#------------------------------------------------------------------------------ #$Date: 2020-05-04 12:32:27 +0300 (Mon, 04 May 2020) $ #$Revision: 251492 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/12/64/7126491.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_7126491 loop_ _publ_author_name 'Levine, Andrew M.' 'Bu, Guanhong' 'Biswas, Sankarsan' 'Tsai, Esther H. R.' 'Braunschweig, Adam B.' 'Nannenga, Brent L.' _publ_section_title ; Crystal structure and orientation of organic semiconductor thin films by microcrystal electron diffraction and grazing-incidence wide-angle X-ray scattering. ; _journal_issue 30 _journal_name_full 'Chemical communications (Cambridge, England)' _journal_page_first 4204 _journal_page_last 4207 _journal_paper_doi 10.1039/d0cc00119h _journal_volume 56 _journal_year 2020 _chemical_formula_sum 'C128 H96 N16 O16' _chemical_formula_weight 2114.27 _chemical_name_common 'dPyr PDI' _chemical_name_systematic 'dipyrrolodine perylene diimide' _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_Hall 'C -2yc' _space_group_name_H-M_alt 'C 1 c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2019-11-05 deposited with the CCDC. 2020-03-13 downloaded from the CCDC. ; _cell_angle_alpha 90.00(3) _cell_angle_beta 101.29(3) _cell_angle_gamma 90.00(3) _cell_formula_units_Z 1 _cell_length_a 22.050(4) _cell_length_b 10.760(2) _cell_length_c 9.340(2) _cell_measurement_temperature 77 _cell_volume 2173.1(8) _computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 77 _diffrn_measured_fraction_theta_full 0.908 _diffrn_measured_fraction_theta_max 0.861 _diffrn_measurement_device_type Titan_Krios _diffrn_radiation_type electron _diffrn_radiation_wavelength 1.000 _diffrn_reflns_av_R_equivalents 0.1844 _diffrn_reflns_av_unetI/netI 0.2247 _diffrn_reflns_Laue_measured_fraction_full 0.908 _diffrn_reflns_Laue_measured_fraction_max 0.861 _diffrn_reflns_limit_h_max 35 _diffrn_reflns_limit_h_min -36 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 23427 _diffrn_reflns_point_group_measured_fraction_full 0.903 _diffrn_reflns_point_group_measured_fraction_max 0.828 _diffrn_reflns_theta_full 36.870 _diffrn_reflns_theta_max 56.438 _diffrn_reflns_theta_min 4.504 _exptl_absorpt_coefficient_mu 0.000 _exptl_crystal_density_diffrn 1.616 _exptl_crystal_description Micro/Nanocrystals _exptl_crystal_F_000 439 _refine_diff_density_max 0.453 _refine_diff_density_min -0.385 _refine_diff_density_rms 0.072 _refine_ls_abs_structure_details ; All f" are zero, so absolute structure could not be determined ; _refine_ls_extinction_coef 0.12(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 1.423 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 162 _refine_ls_number_reflns 8728 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.422 _refine_ls_R_factor_all 0.2355 _refine_ls_R_factor_gt 