#------------------------------------------------------------------------------ #$Date: 2020-06-05 14:29:34 +0300 (Fri, 05 Jun 2020) $ #$Revision: 252916 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157493.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_7157493 loop_ _publ_author_name 'Ravindran, Jaice' 'Yadhukrishnan, Velickakathu O.' 'Asha, Reghuvaran S.' 'Lankalapalli, Ravi S.' _publ_section_title ; Dienaminodioate based multicomponent reactions with post-benzylic oxidative transformations mediated by DDQ. ; _journal_issue 20 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 3927 _journal_page_last 3937 _journal_paper_doi 10.1039/d0ob00721h _journal_volume 18 _journal_year 2020 _chemical_formula_moiety 'C24 H19 N O6' _chemical_formula_sum 'C24 H19 N O6' _chemical_formula_weight 417.40 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2018-12-12 deposited with the CCDC. 2020-05-06 downloaded from the CCDC. ; _cell_angle_alpha 83.258(4) _cell_angle_beta 82.820(4) _cell_angle_gamma 84.193(4) _cell_formula_units_Z 2 _cell_length_a 8.2622(7) _cell_length_b 10.8562(10) _cell_length_c 11.4554(8) _cell_measurement_reflns_used 4080 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 24.38 _cell_measurement_theta_min 2.49 _cell_volume 1008.49(15) _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT-2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 296(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0343 _diffrn_reflns_av_unetI/netI 0.0371 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 15132 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 24.997 _diffrn_reflns_theta_max 24.997 _diffrn_reflns_theta_min 2.474 _exptl_absorpt_coefficient_mu 0.100 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_correction_T_min 0.6961 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2004)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.375 _exptl_crystal_description block _exptl_crystal_F_000 436 _exptl_crystal_size_max 0.200 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.150 _refine_diff_density_max 0.242 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.039 _refine_ls_extinction_coef 0.008(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 284 _refine_ls_number_reflns 3551 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.051 _refine_ls_R_factor_all 0.0828 _refine_ls_R_factor_gt 0.0433 _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^)+(0.0550P)^2^+0.2718P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1025 _refine_ls_wR_factor_ref 0.1287 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2255 _reflns_number_total 3551 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ob00721h2.cif _cod_data_source_block JR749 _cod_depositor_comments 'Adding full bibliography for 