#------------------------------------------------------------------------------ #$Date: 2021-03-04 06:49:59 +0200 (Thu, 04 Mar 2021) $ #$Revision: 262454 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/79/7157923.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_7157923 loop_ _publ_author_name 'Liang, Leilei' 'Li, Ji' 'shen, baochun' 'Zhang, Yili' 'Liu, Jianping' 'Chen, Jingbo' 'Liu, Dandan' _publ_section_title ; The Effect of Carbonyl on the Isomerization of Galanthan Ring System and Total Synthesis of (+-)-\b-lycorane via a Double Michael Addition Approach ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB02398A _journal_year 2021 _chemical_absolute_configuration ad _chemical_formula_moiety 'C16 H17 N O4' _chemical_formula_sum 'C16 H17 N O4' _chemical_formula_weight 287.30 _space_group_crystal_system orthorhombic _space_group_IT_number 19 _space_group_name_Hall 'P 2ac 2ab' _space_group_name_H-M_alt 'P 21 21 21' _atom_sites_solution_hydrogens geom _audit_block_doi 10.5517/ccdc.csd.cc25fpfr _audit_update_record ; 2020-06-10 deposited with the CCDC. 2021-03-02 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 5.2488(2) _cell_length_b 7.5956(3) _cell_length_c 33.4224(12) _cell_measurement_reflns_used 9977 _cell_measurement_temperature 100.(2) _cell_measurement_theta_max 72.3507 _cell_measurement_theta_min 2.6441 _cell_volume 1332.48(9) _computing_cell_refinement 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_data_collection 'Bruker Instrument Service vV6.2.9' _computing_data_reduction 'SAINT V8.38A (Bruker AXS Inc., 2017)' _computing_structure_refinement 'SHELXL-2017/1 (Sheldrick, 2017)' _computing_structure_solution 'SHELXT 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 100.(2) _diffrn_detector_area_resol_mean 7.3910 _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.996 _diffrn_measurement_device_type 'Bruker D8 QUEST PHOTON II' _diffrn_radiation_monochromator 'Helixos MX multilayer Optic' _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents 0.0324 _diffrn_reflns_av_unetI/netI 0.0227 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 41 _diffrn_reflns_limit_l_min -34 _diffrn_reflns_number 11774 _diffrn_reflns_theta_full 72.34 _diffrn_reflns_theta_max 72.34 _diffrn_reflns_theta_min 2.64 _diffrn_source 'Ius Diamond' _diffrn_source_type Microfocus _exptl_absorpt_coefficient_mu 0.852 _exptl_absorpt_correction_T_max 0.94 _exptl_absorpt_correction_T_min 0.75 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.432 _exptl_crystal_density_method 'not measured' _exptl_crystal_description prism _exptl_crystal_F_000 608 _exptl_crystal_size_max 0.560 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_min 0.070 _refine_diff_density_max 0.222 _refine_diff_density_min -0.169 _refine_ls_abs_structure_details ; Flack x determined using 1031 