# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_Cambridge 1475 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name _publ_author_address E.E.Maciver ; Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA. UK. ; P.C.Knipe ; Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA. UK. ; A.Cridland ; GlaxoSmithKline, New Frontiers Science Park, Third Avenue, Harlow, CM19 5AW. UK. ; A.L.Thompson ; Chemical Crystallography Department, Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA. UK. ; M.D.Smith ; Chemistry Research Laboratory, University of Oxford, 12 Mansfield Road, Oxford OX1 3TA. UK. ; _publ_contact_author_name 'Dr Martin Smith' _publ_contact_author_email martin.smith@chem.ox.ac.uk _publ_section_title ; Catalytic Enantioselective Electrocyclic Cascades ; _publ_section_abstract ; A catalytic enantioselective electrocyclic cascade leads to the construction of topologically complex systems comprising multiple rings with up to three stereocentres. This phase-transfer catalysed process offers a new strategy for the rapid and enantioselective generation of complex products bearing all-carbon quaternary stereogenic centres. ; # Attachment '- CrystallographicData.cif' #============================================================================== data_14 _database_code_depnum_ccdc_archive 'CCDC 845080' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 10-03-15 _audit_creation_method CRYSTALS_ver_14.06 _oxford_structure_analysis_title 6216 _chemical_name_systematic . _chemical_melting_point . _refine_special_details ; The crystal quality was sub-optimal giving weak, noisy data. Despite this, it seems there is little doubt that the connectivity and relative stereochemistry are correct. The largest peak in the difference map is associated with the disordered CF3 group. ; _cell_length_a 8.6711(3) _cell_length_b 9.4306(4) _cell_length_c 29.5986(13) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2420.39(17) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C26 H25 F3 N2 O4 # Dc = 1.33 Fooo = 1016.00 Mu = 1.05 M = 486.49 # Found Formula = C26 H25 F3.00 N2 O4 # Dc = 1.33 FOOO = 1016.00 Mu = 1.05 M = 486.49 _chemical_formula_sum 'C26 H25 F3 N2 O4' _chemical_formula_moiety 'C26 H25 F3 N2 O4' _chemical_compound_source . _chemical_formula_weight 486.49 _cell_measurement_reflns_used 2188 _cell_measurement_theta_min 5 _cell_measurement_theta_max 26 _cell_measurement_temperature 150 _exptl_crystal_description lath _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.03 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_max 0.34 _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 0.105 # Sheldrick geometric approximatio 0.99 1.00 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 10506 _reflns_number_total 2566 _diffrn_reflns_av_R_equivalents 0.047 # Number of reflections without Friedels Law is 3987 # Number of reflections with Friedels Law is 2566 # Theoretical number of reflections is about 1830 _diffrn_reflns_theta_min 5.111 _diffrn_reflns_theta_max 26.023 _diffrn_measured_fraction_theta_max 0.936 _diffrn_reflns_theta_full 25.000 _diffrn_measured_fraction_theta_full 0.941 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 36 _reflns_limit_h_min 0 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 36 _oxford_diffrn_Wilson_B_factor 2.43 _oxford_diffrn_Wilson_scale 6.01 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.73 _refine_diff_density_max 1.06 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 2015 _refine_ls_number_restraints 306 _refine_ls_number_parameters 381 _oxford_refine_ls_R_factor_ref 0.1086 _refine_ls_wR_factor_ref 0.2218 _refine_ls_goodness_of_fit_ref 0.9893 _refine_ls_shift/su_max 0.0040432 _refine_ls_shift/su_mean 0.0002158 # The values computed from all data _oxford_reflns_number_all 2016 _refine_ls_R_factor_all 0.1087 _refine_ls_wR_factor_all 0.2219 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1567 _refine_ls_R_factor_gt 0.0835 _refine_ls_wR_factor_gt 0.1962 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration unk _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 31.7 43.6 21.7 4.93 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens C4 C -0.2230(8) 0.0142(6) 0.3103(2) 0.0641 1.0000 Uani D . . . . . C5 C -0.1282(11) 0.1294(8) 0.3282(3) 0.0348 1.0000 Uani . . . . . . C6 C -0.1418(10) 0.1698(9) 0.3729(3) 0.0350 1.0000 Uani . . . . . . C7 C -0.0519(10) 0.2859(8) 0.3871(3) 0.0296 1.0000 Uani . . . . . . N8 N -0.0463(8) 0.3427(7) 0.4310(2) 0.0294 1.0000 Uani . . . . . . C9 C -0.1955(10) 0.3621(9) 0.4547(3) 0.0294 1.0000 Uani . . . . . . C10 C -0.1892(10) 0.2976(9) 0.5024(3) 0.0326 1.0000 Uani . . . . . . C11 C -0.0606(10) 0.3534(8) 0.5282(3) 0.0285 1.0000 Uani . . . . . . N12 N 0.0452(10) 0.3975(8) 0.5468(3) 0.0393 1.0000 Uani . . . . . . C13 C -0.2171(10) 0.5195(9) 0.4548(3) 0.0301 1.0000 Uani . . . . . . C14 C -0.3479(12) 0.5971(10) 0.4691(3) 0.0424 1.0000 Uani . . . . . . C15 C -0.3403(12) 0.7452(11) 0.4662(3) 0.0473 1.0000 Uani . . . . . . C16 C -0.2104(12) 0.8117(10) 0.4519(3) 0.0468 1.0000 Uani . . . . . . C17 C -0.0815(11) 0.7383(9) 0.4382(3) 0.0363 1.0000 Uani . . . . . . C18 C -0.0855(10) 0.5893(9) 0.4390(3) 0.0311 1.0000 Uani . . . . . . C19 C 0.0396(10) 0.4818(9) 0.4287(3) 0.0317 1.0000 Uani . . . . . . C20 C 0.1194(9) 0.4815(8) 0.3815(3) 0.0269 1.0000 Uani . . . . . . C21 C 0.0429(10) 0.3574(8) 0.3570(3) 0.0288 1.0000 Uani . . . . . . C22 C 0.0563(10) 0.3147(9) 0.3131(3) 0.0321 1.0000 Uani . . . . . . C23 C -0.0292(11) 0.1979(9) 0.2978(3) 0.0380 1.0000 Uani . . . . . . C24 C 0.1002(9) 0.6212(9) 0.3556(3) 0.0271 1.0000 Uani . . . . . . O25 O 0.0093(7) 0.6392(6) 0.3255(2) 0.0354 1.0000 Uani . . . . . . O26 O 0.1988(7) 0.7179(6) 0.37145(19) 0.0344 1.0000 Uani . . . . . . C27 C 0.1875(11) 0.8631(8) 0.3528(3) 0.0374 1.0000 Uani . . . . . . C28 C 0.2663(14) 0.8656(12) 0.3075(3) 0.0571 1.0000 Uani . . . . . . C29 C 0.2639(14) 0.9571(11) 0.3867(4) 0.0612 1.0000 Uani . . . . . . C30 C 0.2938(7) 0.4503(10) 0.3858(2) 0.0385 1.0000 Uani D . . . . . O31 O 0.3584(7) 0.4215(7) 0.4204(2) 0.0420 1.0000 Uani . . . . . . F10 F -0.1482(15) -0.0714(13) 0.2815(4) 0.0660 0.424(10) Uani D . P 1 1 . F20 F -0.2616(18) -0.0733(12) 0.3449(3) 0.0646 0.424(10) Uani D . P 1 1 . F30 F -0.3578(12) 0.0386(14) 0.2897(5) 0.0757 0.424(10) Uani D . P 1 1 . F11 F -0.1530(12) -0.1108(9) 0.3039(4) 0.0702 0.576(10) Uani D . P 1 2 . F21 F -0.3490(12) -0.0196(12) 0.3343(3) 0.0743 0.576(10) Uani D . P 1 2 . F31 F -0.2801(13) 0.0464(10) 0.2689(3) 0.0601 0.576(10) Uani D . P 1 2 . O320 O 0.3578(7) 0.4609(18) 0.3455(2) 0.0415 0.73(3) Uani D . P 2 1 . C330 C 0.5254(8) 0.4367(12) 0.3410(3) 0.0483 0.73(3) Uani D . P 2 1 . C340 C 0.6006(14) 0.5794(14) 0.3463(6) 0.0510 0.73(3) Uani D . P 2 1 . C350 C 0.5480(13) 0.3670(17) 0.2962(5) 0.0508 0.73(3) Uani D . P 2 1 . O321 O 0.3622(12) 0.463(5) 0.3461(3) 0.0399 0.27(3) Uani D . P 2 2 . C331 C 0.5322(13) 0.451(3) 0.3435(5) 0.0421 0.27(3) Uani D . P 2 2 . C341 C 0.589(4) 0.591(3) 0.3261(14) 0.0434 0.27(3) Uani D . P 2 2 . C351 C 0.565(4) 0.326(3) 0.3138(13) 0.0428 0.27(3) Uani D . P 2 2 . H61 H -0.2054 0.1227 0.3929 0.0439 1.0000 Uiso R . . . . . H91 H -0.2758 0.3148 0.4374 0.0360 1.0000 Uiso R . . . . . H102 H -0.2836 0.3208 0.5179 0.0405 1.0000 Uiso R . . . . . H101 H -0.1811 0.1959 0.5003 0.0404 1.0000 Uiso R . . . . . H141 H -0.4335 0.5506 0.4807 0.0513 1.0000 Uiso R . . . . . H151 H -0.4267 0.7993 0.4742 0.0656 1.0000 Uiso R . . . . . H161 H -0.2082 0.9102 0.4514 0.0617 1.0000 Uiso R . . . . . H171 H 0.0037 0.7862 0.4286 0.0478 1.0000 Uiso R . . . . . H191 H 0.1223 0.4834 0.4521 0.0384 1.0000 Uiso R . . . . . H221 H 0.1220 0.3612 0.2933 0.0428 1.0000 Uiso R . . . . . H231 H -0.0179 0.1647 0.2682 0.0470 1.0000 Uiso R . . . . . H271 H 0.0780 0.8887 0.3494 0.0496 1.0000 Uiso R . . . . . H283 H 0.2372 0.9494 0.2912 0.0927 1.0000 Uiso R . . . . . H281 H 0.3755 0.8669 0.3123 0.0927 1.0000 Uiso R . . . . . H282 H 0.2398 0.7838 0.2903 0.0932 1.0000 Uiso R . . . . . H291 H 0.2503 1.0541 0.3769 0.0950 1.0000 Uiso R . . . . . H293 H 0.2151 0.9436 0.4158 0.0950 1.0000 Uiso R . . . . . H292 H 0.3708 0.9340 0.3889 0.0951 1.0000 Uiso R . . . . . H3301 H 0.5581 0.3676 0.3639 0.0556 0.73(3) Uiso R . P 2 1 . H3401 H 0.7100 0.5674 0.3417 0.0700 0.73(3) Uiso R . P 2 1 . H3403 H 0.5820 0.6110 0.3767 0.0701 0.73(3) Uiso R . P 2 1 . H3402 H 0.5625 0.6500 0.3253 0.0702 0.73(3) Uiso R . P 2 1 . H3502 H 0.6564 0.3563 0.2898 0.0700 0.73(3) Uiso R . P 2 1 . H3501 H 0.5017 0.4291 0.2742 0.0698 0.73(3) Uiso R . P 2 1 . H3503 H 0.4994 0.2761 0.2944 0.0697 0.73(3) Uiso R . P 2 1 . H3311 H 0.5715 0.4219 0.3730 0.0548 0.27(3) Uiso R . P 2 2 . H3412 H 0.6987 0.5867 0.3223 0.0689 0.27(3) Uiso R . P 2 2 . H3411 H 0.5656 0.6559 0.3505 0.0689 0.27(3) Uiso R . P 2 2 . H3413 H 0.5428 0.6242 0.2986 0.0689 0.27(3) Uiso R . P 2 2 . H3512 H 0.6672 0.2886 0.3180 0.0690 0.27(3) Uiso R . P 2 2 . H3513 H 0.4910 0.2513 0.3166 0.0689 0.27(3) Uiso R . P 2 2 . H3511 H 0.5563 0.3665 0.2838 0.0692 0.27(3) Uiso R . P 2 2 . