# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Professor R.E.Grigg' _publ_contact_author_address ; Department of Chemistry University of Leeds Leeds LS2 9JT UK ; _publ_contact_author_email R.Grigg@chemistry.leeds.ac.uk _publ_contact_author_phone '+44 (0)113 34 36501' loop_ _publ_author_name _publ_author_address R.E.Grigg ; Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; 'Laura Cleghorn' ; Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; 'Colin Kilner' ; Department of Chemistry University of Leeds Leeds, LS2 9JT, UK ; 'William S. MacLachlan' ; ? ; 'V. Sridharan' ; ? ; _publ_section_title ; Bimetallic Catalytic Synthesis of Annelated Benzazepines ; data_lac582 _database_code_depnum_ccdc_archive 'CCDC 266424' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 N O' _chemical_formula_sum 'C19 H19 N O' _chemical_formula_weight 277.35 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/c _symmetry_space_group_name_Hall '-P 2ybc' 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 10.0020(3) _cell_length_b 13.1350(4) _cell_length_c 10.9480(4) _cell_angle_alpha 90.00 _cell_angle_beta 92.8250(12) _cell_angle_gamma 90.00 _cell_volume 1436.56(8) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8073 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.26 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.282 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 12805 _diffrn_reflns_av_R_equivalents 0.0793 _diffrn_reflns_av_sigmaI/netI 0.0497 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 3.10 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2816 _reflns_number_gt 2165 _reflns_threshold_expression >2sigma(I) _computing_data_collection COLLECT _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLECT (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-III Version 1.08 (Farrugia, 2005)' _computing_publication_material 'local program' _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^)+(0.0580P)^2^+0.2046P] 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 2816 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0587 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1166 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.039 _refine_ls_restrained_S_all 1.039 _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 O53 O 0.27087(11) 0.54430(8) 0.25482(10) 0.0387(3) Uani 1 1 d . . . N1 N 0.25251(11) 0.14610(8) 0.05182(10) 0.0273(3) Uani 1 1 d . . . C2 C 0.12091(14) 0.09936(11) 0.02850(13) 0.0304(3) Uani 1 1 d . . . H2A H 0.0913 0.0675 0.1045 0.036 Uiso 1 1 calc R . . H2B H 0.1271 0.0454 -0.0341 0.036 Uiso 1 1 calc R . . C13 C 0.34005(15) -0.11560(11) 0.11865(15) 0.0361(4) Uani 1 1 d . . . H13 H 0.3502 -0.1298 0.0345 0.043 Uiso 1 1 calc R . . C6 C 0.25356(13) 0.22417(10) 0.14742(12) 0.0268(3) Uani 1 1 d . . . H6 H 0.3432 0.2580 0.1488 0.032 Uiso 1 1 calc R . . C3 C 0.01882(15) 0.17914(11) -0.01589(13) 0.0328(3) Uani 1 1 d . . . H3A H 0.0225 0.1864 -0.1057 0.039 Uiso 1 1 calc R . . H3B H -0.0720 0.1551 0.0019 0.039 Uiso 1 1 calc R . . C9 C 0.32682(14) 0.00523(11) 0.28310(13) 0.0306(3) Uani 