# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_imai###_1 _database_code_depnum_ccdc_archive 'CCDC 881755' #TrackingRef 'imai ver.2.cif' #data_im1655a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H24 F N O4' _chemical_formula_weight 469.49 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 monoclinic _symmetry_space_group_name_H-M P21/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 12.643(3) _cell_length_b 6.0744(16) _cell_length_c 31.164(9) _cell_angle_alpha 90.00 _cell_angle_beta 101.399(5) _cell_angle_gamma 90.00 _cell_volume 2346.1(11) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 2478 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 25.03 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.80 _exptl_crystal_size_mid 0.60 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9288 _exptl_absorpt_correction_T_max 0.9724 _exptl_absorpt_process_details mult-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type \w-scans _diffrn_measurement_method ? _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10785 _diffrn_reflns_av_R_equivalents 0.0404 _diffrn_reflns_av_sigmaI/netI 0.0498 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -36 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 2.32 _diffrn_reflns_theta_max 25.03 _reflns_number_total 3744 _reflns_number_gt 2478 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. The used crystal did not diffract to very high angles, because of its poor quality. ; _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^)+(0.0625P)^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 3744 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0687 _refine_ls_R_factor_gt 0.0411 _refine_ls_wR_factor_ref 0.1136 _refine_ls_wR_factor_gt 0.0985 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _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 0.71691(17) 0.3070(3) 0.38249(7) 0.0220(5) Uani 1 1 d . . . H1 H 0.6839 0.1710 0.3725 0.026 Uiso 1 1 calc R . . C2 C 0.71259(16) 0.3785(3) 0.42382(7) 0.0184(5) Uani 1 1 d . . . C3 C 0.76374(17) 0.5804(3) 0.43879(7) 0.0229(5) Uani 1 1 d . . . H3 H 0.7627 0.6297 0.4676 0.028 Uiso 1 1 calc R . . C4 C 0.81412(17) 0.7039(4) 0.41255(7) 0.0241(5) Uani 1 1 d . . . H4 H 0.8472 0.8388 0.4232 0.029 Uiso 1 1 calc R . . C5 C 0.87026(18) 0.7591(4) 0.34101(8) 0.0283(6) Uani 1 1 d . . . H5 H 0.9035 0.8954 0.3507 0.034 Uiso 1 1 calc R . . C6 C 0.87302(19) 0.6843(4) 0.29984(8) 0.0332(6) Uani 1 1 d . . . H6 H 0.9083 0.7684 0.2811 0.040 Uiso 1 1 calc R . . C7 C 0.82374(18) 0.4827(4) 0.28510(8) 0.0331(6) Uani 1 1 d . . . H7 H 0.8253 0.4328 0.2564 0.040 Uiso 1 1 calc R . . C8 C 0.77381(19) 0.3586(4) 0.31163(7) 0.0289(6) Uani 1 1 d . . . H8 H 0.7417 0.2224 0.3012 0.035 Uiso 1 1 calc R . . C9 C 0.76908(17) 0.4300(4) 0.35454(7) 0.0227(5) Uani 1 1 d . . . C10 C 0.81813(17) 0.6348(4) 0.36947(7) 0.0225(5) Uani 1 1 d . . . C11 C 0.65049(16) 0.2547(3) 0.45235(7) 0.0191(5) Uani 1 1 d . . . O12 O 0.63628(11) 0.3426(2) 0.48745(5) 0.0211(3) Uani 1 1 d . . . O13 O 0.61487(12) 0.0639(2) 0.44080(5) 0.0237(4) Uani 1 1 d . . . C21 C 0.46416(16) 0.6556(3) 0.29019(7) 0.0199(5) Uani 1 1 d . . . H21 H 0.4977 0.7955 0.2899 0.024 Uiso 1 1 calc R . . C22 C 0.45776(16) 0.5602(3) 0.32948(7) 0.0196(5) Uani 1 1 