# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_name 'Manojit Pal' _publ_contact_author_email manojitpal@rediffmail.com _publ_author_name M.Pal data_cpsu4_010_1 _database_code_depnum_ccdc_archive 'CCDC 822101' #TrackingRef 'A004CPSU-4010.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H22 F3 N O' _chemical_formula_weight 433.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7605(5) _cell_length_b 10.2660(8) _cell_length_c 14.6746(11) _cell_angle_alpha 73.704(3) _cell_angle_beta 86.924(3) _cell_angle_gamma 70.205(3) _cell_volume 1054.73(13) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9928 _cell_measurement_theta_min 2.79 _cell_measurement_theta_max 32.89 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.0108 _exptl_crystal_size_mid 0.008 _exptl_crystal_size_min 0.00236 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.365 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.101 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.999 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16632 _diffrn_reflns_av_R_equivalents 0.0369 _diffrn_reflns_av_sigmaI/netI 0.0334 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.45 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4592 _reflns_number_gt 4091 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+0.5147P] 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 4592 _refine_ls_number_parameters 291 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0437 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1221 _refine_ls_wR_factor_gt 0.1170 _refine_ls_goodness_of_fit_ref 0.803 _refine_ls_restrained_S_all 0.803 _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 C3 C 0.84372(15) 0.76222(12) 0.97194(8) 0.0149(2) Uani 1 1 d . . . C5 C 1.13132(16) 0.76533(12) 0.97639(8) 0.0160(2) Uani 1 1 d . . . H5 H 1.2526 0.7565 0.9631 0.019 Uiso 1 1 calc R . . C20 C 0.97046(15) 0.76200(13) 0.75364(8) 0.0157(2) Uani 1 1 d . . . H20 H 0.8623 0.8379 0.7528 0.019 Uiso 1 1 calc R . . C9 C 1.18764(16) 0.75513(13) 1.20984(8) 0.0165(2) Uani 1 1 d . . . C15 C 1.07053(16) 0.68540(12) 0.83965(8) 0.0153(2) Uani 1 1 d . . . C6 C 1.01662(15) 0.73122(12) 0.92685(8) 0.0144(2) Uani 1 1 d . . . C24 C 0.72070(17) 0.98033(14) 0.40747(8) 0.0186(3) Uani 1 1 d . . . C16 C 1.23134(16) 0.57052(13) 0.83987(9) 0.0189(3) Uani 1 1 d . . . H16 H 1.2996 0.5177 0.8965 0.023 Uiso 1 1 calc R . . C21 C 0.92204(16) 0.81503(13) 0.57796(8) 0.0170(2) Uani 1 1 d . . . C19 C 1.02812(16) 0.72787(13) 0.66882(8) 0.0171(2) Uani 1 1 d . . . C14 C 1.28986(17) 0.78791(14) 1.26976(9) 0.0206(3) Uani 1 1 d . . . H14 H 1.3147 0.8738 1.2499 0.025 Uiso 1 1 calc R . . C25 C 0.72243(17) 1.04321(14) 0.47934(9) 0.0191(3) Uani 1 1 d . . . H25 H 0.6560 