# Electronic Supplementary Material (ESI) for Dalton Transactions # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_6906_2 _database_code_depnum_ccdc_archive 'CCDC 864412' _audit_creation_date 2012-01-18 _audit_block_code INE-IA-025-02 _chemical_formula_moiety 'C54 H32, C H2 Cl2 ' _chemical_compound_source dichloromethane,hexane _chemical_formula_sum 'C55 H34 Cl2' _chemical_formula_weight 765.72 _chemical_melting_point ? _chemical_name_systematic ; 1,2-di(fluoren-9'-ylidene)-3,4-di(spiro-9H-fluorene)-cyclobutane dichloromethane solvate ; 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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-p 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, z' 'x-1/2, y, -z-1/2' 'x+1/2, -y+1/2, -z' '-x-1/2, y-1/2, z' '-x+1/2, -y, z+1/2' 'x, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 18.3571(17) _cell_length_b 17.9992(19) _cell_length_c 23.152(4) _cell_measurement_reflns_used 75545 _cell_measurement_temperature 100 _cell_measurement_theta_max 33.0999 _cell_measurement_theta_min 2.6312 _cell_volume 7649.8(17) _exptl_absorpt_coefficient_mu 0.210 _exptl_absorpt_correction_T_max 0.99458 _exptl_absorpt_correction_T_min 0.98201 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 0.00 0.0690 1.00 0.00 0.00 0.0450 0.00 0.00 1.00 0.0500 0.00 0.00 -1.00 0.0450 0.00 -1.00 0.00 0.2430 0.00 1.00 0.00 0.2690 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_F_000 3184 _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_size_max 0.512 _exptl_crystal_size_mid 0.114 _exptl_crystal_size_min 0.095 _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 18.02 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0821 _diffrn_reflns_av_sigmaI/netI 0.0870 _diffrn_reflns_limit_h_max 28 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_number 66746 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 33.20 _diffrn_reflns_theta_min 2.64 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 8578 _reflns_number_total 14624 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.528 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.074 _refine_ls_R_factor_all 0.1348 _refine_ls_R_factor_gt 0.0651 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 514 _refine_ls_number_reflns 14624 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1191 _refine_ls_wR_factor_ref 0.1437 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0342P)^2^+7.2818P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.8254 and 1.0000 (SADABS). Highest peak 0.53 at 0.0875 0.0352 0.3086 [ 0.85 A from CL2 ] Deepest hole -0.60 at 0.1027 0.0774 0.2998 [ 0.59 A from CL2 ] ; _iucr_refine_instructions_details ; TITL 6906 CELL 0.71073 18.3571 17.9992 23.1522 90 90 90 ZERR 8 0.0017 0.0019 0.0039 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H Cl UNIT 440 272 16 L.S. 20 PLAN 20 BOND FMAP 2 ACTA 55 WGHT 0.0342 7.2818 FVAR 0.06654 CL1 3 0.59821 0.59098 0.66973 11.00000 0.02729 0.02873 0.05676 = -0.01175 -0.00405 0.00535 CL2 3 0.61333 0.43015 0.67683 11.00000 0.03753 0.02887 0.06897 = -0.00027 0.00792 -0.00028 C1 1 0.86176 0.63091 0.45049 11.00000 0.01738 0.00982 0.01662 = 0.00079 -0.00231 0.00079 C2 1 0.79285 0.59127 0.44077 11.00000 0.01568 0.01075 0.01367 = -0.00081 -0.00202 0.00020 C11 1 0.89267 0.66640 0.49597 11.00000 0.01891 0.01205 0.01775 = 0.00026 -0.00431 0.00181 C12 1 0.96337 0.70729 0.49640 11.00000 0.01913 0.01117 0.02201 = -0.00025 -0.00760 0.00149 C13 1 1.01759 0.71469 0.45504 11.00000 0.01846 0.02077 0.02653 = -0.00291 -0.00534 -0.00055 AFIX 43 H13 2 1.01404 0.68984 0.41994 11.00000 -1.20000 AFIX 0 C14 1 1.07774 0.76010 0.46687 11.00000 0.01749 0.02425 0.03823 = -0.00120 -0.00619 -0.00154 AFIX 43 H14 2 1.11376 0.76619 0.43902 11.00000 -1.20000 AFIX 0 C15 1 1.08428 0.79615 0.51967 11.00000 0.02296 0.01968 0.04211 = -0.00203 -0.01438 -0.00330 AFIX 43 H15 2 1.12401 0.82700 0.52646 11.00000 -1.20000 AFIX 0 C16 1 1.03194 0.78655 0.56248 11.00000 0.02949 0.01614 0.03211 = -0.00422 -0.01719 -0.00045 AFIX 43 H16 2 1.03710 0.80943 0.59826 11.00000 -1.20000 AFIX 0 C17 1 0.97164 0.74202 0.55076 11.00000 0.02506 0.01192 0.02400 = 0.00027 -0.01127 0.00181 C18 1 0.90827 0.72384 0.58647 11.00000 0.02954 0.01252 0.02016 = 0.00044 -0.00992 0.00241 C19 1 0.89101 0.74500 0.64257 11.00000 0.04411 0.01993 0.01888 = -0.00304 -0.01127 0.00132 AFIX 43 H19 2 0.92319 0.77389 0.66396 11.00000 -1.20000 AFIX 0 C20 1 0.82517 0.72247 0.66624 11.00000 0.05029 0.02342 0.01659 = -0.00226 -0.00160 0.00330 AFIX 43 H20 2 0.81343 0.73573 0.70393 11.00000 -1.20000 AFIX 0 C21 1 0.77676 0.68026 0.63394 11.00000 0.04021 0.02050 0.01930 = 0.00063 0.00351 0.00071 AFIX 43 H21 2 0.73228 0.66663 0.65000 11.00000 -1.20000 AFIX 0 C22 1 0.79371 0.65783 0.57762 11.00000 0.03050 0.01503 0.01859 = -0.00025 -0.00100 -0.00071 AFIX 43 H22 2 0.76096 0.62939 0.55639 11.00000 -1.20000 AFIX 0 C23 1 0.86021 0.67870 0.55389 11.00000 0.02717 0.01194 0.01599 = -0.00028 -0.00502 0.00227 C31 1 0.75476 0.53643 0.46732 11.00000 0.01787 0.01296 0.01353 = -0.00112 0.00138 0.00009 C32 1 0.77930 0.48795 0.51543 11.00000 0.02310 0.01242 0.01255 = -0.00096 0.00080 -0.00034 C33 1 0.84350 0.48790 0.54757 11.00000 0.02654 0.01494 0.01806 = 0.00076 -0.00309 0.00008 AFIX 43 H33 2 0.87744 0.52590 0.54346 11.00000 -1.20000 AFIX 0 C34 1 0.85574 0.42938 0.58617 11.00000 0.03614 0.01777 0.01882 = 0.00051 -0.00637 0.00394 AFIX 43 H34 2 0.89837 0.42849 0.60786 11.00000 -1.20000 AFIX 0 C35 1 0.80501 0.37245 0.59256 11.00000 0.04735 0.01546 0.01595 = 0.00263 -0.00264 0.00089 AFIX 43 H35 2 0.81411 0.33440 0.61876 11.00000 -1.20000 AFIX 0 C36 1 0.74113 0.37152 0.56054 11.00000 0.03810 0.01493 0.01963 = 0.00201 0.00331 -0.00314 AFIX 43 H36 2 0.70769 0.33308 0.56471 11.00000 -1.20000 AFIX 0 C37 1 0.72822 0.42952 0.52197 11.00000 0.02606 0.01315 0.01441 = -0.00067 0.00308 -0.00247 C38 1 0.66746 0.44216 0.48200 11.00000 0.02440 0.01478 0.01834 = -0.00178 0.00308 -0.00258 C39 1 0.60211 0.40453 0.47482 11.00000 0.02939 0.02084 0.03043 = 0.00277 0.00328 -0.00997 AFIX 43 H39 2 0.59174 0.36258 0.49677 11.00000 -1.20000 AFIX 0 C40 1 0.55254 0.43047 0.43441 11.00000 0.02084 0.02994 0.03653 = -0.00053 -0.00079 -0.01178 AFIX 43 H40 2 0.50872 0.40545 0.42911 11.00000 -1.20000 AFIX 0 C41 1 0.56750 0.49346 0.40167 11.00000 0.01929 0.02727 0.02831 = -0.00167 -0.00291 -0.00423 AFIX 43 H41 2 0.53362 0.50992 0.37469 11.00000 -1.20000 AFIX 0 C42 1 0.63267 0.53225 0.40880 11.00000 0.01963 0.01711 0.02057 = -0.00062 0.00181 -0.00188 AFIX 43 H42 2 0.64199 0.57495 0.38743 11.00000 -1.20000 AFIX 0 C43 1 0.68358 0.50595 0.44848 11.00000 0.01685 0.01327 0.01542 = -0.00224 0.00180 -0.00223 C51 1 0.79008 0.61694 0.37765 11.00000 0.01353 0.01105 0.01388 = 0.00011 -0.00136 0.00008 C52 1 0.76530 0.56962 0.32729 11.00000 0.01264 0.01343 0.01382 = -0.00071 -0.00064 -0.00081 C53 1 0.77500 0.49432 0.31697 11.00000 0.01589 0.01251 0.01941 = -0.00161 -0.00204 0.00059 AFIX 43 H53 2 0.80182 0.46531 0.34251 11.00000 -1.20000 AFIX 0 C54 1 0.74396 0.46275 0.26777 11.00000 0.01950 0.01615 0.02309 = -0.00722 -0.00281 0.00017 AFIX 43 H54 2 0.74957 0.41218 0.26083 11.00000 -1.20000 AFIX 0 C55 1 0.70462 0.50622 0.22886 11.00000 0.02066 0.02369 0.01927 = -0.00764 -0.00467 0.00034 AFIX 43 H55 2 0.68528 0.48471 0.19571 11.00000 -1.20000 AFIX 0 C56 1 0.69411 0.58170 0.23937 11.00000 0.01905 0.02220 0.01597 = -0.00124 -0.00447 0.00205 AFIX 43 H56 2 0.66728 0.61062 0.21376 11.00000 -1.20000 AFIX 0 C57 1 0.72432 0.61312 0.28868 11.00000 0.01379 0.01381 0.01653 = 0.00061 -0.00008 -0.00047 C58 1 0.71453 0.68750 0.31373 11.00000 0.01299 0.01110 0.01703 = 0.00121 0.00100 -0.00093 C59 1 0.67387 0.74819 0.29455 11.00000 0.01596 0.01446 0.02147 = 0.00446 -0.00271 0.00001 AFIX 43 H59 2 0.65254 0.74786 0.25811 11.00000 -1.20000 AFIX 0 C60 1 0.66578 0.80932 0.33094 11.00000 0.01774 0.01082 0.03092 = 0.00307 0.00052 0.00094 AFIX 43 H60 2 0.63851 0.84997 0.31880 11.00000 -1.20000 AFIX 0 C61 1 0.69816 0.81007 0.38531 11.00000 0.01962 0.01189 0.02870 = -0.00353 0.00192 -0.00073 AFIX 43 H61 2 0.69155 0.85090 0.40936 11.00000 -1.20000 AFIX 0 C62 1 0.74046 0.75028 0.40424 11.00000 0.01772 0.01347 0.01859 = -0.00105 0.00115 -0.00161 AFIX 43 H62 2 0.76232 0.75114 0.44047 11.00000 -1.20000 AFIX 0 C63 1 0.74925 0.68941 0.36779 11.00000 0.01299 0.01116 0.01658 = 0.00147 0.00114 -0.00089 C71 1 0.87840 0.62921 0.38539 11.00000 0.01402 0.01013 0.01661 = -0.00003 -0.00082 -0.00106 C72 1 0.91188 0.68897 0.34743 11.00000 0.01354 0.01290 0.01744 = 0.00047 -0.00361 -0.00322 C73 1 0.90216 0.76545 0.34698 11.00000 0.01687 0.01286 0.02338 = -0.00019 -0.00171 -0.00098 AFIX 43 H73 2 0.87088 0.78797 0.37328 11.00000 -1.20000 AFIX 0 C74 1 0.93999 0.80816 0.30649 11.00000 0.01990 0.01483 0.02959 = 0.00370 -0.00295 -0.00381 AFIX 43 H74 2 0.93346 0.85938 0.30570 11.00000 -1.20000 AFIX 0 C75 1 0.98728 0.77493 0.26738 11.00000 0.02035 0.01954 0.02159 = 0.00658 -0.00143 -0.00481 AFIX 43 H75 2 1.01236 0.80417 0.24090 11.00000 -1.20000 AFIX 0 C76 1 0.99751 0.69806 0.26747 11.00000 0.01747 0.02105 0.01788 = 0.00072 0.00039 -0.00159 AFIX 43 H76 2 1.02895 0.67583 0.24114 11.00000 -1.20000 AFIX 0 C77 1 0.95988 0.65537 0.30760 11.00000 0.01388 0.01523 0.01594 = -0.00057 -0.00257 -0.00149 C78 1 0.96671 0.57581 0.32117 11.00000 0.01453 0.01457 0.01752 = -0.00200 -0.00261 -0.00072 C79 1 1.01210 0.52123 0.29799 11.00000 0.01898 0.01840 0.02280 = -0.00464 -0.00018 -0.00081 AFIX 43 H79 2 1.03947 0.53066 0.26500 11.00000 -1.20000 AFIX 0 C80 1 1.01558 0.45229 0.32530 11.00000 0.01849 0.01541 0.03194 = -0.00705 -0.00259 0.00252 AFIX 43 H80 2 1.04560 0.41540 0.31032 11.00000 -1.20000 AFIX 0 C81 1 0.97481 0.43798 0.37457 11.00000 0.01969 0.01192 0.02906 = -0.00029 -0.00474 0.00189 AFIX 43 H81 2 0.97892 0.39218 0.39288 11.00000 -1.20000 AFIX 0 C82 1 0.92751 0.49189 0.39699 11.00000 0.01757 0.01352 0.02224 = 0.00132 -0.00347 -0.00136 AFIX 43 H82 2 0.89978 0.48210 0.42974 11.00000 -1.20000 AFIX 0 C83 1 0.92285 0.56047 0.36926 11.00000 0.01392 0.01193 0.01852 = -0.00178 -0.00291 -0.00095 C99 1 0.63739 0.51074 0.63814 11.00000 0.02845 0.03265 0.03826 = -0.00678 0.00309 0.00311 AFIX 23 H99a 2 0.62083 0.50617 0.59852 11.00000 -1.20000 H99b 2 0.69000 0.51579 0.63768 11.00000 -1.20000 AFIX 0 HKLF 4 END ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cl1 Cl 0.59821(3) 0.59098(3) 0.66973(3) 0.03759(14) Uani 1 1 d . . . Cl2 Cl 0.61333(4) 0.43014(3) 0.67682(3) 0.04512(17) Uani 1 1 d . . . C1 C 0.86175(10) 0.63090(9) 0.45049(8) 0.0146(3) Uani 1 1 d . . . C2 C 0.79285(9) 0.59127(9) 0.44077(7) 0.0134(3) Uani 1 1 d . . . C11 C 0.89267(10) 0.66640(9) 0.49597(8) 0.0162(3) Uani 1 1 d . . . C12 C 0.96336(10) 0.70729(9) 0.49641(8) 0.0174(3) Uani 1 1 d . . . C13 C 1.01758(11) 0.71469(10) 0.45504(9) 0.0219(4) Uani 1 1 d . . . H13 H 1.0140 0.6898 0.4199 0.026 Uiso 1 1 calc R . . C14 C 1.07774(11) 0.76010(11) 0.46687(10) 0.0267(4) Uani 1 1 d . . . H14 H 1.1138 0.7662 0.4390 0.032 Uiso 1 1 calc R . . C15 C 1.08428(12) 0.79615(11) 0.51967(10) 0.0283(5) Uani 1 1 d . . . H15 H 1.1240 0.8270 0.5265 0.034 Uiso 1 1 calc R . . C16 C 1.03194(12) 0.78655(10) 0.56248(10) 0.0259(4) Uani 1 1 d . . . H16 H 1.0371 0.8094 0.5983 0.031 Uiso 1 1 calc R . . C17 C 0.97164(11) 0.74202(10) 0.55076(8) 0.0203(4) Uani 1 1 d . . . C18 C 0.90827(11) 0.72384(10) 0.58647(8) 0.0207(4) Uani 1 1 d . . . C19 C 0.89101(13) 0.74500(11) 0.64256(9) 0.0276(5) Uani 1 1 d . . . H19 H 0.9232 0.7739 0.6640 0.033 Uiso 1 1 calc R . . C20 C 0.82517(14) 0.72248(11) 0.66624(9) 0.0301(5) Uani 1 1 d . . . H20 H 0.8134 0.7357 0.7039 0.036 Uiso 1 1 calc R . . C21 C 0.77676(13) 0.68026(11) 0.63394(9) 0.0267(4) Uani 1 1 d . . . H21 H 0.7323 0.6666 0.6500 0.032 Uiso 1 1 calc R . . C22 C 0.79371(12) 0.65783(10) 0.57762(8) 0.0214(4) Uani 1 1 d . . . H22 H 0.7610 0.6294 0.5564 0.026 Uiso 1 1 calc R . . C23 C 0.86021(11) 0.67870(9) 0.55389(8) 0.0184(4) Uani 1 1 d . . . C31 C 0.75476(10) 0.53643(9) 0.46732(7) 0.0148(3) Uani 1 1 d . . . C32 C 0.77930(10) 0.48795(9) 0.51543(7) 0.0160(3) Uani 1 1 d . . . C33 C 0.84350(11) 0.48790(10) 0.54757(8) 0.0198(4) Uani 1 1 d . . . H33 H 0.8774 0.5259 0.5435 0.024 Uiso 1 1 calc R . . C34 C 0.85573(12) 0.42938(10) 0.58617(8) 0.0242(4) Uani 1 1 d . . . H34 H 0.8984 0.4285 0.6079 0.029 Uiso 1 1 calc R . . C35 C 0.80501(13) 0.37246(10) 0.59256(8) 0.0263(4) Uani 1 1 d . . . H35 H 0.8141 0.3344 0.6188 0.032 Uiso 1 1 calc R . . C36 C 0.74113(12) 0.37152(10) 0.56054(8) 0.0242(4) Uani 1 1 d . . . H36 H 0.7077 0.3331 0.5647 0.029 Uiso 1 1 calc R . . C37 C 0.72822(11) 0.42952(10) 0.52197(8) 0.0179(4) Uani 1 1 d . . . C38 C 0.66746(11) 0.44216(10) 0.48200(8) 0.0192(4) Uani 1 1 d . . . C39 C 0.60211(12) 0.40453(11) 0.47482(9) 0.0269(4) Uani 1 1 d . . . H39 H 0.5917 0.3626 0.4968 0.032 Uiso 1 1 calc R . . C40 C 0.55254(12) 0.43047(12) 0.43441(10) 0.0291(5) Uani 1 1 d . . . H40 H 0.5087 0.4054 0.4291 0.035 Uiso 1 1 calc R . . C41 C 0.56750(11) 0.49346(11) 0.40167(9) 0.0250(4) Uani 1 1 d . . . H41 H 0.5336 0.5099 0.3747 0.030 Uiso 1 1 calc R . . C42 C 0.63267(10) 0.53225(10) 0.40880(8) 0.0191(4) Uani 1 1 d . . . H42 H 0.6420 0.5750 0.3874 0.023 Uiso 1 1 calc R . . C43 C 0.68358(10) 0.50595(9) 0.44848(7) 0.0152(3) Uani 1 1 d . . . C51 C 0.79008(9) 0.61694(9) 0.37766(7) 0.0128(3) Uani 1 1 d . . . C52 C 0.76530(9) 0.56962(9) 0.32729(7) 0.0133(3) Uani 1 1 d . . . C53 C 0.77500(10) 0.49432(9) 0.31697(8) 0.0159(3) Uani 1 1 d . . . H53 H 0.8018 0.4653 0.3425 0.019 Uiso 1 1 calc R . . C54 C 0.74396(10) 0.46275(10) 0.26777(8) 0.0196(4) Uani 1 1 d . . . H54 H 0.7496 0.4122 0.2608 0.023 Uiso 1 1 calc R . . C55 C 0.70462(11) 0.50622(11) 0.22886(8) 0.0212(4) Uani 1 1 d . . . H55 H 0.6853 0.4847 0.1957 0.025 Uiso 1 1 calc R . . C56 C 0.69411(10) 0.58170(10) 0.23937(8) 0.0191(4) Uani 1 1 d . . . H56 H 0.6673 0.6106 0.2138 0.023 Uiso 1 1 calc R . . C57 C 0.72432(9) 0.61312(9) 0.28868(8) 0.0147(3) Uani 1 1 d . . . C58 C 0.71453(9) 0.68750(9) 0.31373(7) 0.0137(3) Uani 1 1 d . . . C59 C 0.67387(10) 0.74819(10) 0.29455(8) 0.0173(3) Uani 1 1 d . . . H59 H 0.6525 0.7479 0.2581 0.021 Uiso 1 1 calc R . . C60 C 0.66578(10) 0.80932(10) 0.33094(9) 0.0198(4) Uani 1 1 d . . . H60 H 0.6385 0.8500 0.3188 0.024 Uiso 1 1 calc R . . C61 C 0.69816(10) 0.81007(10) 0.38531(9) 0.0201(4) Uani 1 1 d . . . H61 H 0.6915 0.8509 0.4094 0.024 Uiso 1 1 calc R . . C62 C 0.74047(10) 0.75028(9) 0.40424(8) 0.0166(3) Uani 1 1 d . . . H62 H 0.7623 0.7511 0.4405 0.020 Uiso 1 1 calc R . . C63 C 0.74925(9) 0.68941(9) 0.36779(7) 0.0136(3) Uani 1 1 d . . . C71 C 0.87840(9) 0.62921(9) 0.38539(7) 0.0136(3) Uani 1 1 d . . . C72 C 0.91188(9) 0.68897(9) 0.34743(8) 0.0146(3) Uani 1 1 d . . . C73 C 0.90216(10) 0.76545(9) 0.34698(8) 0.0177(3) Uani 1 1 d . . . H73 H 0.8709 0.7880 0.3733 0.021 Uiso 1 1 calc R . . C74 C 0.93999(10) 0.80816(10) 0.30649(9) 0.0214(4) Uani 1 1 d . . . H74 H 0.9335 0.8594 0.3057 0.026 Uiso 1 1 calc R . . C75 C 0.98729(11) 0.77493(10) 0.26738(8) 0.0205(4) Uani 1 1 d . . . H75 H 1.0124 0.8042 0.2409 0.025 Uiso 1 1 calc R . . C76 C 0.99751(10) 0.69806(10) 0.26747(8) 0.0188(4) Uani 1 1 d . . . H76 H 1.0289 0.6758 0.2411 0.023 Uiso 1 1 calc R . . C77 C 0.95988(10) 0.65537(9) 0.30760(8) 0.0150(3) Uani 1 1 d . . . C78 C 0.96671(10) 0.57581(9) 0.32117(8) 0.0155(3) Uani 1 1 d . . . C79 C 1.01210(10) 0.52123(10) 0.29799(9) 0.0201(4) Uani 1 1 d . . . H79 H 1.0395 0.5307 0.2650 0.024 Uiso 1 1 calc R . . C80 C 1.01558(11) 0.45229(10) 0.32530(9) 0.0219(4) Uani 1 1 d . . . H80 H 1.0456 0.4154 0.3103 0.026 Uiso 1 1 calc R . . C81 C 0.97481(10) 0.43798(10) 0.37457(9) 0.0202(4) Uani 1 1 d . . . H81 H 0.9789 0.3922 0.3929 0.024 Uiso 1 1 calc R . . C82 C 0.92751(10) 0.49189(9) 0.39699(8) 0.0178(3) Uani 1 1 d . . . H82 H 0.8998 0.4821 0.4297 0.021 Uiso 1 1 calc R . . C83 C 0.92285(9) 0.56047(9) 0.36926(8) 0.0148(3) Uani 1 1 d . . . C99 C 0.63739(13) 0.51074(12) 0.63814(11) 0.0331(5) Uani 1 1 d . . . H99A H 0.6208 0.5062 0.5985 0.040 Uiso 1 1 calc R . . H99B H 0.6900 0.5158 0.6377 0.040 Uiso 1 1 calc R . . 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 Cl1 0.0273(3) 0.0287(3) 0.0568(4) -0.0117(3) -0.0040(3) 0.0053(2) Cl2 0.0375(3) 0.0289(3) 0.0690(5) -0.0003(3) 0.0079(3) -0.0003(2) C1 0.0174(8) 0.0098(7) 0.0166(8) 0.0008(6) -0.0023(7) 0.0008(6) C2 0.0157(8) 0.0108(7) 0.0137(7) -0.0008(6) -0.0020(6) 0.0002(6) C11 0.0189(9) 0.0120(7) 0.0177(8) 0.0003(6) -0.0043(7) 0.0018(6) C12 0.0191(9) 0.0112(7) 0.0220(9) -0.0002(6) -0.0076(7) 0.0015(6) C13 0.0185(9) 0.0208(9) 0.0265(10) -0.0029(7) -0.0053(8) -0.0006(7) C14 0.0175(9) 0.0242(10) 0.0382(12) -0.0012(9) -0.0062(9) -0.0015(8) C15 0.0230(10) 0.0197(9) 0.0421(13) -0.0020(9) -0.0144(9) -0.0033(8) C16 0.0295(11) 0.0161(8) 0.0321(11) -0.0042(8) -0.0172(9) -0.0004(8) C17 0.0251(9) 0.0119(8) 0.0240(9) 0.0003(7) -0.0113(8) 0.0018(7) C18 0.0295(10) 0.0125(8) 0.0202(9) 0.0004(7) -0.0099(8) 0.0024(7) C19 0.0441(13) 0.0199(9) 0.0189(9) -0.0030(7) -0.0113(9) 0.0013(9) C20 0.0503(14) 0.0234(10) 0.0166(9) -0.0023(7) -0.0016(9) 0.0033(9) C21 0.0402(12) 0.0205(9) 0.0193(9) 0.0006(7) 0.0035(9) 0.0007(8) C22 0.0305(10) 0.0150(8) 0.0186(9) -0.0003(7) -0.0010(8) -0.0007(7) C23 0.0272(10) 0.0119(7) 0.0160(8) -0.0003(6) -0.0050(8) 0.0023(7) C31 0.0179(8) 0.0130(7) 0.0135(7) -0.0011(6) 0.0014(7) 0.0001(6) C32 0.0231(9) 0.0124(7) 0.0125(7) -0.0010(6) 0.0008(7) -0.0003(7) C33 0.0265(10) 0.0149(8) 0.0181(8) 0.0008(7) -0.0031(8) 0.0001(7) C34 0.0361(11) 0.0178(8) 0.0188(9) 0.0005(7) -0.0064(9) 0.0039(8) C35 0.0474(13) 0.0155(8) 0.0160(8) 0.0026(7) -0.0026(9) 0.0009(8) C36 0.0381(12) 0.0149(8) 0.0196(9) 0.0020(7) 0.0033(9) -0.0031(8) C37 0.0261(9) 0.0132(8) 0.0144(8) -0.0007(6) 0.0031(7) -0.0025(7) C38 0.0244(9) 0.0148(8) 0.0183(8) -0.0018(6) 0.0031(7) -0.0026(7) C39 0.0294(11) 0.0208(9) 0.0304(11) 0.0028(8) 0.0033(9) -0.0100(8) C40 0.0208(10) 0.0299(11) 0.0365(12) -0.0005(9) -0.0008(9) -0.0118(8) C41 0.0193(9) 0.0273(10) 0.0283(10) -0.0017(8) -0.0029(8) -0.0042(8) C42 0.0196(9) 0.0171(8) 0.0206(9) -0.0006(7) 0.0018(8) -0.0019(7) C43 0.0168(8) 0.0133(7) 0.0154(8) -0.0022(6) 0.0018(7) -0.0022(6) C51 0.0135(7) 0.0110(7) 0.0139(7) 0.0001(6) -0.0014(6) 0.0001(6) C52 0.0126(7) 0.0134(7) 0.0138(7) -0.0007(6) -0.0006(6) -0.0008(6) C53 0.0159(8) 0.0125(7) 0.0194(8) -0.0016(6) -0.0020(7) 0.0006(6) C54 0.0195(9) 0.0161(8) 0.0231(9) -0.0072(7) -0.0028(8) 0.0002(7) C55 0.0207(9) 0.0237(9) 0.0193(9) -0.0076(7) -0.0047(8) 0.0003(7) C56 0.0190(9) 0.0222(9) 0.0160(8) -0.0012(7) -0.0045(7) 0.0021(7) C57 0.0138(8) 0.0138(7) 0.0165(8) 0.0006(6) -0.0001(7) -0.0005(6) C58 0.0130(7) 0.0111(7) 0.0170(8) 0.0012(6) 0.0010(6) -0.0009(6) C59 0.0160(8) 0.0145(7) 0.0215(9) 0.0045(7) -0.0027(7) 0.0000(6) C60 0.0177(8) 0.0108(7) 0.0309(10) 0.0031(7) 0.0005(8) 0.0009(6) C61 0.0196(9) 0.0119(8) 0.0287(10) -0.0035(7) 0.0019(8) -0.0007(7) C62 0.0177(8) 0.0135(7) 0.0186(8) -0.0010(6) 0.0011(7) -0.0016(6) C63 0.0130(7) 0.0112(7) 0.0166(8) 0.0015(6) 0.0011(7) -0.0009(6) C71 0.0140(8) 0.0101(7) 0.0166(8) 0.0000(6) -0.0008(6) -0.0011(6) C72 0.0135(8) 0.0129(7) 0.0174(8) 0.0005(6) -0.0036(7) -0.0032(6) C73 0.0169(8) 0.0129(8) 0.0234(9) -0.0002(6) -0.0017(7) -0.0010(6) C74 0.0199(9) 0.0148(8) 0.0296(10) 0.0037(7) -0.0030(8) -0.0038(7) C75 0.0203(9) 0.0195(9) 0.0216(9) 0.0066(7) -0.0014(8) -0.0048(7) C76 0.0175(9) 0.0210(9) 0.0179(8) 0.0007(7) 0.0004(7) -0.0016(7) C77 0.0139(8) 0.0152(8) 0.0159(8) -0.0006(6) -0.0026(7) -0.0015(6) C78 0.0145(8) 0.0146(7) 0.0175(8) -0.0020(6) -0.0026(7) -0.0007(6) C79 0.0190(9) 0.0184(8) 0.0228(9) -0.0046(7) -0.0002(8) -0.0008(7) C80 0.0185(9) 0.0154(8) 0.0319(10) -0.0071(7) -0.0026(8) 0.0025(7) C81 0.0197(9) 0.0119(8) 0.0291(10) -0.0003(7) -0.0047(8) 0.0019(7) C82 0.0176(8) 0.0135(7) 0.0222(9) 0.0013(6) -0.0035(7) -0.0014(6) C83 0.0139(8) 0.0119(7) 0.0185(8) -0.0018(6) -0.0029(7) -0.0010(6) C99 0.0284(11) 0.0326(11) 0.0383(12) -0.0068(10) 0.0031(10) 0.0031(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl1 C99 1.771(2) . y Cl2 C99 1.761(2) . y C1 C2 1.469(2) . y C1 C11 1.356(2) . y C1 C71 1.538(2) . y C2 C31 1.357(2) . y C2 C51 1.533(2) . y C11 C12 1.492(3) . y C11 C23 1.484(3) . y C12 C13 1.388(3) . y C12 C17 1.413(3) . y C13 C14 1.401(3) . y C14 C15 1.389(3) . y C15 C16 1.391(3) . y C16 C17 1.393(3) . y C17 C18 1.464(3) . y C18 C19 1.390(3) . y C18 C23 1.417(3) . y C19 C20 1.388(3) . y C20 C21 1.388(3) . y C21 C22 1.400(3) . y C22 C23 1.390(3) . y C31 C32 1.485(2) . y C31 C43 1.483(2) . y C32 C33 1.394(3) . y C32 C37 1.417(2) . y C33 C34 1.400(3) . y C34 C35 1.392(3) . y C35 C36 1.387(3) . y C36 C37 1.394(3) . y C37 C38 1.467(3) . y C38 C39 1.388(3) . y C38 C43 1.417(2) . y C39 C40 1.386(3) . y C40 C41 1.391(3) . y C41 C42 1.395(3) . y C42 C43 1.393(3) . y C51 C52 1.514(2) . y C51 C63 1.522(2) . y C51 C71 1.646(2) . y C52 C53 1.388(2) . y C52 C57 1.406(2) . y C53 C54 1.395(2) . y C54 C55 1.395(3) . y C55 C56 1.394(3) . y C56 C57 1.389(2) . y C57 C58 1.470(2) . y C58 C59 1.396(2) . y C58 C63 1.405(2) . y C59 C60 1.394(3) . y C60 C61 1.392(3) . y C61 C62 1.398(3) . y C62 C63 1.392(2) . y C71 C72 1.519(2) . y C71 C83 1.528(2) . y C72 C73 1.388(2) . y C72 C77 1.412(2) . y C73 C74 1.397(3) . y C74 C75 1.390(3) . y C75 C76 1.396(3) . y C76 C77 1.390(3) . y C77 C78 1.471(2) . y C78 C79 1.395(3) . y C78 C83 1.401(3) . y C79 C80 1.394(3) . y C80 C81 1.388(3) . y C81 C82 1.402(3) . y C82 C83 1.394(2) . y 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 Cl2 C99 Cl1 111.09(13) . . y C1 C2 C51 91.62(13) . . y C1 C11 C12 126.98(17) . . y C1 C11 C23 127.15(17) . . y C1 C71 C51 85.04(12) . . y C2 C1 C71 90.65(13) . . y C2 C31 C32 127.67(17) . . y C2 C31 C43 126.16(16) . . y C2 C51 C71 84.50(12) . . y C11 C1 C2 135.06(17) . . y C11 C1 C71 133.40(16) . . y C12 C13 C14 119.11(19) . . y C12 C17 C18 108.57(16) . . y C13 C12 C11 131.81(17) . . y C13 C12 C17 119.67(17) . . y C14 C15 C16 120.61(19) . . y C15 C14 C13 120.8(2) . . y C15 C16 C17 118.78(19) . . y C16 C17 C12 120.88(19) . . y C16 C17 C18 130.53(19) . . y C17 C12 C11 108.52(17) . . y C18 C23 C11 108.46(17) . . y C19 C18 C17 130.34(18) . . y C19 C18 C23 120.8(2) . . y C19 C20 C21 120.32(19) . . y C20 C19 C18 119.18(19) . . y C20 C21 C22 121.2(2) . . y C22 C23 C11 132.02(17) . . y C22 C23 C18 119.42(17) . . y C23 C11 C12 105.64(15) . . y C23 C18 C17 108.80(17) . . y C23 C22 C21 119.03(19) . . y C31 C2 C1 136.66(16) . . y C31 C2 C51 129.34(15) . . y C32 C33 C34 118.49(18) . . y C32 C37 C38 108.70(15) . . y C33 C32 C31 131.09(17) . . y C33 C32 C37 