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.00(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.057 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 191 _refine_ls_number_reflns 2637 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.057 _refine_ls_R_factor_all 0.0282 _refine_ls_R_factor_gt 0.0278 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0417P)^2^+0.2445P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0734 _refine_ls_wR_factor_ref 0.0737 _reflns_number_gt 2600 _reflns_number_total 2637 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob02398a2.cif _cod_data_source_block qlll1 _cod_depositor_comments ; The following automatic conversions were performed: data item '_exptl_absorpt_correction_type' value 'Multi-Scan' was changed to 'multi-scan' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_database_code 7157923 _shelx_res_file ; TITL qlll1_0m_a.res in P2(1)2(1)2(1) qlll1_0m.res created by SHELXL-2017/1 at 14:53:11 on 20-Nov-2019 CELL 1.54178 5.2488 7.5956 33.4224 90.000 90.000 90.000 ZERR 4.00 0.0002 0.0003 0.0012 0.000 0.000 0.000 LATT -1 SYMM x+1/2, -y+1/2, -z SYMM -x, y+1/2, -z+1/2 SYMM -x+1/2, -y, z+1/2 SFAC C H N O UNIT 64 68 4 16 LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! TEMP -173.130 SIZE 0.070 0.130 0.560 ACTA EQIV $1 x-1/2, -y+3/2, -z+1 HTAB O3 O3_$1 HTAB O3 O4_$1 EQIV $2 x, y-1, z HTAB C11 O4_$2 HTAB C15 O3_$1 EQIV $3 x-1, y, z HTAB C15 O4_$3 L.S. 4 FMAP 2 PLAN -4 0 0.00 HTAB BOND $H CONF WGHT 0.041700 0.244500 FVAR 1.00208 O1 4 0.671177 0.846892 0.711802 11.00000 0.03703 0.02713 = 0.02636 -0.00750 -0.00723 -0.00149 O2 4 0.811246 0.587875 0.740735 11.00000 0.03227 0.03344 = 0.02443 -0.00299 -0.00778 -0.00014 O3 4 0.129073 0.693004 0.507536 11.00000 0.02041 0.03366 = 0.01846 0.00964 0.00053 -0.00034 AFIX 147 H17 2 0.011007 0.724947 0.492200 11.00000 -1.50000 AFIX 0 O4 4 0.424245 0.674838 0.571840 11.00000 0.01933 0.02388 = 0.02155 0.00149 0.00109 -0.00027 N1 3 0.194013 0.224773 0.608355 11.00000 0.02295 0.01631 = 0.02262 -0.00060 -0.00150 0.00126 C1 1 -0.026079 0.410915 0.533341 11.00000 0.02601 0.02706 = 0.01791 -0.00008 -0.00255 -0.00139 AFIX 23 H13 2 -0.137761 0.398915 0.509627 11.00000 -1.20000 H1 2 0.137172 0.351236 0.527328 11.00000 -1.20000 AFIX 0 C2 1 -0.152306 0.321110 0.569202 11.00000 0.01997 0.02219 = 0.02347 0.00126 -0.00174 -0.00104 AFIX 13 H5 2 -0.333709 0.359946 0.571596 11.00000 -1.20000 AFIX 0 C3 1 -0.009677 0.356404 0.608598 11.00000 0.01827 0.02057 = 0.01877 0.00235 0.00252 0.00051 AFIX 13 H15 2 -0.126900 0.330715 0.631450 11.00000 -1.20000 AFIX 0 C4 1 0.104939 0.540496 0.614523 11.00000 0.01995 0.01920 = 0.01775 0.00046 0.00251 0.00256 AFIX 13 H16 2 -0.037196 0.619741 0.623045 11.00000 -1.20000 AFIX 0 C5 1 0.300809 0.541719 0.647881 11.00000 0.02122 0.02222 = 0.01477 0.00082 0.00381 0.00147 C6 1 0.387340 0.705649 0.662228 11.00000 0.02918 0.02183 = 0.01904 -0.00064 0.00167 0.00318 AFIX 43 H4 2 0.325607 0.812915 0.651288 11.00000 -1.20000 AFIX 0 C7 1 0.563284 0.705106 0.692449 11.00000 0.02717 0.02507 = 0.01910 -0.00400 0.00306 -0.00107 C8 1 0.869699 0.771466 0.735827 11.00000 0.02600 0.03424 = 0.02481 -0.00638 -0.00170 -0.00239 AFIX 23 H3 2 0.877213 0.830516 0.762207 11.00000 -1.20000 H2 2 1.036685 0.785686 0.722439 11.00000 -1.20000 AFIX 0 C9 1 0.649299 0.549598 0.709558 11.00000 0.02275 0.03219 = 0.01632 -0.00164 -0.00020 0.00114 C10 1 -0.138752 0.118035 0.565804 11.00000 0.03057 0.02402 = 0.02835 0.00059 -0.00699 -0.00291 AFIX 23 H6 2 -0.304504 0.064303 0.572924 11.00000 -1.20000 H12 2 -0.093446 0.082272 0.538223 11.00000 -1.20000 AFIX 0 C11 1 0.068664 0.061096 0.595395 11.00000 0.03234 0.01954 = 0.03295 0.00006 -0.00674 -0.00055 AFIX 23 H7 2 -0.007390 -0.000925 0.618548 11.00000 -1.20000 H11 2 0.192527 -0.018387 0.582252 11.00000 -1.20000 AFIX 0 C12 1 0.311335 0.208506 0.647597 11.00000 0.02615 0.01915 = 0.02404 0.00343 -0.00145 0.00080 AFIX 23 H8 2 0.461139 0.129751 0.645701 11.00000 -1.20000 H9 2 0.188188 0.154336 0.666354 11.00000 -1.20000 AFIX 0 C13 1 0.394637 0.385459 0.663870 11.00000 0.02210 0.02280 = 0.01709 0.00103 0.00381 0.00042 C14 1 0.570274 0.388283 0.695905 11.00000 0.02454 0.02588 = 0.01978 0.00289 0.00019 0.00256 AFIX 43 H10 2 0.631397 0.282321 0.707563 11.00000 -1.20000 AFIX 0 C15 1 0.024382 0.606858 0.541270 11.00000 0.01835 0.02420 = 0.01826 0.00456 0.00229 0.00151 AFIX 13 H14 2 -0.138040 0.666090 0.549231 11.00000 -1.20000 AFIX 0 C16 1 0.211157 0.614993 0.575400 11.00000 0.01913 0.01477 = 0.01924 0.00021 0.00293 0.00469 HKLF 4 1 1 0 0 0 1 0 0 0 1 REM qlll1_0m_a.res in P2(1)2(1)2(1) REM R1 = 0.0278 for 2600 Fo > 4sig(Fo) and 0.0282 for all 2637 data REM 191 parameters refined using 0 restraints END WGHT 0.0417 0.2445 REM Instructions for potential hydrogen bonds HTAB O3 O3_$1 HTAB O3 O4_$1 HTAB C11 O4_$2 HTAB C15 O3_$1 HTAB C15 O4_$3 REM Highest difference peak 0.222, deepest hole -0.169, 1-sigma level 0.037 Q1 1 -0.0873 0.3477 0.5885 11.00000 0.05 0.22 Q2 1 0.1668 0.5698 0.5954 11.00000 0.05 0.20 Q3 1 -0.0957 0.3753 0.5515 11.00000 0.05 0.18 Q4 1 0.2001 0.5373 0.6295 11.00000 0.05 0.17 ; _shelx_res_checksum 16903 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' loop_ _atom_site_type_symbol _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_refinement_flags_posn _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O O1 0.6712(3) 0.84689(16) 0.71180(4) 0.0302(3) Uani d . . . 1 . . O O2 0.8112(3) 0.58788(17) 0.74074(4) 0.0300(3) Uani d . . . 1 . . O O3 0.1291(2) 0.69300(17) 0.50754(3) 0.0242(3) Uani d . . . 1 . . H H17 0.011007 0.724947 0.4922 0.036 Uiso calc U . R 1 . . O O4 0.4242(2) 0.67484(15) 0.57184(3) 0.0216(2) Uani d . . . 1 . . N N1 0.1940(3) 0.22477(18) 0.60836(4) 0.0206(3) Uani d . . . 