# Supplementary Material (ESI) for Chemical Communications # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'John Slattery' 'Patrick S. Bauerlein' 'Ian Fairlamb' 'Adam Lee' 'Christian Muller' 'Robert Thatcher' 'Dieter Vogt' 'Adrian C Whitwood' _publ_contact_author_name 'John Slattery' _publ_contact_author_email JS633@YORK.AC.UK _publ_section_title ; What can ionic pi-acidic alkene ligands do for you? Applications in ionic-liquid-supported Hiyama cross-couplings ; # Attachment 'fairlamb_slattery_xrd.cif' data_jms0803m _database_code_depnum_ccdc_archive 'CCDC 726739' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 N O2 Br' _chemical_formula_sum 'C22 H26 N O2 Br' _chemical_formula_weight 416.35 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.2923(5) _cell_length_b 10.5937(6) _cell_length_c 13.0176(8) _cell_angle_alpha 102.0820(10) _cell_angle_beta 94.3980(10) _cell_angle_gamma 112.7110(10) _cell_volume 1015.67(10) _cell_formula_units_Z 2 _cell_measurement_temperature 383(2) _cell_measurement_reflns_used 5304 _cell_measurement_theta_min 2.68 _cell_measurement_theta_max 28.29 _exptl_crystal_description blocks _exptl_crystal_colour colourless _exptl_crystal_size_max 0.13 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.361 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 432 _exptl_absorpt_coefficient_mu 2.039 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.765 _exptl_absorpt_correction_T_max 0.849 _exptl_absorpt_process_details 'SADABS v1.03 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _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 10520 _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_sigmaI/netI 0.0278 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.16 _diffrn_reflns_theta_max 28.32 _reflns_number_total 4982 _reflns_number_gt 4480 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. Bromine atom showed disorder - modelled as 86:14 ratio over two positions. ; _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^)+(0.0576P)^2^+1.1647P] 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 4982 _refine_ls_number_parameters 246 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0446 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1203 _refine_ls_wR_factor_gt 0.1174 _refine_ls_goodness_of_fit_ref 1.111 _refine_ls_restrained_S_all 1.111 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 1.4356(4) 1.2484(3) -0.1887(2) 0.0354(6) Uani 1 1 d . . . H1 H 1.5325 1.2857 -0.1335 0.042 Uiso 1 1 calc R . . C2 C 1.4427(4) 1.3108(3) -0.2736(3) 0.0380(7) Uani 1 1 d . . . H2 H 1.5452 1.3875 -0.2760 0.046 Uiso 1 1 calc R . . C3 C 1.2977(5) 1.2587(3) -0.3536(3) 0.0394(7) Uani 1 1 d . . . H3 H 1.3015 1.3015 -0.4094 0.047 Uiso 1 1 calc R . . C4 C 1.1458(4) 1.1424(4) -0.3514(3) 0.0406(7) Uani 1 1 d . . . H4 H 1.0476 1.1080 -0.4054 0.049 Uiso 1 1 calc R . . C5 C 1.1402(4) 1.0773(3) -0.2688(2) 0.0362(6) Uani 1 1 d . . . H5 H 1.0393 0.9977 -0.2689 0.043 Uiso 1 1 calc R . . C6 C 1.2840(4) 1.1301(3) -0.1857(2) 0.0292(5) Uani 1 1 d . . . C7 C 1.2873(4) 1.0675(3) -0.0961(2) 0.0298(5) Uani 1 1 d . . . H7 H 1.3850 1.1172 -0.0414 0.036 Uiso 1 1 calc R . . C8 C 1.1657(4) 0.9466(3) -0.0835(2) 0.0299(5) Uani 1 1 d . . . H8 H 1.0632 0.8936 -0.1343 0.036 Uiso 1 1 calc R . . C9 C 1.1965(3) 0.8983(3) 0.0121(2) 0.0277(5) Uani 1 1 d . . . C10 C 1.0577(3) 0.7701(3) 0.0311(2) 0.0268(5) Uani 1 1 d . . . C11 C 0.8885(3) 0.6980(3) -0.0309(2) 0.0275(5) Uani 1 1 d . . . H11 H 0.8610 0.7260 -0.0906 0.033 Uiso 1 1 calc R . . C12 C 0.7611(4) 0.5853(3) -0.0046(2) 0.0285(5) Uani 1 1 d . . . H12 H 0.6479 0.5390 -0.0456 0.034 Uiso 1 1 calc R . . C13 C 0.8029(3) 0.5416(3) 0.0834(2) 0.0262(5) Uani 1 1 d . . . C14 C 0.9720(4) 0.6086(3) 0.1441(2) 0.0322(6) Uani 1 1 d . . . H14 H 1.0012 0.5770 0.2013 0.039 Uiso 1 1 calc R . . C15 C 1.0967(4) 0.7233(3) 0.1180(2) 0.0323(6) Uani 1 1 d . . . H15 H 1.2094 0.7702 0.1597 0.039 Uiso 1 1 calc R . . C16 C 0.7007(3) 0.3970(3) 0.2026(2) 0.0278(5) Uani 1 1 d . . . H16A H 0.7509 0.4813 0.2618 0.033 Uiso 1 1 calc R . . H16B H 0.7811 0.3503 0.1980 0.033 Uiso 1 1 calc R . . C17 C 0.5177(3) 0.2974(3) 0.2153(2) 0.0264(5) Uani 1 1 d . . . H17A H 0.4409 0.3473 0.2200 0.032 Uiso 1 1 calc R . . H17B H 0.4674 0.2180 0.1524 0.032 Uiso 1 1 calc R . . C18 C 0.5894(4) 0.3611(3) 0.4123(2) 0.0301(5) Uani 1 1 d . . . H18A H 0.7115 0.4206 0.4138 0.045 Uiso 1 1 calc R . . H18B H 0.5799 0.3228 0.4734 0.045 Uiso 1 1 calc R . . H18C H 0.5203 0.4160 0.4138 0.045 Uiso 1 1 calc R . . C19 C 0.6252(4) 0.1514(3) 0.3072(2) 0.0281(5) Uani 1 1 d . . . H19A H 0.7516 0.2098 0.3279 0.034 Uiso 1 1 calc R . . H19B H 0.6024 0.0906 0.2359 0.034 Uiso 1 1 calc R . . C20 C 0.5568(4) 0.0640(3) 0.3867(2) 0.0331(6) Uani 1 1 d . . . H20A H 0.6287 0.1120 0.4571 0.040 Uiso 1 1 calc R . . H20B H 0.5593 -0.0284 0.3640 0.040 Uiso 1 1 calc R . . C21 C 0.3645(4) 0.0492(3) 0.3878(2) 0.0335(6) Uani 1 1 d . . . H21A H 0.2811 -0.0492 0.3607 0.040 Uiso 1 1 calc R . . H21B H 0.3489 0.0843 0.4596 0.040 Uiso 1 1 calc R . . C22 C 0.3362(3) 0.1377(3) 0.3156(2) 0.0291(5) Uani 1 1 d . . . H22A H 0.2758 0.0784 0.2447 0.035 Uiso 1 1 calc R . . H22B H 0.2662 0.1872 0.3447 0.035 Uiso 1 1 calc R . . O1 O 1.3362(3) 0.9654(2) 0.07711(16) 0.0377(5) Uani 1 1 d . . . O2 O 0.6674(2) 0.4315(2) 0.10468(15) 0.0305(4) Uani 1 1 d . . . N1 N 0.5214(3) 0.2420(2) 0.31214(17) 0.0248(4) Uani 1 1 d . . . Br1 Br 0.13366(4) 0.39257(3) 0.34067(2) 0.02610(10) Uani 0.8561(13) 1 d P A 1 Br1A Br 0.9457(4) 0.3234(3) 0.5574(2) 0.0575(9) Uani 0.1439(13) 1 d P A 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 C1 0.0385(15) 0.0255(13) 0.0377(15) 0.0066(11) 0.0095(12) 0.0088(11) C2 0.0458(17) 0.0247(13) 0.0458(16) 0.0133(12) 0.0211(13) 0.0124(12) C3 0.0548(19) 0.0397(16) 0.0429(16) 0.0238(13) 0.0257(14) 0.0296(14) C4 0.0367(15) 0.0510(18) 0.0445(16) 0.0234(14) 0.0115(13) 0.0226(14) C5 0.0300(14) 0.0412(15) 0.0422(16) 0.0191(13) 0.0123(12) 0.0143(12) C6 0.0321(13) 0.0255(12) 0.0328(13) 0.0087(10) 0.0131(10) 0.0127(10) C7 0.0322(13) 0.0279(12) 0.0281(12) 0.0054(10) 0.0071(10) 0.0118(11) C8 0.0290(13) 0.0292(13) 0.0289(13) 0.0085(10) 0.0063(10) 0.0087(10) C9 0.0276(12) 0.0262(12) 0.0255(12) 0.0043(9) 0.0051(9) 0.0082(10) C10 0.0281(12) 0.0252(12) 0.0260(12) 0.0065(9) 0.0067(9) 0.0097(10) C11 0.0302(13) 0.0274(12) 0.0236(11) 0.0090(9) 0.0033(9) 0.0096(10) C12 0.0274(12) 0.0286(12) 0.0244(12) 0.0072(10) -0.0008(9) 0.0070(10) C13 0.0278(12) 0.0247(12) 0.0261(12) 0.0080(9) 0.0064(9) 0.0099(10) C14 0.0302(13) 0.0372(14) 0.0299(13) 0.0157(11) 0.0027(10) 0.0116(11) C15 0.0243(12) 0.0376(14) 0.0307(13) 0.0118(11) 0.0015(10) 0.0073(11) C16 0.0270(12) 0.0297(12) 0.0265(12) 0.0123(10) 0.0037(9) 0.0090(10) C17 0.0264(12) 0.0265(12) 0.0250(11) 0.0103(9) 0.0023(9) 0.0082(10) C18 0.0356(14) 0.0282(12) 0.0240(12) 0.0051(10) 0.0032(10) 0.0117(11) C19 0.0289(12) 0.0298(12) 0.0305(13) 