120.13(16) . . y C35 C34 C33 120.96(19) . . y C35 C36 C37 118.49(18) . . y C36 C35 C34 121.15(18) . . y C36 C37 C32 120.77(18) . . y C36 C37 C38 130.50(17) . . y C37 C32 C31 108.39(16) . . y C38 C43 C31 108.83(16) . . y C39 C38 C37 131.09(18) . . y C39 C38 C43 120.69(18) . . y C39 C40 C41 120.83(19) . . y C40 C39 C38 118.96(18) . . y C40 C41 C42 120.85(19) . . y C42 C43 C31 131.24(16) . . y C42 C43 C38 119.75(17) . . y C43 C31 C32 105.69(14) . . y C43 C38 C37 108.20(16) . . y C43 C42 C41 118.89(17) . . y C52 C51 C2 125.05(14) . . y C52 C51 C63 102.63(13) . . y C52 C51 C71 117.08(14) . . y C52 C53 C54 119.09(17) . . y C52 C57 C58 108.77(15) . . y C53 C52 C51 130.06(16) . . y C53 C52 C57 120.19(16) . . y C53 C54 C55 120.70(17) . . y C56 C55 C54 120.38(17) . . y C56 C57 C52 120.61(16) . . y C56 C57 C58 130.23(16) . . y C57 C52 C51 109.70(14) . . y C57 C56 C55 119.00(17) . . y C58 C63 C51 109.65(14) . . y C59 C58 C57 130.76(16) . . y C59 C58 C63 120.46(16) . . y C60 C59 C58 118.86(17) . . y C60 C61 C62 120.89(17) . . y C61 C60 C59 120.58(17) . . y C62 C63 C51 129.85(16) . . y C62 C63 C58 120.44(16) . . y C63 C51 C2 114.69(14) . . y C63 C51 C71 112.74(13) . . y C63 C58 C57 108.55(14) . . y C63 C62 C61 118.70(17) . . y C72 C71 C1 129.29(14) . . y C72 C71 C51 115.51(14) . . y C72 C71 C83 102.47(14) . . y C72 C73 C74 119.13(18) . . y C72 C77 C78 109.31(15) . . y C73 C72 C71 130.90(17) . . y C73 C72 C77 120.01(16) . . y C74 C75 C76 120.63(17) . . y C75 C74 C73 120.72(17) . . y C76 C77 C72 120.68(16) . . y C76 C77 C78 129.68(17) . . y C77 C72 C71 109.09(14) . . y C77 C76 C75 118.82(18) . . y C78 C83 C71 109.95(14) . . y C79 C78 C77 130.84(17) . . y C79 C78 C83 120.65(16) . . y C80 C79 C78 118.66(18) . . y C80 C81 C82 120.64(17) . . y C81 C80 C79 120.86(17) . . y C82 C83 C71 129.57(16) . . y C82 C83 C78 120.34(16) . . y C83 C71 C1 111.20(14) . . y C83 C71 C51 113.00(13) . . y C83 C78 C77 108.20(15) . . y C83 C82 C81 118.71(18) . . y data_6946_17 _database_code_depnum_ccdc_archive 'CCDC 864413' _audit_creation_date 2012-01-18 _audit_block_code BHC-BB-024-02 _chemical_name_systematic ; 2-(1,2,3,4-(tetramethyl)imidazol-3-ium-2-yl)- 1,1,3,3-tetra(trifluoromethyl)-propan-2-ide ; _chemical_melting_point ? _chemical_compound_source pentane _chemical_formula_moiety 'C14 H12 F12 N2' _chemical_formula_sum 'C14 H12 F12 N2' _chemical_formula_weight 436.26 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 21/n' _symmetry_space_group_name_Hall '-p 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.0303(8) _cell_length_b 8.0790(8) _cell_length_c 15.6424(12) _cell_angle_alpha 90.00 _cell_angle_beta 111.802(4) _cell_angle_gamma 90.00 _cell_volume 1646.3(2) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 36858 _cell_measurement_theta_min 2.6488 _cell_measurement_theta_max 33.0996 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 1.00 0.0700 1.00 0.00 -1.00 0.0700 -1.00 0.00 -3.00 0.1300 1.00 0.00 1.00 0.1400 -1.00 3.00 -1.00 0.0700 1.00 -1.00 1.00 0.1400 1.00 1.00 1.00 0.1500 -1.00 -3.00 -1.00 0.1100 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.29 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.760 _exptl_crystal_density_method ? _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.201 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.95608 _exptl_absorpt_correction_T_max 0.97398 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_detector_area_resol_mean 18.02 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 33671 _diffrn_reflns_av_R_equivalents 0.0422 _diffrn_reflns_av_sigmaI/netI 0.0311 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.80 _diffrn_reflns_theta_max 33.23 _reflns_number_total 6308 _reflns_number_gt 4676 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.8301 and 1.0000 (SADABS). Highest peak 0.73 at 0.7597 0.7235 0.2041 [ 0.83 A from F4 ] Deepest hole -0.64 at 0.8396 0.9138 0.2067 [ 0.57 A from F5 ] ; _iucr_refine_instructions_details ; TITL 6946evalsad in P21/n #14 CELL 0.71073 14.0303 8.079 15.6424 90 111.802 90 ZERR 4 0.0008 0.0008 0.0012 0 0.004 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N F UNIT 56 48 8 48 L.S. 4 PLAN 20 TEMP -173 BOND $H FMAP 2 ACTA 60 WGHT 0.0927 1.0104 FVAR 0.21110 C1 1 0.085626 0.456077 0.332276 11.00000 0.01558 0.01865 = 0.01709 -0.00127 0.00574 0.00074 C2 1 0.204352 0.331968 0.451713 11.00000 0.02036 0.02266 = 0.01629 0.00070 0.00787 0.00427 C3 1 0.125743 0.222880 0.413713 11.00000 0.02333 0.02007 = 0.02155 0.00204 0.01059 0.00382 C4 1 0.239083 0.627967 0.418956 11.00000 0.02338 0.02362 = 0.02630 -0.00421 0.00538 -0.00614 AFIX 137 H4C 2 0.242690 0.672562 0.478343 11.00000 -1.50000 H4A 2 0.206612 0.709411 0.370398 11.00000 -1.50000 H4B 2 0.308570 0.604024 0.421525 11.00000 -1.50000 AFIX 0 C5 1 0.300229 0.317144 0.534896 11.00000 0.02488 0.03575 = 0.01677 -0.00016 0.00469 0.00583 AFIX 137 H5A 2 0.359216 0.348617 0.519224 11.00000 -1.50000 H5B 2 0.308434 0.202499 0.556925 11.00000 -1.50000 H5C 2 0.296142 0.390558 0.583292 11.00000 -1.50000 AFIX 0 C6 1 0.112231 0.047657 0.437625 11.00000 0.03816 0.02021 = 0.03636 0.00610 0.01677 0.00250 AFIX 137 H6A 2 0.105602 -0.024192 0.385242 11.00000 -1.50000 H6B 2 0.050200 0.038784 0.452110 11.00000 -1.50000 H6C 2 0.172028 0.013454 0.491207 11.00000 -1.50000 AFIX 0 C7 1 -0.042428 0.227648 0.277161 11.00000 0.02267 0.02470 = 0.03603 -0.00469 0.00290 -0.00634 AFIX 137 H7A 2 -0.025572 0.141111 0.241178 11.00000 -1.50000 H7B 2 -0.085046 0.312268 0.235481 11.00000 -1.50000 H7C 2 -0.080112 0.178766 0.312595 11.00000 -1.50000 AFIX 0 C8 1 0.027283 0.580048 0.261120 11.00000 0.01771 0.01730 = 0.01720 -0.00073 0.00514 0.00031 C9 1 -0.060816 0.644324 0.272385 11.00000 0.01923 0.02132 = 0.02189 0.00339 0.01028 0.00355 C10 1 -0.070182 0.648829 0.363700 11.00000 0.02902 0.03199 = 0.02835 0.00230 0.01525 0.00874 C11 1 -0.155535 0.687648 0.194368 11.00000 0.02143 0.04234 = 0.03094 0.01205 0.01023 0.00567 C12 1 0.063747 0.613794 0.191558 11.00000 0.02066 0.02217 = 0.01879 0.00055 0.00875 0.00170 C13 1 0.043626 0.770270 0.137916 11.00000 0.03112 0.02724 = 0.03424 0.00470 0.01791 0.00016 C14 1 0.137588 0.502189 0.171463 11.00000 0.03290 0.03723 = 0.02070 0.00170 0.01368 0.01046 F1 4 0.018979 0.666014 0.434383 11.00000 0.03804 0.03802 = 0.02275 -0.00395 0.01254 0.00306 F2 4 -0.112566 0.508666 0.385887 11.00000 0.04828 0.05252 = 0.04197 0.01132 0.02685 -0.00547 F3 4 -0.132300 0.770179 0.369970 11.00000 0.05978 0.05599 = 0.04303 0.01266 0.03458 0.03521 F4 4 -0.238738 0.621094 0.203224 11.00000 0.01911 0.09284 = 0.05489 0.02831 0.01187 0.00178 F5 4 -0.180275 0.855175 0.188233 11.00000 0.05666 0.04884 = 0.06425 0.02381 0.03120 0.02714 F6 4 -0.156182 0.644619 0.112414 11.00000 0.02946 0.04945 = 0.02551 0.00759 0.00318 0.00589 F7 4 0.000285 0.887764 0.171266 11.00000 0.05896 0.02403 = 0.04914 0.00796 0.03626 0.00837 F8 4 -0.015837 0.755723 0.046069 11.00000 0.04102 0.04871 = 0.02859 0.01165 0.00831 0.00154 F9 4 0.131700 0.834334 0.136061 11.00000 0.04055 0.04146 = 0.04113 0.00394 0.02397 -0.01038 F10 4 0.130920 0.513506 0.083777 11.00000 0.05288 0.04794 = 0.02464 -0.00098 0.02340 0.01131 F11 4 0.238369 0.538100 0.221185 11.00000 0.02667 0.08419 = 0.04038 -0.00116 0.01205 0.01476 F12 4 0.126535 0.343130 0.188384 11.00000 0.07024 0.03024 = 0.05147 0.00619 0.04214 0.01867 N1 3 0.178399 0.475450 0.398940 11.00000 0.01692 0.02018 = 0.01584 -0.00168 0.00511 0.00002 N2 3 0.052330 0.303515 0.340230 11.00000 0.01850 0.01705 = 0.02226 -0.00105 0.00741 -0.00054 HKLF 4 END ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0927P)^2^+1.0104P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 6308 _refine_ls_number_parameters 257 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0786 _refine_ls_R_factor_gt 0.0557 _refine_ls_wR_factor_ref 0.1772 _refine_ls_wR_factor_gt 0.1597 _refine_ls_goodness_of_fit_ref 1.038 _refine_ls_restrained_S_all 1.038 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 0.08563(10) 0.45608(17) 0.33228(9) 0.0172(2) Uani 1 1 d . . . C2 C 0.20435(11) 0.33197(18) 0.45171(10) 0.0195(3) Uani 1 1 d . . . C3 C 0.12574(12) 0.22288(18) 0.41371(10) 0.0210(3) Uani 1 1 d . . . C4 C 0.23908(12) 0.6280(2) 0.41896(12) 0.0255(3) Uani 1 1 d . . . H4C H 0.2427 0.6726 0.4783 0.038 Uiso 1 1 calc R . . H4A H 0.2066 0.7094 0.3704 0.038 Uiso 1 1 calc R . . H4B H 0.3086 0.6040 0.4215 0.038 Uiso 1 1 calc R . . C5 C 0.30023(13) 0.3171(2) 0.53490(11) 0.0267(3) Uani 1 1 d . . . H5A H 0.3592 0.3486 0.5192 0.040 Uiso 1 1 calc R . . H5B H 0.3084 0.2025 0.5569 0.040 Uiso 1 1 calc R . . H5C H 0.2961 0.3906 0.5833 0.040 Uiso 1 1 calc R . . C6 C 0.11223(15) 0.0477(2) 0.43762(13) 0.0307(3) Uani 1 1 d . . . H6A H 0.1056 -0.0242 0.3852 0.046 Uiso 1 1 calc R . . H6B H 0.0502 0.0388 0.4521 0.046 Uiso 1 1 calc R . . H6C H 0.1720 0.0135 0.4912 0.046 Uiso 1 1 calc R . . C7 C -0.04243(13) 0.2276(2) 0.27716(13) 0.0301(3) Uani 1 1 d . . . H7A H -0.0256 0.1411 0.2412 0.045 Uiso 1 1 calc R . . H7B H -0.0850 0.3123 0.2355 0.045 Uiso 1 1 calc R . . H7C H -0.0801 0.1788 0.3126 0.045 Uiso 1 1 calc R . . C8 C 0.02728(10) 0.58005(17) 0.26112(9) 0.0178(2) Uani 1 1 d . . . C9 C -0.06082(11) 0.64432(18) 0.27239(10) 0.0201(3) Uani 1 1 d . . . C10 C -0.07018(13) 0.6488(2) 0.36370(12) 0.0285(3) Uani 1 1 d . . . C11 C -0.15553(13) 0.6876(3) 0.19437(13) 0.0314(4) Uani 1 1 d . . . C12 C 0.06375(11) 0.61379(18) 0.19156(10) 0.0201(3) Uani 1 1 d . . . C13 C 0.04363(14) 0.7703(2) 0.13792(13) 0.0292(3) Uani 1 1 d . . . C14 C 0.13759(14) 0.5022(2) 0.17146(11) 0.0292(3) Uani 1 1 d . . . F1 F 0.01898(9) 0.66601(14) 0.43438(7) 0.0326(2) Uani 1 1 d . . . F2 F -0.11257(11) 0.50867(18) 0.38589(9) 0.0447(3) Uani 1 1 d . . . F3 F -0.13230(11) 0.77018(18) 0.36997(9) 0.0485(4) Uani 1 1 d . . . F4 F -0.23874(9) 0.6211(2) 0.20322(11) 0.0561(4) Uani 1 1 d . . . F5 F -0.18027(12) 0.85517(19) 0.18823(12) 0.0541(4) Uani 1 1 d . . . F6 F -0.15618(9) 0.64462(16) 0.11241(8) 0.0368(3) Uani 1 1 d . . . F7 F 0.00029(11) 0.88776(14) 0.17127(9) 0.0394(3) Uani 1 1 d . . . F8 F -0.01584(10) 0.75572(17) 0.04607(8) 0.0408(3) Uani 1 1 d . . . F9 F 0.13170(10) 0.83433(16) 0.13606(9) 0.0385(3) Uani 1 1 d . . . F10 F 0.13092(10) 0.51351(16) 0.08378(8) 0.0392(3) Uani 1 1 d . . . F11 F 0.23837(9) 0.5381(2) 0.22118(9) 0.0505(4) Uani 1 1 d . . . F12 F 0.12654(12) 0.34313(15) 0.18838(10) 0.0450(3) Uani 1 1 d . . . N1 N 0.17840(9) 0.47545(15) 0.39894(8) 0.0179(2) Uani 1 1 d . . . N2 N 0.05233(9) 0.30352(15) 0.34023(9) 0.0193(2) Uani 1 1 d . . . 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 0.0156(5) 0.0187(6) 0.0171(6) -0.0013(4) 0.0057(4) 0.0007(4) C2 0.0204(6) 0.0227(6) 0.0163(6) 0.0007(5) 0.0079(5) 0.0043(5) C3 0.0233(6) 0.0201(6) 0.0216(6) 0.0020(5) 0.0106(5) 0.0038(5) C4 0.0234(7) 0.0236(7) 0.0263(7) -0.0042(5) 0.0054(6) -0.0061(5) C5 0.0249(7) 0.0357(8) 0.0168(6) -0.0002(6) 0.0047(5) 0.0058(6) C6 0.0382(9) 0.0202(7) 0.0364(9) 0.0061(6) 0.0168(7) 0.0025(6) C7 0.0227(7) 0.0247(7) 0.0360(9) -0.0047(6) 0.0029(6) -0.0063(6) C8 0.0177(5) 0.0173(5) 0.0172(6) -0.0007(4) 0.0051(4) 0.0003(4) C9 0.0192(6) 0.0213(6) 0.0219(6) 0.0034(5) 0.0103(5) 0.0036(5) C10 0.0290(8) 0.0320(8) 0.0283(8) 0.0023(6) 0.0153(6) 0.0087(6) C11 0.0214(7) 0.0423(9) 0.0309(8) 0.0120(7) 0.0102(6) 0.0057(6) C12 0.0207(6) 0.0222(6) 0.0188(6) 0.0005(5) 0.0088(5) 0.0017(5) C13 0.0311(8) 0.0272(7) 0.0342(8) 0.0047(6) 0.0179(7) 0.0002(6) C14 0.0329(8) 0.0372(9) 0.0207(7) 0.0017(6) 0.0137(6) 0.0105(7) F1 0.0380(6) 0.0380(6) 0.0228(5) -0.0039(4) 0.0125(4) 0.0031(4) F2 0.0483(7) 0.0525(8) 0.0420(7) 0.0113(6) 0.0268(6) -0.0055(6) F3 0.0598(8) 0.0560(8) 0.0430(7) 0.0127(6) 0.0346(6) 0.0352(7) F4 0.0191(5) 0.0928(12) 0.0549(8) 0.0283(8) 0.0119(5) 0.0018(6) F5 0.0567(8) 0.0488(8) 0.0642(9) 0.0238(7) 0.0312(7) 0.0271(6) F6 0.0295(5) 0.0494(7) 0.0255(5) 0.0076(5) 0.0032(4) 0.0059(5) F7 0.0590(8) 0.0240(5) 0.0491(7) 0.0080(5) 0.0363(6) 0.0084(5) F8 0.0410(6) 0.0487(7) 0.0286(6) 0.0117(5) 0.0083(5) 0.0015(5) F9 0.0406(6) 0.0415(6) 0.0411(6) 0.0039(5) 0.0240(5) -0.0104(5) F10 0.0529(7) 0.0479(7) 0.0246(5) -0.0010(5) 0.0234(5) 0.0113(5) F11 0.0267(5) 0.0842(11) 0.0404(7) -0.0012(7) 0.0120(5) 0.0148(6) F12 0.0702(9) 0.0302(6) 0.0515(7) 0.0062(5) 0.0421(7) 0.0187(6) N1 0.0169(5) 0.0202(5) 0.0158(5) -0.0017(4) 0.0051(4) 0.0000(4) N2 0.0185(5) 0.0170(5) 0.0223(6) -0.0010(4) 0.0074(4) -0.0005(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 N2 1.3402(18) . y C1 N1 1.3409(17) . y C1 C8 1.4951(19) . y C2 C3 1.364(2) . y C2 N1 1.3909(19) . y C2 C5 1.489(2) . y C3 N2 1.3882(19) . y C3 C6 1.494(2) . y C4 N1 1.4640(19) . y C4 H4C 0.9800 . n C4 H4A 0.9800 . n C4 H4B 0.9800 . n C5 H5A 0.9800 . n C5 H5B 0.9800 . n C5 H5C 0.9800 . n C6 H6A 0.9800 . n C6 H6B 0.9800 . n C6 H6C 0.9800 . n C7 N2 1.464(2) . y C7 H7A 0.9800 . n C7 H7B 0.9800 . n C7 H7C 0.9800 . n C8 C12 1.391(2) . y C8 C9 1.4108(19) . y C9 C11 1.474(2) . y C9 C10 1.483(2) . y C10 F1 1.334(2) . y C10 F3 1.3393(19) . y C10 F2 1.382(2) . y C11 F6 1.325(2) . y C11 F4 1.338(2) . y C11 F5 1.392(2) . y C12 C13 1.485(2) . y C12 C14 1.492(2) . y C13 F7 1.334(2) . y C13 F9 1.350(2) . y C13 F8 1.372(2) . y C14 F12 1.333(2) . y C14 F10 1.3428(19) . y C14 F11 1.368(2) . y 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 N2 C1 N1 107.84(12) . . y N2 C1 C8 124.88(12) . . y N1 C1 C8 127.28(12) . . y C3 C2 N1 106.79(12) . . y C3 C2 C5 130.61(14) . . y N1 C2 C5 122.56(14) . . y C2 C3 N2 106.79(13) . . y C2 C3 C6 131.34(15) . . y N2 C3 C6 121.86(14) . . y N1 C4 H4C 109.5 . . n N1 C4 H4A 109.5 . . n H4C C4 H4A 109.5 . . n N1 C4 H4B 109.5 . . n H4C C4 H4B 109.5 . . n H4A C4 H4B 109.5 . . n C2 C5 H5A 109.5 . . n C2 C5 H5B 109.5 . . n H5A C5 H5B 109.5 . . n C2 C5 H5C 109.5 . . n H5A C5 H5C 109.5 . . n H5B C5 H5C 109.5 . . n C3 C6 H6A 109.5 . . n C3 C6 H6B 109.5 . . n H6A C6 H6B 109.5 . . n C3 C6 H6C 109.5 . . n H6A C6 H6C 109.5 . . n H6B C6 H6C 109.5 . . n N2 C7 H7A 109.5 . . n N2 C7 H7B 109.5 . . n H7A C7 H7B 109.5 . . n N2 C7 H7C 109.5 . . n H7A C7 H7C 109.5 . . n H7B C7 H7C 109.5 . . n C12 C8 C9 128.29(13) . . y C12 C8 C1 117.07(12) . . y C9 C8 C1 114.61(12) . . y C8 C9 C11 123.11(14) . . y C8 C9 C10 121.64(13) . . y C11 C9 C10 114.61(13) . . y F1 C10 F3 107.37(15) . . y F1 C10 F2 103.63(14) . . y F3 C10 F2 103.24(14) . . y F1 C10 C9 114.19(14) . . y F3 C10 C9 112.42(14) . . y F2 C10 C9 114.97(15) . . y F6 C11 F4 107.57(17) . . y F6 C11 F5 106.05(15) . . y F4 C11 F5 101.13(15) . . y F6 C11 C9 114.76(14) . . y F4 C11 C9 111.82(14) . . y F5 C11 C9 114.40(17) . . y C8 C12 C13 124.12(13) . . y C8 C12 C14 122.16(13) . . y C13 C12 C14 113.35(13) . . y F7 C13 F9 106.83(15) . . y F7 C13 F8 106.39(15) . . y F9 C13 F8 102.46(14) . . y F7 C13 C12 113.79(14) . . y F9 C13 C12 110.80(14) . . y F8 C13 C12 115.63(15) . . y F12 C14 F10 107.42(15) . . y F12 C14 F11 105.28(15) . . y F10 C14 F11 103.38(15) . . y F12 C14 C12 113.56(15) . . y F10 C14 C12 112.56(14) . . y F11 C14 C12 113.82(15) . . y C1 N1 C2 109.20(12) . . y C1 N1 C4 125.74(13) . . y C2 N1 C4 124.84(12) . . y C1 N2 C3 109.36(12) . . y C1 N2 C7 125.68(13) . . y C3 N2 C7 124.78(13) . . y _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.732 _refine_diff_density_min -0.643 _refine_diff_density_rms 0.080 data_6966_18 _database_code_depnum_ccdc_archive 'CCDC 864414' _audit_creation_date 2012-01-18 _audit_block_code HOS-HG-002-01 _chemical_compound_source dichloromethane _chemical_formula_moiety 'C26 H40 N2 O8' _chemical_formula_sum 'C26 H40 N2 O8' _chemical_formula_weight 508.60 _chemical_melting_point ? _chemical_name_systematic ; 2-(1,3-di(tert-butyl)imidazol-3-ium-2-yl)- 1,1,3,3-tetra-ethyloxycarbonyl-propan-2-ide ; _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2/c' _symmetry_space_group_name_Hall '-c 2yc' _symmetry_Int_Tables_number 15 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.1300 0.00 0.00 -1.00 0.1300 0.00 -1.00 0.00 0.0800 0.00 1.00 0.00 0.0900 -1.00 -1.00 0.00 0.2200 1.00 1.00 0.00 0.1800 1.00 -1.00 0.00 0.2100 -1.00 1.00 0.00 0.2000 1.00 -1.00 0.00 0.2000 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _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' _cell_angle_alpha 90.00 _cell_angle_beta 95.356(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.3691(5) _cell_length_b 16.1875(9) _cell_length_c 15.839(1) _cell_measurement_reflns_used 51445 _cell_measurement_temperature 100 _cell_measurement_theta_max 35.9997 _cell_measurement_theta_min 2.7537 _cell_volume 2647.0(3) _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.98596 _exptl_absorpt_correction_T_min 0.96822 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_F_000 1096 _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.276 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.17 _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 18.02 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0207 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 26 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_number 48455 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 36.10 _diffrn_reflns_theta_min 2.76 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _reflns_number_gt 5257 _reflns_number_total 6305 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.499 _refine_diff_density_min -0.270 _refine_diff_density_rms 0.047 _refine_ls_R_factor_all 0.0476 _refine_ls_R_factor_gt 0.0360 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 169 _refine_ls_number_reflns 6305 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.0919 _refine_ls_wR_factor_ref 0.0979 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0490P)^2^+1.0780P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.8812 and 1.0000 (SADABS). Highest peak 0.50 at 1.0000 0.3141 0.2500 [ 0.68 A from C2 ] Deepest hole -0.27 at 0.5756 0.1618 0.2378 [ 0.67 A from C5 ] ; _iucr_refine_instructions_details ; TITL 6966sadabs in C2/c #15 CELL 0.71073 10.3691 16.1875 15.839 90 95.356 90 ZERR 4 0.0005 0.0009 0.001 0 0.004 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 104 160 8 32 L.S. 10 PLAN 5 BOND FMAP 2 ACTA 55 WGHT 0.049 1.078 FVAR 0.1677 O1 4 0.31897 0.20950 0.31591 11.00000 0.02110 0.01368 0.02207 = -0.00171 0.00885 0.00316 O2 4 0.38141 0.18645 0.18543 11.00000 0.02047 0.01145 0.01731 = 0.00342 0.00575 0.00349 O3 4 0.30859 -0.04403 0.35011 11.00000 0.01646 0.01330 0.02085 = 0.00310 0.00652 -0.00009 O4 4 0.18247 0.06837 0.32448 11.00000 0.01037 0.01906 0.02359 = 0.00509 0.00637 0.00177 N1 3 0.43396 -0.10581 0.19166 11.00000 0.01088 0.01024 0.01330 = -0.00083 0.00047 0.00004 C1 1 0.50000 -0.05702 0.25000 10.50000 0.00979 0.00999 0.01201 = 0.00000 0.00186 0.00000 C2 1 0.45868 -0.18726 0.21443 11.00000 0.01617 0.00969 0.01872 = -0.00107 0.00013 -0.00048 AFIX 43 H2 2 0.42449 -0.23366 0.18585 11.00000 -1.20000 AFIX 0 C3 1 0.50000 0.03547 0.25000 10.50000 0.01004 0.00994 0.01079 = 0.00000 0.00160 0.00000 C4 1 0.39000 0.07346 0.27855 11.00000 0.01045 0.01030 0.01349 = 0.00068 0.00345 0.00019 C5 1 0.36050 0.16262 0.26499 11.00000 0.01202 0.01160 0.01634 = 0.00077 0.00367 0.00097 C6 1 0.35190 0.27214 0.16392 11.00000 0.03193 0.01357 0.02580 = 0.00672 0.01095 0.00729 AFIX 23 H6B 2 0.39759 0.30880 0.20492 11.00000 -1.20000 H6A 2 0.25967 0.28226 0.16370 11.00000 -1.20000 AFIX 0 C7 1 0.39519 0.28670 0.07688 11.00000 0.02628 0.01958 0.02123 = 0.00660 0.00325 0.00014 AFIX 137 H7A 2 0.35344 0.24767 0.03771 11.00000 -1.50000 H7C 2 0.48740 0.27993 0.07884 11.00000 -1.50000 H7B 2 0.37230 0.34178 0.05869 11.00000 -1.50000 AFIX 0 C8 1 0.29534 0.02584 0.32115 11.00000 0.01020 0.01361 0.01204 = -0.00078 0.00195 -0.00060 C9 1 0.08508 0.03010 0.37067 11.00000 0.01247 0.01864 0.02265 = -0.00091 0.00740 -0.00252 AFIX 23 H9B 2 0.12353 0.00880 0.42448 11.00000 -1.20000 H9A 2 0.04421 -0.01523 0.33826 11.00000 -1.20000 AFIX 0 C10 1 -0.01334 0.09652 0.38492 11.00000 0.01588 0.02223 0.02957 = -0.00543 0.00921 -0.00088 AFIX 137 H10A 2 -0.05129 0.11650 0.33118 11.00000 -1.50000 H10C 2 0.02871 0.14128 0.41630 11.00000 -1.50000 H10B 2 -0.07986 0.07388 0.41634 11.00000 -1.50000 AFIX 0 C11 1 0.34850 -0.08432 0.11172 11.00000 0.01341 0.01327 0.01272 = -0.00137 -0.00115 0.00025 C12 1 0.20791 -0.09039 0.13304 11.00000 0.01236 0.02178 0.02535 = 0.00722 -0.00191 -0.00275 AFIX 137 H12B 2 0.19228 -0.04950 0.17479 11.00000 -1.50000 H12C 2 0.19244 -0.14439 0.15503 11.00000 -1.50000 H12A 2 0.15078 -0.08108 0.08268 11.00000 -1.50000 AFIX 0 C13 1 0.37535 -0.14794 0.04378 11.00000 0.04093 0.02696 0.01868 = -0.01004 -0.00620 0.01286 AFIX 137 H13B 2 0.34733 -0.20152 0.06053 11.00000 -1.50000 H13C 2 0.46652 -0.14935 0.03753 11.00000 -1.50000 H13A 2 0.32899 -0.13276 -0.00925 11.00000 -1.50000 AFIX 0 C14 1 0.37712 0.00168 0.07833 11.00000 0.01821 0.01974 0.01379 = 0.00360 -0.00124 -0.00519 AFIX 137 H14A 2 0.33193 0.00898 0.02313 11.00000 -1.50000 H14C 2 0.46857 0.00736 0.07462 11.00000 -1.50000 H14B 2 0.34884 0.04273 0.11628 11.00000 -1.50000 AFIX 0 HKLF 4 END ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.31897(5) 0.20950(3) 0.31591(3) 0.01852(10) Uani 1 1 d . . . O2 O 0.38141(5) 0.18645(3) 0.18543(3) 0.01616(9) Uani 1 1 d . . . O3 O 0.30859(5) -0.04402(3) 0.35011(3) 0.01657(9) Uani 1 1 d . . . O4 O 0.18247(4) 0.06837(3) 0.32447(3) 0.01737(9) Uani 1 1 d . . . N1 N 0.43396(5) -0.10581(3) 0.19166(3) 0.01152(8) Uani 1 1 d . . . C1 C 0.5000 -0.05702(5) 0.2500 0.01054(12) Uani 1 2 d S . . C2 C 0.45868(6) -0.18726(4) 0.21443(4) 0.01495(10) Uani 1 1 d . . . H2 H 0.4245 -0.2337 0.1858 0.018 Uiso 1 1 calc R . . C3 C 0.5000 0.03547(5) 0.2500 0.01022(12) Uani 1 2 d S . . C4 C 0.39000(5) 0.07346(3) 0.27855(4) 0.01127(9) Uani 1 1 d . . . C5 C 0.36050(6) 0.16262(4) 0.26499(4) 0.01317(10) Uani 1 1 d . . . C6 C 0.35190(8) 0.27214(4) 0.16392(5) 0.02325(14) Uani 1 1 d . . . H6B H 0.3976 0.3088 0.2049 0.028 Uiso 1 1 calc R . . H6A H 0.2597 0.2823 0.1637 0.028 Uiso 1 1 calc R . . C7 C 0.39519(8) 0.28670(4) 0.07688(5) 0.02230(13) Uani 1 1 d . . . H7A H 0.3534 0.2477 0.0377 0.033 Uiso 1 1 calc R . . H7C H 0.4874 0.2799 0.0788 0.033 Uiso 1 1 calc R . . H7B H 0.3723 0.3418 0.0587 0.033 Uiso 1 1 calc R . . C8 C 0.29534(5) 0.02584(4) 0.32115(4) 0.01189(9) Uani 1 1 d . . . C9 C 0.08508(6) 0.03010(4) 0.37066(4) 0.01756(11) Uani 1 1 d . . . H9B H 0.1235 0.0088 0.4245 0.021 Uiso 1 1 calc R . . H9A H 0.0442 -0.0152 0.3383 0.021 Uiso 1 1 calc R . . C10 C -0.01334(7) 0.09652(5) 0.38492(5) 0.02211(13) Uani 1 1 d . . . H10A H -0.0513 0.1165 0.3312 0.033 Uiso 1 1 calc R . . H10C H 0.0287 0.1413 0.4163 0.033 Uiso 1 1 calc R . . H10B H -0.0799 0.0739 0.4163 0.033 Uiso 1 1 calc R . . C11 C 0.34850(6) -0.08432(4) 0.11172(4) 0.01328(10) Uani 1 1 d . . . C12 C 0.20791(6) -0.09039(4) 0.13304(5) 0.02006(12) Uani 1 1 d . . . H12B H 0.1923 -0.0495 0.1748 0.030 Uiso 1 1 calc R . . H12C H 0.1924 -0.1444 0.1550 0.030 Uiso 1 1 calc R . . H12A H 0.1508 -0.0811 0.0827 0.030 Uiso 1 1 calc R . . C13 C 0.37535(9) -0.14794(5) 0.04378(5) 0.02942(17) Uani 1 1 d . . . H13B H 0.3473 -0.2015 0.0605 0.044 Uiso 1 1 calc R . . H13C H 0.4665 -0.1494 0.0375 0.044 Uiso 1 1 calc R . . H13A H 0.3290 -0.1328 -0.0093 0.044 Uiso 1 1 calc R . . C14 C 0.37712(6) 0.00168(4) 0.07833(4) 0.01742(11) Uani 1 1 d . . . H14A H 0.3319 0.0090 0.0231 0.026 Uiso 1 1 calc R . . H14C H 0.4686 0.0074 0.0746 0.026 Uiso 1 1 calc R . . H14B H 0.3488 0.0427 0.1163 0.026 Uiso 1 1 calc R . . 