#------------------------------------------------------------------------------ #$Date: 2018-02-24 05:10:07 +0200 (Sat, 24 Feb 2018) $ #$Revision: 206634 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/13/7121320.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_7121320 loop_ _publ_author_name 'V, Santhini P' 'A. S., Smrithy' 'C. P., Irfana Jesin' 'Varughese, Sunil' 'John, Jubi' 'K. V., Radhakrishnan' _publ_section_title ; Accessing Highly Functionalized Cyclopentanoids via Cascade Palladation Approach: Unprecedented Benzylic C-H Activation towards Cyclopentenoindanes ; _journal_name_full 'Chemical Communications' _journal_paper_doi 10.1039/C7CC09521J _journal_year 2018 _chemical_formula_moiety 'C24 H32 N2 O6' _chemical_formula_sum 'C24 H32 N2 O6' _chemical_formula_weight 444.51 _chemical_name_systematic ; ? ; _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _audit_update_record ; 2017-10-02 deposited with the CCDC. 2018-02-21 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 106.085(14) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.677(9) _cell_length_b 17.670(12) _cell_length_c 10.710(7) _cell_measurement_reflns_used 3286 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 3.0 _cell_volume 2487(3) _computing_cell_refinement ; CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012) ; _computing_data_collection ; CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012) ; _computing_data_reduction ; CrystalClear-SM Expert 2.0 r14k (Rigaku, 2012) ; _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _computing_structure_solution 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.993 _diffrn_measurement_device_type ; Rigaku Saturn724+ (4x4 bin mode) ; _diffrn_measurement_method 'profile data from \w-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0778 _diffrn_reflns_av_unetI/netI 0.0871 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.993 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 20346 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.993 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.479 _diffrn_reflns_theta_min 3.058 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.836 _exptl_absorpt_correction_type empirical _exptl_absorpt_process_details ; R. H. Blessing Acta Crystallogr., Sect. A, 1995, 51, 33-58 ; _exptl_crystal_colour Colorless _exptl_crystal_density_diffrn 1.187 _exptl_crystal_description Block _exptl_crystal_F_000 952 _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_min 0.170 _refine_diff_density_max 0.170 _refine_diff_density_min -0.186 _refine_diff_density_rms 0.031 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.683 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 296 _refine_ls_number_reflns 5652 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.683 _refine_ls_R_factor_all 0.1041 _refine_ls_R_factor_gt 