1 1 d . . . C14 C 0.34052(14) -0.01497(11) 0.15794(13) 0.0303(3) Uani 1 1 d . . . C5 C 0.14978(14) 0.30463(10) 0.11418(12) 0.0275(3) Uani 1 1 d . . . C4 C 0.04193(14) 0.28130(11) 0.04247(13) 0.0306(3) Uani 1 1 d . . . H4 H -0.0239 0.3325 0.0276 0.037 Uiso 1 1 calc R . . C7 C 0.23129(14) 0.18665(11) 0.27904(12) 0.0284(3) Uani 1 1 d . . . H7A H 0.2313 0.2466 0.3339 0.034 Uiso 1 1 calc R . . H7B H 0.1415 0.1550 0.2800 0.034 Uiso 1 1 calc R . . C15 C 0.36028(14) 0.07066(11) 0.06764(13) 0.0301(3) Uani 1 1 d . . . H15A H 0.4435 0.1072 0.0934 0.036 Uiso 1 1 calc R . . H15B H 0.3746 0.0398 -0.0132 0.036 Uiso 1 1 calc R . . C8 C 0.33282(14) 0.11142(11) 0.33029(12) 0.0291(3) Uani 1 1 d . . . C81 C 0.42428(16) 0.13838(12) 0.41571(13) 0.0383(4) Uani 1 1 d . . . H81A H 0.4870 0.0897 0.4475 0.046 Uiso 1 1 calc R . . H81B H 0.4272 0.2064 0.4452 0.046 Uiso 1 1 calc R . . C55 C 0.07704(16) 0.48883(11) 0.17144(14) 0.0354(4) Uani 1 1 d . . . H55 H -0.0140 0.4870 0.1425 0.043 Uiso 1 1 calc R . . C12 C 0.32518(16) -0.19603(12) 0.19933(16) 0.0428(4) Uani 1 1 d . . . H12 H 0.3270 -0.2643 0.1709 0.051 Uiso 1 1 calc R . . C51 C 0.17181(14) 0.40689(10) 0.16622(12) 0.0287(3) Uani 1 1 d . . . C10 C 0.30780(15) -0.07574(12) 0.36289(15) 0.0373(4) Uani 1 1 d . . . H10 H 0.2947 -0.0624 0.4467 0.045 Uiso 1 1 calc R . . C52 C 0.28706(15) 0.44532(11) 0.21821(14) 0.0356(4) Uani 1 1 d . . . H52 H 0.3685 0.4084 0.2280 0.043 Uiso 1 1 calc R . . C54 C 0.14041(15) 0.56799(11) 0.22437(14) 0.0366(4) Uani 1 1 d . . . H54 H 0.1002 0.6321 0.2389 0.044 Uiso 1 1 calc R . . C11 C 0.30774(16) -0.17556(12) 0.32139(16) 0.0432(4) Uani 1 1 d . . . H11 H 0.2957 -0.2300 0.3770 0.052 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O53 0.0401(7) 0.0292(6) 0.0467(7) -0.0056(5) -0.0003(5) -0.0007(5) N1 0.0282(6) 0.0263(6) 0.0273(6) -0.0013(5) 0.0008(5) 0.0000(5) C2 0.0329(8) 0.0289(8) 0.0292(8) -0.0023(6) 0.0003(6) -0.0045(6) C13 0.0294(8) 0.0323(8) 0.0467(9) -0.0036(7) 0.0024(6) -0.0001(6) C6 0.0257(7) 0.0269(7) 0.0276(7) -0.0008(5) 0.0003(5) -0.0011(6) C3 0.0299(8) 0.0351(8) 0.0331(8) 0.0010(6) -0.0026(6) -0.0034(6) C9 0.0225(7) 0.0322(8) 0.0367(8) 0.0040(6) -0.0019(6) 0.0019(6) C14 0.0227(7) 0.0293(8) 0.0387(8) 0.0002(6) 0.0002(6) 0.0016(6) C5 0.0283(8) 0.0284(8) 0.0258(7) 0.0027(5) 0.0032(6) 0.0001(6) C4 0.0286(8) 0.0307(8) 0.0323(8) 0.0032(6) 0.0002(6) 0.0023(6) C7 0.0300(8) 0.0282(8) 0.0270(7) 0.0002(6) 0.0006(6) 0.0013(6) C15 0.0291(8) 0.0300(8) 0.0315(8) -0.0021(6) 0.0039(6) 0.0016(6) C8 0.0290(7) 0.0318(8) 0.0266(7) 0.0024(6) 0.0029(6) 0.0008(6) C81 0.0398(9) 0.0398(9) 0.0347(8) 0.0007(7) -0.0046(7) 0.0043(7) C55 0.0316(8) 0.0311(8) 0.0436(9) -0.0001(6) 0.0012(7) 0.0035(6) C12 0.0361(9) 0.0271(8) 0.0651(11) 0.0009(7) 0.0012(8) -0.0008(6) C51 0.0315(8) 0.0274(8) 0.0272(7) 0.0036(6) 0.0027(6) 0.0008(6) C10 0.0319(8) 0.0390(9) 0.0404(9) 0.0088(7) -0.0030(6) 0.0017(7) C52 0.0368(9) 0.0270(8) 0.0428(9) -0.0039(6) -0.0015(7) 0.0028(6) C54 0.0381(9) 0.0287(8) 0.0431(9) 0.0003(6) 0.0033(7) 0.0054(6) C11 0.0380(9) 0.0330(9) 0.0581(11) 0.0139(7) -0.0018(7) 