#------------------------------------------------------------------------------ #$Date: 2017-09-14 05:44:07 +0300 (Thu, 14 Sep 2017) $ #$Revision: 200875 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/04/42/7044224.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_7044224 loop_ _publ_author_name 'Schmid, Paul' 'Maier, Matthias' 'Pfeiffer, Hendrik' 'Belz, Anja' 'Henry, Lucas' 'Friedrich, Alexandra' 'Sch\"onfeld, Fabian' 'Edkins, Katharina' 'Schatzschneider, Ulrich' _publ_section_title ; Catalyst-free room-temperature iClick reaction of molybdenum(II) and tungsten(II) azide complexes with electron-poor alkynes: Structural preferences and kinetic studies ; _journal_name_full 'Dalton Trans.' _journal_paper_doi 10.1039/C7DT03096G _journal_year 2017 _chemical_formula_moiety 'C21 H18 F3 N5 O4 W' _chemical_formula_sum 'C21 H18 F3 N5 O4 W' _chemical_formula_weight 645.25 _chemical_name_common '[W(allyl)(triazolateCF3,COOEt)(bpy)(CO)2]' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_date 2016-07-01 _audit_update_record ; 2017-07-17 deposited with the CCDC. 2017-09-13 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 91.10(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.078(5) _cell_length_b 9.984(5) _cell_length_c 19.167(11) _cell_measurement_reflns_used 9392 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 36.34 _cell_measurement_theta_min 2.30 _cell_volume 2119.5(19) _computing_cell_refinement 'Saint+ ver. V8.34A (Bruker AXS)' _computing_data_collection 'APEX2 ver. 2014.11-0 (Bruker AXS)' _computing_data_reduction 'Saint+ ver. V8.34A (Bruker AXS)' _computing_molecular_graphics 'ShelXLe (Huebschle et all, 2011)' _computing_publication_material 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXT (Sheldrick, 2014)' _diffrn_ambient_temperature 100(2) _diffrn_detector 'CCD area detector (Apex2)' _diffrn_detector_area_resol_mean 8.333 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker X8-APEX II' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0305 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 24833 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.022 _diffrn_reflns_theta_min 1.839 _diffrn_source 'rotating-anode (Nonius FR-591)' _exptl_absorpt_coefficient_mu 5.517 _exptl_absorpt_correction_T_max 0.7471 _exptl_absorpt_correction_T_min 0.5169 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SadAbs 2014/5 (Bruker AXS)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 2.022 _exptl_crystal_description block _exptl_crystal_F_000 1248 _exptl_crystal_preparation 'Crystal fragment soaked in perfluoro polyether