0.0439 _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^)+(0.0643P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1050 _refine_ls_wR_factor_ref 0.1219 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2455 _reflns_number_total 5652 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7cc09521j2.cif _cod_data_source_block shelx_CCDC1 _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Empirical' changed to 'empirical' according to /home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas ; _cod_database_code 7121320 _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 0.979 _shelx_estimated_absorpt_t_max 0.986 _shelxl_version_number 2013-4 _shelx_res_file ; TITL datam in P2(1)/c REM Shelx file produced by Sir2014 on Sat Sep 24 2016 at 10:08:38 REM Structure name: datam CELL 0.71073 13.6771 17.6698 10.7099 90 106.085 90 ZERR 4 0.009 0.0115 0.0072 0 0.014 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 96 128 8 24 L.S. 15 PLAN 5 FMAP 2 TEMP -123 SIZE 0.25 0.22 0.17 ACTA REM REM REM WGHT 0.064266 FVAR 0.39638 O16 4 1.298196 0.181361 1.069824 11.00000 0.08212 0.09496 = 0.05798 0.00476 0.02438 -0.02930 O17 4 1.273368 0.128658 1.252199 11.00000 0.05488 0.09498 = 0.03856 0.00517 0.00233 -0.02023 O23 4 1.120813 0.076688 0.738730 11.00000 0.08254 0.07133 = 0.03995 -0.00069 0.01403 0.01409 O24 4 1.223442 0.026319 0.924604 11.00000 0.06629 0.06560 = 0.05416 0.00796 0.01589 0.01823 O30 4 0.920340 0.013942 0.814731 11.00000 0.07156 0.04576 = 0.05337 -0.00123 0.01286 0.00088 O31 4 0.835373 0.029302 0.606486 11.00000 0.09185 0.06330 = 0.04703 -0.00915 0.01408 -0.00228 N13 3 1.115730 0.118032 0.936130 11.00000 0.05876 0.05566 = 0.03298 0.00206 0.00738 0.00680 N14 3 1.155575 0.114420 1.069469 11.00000 0.05082 0.06565 = 0.03300 0.00506 0.00671 -0.00765 AFIX 43 H14 2 1.121190 0.092557 1.117883 11.00000 -1.20000 AFIX 0 C1 1 0.798386 0.113108 0.757352 11.00000 0.05524 0.04439 = 0.05021 0.00605 0.01285 -0.00527 C2 1 0.699919 0.126509 0.681401 11.00000 0.06092 0.06616 = 0.07133 0.00488 0.00523 -0.01159 AFIX 43 H2 2 0.670902 0.095054 0.608626 11.00000 -1.20000 AFIX 0 C3 1 0.643815 0.185528 0.711267 11.00000 0.05364 0.07891 = 0.11057 0.01270 0.00649 0.00180 AFIX 43 H3 2 0.576437 0.194234 0.658679 11.00000 -1.20000 AFIX 0 C4 1 0.684035 0.231303 0.815177 11.00000 0.06176 0.06345 = 0.11629 0.00923 0.03075 0.01273 AFIX 43 H4 2 0.644628 0.271496 0.834888 11.00000 -1.20000 AFIX 0 C5 1 0.782439 0.219252 0.892153 11.00000 0.06672 0.04824 = 0.07576 0.00125 0.03020 0.00334 C6 1 0.840301 0.160548 0.863315 11.00000 0.05572 0.04197 = 0.04880 0.00440 0.01806 -0.00176 C7 1 0.945130 0.158478 0.955497 11.00000 0.06046 0.04143 = 0.03939 -0.00138 0.01309 -0.00009 AFIX 13 H7 2 0.956052 0.110879 1.008060 11.00000 -1.20000 AFIX 0 C8 1 0.948100 0.229073 1.043609 11.00000 0.08294 0.05418 = 0.04764 -0.01173 0.01939 