#------------------------------------------------------------------------------ #$Date: 2024-11-08 03:42:37 +0200 (Fri, 08 Nov 2024) $ #$Revision: 295830 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/16/02/7160223.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_7160223 loop_ _publ_author_name 'Koike, Daiki' 'Masu, Hyuma' 'Kikkawa, Shoko' 'Chiba, Ayako' 'Kamohara, Kaho' 'Okuda, Arisa' 'Hikawa, Hidemasa' 'Azumaya, Isao' _publ_section_title ; Chiral spherical aromatic amides: one-step synthesis and their stereochemical/chiroptical properties ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D4OB01458H _journal_year 2024 _chemical_formula_sum 'C36 H30 N6 O6' _chemical_formula_weight 642.66 _space_group_crystal_system trigonal _space_group_IT_number 161 _space_group_name_Hall 'R 3 -2"c' _space_group_name_H-M_alt 'R 3 c :H' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2019/1 _audit_update_record ; 2024-09-04 deposited with the CCDC. 2024-11-04 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 120 _cell_formula_units_Z 18 _cell_length_a 29.5567(6) _cell_length_b 29.5567(6) _cell_length_c 18.0997(5) _cell_measurement_reflns_used 4874 _cell_measurement_temperature 93(2) _cell_measurement_theta_max 18.7500 _cell_measurement_theta_min 2.7530 _cell_volume 13693.5(5) _computing_structure_refinement 'SHELXL-2019/1 (Sheldrick, 2019)' _diffrn_ambient_temperature 93(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.941 _diffrn_measurement_device_type 'dtrek-CrysAlisPro-abstract goniometer imported rigaku-d*trek images' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.1068 _diffrn_reflns_av_unetI/netI 0.1239 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.941 _diffrn_reflns_limit_h_max 40 _diffrn_reflns_limit_h_min -40 _diffrn_reflns_limit_k_max 39 _diffrn_reflns_limit_k_min -40 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_number 49036 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.909 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.564 _diffrn_reflns_theta_min 2.387 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83642 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.403 _exptl_crystal_description prismatic _exptl_crystal_F_000 6048 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.350 _exptl_crystal_size_min 0.250 _refine_diff_density_max 0.740 _refine_diff_density_min -0.386 _refine_diff_density_rms 0.119 _refine_ls_abs_structure_details ; Flack x determined using 1137 quotients [(I+)-(I-)]/[(I+)+(I-)] (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). ; _refine_ls_abs_structure_Flack 0.3(10) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 438 _refine_ls_number_reflns 7759 _refine_ls_number_restraints 11 _refine_ls_restrained_S_all 1.029 _refine_ls_R_factor_all 0.2395 _refine_ls_R_factor_gt 0.0931 _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^)+(0.1248P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1965 _refine_ls_wR_factor_ref 0.2615 _reflns_Friedel_coverage 0.928 _reflns_Friedel_fraction_full 0.999 _reflns_Friedel_fraction_max 0.877 _reflns_number_gt 3145 _reflns_number_total 7759 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4ob01458h2.cif _cod_data_source_block Me_sphe1_a _cod_original_cell_volume 13693.5(7) _cod_database_code 7160223 _shelx_shelxl_version_number 2019/1 _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_res_file ; TITL