#------------------------------------------------------------------------------ #$Date: 2019-10-07 11:58:45 +0300 (Mon, 07 Oct 2019) $ #$Revision: 219126 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/23/44/7234414.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_7234414 loop_ _publ_author_name 'Arthur D. Hendsbee' 'Seth M. McAfee' 'Jon-Paul Sun' 'Theresa M. McCormick' 'Ian G. Hill' 'Gregory C. Welch' _publ_section_title ; Phthalimide-based pi-conjugated small molecules with tailored electronic energy levels for use as acceptors in organic solar cells ; _journal_name_full 'Journal of Materials Chemistry C' _journal_page_first 8904 _journal_page_last 8915 _journal_paper_doi 10.1039/C5TC01877C _journal_volume 3 _journal_year 2015 _chemical_formula_sum 'C58 H56 N4 O8 S2' _chemical_formula_weight 1001.19 _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _cell_angle_alpha 90.00 _cell_angle_beta 99.160(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 22.612(3) _cell_length_b 11.4854(13) _cell_length_c 20.156(2) _cell_measurement_reflns_used 5593 _cell_measurement_temperature 125(2) _cell_measurement_theta_max 25.03 _cell_measurement_theta_min 2.17 _cell_volume 5167.9(10) _computing_cell_refinement 'Bruker SAINT' _computing_data_collection 'Bruker APEX2' _computing_data_reduction 'Bruker SAINT' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _diffrn_ambient_temperature 125(2) _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0695 _diffrn_reflns_av_sigmaI/netI 0.0534 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_number 26224 _diffrn_reflns_theta_full 25.84 _diffrn_reflns_theta_max 25.84 _diffrn_reflns_theta_min 1.99 _exptl_absorpt_coefficient_mu 0.163 _exptl_absorpt_correction_T_max 0.7453 _exptl_absorpt_correction_T_min 0.6941 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS (Bruker 2008)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.287 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 2112 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: CH2Cl2' _exptl_crystal_size_max .298 _exptl_crystal_size_mid .241 _exptl_crystal_size_min .232 _refine_diff_density_max 0.819 _refine_diff_density_min -0.344 _refine_diff_density_rms 0.062 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 377 _refine_ls_number_reflns 4982 _refine_ls_number_restraints 37 _refine_ls_restrained_S_all 1.068 _refine_ls_R_factor_all 0.0918 _refine_ls_R_factor_gt 0.0556 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0796P)^2^+4.5009P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1422 _refine_ls_wR_factor_ref 0.1623 _reflns_number_gt 3334 _reflns_number_total 4982 _reflns_threshold_expression >2sigma(I) _iucr_refine_instructions_details ; TITL 20150109_Art2_0m in C2/c CELL 0.71073 22.6118 11.4854 20.156 90 99.16 90 ZERR 4 0.0026 0.0013 0.0023 0 0.002 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O S UNIT 232 224 16 32 8 L.S. 35 ACTA BOND $H FMAP 2 PLAN 3 DFIX 1.50 .01 C25 C26 DFIX 1.50 .01 C25 C28 DFIX 1.50 .01 C28 C29 DFIX 1.50 .01 C26 C27 DFIX 1.50 .01 C25 C26B