d . . . C23 C 0.40913(17) 0.3513(4) 0.33000(7) 0.0240(5) Uani 1 1 d . . . H23 H 0.4049 0.2845 0.3572 0.029 Uiso 1 1 calc R . . C24 C 0.36812(18) 0.2443(4) 0.29186(7) 0.0249(5) Uani 1 1 d . . . H24 H 0.3365 0.1030 0.2929 0.030 Uiso 1 1 calc R . . C25 C 0.32706(18) 0.2364(4) 0.21047(7) 0.0270(5) Uani 1 1 d . . . H25 H 0.2935 0.0964 0.2104 0.032 Uiso 1 1 calc R . . C26 C 0.33184(18) 0.3364(4) 0.17172(8) 0.0301(6) Uani 1 1 d . . . H26 H 0.3011 0.2657 0.1450 0.036 Uiso 1 1 calc R . . C27 C 0.38165(18) 0.5426(4) 0.17091(8) 0.0299(6) Uani 1 1 d . . . H27 H 0.3848 0.6096 0.1436 0.036 Uiso 1 1 calc R . . C28 C 0.42541(18) 0.6469(4) 0.20882(7) 0.0249(5) Uani 1 1 d . . . H28 H 0.4588 0.7864 0.2078 0.030 Uiso 1 1 calc R . . C29 C 0.42182(17) 0.5497(3) 0.24999(7) 0.0214(5) Uani 1 1 d . . . C30 C 0.37166(17) 0.3394(4) 0.25081(7) 0.0226(5) Uani 1 1 d . . . C31 C 0.49709(17) 0.6765(4) 0.37162(7) 0.0220(5) Uani 1 1 d . . . O32 O 0.48339(12) 0.6100(3) 0.40700(5) 0.0279(4) Uani 1 1 d . . . O33 O 0.54875(13) 0.8623(3) 0.36647(5) 0.0313(4) Uani 1 1 d . . . H33 H 0.5695 0.9226 0.3909 0.047 Uiso 1 1 calc R . . C41 C 0.75412(17) 0.8061(3) 0.55279(7) 0.0218(5) Uani 1 1 d . . . C42 C 0.80637(18) 0.6132(4) 0.56786(7) 0.0247(5) Uani 1 1 d . . . C43 C 0.91591(18) 0.5827(4) 0.57187(8) 0.0329(6) Uani 1 1 d . . . H43 H 0.9490 0.4478 0.5826 0.039 Uiso 1 1 calc R . . C44 C 0.9763(2) 0.7527(4) 0.55996(8) 0.0358(6) Uani 1 1 d . . . H44 H 1.0519 0.7351 0.5622 0.043 Uiso 1 1 calc R . . C45 C 0.92742(19) 0.9483(4) 0.54471(8) 0.0333(6) Uani 1 1 d . . . H45 H 0.9695 1.0646 0.5365 0.040 Uiso 1 1 calc R . . C46 C 0.81725(18) 0.9760(4) 0.54134(7) 0.0266(5) Uani 1 1 d . . . H46 H 0.7845 1.1120 0.5312 0.032 Uiso 1 1 calc R . . C47 C 0.63390(17) 0.8294(4) 0.54858(7) 0.0240(5) Uani 1 1 d . . . H47A H 0.6095 0.7345 0.5705 0.029 Uiso 1 1 calc R . . H47B H 0.6164 0.9838 0.5546 0.029 Uiso 1 1 calc R . . N48 N 0.57532(14) 0.7658(3) 0.50353(5) 0.0205(4) Uani 1 1 d . . . H48A H 0.5876 0.8689 0.4839 0.031 Uiso 1 1 calc R . . H48B H 0.5033 0.7574 0.5032 0.031 Uiso 1 1 calc R . . H48C H 0.5996 0.6326 0.4962 0.031 Uiso 1 1 calc R . . F49 F 0.74755(11) 0.4470(2) 0.57982(4) 0.0357(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 C1 0.0216(12) 0.0212(11) 0.0234(13) 0.0006(10) 0.0052(10) -0.0002(10) C2 0.0142(11) 0.0179(11) 0.0230(12) 0.0015(10) 0.0035(9) 0.0030(9) C3 0.0201(12) 0.0256(12) 0.0236(12) -0.0040(10) 0.0055(10) -0.0004(10) C4 0.0201(12) 0.0242(12) 0.0279(13) -0.0020(10) 0.0047(10) -0.0019(10) C5 0.0235(13) 0.0292(13) 0.0326(14) 0.0055(12) 0.0064(10) -0.0044(11) C6 0.0265(13) 0.0422(15) 0.0318(15) 0.0119(12) 0.0077(11) -0.0021(12) C7 0.0336(14) 0.0444(15) 0.0228(13) 0.0055(12) 0.0091(11) 0.0013(12) C8 0.0342(14) 0.0309(13) 0.0225(13) -0.0002(11) 0.0075(11) -0.0022(11) C9 0.0197(11) 0.0271(12) 0.0206(12) 0.0020(10) 0.0025(9) 0.0032(10) C10 0.0161(11) 0.0234(12) 0.0276(13) 0.0027(10) 0.0031(10) 0.0005(10) C11 0.0159(11) 0.0194(11) 0.0197(12) 0.0033(10) -0.0020(9) 0.0033(9) O12 0.0235(8) 0.0231(8) 0.0174(8) -0.0020(7) 0.0055(6) -0.0002(7) O13 0.0310(9) 0.0195(8) 0.0211(8) -0.0007(7) 0.0064(7) -0.0067(7) C21 0.0200(11) 0.0200(11) 0.0201(12) -0.0019(10) 0.0046(9) 0.0000(9) C22 0.0161(11) 0.0222(11) 0.0200(12) -0.0002(10) 0.0027(9) 0.0018(9) C23 