#------------------------------------------------------------------------------ #$Date: 2024-10-15 03:41:49 +0300 (Tue, 15 Oct 2024) $ #$Revision: 295487 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/01/7160181.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_7160181 loop_ _publ_author_name 'Zou, Ning' 'Wu, Yu-Zheng' 'Shang, Zi-Wei' 'Cao, Yu-Wei' 'Liao, Limin' 'Wei, Cui' 'Mo, Dong-Liang' 'Zhou, Wen-Jun' _publ_section_title ; Asymmetric [3+3] Cycloaddition of Cinnamaldehyde-derived N-Aryl Nitrones with 2-Indolemethanols Enabled by Chiral Phosphoric Acid ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01365D _journal_year 2024 _chemical_formula_moiety 'C36 H28 N2 O' _chemical_formula_sum 'C36 H28 N2 O' _chemical_formula_weight 504.60 _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_date 2024-07-19 _audit_creation_method ; Olex2 1.5 (compiled 2023.03.06 svn.rbb2c1857 for OlexSys, GUI svn.r6748) ; _audit_update_record ; 2024-07-20 deposited with the CCDC. 2024-10-14 downloaded from the CCDC. ; _cell_angle_alpha 69.772(4) _cell_angle_beta 69.194(5) _cell_angle_gamma 76.134(4) _cell_formula_units_Z 2 _cell_length_a 10.2072(6) _cell_length_b 10.9695(5) _cell_length_c 13.5745(6) _cell_measurement_reflns_used 11114 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 76.7850 _cell_measurement_theta_min 3.6150 _cell_volume 1321.28(13) _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.948 _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_unetI/netI 0.0238 _diffrn_reflns_Laue_measured_fraction_full 0.997 _diffrn_reflns_Laue_measured_fraction_max 0.948 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 17613 _diffrn_reflns_point_group_measured_fraction_full 0.997 _diffrn_reflns_point_group_measured_fraction_max 0.948 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 77.379 _diffrn_reflns_theta_min 3.636 _exptl_absorpt_coefficient_mu 0.591 _exptl_crystal_colour white _exptl_crystal_density_diffrn 1.268 _exptl_crystal_description block _exptl_crystal_F_000 532 _refine_diff_density_max 0.231 _refine_diff_density_min -0.138 _refine_diff_density_rms 0.028 _refine_ls_extinction_coef 0.0027(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.055 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 353 _refine_ls_number_reflns 5321 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.055 _refine_ls_R_factor_all 0.0424 _refine_ls_R_factor_gt 0.0384 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.2175P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1016 _refine_ls_wR_factor_ref 0.1046 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4723 _reflns_number_total 5321 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01365d2.cif _cod_data_source_block 20211206-mdl-wyz-1 _cod_database_code 7160181 _shelx_shelxl_version_number 2018/3 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _olex2_refinement_description ; 1.a Ternary CH refined with riding coordinates: C2(H2) 1.b Aromatic/amide H refined with riding coordinates: N6(H6), C27(H27), C32(H32), C31(H31), C33(H33), C15(H15), C18(H18), C11(H11), C16(H16), C19(H19), C25(H25), C14(H14), C24(H24), C17(H17), C30(H30), C13(H13), C39(H39), C29(H29), C21(H21), C23(H23), C28(H28), C12(H12), C22(H22), C35(H35), C37(H37), C38(H38), C36(H36) ; _shelx_res_file ; TITL 20211206-mdl-wyz-1_a.res in P-1 20211206-mdl-wyz-1.res created by SHELXL-2018/3 at 11:50:06 on 06-Dec-2021 REM Old TITL 20211206-mdl-wyz-1 in P-1 REM SHELXT solution in P-1: R1 0.140, Rweak 0.007, Alpha 0.043 REM 0.000 for 0 systematic absences, Orientation as input REM Formula found by SHELXT: C36 N6 O CELL 1.54184 10.2072 10.9695 13.5745 69.772 69.194 76.134 ZERR 2 0.0006 0.0005 0.0006 0.004 0.005 0.004 LATT 1 SFAC C H N O UNIT 72 56 4 2 L.S. 4 PLAN 5 CONF BOND $H fmap 2 MORE -1 ACTA REM REM REM WGHT 0.046400 0.217500 EXTI 0.002729 FVAR 0.76601 O9 4 0.404128 0.443613 0.714450 11.00000 0.04978 0.04056 = 0.04461 -0.01284 -0.01856 -0.00531 N1 3 0.330085 0.330562 0.765659 11.00000 0.04257 0.03810 = 0.04851 -0.01461 -0.01694 -0.00217 N6 3 0.635190 0.316994 0.892881 11.00000 0.05277 0.04266 = 0.05341 -0.01497 -0.02443 -0.00499 AFIX 43 H6 2 0.655331 0.376124 0.911402 11.00000 -1.20000 AFIX 0 C5 1 0.691093 0.186275 0.916648 11.00000 0.04314 0.04269 = 0.04467 -0.00926 -0.01473 -0.00507 C4 1 0.628346 0.122994 0.873657 11.00000 0.04161 0.04389 = 0.04506 -0.01296 -0.01471 -0.00237 C7 1 0.541441 0.337200 0.834368 11.00000 0.04288 0.04203 = 0.04288 -0.01532 -0.01452 -0.00282 C8 1 0.452651 0.464091 0.795377 11.00000 0.04565 0.03917 = 0.04162 -0.01421 -0.01638 -0.00258 C20 1 0.543054 0.575200 0.729483 11.00000 0.04386 0.03917 = 0.04553 -0.01134 -0.01737 -0.00216 C26 1 0.326032 0.498915 0.887448 11.00000 0.04648 0.04092 = 0.04744 -0.01739 -0.01271 -0.00667 C3 1 0.533209 0.221715 0.822421 11.00000 0.04419 0.04041 = 0.04604 -0.01471 -0.01726 -0.00092 C10 1 0.217149 0.348738 0.722769 11.00000 0.03892 0.04989 = 0.04020 -0.01806 -0.01185 -0.00001 C2 1 0.435678 0.210985 0.766223 11.00000 0.04410 0.03968 = 0.04992 -0.01689 -0.01851 0.00015 AFIX 13 H2 2 0.385275 0.135716 0.813395 11.00000 -1.20000 AFIX 0 C27 1 0.306705 0.430949 0.997192 11.00000 0.05823 0.05173 = 0.04833 -0.01687 -0.01239 -0.01155 AFIX 43 H27 2 0.372418 0.359973 1.017530 11.00000 -1.20000 AFIX 0 C32 1 0.507832 0.188719 0.654404 11.00000 0.04969 0.05254 = 0.05770 -0.02696 -0.02273 0.00247 AFIX 43 H32 2 0.450595 0.179636 0.617880 11.00000 -1.20000 AFIX 0 C34 1 0.720550 0.150299 0.499538 11.00000 0.05654 0.04561 = 0.05250 -0.01431 -0.01592 0.00408 C31 1 0.225783 0.603789 0.858805 11.00000 0.05173 0.04896 = 0.06133 -0.02234 -0.01593 -0.00010 AFIX 43 H31 2 0.237368 0.649980 0.785144 11.00000 -1.20000 AFIX 0 C33 1 0.644563 0.181095 0.604362 11.00000 0.05293 0.05380 = 0.05533 -0.02047 -0.01993 -0.00232 AFIX 43 H33 2 0.699677 0.197011 0.639257 11.00000 -1.20000 AFIX 0 C15 1 0.148325 0.243116 0.743565 11.00000 0.04556 0.05356 = 0.04750 -0.01375 -0.01428 -0.00548 AFIX 43 H15 2 0.184626 0.158898 0.777370 11.00000 -1.20000 AFIX 0 C18 1 0.825890 -0.014445 0.983424 11.00000 0.04930 0.05480 = 0.05885 -0.00386 -0.02435 -0.00031 AFIX 43 H18 2 0.893420 -0.061741 1.018702 11.00000 -1.20000 AFIX 0 C11 1 0.163098 0.472947 0.668705 11.00000 0.05415 0.05115 = 0.05775 -0.01747 -0.02493 0.00109 AFIX 43 H11 2 0.209020 0.544632 0.651572 11.00000 -1.20000 AFIX 0 