DFIX 1.50 .01 C25 C28B DFIX 1.50 .01 C28B C29B DFIX 1.50 .01 C26B C27B DFIX 1.40 .02 N2 C25B DELU .001 .002 C29 C28 DELU .001 .002 C29B C28B DELU .001 .002 N2 C25B DELU .001 .002 N2 C25 SIMU .001 .002 C29 C28 SIMU .001 .002 C29B C28B SIMU .001 .002 N2 C25B SIMU .001 .002 N2 C25 TEMP -148.15 WGHT 0.079600 4.500900 FVAR 0.04576 0.50146 PART 0 C1 1 0.663262 0.371101 0.529141 11.00000 0.02351 0.02291 = 0.02716 -0.00195 0.00206 0.00188 C2 1 0.686399 0.302185 0.585673 11.00000 0.02858 0.02838 = 0.02187 -0.00109 0.00700 0.00035 AFIX 43 H2 2 0.668125 0.307655 0.624861 11.00000 -1.20000 AFIX 0 C3 1 0.733684 0.228437 0.586311 11.00000 0.02574 0.02345 = 0.02329 -0.00003 0.00291 0.00221 C4 1 0.756361 0.164035 0.648778 11.00000 0.02947 0.02626 = 0.02440 0.00097 0.00411 0.00228 C5 1 0.834665 0.077783 0.592111 11.00000 0.02848 0.02767 = 0.02454 -0.00115 0.00159 0.00467 C6 1 0.738444 0.283521 0.471575 11.00000 0.02053 0.02212 = 0.02242 -0.00328 0.00174 0.00039 C7 1 0.689313 0.359869 0.471043 11.00000 0.02345 0.02303 = 0.02054 -0.00203 0.00123 0.00143 C8 1 0.823787 0.013347 0.707623 11.00000 0.04398 0.03417 = 0.02208 0.00654 0.00394 0.01270 AFIX 13 H8 2 0.852162 -0.045244 0.693740 11.00000 -1.20000 AFIX 0 C9 1 0.773276 -0.056132 0.730605 11.00000 0.07112 0.04002 = 0.04570 0.01325 0.00261 0.00161 AFIX 23 H9A 2 0.791384 -0.119221 0.760632 11.00000 -1.20000 H9B 2 0.751599 -0.004089 0.757663 11.00000 -1.20000 AFIX 0 C10 1 0.859407 0.083235 0.763808 11.00000 0.05670 0.06251 = 0.03116 0.00693 -0.00608 0.00325 AFIX 23 H10A 2 0.832354 0.140887 0.779844 11.00000 -1.20000 H10B 2 0.873437 0.029975 0.801669 11.00000 -1.20000 AFIX 0 C11 1 0.728231 -0.109802 0.676168 11.00000 0.09194 0.04763 = 0.05260 0.01332 -0.00274 -0.02056 AFIX 137 H11A 2 0.749071 -0.158147 0.647143 11.00000 -1.50000 H11B 2 0.706043 -0.048061 0.649352 11.00000 -1.50000 H11C 2 0.700252 -0.158145 0.696567 11.00000 -1.50000 AFIX 0 C12 1 0.912843 0.146838 0.745585 11.00000 0.05954 0.11404 = 0.03632 0.01379 -0.00875 -0.02616 AFIX 137 H12A 2 0.899460 0.202887 0.709665 11.00000 -1.50000 H12B 2 0.940349 0.090784 0.730108 11.00000 -1.50000 H12C 2 0.933478 0.188215 0.785128 11.00000 -1.50000 AFIX 0 C13 1 0.614584 0.451460 0.540377 11.00000 0.02667 0.02960 = 0.02307 -0.00078 0.00161 0.00588 C14 1 0.564128 0.422793 0.566342 11.00000 0.02399 0.03110 = 0.02621 -0.00208 0.00184 0.00345 AFIX 43 H14 2 0.553136 0.344969 0.574706 11.00000 -1.20000 AFIX 0 C15 1 0.530031 0.521089 0.579438 11.00000 0.02257 0.03461 = 0.02856 -0.00300 0.00346 0.00566 AFIX 43 H15 2 0.493073 0.515734 0.596005 11.00000 -1.20000 AFIX 0 C16 1 0.555447 0.624017 0.565942 11.00000 0.02197 0.03176 = 0.02231 -0.00229 0.00188 0.00913 C17 1 0.533933 0.742920 0.574235 11.00000 0.02746 0.03174 = 0.02473 -0.00345 -0.00004 0.00530 C18 1 0.570660 0.839903 0.570398 11.00000 0.02549 0.03887 = 0.04341 -0.00246 0.00705 0.00705 AFIX 43 H18 2 0.610460 0.827973 0.562267 11.00000 -1.20000 AFIX 0 C19 1 0.551068 0.952991 0.578040 11.00000 0.03018 0.03233 = 0.05235 -0.00592 0.01169 0.00143 AFIX 43 H19 2 0.576442 1.017804 