0.1991 _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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.4813 _refine_ls_wR_factor_ref 0.5085 _reflns_Friedel_coverage 0.922 _reflns_Friedel_fraction_full 0.898 _reflns_Friedel_fraction_max 0.795 _reflns_number_gt 5207 _reflns_number_total 8728 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0cc00119h2.cif _cod_data_source_block dPyr_all_b _cod_original_sg_symbol_H-M 'C c' _cod_database_code 7126491 _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. ; _shelx_res_file ; TITL dPyr_all_b.res in Cc dPyr_all_b.res created by SHELXL-2018/3 at 22:52:02 on 23-Sep-2019 REM Old TITL all merge REM SHELXT solution in Cc: R1 0.251, Rweak 0.336, Alpha 0.129 REM 4.501 for 70 systematic absences, Orientation as input REM Flack x = 0.458 ( 0.124 ) from 1584 Parsons' quotients REM Formula found by SHELXT: C22 N8 O9 CELL 1.000 22.0500 10.7600 9.3400 90.000 101.287 90.000 ZERR 1.000 0.0040 0.0020 0.0020 0.030 0.030 0.030 LATT -7 SYMM X, -Y, 1/2+Z SFAC H 0.042 0.991 0.103 3.924 0.205 11.597 0.170 31.984 0.006 = 0.0 0.0 0.000 0.310 1.008 SFAC C 0.208 0.922 0.702 5.018 1.144 16.523 0.425 47.300 0.030 = 0.0 0.0 0.000 0.770 12.011 SFAC N 0.216 0.843 0.649 4.055 0.968 12.693 0.345 36.058 0.032 = 0.0 0.0 0.000 0.700 14.007 SFAC O 0.308 1.088 0.733 4.593 0.710 13.052 0.185 33.768 0.048 = 0.0 0.0 0.000 0.660 15.999 UNIT 96 128 16 16 ACTA L.S. 100 BOND LIST 6 FMAP 2 PLAN 20 WGHT 0.200000 EXTI 0.120142 FVAR 1.26446 C1 2 0.452329 0.387381 0.802061 11.00000 0.01527 AFIX 23 H1A 1 0.485092 0.350019 0.873588 11.00000 -1.20000 H1AB 1 0.469718 0.423630 0.723950 11.00000 -1.20000 AFIX 0 C2 2 0.617513 0.157738 0.661609 11.00000 0.00670 N3 3 0.736697 0.094799 0.828380 11.00000 0.01256 AFIX 43 H3 1 0.771041 0.064150 0.874404 11.00000 -1.20000 AFIX 0 C3 2 0.556715 0.388708 0.206107 11.00000 0.02235 AFIX 23 H3A 1 0.541166 0.416084 0.291092 11.00000 -1.20000 H3AB 1 0.522981 0.351008 0.137606 11.00000 -1.20000 AFIX 0 C4 2 0.336312 0.206165 0.527520 11.00000 0.02158 AFIX 43 H4 1 0.300970 0.221574 0.565084 11.00000 -1.20000 AFIX 0 C5 2 0.418370 0.475327 0.866283 11.00000 0.02984 AFIX 23 H5A 1 0.447193 0.520032 0.940267 11.00000 -1.20000 H5B 1 0.400950 0.535022 0.791677 11.00000 -1.20000 AFIX 0 C6 2 0.732457 0.123258 0.686717 11.00000 0.02000 C7 2 0.522261 0.144264 0.798939 11.00000 0.01135 AFIX 43 H7 1 0.488087 0.140551 0.843451 11.00000 -1.20000 AFIX 0 C008 2 0.563684 0.186571 0.581009 11.00000 0.01060 C8 2 0.454626 0.202831 0.566113 11.00000 0.01562 C9 2 0.603883 0.244339 0.367032 11.00000 0.01444 C00A 2 0.315082 0.093094 0.101378 11.00000 0.03473 O00B 4 0.780146 0.128151 0.636704 11.00000 0.02636 N00C 3 0.604396 0.304052 0.246501 11.00000 0.01846 C00G 2 0.509378 0.175102 0.642889 11.00000 0.01461 C00J 2 0.671006 0.164958 0.589532 11.00000 0.01711 