0.0116(10) 0.0079(10) 0.0148(10) C20 0.0408(15) 0.0335(14) 0.0331(14) 0.0162(11) 0.0109(11) 0.0192(12) C21 0.0389(15) 0.0330(14) 0.0344(14) 0.0162(11) 0.0148(11) 0.0157(12) C22 0.0263(12) 0.0303(13) 0.0305(13) 0.0111(10) 0.0065(10) 0.0095(10) O1 0.0337(10) 0.0349(10) 0.0322(10) 0.0094(8) 0.0006(8) 0.0020(8) O2 0.0286(9) 0.0307(9) 0.0282(9) 0.0133(7) 0.0010(7) 0.0059(8) N1 0.0266(10) 0.0247(10) 0.0243(10) 0.0083(8) 0.0045(8) 0.0106(8) Br1 0.02079(15) 0.02805(16) 0.02632(16) 0.00116(11) 0.00140(10) 0.01031(11) Br1A 0.0719(19) 0.0609(17) 0.0540(16) 0.0209(12) 0.0103(12) 0.0394(14) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.396(4) . ? C1 C6 1.402(4) . ? C1 H1 0.9300 . ? C2 C3 1.374(5) . ? C2 H2 0.9300 . ? C3 C4 1.388(4) . ? C3 H3 0.9300 . ? C4 C5 1.389(4) . ? C4 H4 0.9300 . ? C5 C6 1.392(4) . ? C5 H5 0.9300 . ? C6 C7 1.461(4) . ? C7 C8 1.342(4) . ? C7 H7 0.9300 . ? C8 C9 1.481(4) . ? C8 H8 0.9300 . ? C9 O1 1.235(3) . ? C9 C10 1.486(4) . ? C10 C15 1.392(4) . ? C10 C11 1.394(4) . ? C11 C12 1.383(3) . ? C11 H11 0.9300 . ? C12 C13 1.389(3) . ? C12 H12 0.9300 . ? C13 O2 1.368(3) . ? C13 C14 1.386(4) . ? C14 C15 1.384(4) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? C16 O2 1.433(3) . ? C16 C17 1.522(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 N1 1.500(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 N1 1.503(3) . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 N1 1.512(3) . ? C19 C20 1.529(4) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.542(4) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.525(4) . ? C21 H21A 0.9700 . ? C21 H21B 0.9700 . ? C22 N1 1.517(3) . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C6 120.7(3) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? C3 C2 C1 119.8(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.2(3) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C3 C4 C5 120.1(3) . . ? C3 C4 H4 120.0 . . ? C5 C4 H4 120.0 . . ? C4 C5 C6 120.6(3) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 118.5(3) . . ? C5 C6 C7 123.7(2) . . ? C1 C6 C7 117.8(3) . . ? C8 C7 C6 127.5(3) . . ? C8 C7 H7 116.3 . . ? C6 C7 H7 116.3 . . ? C7 C8 C9 119.3(2) . . ? C7 C8 H8 120.4 . . ? C9 C8 H8 120.4 . . ? O1 C9 C8 120.3(2) . . ? O1 C9 C10 119.7(2) . . ? C8 C9 C10 120.0(2) . . ? C15 C10 C11 118.4(2) . . ? C15 C10 C9 118.0(2) . . ? C11 C10 C9 123.5(2) . . ? C12 C11 C10 120.7(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 119.8(2) . . ? C11 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? O2 C13 C14 123.8(2) . . ? O2 C13 C12 115.6(2) . . ? C14 C13 C12 120.6(2) . . ? C15 C14 C13 118.9(2) . . ? C15 C14 H14 120.6 . . ? C13 C14 H14 120.6 . . ? C14 C15 C10 121.6(2) . . ? C14 C15 H15 119.2 . . ? C10 C15 H15 119.2 . . ? O2 C16 C17 103.6(2) . . ? O2 C16 H16A 111.0 . . ? C17 C16 H16A 111.0 . . ? O2 C16 H16B 111.0 . . ? C17 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? N1 C17 C16 113.1(2) . . ? N1 C17 H17A 109.0 . . ? C16 C17 H17A 109.0 . . ? N1 C17 H17B 109.0 . . ? C16 C17 H17B 109.0 . . ? H17A C17 H17B 107.8 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 C20 103.9(2) . . ? N1 C19 H19A 111.0 . . ? C20 C19 H19A 111.0 . . ? N1 C19 H19B 111.0 . . ? C20 C19 H19B 111.0 . . ? H19A C19 H19B 109.0 . . ? C19 C20 C21 105.3(2) . . ? C19 C20 H20A 110.7 . . ? C21 C20 H20A 110.7 . . ? C19 C20 H20B 110.7 . . ? C21 C20 H20B 110.7 . . ? H20A C20 H20B 108.8 . . ? C22 C21 C20 105.5(2) . . ? C22 C21 H21A 110.6 . . ? C20 C21 H21A 110.6 . . ? C22 C21 H21B 110.6 . . ? C20 C21 H21B 110.6 . . ? H21A C21 H21B 108.8 . . ? N1 C22 C21 105.0(2) . . ? N1 C22 H22A 110.8 . . ? C21 C22 H22A 110.8 . . ? N1 C22 H22B 110.8 . . ? C21 C22 H22B 110.8 . . ? H22A C22 H22B 108.8 . . ? C13 O2 C16 116.4(2) . . ? C17 N1 C18 110.89(19) . . ? C17 N1 C19 112.72(19) . . ? C18 N1 C19 111.3(2) . . ? C17 N1 C22 109.71(19) . . ? C18 N1 C22 109.8(2) . . ? C19 N1 C22 102.14(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 2.0(4) . . . . ? C1 C2 C3 C4 -1.4(4) . . . . ? C2 C3 C4 C5 -0.6(5) . . . . ? C3 C4 C5 C6 1.9(5) . . . . ? C4 C5 C6 C1 -1.3(4) . . . . ? C4 C5 C6 C7 179.8(3) . . . . ? C2 C1 C6 C5 -0.7(4) . . . . ? C2 C1 C6 C7 178.3(3) . . . . ? C5 C6 C7 C8 6.5(4) . . . . ? C1 C6 C7 C8 -172.4(3) . . . . ? C6 C7 C8 C9 178.0(2) . . . . ? C7 C8 C9 O1 -3.2(4) . . . . ? C7 C8 C9 C10 175.8(2) . . . . ? O1 C9 C10 C15 -5.2(4) . . . . ? C8 C9 C10 C15 175.9(2) . . . . ? O1 C9 C10 C11 172.1(3) . . . . ? C8 C9 C10 C11 -6.9(4) . . . . ? C15 C10 C11 C12 1.9(4) . . . . ? C9 C10 C11 C12 -175.4(2) . . . . ? C10 C11 C12 C13 -1.2(4) . . . . ? C11 C12 C13 O2 178.5(2) . . . . ? C11 C12 C13 C14 -1.0(4) . . . . ? O2 C13 C14 C15 -177.0(3) . . . . ? C12 C13 C14 C15 2.4(4) . . . . ? C13 C14 C15 C10 -1.8(4) . . . . ? C11 C10 C15 C14 -0.4(4) . . . . ? C9 C10 C15 C14 177.0(3) . . . . ? O2 C16 C17 N1 177.7(2) . . . . ? N1 C19 C20 C21 28.5(3) . . . . ? C19 C20 C21 C22 -4.1(3) . . . . ? C20 C21 C22 N1 -21.7(3) . . . . ? C14 C13 O2 C16 7.4(4) . . . . ? C12 C13 O2 C16 -172.1(2) . . . . ? C17 C16 O2 C13 167.5(2) . . . . ? C16 C17 N1 C18 61.7(3) . . . . ? C16 C17 N1 C19 -63.8(3) . . . . ? C16 C17 N1 C22 -176.9(2) . . . . ? C20 C19 N1 C17 -159.5(2) . . . . ? C20 C19 N1 C18 75.2(3) . . . . ? C20 C19 N1 C22 -41.9(2) . . . . ? C21 C22 N1 C17 159.2(2) . . . . ? C21 C22 N1 C18 -78.7(2) . . . . ? C21 C22 N1 C19 39.4(2) . . . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 1.006 _refine_diff_density_min -0.326 _refine_diff_density_rms 0.090 #===END data_jms0805m _database_code_depnum_ccdc_archive 'CCDC 726740' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H20 N O, Br' _chemical_formula_sum 'C15 H20 Br N O' _chemical_formula_weight 310.23 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 '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)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 10.6662(18) _cell_length_b 13.109(2) _cell_length_c 11.3363(18) _cell_angle_alpha 90.00 _cell_angle_beta 115.960(3) _cell_angle_gamma 90.00 _cell_volume 1425.