oil.' _exptl_crystal_recrystallization_method 'recrystallised from dichloromethane and hexane by evaporation' _exptl_crystal_size_max 0.588 _exptl_crystal_size_mid 0.472 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.873 _refine_diff_density_min -0.626 _refine_diff_density_rms 0.078 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 323 _refine_ls_number_reflns 4178 _refine_ls_number_restraints 5 _refine_ls_restrained_S_all 1.048 _refine_ls_R_factor_all 0.0172 _refine_ls_R_factor_gt 0.0155 _refine_ls_shift/su_max 0.003 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0072P)^2^+2.9018P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0351 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3932 _reflns_number_total 4178 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7dt03096g2.cif _cod_data_source_block AF048 _cod_database_code 7044224 _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 0.140 _shelx_estimated_absorpt_t_max 0.405 _shelx_res_file ; AF048.res created by SHELXL-2014/7 TITL AF0482_a.res in P2(1)/c REM Old TITL AF0482 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.042, Rweak 0.002, Alpha 0.063, Orientation as input REM Formula found by SHELXT: C23 N4 O3 F3 W REM estimated errors from Monte Carlo simulation using 32 cycles CELL 0.71073 11.0776 9.9842 19.1668 90.000 91.101 90.000 ZERR 4.000 0.0047 0.0052 0.0112 0.000 0.020 0.000 REM CELL 0.71073 11.0776 9.9842 19.1668 90.000 91.101 90.000 REM ZERR 4.000 0.0004 0.0004 0.0007 0.000 0.002 0.000 LATT 1 SYMM -X, 1/2+Y, 1/2-Z SFAC C H N O F W UNIT 84 72 20 16 12 4 TEMP -173.000 SIZE 0.200 0.472 0.588 L.S. 10 BOND $H LIST 4 ACTA CONF SHEL 999. 0.81 FMAP 2 PLAN 20 WGHT 0.007200 2.901800 FVAR 0.21399 W1 6 0.156948 0.312372 0.666508 11.00000 0.01051 0.00936 = 0.00926 0.00068 -0.00018 -0.00014 C1 1 0.064122 0.191143 0.605796 11.00000 0.01890 0.01499 = 0.01354 0.00585 -0.00024 0.00080 O1 4 0.013504 0.113754 0.570613 11.00000 0.03092 0.01774 = 0.02202 0.00036 -0.00867 -0.00813 N1 3 0.271924 0.413832 0.526514 11.00000 0.01669 0.01657 = 0.01418 0.00057 -0.00177 -0.00201 F1 5 0.329517 0.371884 0.361794 11.00000 0.04916 0.04865 = 0.01504 0.00036 -0.00886 -0.02573 F2 5 0.479563 0.486500 0.398534 11.00000 0.02535 0.03211 = 0.02142 0.00375 0.00187 -0.01085 O2 4 0.265391 0.032123 0.703790 11.00000 0.02290 0.01194 = 0.02652 0.00185 -0.00346 0.00240 C2 1 0.227911 0.137488 0.690315 11.00000 0.01365 0.01755 = 0.01292 -0.00165 -0.00210 -0.00384 N2 3 0.286707 0.329953 0.581134 11.00000 0.01254 0.01186 = 0.00877 0.00032 -0.00115 -0.00311 F3 5 0.300841 0.561049 0.412067 11.00000 0.04751 0.04589 = 0.03432 0.02272 0.01113 0.02186 C3 1 0.428338 0.278577 0.512940 11.00000 0.01606 0.01666 = 0.01338 -0.00161 0.00020 -0.00217 O3 4 0.561114 0.215347 0.424412 11.00000 0.02445 0.02756 = 0.02134 0.00304 0.00785 0.00499 N3 3 0.379685 0.248391 0.574647 11.00000 0.01624 0.01661 = 0.01584 -0.00079 0.00021 0.00048 N4 3 0.107989 0.516365 0.630797 11.00000 0.01037 0.01326 = 0.00816 -0.00041 0.00101 -0.00064 C4 1 0.360312 0.381273 0.482998 11.00000 0.01602 0.01623 = 0.01290 -0.00168 -0.00116 -0.00344 O4 4 0.587812 0.129177 0.531671 11.00000 0.02018 0.02273 = 0.01985 0.00307 0.00439 0.00619 C8 1 0.158917 0.748435 0.628529 11.00000 0.01467 0.01355 = 0.00997 0.00018 0.00233 -0.00287 AFIX 43 H8 2 0.210419 0.819146 0.643738 11.00000 -1.20000 AFIX 0 C7 1 0.064397 0.773793 0.582216 11.00000 0.01834 0.01195 = 0.01165 0.00195 0.00238 0.00340 AFIX 43 H7 2 0.049487 0.862083 0.565702 11.00000 -1.20000 AFIX 0 C9 1 0.177931 0.619202 0.652567 11.00000 0.01131 0.01448 = 0.00780 -0.00135 0.00229 0.00016 C6 1 -0.008058 0.668469 0.560346 11.00000 0.01261 0.01741 = 0.01004 0.00015 -0.00032 0.00308 AFIX 43 H6 2 -0.073769 0.683185 0.528695 11.00000 -1.20000 AFIX 0 C10 1 0.274861 0.584867 0.703556 11.00000 0.01173 0.01705 = 0.00989 0.00008 0.00196 -0.00141 N5 3 0.286864 0.452951 0.717569 11.00000 0.01146 0.01470 = 0.00973 0.00075 0.00134 0.00187 C5 1 0.016803 0.541720 0.585310 11.00000 0.01376 0.01353 = 0.00971 -0.00209 -0.00003 -0.00164 AFIX 43 H5 2 -0.032454 0.469341 0.569763 11.00000 -1.20000 AFIX 0 DFIX 0.95 0.005 C15 H15A C15 H15B C16 H16 C17 H17A C17 H17B C11 1 0.346417 0.680000 0.737128 11.00000 0.01870 0.01803 = 0.01727 0.00123 -0.00078 -0.00512 AFIX 43 H11 2 0.336118 0.772435 0.726875 11.00000 -1.20000 AFIX 0 C21 1 0.368339 0.450565 0.414518 11.00000 0.01892 0.02166 = 0.01752 0.00218 -0.00286 -0.00417 C12 1 0.432664 0.639315 0.785526 11.00000 0.01867 0.02603 = 0.01669 0.00019 -0.00393 -0.00857 AFIX 43 H12 2 0.480506 0.703419 0.810085 11.00000 -1.20000 AFIX 0 C13 1 0.448420 0.504125 0.797742 11.00000 0.01185 0.03039 = 0.01290 0.00562 -0.00222 -0.00114 AFIX 43 H13 2 0.509406 0.473559 0.829423 11.00000 -1.20000 AFIX 0 C18 1 0.532380 0.206404 0.483666 11.00000 0.01911 0.01631 = 0.01797 -0.00053 0.00054 0.00022 C17 1 0.115760 0.261285 0.781360 11.00000 0.01882 0.01988 = 0.01147 0.00215 0.00211 0.00048 H17A 2 0.174984 0.288984 0.814843 11.00000 -1.20000 H17B 2 0.088306 0.171549 0.786091 11.00000 -1.20000 C16 1 0.034582 0.357138 0.753244 11.00000 0.01675 0.01665 = 0.01625 0.00240 0.00487 0.00094 H16 2 0.038059 0.448720 0.766514 11.00000 -1.20000 C15 1 -0.043249 0.309303 0.699407 