C16 1 0.664918 -0.012187 0.889220 11.00000 0.05437 0.04491 = 0.06371 -0.01893 -0.02286 -0.00028 AFIX 43 H16 2 0.623290 -0.056250 0.863044 11.00000 -1.20000 AFIX 0 C19 1 0.790371 0.118035 0.971772 11.00000 0.05131 0.05521 = 0.05498 -0.00887 -0.02543 -0.00771 AFIX 43 H19 2 0.831377 0.160413 0.999808 11.00000 -1.20000 AFIX 0 C25 1 0.628778 0.579972 0.623133 11.00000 0.05269 0.05331 = 0.05330 -0.02107 -0.00936 -0.00738 AFIX 43 H25 2 0.629796 0.515974 0.592290 11.00000 -1.20000 AFIX 0 C14 1 0.026261 0.262221 0.714394 11.00000 0.04520 0.07034 = 0.05719 -0.02047 -0.01368 -0.01148 AFIX 43 H14 2 -0.018953 0.190747 0.729480 11.00000 -1.20000 AFIX 0 C24 1 0.712524 0.678458 0.562565 11.00000 0.05353 0.06546 = 0.05327 -0.01136 -0.00935 -0.01239 AFIX 43 H24 2 0.768852 0.680437 0.491218 11.00000 -1.20000 AFIX 0 C17 1 0.763121 -0.079044 0.943669 11.00000 0.05600 0.04447 = 0.06782 -0.01149 -0.02170 0.00273 AFIX 43 H17 2 0.787962 -0.168886 0.954077 11.00000 -1.20000 AFIX 0 C30 1 0.109184 0.640022 0.938673 11.00000 0.05072 0.06277 = 0.08261 -0.03839 -0.01426 0.00035 AFIX 43 H30 2 0.042522 0.710125 0.918556 11.00000 -1.20000 AFIX 0 C13 1 -0.028829 0.385768 0.663348 11.00000 0.04523 0.08228 = 0.06546 -0.02624 -0.02502 0.00111 AFIX 43 H13 2 -0.111487 0.398517 0.644793 11.00000 -1.20000 AFIX 0 C39 1 0.654128 0.119214 0.439495 11.00000 0.06724 0.05819 = 0.05822 -0.02366 -0.01980 0.00367 AFIX 43 H39 2 0.556319 0.122025 0.463571 11.00000 -1.20000 AFIX 0 C29 1 0.091230 0.572919 1.047779 11.00000 0.05438 0.07807 = 0.07548 -0.04646 0.00189 -0.01459 AFIX 43 H29 2 0.013043 0.598108 1.101476 11.00000 -1.20000 AFIX 0 C21 1 0.544304 0.671316 0.772920 11.00000 0.07222 0.06137 = 0.05207 -0.02146 -0.01374 -0.02151 AFIX 43 H21 2 0.487799 0.670354 0.844031 11.00000 -1.20000 AFIX 0 C23 1 0.713597 0.772932 0.606184 11.00000 0.05939 0.05410 = 0.06744 -0.00288 -0.02106 -0.01784 AFIX 43 H23 2 0.770734 0.838779 0.565203 11.00000 -1.20000 AFIX 0 C28 1 0.189180 0.468300 1.077519 11.00000 0.06886 0.07404 = 0.05031 -0.02597 -0.00265 -0.02298 AFIX 43 H28 2 0.176847 0.422517 1.151339 11.00000 -1.20000 AFIX 0 C12 1 0.040588 0.489897 0.640321 11.00000 0.05960 0.06153 = 0.06982 -0.01948 -0.03410 0.00928 AFIX 43 H12 2 0.004749 0.573513 0.604970 11.00000 -1.20000 AFIX 0 C22 1 0.629720 0.769744 0.710846 11.00000 0.08984 0.06483 = 0.07800 -0.02676 -0.02187 -0.03017 AFIX 43 H22 2 0.629746 0.834124 0.740919 11.00000 -1.20000 AFIX 0 C35 1 0.866483 0.146789 0.459647 11.00000 0.05867 0.08291 = 0.07134 -0.02548 -0.01463 -0.00027 AFIX 43 H35 2 0.913599 0.167742 0.497815 11.00000 -1.20000 AFIX 0 C37 1 0.876698 0.080291 0.307256 11.00000 0.09823 0.06762 = 0.05904 -0.02287 -0.00679 0.01897 AFIX 43 H37 2 0.928746 0.055697 0.243752 11.00000 -1.20000 AFIX 0 C38 1 0.731909 0.084183 0.344421 11.00000 0.10237 0.06299 = 0.06110 -0.02713 -0.02609 0.00674 AFIX 43 H38 2 0.686147 0.063133 0.305363 11.00000 -1.20000 AFIX 0 C36 1 0.943110 0.112444 0.363582 11.00000 0.06531 0.09645 = 0.07813 -0.02528 -0.00194 0.00899 AFIX 43 H36 2 1.040709 0.111491 0.337691 11.00000 -1.20000 AFIX 0 HKLF 4 REM 20211206-mdl-wyz-1_a.res in P-1 REM wR2 = 0.1046, GooF = S = 1.055, Restrained GooF = 1.055 for all