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 383(2) _cell_measurement_reflns_used 4440 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 28.24 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.09 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.446 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 2.873 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.593 _exptl_absorpt_correction_T_max 0.772 _exptl_absorpt_process_details 'SADABS v2.03; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 383(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 'CCD area detector' _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 13289 _diffrn_reflns_av_R_equivalents 0.0457 _diffrn_reflns_av_sigmaI/netI 0.0444 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.19 _diffrn_reflns_theta_max 28.34 _reflns_number_total 3504 _reflns_number_gt 2800 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0550P)^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 3504 _refine_ls_number_parameters 164 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0481 _refine_ls_R_factor_gt 0.0357 _refine_ls_wR_factor_ref 0.0923 _refine_ls_wR_factor_gt 0.0886 _refine_ls_goodness_of_fit_ref 0.985 _refine_ls_restrained_S_all 0.985 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.04747(3) 0.234211(18) 0.05305(2) 0.02821(10) Uani 1 1 d . . . C1 C 0.7692(2) 0.01646(19) -0.2116(2) 0.0255(5) Uani 1 1 d . . . H1A H 0.8406 -0.0359 -0.1861 0.031 Uiso 1 1 calc R . . H1B H 0.8095 0.0810 -0.2194 0.031 Uiso 1 1 calc R . . C2 C 0.6453(2) -0.01144(18) -0.3408(2) 0.0239(5) Uani 1 1 d . . . H2A H 0.6711 -0.0639 -0.3865 0.029 Uiso 1 1 calc R . . H2B H 0.6122 0.0479 -0.3972 0.029 Uiso 1 1 calc R . . C3 C 0.5327(2) -0.05087(19) -0.3022(2) 0.0269(5) Uani 1 1 d . . . H3A H 0.4561 -0.0028 -0.3280 0.032 Uiso 1 1 calc R . . H3B H 0.4965 -0.1161 -0.3434 0.032 Uiso 1 1 calc R . . C4 C 0.6069(2) -0.06171(18) -0.1534(2) 0.0239(5) Uani 1 1 d . . . H4A H 0.5420 -0.0546 -0.1150 0.029 Uiso 1 1 calc R . . H4B H 0.6536 -0.1271 -0.1281 0.029 Uiso 1 1 calc R . . C5 C 0.6399(3) 0.12631(18) -0.1263(2) 0.0309(5) Uani 1 1 d . . . H5A H 0.5814 0.1247 -0.0817 0.046 Uiso 1 1 calc R . . H5B H 0.5841 0.1408 -0.2176 0.046 Uiso 1 1 calc R . . H5C H 0.7094 0.1784 -0.0885 0.046 Uiso 1 1 calc R . . C6 C 0.8257(2) 0.01453(18) 0.02221(19) 0.0200(4) Uani 1 1 d . . . H6A H 0.8975 0.0638 0.0321 0.024 Uiso 1 1 calc R . . H6B H 0.8663 -0.0529 0.0314 0.024 Uiso 1 1 calc R . . C7 C 0.7832(2) 0.03053(17) 0.1321(2) 0.0208(4) Uani 1 1 d . . . C8 C 0.8933(2) 0.06998(17) 0.2539(2) 0.0207(4) Uani 1 1 d . . . H8 H 0.9813 0.0823 0.2588 0.025 Uiso 1 1 calc R . . C9 C 0.8699(2) 0.08859(16) 0.3580(2) 0.0195(4) Uani 1 1 d . . . H9 H 0.7807 0.0740 0.3486 0.023 Uiso 1 1 calc R . . C10 C 0.9673(2) 0.12901(16) 0.4848(2) 0.0197(4) Uani 1 1 d . . . C11 C 0.9184(2) 0.15130(17) 0.5779(2) 0.0228(5) Uani 1 1 d . . . H11 H 0.8246 0.1420 0.5570 0.027 Uiso 1 1 calc R . . C12 C 1.0080(3) 0.18696(17) 0.7003(2) 0.0264(5) Uani 1 1 d . . . H12 H 0.9746 0.2008 0.7619 0.032 Uiso 1 1 calc R . . C13 C 1.1469(3) 0.20224(18) 0.7318(2) 0.0296(5) Uani 1 1 d . . . H13 H 1.2070 0.2262 0.8147 0.035 Uiso 1 1 calc R . . C14 C 1.1969(3) 0.18207(18) 0.6406(2) 0.0284(5) Uani 1 1 d . . . H14 H 1.2904 0.1932 0.6615 0.034 Uiso 1 1 calc R . . C15 C 1.1076(2) 0.14519(17) 0.5179(2) 0.0236(5) Uani 1 1 d . . . H15 H 1.1418 0.1311 0.4569 0.028 Uiso 1 1 calc R . . N1 N 0.71023(18) 0.02429(14) -0.11242(16) 0.0196(4) Uani 1 1 d . . . O1 O 0.66669(15) 0.00997(14) 0.11834(14) 0.0301(4) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.03733(16) 0.02292(14) 0.02329(15) -0.00314(9) 0.01227(11) -0.00435(10) C1 0.0252(12) 0.0373(13) 0.0164(10) -0.0008(9) 0.0112(10) -0.0032(10) C2 0.0255(12) 0.0300(12) 0.0138(10) -0.0019(9) 0.0064(10) -0.0013(9) C3 0.0234(12) 0.0349(13) 0.0177(11) -0.0027(10) 0.0047(10) -0.0018(10) C4 0.0207(11) 0.0296(12) 0.0202(11) -0.0030(9) 0.0077(10) -0.0057(9) C5 0.0394(14) 0.0268(12) 0.0202(12) 0.0001(9) 0.0072(11) 0.0093(11) C6 0.0158(10) 0.0292(12) 0.0112(10) -0.0027(8) 0.0025(9) -0.0016(8) C7 0.0214(11) 0.0233(11) 0.0158(10) 0.0023(8) 0.0063(9) 0.0045(8) C8 0.0177(10) 0.0237(11) 0.0182(11) 0.0014(8) 0.0054(9) 0.0021(8) C9 0.0180(11) 0.0226(11) 0.0156(10) 0.0024(8) 0.0052(9) 0.0021(8) C10 0.0238(11) 0.0169(10) 0.0148(10) 0.0029(8) 0.0051(9) 0.0011(8) C11 0.0259(12) 0.0219(11) 0.0206(11) 0.0013(9) 0.0101(10) -0.0002(9) C12 0.0424(14) 0.0201(11) 0.0173(11) -0.0008(9) 0.0136(11) -0.0023(10) C13 0.0399(15) 0.0201(11) 0.0184(11) -0.0033(9) 0.0033(11) -0.0077(10) C14 0.0254(12) 0.0255(13) 0.0264(12) 0.0005(10) 0.0040(10) -0.0060(9) C15 0.0265(12) 0.0224(11) 0.0207(11) 0.0005(9) 0.0091(10) -0.0014(9) N1 0.0172(9) 0.0274(10) 0.0109(9) -0.0006(7) 0.0031(8) 0.0011(7) O1 0.0182(8) 0.0539(11) 0.0181(8) -0.0020(8) 0.0078(7) -0.0015(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.513(3) . ? C1 C2 1.527(3) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.536(3) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.525(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 N1 1.501(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.508(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 N1 1.489(2) . ? C6 C7 1.515(3) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O1 1.213(3) . ? C7 C8 1.460(3) . ? C8 C9 1.331(3) . ? C8 H8 0.9300 . ? C9 C10 1.456(3) . ? C9 H9 0.9300 . ? C10 C15 1.391(3) . ? C10 C11 1.397(3) . ? C11 C12 1.377(3) . ? C11 H11 0.9300 . ? C12 C13 1.378(4) . ? C12 H12 0.9300 . ? C13 C14 1.382(3) . ? C13 H13 0.9300 . ? C14 C15 1.384(3) . ? C14 H14 0.9300 . ? C15 H15 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 105.21(17) . . ? N1 C1 H1A 110.7 . . ? C2 C1 H1A 110.7 . . ? N1 C1 H1B 110.7 . . ? C2 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? C1 C2 C3 105.30(17) . . ? C1 C2 H2A 110.7 . . ? C3 C2 H2A 110.7 . . ? C1 C2 H2B 110.7 . . ? C3 C2 H2B 110.7 . . ? H2A C2 H2B 108.8 . . ? C4 C3 C2 104.73(17) . . ? C4 C3 H3A 110.8 . . ? C2 C3 H3A 110.8 . . ? C4 C3 H3B 110.8 . . ? C2 C3 H3B 110.8 . . ? H3A C3 H3B 108.9 . . ? N1 C4 C3 103.16(18) . . ? N1 C4 H4A 111.1 . . ? C3 C4 H4A 111.1 . . ? N1 C4 H4B 111.1 . . ? C3 C4 H4B 111.1 . . ? H4A C4 H4B 109.1 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 114.84(17) . . ? N1 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? N1 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? O1 C7 C8 123.7(2) . . ? O1 C7 C6 121.5(2) . . ? C8 C7 C6 114.85(18) . . ? C9 C8 C7 121.2(2) . . ? C9 C8 H8 119.4 . . ? C7 C8 H8 119.4 . . ? C8 C9 C10 127.8(2) . . ? C8 C9 H9 116.1 . . ? C10 C9 H9 116.1 . . ? C15 C10 C11 118.5(2) . . ? C15 C10 C9 122.71(19) . . ? C11 C10 C9 118.75(19) . . ? C12 C11 C10 120.6(2) . . ? C12 C11 H11 119.7 . . ? C10 C11 H11 119.7 . . ? C11 C12 C13 120.2(2) . . ? C11 C12 H12 119.9 . . ? C13 C12 H12 119.9 . . ? C12 C13 C14 120.1(2) . . ? C12 C13 H13 119.9 . . ? C14 C13 H13 119.9 . . ? C13 C14 C15 119.9(2) . . ? C13 C14 H14 120.1 . . ? C15 C14 H14 120.1 . . ? C14 C15 C10 120.7(2) . . ? C14 C15 H15 119.7 . . ? C10 C15 H15 119.7 . . ? C6 N1 C4 114.73(17) . . ? C6 N1 C5 109.50(17) . . ? C4 N1 C5 111.70(17) . . ? C6 N1 C1 109.24(16) . . ? C4 N1 C1 101.94(17) . . ? C5 N1 C1 109.40(18) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 -17.3(3) . . . . ? C1 C2 C3 C4 -10.0(3) . . . . ? C2 C3 C4 N1 33.9(2) . . . . ? N1 C6 C7 O1 29.6(3) . . . . ? N1 C6 C7 C8 -151.55(19) . . . . ? O1 C7 C8 C9 -1.9(3) . . . . ? C6 C7 C8 C9 179.3(2) . . . . ? C7 C8 C9 C10 -179.0(2) . . . . ? C8 C9 C10 C15 -6.3(4) . . . . ? C8 C9 C10 C11 174.5(2) . . . . ? C15 C10 C11 C12 -1.0(3) . . . . ? C9 C10 C11 C12 178.2(2) . . . . ? C10 C11 C12 C13 0.8(3) . . . . ? C11 C12 C13 C14 0.2(4) . . . . ? C12 C13 C14 C15 -0.8(4) . . . . ? C13 C14 C15 C10 0.6(3) . . . . ? C11 C10 C15 C14 0.3(3) . . . . ? C9 C10 C15 C14 -178.8(2) . . . . ? C7 C6 N1 C4 -71.6(2) . . . . ? C7 C6 N1 C5 54.9(2) . . . . ? C7 C6 N1 C1 174.73(18) . . . . ? C3 C4 N1 C6 -162.40(17) . . . . ? C3 C4 N1 C5 72.2(2) . . . . ? C3 C4 N1 C1 -44.5(2) . . . . ? C2 C1 N1 C6 160.08(19) . . . . ? C2 C1 N1 C4 38.3(2) . . . . ? C2 C1 N1 C5 -80.1(2) . . . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.998 _refine_diff_density_min -0.324 _refine_diff_density_rms 0.087 #===END data_jms0809a _database_code_depnum_ccdc_archive 'CCDC 726741' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H28 N O3, Br' _chemical_formula_sum 'C23 H28 Br N O3' _chemical_formula_weight 446.37 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P21/c loop_ _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 10.5509(6) _cell_length_b 25.7087(16) _cell_length_c 8.2257(5) _cell_angle_alpha 90.00 _cell_angle_beta 111.2720(10) _cell_angle_gamma 90.00 _cell_volume 2079.2(2) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 5151 _cell_measurement_theta_min 2.22 _cell_measurement_theta_max 27.00 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.426 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 928 _exptl_absorpt_coefficient_mu 2.001 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.757 _exptl_absorpt_correction_T_max 0.923 _exptl_absorpt_process_details 'SADABS v2.03 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(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 'CCD area detector' _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 21232 _diffrn_reflns_av_R_equivalents 0.0383 _diffrn_reflns_av_sigmaI/netI 0.0375 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -34 _diffrn_reflns_limit_k_max 34 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 28.29 _reflns_number_total 5141 _reflns_number_gt 4241 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0375P)^2^+0.9114P] 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 5141 _refine_ls_number_parameters 255 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0454 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0794 _refine_ls_wR_factor_gt 0.0747 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.26754(2) 0.840691(7) 0.03352(3) 0.02119(7) Uani 1 1 d . . . C1 C 0.0239(2) 0.84190(8) 0.2554(2) 0.0207(4) Uani 1 1 d . . . H1A H 0.0622 0.8255 0.1744 0.025 Uiso 1 1 calc R . . H1B H -0.0101 0.8770 0.2112 0.025 Uiso 1 1 calc R . . C2 C -0.0905(2) 0.80845(9) 0.2731(3) 0.0267(5) Uani 1 1 d . . . H2A H -0.0875 0.7729 0.2286 0.032 Uiso 1 1 calc R . . H2B H -0.1804 0.8240 0.2067 0.032 Uiso 1 1 calc R . . C3 C -0.0659(2) 0.80714(8) 0.4687(3) 0.0250(4) Uani 1 1 d . . . H3A H -0.1499 0.8163 0.4895 0.030 Uiso 1 1 calc R . . H3B H -0.0355 0.7722 0.5178 0.030 Uiso 1 1 calc R . . C4 C 0.0447(2) 0.84731(8) 0.5503(3) 0.0199(4) Uani 1 1 d . . . H4A H 0.0051 0.8824 0.5471 0.024 Uiso 1 1 calc R . . H4B H 0.0992 0.8382 0.6728 0.024 Uiso 1 1 calc R . . C5 C 0.2161(2) 0.79678(8) 0.4747(3) 0.0262(5) Uani 1 1 d . . . H5A H 0.2717 0.7952 0.5993 0.039 Uiso 1 1 calc R . . H5B H 0.2757 0.7976 0.4068 0.039 Uiso 1 1 calc R . . H5C H 0.1572 0.7661 0.4418 0.039 Uiso 1 1 calc R . . C6 C 0.21578(18) 0.89310(7) 0.4553(2) 0.0169(4) Uani 1 1 d . . . H6A H 0.1559 0.9240 0.4248 0.020 Uiso 1 1 calc R . . H6B H 0.2635 0.8910 0.3718 0.020 Uiso 1 1 calc R . . C7 C 0.31997(19) 0.89959(7) 0.6389(2) 0.0187(4) Uani 1 1 d . . . H7A H 0.2748 0.9014 0.7253 0.022 Uiso 1 1 calc R . . H7B H 0.3853 0.8703 0.6696 0.022 Uiso 1 1 calc R . . C8 C 0.50321(18) 0.95768(7) 0.7762(2) 0.0168(4) Uani 1 1 d . . . C9 C 0.57989(19) 1.00024(7) 0.7605(2) 0.0192(4) Uani 1 1 d . . . H9 H 0.5493 1.0210 0.6579 0.023 Uiso 1 1 calc R . . C10 C 0.70053(19) 1.01226(7) 0.8945(2) 0.0177(4) Uani 1 1 d . . . H10 H 0.7520 1.0415 0.8842 0.021 Uiso 1 1 calc R . . C11 C 0.74732(18) 0.98168(7) 1.0450(2) 0.0162(4) Uani 1 1 d . . . C12 C 0.66723(19) 0.94013(7) 1.0590(2) 0.0193(4) Uani 1 1 d . . . H12 H 0.6975 0.9194 1.1616 0.023 Uiso 1 1 calc R . . C13 C 0.54489(19) 0.92814(7) 0.9280(2) 0.0196(4) Uani 1 1 d . . . H13 H 0.4904 0.9003 0.9416 0.024 Uiso 1 1 calc R . . C14 C 0.88137(19) 0.98991(7) 1.1876(2) 0.0176(4) Uani 1 1 d . . . C15 C 0.96251(19) 1.03643(7) 1.1843(2) 0.0194(4) Uani 1 1 d . . . H15 H 0.9262 1.0618 1.0955 0.023 Uiso 1 1 calc R . . C16 C 1.08670(19) 1.04313(7) 1.3050(3) 0.0184(4) Uani 1 1 d . . . H16 H 1.1188 1.0164 1.3897 0.022 Uiso 1 1 calc R . . C17 C 1.17869(19) 1.08706(7) 1.3212(2) 0.0175(4) Uani 1 1 d . . . C18 C 1.1512(2) 1.12653(8) 1.1974(2) 0.0208(4) Uani 1 1 d . . . H18 H 1.0691 1.1255 1.0985 0.025 Uiso 1 1 calc R . . C19 C 1.2411(2) 1.16736(8) 1.2155(3) 0.0211(4) Uani 1 1 d . . . H19 H 1.2215 1.1936 1.1285 0.025 Uiso 1 1 calc R . . C20 C 1.36070(19) 1.16971(7) 1.3624(3) 0.0189(4) Uani 1 1 d . . . C21 C 1.38849(19) 1.13128(8) 1.4901(3) 0.0202(4) Uani 1 1 d . . . H21 H 1.4685 1.1332 1.5917 0.024 Uiso 1 1 calc R . . C22 C 1.29907(19) 1.09037(7) 1.4681(2) 0.0189(4) Uani 1 1 d . . . H22 H 1.3195 1.0639 1.5544 0.023 Uiso 1 1 calc R . . C23 C 1.4414(2) 1.24391(9) 1.2525(3) 0.0356(6) Uani 1 1 d . . . H23A H 1.4387 1.2248 1.1483 0.053 Uiso 1 1 calc R . . H23B H 1.5187 1.2680 1.2878 0.053 Uiso 1 1 calc R . . H23C H 1.3568 1.2636 1.2266 0.053 Uiso 1 1 calc R . . N1 N 0.13011(15) 0.84505(6) 0.4380(2) 0.0153(3) Uani 1 1 d . . . O1 O 0.38749(13) 0.94756(5) 0.63391(17) 0.0196(3) Uani 1 1 d . . . O2 O 0.92360(14) 0.95793(5) 1.30629(19) 0.0252(3) Uani 1 1 d . . . O3 O 1.45619(14) 1.20794(6) 1.39136(19) 0.0249(3) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.02468(11) 0.01800(10) 0.02118(11) 0.00270(8) 0.00866(8) -0.00038(8) C1 0.0206(9) 0.0230(10) 0.0162(9) -0.0031(8) 0.0039(7) -0.0038(8) C2 0.0246(11) 0.0310(11) 0.0229(10) -0.0079(9) 0.0065(9) -0.0104(9) C3 0.0237(10) 0.0269(11) 0.0271(11) -0.0067(8) 0.0125(9) -0.0090(8) C4 0.0195(9) 0.0242(10) 0.0182(9) -0.0045(7) 0.0094(8) -0.0043(8) C5 0.0191(10) 0.0159(9) 0.0411(12) -0.0010(9) 0.0081(9) 0.0024(8) C6 0.0152(9) 0.0153(9) 0.0181(9) 0.0008(7) 0.0033(8) -0.0032(7) C7 0.0160(9) 0.0196(9) 0.0190(9) 0.0011(7) 0.0043(8) -0.0040(7) C8 0.0129(8) 0.0184(9) 0.0189(9) -0.0031(7) 0.0058(7) -0.0003(7) C9 0.0206(9) 0.0169(9) 0.0180(9) 0.0015(7) 0.0046(8) 0.0005(7) C10 0.0170(9) 0.0143(9) 0.0221(9) -0.0005(7) 0.0076(7) -0.0008(7) C11 0.0157(9) 0.0159(9) 0.0170(9) -0.0030(7) 0.0059(7) 0.0006(7) C12 0.0212(9) 0.0202(9) 0.0155(9) -0.0001(7) 0.0052(8) -0.0014(8) C13 0.0181(9) 0.0206(9) 0.0199(9) 0.0005(7) 0.0066(8) -0.0048(7) C14 0.0169(9) 0.0157(9) 0.0187(9) -0.0021(7) 0.0046(7) 0.0015(7) C15 0.0188(9) 0.0178(9) 0.0196(9) -0.0005(7) 0.0046(8) -0.0003(7) C16 0.0188(9) 0.0154(9) 0.0206(9) -0.0017(7) 0.0067(8) 0.0012(7) C17 0.0162(9) 0.0184(9) 0.0183(9) -0.0032(7) 0.0068(7) 0.0001(7) C18 0.0179(9) 0.0257(10) 0.0158(9) -0.0010(8) 0.0025(7) -0.0013(8) C19 0.0193(9) 