# Electronic Supplementary Material (ESI) for CrystEngComm # 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_1 _database_code_depnum_ccdc_archive 'CCDC 886501' #TrackingRef '11911_web_deposit_cif_file_0_GuillermoMinguezEspallargas_1339668240.1.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H17 F4 I2 N2 O2' _chemical_formula_weight 635.15 _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' I I -0.4742 1.8119 '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_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 10.0452(5) _cell_length_b 10.8471(4) _cell_length_c 11.3100(5) _cell_angle_alpha 109.224(4) _cell_angle_beta 106.972(4) _cell_angle_gamma 100.343(4) _cell_volume 1059.84(10) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8720 _cell_measurement_theta_min 2.2207 _cell_measurement_theta_max 27.4307 _cell_oxdiff_twin_number 2 loop_ _cell_oxdiff_twin_id _cell_oxdiff_twin_matrix_11 _cell_oxdiff_twin_matrix_12 _cell_oxdiff_twin_matrix_13 _cell_oxdiff_twin_matrix_21 _cell_oxdiff_twin_matrix_22 _cell_oxdiff_twin_matrix_23 _cell_oxdiff_twin_matrix_31 _cell_oxdiff_twin_matrix_32 _cell_oxdiff_twin_matrix_33 1 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000 1.0000 2 -0.0624 -0.9356 -0.0015 -1.0646 0.0631 0.0016 0.0531 -0.0527 -1.0004 _exptl_crystal_description plate _exptl_crystal_colour blue _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.990 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 606 _exptl_absorpt_coefficient_mu 3.019 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5835 _exptl_absorpt_correction_T_max 0.9149 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.66 (release 28-04-2010 CrysAlis171 .NET) (compiled Apr 28 2010,14:27:37) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'multiwire proportional' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 27906 _diffrn_reflns_av_R_equivalents 0.0730 _diffrn_reflns_av_sigmaI/netI 0.0561 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.26 _diffrn_reflns_theta_max 27.51 _reflns_number_total 4688 _reflns_number_gt 3448 _reflns_threshold_expression >2sigma(I) loop_ _diffrn_oxdiff_twin_id _diffrn_oxdiff_twin_ratio _diffrn_oxdiff_twin_reflns_isolated _diffrn_oxdiff_twin_reflns_overlapped 1 0.7739 19801 9596 2 0.2261 0 9596 _computing_data_collection 'Bruker FRAMBO' _computing_cell_refinement 'Bruker FRAMBO' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. ; _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^)+(0.0325P)^2^+0.0000P] 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_extinction_coef ? _refine_ls_number_reflns 4688 _refine_ls_number_parameters 262 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0548 _refine_ls_R_factor_gt 0.0312 _refine_ls_wR_factor_ref 0.0679 _refine_ls_wR_factor_gt 0.0625 _refine_ls_goodness_of_fit_ref 0.959 _refine_ls_restrained_S_all 0.959 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _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 0.4972(4) 1.0136(4) 0.7519(4) 0.0158(8) Uani 1 1 d . . . N2 N 0.4580(3) 0.8897(3) 0.7565(3) 0.0148(7) Uani 1 1 d . . . O2 O 0.3352(3) 0.8325(3) 0.7570(3) 0.0232(7) Uani 1 1 d . . . C3 