data REM R1 = 0.0384 for 4723 Fo > 4sig(Fo) and 0.0424 for all 5321 data REM 353 parameters refined using 0 restraints END WGHT 0.0463 0.2176 REM Highest difference peak 0.231, deepest hole -0.138, 1-sigma level 0.028 Q1 1 0.4856 0.2124 0.7963 11.00000 0.05 0.23 Q2 1 0.2341 0.5267 0.7031 11.00000 0.05 0.22 Q3 1 0.5062 0.3989 0.8133 11.00000 0.05 0.21 Q4 1 0.4894 0.2634 0.8646 11.00000 0.05 0.20 Q5 1 0.6552 0.1413 0.9037 11.00000 0.05 0.18 ; _shelx_res_checksum 80550 _olex2_submission_special_instructions 'No special instructions were received' 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 O9 O 0.40413(8) 0.44361(8) 0.71445(6) 0.0437(2) Uani 1 1 d . . . . . N1 N 0.33008(10) 0.33056(9) 0.76566(8) 0.0421(2) Uani 1 1 d . . . . . N6 N 0.63519(11) 0.31699(10) 0.89288(9) 0.0471(2) Uani 1 1 d . . . . . H6 H 0.655331 0.376124 0.911402 0.057 Uiso 1 1 calc R U . . . C5 C 0.69109(12) 0.18627(11) 0.91665(10) 0.0441(3) Uani 1 1 d . . . . . C4 C 0.62835(12) 0.12299(11) 0.87366(10) 0.0436(3) Uani 1 1 d . . . . . C7 C 0.54144(12) 0.33720(11) 0.83437(9) 0.0418(2) Uani 1 1 d . . . . . C8 C 0.45265(12) 0.46409(11) 0.79538(9) 0.0410(2) Uani 1 1 d . . . . . C20 C 0.54305(12) 0.57520(11) 0.72948(10) 0.0426(3) Uani 1 1 d . . . . . C26 C 0.32603(12) 0.49891(11) 0.88745(10) 0.0439(3) Uani 1 1 d . . . . . C3 C 0.53321(12) 0.22171(11) 0.82242(10) 0.0427(3) Uani 1 1 d . . . . . C10 C 0.21715(12) 0.34874(12) 0.72277(9) 0.0427(3) Uani 1 1 d . . . . . C2 C 0.43568(12) 0.21099(11) 0.76622(10) 0.0432(3) Uani 1 1 d . . . . . H2 H 0.385275 0.135716 0.813395 0.052 Uiso 1 1 calc R U . . . C27 C 0.30671(14) 0.43095(13) 0.99719(11) 0.0523(3) Uani 1 1 d . . . . . H27 H 0.372418 0.359973 1.017530 0.063 Uiso 1 1 calc R U . . . C32 C 0.50783(13) 0.18872(13) 0.65440(11) 0.0500(3) Uani 1 1 d . . . . . H32 H 0.450595 0.179636 0.617880 0.060 Uiso 1 1 calc R U . . . C34 C 0.72055(14) 0.15030(13) 0.49954(11) 0.0536(3) Uani 1 1 d . . . . . C31 C 0.22578(14) 0.60379(13) 0.85880(12) 0.0537(3) Uani 1 1 d . . . . . H31 H 0.237368 0.649980 0.785144 0.064 Uiso 1 1 calc R U . . . C33 C 0.64456(14) 0.18109(13) 0.60436(11) 0.0525(3) Uani 1 1 d . . . . . H33 H 0.699677 0.197011 0.639257 0.063 Uiso 1 1 calc R U . . . C15 C 0.14832(13) 0.24312(13) 0.74356(10) 0.0492(3) Uani 1 1 d . . . . . H15 H 0.184626 0.158898 0.777370 0.059 Uiso 1 1 calc R U . . . C18 C 0.82589(14) -0.01444(14) 0.98342(12) 0.0567(3) Uani 1 1 d . . . . . H18 H 0.893420 -0.061741 1.018702 0.068 Uiso 1 1 calc R U . . . C11 C 0.16310(14) 0.47295(13) 0.66870(11) 0.0530(3) Uani 1 1 d . . . . . H11 H 0.209020 0.544632 0.651572 0.064 Uiso 1 1 calc R U . . . C16 C 0.66492(14) -0.01219(13) 0.88922(12) 0.0531(3) Uani 1 1 d . . . . . H16 H 0.623290 -0.056250 0.863044 0.064 Uiso 1 1 calc R U . . . C19 C 0.79037(14) 0.11803(13) 0.97177(11) 0.0529(3) Uani 1 1 d . . . . . H19 H 0.831377 0.160413 0.999808 0.064 Uiso 1 1 calc R U . . . C25 C 0.62878(14) 0.57997(13) 0.62313(11) 0.0533(3) Uani 1 1 d . . . . . H25 H 0.629796 0.515974 0.592290 0.064 Uiso 1 1 calc R U . . . C14 C 0.02626(14) 0.26222(15) 0.71439(12) 0.0567(3) Uani 1 1 d . . . . . H14 H -0.018953 0.190747 0.729480 0.068 Uiso 1 1 calc R U . . . C24 C 