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 O1 0.0211(2) 0.01368(19) 0.0221(2) -0.00171(16) 0.00885(17) 0.00316(16) O2 0.0205(2) 0.01145(18) 0.0173(2) 0.00342(14) 0.00575(16) 0.00349(15) O3 0.0165(2) 0.01330(18) 0.0209(2) 0.00310(15) 0.00652(16) -0.00009(15) O4 0.01037(18) 0.0191(2) 0.0236(2) 0.00509(17) 0.00637(16) 0.00177(15) N1 0.01088(19) 0.01024(18) 0.01330(19) -0.00083(15) 0.00047(15) 0.00004(14) C1 0.0098(3) 0.0100(3) 0.0120(3) 0.000 0.0019(2) 0.000 C2 0.0162(2) 0.0097(2) 0.0187(3) -0.00107(18) 0.00013(19) -0.00048(18) C3 0.0100(3) 0.0099(3) 0.0108(3) 0.000 0.0016(2) 0.000 C4 0.0104(2) 0.0103(2) 0.0135(2) 0.00068(16) 0.00345(16) 0.00019(16) C5 0.0120(2) 0.0116(2) 0.0163(2) 0.00077(18) 0.00367(18) 0.00097(17) C6 0.0319(4) 0.0136(2) 0.0258(3) 0.0067(2) 0.0109(3) 0.0073(2) C7 0.0263(3) 0.0196(3) 0.0212(3) 0.0066(2) 0.0032(2) 0.0001(2) C8 0.0102(2) 0.0136(2) 0.0120(2) -0.00078(17) 0.00195(16) -0.00060(17) C9 0.0125(2) 0.0186(3) 0.0226(3) -0.0009(2) 0.0074(2) -0.00252(19) C10 0.0159(3) 0.0222(3) 0.0296(3) -0.0054(2) 0.0092(2) -0.0009(2) C11 0.0134(2) 0.0133(2) 0.0127(2) -0.00137(17) -0.00115(17) 0.00025(18) C12 0.0124(2) 0.0218(3) 0.0253(3) 0.0072(2) -0.0019(2) -0.0028(2) C13 0.0409(4) 0.0270(3) 0.0187(3) -0.0100(3) -0.0062(3) 0.0129(3) C14 0.0182(3) 0.0197(3) 0.0138(2) 0.0036(2) -0.00124(19) -0.0052(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C5 1.2152(7) . y O2 C5 1.3546(8) . y O2 C6 1.4540(8) . y O3 C8 1.2233(7) . y O4 C8 1.3631(7) . y O4 C9 1.4411(7) . y N1 C1 1.3521(7) . y N1 C2 1.3845(8) . y N1 C11 1.5165(8) . y C1 N1 1.3521(7) 2_655 y C1 C3 1.4972(11) . y C2 C2 1.3505(13) 2_655 y C3 C4 1.4070(6) 2_655 y C3 C4 1.4070(6) . y C4 C5 1.4868(8) . y C4 C8 1.4617(8) . y C6 C7 1.5077(10) . y C9 C10 1.5137(9) . y C11 C12 1.5300(9) . y C11 C13 1.5336(9) . y C11 C14 1.5282(9) . y 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 O1 C5 O2 122.48(5) . . y O1 C5 C4 126.25(6) . . y O2 C5 C4 111.24(5) . . y O2 C6 C7 106.81(6) . . y O3 C8 O4 121.28(5) . . y O3 C8 C4 127.15(5) . . y O4 C8 C4 111.56(5) . . y O4 C9 C10 106.54(5) . . y N1 C1 N1 108.53(7) . 2_655 y N1 C1 C3 125.73(3) 2_655 . y N1 C1 C3 125.73(3) . . y N1 C11 C12 107.19(5) . . y N1 C11 C13 107.56(5) . . y N1 C11 C14 112.37(5) . . y C1 N1 C2 107.97(5) . . y C1 N1 C11 130.98(5) . . y C2 N1 C11 121.02(5) . . y C2 C2 N1 107.75(3) 2_655 . y C3 C4 C5 122.67(5) . . y C3 C4 C8 121.15(5) . . y C4 C3 C1 115.91(4) . . y C4 C3 C1 115.91(4) 2_655 . y C4 C3 C4 128.17(7) 2_655 . y C5 O2 C6 116.18(5) . . y C8 O4 C9 116.58(5) . . y C8 C4 C5 116.14(5) . . y C12 C11 C13 110.54(6) . . y C14 C11 C12 110.77(5) . . y C14 C11 C13 108.37(6) . . y data_6971_6 _database_code_depnum_ccdc_archive 'CCDC 864415' _audit_creation_date 2012-01-18 _audit_block_code HOS-HG-013-01 _chemical_compound_source hexane _chemical_formula_moiety 'C21 H18 O4' _chemical_formula_sum 'C21 H18 O4' _chemical_formula_weight 334.35 _chemical_melting_point ? _chemical_name_systematic ; 1,1-di(ethoxycarbonyl)-2-(9H-fluoren-9-ylidene)-ethene ; 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-p 2ybc' _symmetry_Int_Tables_number 14 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 0.00 0.0600 0.00 1.00 0.00 0.0600 1.00 0.00 0.00 0.0350 -1.00 0.00 0.00 0.0350 1.00 0.00 -1.00 0.1500 -1.00 0.00 1.00 0.1500 loop_ _symmetry_equiv_pos_as_xyz '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, z' 'x, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 115.659(6) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.5811(7) _cell_length_b 20.9360(19) _cell_length_c 9.7491(7) _cell_measurement_reflns_used 41585 _cell_measurement_temperature 100 _cell_measurement_theta_max 33.0992 _cell_measurement_theta_min 2.6698 _cell_volume 1762.7(2) _exptl_absorpt_coefficient_mu 0.087 _exptl_absorpt_correction_T_max 0.99409 _exptl_absorpt_correction_T_min 0.97111 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_F_000 704 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.260 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description plate _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 18.02 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0835 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 36463 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 33.17 _diffrn_reflns_theta_min 2.67 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _reflns_number_gt 4666 _reflns_number_total 6720 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.440 _refine_diff_density_min -0.470 _refine_diff_density_rms 0.101 _refine_ls_R_factor_all 0.1006 _refine_ls_R_factor_gt 0.0656 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.194 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 228 _refine_ls_number_reflns 6720 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.194 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1703 _refine_ls_wR_factor_ref 0.1922 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.5321 and 1.0000 (SADABS). Highest peak 0.44 at 0.8424 0.0841 0.4593 [ 0.63 A from H20A ] Deepest hole -0.47 at 0.6382 0.1631 0.9244 [ 0.75 A from C2 ] ; _iucr_refine_instructions_details ; TITL 6971 CELL 0.71073 9.5811 20.936 9.7491 90 115.659 90 ZERR 4 0.0007 0.0019 0.0007 0 0.006 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H O UNIT 84 72 16 L.S. 4 PLAN 20 FMAP 2.0 ACTA 55 WGHT 0.1 FVAR 0.19751 O1 3 0.75842 0.59903 0.30976 11.00000 0.04398 0.01518 0.03515 = 0.00093 0.02685 -0.00006 O2 3 0.69072 0.53572 0.45879 11.00000 0.02985 0.01837 0.02641 = -0.00370 0.02057 -0.00250 O3 3 0.93662 0.52251 0.19232 11.00000 0.02312 0.02449 0.03323 = -0.00382 0.01899 -0.00627 O4 3 0.75372 0.45222 0.04652 11.00000 0.02295 0.03259 0.02519 = -0.00888 0.01677 -0.00825 C1 1 0.63662 0.37617 0.31248 11.00000 0.02073 0.01530 0.02187 = -0.00136 0.01431 -0.00135 C2 1 0.71520 0.32677 0.42936 11.00000 0.02121 0.01719 0.02104 = 0.00002 0.01366 -0.00092 C3 1 0.86256 0.32640 0.55057 11.00000 0.02168 0.02456 0.02365 = -0.00096 0.01240 -0.00204 AFIX 43 H3 2 0.92860 0.36121 0.56935 11.00000 -1.20000 AFIX 0 C4 1 0.90800 0.27204 0.64306 11.00000 0.02370 0.03254 0.02343 = 0.00294 0.01080 0.00172 AFIX 43 H4 2 1.00647 0.27032 0.72340 11.00000 -1.20000 AFIX 0 C5 1 0.80703 0.22011 0.61622 11.00000 0.03292 0.02604 0.02803 = 0.00906 0.01747 0.00337 AFIX 43 H5 2 0.83894 0.18460 0.67966 11.00000 -1.20000 AFIX 0 C6 1 0.65963 0.22107 0.49577 11.00000 0.02901 0.01965 0.02778 = 0.00337 0.01695 -0.00098 AFIX 43 H6 2 0.59295 0.18657 0.47841 11.00000 -1.20000 AFIX 0 C7 1 0.61376 0.27446 0.40185 11.00000 0.02286 0.01688 0.02227 = -0.00028 0.01506 -0.00127 C8 1 0.46922 0.28866 0.26587 11.00000 0.02238 0.01631 0.02192 = -0.00124 0.01475 -0.00255 C9 1 0.33593 0.25225 0.18798 11.00000 0.02737 0.01743 0.02686 = -0.00367 0.01623 -0.00593 AFIX 43 H9 2 0.32596 0.21186 0.22247 11.00000 -1.20000 AFIX 0 C10 1 0.21791 0.27803 0.05690 11.00000 0.02553 0.02403 0.02436 = -0.00670 0.01286 -0.00796 AFIX 43 H10 2 0.12853 0.25426 0.00379 11.00000 -1.20000 AFIX 0 C11 1 0.23098 0.33876 0.00363 11.00000 0.02389 0.02708 0.02179 = -0.00264 0.01059 -0.00286 AFIX 43 H11 2 0.15074 0.35479 -0.08403 11.00000 -1.20000 AFIX 0 C12 1 0.36395 0.37541 0.08147 11.00000 0.02378 0.01812 0.02368 = 0.00026 0.01362 -0.00113 AFIX 43 H12 2 0.37372 0.41578 0.04677 11.00000 -1.20000 AFIX 0 C13 1 0.48156 0.34988 0.21247 11.00000 0.02121 0.01541 0.02132 = -0.00197 0.01413 -0.00152 C14 1 0.69129 0.43157 0.29533 11.00000 0.01782 0.01837 0.02061 = -0.00130 0.01181 -0.00098 C15 1 0.74590 0.48612 0.27229 11.00000 0.01712 0.01565 0.02033 = -0.00036 0.01110 -0.00081 C16 1 0.73464 0.54696 0.34854 11.00000 0.01794 0.01676 0.02118 = -0.00085 0.01053 -0.00012 C17 1 0.67322 0.59208 0.53850 11.00000 0.02708 0.02357 0.02709 = -0.00572 0.01736 0.00097 AFIX 23 H17a 2 0.60701 0.58181 0.58762 11.00000 -1.20000 H17b 2 0.62416 0.62604 0.46573 11.00000 -1.20000 AFIX 0 C18 1 0.82830 0.61457 0.65617 11.00000 0.02887 0.03120 0.02518 = -0.00808 0.00998 0.00277 AFIX 137 H18b 2 0.89045 0.62842 0.60659 11.00000 -1.50000 H18a 2 0.87959 0.58013 0.72449 11.00000 -1.50000 H18c 2 0.81367 0.64950 0.71241 11.00000 -1.50000 AFIX 0 C19 1 0.82461 0.48969 0.16803 11.00000 0.01786 0.01537 0.02133 = 0.00142 0.01160 0.00030 C20 1 0.82106 0.45157 -0.06307 11.00000 0.02380 0.04491 0.02446 = -0.00674 0.01690 -0.00366 AFIX 23 H20a 2 0.91033 0.42347 -0.02738 11.00000 -1.20000 H20b 2 0.85458 0.49421 -0.07395 11.00000 -1.20000 AFIX 0 C21 1 0.70095 0.42856 -0.21263 11.00000 0.03452 0.05373 0.02578 = -0.00754 0.01670 -0.01004 AFIX 137 H21c 2 0.74291 0.42852 -0.28596 11.00000 -1.50000 H21b 2 0.61266 0.45637 -0.24670 11.00000 -1.50000 H21a 2 0.67006 0.38600 -0.20140 11.00000 -1.50000 AFIX 0 HKLF 4 END ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.75842(14) 0.59903(4) 0.30976(12) 0.0280(2) Uani 1 1 d . . . O2 O 0.69072(12) 0.53572(5) 0.45879(11) 0.0219(2) Uani 1 1 d . . . O3 O 0.93662(12) 0.52251(5) 0.19232(12) 0.0245(2) Uani 1 1 d . . . O4 O 0.75372(12) 0.45222(5) 0.04652(11) 0.0247(2) Uani 1 1 d . . . C1 C 0.63662(15) 0.37617(6) 0.31248(15) 0.0175(2) Uani 1 1 d . . . C2 C 0.71520(15) 0.32677(6) 0.42936(14) 0.0182(2) Uani 1 1 d . . . C3 C 0.86256(16) 0.32640(7) 0.55057(16) 0.0224(3) Uani 1 1 d . . . H3 H 0.9286 0.3612 0.5693 0.027 Uiso 1 1 calc R . . C4 C 0.90800(17) 0.27204(7) 0.64306(17) 0.0263(3) Uani 1 1 d . . . H4 H 1.0065 0.2703 0.7234 0.032 Uiso 1 1 calc R . . C5 C 0.80703(18) 0.22011(7) 0.61622(17) 0.0275(3) Uani 1 1 d . . . H5 H 0.8389 0.1846 0.6797 0.033 Uiso 1 1 calc R . . C6 C 0.65963(17) 0.22107(7) 0.49577(16) 0.0238(3) Uani 1 1 d . . . H6 H 0.5930 0.1866 0.4784 0.029 Uiso 1 1 calc R . . C7 C 0.61376(16) 0.27446(6) 0.40185(15) 0.0188(2) Uani 1 1 d . . . C8 C 0.46922(15) 0.28866(6) 0.26587(15) 0.0184(2) Uani 1 1 d . . . C9 C 0.33593(17) 0.25225(7) 0.18798(16) 0.0223(3) Uani 1 1 d . . . H9 H 0.3260 0.2119 0.2225 0.027 Uiso 1 1 calc R . . C10 C 0.21791(17) 0.27802(7) 0.05690(16) 0.0239(3) Uani 1 1 d . . . H10 H 0.1285 0.2543 0.0038 0.029 Uiso 1 1 calc R . . C11 C 0.23098(17) 0.33876(7) 0.00363(16) 0.0240(3) Uani 1 1 d . . . H11 H 0.1507 0.3548 -0.0840 0.029 Uiso 1 1 calc R . . C12 C 0.36396(16) 0.37541(6) 0.08147(15) 0.0207(3) Uani 1 1 d . . . H12 H 0.3737 0.4158 0.0468 0.025 Uiso 1 1 calc R . . C13 C 0.48156(15) 0.34988(6) 0.21247(14) 0.0176(2) Uani 1 1 d . . . C14 C 0.69129(15) 0.43157(6) 0.29533(15) 0.0177(2) Uani 1 1 d . . . C15 C 0.74590(15) 0.48612(6) 0.27229(14) 0.0166(2) Uani 1 1 d . . . C16 C 0.73464(15) 0.54696(6) 0.34854(15) 0.0179(2) Uani 1 1 d . . . C17 C 0.67322(17) 0.59208(7) 0.53850(17) 0.0239(3) Uani 1 1 d . . . H17A H 0.6070 0.5818 0.5876 0.029 Uiso 1 1 calc R . . H17B H 0.6242 0.6260 0.4657 0.029 Uiso 1 1 calc R . . C18 C 0.82830(18) 0.61457(8) 0.65617(17) 0.0290(3) Uani 1 1 d . . . H18B H 0.8905 0.6284 0.6066 0.044 Uiso 1 1 calc R . . H18A H 0.8796 0.5801 0.7245 0.044 Uiso 1 1 calc R . . H18C H 0.8137 0.6495 0.7124 0.044 Uiso 1 1 calc R . . C19 C 0.82461(15) 0.48969(6) 0.16803(14) 0.0171(2) Uani 1 1 d . . . C20 C 0.82106(18) 0.45157(9) -0.06307(17) 0.0288(3) Uani 1 1 d . . . H20A H 0.9103 0.4235 -0.0274 0.035 Uiso 1 1 calc R . . H20B H 0.8546 0.4942 -0.0740 0.035 Uiso 1 1 calc R . . C21 C 0.7010(2) 0.42856(10) -0.21263(19) 0.0367(4) Uani 1 1 d . . . H21C H 0.7429 0.4285 -0.2860 0.055 Uiso 1 1 calc R . . H21B H 0.6127 0.4564 -0.2467 0.055 Uiso 1 1 calc R . . H21A H 0.6701 0.3860 -0.2014 0.055 Uiso 1 1 calc R . . 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 O1 0.0440(7) 0.0152(5) 0.0352(6) 0.0009(4) 0.0269(5) -0.0001(4) O2 0.0298(5) 0.0184(5) 0.0264(5) -0.0037(3) 0.0206(4) -0.0025(4) O3 0.0231(5) 0.0245(5) 0.0332(5) -0.0038(4) 0.0190(4) -0.0063(4) O4 0.0230(5) 0.0326(6) 0.0252(5) -0.0089(4) 0.0168(4) -0.0083(4) C1 0.0207(6) 0.0153(5) 0.0219(6) -0.0014(4) 0.0143(5) -0.0014(4) C2 0.0212(6) 0.0172(5) 0.0210(6) 0.0000(4) 0.0137(5) -0.0009(4) C3 0.0217(6) 0.0246(6) 0.0237(6) -0.0010(5) 0.0124(5) -0.0020(5) C4 0.0237(7) 0.0325(8) 0.0234(7) 0.0029(5) 0.0108(6) 0.0017(5) C5 0.0329(8) 0.0260(7) 0.0280(7) 0.0091(5) 0.0175(6) 0.0034(6) C6 0.0290(7) 0.0197(6) 0.0278(7) 0.0034(5) 0.0169(6) -0.0010(5) C7 0.0229(6) 0.0169(6) 0.0223(6) -0.0003(4) 0.0151(5) -0.0013(4) C8 0.0224(6) 0.0163(6) 0.0219(6) -0.0012(4) 0.0147(5) -0.0025(4) C9 0.0274(7) 0.0174(6) 0.0269(7) -0.0037(5) 0.0162(5) -0.0059(5) C10 0.0255(7) 0.0240(7) 0.0244(7) -0.0067(5) 0.0129(5) -0.0080(5) C11 0.0239(6) 0.0271(7) 0.0218(6) -0.0026(5) 0.0106(5) -0.0029(5) C12 0.0238(6) 0.0181(6) 0.0237(6) 0.0003(5) 0.0136(5) -0.0011(5) C13 0.0212(6) 0.0154(5) 0.0213(6) -0.0020(4) 0.0141(5) -0.0015(4) C14 0.0178(5) 0.0184(6) 0.0206(6) -0.0013(4) 0.0118(5) -0.0010(4) C15 0.0171(5) 0.0156(5) 0.0203(6) -0.0004(4) 0.0111(4) -0.0008(4) C16 0.0179(5) 0.0168(5) 0.0212(6) -0.0009(4) 0.0105(5) -0.0001(4) C17 0.0271(7) 0.0236(7) 0.0271(7) -0.0057(5) 0.0174(6) 0.0010(5) C18 0.0289(7) 0.0312(8) 0.0252(7) -0.0081(5) 0.0100(6) 0.0028(6) C19 0.0179(5) 0.0154(5) 0.0213(6) 0.0014(4) 0.0116(5) 0.0003(4) C20 0.0238(7) 0.0449(9) 0.0245(7) -0.0067(6) 0.0169(6) -0.0037(6) C21 0.0345(9) 0.0537(11) 0.0258(7) -0.0075(7) 0.0167(7) -0.0100(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C16 1.2075(16) . y O2 C16 1.3339(16) . y O2 C17 1.4619(16) . y O3 C19 1.2083(16) . y O4 C19 1.3354(16) . y O4 C20 1.4679(17) . y C1 C2 1.4805(18) . y C1 C13 1.4854(18) . y C1 C14 1.3128(18) . y C2 C3 1.3946(19) . y C2 C7 1.4108(18) . y C3 C4 1.399(2) . y C4 C5 1.403(2) . y C5 C6 1.392(2) . y C6 C7 1.3901(19) . y C7 C8 1.4744(19) . y C8 C9 1.3960(18) . y C8 C13 1.4076(18) . y C9 C10 1.397(2) . y C10 C11 1.399(2) . y C11 C12 1.3966(19) . y C12 C13 1.3928(18) . y C14 C15 1.3154(17) . y C15 C16 1.5020(17) . y C15 C19 1.5070(18) . y C17 C18 1.506(2) . y C20 C21 1.493(2) . y 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 O1 C16 O2 125.43(12) . . y O1 C16 C15 123.15(12) . . y O2 C16 C15 111.38(11) . . y O2 C17 C18 110.78(12) . . y O3 C19 O4 125.12(12) . . y O3 C19 C15 123.87(12) . . y O4 C19 C15 111.00(11) . . y O4 C20 C21 108.54(12) . . y C1 C14 C15 177.39(14) . . y C2 C1 C13 106.09(10) . . y C2 C3 C4 117.97(13) . . y C2 C7 C8 108.42(11) . . y C3 C2 C1 130.31(12) . . y C3 C2 C7 121.20(12) . . y C3 C4 C5 120.88(13) . . y C6 C5 C4 120.80(13) . . y C6 C7 C2 120.24(13) . . y C6 C7 C8 131.33(12) . . y C7 C2 C1 108.49(11) . . y C7 C6 C5 118.90(13) . . y C8 C9 C10 118.30(13) . . y C8 C13 C1 108.36(11) . . y C9 C8 C7 131.36(12) . . y C9 C8 C13 119.98(12) . . y C9 C10 C11 121.56(13) . . y C12 C11 C10 120.31(13) . . y C12 C13 C1 129.93(12) . . y C12 C13 C8 121.62(12) . . y C13 C8 C7 108.64(11) . . y C13 C12 C11 118.22(12) . . y C14 C1 C2 128.12(12) . . y C14 C1 C13 125.77(12) . . y C14 C15 C16 122.18(12) . . y C14 C15 C19 120.69(11) . . y C16 O2 C17 115.77(11) . . y C16 C15 C19 117.13(11) . . y C19 O4 C20 115.85(11) . . y data_6973_4 _database_code_depnum_ccdc_archive 'CCDC 864416' _audit_creation_date 2012-01-18 _audit_block_code HOS-HF-344-03 _chemical_name_systematic ; 1,1,3,3-tetra(ethoxylcarbonyl)allene ; _chemical_melting_point 276(2) _chemical_compound_source liquid _chemical_formula_moiety 'C15 H20 O8' _chemical_formula_sum 'C15 H20 O8' _chemical_formula_weight 328.31 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_Hall '-p 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.7229(2) _cell_length_b 9.6401(5) _cell_length_c 19.1004(9) _cell_angle_alpha 100.459(2) _cell_angle_beta 95.176(2) _cell_angle_gamma 102.972(2) _cell_volume 825.53(7) _cell_formula_units_Z 2 _cell_measurement_temperature 200(2) _cell_measurement_reflns_used 5048 _cell_measurement_theta_min 4.7514 _cell_measurement_theta_max 64.0634 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method ? _exptl_crystal_F_000 348 _exptl_absorpt_coefficient_mu 0.919 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3001 _exptl_absorpt_correction_T_max 1.0 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal grown from the melt in a 0.5 mm Lindemann glass capillary ; _diffrn_ambient_temperature 200(2) _diffrn_radiation_wavelength 1.54178 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_decay_% 0 _diffrn_radiation_type Cu-K\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'focusing multilayer optic' _diffrn_measurement_device_type 'Bruker AXS X8 Proteum' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_detector_area_resol_mean 66.67 _diffrn_reflns_number 18085 _diffrn_reflns_av_R_equivalents 0.0657 _diffrn_reflns_av_sigmaI/netI 0.0388 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 66.59 _reflns_number_total 2790 _reflns_number_gt 2124 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROTEUM2 (Bruker AXS, 2008)' _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.3001 and 1.0000 (SADABS). The crystal was grown from the liquid in a 0.5 mm capillary. A crystal was grown by lowering the temperature from 280 K to 200 K at a rate of 1 K per hour. It was not possible to see the crystal in the liquid but on the basis of the strength of the diffraction frames it is estimated that it has an approximate diameter of 0.1 mm. Highest peak 0.43 at 0.2853 0.9625 0.2844 [ 0.97 A from O4 ] Deepest hole -0.28 at 0.6246 0.0860 0.2811 [ 0.81 A from O4 ] ; _iucr_refine_instructions_details ; TITL 6973sad in P-1 CELL 1.54178 4.7229 9.6401 19.1004 100.459 95.176 102.972 ZERR 2.00 0.0002 0.0005 0.0009 0.002 0.002 0.002 LATT 1 SFAC C H O UNIT 30 40 16 L.S. 40 BOND ACTA FMAP 2 PLAN 20 TEMP -73.000 WGHT 0.0809 0.6295 FVAR 0.27683 C1 1 0.764706 0.760818 0.749319 11.00000 0.03183 0.03835 = 0.02877 0.01063 0.00638 0.00809 C2 1 0.847491 0.889823 0.792263 11.00000 0.03331 0.02863 = 0.02974 0.00481 0.00929 0.00068 C3 1 0.666439 0.634030 0.705787 11.00000 0.03597 0.03147 = 0.02830 0.00419 -0.00080 0.00762 C4 1 1.073568 0.919257 0.856440 11.00000 0.03586 0.03088 = 0.03440 0.00261 0.00604 0.00149 C5 1 0.704360 1.007650 0.777654 11.00000 0.03914 0.03306 = 0.03410 0.00613 0.00957 0.00371 C6 1 0.420968 0.524161 0.724013 11.00000 0.04032 0.03226 = 0.03468 0.00494 0.00051 0.00694 C7 1 0.781986 0.600756 0.635379 11.00000 0.03885 0.03553 = 0.03108 0.00486 0.00132 0.00965 C8 1 1.385676 0.813618 0.922743 11.00000 0.04234 0.04688 = 0.03473 0.00432 -0.00471 0.00925 AFIX 23 H8A 2 1.504564 0.914847 0.940013 11.00000 -1.20000 H8B 2 1.520932 0.750371 0.911166 11.00000 -1.20000 AFIX 0 C9 1 1.216582 0.766374 0.980656 11.00000 0.06141 0.06340 = 0.03700 0.01041 0.00489 0.01174 AFIX 137 H9A 2 1.085388 0.830168 0.992688 11.00000 -1.50000 H9B 2 1.353333 0.772238 1.023463 11.00000 -1.50000 H9C 2 1.100497 0.665833 0.963671 11.00000 -1.50000 AFIX 0 C10 1 0.383245 1.069497 0.692163 11.00000 0.07060 0.05656 = 0.06058 0.01843 0.00241 0.02960 AFIX 23 H10A 2 0.375286 1.145537 0.733909 11.00000 -1.20000 H10B 2 0.179601 1.018719 0.670397 11.00000 -1.20000 AFIX 0 C11 1 0.541695 1.137608 0.638743 11.00000 0.08423 0.06533 = 0.09602 0.04007 0.01234 0.01910 AFIX 137 H11A 2 0.736846 1.195389 0.661747 11.00000 -1.50000 H11B 2 0.431557 1.200951 0.619974 11.00000 -1.50000 H11C 2 0.561547 1.061561 0.599154 11.00000 -1.50000 AFIX 0 C12 1 0.218369 0.432837 0.820970 11.00000 0.05549 0.04523 = 0.04457 0.01038 0.01366 -0.00307 AFIX 23 H12A 2 0.130290 0.343073 0.784202 11.00000 -1.20000 H12B 2 0.062734 0.483600 0.832534 11.00000 -1.20000 AFIX 0 C13 1 0.351203 0.396116 0.886876 11.00000 0.07923 0.04585 = 0.05222 0.01723 0.01825 0.00855 AFIX 137 H13A 2 0.503380 0.345073 0.874668 11.00000 -1.50000 H13B 2 0.198942 0.333357 0.906552 11.00000 -1.50000 H13C 2 0.438605 0.485778 0.922730 11.00000 -1.50000 AFIX 0 C14 1 1.139611 0.696871 0.565147 11.00000 0.04922 0.05301 = 0.03500 0.00514 0.01489 0.01196 AFIX 23 H14A 2 1.142940 0.593922 0.548411 11.00000 -1.20000 H14B 2 1.344740 0.756157 0.575276 11.00000 -1.20000 AFIX 0 C15 1 0.974584 0.745594 0.507686 11.00000 0.06940 0.06878 = 0.04067 0.01217 0.01602 0.01678 AFIX 137 H15A 2 0.773696 0.684387 0.496384 11.00000 -1.50000 H15B 2 1.072029 0.737160 0.464481 11.00000 -1.50000 H15C 2 0.969725 0.847212 0.524483 11.00000 -1.50000 AFIX 0 O1 3 1.134641 1.028058 0.902011 11.00000 0.07451 0.03971 = 0.06737 -0.01319 -0.02551 0.01137 O2 3 1.186755 0.805265 0.858263 11.00000 0.05071 0.03918 = 0.03179 -0.00034 -0.00171 0.01210 O3 3 0.741651 1.121838 0.816367 11.00000 0.12345 0.05574 = 0.07862 -0.02310 -0.03663 0.04776 O4 3 0.532252 0.966431 0.715780 11.00000 0.08891 0.05153 = 0.04704 0.00156 -0.01126 0.03354 O5 3 0.222745 0.446780 0.681377 11.00000 0.05579 0.06415 = 0.04416 0.01008 -0.00768 -0.01439 O6 3 0.453011 0.527318 0.794009 11.00000 0.05069 0.04245 = 0.03312 0.00565 0.00465 -0.00504 O7 3 0.684844 0.492280 0.590459 11.00000 0.05033 0.04548 = 0.03975 -0.00878 0.00297 0.00576 O8 3 1.002658 0.711696 0.630868 11.00000 0.04978 0.03957 = 0.03219 0.00129 0.01062 0.00457 HKLF 4 END ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0809P)^2^+0.6295P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2790 _refine_ls_number_parameters 212 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0758 _refine_ls_R_factor_gt 0.0612 _refine_ls_wR_factor_ref 0.1692 _refine_ls_wR_factor_gt 0.1588 _refine_ls_goodness_of_fit_ref 1.051 _refine_ls_restrained_S_all 1.051 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.7647(6) 0.7608(3) 0.74932(13) 0.0325(6) Uani 1 1 d . . . C2 C 0.8475(6) 0.8898(3) 0.79226(13) 0.0315(6) Uani 1 1 d . . . C3 C 0.6664(6) 0.6340(3) 0.70579(13) 0.0326(6) Uani 1 1 d . . . C4 C 1.0736(6) 0.9193(3) 0.85644(14) 0.0353(6) Uani 1 1 d . . . C5 C 0.7044(6) 1.0076(3) 0.77765(14) 0.0361(6) Uani 1 1 d . . . C6 C 0.4210(6) 0.5242(3) 0.72401(14) 0.0366(6) Uani 1 1 d . . . C7 C 0.7820(6) 0.6008(3) 0.63538(14) 0.0356(6) Uani 1 1 d . . . C8 C 1.3857(7) 0.8136(3) 0.92274(14) 0.0428(7) Uani 1 1 d . . . H8A H 1.5046 0.9148 0.9400 0.051 Uiso 1 1 calc R . . H8B H 1.5209 0.7504 0.9112 0.051 Uiso 1 1 calc R . . C9 C 1.2166(8) 0.7664(4) 0.98066(16) 0.0546(8) Uani 1 1 d . . . H9A H 1.0854 0.8302 0.9927 0.082 Uiso 1 1 calc R . . H9B H 1.3533 0.7722 1.0235 0.082 Uiso 1 1 calc R . . H9C H 1.1005 0.6658 0.9637 0.082 Uiso 1 1 calc R . . C10 C 0.3833(8) 1.0695(4) 0.69216(19) 0.0599(9) Uani 1 1 d . . . H10A H 0.3753 1.1455 0.7339 0.072 Uiso 1 1 calc R . . H10B H 0.1796 1.0187 0.6704 0.072 Uiso 1 1 calc R . . C11 C 0.5417(10) 1.1376(4) 0.6387(2) 0.0787(12) Uani 1 1 d . . . H11A H 0.7369 1.1954 0.6617 0.118 Uiso 1 1 calc R . . H11B H 0.4316 1.2010 0.6200 0.118 Uiso 1 1 calc R . . H11C H 0.5615 1.0616 0.5991 0.118 Uiso 1 1 calc R . . C12 C 0.2184(7) 0.4328(3) 0.82097(16) 0.0504(8) Uani 1 1 d . . . H12A H 0.1303 0.3431 0.7842 0.060 Uiso 1 1 calc R . . H12B H 0.0627 0.4836 0.8325 0.060 Uiso 1 1 calc R . . C13 C 0.3512(9) 0.3961(4) 0.88688(17) 0.0587(9) Uani 1 1 d . . . H13A H 0.5034 0.3451 0.8747 0.088 Uiso 1 1 calc R . . H13B H 0.1989 0.3334 0.9066 0.088 Uiso 1 1 calc R . . H13C H 0.4386 0.4858 0.9227 0.088 Uiso 1 1 calc R . . C14 C 1.1396(7) 0.6969(3) 0.56515(15) 0.0458(7) Uani 1 1 d . . . H14A H 1.1429 0.5939 0.5484 0.055 Uiso 1 1 calc R . . H14B H 1.3447 0.7562 0.5753 0.055 Uiso 1 1 calc R . . C15 C 0.9746(8) 0.7456(4) 0.50769(17) 0.0590(9) Uani 1 1 d . . . H15A H 0.7737 0.6844 0.4964 0.088 Uiso 1 1 calc R . . H15B H 1.0720 0.7372 0.4645 0.088 Uiso 1 1 calc R . . H15C H 0.9697 0.8472 0.5245 0.088 Uiso 1 1 calc R . . O1 O 1.1346(5) 1.0281(2) 0.90201(13) 0.0664(7) Uani 1 1 d . . . O2 O 1.1868(4) 0.8053(2) 0.85826(9) 0.0419(5) Uani 1 1 d . . . O3 O 0.7416(7) 1.1218(3) 0.81637(15) 0.0898(10) Uani 1 1 d . . . O4 O 0.5323(6) 0.9664(2) 0.71578(12) 0.0623(7) Uani 1 1 d . . . O5 O 0.2227(5) 0.4468(3) 0.68138(11) 0.0605(7) Uani 1 1 d . . . O6 O 0.4530(4) 0.5273(2) 0.79401(10) 0.0451(5) Uani 1 1 d . . . O7 O 0.6848(5) 0.4923(2) 0.59046(10) 0.0487(6) Uani 1 1 d . . . O8 O 1.0027(4) 0.7117(2) 0.63087(9) 0.0420(5) Uani 1 1 d . . . 