#------------------------------------------------------------------------------ #$Date: 2021-11-27 03:19:41 +0200 (Sat, 27 Nov 2021) $ #$Revision: 270895 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/10/7061089.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_7061089 loop_ _publ_author_name 'Wang, Rui' 'Zhang, Wei' 'Tang, Ying' 'Qi, Zehui' 'Yu, Yuanhui' 'Tan, Hongbo' 'Tang, Dianyong' 'Xu, Zhigang' 'Chen, Zhongzhu' _publ_section_title ; A four-component domino reaction for the synthesis of novel bridgehead nitrogen-containing pyrido[1,2-d][1,4]diazepines ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ04233E _journal_year 2021 _chemical_formula_sum 'C34 H32 N2 O6' _chemical_formula_weight 564.61 _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 ; 2021-07-26 deposited with the CCDC. 2021-11-26 downloaded from the CCDC. ; _cell_angle_alpha 95.207(3) _cell_angle_beta 105.767(3) _cell_angle_gamma 94.810(3) _cell_formula_units_Z 2 _cell_length_a 9.5690(17) _cell_length_b 10.7671(18) _cell_length_c 14.771(3) _cell_measurement_reflns_used 1625 _cell_measurement_temperature 273(2) _cell_measurement_theta_max 22.86 _cell_measurement_theta_min 2.29 _cell_volume 1449.2(5) _computing_cell_refinement 'Bruker SMART' _computing_data_collection 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'Bruker SHELXTL' _diffrn_ambient_temperature 273(2) _diffrn_measured_fraction_theta_full 0.991 _diffrn_measured_fraction_theta_max 0.991 _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0226 _diffrn_reflns_av_unetI/netI 0.0577 _diffrn_reflns_Laue_measured_fraction_full 0.991 _diffrn_reflns_Laue_measured_fraction_max 0.991 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 7450 _diffrn_reflns_point_group_measured_fraction_full 0.991 _diffrn_reflns_point_group_measured_fraction_max 0.991 _diffrn_reflns_theta_full 25.000 _diffrn_reflns_theta_max 25.000 _diffrn_reflns_theta_min 2.765 _exptl_absorpt_coefficient_mu 0.089 _exptl_absorpt_correction_type none _exptl_crystal_colour COLORLESS _exptl_crystal_density_diffrn 1.294 _exptl_crystal_description BLOCK _exptl_crystal_F_000 596 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.180 _refine_diff_density_max 0.497 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.041 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.899 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 381 _refine_ls_number_reflns 5062 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.899 _refine_ls_R_factor_all 0.1061 _refine_ls_R_factor_gt 0.0555 _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^)+(0.1037P)^2^+0.0374P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1457 _refine_ls_wR_factor_ref 0.1667 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3005 _reflns_number_total 5062 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj04233e2.cif _cod_data_source_block 1_CCDC1 _cod_original_cell_volume 1449.2(4) _cod_database_code 7061089 _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 0.977 _shelx_estimated_absorpt_t_max 0.984 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1_a.res in P-1 CELL 0.71073 9.569 10.7671 14.7714 95.207 105.767 94.81 ZERR 2 0.0017 0.0018 0.0026 0.003 0.003 0.003 LATT 1 SFAC C H N O UNIT 68 64 4 12 OMIT 0 0 1 