Me_sphe1_a.res in R3c Me_sphe1_a.res created by SHELXL-2019/1 at 17:15:38 on 10-Mar-2023 REM Old TITL Me_sphe1 in R3c REM SHELXT solution in R3c: R1 0.240, Rweak 0.190, Alpha 0.021 REM 0.535 for 184 systematic absences, Orientation as input REM Flack x = 0.419 ( 1.027 ) from 1195 Parsons' quotients REM Formula found by SHELXT: C36 N4 O8 CELL 0.71073 29.5567 29.5567 18.0997 90.000 90.000 120.000 ZERR 18.000 0.0006 0.0006 0.0005 0.000 0.000 0.000 LATT -3 SYMM -Y, X-Y, Z SYMM -X+Y, -X, Z SYMM -Y, -X, 1/2+Z SYMM -X+Y, Y, 1/2+Z SYMM X, X-Y, 1/2+Z SFAC C H N O UNIT 648 540 108 108 L.S. 16 LIST 4 acta FMAP 2 PLAN 20 EXYZ O5A C34B EXYZ O5B C34A EXYZ N5A C33B EXYZ N5B C33A EADP O5A C34B EADP O5B C34A EADP N5A C33B EADP N5B C33A EXYZ O6A C36B EXYZ O6B C36A EXYZ N6A C35B EXYZ N6B C35A EADP O6A C36B EADP O6B C36A EADP N6A C35B EADP N6B C35A WGHT 0.124800 FVAR 0.12202 0.54244 part 1 same O5B C33B N5B C34B O6B C35B N6B C36B O5A 4 0.828816 0.504514 0.660924 21.00000 0.12980 0.13857 = 0.18813 0.02175 -0.04622 0.07360 C33A 1 0.788746 0.502999 0.627952 21.00000 0.09104 0.09678 = 0.07676 -0.00081 -0.01750 0.05753 N5A 3 0.742189 0.462250 0.638114 21.00000 0.10690 0.08186 = 0.07525 0.00162 -0.00804 0.06141 C34A 1 0.737936 0.422731 0.678278 21.00000 0.17090 0.14229 = 0.16203 0.03157 -0.02636 0.09320 AFIX 33 H34A 2 0.701896 0.395879 0.681001 21.00000 -1.50000 H34B 2 0.757867 0.408904 0.655713 21.00000 -1.50000 H34C 2 0.750969 0.434827 0.727171 21.00000 -1.50000 AFIX 0 O6A 4 0.639681 0.597794 0.305502 21.00000 0.20461 0.20214 = 0.12543 0.02425 -0.02500 0.14299 C35A 1 0.654408 0.589421 0.370010 21.00000 0.08205 0.08980 = 0.07639 0.01595 -0.00536 0.04047 N6A 3 0.647476 0.611760 0.428111 21.00000 0.07465 0.09069 = 0.11438 0.02439 0.00395 0.05100 C36A 1 0.625246 0.640042 0.419398 21.00000 0.18568 0.19782 = 0.13375 0.03239 0.00430 0.14727 AFIX 33 H36A 2 0.622793 0.653808 0.466320 21.00000 -1.50000 H36B 2 0.645739 0.668344 0.386172 21.00000 -1.50000 H36C 2 0.590861 0.618770 0.399293 21.00000 -1.50000 AFIX 0 part 2 O5B 4 0.737936 0.422731 0.678278 -21.00000 0.17090 0.14229 = 0.16203 0.03157 -0.02636 0.09320 C33B 1 0.742189 0.462250 0.638114 -21.00000 0.10690 0.08186 = 0.07525 0.00162 -0.00804 0.06141 N5B 3 0.788746 0.502999 0.627952 -21.00000 0.09104 0.09678 = 0.07676 -0.00081 -0.01750 0.05753 C34B 1 0.828816 0.504514 0.660924 -21.00000 0.12980 0.13857 = 0.18813 0.02175 -0.04622 0.07360 AFIX 33 H34D 2 0.859987 0.536438 0.648351 -21.00000 -1.50000 H34E 2 0.823713 0.502899 0.713448 -21.00000 -1.50000 H34F 2 0.832184 0.475317 0.645195 -21.00000 -1.50000 AFIX 0 O6B 4 0.625246 0.640042 0.419398 -21.00000 0.18568 0.19782 = 0.13375 0.03239 0.00430 0.14727 C35B 1 0.647476 0.611760 0.428111 -21.00000 0.07465 0.09069 = 0.11438 0.02439 0.00395 0.05100 N6B 3 0.654408 0.589421 0.370010 -21.00000 0.08205 0.08980 = 0.07639 0.01595 -0.00536 0.04047 C36B 1 0.639681 0.597794 0.305502 -21.00000 0.20461 0.20214 = 0.12543 0.02425 -0.02500 0.14299 AFIX 33 H36D 2 0.646895 0.579316 0.267972 -21.00000 -1.50000 H36E 2 0.602888 0.585665 0.306510 -21.00000 -1.50000 H36F 2 0.658485 0.634528 0.294828 -21.00000 -1.50000 AFIX 0 part 0 O1 4 0.582403 0.544241 0.722823 11.00000 0.11372 0.07993 = 0.10504 -0.00425 0.02130 0.05343 O2 4 0.569440 0.344536 0.449764 11.00000 0.10633 0.07553 = 0.08180 0.01105 0.01062 0.02439 O3 4 0.816947 0.553999 0.276776 11.00000 0.09338 0.11651 = 0.06982 -0.02400 -0.01210 