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 0.0318(14) 0.0383(15) 0.0288(13) 0.0106(12) 0.0064(11) 0.0081(12) C2 0.0333(14) 0.0286(13) 0.0297(13) 0.0048(11) 0.0093(11) 0.0007(11) C3 0.0360(15) 0.0315(14) 0.0283(13) 0.0042(11) -0.0008(11) 0.0076(11) C4 0.0358(15) 0.0309(14) 0.0344(14) 0.0026(11) 0.0060(11) 0.0015(12) C5 0.0391(15) 0.0331(14) 0.0341(14) 0.0061(12) 0.0096(12) 0.0037(12) C6 0.0403(16) 0.0323(14) 0.0347(15) 0.0049(12) 0.0005(12) 0.0069(12) C7 0.0388(15) 0.0355(15) 0.0311(14) 0.0049(12) 0.0013(11) 0.0096(12) C8 0.0423(16) 0.0469(17) 0.0347(15) 0.0043(12) -0.0047(12) 0.0092(13) C9 0.061(2) 0.063(2) 0.0370(16) 0.0104(15) 0.0049(15) 0.0117(17) C10 0.071(2) 0.057(2) 0.061(2) 0.0184(17) 0.0024(17) 0.0296(18) C11 0.084(3) 0.065(2) 0.096(3) 0.040(2) 0.012(2) 0.019(2) C12 0.0555(19) 0.0452(17) 0.0446(17) 0.0104(14) 0.0137(14) -0.0031(15) C13 0.079(2) 0.0458(18) 0.052(2) 0.0172(15) 0.0183(17) 0.0086(17) C14 0.0492(18) 0.0530(18) 0.0350(15) 0.0051(13) 0.0149(13) 0.0120(15) C15 0.069(2) 0.069(2) 0.0407(17) 0.0122(16) 0.0160(16) 0.0168(18) O1 0.0745(17) 0.0397(12) 0.0674(15) -0.0132(11) -0.0255(13) 0.0114(11) O2 0.0507(12) 0.0392(11) 0.0318(10) -0.0003(8) -0.0017(8) 0.0121(9) O3 0.123(3) 0.0557(15) 0.0786(18) -0.0231(14) -0.0366(17) 0.0478(16) O4 0.0889(18) 0.0515(13) 0.0470(13) 0.0016(10) -0.0113(12) 0.0335(12) O5 0.0558(14) 0.0641(14) 0.0442(12) 0.0101(11) -0.0077(11) -0.0144(12) O6 0.0507(12) 0.0424(11) 0.0331(10) 0.0057(8) 0.0046(8) -0.0050(9) O7 0.0503(13) 0.0455(12) 0.0398(11) -0.0088(9) 0.0030(9) 0.0058(10) O8 0.0498(12) 0.0396(11) 0.0322(10) 0.0013(8) 0.0106(8) 0.0046(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C3 1.307(3) . y C1 C2 1.314(3) . y C2 C4 1.492(4) . y C2 C5 1.500(4) . y C3 C6 1.498(4) . y C3 C7 1.505(4) . y C4 O1 1.195(3) . y C4 O2 1.330(3) . y C5 O3 1.176(3) . y C5 O4 1.314(3) . y C6 O5 1.194(3) . y C6 O6 1.326(3) . y C7 O7 1.195(3) . y C7 O8 1.337(3) . y C8 O2 1.459(3) . y C8 C9 1.499(4) . y C10 O4 1.451(4) . y C10 C11 1.481(5) . y C12 O6 1.464(3) . y C12 C13 1.491(5) . y C14 O8 1.462(3) . y C14 C15 1.493(5) . y 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 C3 C1 C2 176.5(3) . . y C1 C2 C4 121.1(2) . . y C1 C2 C5 119.2(2) . . y C4 C2 C5 119.7(2) . . y C1 C3 C6 119.4(2) . . y C1 C3 C7 121.0(2) . . y C6 C3 C7 119.5(2) . . y O1 C4 O2 124.4(3) . . y O1 C4 C2 124.5(3) . . y O2 C4 C2 111.0(2) . . y O3 C5 O4 124.5(3) . . y O3 C5 C2 124.5(3) . . y O4 C5 C2 111.0(2) . . y O5 C6 O6 125.2(3) . . y O5 C6 C3 124.4(2) . . y O6 C6 C3 110.4(2) . . y O7 C7 O8 126.1(2) . . y O7 C7 C3 124.4(2) . . y O8 C7 C3 109.5(2) . . y O2 C8 C9 110.5(2) . . y O4 C10 C11 109.8(3) . . y O6 C12 C13 107.4(3) . . y O8 C14 C15 110.6(3) . . y C4 O2 C8 116.4(2) . . y C5 O4 C10 118.2(2) . . y C6 O6 C12 116.8(2) . . y C7 O8 C14 116.5(2) . . y _diffrn_measured_fraction_theta_max 0.953 _diffrn_reflns_theta_full 66.59 _diffrn_measured_fraction_theta_full 0.953 _refine_diff_density_max 0.428 _refine_diff_density_min -0.276 _refine_diff_density_rms 0.062 data_6975_19 _database_code_depnum_ccdc_archive 'CCDC 864417' _audit_creation_date 2012-01-18 _audit_block_code HOS-HG-015-01 _chemical_compound_source dichloromethane,pentane _chemical_formula_moiety 'C32 H38 N2 O4' _chemical_formula_sum 'C32 H38 N2 O4' _chemical_formula_weight 514.64 _chemical_melting_point ? _chemical_name_systematic ; 1-(1,3-di(tert-butyl)imidazol-3-ium-2-yl)-1-(9H-fluoren-9-yl-8a-ide)- 2,2-di(ethoxycarbonyl)ethane ; 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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-p 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 1.00 0.1000 0.00 0.00 -1.00 0.0800 0.00 -1.00 0.00 0.1800 0.00 1.00 0.00 0.2000 -1.00 0.00 0.00 0.1200 1.00 0.00 0.00 0.0900 2.00 -1.00 0.00 0.0800 -2.00 -1.00 0.00 0.1100 loop_ _symmetry_equiv_pos_as_xyz '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, y, z' 'x-1/2, y, -z-1/2' 'x+1/2, -y+1/2, -z' '-x-1/2, y-1/2, z' '-x+1/2, -y, z+1/2' 'x, -y-1/2, z-1/2' _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 13.7855(13) _cell_length_b 18.3094(12) _cell_length_c 21.682(2) _cell_measurement_reflns_used 99485 _cell_measurement_temperature 100 _cell_measurement_theta_max 33.0994 _cell_measurement_theta_min 2.6311 _cell_volume 5472.7(9) _exptl_absorpt_coefficient_mu 0.082 _exptl_absorpt_correction_T_max 0.98686 _exptl_absorpt_correction_T_min 0.97508 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_F_000 2208 _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 18.02 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0601 _diffrn_reflns_av_sigmaI/netI 0.0361 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 80356 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 33.18 _diffrn_reflns_theta_min 2.64 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _reflns_number_gt 8250 _reflns_number_total 10457 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.604 _refine_diff_density_min -0.499 _refine_diff_density_rms 0.152 _refine_ls_R_factor_all 0.0669 _refine_ls_R_factor_gt 0.0465 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 351 _refine_ls_number_reflns 10457 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.077 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1162 _refine_ls_wR_factor_ref 0.1296 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0584P)^2^+2.4459P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.7623 and 1.0000 (SADABS). Highest peak 0.60 at 0.3796 0.0412 0.2647 [ 0.68 A from C24 ] Deepest hole -0.50 at 0.7019 0.1314 0.6200 [ 0.72 A from C20 ] ; _iucr_refine_instructions_details ; TITL 6975 CELL 0.71073 13.7855 18.3094 21.6821 90 90 90 ZERR 8 0.0013 0.0012 0.0023 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 256 304 16 32 L.S. 10 PLAN 20 FMAP 2.0 ACTA 55 WGHT 0.058400 2.445900 FVAR 0.13168 O1 4 0.274179 0.601036 0.653302 11.00000 0.01086 0.01762 = 0.01552 0.00149 -0.00058 -0.00049 O2 4 0.205228 0.668475 0.578220 11.00000 0.01244 0.01576 = 0.01703 0.00626 0.00324 -0.00060 O3 4 0.018529 0.692442 0.620563 11.00000 0.01395 0.01132 = 0.02548 0.00144 0.00041 0.00131 O4 4 -0.059815 0.585072 0.608554 11.00000 0.00899 0.01326 = 0.01642 0.00173 -0.00047 0.00097 N1 3 -0.057817 0.441371 0.665556 11.00000 0.01068 0.01115 = 0.00925 0.00038 0.00063 -0.00116 N2 3 -0.019579 0.516284 0.740640 11.00000 0.00888 0.01229 = 0.00893 -0.00066 0.00058 -0.00098 C1 1 0.173368 0.454337 0.651413 11.00000 0.01049 0.01125 = 0.00928 0.00040 0.00121 0.00062 C2 1 0.182064 0.390382 0.692643 11.00000 0.01097 0.01110 = 0.01038 -0.00001 -0.00077 0.00035 C3 1 0.128955 0.366832 0.744442 11.00000 0.01284 0.01367 = 0.01340 0.00211 0.00054 -0.00003 AFIX 43 H3 2 0.074962 0.393016 0.757573 11.00000 -1.20000 AFIX 0 C4 1 0.157781 0.303917 0.776025 11.00000 0.01651 0.01501 = 0.01550 0.00430 -0.00051 -0.00141 AFIX 43 H4 2 0.122101 0.288126 0.809897 11.00000 -1.20000 AFIX 0 C5 1 0.239665 0.264289 0.757390 11.00000 0.01898 0.01223 = 0.01812 0.00367 -0.00270 0.00049 AFIX 43 H5 2 0.257875 0.222642 0.779044 11.00000 -1.20000 AFIX 0 C6 1 0.294035 0.286850 0.706616 11.00000 0.01481 0.01148 = 0.01780 0.00006 -0.00177 0.00206 AFIX 43 H6 2 0.348587 0.260800 0.694252 11.00000 -1.20000 AFIX 0 C7 1 0.264913 0.349303 0.674746 11.00000 0.01141 0.01065 = 0.01275 -0.00100 -0.00145 0.00060 C8 1 0.307734 0.384010 0.620550 11.00000 0.01161 0.01244 = 0.01264 -0.00156 0.00050 0.00094 C9 1 0.385228 0.361976 0.583506 11.00000 0.01433 0.01595 = 0.01997 -0.00214 0.00323 0.00356 AFIX 43 H9 2 0.420744 0.320290 0.593027 11.00000 -1.20000 AFIX 0 C10 1 0.408060 0.404001 0.531889 11.00000 0.01732 0.02114 = 0.01997 -0.00239 0.00793 0.00335 AFIX 43 H10 2 0.460537 0.390993 0.507274 11.00000 -1.20000 AFIX 0 C11 1 0.352869 0.465499 0.516757 11.00000 0.01865 0.01904 = 0.01438 0.00033 0.00691 0.00095 AFIX 43 H11 2 0.368142 0.492147 0.481557 11.00000 -1.20000 AFIX 0 C12 1 0.275408 0.487493 0.553536 11.00000 0.01538 0.01509 = 0.01172 0.00038 0.00261 0.00195 AFIX 43 H12 2 0.238846 0.528246 0.542808 11.00000 -1.20000 AFIX 0 C13 1 0.253034 0.447679 0.606856 11.00000 0.01036 0.01235 = 0.01015 -0.00090 0.00115 0.00093 C14 1 0.101979 0.507900 0.652828 11.00000 0.00858 0.01155 = 0.00819 0.00027 0.00051 0.00016 C15 1 0.107686 0.580104 0.627161 11.00000 0.00900 0.01118 = 0.01065 0.00137 0.00094 0.00113 C16 1 0.202550 0.615955 0.622423 11.00000 0.01132 0.01116 = 0.01125 0.00025 0.00257 0.00067 C17 1 0.294371 0.710531 0.574308 11.00000 0.01523 0.01438 = 0.02176 0.00144 0.00666 -0.00280 AFIX 23 H17B 2 0.320966 0.716982 0.615367 11.00000 -1.20000 H17A 2 0.280139 0.758507 0.557628 11.00000 -1.20000 AFIX 0 C18 1 0.368834 0.673123 0.533838 11.00000 0.01452 0.01917 = 0.02074 0.00043 0.00627 -0.00021 AFIX 137 H18B 2 0.387180 0.627421 0.552140 11.00000 -1.50000 H18C 2 0.425004 0.703771 0.529946 11.00000 -1.50000 H18A 2 0.341528 0.664458 0.493770 11.00000 -1.50000 AFIX 0 C19 1 0.022435 0.625651 0.618191 11.00000 0.00978 0.01268 = 0.01053 0.00149 0.00091 0.00019 C20 1 -0.151004 0.623084 0.616463 11.00000 0.00948 0.01950 = 0.02041 0.00118 0.00216 0.00209 AFIX 23 H20B 2 -0.145044 0.657160 0.650508 11.00000 -1.20000 H20A 2 -0.200952 0.587958 0.627099 11.00000 -1.20000 AFIX 0 C21 1 -0.181845 0.664256 0.559446 11.00000 0.01874 0.02688 = 0.02990 0.00551 -0.00702 0.00635 AFIX 137 H21C 2 -0.243763 0.686730 0.566542 11.00000 -1.50000 H21A 2 -0.186700 0.630989 0.525362 11.00000 -1.50000 H21B 2 -0.134690 0.701239 0.550163 11.00000 -1.50000 AFIX 0 C22 1 0.010917 0.488471 0.685811 11.00000 0.00935 0.01004 = 0.00847 0.00075 0.00015 0.00099 C23 1 -0.132767 0.440514 0.708005 11.00000 0.01178 0.01638 = 0.01216 0.00004 0.00216 -0.00322 AFIX 43 H23 2 -0.189011 0.412646 0.705326 11.00000 -1.20000 AFIX 0 C24 1 -0.109982 0.487229 0.754026 11.00000 0.01057 0.01708 = 0.01190 -0.00102 0.00312 -0.00226 AFIX 43 H24 2 -0.147933 0.497903 0.788323 11.00000 -1.20000 AFIX 0 C25 1 -0.066509 0.396026 0.606996 11.00000 0.01460 0.01337 = 0.00950 -0.00230 -0.00087 -0.00108 C26 1 0.005203 0.417360 0.556860 11.00000 0.03371 0.03523 = 0.01143 -0.00739 0.00761 -0.01671 AFIX 137 H26C 2 0.003957 0.469365 0.551279 11.00000 -1.50000 H26A 2 -0.012351 0.393790 0.518917 11.00000 -1.50000 H26B 2 0.069281 0.402395 0.568728 11.00000 -1.50000 AFIX 0 C27 1 -0.051704 0.316253 0.625383 11.00000 0.03934 0.01408 = 0.02104 -0.00282 -0.00155 0.00120 AFIX 137 H27B 2 0.013071 0.309731 0.640678 11.00000 -1.50000 H27A 2 -0.061479 0.285523 0.590051 11.00000 -1.50000 H27C 2 -0.097400 0.303376 0.656975 11.00000 -1.50000 AFIX 0 C28 1 -0.168966 0.407425 0.581671 11.00000 0.02113 0.04552 = 0.02135 -0.01406 -0.00997 0.00829 AFIX 137 H28C 2 -0.215534 0.390013 0.611125 11.00000 -1.50000 H28A 2 -0.176116 0.380917 0.543741 11.00000 -1.50000 H28B 2 -0.179547 0.458498 0.574252 11.00000 -1.50000 AFIX 0 C29 1 0.030474 0.566376 0.786656 11.00000 0.01226 0.01397 = 0.00916 -0.00235 -0.00039 -0.00056 C30 1 0.140424 0.565520 0.779162 11.00000 0.01129 0.02421 = 0.01386 -0.00370 -0.00082 -0.00277 AFIX 137 H30C 2 0.169649 0.593371 0.811750 11.00000 -1.50000 H30A 2 0.157473 0.586584 0.740092 11.00000 -1.50000 H30B 2 0.163389 0.516065 0.780925 11.00000 -1.50000 AFIX 0 C31 1 -0.010584 0.643326 0.778243 11.00000 0.02055 0.01350 = 0.01963 -0.00310 -0.00146 0.00058 AFIX 137 H31B 2 -0.079862 0.642010 0.782606 11.00000 -1.50000 H31A 2 0.005872 0.661092 0.737921 11.00000 -1.50000 H31C 2 0.016462 0.675180 0.808920 11.00000 -1.50000 AFIX 0 C32 1 0.007272 0.537291 0.851584 11.00000 0.01803 0.02449 = 0.00971 -0.00043 -0.00039 -0.00246 AFIX 137 H32A 2 0.025469 0.486776 0.854208 11.00000 -1.50000 H32B 2 -0.060986 0.542061 0.859378 11.00000 -1.50000 H32C 2 0.042856 0.564890 0.881672 11.00000 -1.50000 HKLF 4 END ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 O1 O 0.27418(5) 0.60104(4) 0.65330(4) 0.01467(14) Uani 1 1 d . . . O2 O 0.20523(5) 0.66848(4) 0.57822(4) 0.01508(14) Uani 1 1 d . . . O3 O 0.01853(6) 0.69244(4) 0.62056(4) 0.01692(15) Uani 1 1 d . . . O4 O -0.05981(5) 0.58507(4) 0.60855(3) 0.01289(13) Uani 1 1 d . . . N1 N -0.05782(6) 0.44137(4) 0.66556(4) 0.01036(14) Uani 1 1 d . . . N2 N -0.01958(6) 0.51628(5) 0.74064(4) 0.01003(14) Uani 1 1 d . . . C1 C 0.17337(7) 0.45434(5) 0.65141(4) 0.01034(16) Uani 1 1 d . . . C2 C 0.18206(7) 0.39038(5) 0.69264(4) 0.01082(16) Uani 1 1 d . . . C3 C 0.12896(7) 0.36683(6) 0.74444(5) 0.01330(17) Uani 1 1 d . . . H3 H 0.0750 0.3930 0.7576 0.016 Uiso 1 1 calc R . . C4 C 0.15778(8) 0.30392(6) 0.77603(5) 0.01568(18) Uani 1 1 d . . . H4 H 0.1221 0.2881 0.8099 0.019 Uiso 1 1 calc R . . C5 C 0.23967(8) 0.26429(6) 0.75739(5) 0.01644(19) Uani 1 1 d . . . H5 H 0.2579 0.2226 0.7790 0.020 Uiso 1 1 calc R . . C6 C 0.29403(8) 0.28685(6) 0.70662(5) 0.01469(18) Uani 1 1 d . . . H6 H 0.3486 0.2608 0.6943 0.018 Uiso 1 1 calc R . . C7 C 0.26491(7) 0.34930(5) 0.67475(4) 0.01160(16) Uani 1 1 d . . . C8 C 0.30773(7) 0.38401(5) 0.62055(4) 0.01223(17) Uani 1 1 d . . . C9 C 0.38523(8) 0.36198(6) 0.58351(5) 0.01675(19) Uani 1 1 d . . . H9 H 0.4207 0.3203 0.5930 0.020 Uiso 1 1 calc R . . C10 C 0.40806(8) 0.40400(6) 0.53189(5) 0.0195(2) Uani 1 1 d . . . H10 H 0.4605 0.3910 0.5073 0.023 Uiso 1 1 calc R . . C11 C 0.35287(8) 0.46550(6) 0.51676(5) 0.01736(19) Uani 1 1 d . . . H11 H 0.3681 0.4921 0.4816 0.021 Uiso 1 1 calc R . . C12 C 0.27541(8) 0.48749(6) 0.55354(5) 0.01406(17) Uani 1 1 d . . . H12 H 0.2388 0.5282 0.5428 0.017 Uiso 1 1 calc R . . C13 C 0.25303(7) 0.44768(5) 0.60686(4) 0.01095(16) Uani 1 1 d . . . C14 C 0.10198(7) 0.50790(5) 0.65283(4) 0.00944(15) Uani 1 1 d . . . C15 C 0.10769(7) 0.58010(5) 0.62716(4) 0.01028(16) Uani 1 1 d . . . C16 C 0.20255(7) 0.61595(5) 0.62242(4) 0.01124(16) Uani 1 1 d . . . C17 C 0.29437(8) 0.71053(6) 0.57431(5) 0.01712(19) Uani 1 1 d . . . H17B H 0.3210 0.7170 0.6154 0.021 Uiso 1 1 calc R . . H17A H 0.2801 0.7585 0.5576 0.021 Uiso 1 1 calc R . . C18 C 0.36883(8) 0.67312(6) 0.53384(5) 0.0181(2) Uani 1 1 d . . . H18B H 0.3872 0.6274 0.5521 0.027 Uiso 1 1 calc R . . H18C H 0.4250 0.7038 0.5299 0.027 Uiso 1 1 calc R . . H18A H 0.3415 0.6645 0.4938 0.027 Uiso 1 1 calc R . . C19 C 0.02244(7) 0.62565(5) 0.61819(4) 0.01100(16) Uani 1 1 d . . . C20 C -0.15100(7) 0.62308(6) 0.61646(5) 0.01646(19) Uani 1 1 d . . . H20B H -0.1450 0.6572 0.6505 0.020 Uiso 1 1 calc R . . H20A H -0.2010 0.5880 0.6271 0.020 Uiso 1 1 calc R . . C21 C -0.18184(9) 0.66426(7) 0.55945(6) 0.0252(2) Uani 1 1 d . . . H21C H -0.2438 0.6867 0.5665 0.038 Uiso 1 1 calc R . . H21A H -0.1867 0.6310 0.5254 0.038 Uiso 1 1 calc R . . H21B H -0.1347 0.7012 0.5502 0.038 Uiso 1 1 calc R . . C22 C 0.01092(7) 0.48847(5) 0.68581(4) 0.00929(15) Uani 1 1 d . . . C23 C -0.13277(7) 0.44051(6) 0.70800(5) 0.01344(17) Uani 1 1 d . . . H23 H -0.1890 0.4126 0.7053 0.016 Uiso 1 1 calc R . . C24 C -0.10998(7) 0.48723(6) 0.75403(5) 0.01319(17) Uani 1 1 d . . . H24 H -0.1479 0.4979 0.7883 0.016 Uiso 1 1 calc R . . C25 C -0.06651(7) 0.39603(5) 0.60700(4) 0.01249(17) Uani 1 1 d . . . C26 C 0.00520(10) 0.41736(8) 0.55686(5) 0.0268(3) Uani 1 1 d . . . H26C H 0.0040 0.4694 0.5513 0.040 Uiso 1 1 calc R . . H26A H -0.0124 0.3938 0.5189 0.040 Uiso 1 1 calc R . . H26B H 0.0693 0.4024 0.5687 0.040 Uiso 1 1 calc R . . C27 C -0.05170(11) 0.31625(6) 0.62538(6) 0.0248(2) Uani 1 1 d . . . H27B H 0.0131 0.3097 0.6407 0.037 Uiso 1 1 calc R . . H27A H -0.0615 0.2855 0.5901 0.037 Uiso 1 1 calc R . . H27C H -0.0974 0.3034 0.6570 0.037 Uiso 1 1 calc R . . C28 C -0.16897(10) 0.40742(9) 0.58167(6) 0.0293(3) Uani 1 1 d . . . H28C H -0.2155 0.3900 0.6111 0.044 Uiso 1 1 calc R . . H28A H -0.1761 0.3809 0.5437 0.044 Uiso 1 1 calc R . . H28B H -0.1795 0.4585 0.5743 0.044 Uiso 1 1 calc R . . C29 C 0.03047(7) 0.56638(5) 0.78666(4) 0.01180(16) Uani 1 1 d . . . C30 C 0.14042(7) 0.56552(6) 0.77916(5) 0.01645(19) Uani 1 1 d . . . H30C H 0.1696 0.5934 0.8117 0.025 Uiso 1 1 calc R . . H30A H 0.1575 0.5866 0.7401 0.025 Uiso 1 1 calc R . . H30B H 0.1634 0.5161 0.7809 0.025 Uiso 1 1 calc R . . C31 C -0.01058(8) 0.64333(6) 0.77824(5) 0.01789(19) Uani 1 1 d . . . H31B H -0.0799 0.6420 0.7826 0.027 Uiso 1 1 calc R . . H31A H 0.0059 0.6611 0.7379 0.027 Uiso 1 1 calc R . . H31C H 0.0165 0.6752 0.8089 0.027 Uiso 1 1 calc R . . C32 C 0.00727(8) 0.53729(7) 0.85158(5) 0.0174(2) Uani 1 1 d . . . H32A H 0.0255 0.4868 0.8542 0.026 Uiso 1 1 calc R . . H32B H -0.0610 0.5421 0.8594 0.026 Uiso 1 1 calc R . . H32C H 0.0429 0.5649 0.8817 0.026 Uiso 1 1 calc R . . 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 O1 0.0109(3) 0.0176(3) 0.0155(3) 0.0015(3) -0.0006(3) -0.0005(3) O2 0.0124(3) 0.0158(3) 0.0170(3) 0.0063(3) 0.0032(3) -0.0006(3) O3 0.0139(3) 0.0113(3) 0.0255(4) 0.0014(3) 0.0004(3) 0.0013(3) O4 0.0090(3) 0.0133(3) 0.0164(3) 0.0017(3) -0.0005(2) 0.0010(2) N1 0.0107(3) 0.0112(3) 0.0093(3) 0.0004(3) 0.0006(3) -0.0012(3) N2 0.0089(3) 0.0123(3) 0.0089(3) -0.0007(3) 0.0006(2) -0.0010(3) C1 0.0105(4) 0.0113(4) 0.0093(4) 0.0004(3) 0.0012(3) 0.0006(3) C2 0.0110(4) 0.0111(4) 0.0104(4) 0.0000(3) -0.0008(3) 0.0003(3) C3 0.0128(4) 0.0137(4) 0.0134(4) 0.0021(3) 0.0005(3) 0.0000(3) C4 0.0165(4) 0.0150(4) 0.0155(4) 0.0043(3) -0.0005(3) -0.0014(4) C5 0.0190(5) 0.0122(4) 0.0181(4) 0.0037(3) -0.0027(4) 0.0005(4) C6 0.0148(4) 0.0115(4) 0.0178(4) 0.0001(3) -0.0018(3) 0.0021(3) C7 0.0114(4) 0.0107(4) 0.0127(4) -0.0010(3) -0.0014(3) 0.0006(3) C8 0.0116(4) 0.0124(4) 0.0126(4) -0.0016(3) 0.0005(3) 0.0009(3) C9 0.0143(4) 0.0159(4) 0.0200(5) -0.0021(4) 0.0032(4) 0.0036(4) C10 0.0173(5) 0.0211(5) 0.0200(5) -0.0024(4) 0.0079(4) 0.0033(4) C11 0.0186(5) 0.0190(5) 0.0144(4) 0.0003(4) 0.0069(4) 0.0010(4) C12 0.0154(4) 0.0151(4) 0.0117(4) 0.0004(3) 0.0026(3) 0.0020(3) C13 0.0104(4) 0.0124(4) 0.0102(4) -0.0009(3) 0.0012(3) 0.0009(3) C14 0.0086(3) 0.0116(4) 0.0082(3) 0.0003(3) 0.0005(3) 0.0002(3) C15 0.0090(4) 0.0112(4) 0.0106(4) 0.0014(3) 0.0009(3) 0.0011(3) C16 0.0113(4) 0.0112(4) 0.0112(4) 0.0002(3) 0.0026(3) 0.0007(3) C17 0.0152(4) 0.0144(4) 0.0218(5) 0.0014(4) 0.0067(4) -0.0028(4) C18 0.0145(4) 0.0192(5) 0.0207(5) 0.0004(4) 0.0063(4) -0.0002(4) C19 0.0098(4) 0.0127(4) 0.0105(4) 0.0015(3) 0.0009(3) 0.0002(3) C20 0.0095(4) 0.0195(5) 0.0204(5) 0.0012(4) 0.0022(3) 0.0021(3) C21 0.0187(5) 0.0269(6) 0.0299(6) 0.0055(5) -0.0070(4) 0.0063(4) C22 0.0093(4) 0.0100(4) 0.0085(3) 0.0007(3) 0.0001(3) 0.0010(3) C23 0.0118(4) 0.0164(4) 0.0122(4) 0.0000(3) 0.0022(3) -0.0032(3) C24 0.0106(4) 0.0171(4) 0.0119(4) -0.0010(3) 0.0031(3) -0.0023(3) C25 0.0146(4) 0.0134(4) 0.0095(4) -0.0023(3) -0.0009(3) -0.0011(3) C26 0.0337(6) 0.0352(7) 0.0114(4) -0.0074(4) 0.0076(4) -0.0167(5) C27 0.0393(7) 0.0141(5) 0.0210(5) -0.0028(4) -0.0015(5) 0.0012(5) C28 0.0211(5) 0.0455(8) 0.0214(5) -0.0141(5) -0.0100(4) 0.0083(5) C29 0.0123(4) 0.0140(4) 0.0092(4) -0.0023(3) -0.0004(3) -0.0006(3) C30 0.0113(4) 0.0242(5) 0.0139(4) -0.0037(4) -0.0008(3) -0.0028(4) C31 0.0205(5) 0.0135(4) 0.0196(5) -0.0031(4) -0.0015(4) 0.0006(4) C32 0.0180(5) 0.0245(5) 0.0097(4) -0.0004(4) -0.0004(3) -0.0025(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O1 C16 1.2239(12) . y O2 C16 1.3582(12) . y O2 C17 1.4527(13) . y O3 C19 1.2252(12) . y O4 C19 1.3716(12) . y O4 C20 1.4471(12) . y N1 C22 1.3544(12) . y N1 C23 1.3838(13) . y N1 C25 1.5218(12) . y N2 C22 1.3599(12) . y N2 C24 1.3858(12) . y N2 C29 1.5208(13) . y C1 C2 1.4781(13) . y C1 C13 1.4678(13) . y C1 C14 1.3897(13) . y C2 C3 1.4083(13) . y C2 C7 1.4215(13) . y C3 C4 1.3978(14) . y C4 C5 1.4014(15) . y C5 C6 1.3944(15) . y C6 C7 1.3951(14) . y C7 C8 1.4605(14) . y C8 C9 1.3961(14) . y C8 C13 1.4198(14) . y C9 C10 1.3941(16) . y C10 C11 1.3980(16) . y C11 C12 1.3922(14) . y C12 C13 1.4011(14) . y C14 C15 1.4365(13) . y C14 C22 1.4879(13) . y C15 C16 1.4669(13) . y C15 C19 1.4541(13) . y C17 C18 1.5142(15) . y C20 C21 1.5091(17) . y C23 C24 1.3513(14) . y C25 C26 1.5204(16) . y C25 C27 1.5277(16) . y C25 C28 1.5297(16) . y C29 C30 1.5245(14) . y C29 C31 1.5293(15) . y C29 C32 1.5387(14) . y 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 O1 C16 O2 121.47(9) . . y O1 C16 C15 125.53(9) . . y O2 C16 C15 112.99(8) . . y O2 C17 C18 111.56(9) . . y O3 C19 O4 120.71(9) . . y O3 C19 C15 127.04(9) . . y O4 C19 C15 112.20(8) . . y O4 C20 C21 112.82(9) . . y N1 C22 N2 107.79(8) . . y N1 C22 C14 125.92(8) . . y N1 C25 C27 107.06(8) . . y N1 C25 C28 107.32(8) . . y N2 C22 C14 126.26(8) . . y N2 C29 C30 112.02(8) . . y N2 C29 