OMIT 0 2 1 OMIT 2 1 0 OMIT 0 -1 2 OMIT -1 -1 2 OMIT -1 -1 1 OMIT 0 -3 2 OMIT 1 -3 1 OMIT -2 1 1 OMIT 0 0 4 OMIT 0 0 3 OMIT -1 0 2 OMIT 0 2 2 OMIT 0 -2 1 OMIT 0 -1 4 OMIT -1 3 1 OMIT 0.00 50.00 L.S. 22 ACTA BOND $H FMAP 2 PLAN 20 LIST 4 SIZE 0.26 0.22 0.18 CONF HTAB TEMP 0 WGHT 0.103700 0.037400 FVAR 0.65670 O4 4 0.494104 0.218263 0.275431 11.00000 0.04288 0.08388 = 0.03873 -0.00367 0.01191 0.02184 O2 4 -0.066075 0.843936 0.496654 11.00000 0.04220 0.05970 = 0.04644 -0.00062 0.00316 0.01196 O1 4 0.097867 0.892803 0.639842 11.00000 0.04702 0.05813 = 0.04439 -0.00938 0.00333 0.01708 O3 4 0.286770 0.169874 0.158690 11.00000 0.05492 0.10272 = 0.04380 -0.01663 0.00805 0.02114 O5 4 0.329635 0.452272 0.621914 11.00000 0.07889 0.07589 = 0.04113 -0.00384 0.01857 0.03334 N2 3 0.090460 0.394511 0.334956 11.00000 0.03215 0.04742 = 0.03896 -0.00081 0.00698 0.00930 O6 4 0.577483 0.419913 0.745333 11.00000 0.10156 0.07535 = 0.04436 0.00029 0.00243 0.00171 AFIX 147 H6 2 0.507889 0.458374 0.723568 11.00000 -1.50000 AFIX 0 N1 3 0.005982 0.668012 0.377842 11.00000 0.05527 0.05273 = 0.04140 0.00047 0.00377 0.02302 AFIX 43 H1 2 -0.053684 0.721349 0.384313 11.00000 -1.20000 AFIX 0 C26 1 0.351547 0.299329 0.402630 11.00000 0.03037 0.04371 = 0.03897 0.00588 0.00983 0.00894 AFIX 43 H26 2 0.435693 0.260562 0.424133 11.00000 -1.20000 AFIX 0 C27 1 0.297894 0.361495 0.467138 11.00000 0.03458 0.04438 = 0.03369 0.00356 0.01300 0.00550 C8 1 0.052035 0.831578 0.550636 11.00000 0.03992 0.04199 = 0.04310 0.00273 0.00797 0.00218 C17 1 0.285028 0.290575 0.303332 11.00000 0.03773 0.04959 = 0.02977 0.00126 0.00837 0.00862 C12 1 0.178185 0.442445 0.432844 11.00000 0.03074 0.04947 = 0.03443 0.00079 0.01109 0.00743 AFIX 13 H12 2 0.113345 0.437441 0.473897 11.00000 -1.20000 AFIX 0 C10 1 0.129995 0.672884 0.449451 11.00000 0.03567 0.04329 = 0.04319 0.00804 0.01242 0.00420 C6 1 0.082493 1.051294 0.757719 11.00000 0.04655 0.04732 = 0.03768 0.00074 0.00981 0.01243 C29 1 0.444485 0.268207 0.613075 11.00000 0.03716 0.05948 = 0.02950 0.00787 0.01439 0.01043 C15 1 0.149302 0.335751 0.272248 11.00000 0.04029 0.04969 = 0.03775 0.00026 0.00771 0.00660 C18 1 0.349417 0.222570 0.237379 11.00000 0.04345 0.06528 = 0.03407 0.00213 0.00802 0.01419 C28 1 0.355104 0.364906 0.569150 11.00000 0.04093 0.05298 = 0.03751 0.00172 0.01577 0.01163 C9 1 0.155873 0.751494 0.531087 11.00000 0.03308 0.05240 = 0.04341 -0.00189 0.00417 0.00671 AFIX 43 H9 2 0.245228 0.753578 0.576575 11.00000 -1.20000 AFIX 0 C11 1 0.236588 0.581949 0.438006 11.00000 0.03774 0.04755 = 0.04258 0.00170 0.01198 0.00352 AFIX 23 H11A 2 0.324172 0.601154 0.490871 11.00000 -1.20000 H11B 2 0.264064 0.594223 0.380615 11.00000 -1.20000 AFIX 0 C7 1 -0.000434 0.973607 0.667066 11.00000 0.04267 0.05615 = 0.04832 0.00001 0.01106 0.01450 AFIX 23 H7A 2 -0.084061 0.923809 0.675773 11.00000 -1.20000 H7B 2 -0.035270 1.027212 0.618273 11.00000 -1.20000 AFIX 0 C30 1 0.553596 0.302699 0.699301 11.00000 0.05899 0.06421 = 0.03488 0.01029 0.01673 0.00240 C13 1 -0.049963 0.445028 0.307075 11.00000 0.03461 0.05953 = 0.04686 -0.00163 0.00259 0.01197 AFIX 23 H13A 2 -0.098953 0.435516 0.355956 11.00000 -1.20000 H13B 2 -0.110540 0.396282 0.249182 11.00000 -1.20000 AFIX 0 C34 1 0.421213 0.143163 0.574401 11.00000 0.05405 