O00K 4 0.297659 0.102494 -0.035011 11.00000 0.03527 O00L 4 0.703967 0.090873 1.029829 11.00000 0.01682 C00M 2 0.330202 0.159611 0.389791 11.00000 0.01611 C00N 2 0.631764 0.121865 0.811496 11.00000 0.02684 O00O 4 0.224473 0.136872 0.360934 11.00000 0.02475 N01 3 0.402821 0.297168 0.745973 11.00000 0.02134 N0 3 0.264636 0.092266 0.177787 11.00000 0.02088 AFIX 43 H0 1 0.229287 0.065852 0.132218 11.00000 -1.20000 AFIX 0 C09 2 0.574963 0.121703 0.881949 11.00000 0.01772 AFIX 43 H09 1 0.578254 0.105916 0.981070 11.00000 -1.20000 AFIX 0 C001 2 0.660564 0.331762 0.198335 11.00000 0.01921 AFIX 23 H00A 1 0.678210 0.258303 0.162273 11.00000 -1.20000 H00B 1 0.690930 0.369693 0.275086 11.00000 -1.20000 AFIX 0 C0 2 0.636100 0.425154 0.073515 11.00000 0.01768 AFIX 23 H0A 1 0.618563 0.381774 -0.016073 11.00000 -1.20000 H0AB 1 0.668967 0.479319 0.055505 11.00000 -1.20000 AFIX 0 C00P 2 0.443089 0.171781 0.412280 11.00000 0.00961 C00Q 2 0.393959 0.231266 0.613450 11.00000 0.01518 C00R 2 0.492111 0.182940 0.336213 11.00000 0.01113 C00S 2 0.691589 0.110640 0.902468 11.00000 0.00135 C00T 2 0.421231 0.124346 0.116292 11.00000 0.02102 AFIX 43 H00T 1 0.413926 0.097099 0.019947 11.00000 -1.20000 AFIX 0 C00U 2 0.376781 0.154873 0.320100 11.00000 0.02648 C00V 2 0.347385 0.344478 0.802759 11.00000 0.02629 AFIX 23 H00C 1 0.325751 0.276277 0.838629 11.00000 -1.20000 H00D 1 0.318895 0.387181 0.726231 11.00000 -1.20000 AFIX 0 C00W 2 0.376343 0.133054 0.182734 11.00000 0.00763 C00X 2 0.373392 0.434005 0.926664 11.00000 0.02578 AFIX 23 H00E 1 0.344239 0.498596 0.939524 11.00000 -1.20000 H00F 1 0.388298 0.391693 1.018515 11.00000 -1.20000 AFIX 0 C00Y 2 0.484617 0.156687 0.189345 11.00000 0.02386 AFIX 43 H00Y 1 0.517323 0.159230 0.139864 11.00000 -1.20000 AFIX 0 C010 2 0.269507 0.130523 0.316877 11.00000 0.02141 C011 2 0.584250 0.502355 0.132676 11.00000 0.01116 AFIX 23 H01A 1 0.601682 0.565433 0.202991 11.00000 -1.20000 H01B 1 0.554274 0.539523 0.054512 11.00000 -1.20000 AFIX 0 C012 2 0.559135 0.201335 0.432990 11.00000 0.00872 C013 2 0.665275 0.203541 0.448637 11.00000 0.01894 AFIX 43 H013 1 0.699469 0.204312 0.404048 11.00000 -1.20000 REM ##### AFIX 0 HKLF 4 REM dPyr_all_b.res in Cc REM wR2 = 0.5085, GooF = S = 1.423, Restrained GooF = 1.422 for all data REM R1 = 0.1991 for 5207 Fo > 4sig(Fo) and 0.2355 for all 8728 data REM 162 parameters refined using 2 restraints END WGHT 0.2000 0.0000 REM Highest difference peak 0.453, deepest hole -0.385, 1-sigma level 0.072 Q1 1 0.6998 0.1124 0.8582 11.00000 0.05 0.45 Q2 1 0.7126 0.0856 0.9774 11.00000 0.05 0.41 Q3 1 0.5783 0.4999 0.1771 11.00000 0.05 0.39 Q4 1 0.7442 0.1009 0.7756 11.00000 0.05 0.39 Q5 1 0.6831 0.1100 0.9483 11.00000 0.05 0.37 Q6 1 0.7301 0.0897 0.8755 11.00000 0.05 0.37 Q7 1 0.6127 0.2571 0.3213 11.00000 0.05 0.34 Q8 1 0.5620 0.2002 0.3816 11.00000 