0.04489 O4 4 0.863872 0.721012 0.614717 11.00000 0.06220 0.09437 = 0.12029 -0.01293 -0.00029 0.03153 N1 3 0.588516 0.480879 0.666520 11.00000 0.10470 0.05337 = 0.11444 0.00350 0.03946 0.04141 N2 3 0.626221 0.412600 0.383030 11.00000 0.11688 0.06238 = 0.06380 0.01654 0.02601 0.01393 N3 3 0.839130 0.589784 0.387843 11.00000 0.06902 0.12811 = 0.05630 -0.03012 -0.00520 0.02755 N4 3 0.777391 0.681615 0.625339 11.00000 0.04980 0.08938 = 0.13207 -0.03400 0.00037 0.02929 C1 1 0.603145 0.530948 0.675875 11.00000 0.07335 0.05874 = 0.07666 -0.00924 0.01444 0.03591 C2 1 0.546028 0.442816 0.710950 11.00000 0.18051 0.06066 = 0.24185 -0.00104 0.12911 0.03841 AFIX 137 H2A 2 0.539525 0.408455 0.698790 11.00000 -1.50000 H2B 2 0.515198 0.444941 0.701373 11.00000 -1.50000 H2C 2 0.555056 0.449694 0.762285 11.00000 -1.50000 AFIX 0 C3 1 0.618198 0.463813 0.621682 11.00000 0.08036 0.04669 = 0.08086 0.00929 0.02542 0.02856 C4 1 0.597776 0.437268 0.557913 11.00000 0.06355 0.05138 = 0.07621 0.01124 0.02065 0.02737 AFIX 43 H4 2 0.564748 0.429952 0.542654 11.00000 -1.20000 AFIX 0 C5 1 0.626157 0.420951 0.515257 11.00000 0.06656 0.05819 = 0.05754 0.01624 0.01452 0.02814 C6 1 0.674896 0.431196 0.540038 11.00000 0.08410 0.05669 = 0.05507 0.01203 0.01851 0.03510 AFIX 43 H6 2 0.693951 0.420261 0.511800 11.00000 -1.20000 AFIX 0 C7 1 0.695875 0.457510 0.606305 11.00000 0.07690 0.05857 = 0.07427 0.01570 0.01451 0.03348 C8 1 0.666674 0.474725 0.647519 11.00000 0.09570 0.04844 = 0.07005 -0.00269 0.00627 0.03085 AFIX 43 H8 2 0.679866 0.493113 0.691352 11.00000 -1.20000 AFIX 0 C9 1 0.605089 0.390672 0.447988 11.00000 0.06728 0.04677 = 0.07951 0.00374 0.01503 0.02249 C10 1 0.606662 0.381691 0.317037 11.00000 0.23234 0.08795 = 0.07174 -0.01389 0.04681 -0.03016 AFIX 137 H10A 2 0.621350 0.403707 0.274521 11.00000 -1.50000 H10B 2 0.569291 0.365617 0.315676 11.00000 -1.50000 H10C 2 0.616287 0.355111 0.316853 11.00000 -1.50000 AFIX 0 C11 1 0.662808 0.468532 0.376638 11.00000 0.09435 0.06070 = 0.04359 0.00322 0.00227 0.02301 C12 1 0.642689 0.501264 0.382942 11.00000 0.07641 0.08358 = 0.04883 0.01331 0.00600 0.02501 AFIX 43 H12 2 0.607450 0.487969 0.393273 11.00000 -1.20000 AFIX 0 C13 1 0.675971 0.554934 0.373596 11.00000 0.08572 0.07070 = 0.04803 0.00134 -0.00667 0.03185 C14 1 0.728480 0.573454 0.361196 11.00000 0.06287 0.06036 = 0.05455 0.00242 -0.00884 0.01488 AFIX 43 H14 2 0.750960 0.609245 0.356496 11.00000 -1.20000 AFIX 0 C15 1 0.748460 0.540046 0.355596 11.00000 0.07282 0.06649 = 0.05136 -0.00466 -0.01273 0.02982 C16 1 0.714003 0.486209 0.362710 11.00000 0.07595 0.05999 = 0.04168 -0.00082 0.00434 0.02521 AFIX 43 H16 2 0.726192 0.462808 0.357906 11.00000 -1.20000 AFIX 0 C17 1 0.802950 0.560442 0.337568 11.00000 0.07710 0.07108 = 0.04567 -0.00969 -0.00094 0.02857 C18 1 0.893821 0.612933 0.368925 11.00000 0.06827 0.29802 = 0.08642 -0.07643 0.01218 0.01310 AFIX 137 H18A 2 0.914821 0.632245 0.410448 11.00000 -1.50000 H18B 2 0.901563 0.636046 0.327621 11.00000 -1.50000 H18C 2 0.901374 0.585872 0.356152 11.00000 -1.50000 AFIX 0 C19 1 0.825255 0.590880 0.465707 11.00000 0.05752 0.09784 = 0.05596 -0.01139 -0.00596 0.03055 C20 1 0.810121 0.547317 0.506295 11.00000 0.06470 0.07780 = 0.08425 -0.02456 -0.02104 0.03529 AFIX 43 H20 2 0.807510 0.517566 0.484645 11.00000 -1.20000 AFIX 0 C21 1 0.798126 0.547265 0.582882 11.00000 0.05134 0.08624 = 0.05974 -0.00560 -0.00579 0.02899 C22 1 0.800484 