0.71252(15) 0.67846(15) 0.56257(12) 0.0601(3) Uani 1 1 d . . . . . H24 H 0.768852 0.680437 0.491218 0.072 Uiso 1 1 calc R U . . . C17 C 0.76312(15) -0.07904(13) 0.94367(12) 0.0582(3) Uani 1 1 d . . . . . H17 H 0.787962 -0.168886 0.954077 0.070 Uiso 1 1 calc R U . . . C30 C 0.10918(15) 0.64002(15) 0.93867(14) 0.0636(4) Uani 1 1 d . . . . . H30 H 0.042522 0.710125 0.918556 0.076 Uiso 1 1 calc R U . . . C13 C -0.02883(14) 0.38577(16) 0.66335(13) 0.0623(4) Uani 1 1 d . . . . . H13 H -0.111487 0.398517 0.644793 0.075 Uiso 1 1 calc R U . . . C39 C 0.65413(17) 0.11921(14) 0.43950(12) 0.0612(4) Uani 1 1 d . . . . . H39 H 0.556319 0.122025 0.463571 0.073 Uiso 1 1 calc R U . . . C29 C 0.09123(16) 0.57292(17) 1.04778(14) 0.0676(4) Uani 1 1 d . . . . . H29 H 0.013043 0.598108 1.101476 0.081 Uiso 1 1 calc R U . . . C21 C 0.54430(16) 0.67132(14) 0.77292(12) 0.0595(3) Uani 1 1 d . . . . . H21 H 0.487799 0.670354 0.844031 0.071 Uiso 1 1 calc R U . . . C23 C 0.71360(16) 0.77293(14) 0.60618(13) 0.0618(4) Uani 1 1 d . . . . . H23 H 0.770734 0.838779 0.565203 0.074 Uiso 1 1 calc R U . . . C28 C 0.18918(16) 0.46830(16) 1.07752(12) 0.0640(4) Uani 1 1 d . . . . . H28 H 0.176847 0.422517 1.151339 0.077 Uiso 1 1 calc R U . . . C12 C 0.04059(16) 0.48990(15) 0.64032(13) 0.0625(4) Uani 1 1 d . . . . . H12 H 0.004749 0.573513 0.604970 0.075 Uiso 1 1 calc R U . . . C22 C 0.62972(19) 0.76974(16) 0.71085(15) 0.0731(4) Uani 1 1 d . . . . . H22 H 0.629746 0.834124 0.740919 0.088 Uiso 1 1 calc R U . . . C35 C 0.86648(17) 0.14679(18) 0.45965(14) 0.0731(4) Uani 1 1 d . . . . . H35 H 0.913599 0.167742 0.497815 0.088 Uiso 1 1 calc R U . . . C37 C 0.8767(2) 0.08029(18) 0.30726(14) 0.0840(6) Uani 1 1 d . . . . . H37 H 0.928746 0.055697 0.243752 0.101 Uiso 1 1 calc R U . . . C38 C 0.7319(2) 0.08418(16) 0.34442(14) 0.0757(5) Uani 1 1 d . . . . . H38 H 0.686147 0.063133 0.305363 0.091 Uiso 1 1 calc R U . . . C36 C 0.9431(2) 0.1124(2) 0.36358(17) 0.0891(6) Uani 1 1 d . . . . . H36 H 1.040709 0.111491 0.337691 0.107 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 O9 0.0498(4) 0.0406(4) 0.0446(4) -0.0128(3) -0.0186(4) -0.0053(3) N1 0.0426(5) 0.0381(5) 0.0485(5) -0.0146(4) -0.0169(4) -0.0022(4) N6 0.0528(6) 0.0427(5) 0.0534(6) -0.0150(4) -0.0244(5) -0.0050(4) C5 0.0431(6) 0.0427(6) 0.0447(6) -0.0093(5) -0.0147(5) -0.0051(5) C4 0.0416(6) 0.0439(6) 0.0451(6) -0.0130(5) -0.0147(5) -0.0024(5) C7 0.0429(6) 0.0420(6) 0.0429(6) -0.0153(5) -0.0145(5) -0.0028(4) C8 0.0456(6) 0.0392(6) 0.0416(6) -0.0142(4) -0.0164(5) -0.0026(4) C20 0.0439(6) 0.0392(6) 0.0455(6) -0.0113(5) -0.0174(5) -0.0022(4) C26 0.0465(6) 0.0409(6) 0.0474(6) -0.0174(5) -0.0127(5) -0.0067(5) C3 0.0442(6) 0.0404(6) 0.0460(6) -0.0147(5) -0.0173(5) -0.0009(4) C10 0.0389(5) 0.0499(6) 0.0402(6) -0.0181(5) -0.0119(5) 0.0000(5) C2 0.0441(6) 0.0397(6) 0.0499(6) -0.0169(5) -0.0185(5) 0.0001(5) C27 0.0582(7) 0.0517(7) 0.0483(7) -0.0169(5) -0.0124(6) -0.0116(6) C32 0.0497(6) 0.0525(7) 0.0577(7) -0.0270(6) -0.0227(6) 0.0025(5) C34 0.0565(7) 0.0456(7) 0.0525(7) -0.0143(5) -0.0159(6) 0.0041(5) C31 0.0517(7) 0.0490(7) 0.0613(8) -0.0223(6) -0.0159(6) -0.0001(5) C33 0.0529(7) 0.0538(7) 0.0553(7) -0.0205(6) -0.0199(6) -0.0023(5) C15 