0.05 0.33 Q9 1 0.3328 0.2155 0.5786 11.00000 0.05 0.32 Q10 1 0.6267 0.1609 0.6205 11.00000 0.05 0.32 Q11 1 0.2577 0.0984 0.2257 11.00000 0.05 0.31 Q12 1 0.4117 0.2938 0.6982 11.00000 0.05 0.31 Q13 1 0.6095 0.3033 0.2007 11.00000 0.05 0.30 Q14 1 0.7854 0.1311 0.5817 11.00000 0.05 0.29 Q15 1 0.2195 0.1379 0.4125 11.00000 0.05 0.29 Q16 1 0.3082 0.1066 0.1407 11.00000 0.05 0.29 Q17 1 0.3389 0.1527 0.3518 11.00000 0.05 0.28 Q18 1 0.5911 0.5034 0.0873 11.00000 0.05 0.28 Q19 1 0.7381 0.1332 0.6370 11.00000 0.05 0.28 Q20 1 0.5524 0.2015 0.4744 11.00000 0.05 0.28 ; _shelx_res_checksum 22836 loop_ _space_group_symop_operation_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -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 _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.4523(4) 0.3874(8) 0.8021(11) 0.0153(16) Uiso 1 1 d . . . . . H1A H 0.485092 0.350019 0.873588 0.018 Uiso 1 1 calc R U . . . H1AB H 0.469718 0.423630 0.723950 0.018 Uiso 1 1 calc R U . . . C2 C 0.6175(3) 0.1577(7) 0.6616(9) 0.0067(12) Uiso 1 1 d . . . . . N3 N 0.7367(3) 0.0948(7) 0.8284(9) 0.0126(13) Uiso 1 1 d . . . . . H3 H 0.771041 0.064150 0.874404 0.015 Uiso 1 1 calc R U . . . C3 C 0.5567(5) 0.3887(10) 0.2061(13) 0.022(2) Uiso 1 1 d . . . . . H3A H 0.541166 0.416084 0.291092 0.027 Uiso 1 1 calc R U . . . H3AB H 0.522981 0.351008 0.137606 0.027 Uiso 1 1 calc R U . . . C4 C 0.3363(5) 0.2062(10) 0.5275(12) 0.022(2) Uiso 1 1 d . . . . . H4 H 0.300970 0.221574 0.565084 0.026 Uiso 1 1 calc R U . . . C5 C 0.4184(5) 0.4753(12) 0.8663(14) 0.030(2) Uiso 1 1 d . . . . . H5A H 0.447193 0.520032 0.940267 0.036 Uiso 1 1 calc R U . . . H5B H 0.400950 0.535022 0.791677 0.036 Uiso 1 1 calc R U . . . C6 C 0.7325(5) 0.1233(10) 0.6867(12) 0.0200(19) Uiso 1 1 d . . . . . C7 C 0.5223(4) 0.1443(8) 0.7989(10) 0.0114(15) Uiso 1 1 d . . . . . H7 H 0.488087 0.140551 0.843451 0.014 Uiso 1 1 calc R U . . . C008 C 0.5637(4) 0.1866(8) 0.5810(10) 0.0106(14) Uiso 1 1 d . . . . . C8 C 0.4546(4) 0.2028(9) 0.5661(11) 0.0156(16) Uiso 1 1 d . . . . . C9 C 0.6039(4) 0.2443(8) 0.3670(11) 0.0144(16) Uiso 1 1 d . . . . . C00A C 0.3151(6) 0.0931(13) 0.1014(16) 0.035(3) Uiso 1 1 d . . . . . O00B O 0.7801(4) 0.1282(9) 0.6367(11) 0.0264(17) Uiso 1 1 d . . . . . N00C N 0.6044(4) 0.3041(8) 0.2465(10) 0.0185(15) Uiso 1 1 d . . . . . C00G C 0.5094(4) 0.1751(9) 0.6429(11) 0.0146(17) Uiso 1 1 d . . . . . C00J C 0.6710(4) 0.1650(10) 0.5895(11) 0.0171(17) Uiso 1 1 d . . . . . O00K O 0.2977(5) 0.1025(11) -0.0350(13) 0.035(2) Uiso 1 1 d . . . . . O00L O 0.7040(3) 0.0909(7) 1.0298(9) 0.0168(13) Uiso 1 1 d . . . . . C00M C 0.3302(4) 0.1596(10) 0.3898(11) 0.0161(17) Uiso 1 1 d . . . . . C00N C 0.6318(5) 0.1219(12) 0.8115(15) 0.027(2) Uiso 1 1 d . . . . . O00O O 0.2245(4) 0.1369(9) 0.3609(11) 0.0247(16) Uiso 1 1 d . . . . . N01 N 0.4028(4) 0.2972(9) 0.7460(11) 