0.591559 0.610963 11.00000 0.04877 0.08215 = 0.06451 -0.01889 -0.00405 0.03619 AFIX 43 H22 2 0.791758 0.591883 0.660250 11.00000 -1.20000 AFIX 0 C23 1 0.815414 0.635783 0.568407 11.00000 0.03815 0.07754 = 0.06538 0.00709 0.00694 0.03035 C24 1 0.828889 0.635555 0.494894 11.00000 0.04082 0.07421 = 0.05793 -0.00182 -0.00291 0.01542 AFIX 43 H24 2 0.840218 0.665229 0.465804 11.00000 -1.20000 AFIX 0 C25 1 0.821016 0.682483 0.602647 11.00000 0.05116 0.06485 = 0.07329 -0.00891 0.00089 0.01774 C26 1 0.783074 0.726702 0.664210 11.00000 0.06018 0.15097 = 0.31248 -0.14510 0.00615 0.03157 AFIX 137 H26A 2 0.749226 0.722788 0.672602 11.00000 -1.50000 H26B 2 0.803791 0.757479 0.635176 11.00000 -1.50000 H26C 2 0.799991 0.729884 0.710756 11.00000 -1.50000 AFIX 0 C27 1 0.725628 0.641825 0.600063 11.00000 0.05006 0.07403 = 0.11400 -0.02164 -0.00016 0.03508 C28 1 0.713167 0.642870 0.527233 11.00000 0.07034 0.07437 = 0.09350 0.00407 0.01675 0.04153 AFIX 43 H28 2 0.737557 0.667347 0.494859 11.00000 -1.20000 AFIX 0 C29 1 0.662682 0.606108 0.502535 11.00000 0.06941 0.06380 = 0.08815 -0.01131 -0.00569 0.04303 C30 1 0.628567 0.569130 0.551157 11.00000 0.05851 0.04705 = 0.08683 -0.00531 0.00399 0.02654 AFIX 43 H30 2 0.595723 0.543893 0.534561 11.00000 -1.20000 AFIX 0 C31 1 0.642010 0.568510 0.624945 11.00000 0.06938 0.04775 = 0.08100 -0.01050 -0.00366 0.03437 C32 1 0.691182 0.606136 0.649947 11.00000 0.05710 0.06543 = 0.07602 -0.01869 -0.00037 0.03519 AFIX 43 H32 2 0.700517 0.607113 0.699237 11.00000 -1.20000 AFIX 0 HKLF 4 REM Me_sphe1_a.res in R3c REM wR2 = 0.2615, GooF = S = 1.030, Restrained GooF = 1.029 for all data REM R1 = 0.0931 for 3145 Fo > 4sig(Fo) and 0.2395 for all 7759 data REM 438 parameters refined using 11 restraints END WGHT 0.1440 0.0000 REM Highest difference peak 0.740, deepest hole -0.386, 1-sigma level 0.119 Q1 1 0.6668 0.5826 0.1857 11.00000 0.05 0.74 Q2 1 0.6667 0.3333 0.6771 10.33333 0.05 0.58 Q3 1 0.7886 0.7102 0.6839 11.00000 0.05 0.33 Q4 1 0.8815 0.6287 0.3540 11.00000 0.05 0.33 Q5 1 0.6263 0.3752 0.3389 11.00000 0.05 0.32 Q6 1 0.5436 0.4546 0.6802 11.00000 0.05 0.31 Q7 1 0.5571 0.3722 0.3364 11.00000 0.05 0.31 Q8 1 0.6094 0.6401 0.4454 11.00000 0.05 0.31 Q9 1 0.5790 0.4805 0.7757 11.00000 0.05 0.30 Q10 1 0.7550 0.7155 0.7099 11.00000 0.05 0.29 Q11 1 0.8934 0.6866 0.3194 11.00000 0.05 0.28 Q12 1 0.8173 0.7591 0.5979 11.00000 0.05 0.27 Q13 1 0.6420 0.3370 0.2548 11.00000 0.05 0.27 Q14 1 0.4884 0.4599 0.6210 11.00000 0.05 0.27 Q15 1 0.8411 0.5160 0.6114 11.00000 0.05 0.27 Q16 1 0.4955 0.4422 0.6170 11.00000 0.05 0.26 Q17 1 0.6564 0.6544 0.4424 11.00000 0.05 0.26 Q18 1 0.7203 0.4389 0.7014 11.00000 0.05 0.26 Q19 1 0.8067 0.6881 0.7581 11.00000 0.05 0.26 Q20 1 0.6661 0.3449 0.3109 11.00000 0.05 0.25 ; _shelx_res_checksum 68211 loop_ _space_group_symop_operation_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, z+1/2' '-x+y, y, z+1/2' 'x, x-y, z+1/2' 'x+2/3, y+1/3, z+1/3' '-y+2/3, x-y+1/3, z+1/3' '-x+y+2/3, -x+1/3, z+1/3' '-y+2/3, -x+1/3, z+5/6' '-x+y+2/3, y+1/3, z+5/6' 'x+2/3, x-y+1/3, z+5/6' 'x+1/3, y+2/3, z+2/3' '-y+1/3, x-y+2/3, z+2/3' '-x+y+1/3, -x+2/3, z+2/3' '-y+1/3, -x+2/3, z+7/6' '-x+y+1/3, y+2/3, z+7/6' 'x+1/3, x-y+2/3, z+7/6' 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 O5A O 0.8288(5) 0.5045(5) 0.6609(8) 0.149(5) Uani 0.54(5) 1 d D . P A 1 C33A C 0.7887(4) 0.5030(4) 0.6280(5) 0.083(3) Uani 0.54(5) 1 d D . P A 1 N5A N 