C31 108.03(8) . . y N2 C29 C32 107.29(8) . . y C1 C14 C15 127.02(8) . . y C1 C14 C22 116.06(8) . . y C2 C7 C8 108.31(8) . . y C3 C2 C1 133.06(9) . . y C3 C2 C7 118.26(9) . . y C3 C4 C5 120.96(10) . . y C4 C3 C2 119.68(9) . . y C5 C6 C7 118.63(9) . . y C6 C5 C4 120.48(9) . . y C6 C7 C2 121.98(9) . . y C6 C7 C8 129.71(9) . . y C7 C2 C1 108.62(8) . . y C8 C13 C1 109.14(8) . . y C9 C8 C7 130.27(9) . . y C9 C8 C13 121.56(9) . . y C9 C10 C11 120.67(10) . . y C10 C9 C8 118.37(10) . . y C11 C12 C13 119.40(10) . . y C12 C11 C10 121.06(10) . . y C12 C13 C1 131.65(9) . . y C12 C13 C8 118.87(9) . . y C13 C1 C2 105.76(8) . . y C13 C8 C7 108.11(8) . . y C14 C1 C2 127.10(8) . . y C14 C1 C13 127.09(9) . . y C14 C15 C16 119.20(8) . . y C14 C15 C19 122.37(8) . . y C15 C14 C22 116.90(8) . . y C16 O2 C17 116.07(8) . . y C19 O4 C20 116.08(8) . . y C19 C15 C16 117.03(8) . . y C22 N1 C23 108.30(8) . . y C22 N1 C25 132.30(8) . . y C22 N2 C24 108.50(8) . . y C22 N2 C29 131.23(8) . . y C23 N1 C25 119.34(8) . . y C23 C24 N2 107.30(8) . . y C24 N2 C29 120.14(8) . . y C24 C23 N1 108.08(9) . . y C26 C25 N1 113.90(8) . . y C26 C25 C27 110.20(10) . . y C26 C25 C28 107.98(10) . . y C27 C25 C28 110.33(10) . . y C30 C29 C31 111.39(9) . . y C30 C29 C32 107.50(8) . . y C31 C29 C32 110.55(9) . . y data_6979_8 _database_code_depnum_ccdc_archive 'CCDC 864418' _audit_creation_date 2012-01-18 _audit_block_code HOS-HG-120-02 _chemical_name_systematic ; 1,1-di(ethoxycarbonyl)-2-(9H-3,6-difluoro-fluoren-9-ylidene)-ethene ; _chemical_melting_point ? _chemical_compound_source hexane _chemical_formula_moiety 'C21 H16 F2 O4' _chemical_formula_sum 'C21 H16 F2 O4' _chemical_formula_weight 370.34 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'p 21/n' _symmetry_space_group_name_Hall '-p 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 4.5285(2) _cell_length_b 45.944(2) _cell_length_c 8.2961(4) _cell_angle_alpha 90.00 _cell_angle_beta 101.410(3) _cell_angle_gamma 90.00 _cell_volume 1691.96(14) _cell_formula_units_Z 4 _cell_measurement_temperature 100 _cell_measurement_reflns_used 4296 _cell_measurement_theta_min 3.8485 _cell_measurement_theta_max 55.1395 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 1.00 0.0200 0.00 1.00 -1.00 0.0200 0.00 1.00 0.00 0.0200 0.00 -1.00 0.00 0.0200 1.00 -1.00 0.00 0.1800 -1.00 1.00 0.00 0.1700 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.04 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method ? _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.972 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.83181 _exptl_absorpt_correction_T_max 0.96683 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type Cu-K\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator 'focusing multilayer optic' _diffrn_measurement_device_type 'Bruker AXS X8 Proteum' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_detector_area_resol_mean 66.67 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 18616 _diffrn_reflns_av_R_equivalents 0.0651 _diffrn_reflns_av_sigmaI/netI 0.0672 _diffrn_reflns_limit_h_min -4 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -48 _diffrn_reflns_limit_k_max 48 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_theta_min 1.92 _diffrn_reflns_theta_max 54.79 _reflns_number_total 2071 _reflns_number_gt 1705 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'PROTEUM2 (Bruker AXS, 2008)' _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.8005 and 1.0000 (SADABS). The compound crystallizes as very fine needles. The crystal chosen for diffraction scattered poorly at high angles because it was only 40 microns thick. As a result, it was only possible to measure data to sin(theta max)/ wavelength of 0.53. Data were, however, measured with a high redundany in order to improve the signal to noise ratio (see, intensity statistics). INTENSITY STATISTICS FOR DATASET Resolution #Data #Theory %Complete Redundancy Mean I Mean I/s R(int) Rsigma Inf - 2.67 107 108 99.1 8.38 44.6 15.81 0.0270 0.0526 2.67 - 2.07 108 108 100.0 15.71 14.5 21.22 0.0393 0.0424 2.07 - 1.82 108 108 100.0 15.01 13.8 19.88 0.0354 0.0444 1.82 - 1.64 108 108 100.0 13.99 13.5 17.67 0.0345 0.0473 1.64 - 1.51 109 109 100.0 13.43 8.0 16.17 0.0552 0.0479 1.51 - 1.42 119 119 100.0 12.19 5.4 14.09 0.0723 0.0523 1.42 - 1.35 116 116 100.0 11.48 4.2 12.73 0.1049 0.0572 1.35 - 1.29 116 116 100.0 11.04 4.5 12.98 0.1212 0.0589 1.29 - 1.23 118 118 100.0 10.30 5.1 12.50 0.1264 0.0615 1.23 - 1.18 132 132 100.0 8.78 4.7 10.52 0.1399 0.0748 1.18 - 1.13 146 146 100.0 6.72 4.4 8.56 0.1374 0.0886 1.13 - 1.10 121 122 99.2 5.62 6.4 7.99 0.1078 0.0944 1.10 - 1.07 131 134 97.8 5.65 4.4 8.26 0.1643 0.0946 1.07 - 1.04 133 133 100.0 5.65 2.8 6.52 0.2449 0.1253 1.04 - 1.01 162 166 97.6 4.96 2.5 5.79 0.2531 0.1283 1.01 - 0.99 109 109 100.0 5.08 2.1 5.29 0.2627 0.1411 0.99 - 0.96 162 171 94.7 3.82 1.6 4.24 0.3397 0.1766 0.96 - 0.94 19 44 43.2 0.80 0.8 1.93 0.3482 0.4078 #----------------------------------------------------------------------------- 1.04 - 0.94 500 538 92.9 4.33 2.1 5.09 0.2724 0.1474 Inf - 0.94 2124 2167 98.0 8.71 7.7 11.17 0.0641 0.0636 Merged [A], lowest resolution = 22.97 Angstroms, 814 outliers downweighted #------------------------------------------------------------------------------ Highest peak 0.38 at 0.2184 0.1448 0.3124 [ 0.46 A from H13 ] Deepest hole -0.32 at 0.3421 0.2378 0.4376 [ 0.96 A from F2 ] ; _iucr_refine_instructions_details ; TITL 6979sadabs in P21/n #14 CELL 1.54178 4.5285 45.9441 8.2961 90 101.41 90 ZERR 4 0.0002 0.0024 0.0004 0 0.003 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H O F UNIT 84 64 16 8 L.S. 4 PLAN 20 SIZE 0.048 0.057 0.38 TEMP -173 REM reset to P21/n #14 BOND $H FMAP 2 ACTA WGHT 0.0518 2.6833 FVAR 0.13156 F1 4 1.02606 0.29162 0.58445 11.00000 0.03273 0.03361 0.02865 = 0.00351 -0.00046 0.00315 F2 4 -0.36821 0.26085 -0.11358 11.00000 0.03951 0.02728 0.03824 = -0.00393 0.00190 -0.00376 O4 3 0.49123 0.40548 -0.16579 11.00000 0.03870 0.02690 0.03161 = 0.00398 0.01608 0.00586 O3 3 0.41627 0.45208 -0.11273 11.00000 0.07089 0.02351 0.05212 = 0.00014 0.03418 -0.00587 O1 3 -0.09330 0.42455 0.23297 11.00000 0.03833 0.03072 0.03312 = 0.00201 0.01443 0.00415 O2 3 0.07311 0.46204 0.10517 11.00000 0.06646 0.01846 0.09653 = 0.00204 0.05839 0.00469 C15 1 0.23124 0.41511 0.04624 11.00000 0.02002 0.01838 0.02634 = 0.00168 0.00282 -0.00245 C8 1 0.43598 0.31550 0.25206 11.00000 0.02073 0.02998 0.02114 = -0.00202 0.01187 0.00052 C12 1 -0.32447 0.31147 -0.13483 11.00000 0.02548 0.03528 0.01992 = 0.00016 0.00616 0.00449 AFIX 43 H12 2 -0.49624 0.31155 -0.22168 11.00000 -1.20000 AFIX 0 C16 1 0.05307 0.43422 0.13882 11.00000 0.02054 0.02645 0.02937 = -0.00011 -0.00016 0.00143 C19 1 0.38682 0.42702 -0.08319 11.00000 0.02294 0.02178 0.02850 = -0.00208 0.00140 0.00216 C11 1 -0.21826 0.28583 -0.05942 11.00000 0.03164 0.02655 0.02656 = -0.00762 0.01089 -0.00419 C13 1 -0.17714 0.33712 -0.08215 11.00000 0.03038 0.02615 0.02504 = 0.00220 0.01183 0.00322 AFIX 43 H13 2 -0.24565 0.35513 -0.13223 11.00000 -1.20000 AFIX 0 C1 1 0.25216 0.38745 0.08422 11.00000 0.02004 0.03025 0.02169 = -0.00538 0.00642 -0.00163 C20 1 0.65004 0.41460 -0.29495 11.00000 0.03196 0.03523 0.03026 = 0.00508 0.01478 0.00318 AFIX 23 H20a 2 0.79244 0.39915 -0.31287 11.00000 -1.20000 H20b 2 0.76776 0.43244 -0.25951 11.00000 -1.20000 AFIX 0 C14 1 0.07201 0.33610 0.04488 11.00000 0.02274 0.02491 0.02521 = -0.00099 0.00932 0.00209 C10 1 0.02841 0.28370 0.06772 11.00000 0.03026 0.02196 0.02538 = -0.00083 0.00923 -0.00030 AFIX 43 H10 2 0.09485 0.26550 0.11610 11.00000 -1.20000 AFIX 0 C5 1 0.91425 0.33879 0.47785 11.00000 0.02685 0.02828 0.02286 = -0.00259 0.00793 -0.00059 AFIX 43 H5 2 1.07832 0.34625 0.55639 11.00000 -1.20000 AFIX 0 C7 1 0.61274 0.29692 0.36329 11.00000 0.02731 0.02416 0.02514 = 0.00052 0.01022 0.00245 AFIX 43 H7 2 0.57470 0.27659 0.36378 11.00000 -1.20000 AFIX 0 C6 1 0.84758 0.30959 0.47358 11.00000 0.02815 0.02968 0.02366 = 0.00543 0.00679 0.00659 C9 1 0.17544 0.30971 0.12161 11.00000 0.02402 0.02419 0.02301 = -0.00098 0.01121 0.00442 C2 1 0.27282 0.35964 0.12361 11.00000 0.02444 0.02233 0.02534 = -0.00056 0.01031 0.00270 C3 1 0.49957 0.34547 0.25450 11.00000 0.02167 0.02470 0.02579 = 0.00282 0.00999 0.00176 C21 1 0.43173 0.42048 -0.45316 11.00000 0.03696 0.04490 0.02883 = 0.00027 0.00668 0.00860 AFIX 137 H21b 2 0.54235 0.42702 -0.53680 11.00000 -1.50000 H21c 2 0.28946 0.43564 -0.43518 11.00000 -1.50000 H21a 2 0.32104 0.40261 -0.49064 11.00000 -1.50000 AFIX 0 C18 1 0.13155 0.50056 0.30394 11.00000 0.06113 0.04479 0.04970 = 0.00753 0.02888 0.01443 AFIX 137 H18b 2 0.26940 0.51021 0.24361 11.00000 -1.50000 H18a 2 0.24656 0.48783 0.38845 11.00000 -1.50000 H18c 2 0.02497 0.51526 0.35621 11.00000 -1.50000 AFIX 0 C4 1 0.73806 0.35722 0.36559 11.00000 0.02973 0.02472 0.02799 = -0.00109 0.01404 -0.00291 AFIX 43 H4 2 0.78036 0.37747 0.36506 11.00000 -1.20000 AFIX 0 C17 1 -0.09067 0.48289 0.18777 11.00000 0.05839 0.02554 0.09424 = -0.00420 0.04902 0.00699 AFIX 23 H17a 2 -0.22551 0.47242 0.24853 11.00000 -1.20000 H17b 2 -0.21546 0.49574 0.10560 11.00000 -1.20000 AFIX 0 HKLF 4 END ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+2.6833P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 2071 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_gt 0.0544 _refine_ls_wR_factor_ref 0.1465 _refine_ls_wR_factor_gt 0.1368 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 F1 F 1.0261(4) 0.29162(4) 0.5844(2) 0.0326(6) Uani 1 1 d . . . F2 F -0.3682(5) 0.26085(4) -0.1136(2) 0.0358(6) Uani 1 1 d . . . O4 O 0.4912(5) 0.40548(5) -0.1658(3) 0.0311(7) Uani 1 1 d . . . O3 O 0.4163(7) 0.45208(6) -0.1127(3) 0.0458(8) Uani 1 1 d . . . O1 O -0.0933(6) 0.42455(5) 0.2330(3) 0.0330(7) Uani 1 1 d . . . O2 O 0.0731(7) 0.46204(5) 0.1052(4) 0.0547(9) Uani 1 1 d . . . C15 C 0.2312(7) 0.41511(7) 0.0462(4) 0.0218(8) Uani 1 1 d . . . C8 C 0.4360(8) 0.31550(7) 0.2521(4) 0.0229(9) Uani 1 1 d . . . C12 C -0.3245(8) 0.31147(8) -0.1348(4) 0.0267(9) Uani 1 1 d . . . H12 H -0.4962 0.3115 -0.2217 0.032 Uiso 1 1 calc R . . C16 C 0.0531(8) 0.43422(8) 0.1388(5) 0.0261(9) Uani 1 1 d . . . C19 C 0.3868(8) 0.42702(8) -0.0832(4) 0.0249(9) Uani 1 1 d . . . C11 C -0.2183(8) 0.28583(8) -0.0594(4) 0.0275(9) Uani 1 1 d . . . C13 C -0.1771(8) 0.33712(8) -0.0822(4) 0.0263(9) Uani 1 1 d . . . H13 H -0.2456 0.3551 -0.1322 0.032 Uiso 1 1 calc R . . C1 C 0.2522(7) 0.38745(8) 0.0842(4) 0.0237(9) Uani 1 1 d . . . C20 C 0.6500(8) 0.41460(8) -0.2949(4) 0.0313(10) Uani 1 1 d . . . H20A H 0.7924 0.3991 -0.3129 0.038 Uiso 1 1 calc R . . H20B H 0.7678 0.4324 -0.2595 0.038 Uiso 1 1 calc R . . C14 C 0.0720(8) 0.33610(7) 0.0449(4) 0.0237(9) Uani 1 1 d . . . C10 C 0.0284(8) 0.28370(8) 0.0677(4) 0.0254(9) Uani 1 1 d . . . H10 H 0.0948 0.2655 0.1161 0.030 Uiso 1 1 calc R . . C5 C 0.9142(8) 0.33879(7) 0.4778(4) 0.0256(9) Uani 1 1 d . . . H5 H 1.0783 0.3462 0.5564 0.031 Uiso 1 1 calc R . . C7 C 0.6127(8) 0.29692(8) 0.3633(4) 0.0248(9) Uani 1 1 d . . . H7 H 0.5747 0.2766 0.3638 0.030 Uiso 1 1 calc R . . C6 C 0.8476(8) 0.30959(8) 0.4736(4) 0.0269(9) Uani 1 1 d . . . C9 C 0.1754(8) 0.30971(7) 0.1216(4) 0.0228(9) Uani 1 1 d . . . C2 C 0.2728(8) 0.35964(7) 0.1236(4) 0.0233(9) Uani 1 1 d . . . C3 C 0.4996(8) 0.34547(7) 0.2545(4) 0.0233(9) Uani 1 1 d . . . C21 C 0.4317(9) 0.42048(9) -0.4532(5) 0.0369(10) Uani 1 1 d . . . H21B H 0.5424 0.4270 -0.5368 0.055 Uiso 1 1 calc R . . H21C H 0.2895 0.4356 -0.4352 0.055 Uiso 1 1 calc R . . H21A H 0.3210 0.4026 -0.4906 0.055 Uiso 1 1 calc R . . C18 C 0.1316(10) 0.50056(9) 0.3039(5) 0.0494(12) Uani 1 1 d . . . H18B H 0.2694 0.5102 0.2436 0.074 Uiso 1 1 calc R . . H18A H 0.2466 0.4878 0.3885 0.074 Uiso 1 1 calc R . . H18C H 0.0250 0.5153 0.3562 0.074 Uiso 1 1 calc R . . C4 C 0.7381(8) 0.35722(8) 0.3656(4) 0.0263(9) Uani 1 1 d . . . H4 H 0.7804 0.3775 0.3651 0.032 Uiso 1 1 calc R . . C17 C -0.0907(10) 0.48289(9) 0.1878(6) 0.0547(13) Uani 1 1 d . . . H17A H -0.2255 0.4724 0.2485 0.066 Uiso 1 1 calc R . . H17B H -0.2155 0.4957 0.1056 0.066 Uiso 1 1 calc R . . 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 F1 0.0327(12) 0.0336(12) 0.0286(12) 0.0035(10) -0.0005(10) 0.0031(9) F2 0.0395(13) 0.0273(12) 0.0382(13) -0.0039(10) 0.0019(10) -0.0038(9) O4 0.0387(16) 0.0269(14) 0.0316(15) 0.0040(12) 0.0161(13) 0.0059(11) O3 0.071(2) 0.0235(17) 0.0521(19) 0.0001(13) 0.0342(16) -0.0059(14) O1 0.0383(16) 0.0307(15) 0.0331(16) 0.0020(12) 0.0144(14) 0.0042(12) O2 0.066(2) 0.0185(16) 0.097(2) 0.0020(15) 0.0584(19) 0.0047(13) C15 0.020(2) 0.018(2) 0.026(2) 0.0017(16) 0.0028(16) -0.0024(15) C8 0.021(2) 0.030(2) 0.021(2) -0.0020(17) 0.0119(16) 0.0005(16) C12 0.025(2) 0.035(2) 0.020(2) 0.0002(17) 0.0062(16) 0.0045(17) C16 0.021(2) 0.026(2) 0.029(2) -0.0001(17) -0.0002(18) 0.0014(16) C19 0.023(2) 0.022(2) 0.028(2) -0.0021(18) 0.0014(17) 0.0022(16) C11 0.032(2) 0.027(2) 0.027(2) -0.0076(17) 0.0109(19) -0.0042(17) C13 0.030(2) 0.026(2) 0.025(2) 0.0022(17) 0.0118(19) 0.0032(17) C1 0.020(2) 0.030(3) 0.022(2) -0.0054(17) 0.0064(15) -0.0016(16) C20 0.032(2) 0.035(2) 0.030(2) 0.0051(18) 0.0148(19) 0.0032(17) C14 0.023(2) 0.025(2) 0.025(2) -0.0010(16) 0.0093(17) 0.0021(16) C10 0.030(2) 0.022(2) 0.025(2) -0.0008(16) 0.0092(18) -0.0003(16) C5 0.027(2) 0.028(2) 0.023(2) -0.0026(17) 0.0079(17) -0.0006(17) C7 0.027(2) 0.024(2) 0.025(2) 0.0005(17) 0.0102(18) 0.0024(16) C6 0.028(2) 0.030(2) 0.024(2) 0.0054(18) 0.0068(17) 0.0066(17) C9 0.024(2) 0.024(2) 0.023(2) -0.0010(16) 0.0112(16) 0.0044(16) C2 0.024(2) 0.022(2) 0.025(2) -0.0006(16) 0.0103(16) 0.0027(16) C3 0.022(2) 0.025(2) 0.026(2) 0.0028(16) 0.0100(17) 0.0018(16) C21 0.037(2) 0.045(3) 0.029(2) 0.0003(19) 0.0067(19) 0.0086(19) C18 0.061(3) 0.045(3) 0.050(3) 0.008(2) 0.029(2) 0.014(2) C4 0.030(2) 0.025(2) 0.028(2) -0.0011(17) 0.0140(18) -0.0029(17) C17 0.058(3) 0.026(2) 0.094(4) -0.004(2) 0.049(3) 0.007(2) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 F1 C6 1.373(4) . y F2 C11 1.364(4) . y O4 C19 1.342(4) . y O4 C20 1.465(4) . y O3 C19 1.190(4) . y O1 C16 1.205(4) . y O2 C16 1.315(4) . y O2 C17 1.462(5) . y C15 C1 1.308(5) . y C15 C19 1.499(5) . y C15 C16 1.502(5) . y C8 C7 1.389(5) . y C8 C3 1.406(5) . y C8 C9 1.459(5) . y C12 C11 1.375(5) . y C12 C13 1.382(5) . y C12 H12 0.9500 . n C11 C10 1.380(5) . y C13 C14 1.384(5) . y C13 H13 0.9500 . n C1 C2 1.318(5) . y C20 C21 1.503(5) . y C20 H20A 0.9900 . n C20 H20B 0.9900 . n C14 C9 1.406(5) . y C14 C2 1.479(5) . y C10 C9 1.398(5) . y C10 H10 0.9500 . n C5 C6 1.374(5) . y C5 C4 1.388(5) . y C5 H5 0.9500 . n C7 C6 1.386(5) . y C7 H7 0.9500 . n C2 C3 1.489(5) . y C3 C4 1.383(5) . y C21 H21B 0.9800 . n C21 H21C 0.9800 . n C21 H21A 0.9800 . n C18 C17 1.489(6) . y C18 H18B 0.9800 . n C18 H18A 0.9800 . n C18 H18C 0.9800 . n C4 H4 0.9500 . n C17 H17A 0.9900 . n C17 H17B 0.9900 . n 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 C19 O4 C20 115.8(3) . . y C16 O2 C17 118.3(3) . . y C1 C15 C19 120.3(3) . . y C1 C15 C16 117.7(3) . . y C19 C15 C16 121.9(3) . . y C7 C8 C3 120.2(3) . . y C7 C8 C9 131.0(3) . . y C3 C8 C9 108.8(3) . . y C11 C12 C13 118.9(3) . . y C11 C12 H12 120.6 . . n C13 C12 H12 120.6 . . n O1 C16 O2 124.4(3) . . y O1 C16 C15 122.4(3) . . y O2 C16 C15 113.1(3) . . y O3 C19 O4 122.9(3) . . y O3 C19 C15 126.0(3) . . y O4 C19 C15 111.1(3) . . y F2 C11 C12 117.7(3) . . y F2 C11 C10 117.9(3) . . y C12 C11 C10 124.5(3) . . y C12 C13 C14 118.8(3) . . y C12 C13 H13 120.6 . . n C14 C13 H13 120.6 . . n C15 C1 C2 179.6(4) . . y O4 C20 C21 110.9(3) . . y O4 C20 H20A 109.5 . . n C21 C20 H20A 109.5 . . n O4 C20 H20B 109.5 . . n C21 C20 H20B 109.5 . . n H20A C20 H20B 108.0 . . n C13 C14 C9 121.5(3) . . y C13 C14 C2 130.5(3) . . y C9 C14 C2 108.1(3) . . y C11 C10 C9 116.5(3) . . y C11 C10 H10 121.7 . . n C9 C10 H10 121.7 . . n C6 C5 C4 119.0(3) . . y C6 C5 H5 120.5 . . n C4 C5 H5 120.5 . . n C6 C7 C8 116.5(3) . . y C6 C7 H7 121.7 . . n C8 C7 H7 121.7 . . n F1 C6 C5 118.2(3) . . y F1 C6 C7 117.6(3) . . y C5 C6 C7 124.2(3) . . y C10 C9 C14 119.8(3) . . y C10 C9 C8 131.1(3) . . y C14 C9 C8 109.1(3) . . y C1 C2 C14 126.3(3) . . y C1 C2 C3 127.6(3) . . y C14 C2 C3 106.1(3) . . y C4 C3 C8 121.5(3) . . y C4 C3 C2 130.6(3) . . y C8 C3 C2 107.9(3) . . y C20 C21 H21B 109.5 . . n C20 C21 H21C 109.5 . . n H21B C21 H21C 109.5 . . n C20 C21 H21A 109.5 . . n H21B C21 H21A 109.5 . . n H21C C21 H21A 109.5 . . n C17 C18 H18B 109.5 . . n C17 C18 H18A 109.5 . . n H18B C18 H18A 109.5 . . n C17 C18 H18C 109.5 . . n H18B C18 H18C 109.5 . . n H18A C18 H18C 109.5 . . n C3 C4 C5 118.6(3) . . y C3 C4 H4 120.7 . . n C5 C4 H4 120.7 . . n O2 C17 C18 108.7(4) . . y O2 C17 H17A 110.0 . . n C18 C17 H17A 110.0 . . n O2 C17 H17B 110.0 . . n C18 C17 H17B 110.0 . . n H17A C17 H17B 108.3 . . n _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 54.79 _diffrn_measured_fraction_theta_full 0.981 _refine_diff_density_max 0.376 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.064 data_7000_28 _database_code_depnum_ccdc_archive 'CCDC 864419' _audit_creation_date 2012-01-18 _audit_block_code AVM-AB-777-01 _chemical_compound_source 'methylene chloride, pentane' _chemical_formula_moiety 'C44 H37 P2 S, F6 P' _chemical_formula_sum 'C44 H37 F6 P3 S' _chemical_formula_weight 804.71 _chemical_melting_point ? _chemical_name_systematic ; 1-(4-(methyl)phenylthio)-carbo-bis(triphenyl)phosphonium hexafluorophosphate ; 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' F F 0.0171 0.0103 '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' S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-p 1' _symmetry_Int_Tables_number 2 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x, -y, -z' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist -1.00 1.00 0.00 0.0350 1.00 -1.00 0.00 0.0350 0.00 0.00 -1.00 0.0700 0.00 0.00 1.00 0.0700 0.00 1.00 -1.00 0.0600 0.00 -1.00 1.00 0.0600 0.00 1.00 0.00 0.0700 0.00 -1.00 0.00 0.0700 1.00 -1.00 -1.00 0.0400 1.00 -1.00 1.00 0.0400 _cell_angle_alpha 98.106(5) _cell_angle_beta 97.846(5) _cell_angle_gamma 110.584(5) _cell_formula_units_Z 2 _cell_length_a 10.4125(4) _cell_length_b 12.2494(14) _cell_length_c 16.5886(7) _cell_measurement_reflns_used 53212 _cell_measurement_temperature 100 _cell_measurement_theta_max 33.0973 _cell_measurement_theta_min 2.6885 _cell_volume 1921.0(2) _exptl_absorpt_coefficient_mu 0.271 _exptl_absorpt_correction_T_max 0.98476 _exptl_absorpt_correction_T_min 0.96522 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_F_000 832 _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description prism _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.07 _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 18.02 _diffrn_measured_fraction_theta_full 0.988 _diffrn_measured_fraction_theta_max 0.972 _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0600 _diffrn_reflns_av_sigmaI/netI 0.0863 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 26184 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 30.07 _diffrn_reflns_theta_min 2.69 _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 7538 _reflns_number_total 10957 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.404 _refine_diff_density_min -0.732 _refine_diff_density_rms 0.088 _refine_ls_R_factor_all 0.0948 _refine_ls_R_factor_gt 0.0565 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.030 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 488 _refine_ls_number_reflns 10957 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.030 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1275 _refine_ls_wR_factor_ref 0.1464 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0566P)^2^+1.1490P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.7528 and 1.0000 (SADABS). Highest peak 0.40 at 0.9666 0.5836 0.2112 [ 1.00 A from S1 ] Deepest hole -0.73 at 0.9781 0.5511 0.1154 [ 0.82 A from S1 ] ; _iucr_refine_instructions_details ; TITL 7000 CELL 0.71073 10.4125 12.2494 16.5886 98.106 97.846 110.584 ZERR 2 0.0004 0.0014 0.0007 0.005 0.005 0.005 LATT 1 SFAC C H F P S UNIT 88 74 12 6 2 L.S. 10 PLAN 20 BOND FMAP 2 ACTA 55 WGHT 0.0566 1.149 FVAR 0.16873 S1 5 0.94078 0.57750 0.14976 11.00000 0.01801 0.02138 0.01572 = 0.00427 0.00674 0.01087 P1 4 0.74951 0.69490 0.20850 11.00000 0.01441 0.01526 0.01259 = 0.00326 0.00302 0.00769 P2 4 0.91320 0.58316 0.32268 11.00000 0.01218 0.01461 0.01258 = 0.00323 0.00333 0.00697 P3 4 0.37780 0.12382 0.29240 11.00000 0.01822 0.01881 0.02233 = 0.00110 0.00557 0.00948 F1 3 0.49669 0.06938 0.30387 11.00000 0.02676 0.03495 0.04141 = 0.01577 0.01559 0.02140 F2 3 0.25886 0.17876 0.28228 11.00000 0.02990 0.04128 0.05560 = 0.01372 0.01302 0.02618 F3 3 0.41984 0.15904 0.20776 11.00000 0.03549 0.03584 0.02702 = 0.01167 0.01035 0.01589 F4 3 0.26663 -0.00384 0.24267 11.00000 0.02864 0.02527 0.03566 = -0.00473 0.00528 0.00313 F5 3 0.48869 0.25154 0.34331 11.00000 0.03178 0.02320 0.03680 = -0.00613 0.00231 0.00278 F6 3 0.33657 0.08939 0.37817 11.00000 0.03759 0.03792 0.02724 = 0.00699 0.01697 0.01882 C1 1 0.85289 0.61252 0.22742 11.00000 0.01750 0.01848 0.01280 = 0.00381 0.00494 0.01088 C2 1 0.83777 0.43132 0.09005 11.00000 0.02652 0.02240 0.01429 = 0.00568 0.00630 0.01577 C3 1 0.90999 0.37253 0.04766 11.00000 0.02772 0.02752 0.01800 = 0.00652 0.00873 0.01788 AFIX 43 H3 2 1.00661 0.40839 0.05355 11.00000 -1.20000 AFIX 0 C4 1 0.83753 0.26074 -0.00317 11.00000 0.04219 0.02838 0.02172 = 0.00521 0.01550 0.02361 AFIX 43 H4 2 0.88625 0.22334 -0.03206 11.00000 -1.20000 AFIX 0 C5 1 0.69368 0.20372 -0.01167 11.00000 0.04153 0.02336 0.01783 = 0.00549 0.00851 0.01555 C6 1 0.62270 0.26205 0.03167 11.00000 0.02593 0.02334 0.01928 = 0.00448 0.00324 0.01033 AFIX 43 H6 2 0.52658 0.22468 0.02725 11.00000 -1.20000 AFIX 0 C7 1 0.69330 0.37540 0.08153 11.00000 0.02454 0.02171 0.01678 = 0.00203 0.00566 0.01360 AFIX 43 H7 2 0.64399 0.41366 0.10908 11.00000 -1.20000 AFIX 0 C8 1 0.61409 0.08325 -0.06921 11.00000 0.05546 0.02325 0.03332 = -0.00275 0.01153 0.01442 AFIX 137 H8a 2 0.51651 0.05787 -0.06699 11.00000 -1.50000 H8b 2 0.65001 0.02617 -0.05196 11.00000 -1.50000 H8c 2 0.62538 0.08947 -0.12507 11.00000 -1.50000 AFIX 0 C11 1 0.80174 0.82901 0.28693 11.00000 0.01781 0.01455 0.01423 = 0.00387 0.00210 0.00719 C12 1 0.94435 0.89831 0.31269 11.00000 0.01793 0.01860 0.01949 = 0.00659 0.00449 0.00910 AFIX 43 H12 2 1.00940 0.87728 0.28778 11.00000 -1.20000 AFIX 0 C13 1 0.98889 0.99939 0.37605 11.00000 0.01885 0.01924 0.02456 = 0.00307 0.00026 0.00591 