#------------------------------------------------------------------------------ #$Date: 2023-12-07 04:14:00 +0200 (Thu, 07 Dec 2023) $ #$Revision: 288110 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/78/7247842.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_7247842 loop_ _publ_author_name 'Luo, Zheng' 'Hu, Huayou' 'Wang, Chao' 'Yang, Zhen' 'Wang, Yefei' _publ_section_title ; A domino reaction for the synthesis of pyrrolo[2,1-a]isoquinolines from 2-aryl-pyrrolidines and alkynes promoted by a four-component catalytic system under aerobic conditions ; _journal_issue 50 _journal_name_full 'RSC Advances' _journal_page_first 35617 _journal_page_last 35620 _journal_paper_doi 10.1039/D3RA07653A _journal_volume 13 _journal_year 2023 _chemical_formula_moiety 'C30 H22 N2 O8' _chemical_formula_sum 'C30 H22 N2 O8' _chemical_formula_weight 538.49 _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 ; 2023-10-06 deposited with the CCDC. 2023-12-01 downloaded from the CCDC. ; _cell_angle_alpha 77.9970(10) _cell_angle_beta 76.9340(10) _cell_angle_gamma 62.4550(10) _cell_formula_units_Z 2 _cell_length_a 10.4827(4) _cell_length_b 11.1537(4) _cell_length_c 12.5636(5) _cell_measurement_reflns_used 3973 _cell_measurement_temperature 172(2) _cell_measurement_theta_max 25.35 _cell_measurement_theta_min 2.82 _cell_volume 1259.59(8) _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 172(2) _diffrn_measured_fraction_theta_full 0.985 _diffrn_measured_fraction_theta_max 0.982 _diffrn_measurement_device_type 'PHOTON 100 CMOS detector' _diffrn_measurement_method 'omega scan' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0263 _diffrn_reflns_av_unetI/netI 0.0361 _diffrn_reflns_Laue_measured_fraction_full 0.985 _diffrn_reflns_Laue_measured_fraction_max 0.982 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 9660 _diffrn_reflns_point_group_measured_fraction_full 0.985 _diffrn_reflns_point_group_measured_fraction_max 0.982 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.380 _diffrn_reflns_theta_min 2.819 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.7452 _exptl_absorpt_correction_T_min 0.6614 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker, 2014)' _exptl_crystal_density_diffrn 1.420 _exptl_crystal_description block _exptl_crystal_F_000 560 _exptl_crystal_size_max 0.450 _exptl_crystal_size_mid 0.380 _exptl_crystal_size_min 0.350 _refine_diff_density_max 0.670 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.042 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 364 _refine_ls_number_reflns 4555 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.037 _refine_ls_R_factor_all 0.0584 _refine_ls_R_factor_gt 0.0408 _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^)+(0.0437P)^2^+0.5260P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0932 _refine_ls_wR_factor_ref 0.1050 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3552 _reflns_number_total 4555 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d3ra07653a2.cif _cod_data_source_block 1 _cod_database_code 7247842 _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 0.954 _shelx_estimated_absorpt_t_max 0.964 _shelx_res_file ; 1.res created by SHELXL-2014/7 TITL 1 in P-1 CELL 0.71073 10.4827 11.1537 12.5636 77.997 76.934 62.455 ZERR 2.00 0.0004 0.0004 0.0005 0.001 0.001 0.001 LATT 1 SFAC C H N O UNIT 60 44 4 16 L.S. 10 BOND $h acta size 0.45 0.38 0.35 omit 1 0 1 FMAP 2 PLAN 20 TEMP -100.650 WGHT 0.043706 0.526020 FVAR 0.37805 MOLE 1 C1 1 0.749544 0.541599 0.406537 11.00000 0.02103 0.02131 = 0.02253 -0.00448 -0.00263 -0.00768 C2 1 0.743822 0.603585 0.299941 11.00000 0.02247 0.02248 = 0.02255 -0.00315 -0.00270 -0.00812 C3 1 0.631605 0.738778 0.300675 11.00000 0.02081 0.02277 = 0.02332 -0.00167 -0.00440 -0.00938 C4 1 0.568701 0.756957 0.409409 11.00000 0.02027 0.01970 = 0.02401 -0.00063 -0.00521 -0.01014 C5 1 0.452922 0.869465 0.464189 11.00000 0.01825 0.02162 = 0.02734 -0.00377 -0.00336 -0.01043 C6 1 0.370029 0.994208 0.405131 11.00000 0.02186 0.02306 = 0.03136 -0.00160 -0.00414 -0.00889 AFIX 43 H6 2 0.387650 1.005045 0.326961 11.00000 -1.20000 AFIX 0 C7 1 0.263522 1.100578 0.460173 11.00000 0.02092 0.02226 = 0.04289 -0.00203 -0.00599 -0.00870 AFIX 43 H7 2 0.208615 1.184301 0.419439 11.00000 -1.20000 AFIX 0 C8 1 0.235316 1.086969 0.574706 11.00000 0.01978 0.02595 = 0.04378 -0.01148 -0.00259 -0.00825 AFIX 43 H8 2 0.162102 1.161155 0.611825 11.00000 -1.20000 AFIX 0 C9 1 0.314280 0.965166 0.633958 11.00000 0.02205 0.03061 = 0.03105 -0.01088 -0.00185 -0.01062 AFIX 43 H9 2 0.294631 0.955862 0.712079 11.00000 -1.20000 AFIX 0 C10 1 0.423387 0.854673 0.580316 11.00000 0.01832 0.02487 = 0.02675 -0.00582 -0.00321 -0.01035 C11 1 0.506660 0.725629 0.642252 11.00000 0.02117 0.02647 = 0.02311 -0.00554 -0.00293 -0.01140 C12 1 0.612220 0.620054 0.590833 11.00000 0.02163 0.02405 = 0.01965 -0.00267 -0.00435 -0.01118 C13 1 0.851962 0.397629 0.441099 11.00000 0.02149 0.02197 = 0.01910 -0.00393 -0.00080 -0.00798 C14 1 0.900958 0.168584 0.445354 11.00000 0.03482 0.01962 = 0.05385 -0.00516 -0.01193 -0.00836 AFIX 137 H14A 2 0.984767 0.143872 0.386582 11.00000 -1.50000 H14B 2 0.849060 0.113983 0.447524 11.00000 -1.50000 H14C 2 0.934685 0.151026 0.516159 