0.0257(13) 0.0258(12) 0.0207(13) 0.0052(11) 0.0053(10) 0.0006(10) C24 0.0260(12) 0.0199(11) 0.0291(13) -0.0009(11) 0.0058(10) -0.0010(10) C25 0.0248(12) 0.0242(12) 0.0314(14) -0.0070(11) 0.0043(10) 0.0010(10) C26 0.0276(13) 0.0372(14) 0.0245(14) -0.0102(11) 0.0030(11) 0.0031(11) C27 0.0292(14) 0.0406(14) 0.0207(13) 0.0009(12) 0.0067(10) 0.0054(12) C28 0.0260(12) 0.0272(12) 0.0226(13) 0.0020(11) 0.0071(10) -0.0007(10) C29 0.0196(11) 0.0231(11) 0.0213(12) -0.0025(10) 0.0038(9) 0.0031(10) C30 0.0198(12) 0.0227(12) 0.0254(13) -0.0008(10) 0.0047(9) 0.0038(10) C31 0.0189(12) 0.0242(12) 0.0220(13) 0.0020(10) 0.0017(10) 0.0027(10) O32 0.0299(9) 0.0349(9) 0.0187(9) 0.0017(7) 0.0040(7) -0.0031(7) O33 0.0430(10) 0.0300(9) 0.0198(9) -0.0039(7) 0.0033(8) -0.0131(8) C41 0.0246(12) 0.0246(12) 0.0149(11) -0.0043(10) 0.0008(9) 0.0038(10) C42 0.0264(13) 0.0241(12) 0.0218(13) -0.0010(10) 0.0005(10) -0.0012(10) C43 0.0278(14) 0.0313(13) 0.0352(15) -0.0063(12) -0.0045(11) 0.0132(11) C44 0.0197(13) 0.0423(15) 0.0438(16) -0.0124(13) 0.0025(11) 0.0020(12) C45 0.0267(13) 0.0360(14) 0.0361(15) -0.0043(12) 0.0038(11) -0.0061(12) C46 0.0281(13) 0.0265(12) 0.0235(13) -0.0040(11) 0.0012(10) -0.0003(11) C47 0.0274(13) 0.0265(12) 0.0170(12) 0.0003(10) 0.0019(10) 0.0031(10) N48 0.0195(9) 0.0198(9) 0.0219(10) 0.0013(8) 0.0033(8) 0.0002(8) F49 0.0397(8) 0.0312(8) 0.0342(8) 0.0086(7) 0.0023(7) -0.0001(7) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.370(3) . ? C1 C9 1.407(3) . ? C2 C3 1.421(3) . ? C2 C11 1.500(3) . ? C3 C4 1.358(3) . ? C4 C10 1.417(3) . ? C5 C6 1.368(3) . ? C5 C10 1.422(3) . ? C6 C7 1.409(3) . ? C7 C8 1.362(3) . ? C8 C9 1.418(3) . ? C9 C10 1.426(3) . ? C11 O12 1.262(2) . ? C11 O13 1.269(2) . ? C21 C22 1.372(3) . ? C21 C29 1.416(3) . ? C22 C23 1.412(3) . ? C22 C31 1.488(3) . ? C23 C24 1.364(3) . ? C24 C30 1.412(3) . ? C25 C26 1.364(3) . ? C25 C30 1.418(3) . ? C26 C27 1.404(3) . ? C27 C28 1.358(3) . ? C28 C29 1.421(3) . ? C29 C30 1.428(3) . ? C31 O32 1.218(2) . ? C31 O33 1.330(3) . ? C41 C42 1.381(3) . ? C41 C46 1.394(3) . ? C41 C47 1.506(3) . ? C42 F49 1.349(2) . ? C42 C43 1.378(3) . ? C43 C44 1.378(3) . ? C44 C45 1.379(3) . ? C45 C46 1.386(3) . ? C47 N48 1.503(3) . ? 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 C9 121.6(2) . . ? C1 C2 C3 118.8(2) . . ? C1 C2 C11 121.39(19) . . ? C3 C2 C11 119.71(19) . . ? C4 C3 C2 121.1(2) . . ? C3 C4 C10 121.1(2) . . ? C6 C5 C10 120.6(2) . . ? C5 C6 C7 120.2(2) . . ? C8 C7 C6 120.7(2) . . ? C7 C8 C9 120.9(2) . . ? C1 C9 C8 122.3(2) . . ? C1 C9 C10 119.2(2) . . ? C8 C9 C10 118.5(2) . . ? C4 C10 C5 122.8(2) . . ? C4 C10 C9 118.2(2) . . ? C5 C10 C9 119.0(2) . . ? O12 C11 O13 122.0(2) . . ? O12 C11 C2 118.85(19) . . ? O13 C11 C2 119.20(19) . . ? C22 C21 C29 121.3(2) . . ? C21 C22 C23 119.5(2) . . ? C21 C22 C31 121.3(2) . . ? C23 C22 C31 119.16(19) . . ? C24 C23 C22 120.6(2) . . ? C23 C24 C30 121.3(2) . . ? C26 C25 C30 120.6(2) . . ? C25 C26 C27 120.8(2) . . ? C28 C27 C26 120.5(2) . . ? C27 C28 C29 120.7(2) . . ? C21 C29 C28 122.4(2) . . ? C21 C29 C30 118.8(2) . . ? C28 C29 C30 118.8(2) . . ? C24 C30 C25 123.0(2) . . ? C24 C30 C29 118.4(2) . . ? C25 C30 C29 118.6(2) . . ? O32 C31 O33 123.5(2) . . ? O32 C31 C22 124.0(2) . . ? O33 C31 C22 112.53(19) . . ? C42 