0.7422(4) 0.4622(4) 0.6381(4) 0.082(3) Uani 0.54(5) 1 d D . P A 1 C34A C 0.7379(5) 0.4227(5) 0.6783(8) 0.152(6) Uani 0.54(5) 1 d D . P A 1 H34A H 0.701896 0.395879 0.681001 0.228 Uiso 0.54(5) 1 calc R U P A 1 H34B H 0.757867 0.408904 0.655713 0.228 Uiso 0.54(5) 1 calc R U P A 1 H34C H 0.750969 0.434827 0.727171 0.228 Uiso 0.54(5) 1 calc R U P A 1 O6A O 0.6397(6) 0.5978(6) 0.3055(6) 0.159(6) Uani 0.54(5) 1 d D . P A 1 C35A C 0.6544(4) 0.5894(4) 0.3700(5) 0.084(3) Uani 0.54(5) 1 d D . P A 1 N6A N 0.6475(3) 0.6118(4) 0.4281(6) 0.089(3) Uani 0.54(5) 1 d D . P A 1 C36A C 0.6252(6) 0.6400(6) 0.4194(6) 0.150(6) Uani 0.54(5) 1 d D . P A 1 H36A H 0.622793 0.653808 0.466320 0.224 Uiso 0.54(5) 1 calc R U P A 1 H36B H 0.645739 0.668344 0.386172 0.224 Uiso 0.54(5) 1 calc R U P A 1 H36C H 0.590861 0.618770 0.399293 0.224 Uiso 0.54(5) 1 calc R U P A 1 O5B O 0.7379(5) 0.4227(5) 0.6783(8) 0.152(6) Uani 0.46(5) 1 d D . P A 2 C33B C 0.7422(4) 0.4622(4) 0.6381(4) 0.082(3) Uani 0.46(5) 1 d D . P A 2 N5B N 0.7887(4) 0.5030(4) 0.6280(5) 0.083(3) Uani 0.46(5) 1 d D . P A 2 C34B C 0.8288(5) 0.5045(5) 0.6609(8) 0.149(5) Uani 0.46(5) 1 d D . P A 2 H34D H 0.859987 0.536438 0.648351 0.224 Uiso 0.46(5) 1 calc R U P A 2 H34E H 0.823713 0.502899 0.713448 0.224 Uiso 0.46(5) 1 calc R U P A 2 H34F H 0.832184 0.475317 0.645195 0.224 Uiso 0.46(5) 1 calc R U P A 2 O6B O 0.6252(6) 0.6400(6) 0.4194(6) 0.150(6) Uani 0.46(5) 1 d D . P A 2 C35B C 0.6475(3) 0.6118(4) 0.4281(6) 0.089(3) Uani 0.46(5) 1 d D . P A 2 N6B N 0.6544(4) 0.5894(4) 0.3700(5) 0.084(3) Uani 0.46(5) 1 d D . P A 2 C36B C 0.6397(6) 0.5978(6) 0.3055(6) 0.159(6) Uani 0.46(5) 1 d D . P A 2 H36D H 0.646895 0.579316 0.267972 0.239 Uiso 0.46(5) 1 calc R U P A 2 H36E H 0.602888 0.585665 0.306510 0.239 Uiso 0.46(5) 1 calc R U P A 2 H36F H 0.658485 0.634528 0.294828 0.239 Uiso 0.46(5) 1 calc R U P A 2 O1 O 0.5824(3) 0.5442(3) 0.7228(4) 0.097(2) Uani 1 1 d . . . . . O2 O 0.5694(3) 0.3445(3) 0.4498(4) 0.097(2) Uani 1 1 d . . . . . O3 O 0.8169(3) 0.5540(3) 0.2768(4) 0.097(2) Uani 1 1 d . . . . . O4 O 0.8639(3) 0.7210(3) 0.6147(4) 0.0957(19) Uani 1 1 d . . . . . N1 N 0.5885(3) 0.4809(3) 0.6665(5) 0.090(2) Uani 1 1 d . . . . . N2 N 0.6262(3) 0.4126(3) 0.3830(4) 0.095(3) Uani 1 1 d . . . . . N3 N 0.8391(3) 0.5898(4) 0.3878(4) 0.094(3) Uani 1 1 d . . . . . N4 N 0.7774(3) 0.6816(3) 0.6253(6) 0.093(3) Uani 1 1 d . . . . . C1 C 0.6031(4) 0.5309(3) 0.6759(5) 0.068(2) Uani 1 1 d . . . . . C2 C 0.5460(6) 0.4428(5) 0.7110(10) 0.171(8) Uani 1 1 d . . . . . H2A H 0.539525 0.408455 0.698790 0.256 Uiso 1 1 calc R U . . . H2B H 0.515198 0.444941 0.701373 0.256 Uiso 1 1 calc R U . . . H2C H 0.555056 0.449694 0.762285 0.256 Uiso 1 1 calc R U . . . C3 C 0.6182(4) 0.4638(3) 0.6217(5) 0.071(2) Uani 1 1 d . . . . . C4 C 0.5978(3) 0.4373(3) 0.5579(5) 0.064(2) Uani 1 1 d . . . . . H4 H 0.564748 0.429952 0.542654 0.077 Uiso 1 1 calc R U . . . C5 C 0.6262(3) 0.4210(3) 0.5153(4) 0.062(2) Uani 1 1 d . . . . . C6 C 0.6749(4) 0.4312(3) 0.5400(4) 0.065(2) Uani 1 1 d . . . . . H6 H 0.693951 0.420261 0.511800 0.078 Uiso 1 1 calc R U . . . C7 C 0.6959(4) 0.4575(3) 0.6063(5) 0.070(2) Uani 1 1 d . . . . . C8 C 0.6667(4) 0.4747(3) 0.6475(5) 0.074(2) Uani 1 1 d . . . . . H8 H 0.679866 0.493113 0.691352 0.088 Uiso 1 1 calc R U . . . C9 C 0.6051(3) 0.3907(3) 0.4480(5) 0.067(2) Uani 1 1 d . . . . . C10 C 0.6067(7) 0.3817(5) 0.3170(6) 0.180(9) Uani 1 1 d . . . . . H10A