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C4 0.071(4) 0.054(3) 0.067(4) -0.013(3) -0.014(3) -0.017(3) C5 0.047(5) 0.023(4) 0.035(5) -0.007(4) -0.007(4) 0.006(4) C6 0.039(5) 0.023(4) 0.043(5) 0.001(4) 0.004(4) 0.003(4) C7 0.035(5) 0.029(4) 0.025(4) -0.004(4) -0.006(4) 0.000(4) N8 0.033(4) 0.024(3) 0.031(4) 0.004(3) -0.001(3) -0.005(3) C9 0.031(5) 0.030(4) 0.026(4) -0.004(4) 0.001(4) 0.002(4) C10 0.045(5) 0.027(4) 0.026(4) 0.007(4) 0.001(4) -0.005(4) C11 0.039(5) 0.024(4) 0.023(4) 0.007(4) 0.002(4) -0.005(4) N12 0.042(5) 0.038(4) 0.038(4) 0.000(4) -0.003(4) 0.010(4) C13 0.037(5) 0.029(4) 0.024(4) 0.007(4) 0.002(4) 0.002(4) C14 0.041(5) 0.046(5) 0.041(5) 0.006(4) 0.011(4) 0.007(5) C15 0.042(6) 0.044(6) 0.056(6) 0.001(5) 0.005(5) 0.018(5) C16 0.055(6) 0.036(5) 0.050(6) 0.000(5) 0.016(5) 0.001(5) C17 0.049(6) 0.030(4) 0.030(5) 0.003(4) 0.004(4) -0.010(4) C18 0.037(5) 0.029(4) 0.027(4) 0.001(3) 0.003(4) 0.002(4) C19 0.034(5) 0.029(4) 0.031(4) 0.005(4) 0.005(4) -0.003(4) C20 0.027(4) 0.026(4) 0.028(4) -0.001(4) 0.001(3) -0.005(4) C21 0.032(4) 0.024(4) 0.031(4) -0.003(4) 0.002(4) 0.001(4) C22 0.038(5) 0.029(4) 0.029(4) 0.006(4) 0.000(4) -0.001(4) C23 0.042(5) 0.039(5) 0.033(4) -0.004(4) -0.007(4) 0.008(5) C24 0.019(4) 0.032(5) 0.031(4) 0.002(4) 0.002(3) -0.001(4) O25 0.037(3) 0.026(3) 0.044(4) 0.008(3) -0.008(3) -0.001(3) O26 0.034(3) 0.032(3) 0.037(3) 0.010(3) -0.002(3) -0.006(3) C27 0.048(6) 0.019(4) 0.045(5) 0.006(4) -0.004(4) -0.006(4) C28 0.080(8) 0.046(5) 0.046(6) 0.003(5) 0.012(5) -0.017(6) C29 0.074(8) 0.050(6) 0.060(6) 0.005(6) 0.003(6) -0.025(6) C30 0.035(3) 0.053(3) 0.027(3) 0.014(3) 0.002(3) 0.006(3) O31 0.040(4) 0.056(4) 0.030(3) 0.017(3) -0.001(3) 0.002(3) F10 0.086(6) 0.052(5) 0.060(6) -0.015(5) -0.003(5) -0.018(5) F20 0.074(6) 0.056(5) 0.065(5) -0.014(4) -0.016(5) -0.027(5) F30 0.073(6) 0.062(5) 0.092(6) -0.005(5) -0.022(5) -0.015(5) F11 0.082(5) 0.046(4) 0.083(6) -0.013(5) -0.024(5) -0.008(4) F21 0.071(5) 0.077(5) 0.075(5) -0.026(5) -0.006(4) -0.031(5) F31 0.064(5) 0.058(4) 0.058(5) -0.013(4) -0.014(4) -0.022(5) O320 0.035(3) 0.060(3) 0.030(2) 0.015(3) 0.003(2) 0.011(3) C330 0.038(3) 0.070(4) 0.037(3) 0.019(3) 0.002(3) 0.015(3) C340 0.040(4) 0.074(4) 0.039(4) 0.021(4) -0.002(4) 0.012(4) C350 0.041(4) 0.073(5) 0.039(4) 0.019(4) 0.004(4) 0.019(4) O321 0.037(4) 0.055(4) 0.027(3) 0.014(4) 0.002(3) 0.006(4) C331 0.039(4) 0.058(5) 0.029(5) 0.015(5) 0.003(4) 0.004(5) C341 0.041(5) 0.060(6) 0.030(6) 0.015(5) 0.002(5) 0.003(6) C351 0.041(5) 0.059(6) 0.028(6) 0.016(5) 0.002(5) 0.004(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.478(2) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C4 . C5 . 1.462(10) yes C4 . F10 . 1.342(5) yes C4 . F20 . 1.357(5) yes C4 . F30 . 1.339(5) yes C4 . C5 . 1.462(10) yes C4 . F11 . 1.340(5) yes C4 . F21 . 1.341(5) yes C4 . F31 . 1.356(5) yes C5 . C6 . 1.380(12) yes C5 . C23 . 1.402(13) yes C6 . C7 . 1.409(12) yes C6 . H61 . 0.923 no C7 . N8 . 1.406(10) yes C7 . C21 . 1.388(12) yes N8 . C9 . 1.484(11) yes N8 . C19 . 1.510(11) yes C9 . C10 . 1.536(11) yes C9 . C13 . 1.496(12) yes C9 . H91 . 0.972 no C10 . C11 . 1.451(12) yes C10 . H102 . 0.965 no C10 . H101 . 0.963 no C11 . N12 . 1.149(11) yes C13 . C14 . 1.415(13) yes C13 . C18 . 1.398(12) yes C14 . C15 . 1.401(14) yes C14 . H141 . 0.928 no C15 . C16 . 1.357(14) yes C15 . H151 . 0.936 no C16 . C17 . 1.376(13) yes C16 . H161 . 0.930 no C17 . C18 . 1.406(12) yes C17 . H171 . 0.912 no C18 . C19 . 1.515(12) yes C19 . C20 . 1.559(11) yes C19 . H191 . 0.997 no C20 . C21 . 1.529(11) yes C20 . C24 . 1.534(11) yes C20 . C30 . 1.546(10) yes C21 . C22 . 1.366(11) yes C22 . C23 . 1.403(12) yes C22 . H221 . 0.927 no C23 . H231 . 0.935 no C24 . O25 . 1.202(10) yes C24 . O26 . 1.335(10) yes O26 . C27 . 1.480(10) yes C27 . C28 . 1.503(13) yes C27 . C29 . 1.495(14) yes C27 . H271 . 0.985 no C28 . H283 . 0.960 no C28 . H281 . 0.958 no C28 . H282 . 0.952 no C29 . H291 . 0.967 no C29 . H293 . 0.967 no C29 . H292 . 0.955 no C30 . O31 . 1.199(9) yes C30 . O320 . 1.318(6) yes C30 . O31 . 1.199(9) yes C30 . O321 . 1.322(7) yes O320 . C330 . 1.477(6) yes C330 . C340 . 1.503(6) yes C330 . C350 . 1.494(6) yes C330 . H3301 . 0.982 no C340 . H3401 . 0.964 no C340 . H3403 . 0.964 no C340 . H3402 . 0.969 no C350 . H3502 . 0.964 no C350 . H3501 . 0.962 no C350 . H3503 . 0.957 no O321 . C331 . 1.480(7) yes C331 . C341 . 1.502(7) yes C331 . C351 . 1.499(7) yes C331 . H3311 . 0.978 no C341 . H3412 . 0.957 no C341 . H3411 . 0.966 no C341 . H3413 . 0.961 no C351 . H3512 . 0.962 no C351 . H3513 . 0.957 no C351 . H3511 . 0.969 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C5 . C4 . F10 . 113.9(8) yes C5 . C4 . F20 . 108.5(7) yes F10 . C4 . F20 . 103.54(6) yes C5 . C4 . F30 . 121.9(7) yes F10 . C4 . F30 . 103.58(6) yes F20 . C4 . F30 . 103.57(6) yes C5 . C4 . F11 . 116.8(7) yes C5 . C4 . F21 . 116.3(6) yes F11 . C4 . F21 . 103.60(6) yes C5 . C4 . F31 . 111.5(6) yes F11 . C4 . F31 . 103.54(6) yes F21 . C4 . F31 . 103.56(6) yes C4 . C5 . C6 . 120.2(8) yes C4 . C5 . C23 . 117.0(7) yes C6 . C5 . C23 . 122.8(8) yes C5 . C6 . C7 . 117.0(8) yes C5 . C6 . H61 . 122.2 no C7 . C6 . H61 . 120.8 no C6 . C7 . N8 . 126.3(8) yes C6 . C7 . C21 . 120.8(8) yes N8 . C7 . C21 . 112.9(7) yes C7 . N8 . C9 . 117.0(7) yes C7 . N8 . C19 . 107.8(6) yes C9 . N8 . C19 . 110.2(6) yes N8 . C9 . C10 . 110.8(7) yes N8 . C9 . C13 . 103.4(7) yes C10 . C9 . C13 . 113.4(7) yes N8 . C9 . H91 . 108.6 no C10 . C9 . H91 . 109.1 no C13 . C9 . H91 . 111.4 no C9 . C10 . C11 . 111.5(7) yes C9 . C10 . H102 . 108.6 no C11 . C10 . H102 . 108.5 no C9 . C10 . H101 . 109.8 no C11 . C10 . H101 . 109.8 no H102 . C10 . H101 . 108.6 no C10 . C11 . N12 . 176.8(9) yes C9 . C13 . C14 . 127.8(8) yes C9 . C13 . C18 . 111.4(8) yes C14 . C13 . C18 . 120.8(8) yes C13 . C14 . C15 . 117.4(10) yes C13 . C14 . H141 . 120.5 no C15 . C14 . H141 . 122.1 no C14 . C15 . C16 . 121.2(10) yes C14 . C15 . H151 . 119.4 no C16 . C15 . H151 . 119.4 no C15 . C16 . C17 . 122.2(9) yes C15 . C16 . H161 . 118.9 no C17 . C16 . H161 . 118.8 no C16 . C17 . C18 . 118.6(9) yes C16 . C17 . H171 . 120.1 no C18 . C17 . H171 . 121.3 no C17 . C18 . C13 . 119.7(8) yes C17 . C18 . C19 . 130.4(9) yes C13 . C18 . C19 . 109.7(7) yes C18 . C19 . N8 . 102.6(6) yes C18 . C19 . C20 . 119.9(7) yes N8 . C19 . C20 . 104.9(6) yes C18 . C19 . H191 . 111.4 no N8 . C19 . H191 . 109.6 no C20 . C19 . H191 . 107.7 no C19 . C20 . C21 . 103.6(7) yes C19 . C20 . C24 . 113.5(7) yes C21 . C20 . C24 . 111.9(7) yes C19 . C20 . C30 . 111.1(6) yes C21 . C20 . C30 . 108.6(7) yes C24 . C20 . C30 . 108.1(7) yes C20 . C21 . C7 . 108.9(7) yes C20 . C21 . C22 . 129.9(8) yes C7 . C21 . C22 . 121.3(8) yes C21 . C22 . C23 . 119.6(8) yes C21 . C22 . H221 . 120.9 no C23 . C22 . H221 . 119.5 no C22 . C23 . C5 . 118.5(8) yes C22 . C23 . H231 . 120.6 no C5 . C23 . H231 . 120.8 no C20 . C24 . O25 . 124.3(7) yes C20 . C24 . O26 . 109.9(6) yes O25 . C24 . O26 . 125.8(7) yes C24 . O26 . C27 . 117.2(6) yes O26 . C27 . C28 . 108.5(8) yes O26 . C27 . C29 . 105.5(7) yes C28 . C27 . C29 . 112.9(9) yes O26 . C27 . H271 . 109.1 no C28 . C27 . H271 . 110.2 no C29 . C27 . H271 . 110.4 no C27 . C28 . H283 . 110.0 no C27 . C28 . H281 . 108.6 no H283 . C28 . H281 . 108.8 no C27 . C28 . H282 . 110.8 no H283 . C28 . H282 . 109.5 no H281 . C28 . H282 . 109.1 no C27 . C29 . H291 . 107.8 no C27 . C29 . H293 . 109.1 no H291 . C29 . H293 . 109.8 no C27 . C29 . H292 . 109.8 no H291 . C29 . H292 . 110.8 no H293 . C29 . H292 . 109.6 no C20 . C30 . O31 . 124.8(6) yes C20 . C30 . O320 . 108.8(5) yes O31 . C30 . O320 . 