0.574346 11.00000 -1.20000 AFIX 0 C20 1 0.493199 0.968119 0.591250 11.00000 0.02743 0.02840 = 0.04368 -0.00527 0.00396 0.00394 C21 1 0.456826 0.872369 0.596251 11.00000 0.02262 0.03717 = 0.03553 -0.00578 0.00163 0.00621 C22 1 0.475549 0.759944 0.587720 11.00000 0.02459 0.02725 = 0.03090 -0.00408 -0.00055 0.00434 AFIX 43 H22 2 0.449648 0.695752 0.590880 11.00000 -1.20000 AFIX 0 C23 1 0.398877 0.914997 0.612999 11.00000 0.02786 0.03251 = 0.05105 -0.00873 0.00612 0.00443 C24 1 0.459125 1.075091 0.602348 11.00000 0.03257 0.03321 = 0.05441 -0.00555 0.00826 0.00406 N1 3 0.802807 0.086120 0.646493 11.00000 0.02938 0.02876 = 0.02135 0.00455 0.00171 0.00874 N2 3 0.403015 1.036216 0.615126 11.00000 0.02729 0.03133 = 0.08013 -0.01696 0.01307 0.00334 O1 4 0.734596 0.178128 0.699746 11.00000 0.04682 0.03982 = 0.02558 0.00549 0.01242 0.01455 O2 4 0.880462 0.021010 0.597647 11.00000 0.03402 0.04586 = 0.02982 0.00380 0.00323 0.01896 O3 4 0.355993 0.858295 0.623077 11.00000 0.02852 0.03833 = 0.06564 -0.00759 0.01061 0.00247 O4 4 0.474520 1.175862 0.601316 11.00000 0.03833 0.02907 = 0.07993 -0.00790 0.01855 0.00152 S1 5 0.621487 0.600579 0.534871 11.00000 0.03247 0.02744 = 0.03828 0.00098 0.01306 0.00678 PART 1 C25 1 0.354258 1.105520 0.634988 21.00000 0.02769 0.03148 = 0.08098 -0.01751 0.01284 0.00347 AFIX 13 H25 2 0.367151 1.186954 0.627077 21.00000 -1.20000 AFIX 0 C26 1 0.294852 1.095283 0.585362 21.00000 0.02673 0.03037 = 0.03903 -0.00169 0.01180 0.00351 AFIX 23 H26A 2 0.276254 1.020798 0.595706 21.00000 -1.20000 H26B 2 0.268396 1.157985 0.597292 21.00000 -1.20000 AFIX 0 C28 1 0.352654 1.105515 0.703479 21.00000 0.05134 0.08985 = 0.04762 -0.01050 0.02035 0.00457 AFIX 23 H28A 2 0.347705 1.024770 0.718888 21.00000 -1.20000 H28B 2 0.317918 1.151741 0.712720 21.00000 -1.20000 AFIX 0 C27 1 0.291360 1.099509 0.510499 21.00000 0.04084 0.03284 = 0.04975 0.00004 0.01460 -0.00484 AFIX 137 H27A 2 0.306672 1.174558 0.497499 21.00000 -1.50000 H27B 2 0.249584 1.090335 0.489042 21.00000 -1.50000 H27C 2 0.315541 1.036397 0.496018 21.00000 -1.50000 AFIX 0 C29 1 0.409915 1.156838 0.741734 21.00000 0.05567 0.09217 = 0.04919 -0.01189 0.01642 0.00350 AFIX 137 H29A 2 0.442201 1.099294 0.744319 21.00000 -1.50000 H29B 2 0.403686 1.177874 0.787234 21.00000 -1.50000 H29C 2 0.420853 1.226508 0.718367 21.00000 -1.50000 PART 2 AFIX 0 C25B 1 0.357709 1.119500 0.633455 21.00000 0.02783 0.03133 = 0.08089 -0.01783 0.01267 0.00350 AFIX 13 H25B 2 0.326477 1.063359 0.643420 21.00000 -1.20000 AFIX 0 C26B 1 0.326527 1.176446 0.581618 -21.00000 0.06493 0.04953 = 0.05145 0.00489 0.01963 0.02984 AFIX 23 H26C 2 0.354093 1.230589 0.563551 -21.00000 -1.20000 H26D 2 0.295837 1.224306 0.598796 -21.00000 -1.20000 AFIX 0 C28B 1 0.375776 1.173048 0.702764 -21.00000 0.04548 0.06476 = 0.04176 0.01282 0.01053 0.02728 AFIX 23 H28C 2 0.338561 1.204895 0.715722 -21.00000 -1.20000 H28D 2 0.401294 1.240897 0.696415 -21.00000 -1.20000 AFIX 0 C27B 1 0.295732 1.103939 0.524673 -21.00000 0.02710 0.05550 = 0.07972 -0.00884 -0.00247 0.01657 AFIX 137 H27D 2 0.325384 1.056047 