0.00060 AFIX 13 H8 2 0.974180 0.215283 1.137551 11.00000 -1.20000 AFIX 0 C9 1 0.839000 0.260166 1.012937 11.00000 0.09738 0.05577 = 0.08299 -0.01328 0.04301 0.00211 AFIX 23 H9A 2 0.808789 0.249577 1.085104 11.00000 -1.20000 H9B 2 0.838033 0.315478 0.997906 11.00000 -1.20000 AFIX 0 C10 1 1.020732 0.280463 1.003619 11.00000 0.08617 0.04696 = 0.07146 -0.01251 0.01645 -0.01336 AFIX 43 H10 2 1.035335 0.330385 1.036412 11.00000 -1.20000 AFIX 0 C11 1 1.062373 0.250261 0.919153 11.00000 0.06840 0.04930 = 0.06168 0.00384 0.01554 -0.01011 AFIX 43 H11 2 1.107824 0.276543 0.881591 11.00000 -1.20000 AFIX 0 C12 1 1.030631 0.169918 0.888230 11.00000 0.05490 0.04469 = 0.03852 0.00223 0.00823 0.00147 AFIX 13 H12 2 1.002294 0.163753 0.792147 11.00000 -1.20000 AFIX 0 C15 1 1.248626 0.145113 1.124785 11.00000 0.06060 0.06383 = 0.04490 0.00091 0.01531 -0.00671 C18 1 1.373225 0.149203 1.338208 11.00000 0.05061 0.09022 = 0.05417 -0.01022 0.00324 -0.01569 C19 1 1.364873 0.121714 1.469310 11.00000 0.09313 0.15206 = 0.05113 0.00703 -0.01248 -0.03505 AFIX 137 H19A 2 1.309919 0.149026 1.492240 11.00000 -1.50000 H19B 2 1.429263 0.131029 1.535616 11.00000 -1.50000 H19C 2 1.350052 0.067360 1.464621 11.00000 -1.50000 AFIX 0 C20 1 1.387436 0.234396 1.339794 11.00000 0.10019 0.10059 = 0.08515 -0.02852 0.02830 -0.02926 AFIX 137 H20A 2 1.393368 0.251193 1.254991 11.00000 -1.50000 H20B 2 1.449433 0.247987 1.407370 11.00000 -1.50000 H20C 2 1.328685 0.259031 1.358047 11.00000 -1.50000 AFIX 0 C21 1 1.454635 0.107500 1.295813 11.00000 0.06775 0.12466 = 0.11393 -0.02083 0.01241 0.00428 AFIX 137 H21A 2 1.437161 0.053651 1.285148 11.00000 -1.50000 H21B 2 1.520048 0.113491 1.361768 11.00000 -1.50000 H21C 2 1.459659 0.128228 1.212941 11.00000 -1.50000 AFIX 0 C22 1 1.151687 0.073112 0.855818 11.00000 0.05506 0.05106 = 0.04609 0.00558 0.01177 0.00276 C25 1 1.283901 -0.019445 0.860833 11.00000 0.07930 0.07179 = 0.06973 0.01140 0.02927 0.02609 C26 1 1.216524 -0.077400 0.774501 11.00000 0.15342 0.07431 = 0.11430 -0.02616 0.01226 0.02482 AFIX 137 H26A 2 1.180979 -0.107084 0.825738 11.00000 -1.50000 H26B 2 1.258294 -0.111148 0.737843 11.00000 -1.50000 H26C 2 1.166577 -0.051576 0.703899 11.00000 -1.50000 AFIX 0 C27 1 1.338416 0.031648 0.788569 11.00000 0.10013 0.13171 = 0.12411 0.05036 0.06584 0.03823 AFIX 137 H27A 2 1.288316 0.057755 0.718513 11.00000 -1.50000 H27B 2 1.383456 0.001224 0.751598 11.00000 -1.50000 H27C 2 1.378783 0.069054 0.848795 11.00000 -1.50000 AFIX 0 C28 1 1.358207 -0.057701 0.974807 11.00000 0.08762 0.09884 = 0.10023 0.03098 0.03296 0.03974 AFIX 137 H28A 2 1.398915 -0.019208 1.032160 11.00000 -1.50000 H28B 2 1.403235 -0.091050 0.942855 11.00000 -1.50000 H28C 2 1.320567 -0.087606 1.023178 11.00000 -1.50000 AFIX 0 C29 1 0.857994 0.047575 0.731960 11.00000 0.06140 0.04575 = 0.04273 -0.00153 0.01269 -0.01535 C32 1 0.891997 -0.035376 