0.0012(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 O53 C54 1.3667(18) . ? O53 C52 1.3724(18) . ? N1 C2 1.4634(18) . ? N1 C6 1.4649(17) . ? N1 C15 1.4682(17) . ? C2 C3 1.526(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C13 C12 1.390(2) . ? C13 C14 1.390(2) . ? C13 H13 0.9500 . ? C6 C5 1.5131(19) . ? C6 C7 1.5494(18) . ? C6 H6 1.0000 . ? C3 C4 1.499(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C9 C10 1.395(2) . ? C9 C14 1.409(2) . ? C9 C8 1.488(2) . ? C14 C15 1.517(2) . ? C5 C4 1.3381(19) . ? C5 C51 1.4713(19) . ? C4 H4 0.9500 . ? C7 C8 1.5054(19) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C8 C81 1.324(2) . ? C81 H81A 0.9500 . ? C81 H81B 0.9500 . ? C55 C54 1.335(2) . ? C55 C51 1.437(2) . ? C55 H55 0.9500 . ? C12 C11 1.383(2) . ? C12 H12 0.9500 . ? C51 C52 1.358(2) . ? C10 C11 1.388(2) . ? C10 H10 0.9500 . ? C52 H52 0.9500 . ? C54 H54 0.9500 . ? C11 H11 0.9500 . ? 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 C54 O53 C52 105.63(11) . . ? C2 N1 C6 113.14(11) . . ? C2 N1 C15 112.72(11) . . ? C6 N1 C15 114.13(10) . . ? N1 C2 C3 110.45(11) . . ? N1 C2 H2A 109.6 . . ? C3 C2 H2A 109.6 . . ? N1 C2 H2B 109.6 . . ? C3 C2 H2B 109.6 . . ? H2A C2 H2B 108.1 . . ? C12 C13 C14 121.68(15) . . ? C12 C13 H13 119.2 . . ? C14 C13 H13 119.2 . . ? N1 C6 C5 109.66(10) . . ? N1 C6 C7 116.46(11) . . ? C5 C6 C7 108.51(11) . . ? N1 C6 H6 107.3 . . ? C5 C6 H6 107.3 . . ? C7 C6 H6 107.3 . . ? C4 C3 C2 113.10(11) . . ? C4 C3 H3A 109.0 . . ? C2 C3 H3A 109.0 . . ? C4 C3 H3B 109.0 . . ? C2 C3 H3B 109.0 . . ? H3A C3 H3B 107.8 . . ? C10 C9 C14 119.22(14) . . ? C10 C9 C8 120.11(14) . . ? C14 C9 C8 120.67(13) . . ? C13 C14 C9 118.75(14) . . ? C13 C14 C15 120.14(13) . . ? C9 C14 C15 121.08(13) . . ? C4 C5 C51 122.50(13) . . ? C4 C5 C6 120.32(12) . . ? C51 C5 C6 117.17(11) . . ? C5 C4 C3 123.91(13) . . ? C5 C4 H4 118.0 . . ? C3 C4 H4 118.0 . . ? C8 C7 C6 115.48(11) . . ? C8 C7 H7A 108.4 . . ? C6 C7 H7A 108.4 . . ? C8 C7 H7B 108.4 . . ? C6 C7 H7B 108.4 . . ? H7A C7 H7B 107.5 . . ? N1 C15 C14 117.32(12) . . ? N1 C15 H15A 108.0 . . ? C14 C15 H15A 108.0 . . ? N1 C15 H15B 108.0 . . ? C14 C15 H15B 108.0 . . ? H15A C15 H15B 107.2 . . ? C81 C8 C9 120.71(13) . . ? C81 C8 C7 121.18(13) . . ? C9 C8 C7 118.11(12) . . ? C8 C81 H81A 120.0 . . ? C8 C81 H81B 120.0 . . ? H81A C81 H81B 120.0 . . ? C54 C55 C51 107.50(14) . . ? C54 C55 H55 126.3 . . ? C51 C55 H55 126.3 . . ? C11 C12 C13 119.28(14) . . ? C11 C12 H12 120.4 . . ? C13 C12 H12 120.4 . . ? C52 C51 C55 104.65(13) . . ? C52 C51 C5 127.57(13) . . ? C55 C51 C5 127.78(13) . . ? C11 C10 C9 120.87(16) . . ? C11 C10 H10 119.6 . . ? C9 C10 H10 119.6 . . ? C51 C52 O53 111.39(13) . . ? C51 C52 H52 124.3 . . ? O53 C52 H52 124.3 . . ? C55 C54 O53 110.83(13) . . ? C55 C54 H54 124.6 . . ? O53 C54 H54 124.6 . . ? C12 C11 C10 120.14(15) . . ? C12 C11 H11 119.9 . . ? C10 C11 H11 119.9 . . ? 