11.00000 0.01484 0.02101 = 0.02014 0.00690 0.00150 0.00118 H15A 2 -0.094457 0.371394 0.675703 11.00000 -1.20000 H15B 2 -0.074657 0.221022 0.703119 11.00000 -1.20000 C14 1 0.374276 0.414393 0.763242 11.00000 0.01522 0.01939 = 0.01267 0.00382 -0.00053 0.00232 AFIX 43 H14 2 0.385098 0.321454 0.771950 11.00000 -1.20000 AFIX 0 C19 1 0.693667 0.059056 0.506773 11.00000 0.01889 0.02303 = 0.03283 0.00410 0.01125 0.00488 AFIX 23 H19A 2 0.754716 0.124407 0.491185 11.00000 -1.20000 H19B 2 0.670994 0.001200 0.466671 11.00000 -1.20000 AFIX 0 C20 1 0.744749 -0.024376 0.565057 11.00000 0.01828 0.02726 = 0.02841 0.00128 0.00365 0.00124 AFIX 137 H20A 2 0.770276 0.033958 0.603725 11.00000 -1.50000 H20B 2 0.814430 -0.074872 0.548478 11.00000 -1.50000 H20C 2 0.683007 -0.086872 0.581151 11.00000 -1.50000 REM ##### AFIX 0 HKLF 4 REM AF0482_a.res in P2(1)/c REM R1 = 0.0155 for 3932 Fo > 4sig(Fo) and 0.0172 for all 4178 data REM 323 parameters refined using 5 restraints END WGHT 0.0072 2.9018 REM Highest difference peak 0.873, deepest hole -0.626, 1-sigma level 0.078 Q1 1 0.0976 0.3097 0.6954 11.00000 0.05 0.87 Q2 1 0.2246 0.3112 0.6391 11.00000 0.05 0.74 Q3 1 0.2592 0.6107 0.4548 11.00000 0.05 0.74 Q4 1 0.4033 0.4781 0.3467 11.00000 0.05 0.66 Q5 1 0.1068 0.3077 0.6264 11.00000 0.05 0.43 Q6 1 0.2083 0.3080 0.7065 11.00000 0.05 0.42 Q7 1 0.5828 0.2541 0.4589 11.00000 0.05 0.36 Q8 1 0.6330 0.0548 0.4637 11.00000 0.05 0.34 Q9 1 0.7328 0.1130 0.5554 11.00000 0.05 0.32 Q10 1 0.1751 0.1987 0.6757 11.00000 0.05 0.31 Q11 1 0.2581 0.3386 0.5625 11.00000 0.05 0.30 Q12 1 0.2334 0.5992 0.6727 11.00000 0.05 0.30 Q13 1 0.1215 0.4454 0.6444 11.00000 0.05 0.30 Q14 1 0.2935 0.3407 0.6079 11.00000 0.05 0.30 Q15 1 0.3250 0.2985 0.5730 11.00000 0.05 0.29 Q16 1 0.1304 0.7536 0.5922 11.00000 0.05 0.28 Q17 1 0.1627 0.4169 0.6647 11.00000 0.05 0.28 Q18 1 0.0135 0.3244 0.7244 11.00000 0.05 0.27 Q19 1 -0.0157 0.3141 0.7595 11.00000 0.05 0.26 Q20 1 0.4336 0.5666 0.7913 11.00000 0.05 0.26 ; _shelx_res_checksum 33859 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -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 W1 W 0.15695(2) 0.31237(2) 0.66651(2) 0.00971(4) Uani 1 1 d . . C1 C 0.0641(2) 0.1911(2) 0.60580(12) 0.0158(5) Uani 1 1 d . . O1 O 0.01350(17) 0.11375(18) 0.57061(9) 0.0237(4) Uani 1 1 d . . N1 N 0.27192(18) 0.4138(2) 0.52651(10) 0.0158(4) Uani 1 1 d . . F1 F 0.32952(17) 0.37188(19) 0.36179(8) 0.0377(4) Uani 1 1 d . . F2 F 0.47956(14) 0.48650(16) 0.39853(8) 0.0263(4) Uani 1 1 d . . O2 O 0.26539(16) 0.03212(17) 0.70379(9) 0.0205(4) Uani 1 1 d . . C2 C 0.2279(2) 0.1375(2) 0.69031(12) 0.0147(5) Uani 