7157493--7157494.cif.' _cod_database_code 7157493 _shelx_shelxl_version_number 2014/7 _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_min 0.980 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; JR749.res created by SHELXL-2014/7 TITL jr749_a.res in P-1 CELL 0.71073 8.2622 10.8562 11.4554 83.258 82.820 84.193 ZERR 2.00 0.0007 0.0010 0.0008 0.004 0.004 0.004 LATT 1 SFAC C H N O UNIT 48 38 2 12 MERG 2 OMIT -3.00 50.00 DELU 0.005 N1 C7 FMAP 2 PLAN 20 SIZE 0.15 0.15 0.20 ACTA BOND $H CONF L.S. 4 TEMP 23.00 WGHT 0.055000 0.271800 EXTI 0.008080 FVAR 0.62370 C1 1 0.129764 0.610769 0.569287 11.00000 0.03813 0.03348 = 0.04712 -0.00485 -0.00542 0.00331 C2 1 0.038348 0.701727 0.627784 11.00000 0.05282 0.04711 = 0.05202 -0.01394 0.00309 0.00801 AFIX 43 H2 2 0.025227 0.698473 0.709879 11.00000 -1.20000 AFIX 0 C3 1 -0.032874 0.798270 0.557323 11.00000 0.04968 0.04824 = 0.08055 -0.01979 -0.00495 0.01098 AFIX 43 H3 2 -0.094964 0.863002 0.592874 11.00000 -1.20000 AFIX 0 C4 1 -0.015209 0.802201 0.435684 11.00000 0.05371 0.04643 = 0.07435 -0.00480 -0.02295 0.01023 AFIX 43 H4 2 -0.066128 0.868985 0.391433 11.00000 -1.20000 AFIX 0 C5 1 0.076323 0.709239 0.378291 11.00000 0.05932 0.04646 = 0.05163 -0.00567 -0.01811 0.00908 AFIX 43 H5 2 0.087510 0.711438 0.296293 11.00000 -1.20000 AFIX 0 C6 1 0.150645 0.612758 0.447799 11.00000 0.03855 0.03551 = 0.04403 -0.00719 -0.00787 0.00321 C7 1 0.287719 0.449765 0.518851 11.00000 0.03719 0.03371 = 0.03856 -0.00979 -0.00312 0.00007 C8 1 0.399417 0.335880 0.529064 11.00000 0.03430 0.02952 = 0.03489 -0.00497 -0.00314 -0.00094 C9 1 0.467596 0.293399 0.422104 11.00000 0.04319 0.03225 = 0.03106 -0.00248 -0.00349 -0.00113 AFIX 43 H9 2 0.440004 0.337452 0.351677 11.00000 -1.20000 AFIX 0 C10 1 0.574587 0.188087 0.417869 11.00000 0.04098 0.03231 = 0.03565 -0.00769 -0.00054 -0.00201 C11 1 0.616834 0.123356 0.522570 11.00000 0.04217 0.03105 = 0.04222 -0.00657 -0.00484 0.00475 AFIX 43 H11 2 0.688239 0.051484 0.520730 11.00000 -1.20000 AFIX 0 C12 1 0.553505 0.164859 0.630141 11.00000 0.04011 0.03509 = 0.03341 -0.00440 -0.00569 0.00345 C13 1 0.441240 0.270853 0.636513 11.00000 0.03627 0.03071 = 0.03272 -0.00587 -0.00455 -0.00223 C14 1 0.364048 0.305499 0.753952 11.00000 0.03860 0.03518 = 0.03089 -0.00499 -0.00625 0.00376 C15 1 0.245336 0.234675 0.816680 11.00000 0.05207 0.03567 = 0.03525 -0.00685 -0.00615 -0.00203 AFIX 43 H15 2 0.216711 0.165582 0.785607 11.00000 -1.20000 AFIX 0 C16 1 0.169211 0.265455 0.924582 11.00000 0.05319 0.04592 = 0.03600 -0.00087 0.00020 -0.00454 AFIX 43 H16 2 0.089277 0.217293 0.965591 11.00000 -1.20000 AFIX 0 C17 1 0.210660 0.367147 0.972225 11.00000 0.05238 0.04502 = 0.02743 -0.00635 -0.00451 0.00743 C18 1 0.331004 0.436699 0.912166 11.00000 0.05947 0.04398 = 0.03953 -0.01403 -0.00700 -0.00184 AFIX 43 H18 2 0.361822 0.504279 0.944448 