0.06139 = 0.03968 0.00623 0.01653 0.01171 AFIX 43 H34 2 0.345731 0.117690 0.519372 11.00000 -1.20000 AFIX 0 C5 1 0.211286 1.125624 0.763732 11.00000 0.05454 0.05489 = 0.05060 0.00537 0.01895 0.00846 AFIX 43 H5 2 0.245252 1.126748 0.710466 11.00000 -1.20000 AFIX 0 C19 1 0.566750 0.147263 0.216327 11.00000 0.05296 0.08085 = 0.04507 0.00319 0.01926 0.03056 AFIX 23 H19A 2 0.504193 0.070646 0.186495 11.00000 -1.20000 H19B 2 0.656392 0.123610 0.256560 11.00000 -1.20000 AFIX 0 C14 1 -0.036457 0.581898 0.291269 11.00000 0.05647 0.05930 = 0.03805 0.00613 0.00534 0.01839 AFIX 23 H14A 2 0.035259 0.595623 0.256688 11.00000 -1.20000 H14B 2 -0.129562 0.600747 0.252127 11.00000 -1.20000 AFIX 0 C20 1 0.602398 0.216156 0.141733 11.00000 0.04346 0.07298 = 0.04826 -0.00061 0.00752 0.01572 C1 1 0.033491 1.052007 0.837963 11.00000 0.05607 0.08626 = 0.05616 0.00410 0.02221 0.00798 AFIX 43 H1A 2 -0.052437 1.003204 0.836005 11.00000 -1.20000 AFIX 0 C31 1 0.645029 0.215995 0.738258 11.00000 0.05564 0.10167 = 0.04416 0.02881 0.00630 0.01389 AFIX 43 H31 2 0.722001 0.240261 0.792685 11.00000 -1.20000 AFIX 0 C4 1 0.289217 1.197051 0.845885 11.00000 0.05430 0.06531 = 0.06561 0.00212 0.00739 0.00030 AFIX 43 H4 2 0.375529 1.245460 0.848102 11.00000 -1.20000 AFIX 0 C16 1 0.061657 0.320355 0.169198 11.00000 0.06550 0.09475 = 0.04156 -0.00940 -0.00329 0.03611 AFIX 137 H16A 2 -0.019834 0.257224 0.159030 11.00000 -1.50000 H16B 2 0.122559 0.295448 0.130313 11.00000 -1.50000 H16C 2 0.026586 0.398616 0.152805 11.00000 -1.50000 AFIX 0 C33 1 0.507250 0.056583 0.615709 11.00000 0.08718 0.06028 = 0.05518 0.01437 0.02269 0.02815 AFIX 43 H33 2 0.488780 -0.027121 0.589663 11.00000 -1.20000 AFIX 0 C32 1 0.621075 0.094211 0.695913 11.00000 0.08003 0.08440 = 0.06983 0.03552 0.02635 0.03749 AFIX 43 H32 2 0.682709 0.036347 0.721845 11.00000 -1.20000 AFIX 0 C3 1 0.240500 1.197742 0.925637 11.00000 0.08121 0.08345 = 0.05382 -0.01167 0.00264 0.00866 AFIX 43 H3 2 0.293532 1.246442 0.981619 11.00000 -1.20000 AFIX 0 C2 1 0.113064 1.125907 0.921604 11.00000 0.09157 0.11057 = 0.04325 -0.00389 0.02770 0.01449 AFIX 43 H2 2 0.079422 1.126465 0.975065 11.00000 -1.20000 AFIX 0 C25 1 0.648452 0.150349 0.071907 11.00000 0.08209 0.09703 = 0.05624 0.00762 0.02589 0.03018 AFIX 43 H25 2 0.652046 0.064306 0.071950 11.00000 -1.20000 AFIX 0 C21 1 0.597951 0.343839 0.139444 11.00000 0.07161 0.08304 = 0.07166 -0.00284 0.01371 0.01538 AFIX 43 H21 2 0.566913 0.389988 0.185204 11.00000 -1.20000 AFIX 0 C22 1 0.639969 0.405882 0.068402 11.00000 0.09042 0.08828 = 0.07149 0.02064 0.00348 0.00538 AFIX 43 H22 2 0.639279 0.492180 0.068217 11.00000 -1.20000 AFIX 0 C23 1 0.680219 0.337643 0.002323 11.00000 0.08246 0.14301 = 0.07435 0.04058 0.01943 -0.00163 AFIX 43 H23 2 0.703442 0.377198 -0.045964 11.00000 -1.20000 AFIX 0 C24 1 0.689038 0.209568 0.002412 11.00000 0.10532 0.13534 = 0.06227 0.01836 0.03844 0.02511 AFIX 43 H24 2 0.721523 0.164758 -0.043275 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1_a.res in P-1 REM R1 = 0.0555 for 3005 Fo > 4sig(Fo) and 0.1061 for all 5062 data REM 381 parameters refined using 0 restraints END WGHT 0.0837 0.0000 REM Instructions for potential hydrogen bonds HTAB O6 O5 HTAB N1 O2 HTAB C11 O5 EQIV $1 -x, -y+2, -z+1 HTAB C7 O2_$1 EQIV $2 -x+1, -y+1, -z+1 