H 0.621350 0.403707 0.274521 0.270 Uiso 1 1 calc R U . . . H10B H 0.569291 0.365617 0.315676 0.270 Uiso 1 1 calc R U . . . H10C H 0.616287 0.355111 0.316853 0.270 Uiso 1 1 calc R U . . . C11 C 0.6628(4) 0.4685(3) 0.3766(4) 0.073(3) Uani 1 1 d . . . . . C12 C 0.6427(4) 0.5013(4) 0.3829(4) 0.076(3) Uani 1 1 d . . . . . H12 H 0.607450 0.487969 0.393273 0.092 Uiso 1 1 calc R U . . . C13 C 0.6760(4) 0.5549(4) 0.3736(4) 0.071(2) Uani 1 1 d . . . . . C14 C 0.7285(3) 0.5735(3) 0.3612(4) 0.066(2) Uani 1 1 d . . . . . H14 H 0.750960 0.609245 0.356496 0.080 Uiso 1 1 calc R U . . . C15 C 0.7485(3) 0.5400(3) 0.3556(4) 0.066(2) Uani 1 1 d . . . . . C16 C 0.7140(4) 0.4862(3) 0.3627(4) 0.063(2) Uani 1 1 d . . . . . H16 H 0.726192 0.462808 0.357906 0.076 Uiso 1 1 calc R U . . . C17 C 0.8029(4) 0.5604(3) 0.3376(5) 0.068(2) Uani 1 1 d . . . . . C18 C 0.8938(5) 0.6129(9) 0.3689(7) 0.186(10) Uani 1 1 d . . . . . H18A H 0.914821 0.632245 0.410448 0.279 Uiso 1 1 calc R U . . . H18B H 0.901563 0.636046 0.327621 0.279 Uiso 1 1 calc R U . . . H18C H 0.901374 0.585872 0.356152 0.279 Uiso 1 1 calc R U . . . C19 C 0.8253(3) 0.5909(4) 0.4657(5) 0.074(3) Uani 1 1 d . . . . . C20 C 0.8101(3) 0.5473(4) 0.5063(6) 0.076(3) Uani 1 1 d . . . . . H20 H 0.807510 0.517566 0.484645 0.091 Uiso 1 1 calc R U . . . C21 C 0.7981(3) 0.5473(4) 0.5829(4) 0.068(2) Uani 1 1 d . . . . . C22 C 0.8005(3) 0.5916(4) 0.6110(5) 0.064(2) Uani 1 1 d . . . . . H22 H 0.791758 0.591883 0.660250 0.076 Uiso 1 1 calc R U . . . C23 C 0.8154(3) 0.6358(3) 0.5684(4) 0.060(2) Uani 1 1 d . . . . . C24 C 0.8289(3) 0.6356(4) 0.4949(4) 0.064(2) Uani 1 1 d . . . . . H24 H 0.840218 0.665229 0.465804 0.076 Uiso 1 1 calc R U . . . C25 C 0.8210(4) 0.6825(4) 0.6026(5) 0.068(2) Uani 1 1 d . . . . . C26 C 0.7831(4) 0.7267(6) 0.6642(12) 0.184(9) Uani 1 1 d . . . . . H26A H 0.749226 0.722788 0.672602 0.276 Uiso 1 1 calc R U . . . H26B H 0.803791 0.757479 0.635176 0.276 Uiso 1 1 calc R U . . . H26C H 0.799991 0.729884 0.710756 0.276 Uiso 1 1 calc R U . . . C27 C 0.7256(3) 0.6418(4) 0.6001(6) 0.078(3) Uani 1 1 d . . . . . C28 C 0.7132(4) 0.6429(4) 0.5272(6) 0.077(2) Uani 1 1 d . . . . . H28 H 0.737557 0.667347 0.494859 0.092 Uiso 1 1 calc R U . . . C29 C 0.6627(3) 0.6061(4) 0.5025(5) 0.069(2) Uani 1 1 d . . . . . C30 C 0.6286(3) 0.5691(3) 0.5512(5) 0.064(2) Uani 1 1 d . . . . . H30 H 0.595723 0.543893 0.534561 0.077 Uiso 1 1 calc R U . . . C31 C 0.6420(3) 0.5685(3) 0.6249(5) 0.064(2) Uani 1 1 d . . . . . C32 C 0.6912(3) 0.6061(3) 0.6499(5) 0.064(2) Uani 1 1 d . . . . . H32 H 0.700517 0.607113 0.699237 0.077 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 O5A 0.130(9) 0.139(10) 0.188(12) 0.022(8) -0.046(8) 0.074(8) C33A 0.091(8) 0.097(7) 0.077(6) -0.001(5) -0.018(5) 0.058(7) N5A 0.107(8) 0.082(6) 0.075(5) 0.002(5) -0.008(5) 0.061(6) C34A 0.171(12) 0.142(10) 0.162(11) 0.032(8) -0.026(9) 0.093(9) O6A 0.205(13) 0.202(13) 0.125(9) 0.024(8) -0.025(9) 0.143(11) C35A 0.082(6) 0.090(6) 0.076(6) 0.016(5) -0.005(5) 0.040(5) N6A 0.075(6) 0.091(6) 0.114(8) 0.024(6) 0.004(5) 0.051(5) C36A 0.186(12) 0.198(13) 0.134(10) 0.032(8) 0.004(8) 0.147(12) O5B 0.171(12) 0.142(10) 0.162(11) 0.032(8) -0.026(9) 0.093(9) C33B 0.107(8) 0.082(6) 0.075(5) 0.002(5) -0.008(5) 0.061(6) N5B 0.091(8) 0.097(7) 0.077(6) -0.001(5) -0.018(5) 0.058(7) C34B 0.130(9) 0.139(10) 0.188(12) 0.022(8) -0.046(8) 0.074(8) O6B 0.186(12) 0.198(13) 0.134(10) 0.032(8) 