126.4(5) yes C20 . C30 . O31 . 124.8(6) yes C20 . C30 . O321 . 110.4(7) yes O31 . C30 . O321 . 124.8(7) yes C30 . O320 . C330 . 119.03(7) yes O320 . C330 . C340 . 106.21(7) yes O320 . C330 . C350 . 106.19(7) yes C340 . C330 . C350 . 115.41(7) yes O320 . C330 . H3301 . 108.9 no C340 . C330 . H3301 . 113.4 no C350 . C330 . H3301 . 106.5 no C330 . C340 . H3401 . 108.0 no C330 . C340 . H3403 . 107.6 no H3401 . C340 . H3403 . 109.3 no C330 . C340 . H3402 . 113.6 no H3401 . C340 . H3402 . 109.1 no H3403 . C340 . H3402 . 109.2 no C330 . C350 . H3502 . 110.3 no C330 . C350 . H3501 . 106.1 no H3502 . C350 . H3501 . 109.9 no C330 . C350 . H3503 . 112.7 no H3502 . C350 . H3503 . 108.9 no H3501 . C350 . H3503 . 108.9 no C30 . O321 . C331 . 119.03(7) yes O321 . C331 . C341 . 106.21(7) yes O321 . C331 . C351 . 106.20(7) yes C341 . C331 . C351 . 115.41(7) yes O321 . C331 . H3311 . 108.9 no C341 . C331 . H3311 . 116.1 no C351 . C331 . H3311 . 103.6 no C331 . C341 . H3412 . 109.1 no C331 . C341 . H3411 . 103.2 no H3412 . C341 . H3411 . 109.3 no C331 . C341 . H3413 . 115.9 no H3412 . C341 . H3413 . 109.2 no H3411 . C341 . H3413 . 109.9 no C331 . C351 . H3512 . 112.8 no C331 . C351 . H3513 . 113.7 no H3512 . C351 . H3513 . 109.6 no C331 . C351 . H3511 . 102.3 no H3512 . C351 . H3511 . 109.5 no H3513 . C351 . H3511 . 108.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C9 . H91 . N12 2_456 133.8 0.972 2.576 3.324(16) yes C17 . H171 . O26 . 129.6 0.912 2.477 3.139(16) yes C351 . H3512 . C5 1_655 161.6 0.962 2.344 3.271(16) yes C351 . H3512 . C6 1_655 146.5 0.962 2.576 3.420(16) yes _chemical_name_common . #============================================================================== data_15 _database_code_depnum_ccdc_archive 'CCDC 845081' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 10-03-15 _audit_creation_method CRYSTALS_ver_14.06 _oxford_structure_analysis_title 6214 _chemical_name_systematic . _chemical_melting_point . _cell_length_a 11.9727(3) _cell_length_b 24.2406(7) _cell_length_c 10.4810(3) _cell_angle_alpha 90 _cell_angle_beta 107.399(1) _cell_angle_gamma 90 _cell_volume 2902.67(14) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0171 0.0103 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C31 H30 F3 N1 O6 S1 # Dc = 1.38 Fooo = 1256.00 Mu = 1.76 M = 601.64 # Found Formula = C31 H30 F3 N1 O6 S1 # Dc = 1.38 FOOO = 1256.00 Mu = 1.76 M = 601.64 _chemical_formula_sum 'C31 H30 F3 N1 O6 S1' _chemical_formula_moiety 'C31 H30 F3 N1 O6 S1' _chemical_compound_source . _chemical_formula_weight 601.64 _cell_measurement_reflns_used 5248 _cell_measurement_theta_min 5 _cell_measurement_theta_max 26 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.120 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_max 0.140 _exptl_crystal_density_diffrn 1.377 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1256 _exptl_absorpt_coefficient_mu 0.176 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.89 _exptl_absorpt_correction_T_max 0.98 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 24515 _reflns_number_total 5858 _diffrn_reflns_av_R_equivalents 0.041 # Number of reflections without Friedels Law is 10163 # Number of reflections with Friedels Law is 5858 # Theoretical number of reflections is about 3993 _diffrn_reflns_theta_min 5.174 _diffrn_reflns_theta_max 26.562 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.234 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -26 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min 0 _reflns_limit_h_max 14 _reflns_limit_k_min -30 _reflns_limit_k_max 0 _reflns_limit_l_min -13 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 2.60 _oxford_diffrn_Wilson_scale 9.28 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.42 _refine_diff_density_max 0.53 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 3945 _refine_ls_number_restraints 0 _refine_ls_number_parameters 379 _oxford_refine_ls_R_factor_ref 0.0656 _refine_ls_wR_factor_ref 0.1326 _refine_ls_goodness_of_fit_ref 0.9241 _refine_ls_shift/su_max 0.0003958 _refine_ls_shift/su_mean 0.0000328 # The values computed from all data _oxford_reflns_number_all 3946 _refine_ls_R_factor_all 0.0656 _refine_ls_wR_factor_all 0.1327 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3067 _refine_ls_R_factor_gt 0.0462 _refine_ls_wR_factor_gt 0.1132 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 29.3 44.2 21.8 5.50 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens S1 S 0.08670(7) 0.50931(3) 0.34389(8) 0.0350 1.0000 Uani . . . . . . . O2 O 0.0672(2) 0.45175(10) 0.3636(2) 0.0476 1.0000 Uani . . . . . . . O3 O -0.01391(19) 0.54469(11) 0.2996(2) 0.0494 1.0000 Uani . . . . . . . C4 C 0.1663(3) 0.51511(13) 0.2269(3) 0.0332 1.0000 Uani . . . . . . . C5 C 0.2814(3) 0.49598(14) 0.2588(4) 0.0411 1.0000 Uani . . . . . . . C6 C 0.3408(4) 0.50108(15) 0.1647(4) 0.0491 1.0000 Uani . . . . . . . C7 C 0.2866(4) 0.52363(17) 0.0415(4) 0.0565 1.0000 Uani . . . . . . . C8 C 0.1717(4) 0.54156(17) 0.0098(4) 0.0557 1.0000 Uani . . . . . . . C9 C 0.1112(3) 0.53815(15) 0.1036(3) 0.0429 1.0000 Uani . . . . . . . C10 C 0.1774(3) 0.53520(13) 0.4990(3) 0.0311 1.0000 Uani . . . . . . . C11 C 0.2170(3) 0.59504(12) 0.4980(3) 0.0285 1.0000 Uani . . . . . . . N12 N 0.3109(2) 0.59992(10) 0.4345(2) 0.0263 1.0000 Uani . . . . . . . C13 C 0.4268(2) 0.60021(12) 0.5402(3) 0.0276 1.0000 Uani . . . . . . . C14 C 0.3955(3) 0.61861(12) 0.6642(3) 0.0295 1.0000 Uani . . . . . . . C15 C 0.2744(3) 0.61534(12) 0.6390(3) 0.0300 1.0000 Uani . . . . . . . C16 C 0.2218(3) 0.62824(13) 0.7364(3) 0.0364 1.0000 Uani . . . . . . . C17 C 0.2921(3) 0.64542(14) 0.8601(3) 0.0420 1.0000 Uani . . . . . . . C18 C 0.4124(3) 0.64822(15) 0.8867(3) 0.0423 1.0000 Uani . . . . . . . C19 C 0.4654(3) 0.63404(14) 0.7901(3) 0.0369 1.0000 Uani . . . . . . . C20 C 0.5064(2) 0.63755(12) 0.4809(3) 0.0268 1.0000 Uani . . . . . . . C21 C 0.4187(2) 0.66749(12) 0.3679(3) 0.0260 1.0000 Uani . . . . . . . C22 C 0.3084(3) 0.64480(12) 0.3484(3) 0.0262 1.0000 Uani . . . . . . . C23 C 0.2121(2) 0.66452(12) 0.2504(3) 0.0284 1.0000 Uani . . . . . . . C24 C 0.2302(3) 0.70792(12) 0.1708(3) 0.0294 1.0000 Uani . . . . . . . C25 C 0.3403(3) 0.72986(13) 0.1873(3) 0.0330 1.0000 Uani . . . . . . . C26 C 0.4355(3) 0.70989(12) 0.2871(3) 0.0317 1.0000 Uani . . . . . . . C27 C 0.1266(3) 0.72937(14) 0.0653(3) 0.0390 1.0000 Uani . . . . . . . F28 F 0.07385(19) 0.68921(10) -0.0201(2) 0.0693 1.0000 Uani . . . . . . . F29 F 0.1521(2) 0.76712(10) -0.0129(2) 0.0671 1.0000 Uani . . . . . . . F30 F 0.0453(2) 0.74920(16) 0.1116(3) 0.1032 1.0000 Uani . . . . . . . C31 C 0.5860(2) 0.67590(13) 0.5840(3) 0.0288 1.0000 Uani . . . . . . . O32 O 0.57240(19) 0.72482(9) 0.5914(2) 0.0379 1.0000 Uani . . . . . . . O33 O 0.67310(17) 0.64676(9) 0.6662(2) 0.0331 1.0000 Uani . . . . . . . C34 C 0.7634(3) 0.67731(15) 0.7674(3) 0.0384 1.0000 Uani . . . . . . . C35 C 0.8520(3) 0.69805(16) 0.7038(4) 0.0477 1.0000 Uani . . . . . . . C36 C 0.8134(3) 0.63752(17) 0.8804(4) 0.0534 1.0000 Uani . . . . . . . C37 C 0.5876(2) 0.60215(13) 0.4247(3) 0.0283 1.0000 Uani . . . . . . . O38 O 0.59049(18) 0.55236(9) 0.4240(2) 0.0341 1.0000 Uani . . . . . . . O39 O 0.65329(18) 0.63521(9) 0.3753(2) 0.0351 1.0000 Uani . . . . . . . C40 C 0.7420(3) 0.61054(13) 0.3211(3) 0.0347 1.0000 Uani . . . . . . . C41 C 0.8217(4) 0.65732(17) 0.3133(5) 0.0651 1.0000 Uani . . . . . . . C42 C 0.6854(4) 0.5842(2) 0.1885(4) 0.0769 1.0000 Uani . . . . . . . H51 H 0.3179 0.4810 0.3430 0.0491 1.0000 Uiso R . . . . . . H61 H 0.4175 0.4884 0.1853 0.0590 1.0000 Uiso R . . . . . . H71 H 0.3269 0.5268 -0.0217 0.0677 1.0000 Uiso R . . . . . . H81 H 0.1337 0.5561 -0.0747 0.0674 1.0000 Uiso R . . . . . . H91 H 0.0340 0.5510 0.0845 0.0517 1.0000 Uiso R . . . . . . H102 H 0.1299 0.5313 0.5589 0.0371 1.0000 Uiso R . . . . . . H101 H 0.2442 0.5112 0.5290 0.0365 1.0000 Uiso R . . . . . . H111 H 0.1494 0.6184 0.4503 0.0331 1.0000 Uiso R . . . . . . H131 H 0.4591 0.5632 0.5524 0.0321 1.0000 Uiso R . . . . . . H161 H 0.1409 0.6262 0.7170 0.0440 1.0000 Uiso R . . . . . . H171 H 0.2587 0.6542 0.9285 0.0500 1.0000 Uiso R . . . . . . H181 H 0.4592 0.6599 0.9709 0.0506 1.0000 Uiso R . . . . . . H191 H 0.5475 0.6356 0.8107 0.0440 1.0000 Uiso R . . . . . . H231 H 0.1379 0.6493 0.2371 0.0341 1.0000 Uiso R . . . . . . H251 H 0.3499 0.7583 0.1311 0.0400 1.0000 Uiso R . . . . . . H261 H 0.5105 0.7243 0.2998 0.0380 1.0000 Uiso R . . . . . . H341 H 0.7269 0.7083 0.7981 0.0462 1.0000 Uiso R . . . . . . H352 H 0.9131 0.7190 0.7679 0.0719 1.0000 Uiso R . . . . . . H351 H 0.8133 0.7215 0.6287 0.0711 1.0000 Uiso R . . . . . . H353 H 0.8885 0.6667 0.6743 0.0717 1.0000 Uiso R . . . . . . H362 H 0.8666 0.6577 0.9536 0.0796 1.0000 Uiso R . . . . . . H361 H 0.7509 0.6210 0.9084 0.0799 1.0000 Uiso R . . . . . . H363 H 0.8569 0.6088 0.8503 0.0801 1.0000 Uiso R . . . . . . H401 H 0.7850 0.5831 0.3854 0.0415 1.0000 Uiso R . . . . . . H412 H 0.8831 0.6433 0.2784 0.0964 1.0000 Uiso R . . . . . . H411 H 0.8575 0.6710 0.4016 0.0970 1.0000 Uiso R . . . . . . H413 H 0.7779 0.6862 0.2572 0.0973 1.0000 Uiso R . . . . . . H422 H 0.7451 0.5698 0.1519 0.1145 1.0000 Uiso R . . . . . . H421 H 0.6396 0.6120 0.1282 0.1148 1.0000 Uiso R . . . . . . H423 H 0.6339 0.5552 0.1983 0.1151 1.0000 Uiso 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 0.0301(4) 0.0411(5) 0.0358(4) -0.0048(4) 0.0127(3) -0.0068(3) O2 0.0574(15) 0.0429(14) 0.0486(14) -0.0079(11) 0.0253(12) -0.0211(12) O3 0.0301(12) 0.0696(17) 0.0452(14) -0.0093(12) 0.0062(11) 0.0046(12) C4 0.0389(18) 0.0309(17) 0.0319(17) -0.0060(13) 0.0140(15) -0.0073(14) C5 0.046(2) 0.0406(19) 0.0421(19) 0.0002(16) 0.0218(16) -0.0001(15) C6 0.057(2) 0.045(2) 0.056(2) -0.0077(18) 0.032(2) -0.0062(17) C7 0.076(3) 0.058(2) 0.049(2) -0.014(2) 0.041(2) -0.021(2) C8 0.076(3) 0.059(2) 0.0333(19) -0.0024(17) 0.018(2) -0.023(2) C9 0.0439(19) 0.046(2) 0.0360(19) -0.0023(16) 0.0071(16) -0.0105(16) C10 0.0289(16) 0.0339(17) 0.0343(17) 0.0001(14) 0.0155(14) -0.0030(13) C11 0.0256(15) 0.0340(17) 0.0291(16) 0.0030(13) 0.0129(13) 0.0012(13) N12 0.0230(12) 0.0303(14) 0.0269(13) 0.0012(11) 0.0094(10) -0.0024(10) C13 0.0268(15) 0.0279(16) 0.0292(16) 0.0005(13) 0.0101(13) 0.0007(12) C14 0.0334(17) 0.0279(16) 0.0300(16) 0.0034(13) 0.0135(14) -0.0005(13) C15 0.0293(16) 0.0317(16) 0.0311(16) 0.0002(13) 0.0126(14) -0.0017(13) C16 0.0376(18) 0.0406(19) 0.0362(18) 0.0013(15) 0.0190(15) -0.0027(14) C17 0.052(2) 0.046(2) 0.0365(19) -0.0048(16) 0.0267(17) -0.0058(17) C18 0.049(2) 0.053(2) 0.0261(17) -0.0034(15) 0.0130(16) -0.0088(16) C19 0.0320(17) 0.047(2) 0.0310(17) 0.0024(15) 0.0083(14) -0.0052(15) C20 0.0261(15) 0.0277(15) 0.0281(16) 0.0005(12) 0.0102(13) -0.0003(12) C21 0.0253(15) 0.0264(15) 0.0296(16) -0.0038(13) 0.0133(13) 0.0014(12) C22 0.0303(16) 0.0281(16) 0.0229(15) -0.0016(12) 0.0121(13) -0.0016(13) C23 0.0254(15) 0.0320(17) 0.0284(16) -0.0018(13) 0.0088(13) -0.0034(13) C24 0.0318(17) 0.0314(17) 0.0250(15) -0.0009(13) 0.0087(13) 0.0025(13) C25 0.0384(18) 0.0290(16) 0.0339(17) 0.0065(13) 0.0144(15) -0.0002(14) C26 0.0296(16) 0.0329(17) 0.0363(18) 0.0009(14) 0.0154(14) -0.0049(13) C27 0.0349(18) 0.045(2) 0.0380(19) 0.0052(16) 0.0119(15) -0.0014(16) F28 0.0465(13) 0.0676(15) 0.0701(15) 0.0012(13) -0.0189(11) -0.0061(11) F29 0.0552(13) 0.0727(15) 0.0600(14) 0.0341(12) -0.0033(11) -0.0101(11) F30 0.0765(18) 0.183(3) 0.0596(16) 0.0353(18) 0.0345(14) 0.090(2) C31 0.0254(16) 0.0355(19) 0.0299(16) -0.0012(14) 0.0150(14) -0.0034(13) O32 0.0388(13) 0.0348(14) 0.0404(13) -0.0059(10) 0.0122(10) 0.0010(10) O33 0.0241(11) 0.0363(12) 0.0356(12) -0.0004(10) 0.0041(9) -0.0025(9) C34 0.0278(16) 0.048(2) 0.0362(18) -0.0070(15) 0.0047(14) -0.0090(15) C35 0.0332(18) 0.058(2) 0.051(2) -0.0002(18) 0.0120(17) -0.0119(16) C36 0.043(2) 0.065(3) 0.043(2) 0.0061(18) -0.0018(17) -0.0190(18) C37 0.0226(15) 0.0362(19) 0.0249(16) 0.0027(13) 0.0051(12) 0.0028(13) O38 0.0319(12) 0.0301(13) 0.0441(13) -0.0001(10) 0.0173(10) 0.0024(9) O39 0.0348(12) 0.0326(12) 0.0468(13) 0.0043(10) 0.0256(11) 0.0028(9) C40 0.0320(17) 0.0375(18) 0.0411(19) 0.0043(14) 0.0210(15) 0.0061(14) C41 0.068(3) 0.048(2) 0.104(3) -0.003(2) 0.064(3) -0.004(2) C42 0.054(3) 0.134(5) 0.050(2) -0.025(3) 0.027(2) -0.008(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3523(6) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O2 . 1.440(2) yes S1 . O3 . 1.438(3) yes S1 . C4 . 1.770(3) yes S1 . C10 . 1.778(3) yes C4 . C5 . 1.396(5) yes C4 . C9 . 1.381(5) yes C5 . C6 . 1.383(5) yes C5 . H51 . 0.933 no C6 . C7 . 1.373(6) yes C6 . H61 . 0.932 no C7 . C8 . 1.385(6) yes C7 . H71 . 0.932 no C8 . C9 . 1.387(5) yes C8 . H81 . 0.936 no C9 . H91 . 0.938 no C10 . C11 . 1.527(4) yes C10 . H102 . 0.970 no C10 . H101 . 0.963 no C11 . N12 . 1.472(4) yes C11 . C15 . 1.514(4) yes C11 . H111 . 0.992 no N12 . C13 . 1.495(4) yes N12 . C22 . 1.408(4) yes C13 . C14 . 1.523(4) yes C13 . C20 . 1.572(4) yes C13 . H131 . 0.971 no C14 . C15 . 1.396(4) yes C14 . C19 . 1.386(4) yes C15 . C16 . 1.385(4) yes C16 . C17 . 1.383(5) yes C16 . H161 . 0.930 no C17 . C18 . 1.384(5) yes C17 . H171 . 0.943 no C18 . C19 . 1.390(5) yes C18 . H181 . 0.936 no C19 . H191 . 0.942 no C20 . C21 . 1.513(4) yes C20 . C31 . 1.524(4) yes C20 . C37 . 1.540(4) yes C21 . C22 . 1.388(4) yes C21 . C26 . 1.385(4) yes C22 . C23 . 1.381(4) yes C23 . C24 . 1.399(4) yes C23 . H231 . 0.932 no C24 . C25 . 1.383(4) yes C24 . C27 . 1.487(4) yes C25 . C26 . 1.384(4) yes C25 . H251 . 0.935 no C26 . H261 . 0.935 no C27 . F28 . 1.345(4) yes C27 . F29 . 1.324(4) yes C27 . F30 . 1.304(4) yes C31 . O32 . 1.203(4) yes C31 . O33 . 1.338(4) yes O33 . C34 . 1.469(4) yes C34 . C35 . 1.499(5) yes C34 . C36 . 1.505(5) yes C34 . H341 . 0.971 no C35 . H352 . 0.975 no C35 . H351 . 0.969 no C35 . H353 . 0.971 no C36 . H362 . 0.971 no C36 . H361 . 0.968 no C36 . H363 . 0.977 no C37 . O38 . 1.208(4) yes C37 . O39 . 1.331(4) yes O39 . C40 . 1.472(4) yes C40 . C41 . 1.501(5) yes C40 . C42 . 1.495(5) yes C40 . H401 . 0.976 no C41 . H412 . 0.974 no C41 . H411 . 0.956 no C41 . H413 . 0.963 no C42 . H422 . 0.972 no C42 . H421 . 0.974 no C42 . H423 . 0.961 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 . S1 . O3 . 117.94(16) yes O2 . S1 . C4 . 108.67(14) yes O3 . S1 . C4 . 107.55(15) yes O2 . S1 . C10 . 106.99(15) yes O3 . S1 . C10 . 107.96(15) yes C4 . S1 . C10 . 107.30(14) yes S1 . C4 . C5 . 120.3(2) yes S1 . C4 . C9 . 118.3(3) yes C5 . C4 . C9 . 121.3(3) yes C4 . C5 . C6 . 118.7(3) yes C4 . C5 . H51 . 120.3 no C6 . C5 . H51 . 121.0 no C5 . C6 . C7 . 120.5(4) yes C5 . C6 . H61 . 119.2 no C7 . C6 . H61 . 120.3 no C6 . C7 . C8 . 120.4(3) yes C6 . C7 . H71 . 120.1 no C8 . C7 . H71 . 119.4 no C7 . C8 . C9 . 120.2(4) yes C7 . C8 . H81 . 120.8 no C9 . C8 . H81 . 119.0 no C8 . C9 . C4 . 118.8(4) yes C8 . C9 . H91 . 121.3 no C4 . C9 . H91 . 119.9 no S1 . C10 . C11 . 115.8(2) yes S1 . C10 . H102 . 104.0 no C11 . C10 . H102 . 110.0 no S1 . C10 . H101 . 107.8 no C11 . C10 . H101 . 110.3 no H102 . C10 . H101 . 108.6 no C10 . C11 . N12 . 111.1(2) yes C10 . C11 . C15 . 110.7(2) yes N12 . C11 . C15 . 103.3(2) yes C10 . C11 . H111 . 109.7 no N12 . C11 . H111 . 110.1 no C15 . C11 . H111 . 111.8 no C11 . N12 . C13 . 109.3(2) yes C11 . N12 . C22 . 118.6(2) yes C13 . N12 . C22 . 108.0(2) yes N12 . C13 . C14 . 102.9(2) yes N12 . C13 . C20 . 104.4(2) yes C14 . C13 . C20 . 120.1(2) yes N12 . C13 . H131 . 109.8 no C14 . C13 . H131 . 110.5 no C20 . C13 . H131 . 108.6 no C13 . C14 . C15 . 109.2(3) yes C13 . C14 . C19 . 131.2(3) yes C15 . C14 . C19 . 119.5(3) yes C11 . C15 . C14 . 110.2(3) yes C11 . C15 . C16 . 128.3(3) yes C14 . C15 . C16 . 121.5(3) yes C15 . C16 . C17 . 118.4(3) yes C15 . C16 . H161 . 120.0 no C17 . C16 . H161 . 121.6 no C16 . C17 . C18 . 120.6(3) yes C16 . C17 . H171 . 120.2 no C18 . C17 . H171 . 119.2 no C17 . C18 . C19 . 121.0(3) yes C17 . C18 . H181 . 119.8 no C19 . C18 . H181 . 119.1 no C18 . C19 . C14 . 118.8(3) yes C18 . C19 . H191 . 119.7 no C14 . C19 . H191 . 121.4 no C13 . C20 . C21 . 103.0(2) yes C13 . C20 . C31 . 113.3(2) yes C21 . C20 . C31 . 113.8(2) yes C13 . C20 . C37 . 111.0(2) yes C21 . C20 . C37 . 109.7(2) yes C31 . C20 . C37 . 106.2(2) yes C20 . C21 . C22 . 109.4(2) yes C20 . C21 . C26 . 129.9(3) yes C22 . C21 . C26 . 120.6(3) yes N12 . C22 . C21 . 112.0(2) yes N12 . C22 . C23 . 126.7(3) yes C21 . C22 . C23 . 121.3(3) yes C22 . C23 . C24 . 117.4(3) yes C22 . C23 . H231 . 121.4 no C24 . C23 . H231 . 121.3 no C23 . C24 . C25 . 121.8(3) yes C23 . C24 . C27 . 117.6(3) yes C25 . C24 . C27 . 120.7(3) yes C24 . C25 . C26 . 119.9(3) yes C24 . C25 . H251 . 119.8 no C26 . C25 . H251 . 