#------------------------------------------------------------------------------ #$Date: 2021-07-31 04:52:40 +0300 (Sat, 31 Jul 2021) $ #$Revision: 267842 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/56/42/1564280.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_1564280 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_formula_moiety 'C16 H26 N2 O3' _chemical_formula_sum 'C16 H26 N2 O3' _chemical_formula_weight 294.39 _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 mixed _atom_sites_solution_primary iterative _audit_creation_date 2018-07-03 _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 97.9895(15) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 5.94680(10) _cell_length_b 13.2423(3) _cell_length_c 10.0750(3) _cell_measurement_reflns_used 8311 _cell_measurement_temperature 100 _cell_measurement_theta_max 27.94 _cell_measurement_theta_min 2.56 _cell_volume 785.70(3) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 99.97 _diffrn_detector 'Bruker area detector' _diffrn_detector_type 'CCD area detector' _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device 'Bruker Apex II kappa CCD area detector' _diffrn_measurement_device_type 'Bruker Apex II kappa CCD area detector' _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 0.0301 _diffrn_reflns_av_unetI/netI 0.0227 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 18866 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.966 _diffrn_reflns_theta_min 2.041 _diffrn_source 'fine-focus sealed tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.6316 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0630 before and 0.0421 after correction. The Ratio of minimum to maximum transmission is 0.8471. The \l/2 correction factor is Not present.' _exptl_crystal_colour 'clear colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.244 _exptl_crystal_description plate _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.424 _exptl_crystal_size_mid 0.266 _exptl_crystal_size_min 0.074 _refine_diff_density_max 0.250 _refine_diff_density_min -0.169 _refine_diff_density_rms 0.035 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 198 _refine_ls_number_reflns 3773 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0339 _refine_ls_R_factor_gt 0.0318 _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^)+(0.0510P)^2^+0.0717P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0801 _refine_ls_wR_factor_ref 0.0812 _reflns_Friedel_coverage 0.917 _reflns_Friedel_fraction_full 1.000 _reflns_Friedel_fraction_max 0.998 _reflns_number_gt 3588 _reflns_number_total 3773 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1sc03554a2.cif _cod_data_source_block le172_f23_27 _cod_database_code 1564280 _shelxl_version_number 2013-4 _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. ; _shelx_estimated_absorpt_t_max 0.994 _shelx_estimated_absorpt_t_min 0.965 _olex2_refinement_description ; ; _shelx_res_file ; TITL testm1 in P2(1) CELL 0.71073 5.9468 13.2423 10.075 90 97.9895 90 ZERR 2 0.0001 0.0003 0.0003 0 0.0015 0 LATT -1 SYMM -X,0.5+Y,-Z SFAC C H N O UNIT 32 52 4 6 EQIV $1 2-X,-0.5+Y,1-Z L.S. 10 PLAN 5 SIZE 0.074 0.266 0.424 TEMP -173.18 HTAB O2 O1_$1 BOND $H CONF fmap 2 53 acta REM REM REM WGHT 0.051000 0.071700 FVAR 0.46342 C1 1 0.715115 0.690175 0.966663 11.00000 0.01102 0.01226 = 0.01529 -0.00124 0.00225 0.00041 AFIX 13 H1 2 0.549562 0.700939 0.970026 11.00000 -1.20000 AFIX 0 C2 1 0.907137 0.759979 0.797911 11.00000 0.01074 0.01415 = 0.01671 0.00124 -0.00064 0.00121 C3 1 0.894714 0.647423 0.772239 11.00000 0.00989 0.01539 = 0.01431 0.00042 0.00397 -0.00043 AFIX 13 H3 2 1.047801 0.615578 0.794416 11.00000 -1.20000 AFIX 0 C4 1 0.778250 0.612393 0.633629 11.00000 0.01665 0.01594 = 0.01374 -0.00018 0.00445 -0.00082 AFIX 23 H4A 2 0.891303 0.587288 0.578097 11.00000 -1.20000 H4B 2 0.690868 0.668155 0.585533 11.00000 -1.20000 AFIX 0 C5 1 0.619097 0.526546 0.666381 11.00000 0.01395 0.01301 = 0.01261 -0.00037 0.00217 0.00058 C6 1 0.400273 0.516500 0.567401 11.00000 0.01399 0.02109 = 0.01473 -0.00079 -0.00060 0.00126 AFIX 23 H6A 2 0.289293 0.475873 0.609247 11.00000 -1.20000 H6B 2 0.334095 0.584436 0.548331 11.00000 -1.20000 AFIX 0 C7 1 0.439024 0.466877 0.435676 11.00000 0.01695 0.02868 = 0.01400 -0.00400 -0.00085 -0.00169 AFIX 23 H7A 2 0.292103 0.459746 0.376798 11.00000 -1.20000 H7B 2 0.539129 0.510216 0.389236 11.00000 -1.20000 AFIX 0 C8 1 0.547442 0.363451 0.461547 11.00000 0.01839 0.02453 = 0.01682 -0.00747 0.00468 -0.00417 AFIX 13 H8 2 0.444972 0.322610 0.511298 11.00000 -1.20000 AFIX 0 C9 1 0.773920 0.373877 0.551813 11.00000 0.01882 0.01832 = 0.02186 -0.00691 0.00112 0.00242 AFIX 23 H9A 2 0.878742 0.415018 0.505848 11.00000 -1.20000 H9B 2 0.842624 0.306234 0.569203 11.00000 -1.20000 AFIX 0 C10 1 0.743105 0.423773 0.684945 11.00000 0.01855 0.01379 = 0.01685 -0.00199 -0.00001 0.00243 AFIX 23 H10A 2 0.894097 0.434037 0.738370 11.00000 -1.20000 H10B 2 0.655365 0.377878 0.735941 11.00000 -1.20000 AFIX 0 C11 1 0.563441 0.558815 0.803754 11.00000 0.01320 0.01040 = 0.01235 0.00189 0.00074 0.00235 C12 1 0.833053 0.661628 1.108688 11.00000 0.01449 0.01648 = 0.01211 -0.00060 0.00144 -0.00052 C13 1 0.756668 0.733522 1.212941 11.00000 0.02247 0.02316 = 0.01440 -0.00396 0.00344 -0.00145 AFIX 137 H13A 2 0.810200 0.801978 1.197669 11.00000 -1.50000 H13B 2 0.820438 0.711104 1.303049 11.00000 -1.50000 H13C 2 0.590521 0.733457 1.204773 11.00000 -1.50000 AFIX 0 C14 1 1.091703 0.664592 1.114448 11.00000 0.01503 0.02411 = 0.01836 0.00154 0.00026 0.00035 AFIX 137 H14A 2 1.137453 0.619435 1.045927 11.00000 -1.50000 H14B 