0.0226(10) 0.0200(9) 0.0016(7) 0.0056(8) -0.0013(8) C20 0.0159(9) 0.0199(9) 0.0224(10) -0.0033(7) 0.0088(8) -0.0015(7) C21 0.0139(9) 0.0246(10) 0.0194(9) -0.0026(8) 0.0026(7) 0.0008(7) C22 0.0169(9) 0.0211(10) 0.0177(9) 0.0006(7) 0.0052(8) 0.0017(7) C23 0.0233(11) 0.0320(12) 0.0458(14) 0.0143(11) 0.0057(10) -0.0059(9) N1 0.0141(7) 0.0151(7) 0.0159(7) -0.0004(6) 0.0044(6) -0.0012(6) O1 0.0157(6) 0.0193(7) 0.0191(7) 0.0016(5) 0.0008(5) -0.0054(5) O2 0.0234(7) 0.0202(7) 0.0246(7) 0.0042(6) -0.0003(6) -0.0023(6) O3 0.0177(7) 0.0254(8) 0.0291(8) 0.0005(6) 0.0053(6) -0.0061(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.516(2) . ? C1 C2 1.532(3) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.534(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.519(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 N1 1.508(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 N1 1.502(2) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 N1 1.507(2) . ? C6 C7 1.521(3) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 O1 1.432(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 O1 1.375(2) . ? C8 C13 1.390(3) . ? C8 C9 1.394(3) . ? C9 C10 1.383(3) . ? C9 H9 0.9500 . ? C10 C11 1.396(3) . ? C10 H10 0.9500 . ? C11 C12 1.393(3) . ? C11 C14 1.489(3) . ? C12 C13 1.383(3) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O2 1.230(2) . ? C14 C15 1.477(3) . ? C15 C16 1.337(3) . ? C15 H15 0.9500 . ? C16 C17 1.463(3) . ? C16 H16 0.9500 . ? C17 C18 1.391(3) . ? C17 C22 1.403(3) . ? C18 C19 1.386(3) . ? C18 H18 0.9500 . ? C19 C20 1.396(3) . ? C19 H19 0.9500 . ? C20 O3 1.365(2) . ? C20 C21 1.394(3) . ? C21 C22 1.380(3) . ? C21 H21 0.9500 . ? C22 H22 0.9500 . ? C23 O3 1.433(3) . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C2 105.12(15) . . ? N1 C1 H1A 110.7 . . ? C2 C1 H1A 110.7 . . ? N1 C1 H1B 110.7 . . ? C2 C1 H1B 110.7 . . ? H1A C1 H1B 108.8 . . ? C1 C2 C3 105.81(16) . . ? C1 C2 H2A 110.6 . . ? C3 C2 H2A 110.6 . . ? C1 C2 H2B 110.6 . . ? C3 C2 H2B 110.6 . . ? H2A C2 H2B 108.7 . . ? C4 C3 C2 105.03(16) . . ? C4 C3 H3A 110.7 . . ? C2 C3 H3A 110.7 . . ? C4 C3 H3B 110.7 . . ? C2 C3 H3B 110.7 . . ? H3A C3 H3B 108.8 . . ? N1 C4 C3 103.71(15) . . ? N1 C4 H4A 111.0 . . ? C3 C4 H4A 111.0 . . ? N1 C4 H4B 111.0 . . ? C3 C4 H4B 111.0 . . ? H4A C4 H4B 109.0 . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C6 C7 112.14(15) . . ? N1 C6 H6A 109.2 . . ? C7 C6 H6A 109.2 . . ? N1 C6 H6B 109.2 . . ? C7 C6 H6B 109.2 . . ? H6A C6 H6B 107.9 . . ? O1 C7 C6 104.70(14) . . ? O1 C7 H7A 110.8 . . ? C6 C7 H7A 110.8 . . ? O1 C7 H7B 110.8 . . ? C6 C7 H7B 110.8 . . ? H7A C7 H7B 108.9 . . ? O1 C8 C13 123.73(17) . . ? O1 C8 C9 115.83(16) . . ? C13 C8 C9 120.45(17) . . ? C10 C9 C8 119.92(17) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.53(17) . . ? C9 C10 H10 119.7 . . ? C11 C10 H10 119.7 . . ? C12 C11 C10 118.37(17) . . ? C12 C11 C14 118.36(17) . . ? C10 C11 C14 123.21(17) . . ? C13 C12 C11 121.95(18) . . ? C13 C12 H12 119.0 . . ? C11 C12 H12 119.0 . . ? C12 C13 C8 118.68(18) . . ? C12 C13 H13 120.7 . . ? C8 C13 H13 120.7 . . ? O2 C14 C15 120.72(17) . . ? O2 C14 C11 119.84(17) . . ? C15 C14 C11 119.44(16) . . ? C16 C15 C14 120.59(18) . . ? C16 C15 H15 119.7 . . ? C14 C15 H15 119.7 . . ? C15 C16 C17 127.30(18) . . ? C15 C16 H16 116.4 . . ? C17 C16 H16 116.4 . . ? C18 C17 C22 117.99(17) . . ? C18 C17 C16 122.74(17) . . ? C22 C17 C16 119.26(17) . . ? C19 C18 C17 121.40(18) . . ? C19 C18 H18 119.3 . . ? C17 C18 H18 119.3 . . ? C18 C19 C20 119.59(18) . . ? C18 C19 H19 120.2 . . ? C20 C19 H19 120.2 . . ? O3 C20 C21 116.03(17) . . ? O3 C20 C19 124.06(18) . . ? C21 C20 C19 119.91(17) . . ? C22 C21 C20 119.64(18) . . ? C22 C21 H21 120.2 . . ? C20 C21 H21 120.2 . . ? C21 C22 C17 121.42(18) . . ? C21 C22 H22 119.3 . . ? C17 C22 H22 119.3 . . ? O3 C23 H23A 109.5 . . ? O3 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? O3 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C5 N1 C6 111.12(14) . . ? C5 N1 C4 111.14(15) . . ? C6 N1 C4 112.45(14) . . ? C5 N1 C1 109.31(15) . . ? C6 N1 C1 109.90(14) . . ? C4 N1 C1 102.57(14) . . ? C8 O1 C7 115.83(14) . . ? C20 O3 C23 117.74(16) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C2 C3 16.2(2) . . . . ? C1 C2 C3 C4 9.9(2) . . . . ? C2 C3 C4 N1 -32.5(2) . . . . ? N1 C6 C7 O1 -177.67(14) . . . . ? O1 C8 C9 C10 -177.66(16) . . . . ? C13 C8 C9 C10 2.1(3) . . . . ? C8 C9 C10 C11 0.8(3) . . . . ? C9 C10 C11 C12 -2.3(3) . . . . ? C9 C10 C11 C14 174.97(17) . . . . ? C10 C11 C12 C13 0.9(3) . . . . ? C14 C11 C12 C13 -176.46(17) . . . . ? C11 C12 C13 C8 1.9(3) . . . . ? O1 C8 C13 C12 176.33(17) . . . . ? C9 C8 C13 C12 -3.4(3) . . . . ? C12 C11 C14 O2 6.0(3) . . . . ? C10 C11 C14 O2 -171.23(18) . . . . ? C12 C11 C14 C15 -174.30(17) . . . . ? C10 C11 C14 C15 8.4(3) . . . . ? O2 C14 C15 C16 3.7(3) . . . . ? C11 C14 C15 C16 -175.96(17) . . . . ? C14 C15 C16 C17 -179.10(17) . . . . ? C15 C16 C17 C18 -6.4(3) . . . . ? C15 C16 C17 C22 172.74(19) . . . . ? C22 C17 C18 C19 1.6(3) . . . . ? C16 C17 C18 C19 -179.28(18) . . . . ? C17 C18 C19 C20 -1.3(3) . . . . ? C18 C19 C20 O3 179.31(18) . . . . ? C18 C19 C20 C21 -0.4(3) . . . . ? O3 C20 C21 C22 -178.03(17) . . . . ? C19 C20 C21 C22 1.7(3) . . . . ? C20 C21 C22 C17 -1.4(3) . . . . ? C18 C17 C22 C21 -0.3(3) . . . . ? C16 C17 C22 C21 -179.42(18) . . . . ? C7 C6 N1 C5 -61.6(2) . . . . ? C7 C6 N1 C4 63.7(2) . . . . ? C7 C6 N1 C1 177.29(15) . . . . ? C3 C4 N1 C5 -74.18(19) . . . . ? C3 C4 N1 C6 160.53(15) . . . . ? C3 C4 N1 C1 42.54(18) . . . . ? C2 C1 N1 C5 81.82(19) . . . . ? C2 C1 N1 C6 -155.98(16) . . . . ? C2 C1 N1 C4 -36.19(18) . . . . ? C13 C8 O1 C7 -8.9(3) . . . . ? C9 C8 O1 C7 170.87(16) . . . . ? C6 C7 O1 C8 -168.80(15) . . . . ? C21 C20 O3 C23 171.25(19) . . . . ? C19 C20 O3 C23 -8.5(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.510 _refine_diff_density_min -0.265 _refine_diff_density_rms 0.069 #===END data_jms0810 _database_code_depnum_ccdc_archive 'CCDC 726742' _audit_creation_method ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 N O2, F6 P' _chemical_formula_sum 'C22 H26 F6 N O2 P' _chemical_formula_weight 481.41 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _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 9.9133(4) _cell_length_b 21.1994(7) _cell_length_c 10.4816(4) _cell_angle_alpha 90.00 _cell_angle_beta 94.152(4) _cell_angle_gamma 90.00 _cell_volume 2196.99(14) _cell_formula_units_Z 4 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 7913 _cell_measurement_theta_min 4.1648 _cell_measurement_theta_max 70.4323 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.455 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1000 _exptl_absorpt_coefficient_mu 1.756 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.498 _exptl_absorpt_correction_T_max 0.869 _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 1.5418 