0.0456(6) 0.0536(7) 0.0475(6) -0.0138(5) -0.0143(5) -0.0055(5) C18 0.0493(7) 0.0548(7) 0.0588(8) -0.0039(6) -0.0243(6) -0.0003(6) C11 0.0541(7) 0.0511(7) 0.0578(7) -0.0175(6) -0.0249(6) 0.0011(5) C16 0.0544(7) 0.0449(7) 0.0637(8) -0.0189(6) -0.0229(6) -0.0003(5) C19 0.0513(7) 0.0552(7) 0.0550(7) -0.0089(6) -0.0254(6) -0.0077(5) C25 0.0527(7) 0.0533(7) 0.0533(7) -0.0211(6) -0.0094(6) -0.0074(6) C14 0.0452(6) 0.0703(9) 0.0572(8) -0.0205(6) -0.0137(6) -0.0115(6) C24 0.0535(7) 0.0655(9) 0.0533(7) -0.0114(6) -0.0093(6) -0.0124(6) C17 0.0560(7) 0.0445(7) 0.0678(9) -0.0115(6) -0.0217(7) 0.0027(5) C30 0.0507(7) 0.0628(8) 0.0826(10) -0.0384(8) -0.0143(7) 0.0004(6) C13 0.0452(7) 0.0823(10) 0.0655(9) -0.0262(7) -0.0250(6) 0.0011(7) C39 0.0672(8) 0.0582(8) 0.0582(8) -0.0237(6) -0.0198(7) 0.0037(6) C29 0.0544(8) 0.0781(10) 0.0755(10) -0.0465(9) 0.0019(7) -0.0146(7) C21 0.0722(9) 0.0614(8) 0.0521(7) -0.0215(6) -0.0137(7) -0.0215(7) C23 0.0594(8) 0.0541(8) 0.0674(9) -0.0029(6) -0.0211(7) -0.0178(6) C28 0.0689(9) 0.0740(10) 0.0503(7) -0.0260(7) -0.0026(6) -0.0230(7) C12 0.0596(8) 0.0615(8) 0.0698(9) -0.0195(7) -0.0341(7) 0.0093(6) C22 0.0898(11) 0.0648(9) 0.0780(10) -0.0268(8) -0.0219(9) -0.0302(8) C35 0.0587(8) 0.0829(11) 0.0713(10) -0.0255(8) -0.0146(7) -0.0003(8) C37 0.0982(13) 0.0676(10) 0.0590(9) -0.0229(8) -0.0068(9) 0.0190(9) C38 0.1024(13) 0.0630(9) 0.0611(9) -0.0271(7) -0.0261(9) 0.0067(8) C36 0.0653(10) 0.0964(14) 0.0781(12) -0.0253(10) -0.0019(9) 0.0090(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 N1 O9 C8 108.58(8) . . ? O9 N1 C2 108.56(8) . . ? C10 N1 O9 109.99(9) . . ? C10 N1 C2 120.25(9) . . ? C5 N6 H6 125.6 . . ? C5 N6 C7 108.74(9) . . ? C7 N6 H6 125.6 . . ? N6 C5 C4 107.54(10) . . ? N6 C5 C19 130.85(12) . . ? C19 C5 C4 121.60(11) . . ? C5 C4 C3 106.65(10) . . ? C16 C4 C5 118.95(11) . . ? C16 C4 C3 134.39(11) . . ? N6 C7 C8 126.62(10) . . ? C3 C7 N6 109.58(10) . . ? C3 C7 C8 123.67(10) . . ? O9 C8 C7 104.84(8) . . ? O9 C8 C20 104.03(9) . . ? O9 C8 C26 109.84(9) . . ? C7 C8 C20 111.35(9) . . ? C7 C8 C26 113.08(10) . . ? C26 C8 C20 112.97(9) . . ? C25 C20 C8 119.80(10) . . ? C21 C20 C8 122.04(11) . . ? C21 C20 C25 118.15(12) . . ? C27 C26 C8 123.04(11) . . ? C27 C26 C31 118.92(12) . . ? C31 C26 C8 118.04(11) . . ? C4 C3 C2 130.36(10) . . ? C7 C3 C4 107.47(10) . . ? C7 C3 C2 122.16(10) . . ? C15 C10 N1 120.01(11) . . ? C11 C10 N1 121.35(11) . . ? C11 C10 C15 118.34(11) . . ? N1 C2 C3 105.41(9) . . ? N1 C2 H2 107.3 . . ? N1 C2 C32 114.13(10) . . ? C3 C2 H2 107.3 . . ? C3 C2 C32 114.94(10) . . ? C32 C2 H2 107.3 . . ? C26 C27 H27 119.9 . . ? C26 C27 C28 120.26(13) . . ? C28 C27 H27 119.9 . . ? C2 C32 H32 117.2 . . ? C33 C32 C2 125.55(11) . . ? C33 C32 H32 117.2 . . ? C39 C34 C33 123.24(13) . . ? C35 C34 C33 119.04(14) . . ? C35 C34 C39 117.67(14) . . ? C26 C31 H31 119.7 . . ? C30 C31 C26 120.60(14) . . ? C30 C31 H31 119.7 . . ? C32 C33 C34 127.52(13) . . ? C32 C33 H33 116.2 . . ? C34 C33 H33 116.2 . . ? C10 C15 H15 119.7 . . ? C14 C15 C10 120.67(12) . . ? C14 C15 H15 119.7 . . ? C19 C18 H18 119.2 . . ? C19 C18 C17 121.51(12) . . ? C17 C18 H18 119.2 . . ? C10 C11 H11 120.0 . . ? C12 C11 C10 