1.1403 0.4711 0.023 Uiso 1 1 calc R . . C18 C 1.19005(18) 0.61208(14) 0.67169(9) 0.0215(3) Uani 1 1 d . . . H18 H 1.2307 0.5871 0.6161 0.026 Uiso 1 1 calc R . . C4 C 0.86265(16) 0.81443(12) 1.04743(8) 0.0162(2) Uani 1 1 d . . . C22 C 0.91977(18) 0.75357(14) 0.50439(9) 0.0216(3) Uani 1 1 d . . . H22 H 0.9857 0.6564 0.5124 0.026 Uiso 1 1 calc R . . C26 C 0.82325(17) 0.96136(13) 0.56346(8) 0.0185(2) Uani 1 1 d . . . H26 H 0.8251 1.0046 0.6111 0.022 Uiso 1 1 calc R . . C8 C 1.11899(18) 0.86420(13) 1.11445(9) 0.0203(3) Uani 1 1 d . . . H8A H 1.0283 0.9499 1.1252 0.024 Uiso 1 1 calc R . . H8B H 1.2207 0.8916 1.0843 0.024 Uiso 1 1 calc R . . C2 C 0.67982(16) 0.73089(13) 0.95478(8) 0.0173(2) Uani 1 1 d . . . C10 C 1.15331(17) 0.62584(14) 1.24017(9) 0.0198(3) Uani 1 1 d . . . H10 H 1.0848 0.6027 1.2009 0.024 Uiso 1 1 calc R . . C17 C 1.29014(17) 0.53455(14) 0.75654(9) 0.0226(3) Uani 1 1 d . . . H17 H 1.3975 0.4578 0.7576 0.027 Uiso 1 1 calc R . . C11 C 1.22065(18) 0.53064(14) 1.32884(9) 0.0235(3) Uani 1 1 d . . . H11 H 1.1986 0.4436 1.3482 0.028 Uiso 1 1 calc R . . C12 C 1.32030(18) 0.56488(15) 1.38838(9) 0.0249(3) Uani 1 1 d . . . H12 H 1.3638 0.5017 1.4480 0.030 Uiso 1 1 calc R . . C23 C 0.82068(19) 0.83544(14) 0.41969(9) 0.0228(3) Uani 1 1 d . . . H23 H 0.8211 0.7935 0.3711 0.027 Uiso 1 1 calc R . . C1 C 0.69569(18) 0.62356(14) 0.90031(9) 0.0218(3) Uani 1 1 d . . . H1A H 0.5909 0.5925 0.9106 0.033 Uiso 1 1 calc R . . H1B H 0.8051 0.5419 0.9218 0.033 Uiso 1 1 calc R . . H1C H 0.7012 0.6678 0.8337 0.033 Uiso 1 1 calc R . . C27 C 0.61511(18) 1.06820(14) 0.31578(9) 0.0221(3) Uani 1 1 d . . . C13 C 1.35507(18) 0.69406(15) 1.35862(9) 0.0250(3) Uani 1 1 d . . . H13 H 1.4221 0.7176 1.3983 0.030 Uiso 1 1 calc R . . C7 C 0.73039(18) 0.85924(14) 1.11938(9) 0.0229(3) Uani 1 1 d . . . H7A H 0.7963 0.8545 1.1744 0.034 Uiso 1 1 calc R . . H7B H 0.6598 0.7959 1.1373 0.034 Uiso 1 1 calc R . . H7C H 0.6498 0.9563 1.0928 0.034 Uiso 1 1 calc R . . O1 O 0.53308(12) 0.78515(11) 0.98784(7) 0.0278(2) Uani 1 1 d . . . F1 F 0.51339(11) 1.00126(9) 0.28832(6) 0.0289(2) Uani 1 1 d . . . F2 F 0.72415(12) 1.09298(10) 0.24403(5) 0.0327(2) Uani 1 1 d . . . F3 F 0.49933(13) 1.19599(9) 0.32058(6) 0.0376(2) Uani 1 1 d . . . N1 N 1.03794(14) 0.81486(11) 1.04912(7) 0.0160(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C3 0.0155(5) 0.0135(5) 0.0133(5) -0.0016(4) 0.0000(4) -0.0035(4) C5 0.0155(5) 0.0154(5) 0.0147(5) -0.0012(4) -0.0001(4) -0.0048(4) C20 0.0150(5) 0.0152(5) 0.0162(6) -0.0043(4) 0.0020(4) -0.0046(4) C9 0.0174(5) 0.0165(6) 0.0148(6) -0.0063(4) 0.0005(4) -0.0033(4) C15 0.0161(5) 0.0157(5) 0.0146(6) -0.0035(4) 0.0022(4) -0.0069(4) C6 0.0151(5) 0.0131(5) 0.0126(5) -0.0008(4) -0.0001(4) -0.0038(4) C24 