C 0.5846(4) 0.8323(4) 0.7833(4) 0.0194(9) Uani 1 1 d . . . C4 C 0.6869(4) 0.9137(4) 0.7360(4) 0.0198(9) Uani 1 1 d . . . N5 N 0.6352(4) 1.0375(3) 0.7527(3) 0.0182(8) Uani 1 1 d . . . O5 O 0.7119(3) 1.1453(3) 0.7529(3) 0.0254(7) Uani 1 1 d . . . C6 C 0.6424(5) 0.8663(4) 0.9341(4) 0.0246(10) Uani 1 1 d . . . H6A H 0.6780 0.9661 0.9848 0.037 Uiso 1 1 calc R . . H6B H 0.7227 0.8278 0.9565 0.037 Uiso 1 1 calc R . . H6C H 0.5637 0.8269 0.9580 0.037 Uiso 1 1 calc R . . C7 C 0.5286(5) 0.6774(4) 0.7017(5) 0.0255(10) Uani 1 1 d . . . H7A H 0.4923 0.6574 0.6049 0.038 Uiso 1 1 calc R . . H7B H 0.4492 0.6371 0.7242 0.038 Uiso 1 1 calc R . . H7C H 0.6084 0.6382 0.7235 0.038 Uiso 1 1 calc R . . C8 C 0.8496(5) 0.9571(5) 0.8210(5) 0.0269(10) Uani 1 1 d . . . H8A H 0.8657 1.0005 0.9170 0.040 Uiso 1 1 calc R . . H8B H 0.9036 1.0223 0.7959 0.040 Uiso 1 1 calc R . . H8C H 0.8838 0.8762 0.8046 0.040 Uiso 1 1 calc R . . C9 C 0.6605(5) 0.8462(4) 0.5866(5) 0.0266(10) Uani 1 1 d . . . H9A H 0.5559 0.8189 0.5327 0.040 Uiso 1 1 calc R . . H9B H 0.6941 0.7649 0.5697 0.040 Uiso 1 1 calc R . . H9C H 0.7147 0.9112 0.5614 0.040 Uiso 1 1 calc R . . C10 C 0.4069(5) 1.1051(4) 0.7442(4) 0.0178(9) Uani 1 1 d . . . C11 C 0.2538(5) 1.0542(4) 0.7003(4) 0.0215(9) Uani 1 1 d . . . H11 H 0.2081 0.9599 0.6753 0.026 Uiso 1 1 calc R . . C12 C 0.1699(5) 1.1421(4) 0.6936(5) 0.0254(10) Uani 1 1 d . . . H12 H 0.0665 1.1071 0.6614 0.030 Uiso 1 1 calc R . . C13 C 0.2355(5) 1.2800(4) 0.7333(4) 0.0258(10) Uani 1 1 d . . . H13 H 0.1774 1.3398 0.7300 0.031 Uiso 1 1 calc R . . C14 C 0.3845(5) 1.3309(5) 0.7774(5) 0.0294(11) Uani 1 1 d . . . H14 H 0.4290 1.4259 0.8048 0.035 Uiso 1 1 calc R . . C15 C 0.4707(5) 1.2452(4) 0.7824(4) 0.0223(10) Uani 1 1 d . . . H15 H 0.5737 1.2815 0.8119 0.027 Uiso 1 1 calc R . . C21 C 0.9188(4) 0.4110(4) 0.5384(4) 0.0172(9) Uani 1 1 d . . . I21 I 0.81289(3) 0.28656(3) 0.61153(3) 0.01836(8) Uani 1 1 d . . . C22 C 0.9071(4) 0.5414(4) 0.5605(4) 0.0165(9) Uani 1 1 d . . . F22 F 0.8178(3) 0.5857(2) 0.6215(3) 0.0258(6) Uani 1 1 d . . . C23 C 1.0137(4) 0.3718(4) 0.4766(4) 0.0159(8) Uani 1 1 d . . . F23 F 1.0284(3) 0.2457(2) 0.4486(3) 0.0241(6) Uani 1 1 d . . . C31 C 0.0904(4) 0.5796(4) 0.9597(4) 0.0180(9) Uani 1 1 d . . . I31 I 0.21397(3) 0.68901(3) 0.88657(3) 0.01907(8) Uani 1 1 d . . . C32 C -0.0457(4) 0.5937(4) 0.9566(4) 0.0146(8) Uani 1 1 d . . . F32 F -0.0939(3) 0.6864(2) 0.9140(3) 0.0258(6) Uani 1 1 d . . . C33 C 0.1327(4) 0.4843(4) 1.0052(4) 0.0181(9) Uani 1 1 d . . . F33 F 0.2648(2) 0.4665(2) 1.0148(3) 0.0246(6) Uani 1 1 d . . . _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 0.021(2) 0.0131(19) 0.012(2) 0.0058(16) 0.0061(17) 0.0020(17) N2 0.0165(17) 0.0144(16) 0.0171(19) 0.0094(14) 0.0082(15) 0.0041(15) O2 0.0211(15) 0.0268(16) 0.0298(19) 0.0185(15) 0.0140(14) 0.0052(14) C3 0.019(2) 0.020(2) 0.022(2) 0.0103(19) 0.0076(19) 0.0081(19) C4 0.020(2) 0.021(2) 0.022(2) 0.0100(19) 0.0099(19) 0.0100(19) N5 0.0193(18) 0.0172(18) 0.020(2) 0.0111(15) 0.0075(16) 0.0017(16) O5 0.0270(16) 0.0232(16) 0.0331(19) 0.0168(14) 0.0167(15) 0.0046(14) C6 0.027(2) 0.029(2) 0.023(3) 0.017(2) 0.009(2) 0.011(2) C7 0.028(2) 