1 1 d . . N2 N 0.28671(18) 0.32995(19) 0.58113(10) 0.0111(4) Uani 1 1 d . . F3 F 0.30084(17) 0.56105(19) 0.41207(9) 0.0424(5) Uani 1 1 d . . C3 C 0.4283(2) 0.2786(2) 0.51294(12) 0.0154(5) Uani 1 1 d . . O3 O 0.56111(17) 0.21535(19) 0.42441(9) 0.0244(4) Uani 1 1 d . . N3 N 0.37968(19) 0.2484(2) 0.57465(10) 0.0162(4) Uani 1 1 d . . N4 N 0.10799(17) 0.51636(19) 0.63080(9) 0.0106(4) Uani 1 1 d . . C4 C 0.3603(2) 0.3813(2) 0.48300(12) 0.0151(5) Uani 1 1 d . . O4 O 0.58781(16) 0.12918(18) 0.53167(9) 0.0209(4) Uani 1 1 d . . C8 C 0.1589(2) 0.7484(2) 0.62853(12) 0.0127(5) Uani 1 1 d . . H8 H 0.2104 0.8191 0.6437 0.015 Uiso 1 1 calc R U C7 C 0.0644(2) 0.7738(2) 0.58222(12) 0.0140(5) Uani 1 1 d . . H7 H 0.0495 0.8621 0.5657 0.017 Uiso 1 1 calc R U C9 C 0.1779(2) 0.6192(2) 0.65257(11) 0.0112(5) Uani 1 1 d . . C6 C -0.0081(2) 0.6685(2) 0.56035(12) 0.0134(5) Uani 1 1 d . . H6 H -0.0738 0.6832 0.5287 0.016 Uiso 1 1 calc R U C10 C 0.2749(2) 0.5849(2) 0.70356(11) 0.0129(5) Uani 1 1 d . . N5 N 0.28686(17) 0.45295(19) 0.71757(10) 0.0119(4) Uani 1 1 d . . C5 C 0.0168(2) 0.5417(2) 0.58531(11) 0.0123(5) Uani 1 1 d . . H5 H -0.0325 0.4693 0.5698 0.015 Uiso 1 1 calc R U C11 C 0.3464(2) 0.6800(3) 0.73713(13) 0.0180(5) Uani 1 1 d . . H11 H 0.3361 0.7724 0.7269 0.022 Uiso 1 1 calc R U C21 C 0.3683(2) 0.4506(3) 0.41452(13) 0.0194(5) Uani 1 1 d . . C12 C 0.4327(2) 0.6393(3) 0.78553(13) 0.0205(5) Uani 1 1 d . . H12 H 0.4805 0.7034 0.8101 0.025 Uiso 1 1 calc R U C13 C 0.4484(2) 0.5041(3) 0.79774(12) 0.0184(5) Uani 1 1 d . . H13 H 0.5094 0.4736 0.8294 0.022 Uiso 1 1 calc R U C18 C 0.5324(2) 0.2064(2) 0.48367(13) 0.0178(5) Uani 1 1 d . . C17 C 0.1158(2) 0.2613(3) 0.78136(12) 0.0167(5) Uani 1 1 d D . H17A H 0.1750(19) 0.289(3) 0.8148(11) 0.020 Uiso 1 1 d D U H17B H 0.088(2) 0.1715(11) 0.7861(14) 0.020 Uiso 1 1 d D U C16 C 0.0346(2) 0.3571(3) 0.75324(13) 0.0165(5) Uani 1 1 d D . H16 H 0.038(3) 0.4487(9) 0.7665(13) 0.020 Uiso 1 1 d D U C15 C -0.0432(2) 0.3093(3) 0.69941(13) 0.0187(5) Uani 1 1 d D . H15A H -0.094(2) 0.371(2) 0.6757(13) 0.022 Uiso 1 1 d D U H15B H -0.075(2) 0.2210(12) 0.7031(15) 0.022 Uiso 1 1 d D U C14 C 0.3743(2) 0.4144(3) 0.76324(12) 0.0158(5) Uani 1 1 d . . H14 H 0.3851 0.3215 0.7719 0.019 Uiso 1 1 calc R U C19 C 0.6937(2) 0.0591(3) 0.50677(15) 0.0248(6) Uani 1 1 d . . H19A H 0.7547 0.1244 0.4912 0.030 Uiso 1 1 calc R U H19B H 0.6710 0.0012 0.4667 0.030 Uiso 1 1 calc R U C20 C 0.7447(2) -0.0244(3) 0.56506(14) 0.0246(6) Uani 1 1 d . . H20A H 0.7703 0.0340 0.6037 0.037 Uiso 1 1 calc R U H20B H 0.8144 -0.0749 0.5485 0.037 Uiso 1 1 calc R U H20C H 0.6830 -0.0869 0.5812 