0.004(8) 0.147(12) C35B 0.075(6) 0.091(6) 0.114(8) 0.024(6) 0.004(5) 0.051(5) N6B 0.082(6) 0.090(6) 0.076(6) 0.016(5) -0.005(5) 0.040(5) C36B 0.205(13) 0.202(13) 0.125(9) 0.024(8) -0.025(9) 0.143(11) O1 0.114(5) 0.080(4) 0.105(5) -0.004(4) 0.021(4) 0.053(4) O2 0.106(5) 0.076(5) 0.082(4) 0.011(4) 0.011(4) 0.024(4) O3 0.093(5) 0.117(5) 0.070(4) -0.024(4) -0.012(4) 0.045(4) O4 0.062(4) 0.094(5) 0.120(5) -0.013(4) 0.000(4) 0.032(4) N1 0.105(6) 0.053(5) 0.114(6) 0.004(4) 0.039(5) 0.041(4) N2 0.117(6) 0.062(5) 0.064(5) 0.017(4) 0.026(5) 0.014(5) N3 0.069(5) 0.128(7) 0.056(4) -0.030(5) -0.005(4) 0.028(5) N4 0.050(4) 0.089(6) 0.132(7) -0.034(5) 0.000(4) 0.029(4) C1 0.073(6) 0.059(6) 0.077(6) -0.009(4) 0.014(5) 0.036(5) C2 0.181(15) 0.061(7) 0.242(18) -0.001(9) 0.129(14) 0.038(8) C3 0.080(7) 0.047(5) 0.081(6) 0.009(4) 0.025(5) 0.029(5) C4 0.064(5) 0.051(5) 0.076(6) 0.011(4) 0.021(4) 0.027(4) C5 0.067(6) 0.058(5) 0.058(5) 0.016(4) 0.015(4) 0.028(4) C6 0.084(6) 0.057(5) 0.055(5) 0.012(4) 0.019(4) 0.035(5) C7 0.077(6) 0.059(5) 0.074(6) 0.016(4) 0.015(5) 0.033(5) C8 0.096(7) 0.048(5) 0.070(5) -0.003(4) 0.006(5) 0.031(5) C9 0.067(5) 0.047(5) 0.080(6) 0.004(4) 0.015(5) 0.022(5) C10 0.232(17) 0.088(9) 0.072(7) -0.014(6) 0.047(9) -0.030(9) C11 0.094(7) 0.061(5) 0.044(4) 0.003(4) 0.002(4) 0.023(5) C12 0.076(6) 0.084(7) 0.049(5) 0.013(4) 0.006(4) 0.025(6) C13 0.086(7) 0.071(6) 0.048(4) 0.001(4) -0.007(4) 0.032(6) C14 0.063(6) 0.060(5) 0.055(4) 0.002(4) -0.009(4) 0.015(5) C15 0.073(6) 0.066(6) 0.051(4) -0.005(4) -0.013(4) 0.030(5) C16 0.076(6) 0.060(6) 0.042(4) -0.001(4) 0.004(4) 0.025(5) C17 0.077(6) 0.071(5) 0.046(5) -0.010(4) -0.001(4) 0.029(5) C18 0.068(8) 0.30(2) 0.086(8) -0.076(11) 0.012(6) 0.013(10) C19 0.058(5) 0.098(8) 0.056(5) -0.011(5) -0.006(4) 0.031(5) C20 0.065(5) 0.078(6) 0.084(6) -0.025(6) -0.021(5) 0.035(5) C21 0.051(5) 0.086(6) 0.060(6) -0.006(5) -0.006(4) 0.029(4) C22 0.049(4) 0.082(6) 0.065(5) -0.019(5) -0.004(4) 0.036(4) C23 0.038(4) 0.078(6) 0.065(5) 0.007(5) 0.007(4) 0.030(4) C24 0.041(4) 0.074(6) 0.058(5) -0.002(4) -0.003(4) 0.015(4) C25 0.051(6) 0.065(6) 0.073(5) -0.009(4) 0.001(4) 0.018(5) C26 0.060(7) 0.151(13) 0.31(2) -0.145(15) 0.006(10) 0.032(7) C27 0.050(5) 0.074(6) 0.114(8) -0.022(6) 0.000(5) 0.035(5) C28 0.070(6) 0.074(6) 0.093(7) 0.004(5) 0.017(5) 0.042(5) C29 0.069(6) 0.064(6) 0.088(6) -0.011(5) -0.006(5) 0.043(5) C30 0.059(5) 0.047(5) 0.087(6) -0.005(4) 0.004(5) 0.027(4) C31 0.069(6) 0.048(5) 0.081(6) -0.010(4) -0.004(5) 0.034(4) C32 0.057(5) 0.065(5) 0.076(5) -0.019(5) 0.000(4) 0.035(5) 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 O5A C33A N5A 119.0(9) . . ? O5A C33A C21 117.8(10) . . ? N5A C33A C21 123.3(8) . . ? C33A N5A C34A 118.6(9) . . ? C33A N5A C7 123.3(7) . . ? C34A N5A C7 118.1(10) . . ? N6A C35A O6A 117.9(10) . . ? N6A C35A C13 123.6(8) . . ? O6A C35A C13 118.5(10) . . ? C36A N6A C35A 118.7(10) . . ? C36A N6A C29 117.9(10) . . ? C35A N6A C29 123.3(8) . . ? N5B C33B O5B 118.6(9) . . ? N5B C33B C7 123.3(7) . . ? O5B C33B C7 118.1(10) . . ? C34B N5B C33B 119.0(9) . . ? C34B N5B C21 117.8(10) . . ? C33B N5B C21 123.3(8) . . ? O6B C35B N6B 118.7(10) . . ? O6B C35B C29 117.9(10) . . ? N6B C35B C29 123.3(8) . . ? C35B N6B C36B 117.9(10) . . ? C35B N6B C13 123.6(8) . . ? C36B N6B C13 118.5(10) . . ? C1 N1 C2 118.0(8) . . ? C1 N1 C3 122.6(7) . . ? C2 N1 C3 118.7(8) . . ? C9 N2 C10 118.7(8) . . ? C9 N2 C11 