0.578259 11.00000 0.10495 0.07732 = 0.06664 -0.02255 0.02899 0.00462 AFIX 137 H32A 2 0.873695 -0.043816 0.484177 11.00000 -1.50000 H32B 2 0.875205 -0.080527 0.621298 11.00000 -1.50000 H32C 2 0.965141 -0.025245 0.610333 11.00000 -1.50000 AFIX 0 HKLF 4 REM datam in P2(1)/c REM R1 = 0.0439 for 2455 Fo > 4sig(Fo) and 0.1041 for all 5652 data REM 296 parameters refined using 0 restraints END WGHT 0.0427 0.0000 REM Highest difference peak 0.170, deepest hole -0.186, 1-sigma level 0.031 Q1 1 1.1511 0.0600 1.1181 11.00000 0.05 0.17 Q2 1 0.7940 0.1795 0.8929 11.00000 0.05 0.14 Q3 1 1.1861 0.1248 0.7725 11.00000 0.05 0.14 Q4 1 1.4094 0.0279 0.7982 11.00000 0.05 0.13 Q5 1 1.0238 0.1517 0.7989 11.00000 0.05 0.13 ; _shelx_res_checksum 57832 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 O16 O 1.29820(11) 0.18136(9) 1.06982(12) 0.0774(5) Uani 1 1 d . . O17 O 1.27337(9) 0.12866(8) 1.25220(10) 0.0649(4) Uani 1 1 d . . O23 O 1.12081(10) 0.07669(8) 0.73873(11) 0.0652(4) Uani 1 1 d . . O24 O 1.22344(9) 0.02632(8) 0.92460(11) 0.0622(4) Uani 1 1 d . . O30 O 0.92034(10) 0.01394(7) 0.81473(11) 0.0578(3) Uani 1 1 d . . O31 O 0.83537(11) 0.02930(8) 0.60649(11) 0.0684(4) Uani 1 1 d . . N13 N 1.11573(11) 0.11803(8) 0.93613(12) 0.0502(4) Uani 1 1 d . . N14 N 1.15558(10) 0.11442(9) 1.06947(11) 0.0508(4) Uani 1 1 d . . H14 H 1.1212 0.0926 1.1179 0.061 Uiso 1 1 calc R U C1 C 0.79839(13) 0.11311(11) 0.75735(16) 0.0503(4) Uani 1 1 d . . C2 C 0.69992(15) 0.12651(13) 0.68140(19) 0.0688(6) Uani 1 1 d . . H2 H 0.6709 0.0951 0.6086 0.083 Uiso 1 1 calc R U C3 C 0.64381(17) 0.18553(15) 0.7113(3) 0.0843(7) Uani 1 1 d . . H3 H 0.5764 0.1942 0.6587 0.101 Uiso 1 1 calc R U C4 C 0.68404(17) 0.23130(14) 0.8152(2) 0.0793(7) Uani 1 1 d . . H4 H 0.6446 0.2715 0.8349 0.095 Uiso 1 1 calc R U C5 C 0.78244(15) 0.21925(11) 0.89215(19) 0.0615(5) Uani 1 1 d . . C6 C 0.84030(13) 0.16055(10) 0.86332(16) 0.0481(4) Uani 1 1 d . . C7 C 0.94513(13) 0.15848(10) 0.95550(15) 0.0472(4) Uani 1 1 d . . H7 H 0.9561 0.1109 1.0081 0.057 Uiso 1 1 calc R U C8 C 0.94810(15) 0.22907(11) 1.04361(17) 0.0613(5) Uani 1 1 d . . H8 H 0.9742 0.2153 1.1376 0.074 Uiso 1 1 calc R U C9 C 0.83900(17) 0.26017(13) 1.0129(2) 0.0751(6) Uani 1 1 d . . H9A H 0.8088 0.2496 1.0851 0.090 Uiso 1 1 calc R U H9B H 0.8380 0.3155 0.9979 0.090 Uiso 1 1 calc R U C10 C 1.02073(16) 0.28046(12) 1.00362(19) 0.0693(6) Uani 1 1 d . . H10 H 1.0353 0.3304 1.0364 0.083 Uiso 1 1 calc R U C11 C 1.06237(15) 0.25026(11) 0.91915(18) 0.0603(5) Uani 1 1 d . . H11 H 1.1078 0.2765 0.8816 0.072 Uiso 1 1 calc R U C12 C 1.03063(13) 0.16992(10) 0.88823(15) 0.0470(4) Uani 1 1 d . . H12 H 1.0023 0.1638 0.7921 0.056 Uiso 1 1 calc R U C15 C 1.24863(14) 0.14511(12) 1.12479(16) 0.0563(5) Uani 1 1 d . . C18 C 1.37322(14) 0.14920(14) 1.33821(18) 0.0673(6) Uani 1 1 d . . C19 C 1.36487(18) 0.12171(17) 1.46931(18) 0.1053(10) Uani 