11.00000 -1.50000 AFIX 0 C15 1 0.829860 0.536170 0.200707 11.00000 0.02641 0.02564 = 0.02412 -0.00251 -0.00152 -0.01149 C16 1 1.038166 0.343345 0.136481 11.00000 0.03885 0.04209 = 0.03689 -0.01683 0.00530 -0.00440 AFIX 137 H16A 2 0.975811 0.320561 0.105014 11.00000 -1.50000 H16B 2 1.115989 0.259362 0.165371 11.00000 -1.50000 H16C 2 1.080925 0.394282 0.079265 11.00000 -1.50000 AFIX 0 C17 1 0.603106 0.839075 0.200042 11.00000 0.02835 0.02431 = 0.02266 -0.00156 -0.00499 -0.01078 C18 1 0.716763 0.930318 0.043032 11.00000 0.05086 0.04260 = 0.02763 0.00972 -0.00196 -0.02232 AFIX 137 H18A 2 0.677164 0.900872 -0.004701 11.00000 -1.50000 H18B 2 0.814170 0.920870 0.008632 11.00000 -1.50000 H18C 2 0.652957 1.025828 0.053774 11.00000 -1.50000 AFIX 0 C19 1 0.474023 0.709071 0.765217 11.00000 0.02766 0.02514 = 0.02468 -0.00542 -0.00311 -0.00718 C20 1 0.560676 0.719776 0.828199 11.00000 0.03815 0.03921 = 0.03206 -0.00742 -0.00815 -0.01509 AFIX 43 H20 2 0.639564 0.740501 0.792866 11.00000 -1.20000 AFIX 0 C21 1 0.533092 0.700514 0.941961 11.00000 0.05320 0.04715 = 0.03161 -0.01101 -0.01596 -0.01216 AFIX 43 H21 2 0.593671 0.706825 0.984397 11.00000 -1.20000 AFIX 0 C22 1 0.417616 0.672163 0.993616 11.00000 0.06102 0.04972 = 0.02114 -0.00536 -0.00198 -0.01128 AFIX 43 H22 2 0.399391 0.657836 1.071691 11.00000 -1.20000 AFIX 0 C23 1 0.329016 0.664595 0.932588 11.00000 0.05274 0.07120 = 0.03088 -0.00254 0.00580 -0.02980 AFIX 43 H23 2 0.248128 0.647234 0.968485 11.00000 -1.20000 AFIX 0 C24 1 0.357204 0.682235 0.818488 11.00000 0.04003 0.06212 = 0.02899 -0.00551 -0.00001 -0.02832 AFIX 43 H24 2 0.296065 0.675882 0.776615 11.00000 -1.20000 AFIX 0 C25 1 0.694590 0.483228 0.650408 11.00000 0.02316 0.02386 = 0.01767 -0.00493 -0.00080 -0.00866 C26 1 0.817113 0.454569 0.695257 11.00000 0.02840 0.02697 = 0.03063 -0.00356 -0.00780 -0.01256 AFIX 43 H26 2 0.849370 0.522992 0.688439 11.00000 -1.20000 AFIX 0 C27 1 0.892156 0.326697 0.749773 11.00000 0.02801 0.03452 = 0.02730 -0.00157 -0.00976 -0.00995 AFIX 43 H27 2 0.974772 0.306765 0.781718 11.00000 -1.20000 AFIX 0 C28 1 0.843594 0.228970 0.756418 11.00000 0.03004 0.02402 = 0.02175 0.00165 -0.00240 -0.00696 C29 1 0.721950 0.254286 0.714588 11.00000 0.03536 0.02801 = 0.02965 -0.00085 -0.00119 -0.01789 AFIX 43 H29 2 0.690647 0.185189 0.721464 11.00000 -1.20000 AFIX 0 C30 1 0.646018 0.383618 0.661989 11.00000 0.02613 0.03105 = 0.02548 -0.00006 -0.00546 -0.01398 AFIX 43 H30 2 0.560457 0.404176 0.633768 11.00000 -1.20000 AFIX 0 N1 3 0.644048 0.634486 0.474522 11.00000 0.02013 0.01920 = 0.01990 -0.00195 -0.00320 -0.00718 N2 3 0.926592 0.090481 0.809364 11.00000 