#------------------------------------------------------------------------------ #$Date: 2019-06-14 03:10:49 +0300 (Fri, 14 Jun 2019) $ #$Revision: 215938 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/14/1551406.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_1551406 loop_ _publ_author_name 'Gross, Zeev' 'Zhao, Jianzhang' 'Mahammed, Atif' 'Chen, Kepeng' 'Vestfrid, Jenya' _publ_section_title ; Phosphorus Corrole Complexes: From Property Tuning to Applications in Photocatalysis and Triplet-Triplet Annihilation Upconversion ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/C9SC01463B _journal_year 2019 _chemical_formula_moiety 'C37 H4 F17 I4 N4 P, 2(C Cl2)' _chemical_formula_sum 'C39 H4 Cl4 F17 I4 N4 P' _chemical_formula_weight 1531.83 _chemical_name_common 'Gross95 (Zhenya)' _space_group_crystal_system monoclinic _space_group_IT_number 11 _space_group_name_Hall '-P 2yb' _space_group_name_H-M_alt 'P 1 21/m 1' _symmetry_space_group_name_Hall '-P 2yb' _symmetry_space_group_name_H-M 'P 1 21/m 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2019-01-03 deposited with the CCDC. 2019-06-12 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 110.42(3) _cell_angle_gamma 90 _cell_formula_units_Z 2 _cell_length_a 17.2430(13) _cell_length_b 7.806(5) _cell_length_c 17.503(3) _cell_measurement_reflns_used 3932 _cell_measurement_temperature 200(2) _cell_measurement_theta_max 24.710 _cell_measurement_theta_min 2.055 _cell_volume 2207.8(15) _computing_cell_refinement 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Nonius, 2006)' _computing_data_reduction 'DENZO HKL2000 (Otwinowski & Minor 1997)' _computing_molecular_graphics 'Mercury 3.10.1' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXL-2014/7 (Sheldrick, 2014)' _diffrn_ambient_temperature 200(2) _diffrn_detector_area_resol_mean 95 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.984 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'phi- and omega-scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0770 _diffrn_reflns_av_unetI/netI 0.0485 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.984 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 3932 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.984 _diffrn_reflns_theta_full 24.710 _diffrn_reflns_theta_max 24.710 _diffrn_reflns_theta_min 2.055 _diffrn_source 'fine-focus sealed tube' _exptl_absorpt_coefficient_mu 3.211 _exptl_absorpt_correction_T_max 0.678 _exptl_absorpt_correction_T_min 0.532 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' ; _exptl_crystal_colour red _exptl_crystal_density_diffrn 2.