0.506714 -21.00000 -1.50000 H27E 2 0.275493 1.154952 0.489174 -21.00000 -1.50000 H27F 2 0.266161 1.053357 0.540852 -21.00000 -1.50000 AFIX 0 C29B 1 0.407838 1.108510 0.764625 -21.00000 0.04565 0.06409 = 0.04253 0.01329 0.00798 0.02268 AFIX 137 H29D 2 0.379304 1.057664 0.782460 -21.00000 -1.50000 H29E 2 0.424305 1.165080 0.799067 -21.00000 -1.50000 H29F 2 0.440437 1.061459 0.751965 -21.00000 -1.50000 PART HKLF 4 REM 20150109_Art2_0m in C2/c REM R1 = 0.0556 for 3334 Fo > 4sig(Fo) and 0.0918 for all 4982 data REM 377 parameters refined using 37 restraints END WGHT 0.0801 4.3962 REM Highest difference peak 0.819, deepest hole -0.344, 1-sigma level 0.062 Q1 1 0.4937 1.3744 0.7770 11.00000 0.05 0.82 Q2 1 0.8094 -0.1015 0.6989 11.00000 0.05 0.52 Q3 1 0.8909 0.0367 0.7398 11.00000 0.05 0.39 ; _cod_data_source_file J-Mater-Chem-C-2015-3-8904.cif _cod_data_source_block 20150109_art2_0m _cod_depositor_comments ; The following automatic conversions were performed: data item '_symmetry_cell_setting' value 'Monoclinic' was changed to 'monoclinic' in accordance with the built-in table derived from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last updated on 2014-11-21. data item '_exptl_crystal_density_meas' value 'not measured' was changed to '?' -- the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_original_sg_symbol_H-M C2/c _cod_database_code 7234414 _publ_section_expl_refinement ; The H atoms were placed in geometrically idealized positions with C-H distances of 0.95\%A (aromatic),1.0\%A (idealized CH), 0.99\%A (idealized CH~2~) and 0.98\%A (idealized CH~3~) and were constrained to ride on the parent C atom with Uiso(H) = 1.2Ueq(C) for the aromatic, CH~2~ and C-H protons and Uiso(H) = 1.5Ueq(C) for the idealized CH~3~ protons. For the 2-ethylpropyl alkyl chain containing carbon atoms C25-C29 a disorder was modelled with a ratio of 1:1.The atomic displacement parameters for carbon atoms on the disordered fragment were restraied to be of similar size using the DELU and SIMU commands. ; loop_ _symmetry_equiv_pos_as_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' '-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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.66326(12) 0.3711(2) 0.52914(13) 0.0247(6) Uani 1 1 d . . . C2 C 0.68640(12) 0.3022(2) 0.58567(13) 0.0260(6) Uani 1 1 d . . . H2 H 0.6681 0.3077 0.6249 0.031 Uiso 1 1 calc R . . C3 C 0.73368(12) 0.2284(2) 0.58631(13) 0.0243(6) Uani 1 1 d . . . C4 C 0.75636(13) 0.1640(2) 0.64878(14) 0.0267(6) Uani 1 1 d . . . C5 C 0.83467(13) 0.0778(2) 0.59211(13) 0.0272(6) Uani 1 1 d . . . C6 C 0.73844(11) 0.2835(2) 0.47157(13) 0.0219(6) Uani 1 1 d . . . C7 C 0.68931(12) 0.3599(2) 0.47104(13) 0.0226(6) Uani 1 1 d . . . C8 C 0.82379(14) 0.0133(3) 0.70762(14) 0.0336(7) Uani 1 1 d . . . H8 H 0.8522 -0.0452 0.6937 0.040 Uiso 1 1 calc R . . C9 C 0.77328(18) -0.0561(3) 0.73060(18) 0.0530(10) Uani 1 1 d . . . H9A H 0.7914 -0.1192 0.7606 0.064 Uiso 1 1 calc R . . H9B H 0.7516 -0.0041 0.7577 0.064 Uiso 1 1 calc R . . C10 C 0.85941(17) 0.0832(3) 0.76381(16) 