2 1.163260 0.642553 1.203221 11.00000 -1.50000 H14C 2 1.139888 0.733685 1.097880 11.00000 -1.50000 AFIX 0 C15 1 0.756756 0.554617 1.139920 11.00000 0.02223 0.01835 = 0.01773 0.00397 0.00222 -0.00101 AFIX 137 H15A 2 0.591361 0.553389 1.136957 11.00000 -1.50000 H15B 2 0.829008 0.534685 1.229463 11.00000 -1.50000 H15C 2 0.801150 0.507405 1.073295 11.00000 -1.50000 AFIX 0 C16 1 0.762779 0.881787 0.948416 11.00000 0.02946 0.01136 = 0.02297 -0.00148 0.00436 0.00250 AFIX 137 H16A 2 0.878699 0.901904 1.022511 11.00000 -1.50000 H16B 2 0.612586 0.884689 0.977804 11.00000 -1.50000 H16C 2 0.766870 0.927829 0.872636 11.00000 -1.50000 AFIX 0 N1 3 0.807440 0.779594 0.907422 11.00000 0.01576 0.01154 = 0.01589 0.00100 0.00175 0.00032 N2 3 0.741582 0.613857 0.865672 11.00000 0.01187 0.01318 = 0.01214 -0.00070 0.00380 -0.00066 O1 4 0.995524 0.823349 0.732432 11.00000 0.01953 0.01704 = 0.02390 0.00367 0.00615 -0.00328 O2 4 0.569360 0.310858 0.340245 11.00000 0.02066 0.03884 = 0.02492 -0.01856 0.00648 -0.00649 H2 2 0.702304 0.318456 0.321379 11.00000 0.03761 O3 4 0.392805 0.537978 0.852859 11.00000 0.01404 0.01880 = 0.01691 0.00032 0.00427 -0.00276 HKLF 4 REM testm1 in P2(1) REM R1 = 0.0318 for 3588 Fo > 4sig(Fo) and 0.0339 for all 3773 data REM 198 parameters refined using 1 restraints END WGHT 0.0510 0.0717 REM Highest difference peak 0.250, deepest hole -0.169, 1-sigma level 0.035 Q1 1 0.8980 0.7030 0.7803 11.00000 0.05 0.25 Q2 1 0.5113 0.5226 0.6184 11.00000 0.05 0.23 Q3 1 0.7721 0.6780 1.0426 11.00000 0.05 0.23 Q4 1 0.6620 0.3712 0.5042 11.00000 0.05 0.23 Q5 1 0.6798 0.4797 0.6682 11.00000 0.05 0.21 ; _shelx_res_checksum 52983 _olex2_exptl_crystal_mounting_method 'Oil on glass fiber' _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 C1 C 0.7151(3) 0.69017(12) 0.96666(17) 0.0128(3) Uani 1 1 d . . . . . H1 H 0.5496 0.7009 0.9700 0.015 Uiso 1 1 calc R . . . . C2 C 0.9071(3) 0.75998(13) 0.79791(18) 0.0141(3) Uani 1 1 d . . . . . C3 C 0.8947(3) 0.64742(13) 0.77224(17) 0.0130(3) Uani 1 1 d . . . . . H3 H 1.0478 0.6156 0.7944 0.016 Uiso 1 1 calc R . . . . C4 C 0.7783(3) 0.61239(13) 0.63363(17) 0.0152(3) Uani 1 1 d . . . . . H4A H 0.8913 0.5873 0.5781 0.018 Uiso 1 1 calc R . . . . H4B H 0.6909 0.6682 0.5855 0.018 Uiso 1 1 calc R . . . . C5 C 0.6191(3) 0.52655(13) 0.66638(17) 0.0132(3) Uani 1 1 d . . . . . C6 C 0.4003(3) 0.51650(14) 0.56740(18) 0.0168(4) Uani 1 1 d . . . . . H6A H 0.2893 0.4759 0.6092 0.020 Uiso 1 1 calc R . . . . H6B H 0.3341 0.5844 0.5483 0.020 Uiso 1 1 calc R . . . . C7 C 0.4390(3) 0.46688(15) 0.43568(19) 0.0202(4) Uani 1 1 d . . . . . H7A H 0.2921 0.4597 0.3768 0.024 Uiso 1 1 calc R . . . . H7B H 0.5391 0.5102 0.3892 0.024 Uiso 1 1 calc R . . . . C8 C 0.5474(3) 0.36345(15) 0.46155(19) 0.0197(4) Uani 1 1 d . . . . . H8 H 0.4450 0.3226 0.5113 