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 1428 _exptl_crystal_size_max 0.210 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.120 _refine_diff_density_max 2.573 _refine_diff_density_min -1.410 _refine_diff_density_rms 0.153 _refine_ls_extinction_coef 0.0036(12) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.124 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 370 _refine_ls_number_reflns 3932 _refine_ls_number_restraints 6 _refine_ls_restrained_S_all 1.123 _refine_ls_R_factor_all 0.1284 _refine_ls_R_factor_gt 0.1059 _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^)+(0.0857P)^2^+30.3420P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2335 _refine_ls_wR_factor_ref 0.2458 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3128 _reflns_number_total 3932 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c9sc01463b2.cif _cod_data_source_block Gross95 _cod_original_cell_volume 2207.9(15) _cod_database_code 1551406 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.552 _shelx_estimated_absorpt_t_max 0.699 _shelx_res_file ; shelxl.res created by SHELXL-2014/7 TITL Gross95 (Zhenya), red needls, monoclinic, P21/m, Rint=0.077 CELL 0.71073 17.243 7.806 17.503 90 110.419 90 ZERR 2 0.0013 0.0048 0.0029 0 0.0256 0 LATT 1 SYMM -X,0.5+Y,-Z SFAC C H Cl F I N P DISP C 0.0033 0.0016 DISP Cl 0.1484 0.1585 DISP F 0.0171 0.0103 DISP I -0.4742 1.8119 DISP N 0.0061 0.0033 DISP P 0.1023 0.0942 UNIT 78 8 8 34 8 8 2 EQIV $1 +X,0.5-Y,+Z DFIX 1.4 0.001 C28 C29 DFIX 1.39 0.001 C30 C31 DFIX 1.7 0.001 Cl4 C33 DFIX 1.7 0.001 C33 Cl3 DFIX 1.7 0.001 Cl2 C32 DFIX 1.7 0.001 Cl1 C32 EADP C30 C31 EADP Cl1 C32 L.S. 8 PLAN -10 SIZE 0.12 0.15 0.21 TEMP -73 FREE I3 I4A FREE I3A I4 FREE I2 I3A FREE I2 I3A_$1 LIST 4 fmap 2 acta OMIT 0 50.1 OMIT -1 3 3 OMIT -5 1 3 OMIT 4 3 5 OMIT -12 1 6 OMIT -7 1 3 OMIT 1 3 1 OMIT -9 1 5 OMIT -9 1 4 OMIT -8 1 3 OMIT -4 0 8 OMIT 11 0 1 OMIT -1 0 1 OMIT 8 1 1 OMIT -5 6 14 OMIT -1 0 1 OMIT 5 0 1 OMIT 0 3 3 OMIT 1 0 6 OMIT -7 4 1 OMIT -13 5 1 OMIT 4 1 1 OMIT 0 5 3 OMIT 8 7 3 OMIT -2 2 7 OMIT -4 4 2 OMIT 2 1 0 OMIT 1 1 0 OMIT -5 0 4 OMIT 1 1 1 OMIT -8 8 8 OMIT 3 1 2 OMIT -6 2 5 OMIT 5 4 8 OMIT 0 4 3 OMIT 5 1 5 OMIT -2 0 6 OMIT -2 0 10 OMIT -10 1 6 OMIT -5 3 3 OMIT 5 5 3 OMIT 1 0 8 OMIT -11 1 3 OMIT -4 3 1 OMIT -3 1 2 OMIT -19 3 7 OMIT -9 0 5 OMIT -8 4 2 OMIT 5 4 5 OMIT 8 0 1 OMIT 1 8 7 OMIT 4 1 3 OMIT -7 6 1 OMIT -5 5 1 OMIT -7 2 4 OMIT -9 1 6 OMIT 5 3 3 OMIT -2 0 8 OMIT -3 3 2 OMIT -2 9 3 OMIT 5 6 4 OMIT -18 0 13 OMIT 3 1 6 REM REM REM WGHT 0.085700 30.342001 EXTI 0.003628 FVAR 0.49316 0.53394 0.47315 I1 5 0.435950 10.250000 0.273674 10.50000 0.04311 0.09998 = 0.10800 0.00000 0.03710 0.00000 I2 5 0.366176 10.250000 0.045955 10.50000 0.03744 0.10913 = 0.10829 0.00000 0.00961 0.00000 PART 1 I3 5 0.428238 10.250000 -0.136045 20.50000 0.03186 0.11930 = 0.06347 0.00000 -0.00677 0.00000 PART 0 PART 2 I3A 5 0.419451 0.250000 -0.115457 -20.50000 0.09593 0.26753 = 0.26126 0.00000 -0.03693 0.00000 I4A 5 0.582175 0.250000 -0.200984 -30.50000 0.14204 0.11723 = 0.07345 0.00000 0.01948 0.00000 PART 0 PART 1 I4 5 0.597735 10.250000 -0.206901 30.50000 0.05238 0.11808 = 0.03800 0.00000 -0.00314 0.00000 PART 0 P1 7 0.728537 10.250000 0.161044 10.50000 0.02822 0.06093 = 0.05019 0.00000 0.01102 0.00000 F1 