0.0515(10) Uani 1 1 d . . . H10A H 0.8324 0.1409 0.7798 0.062 Uiso 1 1 calc R . . H10B H 0.8734 0.0300 0.8017 0.062 Uiso 1 1 calc R . . C11 C 0.7282(2) -0.1098(4) 0.6762(2) 0.0656(12) Uani 1 1 d . . . H11A H 0.7491 -0.1581 0.6471 0.098 Uiso 1 1 calc R . . H11B H 0.7060 -0.0481 0.6494 0.098 Uiso 1 1 calc R . . H11C H 0.7003 -0.1581 0.6966 0.098 Uiso 1 1 calc R . . C12 C 0.91284(18) 0.1468(4) 0.74558(19) 0.0717(13) Uani 1 1 d . . . H12A H 0.8995 0.2029 0.7097 0.108 Uiso 1 1 calc R . . H12B H 0.9403 0.0908 0.7301 0.108 Uiso 1 1 calc R . . H12C H 0.9335 0.1882 0.7851 0.108 Uiso 1 1 calc R . . C13 C 0.61458(12) 0.4515(3) 0.54038(13) 0.0267(6) Uani 1 1 d . . . C14 C 0.56413(12) 0.4228(3) 0.56634(13) 0.0273(6) Uani 1 1 d . . . H14 H 0.5531 0.3450 0.5747 0.033 Uiso 1 1 calc R . . C15 C 0.53003(13) 0.5211(3) 0.57944(14) 0.0286(7) Uani 1 1 d . . . H15 H 0.4931 0.5157 0.5960 0.034 Uiso 1 1 calc R . . C16 C 0.55545(12) 0.6240(2) 0.56594(13) 0.0255(6) Uani 1 1 d . . . C17 C 0.53393(13) 0.7429(3) 0.57424(14) 0.0284(7) Uani 1 1 d . . . C18 C 0.57066(13) 0.8399(3) 0.57040(15) 0.0358(7) Uani 1 1 d . . . H18 H 0.6105 0.8280 0.5623 0.043 Uiso 1 1 calc R . . C19 C 0.55107(14) 0.9530(3) 0.57804(16) 0.0377(8) Uani 1 1 d . . . H19 H 0.5764 1.0178 0.5743 0.045 Uiso 1 1 calc R . . C20 C 0.49320(13) 0.9681(3) 0.59125(16) 0.0334(7) Uani 1 1 d . . . C21 C 0.45683(13) 0.8724(3) 0.59625(15) 0.0321(7) Uani 1 1 d . . . C22 C 0.47555(12) 0.7599(3) 0.58772(14) 0.0281(7) Uani 1 1 d . . . H22 H 0.4496 0.6958 0.5909 0.034 Uiso 1 1 calc R . . C23 C 0.39888(14) 0.9150(3) 0.61300(17) 0.0372(8) Uani 1 1 d . A . C24 C 0.45913(14) 1.0751(3) 0.60235(17) 0.0399(8) Uani 1 1 d . A . N1 N 0.80281(10) 0.0861(2) 0.64649(11) 0.0267(5) Uani 1 1 d . . . N2 N 0.40301(11) 1.0362(2) 0.61513(16) 0.0458(7) Uani 1 1 d DU . . O1 O 0.73460(9) 0.17813(19) 0.69975(10) 0.0367(5) Uani 1 1 d . . . O2 O 0.88046(9) 0.02101(19) 0.59765(10) 0.0368(5) Uani 1 1 d . . . O3 O 0.35599(9) 0.8583(2) 0.62308(12) 0.0438(6) Uani 1 1 d . . . O4 O 0.47452(10) 1.1759(2) 0.60132(13) 0.0481(6) Uani 1 1 d . . . S1 S 0.62149(3) 0.60058(7) 0.53487(4) 0.0319(2) Uani 1 1 d . . . C25 C 0.3543(5) 1.1055(10) 0.6350(4) 0.0463(9) Uani 0.501(4) 1 d PDU A 1 H25 H 0.3672 1.1870 0.6271 0.056 Uiso 0.501(4) 1 calc PR A 1 C26 C 0.2949(3) 1.0953(6) 0.5854(3) 0.0313(15) Uani 0.501(4) 1 d PD A 1 H26A H 0.2763 1.0208 0.5957 0.038 Uiso 0.501(4) 1 calc PR A 1 H26B H 0.2684 1.1580 0.5973 0.038 Uiso 0.501(4) 1 calc PR A 1 C28 C 0.3527(3) 1.1055(10) 0.7035(3) 0.062(2) Uani 0.501(4) 1 d PDU A 1 H28A H 0.3477 1.0248 0.7189 0.074 Uiso 0.501(4) 1 calc PR A 1 H28B H 0.3179 1.1517 0.7127 0.074 Uiso 0.501(4) 1 calc PR A 1 C27 C 0.2914(12) 1.100(2) 0.5105(6) 0.040(4) Uani 0.501(4) 1 d PD A 1 H27A H 0.3067 1.1746 0.4975 0.061 Uiso 0.501(4) 1 calc PR A 1 H27B H 0.2496 1.0903 0.4890 0.061 Uiso 0.501(4) 1 calc PR A 1 H27C H 0.3155 1.0364 0.4960 0.061 Uiso 0.501(4) 1 calc PR A 1 C29 C 0.4099(4) 1.1568(10) 0.7417(5) 0.065(2) Uani 0.501(4) 1 d PDU A 1 H29A H 0.4422 1.0993 0.7443 0.097 Uiso 0.501(4) 1 calc PR A 1 H29B