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 N1 C2 C3 61.63(14) . . . . ? C15 N1 C2 C3 -167.00(11) . . . . ? C2 N1 C6 C5 -56.21(14) . . . . ? C15 N1 C6 C5 173.12(11) . . . . ? C2 N1 C6 C7 67.46(14) . . . . ? C15 N1 C6 C7 -63.21(15) . . . . ? N1 C2 C3 C4 -35.07(16) . . . . ? C12 C13 C14 C9 0.6(2) . . . . ? C12 C13 C14 C15 178.56(13) . . . . ? C10 C9 C14 C13 -2.6(2) . . . . ? C8 C9 C14 C13 177.27(13) . . . . ? C10 C9 C14 C15 179.52(13) . . . . ? C8 C9 C14 C15 -0.6(2) . . . . ? N1 C6 C5 C4 26.66(17) . . . . ? C7 C6 C5 C4 -101.55(15) . . . . ? N1 C6 C5 C51 -154.74(12) . . . . ? C7 C6 C5 C51 77.05(15) . . . . ? C51 C5 C4 C3 177.60(13) . . . . ? C6 C5 C4 C3 -3.9(2) . . . . ? C2 C3 C4 C5 8.0(2) . . . . ? N1 C6 C7 C8 60.02(16) . . . . ? C5 C6 C7 C8 -175.73(11) . . . . ? C2 N1 C15 C14 -50.65(15) . . . . ? C6 N1 C15 C14 80.23(15) . . . . ? C13 C14 C15 N1 119.96(14) . . . . ? C9 C14 C15 N1 -62.17(18) . . . . ? C10 C9 C8 C81 58.9(2) . . . . ? C14 C9 C8 C81 -120.91(16) . . . . ? C10 C9 C8 C7 -120.48(15) . . . . ? C14 C9 C8 C7 59.67(18) . . . . ? C6 C7 C8 C81 106.79(16) . . . . ? C6 C7 C8 C9 -73.79(16) . . . . ? C14 C13 C12 C11 1.3(2) . . . . ? C54 C55 C51 C52 0.08(17) . . . . ? C54 C55 C51 C5 -178.94(14) . . . . ? C4 C5 C51 C52 -165.40(15) . . . . ? C6 C5 C51 C52 16.0(2) . . . . ? C4 C5 C51 C55 13.4(2) . . . . ? C6 C5 C51 C55 -165.16(13) . . . . ? C14 C9 C10 C11 2.7(2) . . . . ? C8 C9 C10 C11 -177.19(14) . . . . ? C55 C51 C52 O53 -0.09(17) . . . . ? C5 C51 C52 O53 178.94(13) . . . . ? C54 O53 C52 C51 0.06(17) . . . . ? C51 C55 C54 O53 -0.05(17) . . . . ? C52 O53 C54 C55 0.00(17) . . . . ? C13 C12 C11 C10 -1.3(2) . . . . ? C9 C10 C11 C12 -0.7(2) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.176 _refine_diff_density_min -0.224 _refine_diff_density_rms 0.041 data_lac468 _database_code_depnum_ccdc_archive 'CCDC 266425' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C26 H25 N' _chemical_formula_sum 'C26 H25 N' _chemical_formula_weight 351.47 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P n a 21' _symmetry_space_group_name_Hall 'P 2c -2n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, z' '-x, -y, z+1/2' _cell_length_a 10.3740(2) _cell_length_b 19.2830(7) _cell_length_c 9.7330(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1947.01(10) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 8032 _cell_measurement_theta_min 1.00 _cell_measurement_theta_max 27.48 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.26 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.199 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 752 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type none _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relevant to area detector data since the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree range. The crystal temperature was held constant using an Oxford Cryosystems Cryostream 600 system. ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_probe x-ray _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 ; Nonius KappaCCD area-detector diffractometer ; _diffrn_radiation_detector 'CCD plate' _diffrn_measurement_method ; phi and omega scans to fill the asymmetric unit ; _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 10989 _diffrn_reflns_av_R_equivalents 0.0606 _diffrn_reflns_av_sigmaI/netI 0.0390 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 26.00 _reflns_number_total 2025 _reflns_number_gt 1834 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'DENZO-SMN (Otwinowski & Minor, 1996)' _computing_data_reduction ; DENZO-SMN and COLLE_computing_data_collection COLLECT CT (Otwinowski & Minor, 1996) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ORTEP-III _computing_publication_material 'local program' _refine_special_details ; H atoms were positioned geometrically and refined using a riding model (including free rotation about C-C bonds), with Uiso constrained to be 1.2 times Ueq of the carrier atom. In the absence of significant anomalous scattering effects, the absolute configuration could not be confirmed from the diffraction data and Friedel pairs were merged. C.Kilner 8 February 2005 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^)+(0.0656P)^2^+0.1518P] 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 2025 _refine_ls_number_parameters 244 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0448 _refine_ls_R_factor_gt 0.0395 _refine_ls_wR_factor_ref 0.1031 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_restrained_S_all 1.048 _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 C10 C -0.67209(18) -0.76000(10) 0.3807(2) 0.0297(4) Uani 1 1 d . . . H10 H -0.7422 -0.7673 0.3118 0.036 Uiso 1 1 calc R . . C13 C -0.47164(19) -0.67531(11) 0.1771(2) 0.0318(4) Uani 1 1 d . . . C4 C -0.69599(17) -0.77717(10) 0.6384(2) 0.0301(4) Uani 1 1 d . . . C5 C -0.7405(2) -0.81705(12) 0.7480(2) 0.0353(5) Uani 1 1 d . . . H5 H -0.7354 -0.7989 0.8386 0.042 Uiso 1 1 calc R . . C3 C -0.6406(2) -0.70579(10) 0.6672(2) 0.0323(4) Uani 1 1 d . . . H3 H -0.5657 -0.7119 0.7308 0.039 Uiso 1 1 calc R . . C19 C -0.6736(2) -0.63793(11) 0.3084(2) 0.0381(5) Uani 1 1 d . . . H19A H -0.7093 -0.5935 0.3425 0.046 Uiso 1 1 calc R . . H19B H -0.7323 -0.6549 0.2357 0.046 Uiso 1 1 calc R . . C6 C -0.7917(2) -0.88229(11) 0.7277(2) 0.0365(5) Uani 1 1 d . . . H6 H -0.8233 -0.9082 0.8036 0.044 Uiso 1 1 calc R . . C9 C -0.70549(17) -0.80369(11) 0.5051(2) 0.0288(4) Uani 1 1 d . . . C11 C -0.54421(19) -0.78407(11) 0.3122(2) 0.0319(4) Uani 1 1 d . . . H11A H -0.4726 -0.7755 0.3773 0.038 Uiso 1 1 calc R . . H11B H -0.5491 -0.8347 0.2968 0.038 Uiso 1 1 calc R . . C31 C -0.73719(19) -0.65847(10) 0.7381(2) 0.0321(4) Uani 1 1 d . . . C32 C -0.8543(2) -0.64227(12) 0.6770(2) 0.0396(5) Uani 1 1 d . . . H32 H -0.8772 -0.6637 0.5926 0.048 Uiso 1 1 calc R . . C18 C -0.54357(19) -0.62273(11) 0.2423(2) 0.0346(5) Uani 1 1 d . . . C14 C -0.35713(19) -0.65675(12) 0.1111(2) 0.0373(5) Uani 1 1 d . . . H14 H -0.3078 -0.6917 0.0666 0.045 Uiso 1 1 calc R . . C22 C -0.5114(2) -0.78544(12) 0.0605(2) 0.0412(5) Uani 1 1 d . . . H22A H -0.4852 -0.7640 -0.0228 0.049 Uiso 1 1 calc R . . H22B H -0.5372 -0.8327 0.0607 0.049 Uiso 1 1 calc R . . C8 C -0.75424(19) -0.87078(11) 0.4863(2) 0.0331(5) Uani 1 1 d . . . H8 H -0.7581 -0.8898 0.3964 0.040 Uiso 1 1 calc R . . C17 C -0.4975(2) -0.55500(11) 0.2410(2) 0.0411(5) Uani 1 1 d . . . H17 