121.4(7) . . ? C10 N2 C11 119.3(7) . . ? C17 N3 C18 119.1(8) . . ? C17 N3 C19 121.5(7) . . ? C18 N3 C19 118.3(7) . . ? C25 N4 C26 117.7(8) . . ? C25 N4 C27 122.0(8) . . ? C26 N4 C27 119.2(8) . . ? O1 C1 N1 120.7(8) . . ? O1 C1 C31 121.7(7) . . ? N1 C1 C31 117.5(7) . . ? C4 C3 C8 122.2(8) . . ? C4 C3 N1 120.2(9) . . ? C8 C3 N1 117.6(9) . . ? C3 C4 C5 120.1(8) . . ? C6 C5 C4 119.0(8) . . ? C6 C5 C9 118.9(8) . . ? C4 C5 C9 122.1(8) . . ? C5 C6 C7 121.5(8) . . ? C6 C7 C8 118.2(9) . . ? C6 C7 C33B 122.6(8) . . ? C8 C7 C33B 118.7(8) . . ? C6 C7 N5A 122.6(8) . . ? C8 C7 N5A 118.7(8) . . ? C3 C8 C7 119.0(8) . . ? O2 C9 N2 119.4(8) . . ? O2 C9 C5 121.5(8) . . ? N2 C9 C5 119.0(7) . . ? C16 C11 C12 122.6(8) . . ? C16 C11 N2 120.3(10) . . ? C12 C11 N2 117.1(10) . . ? C11 C12 C13 118.9(9) . . ? C14 C13 C12 118.9(9) . . ? C14 C13 C35A 121.1(8) . . ? C12 C13 C35A 119.8(9) . . ? C14 C13 N6B 121.1(8) . . ? C12 C13 N6B 119.8(9) . . ? C13 C14 C15 121.6(8) . . ? C14 C15 C16 118.4(8) . . ? C14 C15 C17 120.1(8) . . ? C16 C15 C17 121.3(8) . . ? C11 C16 C15 119.5(8) . . ? O3 C17 N3 119.3(8) . . ? O3 C17 C15 122.0(8) . . ? N3 C17 C15 118.6(8) . . ? C20 C19 C24 122.4(8) . . ? C20 C19 N3 117.6(10) . . ? C24 C19 N3 120.0(9) . . ? C19 C20 C21 119.5(9) . . ? C22 C21 C20 117.6(8) . . ? C22 C21 C33A 123.3(8) . . ? C20 C21 C33A 118.9(9) . . ? C22 C21 N5B 123.3(8) . . ? C20 C21 N5B 118.9(9) . . ? C21 C22 C23 122.3(7) . . ? C22 C23 C24 119.0(8) . . ? C22 C23 C25 119.5(7) . . ? C24 C23 C25 121.3(8) . . ? C19 C24 C23 119.2(8) . . ? O4 C25 N4 120.0(8) . . ? O4 C25 C23 122.3(8) . . ? N4 C25 C23 117.6(8) . . ? C28 C27 C32 122.9(9) . . ? C28 C27 N4 117.9(10) . . ? C32 C27 N4 119.2(10) . . ? C27 C28 C29 118.7(9) . . ? C30 C29 C28 118.9(9) . . ? C30 C29 N6A 122.6(8) . . ? C28 C29 N6A 118.3(9) . . ? C30 C29 C35B 122.6(8) . . ? C28 C29 C35B 118.3(9) . . ? C29 C30 C31 121.6(8) . . ? C32 C31 C30 119.4(8) . . ? C32 C31 C1 120.9(8) . . ? C30 C31 C1 119.6(8) . . ? C27 C32 C31 118.4(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 O5A C33A 1.307(12) . ? C33A N5A 1.312(13) . ? C33A C21 1.446(13) . ? N5A C34A 1.327(12) . ? N5A C7 1.426(13) . ? O6A C35A 1.312(12) . ? C35A N6A 1.311(13) . ? C35A C13 1.449(13) . ? N6A C36A 1.306(12) . ? N6A C29 1.456(13) . ? O5B C33B 1.327(12) . ? C33B N5B 1.312(13) . ? C33B C7 1.426(13) . ? N5B C34B 1.307(12) . ? N5B C21 1.446(13) . ? O6B C35B 1.306(12) . ? C35B N6B 1.311(13) . ? C35B C29 1.456(13) . ? N6B C36B 1.312(12) . ? N6B C13 1.449(13) . ? O1 C1 1.222(10) . ? O2 C9 1.239(10) . ? O3 C17 1.223(10) . ? O4 C25 1.227(10) . ? N1 C1 1.329(11) . ? N1 C2 1.441(14) . ? N1 C3 1.458(11) . ? N2 C9 1.337(11) . ? N2 C10 1.438(14) . ? N2 C11 1.459(11) . ? N3 C17 1.340(12) . ? N3 C18 1.447(14) . ? N3 C19 1.473(11) . ? N4 C25 1.341(11) . ? N4 C26 1.441(14) . ? N4 C27 1.461(12) . ? C1 C31 1.458(12) . ? C3 C4 1.356(13) . ? C3 C8 1.383(13) . ? C4 C5 1.392(12) . ? C5 C6 1.390(12) . ? C5 C9 1.454(12) . ? C6 C7 1.395(12) . ? C7 C8 1.414(12) . ? C11 C16 1.355(13) . ? C11 C12 1.370(13) . ? C12 C13 1.397(13) . ? C13 C14 1.382(13) . ? C14 C15 1.385(12) . ? C15 C16 1.402(12) . ? C15 C17 1.447(12) . ? C19 C20 1.350(13) . ? C19 C24 1.376(13) . ? C20 C21 1.431(13) . ? C21 C22 1.373(12) . ? C22 C23 1.386(11) . ? C23 C24 1.390(11) . ? C23 C25 1.445(12) . ? C27 C28 1.373(14) . ? C27 C32 1.375(13) . ? C28 C29 1.409(13) . ? C29 C30 1.372(12) . ? C30 C31 1.396(12) . ? C31 C32 1.392(11) . ?