H 0.4037 1.1779 0.7872 0.097 Uiso 0.501(4) 1 calc PR A 1 H29C H 0.4209 1.2265 0.7184 0.097 Uiso 0.501(4) 1 calc PR A 1 C25B C 0.3577(5) 1.1195(10) 0.6335(5) 0.0462(9) Uani 0.501(4) 1 d PDU A 2 H25B H 0.3265 1.0634 0.6434 0.055 Uiso 0.501(4) 1 calc PR A 2 C26B C 0.3265(4) 1.1764(7) 0.5816(3) 0.054(2) Uani 0.499(4) 1 d PD A 2 H26C H 0.3541 1.2306 0.5636 0.065 Uiso 0.499(4) 1 calc PR A 2 H26D H 0.2958 1.2243 0.5988 0.065 Uiso 0.499(4) 1 calc PR A 2 C28B C 0.3758(4) 1.1730(7) 0.7028(3) 0.0503(17) Uani 0.499(4) 1 d PDU A 2 H28C H 0.3386 1.2049 0.7157 0.060 Uiso 0.499(4) 1 calc PR A 2 H28D H 0.4013 1.2409 0.6964 0.060 Uiso 0.499(4) 1 calc PR A 2 C27B C 0.2957(12) 1.104(2) 0.5247(8) 0.055(5) Uani 0.499(4) 1 d PD A 2 H27D H 0.3254 1.0560 0.5067 0.083 Uiso 0.499(4) 1 calc PR A 2 H27E H 0.2755 1.1550 0.4892 0.083 Uiso 0.499(4) 1 calc PR A 2 H27F H 0.2662 1.0534 0.5409 0.083 Uiso 0.499(4) 1 calc PR A 2 C29B C 0.4078(4) 1.1085(8) 0.7646(4) 0.0507(17) Uani 0.499(4) 1 d PDU A 2 H29D H 0.3793 1.0577 0.7825 0.076 Uiso 0.499(4) 1 calc PR A 2 H29E H 0.4243 1.1651 0.7991 0.076 Uiso 0.499(4) 1 calc PR A 2 H29F H 0.4404 1.0615 0.7520 0.076 Uiso 0.499(4) 1 calc PR A 2 loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0235(15) 0.0229(15) 0.0272(15) -0.0019(11) 0.0021(11) 0.0019(11) C2 0.0286(16) 0.0284(16) 0.0219(14) -0.0011(12) 0.0070(12) 0.0003(12) C3 0.0257(15) 0.0235(15) 0.0233(14) 0.0000(12) 0.0029(11) 0.0022(12) C4 0.0295(15) 0.0263(16) 0.0244(15) 0.0010(12) 0.0041(12) 0.0023(13) C5 0.0285(16) 0.0277(16) 0.0245(15) -0.0012(12) 0.0016(12) 0.0047(13) C6 0.0205(14) 0.0221(14) 0.0224(14) -0.0033(11) 0.0017(11) 0.0004(11) C7 0.0234(14) 0.0230(14) 0.0205(14) -0.0020(11) 0.0012(11) 0.0014(11) C8 0.0440(19) 0.0342(17) 0.0221(15) 0.0065(13) 0.0039(13) 0.0127(14) C9 0.071(3) 0.040(2) 0.046(2) 0.0132(17) 0.0026(19) 0.0016(19) C10 0.057(2) 0.063(3) 0.0312(18) 0.0069(17) -0.0061(16) 0.0032(19) C11 0.092(3) 0.048(2) 0.053(2) 0.0133(19) -0.003(2) -0.021(2) C12 0.060(3) 0.114(4) 0.036(2) 0.014(2) -0.0088(19) -0.026(3) C13 0.0267(16) 0.0296(16) 0.0231(15) -0.0008(12) 0.0016(12) 0.0059(12) C14 0.0240(15) 0.0311(17) 0.0262(15) -0.0021(12) 0.0018(12) 0.0035(12) C15 0.0226(15) 0.0346(17) 0.0286(15) -0.0030(13) 0.0035(12) 0.0057(13) C16 0.0220(14) 0.0318(17) 0.0223(14) -0.0023(12) 0.0019(11) 0.0091(12) C17 0.0275(15) 0.0317(17) 0.0247(14) -0.0035(12) 0.0000(12) 0.0053(13) C18 0.0255(16) 0.0389(19) 0.0434(19) -0.0025(15) 0.0070(13) 0.0071(14) C19 0.0302(17) 0.0323(18) 0.052(2) -0.0059(15) 0.0117(15) 0.0014(14) C20 0.0274(16) 0.0284(17) 0.0437(18) -0.0053(14) 0.0040(13) 0.0039(13) C21 0.0226(15) 0.0372(18) 0.0355(17) -0.0058(14) 0.0016(12) 0.0062(13) C22 0.0246(15) 0.0272(16) 0.0309(16) -0.0041(13) -0.0006(12) 0.0043(12) C23 0.0279(17) 0.0325(18) 0.051(2) -0.0087(15) 0.0061(14) 0.0044(14) C24 0.0326(18) 0.0332(19) 0.054(2) -0.0056(15) 0.0083(15) 0.0041(14) N1 0.0294(13) 0.0288(14) 0.0213(12) 0.0045(10) 0.0017(10) 0.0087(11) N2 0.0273(12) 0.0313(14) 0.0801(18) -0.0170(12) 0.0131(11) 0.0033(10) O1 0.0468(13) 0.0398(13) 0.0256(11) 