120.00(13) . . ? C12 C11 H11 120.0 . . ? C4 C16 H16 120.4 . . ? C17 C16 C4 119.16(12) . . ? C17 C16 H16 120.4 . . ? C5 C19 H19 121.1 . . ? C18 C19 C5 117.74(12) . . ? C18 C19 H19 121.1 . . ? C20 C25 H25 119.6 . . ? C24 C25 C20 120.83(13) . . ? C24 C25 H25 119.6 . . ? C15 C14 H14 119.6 . . ? C13 C14 C15 120.77(13) . . ? C13 C14 H14 119.6 . . ? C25 C24 H24 119.6 . . ? C23 C24 C25 120.71(14) . . ? C23 C24 H24 119.6 . . ? C18 C17 H17 119.5 . . ? C16 C17 C18 121.00(13) . . ? C16 C17 H17 119.5 . . ? C31 C30 H30 119.9 . . ? C29 C30 C31 120.24(14) . . ? C29 C30 H30 119.9 . . ? C14 C13 H13 120.6 . . ? C12 C13 C14 118.76(12) . . ? C12 C13 H13 120.6 . . ? C34 C39 H39 119.6 . . ? C38 C39 C34 120.75(16) . . ? C38 C39 H39 119.6 . . ? C30 C29 H29 120.1 . . ? C30 C29 C28 119.90(13) . . ? C28 C29 H29 120.1 . . ? C20 C21 H21 119.8 . . ? C20 C21 C22 120.30(14) . . ? C22 C21 H21 119.8 . . ? C24 C23 H23 120.4 . . ? C24 C23 C22 119.23(13) . . ? C22 C23 H23 120.4 . . ? C27 C28 H28 120.0 . . ? C29 C28 C27 120.09(14) . . ? C29 C28 H28 120.0 . . ? C11 C12 H12 119.3 . . ? C13 C12 C11 121.41(13) . . ? C13 C12 H12 119.3 . . ? C21 C22 H22 119.6 . . ? C23 C22 C21 120.78(14) . . ? C23 C22 H22 119.6 . . ? C34 C35 H35 119.5 . . ? C34 C35 C36 120.95(17) . . ? C36 C35 H35 119.5 . . ? C38 C37 H37 120.1 . . ? C36 C37 H37 120.1 . . ? C36 C37 C38 119.75(16) . . ? C39 C38 H38 119.8 . . ? C37 C38 C39 120.38(18) . . ? C37 C38 H38 119.8 . . ? C35 C36 H36 119.8 . . ? C37 C36 C35 120.49(17) . . ? C37 C36 H36 119.8 . . ? 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 O9 N1 1.4395(12) . ? O9 C8 1.4536(13) . ? N1 C10 1.4121(14) . ? N1 C2 1.4844(14) . ? N6 H6 0.8600 . ? N6 C5 1.3800(15) . ? N6 C7 1.3828(15) . ? C5 C4 1.4112(17) . ? C5 C19 1.3910(17) . ? C4 C3 1.4333(16) . ? C4 C16 1.3989(17) . ? C7 C8 1.5052(15) . ? C7 C3 1.3568(16) . ? C8 C20 1.5284(16) . ? C8 C26 1.5246(16) . ? C20 C25 1.3874(18) . ? C20 C21 1.3788(18) . ? C26 C27 1.3812(18) . ? C26 C31 1.3895(17) . ? C3 C2 1.4982(15) . ? C10 C15 1.3924(17) . ? C10 C11 1.3911(17) . ? C2 H2 0.9800 . ? C2 C32 1.5106(17) . ? C27 H27 0.9300 . ? C27 C28 1.3928(19) . ? C32 H32 0.9300 . ? C32 C33 1.3138(19) . ? C34 C33 1.4708(18) . ? C34 C39 1.391(2) . ? C34 C35 1.388(2) . ? C31 H31 0.9300 . ? C31 C30 1.380(2) . ? C33 H33 0.9300 . ? C15 H15 0.9300 . ? C15 C14 1.3860(18) . ? C18 H18 0.9300 . ? C18 C19 1.378(2) . ? C18 C17 1.390(2) . ? C11 H11 0.9300 . ? C11 C12 1.3885(19) . ? C16 H16 0.9300 . ? C16 C17 1.3741(19) . ? C19 H19 0.9300 . ? C25 H25 0.9300 . ? C25 C24 1.3795(19) . ? C14 H14 0.9300 . ? C14 C13 1.377(2) . ? C24 H24 0.9300 . ? C24 C23 1.363(2) . ? C17 H17 0.9300 . ? C30 H30 0.9300 . ? C30 C29 1.374(2) . ? C13 H13 0.9300 . ? C13 C12 1.374(2) . ? C39 H39 0.9300 . ? C39 C38 1.383(2) . ? C29 H29 0.9300 . ? C29 C28 1.377(2) . ? C21 H21 0.9300 . ? C21 C22 1.391(2) . ? C23 H23 0.9300 . ? C23 C22 1.367(2) . ? C28 H28 0.9300 . ? C12 H12 0.9300 . ? C22 H22 0.9300 . ? C35 H35 0.9300 . ? C35 C36 1.389(3) . ? C37 H37 0.9300 . ? C37 C38 1.377(3) . ? C37 C36 1.356(3) . ? C38 H38 0.9300 . ? C36 H36 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 O9 N1 C10 C15 167.30(10) . . . . ? O9 N1 C10 C11 -19.08(14) . . . . ? O9 