0.018(2) 0.037(3) 0.014(2) 0.017(2) 0.012(2) C8 0.021(2) 0.035(3) 0.033(3) 0.021(2) 0.012(2) 0.011(2) C9 0.029(2) 0.028(2) 0.029(3) 0.013(2) 0.018(2) 0.009(2) C10 0.024(2) 0.017(2) 0.010(2) 0.0037(17) 0.0045(18) 0.0083(19) C11 0.021(2) 0.019(2) 0.023(2) 0.0070(19) 0.0082(19) 0.0053(19) C12 0.021(2) 0.031(3) 0.025(3) 0.010(2) 0.007(2) 0.014(2) C13 0.031(2) 0.025(2) 0.019(2) 0.0061(19) 0.006(2) 0.017(2) C14 0.036(3) 0.018(2) 0.029(3) 0.009(2) 0.006(2) 0.010(2) C15 0.026(2) 0.020(2) 0.019(2) 0.0088(19) 0.0031(19) 0.008(2) C21 0.014(2) 0.023(2) 0.013(2) 0.0110(18) 0.0029(17) 0.0006(18) I21 0.01887(15) 0.01861(15) 0.01670(16) 0.00795(12) 0.00718(12) 0.00143(12) C22 0.0129(19) 0.020(2) 0.019(2) 0.0082(18) 0.0063(17) 0.0081(18) F22 0.0296(14) 0.0261(13) 0.0350(16) 0.0160(12) 0.0227(13) 0.0147(12) C23 0.016(2) 0.0128(19) 0.015(2) 0.0034(17) 0.0023(17) 0.0047(17) F23 0.0301(14) 0.0176(12) 0.0312(15) 0.0118(11) 0.0170(12) 0.0098(11) C31 0.018(2) 0.021(2) 0.015(2) 0.0084(18) 0.0066(18) 0.0035(19) I31 0.01956(15) 0.01926(15) 0.01663(16) 0.00821(12) 0.00695(12) -0.00010(12) C32 0.017(2) 0.0122(19) 0.015(2) 0.0057(17) 0.0040(17) 0.0067(17) F32 0.0284(14) 0.0261(13) 0.0328(16) 0.0197(12) 0.0134(12) 0.0131(12) C33 0.016(2) 0.021(2) 0.019(2) 0.0067(18) 0.0091(18) 0.0064(18) F33 0.0186(12) 0.0279(13) 0.0313(15) 0.0137(12) 0.0122(11) 0.0080(11) _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. ; _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 1.353(5) . ? C1 N5 1.362(5) . ? C1 C10 1.466(5) . ? N2 O2 1.280(4) . ? N2 C3 1.510(5) . ? C3 C6 1.521(6) . ? C3 C7 1.526(6) . ? C3 C4 1.557(6) . ? C4 N5 1.500(5) . ? C4 C9 1.522(6) . ? C4 C8 1.524(6) . ? N5 O5 1.278(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.402(6) . ? C10 C11 1.409(6) . ? C11 C12 1.386(6) . ? C11 H11 0.9500 . ? C12 C13 1.381(6) . ? C12 H12 0.9500 . ? C13 C14 1.371(6) . ? C13 H13 0.9500 . ? C14 C15 1.382(6) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C21 C23 1.385(6) . ? C21 C22 1.385(6) . ? C21 I21 2.091(4) . ? C22 F22 1.345(4) . ? C22 C23 1.372(6) 2_766 ? C23 F23 1.344(4) . ? C23 C22 1.372(6) 2_766 ? C31 C33 1.377(6) . ? C31 C32 1.394(5) . ? C31 I31 2.086(4) . ? C32 F32 1.355(4) . ? C32 C33 1.365(6) 2_567 ? C33 F33 1.353(4) . ? C33 C32 1.365(6) 2_567 ? _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 N5 107.7(3) . . ? N2 C1 C10 126.6(4) . . ? N5 C1 C10 125.7(3) . . ? O2 N2 C1 125.7(3) . . ? O2 N2 C3 121.4(3) . . ? C1 N2 C3 112.3(3) . . ? N2 C3 C6 106.0(3) . . ? N2 C3 C7 108.8(3) . . ? C6 C3 C7 110.6(3) . . ? N2 C3 C4 100.3(3) . . ? C6 C3 C4 115.0(3) . . ? C7 C3 C4 115.1(4) . . ? N5 C4 C9 105.7(3) . . ? N5 C4 C8 110.0(3) . . ? C9 C4 C8 109.9(4) . . ? N5 C4 C3 100.6(3) . . ? C9 C4 C3 114.7(4) . . ? C8 C4 C3 115.1(3) . . ? O5 N5 C1 126.6(3) . . ? O5 N5 C4 120.7(3) . . ? C1 N5 C4 112.3(3) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 118.5(4) . . ? C15 C10 C1 120.9(4) . . ? C11 C10 C1 120.6(4) . . ? C12 C11 C10 119.9(4) . . ? C12 C11 H11 120.1 . . ? C10 C11 H11 120.1 . . ? C13 C12 C11 120.5(4) . . ? C13 C12 H12 119.7 . . ? C11 C12 H12 119.7 . . ? C14 C13 C12 120.1(4) . . ? C14 C13 H13 120.0 . . ? C12 C13 H13 120.0 . . ? C13 C14 C15 120.7(4) . . ? C13 C14 H14 119.7 . . ? C15 C14 H14 119.7 . . ? C14 C15 C10 120.3(4) . . ? C14 C15 H15 119.8 . . ? C10 C15 H15 119.8 . . ? C23 C21 C22 117.1(4) . . ? C23 C21 I21 121.4(3) . . ? C22 C21 I21 121.3(3) . . ? F22 C22 C23 118.6(3) . 