0.024 Uiso 1 1 calc R . . . . C9 C 0.7739(3) 0.37388(15) 0.55181(19) 0.0198(4) Uani 1 1 d . . . . . H9A H 0.8787 0.4150 0.5058 0.024 Uiso 1 1 calc R . . . . H9B H 0.8426 0.3062 0.5692 0.024 Uiso 1 1 calc R . . . . C10 C 0.7431(3) 0.42377(13) 0.68495(18) 0.0166(4) Uani 1 1 d . . . . . H10A H 0.8941 0.4340 0.7384 0.020 Uiso 1 1 calc R . . . . H10B H 0.6554 0.3779 0.7359 0.020 Uiso 1 1 calc R . . . . C11 C 0.5634(3) 0.55882(12) 0.80375(16) 0.0121(3) Uani 1 1 d . . . . . C12 C 0.8331(3) 0.66163(13) 1.10869(17) 0.0144(3) Uani 1 1 d . . . . . C13 C 0.7567(3) 0.73352(15) 1.21294(19) 0.0199(4) Uani 1 1 d . . . . . H13A H 0.8102 0.8020 1.1977 0.030 Uiso 1 1 calc GR . . . . H13B H 0.8204 0.7111 1.3030 0.030 Uiso 1 1 calc GR . . . . H13C H 0.5905 0.7335 1.2048 0.030 Uiso 1 1 calc GR . . . . C14 C 1.0917(3) 0.66459(15) 1.11445(19) 0.0194(4) Uani 1 1 d . . . . . H14A H 1.1375 0.6194 1.0459 0.029 Uiso 1 1 calc GR . . . . H14B H 1.1633 0.6426 1.2032 0.029 Uiso 1 1 calc GR . . . . H14C H 1.1399 0.7337 1.0979 0.029 Uiso 1 1 calc GR . . . . C15 C 0.7568(3) 0.55462(14) 1.13992(19) 0.0195(4) Uani 1 1 d . . . . . H15A H 0.5914 0.5534 1.1370 0.029 Uiso 1 1 calc GR . . . . H15B H 0.8290 0.5347 1.2295 0.029 Uiso 1 1 calc GR . . . . H15C H 0.8012 0.5074 1.0733 0.029 Uiso 1 1 calc GR . . . . C16 C 0.7628(3) 0.88179(14) 0.9484(2) 0.0212(4) Uani 1 1 d . . . . . H16A H 0.8787 0.9019 1.0225 0.032 Uiso 1 1 calc GR . . . . H16B H 0.6126 0.8847 0.9778 0.032 Uiso 1 1 calc GR . . . . H16C H 0.7669 0.9278 0.8726 0.032 Uiso 1 1 calc GR . . . . N1 N 0.8074(3) 0.77959(11) 0.90742(15) 0.0144(3) Uani 1 1 d . . . . . N2 N 0.7416(2) 0.61386(11) 0.86567(14) 0.0122(3) Uani 1 1 d . . . . . O1 O 0.9955(2) 0.82335(10) 0.73243(14) 0.0199(3) Uani 1 1 d . . . . . O2 O 0.5694(3) 0.31086(12) 0.34024(15) 0.0278(3) Uani 1 1 d . . . . . H2 H 0.702(5) 0.318(2) 0.321(3) 0.038(7) Uiso 1 1 d . . . . . O3 O 0.3928(2) 0.53798(10) 0.85286(13) 0.0164(3) 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 C1 0.0110(8) 0.0123(8) 0.0153(8) -0.0012(6) 0.0022(6) 0.0004(6) C2 0.0107(8) 0.0141(8) 0.0167(8) 0.0012(6) -0.0006(6) 0.0012(6) C3 0.0099(7) 0.0154(8) 0.0143(8) 0.0004(6) 0.0040(6) -0.0004(6) C4 0.0167(8) 0.0159(8) 0.0137(8) -0.0002(6) 0.0044(6) -0.0008(6) C5 0.0139(8) 0.0130(8) 0.0126(8) -0.0004(6) 0.0022(6) 0.0006(6) C6 0.0140(8) 0.0211(8) 0.0147(8) -0.0008(7) -0.0006(7) 0.0013(6) C7 0.0169(8) 0.0287(10) 0.0140(8) -0.0040(7) -0.0008(7) -0.0017(7) C8 0.0184(9) 0.0245(9) 0.0168(9) -0.0075(7) 0.0047(7) -0.0042(7) C9 0.0188(9) 0.0183(9) 0.0219(9) -0.0069(7) 0.0011(7) 0.0024(7) C10 0.0186(9) 0.0138(8) 0.0169(9) -0.0020(6) 0.0000(7) 0.0024(7) C11 0.0132(7) 0.0104(7) 0.0124(7) 0.0019(6) 0.0007(6) 0.0023(6) C12 0.0145(8) 0.0165(8) 0.0121(7) -0.0006(6) 0.0014(6) -0.0005(7) C13 0.0225(9) 0.0232(9) 