H -0.5454 -0.5198 0.2862 0.049 Uiso 1 1 calc R . . N1 N -0.67711(16) -0.68744(9) 0.42096(18) 0.0324(4) Uani 1 1 d . . . C33 C -0.9382(2) -0.59551(12) 0.7368(3) 0.0430(5) Uani 1 1 d . . . H33 H -1.0172 -0.5849 0.6920 0.052 Uiso 1 1 calc R . . C36 C -0.7091(2) -0.62794(11) 0.8641(2) 0.0390(5) Uani 1 1 d . . . H36 H -0.6304 -0.6390 0.9091 0.047 Uiso 1 1 calc R . . C7 C -0.79697(19) -0.90988(11) 0.5968(2) 0.0351(5) Uani 1 1 d . . . H7 H -0.8297 -0.9553 0.5826 0.042 Uiso 1 1 calc R . . C16 C -0.3828(2) -0.53749(13) 0.1749(3) 0.0455(5) Uani 1 1 d . . . H16 H -0.3528 -0.4910 0.1754 0.055 Uiso 1 1 calc R . . C34 C -0.9094(2) -0.56374(12) 0.8610(3) 0.0444(5) Uani 1 1 d . . . C2 C -0.58926(19) -0.67202(11) 0.5340(2) 0.0347(5) Uani 1 1 d . . . H2A H -0.5825 -0.6212 0.5465 0.042 Uiso 1 1 calc R . . H2B H -0.5023 -0.6903 0.5128 0.042 Uiso 1 1 calc R . . C12 C -0.51196(18) -0.74927(11) 0.1770(2) 0.0319(4) Uani 1 1 d . . . C15 C -0.3135(2) -0.58879(13) 0.1088(2) 0.0436(6) Uani 1 1 d . . . H15 H -0.2361 -0.5775 0.0617 0.052 Uiso 1 1 calc R . . C35 C -0.7938(2) -0.58171(13) 0.9250(3) 0.0459(6) Uani 1 1 d . . . H35 H -0.7729 -0.5620 1.0116 0.055 Uiso 1 1 calc R . . C44 C -1.0003(3) -0.51169(14) 0.9242(4) 0.0649(8) Uani 1 1 d . . . H44A H -1.0060 -0.5198 1.0234 0.078 Uiso 1 1 calc R . . H44B H -1.0860 -0.5168 0.8829 0.078 Uiso 1 1 calc R . . H44C H -0.9681 -0.4647 0.9072 0.078 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C10 0.0269(9) 0.0338(11) 0.0284(9) 0.0004(9) 0.0000(7) 0.0002(8) C13 0.0333(9) 0.0374(11) 0.0246(9) 0.0057(9) -0.0015(8) 0.0021(8) C4 0.0252(9) 0.0337(11) 0.0314(10) 0.0008(9) -0.0004(8) 0.0009(8) C5 0.0355(11) 0.0417(12) 0.0287(10) -0.0009(10) 0.0020(9) 0.0002(9) C3 0.0309(10) 0.0359(11) 0.0303(10) -0.0020(9) -0.0015(8) -0.0016(8) C19 0.0375(11) 0.0367(12) 0.0400(12) 0.0078(10) 0.0071(9) 0.0099(9) C6 0.0372(11) 0.0375(12) 0.0348(11) 0.0074(10) 0.0046(9) -0.0019(9) C9 0.0240(9) 0.0325(11) 0.0300(10) -0.0002(9) 0.0012(8) 0.0010(7) C11 0.0334(10) 0.0317(11) 0.0308(10) 0.0010(9) 0.0045(8) 0.0030(8) C31 0.0346(10) 0.0307(11) 0.0309(10) -0.0001(9) 0.0011(8) -0.0047(8) C32 0.0371(11) 0.0482(13) 0.0336(11) -0.0071(11) 0.0010(9) 0.0003(10) C18 0.0375(11) 0.0364(11) 0.0298(10) 0.0081(10) -0.0012(9) 0.0020(9) C14 0.0364(11) 0.0480(13) 0.0276(10) 0.0046(10) 0.0008(9) 0.0001(9) C22 0.0432(12) 0.0442(14) 0.0362(12) -0.0023(10) 0.0071(10) -0.0011(10) C8 0.0300(10) 0.0350(12) 0.0343(11) -0.0020(10) 0.0013(8) -0.0001(8) C17 0.0507(13) 0.0356(11) 0.0369(12) 0.0080(11) 0.0006(10) 0.0057(9) N1 0.0345(8) 0.0315(9) 0.0312(9) 0.0015(8) 0.0031(7) 0.0022(7) C33 0.0382(11) 0.0437(13) 0.0472(13) 0.0013(11) 0.0086(11) 0.0001(9) C36 0.0449(12) 0.0382(12) 0.0340(11) -0.0029(10) -0.0011(10) -0.0061(9) C7 0.0316(10) 0.0300(11) 0.0436(12) 0.0008(9) 0.0024(9) -0.0002(8) C16 0.0519(13) 0.0423(12) 0.0421(12) 0.0134(11) -0.0031(11) -0.0094(10) C34 0.0487(12) 0.0315(11) 0.0531(13) -0.0034(11) 0.0192(11) -0.0087(9) C2 0.0332(10) 0.0326(11) 0.0381(11) -0.0022(9) 0.0038(9) -0.0026(8) C12 0.0269(10) 0.0374(11) 0.0314(10) -0.0003(9) 0.0010(8) 0.0037(8) C15 