2_766 ? F22 C22 C21 119.7(4) . . ? C23 C22 C21 121.6(4) 2_766 . ? F23 C23 C22 118.1(4) . 2_766 ? F23 C23 C21 120.6(4) . . ? C22 C23 C21 121.3(4) 2_766 . ? C33 C31 C32 116.3(4) . . ? C33 C31 I31 122.7(3) . . ? C32 C31 I31 120.9(3) . . ? F32 C32 C33 118.8(3) . 2_567 ? F32 C32 C31 119.5(4) . . ? C33 C32 C31 121.7(4) 2_567 . ? F33 C33 C32 117.8(3) . 2_567 ? F33 C33 C31 120.2(4) . . ? C32 C33 C31 122.0(4) 2_567 . ? _diffrn_measured_fraction_theta_max 0.961 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.961 _refine_diff_density_max 1.335 _refine_diff_density_min -0.725 _refine_diff_density_rms 0.140 data_2 _database_code_depnum_ccdc_archive 'CCDC 886502' #TrackingRef '11912_web_deposit_cif_file_1_GuillermoMinguezEspallargas_1339668240.2.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C25 H17 F8 I2 N2 O2' _chemical_formula_weight 783.21 _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' I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.1945(2) _cell_length_b 14.5047(3) _cell_length_c 16.7801(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.577(2) _cell_angle_gamma 90.00 _cell_volume 2711.74(9) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 5822 _cell_measurement_theta_min 2.8970 _cell_measurement_theta_max 24.9791 _exptl_crystal_description needle _exptl_crystal_colour blue _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.918 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1500 _exptl_absorpt_coefficient_mu 2.401 _exptl_absorpt_correction_T_min 0.89760 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'SuperNova (Mo) X-ray Source' _diffrn_radiation_monochromator mirror _diffrn_measurement_device_type 'SuperNova, Single source at offset), Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.0267 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19964 _diffrn_reflns_av_R_equivalents 0.0504 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 2.90 _diffrn_reflns_theta_max 25.03 _reflns_number_total 4786 _reflns_number_gt 3814 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _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. ; _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^)+(0.0203P)^2^+0.0000P] 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_extinction_coef ? _refine_ls_number_reflns 4786 _refine_ls_number_parameters 356 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0477 _refine_ls_R_factor_gt 0.0324 _refine_ls_wR_factor_ref 0.0644 _refine_ls_wR_factor_gt 0.0573 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 _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 0.7799(3) -0.0144(3) -0.0914(2) 0.0203(9) Uani 1 1 d . . . N2 N 0.8226(3) 0.0531(2) -0.1369(2) 0.0235(8) Uani 1 1 d . . . O2 O 0.8371(2) 0.04748(19) -0.21138(16) 0.0304(7) Uani 1 1 d . . . C3 C 0.8651(4) 0.1364(3) -0.0882(2) 0.0259(10) Uani 1 1 d . . . C4 C 0.7912(4) 0.1247(3) -0.0147(2) 