AFIX 43 H13 2 1.08385 1.04576 0.39362 11.00000 -1.20000 AFIX 0 C14 1 0.89126 1.03066 0.41283 11.00000 0.02825 0.01741 0.02248 = -0.00056 0.00240 0.00802 AFIX 43 H14 2 0.92154 1.09721 0.45573 11.00000 -1.20000 AFIX 0 C15 1 0.74957 0.96395 0.38638 11.00000 0.02613 0.02299 0.02466 = 0.00019 0.00814 0.01343 AFIX 43 H15 2 0.68490 0.98652 0.41060 11.00000 -1.20000 AFIX 0 C16 1 0.70379 0.86229 0.32299 11.00000 0.01825 0.02121 0.02070 = 0.00175 0.00476 0.00977 AFIX 43 H16 2 0.60860 0.81709 0.30494 11.00000 -1.20000 AFIX 0 C21 1 0.56344 0.61884 0.20299 11.00000 0.01488 0.01613 0.01383 = 0.00066 0.00271 0.00712 C22 1 0.51436 0.52712 0.24636 11.00000 0.01691 0.02243 0.01422 = 0.00316 0.00154 0.01070 AFIX 43 H22 2 0.57661 0.49954 0.27427 11.00000 -1.20000 AFIX 0 C23 1 0.37198 0.47731 0.24759 11.00000 0.02133 0.02664 0.01699 = 0.00717 0.00478 0.01033 AFIX 43 H23 2 0.33928 0.41651 0.27637 11.00000 -1.20000 AFIX 0 C24 1 0.27916 0.51843 0.20590 11.00000 0.01581 0.02927 0.02245 = 0.00544 0.00571 0.00852 AFIX 43 H24 2 0.18459 0.48601 0.20773 11.00000 -1.20000 AFIX 0 C25 1 0.32654 0.60784 0.16136 11.00000 0.01602 0.02505 0.02457 = 0.00447 0.00149 0.01073 AFIX 43 H25 2 0.26347 0.63376 0.13251 11.00000 -1.20000 AFIX 0 C26 1 0.46815 0.65829 0.16007 11.00000 0.01863 0.02076 0.01862 = 0.00431 0.00196 0.00880 AFIX 43 H26 2 0.49990 0.71845 0.13064 11.00000 -1.20000 AFIX 0 C31 1 0.76419 0.74104 0.10974 11.00000 0.01835 0.02497 0.01402 = 0.00581 0.00360 0.01231 C32 1 0.70043 0.65713 0.03562 11.00000 0.03558 0.03265 0.01855 = 0.00447 0.00484 0.02186 AFIX 43 H32 2 0.65326 0.57748 0.03684 11.00000 -1.20000 AFIX 0 C33 1 0.70771 0.69305 -0.03989 11.00000 0.04899 0.05933 0.01510 = 0.00643 0.00641 0.03733 AFIX 43 H33 2 0.66612 0.63702 -0.08926 11.00000 -1.20000 AFIX 0 C34 1 0.77642 0.81165 -0.04231 11.00000 0.03948 0.06941 0.02546 = 0.02737 0.01534 0.03142 AFIX 43 H34 2 0.78044 0.83523 -0.09310 11.00000 -1.20000 AFIX 0 C35 1 0.83872 0.89450 0.03070 11.00000 0.04156 0.04914 0.03723 = 0.02937 0.01330 0.01188 AFIX 43 H35 2 0.88440 0.97418 0.02896 11.00000 -1.20000 AFIX 0 C36 1 0.83407 0.86012 0.10755 11.00000 0.03604 0.03154 0.02340 = 0.01264 0.00639 0.00975 AFIX 43 H36 2 0.87729 0.91636 0.15668 11.00000 -1.20000 AFIX 0 C41 1 0.81223 0.59222 0.40292 11.00000 0.01156 0.01654 0.01228 = 0.00225 0.00214 0.00504 C42 1 0.81488 0.70249 0.44134 11.00000 0.01769 0.01676 0.01395 = 0.00184 0.00416 0.00608 AFIX 43 H42 2 0.86620 0.77155 0.42474 11.00000 -1.20000 AFIX 0 C43 1 0.74062 0.70879 0.50444 11.00000 0.02070 0.02155 0.01598 = -0.00036 0.00443 0.00983 AFIX 43 H43 2 0.73843 0.78153 0.52791 11.00000 -1.20000 AFIX 0 C44 1 0.67013 0.60726 0.53235 11.00000 0.01715 0.02670 0.01362 = 0.00079 0.00396 0.00825 AFIX 43 H44 2 0.62289 0.61240 0.57555 11.00000 -1.20000 AFIX 0 C45 1 0.66957 0.49736 0.49605 11.00000 0.01600 0.02226 0.01769 = 0.00599 0.00477 0.00504 AFIX 43 H45 2 0.62265 0.42939 0.51526 11.00000 -1.20000 AFIX 0 C46 1 0.73940 0.48944 0.43093 11.00000 0.01703 0.01562 0.01832 = 0.00446 0.00474 0.00681 AFIX 43 H46 2 0.73772 0.41590 0.40600 11.00000 -1.20000 AFIX 0 C51 1 1.09102 0.68203 0.37371 11.00000 0.01553 0.01427 0.02014 = 0.00386 0.00386 0.00911 C52 1 1.13380 0.69342 0.45896 11.00000 0.01934 0.01761 0.01940 = 0.00459 0.00216 0.00854 AFIX 43 H52 2 1.07116 0.65158 0.48912 11.00000 -1.20000 AFIX 0 C53 1 1.27016 0.76734 0.49918 11.00000 0.02321 0.01793 0.02040 = 0.00155 -0.00295 0.00911 AFIX 43 H53 2 1.29805 0.77566 0.55615 11.00000 -1.20000 AFIX 0 C54 1 1.36423 0.82854 0.45364 11.00000 0.01642 0.01557 0.03350 = 0.00252 -0.00169 0.00579 AFIX 43 H54 2 1.45554 0.87692 0.48017 11.00000 -1.20000 AFIX 0 C55 1 1.32255 0.81774 0.36914 11.00000 0.01542 0.01935 0.03160 = 0.00634 0.00699 0.00533 AFIX 43 H55 2 1.38575 0.85921 0.33911 11.00000 -1.20000 AFIX 0 C56 1 1.18612 0.74490 0.32883 11.00000 0.01829 0.02171 0.02062 = 0.00409 0.00504 0.01009 AFIX 43 H56 2 1.15832 0.73811 0.27204 11.00000 -1.20000 AFIX 0 C61 1 0.90941 0.43274 0.30303 11.00000 0.01864 0.01520 0.01419 = 0.00396 0.00626 0.00834 C62 1 1.02808 0.40766 0.32736 11.00000 0.01747 0.01931 0.02079 = 0.00492 0.00461 0.00999 AFIX 43 H62 2 1.11087 0.46831 0.35669 11.00000 -1.20000 AFIX 0 C63 1 1.02182 0.29145 0.30749 11.00000 0.02457 0.02393 0.02519 = 0.00632 0.00552 0.01788 AFIX 43 H63 2 1.10093 0.27458 0.32311 11.00000 -1.20000 AFIX 0 C64 1 0.89818 0.20073 0.26453 11.00000 0.03242 0.01665 0.02421 = 0.00449 0.00734 0.01417 AFIX 43 H64 2 0.89527 0.12355 0.25041 11.00000 -1.20000 AFIX 0 C65 1 0.77816 0.22453 0.24235 11.00000 0.02195 0.01657 0.01900 = 0.00196 0.00461 0.00540 AFIX 43 H65 2 0.69457 0.16315 0.21495 11.00000 -1.20000 AFIX 0 C66 1 0.78430 0.34009 0.26139 11.00000 0.01610 0.01829 0.01915 = 0.00236 0.00383 0.00790 AFIX 43 H66 2 0.70455 0.35634 0.24637 11.00000 -1.20000 AFIX 0 HKLF 4 END ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 S1 S 0.94079(6) 0.57750(6) 0.14976(3) 0.01702(13) Uani 1 1 d . . . P1 P 0.74951(6) 0.69490(5) 0.20850(3) 0.01343(13) Uani 1 1 d . . . P2 P 0.91320(6) 0.58316(5) 0.32268(3) 0.01246(12) Uani 1 1 d . . . P3 P 0.37780(7) 0.12382(6) 0.29240(4) 0.01927(14) Uani 1 1 d . . . F1 F 0.49669(16) 0.06938(15) 0.30387(10) 0.0299(4) Uani 1 1 d . . . F2 F 0.25886(18) 0.17876(17) 0.28228(11) 0.0379(4) Uani 1 1 d . . . F3 F 0.41984(17) 0.15903(16) 0.20776(9) 0.0311(4) Uani 1 1 d . . . F4 F 0.26663(17) -0.00384(15) 0.24267(10) 0.0331(4) Uani 1 1 d . . . F5 F 0.48870(18) 0.25154(15) 0.34331(10) 0.0345(4) Uani 1 1 d . . . F6 F 0.33658(18) 0.08939(16) 0.37818(9) 0.0319(4) Uani 1 1 d . . . C1 C 0.8529(2) 0.6125(2) 0.22742(13) 0.0149(4) Uani 1 1 d . . . C2 C 0.8378(3) 0.4313(2) 0.09005(14) 0.0188(5) Uani 1 1 d . . . C3 C 0.9100(3) 0.3725(2) 0.04766(14) 0.0217(5) Uani 1 1 d . . . H3 H 1.0066 0.4084 0.0536 0.026 Uiso 1 1 calc R . . C4 C 0.8375(3) 0.2607(3) -0.00317(16) 0.0270(6) Uani 1 1 d . . . H4 H 0.8863 0.2233 -0.0321 0.032 Uiso 1 1 calc R . . C5 C 0.6937(3) 0.2037(3) -0.01167(15) 0.0263(6) Uani 1 1 d . . . C6 C 0.6227(3) 0.2620(2) 0.03167(15) 0.0227(5) Uani 1 1 d . . . H6 H 0.5266 0.2247 0.0272 0.027 Uiso 1 1 calc R . . C7 C 0.6933(3) 0.3754(2) 0.08153(14) 0.0197(5) Uani 1 1 d . . . H7 H 0.6440 0.4137 0.1091 0.024 Uiso 1 1 calc R . . C8 C 0.6141(4) 0.0832(3) -0.06921(19) 0.0381(7) Uani 1 1 d . . . H8A H 0.5165 0.0579 -0.0670 0.057 Uiso 1 1 calc R . . H8B H 0.6500 0.0262 -0.0520 0.057 Uiso 1 1 calc R . . H8C H 0.6254 0.0895 -0.1251 0.057 Uiso 1 1 calc R . . C11 C 0.8017(2) 0.8290(2) 0.28693(13) 0.0152(4) Uani 1 1 d . . . C12 C 0.9443(3) 0.8983(2) 0.31269(14) 0.0177(5) Uani 1 1 d . . . H12 H 1.0094 0.8773 0.2878 0.021 Uiso 1 1 calc R . . C13 C 0.9889(3) 0.9994(2) 0.37605(15) 0.0218(5) Uani 1 1 d . . . H13 H 1.0838 1.0458 0.3936 0.026 Uiso 1 1 calc R . . C14 C 0.8913(3) 1.0307(2) 0.41283(16) 0.0237(5) Uani 1 1 d . . . H14 H 0.9215 1.0972 0.4557 0.028 Uiso 1 1 calc R . . C15 C 0.7496(3) 0.9639(2) 0.38638(16) 0.0236(5) Uani 1 1 d . . . H15 H 0.6849 0.9865 0.4106 0.028 Uiso 1 1 calc R . . C16 C 0.7038(3) 0.8623(2) 0.32299(15) 0.0196(5) Uani 1 1 d . . . H16 H 0.6086 0.8171 0.3049 0.024 Uiso 1 1 calc R . . C21 C 0.5634(2) 0.6188(2) 0.20299(13) 0.0149(4) Uani 1 1 d . . . C22 C 0.5144(2) 0.5271(2) 0.24636(14) 0.0172(5) Uani 1 1 d . . . H22 H 0.5766 0.4995 0.2743 0.021 Uiso 1 1 calc R . . C23 C 0.3720(3) 0.4773(2) 0.24759(14) 0.0209(5) Uani 1 1 d . . . H23 H 0.3393 0.4165 0.2764 0.025 Uiso 1 1 calc R . . C24 C 0.2792(3) 0.5184(2) 0.20590(15) 0.0223(5) Uani 1 1 d . . . H24 H 0.1846 0.4860 0.2077 0.027 Uiso 1 1 calc R . . C25 C 0.3265(3) 0.6078(2) 0.16136(15) 0.0214(5) Uani 1 1 d . . . H25 H 0.2635 0.6338 0.1325 0.026 Uiso 1 1 calc R . . C26 C 0.4681(3) 0.6583(2) 0.16007(14) 0.0191(5) Uani 1 1 d . . . H26 H 0.4999 0.7184 0.1306 0.023 Uiso 1 1 calc R . . C31 C 0.7642(3) 0.7410(2) 0.10974(14) 0.0177(5) Uani 1 1 d . . . C32 C 0.7004(3) 0.6571(3) 0.03562(15) 0.0266(6) Uani 1 1 d . . . H32 H 0.6533 0.5775 0.0368 0.032 Uiso 1 1 calc R . . C33 C 0.7077(3) 0.6931(3) -0.03989(17) 0.0366(8) Uani 1 1 d . . . H33 H 0.6661 0.6370 -0.0893 0.044 Uiso 1 1 calc R . . C34 C 0.7764(3) 0.8116(3) -0.04231(18) 0.0390(8) Uani 1 1 d . . . H34 H 0.7804 0.8352 -0.0931 0.047 Uiso 1 1 calc R . . C35 C 0.8387(3) 0.8945(3) 0.03070(19) 0.0414(8) Uani 1 1 d . . . H35 H 0.8844 0.9742 0.0290 0.050 Uiso 1 1 calc R . . C36 C 0.8341(3) 0.8601(3) 0.10754(17) 0.0304(6) Uani 1 1 d . . . H36 H 0.8773 0.9164 0.1567 0.036 Uiso 1 1 calc R . . C41 C 0.8122(2) 0.5922(2) 0.40292(13) 0.0136(4) Uani 1 1 d . . . C42 C 0.8149(2) 0.7025(2) 0.44134(13) 0.0163(5) Uani 1 1 d . . . H42 H 0.8662 0.7716 0.4247 0.020 Uiso 1 1 calc R . . C43 C 0.7406(3) 0.7088(2) 0.50444(14) 0.0193(5) Uani 1 1 d . . . H43 H 0.7384 0.7815 0.5279 0.023 Uiso 1 1 calc R . . C44 C 0.6701(3) 0.6073(2) 0.53235(14) 0.0194(5) Uani 1 1 d . . . H44 H 0.6229 0.6124 0.5756 0.023 Uiso 1 1 calc R . . C45 C 0.6696(2) 0.4974(2) 0.49605(14) 0.0189(5) Uani 1 1 d . . . H45 H 0.6227 0.4294 0.5153 0.023 Uiso 1 1 calc R . . C46 C 0.7394(2) 0.4894(2) 0.43093(14) 0.0166(5) Uani 1 1 d . . . H46 H 0.7377 0.4159 0.4060 0.020 Uiso 1 1 calc R . . C51 C 1.0910(2) 0.6820(2) 0.37371(14) 0.0156(4) Uani 1 1 d . . . C52 C 1.1338(3) 0.6934(2) 0.45896(14) 0.0184(5) Uani 1 1 d . . . H52 H 1.0712 0.6516 0.4891 0.022 Uiso 1 1 calc R . . C53 C 1.2702(3) 0.7673(2) 0.49918(15) 0.0211(5) Uani 1 1 d . . . H53 H 1.2981 0.7757 0.5561 0.025 Uiso 1 1 calc R . . C54 C 1.3642(3) 0.8285(2) 0.45364(17) 0.0228(5) Uani 1 1 d . . . H54 H 1.4555 0.8769 0.4802 0.027 Uiso 1 1 calc R . . C55 C 1.3226(3) 0.8177(2) 0.36914(16) 0.0221(5) Uani 1 1 d . . . H55 H 1.3857 0.8592 0.3391 0.027 Uiso 1 1 calc R . . C56 C 1.1861(3) 0.7449(2) 0.32883(15) 0.0194(5) Uani 1 1 d . . . H56 H 1.1583 0.7381 0.2720 0.023 Uiso 1 1 calc R . . C61 C 0.9094(2) 0.4327(2) 0.30303(13) 0.0151(4) Uani 1 1 d . . . C62 C 1.0281(3) 0.4077(2) 0.32736(15) 0.0182(5) Uani 1 1 d . . . H62 H 1.1109 0.4683 0.3567 0.022 Uiso 1 1 calc R . . C63 C 1.0218(3) 0.2914(2) 0.30749(15) 0.0219(5) Uani 1 1 d . . . H63 H 1.1009 0.2746 0.3231 0.026 Uiso 1 1 calc R . . C64 C 0.8982(3) 0.2007(2) 0.26453(15) 0.0229(5) Uani 1 1 d . . . H64 H 0.8953 0.1236 0.2504 0.027 Uiso 1 1 calc R . . C65 C 0.7782(3) 0.2245(2) 0.24235(15) 0.0198(5) Uani 1 1 d . . . H65 H 0.6946 0.1632 0.2150 0.024 Uiso 1 1 calc R . . C66 C 0.7843(3) 0.3401(2) 0.26139(14) 0.0176(5) Uani 1 1 d . . . H66 H 0.7045 0.3563 0.2464 0.021 Uiso 1 1 calc R . . 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 S1 0.0180(3) 0.0214(3) 0.0157(3) 0.0043(2) 0.0067(2) 0.0109(2) P1 0.0144(3) 0.0153(3) 0.0126(3) 0.0033(2) 0.0030(2) 0.0077(2) P2 0.0122(3) 0.0146(3) 0.0126(3) 0.0032(2) 0.0033(2) 0.0070(2) P3 0.0182(3) 0.0188(3) 0.0223(3) 0.0011(2) 0.0056(2) 0.0095(3) F1 0.0268(8) 0.0349(10) 0.0414(9) 0.0158(8) 0.0156(7) 0.0214(8) F2 0.0299(9) 0.0413(11) 0.0556(11) 0.0137(9) 0.0130(8) 0.0262(8) F3 0.0355(9) 0.0358(10) 0.0270(8) 0.0117(7) 0.0103(7) 0.0159(8) F4 0.0286(9) 0.0253(9) 0.0357(9) -0.0047(7) 0.0053(7) 0.0031(7) F5 0.0318(9) 0.0232(9) 0.0368(9) -0.0061(7) 0.0023(7) 0.0028(7) F6 0.0376(10) 0.0379(10) 0.0272(8) 0.0070(7) 0.0170(7) 0.0188(8) C1 0.0175(11) 0.0185(12) 0.0128(10) 0.0038(8) 0.0049(8) 0.0109(10) C2 0.0265(13) 0.0224(13) 0.0143(10) 0.0057(9) 0.0063(9) 0.0158(11) C3 0.0277(14) 0.0275(14) 0.0180(11) 0.0065(10) 0.0087(10) 0.0179(12) C4 0.0422(17) 0.0284(15) 0.0217(12) 0.0052(11) 0.0155(12) 0.0236(13) C5 0.0415(16) 0.0234(14) 0.0178(12) 0.0055(10) 0.0085(11) 0.0155(13) C6 0.0259(13) 0.0233(13) 0.0193(11) 0.0045(10) 0.0032(10) 0.0103(11) C7 0.0245(13) 0.0217(13) 0.0168(11) 0.0020(9) 0.0057(10) 0.0136(11) C8 0.055(2) 0.0232(15) 0.0333(15) -0.0028(12) 0.0115(15) 0.0144(15) C11 0.0178(11) 0.0145(11) 0.0142(10) 0.0039(8) 0.0021(9) 0.0072(9) C12 0.0179(12) 0.0186(12) 0.0195(11) 0.0066(9) 0.0045(9) 0.0091(10) C13 0.0188(12) 0.0192(13) 0.0246(12) 0.0031(10) 0.0003(10) 0.0059(10) C14 0.0282(14) 0.0174(13) 0.0225(12) -0.0006(10) 0.0024(10) 0.0080(11) C15 0.0261(14) 0.0230(14) 0.0247(12) 0.0002(10) 0.0081(11) 0.0134(11) C16 0.0182(12) 0.0212(13) 0.0207(11) 0.0018(9) 0.0048(9) 0.0098(10) C21 0.0149(11) 0.0161(11) 0.0138(10) 0.0007(8) 0.0027(8) 0.0071(9) C22 0.0169(12) 0.0224(13) 0.0142(10) 0.0032(9) 0.0015(9) 0.0107(10) C23 0.0213(12) 0.0266(14) 0.0170(11) 0.0072(10) 0.0048(9) 0.0103(11) C24 0.0158(12) 0.0293(14) 0.0225(12) 0.0054(10) 0.0057(10) 0.0085(11) C25 0.0160(12) 0.0250(14) 0.0246(12) 0.0045(10) 0.0015(10) 0.0107(11) C26 0.0186(12) 0.0208(13) 0.0186(11) 0.0043(9) 0.0020(9) 0.0088(10) C31 0.0183(12) 0.0250(13) 0.0140(10) 0.0058(9) 0.0036(9) 0.0123(10) C32 0.0356(16) 0.0327(15) 0.0185(12) 0.0045(11) 0.0048(11) 0.0219(13) C33 0.0490(19) 0.059(2) 0.0151(12) 0.0064(13) 0.0064(12) 0.0373(18) C34 0.0395(18) 0.069(2) 0.0255(14) 0.0274(15) 0.0153(13) 0.0314(17) C35 0.0416(18) 0.049(2) 0.0372(17) 0.0294(16) 0.0133(14) 0.0119(16) C36 0.0360(16) 0.0315(16) 0.0234(13) 0.0126(12) 0.0064(12) 0.0097(13) C41 0.0116(10) 0.0165(11) 0.0123(10) 0.0023(8) 0.0021(8) 0.0050(9) C42 0.0177(11) 0.0168(12) 0.0139(10) 0.0018(9) 0.0042(9) 0.0061(10) C43 0.0207(12) 0.0215(13) 0.0160(11) -0.0004(9) 0.0044(9) 0.0098(10) C44 0.0172(12) 0.0267(14) 0.0136(10) 0.0008(9) 0.0040(9) 0.0082(10) C45 0.0160(11) 0.0223(13) 0.0177(11) 0.0060(9) 0.0048(9) 0.0050(10) C46 0.0170(11) 0.0156(12) 0.0183(11) 0.0045(9) 0.0047(9) 0.0068(10) C51 0.0155(11) 0.0143(11) 0.0201(11) 0.0039(9) 0.0039(9) 0.0091(9) C52 0.0193(12) 0.0176(12) 0.0194(11) 0.0046(9) 0.0022(9) 0.0085(10) C53 0.0232(13) 0.0179(12) 0.0204(12) 0.0016(9) -0.0030(10) 0.0091(10) C54 0.0164(12) 0.0156(12) 0.0335(14) 0.0025(10) -0.0017(10) 0.0058(10) C55 0.0154(12) 0.0193(13) 0.0316(13) 0.0063(10) 0.0070(10) 0.0053(10) C56 0.0183(12) 0.0217(13) 0.0206(11) 0.0041(10) 0.0050(9) 0.0101(10) C61 0.0186(11) 0.0152(11) 0.0142(10) 0.0040(8) 0.0063(9) 0.0083(9) C62 0.0175(12) 0.0193(12) 0.0208(11) 0.0049(9) 0.0046(9) 0.0100(10) C63 0.0246(13) 0.0239(13) 0.0252(12) 0.0063(10) 0.0055(10) 0.0179(11) C64 0.0324(15) 0.0167(12) 0.0242(12) 0.0045(10) 0.0073(11) 0.0142(11) C65 0.0220(12) 0.0166(12) 0.0190(11) 0.0020(9) 0.0046(10) 0.0054(10) C66 0.0161(11) 0.0183(12) 0.0192(11) 0.0024(9) 0.0038(9) 0.0079(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 S1 C1 1.767(2) . y S1 C2 1.788(3) . y P1 C1 1.743(2) . y P1 C11 1.806(2) . y P1 C21 1.813(2) . y P1 C31 1.815(2) . y P2 C1 1.752(2) . y P2 C41 1.820(2) . y P2 C51 1.822(2) . y P2 C61 1.811(2) . y P3 F1 1.6016(17) . y P3 F2 1.6050(17) . y P3 F3 1.5984(15) . y P3 F4 1.6026(17) . y P3 F5 1.6078(17) . y P3 F6 1.6111(15) . y C2 C3 1.400(3) . y C2 C7 1.394(4) . y C3 C4 1.389(4) . y C4 C5 1.389(4) . y C5 C6 1.395(4) . y C5 C8 1.517(4) . y C6 C7 1.395(4) . y C11 C12 1.395(3) . y C11 C16 1.398(3) . y C12 C13 1.396(4) . y C13 C14 1.389(4) . y C14 C15 1.382(4) . y C15 C16 1.400(4) . y C21 C22 1.402(3) . y C21 C26 1.402(3) . y C22 C23 1.395(3) . y C23 C24 1.387(4) . y C24 C25 1.392(3) . y C25 C26 1.389(3) . y C31 C32 1.396(4) . y C31 C36 1.391(4) . y C32 C33 1.388(4) . y C33 C34 1.385(5) . y C34 C35 1.376(5) . y C35 C36 1.399(3) . y C41 C42 1.399(3) . y C41 C46 1.402(3) . y C42 C43 1.393(3) . y C43 C44 1.383(3) . y C44 C45 1.393(4) . y C45 C46 1.393(3) . y C51 C52 1.395(3) . y C51 C56 1.398(3) . y C52 C53 1.396(3) . y C53 C54 1.392(4) . y C54 C55 1.383(4) . y C55 C56 1.394(3) . y C61 C62 1.396(3) . y C61 C66 1.399(3) . y C62 C63 1.391(3) . y C63 C64 1.386(4) . y C64 C65 1.394(4) . y C65 C66 1.383(3) . y 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 P1 C1 S1 118.86(12) . . y P1 C1 P2 127.91(13) . . y P2 C1 S1 111.87(13) . . y F1 P3 F2 179.20(10) . . y F1 P3 F4 90.09(10) . . y F1 P3 F5 89.97(10) . . y F1 P3 F6 89.57(9) . . y F2 P3 F5 89.66(10) . . y F2 P3 F6 89.72(9) . . y F3 P3 F1 90.36(9) . . y F3 P3 F2 90.35(9) . . y F3 P3 F4 90.87(9) . . y F3 P3 F5 89.83(9) . . y F3 P3 F6 179.49(11) . . y F4 P3 F2 90.27(10) . . y F4 P3 F5 179.30(10) . . y F4 P3 F6 89.64(9) . . y F5 P3 F6 89.66(9) . . y C1 S1 C2 108.96(11) . . y C1 P1 C11 112.31(11) . . y C1 P1 C21 115.98(11) . . y C1 P1 C31 110.42(11) . . y C1 P2 C41 116.07(11) . . y C1 P2 C51 114.69(11) . . y C1 P2 C61 107.52(11) . . y C2 C7 C6 120.0(2) . . y C3 C2 S1 116.1(2) . . y C3 C4 C5 121.3(2) . . y C4 C3 C2 120.1(3) . . y C4 C5 C6 118.3(3) . . y C4 C5 C8 121.2(3) . . y C6 C5 C8 120.5(3) . . y C7 C2 S1 124.72(19) . . y C7 C2 C3 119.2(2) . . y C7 C6 C5 121.2(3) . . y C11 P1 C21 105.28(11) . . y C11 P1 C31 106.77(11) . . y C11 C12 C13 119.7(2) . . y C11 C16 C15 119.7(2) . . y C12 C11 P1 118.13(18) . . y C12 C11 C16 120.1(2) . . y C14 C13 C12 119.9(2) . . y C14 C15 C16 119.8(2) . . y C15 C14 C13 120.7(2) . . y C16 C11 P1 121.72(19) . . y C21 P1 C31 105.45(11) . . y C22 C21 P1 120.82(18) . . y C22 C21 C26 119.5(2) . . y C23 C22 C21 119.9(2) . . y C23 C24 C25 120.5(2) . . y C24 C23 C22 120.0(2) . . y C25 C26 C21 120.2(2) . . y C26 C21 P1 119.53(17) . . y C26 C25 C24 119.9(2) . . y C31 C36 C35 119.4(3) . . y C32 C31 P1 119.7(2) . . y C33 C32 C31 119.7(3) . . y C34 C33 C32 120.5(3) . . y C34 C35 C36 120.7(3) . . y C35 C34 C33 119.8(2) . . y C36 C31 P1 120.35(19) . . y C36 C31 C32 119.9(2) . . y C41 P2 C51 103.35(10) . . y C42 C41 P2 120.45(16) . . y C42 C41 C46 119.4(2) . . y C43 C42 C41 120.0(2) . . y C43 C44 C45 120.3(2) . . y C44 C43 C42 120.2(2) . . y C45 C46 C41 120.1(2) . . y C46 C41 P2 119.95(18) . . y C46 C45 C44 119.9(2) . . y C51 C52 C53 120.3(2) . . y C52 C51 P2 119.29(17) . . y C52 C51 C56 119.4(2) . . y C54 C53 C52 119.7(2) . . y C54 C55 C56 120.2(2) . . y C55 C54 C53 120.3(2) . . y C55 C56 C51 120.1(2) . . y C56 C51 P2 121.27(18) . . y C61 P2 C41 107.03(10) . . y C61 P2 C51 107.68(11) . . y C62 C61 P2 121.73(19) . . y C62 C61 C66 119.6(2) . . y C63 C62 C61 119.6(2) . . y C63 C64 C65 120.4(2) . . y C64 C63 C62 120.3(2) . . y C65 C66 C61 120.6(2) . . y C66 C61 P2 118.66(18) . . y C66 C65 C64 119.5(2) . . y data_7008_20 _database_code_depnum_ccdc_archive 'CCDC 864420' _audit_creation_date 2012-01-18 _audit_block_code HOS-HG-017-01 _chemical_compound_source diethylether _chemical_formula_moiety 'C32 H36 F2 N2 O4 ' _chemical_formula_sum 'C32 H36 F2 N2 O4' _chemical_formula_weight 550.63 _chemical_melting_point ? _chemical_name_common ? _chemical_name_systematic ; 1-(1,3-di(tert-butyl)imidazol-3-ium-2-yl)-1-(9H-3,6-difluoro- fluoren-9-yl-8a-ide)-2,2-di(ethoxycarbonyl)ethane ; 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca _symmetry_space_group_name_Hall '-p 2ac 2ab' _symmetry_Int_Tables_number 61 loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 0.00 0.1600 -1.00 3.00 0.00 0.1500 1.00 0.00 -1.00 0.1100 -1.00 0.00 1.00 0.1000 0.00 0.00 1.00 0.0600 -1.00 0.00 -1.00 0.1100 1.00 0.00 1.00 0.0800 0.00 0.00 -1.00 0.0800 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 13.9352(18) _cell_length_b 18.6325(14) _cell_length_c 21.797(3) _cell_measurement_reflns_used 108759 _cell_measurement_temperature 100 _cell_measurement_theta_max 33.0999 _cell_measurement_theta_min 2.6042 _cell_volume 5659.6(11) _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_T_max 0.98876 _exptl_absorpt_correction_T_min 0.97699 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_crystal_F_000 2336 _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.292 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_description block _exptl_crystal_size_max 0.31 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.14 _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 18.02 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0717 _diffrn_reflns_av_sigmaI/netI 0.0425 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 28 _diffrn_reflns_limit_k_min -28 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_number 96395 _diffrn_reflns_theta_full 27.50 _diffrn_reflns_theta_max 33.22 _diffrn_reflns_theta_min 2.61 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _reflns_number_gt 7534 _reflns_number_total 10840 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-341 ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _refine_diff_density_max 0.463 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.061 _refine_ls_R_factor_all 0.0881 _refine_ls_R_factor_gt 0.0514 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 369 _refine_ls_number_reflns 10840 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1081 _refine_ls_wR_factor_ref 0.1245 _refine_ls_weighting_details ; calc w=1/[\s^2^(Fo^2^)+(0.0410P)^2^+3.4235P] where P=(Fo^2^+2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.8412 and 1.0000 (SADABS). Highest peak 0.46 at 0.6467 0.0234 0.3511 [ 0.68 A from C1 ] Deepest hole -0.32 at 0.6836 0.2459 0.5034 [ 0.57 A from C32 ] ; _iucr_refine_instructions_details ; TITL 7008 CELL 0.71073 13.9352 18.6325 21.7974 90 90 90 ZERR 8 0.0018 0.0014 0.0026 0 0 0 LATT 1 SYMM 0.5-X,-Y,0.5+Z SYMM 0.5+X,0.5-Y,-Z SYMM -X,0.5+Y,0.5-Z SFAC C H N O F UNIT 256 288 16 32 16 L.S. 20 PLAN 20 FMAP 2 ACTA 55 WGHT 0.041 3.4235 FVAR 0.11533 F1 5 0.22694 0.71482 0.79844 11.00000 0.02713 0.02456 0.05392 = 0.02520 -0.01139 -0.00957 F2 5 0.00413 0.87854 0.50555 11.00000 0.02958 0.03389 0.03707 = 0.00222 -0.02127 -0.00721 O1 4 0.45362 1.18996 0.62076 11.00000 0.01876 0.01208 0.03496 = 0.00344 0.00053 -0.00017 O2 4 0.54466 1.09058 0.61067 11.00000 0.01135 0.01418 0.01932 = -0.00098 0.00227 -0.00177 O3 4 0.21588 1.09486 0.65921 11.00000 0.01275 0.01872 0.01867 = 0.00233 0.00169 0.00086 O4 4 0.27340 1.15588 0.57839 11.00000 0.01419 0.01880 0.01910 = 0.00622 -0.00026 0.00437 N1 3 0.51303 1.01409 0.73710 11.00000 0.01046 0.01218 0.01271 = -0.00105 -0.00076 0.00043 N2 3 0.54931 0.94148 0.66121 11.00000 0.01249 0.01205 0.01362 = -0.00067 0.00047 0.00144 C1 1 0.31849 0.95103 0.65221 11.00000 0.01259 0.01175 0.01271 = -0.00017 -0.00098 0.00008 C2 1 0.31220 0.88913 0.69395 11.00000 0.01231 0.01066 0.01659 = -0.00036 -0.00084 0.00060 C3 1 0.36591 0.86783 0.74536 11.00000 0.01381 0.01495 0.01981 = 0.00282 -0.00243 -0.00088 AFIX 43 H3 2 0.42052 0.89340 0.75649 11.00000 -1.20000 AFIX 0 C4 1 0.33740 0.80831 0.77979 11.00000 0.01709 0.01695 0.02600 = 0.00752 -0.00389 -0.00042 AFIX 43 H4 2 0.37268 0.79395 0.81386 11.00000 -1.20000 AFIX 0 C5 1 0.25564 0.77087 0.76242 11.00000 0.01829 0.01402 0.03307 = 0.00999 -0.00238 -0.00238 C6 1 0.20107 0.78799 0.71165 11.00000 0.01608 0.01321 0.03146 = 0.00312 -0.00322 -0.00279 AFIX 43 H6 2 0.14762 0.76108 0.70055 11.00000 -1.20000 AFIX 0 C7 1 0.23016 0.84770 0.67784 11.00000 0.01395 0.01090 0.02015 = -0.00043 -0.00142 0.00001 C8 1 0.18504 0.88054 0.62452 11.00000 0.01336 0.01228 