C41 C46 117.1(2) . . ? C42 C41 C47 121.1(2) . . ? C46 C41 C47 121.81(19) . . ? F49 C42 C43 118.2(2) . . ? F49 C42 C41 118.42(19) . . ? C43 C42 C41 123.3(2) . . ? C44 C43 C42 118.4(2) . . ? C43 C44 C45 120.3(2) . . ? C44 C45 C46 120.4(2) . . ? C45 C46 C41 120.6(2) . . ? N48 C47 C41 111.08(17) . . ? _diffrn_measured_fraction_theta_max 0.905 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.905 _refine_diff_density_max 0.234 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.048 data_imai###_2 _database_code_depnum_ccdc_archive 'CCDC 881756' #TrackingRef 'imai ver.2.cif' #data_im1687a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 F N O2' _chemical_formula_weight 297.32 _chemical_absolute_configuration rm 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 monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 10.010(2) _cell_length_b 6.1790(13) _cell_length_c 12.767(3) _cell_angle_alpha 90.00 _cell_angle_beta 107.203(3) _cell_angle_gamma 90.00 _cell_volume 754.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3016 _cell_measurement_theta_min 3.34 _cell_measurement_theta_max 27.47 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.27 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.309 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 312 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9752 _exptl_absorpt_correction_T_max 0.9889 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5484 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0310 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.34 _diffrn_reflns_theta_max 27.47 _reflns_number_total 3125 _reflns_number_gt 3016 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0413P)^2^+0.2314P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.3(8) _refine_ls_number_reflns 3125 _refine_ls_number_parameters 200 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0388 _refine_ls_R_factor_gt 0.0374 _refine_ls_wR_factor_ref 0.0927 _refine_ls_wR_factor_gt 0.0915 _refine_ls_goodness_of_fit_ref 1.059 _refine_ls_restrained_S_all 1.059 _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 C1 C 0.52516(16) 0.2163(3) 0.70940(13) 0.0209(3) Uani 1 1 d . . . H1 H 0.5213 0.0760 0.7388 0.025 Uiso 1 1 calc R . . C2 C 0.64641(16) 0.3353(3) 0.74538(13) 0.0194(3) Uani 1 1 d . . . C3 C 0.65186(16) 0.5461(3) 0.70328(13) 0.0216(3) Uani 1 1 d . . . H3 H 0.7346 0.6300 0.7296 0.026 Uiso 1 1 calc R . . C4 C 0.53886(16) 0.6304(3) 0.62486(13) 0.0222(3) Uani 1 1 d . . . H4 H 0.5445 0.7716 0.5971 0.027 Uiso 1 1 calc R . . C5 C 0.29586(18) 0.5897(3) 0.50123(14) 0.0261(4) Uani 1 1 d . . . H5 H 0.2996 0.7290 0.4707 0.031 Uiso 1 1 calc R . . C6 C 0.17711(18) 0.4674(3) 0.46473(14) 0.0294(4) Uani 1 1 d . . . H6 H 0.0996 0.5215 0.4083 0.035 Uiso 1 1 calc R . . C7 C 0.16874(18) 0.2610(3) 0.51034(14) 0.0297(4) Uani 1 1 d . . . H7 H 0.0851 0.1788 0.4851 0.036 Uiso 1 1 calc R . . C8 C 0.28021(17) 0.1787(3) 0.59060(14) 0.0266(4) Uani 1 1 d . . . H8 H 0.2733 0.0398 0.6206 0.032 Uiso 1 1 calc R . . C9 C 0.40598(16) 0.2993(3) 0.62933(13) 0.0218(3) Uani 1 1 d . . . C10 C 0.41416(16) 0.5094(3) 0.58490(13) 0.0214(3) Uani 1 1 d . . . C11 C 0.77411(16) 0.2343(3) 0.82527(13) 0.0221(3) Uani 1 1 d . . . O12 O 0.76870(13) 0.0366(2) 0.84370(11) 