0.0268(10) Uani 1 1 d . . . N5 N 0.7706(3) 0.0219(2) -0.0176(2) 0.0223(8) Uani 1 1 d . . . O5 O 0.7407(3) -0.02350(19) 0.04245(17) 0.0312(7) Uani 1 1 d . . . C6 C 0.9998(3) 0.1237(3) -0.0695(2) 0.0293(10) Uani 1 1 d . . . H6A H 1.0156 0.0648 -0.0417 0.044 Uiso 1 1 calc R . . H6B H 1.0322 0.1742 -0.0352 0.044 Uiso 1 1 calc R . . H6C H 1.0384 0.1237 -0.1194 0.044 Uiso 1 1 calc R . . C7 C 0.8374(4) 0.2234(3) -0.1372(3) 0.0365(12) Uani 1 1 d . . . H7A H 0.8872 0.2250 -0.1821 0.055 Uiso 1 1 calc R . . H7B H 0.8547 0.2777 -0.1032 0.055 Uiso 1 1 calc R . . H7C H 0.7524 0.2237 -0.1578 0.055 Uiso 1 1 calc R . . C8 C 0.8576(4) 0.1502(3) 0.0659(2) 0.0371(12) Uani 1 1 d . . . H8A H 0.8080 0.1342 0.1089 0.056 Uiso 1 1 calc R . . H8B H 0.8741 0.2165 0.0673 0.056 Uiso 1 1 calc R . . H8C H 0.9335 0.1161 0.0734 0.056 Uiso 1 1 calc R . . C9 C 0.6669(4) 0.1694(3) -0.0249(3) 0.0355(11) Uani 1 1 d . . . H9A H 0.6257 0.1518 -0.0769 0.053 Uiso 1 1 calc R . . H9B H 0.6754 0.2366 -0.0223 0.053 Uiso 1 1 calc R . . H9C H 0.6199 0.1484 0.0180 0.053 Uiso 1 1 calc R . . C10 C 0.7507(3) -0.1088(3) -0.1171(2) 0.0218(10) Uani 1 1 d . . . C11 C 0.6701(4) -0.1612(3) -0.0769(2) 0.0292(10) Uani 1 1 d . . . H11 H 0.6363 -0.1366 -0.0317 0.035 Uiso 1 1 calc R . . C12 C 0.6405(4) -0.2492(3) -0.1038(3) 0.0357(12) Uani 1 1 d . . . H12 H 0.5849 -0.2845 -0.0772 0.043 Uiso 1 1 calc R . . C13 C 0.6903(4) -0.2868(3) -0.1687(3) 0.0377(12) Uani 1 1 d . . . H13 H 0.6693 -0.3474 -0.1863 0.045 Uiso 1 1 calc R . . C14 C 0.7709(4) -0.2356(3) -0.2078(3) 0.0341(12) Uani 1 1 d . . . H14 H 0.8056 -0.2613 -0.2522 0.041 Uiso 1 1 calc R . . C15 C 0.8014(4) -0.1466(3) -0.1826(2) 0.0280(10) Uani 1 1 d . . . H15 H 0.8566 -0.1117 -0.2098 0.034 Uiso 1 1 calc R . . C21 C 0.2689(3) 0.0380(3) 0.4578(2) 0.0206(9) Uani 1 1 d . . . C22 C 0.1724(4) 0.0985(3) 0.4594(2) 0.0226(10) Uani 1 1 d . . . F22 F 0.1451(2) 0.15504(15) 0.39649(13) 0.0315(6) Uani 1 1 d . . . C23 C 0.1023(4) 0.1007(3) 0.5220(2) 0.0245(10) Uani 1 1 d . . . F23 F 0.0083(2) 0.15899(16) 0.51757(13) 0.0370(6) Uani 1 1 d . . . C24 C 0.1257(3) 0.0445(3) 0.5879(2) 0.0221(9) Uani 1 1 d . . . I24 I 0.01716(2) 0.048847(19) 0.682709(16) 0.02900(9) Uani 1 1 d . . . C25 C 0.2213(4) -0.0156(3) 0.5882(2) 0.0245(10) Uani 1 1 d . . . F25 F 0.2503(2) -0.07151(15) 0.65104(13) 0.0323(6) Uani 1 1 d . . . C26 C 0.2905(4) -0.0184(3) 0.5244(2) 0.0225(10) Uani 1 1 d . . . F26 F 0.38272(19) -0.07877(15) 0.52709(13) 0.0293(6) Uani 1 1 d . . . C31 C 0.3407(3) 0.0306(3) 0.3893(2) 0.0216(9) Uani 1 1 d . . . C32 C 0.4020(3) 0.1056(3) 0.3603(2) 0.0232(10) Uani 1 1 d . . . F32 F 0.3977(2) 0.18737(14) 0.39850(13) 0.0308(6) Uani 1 1 d . . . C33 C 0.4714(4) 0.0982(3) 0.2984(2) 0.0227(10) Uani 1 1 d . . . F33 F 0.5316(2) 0.17300(14) 0.27594(13) 0.0305(6) Uani 1 1 d . . . C34 C 0.4822(4) 0.0145(3) 0.2590(2) 0.0230(10) Uani 1 1 d . . . I34 I 0.58950(2) 0.001578(19) 0.164269(16) 0.02730(9) Uani 1 1 d . . . C35 C 0.4199(4) -0.0600(3) 0.2855(2) 0.0238(10) Uani 1 1 d . . . F35 F 0.4245(2) -0.14210(15) 0.24816(13) 0.0316(6) Uani 1 1 d . . . C36 C 0.3529(4) -0.0522(3) 0.3491(2) 0.0227(10) Uani 1 1 d . . . F36 F 0.2941(2) -0.12747(14) 