1 1 d . . H19A H 1.3099 0.1490 1.4922 0.158 Uiso 1 1 calc R U H19B H 1.4293 0.1310 1.5356 0.158 Uiso 1 1 calc R U H19C H 1.3501 0.0674 1.4646 0.158 Uiso 1 1 calc R U C20 C 1.38744(19) 0.23440(15) 1.3398(2) 0.0948(8) Uani 1 1 d . . H20A H 1.3934 0.2512 1.2550 0.142 Uiso 1 1 calc R U H20B H 1.4494 0.2480 1.4074 0.142 Uiso 1 1 calc R U H20C H 1.3287 0.2590 1.3580 0.142 Uiso 1 1 calc R U C21 C 1.45463(17) 0.10750(16) 1.2958(2) 0.1047(9) Uani 1 1 d . . H21A H 1.4372 0.0537 1.2851 0.157 Uiso 1 1 calc R U H21B H 1.5200 0.1135 1.3618 0.157 Uiso 1 1 calc R U H21C H 1.4597 0.1282 1.2129 0.157 Uiso 1 1 calc R U C22 C 1.15169(13) 0.07311(11) 0.85582(17) 0.0512(5) Uani 1 1 d . . C25 C 1.28390(16) -0.01944(13) 0.86083(19) 0.0719(6) Uani 1 1 d . . C26 C 1.2165(2) -0.07740(15) 0.7745(3) 0.1190(10) Uani 1 1 d . . H26A H 1.1810 -0.1071 0.8257 0.178 Uiso 1 1 calc R U H26B H 1.2583 -0.1111 0.7378 0.178 Uiso 1 1 calc R U H26C H 1.1666 -0.0516 0.7039 0.178 Uiso 1 1 calc R U C27 C 1.33842(19) 0.03165(17) 0.7886(2) 0.1117(10) Uani 1 1 d . . H27A H 1.2883 0.0578 0.7185 0.168 Uiso 1 1 calc R U H27B H 1.3835 0.0012 0.7516 0.168 Uiso 1 1 calc R U H27C H 1.3788 0.0691 0.8488 0.168 Uiso 1 1 calc R U C28 C 1.35821(17) -0.05770(15) 0.9748(2) 0.0942(8) Uani 1 1 d . . H28A H 1.3989 -0.0192 1.0322 0.141 Uiso 1 1 calc R U H28B H 1.4032 -0.0911 0.9429 0.141 Uiso 1 1 calc R U H28C H 1.3206 -0.0876 1.0232 0.141 Uiso 1 1 calc R U C29 C 0.85799(14) 0.04758(11) 0.73196(16) 0.0503(5) Uani 1 1 d . . C32 C 0.89200(18) -0.03538(13) 0.57826(19) 0.0819(7) Uani 1 1 d . . H32A H 0.8737 -0.0438 0.4842 0.123 Uiso 1 1 calc R U H32B H 0.8752 -0.0805 0.6213 0.123 Uiso 1 1 calc R U H32C H 0.9651 -0.0252 0.6103 0.123 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 O16 0.0821(10) 0.0950(12) 0.0580(8) 0.0048(7) 0.0244(7) -0.0293(9) O17 0.0549(8) 0.0950(12) 0.0386(7) 0.0052(6) 0.0023(5) -0.0202(7) O23 0.0825(9) 0.0713(10) 0.0400(7) -0.0007(6) 0.0140(6) 0.0141(7) O24 0.0663(8) 0.0656(10) 0.0542(7) 0.0080(6) 0.0159(6) 0.0182(7) O30 0.0716(8) 0.0458(8) 0.0534(7) -0.0012(6) 0.0129(6) 0.0009(7) O31 0.0919(10) 0.0633(10) 0.0470(7) -0.0092(6) 0.0141(7) -0.0023(8) N13 0.0588(9) 0.0557(10) 0.0330(7) 0.0021(7) 0.0074(6) 0.0068(8) N14 0.0508(9) 0.0656(11) 0.0330(7) 0.0051(7) 0.0067(6) -0.0077(8) C1 0.0552(11) 0.0444(12) 0.0502(10) 0.0060(8) 0.0129(8) -0.0053(9) C2 0.0609(13) 0.0662(16) 0.0713(13) 0.0049(11) 0.0052(10) -0.0116(12) C3 0.0536(13) 0.0789(19) 0.111(2) 0.0127(15) 0.0065(13) 0.0018(13) C4 0.0618(14) 0.0634(16) 0.1163(19) 0.0092(14) 0.0307(13) 0.0127(12) C5 0.0667(13) 0.0482(13) 0.0758(13) 0.0012(10) 0.0302(11) 0.0033(10) C6 0.0557(11) 0.0420(11) 0.0488(10) 0.0044(8) 0.0181(8) -0.0018(9) C7 0.0605(11) 0.0414(11) 0.0394(9) -0.0014(8) 0.0131(8) -0.0001(9) C8 0.0829(14) 0.0542(13) 0.0476(10) -0.0117(9) 0.0194(9) 0.0006(11) C9 0.0974(17) 0.0558(15) 