0.0325(3) Uani 1 1 d . . . O13 O 0.87935(11) 0.3551(2) 0.86561(10) 0.0275(3) Uani 1 1 d . . . C21 C 0.22663(16) -0.0114(3) 0.89530(13) 0.0231(3) Uani 1 1 d . . . C22 C 0.34420(17) -0.1184(3) 0.88439(14) 0.0272(4) Uani 1 1 d . . . C23 C 0.33802(18) -0.2979(3) 0.81931(14) 0.0309(4) Uani 1 1 d . . . H23 H 0.4210 -0.3652 0.8138 0.037 Uiso 1 1 calc R . . C24 C 0.20721(18) -0.3782(3) 0.76191(14) 0.0298(4) Uani 1 1 d . . . H24 H 0.2000 -0.5023 0.7166 0.036 Uiso 1 1 calc R . . C25 C 0.08729(17) -0.2775(3) 0.77073(13) 0.0282(4) Uani 1 1 d . . . H25 H -0.0020 -0.3337 0.7320 0.034 Uiso 1 1 calc R . . C26 C 0.09700(17) -0.0949(3) 0.83583(14) 0.0272(4) Uani 1 1 d . . . H26 H 0.0140 -0.0256 0.8399 0.033 Uiso 1 1 calc R . . C27 C 0.24567(18) 0.1866(3) 0.96693(16) 0.0288(4) Uani 1 1 d . . . H27A H 0.3332 0.1716 1.0280 0.035 Uiso 1 1 calc R . . H27B H 0.2554 0.3150 0.9234 0.035 Uiso 1 1 calc R . . N28 N 0.12731(13) 0.2217(2) 1.01273(11) 0.0236(3) Uani 1 1 d . . . H28A H 0.0476 0.2453 0.9570 0.035 Uiso 1 1 calc R . . H28B H 0.1455 0.3389 1.0580 0.035 Uiso 1 1 calc R . . H28C H 0.1163 0.1026 1.0513 0.035 Uiso 1 1 calc R . . F29 F 0.47153(10) -0.0388(2) 0.94102(9) 0.0386(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 C1 0.0226(7) 0.0185(7) 0.0225(7) 0.0001(6) 0.0082(6) 0.0012(6) C2 0.0182(7) 0.0193(8) 0.0205(7) -0.0002(6) 0.0056(6) 0.0045(6) C3 0.0210(7) 0.0220(8) 0.0229(8) -0.0024(6) 0.0084(6) -0.0022(6) C4 0.0275(8) 0.0175(7) 0.0232(8) 0.0022(6) 0.0101(6) 0.0014(6) C5 0.0280(8) 0.0269(9) 0.0228(8) 0.0004(7) 0.0065(6) 0.0057(7) C6 0.0229(8) 0.0391(10) 0.0227(8) -0.0035(7) 0.0011(6) 0.0073(7) C7 0.0218(8) 0.0365(11) 0.0291(9) -0.0058(8) 0.0052(7) -0.0014(7) C8 0.0256(8) 0.0262(9) 0.0279(8) -0.0028(6) 0.0078(7) -0.0011(6) C9 0.0218(7) 0.0233(8) 0.0213(7) -0.0031(6) 0.0079(6) 0.0024(6) C10 0.0215(7) 0.0232(8) 0.0203(7) -0.0004(6) 0.0075(6) 0.0024(6) C11 0.0199(7) 0.0238(9) 0.0232(7) 0.0008(6) 0.0072(6) 0.0033(6) O12 0.0248(6) 0.0254(7) 0.0433(8) 0.0079(5) 0.0036(5) 0.0045(5) O13 0.0203(5) 0.0273(6) 0.0311(6) -0.0013(5) 0.0020(5) 0.0024(5) C21 0.0213(7) 0.0246(8) 0.0243(8) 0.0030(7) 0.0080(6) -0.0009(6) C22 0.0192(7) 0.0347(10) 0.0270(8) 0.0043(7) 0.0056(6) 0.0023(7) C23 0.0247(8) 0.0406(10) 0.0286(9) 0.0008(8) 0.0096(7) 0.0095(7) C24 0.0323(9) 0.0318(9) 0.0261(8) -0.0029(7) 0.0099(7) 0.0036(8) C25 0.0243(8) 0.0347(10) 0.0248(8) -0.0011(7) 0.0062(6) -0.0004(7) C26 0.0202(7) 0.0312(9) 0.0306(9) -0.0016(7) 0.0081(6) 0.0024(6) C27 0.0222(7) 0.0259(9) 0.0388(10) -0.0017(7) 0.0098(7) -0.0037(6) N28 0.0188(6) 0.0199(7) 0.0295(7) -0.0025(6) 0.0031(5) 0.0005(5) F29 0.0167(5) 0.0515(7) 0.0446(7) -0.0079(6) 0.0042(4) 0.0020(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.376(2) . ? C1 C9 1.418(2) . ? C2 C3 1.416(2) . ? C2 C11 1.514(2) . ? C3 C4 1.372(2) . ? C4 C10 1.414(2) . ? C5 C6 1.369(3) . ? C5 C10 1.429(2) . ? C6 C7 1.415(3) . ? C7 C8 1.370(2) . ? C8 C9 1.420(2) . ? C9 C10 1.429(2) . ? C11 O12 1.248(2) . ? C11 O13 1.270(2) . ? C21 C22 1.392(2) . ? C21 C26 1.394(2) . ? C21 C27 1.505(2) . ? C22 F29 1.3578(19) . ? C22 C23 1.377(3) . ? C23 C24 1.389(2) . ? C24 C25 1.386(2) . ? C25 C26 1.388(3) . ? C27 N28 1.484(2) . ? 