1 . . C C1 -0.0261(3) 0.4109(2) 0.53334(5) 0.0237(3) Uani d . . . 1 . . H H13 -0.137761 0.398915 0.509627 0.028 Uiso calc U . R 1 . . H H1 0.137172 0.351236 0.527328 0.028 Uiso calc U . R 1 . . C C2 -0.1523(3) 0.3211(2) 0.56920(5) 0.0219(3) Uani d . . . 1 . . H H5 -0.333709 0.359946 0.571596 0.026 Uiso calc U . R 1 . . C C3 -0.0097(3) 0.3564(2) 0.60860(5) 0.0192(3) Uani d . . . 1 . . H H15 -0.1269 0.330715 0.63145 0.023 Uiso calc U . R 1 . . C C4 0.1049(3) 0.5405(2) 0.61452(4) 0.0190(3) Uani d . . . 1 . . H H16 -0.037196 0.619741 0.623045 0.023 Uiso calc U . R 1 . . C C5 0.3008(3) 0.5417(2) 0.64788(4) 0.0194(3) Uani d . . . 1 . . C C6 0.3873(3) 0.7056(2) 0.66223(5) 0.0233(3) Uani d . . . 1 . . H H4 0.325607 0.812915 0.651288 0.028 Uiso calc U . R 1 . . C C7 0.5633(3) 0.7051(2) 0.69245(5) 0.0238(3) Uani d . . . 1 . . C C8 0.8697(3) 0.7715(2) 0.73583(5) 0.0284(4) Uani d . . . 1 . . H H3 0.877213 0.830516 0.762207 0.034 Uiso calc U . R 1 . . H H2 1.036685 0.785686 0.722439 0.034 Uiso calc U . R 1 . . C C9 0.6493(3) 0.5496(2) 0.70956(5) 0.0238(3) Uani d . . . 1 . . C C10 -0.1388(4) 0.1180(2) 0.56580(5) 0.0276(4) Uani d . . . 1 . . H H6 -0.304504 0.064303 0.572924 0.033 Uiso calc U . R 1 . . H H12 -0.093446 0.082272 0.538223 0.033 Uiso calc U . R 1 . . C C11 0.0687(4) 0.0611(2) 0.59539(5) 0.0283(4) Uani d . . . 1 . . H H7 -0.00739 -0.000925 0.618548 0.034 Uiso calc U . R 1 . . H H11 0.192527 -0.018387 0.582252 0.034 Uiso calc U . R 1 . . C C12 0.3113(3) 0.2085(2) 0.64760(5) 0.0231(3) Uani d . . . 1 . . H H8 0.461139 0.129751 0.645701 0.028 Uiso calc U . R 1 . . H H9 0.188188 0.154336 0.666354 0.028 Uiso calc U . R 1 . . C C13 0.3946(3) 0.3855(2) 0.66387(4) 0.0207(3) Uani d . . . 1 . . C C14 0.5703(3) 0.3883(2) 0.69591(5) 0.0234(3) Uani d . . . 1 . . H H10 0.631397 0.282321 0.707563 0.028 Uiso calc U . R 1 . . C C15 0.0244(3) 0.6069(2) 0.54127(4) 0.0203(3) Uani d . . . 1 . . H H14 -0.13804 0.66609 0.549231 0.024 Uiso calc U . R 1 . . C C16 0.2112(3) 0.6150(2) 0.57540(5) 0.0177(3) Uani d . . . 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 O1 0.0370(7) 0.0271(6) 0.0264(6) -0.0015(5) -0.0072(5) -0.0075(5) O2 0.0323(7) 0.0334(6) 0.0244(6) -0.0001(6) -0.0078(5) -0.0030(5) O3 0.0204(5) 0.0337(6) 0.0185(5) -0.0003(5) 0.0005(4) 0.0096(5) O4 0.0193(5) 0.0239(5) 0.0215(5) -0.0003(5) 0.0011(4) 0.0015(4) N1 0.0230(6) 0.0163(6) 0.0226(6) 0.0013(6) -0.0015(5) -0.0006(5) C1 0.0260(8) 0.0271(8) 0.0179(7) -0.0014(7) -0.0026(6) -0.0001(6) C2 0.0200(7) 0.0222(7) 0.0235(8) -0.0010(6) -0.0017(6) 0.0013(6) C3 0.0183(7) 0.0206(8) 0.0188(7) 0.0005(6) 0.0025(6) 0.0024(5) C4 0.0199(7) 0.0192(7) 0.0178(7) 0.0026(6) 0.0025(6) 0.0005(6) C5 0.0212(8) 0.0222(7) 0.0148(6) 0.0015(6) 0.0038(6) 0.0008(6) C6 0.0292(8) 0.0218(7) 0.0190(7) 0.0032(7) 0.0017(6) -0.0006(6) C7 0.0272(8) 0.0251(8) 0.0191(7) -0.0011(7) 0.0031(6) -0.0040(6) C8 0.0260(8) 0.0342(9) 