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_source 'Enhance (Cu) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type ? _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 8.2707 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 18215 _diffrn_reflns_av_R_equivalents 0.0483 _diffrn_reflns_av_sigmaI/netI 0.0531 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_k_max 24 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 4.17 _diffrn_reflns_theta_max 70.56 _reflns_number_total 4086 _reflns_number_gt 3291 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.32.24 (release 21-04-2008 CrysAlis171 .NET) (compiled Apr 21 2008,18:23:10) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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. Ethyl group, heterocyclic ring and PF6 anion modelled as disordered over 2 positions in 54:46 ratio. Atoms C2 and C2a constrained as same position and ADP. Atoms C3 and C3a constrained as same position and ADP. ; _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^)+(0.0901P)^2^+3.5305P] 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 4086 _refine_ls_number_parameters 400 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0827 _refine_ls_wR_factor_ref 0.2166 _refine_ls_wR_factor_gt 0.2053 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.1419(13) 0.5868(6) 0.3789(15) 0.061(3) Uani 0.543(6) 1 d P A 1 H1A H 0.0455 0.5858 0.3616 0.091 Uiso 0.543(6) 1 calc PR A 1 H1B H 0.1782 0.6230 0.3384 0.091 Uiso 0.543(6) 1 calc PR A 1 H1C H 0.1632 0.5891 0.4696 0.091 Uiso 0.543(6) 1 calc PR A 1 C2 C 0.1532(4) 0.4665(2) 0.3847(4) 0.0623(11) Uani 0.543(6) 1 d P A 1 H2A H 0.0574 0.4696 0.3969 0.075 Uiso 0.543(6) 1 calc PR A 1 H2B H 0.2014 0.4586 0.4670 0.075 Uiso 0.543(6) 1 calc PR A 1 C3 C 0.1794(5) 0.4133(2) 0.2911(5) 0.0684(12) Uani 0.543(6) 1 d P A 1 H3A H 0.1027 0.3848 0.2809 0.082 Uiso 0.543(6) 1 calc PR A 1 H3B H 0.2595 0.3894 0.3194 0.082 Uiso 0.543(6) 1 calc PR A 1 C4 C 0.2001(11) 0.4498(4) 0.1633(8) 0.064(2) Uani 0.543(6) 1 d P A 1 H4A H 0.2940 0.4482 0.1432 0.076 Uiso 0.543(6) 1 calc PR A 1 H4B H 0.1444 0.4318 0.0926 0.076 Uiso 0.543(6) 1 calc PR A 1 C5 C 0.1584(7) 0.5161(3) 0.1882(6) 0.0495(17) Uani 0.543(6) 1 d P A 1 H5A H 0.0612 0.5209 0.1736 0.059 Uiso 0.543(6) 1 calc PR A 1 H5B H 0.2025 0.5453 0.1335 0.059 Uiso 0.543(6) 1 calc PR A 1 C6 C 0.3545(8) 0.5321(4) 0.3501(8) 0.0484(16) Uani 0.543(6) 1 d P A 1 H6A H 0.3753 0.5521 0.4325 0.058 Uiso 0.543(6) 1 calc PR A 1 H6B H 0.3920 0.4899 0.3549 0.058 Uiso 0.543(6) 1 calc PR A 1 C7 C 0.4237(6) 0.5685(3) 0.2503(7) 0.0511(17) Uani 0.543(6) 1 d P A 1 H7A H 0.5198 0.5715 0.2743 0.061 Uiso 0.543(6) 1 calc PR A 1 H7B H 0.4116 0.5471 0.1685 0.061 Uiso 0.543(6) 1 calc PR A 1 C1A C 0.3796(7) 0.5104(4) 0.4226(10) 0.047(2) Uani 0.457(6) 1 d P A 2 H1A1 H 0.4495 0.5334 0.3841 0.071 Uiso 0.457(6) 1 calc PR A 2 H1A2 H 0.4035 0.4666 0.4280 0.071 Uiso 0.457(6) 1 calc PR A 2 H1A3 H 0.3695 0.5266 0.5070 0.071 Uiso 0.457(6) 1 calc PR A 2 C2A C 0.1532(4) 0.4665(2) 0.3847(4) 0.0623(11) Uani 0.457(6) 1 d P A 2 H2A1 H 0.0598 0.4804 0.3755 0.075 Uiso 0.457(6) 1 calc PR A 2 H2A2 H 0.1757 0.4538 0.4725 0.075 Uiso 0.457(6) 1 calc PR A 2 C3A C 0.1794(5) 0.4133(2) 0.2911(5) 0.0684(12) Uani 0.457(6) 1 d P A 2 H3A1 H 0.2170 0.3773 0.3386 0.082 Uiso 0.457(6) 1 calc PR A 2 H3A2 H 0.0941 0.4003 0.2477 0.082 Uiso 0.457(6) 1 calc PR A 2 C4A C 0.2658(15) 0.4309(6) 0.2023(14) 0.083(4) Uani 0.457(6) 1 d P A 2 H4A1 H 0.2353 0.4153 0.1181 0.100 Uiso 0.457(6) 1 calc PR A 2 H4A2 H 0.3564 0.4152 0.2247 0.100 Uiso 0.457(6) 1 calc PR A 2 C5A C 0.2626(10) 0.4992(5) 0.2058(9) 0.062(2) Uani 0.457(6) 1 d P A 2 H5A1 H 0.1866 0.5150 0.1517 0.074 Uiso 0.457(6) 1 calc PR A 2 H5A2 H 0.3453 0.5164 0.1757 0.074 Uiso 0.457(6) 1 calc PR A 2 C6A C 0.186(2) 0.5790(9) 0.3558(17) 0.112(9) Uani 0.457(6) 1 d P A 2 H6A1 H 0.1476 0.5806 0.4385 0.135 Uiso 0.457(6) 1 calc PR A 2 H6A2 H 0.1110 0.5824 0.2910 0.135 Uiso 0.457(6) 1 calc PR A 2 C7A C 0.2784(10) 0.6367(5) 0.3442(10) 0.065(2) Uani 0.457(6) 1 d P A 2 H7A1 H 0.2231 0.6742 0.3307 0.079 Uiso 0.457(6) 1 calc PR A 2 H7A2 H 0.3335 0.6420 0.4237 0.079 Uiso 0.457(6) 1 calc PR A 2 C8 C 0.4338(5) 0.6756(2) 0.1766(4) 0.0640(11) Uani 1 1 d . A . C9 C 0.5139(5) 0.6572(2) 0.0809(4) 0.0697(12) Uani 1 1 d . . . H9 H 0.5214 0.6146 0.0610 0.084 Uiso 1 1 calc R . . C10 C 0.5829(4) 0.7014(2) 0.0148(4) 0.0618(10) Uani 1 1 d . . . H10 H 0.6378 0.6882 -0.0484 0.074 Uiso 1 1 calc R . . C11 C 0.5717(4) 0.76541(18) 0.0408(4) 0.0565(9) Uani 1 1 d . . . C12 C 0.4886(4) 0.78331(19) 0.1389(4) 0.0635(11) Uani 1 1 d . . . H12 H 0.4783 0.8257 0.1586 0.076 Uiso 1 1 calc R . . C13 C 0.4229(4) 0.7379(2) 0.2054(4) 0.0624(10) Uani 1 1 d . . . H13 H 0.3703 0.7500 0.2711 0.075 Uiso 1 1 calc R . . C14 C 0.6416(4) 0.81323(19) -0.0331(4) 0.0607(10) Uani 1 1 d . . . C15 C 0.7527(4) 0.79241(19) -0.1109(4) 0.0625(11) Uani 1 1 d . . . H15 H 0.7933 0.7534 -0.0941 0.075 Uiso 1 1 calc R . . C16 C 0.7955(5) 0.82809(19) -0.2038(4) 0.0641(11) Uani 1 1 d . . . H16 H 0.7549 0.8674 -0.2154 0.077 Uiso 1 1 calc R . . C17 C 0.9001(5) 0.81177(18) -0.2898(4) 0.0622(11) Uani 1 1 d . . . C18 C 0.9705(4) 0.7548(2) -0.2843(4) 0.0650(11) Uani 1 1 d . . . H18 H 0.9502 0.7247 -0.2241 0.078 Uiso 1 1 calc R . . C19 C 1.0688(5) 0.7424(2) -0.3656(5) 0.0739(13) Uani 1 1 d . . . H19 H 1.1149 0.7042 -0.3600 0.089 Uiso 1 1 calc R . . C20 C 1.1000(5) 0.7866(2) -0.4565(5) 0.0748(13) Uani 1 1 d . . . H20 H 1.1679 0.7787 -0.5111 0.090 Uiso 1 1 calc R . . C21 C 1.0290(6) 0.8421(2) -0.4644(4) 0.0787(14) Uani 1 1 d . . . H21 H 1.0477 0.8715 -0.5266 0.094 Uiso 1 1 calc R . . C22 C 0.9312(6) 0.8553(2) -0.3828(4) 0.0754(14) Uani 1 1 d . . . H22 H 0.8852 0.8935 -0.3895 0.090 Uiso 1 1 calc R . . N1 N 0.2032(10) 0.5272(5) 0.3270(11) 0.0387(19) Uani 0.543(6) 1 d P A 1 N1A N 0.2490(10) 0.5178(7) 0.3429(14) 0.040(3) Uani 0.457(6) 1 d P A 2 O1 O 0.3651(3) 0.63049(14) 0.2409(3) 0.0727(9) Uani 1 1 d . . . O2 O 0.6072(3) 0.86910(14) -0.0293(3) 0.0737(9) Uani 1 1 d . . . P1 P 0.26159(10) 0.54362(5) 0.79398(10) 0.0545(3) Uani 1 1 d . . . F1 F 0.3990(5) 0.5599(2) 0.7462(6) 0.0696(15) Uani 0.543(6) 1 d P A 1 F2 F 0.1149(5) 0.5320(3) 0.8592(6) 0.0651(14) Uani 0.543(6) 1 d P A 1 F3 F 0.3311(6) 0.5035(4) 0.9112(6) 0.106(2) Uani 0.543(6) 1 d P A 1 F4 F 0.1798(10) 0.5852(5) 0.6936(8) 0.080(2) Uani 0.543(6) 1 d P A 1 F5 F 0.2731(6) 0.6054(4) 0.8882(10) 0.113(3) Uani 0.543(6) 1 d P A 1 F6 F 0.2406(8) 0.4846(3) 0.7140(8) 0.0742(19) Uani 0.543(6) 1 d P A 1 F1A F 0.3421(7) 0.5579(4) 0.6597(8) 0.090(2) Uani 0.457(6) 1 d P A 2 F2A F 0.1836(9) 0.5226(3) 0.9005(6) 0.076(2) Uani 0.457(6) 1 d P A 2 F3A F 0.3718(8) 0.4864(4) 0.8202(9) 0.103(3) Uani 0.457(6) 1 d P A 2 F4A F 0.1609(16) 0.5949(7) 0.7435(12) 0.105(4) Uani 0.457(6) 1 d P A 2 F5A F 0.3479(14) 0.5909(6) 0.8642(11) 0.153(5) Uani 0.457(6) 1 d P A 2 F6A F 0.1765(7) 0.4918(5) 