#------------------------------------------------------------------------------ #$Date: 2021-09-23 04:08:04 +0300 (Thu, 23 Sep 2021) $ #$Revision: 269251 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/35/7243572.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_7243572 loop_ _publ_author_name 'Wang, Tingshu' 'Zhang, Miao' 'Zheng, Yifan' 'Seong, Junmo' 'Lah, Myoung Soo' 'Koo, Sangho' _publ_section_title ; Furan oxidation by Mn(iii)/Co(ii) catalysts -- application to benzofuran synthesis ; _journal_issue 50 _journal_name_full 'RSC Advances' _journal_page_first 31395 _journal_page_last 31399 _journal_paper_doi 10.1039/D1RA05305A _journal_volume 11 _journal_year 2021 _chemical_formula_sum 'C19 H19 N O8' _chemical_formula_weight 389.35 _chemical_name_systematic 'Ethyl (2R,3aR,4S,5S)-4-acetyl-2-(4-nitrophenyl)-6-oxohexahydro-2,5-methanobenzo[d][1,3]dioxole-4-carboxylate' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-04-08 deposited with the CCDC. 2021-09-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 98.37(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 7.9677(16) _cell_length_b 8.9993(18) _cell_length_c 24.879(5) _cell_measurement_reflns_used 13187 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 27.48 _cell_measurement_theta_min 2.265 _cell_volume 1764.9(6) _computing_cell_refinement 'Rigaku Rapid Auto' _computing_data_collection 'Rigaku Rapid Auto' _computing_data_reduction 'Rigaku Rapid Auto' _computing_molecular_graphics ORTEP _computing_publication_material CIFTAB _computing_structure_refinement SHELXL _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'imaging plate' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0573 _diffrn_reflns_av_unetI/netI 0.0623 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_number 16531 _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 27.478 _diffrn_reflns_theta_min 2.410 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.116 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_correction_T_min 0.6946 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Rigaku Rapid Auto' _exptl_crystal_colour colorless _exptl_crystal_density_diffrn 1.465 _exptl_crystal_description block _exptl_crystal_F_000 816 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.700 _exptl_crystal_size_mid 0.515 _exptl_crystal_size_min 0.343 _refine_diff_density_max 0.334 _refine_diff_density_min -0.239 _refine_diff_density_rms 0.050 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.085 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 329 _refine_ls_number_reflns 4049 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.085 _refine_ls_R_factor_all 0.0819 _refine_ls_R_factor_gt 0.0584 _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^)+(0.0445P)^2^+1.2447P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1197 _refine_ls_wR_factor_ref 0.1306 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3180 _reflns_number_total 4049 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ra05305a2.cif _cod_data_source_block O20_003_P2(1)n _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_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7243572 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_res_file ; TITL O20_003_P2(1)n.res in P2(1)/n O20_003_P2(1)n.res created by SHELXL-2018/3 at 17:55:05 on 24-Sep-2020 CELL 0.71073 7.9677 8.9993 24.8794 90.000 98.374 90.000 ZERR 4.000 0.0016 0.0018 0.0050 0.000 0.030 0.000 LATT 1 SYMM 1/2-X, 1/2+Y, 1/2-Z SFAC C H N O UNIT 76 76 4 32 L.S. 10 ACTA BOND $H FMAP 2 PLAN 10 LIST 4 WGHT 0.044500 1.244700 FVAR 0.43374 C1 1 0.773287 0.407188 0.313842 11.00000 0.03085 0.03044 = 0.03324 -0.01188 0.00822 -0.00531 O1 4 0.902887 0.342721 0.309179 11.00000 0.03516 0.06410 = 0.04833 -0.02037 0.01043 0.01023 C2 1 0.669636 0.491551 0.267821 11.00000 0.04035 0.03765 = 0.02518 -0.00627 0.01222 -0.00827 H21 2 0.594056 0.418116 0.246148 11.00000 0.03810 H22 2 0.742761 0.529193 0.244144 11.00000 0.03741 O2 4 0.694658 0.713884 0.321769 11.00000 0.03778 0.02936 = 0.02212 -0.00102 0.00814 -0.00760 C3 1 0.572441 0.616089 0.290399 11.00000 0.03719 0.02563 = 0.02432 0.00213 0.00122 -0.00596 H3 2 0.509318 0.675255 0.261291 11.00000 0.03756 O3 4 0.496016 0.671849 0.375339 11.00000 0.02366 0.02403 = 0.02972 -0.00193 0.00451 0.00057 C4 1 0.457829 0.565938 0.332304 11.00000 0.02626 0.02319 = 0.02587 0.00011 0.00134 0.00064 H4 2 0.334577 0.572180 0.318242 11.00000 0.02704 C5 1 0.674582 0.692509 0.377176 11.00000 0.02601 0.02571 = 0.02317 0.00046 0.00739 -0.00091 C6 1 0.767863 0.552567 0.399974 11.00000 0.02347 0.02644 = 0.02589 -0.00322 0.00353 0.00129 H61 2 0.750838 0.540274 0.437941 11.00000 0.01617 H62 2 0.886588 0.564514 0.399669 11.00000 0.02188 C7 1 0.703383 0.410958 0.367532 11.00000 0.02703 0.02336 = 0.02625 -0.00060 0.00347 0.00288 H7 2 0.743356 0.323678 0.387962 11.00000 0.01769 C8 1 0.508017 0.412332 0.356659 11.00000 0.02390 0.02341 = 0.02535 0.00127 0.00486 0.00058 O4 4 0.316485 0.306355 0.282273 11.00000 0.04303 0.03143 = 0.03445 0.00122 -0.00910 -0.00118 O5 4 0.498968 0.157882 0.334420 11.00000 0.03483 0.02380 = 0.04370 -0.00443 -0.00740 0.00149 C9 1 0.430346 0.288001 0.319187 11.00000 0.02680 0.02573 = 0.02629 0.00253 0.00695 -0.00062 C10 1 0.414464 0.025809 0.308478 11.00000 0.03952 0.02376 = 0.03694 -0.00469 -0.00129 -0.00010 H101 2 0.380650 0.046208 0.270531 11.00000 0.03117 H102 2 0.502643 -0.049119 0.315510 11.00000 0.03893 C11 1 0.265970 -0.015238 0.335739 11.00000 0.05400 0.03747 = 0.03953 -0.00145 0.00659 -0.00944 H111 2 0.181678 0.063841 0.332560 11.00000 