HTAB C19 O1_$2 HTAB C16 O3 REM Highest difference peak 0.497, deepest hole -0.171, 1-sigma level 0.041 Q1 1 0.9159 0.4219 -0.0473 11.00000 0.05 0.50 Q2 1 0.3573 0.2651 0.1570 11.00000 0.05 0.29 Q3 1 0.7172 0.4538 0.0438 11.00000 0.05 0.22 Q4 1 0.8049 0.4994 -0.0232 11.00000 0.05 0.21 Q5 1 0.3030 0.0909 0.5232 11.00000 0.05 0.20 Q6 1 0.5976 0.1065 0.6307 11.00000 0.05 0.16 Q7 1 -0.0337 0.3610 0.1433 11.00000 0.05 0.15 Q8 1 0.0753 0.6755 0.4175 11.00000 0.05 0.15 Q9 1 0.5184 0.2889 0.6384 11.00000 0.05 0.14 Q10 1 0.2215 0.7316 0.5822 11.00000 0.05 0.13 Q11 1 0.4275 0.3226 0.5967 11.00000 0.05 0.13 Q12 1 0.7008 0.1505 0.6929 11.00000 0.05 0.13 Q13 1 0.1570 0.4236 0.3787 11.00000 0.05 0.13 Q14 1 0.2522 0.3414 0.2798 11.00000 0.05 0.13 Q15 1 0.5917 0.2547 -0.0589 11.00000 0.05 0.13 Q16 1 0.6984 0.3393 -0.0169 11.00000 0.05 0.12 Q17 1 0.5320 0.1730 0.0416 11.00000 0.05 0.12 Q18 1 0.3217 0.3616 0.5158 11.00000 0.05 0.12 Q19 1 0.5021 0.1389 0.5783 11.00000 0.05 0.12 Q20 1 0.3483 0.0956 0.1059 11.00000 0.05 0.12 ; _shelx_res_checksum 24024 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 O4 O 0.49410(19) 0.21826(18) 0.27543(12) 0.0549(5) Uani 1 1 d . . . . . O2 O -0.06608(19) 0.84394(17) 0.49665(13) 0.0514(5) Uani 1 1 d . . . . . O1 O 0.09787(18) 0.89280(17) 0.63984(12) 0.0521(5) Uani 1 1 d . . . . . O3 O 0.2868(2) 0.1699(2) 0.15869(14) 0.0692(6) Uani 1 1 d . . . . . O5 O 0.3296(2) 0.45227(19) 0.62191(13) 0.0642(6) Uani 1 1 d . . . . . N2 N 0.0905(2) 0.39451(19) 0.33496(14) 0.0402(5) Uani 1 1 d . . . . . O6 O 0.5775(3) 0.4199(2) 0.74533(15) 0.0783(7) Uani 1 1 d . . . . . H6 H 0.5079 0.4584 0.7236 0.117 Uiso 1 1 calc R U . . . N1 N 0.0060(2) 0.6680(2) 0.37784(15) 0.0511(6) Uani 1 1 d . . . . . H1 H -0.0537 0.7213 0.3843 0.061 Uiso 1 1 calc R U . . . C26 C 0.3515(2) 0.2993(2) 0.40263(17) 0.0373(6) Uani 1 1 d . . . . . H26 H 0.4357 0.2606 0.4241 0.045 Uiso 1 1 calc R U . . . C27 C 0.2979(2) 0.3615(2) 0.46714(16) 0.0369(6) Uani 1 1 d . . . . . C8 C 0.0520(3) 0.8316(2) 0.55064(18) 0.0427(6) Uani 1 1 d . . . . . C17 C 0.2850(3) 0.2906(2) 0.30333(16) 0.0393(6) Uani 1 1 d . . . . . C12 C 0.1782(2) 0.4424(2) 0.43284(17) 0.0379(6) Uani 1 1 d . . . . . H12 H 0.1133 0.4374 0.4739 0.046 Uiso 1 1 calc R U . . . C10 C 0.1300(3) 0.6729(2) 0.44945(18) 0.0403(6) Uani 1 1 d . . . . . C6 C 0.0825(3) 1.0513(2) 0.75772(18) 0.0441(6) Uani 1 1 d . . . . . C29 C 0.4445(3) 0.2682(3) 0.61307(17) 0.0406(6) Uani 1 1 d . . . . . C15 C 0.1493(3) 0.3358(2) 0.27225(18) 0.0435(6) Uani 1 1 d . . . . . C18 C 0.3494(3) 0.2226(3) 0.23738(18) 0.0479(7) Uani 1 1 d . . . . . C28 C 0.3551(3) 0.3649(3) 0.56915(18) 0.0427(6) Uani 1 1 d . . . . . C9 C 0.1559(3) 0.7515(2) 0.53109(18) 0.0446(7) Uani 1 1 d . . . . . H9 H 0.2452 0.7536 0.5766 0.054 Uiso 1 1 calc R U . . . C11 C 0.2366(3) 0.5819(2) 0.43801(19) 0.0428(6) Uani 1 1 d . . . . . H11A H 0.3242 0.6012 0.4909 0.051 Uiso 1 1 calc R U . . . H11B H 0.2641 0.5942 0.3806 0.051 Uiso 1 1 calc R U . . . C7 C -0.0004(3) 0.9736(3) 0.66707(19) 0.0493(7) Uani 1 1 d . . . . . H7A H -0.0841 0.9238 0.6758 0.059 Uiso 1 1 calc R U . . . H7B H -0.0353 1.0272 0.6183 0.059 Uiso 1 1 calc R U . . . C30 C 0.5536(3) 0.3027(3) 0.69930(19) 0.0520(7) Uani 1 1 d . . . . . C13 C -0.0500(3) 0.4450(3) 0.30708(19) 