0.6989(10) 0.074(2) Uani 0.457(6) 1 d P A 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 C1 0.067(5) 0.032(5) 0.083(7) -0.010(5) 0.002(5) 0.006(5) C2 0.048(2) 0.077(3) 0.062(2) 0.012(2) 0.0059(18) -0.0156(19) C3 0.069(3) 0.053(2) 0.082(3) 0.003(2) -0.011(2) -0.003(2) C4 0.076(6) 0.059(5) 0.055(5) 0.003(4) -0.003(4) -0.008(4) C5 0.047(4) 0.054(4) 0.047(4) 0.010(3) -0.004(3) -0.002(3) C6 0.030(4) 0.054(4) 0.060(5) 0.001(3) -0.001(3) 0.002(3) C7 0.031(3) 0.043(3) 0.080(5) 0.001(3) 0.007(3) 0.000(2) C1A 0.020(3) 0.046(4) 0.073(6) 0.001(4) -0.008(4) -0.001(3) C2A 0.048(2) 0.077(3) 0.062(2) 0.012(2) 0.0059(18) -0.0156(19) C3A 0.069(3) 0.053(2) 0.082(3) 0.003(2) -0.011(2) -0.003(2) C4A 0.092(9) 0.061(7) 0.094(9) -0.009(6) -0.011(8) -0.020(6) C5A 0.051(5) 0.066(6) 0.067(5) -0.020(4) -0.001(4) -0.002(4) C6A 0.21(2) 0.058(8) 0.062(9) -0.023(6) -0.062(12) 0.072(12) C7A 0.057(5) 0.070(6) 0.069(6) 0.004(5) 0.005(4) -0.001(4) C8 0.071(3) 0.058(2) 0.062(2) 0.0071(19) -0.006(2) -0.014(2) C9 0.090(3) 0.064(3) 0.056(2) -0.0009(19) 0.011(2) -0.019(2) C10 0.067(3) 0.061(2) 0.057(2) -0.0003(18) -0.0004(19) -0.0060(19) C11 0.044(2) 0.056(2) 0.067(2) 0.0013(18) -0.0126(18) -0.0037(16) C12 0.050(2) 0.050(2) 0.087(3) -0.003(2) -0.017(2) -0.0019(17) C13 0.043(2) 0.069(3) 0.073(3) 0.010(2) -0.0124(18) -0.0087(18) C14 0.054(2) 0.053(2) 0.072(3) -0.0007(19) -0.0192(19) -0.0039(17) C15 0.053(2) 0.049(2) 0.082(3) 0.014(2) -0.014(2) -0.0073(17) C16 0.075(3) 0.046(2) 0.068(3) 0.0019(18) -0.016(2) -0.0124(19) C17 0.073(3) 0.046(2) 0.063(2) 0.0112(17) -0.022(2) -0.0223(19) C18 0.058(2) 0.054(2) 0.079(3) 0.019(2) -0.017(2) -0.0170(18) C19 0.058(3) 0.065(3) 0.096(3) 0.019(2) -0.016(2) -0.011(2) C20 0.066(3) 0.086(3) 0.070(3) 0.005(2) -0.014(2) -0.022(2) C21 0.108(4) 0.066(3) 0.058(3) 0.017(2) -0.018(3) -0.023(3) C22 0.115(4) 0.052(2) 0.057(2) 0.0124(19) -0.006(3) -0.015(2) N1 0.029(5) 0.038(5) 0.049(4) 0.012(3) 0.002(4) 0.004(4) N1A 0.025(7) 0.042(5) 0.051(5) 0.008(4) -0.001(5) 0.011(5) O1 0.083(2) 0.0566(17) 0.083(2) 0.0089(14) 0.0373(17) 0.0038(15) O2 0.079(2) 0.0518(17) 0.087(2) 0.0037(14) -0.0133(17) -0.0055(14) P1 0.0487(6) 0.0478(6) 0.0662(6) 0.0017(4) -0.0007(4) 0.0001(4) F1 0.059(3) 0.059(3) 0.095(4) -0.001(3) 0.028(3) 0.002(2) F2 0.045(3) 0.064(3) 0.087(4) 0.000(3) 0.012(2) 0.003(2) F3 0.078(4) 0.160(6) 0.082(4) 0.049(4) 0.015(3) 0.050(4) F4 0.089(5) 0.061(4) 0.087(6) 0.013(4) -0.013(4) 0.022(3) F5 0.052(3) 0.110(5) 0.179(7) -0.098(5) 0.017(4) -0.019(3) F6 0.085(5) 0.048(3) 0.091(4) -0.028(3) 0.016(4) -0.001(4) F1A 0.063(4) 0.133(6) 0.078(5) 0.019(4) 0.026(3) -0.014(4) F2A 0.102(6) 0.076(4) 0.054(4) 0.005(3) 0.028(4) 0.007(4) F3A 0.080(5) 0.117(6) 0.109(6) 0.022(5) -0.005(4) 0.042(4) F4A 0.144(8) 0.065(5) 0.111(9) 0.006(6) 0.038(7) 0.052(5) F5A 0.158(11) 0.164(11) 0.133(9) -0.009(8) -0.030(9) -0.110(10) F6A 0.055(4) 0.089(5) 0.077(4) -0.018(3) 0.001(4) -0.004(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 N1 1.518(15) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 N1 1.520(12) . ? C2 C3 1.530(6) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.574(10) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.492(11) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 N1 1.509(14) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.504(10) . ? C6 N1 1.506(9) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 O1 1.437(7) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C1A N1A 1.497(11) . ? C1A H1A1 0.9600 . ? C1A H1A2 0.9600 . ? C1A H1A3 0.9600 . ? C4A C5A 1.450(16) . ? C4A H4A1 0.9700 . ? C4A H4A2 0.9700 . ? C5A N1A 1.506(17) . ? C5A H5A1 0.9700 . ? C5A H5A2 0.9700 . ? C6A N1A 1.453(18) . ? C6A C7A 1.54(3) . ? C6A H6A1 0.9700 . ? C6A H6A2 0.9700 . ? C7A O1 1.437(10) . ? C7A H7A1 0.9700 . ? C7A H7A2 0.9700 . ? C8 C13 1.359(6) . ? C8 O1 1.378(5) . ? C8 C9 1.380(6) . ? C9 C10 1.376(6) . ? C9 H9 0.9300 . ? C10 C11 1.391(6) . ? C10 H10 0.9300 . ? C11 C12 1.415(6) . ? C11 C14 1.479(6) . ? C12 C13 1.380(6) . ? C12 H12 0.9300 . ? C13 H13 0.9300 . ? C14 O2 1.234(5) . ? C14 C15 1.484(6) . ? C15 C16 1.326(6) . ? C15 H15 0.9300 . ? C16 C17 1.464(7) . ? C16 H16 0.9300 . ? C17 C22 1.393(6) . ? C17 C18 1.394(6) . ? C18 C19 1.366(7) . ? C18 H18 0.9300 . ? C19 C20 1.386(6) . ? C19 H19 0.9300 . ? C20 C21 1.371(7) . ? C20 H20 0.9300 . ? C21 C22 1.367(8) . ? C21 H21 0.9300 . ? C22 H22 0.9300 . ? P1 F2A 1.473(7) . ? P1 F5A 1.479(9) . ? P1 F6 1.512(7) . ? P1 F1 1.524(5) . ? P1 F4A 1.543(14) . ? P1 F4 1.555(9) . ? P1 F3 1.608(5) . ? P1 F5 1.639(6) . ? P1 F3A 1.642(6) . ? P1 F2 1.669(5) . ? P1 F6A 1.671(9) . ? P1 F1A 1.695(6) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C2 C3 107.1(6) . . ? N1 C2 H2A 110.3 . . ? C3 C2 H2A 110.3 . . ? N1 C2 H2B 110.3 . . ? C3 C2 H2B 110.3 . . ? H2A C2 H2B 108.5 . . ? C2 C3 C4 102.7(4) . . ? C2 C3 H3A 111.2 . . ? C4 C3 H3A 111.2 . . ? C2 C3 H3B 111.2 . . ? C4 C3 H3B 111.2 . . ? H3A C3 H3B 109.1 . . ? C5 C4 C3 105.1(6) . . ? C5 C4 H4A 110.7 . . ? C3 C4 H4A 110.7 . . ? C5 C4 H4B 110.7 . . ? C3 C4 H4B 110.7 . . ? H4A C4 H4B 108.8 . . ? C4 C5 N1 104.5(6) . . ? C4 C5 H5A 110.8 . . ? N1 C5 H5A 110.8 . . ? C4 C5 H5B 110.8 . . ? N1 C5 H5B 110.8 . . ? H5A C5 H5B 108.9 . . ? C7 C6 N1 115.0(8) . . ? C7 C6 H6A 108.5 . . ? N1 C6 H6A 108.5 . . ? C7 C6 H6B 108.5 . . ? N1 C6 H6B 108.5 . . ? H6A C6 H6B 107.5 . . ? O1 C7 C6 108.3(5) . . ? O1 C7 H7A 110.0 . . ? C6 C7 H7A 110.0 . . ? O1 C7 H7B 110.0 . . ? C6 C7 H7B 110.0 . . ? H7A C7 H7B 108.4 . . ? N1A C1A H1A1 109.5 . . ? N1A C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? N1A C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C5A C4A H4A1 111.0 . . ? C5A C4A H4A2 111.0 . . ? H4A1 C4A H4A2 109.0 . . ? C4A C5A N1A 106.8(10) . . ? C4A C5A H5A1 110.4 . . ? N1A C5A H5A1 110.4 . . ? C4A C5A H5A2 110.4 . . ? N1A C5A H5A2 110.4 . . ? H5A1 C5A H5A2 108.6 . . ? N1A C6A C7A 115.9(17) . . ? N1A C6A H6A1 108.3 . . ? C7A C6A H6A1 108.3 . . ? N1A C6A H6A2 108.3 . . ? C7A C6A H6A2 108.3 . . ? H6A1 C6A H6A2 107.4 . . ? O1 C7A C6A 112.4(10) . . ? O1 C7A H7A1 109.1 . . ? C6A C7A H7A1 109.1 . . ? O1 C7A H7A2 109.1 . . ? C6A C7A H7A2 109.1 . . ? H7A1 C7A H7A2 107.9 . . ? C13 C8 O1 121.0(4) . . ? C13 C8 C9 119.7(4) . . ? O1 C8 C9 119.3(4) . . ? C10 C9 C8 120.4(4) . . ? C10 C9 H9 119.8 . . ? C8 C9 H9 119.8 . . ? C9 C10 C11 121.1(4) . . ? C9 C10 H10 119.5 . . ? C11 C10 H10 119.5 . . ? C10 C11 C12 117.6(4) . . ? C10 C11 C14 121.3(4) . . ? C12 C11 C14 121.1(4) . . ? C13 C12 C11 120.0(4) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C8 C13 C12 121.2(4) . . ? C8 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? O2 C14 C11 120.0(4) . . ? O2 C14 C15 121.4(4) . . ? C11 C14 C15 118.6(4) . . ? C16 C15 C14 121.5(4) . . ? C16 C15 H15 119.2 . . ? C14 C15 H15 119.2 . . ? C15 C16 C17 126.5(4) . . ? C15 C16 H16 116.7 . . ? C17 C16 H16 116.7 . . ? C22 C17 C18 117.8(5) . . ? C22 C17 C16 