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 C9 121.22(15) . . ? C1 C2 C3 119.58(14) . . ? C1 C2 C11 119.35(14) . . ? C3 C2 C11 121.01(14) . . ? C4 C3 C2 120.67(15) . . ? C3 C4 C10 120.77(15) . . ? C6 C5 C10 120.45(17) . . ? C5 C6 C7 120.59(16) . . ? C8 C7 C6 120.54(17) . . ? C7 C8 C9 120.49(17) . . ? C1 C9 C8 122.10(15) . . ? C1 C9 C10 118.69(14) . . ? C8 C9 C10 119.20(15) . . ? C4 C10 C5 122.27(15) . . ? C4 C10 C9 119.02(14) . . ? C5 C10 C9 118.70(15) . . ? O12 C11 O13 125.19(15) . . ? O12 C11 C2 117.09(15) . . ? O13 C11 C2 117.69(15) . . ? C22 C21 C26 116.62(16) . . ? C22 C21 C27 119.19(15) . . ? C26 C21 C27 124.18(14) . . ? F29 C22 C23 118.74(15) . . ? F29 C22 C21 117.58(16) . . ? C23 C22 C21 123.68(16) . . ? C22 C23 C24 118.26(16) . . ? C25 C24 C23 120.03(18) . . ? C24 C25 C26 120.33(16) . . ? C25 C26 C21 121.07(15) . . ? N28 C27 C21 112.70(14) . . ? _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.955 _refine_diff_density_max 0.239 _refine_diff_density_min -0.152 _refine_diff_density_rms 0.039 data_imai###_3 _database_code_depnum_ccdc_archive 'CCDC 881757' #TrackingRef 'imai ver.2.cif' #data_im1658a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C29 H24 F N O4' _chemical_formula_weight 469.49 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 monoclinic _symmetry_space_group_name_H-M P21/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 12.742(3) _cell_length_b 6.0989(13) _cell_length_c 30.926(7) _cell_angle_alpha 90.00 _cell_angle_beta 101.313(3) _cell_angle_gamma 90.00 _cell_volume 2356.7(9) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 4386 _cell_measurement_theta_min 3.26 _cell_measurement_theta_max 27.49 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 984 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9744 _exptl_absorpt_correction_T_max 0.9907 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16190 _diffrn_reflns_av_R_equivalents 0.0328 _diffrn_reflns_av_sigmaI/netI 0.0289 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 39 _diffrn_reflns_theta_min 3.26 _diffrn_reflns_theta_max 27.49 _reflns_number_total 5232 _reflns_number_gt 4386 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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. The maximum residual peak, located 0.41 angstrom away from H45, may indicate the presence of a small fraction of the benzene ring rotated by 180 degrees around the C41-C44 axis, but the fraction was ignored. ; _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^)+(0.0766P)^2^+1.0109P] 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 5232 _refine_ls_number_parameters 318 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0558 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1409 _refine_ls_wR_factor_gt 0.1341 _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_restrained_S_all 1.090 _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 C1 C 0.46090(11) -0.1488(2) 0.28894(5) 0.0188(3) Uani 1 1 d . . . H1 H 0.4946 -0.2873 0.2882 0.023 Uiso 1 1 calc R . . C2 C 0.45324(11) -0.0569(2) 0.32887(5) 0.0186(3) Uani 1 1 d . . . C3 C 0.40538(12) 0.1524(2) 0.33037(5) 0.0210(3) Uani 1 1 d . . . H3 H 0.4008 0.2158 0.3580 0.025 Uiso 1 1 calc R . . C4 C 0.36569(12) 0.2634(2) 0.29210(5) 0.0215(3) Uani 1 1 d . . . H4 H 0.3348 0.4044 0.2935 0.026 Uiso 1 1 calc R . . C5 C 0.32600(12) 