0.01880 = -0.00185 -0.00253 0.00032 C9 1 0.10662 0.85726 0.58996 11.00000 0.01693 0.01601 0.02714 = -0.00227 -0.00525 -0.00231 AFIX 43 H9 2 0.07313 0.81566 0.59982 11.00000 -1.20000 AFIX 0 C10 1 0.08150 0.89928 0.54046 11.00000 0.01737 0.02213 0.02363 = -0.00488 -0.00855 -0.00070 C11 1 0.13021 0.96093 0.52349 11.00000 0.01992 0.02113 0.01652 = -0.00187 -0.00472 0.00252 AFIX 43 H11 2 0.11036 0.98731 0.48956 11.00000 -1.20000 AFIX 0 C12 1 0.20921 0.98304 0.55771 11.00000 0.01608 0.01730 0.01425 = -0.00080 -0.00118 -0.00026 AFIX 43 H12 2 0.24344 1.02370 0.54616 11.00000 -1.20000 AFIX 0 C13 1 0.23703 0.94380 0.60969 11.00000 0.01337 0.01321 0.01479 = -0.00144 -0.00106 0.00037 C14 1 0.38818 1.00457 0.65253 11.00000 0.01147 0.01251 0.01119 = -0.00091 -0.00021 0.00077 C15 1 0.48075 0.98636 0.68322 11.00000 0.01233 0.01005 0.01209 = 0.00107 0.00039 -0.00163 C16 1 0.60411 0.98767 0.74792 11.00000 0.01151 0.01995 0.01719 = -0.00180 -0.00287 0.00237 AFIX 43 H16 2 0.64326 0.99891 0.78112 11.00000 -1.20000 AFIX 0 C17 1 0.62587 0.94254 0.70148 11.00000 0.01258 0.01840 0.01925 = -0.00151 -0.00118 0.00351 AFIX 43 H17 2 0.68257 0.91666 0.69732 11.00000 -1.20000 AFIX 0 C18 1 0.46357 1.06167 0.78435 11.00000 0.01282 0.01397 0.01243 = -0.00303 0.00017 0.00159 C19 1 0.49013 1.03281 0.84820 11.00000 0.01850 0.02392 0.01375 = 0.00082 -0.00094 0.00251 AFIX 137 H19a 2 0.47329 0.98295 0.85081 11.00000 -1.50000 H19c 2 0.45581 1.05925 0.87898 11.00000 -1.50000 H19b 2 0.55789 1.03822 0.85468 11.00000 -1.50000 AFIX 0 C20 1 0.50124 1.13819 0.77641 11.00000 0.02151 0.01395 0.02092 = -0.00326 0.00081 -0.00020 AFIX 137 H20b 2 0.56996 1.13813 0.77947 11.00000 -1.50000 H20c 2 0.47485 1.16835 0.80789 11.00000 -1.50000 H20a 2 0.48255 1.15615 0.73690 11.00000 -1.50000 AFIX 0 C21 1 0.35459 1.05842 0.77868 11.00000 0.01248 0.02301 0.01607 = -0.00404 0.00079 0.00230 AFIX 137 H21b 2 0.33522 1.08015 0.74071 11.00000 -1.50000 H21c 2 0.32589 1.08382 0.81232 11.00000 -1.50000 H21a 2 0.33406 1.00925 0.77943 11.00000 -1.50000 AFIX 0 C22 1 0.55285 0.89487 0.60383 11.00000 0.01768 0.01409 0.01573 = -0.00400 0.00170 0.00104 C23 1 0.52825 0.81834 0.62317 11.00000 0.06086 0.01584 0.02556 = -0.00566 0.00143 -0.00574 AFIX 137 H23b 2 0.46359 0.81683 0.63831 11.00000 -1.50000 H23c 2 0.57152 0.80315 0.65489 11.00000 -1.50000 H23a 2 0.53417 0.78690 0.58849 11.00000 -1.50000 AFIX 0 C24 1 0.48550 0.92068 0.55394 11.00000 0.05278 0.04565 0.01543 = -0.01096 -0.00753 0.02803 AFIX 137 H24a 2 0.50039 0.89662 0.51618 11.00000 -1.50000 H24c 2 0.49296 0.97152 0.54860 11.00000 -1.50000 H24b 2 0.42047 0.91027 0.56543 11.00000 -1.50000 AFIX 0 C25 1 0.65496 0.89697 0.57866 11.00000 0.02609 0.06007 0.04177 = -0.03080 0.01589 -0.01064 AFIX 137 H25b 2 0.69818 0.87672 0.60827 11.00000 -1.50000 H25c 2 0.67288 0.94581 0.57054 11.00000 -1.50000 H25a 2 0.65808 0.86972 0.54134 11.00000 -1.50000 AFIX 0 C26 1 0.37880 1.07519 0.62784 11.00000 0.01153 0.01252 0.01320 = 0.00050 0.00015 0.00099 C27 1 0.45847 1.12427 0.61923 11.00000 0.01329 0.01381 0.01368 = 0.00162 0.00075 0.00025 C28 1 0.62804 1.13706 0.61457 11.00000 0.01469 0.02106 0.02784 = -0.00362 0.00396 -0.00543 AFIX 23 H28b 2 0.64572 1.14424 0.65717 11.00000 -1.20000 H28a 2 0.61355 1.18347 0.59667 11.00000 -1.20000 AFIX 0 C29 1 0.70923 1.10243 0.58053 11.00000 0.01519 0.02742 0.02194 = -0.00074 0.00195 -0.00000 AFIX 137 H29a 2 0.69072 1.09463 0.53863 11.00000 -1.50000 H29b 2 0.72452 1.05728 0.59934 11.00000 -1.50000 H29c 2 0.76443 1.13322 0.58180 11.00000 -1.50000 AFIX 0 C30 1 0.28282 1.10828 0.62490 11.00000 0.01330 0.01204 0.01447 = 0.00012 -0.00106 0.00045 C31 1 0.18191 1.19298 0.57583 11.00000 0.01824 0.02257 0.02208 = 0.00272 -0.00187 0.00786 AFIX 23 H31b 2 0.17283 1.22188 0.61239 11.00000 -1.20000 H31a 2 0.12971 1.15869 0.57309 11.00000 -1.20000 AFIX 0 C32 1 0.18400 1.24004 0.51958 11.00000 0.03072 0.03264 0.03104 = 0.01161 -0.00192 0.01312 AFIX 137 H32a 2 0.19182 1.21072 0.48372 11.00000 -1.50000 H32c 2 0.23662 1.27311 0.52255 11.00000 -1.50000 H32b 2 0.12488 1.26627 0.51667 11.00000 -1.50000 AFIX 0 HKLF 4 END ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 F1 F 0.22694(7) 0.71482(5) 0.79844(5) 0.0352(2) Uani 1 1 d . . . F2 F 0.00413(7) 0.87854(5) 0.50555(5) 0.0335(2) Uani 1 1 d . . . O1 O 0.45362(7) 1.18996(5) 0.62076(5) 0.0219(2) Uani 1 1 d . . . O2 O 0.54466(6) 1.09058(5) 0.61067(4) 0.01495(17) Uani 1 1 d . . . O3 O 0.21589(6) 1.09486(5) 0.65921(4) 0.01672(17) Uani 1 1 d . . . O4 O 0.27340(6) 1.15588(5) 0.57839(4) 0.01736(18) Uani 1 1 d . . . N1 N 0.51303(7) 1.01409(5) 0.73710(4) 0.01178(18) Uani 1 1 d . . . N2 N 0.54931(7) 0.94148(5) 0.66121(5) 0.01272(18) Uani 1 1 d . . . C1 C 0.31850(8) 0.95103(6) 0.65221(5) 0.0123(2) Uani 1 1 d . . . C2 C 0.31220(9) 0.88913(6) 0.69394(5) 0.0132(2) Uani 1 1 d . . . C3 C 0.36591(9) 0.86783(7) 0.74536(6) 0.0162(2) Uani 1 1 d . . . H3 H 0.4205 0.8934 0.7565 0.019 Uiso 1 1 calc R . . C4 C 0.33739(10) 0.80830(7) 0.77979(6) 0.0200(2) Uani 1 1 d . . . H4 H 0.3727 0.7939 0.8139 0.024 Uiso 1 1 calc R . . C5 C 0.25564(10) 0.77087(7) 0.76242(7) 0.0218(3) Uani 1 1 d . . . C6 C 0.20107(10) 0.78799(7) 0.71165(7) 0.0202(3) Uani 1 1 d . . . H6 H 0.1476 0.7611 0.7005 0.024 Uiso 1 1 calc R . . C7 C 0.23016(9) 0.84770(6) 0.67784(6) 0.0150(2) Uani 1 1 d . . . C8 C 0.18504(9) 0.88054(6) 0.62452(6) 0.0148(2) Uani 1 1 d . . . C9 C 0.10662(10) 0.85726(7) 0.58996(6) 0.0200(2) Uani 1 1 d . . . H9 H 0.0731 0.8157 0.5998 0.024 Uiso 1 1 calc R . . C10 C 0.08150(10) 0.89928(8) 0.54047(6) 0.0210(3) Uani 1 1 d . . . C11 C 0.13021(10) 0.96093(7) 0.52349(6) 0.0192(2) Uani 1 1 d . . . H11 H 0.1104 0.9873 0.4896 0.023 Uiso 1 1 calc R . . C12 C 0.20921(9) 0.98304(7) 0.55771(5) 0.0159(2) Uani 1 1 d . . . H12 H 0.2434 1.0237 0.5462 0.019 Uiso 1 1 calc R . . C13 C 0.23703(9) 0.94379(6) 0.60969(5) 0.0138(2) Uani 1 1 d . . . C14 C 0.38818(8) 1.00457(6) 0.65253(5) 0.0117(2) Uani 1 1 d . . . C15 C 0.48075(8) 0.98636(6) 0.68322(5) 0.01149(19) Uani 1 1 d . . . C16 C 0.60411(9) 0.98767(7) 0.74792(6) 0.0162(2) Uani 1 1 d . . . H16 H 0.6433 0.9989 0.7811 0.019 Uiso 1 1 calc R . . C17 C 0.62587(9) 0.94254(7) 0.70148(6) 0.0167(2) Uani 1 1 d . . . H17 H 0.6826 0.9167 0.6973 0.020 Uiso 1 1 calc R . . C18 C 0.46357(9) 1.06167(6) 0.78435(5) 0.0131(2) Uani 1 1 d . . . C19 C 0.49013(10) 1.03281(7) 0.84820(6) 0.0187(2) Uani 1 1 d . . . H19A H 0.4733 0.9829 0.8508 0.028 Uiso 1 1 calc R . . H19C H 0.4558 1.0592 0.8790 0.028 Uiso 1 1 calc R . . H19B H 0.5579 1.0382 0.8547 0.028 Uiso 1 1 calc R . . C20 C 0.50124(10) 1.13819(7) 0.77641(6) 0.0188(2) Uani 1 1 d . . . H20B H 0.5700 1.1381 0.7795 0.028 Uiso 1 1 calc R . . H20C H 0.4748 1.1683 0.8079 0.028 Uiso 1 1 calc R . . H20A H 0.4825 1.1561 0.7369 0.028 Uiso 1 1 calc R . . C21 C 0.35459(9) 1.05842(7) 0.77867(6) 0.0172(2) Uani 1 1 d . . . H21B H 0.3352 1.0801 0.7407 0.026 Uiso 1 1 calc R . . H21C H 0.3259 1.0838 0.8123 0.026 Uiso 1 1 calc R . . H21A H 0.3341 1.0092 0.7794 0.026 Uiso 1 1 calc R . . C22 C 0.55285(9) 0.89487(7) 0.60383(6) 0.0158(2) Uani 1 1 d . . . C23 C 0.52825(15) 0.81834(8) 0.62317(7) 0.0341(4) Uani 1 1 d . . . H23B H 0.4636 0.8168 0.6383 0.051 Uiso 1 1 calc R . . H23C H 0.5715 0.8032 0.6549 0.051 Uiso 1 1 calc R . . H23A H 0.5342 0.7869 0.5885 0.051 Uiso 1 1 calc R . . C24 C 0.48550(14) 0.92068(10) 0.55394(7) 0.0380(4) Uani 1 1 d . . . H24A H 0.5004 0.8966 0.5162 0.057 Uiso 1 1 calc R . . H24C H 0.4930 0.9715 0.5486 0.057 Uiso 1 1 calc R . . H24B H 0.4205 0.9103 0.5654 0.057 Uiso 1 1 calc R . . C25 C 0.65496(12) 0.89697(11) 0.57866(9) 0.0426(5) Uani 1 1 d . . . H25B H 0.6982 0.8767 0.6083 0.064 Uiso 1 1 calc R . . H25C H 0.6729 0.9458 0.5705 0.064 Uiso 1 1 calc R . . H25A H 0.6581 0.8697 0.5413 0.064 Uiso 1 1 calc R . . C26 C 0.37880(8) 1.07519(6) 0.62784(5) 0.0124(2) Uani 1 1 d . . . C27 C 0.45847(9) 1.12427(6) 0.61923(5) 0.0136(2) Uani 1 1 d . . . C28 C 0.62804(9) 1.13706(7) 0.61457(7) 0.0212(3) Uani 1 1 d . . . H28B H 0.6457 1.1442 0.6572 0.025 Uiso 1 1 calc R . . H28A H 0.6136 1.1835 0.5967 0.025 Uiso 1 1 calc R . . C29 C 0.70923(10) 1.10243(8) 0.58053(6) 0.0215(3) Uani 1 1 d . . . H29A H 0.6907 1.0946 0.5386 0.032 Uiso 1 1 calc R . . H29B H 0.7245 1.0573 0.5993 0.032 Uiso 1 1 calc R . . H29C H 0.7644 1.1332 0.5818 0.032 Uiso 1 1 calc R . . C30 C 0.28282(9) 1.10828(6) 0.62490(5) 0.0133(2) Uani 1 1 d . . . C31 C 0.18191(10) 1.19298(8) 0.57583(6) 0.0210(3) Uani 1 1 d . . . H31B H 0.1728 1.2219 0.6124 0.025 Uiso 1 1 calc R . . H31A H 0.1297 1.1587 0.5731 0.025 Uiso 1 1 calc R . . C32 C 0.18400(12) 1.24004(9) 0.51958(7) 0.0315(3) Uani 1 1 d . . . H32A H 0.1918 1.2107 0.4837 0.047 Uiso 1 1 calc R . . H32C H 0.2366 1.2731 0.5225 0.047 Uiso 1 1 calc R . . H32B H 0.1249 1.2663 0.5167 0.047 Uiso 1 1 calc R . . 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 F1 0.0271(5) 0.0246(4) 0.0539(6) 0.0252(4) -0.0114(4) -0.0096(4) F2 0.0296(5) 0.0339(5) 0.0371(5) 0.0022(4) -0.0213(4) -0.0072(4) O1 0.0188(4) 0.0121(4) 0.0350(5) 0.0034(4) 0.0005(4) -0.0002(3) O2 0.0114(4) 0.0142(4) 0.0193(4) -0.0010(3) 0.0023(3) -0.0018(3) O3 0.0128(4) 0.0187(4) 0.0187(4) 0.0023(3) 0.0017(3) 0.0009(3) O4 0.0142(4) 0.0188(4) 0.0191(4) 0.0062(3) -0.0003(3) 0.0044(3) N1 0.0105(4) 0.0122(4) 0.0127(4) -0.0010(3) -0.0008(3) 0.0004(3) N2 0.0125(4) 0.0120(4) 0.0136(4) -0.0007(3) 0.0005(3) 0.0014(3) C1 0.0126(5) 0.0117(5) 0.0127(5) -0.0002(4) -0.0010(4) 0.0001(4) C2 0.0123(5) 0.0107(5) 0.0166(5) -0.0004(4) -0.0008(4) 0.0006(4) C3 0.0138(5) 0.0149(5) 0.0198(5) 0.0028(4) -0.0024(4) -0.0009(4) C4 0.0171(6) 0.0170(6) 0.0260(6) 0.0075(5) -0.0039(5) -0.0004(5) C5 0.0183(6) 0.0140(5) 0.0331(7) 0.0100(5) -0.0024(5) -0.0024(5) C6 0.0161(6) 0.0132(5) 0.0315(7) 0.0031(5) -0.0032(5) -0.0028(4) C7 0.0140(5) 0.0109(5) 0.0202(5) -0.0004(4) -0.0014(4) 0.0000(4) C8 0.0134(5) 0.0123(5) 0.0188(5) -0.0018(4) -0.0025(4) 0.0003(4) C9 0.0169(6) 0.0160(5) 0.0271(6) -0.0023(5) -0.0052(5) -0.0023(5) C10 0.0174(6) 0.0221(6) 0.0236(6) -0.0049(5) -0.0086(5) -0.0007(5) C11 0.0199(6) 0.0211(6) 0.0165(5) -0.0019(5) -0.0047(5) 0.0025(5) C12 0.0161(5) 0.0173(5) 0.0142(5) -0.0008(4) -0.0012(4) -0.0003(4) C13 0.0134(5) 0.0132(5) 0.0148(5) -0.0014(4) -0.0011(4) 0.0004(4) C14 0.0115(5) 0.0125(5) 0.0112(4) -0.0009(4) -0.0002(4) 0.0008(4) C15 0.0123(5) 0.0101(5) 0.0121(4) 0.0011(4) 0.0004(4) -0.0016(4) C16 0.0115(5) 0.0200(5) 0.0172(5) -0.0018(5) -0.0029(4) 0.0024(4) C17 0.0126(5) 0.0184(6) 0.0193(5) -0.0015(4) -0.0012(4) 0.0035(4) C18 0.0128(5) 0.0140(5) 0.0124(5) -0.0030(4) 0.0002(4) 0.0016(4) C19 0.0185(6) 0.0239(6) 0.0138(5) 0.0008(5) -0.0009(4) 0.0025(5) C20 0.0215(6) 0.0139(5) 0.0209(6) -0.0033(4) 0.0008(5) -0.0002(5) C21 0.0125(5) 0.0230(6) 0.0161(5) -0.0040(5) 0.0008(4) 0.0023(5) C22 0.0177(5) 0.0141(5) 0.0157(5) -0.0040(4) 0.0017(4) 0.0010(4) C23 0.0609(12) 0.0158(6) 0.0256(7) -0.0057(5) 0.0014(7) -0.0057(7) C24 0.0528(11) 0.0456(10) 0.0154(6) -0.0110(6) -0.0075(6) 0.0280(8) C25 0.0261(8) 0.0601(12) 0.0418(9) -0.0308(9) 0.0159(7) -0.0106(8) C26 0.0115(5) 0.0125(5) 0.0132(5) 0.0005(4) 0.0002(4) 0.0010(4) C27 0.0133(5) 0.0138(5) 0.0137(5) 0.0016(4) 0.0008(4) 0.0002(4) C28 0.0147(5) 0.0211(6) 0.0278(6) -0.0036(5) 0.0040(5) -0.0054(5) C29 0.0152(6) 0.0274(7) 0.0219(6) -0.0007(5) 0.0019(5) 0.0000(5) C30 0.0133(5) 0.0120(5) 0.0145(5) 0.0001(4) -0.0011(4) 0.0005(4) C31 0.0182(6) 0.0226(6) 0.0221(6) 0.0027(5) -0.0019(5) 0.0079(5) C32 0.0307(8) 0.0326(8) 0.0310(7) 0.0116(6) -0.0019(6) 0.0131(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 F1 C5 1.3664(15) . y F2 C10 1.3752(15) . y O1 C27 1.2263(15) . y O2 C27 1.3680(15) . y O2 C28 1.4516(15) . y O3 C30 1.2214(15) . y O4 C30 1.3533(14) . y O4 C31 1.4513(16) . y N1 C15 1.3596(15) . y N1 C16 1.3816(15) . y N1 C18 1.5237(15) . y N2 C15 1.3574(15) . y N2 C17 1.3818(16) . y N2 C22 1.5235(15) . y C1 C2 1.4716(16) . y C1 C13 1.4717(16) . y C1 C14 1.3922(16) . y C2 C3 1.4049(17) . y C2 C7 1.4234(17) . y C3 C4 1.3968(17) . y C4 C5 1.3885(19) . y C5 C6 1.3801(19) . y C6 C7 1.3948(17) . y C7 C8 1.4562(17) . y C8 C9 1.3964(17) . y C8 C13 1.4207(17) . y C9 C10 1.3781(19) . y C10 C11 1.385(2) . y C11 C12 1.3921(18) . y C12 C13 1.4031(17) . y C14 C15 1.4923(16) . y C14 C26 1.4276(16) . y C16 C17 1.3505(17) . y C18 C19 1.5372(17) . y C18 C20 1.5292(17) . y C18 C21 1.5248(17) . y C22 C23 1.5259(19) . y C22 C24 1.515(2) . y C22 C25 1.525(2) . y C26 C27 1.4505(16) . y C26 C30 1.4742(16) . y C28 C29 1.4990(19) . y C31 C32 1.508(2) . y 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 F1 C5 C4 117.87(12) . . y F1 C5 C6 118.43(12) . . y F2 C10 C9 118.22(12) . . y F2 C10 C11 118.00(12) . . y O1 C27 O2 120.66(11) . . y O1 C27 C26 125.70(11) . . y O2 C27 C26 113.61(10) . . y O2 C28 C29 108.56(11) . . y O3 C30 O4 121.25(11) . . y O3 C30 C26 125.49(11) . . y O4 C30 C26 113.25(10) . . y O4 C31 C32 106.94(11) . . y N1 C15 C14 125.94(10) . . y N1 C18 C19 107.43(9) . . y N1 C18 C20 108.10(10) . . y N1 C18 C21 111.87(9) . . y N2 C15 N1 107.85(10) . . y N2 C15 C14 126.16(10) . . y N2 C22 C23 107.38(10) . . y N2 C22 C25 108.11(11) . . y C1 C14 C15 116.25(10) . . y C1 C14 C26 126.50(11) . . y C2 C1 C13 105.76(10) . . y C2 C7 C8 108.41(10) . . y C3 C2 C1 133.07(11) . . y C3 C2 C7 118.13(11) . . y C4 C3 C2 120.09(11) . . y C5 C4 C3 119.06(12) . . y C5 C6 C7 116.62(12) . . y C6 C5 C4 123.69(12) . . y C6 C7 C2 122.39(11) . . y C6 C7 C8 129.16(11) . . y C7 C2 C1 108.69(10) . . y C8 C13 C1 109.03(10) . . y C9 C8 C7 129.64(12) . . y C9 C8 C13 122.28(11) . . y C9 C10 C11 123.78(12) . . y C10 C9 C8 116.40(12) . . y C10 C11 C12 119.33(12) . . y C11 C12 C13 119.80(12) . . y C12 C13 C1 132.37(11) . . y C12 C13 C8 118.37(11) . . y C13 C8 C7 108.06(10) . . y C14 C1 C2 126.87(10) . . y C14 C1 C13 127.36(10) . . y C14 C26 C27 124.04(10) . . y C14 C26 C30 119.00(10) . . y C15 N1 C16 108.42(10) . . y C15 N1 C18 130.94(10) . . y C15 N2 C17 108.06(10) . . y C15 N2 C22 131.63(10) . . y C16 N1 C18 120.49(10) . . y C16 C17 N2 108.16(11) . . y C17 N2 C22 120.31(10) . . y C17 C16 N1 107.47(11) . . y C20 C18 C19 110.24(10) . . y C21 C18 C19 107.42(10) . . y C21 C18 C20 111.70(10) . . y C24 C22 N2 112.84(10) . . y C24 C22 C23 110.85(14) . . y C24 C22 C25 108.15(14) . . y C25 C22 C23 109.45(14) . . y C26 C14 C15 117.23(10) . . y C27 O2 C28 114.90(9) . . y C27 C26 C30 115.16(10) . . y C30 O4 C31 115.22(10) . . y data_7053_5 _database_code_depnum_ccdc_archive 'CCDC 864421' _audit_creation_date 2012-01-18 _audit_block_code HOS-HG-041-01 _chemical_name_systematic ; 1,1-di(trifluoromethyl)-2-(9H-fluoren-9-ylidene)-ethene ; _chemical_melting_point 100 _chemical_formula_moiety 'C17 H8 F6' _chemical_formula_sum 'C17 H8 F6' _chemical_formula_weight 326.23 _chemical_compound_source hexane,dichloromethane loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'p n a 21' _symmetry_space_group_name_Hall 'p 2c -2n' _symmetry_Int_Tables_number 33 loop_ _symmetry_equiv_pos_as_xyz '-x+1/2, y+1/2, z+1/2' 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, z' _cell_length_a 7.266(2) _cell_length_b 20.145(6) _cell_length_c 9.725(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_volume 1423.4(7) _cell_measurement_reflns_used 9684 _cell_measurement_temperature 100 _cell_measurement_theta_max 25.6210 _cell_measurement_theta_min 2.3256 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 -1.00 0.00 0.0130 0.00 1.00 0.00 0.0130 0.00 0.00 -1.00 0.0130 0.00 0.00 1.00 0.0130 1.00 0.00 0.00 0.0450 -1.00 0.00 0.00 0.0450 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.09 _exptl_crystal_size_mid 0.026 _exptl_crystal_size_min 0.026 _exptl_crystal_density_diffrn 1.522 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.143 _exptl_absorpt_correction_T_max 0.99663 _exptl_absorpt_correction_T_min 0.98912 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 100 _diffrn_detector_area_resol_mean 66.67 _diffrn_measurement_device_type 'Bruker-AXS Kappa Mach3 APEX-II' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_radiation_monochromator 'Incoatec Helios mirrors' _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_type Mo-K\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0786 _diffrn_reflns_av_sigmaI/netI 0.0385 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 25958 _diffrn_reflns_theta_max 26.44 _diffrn_reflns_theta_min 2.33 _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_number 0 _reflns_number_gt 2559 _reflns_number_total 2869 _reflns_threshold_expression >2sigma(I) _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick, 2008)' _computing_structure_solution 'SHELXS-97 (G. M. Sheldrick, 2008)' _computing_cell_refinement 'SAINT software (Bruker AXS, 2004)' _computing_data_collection 'APEX2 (Bruker AXS, 2008)' _computing_data_reduction 'SAINT software (Bruker AXS, 2004)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _computing_publication_material ; OLEX2: a complete structure solution, refinement and analysis program. Dolomanov et al., J. Appl. Cryst. (2009). 42, 339-34 ; _refine_diff_density_max 0.874 _refine_diff_density_min -0.363 _refine_diff_density_rms 0.075 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0643 _refine_ls_abs_structure_Flack 0.4(13) _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2869 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.025 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_wR_factor_gt 0.1737 _refine_ls_wR_factor_ref 0.1819 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1132P)^2^+1.2392P] where P=(Fo^2^+2Fc^2^)/3' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.3400 and 1.0000 (SADABS). Highest peak 0.87 at 0.1795 0.5896 0.0308 [ 1.72 A from H4 ] Deepest hole -0.36 at 0.4874 0.5318 0.0431 [ 0.82 A from F6 ] ; _iucr_refine_instructions_details ; TITL 7053 CELL 0.71073 7.2661 20.1445 9.7246 90 90 90 ZERR 4 0.0022 0.006 0.0029 0 0 0 LATT -1 SYMM -X,-Y,0.5+Z SYMM 0.5-X,0.5+Y,0.5+Z SYMM 0.5+X,0.5-Y,+Z SFAC C H F UNIT 68 32 24 L.S. 100 PLAN 20 SIZE 0.027 0.029 0.091 TEMP -173 BOND $H FMAP 2 ACTA 55 OMIT 0 2 0 WGHT 0.1133 1.2387 FVAR 0.16036 F1 3 0.54921 1.06760 0.29078 11.00000 0.05524 0.04483 0.20768 = -0.04997 0.01626 0.00659 F2 3 0.40280 0.97721 0.29357 11.00000 0.04125 0.05221 0.09825 = -0.00282 0.02116 0.00377 F3 3 0.45076 1.02473 0.10360 11.00000 0.08092 0.17569 0.09179 = 0.05012 0.00810 0.08110 F4 3 0.92518 1.05681 0.24859 11.00000 0.09271 0.10682 0.09995 = -0.05638 0.03267 -0.06976 F5 3 0.82910 1.04711 0.04412 11.00000 0.06947 0.09536 0.09863 = 0.05630 -0.01366 -0.02589 F6 3 1.00950 0.97637 0.12442 11.00000 0.04541 0.04594 0.12864 = 0.02226 0.02554 0.00460 C1 1 0.71434 0.91086 0.22794 11.00000 0.02857 0.03283 0.04809 = 0.00638 0.00114 0.00185 C2 1 0.72935 0.84654 0.25165 11.00000 0.01514 0.02522 0.04067 = 0.00582 0.00361 0.00132 C3 1 0.70260 0.79131 0.15284 11.00000 0.01774 0.03219 0.02915 = 0.00440 0.00323 0.00092 C4 1 0.65585 0.79208 0.01450 11.00000 0.02040 0.05808 0.03382 = 0.01437 -0.00329 -0.00255 AFIX 43 H4 2 0.63758 0.83190 -0.03191 11.00000 -1.20000 AFIX 0 C5 1 0.63735 0.73216 -0.05194 11.00000 0.02737 0.08296 0.02865 = -0.00237 0.00178 -0.00983 AFIX 43 H5 2 0.60592 0.73161 -0.14464 11.00000 -1.20000 AFIX 0 C6 1 0.66460 0.67257 0.01644 11.00000 0.02453 0.06037 0.04238 = -0.02263 0.00508 -0.00567 AFIX 43 H6 2 0.65240 0.63283 -0.03136 11.00000 -1.20000 AFIX 0 C7 1 0.71024 0.67126 0.15648 11.00000 0.02180 0.02972 0.03864 = -0.00629 0.00212 -0.00312 AFIX 43 H7 2 0.72693 0.63126 0.20254 11.00000 -1.20000 AFIX 0 C8 1 0.72968 0.73126 0.22408 11.00000 0.01383 0.02639 0.02656 = -0.00069 0.00345 0.00175 C9 1 0.77700 0.74692 0.36801 11.00000 0.01429 0.02177 0.03115 = -0.00066 0.00269 0.00040 C10 1 0.81762 0.70659 0.47719 11.00000 0.02114 0.02761 0.03135 = 0.00348 0.00103 -0.00138 AFIX 43 H10 2 0.81989 0.66073 0.46650 11.00000 -1.20000 AFIX 0 C11 1 0.85594 0.73549 0.60591 11.00000 0.02524 0.04010 0.03025 = 0.00513 -0.00272 -0.00231 AFIX 43 H11 2 0.88457 0.70857 0.68059 11.00000 -1.20000 AFIX 0 C12 1 0.85122 0.80355 0.62182 11.00000 0.02715 0.04395 0.03050 = -0.00287 0.00053 -0.00279 AFIX 43 H12 2 0.87401 0.82200 0.70781 11.00000 -1.20000 AFIX 0 C13 1 0.81278 0.84498 0.51084 11.00000 0.02483 0.02848 0.04188 = -0.00366 -0.00061 -0.00273 AFIX 43 H13 2 0.81219 0.89087 0.52136 11.00000 -1.20000 AFIX 0 C14 1 0.77561 0.81642 0.38501 11.00000 0.01448 0.02089 0.03471 = -0.00012 0.00074 0.00206 C15 1 0.70553 0.97421 0.20847 11.00000 0.03506 0.02604 0.04973 = -0.00121 0.00439 0.00154 C16 1 0.52506 1.01149 0.22265 11.00000 0.03916 0.03319 0.06944 = 0.00098 0.00562 0.00723 C17 1 0.87153 1.01312 0.15626 11.00000 0.03692 0.02224 0.05964 = 0.00592 -0.00504 0.00157 HKLF 4 END ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom 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 F1 F 0.5492(4) 1.06760(14) 0.2908(6) 0.1026(16) Uani 1 1 d . . . F2 F 0.4028(3) 0.97721(12) 0.2936(4) 0.0639(8) Uani 1 1 d . . . F3 F 0.4508(5) 1.0247(3) 0.1036(4) 0.1161(18) Uani 1 1 d . . . F4 F 0.9252(5) 1.05681(19) 0.2486(4) 0.0998(14) Uani 1 1 d . . . F5 F 0.8291(5) 1.04711(19) 0.0441(4) 0.0878(12) Uani 1 1 d . . . F6 F 1.0095(4) 0.97637(12) 0.1244(4) 0.0733(10) Uani 1 1 d . . . C1 C 0.7143(5) 0.91086(18) 0.2279(5) 0.0365(8) Uani 1 1 d . . . C2 C 0.7294(4) 0.84654(15) 0.2516(3) 0.0270(7) Uani 1 1 d . . . C3 C 0.7026(4) 0.79131(15) 0.1528(3) 0.0264(7) Uani 1 1 d . . . C4 C 0.6559(4) 0.7921(2) 0.0145(4) 0.0374(8) Uani 1 1 d . . . H4 H 0.6376 0.8319 -0.0319 0.045 Uiso 1 1 calc R . . C5 C 0.6374(5) 0.7322(2) -0.0519(4) 0.0463(10) Uani 1 1 d . . . H5 H 0.6059 0.7316 -0.1446 0.056 Uiso 1 1 calc R . . C6 C 0.6646(5) 0.6726(2) 0.0164(4) 0.0424(9) Uani 1 1 d . . . H6 H 0.6524 0.6328 -0.0314 0.051 Uiso 1 1 calc R . . C7 C 0.7102(4) 0.67126(16) 0.1565(4) 0.0301(7) Uani 1 1 d . . . H7 H 0.7269 0.6313 0.2025 0.036 Uiso 1 1 calc R . . C8 C 0.7297(4) 0.73126(14) 0.2241(3) 0.0223(6) Uani 1 1 d . . . C9 C 0.7770(4) 0.74691(14) 0.3680(3) 0.0224(6) Uani 1 1 d . . . C10 C 0.8176(4) 0.70659(16) 0.4772(3) 0.0267(7) Uani 1 1 d . . . H10 H 0.8199 0.6607 0.4665 0.032 Uiso 1 1 calc R . . C11 C 0.8559(4) 0.73549(17) 0.6059(4) 0.0319(7) Uani 1 1 d . . . H11 H 0.8846 0.7086 0.6806 0.038 Uiso 1 1 calc R . . C12 C 0.8512(4) 0.80355(18) 0.6218(4) 0.0339(7) Uani 1 1 d . . . H12 H 0.8740 0.8220 0.7078 0.041 Uiso 1 1 calc R . . C13 C 0.8128(4) 0.84498(16) 0.5108(4) 0.0317(7) Uani 1 1 d . . . H13 H 0.8122 0.8909 0.5214 0.038 Uiso 1 1 calc R . . C14 C 0.7756(4) 0.81642(14) 0.3850(3) 0.0234(6) Uani 1 1 d . . . C15 C 0.7055(5) 0.97421(17) 0.2085(5) 0.0369(8) Uani 1 1 d . . . C16 C 0.5251(6) 1.01149(19) 0.2227(5) 0.0473(10) Uani 1 1 d . . . C17 C 0.8715(5) 1.01312(16) 0.1563(5) 0.0396(8) Uani 1 1 d . . . 