0.04336 H112 2 0.221181 -0.108202 0.319608 11.00000 0.04893 H113 2 0.303345 -0.031058 0.375440 11.00000 0.06560 O6 4 0.523927 0.340578 0.450166 11.00000 0.04638 0.05435 = 0.03134 0.01209 0.00864 0.00049 C12 1 0.433915 0.387898 0.410769 11.00000 0.03639 0.02284 = 0.03026 0.00016 0.01121 -0.00379 C13 1 0.250783 0.422133 0.410499 11.00000 0.03432 0.04299 = 0.04466 -0.00550 0.01566 -0.00465 H131 2 0.238115 0.529655 0.413619 11.00000 0.06181 H132 2 0.188788 0.378318 0.377726 11.00000 0.05798 H133 2 0.212871 0.375513 0.440839 11.00000 0.07331 C14 1 0.725595 0.829511 0.410012 11.00000 0.02472 0.02387 = 0.02351 0.00181 0.00184 0.00283 C15 1 0.837267 0.932614 0.393635 11.00000 0.02927 0.03035 = 0.02546 0.00173 0.00847 0.00179 H15 2 0.880914 0.915584 0.362568 11.00000 0.02422 C16 1 0.883290 1.058109 0.424431 11.00000 0.02494 0.02548 = 0.03028 0.00330 0.00438 -0.00069 H16 2 0.960683 1.128974 0.413883 11.00000 0.03373 O1N 4 0.952123 1.304075 0.488049 11.00000 0.04049 0.03381 = 0.04709 -0.00577 0.00299 -0.00992 O2N 4 0.809562 1.220672 0.549042 11.00000 0.05582 0.03959 = 0.03214 -0.01047 0.00983 0.00095 N1 3 0.862469 1.210254 0.505413 11.00000 0.02861 0.02723 = 0.03363 -0.00141 -0.00086 0.00354 C17 1 0.815160 1.077721 0.472081 11.00000 0.02439 0.02390 = 0.02720 0.00036 -0.00055 0.00281 C18 1 0.706579 0.975720 0.489799 11.00000 0.03016 0.03302 = 0.02533 -0.00129 0.00833 0.00156 H18 2 0.667023 0.992510 0.522385 11.00000 0.03677 C19 1 0.661111 0.851484 0.458625 11.00000 0.03045 0.02798 = 0.03044 0.00066 0.00823 -0.00358 H19 2 0.586384 0.777797 0.469390 11.00000 0.04125 HKLF 4 REM O20_003_P2(1)n.res in P2(1)/n REM wR2 = 0.1306, GooF = S = 1.085, Restrained GooF = 1.085 for all data REM R1 = 0.0584 for 3180 Fo > 4sig(Fo) and 0.0819 for all 4049 data REM 329 parameters refined using 0 restraints END WGHT 0.0445 1.2448 REM Highest difference peak 0.334, deepest hole -0.239, 1-sigma level 0.050 Q1 1 0.4860 0.4858 0.3442 11.00000 0.05 0.33 Q2 1 0.6992 0.7628 0.3959 11.00000 0.05 0.33 Q3 1 0.7257 0.4853 0.3826 11.00000 0.05 0.31 Q4 1 0.4654 0.4123 0.3819 11.00000 0.05 0.31 Q5 1 0.6050 0.4108 0.3609 11.00000 0.05 0.30 Q6 1 0.5060 0.5810 0.3069 11.00000 0.05 0.30 Q7 1 0.7362 0.4172 0.3401 11.00000 0.05 0.30 Q8 1 0.4705 0.3592 0.3338 11.00000 0.05 0.29 Q9 1 0.7204 1.0670 0.4698 11.00000 0.05 0.28 Q10 1 0.7215 0.6248 0.3880 11.00000 0.05 0.27 ; _shelx_res_checksum 78056 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' 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 0.7733(3) 0.4072(2) 0.31384(9) 0.0312(5) Uani 1 1 d . . . . . O1 O 0.9029(2) 0.3427(2) 0.30918(7) 0.0488(5) Uani 1 1 d . . . . . C2 C 0.6696(3) 0.4916(3) 0.26782(9) 0.0337(5) Uani 1 1 d . . . . . H21 H 0.594(3) 0.418(3) 0.2461(10) 0.038(7) Uiso 1 1 d . . . . . H22 H 0.743(3) 0.529(3) 0.2441(10) 