N1 C2 C3 55.18(11) . . . . ? O9 N1 C2 C32 -71.89(11) . . . . ? O9 C8 C20 C25 -38.14(13) . . . . ? O9 C8 C20 C21 142.85(12) . . . . ? O9 C8 C26 C27 125.45(12) . . . . ? O9 C8 C26 C31 -54.35(13) . . . . ? N1 O9 C8 C7 56.74(10) . . . . ? N1 O9 C8 C20 173.77(8) . . . . ? N1 O9 C8 C26 -65.05(10) . . . . ? N1 C10 C15 C14 171.63(11) . . . . ? N1 C10 C11 C12 -171.48(12) . . . . ? N1 C2 C32 C33 120.57(14) . . . . ? N6 C5 C4 C3 0.41(13) . . . . ? N6 C5 C4 C16 -178.49(11) . . . . ? N6 C5 C19 C18 179.83(13) . . . . ? N6 C7 C8 O9 164.86(11) . . . . ? N6 C7 C8 C20 52.97(15) . . . . ? N6 C7 C8 C26 -75.49(15) . . . . ? N6 C7 C3 C4 -1.24(14) . . . . ? N6 C7 C3 C2 177.58(11) . . . . ? C5 N6 C7 C8 177.56(11) . . . . ? C5 N6 C7 C3 1.52(14) . . . . ? C5 C4 C3 C7 0.51(13) . . . . ? C5 C4 C3 C2 -178.18(12) . . . . ? C5 C4 C16 C17 -1.45(19) . . . . ? C4 C5 C19 C18 -0.08(19) . . . . ? C4 C3 C2 N1 160.35(12) . . . . ? C4 C3 C2 C32 -73.09(17) . . . . ? C4 C16 C17 C18 0.1(2) . . . . ? C7 N6 C5 C4 -1.17(13) . . . . ? C7 N6 C5 C19 178.92(13) . . . . ? C7 C8 C20 C25 74.27(13) . . . . ? C7 C8 C20 C21 -104.74(13) . . . . ? C7 C8 C26 C27 8.73(16) . . . . ? C7 C8 C26 C31 -171.08(10) . . . . ? C7 C3 C2 N1 -18.18(15) . . . . ? C7 C3 C2 C32 108.39(13) . . . . ? C8 O9 N1 C10 145.25(9) . . . . ? C8 O9 N1 C2 -81.31(10) . . . . ? C8 C7 C3 C4 -177.42(10) . . . . ? C8 C7 C3 C2 1.40(18) . . . . ? C8 C20 C25 C24 -179.24(12) . . . . ? C8 C20 C21 C22 179.02(13) . . . . ? C8 C26 C27 C28 179.53(11) . . . . ? C8 C26 C31 C30 -179.82(12) . . . . ? C20 C8 C26 C27 -118.90(12) . . . . ? C20 C8 C26 C31 61.30(14) . . . . ? C20 C25 C24 C23 0.4(2) . . . . ? C20 C21 C22 C23 0.0(3) . . . . ? C26 C8 C20 C25 -157.21(11) . . . . ? C26 C8 C20 C21 23.78(16) . . . . ? C26 C27 C28 C29 0.3(2) . . . . ? C26 C31 C30 C29 0.3(2) . . . . ? C3 C4 C16 C17 -179.97(14) . . . . ? C3 C7 C8 O9 -19.63(15) . . . . ? C3 C7 C8 C20 -131.52(12) . . . . ? C3 C7 C8 C26 100.01(13) . . . . ? C3 C2 C32 C33 -1.39(19) . . . . ? C10 N1 C2 C3 -176.99(10) . . . . ? C10 N1 C2 C32 55.95(14) . . . . ? C10 C15 C14 C13 0.6(2) . . . . ? C10 C11 C12 C13 -0.8(2) . . . . ? C2 N1 C10 C15 40.13(15) . . . . ? C2 N1 C10 C11 -146.26(12) . . . . ? C2 C32 C33 C34 175.25(12) . . . . ? C27 C26 C31 C30 0.37(19) . . . . ? C34 C39 C38 C37 -0.4(2) . . . . ? C34 C35 C36 C37 -0.7(3) . . . . ? C31 C26 C27 C28 -0.67(19) . . . . ? C31 C30 C29 C28 -0.6(2) . . . . ? C33 C34 C39 C38 -176.49(13) . . . . ? C33 C34 C35 C36 177.11(15) . . . . ? C15 C10 C11 C12 2.24(19) . . . . ? C15 C14 C13 C12 0.9(2) . . . . ? C11 C10 C15 C14 -2.18(18) . . . . ? C16 C4 C3 C7 179.15(14) . . . . ? C16 C4 C3 C2 0.5(2) . . . . ? C19 C5 C4 C3 -179.66(12) . . . . ? C19 C5 C4 C16 1.44(18) . . . . ? C19 C18 C17 C16 1.3(2) . . . . ? C25 C20 C21 C22 0.0(2) . . . . ? C25 C24 C23 C22 -0.4(2) . . . . ? C14 C13 C12 C11 -0.8(2) . . . . ? C24 C23 C22 C21 0.2(3) . . . . ? C17 C18 C19 C5 -1.3(2) . . . . ? C30 C29 C28 C27 0.3(2) . . . . ? C39 C34 C33 C32 -2.5(2) . . . . ? C39 C34 C35 C36 -0.5(2) . . . . ? C21 C20 C25 C24 -0.19(19) . . . . ? C35 C34 C33 C32 -179.99(15) . . . . ? C35 C34 C39 C38 1.0(2) . . . . ? C38 C37 C36 C35 1.3(3) . . . . ? C36 C37 C38 C39 -0.7(3) . . . . ?