4 0.794698 10.551910 -0.088631 11.00000 0.15470 0.13152 = 0.10412 0.01083 0.07120 -0.01584 F2 4 0.832901 0.554477 -0.222920 11.00000 0.22000 0.21550 = 0.11708 0.04356 0.09796 -0.02057 F3 4 0.852145 0.250000 -0.289044 10.50000 0.19951 0.38686 = 0.10144 0.00000 0.10144 0.00000 F4 4 1.018820 -0.048525 0.331100 11.00000 0.05588 0.06311 = 0.16384 0.00202 0.00211 -0.00232 F5 4 1.180413 -0.047445 0.423572 11.00000 0.06169 0.08435 = 0.16648 0.02214 -0.00971 0.02542 F6 4 1.260559 10.250000 0.469724 10.50000 0.03744 0.13231 = 0.07894 0.00000 0.00539 0.00000 F7 4 0.629460 10.544600 0.392069 11.00000 0.13874 0.13362 = 0.15998 -0.06447 0.10862 -0.06684 F8 4 0.587874 10.564500 0.521477 11.00000 0.16345 0.24175 = 0.20313 -0.15075 0.14161 -0.12944 F9 4 0.574513 10.250000 0.598362 10.50000 0.09509 0.38369 = 0.09008 0.00000 0.06555 0.00000 F10 4 0.731410 0.044219 0.162872 11.00000 0.05140 0.07216 = 0.08305 0.00671 0.01752 -0.00113 N1 6 0.824302 10.250000 0.138247 10.50000 0.03601 0.06047 = 0.03902 0.00000 0.01632 0.00000 N2 6 0.780819 10.250000 0.271167 10.50000 0.02288 0.06781 = 0.03535 0.00000 0.00527 0.00000 N3 6 0.627472 10.250000 0.172315 10.50000 0.03973 0.07638 = 0.06161 0.00000 0.02051 0.00000 N4 6 0.667365 10.250000 0.054307 10.50000 0.04164 0.04362 = 0.06215 0.00000 0.00521 0.00000 C1 1 0.766685 10.250000 -0.010636 10.50000 0.04127 0.08228 = 0.06260 0.00000 0.00251 0.00000 C2 1 0.832042 10.250000 0.062537 10.50000 0.05316 0.07924 = 0.03107 0.00000 0.01766 0.00000 C3 1 0.914472 10.250000 0.072457 10.50000 0.04931 0.12567 = 0.07584 0.00000 0.02942 0.00000 AFIX 43 H3 2 0.936072 0.250000 0.029401 10.50000 -1.20000 AFIX 0 C4 1 0.960021 10.250000 0.152168 10.50000 0.04448 0.09494 = 0.04450 0.00000 0.01465 0.00000 AFIX 43 H4 2 1.018747 0.250000 0.174868 10.50000 -1.20000 AFIX 0 C5 1 0.905527 10.250000 0.196460 10.50000 0.02648 0.08189 = 0.04544 0.00000 0.00066 0.00000 C6 1 0.923779 10.250000 0.277741 10.50000 0.03128 0.04763 = 0.06631 0.00000 0.02414 0.00000 C7 1 0.863166 10.250000 0.311904 10.50000 0.05012 0.06722 = 0.05256 0.00000 0.02273 0.00000 C8 1 0.879268 10.250000 0.399208 10.50000 0.02470 0.13255 = 0.03883 0.00000 0.00520 0.00000 AFIX 43 H8 2 0.931604 0.250000 0.441919 10.50000 -1.20000 AFIX 0 C9 1 0.805730 10.250000 0.406318 10.50000 0.06020 0.15145 = 0.04385 0.00000 0.02608 0.00000 AFIX 43 H9 2 0.797194 0.250000 0.457086 10.50000 -1.20000 AFIX 0 C10 1 0.741487 10.250000 0.330459 10.50000 0.03811 0.09148 = 0.04502 0.00000 0.01909 0.00000 C11 1 0.659749 10.250000 0.318000 10.50000 0.04592 0.09395 = 0.05502 0.00000 0.01437 0.00000 C12 1 0.600729 10.250000 0.238127 10.50000 0.04459 0.07372 = 0.05517 0.00000 0.01983 0.00000 C13 1 0.512433 10.250000 0.207741 10.50000 0.04192 0.06854 = 0.09663 0.00000 0.01865 0.00000 C14 1 0.486361 10.250000 0.124320 10.50000 0.04482 0.05861 = 0.10532 0.00000 0.04103 0.00000 C15 1 0.561044 10.250000 0.101943 10.50000 0.03029 0.09700 = 0.04172 0.00000 0.00464 