0.03964 0.03425 = 0.03474 0.00618 -0.00494 -0.00968 O1 4 0.803787 0.311988 0.424326 11.00000 0.02609 0.02093 = 0.03648 -0.00305 -0.00867 -0.00800 O2 4 0.963993 0.364511 0.473452 11.00000 0.02467 0.02665 = 0.03760 -0.00648 -0.01018 -0.00598 O3 4 0.952120 0.425849 0.224844 11.00000 0.03107 0.03268 = 0.02464 -0.00770 0.00139 -0.00227 O4 4 0.795433 0.572746 0.110416 11.00000 0.04431 0.04392 = 0.02357 -0.00729 -0.00683 -0.00781 O5 4 0.725665 0.846301 0.148979 11.00000 0.03424 0.03703 = 0.02677 0.00600 -0.00330 -0.01850 O6 4 0.487367 0.904389 0.167792 11.00000 0.03208 0.04659 = 0.03241 0.01024 -0.01045 -0.01182 O7 4 1.017031 0.073776 0.863891 11.00000 0.06940 0.05472 = 0.08428 0.02556 -0.05019 -0.01944 O8 4 0.901768 -0.001433 0.794642 11.00000 0.07312 0.02853 = 0.06747 0.00658 -0.01730 -0.01831 HKLF 4 REM 1 in P-1 REM R1 = 0.0408 for 3552 Fo > 4sig(Fo) and 0.0584 for all 4555 data REM 364 parameters refined using 0 restraints END WGHT 0.0477 0.4481 REM Highest difference peak 0.670, deepest hole -0.200, 1-sigma level 0.042 Q1 1 0.1199 1.2011 0.6483 11.00000 0.05 0.67 Q2 1 0.6167 0.7859 0.2595 11.00000 0.05 0.21 Q3 1 0.6903 0.6760 0.2914 11.00000 0.05 0.19 Q4 1 0.8799 0.1264 0.3895 11.00000 0.05 0.19 Q5 1 0.7074 0.4187 0.6199 11.00000 0.05 0.19 Q6 1 0.4500 0.7763 0.6088 11.00000 0.05 0.19 Q7 1 0.7820 0.5752 0.3525 11.00000 0.05 0.18 Q8 1 0.6330 0.7635 0.3502 11.00000 0.05 0.18 Q9 1 0.7723 0.5763 0.2595 11.00000 0.05 0.18 Q10 1 1.0023 0.3790 0.0633 11.00000 0.05 0.18 Q11 1 0.5862 0.6982 0.6158 11.00000 0.05 0.17 Q12 1 0.7333 0.5450 0.3505 11.00000 0.05 0.16 Q13 1 0.5706 0.7423 0.3407 11.00000 0.05 0.16 Q14 1 0.4291 0.8552 0.5199 11.00000 0.05 0.16 Q15 1 0.8825 0.3666 0.6913 11.00000 0.05 0.15 Q16 1 0.9489 0.1446 0.9180 11.00000 0.05 0.15 Q17 1 0.6788 0.4374 0.6433 11.00000 0.05 0.15 Q18 1 0.7192 0.4813 0.7053 11.00000 0.05 0.15 Q19 1 0.6565 0.5415 0.6205 11.00000 0.05 0.14 Q20 1 0.7993 0.4884 0.4217 11.00000 0.05 0.14 ; _shelx_res_checksum 23099 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 0.74954(18) 0.54160(17) 0.40654(14) 0.0221(4) Uani 1 1 d . . . . . C2 C 0.74382(18) 0.60359(17) 0.29994(14) 0.0232(4) Uani 1 1 d . . . . . C3 C 0.63160(18) 0.73878(17) 0.30067(14) 0.0223(4) Uani 1 1 d . . . . . C4 C 0.56870(18) 0.75696(16) 0.40941(14) 0.0207(4) Uani 1 1 d . . . . . C5 C 0.45292(17) 0.86947(16) 0.46419(14) 0.0216(4) Uani 1 1 d . . . . . C6 C 0.37003(18) 0.99421(17) 0.40513(16) 0.0260(4) Uani 1 1 d . . . . . H6 H 0.3877 1.0050 0.3270 0.031 Uiso 1 1 calc R U . . . C7 C 0.26352(19) 1.10058(18) 0.46017(16) 0.0291(4) Uani 1 1 d . . . . . H7 H 0.2086 1.1843 0.4194 