0.0489(7) Uani 1 1 d . . . . . H13A H -0.0990 0.4355 0.3560 0.059 Uiso 1 1 calc R U . . . H13B H -0.1105 0.3963 0.2492 0.059 Uiso 1 1 calc R U . . . C34 C 0.4212(3) 0.1432(3) 0.57440(19) 0.0507(7) Uani 1 1 d . . . . . H34 H 0.3457 0.1177 0.5194 0.061 Uiso 1 1 calc R U . . . C5 C 0.2113(3) 1.1256(3) 0.7637(2) 0.0524(7) Uani 1 1 d . . . . . H5 H 0.2453 1.1267 0.7105 0.063 Uiso 1 1 calc R U . . . C19 C 0.5668(3) 0.1473(3) 0.2163(2) 0.0575(8) Uani 1 1 d . . . . . H19A H 0.5042 0.0706 0.1865 0.069 Uiso 1 1 calc R U . . . H19B H 0.6564 0.1236 0.2566 0.069 Uiso 1 1 calc R U . . . C14 C -0.0365(3) 0.5819(3) 0.29127(18) 0.0521(7) Uani 1 1 d . . . . . H14A H 0.0353 0.5956 0.2567 0.063 Uiso 1 1 calc R U . . . H14B H -0.1296 0.6007 0.2521 0.063 Uiso 1 1 calc R U . . . C20 C 0.6024(3) 0.2162(3) 0.1417(2) 0.0559(8) Uani 1 1 d . . . . . C1 C 0.0335(3) 1.0520(3) 0.8380(2) 0.0652(9) Uani 1 1 d . . . . . H1A H -0.0524 1.0032 0.8360 0.078 Uiso 1 1 calc R U . . . C31 C 0.6450(3) 0.2160(4) 0.7383(2) 0.0671(9) Uani 1 1 d . . . . . H31 H 0.7220 0.2403 0.7927 0.081 Uiso 1 1 calc R U . . . C4 C 0.2892(3) 1.1971(3) 0.8459(2) 0.0644(9) Uani 1 1 d . . . . . H4 H 0.3755 1.2455 0.8481 0.077 Uiso 1 1 calc R U . . . C16 C 0.0617(3) 0.3204(3) 0.16920(19) 0.0704(10) Uani 1 1 d . . . . . H16A H -0.0198 0.2572 0.1590 0.106 Uiso 1 1 calc R U . . . H16B H 0.1226 0.2954 0.1303 0.106 Uiso 1 1 calc R U . . . H16C H 0.0266 0.3986 0.1528 0.106 Uiso 1 1 calc R U . . . C33 C 0.5073(4) 0.0566(3) 0.6157(2) 0.0654(9) Uani 1 1 d . . . . . H33 H 0.4888 -0.0271 0.5897 0.078 Uiso 1 1 calc R U . . . C32 C 0.6211(4) 0.0942(4) 0.6959(3) 0.0737(10) Uani 1 1 d . . . . . H32 H 0.6827 0.0363 0.7218 0.088 Uiso 1 1 calc R U . . . C3 C 0.2405(4) 1.1977(3) 0.9256(2) 0.0774(10) Uani 1 1 d . . . . . H3 H 0.2935 1.2464 0.9816 0.093 Uiso 1 1 calc R U . . . C2 C 0.1131(4) 1.1259(4) 0.9216(2) 0.0807(11) Uani 1 1 d . . . . . H2 H 0.0794 1.1265 0.9751 0.097 Uiso 1 1 calc R U . . . C25 C 0.6485(4) 0.1503(4) 0.0719(2) 0.0761(10) Uani 1 1 d . . . . . H25 H 0.6520 0.0643 0.0720 0.091 Uiso 1 1 calc R U . . . C21 C 0.5980(4) 0.3438(4) 0.1394(3) 0.0771(10) Uani 1 1 d . . . . . H21 H 0.5669 0.3900 0.1852 0.093 Uiso 1 1 calc R U . . . C22 C 0.6400(4) 0.4059(4) 0.0684(3) 0.0868(11) Uani 1 1 d . . . . . H22 H 0.6393 0.4922 0.0682 0.104 Uiso 1 1 calc R U . . . C23 C 0.6802(4) 0.3376(6) 0.0023(3) 0.0995(14) Uani 1 1 d . . . . . H23 H 0.7034 0.3772 -0.0460 0.119 Uiso 1 1 calc R U . . . C24 C 0.6890(5) 0.2096(5) 0.0024(3) 0.0969(13) Uani 1 1 d . . . . . H24 H 0.7215 0.1648 -0.0433 0.116 Uiso 1 1 calc R U . . . 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 O4 0.0429(11) 0.0839(15) 0.0387(10) -0.0037(10) 0.0119(8) 0.0218(10) O2 0.0422(11) 0.0597(12) 0.0464(11) -0.0006(9) 0.0032(9) 0.0120(9) O1 0.0470(11) 0.0581(12) 0.0444(11) -0.0094(9) 0.0033(9) 0.0171(9) O3 0.0549(12) 0.1027(17) 0.0438(12) -0.0166(12) 0.0080(10) 0.0211(11) O5 0.0789(14) 0.0759(14) 0.0411(11) -0.0038(10) 0.0186(10) 0.0333(11) N2 0.0321(11) 0.0474(13) 0.0390(12) -0.0008(10) 0.0070(9) 0.0093(9) O6 0.1016(19) 0.0753(16) 0.0444(13) 0.0003(12) 0.0024(12) 0.0017(13) N1 0.0553(14) 0.0527(14) 0.0414(13) 0.0005(11) 0.0038(11) 0.0230(11) C26 0.0304(12) 0.0437(15) 0.0390(14) 0.0059(12) 0.0098(11) 0.0089(11) C27 0.0346(13) 