120.3 no C21 . C26 . C25 . 119.0(3) yes C21 . C26 . H261 . 119.9 no C25 . C26 . H261 . 121.1 no C24 . C27 . F28 . 111.3(3) yes C24 . C27 . F29 . 114.0(3) yes F28 . C27 . F29 . 103.8(3) yes C24 . C27 . F30 . 113.7(3) yes F28 . C27 . F30 . 105.1(3) yes F29 . C27 . F30 . 108.2(3) yes C20 . C31 . O32 . 125.4(3) yes C20 . C31 . O33 . 109.6(3) yes O32 . C31 . O33 . 125.0(3) yes C31 . O33 . C34 . 117.6(2) yes O33 . C34 . C35 . 108.3(3) yes O33 . C34 . C36 . 106.2(3) yes C35 . C34 . C36 . 113.4(3) yes O33 . C34 . H341 . 108.8 no C35 . C34 . H341 . 109.7 no C36 . C34 . H341 . 110.4 no C34 . C35 . H352 . 110.6 no C34 . C35 . H351 . 109.2 no H352 . C35 . H351 . 109.5 no C34 . C35 . H353 . 109.0 no H352 . C35 . H353 . 108.0 no H351 . C35 . H353 . 110.5 no C34 . C36 . H362 . 108.1 no C34 . C36 . H361 . 110.0 no H362 . C36 . H361 . 110.6 no C34 . C36 . H363 . 109.1 no H362 . C36 . H363 . 109.2 no H361 . C36 . H363 . 109.8 no C20 . C37 . O38 . 125.6(3) yes C20 . C37 . O39 . 109.1(2) yes O38 . C37 . O39 . 125.3(3) yes C37 . O39 . C40 . 118.9(2) yes O39 . C40 . C41 . 105.0(3) yes O39 . C40 . C42 . 110.7(3) yes C41 . C40 . C42 . 113.0(3) yes O39 . C40 . H401 . 107.6 no C41 . C40 . H401 . 109.8 no C42 . C40 . H401 . 110.5 no C40 . C41 . H412 . 108.8 no C40 . C41 . H411 . 108.5 no H412 . C41 . H411 . 108.3 no C40 . C41 . H413 . 110.1 no H412 . C41 . H413 . 111.0 no H411 . C41 . H413 . 110.0 no C40 . C42 . H422 . 109.8 no C40 . C42 . H421 . 108.6 no H422 . C42 . H421 . 109.3 no C40 . C42 . H423 . 109.8 no H422 . C42 . H423 . 110.5 no H421 . C42 . H423 . 108.8 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C5 . H51 . O38 2_666 175 0.93 2.49 3.425(5) yes C10 . H101 . O38 2_666 173 0.96 2.44 3.397(5) yes C19 . H191 . O33 . 131 0.94 2.45 3.146(5) yes _chemical_name_common . #============================================================================== data_18 _database_code_depnum_ccdc_archive 'CCDC 845082' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 11-02-14 _audit_creation_method CRYSTALS_ver_14.18 _oxford_structure_analysis_title 6308 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 10.8509(1) _cell_length_b 9.3445(1) _cell_length_c 12.7734(2) _cell_angle_alpha 90 _cell_angle_beta 107.2971(15) _cell_angle_gamma 90 _cell_volume 1236.60(3) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1 ' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C27 H27 F3 N2 O2 # Dc = 1.26 Fooo = 524.00 Mu = 7.91 M = 468.52 # Found Formula = C27 H27 F3 N2 O4 # Dc = 1.34 FOOO = 524.00 Mu = 8.90 M = 500.52 _chemical_formula_sum 'C27 H27 F3 N2 O4' _chemical_formula_moiety 'C27 H27 F3 N2 O4' _chemical_compound_source . _chemical_formula_weight 500.52 _cell_measurement_reflns_used 16453 _cell_measurement_theta_min 4 _cell_measurement_theta_max 76 _cell_measurement_temperature 150 _exptl_crystal_description needle _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_max 0.320 _exptl_crystal_density_diffrn 1.344 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 524 _exptl_absorpt_coefficient_mu 0.890 # Sheldrick geometric approximatio 0.94 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies (Oxford Diffraction, 2002), Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.71 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 29332 _reflns_number_total 5108 _diffrn_reflns_av_R_equivalents 0.031 # Number of reflections without Friedels Law is 5108 # Number of reflections with Friedels Law is 2730 # Theoretical number of reflections is about 2579 _diffrn_reflns_theta_min 3.624 _diffrn_reflns_theta_max 75.913 _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 75.913 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 2.74 _oxford_diffrn_Wilson_scale 0.02 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.21 _refine_diff_density_max 0.29 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 5106 _refine_ls_number_restraints 1 _refine_ls_number_parameters 326 _oxford_refine_ls_R_factor_ref 0.0369 _refine_ls_wR_factor_ref 0.0957 _refine_ls_goodness_of_fit_ref 0.9957 _refine_ls_shift/su_max 0.0004044 _refine_ls_shift/su_mean 0.0000429 # The values computed from all data _oxford_reflns_number_all 5106 _refine_ls_R_factor_all 0.0369 _refine_ls_wR_factor_all 0.0957 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4985 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_gt 0.0946 _refine_ls_abs_structure_Flack 0.01(10) _refine_ls_abs_structure_details 'Flack (1983), 2378 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.06P)^2^ + 0.26P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Oxford Diffraction, (2010). CrysAlisPro. Oxford Diffraction, (2010). Supernova User Manual. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens F1 F 0.58193(9) 0.32806(13) 0.16347(8) 0.0406 1.0000 Uani . . . . . . C2 C 0.70623(15) 0.29141(18) 0.20507(13) 0.0316 1.0000 Uani . . . . . . F3 F 0.77029(11) 0.35986(16) 0.14581(8) 0.0516 1.0000 Uani . . . . . . F4 F 0.71138(12) 0.15088(13) 0.18258(9) 0.0487 1.0000 Uani . . . . . . C5 C 0.75907(14) 0.31933(16) 0.32549(12) 0.0259 1.0000 Uani . . . . . . C6 C 0.89325(14) 0.32400(17) 0.37204(12) 0.0265 1.0000 Uani . . . . . . C7 C 0.94041(13) 0.33983(16) 0.48540(12) 0.0244 1.0000 Uani . . . . . . N8 N 1.06550(12) 0.34209(19) 0.55118(11) 0.0347 1.0000 Uani . . . . . . C9 C 1.18199(13) 0.33559(17) 0.51891(12) 0.0267 1.0000 Uani . . . . . . C10 C 1.25101(14) 0.48193(17) 0.53823(14) 0.0289 1.0000 Uani . . . . . . C11 C 1.34770(16) 0.49552(18) 0.47975(16) 0.0358 1.0000 Uani . . . . . . N12 N 1.42174(18) 0.5065(2) 0.43297(18) 0.0551 1.0000 Uani . . . . . . C13 C 1.26482(16) 0.21641(17) 0.58614(14) 0.0314 1.0000 Uani . . . . . . C14 C 1.27866(14) 0.23181(16) 0.70671(13) 0.0275 1.0000 Uani . . . . . . C15 C 1.18741(13) 0.30600(16) 0.74418(13) 0.0263 1.0000 Uani . . . . . . C16 C 1.07443(13) 0.38137(17) 0.66337(12) 0.0257 1.0000 Uani . . . . . . C17 C 0.93478(13) 0.35232(16) 0.67117(11) 0.0236 1.0000 Uani . . . . . . C18 C 0.85536(13) 0.35012(15) 0.54957(11) 0.0223 1.0000 Uani . . . . . . C19 C 0.72381(13) 0.34719(16) 0.50200(12) 0.0251 1.0000 Uani . . . . . . C20 C 0.67451(13) 0.33292(17) 0.38798(12) 0.0270 1.0000 Uani . . . . . . C21 C 0.89192(14) 0.47159(17) 0.73477(13) 0.0268 1.0000 Uani . . . . . . O22 O 0.76858(10) 0.45682(13) 0.72904(9) 0.0318 1.0000 Uani . . . . . . C23 C 0.71174(16) 0.56187(19) 0.78665(14) 0.0324 1.0000 Uani . . . . . . C24 C 0.5956(2) 0.4900(3) 0.8032(2) 0.0565 1.0000 Uani . . . . . . C25 C 0.6812(2) 0.6971(3) 0.7201(2) 0.0601 1.0000 Uani . . . . . . O26 O 0.96067(12) 0.56630(15) 0.78230(12) 0.0447 1.0000 Uani . . . . . . C27 C 0.92562(13) 0.20298(17) 0.71855(12) 0.0260 1.0000 Uani . . . . . . O28 O 0.93949(14) 0.09567(14) 0.67195(10) 0.0392 1.0000 Uani . . . . . . O29 O 0.90067(13) 0.20814(14) 0.81404(10) 0.0376 1.0000 Uani . . . . . . C30 C 0.8729(2) 0.0715(2) 0.86005(17) 0.0509 1.0000 Uani . . . . . . C31 C 0.7718(3) 0.1040(4) 0.9137(3) 0.0933 1.0000 Uani . . . . . . C32 C 0.9932(3) 0.0152(4) 0.9359(3) 0.0933 1.0000 Uani . . . . . . C33 C 1.20586(15) 0.3200(2) 0.85655(13) 0.0343 1.0000 Uani . . . . . . C34 C 1.31198(17) 0.2578(2) 0.93189(15) 0.0391 1.0000 Uani . . . . . . C35 C 1.40183(17) 0.1833(2) 0.89535(16) 0.0390 1.0000 Uani . . . . . . C36 C 1.38509(16) 0.17133(18) 0.78404(16) 0.0349 1.0000 Uani . . . . . . H61 H 0.9496 0.3138 0.3277 0.0321 1.0000 Uiso R . . . . . H91 H 1.1585 0.3124 0.4394 0.0322 1.0000 Uiso R . . . . . H102 H 1.2927 0.4960 0.6147 0.0346 1.0000 Uiso R . . . . . H101 H 1.1897 0.5560 0.5105 0.0369 1.0000 Uiso R . . . . . H132 H 1.3493 0.2189 0.5759 0.0375 1.0000 Uiso R . . . . . H131 H 1.2206 0.1264 0.5597 0.0385 1.0000 Uiso R . . . . . H161 H 1.0886 0.4842 0.6735 0.0305 1.0000 Uiso R . . . . . H191 H 0.6654 0.3566 0.5460 0.0317 1.0000 Uiso R . . . . . H201 H 0.5838 0.3321 0.3536 0.0307 1.0000 Uiso R . . . . . H231 H 0.7765 0.5854 0.8578 0.0377 1.0000 Uiso R . . . . . H243 H 0.5496 0.5557 0.8386 0.0838 1.0000 Uiso R . . . . . H242 H 0.6207 0.4065 0.8468 0.0844 1.0000 Uiso R . . . . . H241 H 0.5383 0.4635 0.7315 0.0853 1.0000 Uiso R . . . . . H251 H 0.6379 0.7623 0.7565 0.0887 1.0000 Uiso R . . . . . H253 H 0.7617 0.7400 0.7146 0.0902 1.0000 Uiso R . . . . . H252 H 0.6261 0.6776 0.6467 0.0890 1.0000 Uiso R . . . . . H301 H 0.8361 0.0040 0.7993 0.0629 1.0000 Uiso R . . . . . H313 H 0.7476 0.0153 0.9401 0.1382 1.0000 Uiso R . . . . . H312 H 0.8120 0.1693 0.9745 0.1392 1.0000 Uiso R . . . . . H311 H 0.6973 0.1500 0.8613 0.1390 1.0000 Uiso R . . . . . H323 H 0.9806 -0.0796 0.9647 0.1384 1.0000 Uiso R . . . . . H322 H 1.0212 0.0836 0.9958 0.1377 1.0000 Uiso R . . . . . H321 H 1.0579 0.0082 0.8986 0.1391 1.0000 Uiso R . . . . . H331 H 1.1452 0.3708 0.8824 0.0394 1.0000 Uiso R . . . . . H341 H 1.3209 0.2643 1.0082 0.0476 1.0000 Uiso R . . . . . H351 H 1.4732 0.1387 0.9464 0.0469 1.0000 Uiso R . . . . . H361 H 1.4476 0.1230 0.7587 0.0420 1.0000 Uiso 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 0.0326(5) 0.0479(6) 0.0337(5) -0.0023(4) -0.0018(4) 0.0029(4) C2 0.0305(7) 0.0306(8) 0.0321(8) 0.0015(6) 0.0067(6) -0.0012(6) F3 0.0479(6) 0.0762(9) 0.0306(5) 0.0066(5) 0.0114(4) -0.0164(6) F4 0.0617(7) 0.0363(6) 0.0396(6) -0.0122(4) 0.0019(5) 0.0079(5) C5 0.0274(7) 0.0205(7) 0.0283(7) 0.0017(5) 0.0059(5) -0.0010(5) C6 0.0260(7) 0.0260(7) 0.0289(7) -0.0003(6) 0.0105(5) -0.0031(6) C7 0.0220(6) 0.0230(7) 0.0289(7) -0.0001(6) 0.0084(5) -0.0025(5) N8 0.0189(5) 0.0585(9) 0.0275(6) -0.0069(6) 0.0081(5) -0.0034(6) C9 0.0217(6) 0.0310(7) 0.0302(7) -0.0042(6) 0.0117(5) -0.0016(6) C10 0.0296(7) 0.0228(7) 0.0377(8) 0.0024(6) 0.0151(6) 0.0037(6) C11 0.0323(8) 0.0273(8) 0.0517(10) -0.0022(7) 0.0186(7) -0.0013(6) N12 0.0491(9) 0.0463(10) 0.0846(14) -0.0050(9) 0.0423(10) -0.0070(8) C13 0.0349(8) 0.0207(6) 0.0424(9) -0.0042(6) 0.0174(6) 0.0006(6) C14 0.0271(7) 0.0183(6) 0.0380(8) -0.0008(6) 0.0112(6) -0.0007(5) C15 0.0216(6) 0.0239(7) 0.0325(7) -0.0025(6) 0.0066(5) -0.0026(5) C16 0.0217(6) 0.0284(7) 0.0275(7) -0.0038(6) 0.0081(5) -0.0014(5) C17 0.0216(6) 0.0232(7) 0.0268(6) -0.0018(5) 0.0084(5) 0.0002(5) C18 0.0228(6) 0.0184(6) 0.0261(6) -0.0002(5) 0.0081(5) -0.0009(5) C19 0.0238(6) 0.0195(6) 0.0332(7) -0.0001(6) 0.0103(5) -0.0002(5) C20 0.0225(6) 0.0239(7) 0.0331(7) -0.0007(6) 0.0057(5) 0.0000(5) C21 0.0254(7) 0.0270(7) 0.0295(7) -0.0015(6) 0.0107(5) 0.0007(6) O22 0.0246(5) 0.0342(6) 0.0387(6) -0.0111(5) 0.0125(4) -0.0008(4) C23 0.0291(7) 0.0360(8) 0.0350(8) -0.0078(7) 0.0139(6) 0.0034(6) C24 0.0438(10) 0.0542(12) 0.0860(16) -0.0133(12) 0.0413(11) -0.0027(10) C25 0.0665(14) 0.0509(13) 0.0751(15) 0.0142(11) 0.0398(12) 0.0287(11) O26 0.0354(6) 0.0411(7) 0.0638(9) -0.0249(7) 0.0240(6) -0.0115(5) C27 0.0236(6) 0.0269(7) 0.0263(7) 0.0008(6) 0.0056(5) 0.0010(6) O28 0.0576(8) 0.0250(6) 0.0370(6) -0.0004(5) 0.0169(6) 0.0064(5) O29 0.0540(7) 0.0315(6) 0.0302(6) 0.0017(5) 0.0170(5) -0.0022(5) C30 0.0761(14) 0.0393(10) 0.0397(10) 0.0119(8) 0.0210(9) -0.0027(10) C31 0.0696(17) 0.097(2) 0.129(3) 0.074(2) 0.0537(19) 0.0223(16) C32 0.0771(18) 0.111(3) 0.109(2) 0.075(2) 0.0547(18) 0.0471(18) C33 0.0282(7) 0.0385(9) 0.0336(8) -0.0069(7) 0.0055(6) 0.0012(6) C34 0.0341(8) 0.0444(10) 0.0335(8) -0.0023(7) 0.0019(7) 0.0012(7) C35 0.0303(7) 0.0370(9) 0.0441(9) 0.0035(7) 0.0022(7) 0.0050(7) C36 0.0285(7) 0.0264(7) 0.0503(10) 0.0029(7) 0.0125(7) 0.0033(6) _refine_ls_extinction_method None _oxford_refine_ls_scale 6.77(14) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag F1 . C2 . 1.3389(19) yes C2 . F3 . 1.333(2) yes C2 . F4 . 1.3490(19) yes C2 . C5 . 1.496(2) yes C5 . C6 . 1.400(2) yes C5 . C20 . 1.389(2) yes C6 . C7 . 1.393(2) yes C6 . H61 . 0.954 no C7 . N8 . 1.3677(18) yes C7 . C18 . 1.4082(19) yes N8 . C9 . 1.4427(17) yes N8 . C16 . 1.4544(19) yes C9 . C10 . 1.543(2) yes C9 . C13 . 1.525(2) yes C9 . H91 . 0.994 no C10 . C11 . 1.463(2) yes C10 . H102 . 0.955 no C10 . H101 . 0.952 no C11 . N12 . 1.139(2) yes C13 . C14 . 1.509(2) yes C13 . H132 . 0.964 no C13 . H131 . 0.977 no C14 . C15 . 1.404(2) yes C14 . C36 . 1.397(2) yes C15 . C16 . 1.520(2) yes C15 . C33 . 1.395(2) yes C16 . C17 . 1.5716(18) yes C16 . H161 . 0.976 no C17 . C18 . 1.5361(19) yes C17 . C21 . 1.531(2) yes C17 . C27 . 1.536(2) yes C18 . C19 . 1.3754(19) yes C19 . C20 . 1.401(2) yes C19 . H191 . 0.969 no C20 . H201 . 0.951 no C21 . O22 . 1.3257(18) yes C21 . O26 . 1.200(2) yes O22 . C23 . 1.4681(18) yes C23 . C24 . 1.497(2) yes C23 . C25 . 1.504(3) yes C23 . H231 . 0.994 no C24 . H243 . 0.982 no C24 . H242 . 0.950 no C24 . H241 . 0.973 no C25 . H251 . 0.969 no C25 . H253 . 0.983 no C25 . H252 . 0.967 no C27 . O28 . 1.198(2) yes C27 . O29 . 1.3266(19) yes O29 . C30 . 1.474(2) yes C30 . C31 . 1.488(4) yes C30 . C32 . 1.472(4) yes C30 . H301 . 0.987 no C31 . H313 . 0.961 no C31 . H312 . 0.982 no C31 . H311 . 0.981 no C32 . H323 . 0.984 no C32 . H322 . 0.974 no C32 . H321 . 0.961 no C33 . C34 . 1.390(2) yes C33 . H331 . 0.947 no C34 . C35 . 1.387(3) yes C34 . H341 . 0.952 no C35 . C36 . 1.383(3) yes C35 . H351 . 0.948 no C36 . H361 . 0.948 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag F1 . C2 . F3 . 106.59(13) yes F1 . C2 . F4 . 105.38(13) yes F3 . C2 . F4 . 106.53(15) yes F1 . C2 . C5 . 113.35(13) yes F3 . C2 . C5 . 113.26(13) yes F4 . C2 . C5 . 111.18(13) yes C2 . C5 . C6 . 118.31(13) yes C2 . C5 . C20 . 119.33(13) yes C6 . C5 . C20 . 122.28(13) yes C5 . C6 . C7 . 117.33(13) yes C5 . C6 . H61 . 120.9 no C7 . C6 . H61 . 121.8 no C6 . C7 . N8 . 129.14(13) yes C6 . C7 . C18 . 120.71(12) yes N8 . C7 . C18 . 110.10(12) yes C7 . N8 . C9 . 128.14(13) yes C7 . N8 . C16 . 111.87(12) yes C9 . N8 . C16 . 119.00(12) yes N8 . C9 . C10 . 109.98(12) yes N8 . C9 . C13 . 106.83(13) yes C10 . C9 . C13 . 112.34(12) yes N8 . C9 . H91 . 108.7 no C10 . C9 . H91 . 108.8 no C13 . C9 . H91 . 110.2 no C9 . C10 . C11 . 112.51(13) yes C9 . C10 . H102 . 110.2 no C11 . C10 . H102 . 108.4 no C9 . C10 . H101 . 109.4 no C11 . C10 . H101 . 106.0 no H102 . C10 . H101 . 110.3 no C10 . C11 . N12 . 179.1(2) yes C9 . C13 . C14 . 111.59(12) yes C9 . C13 . H132 . 109.3 no C14 . C13 . H132 . 109.0 no C9 . C13 . H131 . 106.7 no C14 . C13 . H131 . 108.9 no H132 . C13 . H131 . 111.3 no C13 . C14 . C15 . 121.91(14) yes C13 . C14 . C36 . 119.57(14) yes C15 . C14 . C36 . 118.52(15) yes C14 . C15 . C16 . 120.35(13) yes C14 . C15 . C33 . 119.80(14) yes C16 . C15 . C33 . 119.66(13) yes C15 . C16 . N8 . 110.86(12) yes C15 . C16 . C17 . 118.36(12) yes N8 . C16 . C17 . 103.64(11) yes C15 . C16 . H161 . 107.6 no N8 . C16 . H161 . 109.9 no C17 . C16 . H161 . 106.2 no C16 . C17 . C18 . 101.53(11) yes C16 . C17 . C21 . 111.02(11) yes C18 . C17 . C21 . 112.25(12) yes C16 . C17 . C27 . 111.01(11) yes C18 . C17 . C27 . 107.68(11) yes C21 . C17 . C27 . 112.77(12) yes C17 . C18 . C7 . 108.77(11) yes C17 . C18 . C19 . 130.06(12) yes C7 . C18 . C19 . 121.01(13) yes C18 . C19 . C20 . 119.12(13) yes C18 . C19 . H191 . 120.9 no C20 . C19 . H191 . 119.9 no C19 . C20 . C5 . 119.52(13) yes C19 . C20 . H201 . 120.2 no C5 . C20 . H201 . 120.3 no C17 . C21 . O22 . 110.85(12) yes C17 . C21 . O26 . 124.37(13) yes O22 . C21 . O26 . 124.78(14) yes C21 . O22 . C23 . 118.06(12) yes O22 . C23 . C24 . 105.51(14) yes O22 . C23 . C25 . 109.47(14) yes C24 . C23 . C25 . 113.78(18) yes O22 . C23 . H231 . 108.5 no C24 . C23 . H231 . 111.5 no C25 . C23 . H231 . 107.9 no C23 . C24 . H243 . 110.4 no C23 . C24 . H242 . 110.1 no H243 . C24 . H242 . 109.9 no C23 . C24 . H241 . 108.1 no H243 . C24 . H241 . 108.8 no H242 . C24 . H241 . 109.5 no C23 . C25 . H251 . 108.3 no C23 . C25 . H253 . 109.4 no H251 . C25 . H253 . 110.2 no C23 . C25 . H252 . 111.0 no H251 . C25 . H252 . 109.6 no H253 . C25 . H252 . 108.3 no C17 . C27 . O28 . 122.15(13) yes C17 . C27 . O29 . 112.58(13) yes O28 . C27 . O29 . 125.26(15) yes C27 . O29 . C30 . 117.19(14) yes O29 . C30 . C31 . 105.81(19) yes O29 . C30 . C32 . 109.0(2) yes C31 . C30 . C32 . 113.6(2) yes O29 . C30 . H301 . 108.8 no C31 . C30 . H301 . 108.1 no C32 . C30 . H301 . 111.2 no C30 . C31 . H313 . 107.5 no C30 . C31 . H312 . 106.1 no H313 . C31 . H312 . 111.2 no C30 . C31 . H311 . 110.3 no H313 . C31 . H311 . 111.1 no H312 . C31 . H311 . 110.4 no C30 . C32 . H323 . 111.9 no C30 . C32 . H322 . 106.9 no H323 . C32 . H322 . 110.1 no C30 . C32 . H321 . 109.4 no H323 . C32 . H321 . 109.2 no H322 . C32 . H321 . 109.3 no C15 . C33 . C34 . 120.59(16) yes C15 . C33 . H331 . 120.3 no C34 . C33 . H331 . 119.1 no C33 . C34 . C35 . 119.85(17) yes C33 . C34 . H341 . 119.5 no C35 . C34 . H341 . 120.6 no C34 . C35 . C36 . 119.72(15) yes C34 . C35 . H351 . 120.1 no C36 . C35 . H351 . 120.2 no C14 . C36 . C35 . 121.50(15) yes C14 . C36 . H361 . 