11.00000 -1.20000 AFIX 0 C19 1 0.406077 0.405431 0.803207 11.00000 0.04950 0.04388 = 0.03838 -0.00947 -0.00094 -0.00576 AFIX 43 H19 2 0.486689 0.453197 0.762571 11.00000 -1.20000 AFIX 0 C20 1 0.164936 0.494032 1.131593 11.00000 0.10560 0.08234 = 0.04923 -0.03302 0.00586 -0.00601 AFIX 137 H20A 2 0.275514 0.480083 1.150955 11.00000 -1.50000 H20B 2 0.091539 0.504153 1.202364 11.00000 -1.50000 H20C 2 0.154174 0.567883 1.077157 11.00000 -1.50000 AFIX 0 C21 1 0.618562 0.100484 0.739756 11.00000 0.05367 0.04985 = 0.03882 -0.00548 -0.00664 0.01622 C22 1 0.739798 -0.086559 0.827526 11.00000 0.14901 0.08729 = 0.06407 0.00980 -0.03699 0.05884 AFIX 137 H22A 2 0.843619 -0.055107 0.830196 11.00000 -1.50000 H22B 2 0.756300 -0.173522 0.816878 11.00000 -1.50000 H22C 2 0.671310 -0.075560 0.900322 11.00000 -1.50000 AFIX 0 C23 1 0.652075 0.143666 0.304427 11.00000 0.05722 0.03784 = 0.04047 -0.00910 -0.00007 0.00280 C24 1 0.676597 0.182126 0.095957 11.00000 0.15721 0.09116 = 0.03490 -0.01319 0.01624 0.01994 AFIX 137 H24A 2 0.791936 0.191659 0.084963 11.00000 -1.50000 H24B 2 0.624469 0.234200 0.035274 11.00000 -1.50000 H24C 2 0.659309 0.096762 0.091490 11.00000 -1.50000 AFIX 0 N1 3 0.253175 0.508445 0.418522 11.00000 0.04483 0.03301 = 0.03274 -0.00577 -0.00775 0.00763 O1 4 0.126017 0.390880 1.079008 11.00000 0.08187 0.06198 = 0.03571 -0.01566 0.00800 -0.00011 O2 4 0.217430 0.504992 0.615290 11.00000 0.05552 0.04143 = 0.04069 -0.00647 -0.00313 0.00835 O3 4 0.639286 0.149256 0.823538 11.00000 0.11902 0.08187 = 0.05022 -0.02146 -0.03889 0.03800 O4 4 0.661434 -0.019266 0.729534 11.00000 0.10871 0.05454 = 0.05258 -0.00081 -0.02423 0.03264 O5 4 0.745224 0.051781 0.296860 11.00000 0.08199 0.05371 = 0.05264 -0.01840 0.00115 0.02044 O6 4 0.607356 0.217947 0.210760 11.00000 0.10073 0.05422 = 0.03292 -0.00532 0.00569 0.01486 HKLF 4 REM jr749_a.res in P-1 REM R1 = 0.0433 for 2255 Fo > 4sig(Fo) and 0.0828 for all 3551 data REM 284 parameters refined using 1 restraints END WGHT 0.0547 0.2758 REM Highest difference peak 0.242, deepest hole -0.195, 1-sigma level 0.039 Q1 1 0.5283 0.0955 0.8419 11.00000 0.05 0.24 Q2 1 0.7649 0.0280 0.7180 11.00000 0.05 0.20 Q3 1 -0.0669 0.8785 0.4212 11.00000 0.05 0.19 Q4 1 0.4715 0.3225 0.5790 11.00000 0.05 0.19 Q5 1 0.3069 0.5216 0.4470 11.00000 0.05 0.18 Q6 1 0.2984 0.4896 0.3620 11.00000 0.05 0.18 Q7 1 -0.0050 0.8951 0.4035 11.00000 0.05 0.17 Q8 1 0.3650 0.3957 0.5229 11.00000 0.05 0.17 Q9 1 0.2350 0.5478 0.4253 11.00000 0.05 0.16 Q10 1 0.4814 0.2029 0.6376 11.00000 0.05 0.16 Q11 1 0.2122 0.4641 0.4515 11.00000 0.05 0.16 Q12 1 0.7428 0.0989 0.1018 11.00000 0.05 0.16 Q13 1 0.7351 0.0461 0.5145 11.00000 0.05 0.15 Q14 1 0.5321 0.1195 0.5923 11.00000 0.05 0.15 Q15 1 0.4056 0.3846 0.3049 11.00000 0.05 0.15 Q16 1 0.6053 0.1623 0.6724 11.00000 0.05 0.15 Q17 