118.5(4) . . ? C18 C17 C16 123.6(4) . . ? C19 C18 C17 121.2(4) . . ? C19 C18 H18 119.4 . . ? C17 C18 H18 119.4 . . ? C18 C19 C20 120.3(5) . . ? C18 C19 H19 119.9 . . ? C20 C19 H19 119.9 . . ? C21 C20 C19 118.8(5) . . ? C21 C20 H20 120.6 . . ? C19 C20 H20 120.6 . . ? C22 C21 C20 121.4(4) . . ? C22 C21 H21 119.3 . . ? C20 C21 H21 119.3 . . ? C21 C22 C17 120.4(5) . . ? C21 C22 H22 119.8 . . ? C17 C22 H22 119.8 . . ? C6 N1 C5 112.7(8) . . ? C6 N1 C1 107.8(10) . . ? C5 N1 C1 112.2(9) . . ? C6 N1 C2 110.2(6) . . ? C5 N1 C2 99.7(8) . . ? C1 N1 C2 114.2(9) . . ? C6A N1A C1A 113.8(13) . . ? C6A N1A C5A 113.1(12) . . ? C1A N1A C5A 111.8(9) . . ? C8 O1 C7A 130.4(5) . . ? C8 O1 C7 117.2(4) . . ? C7A O1 C7 107.0(5) . . ? F2A P1 F5A 98.3(6) . . ? F2A P1 F6 96.4(4) . . ? F5A P1 F6 152.6(7) . . ? F2A P1 F1 148.0(4) . . ? F5A P1 F1 60.8(6) . . ? F6 P1 F1 95.5(4) . . ? F2A P1 F4A 96.4(6) . . ? F5A P1 F4A 91.7(9) . . ? F6 P1 F4A 109.4(6) . . ? F1 P1 F4A 107.5(6) . . ? F2A P1 F4 114.1(5) . . ? F5A P1 F4 102.0(7) . . ? F6 P1 F4 92.8(5) . . ? F1 P1 F4 94.9(4) . . ? F4A P1 F4 22.5(4) . . ? F2A P1 F3 58.7(4) . . ? F5A P1 F3 77.2(6) . . ? F6 P1 F3 91.1(4) . . ? F1 P1 F3 91.5(3) . . ? F4A P1 F3 149.9(5) . . ? F4 P1 F3 172.1(4) . . ? F2A P1 F5 78.6(5) . . ? F5A P1 F5 31.4(6) . . ? F6 P1 F5 174.8(4) . . ? F1 P1 F5 89.6(3) . . ? F4A P1 F5 70.1(6) . . ? F4 P1 F5 88.0(5) . . ? F3 P1 F5 87.4(5) . . ? F2A P1 F3A 91.7(4) . . ? F5A P1 F3A 93.6(7) . . ? F6 P1 F3A 62.9(4) . . ? F1 P1 F3A 67.8(4) . . ? F4A P1 F3A 169.6(5) . . ? F4 P1 F3A 147.1(4) . . ? F3 P1 F3A 40.4(3) . . ? F5 P1 F3A 118.2(5) . . ? F2A P1 F2 28.8(3) . . ? F5A P1 F2 112.7(6) . . ? F6 P1 F2 90.9(4) . . ? F1 P1 F2 173.5(3) . . ? F4A P1 F2 71.5(6) . . ? F4 P1 F2 86.2(4) . . ? F3 P1 F2 86.9(3) . . ? F5 P1 F2 84.0(3) . . ? F3A P1 F2 114.3(4) . . ? F2A P1 F6A 89.0(5) . . ? F5A P1 F6A 172.6(6) . . ? F6 P1 F6A 23.3(3) . . ? F1 P1 F6A 112.2(4) . . ? F4A P1 F6A 88.4(7) . . ? F4 P1 F6A 75.7(5) . . ? F3 P1 F6A 106.1(5) . . ? F5 P1 F6A 153.5(4) . . ? F3A P1 F6A 85.1(4) . . ? F2 P1 F6A 74.3(4) . . ? F2A P1 F1A 171.3(4) . . ? F5A P1 F1A 90.1(6) . . ? F6 P1 F1A 75.0(4) . . ? F1 P1 F1A 37.0(3) . . ? F4A P1 F1A 85.5(5) . . ? F4 P1 F1A 65.8(4) . . ? F3 P1 F1A 121.8(3) . . ? F5 P1 F1A 109.9(5) . . ? F3A P1 F1A 85.6(4) . . ? F2 P1 F1A 147.5(3) . . ? F6A P1 F1A 82.5(5) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C2 C3 C4 -17.9(6) . . . . ? C2 C3 C4 C5 -10.6(7) . . . . ? C3 C4 C5 N1 35.5(9) . . . . ? N1 C6 C7 O1 56.6(9) . . . . ? N1A C6A C7A O1 43.3(16) . . . . ? C13 C8 C9 C10 0.1(7) . . . . ? O1 C8 C9 C10 179.6(4) . . . . ? C8 C9 C10 C11 -1.2(7) . . . . ? C9 C10 C11 C12 0.9(6) . . . . ? C9 C10 C11 C14 -177.8(4) . . . . ? C10 C11 C12 C13 0.4(5) . . . . ? C14 C11 C12 C13 179.1(3) . . . . ? O1 C8 C13 C12 -178.2(4) . . . . ? C9 C8 C13 C12 1.3(6) . . . . ? C11 C12 C13 C8 -1.6(6) . . . . ? C10 C11 C14 O2 163.5(4) . . . . ? C12 C11 C14 O2 -15.1(6) . . . . ? C10 C11 C14 C15 -16.4(5) . . . . ? C12 C11 C14 C15 164.9(3) . . . . ? O2 C14 C15 C16 -17.8(6) . . . . ? C11 C14 C15 C16 162.1(4) . . . . ? C14 C15 C16 C17 -177.5(4) . . . . ? C15 C16 C17 C22 179.6(4) . . . . ? C15 C16 C17 C18 -0.3(6) . . . . ? C22 C17 C18 C19 1.3(6) . . . . ? C16 C17 C18 C19 -178.9(4) . . . . ? C17 C18 C19 C20 -0.4(7) . . . . ? C18 C19 C20 C21 -1.1(7) . . . . ? C19 C20 C21 C22 1.7(7) . . . . ? C20 C21 C22 C17 -0.8(7) . . . . ? C18 C17 C22 C21 -0.7(6) . . . . ? C16 C17 C22 C21 179.5(4) . . . . ? C7 C6 N1 C5 40.5(10) . . . . ? C7 C6 N1 C1 -83.9(11) . . . . ? C7 C6 N1 C2 150.8(7) . . . . ? C4 C5 N1 C6 71.1(9) . . . . ? C4 C5 N1 C1 -167.0(9) . . . . ? C4 C5 N1 C2 -45.7(7) . . . . ? C3 C2 N1 C6 -79.7(8) . . . . ? C3 C2 N1 C5 39.0(6) . . . . ? C3 C2 N1 C1 158.9(9) . . . . ? C7A C6A N1A C1A 48.4(18) . . . . ? C7A C6A N1A C5A -80.6(15) . . . . ? C4A C5A N1A C6A -154.1(15) . . . . ? C4A C5A N1A C1A 75.9(13) . . . . ? C13 C8 O1 C7A -1.7(8) . . . . ? C9 C8 O1 C7A 178.7(6) . . . . ? C13 C8 O1 C7 -152.2(5) . . . . ? C9 C8 O1 C7 28.2(6) . . . . ? C6A C7A O1 C8 160.1(8) . . . . ? C6A C7A O1 C7 -47.1(10) . . . . ? C6 C7 O1 C8 165.7(5) . . . . ? C6 C7 O1 C7A 8.8(7) . . . . ? _diffrn_measured_fraction_theta_max 0.972 _diffrn_reflns_theta_full 70.56 _diffrn_measured_fraction_theta_full 0.972 _refine_diff_density_max 0.853 _refine_diff_density_min -0.472 _refine_diff_density_rms 0.056 _audit_creation_date ; 'Sat Sep 20 00:19:37 2008' ; _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 7.00 65.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -13.7937 77.0000 300.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 2 omega -20.00 38.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 13.7937 77.0000 210.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 3 omega -50.00 -2.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -13.7937 85.0000 8.0000 0.0000 0.0000 48 #__ type_ start__ end____ width___ exp.time_ 4 omega -60.00 -7.00 1.0000 4.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 13.7937 -45.0000 270.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 5 omega -167.00 -65.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 -45.0000 240.0000 0.0000 0.0000 102 #__ type_ start__ end____ width___ exp.time_ 6 omega -118.00 -65.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 -45.0000 330.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 7 omega -178.00 -6.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 0.0000 0.0000 0.0000 0.0000 172 #__ type_ start__ end____ width___ exp.time_ 8 omega -127.00 -68.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 77.0000 150.0000 0.0000 0.0000 59 #__ type_ start__ end____ width___ exp.time_ 9 omega 21.00 80.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 -77.0000 0.0000 0.0000 0.0000 59 #__ type_ start__ end____ width___ exp.time_ 10 omega 13.00 70.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 0.0000 30.0000 0.0000 0.0000 57 #__ type_ start__ end____ width___ exp.time_ 11 omega 21.00 80.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 -77.0000 60.0000 0.0000 0.0000 59 #__ type_ start__ end____ width___ exp.time_ 12 omega 72.00 125.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 45.0000 240.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 13 omega 66.00 124.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 77.0000 300.0000 0.0000 0.0000 58 #__ type_ start__ end____ width___ exp.time_ 14 omega 72.00 125.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - 100.0000 45.0000 120.0000 0.0000 0.0000 53 #__ type_ start__ end____ width___ exp.time_ 15 omega -178.00 -6.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 0.0000 180.0000 0.0000 0.0000 172 #__ type_ start__ end____ width___ exp.time_ 16 omega -178.00 -6.00 1.0000 16.0000 omega____ theta____ kappa____ phi______ omega'___ theta'___ frames - -93.0000 0.0000 30.0000 0.0000 0.0000 172 ; #===END