0.37227(13) 0.0290(6) Uani 1 1 d . . . _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 0.014(2) 0.023(2) 0.025(2) -0.0015(19) 0.0028(17) -0.0011(18) N2 0.022(2) 0.025(2) 0.025(2) -0.0023(17) 0.0059(15) -0.0009(16) O2 0.0320(18) 0.0352(18) 0.0259(18) 0.0006(14) 0.0115(14) -0.0006(14) C3 0.030(3) 0.022(2) 0.026(2) -0.001(2) 0.0037(19) 0.001(2) C4 0.029(3) 0.018(2) 0.035(3) -0.003(2) 0.009(2) -0.0013(19) N5 0.0196(19) 0.026(2) 0.022(2) 0.0017(16) 0.0044(15) 0.0044(16) O5 0.0356(19) 0.0343(18) 0.0254(18) 0.0015(14) 0.0111(14) -0.0001(15) C6 0.026(3) 0.029(2) 0.033(3) 0.003(2) 0.0052(19) -0.006(2) C7 0.040(3) 0.023(2) 0.045(3) 0.008(2) 0.000(2) -0.004(2) C8 0.045(3) 0.036(3) 0.031(3) -0.009(2) 0.005(2) -0.010(2) C9 0.034(3) 0.025(2) 0.049(3) -0.005(2) 0.009(2) 0.000(2) C10 0.019(2) 0.023(2) 0.022(2) 0.0029(19) -0.0055(18) 0.0032(19) C11 0.027(3) 0.027(2) 0.032(3) 0.004(2) -0.002(2) 0.000(2) C12 0.031(3) 0.027(3) 0.048(3) 0.005(2) -0.001(2) -0.004(2) C13 0.038(3) 0.022(2) 0.049(3) 0.000(2) -0.018(2) 0.002(2) C14 0.043(3) 0.027(3) 0.030(3) -0.004(2) -0.007(2) 0.011(2) C15 0.029(3) 0.029(3) 0.026(3) 0.005(2) -0.0007(19) 0.008(2) C21 0.021(2) 0.023(2) 0.018(2) -0.0012(19) 0.0018(17) -0.0043(19) C22 0.024(2) 0.020(2) 0.024(2) 0.0020(19) 0.0034(18) 0.0005(19) F22 0.0370(15) 0.0298(14) 0.0277(14) 0.0075(11) 0.0034(11) 0.0124(12) C23 0.023(2) 0.022(2) 0.028(3) -0.001(2) 0.0029(19) 0.0084(19) F23 0.0371(16) 0.0389(15) 0.0363(15) 0.0049(12) 0.0105(12) 0.0171(13) C24 0.020(2) 0.023(2) 0.024(2) -0.0049(19) 0.0055(18) -0.0045(19) I24 0.02836(17) 0.03317(18) 0.02646(17) -0.00238(13) 0.00772(12) -0.00599(13) C25 0.026(3) 0.025(2) 0.021(2) 0.001(2) -0.0036(19) -0.005(2) F25 0.0348(15) 0.0351(14) 0.0264(14) 0.0118(12) -0.0001(11) -0.0006(12) C26 0.018(2) 0.020(2) 0.030(3) -0.002(2) -0.0005(18) 0.0024(18) F26 0.0279(14) 0.0318(14) 0.0278(14) 0.0042(11) 0.0007(10) 0.0102(11) C31 0.017(2) 0.026(2) 0.021(2) -0.0008(19) -0.0007(17) 0.0038(19) C32 0.022(2) 0.023(2) 0.024(2) -0.003(2) 0.0005(18) 0.0019(19) F32 0.0377(15) 0.0211(13) 0.0345(15) -0.0066(11) 0.0084(11) -0.0014(11) C33 0.023(2) 0.017(2) 0.027(2) 0.005(2) 0.0011(18) 0.0049(19) F33 0.0354(15) 0.0218(13) 0.0358(15) 0.0049(11) 0.0104(11) -0.0033(11) C34 0.022(2) 0.028(2) 0.020(2) -0.0005(19) 0.0031(18) 0.0033(19) I34 0.02543(17) 0.03276(18) 0.02438(17) 0.00045(13) 0.00580(12) 0.00349(13) C35 0.023(2) 0.021(2) 0.027(3) -0.006(2) 0.0014(19) 0.0025(19) F35 0.0338(15) 0.0249(13) 0.0373(15) -0.0082(11) 0.0089(11) 0.0013(11) C36 0.021(2) 0.019(2) 0.029(3) 0.004(2) 0.0012(18) -0.0045(19) F36 0.0295(14) 0.0231(13) 0.0358(15) -0.0016(11) 0.0098(11) -0.0026(11) _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. ; _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 1.356(5) . ? C1 N5 1.359(5) . ? C1 C10 1.463(5) . ? N2 O2 1.279(4) . ? N2 C3 1.509(5) . ? C3 C6 1.521(5) . ? C3 C7 1.522(5) . ? C3 C4 1.560(6) . ? C4 N5 1.509(5) . ? C4 C8 1.524(5) . ? C4 C9 1.530(5) . ? N5 O5 1.276(4) . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C15 1.398(5) . ? C10 C11 1.402(5) . ? C11 C12 1.384(5) . ? C11 H11 0.9500 . ? C12 C13 1.382(6) . ? C12 H12 0.9500 . ? C13 C14 1.383(6) . ? C13 H13 0.9500 . ? C14 C15 1.390(5) . ? C14 H14 0.9500 . ? C15 H15 0.9500 . ? C21 C26 1.389(5) . ? C21 C22 1.394(5) . ? C21 C31 1.469(6) . ? C22 F22 1.348(4) . ? C22 C23 1.371(5) . ? C23 F23 1.346(4) . ? C23 C24 1.379(5) . ? C24 C25 1.380(5) . ? C24 I24 2.094(4) . ? C25 F25 1.344(4) . ? C25 C26 1.382(6) . ? C26 F26 1.350(4) . ? C31 C36 1.391(5) . ? C31 C32 1.398(5) . ? C32 F32 1.352(4) . ? C32 C33 1.360(5) . ? C33 F33 1.351(4) . ? C33 C34 1.393(5) . ? C34 C35 1.383(5) . ? C34 I34 2.091(4) . ? C35 F35 1.349(4) . ? C35 C36 1.368(6) . ? C36 F36 1.351(4) . ? _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 N5 107.2(3) . . ? N2 C1 C10 126.3(4) . . ? N5 C1 C10 126.6(4) . . ? O2 N2 C1 126.0(3) . . ? O2 N2 C3 121.1(3) . . ? C1 N2 C3 112.6(3) . . ? N2 C3 C6 105.6(3) . . ? N2 C3 C7 109.6(3) . . ? C6 C3 C7 111.0(3) . . ? N2 C3 C4 100.2(3) . . ? C6 C3 C4 114.4(3) . . ? C7 C3 C4 114.9(3) . . ? N5 C4 C8 109.2(3) . . ? N5 C4 C9 106.3(3) . . ? C8 C4 C9 110.9(4) . . ? N5 C4 C3 99.9(3) . . ? C8 C4 C3 115.2(4) . . ? C9 C4 C3 114.3(3) . . ? O5 N5 C1 124.7(3) . . ? O5 N5 C4 122.3(3) . . ? C1 N5 C4 112.8(3) . . ? C3 C6 H6A 109.5 . . ? C3 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C3 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C4 C8 H8A 109.5 . . ? C4 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C4 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C4 C9 H9A 109.5 . . ? C4 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C4 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 C11 119.7(4) . . ? C15 C10 C1 120.2(4) . . ? C11 C10 C1 120.1(4) . . ? C12 C11 C10 119.2(4) . . ? C12 C11 H11 120.4 . . ? C10 C11 H11 120.4 . . ? C13 C12 C11 121.2(4) . . ? C13 C12 H12 119.4 . . ? C11 C12 H12 119.4 . . ? C12 C13 C14 119.6(4) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C13 C14 C15 120.4(4) . . ? C13 C14 H14 119.8 . . ? C15 C14 H14 119.8 . . ? C14 C15 C10 119.8(4) . . ? C14 C15 H15 120.1 . . ? C10 C15 H15 120.1 . . ? C26 C21 C22 115.5(4) . . ? C26 C21 C31 121.4(4) . . ? C22 C21 C31 123.0(4) . . ? F22 C22 C23 118.8(4) . . ? F22 C22 C21 119.0(4) . . ? C23 C22 C21 122.1(4) . . ? F23 C23 C22 118.4(4) . . ? F23 C23 C24 120.1(4) . . ? C22 C23 C24 121.5(4) . . ? C23 C24 C25 117.6(4) . . ? C23 C24 I24 120.8(3) . . ? C25 C24 I24 121.5(3) . . ? F25 C25 C24 120.8(4) . . ? F25 C25 C26 118.6(4) . . ? C24 C25 C26 120.6(4) . . ? F26 C26 C25 118.6(4) . . ? F26 C26 C21 118.8(4) . . ? C25 C26 C21 122.6(4) . . ? C36 C31 C32 115.4(4) . . ? C36 C31 C21 121.9(4) . . ? C32 C31 C21 122.7(4) . . ? F32 C32 C33 118.8(4) . . ? F32 C32 C31 118.4(4) . . ? C33 C32 C31 122.7(4) . . ? F33 C33 C32 119.1(3) . . ? F33 C33 C34 119.9(4) . . ? C32 C33 C34 120.9(4) . . ? C35 C34 C33 117.2(4) . . ? C35 C34 I34 121.3(3) . . ? C33 C34 I34 121.4(3) . . ? F35 C35 C36 119.0(4) . . ? F35 C35 C34 119.8(4) . . ? C36 C35 C34 121.3(4) . . ? F36 C36 C35 118.5(3) . . ? F36 C36 C31 119.1(4) . . ? C35 C36 C31 122.4(4) . . ? _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N5 C1 N2 O2 -175.7(3) . . . . ? C10 C1 N2 O2 4.9(6) . . . . ? N5 C1 N2 C3 10.2(4) . . . . ? C10 C1 N2 C3 -169.1(4) . . . . ? O2 