0.00000 C16 1 0.582191 10.250000 0.031162 10.50000 0.04176 0.03330 = 0.07125 0.00000 0.01213 0.00000 C17 1 0.546196 10.250000 -0.054273 10.50000 0.05640 0.05579 = 0.05900 0.00000 -0.00820 0.00000 C18 1 0.610139 10.250000 -0.081035 10.50000 0.05938 0.05717 = 0.07738 0.00000 0.01228 0.00000 C19 1 0.687243 10.250000 -0.016042 10.50000 0.04808 0.06170 = 0.04536 0.00000 0.00884 0.00000 C20 1 0.786997 10.250000 -0.088412 10.50000 0.06057 0.13859 = 0.04780 0.00000 0.01883 0.00000 C21 1 0.799762 0.404282 -0.122234 11.00000 0.08728 0.12946 = 0.07135 0.01749 0.03592 0.00887 C22 1 0.821440 10.406679 -0.189117 11.00000 0.14959 0.21989 = 0.05875 0.01037 0.04000 -0.00676 C23 1 0.826783 10.250000 -0.227242 10.50000 0.26700 0.22830 = 0.08227 0.00000 0.10939 0.00000 C24 1 1.012085 10.250000 0.327412 10.50000 0.04305 0.06786 = 0.04563 0.00000 0.03008 0.00000 C25 1 1.057689 0.099154 0.354858 11.00000 0.04195 0.07959 = 0.06910 0.00766 0.01947 -0.00409 C26 1 1.139429 0.100507 0.400269 11.00000 0.04055 0.08481 = 0.05829 0.00848 0.00622 0.01416 C27 1 1.181149 10.250000 0.423894 10.50000 0.02863 0.09278 = 0.02713 0.00000 0.00492 0.00000 C28 1 0.635779 0.250000 0.388031 10.50000 0.03354 0.11109 = 0.09687 0.00000 0.03986 0.00000 C29 1 0.622763 0.399968 0.425741 11.00000 0.06299 0.12612 = 0.10940 -0.01887 0.05342 -0.04087 C30 1 0.602242 10.398601 0.493261 11.00000 0.05840 0.19613 = 0.11133 -0.05566 0.05301 -0.04587 C31 1 0.593184 10.250000 0.533074 10.50000 0.05840 0.19613 = 0.11133 -0.05566 0.05301 -0.04587 CL2 3 1.250442 0.250000 0.678637 10.50000 0.08489 0.20028 = 0.12943 0.00000 0.03697 0.00000 CL1 3 1.083665 0.250000 0.570541 10.50000 0.08070 0.46671 = 0.06789 0.00000 0.01385 0.00000 C32 1 1.148910 0.250000 0.669161 10.50000 0.08070 0.46671 = 0.06789 0.00000 0.01385 0.00000 CL3 3 0.836974 0.678749 0.119166 10.50000 0.11756 CL4 3 0.964207 0.750000 0.066445 10.50000 0.25238 C33 1 0.936339 0.750000 0.150525 10.50000 0.33678 HKLF 4 REM Gross95 (Zhenya), red needls, monoclinic, P21/m, Rint=0.077 REM R1 = 0.1059 for 3128 Fo > 4sig(Fo) and 0.1284 for all 3932 data REM 370 parameters refined using 6 restraints END WGHT 0.0860 30.2812 REM Highest difference peak 2.573, deepest hole -1.410, 1-sigma level 0.153 Q1 1 0.9819 0.2500 0.4993 10.50000 0.05 2.57 Q2 1 1.0774 0.2500 0.1588 10.50000 0.05 1.46 Q3 1 0.9791 0.2500 -0.0074 10.50000 0.05 0.86 Q4 1 0.9954 0.2500 -0.1287 10.50000 0.05 0.81 Q5 1 1.0415 0.3491 -0.0506 11.00000 0.05 0.76 Q6 1 1.1249 0.2500 -0.0723 10.50000 0.05 0.68 Q7 1 1.1065 0.3381 -0.1040 11.00000 0.05 0.60 Q8 1 1.1971 0.3608 0.6531 11.00000 0.05 0.59 Q9 1 0.4650 0.2500 0.2269 10.50000 0.05 0.57 Q10 1 0.4416 0.2500 0.3237 10.50000 0.05 0.56 ; _shelx_res_checksum 35256 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z' '-x, -y, -z' 'x, -y-1/2, 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 I1 I 0.43595(8) 0.2500 0.27367(10) 0.0809(6) Uani 1 2 d S T P . . I2 I 0.36618(8) 0.2500 