0.0201(6) 0.0226(6) 0.0145(6) -0.0036(5) 0.0022(4) -0.0103(5) C16 0.0178(6) 0.0174(6) 0.0172(6) -0.0013(5) 0.0004(4) -0.0035(5) C21 0.0179(5) 0.0201(6) 0.0135(5) -0.0045(4) 0.0046(4) -0.0080(5) C19 0.0194(6) 0.0174(6) 0.0152(6) -0.0042(4) 0.0025(4) -0.0076(5) C14 0.0224(6) 0.0191(6) 0.0213(6) -0.0088(5) -0.0015(5) -0.0054(5) C25 0.0210(6) 0.0187(6) 0.0172(6) -0.0053(5) 0.0026(5) -0.0064(5) C18 0.0240(6) 0.0220(6) 0.0171(6) -0.0080(5) 0.0064(5) -0.0048(5) C4 0.0169(5) 0.0145(5) 0.0143(5) -0.0013(4) -0.0006(4) -0.0036(4) C22 0.0285(6) 0.0182(6) 0.0170(6) -0.0058(5) 0.0036(5) -0.0063(5) C26 0.0220(6) 0.0207(6) 0.0144(6) -0.0070(5) 0.0026(4) -0.0078(5) C8 0.0279(6) 0.0167(6) 0.0179(6) -0.0042(5) -0.0051(5) -0.0091(5) C2 0.0160(5) 0.0179(6) 0.0147(5) 0.0003(4) -0.0017(4) -0.0052(4) C10 0.0220(6) 0.0202(6) 0.0180(6) -0.0056(5) -0.0007(5) -0.0076(5) C17 0.0203(6) 0.0194(6) 0.0228(6) -0.0055(5) 0.0046(5) -0.0008(5) C11 0.0261(6) 0.0205(6) 0.0212(6) -0.0021(5) 0.0022(5) -0.0075(5) C12 0.0259(6) 0.0261(7) 0.0142(6) -0.0030(5) -0.0007(5) 0.0002(5) C23 0.0320(7) 0.0239(7) 0.0152(6) -0.0082(5) 0.0030(5) -0.0111(5) C1 0.0241(6) 0.0247(6) 0.0196(6) -0.0045(5) -0.0001(5) -0.0132(5) C27 0.0264(6) 0.0254(6) 0.0180(6) -0.0065(5) -0.0001(5) -0.0124(5) C13 0.0240(6) 0.0298(7) 0.0202(6) -0.0132(5) -0.0048(5) -0.0022(5) C7 0.0243(6) 0.0240(6) 0.0181(6) -0.0077(5) 0.0040(5) -0.0042(5) O1 0.0158(4) 0.0320(5) 0.0361(6) -0.0118(4) 0.0041(4) -0.0072(4) F1 0.0299(4) 0.0386(5) 0.0243(4) -0.0081(3) -0.0029(3) -0.0194(4) F2 0.0406(5) 0.0471(5) 0.0151(4) -0.0004(3) 0.0017(3) -0.0275(4) F3 0.0489(6) 0.0270(5) 0.0270(5) -0.0075(4) -0.0150(4) 0.0020(4) N1 0.0186(5) 0.0160(5) 0.0131(5) -0.0029(4) -0.0017(4) -0.0059(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 C3 C4 1.3928(16) . ? C3 C6 1.4399(15) . ? C3 C2 1.4635(16) . ? C5 C6 1.3663(16) . ? C5 N1 1.3765(15) . ? C20 C15 1.3961(16) . ? C20 C19 1.3968(16) . ? C9 C10 1.3877(18) . ? C9 C14 1.3919(17) . ? C9 C8 1.5144(16) . ? C15 C16 1.3963(17) . ? C15 C6 1.4767(16) . ? C24 C25 1.3851(17) . ? C24 C23 1.3893(18) . ? C24 C27 1.4941(17) . ? C16 C17 1.3854(18) . ? C21 C26 1.3956(18) . ? C21 C22 1.3984(17) . ? C21 C19 1.4851(16) . ? C19 C18 1.3999(17) . ? C14 C13 1.3857(18) . ? C25 C26 1.3850(17) . ? C18 C17 1.3842(18) . ? C4 N1 1.3634(15) . ? C4 C7 1.4888(17) . ? C22 C23 1.3861(18) . ? C8 N1 1.4575(14) . ? C2 O1 1.2268(15) . ? C2 C1 1.5033(17) . ? C10 C11 1.3911(18) . ? C11 C12 1.3834(19) . ? C12 C13 1.388(2) . ? C27 F3 1.3342(16) . ? C27 F2 1.3376(15) . ? C27 F1 1.3471(14) . ? 