0.0055(9) 0.0124(10) 0.0145(10) O2 0.0340(12) 0.0459(13) 0.0298(12) 0.0038(10) 0.0032(9) 0.0190(10) O3 0.0285(12) 0.0383(13) 0.0656(16) -0.0076(11) 0.0106(11) 0.0025(10) O4 0.0383(13) 0.0291(13) 0.0799(18) -0.0079(12) 0.0186(12) 0.0015(10) S1 0.0325(4) 0.0274(4) 0.0383(4) 0.0010(3) 0.0131(3) 0.0068(3) C25 0.0277(15) 0.0315(17) 0.081(2) -0.0175(14) 0.0128(14) 0.0035(13) C26 0.027(3) 0.030(4) 0.039(4) -0.002(3) 0.012(3) 0.004(3) C28 0.051(4) 0.090(6) 0.048(4) -0.011(4) 0.020(3) 0.005(4) C27 0.041(9) 0.033(7) 0.050(6) 0.000(5) 0.015(5) -0.005(6) C29 0.056(4) 0.092(6) 0.049(4) -0.012(4) 0.016(3) 0.004(4) C25B 0.0278(15) 0.0313(17) 0.081(2) -0.0178(14) 0.0127(14) 0.0035(13) C26B 0.065(5) 0.050(5) 0.051(5) 0.005(4) 0.020(4) 0.030(4) C28B 0.045(4) 0.065(4) 0.042(3) 0.013(3) 0.011(3) 0.027(3) C27B 0.027(7) 0.056(9) 0.080(11) -0.009(8) -0.002(8) 0.017(6) C29B 0.046(4) 0.064(4) 0.043(3) 0.013(3) 0.008(3) 0.023(3) 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' S S 0.1246 0.1234 '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 C7 C1 C2 118.1(2) . . C7 C1 C13 127.4(2) . . C2 C1 C13 114.4(2) . . C3 C2 C1 122.9(3) . . C3 C2 H2 118.5 . . C1 C2 H2 118.5 . . C2 C3 C6 120.2(2) . 7_656 C2 C3 C4 118.9(2) . . C6 C3 C4 120.8(2) 7_656 . O1 C4 N1 121.6(2) . . O1 C4 C3 121.3(3) . . N1 C4 C3 117.1(2) . . O2 C5 N1 120.0(2) . . O2 C5 C7 121.8(3) . 7_656 N1 C5 C7 118.2(2) . 7_656 C6 C6 C7 122.3(3) 7_656 . C6 C6 C3 117.4(3) 7_656 7_656 C7 C6 C3 120.4(2) . 7_656 C1 C7 C6 119.1(2) . . C1 C7 C5 121.9(2) . 7_656 C6 C7 C5 119.0(2) . 7_656 N1 C8 C10 112.3(3) . . N1 C8 C9 112.7(3) . . C10 C8 C9 112.7(3) . . N1 C8 H8 106.1 . . C10 C8 H8 106.1 . . C9 C8 H8 106.1 . . C11 C9 C8 116.5(3) . . C11 C9 H9A 108.2 . . C8 C9 H9A 108.2 . . C11 C9 H9B 108.2 . . C8 C9 H9B 108.2 . . H9A C9 H9B 107.3 . . C12 C10 C8 115.3(3) . . C12 C10 H10A 108.5 . . C8 C10 H10A 108.5 . . C12 C10 H10B 108.5 . . C8 C10 H10B 108.5 . . H10A C10 H10B 107.5 . . C9 C11 H11A 109.5 . . C9 C11 H11B 109.5 . . H11A C11 H11B 109.5 . . C9 C11 H11C 109.5 . . H11A C11 H11C 109.5 . . H11B C11 H11C 109.5 . . C10 C12 H12A 109.5 . . C10 C12 H12B 109.5 . . H12A C12 H12B 109.5 . . C10 C12 H12C 109.5 . . H12A C12 H12C 109.5 . . H12B C12 H12C 109.5 . . C14 C13 C1 126.4(3) . . C14 C13 S1 110.7(2) . . C1 C13 S1 122.1(2) . . C13 C14 C15 113.0(3) . . C13 C14 H14 123.5 . . C15 C14 H14 123.5 . . C16 C15 C14 113.3(3) . . C16 C15 H15 123.3 . . C14 C15 H15 123.3 . . C15 C16 C17 128.8(3) . . C15 C16 S1 110.7(2) . . C17 C16 S1 120.4(2) . . C18 C17 C22 119.0(3) . . C18 C17 C16 121.6(3) . . C22 C17 C16 119.4(3) . . C19 C18 C17 122.4(3) . . C19 C18 H18 118.8 . . C17 C18 H18 118.8 . . C20 C19 C18 117.8(3) . . C20 C19 H19 121.1 . . C18 C19 H19 121.1 . . C21 C20 C19 120.2(3) . . C21 C20 C24 108.5(3) . . C19 C20 C24 131.3(3) . . C22 C21 C20 122.4(3) . . C22 C21 C23 129.5(3) . . C20 C21 C23 108.0(3) . . C21 C22 C17 118.2(3) . . C21 C22 H22 120.9 . . C17 C22 H22 120.9 . . O3 C23 N2 125.6(3) . . O3 C23 C21 128.2(3) . . N2 C23 C21 106.2(3) . . O4 C24 N2 125.2(3) . . O4 C24 C20 129.1(3) . . N2 C24 C20 