 0.0018(11) C6 0.0185(15) 0.0215(16) 0.0209(15) 0.0028(12) 0.0042(12) 0.0048(11) C7 0.0170(13) 0.0228(16) 0.0244(16) 0.0050(12) 0.0025(12) -0.0018(12) C8 0.0210(15) 0.0166(16) 0.0221(16) 0.0020(11) -0.0023(13) -0.0006(11) C9 0.0154(13) 0.0185(15) 0.0193(15) -0.0006(11) -0.0023(12) 0.0032(11) C10 0.0169(13) 0.0165(15) 0.0200(15) 0.0005(11) 0.0026(12) 0.0013(11) C11 0.0240(15) 0.0215(17) 0.0324(19) -0.0022(13) 0.0022(14) 0.0032(13) C12 0.0169(14) 0.0139(13) 0.0165(13) -0.0029(12) 0.0053(11) 0.0016(11) C13 0.0186(14) 0.0215(15) 0.0212(15) 0.0058(12) 0.0001(12) -0.0029(11) C14 0.0211(15) 0.0346(19) 0.0236(16) 0.0048(14) 0.0023(13) -0.0026(13) C15 0.0311(17) 0.0292(18) 0.0319(19) 0.0155(15) 0.0006(14) 0.0013(14) C16 0.0286(17) 0.037(2) 0.0197(17) 0.0010(14) 0.0021(14) -0.0050(14) C17 0.065(2) 0.0145(16) 0.036(2) -0.0013(14) -0.0030(18) 0.0076(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O2 H2 109.5 . . ? C2 N1 C1 113.9(2) . . ? C2 N1 C17 122.3(3) . . ? C17 N1 C1 123.6(3) . . ? C3 N2 C1 111.9(2) . . ? C12 N2 C1 122.7(2) . . ? C12 N2 C3 112.5(2) . . ? N1 C1 H1 109.3 . . ? N1 C1 C13 115.5(2) . . ? N2 C1 N1 100.5(2) . . ? N2 C1 H1 109.3 . . ? N2 C1 C13 112.5(2) . . ? C13 C1 H1 109.3 . . ? O1 C2 N1 125.6(3) . . ? O1 C2 C3 125.6(3) . . ? N1 C2 C3 108.8(2) . . ? N2 C3 C2 102.4(2) . . ? N2 C3 H3 111.4 . . ? N2 C3 C4 103.6(2) . . ? C2 C3 H3 111.4 . . ? C2 C3 C4 115.9(2) . . ? C4 C3 H3 111.4 . . ? C3 C4 H4A 111.2 . . ? C3 C4 H4B 111.2 . . ? C3 C4 C5 103.0(2) . . ? H4A C4 H4B 109.1 . . ? C5 C4 H4A 111.2 . . ? C5 C4 H4B 111.2 . . ? C6 C5 C4 113.4(2) . . ? C6 C5 C10 112.6(2) . . ? C6 C5 C12 109.9(2) . . ? C10 C5 C4 110.5(2) . . ? C10 C5 C12 109.8(2) . . ? C12 C5 C4 99.9(2) . . ? C5 C6 H6 118.4 . . ? C7 C6 C5 123.2(3) . . ? C7 C6 H6 118.4 . . ? C6 C7 H7 117.7 . . ? C6 C7 C8 124.5(3) . . ? C8 C7 H7 117.7 . . ? O2 C8 C7 109.9(2) . . ? O2 C8 H8 107.6 . . ? O2 C8 C9 110.8(2) . . ? C7 C8 H8 107.6 . . ? C7 C8 C9 113.0(2) . . ? C9 C8 H8 107.6 . . ? C10 C9 C8 122.2(2) . . ? C10 C9 C11 121.5(3) . . ? C11 C9 C8 116.4(2) . . ? C5 C10 H10 117.9 . . ? C9 C10 C5 124.3(3) . . ? C9 C10 H10 117.9 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11B 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? O3 C12 N2 125.3(3) . . ? O3 C12 C5 127.1(3) . . ? N2 C12 C5 107.7(2) . . ? C14 C13 C1 110.9(2) . . ? C14 C13 C15 109.6(2) . . ? C15 C13 C1 110.4(2) . . ? C16 C13 C1 107.3(2) . . ? C16 C13 C14 109.8(3) . . ? C16 C13 C15 108.8(3) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 H15A 109.5 . . ? C13 C15 H15B 109.5 . . ? C13 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C13 C16 H16A 109.5 . . ? C13 C16 H16B 109.5 . . ? C13 C16 