0.0444(15) 0.0337(13) 0.0036(12) 0.0130(11) 0.0055(11) C8 0.0399(15) 0.0420(16) 0.0431(15) 0.0027(13) 0.0080(12) 0.0022(12) C17 0.0377(14) 0.0496(16) 0.0298(13) 0.0013(12) 0.0084(11) 0.0086(11) C12 0.0307(12) 0.0495(16) 0.0344(13) 0.0008(12) 0.0111(10) 0.0074(11) C10 0.0357(13) 0.0433(15) 0.0432(15) 0.0080(13) 0.0124(12) 0.0042(11) C6 0.0466(15) 0.0473(16) 0.0377(14) 0.0007(12) 0.0098(12) 0.0124(12) C29 0.0372(14) 0.0595(18) 0.0295(13) 0.0079(13) 0.0144(11) 0.0104(12) C15 0.0403(14) 0.0497(16) 0.0377(14) 0.0003(13) 0.0077(12) 0.0066(12) C18 0.0435(15) 0.0653(19) 0.0341(15) 0.0021(14) 0.0080(12) 0.0142(13) C28 0.0409(14) 0.0530(17) 0.0375(14) 0.0017(13) 0.0158(12) 0.0116(12) C9 0.0331(13) 0.0524(17) 0.0434(15) -0.0019(14) 0.0042(12) 0.0067(12) C11 0.0377(14) 0.0475(16) 0.0426(15) 0.0017(13) 0.0120(11) 0.0035(12) C7 0.0427(15) 0.0562(18) 0.0483(16) 0.0000(14) 0.0111(13) 0.0145(13) C30 0.0590(18) 0.064(2) 0.0349(15) 0.0103(15) 0.0167(13) 0.0024(15) C13 0.0346(14) 0.0595(19) 0.0469(16) -0.0016(14) 0.0026(12) 0.0120(12) C34 0.0541(17) 0.0614(19) 0.0397(15) 0.0062(15) 0.0165(13) 0.0117(14) C5 0.0545(17) 0.0549(18) 0.0506(17) 0.0054(15) 0.0190(14) 0.0085(14) C19 0.0530(17) 0.081(2) 0.0451(16) 0.0032(16) 0.0193(14) 0.0306(15) C14 0.0565(17) 0.0593(19) 0.0380(15) 0.0061(14) 0.0053(13) 0.0184(14) C20 0.0435(16) 0.073(2) 0.0483(17) -0.0006(16) 0.0075(13) 0.0157(14) C1 0.0561(18) 0.086(2) 0.0562(19) 0.0041(18) 0.0222(15) 0.0080(16) C31 0.0556(19) 0.102(3) 0.0442(18) 0.0288(19) 0.0063(15) 0.0139(18) C4 0.0543(18) 0.065(2) 0.066(2) 0.0021(18) 0.0074(16) 0.0003(15) C16 0.065(2) 0.095(2) 0.0416(17) -0.0094(17) -0.0033(15) 0.0361(18) C33 0.087(2) 0.060(2) 0.0552(19) 0.0144(16) 0.0227(18) 0.0282(18) C32 0.080(2) 0.084(3) 0.070(2) 0.036(2) 0.026(2) 0.037(2) C3 0.081(3) 0.083(3) 0.054(2) -0.0117(19) 0.0026(19) 0.009(2) C2 0.092(3) 0.111(3) 0.0432(19) -0.004(2) 0.0277(18) 0.014(2) C25 0.082(2) 0.097(3) 0.056(2) 0.008(2) 0.0259(18) 0.030(2) C21 0.072(2) 0.083(3) 0.072(2) -0.003(2) 0.0137(19) 0.0154(19) C22 0.090(3) 0.088(3) 0.071(3) 0.021(2) 0.003(2) 0.005(2) C23 0.082(3) 0.143(5) 0.074(3) 0.041(3) 0.019(2) -0.002(3) C24 0.105(3) 0.135(4) 0.062(2) 0.018(3) 0.038(2) 0.025(3) 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 C18 O4 C19 115.7(2) . . ? C8 O1 C7 116.42(19) . . ? C15 N2 C13 122.9(2) . . ? C15 N2 C12 122.00(19) . . ? C13 N2 C12 113.22(19) . . ? C30 O6 H6 109.5 . . ? C10 N1 C14 126.5(2) . . ? C10 N1 H1 116.7 . . ? C14 N1 H1 116.7 . . ? C27 C26 C17 122.9(2) . . ? C27 C26 H26 118.5 . . ? C17 C26 H26 118.5 . . ? C26 C27 C28 124.9(2) . . ? C26 C27 C12 118.6(2) . . ? C28 C27 C12 116.3(2) . . ? O2 C8 O1 121.7(2) . . ? O2 C8 C9 126.1(2) . . ? O1 C8 C9 112.2(2) . . ? C15 C17 C26 118.0(2) . . ? C15 C17 C18 121.5(2) . . ? C26 C17 C18 120.1(2) . . ? N2 C12 C27 110.53(19) . . ? N2 C12 C11 110.1(2) . . ? C27 C12 C11 112.72(19) . . ? N2 C12 H12 107.8 . . ? C27 C12 H12 107.8 . . ? C11 C12 H12 107.8 . . ? N1 C10 C9 122.3(2) . . ? N1 C10 C11 117.2(2) . . ? C9 C10 C11 120.4(2) . . ? C1 C6 C5 118.1(3) . . ? C1 C6 C7 121.3(3) . . ? C5 C6 C7 120.6(2) . . ? C34 C29 C30 118.1(2) . . ? C34 C29 C28 122.7(2) . . ? C30 C29 C28 119.1(2) . . ? N2 C15 C17 120.2(2) . . ? N2 C15 C16 117.1(2) . . ? C17 C15 C16 122.7(2) . . ? O3 C18 O4 