0.04596(11) 0.0891(7) Uani 1 2 d S T P . . I3 I 0.4282(3) 0.2500 -0.1360(3) 0.078(4) Uani 0.53(4) 2 d S T P A 1 I3A I 0.4195(12) 0.2500 -0.115(2) 0.235(8) Uani 0.47(4) 2 d S T P A 2 I4A I 0.582(3) 0.2500 -0.2010(12) 0.116(4) Uani 0.53(10) 2 d S T P A 2 I4 I 0.5977(7) 0.2500 -0.2069(6) 0.074(5) Uani 0.47(10) 2 d S T P A 1 P1 P 0.7285(2) 0.2500 0.1610(3) 0.0472(11) Uani 1 2 d S T P . . F1 F 0.7947(8) 0.5519 -0.0886(7) 0.123(4) Uani 1 1 d . . . . . F2 F 0.8329(11) 0.554(2) -0.2229(8) 0.174(7) Uani 1 1 d . . . . . F3 F 0.8521(16) 0.2500 -0.2890(12) 0.216(14) Uani 1 2 d S T P . . F4 F 1.0188(5) -0.0485(12) 0.3311(7) 0.104(3) Uani 1 1 d . . . . . F5 F 1.1804(6) -0.0474(14) 0.4236(7) 0.117(4) Uani 1 1 d . . . . . F6 F 1.2606(6) 0.2500 0.4697(7) 0.087(4) Uani 1 2 d S T P . . F7 F 0.6295(7) 0.5446 0.3921(7) 0.129(5) Uani 1 1 d . . . . . F8 F 0.5879(7) 0.5645 0.5215(8) 0.182(8) Uani 1 1 d . . . . . F9 F 0.5745(10) 0.2500 0.5984(10) 0.181(12) Uani 1 2 d S T P . . F10 F 0.7314(4) 0.0442(11) 0.1629(5) 0.070(2) Uani 1 1 d . . . . . N1 N 0.8243(8) 0.2500 0.1382(8) 0.044(3) Uani 1 2 d S T P . . N2 N 0.7808(7) 0.2500 0.2712(7) 0.043(3) Uani 1 2 d S T P . . N3 N 0.6275(9) 0.2500 0.1723(9) 0.058(4) Uani 1 2 d S T P . . N4 N 0.6674(8) 0.2500 0.0543(9) 0.053(4) Uani 1 2 d S T P A . C1 C 0.7667(11) 0.2500 -0.0106(12) 0.066(5) Uani 1 2 d S T P A . C2 C 0.8320(11) 0.2500 0.0625(9) 0.054(4) Uani 1 2 d S T P . . C3 C 0.9145(12) 0.2500 0.0725(14) 0.082(7) Uani 1 2 d S T P . . H3 H 0.9361 0.2500 0.0294 0.098 Uiso 1 2 calc R U P . . C4 C 0.9600(11) 0.2500 0.1522(10) 0.062(5) Uani 1 2 d S T P . . H4 H 1.0187 0.2500 0.1749 0.074 Uiso 1 2 calc R U P . . C5 C 0.9055(9) 0.2500 0.1965(10) 0.054(5) Uani 1 2 d S T P . . C6 C 0.9238(9) 0.2500 0.2777(11) 0.047(4) Uani 1 2 d S T P . . C7 C 0.8632(11) 0.2500 0.3119(11) 0.055(4) Uani 1 2 d S T P . . C8 C 0.8793(10) 0.2500 0.3992(10) 0.067(6) Uani 1 2 d S T P . . H8 H 0.9316 0.2500 0.4419 0.080 Uiso 1 2 calc R U P . . C9 C 0.8057(13) 0.2500 0.4063(12) 0.083(7) Uani 1 2 d S T P . . H9 H 0.7972 0.2500 0.4571 0.100 Uiso 1 2 calc R U P . . C10 C 0.7415(10) 0.2500 0.3305(10) 0.057(5) Uani 1 2 d S T P . . C11 C 0.6597(11) 0.2500 0.3180(11) 0.066(5) Uani 1 2 d S T P . . C12 C 0.6007(11) 0.2500 0.2381(11) 0.057(5) Uani 1 2 d S T P . . C13 C 0.5124(11) 0.2500 0.2077(15) 0.070(6) Uani 1 2 d S T P . . C14 C 0.4864(11) 0.2500 0.1243(15) 0.066(5) Uani 1 2 d S T P . . C15 C 0.5610(10) 0.2500 0.1019(10) 0.058(5) Uani 1 2 d S T P . . C16 C 0.5822(10) 0.2500 0.0312(11) 0.051(4) Uani 1 2 d S T P A . C17 C 0.5462(12) 0.2500 -0.0543(12) 0.065(5) Uani 1 2 d S T P . . C18 C 0.6101(13) 0.2500 -0.0810(13) 0.068(5) Uani 1 2 d S T P A . C19 C 0.6872(11) 0.2500 -0.0160(10) 0.054(4) Uani 1 2 d S T P . . C20 C 0.7870(13) 0.2500 -0.0884(12) 0.082(7) Uani 1 2 d S T P . . C21 C 0.7998(11) 0.404(3) -0.1222(10) 0.094(6) Uani 1 1 d . . . . . C22 C 0.8214(16) 0.4067 -0.1891(12) 0.142(10) Uani 1 1 d . . . . . C23 