0.037 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 W1 0.01051(5) 0.00936(5) 0.00926(5) 0.00068(3) -0.00018(3) -0.00014(4) C1 0.0189(13) 0.0150(12) 0.0135(12) 0.0058(10) -0.0002(10) 0.0008(10) O1 0.0309(11) 0.0177(9) 0.0220(9) 0.0004(8) -0.0087(8) -0.0081(8) N1 0.0167(11) 0.0166(10) 0.0142(10) 0.0006(8) -0.0018(8) -0.0020(8) F1 0.0492(11) 0.0486(11) 0.0150(8) 0.0004(7) -0.0089(7) -0.0257(9) F2 0.0253(9) 0.0321(9) 0.0214(8) 0.0038(7) 0.0019(7) -0.0108(7) O2 0.0229(10) 0.0119(9) 0.0265(10) 0.0019(7) -0.0035(8) 0.0024(7) C2 0.0137(12) 0.0175(13) 0.0129(11) -0.0016(9) -0.0021(9) -0.0038(10) N2 0.0125(10) 0.0119(9) 0.0088(9) 0.0003(7) -0.0011(7) -0.0031(8) F3 0.0475(11) 0.0459(11) 0.0343(10) 0.0227(9) 0.0111(8) 0.0219(9) C3 0.0161(12) 0.0167(12) 0.0134(12) -0.0016(9) 0.0002(9) -0.0022(10) O3 0.0244(10) 0.0276(10) 0.0213(10) 0.0030(8) 0.0079(8) 0.0050(8) N3 0.0162(11) 0.0166(10) 0.0158(10) -0.0008(8) 0.0002(8) 0.0005(9) N4 0.0104(10) 0.0133(10) 0.0082(9) -0.0004(7) 0.0010(7) -0.0006(8) C4 0.0160(12) 0.0162(12) 0.0129(11) -0.0017(9) -0.0012(9) -0.0034(10) O4 0.0202(10) 0.0227(9) 0.0198(9) 0.0031(7) 0.0044(7) 0.0062(8) C8 0.0147(12) 0.0135(11) 0.0100(11) 0.0002(9) 0.0023(9) -0.0029(9) C7 0.0183(13) 0.0120(11) 0.0116(11) 0.0019(9) 0.0024(9) 0.0034(9) C9 0.0113(11) 0.0145(11) 0.0078(10) -0.0013(9) 0.0023(9) 0.0002(9) C6 0.0126(12) 0.0174(12) 0.0100(11) 0.0002(9) -0.0003(9) 0.0031(9) C10 0.0117(11) 0.0170(12) 0.0099(11) 0.0001(9) 0.0020(9) -0.0014(9) N5 0.0115(10) 0.0147(10) 0.0097(9) 0.0007(8) 0.0013(7) 0.0019(8) C5 0.0138(11) 0.0135(12) 0.0097(11) -0.0021(9) 0.0000(9) -0.0016(9) C11 0.0187(13) 0.0180(12) 0.0173(12) 0.0012(10) -0.0008(10) -0.0051(10) C21 0.0189(13) 0.0217(13) 0.0175(12) 0.0022(10) -0.0029(10) -0.0042(11) C12 0.0187(13) 0.0260(14) 0.0167(13) 0.0002(10) -0.0039(10) -0.0086(11) C13 0.0119(12) 0.0304(14) 0.0129(11) 0.0056(10) -0.0022(9) -0.0011(10) C18 0.0191(13) 0.0163(12) 0.0180(13) -0.0005(10) 0.0005(10) 0.0002(10) C17 0.0188(13) 0.0199(13) 0.0115(11) 0.0021(10) 0.0021(9) 0.0005(10) C16 0.0168(13) 0.0167(12) 0.0162(12) 0.0024(10) 0.0049(10) 0.0009(10) C15 0.0148(13) 0.0210(13) 0.0201(13) 0.0069(10) 0.0015(10) 0.0012(10) C14 0.0152(12) 0.0194(13) 0.0127(11) 0.0038(9) -0.0005(9) 0.0023(10) C19 0.0189(13) 0.0230(14) 0.0328(15) 0.0041(12) 0.0112(11) 0.0049(11) C20 0.0183(14) 0.0273(15) 0.0284(14) 0.0013(11) 0.0037(11) 0.0012(11) 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' W W -0.8490 6.8722 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 0.00 2.00 0.0920 1.00 0.00 -2.00 0.1000 0.00 0.00 1.00 0.1760 0.00 0.00 -1.00 0.2080 1.00 