0.2775(3) 0.21023(5) 0.0238(3) Uani 1 1 d . . . H5 H 0.2934 0.4172 0.2108 0.029 Uiso 1 1 calc R . . C6 C 0.32993(13) 0.1814(3) 0.17065(5) 0.0265(3) Uani 1 1 d . . . H6 H 0.2995 0.2544 0.1440 0.032 Uiso 1 1 calc R . . C7 C 0.37891(12) -0.0260(3) 0.16898(5) 0.0250(3) Uani 1 1 d . . . H7 H 0.3815 -0.0909 0.1413 0.030 Uiso 1 1 calc R . . C8 C 0.42260(12) -0.1334(3) 0.20724(5) 0.0220(3) Uani 1 1 d . . . H8 H 0.4555 -0.2723 0.2059 0.026 Uiso 1 1 calc R . . C9 C 0.41901(11) -0.0388(2) 0.24886(5) 0.0185(3) Uani 1 1 d . . . C10 C 0.37021(11) 0.1705(2) 0.25044(5) 0.0188(3) Uani 1 1 d . . . C11 C 0.49098(11) -0.1778(2) 0.37099(5) 0.0192(3) Uani 1 1 d . . . O12 O 0.47032(9) -0.12235(19) 0.40624(3) 0.0255(3) Uani 1 1 d . . . O13 O 0.54841(9) -0.35396(18) 0.36595(3) 0.0253(3) Uani 1 1 d . . . H13 H 0.5697 -0.4139 0.3906 0.038 Uiso 1 1 calc R . . C21 C 0.71501(11) 0.2009(2) 0.38144(5) 0.0192(3) Uani 1 1 d . . . H21 H 0.6823 0.3367 0.3715 0.023 Uiso 1 1 calc R . . C22 C 0.70996(11) 0.1259(2) 0.42286(5) 0.0172(3) Uani 1 1 d . . . C23 C 0.75981(11) -0.0756(2) 0.43779(5) 0.0196(3) Uani 1 1 d . . . H23 H 0.7581 -0.1258 0.4667 0.024 Uiso 1 1 calc R . . C24 C 0.81034(12) -0.1983(3) 0.41102(5) 0.0225(3) Uani 1 1 d . . . H24 H 0.8421 -0.3343 0.4214 0.027 Uiso 1 1 calc R . . C25 C 0.86875(12) -0.2477(3) 0.33956(6) 0.0264(3) Uani 1 1 d . . . H25 H 0.9005 -0.3849 0.3490 0.032 Uiso 1 1 calc R . . C26 C 0.87423(13) -0.1694(3) 0.29853(6) 0.0303(4) Uani 1 1 d . . . H26 H 0.9103 -0.2521 0.2799 0.036 Uiso 1 1 calc R . . C27 C 0.82675(14) 0.0331(3) 0.28381(5) 0.0305(4) Uani 1 1 d . . . H27 H 0.8308 0.0857 0.2553 0.037 Uiso 1 1 calc R . . C28 C 0.77489(13) 0.1544(3) 0.31046(5) 0.0267(3) Uani 1 1 d . . . H28 H 0.7430 0.2904 0.3002 0.032 Uiso 1 1 calc R . . C29 C 0.76842(11) 0.0784(3) 0.35320(5) 0.0203(3) Uani 1 1 d . . . C30 C 0.81597(11) -0.1257(3) 0.36813(5) 0.0215(3) Uani 1 1 d . . . C31 C 0.64891(10) 0.2510(2) 0.45184(4) 0.0159(3) Uani 1 1 d . . . O32 O 0.61352(8) 0.44012(17) 0.44012(3) 0.0203(2) Uani 1 1 d . . . O33 O 0.63542(8) 0.16271(16) 0.48736(3) 0.0176(2) Uani 1 1 d . . . C41 C 0.74674(11) -0.2955(2) 0.55433(4) 0.0191(3) Uani 1 1 d . . . C42 C 0.80901(11) -0.4663(3) 0.54303(5) 0.0211(3) Uani 1 1 d . . . H42 H 0.7773 -0.6017 0.5323 0.025 Uiso 1 1 calc R . . C43 C 0.91786(12) -0.4334(3) 0.54789(5) 0.0267(3) Uani 1 1 d . . . C44 C 0.96784(13) -0.2407(3) 0.56364(6) 0.0328(4) Uani 1 1 d . . . H44 H 1.0430 -0.2235 0.5666 0.039 Uiso 1 1 calc R . . C45 C 0.90525(14) -0.0733(3) 0.57500(6) 0.0332(4) Uani 1 1 d . . . H45 H 0.9378 0.0606 0.5862 0.040 Uiso 1 1 calc R . . C46 C 0.79510(13) -0.0992(3) 0.57016(5) 0.0261(3) Uani 1 1 d . . . H46 H 0.7527 0.0176 0.5777 0.031 Uiso 1 1 calc R . . C47 C 0.62720(11) -0.3209(3) 0.54842(5) 0.0199(3) Uani 1 1 d . . . H47A H 0.6098 -0.4742 0.5548 0.024 Uiso 1 1 calc R . . H47B H 0.6002 -0.2243 0.5695 0.024 Uiso 1 1 calc R . . N48 N 0.57320(9) -0.2633(2) 0.50233(4) 0.0166(2) Uani 1 1 d . . . H48A H 0.5980 -0.1315 0.4948 0.025 Uiso 1 1 calc R . . H48B H 0.5013 -0.2549 0.5008 0.025 Uiso 1 1 calc R . . H48C H 0.5876 -0.3683 0.4834 0.025 Uiso 1 1 calc R . . F49 F 0.97652(9) -0.6008(2) 0.53639(4) 0.0480(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 C1 0.0187(6) 0.0189(7) 0.0190(7) 