118.4 no C35 . C36 . H361 . 120.1 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C10 . H101 . O28 2_756 128.64 0.952 2.365 3.051(3) yes _chemical_name_common . #============================================================================== data_26 _database_code_depnum_ccdc_archive 'CCDC 845083' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 11-04-27 _audit_creation_method CRYSTALS_ver_14.21 _oxford_structure_analysis_title 6338 _chemical_name_systematic . _chemical_melting_point 'not measured' _cell_length_a 9.3165(1) _cell_length_b 14.3322(1) _cell_length_c 19.7050(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2631.13(4) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C32 H29 N1 O4 S1 # Dc = 1.32 Fooo = 1104.00 Mu = 14.07 M = 523.65 # Found Formula = C32 H29 N1 O4 S1 # Dc = 1.32 FOOO = 1104.00 Mu = 14.07 M = 523.65 _chemical_formula_sum 'C32 H29 N1 O4 S1' _chemical_formula_moiety 'C32 H29 N1 O4 S1' _chemical_compound_source . _chemical_formula_weight 523.65 _cell_measurement_reflns_used 31772 _cell_measurement_theta_min 3 _cell_measurement_theta_max 77 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour clear_pale_colourless _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.06 _exptl_crystal_size_max 0.24 _exptl_crystal_density_diffrn 1.322 _exptl_crystal_density_meas 'not measured' _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1104 _exptl_absorpt_coefficient_mu 1.407 # Sheldrick geometric approximatio 0.92 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% . _diffrn_ambient_temperature 150 _diffrn_reflns_number 43647 _reflns_number_total 5518 _diffrn_reflns_av_R_equivalents 0.024 # Number of reflections without Friedels Law is 5518 # Number of reflections with Friedels Law is 3125 # Theoretical number of reflections is about 2777 _diffrn_reflns_theta_min 3.814 _diffrn_reflns_theta_max 76.872 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 76.872 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 18 _reflns_limit_l_min 0 _reflns_limit_l_max 24 _oxford_diffrn_Wilson_B_factor 1.93 _oxford_diffrn_Wilson_scale 0.04 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.41 _refine_diff_density_max 0.26 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 5498 _refine_ls_number_restraints 0 _refine_ls_number_parameters 344 _oxford_refine_ls_R_factor_ref 0.0239 _refine_ls_wR_factor_ref 0.0621 _refine_ls_goodness_of_fit_ref 1.0057 _refine_ls_shift/su_max 0.0011690 _refine_ls_shift/su_mean 0.0000574 # The values computed from all data _oxford_reflns_number_all 5498 _refine_ls_R_factor_all 0.0239 _refine_ls_wR_factor_all 0.0621 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5447 _refine_ls_R_factor_gt 0.0237 _refine_ls_wR_factor_gt 0.0619 _refine_ls_abs_structure_Flack 0.001(9) _refine_ls_abs_structure_details 'Flack (1983), 2393 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.04P)^2^ + 0.49P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Oxford Diffraction, (2010). CrysAlisPro. Oxford Diffraction, (2010). Supernova User Manual. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Flack, H. D. (1983). Acta Cryst. A39, 876-881. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens S1 S 0.47479(3) 0.67719(2) 0.465912(12) 0.0236 1.0000 Uani . . . . . . O2 O 0.42496(10) 0.77023(6) 0.48105(4) 0.0330 1.0000 Uani . . . . . . O3 O 0.52718(11) 0.62017(7) 0.52098(4) 0.0340 1.0000 Uani . . . . . . C4 C 0.33429(12) 0.61605(8) 0.42542(6) 0.0231 1.0000 Uani . . . . . . C5 C 0.20400(13) 0.66026(9) 0.41503(7) 0.0297 1.0000 Uani . . . . . . C6 C 0.09108(14) 0.60932(10) 0.38753(7) 0.0354 1.0000 Uani . . . . . . C7 C 0.11060(14) 0.51718(9) 0.36978(7) 0.0329 1.0000 Uani . . . . . . C8 C 0.24196(15) 0.47374(9) 0.37950(7) 0.0328 1.0000 Uani . . . . . . C9 C 0.35448(13) 0.52259(8) 0.40858(7) 0.0280 1.0000 Uani . . . . . . C10 C 0.61907(11) 0.68487(8) 0.40639(5) 0.0208 1.0000 Uani . . . . . . C11 C 0.60230(11) 0.76071(7) 0.35250(5) 0.0187 1.0000 Uani . . . . . . N12 N 0.48551(9) 0.73962(6) 0.30393(4) 0.0170 1.0000 Uani . . . . . . C13 C 0.40995(11) 0.81892(7) 0.28045(5) 0.0179 1.0000 Uani . . . . . . C14 C 0.39169(11) 0.81827(7) 0.21046(5) 0.0186 1.0000 Uani . . . . . . C15 C 0.45167(11) 0.72753(7) 0.18244(5) 0.0171 1.0000 Uani . . . . . . C16 C 0.55076(10) 0.69540(7) 0.24213(5) 0.0169 1.0000 Uani . . . . . . C17 C 0.70639(11) 0.72876(7) 0.24441(5) 0.0177 1.0000 Uani . . . . . . C18 C 0.73476(11) 0.76537(7) 0.30857(5) 0.0188 1.0000 Uani . . . . . . C19 C 0.87067(12) 0.79681(8) 0.32662(6) 0.0233 1.0000 Uani . . . . . . C20 C 0.98005(13) 0.79151(8) 0.27877(6) 0.0260 1.0000 Uani . . . . . . C21 C 0.95393(12) 0.75413(8) 0.21502(6) 0.0254 1.0000 Uani . . . . . . C22 C 0.81783(12) 0.72168(8) 0.19757(6) 0.0220 1.0000 Uani . . . . . . C23 C 0.53386(12) 0.73797(7) 0.11578(5) 0.0196 1.0000 Uani . . . . . . O24 O 0.54831(10) 0.80934(6) 0.08443(4) 0.0279 1.0000 Uani . . . . . . O25 O 0.58389(9) 0.65481(5) 0.09574(4) 0.0215 1.0000 Uani . . . . . . C26 C 0.65166(13) 0.65076(9) 0.02846(5) 0.0255 1.0000 Uani . . . . . . C27 C 0.53683(14) 0.65570(10) -0.02547(6) 0.0324 1.0000 Uani . . . . . . C28 C 0.7346(2) 0.56065(12) 0.02740(7) 0.0487 1.0000 Uani . . . . . . C29 C 0.32694(11) 0.65963(7) 0.16807(5) 0.0181 1.0000 Uani . . . . . . C30 C 0.27853(13) 0.59495(8) 0.21534(6) 0.0246 1.0000 Uani . . . . . . C31 C 0.16709(14) 0.53429(9) 0.19858(7) 0.0309 1.0000 Uani . . . . . . C32 C 0.10300(14) 0.53746(9) 0.13544(7) 0.0295 1.0000 Uani . . . . . . C33 C 0.14771(13) 0.60318(9) 0.08860(6) 0.0271 1.0000 Uani . . . . . . C34 C 0.25833(12) 0.66388(8) 0.10530(6) 0.0228 1.0000 Uani . . . . . . C35 C 0.31886(12) 0.89030(8) 0.17841(6) 0.0227 1.0000 Uani . . . . . . C36 C 0.26564(13) 0.96382(8) 0.21747(6) 0.0262 1.0000 Uani . . . . . . C37 C 0.28342(12) 0.96342(8) 0.28750(6) 0.0255 1.0000 Uani . . . . . . C38 C 0.35499(12) 0.89115(8) 0.32025(6) 0.0225 1.0000 Uani . . . . . . H51 H 0.1939 0.7260 0.4265 0.0370 1.0000 Uiso R . . . . . H61 H 0.0028 0.6378 0.3818 0.0426 1.0000 Uiso R . . . . . H71 H 0.0350 0.4824 0.3495 0.0382 1.0000 Uiso R . . . . . H81 H 0.2549 0.4085 0.3667 0.0400 1.0000 Uiso R . . . . . H91 H 0.4420 0.4924 0.4161 0.0338 1.0000 Uiso R . . . . . H101 H 0.7023 0.6996 0.4341 0.0269 1.0000 Uiso R . . . . . H102 H 0.6292 0.6251 0.3869 0.0260 1.0000 Uiso R . . . . . H111 H 0.5836 0.8198 0.3747 0.0227 1.0000 Uiso R . . . . . H161 H 0.5471 0.6269 0.2459 0.0207 1.0000 Uiso R . . . . . H191 H 0.8889 0.8210 0.3708 0.0271 1.0000 Uiso R . . . . . H201 H 1.0736 0.8117 0.2908 0.0303 1.0000 Uiso R . . . . . H211 H 1.0298 0.7492 0.1833 0.0314 1.0000 Uiso R . . . . . H221 H 0.8013 0.6951 0.1544 0.0259 1.0000 Uiso R . . . . . H261 H 0.7188 0.7038 0.0257 0.0296 1.0000 Uiso R . . . . . H271 H 0.5792 0.6470 -0.0688 0.0480 1.0000 Uiso R . . . . . H272 H 0.4872 0.7171 -0.0249 0.0478 1.0000 Uiso R . . . . . H273 H 0.4704 0.6054 -0.0181 0.0482 1.0000 Uiso R . . . . . H281 H 0.7887 0.5540 -0.0146 0.0726 1.0000 Uiso R . . . . . H282 H 0.6674 0.5062 0.0315 0.0715 1.0000 Uiso R . . . . . H283 H 0.8023 0.5595 0.0657 0.0720 1.0000 Uiso R . . . . . H301 H 0.3206 0.5927 0.2596 0.0293 1.0000 Uiso R . . . . . H311 H 0.1365 0.4906 0.2320 0.0379 1.0000 Uiso R . . . . . H321 H 0.0283 0.4940 0.1251 0.0347 1.0000 Uiso R . . . . . H331 H 0.1054 0.6078 0.0456 0.0332 1.0000 Uiso R . . . . . H341 H 0.2895 0.7112 0.0716 0.0294 1.0000 Uiso R . . . . . H351 H 0.3076 0.8885 0.1299 0.0273 1.0000 Uiso R . . . . . H361 H 0.2175 1.0149 0.1963 0.0303 1.0000 Uiso R . . . . . H371 H 0.2437 1.0166 0.3136 0.0314 1.0000 Uiso R . . . . . H381 H 0.3674 0.8906 0.3682 0.0278 1.0000 Uiso 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 0.02559(12) 0.02974(14) 0.01544(11) 0.00066(10) 0.00376(10) 0.00028(11) O2 0.0366(5) 0.0338(5) 0.0288(4) -0.0088(4) 0.0082(4) 0.0004(4) O3 0.0362(5) 0.0471(5) 0.0187(4) 0.0092(4) 0.0003(4) -0.0019(4) C4 0.0226(5) 0.0258(5) 0.0210(5) 0.0047(4) 0.0038(4) 0.0007(4) C5 0.0266(6) 0.0283(6) 0.0341(6) 0.0041(5) 0.0045(5) 0.0053(5) C6 0.0217(6) 0.0398(7) 0.0446(7) 0.0124(6) 0.0004(5) 0.0046(5) C7 0.0260(6) 0.0362(6) 0.0365(7) 0.0119(5) -0.0028(5) -0.0066(5) C8 0.0328(6) 0.0259(6) 0.0397(7) 0.0060(5) -0.0024(5) -0.0009(5) C9 0.0233(5) 0.0264(5) 0.0344(6) 0.0053(5) 0.0006(5) 0.0039(5) C10 0.0194(5) 0.0267(5) 0.0163(5) 0.0006(4) 0.0005(4) 