0.035 Uiso 1 1 calc R U . . . C8 C 0.23532(19) 1.08697(18) 0.57471(17) 0.0297(4) Uani 1 1 d . . . . . H8 H 0.1621 1.1612 0.6118 0.036 Uiso 1 1 calc R U . . . C9 C 0.31428(19) 0.96517(18) 0.63396(16) 0.0275(4) Uani 1 1 d . . . . . H9 H 0.2946 0.9559 0.7121 0.033 Uiso 1 1 calc R U . . . C10 C 0.42339(18) 0.85467(17) 0.58032(14) 0.0225(4) Uani 1 1 d . . . . . C11 C 0.50666(18) 0.72563(17) 0.64225(14) 0.0228(4) Uani 1 1 d . . . . . C12 C 0.61222(18) 0.62005(17) 0.59083(14) 0.0211(4) Uani 1 1 d . . . . . C13 C 0.85196(18) 0.39763(17) 0.44110(14) 0.0216(4) Uani 1 1 d . . . . . C14 C 0.9010(2) 0.16858(18) 0.44535(19) 0.0364(5) Uani 1 1 d . . . . . H14A H 0.9848 0.1439 0.3866 0.055 Uiso 1 1 calc R U . . . H14B H 0.8491 0.1140 0.4475 0.055 Uiso 1 1 calc R U . . . H14C H 0.9347 0.1510 0.5162 0.055 Uiso 1 1 calc R U . . . C15 C 0.82986(19) 0.53617(18) 0.20071(15) 0.0258(4) Uani 1 1 d . . . . . C16 C 1.0382(2) 0.3433(2) 0.13648(18) 0.0445(5) Uani 1 1 d . . . . . H16A H 0.9758 0.3206 0.1050 0.067 Uiso 1 1 calc R U . . . H16B H 1.1160 0.2594 0.1654 0.067 Uiso 1 1 calc R U . . . H16C H 1.0809 0.3943 0.0793 0.067 Uiso 1 1 calc R U . . . C17 C 0.60311(19) 0.83907(17) 0.20004(14) 0.0254(4) Uani 1 1 d . . . . . C18 C 0.7168(2) 0.9303(2) 0.04303(16) 0.0426(5) Uani 1 1 d . . . . . H18A H 0.6772 0.9009 -0.0047 0.064 Uiso 1 1 calc R U . . . H18B H 0.8142 0.9209 0.0086 0.064 Uiso 1 1 calc R U . . . H18C H 0.6530 1.0258 0.0538 0.064 Uiso 1 1 calc R U . . . C19 C 0.47402(19) 0.70907(18) 0.76522(15) 0.0273(4) Uani 1 1 d . . . . . C20 C 0.5607(2) 0.7198(2) 0.82820(16) 0.0362(5) Uani 1 1 d . . . . . H20 H 0.6396 0.7405 0.7929 0.043 Uiso 1 1 calc R U . . . C21 C 0.5331(3) 0.7005(2) 0.94196(17) 0.0451(5) Uani 1 1 d . . . . . H21 H 0.5937 0.7068 0.9844 0.054 Uiso 1 1 calc R U . . . C22 C 0.4176(3) 0.6722(2) 0.99362(17) 0.0497(6) Uani 1 1 d . . . . . H22 H 0.3994 0.6578 1.0717 0.060 Uiso 1 1 calc R U . . . C23 C 0.3290(3) 0.6646(3) 0.93259(18) 0.0532(6) Uani 1 1 d . . . . . H23 H 0.2481 0.6472 0.9685 0.064 Uiso 1 1 calc R U . . . C24 C 0.3572(2) 0.6822(2) 0.81849(17) 0.0422(5) Uani 1 1 d . . . . . H24 H 0.2961 0.6759 0.7766 0.051 Uiso 1 1 calc R U . . . C25 C 0.69459(18) 0.48323(17) 0.65041(14) 0.0222(4) Uani 1 1 d . . . . . C26 C 0.81711(19) 0.45457(18) 0.69526(15) 0.0278(4) Uani 1 1 d . . . . . H26 H 0.8494 0.5230 0.6884 0.033 Uiso 1 1 calc R U . . . C27 C 0.8922(2) 0.32670(19) 0.74977(15) 0.0308(4) Uani 1 1 d . . . . . H27 H 0.9748 0.3068 0.7817 0.037 Uiso 1 1 calc R U . . . C28 C 0.8436(2) 0.22897(18) 0.75642(14) 0.0282(4) Uani 1 1 d . . . . . C29 C 0.7220(2) 0.25429(19) 0.71459(15) 