0.037(7) Uiso 1 1 d . . . . . O2 O 0.69466(19) 0.71388(16) 0.32177(5) 0.0294(3) Uani 1 1 d . . . . . C3 C 0.5724(3) 0.6161(2) 0.29040(9) 0.0294(5) Uani 1 1 d . . . . . H3 H 0.509(3) 0.675(3) 0.2613(10) 0.038(7) Uiso 1 1 d . . . . . O3 O 0.49602(17) 0.67185(15) 0.37534(6) 0.0257(3) Uani 1 1 d . . . . . C4 C 0.4578(3) 0.5659(2) 0.33230(8) 0.0254(4) Uani 1 1 d . . . . . H4 H 0.335(3) 0.572(2) 0.3182(9) 0.027(6) Uiso 1 1 d . . . . . C5 C 0.6746(3) 0.6925(2) 0.37718(8) 0.0246(4) Uani 1 1 d . . . . . C6 C 0.7679(3) 0.5526(2) 0.39997(8) 0.0253(4) Uani 1 1 d . . . . . H61 H 0.751(3) 0.540(2) 0.4379(8) 0.016(5) Uiso 1 1 d . . . . . H62 H 0.887(3) 0.565(2) 0.3997(8) 0.022(5) Uiso 1 1 d . . . . . C7 C 0.7034(3) 0.4110(2) 0.36753(8) 0.0256(4) Uani 1 1 d . . . . . H7 H 0.743(3) 0.324(2) 0.3880(8) 0.018(5) Uiso 1 1 d . . . . . C8 C 0.5080(3) 0.4123(2) 0.35666(8) 0.0241(4) Uani 1 1 d . . . . . O4 O 0.3165(2) 0.30635(17) 0.28227(6) 0.0378(4) Uani 1 1 d . . . . . O5 O 0.4990(2) 0.15788(16) 0.33442(6) 0.0354(4) Uani 1 1 d . . . . . C9 C 0.4303(3) 0.2880(2) 0.31919(8) 0.0260(4) Uani 1 1 d . . . . . C10 C 0.4145(3) 0.0258(2) 0.30848(10) 0.0341(5) Uani 1 1 d . . . . . H101 H 0.381(3) 0.046(3) 0.2705(10) 0.031(6) Uiso 1 1 d . . . . . H102 H 0.503(3) -0.049(3) 0.3155(10) 0.039(7) Uiso 1 1 d . . . . . C11 C 0.2660(4) -0.0152(3) 0.33574(11) 0.0437(6) Uani 1 1 d . . . . . H111 H 0.182(3) 0.064(3) 0.3326(10) 0.043(7) Uiso 1 1 d . . . . . H112 H 0.221(3) -0.108(3) 0.3196(11) 0.049(8) Uiso 1 1 d . . . . . H113 H 0.303(4) -0.031(3) 0.3754(14) 0.066(9) Uiso 1 1 d . . . . . O6 O 0.5239(2) 0.3406(2) 0.45017(6) 0.0437(4) Uani 1 1 d . . . . . C12 C 0.4339(3) 0.3879(2) 0.41077(9) 0.0292(5) Uani 1 1 d . . . . . C13 C 0.2508(3) 0.4221(3) 0.41050(12) 0.0397(6) Uani 1 1 d . . . . . H131 H 0.238(4) 0.530(4) 0.4136(12) 0.062(9) Uiso 1 1 d . . . . . H132 H 0.189(4) 0.378(3) 0.3777(13) 0.058(9) Uiso 1 1 d . . . . . H133 H 0.213(4) 0.376(4) 0.4408(14) 0.073(10) Uiso 1 1 d . . . . . C14 C 0.7256(2) 0.8295(2) 0.41001(8) 0.0242(4) Uani 1 1 d . . . . . C15 C 0.8373(3) 0.9326(2) 0.39364(9) 0.0279(4) Uani 1 1 d . . . . . H15 H 0.881(3) 0.916(2) 0.3626(9) 0.024(6) Uiso 1 1 d . . . . . C16 C 0.8833(3) 1.0581(2) 0.42443(8) 0.0269(4) Uani 1 1 d . . . . . H16 H 0.961(3) 1.129(3) 0.4139(10) 0.034(6) Uiso 1 1 d . . . . . O1N O 0.9521(2) 1.30407(18) 0.48805(7) 0.0408(4) Uani 1 1 d . . . . . O2N O 0.8096(2) 1.22067(19) 0.54904(7) 0.0422(4) Uani 1 1 d . . . . . N1 N 0.8625(2) 1.21025(19) 0.50541(8) 0.0304(4) Uani 1 1 d . . . . . C17 C 0.8152(3) 1.0777(2) 0.47208(8) 0.0256(4) Uani 1 1 d . . . . . C18 C 0.7066(3) 0.9757(2) 0.48980(9) 0.0291(5) Uani 1 1 d . . . . . H18 H 0.667(3) 0.993(3) 0.5224(10) 0.037(6) Uiso 1 1 d . . . . . C19 C 0.6611(3) 0.8515(2) 0.45862(9) 0.0292(5) Uani 1 1 d . . . . . H19 H 0.586(3) 0.778(3) 0.4694(10) 0.041(7) Uiso 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 0.0308(11) 0.0304(11) 0.0332(11) -0.0119(9) 0.0082(9) -0.0053(9) O1 0.0352(9) 0.0641(12) 0.0483(10) -0.0204(9) 0.0104(8) 0.0102(9) C2 0.0404(13) 0.0377(12) 0.0252(10) -0.0063(9) 0.0122(10) -0.0083(11) O2 0.0378(8) 0.0294(8) 0.0221(7) -0.0010(6) 0.0081(6) -0.0076(7) C3 0.0372(12) 0.0256(10) 0.0243(10) 0.0021(8) 0.0012(9) -0.0060(9) O3 0.0237(7) 0.0240(7) 0.0297(7) -0.0019(6) 0.0045(6) 0.0006(6) C4 0.0263(11) 0.0232(10) 0.0259(10) 0.0001(8) 0.0013(8) 0.0006(8) C5 0.0260(10) 0.0257(10) 0.0232(9) 0.0005(8) 0.0074(8) -0.0009(8) C6 0.0235(10) 0.0264(10) 0.0259(10) -0.0032(8) 0.0035(8) 0.0013(8) C7 0.0270(10) 0.0234(10) 0.0262(10) -0.0006(8) 0.0035(8) 0.0029(8) C8 0.0239(10) 0.0234(10) 0.0254(10) 0.0013(8) 0.0049(8) 0.0006(8) O4 0.0430(9) 0.0314(8) 0.0344(8) 0.0012(7) -0.0091(7) -0.0012(7) O5 0.0348(8) 0.0238(7) 0.0437(9) -0.0044(7) -0.0074(7) 0.0015(7) C9 0.0268(10) 0.0257(10) 0.0263(10) 0.0025(8) 0.0069(9) -0.0006(8) C10 0.0395(13) 0.0238(10) 0.0369(12) -0.0047(9) -0.0013(10) -0.0001(10) C11 0.0540(16) 0.0375(14) 0.0395(14) -0.0014(11) 0.0066(12) -0.0094(13) O6 0.0464(10) 0.0544(11) 0.0313(8) 0.0121(8) 0.0086(8) 0.0005(9) C12 0.0364(12) 0.0228(10) 0.0303(11) 0.0002(8) 0.0112(9) -0.0038(9) C13 0.0343(13) 0.0430(14) 0.0447(14) -0.0055(12) 0.0157(11) -0.0046(11) C14 0.0247(10) 0.0239(10) 0.0235(10) 0.0018(8) 0.0018(8) 0.0028(8) C15 0.0293(11) 0.0304(11) 0.0255(10) 0.0017(9) 0.0085(9) 0.0018(9) C16 0.0249(10) 0.0255(10) 0.0303(10) 0.0033(9) 0.0044(8) -0.0007(9) O1N 0.0405(9) 0.0338(9) 0.0471(10) -0.0058(7) 0.0030(8) -0.0099(8) O2N 0.0558(11) 0.0396(9) 0.0321(9) -0.0105(7) 0.0098(8) 0.0009(8) N1 0.0286(9) 0.0272(9) 0.0336(10) -0.0014(8) -0.0009(8) 0.0035(8) C17 0.0244(10) 0.0239(10) 0.0272(10) 0.0004(8) -0.0005(8) 0.0028(8) C18 0.0302(11) 0.0330(11) 0.0253(10) -0.0013(9) 0.0083(9) 0.0016(9) C19 0.0304(11) 0.0280(10) 0.0304(11) 0.0007(9) 0.0082(9) -0.0036(9) 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 O1 C1 C2 123.3(2) . . ? O1 C1 C7 121.6(2) . . ? C2 C1 C7 115.07(18) . . ? C1 C2 C3 110.01(17) . . ? C1 C2 H21 107.2(14) . . ? C3 C2 H21 112.9(15) . . ? C1 C2 H22 109.4(15) . . ? C3 C2 H22 111.0(15) . . ? H21 C2 H22 106(2) . . ? C5 O2 C3 106.10(15) . . ? O2 C3 C2 107.96(19) . . ? O2 C3 C4 103.27(15) . . ? C2 C3 C4 114.63(18) . . ? O2 C3 H3 107.5(14) . . ? C2 C3 H3 111.3(14) . . ? C4 C3 H3 111.5(14) . . ? C5 O3 C4 102.27(15) . . ? O3 C4 C8 106.78(15) . . ? O3 C4 C3 103.13(16) . . ? C8 C4 C3 112.44(17) . . ? O3 C4 H4 108.5(13) . . ? C8 C4 H4 112.1(13) . . ? C3 C4 H4 113.3(13) . . ? O2 C5 O3 103.79(15) . . ? O2 C5 C14 110.86(16) . . ? O3 C5 C14 108.27(16) . . ? O2 C5 C6 110.70(16) . . ? O3 C5 C6 109.43(16) . . ? C14 C5 C6 113.33(16) . . ? C5 