120.8(2) . . ? O3 C18 C17 127.4(2) . . ? O4 C18 C17 111.8(2) . . ? O5 C28 C27 119.2(2) . . ? O5 C28 C29 118.7(2) . . ? C27 C28 C29 122.1(2) . . ? C10 C9 C8 123.3(2) . . ? C10 C9 H9 118.3 . . ? C8 C9 H9 118.3 . . ? C10 C11 C12 114.5(2) . . ? C10 C11 H11A 108.6 . . ? C12 C11 H11A 108.6 . . ? C10 C11 H11B 108.6 . . ? C12 C11 H11B 108.6 . . ? H11A C11 H11B 107.6 . . ? O1 C7 C6 107.5(2) . . ? O1 C7 H7A 110.2 . . ? C6 C7 H7A 110.2 . . ? O1 C7 H7B 110.2 . . ? C6 C7 H7B 110.2 . . ? H7A C7 H7B 108.5 . . ? O6 C30 C31 117.6(3) . . ? O6 C30 C29 122.4(3) . . ? C31 C30 C29 120.0(3) . . ? N2 C13 C14 113.5(2) . . ? N2 C13 H13A 108.9 . . ? C14 C13 H13A 108.9 . . ? N2 C13 H13B 108.9 . . ? C14 C13 H13B 108.9 . . ? H13A C13 H13B 107.7 . . ? C33 C34 C29 121.3(3) . . ? C33 C34 H34 119.3 . . ? C29 C34 H34 119.3 . . ? C4 C5 C6 121.6(3) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? O4 C19 C20 114.1(2) . . ? O4 C19 H19A 108.7 . . ? C20 C19 H19A 108.7 . . ? O4 C19 H19B 108.7 . . ? C20 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? N1 C14 C13 113.9(2) . . ? N1 C14 H14A 108.8 . . ? C13 C14 H14A 108.8 . . ? N1 C14 H14B 108.8 . . ? C13 C14 H14B 108.8 . . ? H14A C14 H14B 107.7 . . ? C21 C20 C25 117.7(3) . . ? C21 C20 C19 123.7(3) . . ? C25 C20 C19 118.5(3) . . ? C6 C1 C2 120.1(3) . . ? C6 C1 H1A 120.0 . . ? C2 C1 H1A 120.0 . . ? C32 C31 C30 119.6(3) . . ? C32 C31 H31 120.2 . . ? C30 C31 H31 120.2 . . ? C5 C4 C3 120.3(3) . . ? C5 C4 H4 119.9 . . ? C3 C4 H4 119.9 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C34 C33 C32 119.6(3) . . ? C34 C33 H33 120.2 . . ? C32 C33 H33 120.2 . . ? C31 C32 C33 121.0(3) . . ? C31 C32 H32 119.5 . . ? C33 C32 H32 119.5 . . ? C2 C3 C4 119.4(3) . . ? C2 C3 H3 120.3 . . ? C4 C3 H3 120.3 . . ? C3 C2 C1 120.6(3) . . ? C3 C2 H2 119.7 . . ? C1 C2 H2 119.7 . . ? C24 C25 C20 121.6(4) . . ? C24 C25 H25 119.2 . . ? C20 C25 H25 119.2 . . ? C20 C21 C22 121.2(4) . . ? C20 C21 H21 119.4 . . ? C22 C21 H21 119.4 . . ? C23 C22 C21 118.4(4) . . ? C23 C22 H22 120.8 . . ? C21 C22 H22 120.8 . . ? C22 C23 C24 122.6(4) . . ? C22 C23 H23 118.7 . . ? C24 C23 H23 118.7 . . ? C25 C24 C23 118.4(4) . . ? C25 C24 H24 120.8 . . ? C23 C24 H24 120.8 . . ? 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 O4 C18 1.352(3) . ? O4 C19 1.459(3) . ? O2 C8 1.219(3) . ? O1 C8 1.358(3) . ? O1 C7 1.443(3) . ? O3 C18 1.215(3) . ? O5 C28 1.249(3) . ? N2 C15 1.346(3) . ? N2 C13 1.461(3) . ? N2 C12 1.481(3) . ? O6 C30 1.349(3) . ? O6 H6 0.8200 . ? N1 C10 1.352(3) . ? N1 C14 1.449(3) . ? N1 H1 0.8600 . ? C26 C27 1.352(3) . ? C26 C17 1.422(3) . ? C26 H26 0.9300 . ? C27 C28 1.453(3) . ? C27 C12 1.504(3) . ? C8 C9 1.438(4) . ? C17 C15 1.399(3) . ? C17 C18 1.462(3) . ? C12 C11 1.546(4) . ? C12 H12 0.9800 . ? C10 C9 1.360(3) . ? C10 C11 1.503(3) . ? C6 C1 1.388(4) . ? C6 C5 1.389(4) . ? C6 C7 1.493(3) . ? C29 C34 1.389(4) . ? C29 C30 1.406(4) . ? C29 C28 1.486(4) . ? C15 C16 1.512(3) . ? C9 H9 0.9300 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C30 C31 1.389(4) . ? C13 C14 1.513(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C34 C33 1.370(4) . ? C34 H34 0.9300 . ? C5 C4 1.365(4) . ? C5 H5 0.9300 . ? C19 C20 1.480(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C20 C21 1.382(5) . ? C20 C25 1.388(4) . ? C1 C2 1.396(4) . ? C1 H1A 0.9300 . ? C31 C32 1.373(4) . ? C31 H31 0.9300 . ? C4 C3 1.379(5) . ? C4 H4 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C33 C32 1.375(5) . ? C33 H33 0.9300 . ? C32 H32 0.9300 . ? C3 C2 1.372(5) . ? C3 H3 0.9300 . ? C2 H2 0.9300 . ? C25 C24 1.380(5) . ? C25 H25 0.9300 . ? C21 C22 1.421(5) . ? C21 H21 0.9300 . ? C22 C23 1.328(6) . ? C22 H22 0.9300 . ? C23 C24 1.389(6) . ? C23 H23 0.9300 . ? C24 H24 0.9300 . ? 