1.00 2.00 0.3320 -1.00 -2.00 2.00 0.1090 0.00 -1.00 2.00 0.1240 0.00 1.00 -2.00 0.2390 0.00 1.00 -1.00 0.2310 -1.00 -2.00 -1.00 0.1880 0.00 -2.00 1.00 0.1370 1.00 -1.00 2.00 0.1840 -1.00 1.00 -2.00 0.2710 0.00 -1.00 0.00 0.1360 0.00 1.00 0.00 0.2940 -1.00 -2.00 -2.00 0.2010 -2.00 1.00 -2.00 0.2530 0.00 -2.00 -1.00 0.1500 2.00 -2.00 1.00 0.1660 -2.00 2.00 -1.00 0.2750 -1.00 2.00 0.00 0.2800 1.00 0.00 1.00 0.2270 -1.00 0.00 -1.00 0.2180 2.00 -1.00 1.00 0.1920 1.00 -1.00 0.00 0.1550 1.00 -2.00 -1.00 0.1280 0.00 1.00 1.00 0.3090 2.00 -2.00 -1.00 0.1450 -1.00 2.00 2.00 0.2890 -2.00 -1.00 -2.00 0.2250 1.00 -1.00 -2.00 0.1150 2.00 0.00 -1.00 0.1380 0.00 -1.00 -2.00 0.1890 1.00 0.00 0.00 0.1710 3.00 -1.00 -3.00 0.1120 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C1 W1 C2 77.98(10) C1 W1 N2 87.17(9) C2 W1 N2 88.82(9) C1 W1 C16 104.44(11) C2 W1 C16 104.68(10) N2 W1 C16 163.64(9) C1 W1 N4 105.22(9) C2 W1 N4 169.83(9) N2 W1 N4 81.76(7) C16 W1 N4 84.05(8) C1 W1 N5 168.58(9) C2 W1 N5 101.89(9) N2 W1 N5 81.42(8) C16 W1 N5 86.70(9) N4 W1 N5 73.02(7) C1 W1 C17 108.57(10) C2 W1 C17 70.64(10) N2 W1 C17 150.07(8) C16 W1 C17 36.30(9) N4 W1 C17 116.46(8) N5 W1 C17 81.85(9) C1 W1 C15 70.06(10) C2 W1 C15 107.80(10) N2 W1 C15 147.52(8) C16 W1 C15 36.32(9) N4 W1 C15 82.31(8) N5 W1 C15 120.21(9) C17 W1 C15 62.03(9) O1 C1 W1 176.3(2) C4 N1 N2 104.7(2) O2 C2 W1 177.3(2) N3 N2 N1 113.15(19) N3 N2 W1 122.77(15) N1 N2 W1 123.67(15) N3 C3 C4 107.8(2) N3 C3 C18 123.6(2) C4 C3 C18 128.5(2) N2 N3 C3 105.74(19) C5 N4 C9 118.5(2) C5 N4 W1 123.37(15) C9 N4 W1 118.00(15) N1 C4 C3 108.6(2) N1 C4 C21 119.6(2) C3 C4 C21 131.8(2) C18 O4 C19 114.4(2) C7 C8 C9 119.5(2) C7 C8 H8 120.2 C9 C8 H8 120.2 C8 C7 C6 118.9(2) C8 C7 H7 120.6 C6 C7 H7 120.6 N4 C9 C8 121.6(2) N4 C9 C10 115.7(2) C8 C9 C10 122.7(2) C5 C6 C7 118.8(2) C5 C6 H6 120.6 C7 C6 H6 120.6 N5 C10 C11 121.5(2) N5 C10 C9 115.2(2) C11 C10 C9 123.3(2) C14 N5 C10 118.3(2) C14 N5 W1 123.77(16) C10 N5 W1 117.89(15) N4 C5 C6 122.7(2) N4 C5 H5 118.7 C6 C5 H5 118.7 C12 C11 C10 119.5(2) C12 C11 H11 120.3 C10 C11 H11 120.3 F2 C21 F3 106.9(2) F2 C21 F1 105.7(2) F3 C21 F1 106.6(2) F2 C21 C4 113.7(2) F3 C21 C4 111.9(2) F1 C21 C4 111.6(2) C11 C12 C13 119.0(2) C11 C12 H12 120.5 C13 C12 H12 120.5 C14 C13 C12 118.9(2) C14 C13 H13 120.6 C12 C13 H13 120.6 O3 C18 O4 124.9(2) O3 C18 C3 123.4(2) O4 C18 C3 111.7(2) C16 C17 W1 67.88(14) C16 C17 H17A 119.1(17) W1 C17 H17A 115.6(18) C16 C17 H17B 118.2(17) W1 C17 H17B 111.6(17) H17A C17 H17B 115(2) C17 C16 C15 115.1(2) C17 C16 W1 75.81(15) C15 C16 W1 75.95(15) C17 C16 H16 121.9(17) C15 C16 H16 122.8(16) W1 C16 