C 0.827(3) 0.2500 -0.227(2) 0.18(2) Uani 1 2 d S T P . . C24 C 1.0121(10) 0.2500 0.3274(10) 0.048(4) Uani 1 2 d S T P . . C25 C 1.0577(7) 0.099(2) 0.3549(8) 0.064(4) Uani 1 1 d . . . . . C26 C 1.1394(7) 0.101(2) 0.4003(8) 0.064(4) Uani 1 1 d . . . . . C27 C 1.1811(9) 0.2500 0.4239(9) 0.051(5) Uani 1 2 d S T P . . C28 C 0.6358(11) 0.2500 0.3880(13) 0.076(6) Uani 1 2 d DS T P . . C29 C 0.6228(9) 0.4000(17) 0.4257(11) 0.093(6) Uani 1 1 d D . . . . C30 C 0.6022(9) 0.3986 0.4933(10) 0.116(7) Uani 1 1 d D . . . . C31 C 0.5932(14) 0.2500 0.5331(11) 0.116(7) Uani 1 2 d DS T P . . Cl2 Cl 1.2504(5) 0.2500 0.6786(6) 0.138(3) Uani 1 2 d DS T P . . Cl1 Cl 1.0837(5) 0.2500 0.5705(4) 0.208(7) Uani 1 2 d DS T P . . C32 C 1.1489(4) 0.2500 0.6692(5) 0.208(7) Uani 1 2 d DS T P . . Cl3 Cl 0.8370(6) 0.6787(14) 0.1192(7) 0.118(3) Uiso 0.5 1 d D . P . . Cl4 Cl 0.9642(12) 0.7500 0.0664(10) 0.252(8) Uiso 1 2 d DS . P . . C33 C 0.9363(7) 0.7500 0.1505(11) 0.34(4) Uiso 1 2 d DS . P . . 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 I1 0.0431(7) 0.1000(12) 0.1080(12) 0.000 0.0371(7) 0.000 I2 0.0374(7) 0.1091(14) 0.1083(13) 0.000 0.0096(7) 0.000 I3 0.032(2) 0.119(5) 0.063(4) 0.000 -0.0068(13) 0.000 I3A 0.096(7) 0.268(16) 0.261(15) 0.000 -0.037(8) 0.000 I4A 0.142(9) 0.117(6) 0.073(5) 0.000 0.019(7) 0.000 I4 0.052(9) 0.118(5) 0.038(5) 0.000 -0.003(3) 0.000 P1 0.028(2) 0.061(3) 0.050(2) 0.000 0.0110(17) 0.000 F1 0.155(10) 0.132(10) 0.104(8) 0.011(8) 0.071(8) -0.016(9) F2 0.220(16) 0.215(17) 0.117(10) 0.044(11) 0.098(11) -0.021(14) F3 0.20(2) 0.39(4) 0.101(14) 0.000 0.101(16) 0.000 F4 0.056(5) 0.063(6) 0.164(9) 0.002(6) 0.002(5) -0.002(5) F5 0.062(5) 0.084(7) 0.166(10) 0.022(7) -0.010(6) 0.025(5) F6 0.037(5) 0.132(12) 0.079(8) 0.000 0.005(5) 0.000 F7 0.139(9) 0.134(10) 0.160(10) -0.064(9) 0.109(9) -0.067(8) F8 0.163(11) 0.242(17) 0.203(13) -0.151(13) 0.142(11) -0.129(12) F9 0.095(11) 0.38(4) 0.090(11) 0.000 0.066(10) 0.000 F10 0.051(4) 0.072(5) 0.083(5) 0.007(4) 0.018(4) -0.001(4) N1 0.036(7) 0.060(9) 0.039(7) 0.000 0.016(6) 0.000 N2 0.023(6) 0.068(9) 0.035(6) 0.000 0.005(5) 0.000 N3 0.040(8) 0.076(11) 0.062(9) 0.000 0.021(7) 0.000 N4 0.042(8) 0.044(8) 0.062(9) 0.000 0.005(7) 0.000 C1 0.041(10) 0.082(15) 0.063(11) 0.000 0.003(8) 0.000 C2 0.053(10) 0.079(13) 0.031(8) 0.000 0.018(7) 0.000 C3 0.049(11) 0.13(2) 0.076(14) 0.000 0.029(10) 0.000 C4 0.044(9) 0.095(15) 0.044(10) 0.000 0.015(8) 0.000 C5 0.026(8) 0.082(13) 0.045(9) 0.000 0.001(7) 0.000 C6 0.031(8) 0.048(10) 0.066(11) 0.000 0.024(8) 0.000 C7 0.050(10) 0.067(12) 0.053(10) 0.000 0.023(8) 0.000 C8 0.025(8) 0.133(19) 0.039(9) 0.000 0.005(7) 0.000 C9 0.060(12) 0.15(2) 0.044(10) 0.000 0.026(9) 0.000 C10 0.038(9) 0.091(14) 0.045(9) 0.000 0.019(7) 0.000 C11 0.046(10) 0.094(16) 0.055(11) 0.000 0.014(8) 0.000 C12 0.045(9) 0.074(13) 0.055(10) 0.000 0.020(8) 0.000 C13 0.042(10) 0.069(14) 0.097(16) 0.000 0.019(10) 0.000 C14 0.045(10) 0.059(12) 0.105(17) 0.000 0.041(11) 