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 C17 C26 C27 C28 175.0(2) . . . . ? C17 C26 C27 C12 -10.4(4) . . . . ? C7 O1 C8 O2 -0.3(4) . . . . ? C7 O1 C8 C9 -178.7(2) . . . . ? C27 C26 C17 C15 -7.7(4) . . . . ? C27 C26 C17 C18 179.6(3) . . . . ? C15 N2 C12 C27 -31.4(3) . . . . ? C13 N2 C12 C27 163.6(2) . . . . ? C15 N2 C12 C11 93.8(3) . . . . ? C13 N2 C12 C11 -71.2(3) . . . . ? C26 C27 C12 N2 27.9(3) . . . . ? C28 C27 C12 N2 -157.0(2) . . . . ? C26 C27 C12 C11 -95.8(3) . . . . ? C28 C27 C12 C11 79.3(3) . . . . ? C14 N1 C10 C9 -175.4(3) . . . . ? C14 N1 C10 C11 1.3(4) . . . . ? C13 N2 C15 C17 179.3(2) . . . . ? C12 N2 C15 C17 15.8(4) . . . . ? C13 N2 C15 C16 -1.4(4) . . . . ? C12 N2 C15 C16 -164.9(2) . . . . ? C26 C17 C15 N2 5.2(4) . . . . ? C18 C17 C15 N2 177.9(3) . . . . ? C26 C17 C15 C16 -174.0(3) . . . . ? C18 C17 C15 C16 -1.4(4) . . . . ? C19 O4 C18 O3 -0.1(4) . . . . ? C19 O4 C18 C17 177.3(2) . . . . ? C15 C17 C18 O3 -20.1(5) . . . . ? C26 C17 C18 O3 152.4(3) . . . . ? C15 C17 C18 O4 162.7(2) . . . . ? C26 C17 C18 O4 -24.8(4) . . . . ? C26 C27 C28 O5 158.3(3) . . . . ? C12 C27 C28 O5 -16.4(4) . . . . ? C26 C27 C28 C29 -21.1(4) . . . . ? C12 C27 C28 C29 164.2(2) . . . . ? C34 C29 C28 O5 146.2(3) . . . . ? C30 C29 C28 O5 -31.2(4) . . . . ? C34 C29 C28 C27 -34.4(4) . . . . ? C30 C29 C28 C27 148.2(3) . . . . ? N1 C10 C9 C8 3.1(4) . . . . ? C11 C10 C9 C8 -173.5(2) . . . . ? O2 C8 C9 C10 -3.8(5) . . . . ? O1 C8 C9 C10 174.6(2) . . . . ? N1 C10 C11 C12 -64.2(3) . . . . ? C9 C10 C11 C12 112.5(3) . . . . ? N2 C12 C11 C10 83.3(3) . . . . ? C27 C12 C11 C10 -152.8(2) . . . . ? C8 O1 C7 C6 -168.1(2) . . . . ? C1 C6 C7 O1 -123.8(3) . . . . ? C5 C6 C7 O1 56.5(3) . . . . ? C34 C29 C30 O6 -175.5(3) . . . . ? C28 C29 C30 O6 2.0(4) . . . . ? C34 C29 C30 C31 6.9(4) . . . . ? C28 C29 C30 C31 -175.6(3) . . . . ? C15 N2 C13 C14 -93.2(3) . . . . ? C12 N2 C13 C14 71.7(3) . . . . ? C30 C29 C34 C33 -3.7(4) . . . . ? C28 C29 C34 C33 178.8(3) . . . . ? C1 C6 C5 C4 0.5(4) . . . . ? C7 C6 C5 C4 -179.8(3) . . . . ? C18 O4 C19 C20 79.4(3) . . . . ? C10 N1 C14 C13 59.6(4) . . . . ? N2 C13 C14 N1 -79.0(3) . . . . ? O4 C19 C20 C21 13.5(4) . . . . ? O4 C19 C20 C25 -169.1(3) . . . . ? C5 C6 C1 C2 0.0(4) . . . . ? C7 C6 C1 C2 -179.8(3) . . . . ? O6 C30 C31 C32 177.4(3) . . . . ? C29 C30 C31 C32 -4.9(4) . . . . ? C6 C5 C4 C3 -0.5(5) . . . . ? C29 C34 C33 C32 -1.4(5) . . . . ? C30 C31 C32 C33 -0.4(5) . . . . ? C34 C33 C32 C31 3.6(5) . . . . ? C5 C4 C3 C2 0.0(5) . . . . ? C4 C3 C2 C1 0.4(6) . . . . ? C6 C1 C2 C3 -0.4(5) . . . . ? C21 C20 C25 C24 0.2(5) . . . . ? C19 C20 C25 C24 -177.4(3) . . . . ? C25 C20 C21 C22 -0.4(5) . . . . ? C19 C20 C21 C22 177.0(3) . . . . ? C20 C21 C22 C23 1.8(5) . . . . ? C21 C22 C23 C24 -2.9(6) . . . . ? C20 C25 C24 C23 -1.3(6) . . . . ? C22 C23 C24 C25 2.7(6) . . . . ?