0.0305(4) Uani 1 1 d . . . . . H29 H 0.6906 0.1852 0.7215 0.037 Uiso 1 1 calc R U . . . C30 C 0.64602(19) 0.38362(18) 0.66199(15) 0.0272(4) Uani 1 1 d . . . . . H30 H 0.5605 0.4042 0.6338 0.033 Uiso 1 1 calc R U . . . N1 N 0.64405(14) 0.63449(13) 0.47452(11) 0.0203(3) Uani 1 1 d . . . . . N2 N 0.92659(19) 0.09048(18) 0.80936(14) 0.0406(4) Uani 1 1 d . . . . . O1 O 0.80379(13) 0.31199(12) 0.42433(11) 0.0281(3) Uani 1 1 d . . . . . O2 O 0.96399(13) 0.36451(12) 0.47345(11) 0.0303(3) Uani 1 1 d . . . . . O3 O 0.95212(14) 0.42585(13) 0.22484(10) 0.0344(3) Uani 1 1 d . . . . . O4 O 0.79543(16) 0.57275(15) 0.11042(11) 0.0410(4) Uani 1 1 d . . . . . O5 O 0.72566(14) 0.84630(13) 0.14898(10) 0.0333(3) Uani 1 1 d . . . . . O6 O 0.48737(15) 0.90439(15) 0.16779(11) 0.0406(4) Uani 1 1 d . . . . . O7 O 1.0170(2) 0.07378(18) 0.86389(17) 0.0711(6) Uani 1 1 d . . . . . O8 O 0.9018(2) -0.00143(15) 0.79464(15) 0.0587(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 0.0210(8) 0.0213(8) 0.0225(9) -0.0045(7) -0.0026(7) -0.0077(7) C2 0.0225(9) 0.0225(8) 0.0226(9) -0.0032(7) -0.0027(7) -0.0081(7) C3 0.0208(8) 0.0228(8) 0.0233(9) -0.0017(7) -0.0044(7) -0.0094(7) C4 0.0203(8) 0.0197(8) 0.0240(9) -0.0006(7) -0.0052(7) -0.0101(7) C5 0.0183(8) 0.0216(8) 0.0273(9) -0.0038(7) -0.0034(7) -0.0104(7) C6 0.0219(9) 0.0231(9) 0.0314(10) -0.0016(8) -0.0041(7) -0.0089(7) C7 0.0209(9) 0.0223(9) 0.0429(11) -0.0020(8) -0.0060(8) -0.0087(7) C8 0.0198(9) 0.0259(9) 0.0438(12) -0.0115(8) -0.0026(8) -0.0083(7) C9 0.0221(9) 0.0306(10) 0.0311(10) -0.0109(8) -0.0019(7) -0.0106(8) C10 0.0183(8) 0.0249(9) 0.0267(9) -0.0058(7) -0.0032(7) -0.0103(7) C11 0.0212(8) 0.0265(9) 0.0231(9) -0.0055(7) -0.0029(7) -0.0114(7) C12 0.0216(8) 0.0241(9) 0.0196(8) -0.0027(7) -0.0043(7) -0.0112(7) C13 0.0215(9) 0.0220(8) 0.0191(8) -0.0039(7) -0.0008(7) -0.0080(7) C14 0.0348(11) 0.0196(9) 0.0539(13) -0.0052(9) -0.0119(9) -0.0084(8) C15 0.0264(9) 0.0256(9) 0.0241(10) -0.0025(7) -0.0015(7) -0.0115(8) C16 0.0388(12) 0.0421(12) 0.0369(12) -0.0168(10) 0.0053(9) -0.0044(10) C17 0.0283(10) 0.0243(9) 0.0227(9) -0.0016(7) -0.0050(7) -0.0108(8) C18 0.0509(13) 0.0426(12) 0.0276(11) 0.0097(9) -0.0020(9) -0.0223(10) C19 0.0277(9) 0.0251(9) 0.0247(9) -0.0054(7) -0.0031(7) -0.0072(8) C20 0.0381(11) 0.0392(11) 0.0321(11) -0.0074(9) -0.0082(9) -0.0151(9) C21 0.0532(14) 0.0471(13) 0.0316(11) -0.0110(10) -0.0160(10) -0.0122(11) C22 0.0610(15) 0.0497(13) 0.0211(10) -0.0054(10) -0.0020(10) -0.0113(12) C23 0.0527(14) 0.0712(16) 0.0309(12) -0.0025(11) 0.0058(10) -0.0298(13) C24 0.0400(12) 0.0621(14) 0.0290(11) -0.0055(10) 0.0000(9) -0.0283(11) C25 0.0232(9) 