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 F1 0.0552(17) 0.0448(15) 0.208(5) -0.050(2) 0.016(2) 0.0066(12) F2 0.0413(13) 0.0522(15) 0.098(2) -0.0028(15) 0.0212(14) 0.0038(11) F3 0.081(2) 0.176(4) 0.092(3) 0.050(3) 0.008(2) 0.081(3) F4 0.093(2) 0.107(3) 0.100(3) -0.056(2) 0.033(2) -0.070(2) F5 0.069(2) 0.095(2) 0.099(3) 0.056(2) -0.0137(18) -0.0259(17) F6 0.0454(13) 0.0459(14) 0.129(3) 0.0223(16) 0.0255(17) 0.0046(11) C1 0.0286(16) 0.0328(16) 0.048(2) 0.0064(16) 0.0011(15) 0.0018(13) C2 0.0151(13) 0.0252(15) 0.041(2) 0.0058(13) 0.0036(12) 0.0013(10) C3 0.0177(13) 0.0322(16) 0.0291(16) 0.0044(14) 0.0032(12) 0.0009(10) C4 0.0204(15) 0.058(2) 0.0338(19) 0.0144(18) -0.0033(14) -0.0026(13) C5 0.0274(17) 0.083(3) 0.0286(18) -0.0024(19) 0.0018(14) -0.0098(18) C6 0.0245(16) 0.060(2) 0.042(2) -0.023(2) 0.0051(16) -0.0057(14) C7 0.0218(13) 0.0297(16) 0.0386(18) -0.0063(14) 0.0021(13) -0.0031(11) C8 0.0138(12) 0.0264(14) 0.0266(15) -0.0007(13) 0.0034(11) 0.0018(10) C9 0.0143(11) 0.0218(13) 0.0311(16) -0.0007(13) 0.0027(11) 0.0004(10) C10 0.0211(14) 0.0276(15) 0.0314(18) 0.0035(12) 0.0010(12) -0.0014(11) C11 0.0252(15) 0.0401(18) 0.0303(18) 0.0051(14) -0.0027(13) -0.0023(13) C12 0.0271(15) 0.0439(19) 0.0305(18) -0.0029(15) 0.0005(13) -0.0028(14) C13 0.0248(14) 0.0285(15) 0.0419(19) -0.0037(15) -0.0006(14) -0.0027(12) C14 0.0145(13) 0.0209(13) 0.0347(17) -0.0001(13) 0.0007(11) 0.0021(10) C15 0.0351(17) 0.0260(15) 0.050(2) -0.0012(15) 0.0044(16) 0.0015(13) C16 0.039(2) 0.033(2) 0.069(3) 0.0010(19) 0.006(2) 0.0072(15) C17 0.0369(17) 0.0222(15) 0.060(2) 0.0059(16) -0.0050(17) 0.0016(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 F1 C16 1.322(5) . y F2 C16 1.320(5) . y F3 C16 1.305(6) . y F4 C17 1.316(5) . y F5 C17 1.324(5) . y F6 C17 1.284(5) . y C1 C2 1.321(5) . y C1 C15 1.292(5) . y C2 C3 1.483(5) . y C2 C14 1.471(5) . y C3 C4 1.388(5) . y C3 C8 1.408(4) . y C4 H4 0.9300 . n C4 C5 1.376(6) . y C5 H5 0.9300 . n C5 C6 1.386(6) . y C6 H6 0.9300 . n C6 C7 1.402(6) . y C7 H7 0.9300 . n C7 C8 1.383(4) . y C8 C9 1.475(5) . y C9 C10 1.369(5) . y C9 C14 1.410(4) . y C10 H10 0.9300 . n C10 C11 1.408(5) . y C11 H11 0.9300 . n C11 C12 1.380(5) . y C12 H12 0.9300 . n C12 C13 1.393(5) . y C13 H13 0.9300 . n C13 C14 1.379(5) . y C15 C16 1.517(5) . y C15 C17 1.525(5) . y 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 F1 C16 C15 110.7(3) . . y F2 C16 F1 106.0(4) . . y F2 C16 C15 111.7(3) . . y F3 C16 F1 109.0(4) . . y F3 C16 F2 107.0(4) . . y F3 C16 C15 112.2(4) . . y F4 C17 F5 106.6(3) . . y F4 C17 C15 110.5(4) . . y F5 C17 C15 110.8(3) . . y F6 C17 F4 108.6(4) . . y F6 C17 F5 106.3(4) . . y F6 C17 C15 113.7(3) . . y C1 C2 C3 127.7(3) . . y C1 C2 C14 125.3(3) . . y C1 C15 C16 121.2(3) . . y C1 C15 C17 121.1(3) . . y C3 C4 H4 121.0 . . y C3 C8 C9 108.4(3) . . y C4 C3 C2 130.7(3) . . y C4 C3 C8 121.4(3) . . y C4 C5 H5 119.3 . . y C4 C5 C6 121.4(4) . . y C5 C4 C3 118.0(4) . . y C5 C4 H4 121.0 . . y C5 C6 H6 119.5 . . y C5 C6 C7 121.1(4) . . y C6 C5 H5 119.3 . . y C6 C7 H7 121.0 . . y C7 C6 H6 119.5 . . y C7 C8 C3 120.2(3) . . y C7 C8 C9 131.4(3) . . y C8 C3 C2 107.9(3) . . y C8 C7 C6 118.0(3) . . y C8 C7 H7 121.0 . . y C9 C10 H10 120.4 . . y C9 C10 C11 119.1(3) . . y C9 C14 C2 107.9(3) . . y C10 C9 C8 131.2(3) . . y C10 C9 C14 120.0(3) . . y C10 C11 H11 119.8 . . y C11 C10 H10 120.4 . . y C11 C12 H12 119.6 . . y C11 C12 C13 120.9(3) . . y C12 C11 C10 120.4(3) . . y C12 C11 H11 119.8 . . y C12 C13 H13 120.8 . . y C13 C12 H12 119.6 . . y C13 C14 C2 130.9(3) . . y C13 C14 C9 121.1(3) . . y C14 C2 C3 107.0(3) . . y C14 C9 C8 108.8(3) . . y C14 C13 C12 118.5(3) . . y C14 C13 H13 120.8 . . y C15 C1 C2 177.5(4) . . y C16 C15 C17 117.3(3) . . y _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.986 _diffrn_reflns_theta_full 26.44 data_7080_39 _database_code_depnum_ccdc_archive 'CCDC 864422' _audit_creation_date 2012-01-18 _audit_block_code HOS-HG-043-03 _chemical_name_systematic ; 1-(3,5-difluoro-9H-fluoren-9-ylidene)-1-(4-(methyl)phenylthio)- 2,2-di(ethoxycarbonyl)-ethane ; _chemical_melting_point ? _chemical_compound_source hexane _chemical_formula_moiety 'C28 H24 F2 O4 S' _chemical_formula_sum 'C28 H24 F2 O4 S' _chemical_formula_weight 494.53 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' F F 0.0171 0.0103 '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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'p -1' _symmetry_space_group_name_Hall '-p 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.9304(17) _cell_length_b 12.5572(16) _cell_length_c 13.327(4) _cell_angle_alpha 98.06(2) _cell_angle_beta 104.24(2) _cell_angle_gamma 105.687(12) _cell_volume 1207.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 200 _cell_measurement_reflns_used 23288 _cell_measurement_theta_min 2.6049 _cell_measurement_theta_max 28.0412 loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 1.00 -1.00 0.0700 0.00 -1.00 1.00 0.1000 0.00 -1.00 -1.00 0.1300 0.00 1.00 1.00 0.1400 1.00 -1.00 -1.00 0.1200 -1.00 1.00 1.00 0.1100 3.00 -1.00 -1.00 0.1300 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_density_method ? _exptl_crystal_F_000 516 _exptl_absorpt_coefficient_mu 0.182 _exptl_absorpt_correction_type gaussian _exptl_absorpt_correction_T_min 0.95082 _exptl_absorpt_correction_T_max 0.97247 _exptl_absorpt_process_details 'SADABS (Bruker AXS, 2008)' _exptl_special_details ; Crystal mounted on a MiTeGen loop using Perfluoropolyether PFO-XR75 ; _diffrn_ambient_temperature 200 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source '0.2 x 2mm^2^ focus rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker AXS Enraf-Nonius KappaCCD' _diffrn_measurement_method 'CCD \f- and \w-scans' _diffrn_detector_area_resol_mean 18.02 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21411 _diffrn_reflns_av_R_equivalents 0.0333 _diffrn_reflns_av_sigmaI/netI 0.0304 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.61 _diffrn_reflns_theta_max 28.16 _reflns_number_total 5879 _reflns_number_gt 4668 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'DATCOL (Bruker AXS, 2006)' _computing_cell_refinement 'DENZO (Bruker AXS, 2006)' _computing_data_reduction 'DENZO (Bruker AXS, 2006)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'DIAMOND (Crystal Impact GbR, 2005)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. The minimum and maximum estimated transmissions from the multi-scan scaling are 0.8356 and 1.0000 (SADABS). The location H22 and H13 were refined using isotropic atomic displacements because of the close proximity of the two atoms, otherwise H atoms were refined using a riding model. Highest peak 0.34 at 0.4678 0.6883 0.5568 [ 0.97 A from O4 ] Deepest hole -0.25 at 0.4631 0.8578 0.4795 [ 0.82 A from O3 ] ; _iucr_refine_instructions_details ; TITL 7080 CELL 0.71073 7.9304 12.5572 13.3269 98.055 104.244 105.687 ZERR 2 0.0017 0.0016 0.0044 0.02 0.022 0.012 LATT 1 SFAC C H F S O UNIT 56 48 4 2 8 L.S. 12 PLAN 20 TEMP -173 BOND $H FMAP 2 ACTA WGHT 0.0536 0.4692 FVAR 0.32603 C1 1 0.29778 0.18024 0.25732 11.00000 0.03006 0.02518 0.03478 = 0.00713 0.00746 0.00950 C2 1 0.30187 0.10241 0.17697 11.00000 0.02874 0.02457 0.03345 = 0.00664 0.00722 0.00735 C3 1 0.25787 0.10388 0.06214 11.00000 0.02762 0.02775 0.03281 = 0.00468 0.00723 0.00413 C4 1 0.20467 0.18079 0.00566 11.00000 0.03965 0.03246 0.03792 = 0.00817 0.00588 0.00773 AFIX 43 H4 2 0.20366 0.25102 0.04242 11.00000 -1.20000 AFIX 0 C5 1 0.15323 0.15431 -0.10446 11.00000 0.04268 0.04229 0.03905 = 0.01417 0.00329 0.00314 AFIX 43 H5 2 0.11648 0.20600 -0.14373 11.00000 -1.20000 AFIX 0 C6 1 0.15612 0.05235 -0.15598 11.00000 0.04067 0.04597 0.03018 = 0.00527 0.00480 -0.00484 C7 1 0.20528 -0.02745 -0.10499 11.00000 0.04085 0.03445 0.03664 = -0.00090 0.01124 -0.00149 AFIX 43 H7 2 0.20523 -0.09735 -0.14304 11.00000 -1.20000 AFIX 0 C8 1 0.25503 -0.00036 0.00519 11.00000 0.02827 0.02784 0.03723 = 0.00382 0.01054 0.00174 C9 1 0.30935 -0.06761 0.08074 11.00000 0.03068 0.02347 0.04157 = 0.00405 0.01398 0.00340 C10 1 0.33728 -0.17240 0.06186 11.00000 0.04651 0.02629 0.05361 = 0.00192 0.02278 0.00763 AFIX 43 H10 2 0.31276 -0.21433 -0.00811 11.00000 -1.20000 AFIX 0 C11 1 0.40193 -0.21198 0.14935 11.00000 0.05439 0.02412 0.07437 = 0.01434 0.03358 0.01746 C12 1 0.44392 -0.15292 0.25240 11.00000 0.05800 0.03848 0.06175 = 0.02441 0.02804 0.02596 AFIX 43 H12 2 0.49236 -0.18313 0.31033 11.00000 -1.20000 AFIX 0 C13 1 0.41434 -0.04829 0.27043 11.00000 0.04819 0.03337 0.04408 = 0.01460 0.01996 0.01943 C14 1 0.34102 -0.00647 0.18397 11.00000 0.03106 0.02355 0.04003 = 0.00633 0.01338 0.00767 C15 1 0.50682 0.37069 0.20896 11.00000 0.03538 0.02428 0.03203 = 0.00354 0.00688 0.00819 C16 1 0.51443 0.45844 0.15581 11.00000 0.04040 0.03370 0.05057 = 0.01569 0.00950 0.01371 AFIX 43 H16 2 0.40980 0.48243 0.13466 11.00000 -1.20000 AFIX 0 C17 1 0.67440 0.51132 0.13344 11.00000 0.04824 0.03822 0.04816 = 0.01797 0.01189 0.00979 AFIX 43 H17 2 0.67850 0.57205 0.09789 11.00000 -1.20000 AFIX 0 C18 1 0.82833 0.47706 0.16207 11.00000 0.04112 0.03993 0.03464 = 0.00343 0.01134 0.00598 C19 1 0.81703 0.38718 0.21307 11.00000 0.03636 0.04076 0.03868 = 0.00464 0.00787 0.01335 AFIX 43 H19 2 0.92012 0.36129 0.23184 11.00000 -1.20000 AFIX 0 C20 1 0.65932 0.33456 0.23715 11.00000 0.03969 0.03129 0.03878 = 0.00925 0.00875 0.01332 AFIX 43 H20 2 0.65531 0.27394 0.27284 11.00000 -1.20000 AFIX 0 C21 1 1.00458 0.53754 0.14119 11.00000 0.04971 0.06798 0.05571 = 0.01410 0.02360 0.00696 AFIX 137 H21c 2 1.08752 0.59268 0.20574 11.00000 -1.50000 H21b 2 0.97737 0.57707 0.08382 11.00000 -1.50000 H21a 2 1.06312 0.48210 0.12047 11.00000 -1.50000 AFIX 0 C22 1 0.28675 0.15571 0.36377 11.00000 0.03137 0.02757 0.03331 = 0.00586 0.00952 0.01031 C23 1 0.12831 0.18213 0.39575 11.00000 0.03204 0.03041 0.03654 = 0.00211 0.00779 0.00747 C24 1 -0.02200 0.16129 0.53027 11.00000 0.05684 0.07977 0.05876 = 0.02396 0.03493 0.03297 AFIX 23 H24b 2 -0.07537 0.09375 0.55636 11.00000 -1.20000 H24a 2 -0.12185 0.17321 0.47635 11.00000 -1.20000 AFIX 0 C25 1 0.06108 0.26183 0.61951 11.00000 0.10303 0.09448 0.06278 = 0.01768 0.04334 0.05842 AFIX 137 H25a 2 0.10018 0.32996 0.59217 11.00000 -1.50000 H25b 2 0.16760 0.25304 0.66924 11.00000 -1.50000 H25c 2 -0.02947 0.26914 0.65628 11.00000 -1.50000 AFIX 0 C26 1 0.46491 0.21754 0.45271 11.00000 0.03352 0.04217 0.03331 = 0.00625 0.00862 0.01156 C27 1 0.63699 0.39282 0.57742 11.00000 0.05139 0.05331 0.05186 = -0.00935 -0.00464 0.00168 AFIX 23 H27a 2 0.69707 0.34531 0.61706 11.00000 -1.20000 H27b 2 0.60628 0.44429 0.62828 11.00000 -1.20000 AFIX 0 C28 1 0.76485 0.46077 0.52781 11.00000 0.05916 0.05975 0.06718 = 0.00295 -0.00323 -0.00669 AFIX 137 H28a 2 0.80568 0.40998 0.48352 11.00000 -1.50000 H28c 2 0.87140 0.51424 0.58349 11.00000 -1.50000 H28b 2 0.70167 0.50286 0.48376 11.00000 -1.50000 AFIX 0 F1 3 0.10691 0.02998 -0.26445 11.00000 0.07525 0.05921 0.03086 = 0.00475 0.00419 -0.00095 F2 3 0.43242 -0.31451 0.13448 11.00000 0.09261 0.03178 0.09876 = 0.02070 0.04877 0.03365 O1 5 0.02872 0.22809 0.35009 11.00000 0.04017 0.04587 0.05825 = 0.01906 0.01803 0.02130 O2 5 0.11696 0.14239 0.48249 11.00000 0.04378 0.06040 0.03924 = 0.01364 0.01870 0.02365 O3 5 0.58286 0.17723 0.48079 11.00000 0.05221 0.07456 0.06503 = -0.00420 -0.00777 0.03590 O4 5 0.46893 0.32026 0.49582 11.00000 0.04379 0.04251 0.05922 = -0.00962 -0.00426 0.00952 S1 4 0.30347 0.31989 0.24586 11.00000 0.03978 0.02557 0.04555 = 0.00874 0.01650 0.01430 H22 2 0.26742 0.07795 0.36288 11.00000 0.03211 H13 2 0.44978 -0.00688 0.34060 11.00000 0.04945 HKLF 4 END ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0536P)^2^+0.4692P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 5879 _refine_ls_number_parameters 327 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0610 _refine_ls_R_factor_gt 0.0452 _refine_ls_wR_factor_ref 0.1207 _refine_ls_wR_factor_gt 0.1106 _refine_ls_goodness_of_fit_ref 1.052 _refine_ls_restrained_S_all 1.052 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 0.2978(2) 0.18024(13) 0.25732(13) 0.0302(3) Uani 1 1 d . . . C2 C 0.3019(2) 0.10241(13) 0.17697(13) 0.0295(3) Uani 1 1 d . . . C3 C 0.2579(2) 0.10388(13) 0.06214(13) 0.0309(3) Uani 1 1 d . . . C4 C 0.2047(2) 0.18079(14) 0.00566(14) 0.0385(4) Uani 1 1 d . . . H4 H 0.2037 0.2510 0.0424 0.046 Uiso 1 1 calc R . . C5 C 0.1532(3) 0.15431(16) -0.10446(15) 0.0446(4) Uani 1 1 d . . . H5 H 0.1165 0.2060 -0.1437 0.054 Uiso 1 1 calc R . . C6 C 0.1561(3) 0.05235(16) -0.15598(14) 0.0442(4) Uani 1 1 d . . . C7 C 0.2053(2) -0.02745(15) -0.10499(14) 0.0411(4) Uani 1 1 d . . . H7 H 0.2052 -0.0973 -0.1430 0.049 Uiso 1 1 calc R . . C8 C 0.2550(2) -0.00036(13) 0.00519(13) 0.0328(3) Uani 1 1 d . . . C9 C 0.3094(2) -0.06761(13) 0.08074(14) 0.0327(3) Uani 1 1 d . . . C10 C 0.3373(3) -0.17240(14) 0.06186(16) 0.0422(4) Uani 1 1 d . . . H10 H 0.3128 -0.2143 -0.0081 0.051 Uiso 1 1 calc R . . C11 C 0.4019(3) -0.21198(14) 0.14935(18) 0.0468(5) Uani 1 1 d . . . C12 C 0.4439(3) -0.15292(16) 0.25240(17) 0.0472(5) Uani 1 1 d . . . H12 H 0.4924 -0.1831 0.3103 0.057 Uiso 1 1 calc R . . C13 C 0.4143(3) -0.04829(15) 0.27043(16) 0.0387(4) Uani 1 1 d . . . C14 C 0.3410(2) -0.00647(13) 0.18397(13) 0.0313(3) Uani 1 1 d . . . C15 C 0.5068(2) 0.37069(13) 0.20896(13) 0.0317(3) Uani 1 1 d . . . C16 C 0.5144(3) 0.45845(15) 0.15581(15) 0.0412(4) Uani 1 1 d . . . H16 H 0.4098 0.4824 0.1347 0.049 Uiso 1 1 calc R . . C17 C 0.6744(3) 0.51132(16) 0.13344(16) 0.0453(4) Uani 1 1 d . . . H17 H 0.6785 0.5721 0.0979 0.054 Uiso 1 1 calc R . . C18 C 0.8283(3) 0.47706(15) 0.16207(14) 0.0405(4) Uani 1 1 d . . . C19 C 0.8170(2) 0.38718(15) 0.21308(14) 0.0394(4) Uani 1 1 d . . . H19 H 0.9201 0.3613 0.2318 0.047 Uiso 1 1 calc R . . C20 C 0.6593(2) 0.33456(14) 0.23715(14) 0.0366(4) Uani 1 1 d . . . H20 H 0.6553 0.2739 0.2728 0.044 Uiso 1 1 calc R . . C21 C 1.0046(3) 0.5375(2) 0.14119(19) 0.0587(6) Uani 1 1 d . . . H21C H 1.0875 0.5927 0.2057 0.088 Uiso 1 1 calc R . . H21B H 0.9774 0.5771 0.0838 0.088 Uiso 1 1 calc R . . H21A H 1.0631 0.4821 0.1205 0.088 Uiso 1 1 calc R . . C22 C 0.2868(2) 0.15571(13) 0.36377(13) 0.0307(3) Uani 1 1 d . . . C23 C 0.1283(2) 0.18213(14) 0.39575(13) 0.0345(3) Uani 1 1 d . . . C24 C -0.0220(3) 0.1613(2) 0.53027(19) 0.0585(6) Uani 1 1 d . . . H24B H -0.0754 0.0938 0.5564 0.070 Uiso 1 1 calc R . . H24A H -0.1219 0.1732 0.4764 0.070 Uiso 1 1 calc R . . C25 C 0.0611(4) 0.2618(3) 0.6195(2) 0.0776(8) Uani 1 1 d . . . H25A H 0.1002 0.3300 0.5922 0.116 Uiso 1 1 calc R . . H25B H 0.1676 0.2530 0.6692 0.116 Uiso 1 1 calc R . . H25C H -0.0295 0.2691 0.6563 0.116 Uiso 1 1 calc R . . C26 C 0.4649(2) 0.21754(15) 0.45271(14) 0.0369(4) Uani 1 1 d . . . C27 C 0.6370(3) 0.39282(19) 0.57742(18) 0.0613(6) Uani 1 1 d . . . H27A H 0.6971 0.3453 0.6171 0.074 Uiso 1 1 calc R . . H27B H 0.6063 0.4443 0.6283 0.074 Uiso 1 1 calc R . . C28 C 0.7648(3) 0.4608(2) 0.5278(2) 0.0727(7) Uani 1 1 d . . . H28A H 0.8057 0.4100 0.4835 0.109 Uiso 1 1 calc R . . H28C H 0.8714 0.5142 0.5835 0.109 Uiso 1 1 calc R . . H28B H 0.7017 0.5029 0.4838 0.109 Uiso 1 1 calc R . . F1 F 0.10691(19) 0.02998(11) -0.26445(9) 0.0625(4) Uani 1 1 d . . . F2 F 0.4324(2) -0.31451(9) 0.13448(12) 0.0670(4) Uani 1 1 d . . . O1 O 0.02872(18) 0.22809(11) 0.35009(11) 0.0451(3) Uani 1 1 d . . . O2 O 0.11696(18) 0.14239(12) 0.48249(10) 0.0449(3) Uani 1 1 d . . . O3 O 0.5829(2) 0.17723(15) 0.48079(13) 0.0675(5) Uani 1 1 d . . . O4 O 0.46893(19) 0.32026(12) 0.49582(12) 0.0553(4) Uani 1 1 d . . . S1 S 0.30347(6) 0.31989(3) 0.24586(4) 0.03534(12) Uani 1 1 d . . . H22 H 0.267(2) 0.0780(16) 0.3629(14) 0.032(5) Uiso 1 1 d . . . H13 H 0.450(3) -0.0069(18) 0.3406(18) 0.049(6) Uiso 1 1 d . . . 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 0.0301(8) 0.0252(7) 0.0348(8) 0.0071(6) 0.0075(6) 0.0095(6) C2 0.0287(7) 0.0246(7) 0.0334(8) 0.0066(6) 0.0072(6) 0.0074(6) C3 0.0276(7) 0.0278(7) 0.0328(8) 0.0047(6) 0.0072(6) 0.0041(6) C4 0.0397(9) 0.0325(8) 0.0379(9) 0.0082(7) 0.0059(7) 0.0077(7) C5 0.0427(10) 0.0423(10) 0.0390(10) 0.0142(8) 0.0033(8) 0.0031(8) C6 0.0407(10) 0.0460(10) 0.0302(8) 0.0053(7) 0.0048(7) -0.0048(8) C7 0.0408(9) 0.0345(8) 0.0366(9) -0.0009(7) 0.0112(7) -0.0015(7) C8 0.0283(8) 0.0278(7) 0.0372(8) 0.0038(6) 0.0105(6) 0.0017(6) C9 0.0307(8) 0.0235(7) 0.0416(9) 0.0041(6) 0.0140(7) 0.0034(6) C10 0.0465(10) 0.0263(8) 0.0536(11) 0.0019(7) 0.0228(9) 0.0076(7) C11 0.0544(11) 0.0241(8) 0.0744(14) 0.0143(8) 0.0336(10) 0.0175(8) C12 0.0580(12) 0.0385(9) 0.0617(12) 0.0244(9) 0.0280(10) 0.0260(9) C13 0.0482(10) 0.0334(8) 0.0441(10) 0.0146(8) 0.0200(8) 0.0194(7) C14 0.0311(8) 0.0235(7) 0.0400(9) 0.0063(6) 0.0134(6) 0.0077(6) C15 0.0354(8) 0.0243(7) 0.0320(8) 0.0035(6) 0.0069(6) 0.0082(6) C16 0.0404(9) 0.0337(8) 0.0506(10) 0.0157(8) 0.0095(8) 0.0137(7) C17 0.0482(11) 0.0382(9) 0.0482(11) 0.0180(8) 0.0119(8) 0.0098(8) C18 0.0411(9) 0.0399(9) 0.0346(9) 0.0034(7) 0.0113(7) 0.0060(7) C19 0.0364(9) 0.0408(9) 0.0387(9) 0.0046(7) 0.0079(7) 0.0134(7) C20 0.0397(9) 0.0313(8) 0.0388(9) 0.0093(7) 0.0088(7) 0.0133(7) C21 0.0497(12) 0.0680(14) 0.0557(13) 0.0141(11) 0.0236(10) 0.0070(10) C22 0.0314(8) 0.0276(7) 0.0333(8) 0.0059(6) 0.0095(6) 0.0103(6) C23 0.0320(8) 0.0304(8) 0.0365(9) 0.0021(6) 0.0078(7) 0.0075(6) C24 0.0568(13) 0.0798(16) 0.0588(13) 0.0240(12) 0.0349(11) 0.0330(12) C25 0.103(2) 0.094(2) 0.0628(15) 0.0177(14) 0.0433(15) 0.0584(18) C26 0.0335(8) 0.0422(9) 0.0333(8) 0.0062(7) 0.0086(7) 0.0116(7) C27 0.0514(12) 0.0533(12) 0.0519(12) -0.0093(10) -0.0046(10) 0.0017(10) C28 0.0592(14) 0.0597(14) 0.0672(15) 0.0030(12) -0.0032(12) -0.0067(11) F1 0.0752(9) 0.0592(7) 0.0309(6) 0.0047(5) 0.0042(5) -0.0010(6) F2 0.0926(10) 0.0318(6) 0.0988(11) 0.0207(6) 0.0488(9) 0.0337(6) O1 0.0402(7) 0.0459(7) 0.0582(8) 0.0191(6) 0.0180(6) 0.0213(6) O2 0.0438(7) 0.0604(8) 0.0392(7) 0.0136(6) 0.0187(6) 0.0237(6) O3 0.0522(9) 0.0746(11) 0.0650(10) -0.0042(8) -0.0078(7) 0.0359(8) O4 0.0438(8) 0.0425(7) 0.0592(9) -0.0096(6) -0.0043(6) 0.0095(6) S1 0.0398(2) 0.02557(19) 0.0456(2) 0.00874(16) 0.01650(18) 0.01430(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C2 1.358(2) . y C1 C22 1.511(2) . y C1 S1 1.7708(16) . y C2 C3 1.488(2) . y C2 C14 1.492(2) . y C3 C4 1.395(2) . y C3 C8 1.410(2) . y C4 C5 1.388(3) . y C4 H4 0.9500 . n C5 C6 1.374(3) . y C5 H5 0.9500 . n C6 F1 1.368(2) . y C6 C7 1.375(3) . y C7 C8 1.389(2) . y C7 H7 0.9500 . n C8 C9 1.461(2) . y C9 C10 1.391(2) . y C9 C14 1.405(2) . y C10 C11 1.369(3) . y C10 H10 0.9500 . n C11 F2 1.3696(19) . y C11 C12 1.379(3) . y C12 C13 1.395(2) . y C12 H12 0.9500 . n C13 C14 1.395(2) . y C13 H13 0.94(2) . y C15 C16 1.387(2) . y C15 C20 1.389(2) . y C15 S1 1.7808(18) . y C16 C17 1.387(3) . y C16 H16 0.9500 . n C17 C18 1.386(3) . y C17 H17 0.9500 . n C18 C19 1.391(3) . y C18 C21 1.511(3) . y C19 C20 1.383(3) . y C19 H19 0.9500 . n C20 H20 0.9500 . n C21 H21C 0.9800 . n C21 H21B 0.9800 . n C21 H21A 0.9800 . n C22 C23 1.523(2) . y C22 C26 1.526(2) . y C22 H22 0.944(18) . y C23 O1 1.198(2) . y C23 O2 1.335(2) . y C24 O2 1.456(2) . y C24 C25 1.479(4) . y C24 H24B 0.9900 . n C24 H24A 0.9900 . n C25 H25A 0.9800 . n C25 H25B 0.9800 . n C25 H25C 0.9800 . n C26 O3 1.187(2) . y C26 O4 1.325(2) . y C27 O4 1.463(2) . y C27 C28 1.488(4) . y C27 H27A 0.9900 . n C27 H27B 0.9900 . n C28 H28A 0.9800 . n C28 H28C 0.9800 . n C28 H28B 0.9800 . n 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 C2 C1 C22 123.33(14) . . y C2 C1 S1 122.65(13) . . y C22 C1 S1 114.03(11) . . y C1 C2 C3 127.53(14) . . y C1 C2 C14 127.36(15) . . y C3 C2 C14 105.03(13) . . y C4 C3 C8 118.73(15) . . y C4 C3 C2 132.28(15) . . y C8 C3 C2 108.61(14) . . y C5 C4 C3 119.73(17) . . y C5 C4 H4 120.1 . . n C3 C4 H4 120.1 . . n C6 C5 C4 119.14(18) . . y C6 C5 H5 120.4 . . n C4 C5 H5 120.4 . . n F1 C6 C5 117.42(18) . . y F1 C6 C7 118.66(18) . . y C5 C6 C7 123.92(17) . . y C6 C7 C8 116.39(17) . . y C6 C7 H7 121.8 . . n C8 C7 H7 121.8 . . n C7 C8 C3 122.06(16) . . y C7 C8 C9 129.25(16) . . y C3 C8 C9 108.69(14) . . y C10 C9 C14 121.99(16) . . y C10 C9 C8 129.21(16) . . y C14 C9 C8 108.73(14) . . y C11 C10 C9 116.57(17) . . y C11 C10 H10 121.7 . . n C9 C10 H10 121.7 . . n C10 C11 F2 118.54(18) . . y C10 C11 C12 123.80(16) . . y F2 C11 C12 117.63(18) . . y C11 C12 C13 119.14(18) . . y C11 C12 H12 120.4 . . n C13 C12 H12 120.4 . . n C12 C13 C14 119.28(18) . . y C12 C13 H13 118.4(13) . . y C14 C13 H13 122.2(13) . . y C13 C14 C9 119.06(15) . . y C13 C14 C2 131.95(15) . . y C9 C14 C2 108.70(14) . . y C16 C15 C20 119.33(16) . . y C16 C15 S1 116.07(13) . . y C20 C15 S1 124.39(13) . . y C15 C16 C17 120.21(17) . . y C15 C16 H16 119.9 . . n C17 C16 H16 119.9 . . n C18 C17 C16 121.14(17) . . y C18 C17 H17 119.4 . . n C16 C17 H17 119.4 . . n C17 C18 C19 117.93(17) . . y C17 C18 C21 121.04(18) . . y C19 C18 C21 121.01(18) . . y C20 C19 C18 121.60(17) . . y C20 C19 H19 119.2 . . n C18 C19 H19 119.2 . . n C19 C20 C15 119.77(16) . . y C19 C20 H20 120.1 . . n C15 C20 H20 120.1 . . n C18 C21 H21C 109.5 . . n C18 C21 H21B 109.5 . . n H21C C21 H21B 109.5 . . n C18 C21 H21A 109.5 . . n H21C C21 H21A 109.5 . . n H21B C21 H21A 109.5 . . n C1 C22 C23 113.44(14) . . y C1 C22 C26 112.54(14) . . y C23 C22 C26 109.05(13) . . y C1 C22 H22 110.9(11) . . y C23 C22 H22 105.4(11) . . y C26 C22 H22 104.9(11) . . y O1 C23 O2 125.90(16) . . y O1 C23 C22 126.29(16) . . y O2 C23 C22 107.80(14) . . y O2 C24 C25 109.9(2) . . y O2 C24 H24B 109.7 . . n C25 C24 H24B 109.7 . . n O2 C24 H24A 109.7 . . n C25 C24 H24A 109.7 . . n H24B C24 H24A 108.2 . . n C24 C25 H25A 109.5 . . n C24 C25 H25B 109.5 . . n H25A C25 H25B 109.5 . . n C24 C25 H25C 109.5 . . n H25A C25 H25C 109.5 . . n H25B C25 H25C 109.5 . . n O3 C26 O4 124.56(17) . . y O3 C26 C22 123.88(17) . . y O4 C26 C22 111.54(14) . . y O4 C27 C28 110.22(19) . . y O4 C27 H27A 109.6 . . n C28 C27 H27A 109.6 . . n O4 C27 H27B 109.6 . . n C28 C27 H27B 109.6 . . n H27A C27 H27B 108.1 . . n C27 C28 H28A 109.5 . . n C27 C28 H28C 109.5 . . n H28A C28 H28C 109.5 . . n C27 C28 H28B 109.5 . . n H28A C28 H28B 109.5 . . n H28C C28 H28B 109.5 . . n C23 O2 C24 117.83(15) . . y C26 O4 C27 117.75(16) . . y C1 S1 C15 102.72(8) . . y _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 28.16 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.339 _refine_diff_density_min -0.252 _refine_diff_density_rms 0.044 #===END