H16 111.9(17) C16 C15 W1 67.73(15) C16 C15 H15A 118.6(17) W1 C15 H15A 115.3(18) C16 C15 H15B 118.5(17) W1 C15 H15B 112.7(18) H15A C15 H15B 115(2) N5 C14 C13 122.7(2) N5 C14 H14 118.6 C13 C14 H14 118.6 O4 C19 C20 108.6(2) O4 C19 H19A 110.0 C20 C19 H19A 110.0 O4 C19 H19B 110.0 C20 C19 H19B 110.0 H19A C19 H19B 108.4 C19 C20 H20A 109.5 C19 C20 H20B 109.5 H20A C20 H20B 109.5 C19 C20 H20C 109.5 H20A C20 H20C 109.5 H20B C20 H20C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance W1 C1 1.957(3) W1 C2 1.965(3) W1 N2 2.206(2) W1 C16 2.211(3) W1 N4 2.213(2) W1 N5 2.224(2) W1 C17 2.314(3) W1 C15 2.317(3) C1 O1 1.163(3) N1 C4 1.338(3) N1 N2 1.348(3) F1 C21 1.344(3) F2 C21 1.325(3) O2 C2 1.158(3) N2 N3 1.321(3) F3 C21 1.333(3) C3 N3 1.343(3) C3 C4 1.390(3) C3 C18 1.479(4) O3 C18 1.189(3) N4 C5 1.346(3) N4 C9 1.348(3) C4 C21 1.488(3) O4 C18 1.340(3) O4 C19 1.454(3) C8 C7 1.383(3) C8 C9 1.385(3) C8 H8 0.9500 C7 C6 1.383(3) C7 H7 0.9500 C9 C10 1.478(3) C6 C5 1.379(3) C6 H6 0.9500 C10 N5 1.350(3) C10 C11 1.387(3) N5 C14 1.349(3) C5 H5 0.9500 C11 C12 1.380(3) C11 H11 0.9500 C12 C13 1.380(4) C12 H12 0.9500 C13 C14 1.376(3) C13 H13 0.9500 C17 C16 1.413(4) C17 H17A 0.950(5) C17 H17B 0.951(5) C16 C15 1.415(4) C16 H16 0.950(5) C15 H15A 0.950(5) C15 H15B 0.951(5) C14 H14 0.9500 C19 C20 1.496(4) C19 H19A 0.9900 C19 H19B 0.9900 C20 H20A 0.9800 C20 H20B 0.9800 C20 H20C 0.9800 loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion C4 N1 N2 N3 0.8(2) C4 N1 N2 W1 -172.06(15) N1 N2 N3 C3 -0.4(3) W1 N2 N3 C3 172.49(15) C4 C3 N3 N2 -0.1(3) C18 C3 N3 N2 -177.4(2) N2 N1 C4 C3 -0.8(2) N2 N1 C4 C21 177.2(2) N3 C3 C4 N1 0.6(3) C18 C3 C4 N1 177.7(2) N3 C3 C4 C21 -177.1(2) C18 C3 C4 C21 0.0(4) C9 C8 C7 C6 -0.8(3) C5 N4 C9 C8 -0.9(3) W1 N4 C9 C8 175.12(17) C5 N4 C9 C10 178.8(2) W1 N4 C9 C10 -5.2(3) C7 C8 C9 N4 1.4(3) C7 C8 C9 C10 -178.3(2) C8 C7 C6 C5 -0.2(3) N4 C9 C10 N5 5.0(3) C8 C9 C10 N5 -175.2(2) N4 C9 C10 C11 -172.7(2) C8 C9 C10 C11 7.0(4) C11 C10 N5 C14 -2.8(3) C9 C10 N5 C14 179.5(2) C11 C10 N5 W1 175.20(18) C9 C10 N5 W1 -2.6(3) C9 N4 C5 C6 -0.2(3) W1 N4 C5 C6 -176.01(17) C7 C6 C5 N4 0.8(4) N5 C10 C11 C12 0.6(4) C9 C10 C11 C12 178.1(2) N1 C4 C21 F2 136.2(2) C3 C4 C21 F2 -46.4(4) N1 C4 C21 F3 14.9(3) C3 C4 C21 F3 -167.6(2) N1 C4 C21 F1 -104.4(3) C3 C4 C21 F1 73.0(3) C10 C11 C12 C13 2.1(4) C11 C12 C13 C14 -2.5(4) C19 O4 C18 O3 3.1(4) C19 O4 C18 C3 -177.9(2) N3 C3 C18 O3 165.3(2) C4 C3 C18 O3 -11.3(4) N3 C3 C18 O4 -13.6(3) C4 C3 C18 O4 169.7(2) W1 C17 C16 C15 66.7(2) C17 C16 C15 W1 -66.7(2) C10 N5 C14 C13 2.3(3) W1 N5 C14 C13 -175.51(18) C12 C13 C14 N5 0.3(4) C18 O4 C19 C20 -179.1(2)