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 C4 C3 C6 107.49(10) . . ? C4 C3 C2 122.68(11) . . ? C6 C3 C2 129.40(11) . . ? C6 C5 N1 108.85(10) . . ? C15 C20 C19 121.90(11) . . ? C10 C9 C14 118.87(11) . . ? C10 C9 C8 123.51(11) . . ? C14 C9 C8 117.61(11) . . ? C20 C15 C16 118.30(11) . . ? C20 C15 C6 121.09(10) . . ? C16 C15 C6 120.43(10) . . ? C5 C6 C3 106.41(10) . . ? C5 C6 C15 122.41(10) . . ? C3 C6 C15 130.95(10) . . ? C25 C24 C23 119.98(11) . . ? C25 C24 C27 120.39(11) . . ? C23 C24 C27 119.62(11) . . ? C17 C16 C15 120.62(11) . . ? C26 C21 C22 118.21(11) . . ? C26 C21 C19 120.65(11) . . ? C22 C21 C19 121.14(11) . . ? C20 C19 C18 118.24(11) . . ? C20 C19 C21 120.49(11) . . ? C18 C19 C21 121.25(11) . . ? C13 C14 C9 120.79(12) . . ? C26 C25 C24 119.93(11) . . ? C17 C18 C19 120.53(11) . . ? N1 C4 C3 107.25(10) . . ? N1 C4 C7 122.06(11) . . ? C3 C4 C7 130.66(11) . . ? C23 C22 C21 120.91(12) . . ? C25 C26 C21 121.08(11) . . ? N1 C8 C9 115.06(10) . . ? O1 C2 C3 121.21(11) . . ? O1 C2 C1 119.80(11) . . ? C3 C2 C1 118.90(11) . . ? C9 C10 C11 120.42(12) . . ? C18 C17 C16 120.41(11) . . ? C12 C11 C10 120.30(12) . . ? C11 C12 C13 119.62(12) . . ? C22 C23 C24 119.88(11) . . ? F3 C27 F2 107.30(11) . . ? F3 C27 F1 106.41(11) . . ? F2 C27 F1 105.55(10) . . ? F3 C27 C24 112.75(10) . . ? F2 C27 C24 112.45(10) . . ? F1 C27 C24 111.90(11) . . ? C14 C13 C12 119.98(12) . . ? C4 N1 C5 110.01(10) . . ? C4 N1 C8 126.84(10) . . ? C5 N1 C8 123.12(10) . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.312 _refine_diff_density_min -0.345 _refine_diff_density_rms 0.050 data_cpsu4_008_a_1 _database_code_depnum_ccdc_archive 'CCDC 822229' #TrackingRef 'A004CPSU-4008.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H25 N O2' _chemical_formula_weight 395.18 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 Triclinic _symmetry_space_group_name_H-M 'P-1 ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.7415(4) _cell_length_b 10.0575(5) _cell_length_c 14.2538(7) _cell_angle_alpha 76.801(2) _cell_angle_beta 88.027(2) _cell_angle_gamma 74.254(2) _cell_volume 1039.49(9) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9953 _cell_measurement_theta_min 3.07 _cell_measurement_theta_max 31.91 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.009 _exptl_crystal_size_mid 0.007 _exptl_crystal_size_min 0.00236 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.264 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 420 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.999 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'Multiscan absorption correction' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 'Bruker Kappa APEX-II CCD DUO' _diffrn_measurement_method '\ f and \ w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 16956 _diffrn_reflns_av_R_equivalents 0.0287 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 1.47 _diffrn_reflns_theta_max 