0.0248(8) -0.0024(7) -0.0017(7) -0.0064(7) C9 0.0228(8) 0.0322(9) 0.0163(7) 0.0011(7) -0.0002(6) -0.0016(7) C10 0.0306(9) 0.0240(8) 0.0283(8) -0.0029(7) -0.0070(7) 0.0006(7) C11 0.0323(9) 0.0195(8) 0.0329(9) -0.0005(7) -0.0067(8) 0.0001(7) C12 0.0262(8) 0.0192(7) 0.0240(8) 0.0008(7) -0.0014(7) 0.0034(6) C13 0.0221(8) 0.0228(7) 0.0171(7) 0.0004(7) 0.0038(6) 0.0010(6) C14 0.0245(8) 0.0259(8) 0.0198(7) 0.0026(7) 0.0002(6) 0.0029(6) C15 0.0183(7) 0.0242(8) 0.0183(7) 0.0015(6) 0.0023(6) 0.0046(6) C16 0.0191(7) 0.0148(6) 0.0192(7) 0.0047(6) 0.0029(6) 0.0002(5) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C7 O1 C8 . . 104.42(14) ? C9 O2 C8 . . 104.51(14) ? C15 O3 H17 . . 109.5 ? C12 N1 C3 . . 111.24(12) ? C12 N1 C11 . . 112.52(13) ? C3 N1 C11 . . 104.60(13) ? C2 C1 C15 . . 111.83(13) ? C2 C1 H13 . . 109.3 ? C15 C1 H13 . . 109.3 ? C2 C1 H1 . . 109.3 ? C15 C1 H1 . . 109.3 ? H13 C1 H1 . . 107.9 ? C1 C2 C3 . . 112.47(13) ? C1 C2 C10 . . 111.52(14) ? C3 C2 C10 . . 102.36(13) ? C1 C2 H5 . . 110.1 ? C3 C2 H5 . . 110.1 ? C10 C2 H5 . . 110.1 ? N1 C3 C4 . . 109.67(13) ? N1 C3 C2 . . 103.40(13) ? C4 C3 C2 . . 117.38(13) ? N1 C3 H15 . . 108.7 ? C4 C3 H15 . . 108.7 ? C2 C3 H15 . . 108.7 ? C5 C4 C16 . . 112.27(13) ? C5 C4 C3 . . 111.48(13) ? C16 C4 C3 . . 111.68(12) ? C5 C4 H16 . . 107.0 ? C16 C4 H16 . . 107.0 ? C3 C4 H16 . . 107.0 ? C13 C5 C6 . . 120.58(15) ? C13 C5 C4 . . 121.13(14) ? C6 C5 C4 . . 118.29(14) ? C7 C6 C5 . . 117.77(15) ? C7 C6 H4 . . 121.1 ? C5 C6 H4 . . 121.1 ? C6 C7 O1 . . 128.42(16) ? C6 C7 C9 . . 121.75(16) ? O1 C7 C9 . . 109.76(14) ? O1 C8 O2 . . 107.23(14) ? O1 C8 H3 . . 110.3 ? O2 C8 H3 . . 110.3 ? O1 C8 H2 . . 110.3 ? O2 C8 H2 . . 110.3 ? H3 C8 H2 . . 108.5 ? C14 C9 O2 . . 128.87(16) ? C14 C9 C7 . . 121.66(15) ? O2 C9 C7 . . 109.46(15) ? C11 C10 C2 . . 105.45(14) ? C11 C10 H6 . . 110.7 ? C2 C10 H6 . . 110.7 ? C11 C10 H12 . . 110.7 ? C2 C10 H12 . . 110.7 ? H6 C10 H12 . . 108.8 ? N1 C11 C10 . . 105.61(13) ? N1 C11 H7 . . 110.6 ? C10 C11 H7 . . 110.6 ? N1 C11 H11 . . 110.6 ? C10 C11 H11 . . 110.6 ? H7 C11 H11 . . 108.8 ? N1 C12 C13 . . 111.76(13) ? N1 C12 H8 . . 109.3 ? C13 C12 H8 . . 109.3 ? N1 C12 H9 . . 109.3 ? C13 C12 H9 . . 109.3 ? H8 C12 H9 . . 107.9 ? C5 C13 C14 . . 120.59(15) ? C5 C13 C12 . . 121.12(14) ? C14 C13 C12 . . 118.29(14) ? C9 C14 C13 . . 117.57(15) ? C9 C14 H10 . . 121.2 ? C13 C14 H10 . . 121.2 ? O3 C15 C16 . . 109.39(13) ? O3 C15 C1 . . 112.21(13) ? C16 C15 C1 . . 106.44(13) ? O3 C15 H14 . . 109.6 ? C16 C15 H14 . . 109.6 ? C1 C15 H14 . . 109.6 ? O4 C16 C15 . . 122.78(14) ? O4 C16 C4 . . 123.94(14) ? C15 C16 C4 . . 113.27(13) ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C7 . 1.378(2) ? O1 C8 . 1.435(2) ? O2 C9 . 1.376(2) ? O2 C8 . 1.437(2) ? O3 C15 . 1.4147(18) ? O3 H17 . 0.84 ? O4 C16 . 1.213(2) ? N1 C12 . 1.454(2) ? N1 C3 . 1.464(2) ? N1 C11 . 1.472(2) ? C1 C2 . 1.530(2) ? C1 C15 . 