0.0144(8) -0.0040(7) 0.0034(7) -0.0014(7) C14 0.0150(8) 0.0241(9) 0.0184(8) 0.0015(7) 0.0003(7) 0.0003(7) C15 0.0222(9) 0.0183(9) 0.0177(8) 0.0040(7) 0.0022(7) -0.0010(7) C16 0.0295(10) 0.0114(8) 0.0230(9) -0.0015(7) 0.0044(8) 0.0025(7) N1 0.0158(7) 0.0115(7) 0.0159(7) 0.0010(5) 0.0017(6) 0.0003(5) N2 0.0119(7) 0.0132(7) 0.0121(7) -0.0007(5) 0.0038(5) -0.0007(5) O1 0.0195(6) 0.0170(6) 0.0239(7) 0.0037(5) 0.0061(5) -0.0033(5) O2 0.0207(7) 0.0388(9) 0.0249(7) -0.0186(7) 0.0065(6) -0.0065(6) O3 0.0140(6) 0.0188(6) 0.0169(6) 0.0003(5) 0.0043(5) -0.0028(5) 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 C12 C1 H1 108.9 . . ? N1 C1 H1 108.9 . . ? N1 C1 C12 115.19(14) . . ? N2 C1 H1 108.9 . . ? N2 C1 C12 113.34(14) . . ? N2 C1 N1 101.12(13) . . ? N1 C2 C3 108.25(14) . . ? O1 C2 C3 126.51(16) . . ? O1 C2 N1 125.23(16) . . ? C2 C3 H3 110.9 . . ? C2 C3 C4 117.16(14) . . ? C4 C3 H3 110.9 . . ? N2 C3 C2 102.05(14) . . ? N2 C3 H3 110.9 . . ? N2 C3 C4 104.44(13) . . ? C3 C4 H4A 111.0 . . ? C3 C4 H4B 111.0 . . ? C3 C4 C5 103.86(13) . . ? H4A C4 H4B 109.0 . . ? C5 C4 H4A 111.0 . . ? C5 C4 H4B 111.0 . . ? C4 C5 C10 112.18(14) . . ? C6 C5 C4 114.55(14) . . ? C6 C5 C10 110.49(14) . . ? C11 C5 C4 101.77(13) . . ? C11 C5 C6 110.04(14) . . ? C11 C5 C10 107.23(14) . . ? C5 C6 H6A 109.0 . . ? C5 C6 H6B 109.0 . . ? H6A C6 H6B 107.8 . . ? C7 C6 C5 112.72(14) . . ? C7 C6 H6A 109.0 . . ? C7 C6 H6B 109.0 . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 108.1 . . ? C8 C7 C6 110.50(15) . . ? C8 C7 H7A 109.5 . . ? C8 C7 H7B 109.5 . . ? C7 C8 H8 107.4 . . ? C7 C8 C9 109.84(15) . . ? C9 C8 H8 107.4 . . ? O2 C8 C7 112.30(16) . . ? O2 C8 H8 107.4 . . ? O2 C8 C9 112.14(15) . . ? C8 C9 H9A 109.4 . . ? C8 C9 H9B 109.4 . . ? C8 C9 C10 111.05(15) . . ? H9A C9 H9B 108.0 . . ? C10 C9 H9A 109.4 . . ? C10 C9 H9B 109.4 . . ? C5 C10 H10A 109.0 . . ? C5 C10 H10B 109.0 . . ? C9 C10 C5 112.79(15) . . ? C9 C10 H10A 109.0 . . ? C9 C10 H10B 109.0 . . ? H10A C10 H10B 107.8 . . ? N2 C11 C5 108.15(14) . . ? O3 C11 C5 126.92(15) . . ? O3 C11 N2 124.90(15) . . ? C13 C12 C1 110.00(14) . . ? C13 C12 C15 108.00(14) . . ? C14 C12 C1 110.60(14) . . ? C14 C12 C13 110.48(15) . . ? C14 C12 C15 109.88(15) . . ? C15 C12 C1 107.81(14) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13B 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14B 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15B 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H16A C16 H16B 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C16 H16A 109.5 . . ? N1 C16 H16B 109.5 . . ? N1 C16 H16C 109.5 . . ? C2 N1 C1 114.18(14) . . ? C2 N1 C16 122.11(15) . . ? C16 N1 C1 122.94(15) . . ? C1 N2 C3 112.01(13) . . ? C11 N2 C1 122.51(14) . . ? C11 N2 C3 112.37(14) . . ? C8 O2 H2 110(2) . . ? 