1 0.8346 -0.0189 0.8230 11.00000 0.05 0.14 Q18 1 0.5245 0.2224 0.4241 11.00000 0.05 0.14 Q19 1 0.3860 0.2946 0.5727 11.00000 0.05 0.13 Q20 1 0.5824 0.2564 0.4065 11.00000 0.05 0.13 ; _shelx_res_checksum 4533 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -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 0.1298(3) 0.6108(2) 0.56929(19) 0.0399(5) Uani 1 1 d . . . . . C2 C 0.0383(3) 0.7017(2) 0.6278(2) 0.0516(7) Uani 1 1 d . . . . . H2 H 0.0252 0.6985 0.7099 0.062 Uiso 1 1 calc R U . . . C3 C -0.0329(3) 0.7983(2) 0.5573(3) 0.0597(7) Uani 1 1 d . . . . . H3 H -0.0950 0.8630 0.5929 0.072 Uiso 1 1 calc R U . . . C4 C -0.0152(3) 0.8022(2) 0.4357(2) 0.0580(7) Uani 1 1 d . . . . . H4 H -0.0661 0.8690 0.3914 0.070 Uiso 1 1 calc R U . . . C5 C 0.0763(3) 0.7092(2) 0.3783(2) 0.0524(6) Uani 1 1 d . . . . . H5 H 0.0875 0.7114 0.2963 0.063 Uiso 1 1 calc R U . . . C6 C 0.1506(3) 0.6128(2) 0.44780(19) 0.0393(5) Uani 1 1 d . . . . . C7 C 0.2877(3) 0.44977(19) 0.51885(18) 0.0363(5) Uani 1 1 d . U . . . C8 C 0.3994(2) 0.33588(18) 0.52906(17) 0.0330(5) Uani 1 1 d . . . . . C9 C 0.4676(3) 0.29340(19) 0.42210(18) 0.0358(5) Uani 1 1 d . . . . . H9 H 0.4400 0.3375 0.3517 0.043 Uiso 1 1 calc R U . . . C10 C 0.5746(3) 0.18809(19) 0.41787(17) 0.0364(5) Uani 1 1 d . . . . . C11 C 0.6168(3) 0.12336(19) 0.52257(18) 0.0388(5) Uani 1 1 d . . . . . H11 H 0.6882 0.0515 0.5207 0.047 Uiso 1 1 calc R U . . . C12 C 0.5535(3) 0.16486(19) 0.63014(17) 0.0365(5) Uani 1 1 d . . . . . C13 C 0.4412(3) 0.27085(19) 0.63651(17) 0.0330(5) Uani 1 1 d . . . . . C14 C 0.3640(3) 0.30550(19) 0.75395(17) 0.0351(5) Uani 1 1 d . . . . . C15 C 0.2453(3) 0.2347(2) 0.81668(18) 0.0408(6) Uani 1 1 d . . . . . H15 H 0.2167 0.1656 0.7856 0.049 Uiso 1 1 calc R U . . . C16 C 0.1692(3) 0.2655(2) 0.92458(18) 0.0458(6) Uani 1 1 d . . . . . H16 H 0.0893 0.2173 0.9656 0.055 Uiso 1 1 calc R U . . . C17 C 0.2107(3) 0.3671(2) 0.97223(18) 0.0422(6) Uani 1 1 d . . . . . C18 C 0.3310(3) 0.4367(2) 0.91217(19) 0.0470(6) Uani 1 1 d . . . . . H18 H 0.3618 0.5043 0.9444 0.056 Uiso 1 1 calc R U . . . C19 C 0.4061(3) 0.4054(2) 0.80321(19) 0.0437(6) Uani 1 1 d . . . . . H19 H 0.4867 0.4532 0.7626 0.052 Uiso 1 1 calc R U . . . C20 C 0.1649(4) 0.4940(3) 1.1316(2) 0.0784(9) Uani 1 1 d . . . . . H20A H 0.2755 0.4801 1.1510 0.118 Uiso 1 1 calc R U . . . H20B H 0.0915 0.5042 1.2024 0.118 Uiso 1 1 calc R U . . . H20C H 0.1542 0.5679 1.0772 0.118 Uiso 1 1 calc R U . . . C21 C 0.6186(3) 0.1005(2) 0.7398(2) 0.0487(6) Uani 1 1 d . . . . . C22 C 0.7398(5) -0.0866(3) 0.8275(3) 0.1042(13) Uani 1 1 d . . . . . H22A H 0.8436 -0.0551 0.8302 0.156 Uiso 1 1 calc R U . . . H22B H 0.7563 -0.1735 0.8169 0.156 Uiso 1 1 calc R U . . . H22C H 0.6713 -0.0756 0.9003 0.156 Uiso 1 1 calc R U . . . C23 C 0.6521(3) 0.1437(2) 0.30443(19) 0.0457(6) Uani 1 1 