105.6(3) . . C4 N1 C5 123.7(2) . . C4 N1 C8 118.3(2) . . C5 N1 C8 117.8(2) . . C23 N2 C24 111.7(2) . . C23 N2 C25 120.0(5) . . C24 N2 C25 128.1(5) . . C23 N2 C25B 127.0(5) . . C24 N2 C25B 121.1(5) . . C13 S1 C16 92.24(14) . . C28 C25 N2 114.3(7) . . C28 C25 C26 119.1(9) . . N2 C25 C26 113.3(6) . . C28 C25 H25 102.3 . . N2 C25 H25 102.3 . . C26 C25 H25 102.3 . . C27 C26 C25 123.4(12) . . C27 C26 H26A 106.5 . . C25 C26 H26A 106.5 . . C27 C26 H26B 106.5 . . C25 C26 H26B 106.5 . . H26A C26 H26B 106.5 . . C25 C28 C29 110.5(8) . . C25 C28 H28A 109.5 . . C29 C28 H28A 109.5 . . C25 C28 H28B 109.5 . . C29 C28 H28B 109.5 . . H28A C28 H28B 108.1 . . C26B C25B N2 114.8(8) . . C26B C25B C28B 123.5(9) . . N2 C25B C28B 113.1(7) . . C26B C25B H25B 99.9 . . N2 C25B H25B 99.9 . . C28B C25B H25B 99.9 . . C25B C26B C27B 116.8(13) . . C25B C26B H26C 108.1 . . C27B C26B H26C 108.1 . . C25B C26B H26D 108.1 . . C27B C26B H26D 108.1 . . H26C C26B H26D 107.3 . . C25B C28B C29B 125.1(8) . . C25B C28B H28C 106.0 . . C29B C28B H28C 106.0 . . C25B C28B H28D 106.0 . . C29B C28B H28D 106.0 . . H28C C28B H28D 106.3 . . C26B C27B H27D 109.5 . . C26B C27B H27E 109.5 . . H27D C27B H27E 109.5 . . C26B C27B H27F 109.5 . . H27D C27B H27F 109.5 . . H27E C27B H27F 109.5 . . C28B C29B H29D 109.5 . . C28B C29B H29E 109.5 . . H29D C29B H29E 109.5 . . C28B C29B H29F 109.5 . . H29D C29B H29F 109.5 . . H29E C29B H29F 109.5 . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 C1 C7 1.398(4) . C1 C2 1.417(4) . C1 C13 1.481(4) . C2 C3 1.363(4) . C2 H2 0.9500 . C3 C6 1.418(4) 7_656 C3 C4 1.480(4) . C4 O1 1.218(3) . C4 N1 1.386(4) . C5 O2 1.214(3) . C5 N1 1.407(3) . C5 C7 1.486(4) 7_656 C6 C6 1.410(5) 7_656 C6 C7 1.414(4) . C6 C3 1.418(4) 7_656 C7 C5 1.486(4) 7_656 C8 N1 1.502(3) . C8 C10 1.512(4) . C8 C9 1.525(5) . C8 H8 1.0000 . C9 C11 1.505(5) . C9 H9A 0.9900 . C9 H9B 0.9900 . C10 C12 1.507(5) . C10 H10A 0.9900 . C10 H10B 0.9900 . C11 H11A 0.9800 . C11 H11B 0.9800 . C11 H11C 0.9800 . C12 H12A 0.9800 . C12 H12B 0.9800 . C12 H12C 0.9800 . C13 C14 1.369(4) . C13 S1 1.725(3) . C14 C15 1.415(4) . C14 H14 0.9500 . C15 C16 1.361(4) . C15 H15 0.9500 . C16 C17 1.468(4) . C16 S1 1.730(3) . C17 C18 1.399(4) . C17 C22 1.403(4) . C18 C19 1.389(4) . C18 H18 0.9500 . C19 C20 1.387(4) . C19 H19 0.9500 . C20 C21 1.387(4) . C20 C24 1.486(4) . C21 C22 1.378(4) . C21 C23 1.487(4) . C22 H22 0.9500 . C23 O3 1.212(4) . C23 N2 1.396(4) . C24 O4 1.210(4) . C24 N2 1.407(4) . N2 C25 1.466(12) . N2 C25B 1.490(12) . C25 C28 1.387(9) . C25 C26 1.546(8) . C25 H25 1.0000 . C26 C27 1.499(10) . C26 H26A 0.9900 . C26 H26B 0.9900 . C28 C29 1.517(8) . C28 H28A 0.9900 . C28 H28B 0.9900 . C27 H27A 0.9800 . C27 H27B 0.9800 . C27 H27C 0.9800 . C29 H29A 0.9800 . C29 H29B 0.9800 . C29 H29C 0.9800 . C25B C26B 1.335(13) . C25B C28B 1.522(14) . C25B H25B 1.0000 . C26B C27B 1.497(10) . C26B H26C 0.9900 . C26B H26D 0.9900 . C28B C29B 1.530(7) . C28B H28C 0.9900 . C28B H28D 0.9900 . C27B H27D 0.9800 . C27B H27E 0.9800 . C27B H27F 0.9800 . C29B H29D 0.9800 . C29B H29E 0.9800 . C29B H29F 0.9800 .