0.0830(15) -0.0133(11) 0.0430(12) 0.0021(12) C10 0.0862(15) 0.0470(13) 0.0715(14) -0.0125(10) 0.0164(11) -0.0134(11) C11 0.0684(13) 0.0493(13) 0.0617(12) 0.0038(10) 0.0155(10) -0.0101(10) C12 0.0549(10) 0.0447(11) 0.0385(8) 0.0022(8) 0.0082(7) 0.0015(9) C15 0.0606(12) 0.0638(14) 0.0449(10) 0.0009(9) 0.0153(9) -0.0067(11) C18 0.0506(11) 0.0902(18) 0.0542(11) -0.0102(11) 0.0032(9) -0.0157(12) C19 0.0931(18) 0.152(3) 0.0511(13) 0.0070(14) -0.0125(12) -0.0350(18) C20 0.1002(18) 0.101(2) 0.0851(17) -0.0285(15) 0.0283(13) -0.0293(16) C21 0.0678(15) 0.125(2) 0.114(2) -0.0208(17) 0.0124(14) 0.0043(16) C22 0.0551(11) 0.0511(13) 0.0461(10) 0.0056(9) 0.0118(9) 0.0028(9) C25 0.0793(15) 0.0718(16) 0.0697(13) 0.0114(11) 0.0293(11) 0.0261(13) C26 0.153(3) 0.074(2) 0.114(2) -0.0262(16) 0.0123(19) 0.0248(19) C27 0.1001(19) 0.132(3) 0.124(2) 0.0504(19) 0.0658(17) 0.0382(18) C28 0.0876(17) 0.099(2) 0.1002(17) 0.0310(15) 0.0330(13) 0.0397(15) C29 0.0614(12) 0.0458(12) 0.0427(10) -0.0015(8) 0.0127(8) -0.0154(10) C32 0.1049(17) 0.0773(18) 0.0666(13) -0.0226(12) 0.0290(12) 0.0046(14) 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 C15 O17 C18 120.88(15) C22 O24 C25 120.71(14) C29 O31 C32 114.25(15) C22 N13 N14 121.27(14) C22 N13 C12 122.55(14) N14 N13 C12 116.13(13) C15 N14 N13 119.06(14) C2 C1 C6 119.09(19) C2 C1 C29 121.27(18) C6 C1 C29 119.57(16) C3 C2 C1 120.2(2) C4 C3 C2 120.8(2) C3 C4 C5 120.0(2) C4 C5 C6 120.07(19) C4 C5 C9 128.6(2) C6 C5 C9 111.26(18) C5 C6 C1 119.77(17) C5 C6 C7 111.80(16) C1 C6 C7 128.43(17) C6 C7 C12 113.48(14) C6 C7 C8 103.83(14) C12 C7 C8 106.33(15) C10 C8 C9 113.87(18) C10 C8 C7 102.76(16) C9 C8 C7 107.20(15) C5 C9 C8 104.52(16) C11 C10 C8 113.68(18) C10 C11 C12 112.65(18) N13 C12 C11 111.38(15) N13 C12 C7 112.74(14) C11 C12 C7 103.39(15) O16 C15 O17 126.63(17) O16 C15 N14 126.00(17) O17 C15 N14 107.36(15) O17 C18 C21 109.10(17) O17 C18 C20 110.30(18) C21 C18 C20 112.7(2) O17 C18 C19 101.89(16) C21 C18 C19 111.9(2) C20 C18 C19 110.4(2) O23 C22 O24 126.57(17) O23 C22 N13 122.85(17) O24 C22 N13 110.58(15) O24 C25 C26 109.54(19) O24 C25 C27 109.46(19) C26 C25 C27 113.3(2) O24 C25 C28 102.21(16) C26 C25 C28 110.5(2) C27 C25 C28 111.3(2) O30 C29 O31 122.86(18) O30 C29 C1 124.31(16) O31 C29 C1 112.83(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O16 C15 1.199(2) O17 C15 1.344(2) O17 C18 1.466(2) O23 C22 1.209(2) O24 C22 1.337(2) O24 C25 1.455(2) O30 C29 1.203(2) O31 C29 1.332(2) O31 C32 1.458(2) N13 C22 1.359(2) N13 N14 1.3817(18) N13 C12 1.459(2) N14 C15 1.359(2) C1 C2 1.387(3) C1 C6 1.400(2) C1 C29 1.484(3) C2 C3 1.384(3) C3 C4 1.362(3) C4 C5 1.386(3) C5 C6 1.390(3) C5 C9 1.497(3) C6 C7 1.499(2) C7 C12 1.547(2) C7 C8 1.558(2) C8 C10 1.494(3) C8 C9 1.538(3) C10 C11 1.309(3) C11 C12 1.495(3) C18 C21 1.506(3) C18 C20 1.517(3) C18 C19 1.520(3) C25 C26 1.510(3) C25 C27 1.513(3) C25 C28 1.514(3)