N2 C3 C6 -78.7(4) . . . . ? C1 N2 C3 C6 95.7(4) . . . . ? O2 N2 C3 C7 41.0(5) . . . . ? C1 N2 C3 C7 -144.6(4) . . . . ? O2 N2 C3 C4 162.2(3) . . . . ? C1 N2 C3 C4 -23.4(4) . . . . ? N2 C3 C4 N5 25.0(3) . . . . ? C6 C3 C4 N5 -87.5(4) . . . . ? C7 C3 C4 N5 142.3(3) . . . . ? N2 C3 C4 C8 141.8(3) . . . . ? C6 C3 C4 C8 29.3(5) . . . . ? C7 C3 C4 C8 -100.9(4) . . . . ? N2 C3 C4 C9 -88.1(4) . . . . ? C6 C3 C4 C9 159.4(3) . . . . ? C7 C3 C4 C9 29.2(5) . . . . ? N2 C1 N5 O5 -175.3(3) . . . . ? C10 C1 N5 O5 4.1(6) . . . . ? N2 C1 N5 C4 8.7(4) . . . . ? C10 C1 N5 C4 -171.9(4) . . . . ? C8 C4 N5 O5 40.2(5) . . . . ? C9 C4 N5 O5 -79.4(4) . . . . ? C3 C4 N5 O5 161.4(3) . . . . ? C8 C4 N5 C1 -143.7(3) . . . . ? C9 C4 N5 C1 96.7(4) . . . . ? C3 C4 N5 C1 -22.4(4) . . . . ? N2 C1 C10 C15 21.6(6) . . . . ? N5 C1 C10 C15 -157.7(4) . . . . ? N2 C1 C10 C11 -157.4(4) . . . . ? N5 C1 C10 C11 23.4(6) . . . . ? C15 C10 C11 C12 -1.2(6) . . . . ? C1 C10 C11 C12 177.8(4) . . . . ? C10 C11 C12 C13 1.1(6) . . . . ? C11 C12 C13 C14 -0.3(7) . . . . ? C12 C13 C14 C15 -0.4(6) . . . . ? C13 C14 C15 C10 0.2(6) . . . . ? C11 C10 C15 C14 0.5(6) . . . . ? C1 C10 C15 C14 -178.4(3) . . . . ? C26 C21 C22 F22 -179.5(3) . . . . ? C31 C21 C22 F22 -2.0(6) . . . . ? C26 C21 C22 C23 -1.2(6) . . . . ? C31 C21 C22 C23 176.2(4) . . . . ? F22 C22 C23 F23 0.5(6) . . . . ? C21 C22 C23 F23 -177.8(3) . . . . ? F22 C22 C23 C24 180.0(3) . . . . ? C21 C22 C23 C24 1.7(6) . . . . ? F23 C23 C24 C25 178.3(3) . . . . ? C22 C23 C24 C25 -1.2(6) . . . . ? F23 C23 C24 I24 -0.4(5) . . . . ? C22 C23 C24 I24 -179.9(3) . . . . ? C23 C24 C25 F25 179.0(3) . . . . ? I24 C24 C25 F25 -2.2(5) . . . . ? C23 C24 C25 C26 0.2(6) . . . . ? I24 C24 C25 C26 178.9(3) . . . . ? F25 C25 C26 F26 1.6(5) . . . . ? C24 C25 C26 F26 -179.6(3) . . . . ? F25 C25 C26 C21 -178.6(3) . . . . ? C24 C25 C26 C21 0.2(6) . . . . ? C22 C21 C26 F26 -180.0(3) . . . . ? C31 C21 C26 F26 2.6(6) . . . . ? C22 C21 C26 C25 0.3(6) . . . . ? C31 C21 C26 C25 -177.2(4) . . . . ? C26 C21 C31 C36 55.2(6) . . . . ? C22 C21 C31 C36 -122.1(4) . . . . ? C26 C21 C31 C32 -124.3(4) . . . . ? C22 C21 C31 C32 58.5(6) . . . . ? C36 C31 C32 F32 -177.5(3) . . . . ? C21 C31 C32 F32 2.0(6) . . . . ? C36 C31 C32 C33 -1.5(6) . . . . ? C21 C31 C32 C33 178.0(4) . . . . ? F32 C32 C33 F33 -1.4(6) . . . . ? C31 C32 C33 F33 -177.4(3) . . . . ? F32 C32 C33 C34 177.6(3) . . . . ? C31 C32 C33 C34 1.7(6) . . . . ? F33 C33 C34 C35 179.0(3) . . . . ? C32 C33 C34 C35 -0.1(6) . . . . ? F33 C33 C34 I34 -0.5(5) . . . . ? C32 C33 C34 I34 -179.5(3) . . . . ? C33 C34 C35 F35 178.2(3) . . . . ? I34 C34 C35 F35 -2.4(5) . . . . ? C33 C34 C35 C36 -1.6(6) . . . . ? I34 C34 C35 C36 177.9(3) . . . . ? F35 C35 C36 F36 0.3(6) . . . . ? C34 C35 C36 F36 -180.0(3) . . . . ? F35 C35 C36 C31 -178.0(3) . . . . ? C34 C35 C36 C31 1.7(6) . . . . ? C32 C31 C36 F36 -178.4(3) . . . . ? C21 C31 C36 F36 2.0(6) . . . . ? C32 C31 C36 C35 -0.2(6) . . . . ? C21 C31 C36 C35 -179.7(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 25.03 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.861 _refine_diff_density_min -0.553 _refine_diff_density_rms 0.110