0.000 C15 0.030(8) 0.097(15) 0.042(9) 0.000 0.005(7) 0.000 C16 0.042(9) 0.033(9) 0.071(12) 0.000 0.012(8) 0.000 C17 0.056(11) 0.056(12) 0.059(11) 0.000 -0.008(9) 0.000 C18 0.059(12) 0.057(12) 0.077(13) 0.000 0.012(10) 0.000 C19 0.048(10) 0.062(12) 0.045(9) 0.000 0.009(8) 0.000 C20 0.061(12) 0.14(2) 0.048(11) 0.000 0.019(10) 0.000 C21 0.087(11) 0.129(18) 0.071(11) 0.017(11) 0.036(9) 0.009(12) C22 0.15(2) 0.22(3) 0.059(11) 0.010(16) 0.040(12) -0.01(2) C23 0.27(6) 0.23(5) 0.08(2) 0.000 0.11(3) 0.000 C24 0.043(9) 0.068(12) 0.046(9) 0.000 0.030(7) 0.000 C25 0.042(7) 0.080(10) 0.069(8) 0.008(8) 0.019(6) -0.004(7) C26 0.041(6) 0.085(10) 0.058(7) 0.008(7) 0.006(6) 0.014(7) C27 0.029(8) 0.093(15) 0.027(7) 0.000 0.005(6) 0.000 C28 0.034(9) 0.111(19) 0.097(16) 0.000 0.040(10) 0.000 C29 0.063(9) 0.126(16) 0.109(13) -0.019(12) 0.053(9) -0.041(10) C30 0.058(7) 0.20(2) 0.111(13) -0.056(16) 0.053(8) -0.046(12) C31 0.058(7) 0.20(2) 0.111(13) -0.056(16) 0.053(8) -0.046(12) Cl2 0.085(5) 0.200(10) 0.129(6) 0.000 0.037(5) 0.000 Cl1 0.081(5) 0.47(2) 0.068(4) 0.000 0.014(4) 0.000 C32 0.081(5) 0.47(2) 0.068(4) 0.000 0.014(4) 0.000 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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' P P 0.1023 0.0942 '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 I3A I3A C17 0(10) 4_565 . F10 P1 F10 176.5(6) 4_565 . F10 P1 N4 91.4(3) 4_565 . F10 P1 N4 91.3(3) . . F10 P1 N2 88.8(3) 4_565 . F10 P1 N2 88.8(3) . . N4 P1 N2 174.3(6) . . F10 P1 N3 91.2(3) 4_565 . F10 P1 N3 91.3(3) . . N4 P1 N3 82.9(7) . . N2 P1 N3 91.4(6) . . F10 P1 N1 88.9(3) 4_565 . F10 P1 N1 88.9(3) . . N4 P1 N1 91.2(6) . . N2 P1 N1 94.6(6) . . N3 P1 N1 174.0(7) . . C2 N1 C5 106.8(13) . . C2 N1 P1 127.4(11) . . C5 N1 P1 125.8(11) . . C7 N2 C10 107.2(12) . . C7 N2 P1 126.9(11) . . C10 N2 P1 125.8(10) . . C15 N3 C12 109.6(14) . . C15 N3 P1 116.0(12) . . C12 N3 P1 134.5(12) . . C16 N4 C19 107.8(14) . . C16 N4 P1 118.9(12) . . C19 N4 P1 133.2(12) . . C19 C1 C2 123.3(18) . . C19 C1 C20 119.1(17) . . C2 C1 C20 117.6(17) . . C3 C2 N1 108.8(15) . . C3 C2 C1 126.4(17) . . N1 C2 C1 124.8(16) . . C4 C3 C2 109.7(18) . . C3 C4 C5 108.1(16) . . C6 C5 C4 128.7(14) . . C6 C5 N1 124.7(14) . . C4 C5 N1 106.6(14) . . C5 C6 C7 121.8(15) . . C5 C6 C24 116.0(13) . . C7 C6 C24 122.2(16) . . N2 C7 C6 126.2(16) . . N2 C7 C8 109.6(14) . . C6 C7 C8 124.2(16) . . C9 C8 C7 105.2(15) . . C8 C9 C10 112.3(16) . . C11 C10 C9 126.1(16) . . C11 C10 N2 128.2(16) . . C9 C10 N2 105.7(14) . . C10 C11 C12 120.7(17) . . C10 C11 C28 117.5(17) . . C12 C11 C28 121.8(17) . . N3 C12 C11 119.3(15) . . N3 C12 C13 108.2(16) . . C11 C12 C13 132.5(18) . . C14 C13 C12 107.9(18) . . C14 C13 I1 124.6(14) . . C12 C13 I1 127.4(17) . . C13 C14 C15 107.0(17) . . C13 C14 I2 126.4(13) . . C15 C14 I2 126.7(16) . . N3 C15 C16 113.7(14) . . N3 C15 C14 107.3(16) . . C16 C15 C14 138.9(17) . . N4 C16 C17 110.0(16) . . N4 C16 C15 108.5(15) . . C17 C16 C15 141.5(17) . . C18 C17 C16 105.1(17) . . C18 C17 I3 119.7(15) . . C16 C17 I3 135.2(16) . . C18 C17 I3A 132(2) . 