0.0213(17) Uiso 1 1 d . . . . . N0 N 0.2646(4) 0.0923(8) 0.1778(11) 0.0209(17) Uiso 1 1 d . . . . . H0 H 0.229287 0.065852 0.132218 0.025 Uiso 1 1 calc R U . . . C09 C 0.5750(4) 0.1217(9) 0.8819(12) 0.0177(17) Uiso 1 1 d . . . . . H09 H 0.578254 0.105916 0.981070 0.021 Uiso 1 1 calc R U . . . C001 C 0.6606(4) 0.3318(9) 0.1983(12) 0.0192(18) Uiso 1 1 d . . . . . H00A H 0.678210 0.258303 0.162273 0.023 Uiso 1 1 calc R U . . . H00B H 0.690930 0.369693 0.275086 0.023 Uiso 1 1 calc R U . . . C0 C 0.6361(4) 0.4252(9) 0.0735(11) 0.0177(17) Uiso 1 1 d . . . . . H0A H 0.618563 0.381774 -0.016073 0.021 Uiso 1 1 calc R U . . . H0AB H 0.668967 0.479319 0.055505 0.021 Uiso 1 1 calc R U . . . C00P C 0.4431(4) 0.1718(8) 0.4123(10) 0.0096(14) Uiso 1 1 d . . . . . C00Q C 0.3940(4) 0.2313(9) 0.6134(11) 0.0152(16) Uiso 1 1 d . . . . . C00R C 0.4921(4) 0.1829(8) 0.3362(10) 0.0111(15) Uiso 1 1 d . . . . . C00S C 0.6916(3) 0.1106(6) 0.9025(8) 0.0014(11) Uiso 1 1 d . . . . . C00T C 0.4212(5) 0.1243(10) 0.1163(13) 0.0210(19) Uiso 1 1 d . . . . . H00T H 0.413926 0.097099 0.019947 0.025 Uiso 1 1 calc R U . . . C00U C 0.3768(5) 0.1549(11) 0.3201(14) 0.026(2) Uiso 1 1 d . . . . . C00V C 0.3474(5) 0.3445(11) 0.8028(13) 0.026(2) Uiso 1 1 d . . . . . H00C H 0.325751 0.276277 0.838629 0.032 Uiso 1 1 calc R U . . . H00D H 0.318895 0.387181 0.726231 0.032 Uiso 1 1 calc R U . . . C00W C 0.3763(3) 0.1331(7) 0.1827(9) 0.0076(13) Uiso 1 1 d . . . . . C00X C 0.3734(5) 0.4340(11) 0.9267(13) 0.026(2) Uiso 1 1 d . . . . . H00E H 0.344239 0.498596 0.939524 0.031 Uiso 1 1 calc R U . . . H00F H 0.388298 0.391693 1.018515 0.031 Uiso 1 1 calc R U . . . C00Y C 0.4846(5) 0.1567(11) 0.1893(13) 0.024(2) Uiso 1 1 d . . . . . H00Y H 0.517323 0.159230 0.139864 0.029 Uiso 1 1 calc R U . . . C010 C 0.2695(5) 0.1305(11) 0.3169(13) 0.021(2) Uiso 1 1 d . . . . . C011 C 0.5842(4) 0.5024(7) 0.1327(10) 0.0112(14) Uiso 1 1 d . . . . . H01A H 0.601682 0.565433 0.202991 0.013 Uiso 1 1 calc R U . . . H01B H 0.554274 0.539523 0.054512 0.013 Uiso 1 1 calc R U . . . C012 C 0.5591(3) 0.2013(7) 0.4330(9) 0.0087(13) Uiso 1 1 d . . . . . C013 C 0.6653(4) 0.2035(10) 0.4486(11) 0.0189(18) Uiso 1 1 d . . . . . H013 H 0.699469 0.204312 0.404048 0.023 Uiso 1 1 calc R U . . . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0000 0.0000 '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 C5 C1 N01 100.0(8) . . ? C008 C2 C00N 128.9(9) . . ? C008 C2 C00J 116.2(8) . . ? C00N C2 C00J 114.9(8) . . ? C00S N3 C6 124.7(7) . . ? N00C C3 C011 106.9(8) . . ? C00M C4 C00Q 121.8(10) . . ? C00X C5 C1 117.7(12) . . ? O00B C6 N3 118.9(9) . . ? O00B C6 C00J 118.7(10) . . ? N3 C6 C00J 122.0(9) . . ? C09 C7 C00G 128.1(9) . . ? C2 C008 C012 118.9(8) . . ? C2 C008 C00G 118.8(8) . . ? C012 C008 C00G 120.9(7) . . ? C00G C8 C00P 117.0(9) . . ? C00G C8 C00Q 130.9(9) . . ? C00P