27.00 _reflns_number_total 4505 _reflns_number_gt 4128 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.1000P)^2^+0.6251P] 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 4505 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0493 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.1368 _refine_ls_wR_factor_gt 0.1132 _refine_ls_goodness_of_fit_ref 0.875 _refine_ls_restrained_S_all 0.875 _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 C6 C 1.04692(16) 0.23556(12) 0.92804(8) 0.0152(2) Uani 1 1 d . . . C19 C 1.04219(16) 0.21504(13) 0.66536(9) 0.0173(3) Uani 1 1 d . . . C3 C 0.87669(16) 0.26488(12) 0.97402(8) 0.0154(2) Uani 1 1 d . . . C20 C 0.99670(16) 0.25679(13) 0.75211(9) 0.0166(3) Uani 1 1 d . . . H20 H 0.8982 0.3339 0.7527 0.020 Uiso 1 1 calc R . . C5 C 1.16239(16) 0.27589(13) 0.97897(9) 0.0172(3) Uani 1 1 d . . . H5 H 1.2826 0.2689 0.9657 0.021 Uiso 1 1 calc R . . C4 C 0.89767(16) 0.32310(13) 1.05141(8) 0.0166(3) Uani 1 1 d . . . C26 C 0.84191(17) 0.43331(14) 0.55870(9) 0.0193(3) Uani 1 1 d . . . H26 H 0.8507 0.4840 0.6045 0.023 Uiso 1 1 calc R . . C21 C 0.93363(16) 0.29010(13) 0.57550(9) 0.0174(3) Uani 1 1 d . . . C25 C 0.73738(17) 0.50289(14) 0.47533(9) 0.0205(3) Uani 1 1 d . . . H25 H 0.6772 0.5987 0.4659 0.025 Uiso 1 1 calc R . . C22 C 0.91882(18) 0.21781(14) 0.50405(9) 0.0213(3) Uani 1 1 d . . . H22 H 0.9797 0.1222 0.5131 0.026 Uiso 1 1 calc R . . C15 C 1.09466(16) 0.18625(13) 0.83797(9) 0.0164(3) Uani 1 1 d . . . C14 C 1.32125(17) 0.29756(14) 1.28335(9) 0.0213(3) Uani 1 1 d . . . H14 H 1.3542 0.3821 1.2691 0.026 Uiso 1 1 calc R . . C18 C 1.19185(18) 0.09920(14) 0.66620(9) 0.0214(3) Uani 1 1 d . . . H18 H 1.2255 0.0696 0.6094 0.026 Uiso 1 1 calc R . . C10 C 1.17179(17) 0.14043(14) 1.23876(9) 0.0206(3) Uani 1 1 d . . . H10 H 1.1024 0.1196 1.1951 0.025 Uiso 1 1 calc R . . C1 C 0.72551(18) 0.11114(14) 0.90433(10) 0.0222(3) Uani 1 1 d . . . H1A H 0.6142 0.0855 0.9095 0.033 Uiso 1 1 calc R . . H1B H 0.8210 0.0303 0.9336 0.033 Uiso 1 1 calc R . . H1C H 0.7495 0.1423 0.8376 0.033 Uiso 1 1 calc R . . C23 C 0.81616(19) 0.28507(15) 0.42080(9) 0.0238(3) Uani 1 1 d . . . H23 H 0.8087 0.2350 0.3744 0.029 Uiso 1 1 calc R . . C16 C 1.24227(17) 0.07062(14) 0.83645(9) 0.0197(3) Uani 1 1 d . . . H16 H 1.3087 0.0218 0.8929 0.024 Uiso 1 1 calc R . . C17 C 1.29036(18) 0.02820(14) 0.75090(10) 0.0231(3) Uani 1 1 d . . . H17 H 1.3895 -0.0485 0.7504 0.028 Uiso 1 1 calc R . . C8 C 1.15753(18) 0.37722(13) 1.12346(9) 0.0207(3) Uani 1 1 d . . . H8A H 1.0743 0.4608 1.1379 0.025 Uiso 1 1 calc R . . H8B H 1.2614 0.4050 1.0946 0.025 Uiso 1 1 calc R . . C9 C 1.21705(16) 0.26813(13) 1.21688(9) 0.0177(3) Uani 1 1 d . . . C12 C 1.33063(18) 0.07447(15) 1.39195(9) 0.0247(3) Uani 