C6 C7 112.11(17) . . ? C5 C6 H61 108.8(12) . . ? C7 C6 H61 109.0(12) . . ? C5 C6 H62 109.5(13) . . ? C7 C6 H62 110.0(13) . . ? H61 C6 H62 107.3(17) . . ? C1 C7 C8 109.63(17) . . ? C1 C7 C6 109.79(17) . . ? C8 C7 C6 109.48(16) . . ? C1 C7 H7 108.0(12) . . ? C8 C7 H7 110.3(12) . . ? C6 C7 H7 109.6(12) . . ? C9 C8 C4 111.01(16) . . ? C9 C8 C7 114.22(16) . . ? C4 C8 C7 105.92(16) . . ? C9 C8 C12 104.61(16) . . ? C4 C8 C12 110.89(16) . . ? C7 C8 C12 110.28(17) . . ? C9 O5 C10 116.50(17) . . ? O4 C9 O5 124.97(19) . . ? O4 C9 C8 123.90(19) . . ? O5 C9 C8 111.05(17) . . ? O5 C10 C11 110.1(2) . . ? O5 C10 H101 108.8(14) . . ? C11 C10 H101 111.5(14) . . ? O5 C10 H102 102.1(15) . . ? C11 C10 H102 110.3(15) . . ? H101 C10 H102 114(2) . . ? C10 C11 H111 111.4(16) . . ? C10 C11 H112 107.0(16) . . ? H111 C11 H112 113(2) . . ? C10 C11 H113 110.0(18) . . ? H111 C11 H113 107(2) . . ? H112 C11 H113 109(2) . . ? O6 C12 C13 122.9(2) . . ? O6 C12 C8 119.7(2) . . ? C13 C12 C8 117.36(19) . . ? C12 C13 H131 108.5(18) . . ? C12 C13 H132 107.3(18) . . ? H131 C13 H132 115(3) . . ? C12 C13 H133 109(2) . . ? H131 C13 H133 109(3) . . ? H132 C13 H133 108(3) . . ? C15 C14 C19 119.52(19) . . ? C15 C14 C5 121.58(18) . . ? C19 C14 C5 118.89(18) . . ? C16 C15 C14 120.9(2) . . ? C16 C15 H15 120.5(14) . . ? C14 C15 H15 118.7(14) . . ? C15 C16 C17 118.2(2) . . ? C15 C16 H16 121.7(15) . . ? C17 C16 H16 120.1(15) . . ? O2N N1 O1N 123.64(19) . . ? O2N N1 C17 117.99(18) . . ? O1N N1 C17 118.37(18) . . ? C18 C17 C16 122.13(19) . . ? C18 C17 N1 118.79(19) . . ? C16 C17 N1 119.07(19) . . ? C17 C18 C19 119.1(2) . . ? C17 C18 H18 118.8(16) . . ? C19 C18 H18 122.1(16) . . ? C18 C19 C14 120.2(2) . . ? C18 C19 H19 121.9(15) . . ? C14 C19 H19 117.9(15) . . ? 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 O1 1.205(3) . ? C1 C2 1.515(3) . ? C1 C7 1.521(3) . ? C2 C3 1.516(3) . ? C2 H21 1.00(3) . ? C2 H22 0.95(3) . ? O2 C5 1.424(2) . ? O2 C3 1.453(3) . ? C3 C4 1.550(3) . ? C3 H3 0.98(3) . ? O3 C5 1.429(2) . ? O3 C4 1.433(2) . ? C4 C8 1.539(3) . ? C4 H4 0.99(2) . ? C5 C14 1.502(3) . ? C5 C6 1.529(3) . ? C6 C7 1.555(3) . ? C6 H61 0.98(2) . ? C6 H62 0.95(2) . ? C7 C8 1.541(3) . ? C7 H7 0.96(2) . ? C8 C9 1.528(3) . ? C8 C12 1.562(3) . ? O4 C9 1.205(3) . ? O5 C9 1.324(2) . ? O5 C10 1.468(3) . ? C10 C11 1.493(4) . ? C10 H101 0.96(2) . ? C10 H102 0.97(3) . ? C11 H111 0.97(3) . ? C11 H112 0.97(3) . ? C11 H113 1.00(3) . ? O6 C12 1.205(3) . ? C12 C13 1.490(3) . ? C13 H131 0.98(3) . ? C13 H132 0.97(3) . ? C13 H133 0.95(3) . ? C14 C15 1.387(3) . ? C14 C19 1.395(3) . ? C15 C16 1.384(3) . ? C15 H15 0.91(2) . ? C16 C17 1.385(3) . ? C16 H16 0.95(3) . ? O1N N1 1.225(2) . ? O2N N1 1.224(2) . ? N1 C17 1.470(3) . ? C17 C18 1.377(3) . ? C18 C19 1.379(3) . ? C18 H18 0.92(3) . ? C19 H19 0.96(3) . ?