1.535(2) ? C1 H13 . 0.99 ? C1 H1 . 0.99 ? C2 C3 . 1.538(2) ? C2 C10 . 1.548(2) ? C2 H5 . 1.0 ? C3 C4 . 1.535(2) ? C3 H15 . 1.0 ? C4 C5 . 1.517(2) ? C4 C16 . 1.530(2) ? C4 H16 . 1.0 ? C5 C13 . 1.392(2) ? C5 C6 . 1.409(2) ? C6 C7 . 1.369(2) ? C6 H4 . 0.95 ? C7 C9 . 1.388(3) ? C8 H3 . 0.99 ? C8 H2 . 0.99 ? C9 C14 . 1.372(3) ? C10 C11 . 1.533(2) ? C10 H6 . 0.99 ? C10 H12 . 0.99 ? C11 H7 . 0.99 ? C11 H11 . 0.99 ? C12 C13 . 1.514(2) ? C12 H8 . 0.99 ? C12 H9 . 0.99 ? C13 C14 . 1.413(2) ? C14 H10 . 0.95 ? C15 C16 . 1.505(2) ? C15 H14 . 1.0 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag O3 H17 O3 2_466 0.84 2.10 2.8091(9) 142.0 ? O3 H17 O4 2_466 0.84 2.32 3.0334(15) 143.5 ? C11 H11 O4 1_545 0.99 2.65 3.565(2) 153.6 ? C15 H14 O3 2_466 1.00 2.50 3.0458(19) 114.1 ? C15 H14 O4 1_455 1.00 2.42 3.3516(19) 154.8 ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag C15 C1 C2 C3 . . . . -50.74(19) ? C15 C1 C2 C10 . . . . -165.07(14) ? C12 N1 C3 C4 . . . . 68.13(16) ? C11 N1 C3 C4 . . . . -170.14(12) ? C12 N1 C3 C2 . . . . -165.91(13) ? C11 N1 C3 C2 . . . . -44.18(15) ? C1 C2 C3 N1 . . . . -83.32(16) ? C10 C2 C3 N1 . . . . 36.48(15) ? C1 C2 C3 C4 . . . . 37.55(19) ? C10 C2 C3 C4 . . . . 157.35(14) ? N1 C3 C4 C5 . . . . -45.87(16) ? C2 C3 C4 C5 . . . . -163.41(13) ? N1 C3 C4 C16 . . . . 80.62(15) ? C2 C3 C4 C16 . . . . -36.92(19) ? C16 C4 C5 C13 . . . . -113.73(16) ? C3 C4 C5 C13 . . . . 12.4(2) ? C16 C4 C5 C6 . . . . 65.88(18) ? C3 C4 C5 C6 . . . . -167.96(14) ? C13 C5 C6 C7 . . . . -0.7(2) ? C4 C5 C6 C7 . . . . 179.73(14) ? C5 C6 C7 O1 . . . . -178.48(15) ? C5 C6 C7 C9 . . . . -2.0(2) ? C8 O1 C7 C6 . . . . -171.00(17) ? C8 O1 C7 C9 . . . . 12.20(18) ? C7 O1 C8 O2 . . . . -20.54(17) ? C9 O2 C8 O1 . . . . 21.15(17) ? C8 O2 C9 C14 . . . . 167.57(17) ? C8 O2 C9 C7 . . . . -13.70(17) ? C6 C7 C9 C14 . . . . 2.8(3) ? O1 C7 C9 C14 . . . . 179.83(15) ? C6 C7 C9 O2 . . . . -176.07(15) ? O1 C7 C9 O2 . . . . 0.98(19) ? C1 C2 C10 C11 . . . . 104.59(16) ? C3 C2 C10 C11 . . . . -15.87(17) ? C12 N1 C11 C10 . . . . 154.57(14) ? C3 N1 C11 C10 . . . . 33.68(17) ? C2 C10 C11 N1 . . . . -10.00(19) ? C3 N1 C12 C13 . . . . -52.11(18) ? C11 N1 C12 C13 . . . . -169.11(14) ? C6 C5 C13 C14 . . . . 2.7(2) ? C4 C5 C13 C14 . . . . -177.73(14) ? C6 C5 C13 C12 . . . . -177.49(15) ? C4 C5 C13 C12 . . . . 2.1(2) ? N1 C12 C13 C5 . . . . 17.0(2) ? N1 C12 C13 C14 . . . . -163.14(14) ? O2 C9 C14 C13 . . . . 177.89(16) ? C7 C9 C14 C13 . . . . -0.7(2) ? C5 C13 C14 C9 . . . . -2.0(2) ? C12 C13 C14 C9 . . . . 178.21(14) ? C2 C1 C15 O3 . . . . -176.97(12) ? C2 C1 C15 C16 . . . . 63.41(17) ? O3 C15 C16 O4 . . . . -5.5(2) ? C1 C15 C16 O4 . . . . 115.90(16) ? O3 C15 C16 C4 . . . . 174.53(13) ? C1 C15 C16 C4 . . . . -64.03(16) ? C5 C4 C16 O4 . . . . -2.8(2) ? C3 C4 C16 O4 . . . . -128.86(15) ? C5 C4 C16 C15 . . . . 177.13(13) ? C3 C4 C16 C15 . . . . 51.07(18) ?