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 C1 H1 1.0000 . ? C1 C12 1.550(2) . ? C1 N1 1.467(2) . ? C1 N2 1.458(2) . ? C2 C3 1.513(2) . ? C2 N1 1.348(2) . ? C2 O1 1.230(2) . ? C3 H3 1.0000 . ? C3 C4 1.541(2) . ? C3 N2 1.467(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4 C5 1.544(2) . ? C5 C6 1.531(2) . ? C5 C10 1.547(2) . ? C5 C11 1.528(2) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C6 C7 1.527(3) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C7 C8 1.521(3) . ? C8 H8 1.0000 . ? C8 C9 1.523(3) . ? C8 O2 1.428(2) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C9 C10 1.529(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 N2 1.363(2) . ? C11 O3 1.221(2) . ? C12 C13 1.533(2) . ? C12 C14 1.532(2) . ? C12 C15 1.534(3) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? 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 . ? C16 N1 1.450(2) . ? O2 H2 0.84(3) . ? 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 O2 H2 O1 0.84(3) 1.95(3) 2.790(2) 174(3) 2_746 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 C2 C3 C4 C5 -133.66(15) . . . . ? C2 C3 N2 C1 -15.68(17) . . . . ? C2 C3 N2 C11 126.81(15) . . . . ? C3 C2 N1 C1 -1.07(19) . . . . ? C3 C2 N1 C16 -171.29(16) . . . . ? C3 C4 C5 C6 148.22(14) . . . . ? C3 C4 C5 C10 -84.78(17) . . . . ? C3 C4 C5 C11 29.53(16) . . . . ? C4 C3 N2 C1 -138.15(14) . . . . ? C4 C3 N2 C11 4.33(18) . . . . ? C4 C5 C6 C7 76.18(19) . . . . ? C4 C5 C10 C9 -78.70(18) . . . . ? C4 C5 C11 N2 -28.20(17) . . . . ? C4 C5 C11 O3 153.32(17) . . . . ? C5 C6 C7 C8 57.0(2) . . . . ? C5 C11 N2 C1 153.39(15) . . . . ? C5 C11 N2 C3 15.42(18) . . . . ? C6 C5 C10 C9 50.45(19) . . . . ? C6 C5 C11 N2 -150.06(14) . . . . ? C6 C5 C11 O3 31.5(2) . . . . ? C6 C7 C8 C9 -59.35(19) . . . . ? C6 C7 C8 O2 175.13(15) . . . . ? C7 C8 C9 C10 58.4(2) . . . . ? C8 C9 C10 C5 -54.6(2) . . . . ? C10 C5 C6 C7 -51.7(2) . . . . ? C10 C5 C11 N2 89.73(16) . . . . ? C10 C5 C11 O3 -88.8(2) . . . . ? C11 C5 C6 C7 -169.90(15) . . . . ? C11 C5 C10 C9 170.38(14) . . . . ? C12 C1 N1 C2 114.32(16) . . . . ? C12 C1 N1 C16 -75.6(2) . . . . ? C12 C1 N2 C3 -108.93(16) . . . . ? C12 C1 N2 C11 112.96(17) . . . . ? N1 C1 C12 C13 76.07(18) . . . . ? N1 C1 C12 C14 -46.2(2) . . . . ? N1 C1 C12 C15 -166.40(14) . . . . ? N1 C1 N2 C3 14.93(17) . . . . ? N1 C1 N2 C11 -123.18(16) . . . . ? N1 C2 C3 C4 123.23(16) . . . . ? N1 C2 C3 N2 9.89(17) . . . . ? N2 C1 C12 C13 -168.15(14) . . . . ? N2 C1 C12 C14 69.54(18) . . . . ? N2 C1 C12 C15 -50.61(18) . . . . ? N2 C1 N1 C2 -8.27(18) . . . . ? N2 C1 N1 C16 161.86(16) . . . . ? N2 C3 C4 C5 -21.67(17) . . . . ? O1 C2 C3 C4 -57.8(2) . . . . ? O1 C2 C3 N2 -171.19(17) . . . . ? O1 C2 N1 C1 179.99(16) . . . . ? O1 C2 N1 C16 9.8(3) . . . . ? O2 C8 C9 C10 -176.02(16) . . . . ? O3 C11 N2 C1 -28.1(3) . . . . ? O3 C11 N2 C3 -166.06(16) . . . . ?