d . . . . . C24 C 0.6766(5) 0.1821(3) 0.0960(2) 0.0984(12) Uani 1 1 d . . . . . H24A H 0.7919 0.1917 0.0850 0.148 Uiso 1 1 calc R U . . . H24B H 0.6245 0.2342 0.0353 0.148 Uiso 1 1 calc R U . . . H24C H 0.6593 0.0968 0.0915 0.148 Uiso 1 1 calc R U . . . N1 N 0.2532(2) 0.50845(15) 0.41852(14) 0.0372(4) Uani 1 1 d . U . . . O1 O 0.1260(2) 0.39088(16) 1.07901(13) 0.0607(5) Uani 1 1 d . . . . . O2 O 0.21743(19) 0.50499(14) 0.61529(12) 0.0468(4) Uani 1 1 d . . . . . O3 O 0.6393(3) 0.14926(18) 0.82354(16) 0.0833(7) Uani 1 1 d . . . . . O4 O 0.6614(3) -0.01927(17) 0.72953(15) 0.0738(6) Uani 1 1 d . . . . . O5 O 0.7452(2) 0.05178(16) 0.29686(14) 0.0643(5) Uani 1 1 d . . . . . O6 O 0.6074(2) 0.21795(15) 0.21076(13) 0.0652(5) 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 0.0381(13) 0.0335(12) 0.0471(14) -0.0049(10) -0.0054(10) 0.0033(10) C2 0.0528(16) 0.0471(15) 0.0520(15) -0.0139(12) 0.0031(12) 0.0080(13) C3 0.0497(16) 0.0482(16) 0.081(2) -0.0198(14) -0.0050(14) 0.0110(13) C4 0.0537(16) 0.0464(16) 0.0743(19) -0.0048(13) -0.0230(14) 0.0102(13) C5 0.0593(16) 0.0465(15) 0.0516(14) -0.0057(12) -0.0181(12) 0.0091(13) C6 0.0386(13) 0.0355(13) 0.0440(13) -0.0072(10) -0.0079(10) 0.0032(10) C7 0.0372(12) 0.0337(12) 0.0386(12) -0.0098(10) -0.0031(10) 0.0001(10) C8 0.0343(12) 0.0295(11) 0.0349(12) -0.0050(9) -0.0031(9) -0.0009(9) C9 0.0432(13) 0.0323(12) 0.0311(11) -0.0025(9) -0.0035(9) -0.0011(10) C10 0.0410(13) 0.0323(12) 0.0356(12) -0.0077(9) -0.0005(10) -0.0020(10) C11 0.0422(13) 0.0310(12) 0.0422(13) -0.0066(10) -0.0048(10) 0.0048(10) C12 0.0401(13) 0.0351(12) 0.0334(12) -0.0044(9) -0.0057(9) 0.0034(10) C13 0.0363(12) 0.0307(11) 0.0327(11) -0.0059(9) -0.0045(9) -0.0022(10) C14 0.0386(13) 0.0352(12) 0.0309(11) -0.0050(9) -0.0063(9) 0.0038(10) C15 0.0521(15) 0.0357(13) 0.0353(12) -0.0069(10) -0.0062(11) -0.0020(11) C16 0.0532(15) 0.0459(14) 0.0360(13) -0.0009(11) 0.0002(11) -0.0045(12) C17 0.0524(15) 0.0450(14) 0.0274(12) -0.0064(10) -0.0045(10) 0.0074(12) C18 0.0595(16) 0.0440(14) 0.0395(13) -0.0140(11) -0.0070(12) -0.0018(12) C19 0.0495(15) 0.0439(14) 0.0384(13) -0.0095(10) -0.0009(11) -0.0058(11) C20 0.106(3) 0.082(2) 0.0492(16) -0.0330(15) 0.0059(16) -0.0060(18) C21 0.0537(16) 0.0499(15) 0.0388(14) -0.0055(11) -0.0066(11) 0.0162(12) C22 0.149(3) 0.087(2) 0.064(2) 0.0098(17) -0.037(2) 0.059(2) C23 0.0572(16) 0.0378(14) 0.0405(13) -0.0091(11) -0.0001(11) 0.0028(12) C24 0.157(3) 0.091(2) 0.0349(15) -0.0132(15) 0.0162(18) 0.020(2) N1 0.0448(11) 0.0330(10) 0.0327(10) -0.0058(8) -0.0078(8) 0.0076(8) O1 0.0819(13) 0.0620(11) 0.0357(9) -0.0157(8) 0.0080(8) -0.0001(10) O2 0.0555(10) 0.0414(9) 0.0407(9) -0.0065(7) -0.0031(7) 0.0083(8) O3 0.1190(18) 0.0819(14) 0.0502(11) -0.0215(10) -0.0389(11) 0.0380(12) O4 0.1087(16) 0.0545(12) 0.0526(11) -0.0008(9) -0.0242(10) 