4_565 C16 C17 I3A 123(2) . 4_565 C18 C17 I3A 132(2) . . C16 C17 I3A 123(2) . . I3A C17 I3A 0(2) 4_565 . C17 C18 C19 112.1(19) . . C17 C18 I4A 116(2) . . C19 C18 I4A 132(2) . . C17 C18 I4 124.2(15) . . C19 C18 I4 123.8(16) . . C1 C19 N4 120.0(16) . . C1 C19 C18 135.0(19) . . N4 C19 C18 105.0(16) . . C21 C20 C21 120(2) 4_565 . C21 C20 C1 120.1(11) 4_565 . C21 C20 C1 120.1(11) . . F1 C21 C22 117.4(17) . . F1 C21 C20 121.6(14) . . C22 C21 C20 120.9(19) . . F2 C22 C21 121.5(14) . . F2 C22 C23 119.5(17) . . C21 C22 C23 118.8(16) . . F3 C23 C22 119.3(14) . 4_565 F3 C23 C22 119.3(14) . . C22 C23 C22 120(2) 4_565 . C25 C24 C25 114.0(16) . 4_565 C25 C24 C6 123.0(8) . . C25 C24 C6 123.0(8) 4_565 . F4 C25 C26 120.0(14) . . F4 C25 C24 117.4(11) . . C26 C25 C24 122.5(15) . . F5 C26 C25 120.1(14) . . F5 C26 C27 118.7(10) . . C25 C26 C27 121.2(14) . . F6 C27 C26 120.7(7) . . F6 C27 C26 120.7(7) . 4_565 C26 C27 C26 118.6(15) . 4_565 C29 C28 C29 113(2) . 4_565 C29 C28 C11 123.3(10) . . C29 C28 C11 123.3(10) 4_565 . F7 C29 C30 119.9(9) . . F7 C29 C28 117.3(11) . . C30 C29 C28 122.8(16) . . C29 C30 C31 123.8(6) . . C29 C30 F8 115.1(9) . . C31 C30 F8 121.1(6) . . F9 C31 C30 123.38(12) . 4_565 F9 C31 C30 123.38(12) . . C30 C31 C30 113.16(14) 4_565 . Cl2 C32 Cl1 113.2(7) . . Cl3 Cl3 C33 70.9(4) 4_575 . Cl3 C33 Cl3 38.2(8) 4_575 . Cl3 C33 Cl4 106.1(12) 4_575 . Cl3 C33 Cl4 106.1(12) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 I1 C13 2.03(2) . I2 C14 2.05(2) . I3 C17 2.038(19) . I3A I3A 0.00(4) 4_565 I3A C17 2.07(2) . I4A C18 1.98(3) . I4 C18 2.14(3) . P1 F10 1.607(8) 4_565 P1 F10 1.607(8) . P1 N4 1.797(15) . P1 N2 1.821(12) . P1 N3 1.821(14) . P1 N1 1.829(12) . F1 C21 1.31(2) . F2 C22 1.342(18) . F3 C23 1.30(3) . F4 C25 1.325(17) . F5 C26 1.341(17) . F6 C27 1.324(18) . F7 C29 1.297(16) . F8 C30 1.438(7) . F9 C31 1.29(2) . N1 C2 1.377(19) . N1 C5 1.416(19) . N2 C7 1.35(2) . N2 C10 1.42(2) . N3 C15 1.36(2) . N3 C12 1.38(2) . N4 C16 1.38(2) . N4 C19 1.39(2) . C1 C19 1.34(3) . C1 C2 1.38(2) . C1 C20 1.52(3) . C2 C3 1.37(3) . C3 C4 1.34(3) . C4 C5 1.41(2) . C5 C6 1.35(2) . C6 C7 1.37(2) . C6 C24 1.47(2) . C7 C8 1.45(2) . C8 C9 1.32(3) . C9 C10 1.40(3) . C10 C11 1.35(2) . C11 C12 1.41(3) . C11 C28 1.42(3) . C12 C13 1.43(3) . C13 C14 1.37(3) . C14 C15 1.47(2) . C15 C16 1.41(2) . C16 C17 1.40(3) . C17 C18 1.34(3) . C17 I3A 2.07(2) 4_565 C18 C19 1.42(3) . C20 C21 1.39(2) 4_565 C20 C21 1.39(2) . C21 C22 1.35(3) . C22 C23 1.412(16) . C23 C22 1.412(16) 4_565 C24 C25 1.404(17) . C24 C25 1.404(17) 4_565 C25 C26 1.355(17) . C26 C27 1.357(17) . C27 C26 1.357(17) 4_565 C28 C29 1.3999(12) . C28 C29 1.4000(12) 4_565 C29 C30 1.35(2) . C30 C31 1.3898(12) . C31 C30 1.3897(12) 4_565 Cl2 C32 1.7000(11) . Cl1 C32 1.7001(12) . Cl3 Cl3 1.11(2) 4_575 Cl3 C33 1.7000(11) . Cl4 C33 1.7000(11) . C33 Cl3 1.7000(11) 4_575