C8 C00Q 110.0(7) . . ? N00C C9 C012 134.4(9) . . ? N00C C9 C013 115.5(9) . . ? C012 C9 C013 109.9(8) . . ? O00K C00A N0 113.0(11) . . ? O00K C00A C00W 124.3(13) . . ? N0 C00A C00W 117.8(11) . . ? C9 N00C C3 115.2(10) . . ? C9 N00C C001 122.1(8) . . ? C3 N00C C001 115.8(9) . . ? C8 C00G C008 120.8(9) . . ? C8 C00G C7 124.9(9) . . ? C008 C00G C7 113.9(7) . . ? C013 C00J C2 121.8(8) . . ? C013 C00J C6 124.2(9) . . ? C2 C00J C6 114.0(8) . . ? C00U C00M C4 122.5(9) . . ? C00U C00M C010 120.6(10) . . ? C4 C00M C010 116.5(10) . . ? C2 C00N C00S 127.4(11) . . ? C2 C00N C09 112.5(9) . . ? C00S C00N C09 119.0(10) . . ? C00Q N01 C1 127.5(9) . . ? C00Q N01 C00V 119.7(8) . . ? C1 N01 C00V 104.3(8) . . ? C010 N0 C00A 123.7(9) . . ? C7 C09 C00N 117.4(10) . . ? N00C C001 C0 100.1(7) . . ? C001 C0 C011 104.1(8) . . ? C00R C00P C8 118.5(7) . . ? C00R C00P C00U 117.5(8) . . ? C8 C00P C00U 122.7(8) . . ? C4 C00Q N01 124.0(9) . . ? C4 C00Q C8 123.4(9) . . ? N01 C00Q C8 112.3(8) . . ? C00Y C00R C00P 122.0(8) . . ? C00Y C00R C012 120.6(8) . . ? C00P C00R C012 116.4(7) . . ? O00L C00S N3 116.8(7) . . ? O00L C00S C00N 128.1(9) . . ? N3 C00S C00N 113.5(8) . . ? C00W C00T C00Y 121.1(10) . . ? C00W C00U C00M 129.5(10) . . ? C00W C00U C00P 113.0(9) . . ? C00M C00U C00P 117.4(10) . . ? N01 C00V C00X 105.6(8) . . ? C00T C00W C00U 129.7(9) . . ? C00T C00W C00A 116.6(10) . . ? C00U C00W C00A 112.9(10) . . ? C5 C00X C00V 95.2(10) . . ? C00R C00Y C00T 115.3(10) . . ? O00O C010 N0 116.9(10) . . ? O00O C010 C00M 128.2(11) . . ? N0 C010 C00M 114.9(10) . . ? C3 C011 C0 96.3(7) . . ? C9 C012 C008 125.8(8) . . ? C9 C012 C00R 117.9(8) . . ? C008 C012 C00R 115.8(7) . . ? C00J C013 C9 119.3(9) . . ? 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 C5 1.411(16) . ? C1 N01 1.478(13) . ? C2 C008 1.312(10) . ? C2 C00N 1.427(16) . ? C2 C00J 1.470(13) . ? N3 C00S 1.329(11) . ? N3 C6 1.343(14) . ? C3 N00C 1.386(13) . ? C3 C011 1.580(14) . ? C4 C00M 1.362(15) . ? C4 C00Q 1.390(13) . ? C5 C00X 1.311(17) . ? C6 O00B 1.232(15) . ? C6 C00J 1.543(13) . ? C7 C09 1.288(12) . ? C7 C00G 1.467(13) . ? C008 C012 1.376(13) . ? C008 C00G 1.433(13) . ? C8 C00G 1.312(12) . ? C8 C00P 1.448(14) . ? C8 C00Q 1.520(14) . ? C9 N00C 1.298(15) . ? C9 C012 1.344(13) . ? C9 C013 1.484(13) . ? C00A O00K 1.26(2) . ? C00A N0 1.434(18) . ? C00A C00W 1.478(15) . ? N00C C001 1.429(14) . ? C00J C013 1.362(15) . ? O00L C00S 1.186(11) . ? C00M C00U 1.320(17) . ? C00M C010 1.413(13) . ? C00N C00S 1.428(13) . ? C00N C09 1.525(17) . ? O00O C010 1.149(15) . ? N01 C00Q 1.407(14) . ? N01 C00V 1.513(15) . ? N0 C010 1.347(16) . ? C001 C0 1.554(14) . ? C0 C011 1.597(13) . ? C00P C00R 1.410(13) . ? C00P C00U 1.555(13) . ? C00R C00Y 1.378(16) . ? C00R C012 1.587(11) . ? C00T C00W 1.270(14) . ? C00T C00Y 1.472(14) . ? C00U C00W 1.302(16) . ? C00V C00X 1.529(17) . ?