0.0239(9) 0.0177(8) -0.0049(7) -0.0008(7) -0.0087(7) C26 0.0284(10) 0.0270(9) 0.0306(10) -0.0036(8) -0.0078(8) -0.0126(8) C27 0.0280(10) 0.0345(10) 0.0273(10) -0.0016(8) -0.0098(8) -0.0099(8) C28 0.0300(10) 0.0240(9) 0.0217(9) 0.0016(8) -0.0024(7) -0.0070(8) C29 0.0354(10) 0.0280(9) 0.0297(10) -0.0008(8) -0.0012(8) -0.0179(8) C30 0.0261(9) 0.0311(10) 0.0255(9) -0.0001(8) -0.0055(7) -0.0140(8) N1 0.0201(7) 0.0192(7) 0.0199(7) -0.0020(6) -0.0032(6) -0.0072(6) N2 0.0396(10) 0.0343(10) 0.0347(10) 0.0062(8) -0.0049(8) -0.0097(8) O1 0.0261(6) 0.0209(6) 0.0365(7) -0.0030(5) -0.0087(5) -0.0080(5) O2 0.0247(7) 0.0267(7) 0.0376(8) -0.0065(6) -0.0102(6) -0.0060(5) O3 0.0311(7) 0.0327(7) 0.0246(7) -0.0077(6) 0.0014(6) -0.0023(6) O4 0.0443(8) 0.0439(8) 0.0236(7) -0.0073(6) -0.0068(6) -0.0078(7) O5 0.0342(7) 0.0370(7) 0.0268(7) 0.0060(6) -0.0033(6) -0.0185(6) O6 0.0321(8) 0.0466(8) 0.0324(8) 0.0102(7) -0.0104(6) -0.0118(7) O7 0.0694(12) 0.0547(11) 0.0843(14) 0.0256(10) -0.0502(11) -0.0194(9) O8 0.0731(12) 0.0285(8) 0.0675(12) 0.0066(8) -0.0173(9) -0.0183(8) 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 N1 107.99(14) . . ? C2 C1 C13 125.29(15) . . ? N1 C1 C13 126.72(15) . . ? C1 C2 C3 108.53(15) . . ? C1 C2 C15 125.46(15) . . ? C3 C2 C15 125.74(15) . . ? C4 C3 C2 107.35(14) . . ? C4 C3 C17 129.45(15) . . ? C2 C3 C17 123.01(16) . . ? C3 C4 N1 107.20(14) . . ? C3 C4 C5 134.45(15) . . ? N1 C4 C5 118.33(15) . . ? C6 C5 C10 118.94(16) . . ? C6 C5 C4 121.94(16) . . ? C10 C5 C4 119.11(15) . . ? C7 C6 C5 120.35(17) . . ? C7 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? C6 C7 C8 120.88(17) . . ? C6 C7 H7 119.6 . . ? C8 C7 H7 119.6 . . ? C9 C8 C7 119.63(17) . . ? C9 C8 H8 120.2 . . ? C7 C8 H8 120.2 . . ? C8 C9 C10 120.89(17) . . ? C8 C9 H9 119.6 . . ? C10 C9 H9 119.6 . . ? C9 C10 C5 119.30(16) . . ? C9 C10 C11 121.20(16) . . ? C5 C10 C11 119.49(15) . . ? C12 C11 C10 121.20(16) . . ? C12 C11 C19 119.22(15) . . ? C10 C11 C19 119.58(15) . . ? C11 C12 N1 119.73(15) . . ? C11 C12 C25 123.13(15) . . ? N1 C12 C25 117.06(14) . . ? O2 C13 O1 125.29(15) . . ? O2 C13 C1 124.64(15) . . ? O1 C13 C1 109.96(14) . . ? O1 C14 H14A 109.5 . . ? O1 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? O1 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? O4 C15 O3 123.82(17) . . ? O4 C15 C2 125.07(16) . . ? O3 C15 C2 111.10(15) . . ? O3 C16 H16A 109.5 . . ? O3 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? O3 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O6 C17 O5 124.11(16) . . ? O6 C17 C3 125.89(16) . . ? O5 C17 C3 109.99(14) . . ? O5 C18 H18A 109.5 . . ? O5 