0.0326(11) O5 0.0820(13) 0.0537(11) 0.0526(11) -0.0184(9) 0.0011(9) 0.0204(10) O6 0.1007(15) 0.0542(11) 0.0329(9) -0.0053(8) 0.0057(9) 0.0149(10) 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 C2 C1 C6 123.4(2) . . ? C2 C1 O2 128.9(2) . . ? C6 C1 O2 107.66(18) . . ? C1 C2 C3 115.7(2) . . ? C1 C2 H2 122.2 . . ? C3 C2 H2 122.2 . . ? C2 C3 C4 122.1(2) . . ? C2 C3 H3 118.9 . . ? C4 C3 H3 118.9 . . ? C5 C4 C3 121.4(2) . . ? C5 C4 H4 119.3 . . ? C3 C4 H4 119.3 . . ? C4 C5 C6 117.1(2) . . ? C4 C5 H5 121.5 . . ? C6 C5 H5 121.5 . . ? C1 C6 C5 120.2(2) . . ? C1 C6 N1 108.23(18) . . ? C5 C6 N1 131.5(2) . . ? N1 C7 O2 114.54(18) . . ? N1 C7 C8 123.52(18) . . ? O2 C7 C8 121.88(18) . . ? C9 C8 C13 119.82(18) . . ? C9 C8 C7 115.23(18) . . ? C13 C8 C7 124.95(18) . . ? C10 C9 C8 121.74(19) . . ? C10 C9 H9 119.1 . . ? C8 C9 H9 119.1 . . ? C9 C10 C11 119.10(19) . . ? C9 C10 C23 122.36(19) . . ? C11 C10 C23 118.50(19) . . ? C10 C11 C12 120.41(19) . . ? C10 C11 H11 119.8 . . ? C12 C11 H11 119.8 . . ? C11 C12 C13 121.37(18) . . ? C11 C12 C21 118.18(19) . . ? C13 C12 C21 120.24(18) . . ? C12 C13 C8 117.53(18) . . ? C12 C13 C14 119.69(17) . . ? C8 C13 C14 122.66(18) . . ? C19 C14 C15 118.3(2) . . ? C19 C14 C13 122.5(2) . . ? C15 C14 C13 119.16(19) . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 120.4(2) . . ? C15 C16 H16 119.8 . . ? C17 C16 H16 119.8 . . ? O1 C17 C18 124.6(2) . . ? O1 C17 C16 115.9(2) . . ? C18 C17 C16 119.5(2) . . ? C17 C18 C19 119.6(2) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C14 C19 C18 121.4(2) . . ? C14 C19 H19 119.3 . . ? C18 C19 H19 119.3 . . ? O1 C20 H20A 109.5 . . ? O1 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? O1 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? O3 C21 O4 123.0(2) . . ? O3 C21 C12 125.6(2) . . ? O4 C21 C12 111.31(19) . . ? O4 C22 H22A 109.5 . . ? O4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? O4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? O5 C23 O6 123.3(2) . . ? O5 C23 C10 124.4(2) . . ? O6 C23 C10 112.30(19) . . ? O6 C24 H24A 109.5 . . ? O6 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? O6 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C7 N1 C6 105.18(17) . . ? C17 O1 C20 117.9(2) . . ? C7 O2 C1 104.39(16) . . ? C21 O4 C22 115.0(2) . . ? C23 O6 C24 116.4(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 C2 1.368(3) . ? C1 C6 1.379(3) . ? C1 O2 1.381(2) . ? C2 C3 1.375(3) . ? C2 H2 0.9300 . ? C3 C4 1.379(4) . ? C3 H3 0.9300 . ? C4 C5 1.378(3) . ? C4 H4 0.9300 . ? C5 C6 1.380(3) . ? C5 H5 0.9300 . ? C6 N1 1.392(3) . ? C7 N1 1.297(3) . ? C7 O2 1.357(2) . ? C7 C8 1.468(3) . ? C8 C9 1.392(3) . ? C8 C13 1.409(3) . ? C9 C10 1.374(3) . ? C9 H9 0.9300 . ? C10 C11 1.383(3) . ? C10 C23 1.486(3) . ? C11 C12 1.384(3) . ? C11 H11 0.9300 . ? C12 C13 1.406(3) . ? C12 C21 1.497(3) . ? C13 C14 1.488(3) . ? C14 C19 1.373(3) . ? C14 C15 1.384(3) . ? C15 C16 1.377(3) . ? C15 H15 0.9300 . ? C16 C17 1.378(3) . ? C16 H16 0.9300 . ? C17 O1 1.369(2) . ? C17 C18 1.375(3) . ? C18 C19 1.386(3) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? C20 O1 1.414(3) . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? C21 O3 1.187(3) . ? C21 O4 1.327(3) . ? C22 O4 1.451(3) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 O5 1.201(3) . ? C23 O6 1.332(3) . ? C24 O6 1.447(3) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? 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 C6 C1 C2 C3 -0.4(4) . . . . ? O2 C1 C2 C3 178.6(2) . . . . ? C1 C2 C3 C4 0.9(4) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 C6 -0.6(4) . . . . ? C2 C1 C6 C5 -0.6(4) . . . . ? O2 C1 C6 C5 -179.8(2) . . . . ? C2 C1 C6 N1 178.5(2) . . . . ? O2 C1 C6 N1 -0.7(2) . . . . ? C4 C5 C6 C1 1.1(3) . . . . ? C4 C5 C6 N1 -177.9(2) . . . . ? N1 C7 C8 C9 -0.1(3) . . . . ? O2 C7 C8 C9 -177.21(19) . . . . ? N1 C7 C8 C13 179.1(2) . . . . ? O2 C7 C8 C13 2.0(3) . . . . ? C13 C8 C9 C10 0.6(3) . . . . ? C7 C8 C9 C10 179.9(2) . . . . ? C8 C9 C10 C11 -0.6(3) . . . . ? C8 C9 C10 C23 -178.2(2) . . . . ? C9 C10 C11 C12 -0.7(3) . . . . ? C23 C10 C11 C12 176.9(2) . . . . ? C10 C11 C12 C13 2.0(3) . . . . ? C10 C11 C12 C21 -172.7(2) . . . . ? C11 C12 C13 C8 -2.0(3) . . . . ? C21 C12 C13 C8 172.6(2) . . . . ? C11 C12 C13 C14 174.2(2) . . . . ? C21 C12 C13 C14 -11.1(3) . . . . ? C9 C8 C13 C12 0.7(3) . . . . ? C7 C8 C13 C12 -178.5(2) . . . . ? C9 C8 C13 C14 -175.4(2) . . . . ? C7 C8 C13 C14 5.4(3) . . . . ? C12 C13 C14 C19 107.1(2) . . . . ? C8 C13 C14 C19 -76.9(3) . . . . ? C12 C13 C14 C15 -72.8(3) . . . . ? C8 C13 C14 C15 103.2(2) . . . . ? C19 C14 C15 C16 1.3(3) . . . . ? C13 C14 C15 C16 -178.78(19) . . . . ? C14 C15 C16 C17 -0.3(3) . . . . ? C15 C16 C17 O1 179.03(19) . . . . ? C15 C16 C17 C18 -1.2(3) . . . . ? O1 C17 C18 C19 -178.6(2) . . . . ? C16 C17 C18 C19 1.6(3) . . . . ? C15 C14 C19 C18 -0.9(3) . . . . ? C13 C14 C19 C18 179.2(2) . . . . ? C17 C18 C19 C14 -0.6(3) . . . . ? C11 C12 C21 O3 143.8(3) . . . . ? C13 C12 C21 O3 -31.0(4) . . . . ? C11 C12 C21 O4 -32.1(3) . . . . ? C13 C12 C21 O4 153.0(2) . . . . ? C9 C10 C23 O5 -179.5(2) . . . . ? C11 C10 C23 O5 3.0(4) . . . . ? C9 C10 C23 O6 0.9(3) . . . . ? C11 C10 C23 O6 -176.7(2) . . . . ? O2 C7 N1 C6 0.0(2) . . . . ? C8 C7 N1 C6 -177.32(19) . . . . ? C1 C6 N1 C7 0.4(2) . . . . ? C5 C6 N1 C7 179.5(2) . . . . ? C18 C17 O1 C20 -0.1(3) . . . . ? C16 C17 O1 C20 179.7(2) . . . . ? N1 C7 O2 C1 -0.4(2) . . . . ? C8 C7 O2 C1 176.97(19) . . . . ? C2 C1 O2 C7 -178.5(2) . . . . ? C6 C1 O2 C7 0.6(2) . . . . ? O3 C21 O4 C22 -1.4(4) . . . . ? C12 C21 O4 C22 174.6(2) . . . . ? O5 C23 O6 C24 0.4(4) . . . . ? C10 C23 O6 C24 -179.9(2) . . . . ?