1 1 d . . . H12 H 1.3676 0.0102 1.4504 0.030 Uiso 1 1 calc R . . C2 C 0.71256(16) 0.22926(13) 0.95510(9) 0.0188(3) Uani 1 1 d . . . C13 C 1.37613(18) 0.20154(16) 1.37065(10) 0.0249(3) Uani 1 1 d . . . H13 H 1.4438 0.2228 1.4150 0.030 Uiso 1 1 calc R . . C24 C 0.72357(17) 0.42824(15) 0.40628(9) 0.0208(3) Uani 1 1 d . . . C11 C 1.22952(18) 0.04332(15) 1.32565(10) 0.0236(3) Uani 1 1 d . . . H11 H 1.2002 -0.0427 1.3393 0.028 Uiso 1 1 calc R . . C27 C 0.5515(2) 0.63392(16) 0.29631(11) 0.0306(3) Uani 1 1 d . . . H27A H 0.4624 0.6628 0.3416 0.046 Uiso 1 1 calc R . . H27B H 0.4972 0.6609 0.2328 0.046 Uiso 1 1 calc R . . H27C H 0.6456 0.6792 0.2971 0.046 Uiso 1 1 calc R . . O2 O 0.62427(14) 0.48410(11) 0.32219(7) 0.0283(2) Uani 1 1 d . . . O1 O 0.56757(13) 0.28958(12) 0.98331(8) 0.0324(3) Uani 1 1 d . . . N1 N 1.07162(14) 0.32861(11) 1.05331(7) 0.0169(2) Uani 1 1 d . . . C7 C 0.76698(18) 0.36937(15) 1.12478(9) 0.0231(3) Uani 1 1 d . . . H7A H 0.8305 0.3795 1.1783 0.035 Uiso 1 1 calc R . . H7B H 0.7022 0.2997 1.1469 0.035 Uiso 1 1 calc R . . H7C H 0.6842 0.4587 1.0963 0.035 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 C6 0.0146(5) 0.0143(5) 0.0145(5) -0.0001(4) -0.0004(4) -0.0027(4) C19 0.0181(6) 0.0182(6) 0.0160(6) -0.0035(5) 0.0024(4) -0.0061(5) C3 0.0144(6) 0.0149(5) 0.0149(5) -0.0010(4) -0.0002(4) -0.0028(4) C20 0.0150(5) 0.0168(6) 0.0174(6) -0.0042(5) 0.0019(4) -0.0033(4) C5 0.0150(6) 0.0175(6) 0.0175(6) -0.0015(4) -0.0001(4) -0.0039(4) C4 0.0171(6) 0.0154(5) 0.0149(5) -0.0004(4) -0.0004(4) -0.0027(4) C26 0.0215(6) 0.0211(6) 0.0166(6) -0.0064(5) 0.0021(5) -0.0061(5) C21 0.0176(6) 0.0203(6) 0.0148(6) -0.0039(5) 0.0035(4) -0.0066(5) C25 0.0213(6) 0.0195(6) 0.0196(6) -0.0039(5) 0.0011(5) -0.0040(5) C22 0.0270(7) 0.0185(6) 0.0187(6) -0.0063(5) 0.0025(5) -0.0053(5) C15 0.0150(5) 0.0178(6) 0.0167(6) -0.0034(4) 0.0025(4) -0.0059(4) C14 0.0212(6) 0.0216(6) 0.0229(6) -0.0108(5) -0.0015(5) -0.0039(5) C18 0.0230(6) 0.0222(6) 0.0183(6) -0.0068(5) 0.0053(5) -0.0038(5) C10 0.0213(6) 0.0222(6) 0.0190(6) -0.0046(5) -0.0030(5) -0.0067(5) C1 0.0219(6) 0.0232(6) 0.0228(6) -0.0025(5) -0.0015(5) -0.0102(5) C23 0.0316(7) 0.0251(7) 0.0170(6) -0.0077(5) 0.0007(5) -0.0094(6) C16 0.0170(6) 0.0205(6) 0.0184(6) -0.0007(5) 0.0009(4) -0.0028(5) C17 0.0198(6) 0.0212(6) 0.0237(6) -0.0040(5) 0.0041(5) 0.0007(5) C8 0.0260(7) 0.0175(6) 0.0200(6) -0.0037(5) -0.0057(5) -0.0080(5) C9 0.0172(6) 0.0187(6) 0.0168(6) -0.0060(5) -0.0004(4) -0.0025(5) C12 0.0218(6) 0.0311(7) 0.0150(6) -0.0023(5) -0.0001(5) 0.0005(5) C2 0.0162(6) 0.0205(6) 0.0179(6) -0.0006(5) -0.0013(4) -0.0051(5) C13 0.0212(6) 0.0334(7) 0.0198(6) -0.0124(5) -0.0045(5) -0.0011(5) C24 0.0206(6) 0.0265(7) 0.0154(6) -0.0025(5) 0.0001(5) -0.0085(5) C11 