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? O5 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? C20 C19 C24 118.74(18) . . ? C20 C19 C11 120.57(17) . . ? C24 C19 C11 120.69(17) . . ? C21 C20 C19 120.6(2) . . ? C21 C20 H20 119.7 . . ? C19 C20 H20 119.7 . . ? C22 C21 C20 119.9(2) . . ? C22 C21 H21 120.0 . . ? C20 C21 H21 120.0 . . ? C23 C22 C21 120.2(2) . . ? C23 C22 H22 119.9 . . ? C21 C22 H22 119.9 . . ? C22 C23 C24 120.2(2) . . ? C22 C23 H23 119.9 . . ? C24 C23 H23 119.9 . . ? C19 C24 C23 120.4(2) . . ? C19 C24 H24 119.8 . . ? C23 C24 H24 119.8 . . ? C30 C25 C26 119.80(15) . . ? C30 C25 C12 118.85(15) . . ? C26 C25 C12 121.34(15) . . ? C27 C26 C25 120.32(16) . . ? C27 C26 H26 119.8 . . ? C25 C26 H26 119.8 . . ? C28 C27 C26 118.24(17) . . ? C28 C27 H27 120.9 . . ? C26 C27 H27 120.9 . . ? C29 C28 C27 122.97(16) . . ? C29 C28 N2 118.18(17) . . ? C27 C28 N2 118.84(17) . . ? C28 C29 C30 118.23(16) . . ? C28 C29 H29 120.9 . . ? C30 C29 H29 120.9 . . ? C29 C30 C25 120.38(16) . . ? C29 C30 H30 119.8 . . ? C25 C30 H30 119.8 . . ? C1 N1 C4 108.92(13) . . ? C1 N1 C12 128.96(14) . . ? C4 N1 C12 122.09(14) . . ? O7 N2 O8 123.77(18) . . ? O7 N2 C28 118.18(18) . . ? O8 N2 C28 118.04(17) . . ? C13 O1 C14 115.00(13) . . ? C15 O3 C16 116.16(15) . . ? C17 O5 C18 115.81(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 C2 1.374(2) . ? C1 N1 1.381(2) . ? C1 C13 1.499(2) . ? C2 C3 1.421(2) . ? C2 C15 1.479(2) . ? C3 C4 1.388(2) . ? C3 C17 1.487(2) . ? C4 N1 1.410(2) . ? C4 C5 1.447(2) . ? C5 C6 1.409(2) . ? C5 C10 1.412(2) . ? C6 C7 1.378(3) . ? C6 H6 0.9500 . ? C7 C8 1.393(3) . ? C7 H7 0.9500 . ? C8 C9 1.379(3) . ? C8 H8 0.9500 . ? C9 C10 1.405(2) . ? C9 H9 0.9500 . ? C10 C11 1.455(2) . ? C11 C12 1.348(2) . ? C11 C19 1.496(2) . ? C12 N1 1.416(2) . ? C12 C25 1.494(2) . ? C13 O2 1.197(2) . ? C13 O1 1.338(2) . ? C14 O1 1.451(2) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 O4 1.200(2) . ? C15 O3 1.346(2) . ? C16 O3 1.448(2) . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C17 O6 1.204(2) . ? C17 O5 1.331(2) . ? C18 O5 1.454(2) . ? C18 H18A 0.9800 . ? C18 H18B 0.9800 . ? C18 H18C 0.9800 . ? C19 C20 1.389(3) . ? C19 C24 1.386(3) . ? C20 C21 1.384(3) . ? C20 H20 0.9500 . ? C21 C22 1.378(3) . ? C21 H21 0.9500 . ? C22 C23 1.371(3) . ? C22 H22 0.9500 . ? C23 C24 1.388(3) . ? C23 H23 0.9500 . ? C24 H24 0.9500 . ? C25 C30 1.392(2) . ? C25 C26 1.393(2) . ? C26 C27 1.386(2) . ? C26 H26 0.9500 . ? C27 C28 1.382(3) . ? C27 H27 0.9500 . ? C28 C29 1.375(3) . ? C28 N2 1.475(2) . ? C29 C30 1.389(2) . ? C29 H29 0.9500 . ? C30 H30 0.9500 . ? N2 O7 1.217(2) . ? N2 O8 1.225(2) . ?