0.0405(12) 0.0553(15) 0.0351(12) 0.0111(11) 0.0028(9) -0.0071(10) C35 0.0578(14) 0.0422(13) 0.0377(12) -0.0122(11) 0.0084(11) -0.0139(11) C44 0.0606(15) 0.0457(15) 0.088(2) -0.0201(16) 0.0329(15) -0.0082(12) _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 C10 N1 1.454(3) . ? C10 C9 1.515(3) . ? C10 C11 1.556(3) . ? C10 H10 1.0000 . ? C13 C14 1.397(3) . ? C13 C18 1.410(3) . ? C13 C12 1.486(3) . ? C4 C5 1.393(3) . ? C4 C9 1.399(3) . ? C4 C3 1.518(3) . ? C5 C6 1.380(3) . ? C5 H5 0.9500 . ? C3 C31 1.521(3) . ? C3 C2 1.545(3) . ? C3 H3 1.0000 . ? C19 N1 1.454(3) . ? C19 C18 1.523(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C6 C7 1.382(3) . ? C6 H6 0.9500 . ? C9 C8 1.401(3) . ? C11 C12 1.515(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C31 C32 1.388(3) . ? C31 C36 1.391(3) . ? C32 C33 1.382(3) . ? C32 H32 0.9500 . ? C18 C17 1.391(3) . ? C14 C15 1.387(3) . ? C14 H14 0.9500 . ? C22 C12 1.331(3) . ? C22 H22A 0.9500 . ? C22 H22B 0.9500 . ? C8 C7 1.386(3) . ? C8 H8 0.9500 . ? C17 C16 1.393(3) . ? C17 H17 0.9500 . ? N1 C2 1.459(3) . ? C33 C34 1.388(4) . ? C33 H33 0.9500 . ? C36 C35 1.385(3) . ? C36 H36 0.9500 . ? C7 H7 0.9500 . ? C16 C15 1.382(4) . ? C16 H16 0.9500 . ? C34 C35 1.395(4) . ? C34 C44 1.509(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C15 H15 0.9500 . ? C35 H35 0.9500 . ? C44 H44A 0.9800 . ? C44 H44B 0.9800 . ? C44 H44C 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 C10 C9 108.17(16) . . ? N1 C10 C11 115.66(16) . . ? C9 C10 C11 111.80(16) . . ? N1 C10 H10 106.9 . . ? C9 C10 H10 106.9 . . ? C11 C10 H10 106.9 . . ? C14 C13 C18 118.21(19) . . ? C14 C13 C12 118.99(19) . . ? C18 C13 C12 122.80(18) . . ? C5 C4 C9 119.02(19) . . ? C5 C4 C3 118.99(18) . . ? C9 C4 C3 121.98(18) . . ? C6 C5 C4 121.4(2) . . ? C6 C5 H5 119.3 . . ? C4 C5 H5 119.3 . . ? C4 C3 C31 112.22(17) . . ? C4 C3 C2 110.96(17) . . ? C31 C3 C2 110.77(17) . . ? C4 C3 H3 107.6 . . ? C31 C3 H3 107.6 . . ? C2 C3 H3 107.6 . . ? N1 C19 C18 117.85(17) . . ? N1 C19 H19A 107.8 . . ? C18 C19 H19A 107.8 . . ? N1 C19 H19B 107.8 . . ? C18 C19 H19B 107.8 . . ? H19A C19 H19B 107.2 . . ? C5 C6 C7 119.8(2) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C4 C9 C8 118.94(19) . . ? C4 C9 C10 121.47(18) . . ? C8 C9 C10 119.49(18) . . ? C12 C11 C10 115.37(16) . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C32 C31 C36 117.8(2) . . ? C32 C31 C3 121.18(19) . . ? C36 C31 C3 121.02(19) . . ? C33 C32 C31 121.2(2) . . ? C33 C32 H32 119.4 . . ? C31 C32 H32 119.4 . . ? C17 C18 C13 119.30(19) . . ? C17 C18 C19 119.27(19) . . ? C13 C18 C19 121.37(18) . . ? C15 C14 C13 121.8(2) . . ? C15 C14 H14 119.1 . . ? C13 C14 H14 119.1 . . ? C12 C22 H22A 120.0 . . ? C12 C22 H22B 120.0 . . ? H22A C22 H22B 120.0 . . ? C7 C8 C9 121.13(19) . . ? C7 C8 H8 119.4 . . ? C9 C8 H8 119.4 . . ? C18 C17 C16 121.7(2) . . ? C18 C17 H17 119.2 . . ? C16 C17 H17 119.2 . . ? C19 N1 C10 115.35(17) . . ? C19 N1 C2 114.75(17) . . ? C10 N1 C2 112.15(16) . . ? C32 C33 C34 121.2(2) . . ? C32 C33 H33 119.4 . . ? C34 C33 H33 119.4 . . ? C35 C36 C31 121.1(2) . . ? C35 C36 H36 119.4 . . ? C31 C36 H36 119.4 . . ? C6 C7 C8 119.54(19) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C15 C16 C17 119.0(2) . . ? C15 C16 H16 120.5 . . ? C17 C16 H16 120.5 . . ? C33 C34 C35 117.7(2) . . ? C33 C34 C44 120.9(3) . . ? C35 C34 C44 121.4(2) . . ? N1 C2 C3 109.36(15) . . ? N1 C2 H2A 109.8 . . ? C3 C2 H2A 109.8 . . ? N1 C2 H2B 109.8 . . ? C3 C2 H2B 109.8 . . ? H2A C2 H2B 108.2 . . ? C22 C12 C13 120.16(19) . . ? C22 C12 C11 120.60(18) . . ? C13 C12 C11 119.10(18) . . ? C16 C15 C14 120.0(2) . . ? C16 C15 H15 120.0 . . ? C14 C15 H15 120.0 . . ? C36 C35 C34 120.9(2) . . ? C36 C35 H35 119.5 . . ? C34 C35 H35 119.5 . . ? C34 C44 H44A 109.5 . . ? C34 C44 H44B 109.5 . . ? H44A C44 H44B 109.5 . . ? C34 C44 H44C 109.5 . . ? H44A C44 H44C 109.5 . . ? H44B C44 H44C 109.5 . . ? 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 C9 C4 C5 C6 1.0(3) . . . . ? C3 C4 C5 C6 -179.97(19) . . . . ? C5 C4 C3 C31 -59.0(2) . . . . ? C9 C4 C3 C31 120.1(2) . . . . ? C5 C4 C3 C2 176.52(17) . . . . ? C9 C4 C3 C2 -4.4(3) . . . . ? C4 C5 C6 C7 1.4(3) . . . . ? C5 C4 C9 C8 -2.8(3) . . . . ? C3 C4 C9 C8 178.19(17) . . . . ? C5 C4 C9 C10 173.42(18) . . . . ? C3 C4 C9 C10 -5.6(3) . . . . ? N1 C10 C9 C4 -19.9(2) . . . . ? C11 C10 C9 C4 108.6(2) . . . . ? N1 C10 C9 C8 156.30(17) . . . . ? C11 C10 C9 C8 -75.2(2) . . . . ? N1 C10 C11 C12 -63.0(2) . . . . ? C9 C10 C11 C12 172.61(17) . . . . ? C4 C3 C31 C32 -59.5(3) . . . . ? C2 C3 C31 C32 65.2(2) . . . . ? C4 C3 C31 C36 122.9(2) . . . . ? C2 C3 C31 C36 -112.5(2) . . . . ? C36 C31 C32 C33 2.3(3) . . . . ? C3 C31 C32 C33 -175.4(2) . . . . ? C14 C13 C18 C17 -1.2(3) . . . . ? C12 C13 C18 C17 178.3(2) . . . . ? C14 C13 C18 C19 176.01(19) . . . . ? C12 C13 C18 C19 -4.6(3) . . . . ? N1 C19 C18 C17 -121.6(2) . . . . ? N1 C19 C18 C13 61.2(3) . . . . ? C18 C13 C14 C15 0.1(3) . . . . ? C12 C13 C14 C15 -179.3(2) . . . . ? C4 C9 C8 C7 2.3(3) . . . . ? C10 C9 C8 C7 -174.00(18) . . . . ? C13 C18 C17 C16 1.0(3) . . . . ? C19 C18 C17 C16 -176.2(2) . . . . ? C18 C19 N1 C10 -78.4(2) . . . . ? C18 C19 N1 C2 54.3(3) . . . . ? C9 C10 N1 C19 -167.93(16) . . . . ? C11 C10 N1 C19 65.8(2) . . . . ? C9 C10 N1 C2 58.20(19) . . . . ? C11 C10 N1 C2 -68.1(2) . . . . ? C31 C32 C33 C34 -0.9(4) . . . . ? C32 C31 C36 C35 -1.5(3) . . . . ? C3 C31 C36 C35 176.2(2) . . . . ? C5 C6 C7 C8 -2.0(3) . . . . ? C9 C8 C7 C6 0.1(3) . . . . ? C18 C17 C16 C15 0.2(3) . . . . ? C32 C33 C34 C35 -1.3(3) . . . . ? C32 C33 C34 C44 178.8(2) . . . . ? C19 N1 C2 C3 155.37(17) . . . . ? C10 N1 C2 C3 -70.5(2) . . . . ? C4 C3 C2 N1 39.6(2) . . . . ? C31 C3 C2 N1 -85.8(2) . . . . ? C14 C13 C12 C22 -48.2(3) . . . . ? C18 C13 C12 C22 132.4(2) . . . . ? C14 C13 C12 C11 127.5(2) . . . . ? C18 C13 C12 C11 -52.0(3) . . . . ? C10 C11 C12 C22 -113.2(2) . . . . ? C10 C11 C12 C13 71.2(2) . . . . ? C17 C16 C15 C14 -1.3(3) . . . . ? C13 C14 C15 C16 1.1(3) . . . . ? C31 C36 C35 C34 -0.7(3) . . . . ? C33 C34 C35 C36 2.1(3) . . . . ? C44 C34 C35 C36 -178.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.130 _refine_diff_density_min -0.195 _refine_diff_density_rms 0.037