H16C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? N1 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 _geom_bond_site_symmetry_2 _geom_bond_publ_flag O1 C2 1.232(3) . ? O2 H2 0.8400 . ? O2 C8 1.435(3) . ? O3 C12 1.224(3) . ? N1 C1 1.472(4) . ? N1 C2 1.344(4) . ? N1 C17 1.459(4) . ? N2 C1 1.468(3) . ? N2 C3 1.467(3) . ? N2 C12 1.363(3) . ? C1 H1 1.0000 . ? C1 C13 1.538(4) . ? C2 C3 1.504(4) . ? C3 H3 1.0000 . ? C3 C4 1.537(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.556(4) . ? C5 C6 1.496(4) . ? C5 C10 1.507(4) . ? C5 C12 1.540(4) . ? C6 H6 0.9500 . ? C6 C7 1.318(4) . ? C7 H7 0.9500 . ? C7 C8 1.490(4) . ? C8 H8 1.0000 . ? C8 C9 1.510(4) . ? C9 C10 1.331(4) . ? C9 C11 1.497(4) . ? C10 H10 0.9500 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C13 C14 1.530(4) . ? C13 C15 1.537(4) . ? C13 C16 1.529(4) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 N2 -174.7(3) . . . . ? O1 C2 C3 C4 -62.7(4) . . . . ? O2 C8 C9 C10 121.6(3) . . . . ? O2 C8 C9 C11 -56.5(3) . . . . ? N1 C1 C13 C14 -51.9(3) . . . . ? N1 C1 C13 C15 69.8(3) . . . . ? N1 C1 C13 C16 -171.9(2) . . . . ? N1 C2 C3 N2 4.1(3) . . . . ? N1 C2 C3 C4 116.1(2) . . . . ? N2 C1 C13 C14 62.7(3) . . . . ? N2 C1 C13 C15 -175.6(2) . . . . ? N2 C1 C13 C16 -57.2(3) . . . . ? N2 C3 C4 C5 -28.2(3) . . . . ? C1 N1 C2 O1 -175.1(3) . . . . ? C1 N1 C2 C3 6.1(3) . . . . ? C1 N2 C3 C2 -12.9(3) . . . . ? C1 N2 C3 C4 -133.8(2) . . . . ? C1 N2 C12 O3 -26.1(4) . . . . ? C1 N2 C12 C5 153.0(2) . . . . ? C2 N1 C1 N2 -13.4(3) . . . . ? C2 N1 C1 C13 107.9(3) . . . . ? C2 C3 C4 C5 -139.5(2) . . . . ? C3 N2 C1 N1 15.9(3) . . . . ? C3 N2 C1 C13 -107.5(2) . . . . ? C3 N2 C12 O3 -164.2(2) . . . . ? C3 N2 C12 C5 14.9(3) . . . . ? C3 C4 C5 C6 152.3(2) . . . . ? C3 C4 C5 C10 -80.1(3) . . . . ? C3 C4 C5 C12 35.5(2) . . . . ? C4 C5 C6 C7 126.9(3) . . . . ? C4 C5 C10 C9 -126.1(3) . . . . ? C4 C5 C12 O3 147.6(3) . . . . ? C4 C5 C12 N2 -31.5(3) . . . . ? C5 C6 C7 C8 -3.9(5) . . . . ? C6 C5 C10 C9 1.8(4) . . . . ? C6 C5 C12 O3 28.1(4) . . . . ? C6 C5 C12 N2 -151.0(2) . . . . ? C6 C7 C8 O2 -119.7(3) . . . . ? C6 C7 C8 C9 4.6(4) . . . . ? C7 C8 C9 C10 -2.3(4) . . . . ? C7 C8 C9 C11 179.6(3) . . . . ? C8 C9 C10 C5 -0.8(5) . . . . ? C10 C5 C6 C7 0.5(4) . . . . ? C10 C5 C12 O3 -96.3(3) . . . . ? C10 C5 C12 N2 84.6(3) . . . . ? C11 C9 C10 C5 177.2(3) . . . . ? C12 N2 C1 N1 -122.4(3) . . . . ? C12 N2 C1 C13 114.2(3) . . . . ? C12 N2 C3 C2 129.7(2) . . . . ? C12 N2 C3 C4 8.9(3) . . . . ? C12 C5 C6 C7 -122.3(3) . . . . ? C12 C5 C10 C9 124.7(3) . . . . ? C17 N1 C1 N2 162.0(3) . . . . ? C17 N1 C1 C13 -76.7(3) . . . . ? C17 N1 C2 O1 9.4(4) . . . . ? C17 N1 C2 C3 -169.4(3) . . . . ?