0.0011(4) C11 0.0190(5) 0.0202(5) 0.0170(5) -0.0015(4) -0.0016(4) -0.0005(4) N12 0.0178(4) 0.0181(4) 0.0150(4) -0.0008(3) 0.0002(3) 0.0011(3) C13 0.0146(4) 0.0184(5) 0.0206(5) 0.0011(4) -0.0003(4) -0.0012(4) C14 0.0166(4) 0.0189(5) 0.0202(5) 0.0000(4) -0.0007(4) -0.0022(4) C15 0.0165(5) 0.0186(5) 0.0162(4) 0.0010(4) -0.0011(4) -0.0015(4) C16 0.0169(5) 0.0183(4) 0.0154(4) 0.0006(3) 0.0010(4) -0.0002(4) C17 0.0166(5) 0.0182(4) 0.0183(5) 0.0027(4) -0.0014(4) 0.0000(4) C18 0.0194(5) 0.0185(5) 0.0184(5) 0.0021(4) -0.0016(4) 0.0003(4) C19 0.0230(5) 0.0236(5) 0.0232(5) 0.0014(4) -0.0056(4) -0.0033(4) C20 0.0184(5) 0.0279(5) 0.0318(6) 0.0056(4) -0.0036(5) -0.0044(4) C21 0.0185(5) 0.0303(6) 0.0275(5) 0.0047(4) 0.0039(4) 0.0010(4) C22 0.0200(5) 0.0260(5) 0.0199(5) 0.0010(4) 0.0007(4) 0.0011(4) C23 0.0189(4) 0.0235(5) 0.0162(4) -0.0005(4) -0.0016(4) -0.0042(4) O24 0.0375(5) 0.0240(4) 0.0223(4) 0.0041(3) 0.0040(3) -0.0065(3) O25 0.0241(4) 0.0253(4) 0.0151(3) 0.0005(3) 0.0035(3) -0.0002(3) C26 0.0254(5) 0.0367(6) 0.0144(5) 0.0008(4) 0.0057(4) 0.0000(5) C27 0.0316(6) 0.0484(7) 0.0174(5) -0.0048(5) 0.0015(5) -0.0018(6) C28 0.0600(9) 0.0611(9) 0.0249(6) 0.0041(6) 0.0153(6) 0.0308(8) C29 0.0169(5) 0.0175(5) 0.0198(5) -0.0026(4) 0.0005(4) -0.0003(4) C30 0.0269(6) 0.0264(5) 0.0204(5) 0.0004(4) -0.0029(4) -0.0065(4) C31 0.0336(6) 0.0279(6) 0.0312(6) 0.0030(5) -0.0030(5) -0.0115(5) C32 0.0262(6) 0.0274(6) 0.0350(6) -0.0075(5) -0.0048(5) -0.0076(5) C33 0.0231(5) 0.0339(6) 0.0243(5) -0.0054(5) -0.0051(4) -0.0014(5) C34 0.0202(5) 0.0277(5) 0.0206(5) 0.0008(4) -0.0005(4) -0.0010(4) C35 0.0209(5) 0.0231(5) 0.0242(5) 0.0031(4) -0.0045(4) -0.0015(4) C36 0.0220(5) 0.0200(5) 0.0367(6) 0.0036(4) -0.0040(5) 0.0014(4) C37 0.0223(5) 0.0195(5) 0.0346(6) -0.0045(4) 0.0017(4) 0.0010(4) C38 0.0214(5) 0.0231(5) 0.0231(5) -0.0038(4) 0.0006(4) 0.0001(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 4.94(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag S1 . O2 . 1.4431(9) yes S1 . O3 . 1.4436(9) yes S1 . C4 . 1.7657(12) yes S1 . C10 . 1.7873(11) yes C4 . C5 . 1.3844(16) yes C4 . C9 . 1.3928(16) yes C5 . C6 . 1.3905(19) yes C5 . H51 . 0.973 no C6 . C7 . 1.378(2) yes C6 . H61 . 0.925 no C7 . C8 . 1.3864(18) yes C7 . H71 . 0.951 no C8 . C9 . 1.3847(18) yes C8 . H81 . 0.976 no C9 . H91 . 0.935 no C10 . C11 . 1.5277(14) yes C10 . H101 . 0.972 no C10 . H102 . 0.943 no C11 . N12 . 1.4802(13) yes C11 . C18 . 1.5089(14) yes C11 . H111 . 0.969 no N12 . C13 . 1.4147(13) yes N12 . C16 . 1.5014(12) yes C13 . C14 . 1.3896(14) yes C13 . C38 . 1.3961(15) yes C14 . C15 . 1.5194(14) yes C14 . C35 . 1.3874(15) yes C15 . C16 . 1.5646(13) yes C15 . C23 . 1.5278(14) yes C15 . C29 . 1.5420(14) yes C16 . C17 . 1.5274(13) yes C16 . H161 . 0.985 no C17 . C18 . 1.3941(14) yes C17 . C22 . 1.3929(15) yes C18 . C19 . 1.3903(15) yes C19 . C20 . 1.3904(17) yes C19 . H191 . 0.952 no C20 . C21 . 1.3871(16) yes C20 . H201 . 0.949 no C21 . C22 . 1.3937(16) yes C21 . H211 . 0.946 no C22 . H221 . 0.945 no C23 . O24 . 1.2025(13) yes C23 . O25 . 1.3393(13) yes O25 . C26 . 1.4695(12) yes C26 . C27 . 1.5095(16) yes C26 . C28 . 1.5052(18) yes C26 . H261 . 0.986 no C27 . H271 . 0.949 no C27 . H272 . 0.995 no C27 . H273 . 0.961 no C28 . H281 . 0.973 no C28 . H282 . 1.004 no C28 . H283 . 0.983 no C29 . C30 . 1.3894(15) yes C29 . C34 . 1.3936(15) yes C30 . C31 . 1.3938(16) yes C30 . H301 . 0.957 no C31 . C32 . 1.3808(18) yes C31 . H311 . 0.953 no C32 . C33 . 1.3830(18) yes C32 . H321 . 0.956 no C33 . C34 . 1.3883(16) yes C33 . H331 . 0.937 no C34 . H341 . 0.992 no C35 . C36 . 1.3958(17) yes C35 . H351 . 0.962 no C36 . C37 . 1.3899(18) yes C36 . H361 . 0.955 no C37 . C38 . 1.3907(16) yes C37 . H371 . 0.991 no C38 . H381 . 0.951 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag O2 . S1 . O3 . 118.46(5) yes O2 . S1 . C4 . 108.27(6) yes O3 . S1 . C4 . 108.02(6) yes O2 . S1 . C10 . 108.71(5) yes O3 . S1 . C10 . 105.89(5) yes C4 . S1 . C10 . 106.95(5) yes S1 . C4 . C5 . 119.32(9) yes S1 . C4 . C9 . 119.00(9) yes C5 . C4 . C9 . 121.56(11) yes C4 . C5 . C6 . 118.73(12) yes C4 . C5 . H51 . 119.6 no C6 . C5 . H51 . 121.7 no C5 . C6 . C7 . 120.15(12) yes C5 . C6 . H61 . 119.3 no C7 . C6 . H61 . 120.6 no C6 . C7 . C8 . 120.78(12) yes C6 . C7 . H71 . 120.7 no C8 . C7 . H71 . 118.5 no C7 . C8 . C9 . 119.89(12) yes C7 . C8 . H81 . 120.3 no C9 . C8 . H81 . 119.8 no C4 . C9 . C8 . 118.86(11) yes C4 . C9 . H91 . 121.6 no C8 . C9 . H91 . 119.5 no S1 . C10 . C11 . 115.03(8) yes S1 . C10 . H101 . 104.1 no C11 . C10 . H101 . 108.5 no S1 . C10 . H102 . 106.7 no C11 . C10 . H102 . 111.9 no H101 . C10 . H102 . 110.3 no C10 . C11 . N12 . 112.29(8) yes C10 . C11 . C18 . 110.28(9) yes N12 . C11 . C18 . 103.85(8) yes C10 . C11 . H111 . 109.0 no N12 . C11 . H111 . 109.8 no C18 . C11 . H111 . 111.6 no C11 . N12 . C13 . 114.40(8) yes C11 . N12 . C16 . 108.24(8) yes C13 . N12 . C16 . 105.98(8) yes N12 . C13 . C14 . 112.35(9) yes N12 . C13 . C38 . 126.47(10) yes C14 . C13 . C38 . 121.17(10) yes C13 . C14 . C15 . 108.74(9) yes C13 . C14 . C35 . 120.44(10) yes C15 . C14 . C35 . 130.65(10) yes C14 . C15 . C16 . 101.29(8) yes C14 . C15 . C23 . 114.39(8) yes C16 . C15 . C23 . 112.30(8) yes C14 . C15 . C29 . 109.25(8) yes C16 . C15 . C29 . 113.38(8) yes C23 . C15 . C29 . 106.36(8) yes C15 . C16 . N12 . 104.28(7) yes C15 . C16 . C17 . 119.34(8) yes N12 . C16 . C17 . 103.20(8) yes C15 . C16 . H161 . 109.3 no N12 . C16 . H161 . 110.2 no C17 . C16 . H161 . 110.0 no C16 . C17 . C18 . 108.93(9) yes C16 . C17 . C22 . 131.71(10) yes C18 . C17 . C22 . 119.15(10) yes C11 . C18 . C17 . 110.40(9) yes C11 . C18 . C19 . 127.76(10) yes C17 . C18 . C19 . 121.78(10) yes C18 . C19 . C20 . 118.44(10) yes C18 . C19 . H191 . 121.0 no C20 . C19 . H191 . 120.6 no C19 . C20 . C21 . 120.44(11) yes C19 . C20 . H201 . 119.2 no C21 . C20 . H201 . 120.4 no C20 . C21 . C22 . 120.80(11) yes C20 . C21 . H211 . 119.7 no C22 . C21 . H211 . 119.5 no C21 . C22 . C17 . 119.36(10) yes C21 . C22 . H221 . 120.3 no C17 . C22 . H221 . 120.3 no C15 . C23 . O24 . 125.52(10) yes C15 . C23 . O25 . 109.93(8) yes O24 . C23 . O25 . 124.51(10) yes C23 . O25 . C26 . 116.79(8) yes O25 . C26 . C27 . 109.19(9) yes O25 . C26 . C28 . 105.48(9) yes C27 . C26 . C28 . 113.23(12) yes O25 . C26 . H261 . 106.9 no C27 . C26 . H261 . 112.0 no C28 . C26 . H261 . 109.6 no C26 . C27 . H271 . 109.4 no C26 . C27 . H272 . 111.3 no H271 . C27 . H272 . 108.7 no C26 . C27 . H273 . 108.4 no H271 . C27 . H273 . 107.7 no H272 . C27 . H273 . 111.3 no C26 . C28 . H281 . 111.2 no C26 . C28 . H282 . 110.2 no H281 . C28 . H282 . 108.3 no C26 . C28 . H283 . 109.4 no H281 . C28 . H283 . 108.6 no H282 . C28 . H283 . 109.0 no C15 . C29 . C30 . 122.87(9) yes C15 . C29 . C34 . 118.75(9) yes C30 . C29 . C34 . 118.38(10) yes C29 . C30 . C31 . 119.94(11) yes C29 . C30 . H301 . 120.0 no C31 . C30 . H301 . 120.0 no C30 . C31 . C32 . 121.00(11) yes C30 . C31 . H311 . 118.0 no C32 . C31 . H311 . 121.0 no C31 . C32 . C33 . 119.57(11) yes C31 . C32 . H321 . 119.0 no C33 . C32 . H321 . 121.4 no C32 . C33 . C34 . 119.48(11) yes C32 . C33 . H331 . 121.7 no C34 . C33 . H331 . 118.8 no C29 . C34 . C33 . 121.57(11) yes C29 . C34 . H341 . 119.3 no C33 . C34 . H341 . 119.2 no C14 . C35 . C36 . 118.98(11) yes C14 . C35 . H351 . 119.0 no C36 . C35 . H351 . 122.0 no C35 . C36 . C37 . 120.13(11) yes C35 . C36 . H361 . 120.3 no C37 . C36 . H361 . 119.5 no C36 . C37 . C38 . 121.39(11) yes C36 . C37 . H371 . 117.9 no C38 . C37 . H371 . 120.7 no C13 . C38 . C37 . 117.87(10) yes C13 . C38 . H381 . 120.4 no C37 . C38 . H381 . 121.7 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C8 . H81 . O24 3_645 122.27 0.976 2.511 3.1424(16) yes C22 . H221 . O25 . 131.89 0.945 2.402 3.1137(16) yes #============================================================================== # start Validation Reply Form #============================================================================== _vrf_DIFMX01_14 ; PROBLEM: The maximum difference density is > 0.1*ZMAX*1.00 RESPONSE: The largest peak in the difference map is associated with the disordered CF3 group. ; #============================================================================== # end Validation Reply Form #============================================================================== _chemical_name_common .