0.0234(6) 0.0233(6) 0.0215(6) -0.0005(5) 0.0010(5) -0.0059(5) C27 0.0298(7) 0.0305(8) 0.0262(7) 0.0041(6) -0.0077(6) -0.0070(6) O2 0.0344(6) 0.0296(5) 0.0189(5) -0.0029(4) -0.0072(4) -0.0064(4) O1 0.0146(5) 0.0412(6) 0.0443(6) -0.0181(5) 0.0031(4) -0.0059(4) N1 0.0180(5) 0.0171(5) 0.0154(5) -0.0023(4) -0.0020(4) -0.0050(4) C7 0.0240(7) 0.0257(7) 0.0188(6) -0.0071(5) 0.0046(5) -0.0041(5) _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 C6 C5 1.3662(17) . ? C6 C3 1.4392(16) . ? C6 C15 1.4796(16) . ? C19 C20 1.3987(17) . ? C19 C18 1.4006(18) . ? C19 C21 1.4850(17) . ? C3 C4 1.3945(17) . ? C3 C2 1.4596(17) . ? C20 C15 1.3970(17) . ? C5 N1 1.3787(16) . ? C4 N1 1.3642(16) . ? C4 C7 1.4926(17) . ? C26 C21 1.3911(18) . ? C26 C25 1.3914(17) . ? C21 C22 1.4037(18) . ? C25 C24 1.3899(19) . ? C22 C23 1.3798(18) . ? C15 C16 1.3955(17) . ? C14 C13 1.3879(19) . ? C14 C9 1.3951(17) . ? C18 C17 1.3868(18) . ? C10 C9 1.3869(18) . ? C10 C11 1.3915(18) . ? C1 C2 1.5060(19) . ? C23 C24 1.3943(19) . ? C16 C17 1.3884(18) . ? C8 N1 1.4583(16) . ? C8 C9 1.5132(17) . ? C12 C13 1.382(2) . ? C12 C11 1.387(2) . ? C2 O1 1.2249(16) . ? C24 O2 1.3656(15) . ? C27 O2 1.4226(18) . ? 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 C5 C6 C3 106.52(11) . . ? C5 C6 C15 123.43(11) . . ? C3 C6 C15 129.76(11) . . ? C20 C19 C18 117.93(11) . . ? C20 C19 C21 120.97(11) . . ? C18 C19 C21 121.10(11) . . ? C4 C3 C6 107.42(11) . . ? C4 C3 C2 122.96(11) . . ? C6 C3 C2 129.29(11) . . ? C15 C20 C19 122.05(11) . . ? C6 C5 N1 108.85(11) . . ? N1 C4 C3 107.32(10) . . ? N1 C4 C7 122.36(11) . . ? C3 C4 C7 130.29(12) . . ? C21 C26 C25 121.89(12) . . ? C26 C21 C22 117.32(11) . . ? C26 C21 C19 121.93(11) . . ? C22 C21 C19 120.75(11) . . ? C24 C25 C26 119.54(12) . . ? C23 C22 C21 121.63(12) . . ? C16 C15 C20 118.56(11) . . ? C16 C15 C6 120.53(11) . . ? C20 C15 C6 120.88(11) . . ? C13 C14 C9 120.48(13) . . ? C17 C18 C19 120.64(12) . . ? C9 C10 C11 120.46(12) . . ? C22 C23 C24 119.94(12) . . ? C17 C16 C15 120.24(12) . . ? C18 C17 C16 120.57(12) . . ? N1 C8 C9 114.33(10) . . ? C10 C9 C14 118.94(12) . . ? C10 C9 C8 122.48(11) . . ? C14 C9 C8 118.59(12) . . ? C13 C12 C11 119.65(12) . . ? O1 C2 C3 121.07(12) . . ? O1 C2 C1 120.13(12) . . ? C3 C2 C1 118.73(11) . . ? C12 C13 C14 120.27(12) . . ? O2 C24 C25 125.05(12) . . ? O2 C24 C23 115.27(12) . . ? C25 C24 C23 119.68(12) . . ? C12 C11 C10 120.19(13) . . ? C24 O2 C27 117.44(11) . . ? C4 N1 C5 109.89(10) . . ? C4 N1 C8 127.14(11) . . ? C5 N1 C8 122.94(11) . . ? _diffrn_measured_fraction_theta_max 0.995 _diffrn_reflns_theta_full 27.00 _diffrn_measured_fraction_theta_full 0.995 _refine_diff_density_max 0.642 _refine_diff_density_min -0.586 _refine_diff_density_rms 0.181