0.0009(5) 0.0040(5) 0.0011(5) C2 0.0178(6) 0.0200(7) 0.0172(7) 0.0009(5) 0.0020(5) -0.0003(5) C3 0.0244(7) 0.0212(7) 0.0178(7) -0.0032(6) 0.0048(5) 0.0005(6) C4 0.0230(7) 0.0178(7) 0.0239(7) -0.0001(6) 0.0055(6) 0.0020(6) C5 0.0222(7) 0.0231(7) 0.0263(8) 0.0069(6) 0.0054(6) 0.0014(6) C6 0.0258(7) 0.0333(9) 0.0196(7) 0.0093(6) 0.0024(6) -0.0008(7) C7 0.0258(7) 0.0330(8) 0.0166(7) 0.0001(6) 0.0053(6) -0.0034(7) C8 0.0233(7) 0.0230(7) 0.0205(7) -0.0002(6) 0.0062(5) -0.0002(6) C9 0.0171(6) 0.0211(7) 0.0174(7) 0.0004(5) 0.0038(5) -0.0015(5) C10 0.0173(6) 0.0188(7) 0.0200(7) 0.0028(5) 0.0031(5) -0.0014(5) C11 0.0191(6) 0.0205(7) 0.0175(7) -0.0012(5) 0.0024(5) -0.0006(5) O12 0.0313(6) 0.0292(6) 0.0164(5) 0.0001(4) 0.0055(4) 0.0062(5) O13 0.0336(6) 0.0255(6) 0.0165(5) 0.0034(4) 0.0039(4) 0.0106(5) C21 0.0190(6) 0.0189(7) 0.0198(7) -0.0004(5) 0.0041(5) 0.0018(5) C22 0.0148(6) 0.0183(7) 0.0187(7) -0.0020(5) 0.0039(5) -0.0010(5) C23 0.0169(6) 0.0207(7) 0.0215(7) 0.0027(6) 0.0045(5) -0.0003(5) C24 0.0183(7) 0.0197(7) 0.0294(8) 0.0010(6) 0.0048(6) 0.0029(6) C25 0.0210(7) 0.0273(8) 0.0314(8) -0.0075(7) 0.0061(6) 0.0025(6) C26 0.0247(8) 0.0386(9) 0.0299(8) -0.0127(7) 0.0106(6) 0.0007(7) C27 0.0315(8) 0.0409(10) 0.0211(7) -0.0063(7) 0.0098(6) -0.0020(7) C28 0.0295(8) 0.0293(8) 0.0222(8) -0.0011(6) 0.0073(6) 0.0017(7) C29 0.0188(6) 0.0227(7) 0.0198(7) -0.0033(6) 0.0046(5) -0.0009(6) C30 0.0162(6) 0.0235(7) 0.0248(7) -0.0041(6) 0.0040(5) -0.0005(6) C31 0.0146(6) 0.0172(6) 0.0154(6) -0.0014(5) 0.0015(5) -0.0006(5) O32 0.0259(5) 0.0181(5) 0.0175(5) 0.0017(4) 0.0055(4) 0.0051(4) O33 0.0179(5) 0.0191(5) 0.0159(5) 0.0010(4) 0.0039(4) 0.0002(4) C41 0.0191(6) 0.0228(7) 0.0139(6) 0.0026(5) -0.0002(5) -0.0015(6) C42 0.0213(7) 0.0234(7) 0.0174(7) 0.0010(6) 0.0012(5) -0.0003(6) C43 0.0217(7) 0.0343(9) 0.0242(7) 0.0060(7) 0.0047(6) 0.0045(7) C44 0.0197(7) 0.0428(10) 0.0332(9) 0.0122(8) -0.0016(6) -0.0071(7) C45 0.0323(9) 0.0271(8) 0.0355(9) 0.0040(7) -0.0051(7) -0.0105(7) C46 0.0302(8) 0.0216(7) 0.0238(7) -0.0002(6) -0.0014(6) -0.0009(6) C47 0.0200(7) 0.0252(7) 0.0146(6) 0.0004(6) 0.0038(5) -0.0001(6) N48 0.0162(5) 0.0162(6) 0.0173(6) -0.0002(4) 0.0036(4) 0.0010(4) F49 0.0346(6) 0.0554(8) 0.0552(7) 0.0038(6) 0.0115(5) 0.0138(5) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.377(2) . ? C1 C9 1.419(2) . ? C2 C3 1.419(2) . ? C2 C11 1.492(2) . ? C3 C4 1.371(2) . ? C4 C10 1.419(2) . ? C5 C6 1.367(2) . ? C5 C10 1.420(2) . ? C6 C7 1.416(2) . ? C7 C8 1.371(2) . ? C8 C9 1.420(2) . ? C9 C10 1.425(2) . ? C11 O12 1.2185(18) . ? C11 O13 1.3262(18) . ? C21 C22 1.374(2) . ? C21 C29 1.421(2) . ? C22 C23 1.418(2) . ? C22 C31 1.5044(19) . ? C23 C24 1.367(2) . ? C24 C30 1.414(2) . ? C25 C26 1.370(2) . ? C25 C30 1.421(2) . ? C26 C27 1.411(3) . ? C27 C28 1.370(2) . ? C28 C29 1.419(2) . ? C29 C30 1.421(2) . ? C31 O33 1.2649(17) . ? C31 O32 1.2655(18) . ? C41 C46 1.391(2) . ? C41 C42 1.395(2) . ? C41 C47 1.506(2) . ? C42 C43 1.380(2) . ? C43 F49 1.353(2) . ? C43 C44 1.380(3) . ? C44 C45 1.383(3) . ? C45 C46 1.391(2) . ? C47 N48 1.4979(17) . ? 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 C9 120.69(13) . . ? C1 C2 C3 120.12(13) . . ? C1 C2 C11 120.95(13) . . ? C3 C2 C11 118.88(13) . . ? C4 C3 C2 120.27(13) . . ? C3 C4 C10 120.84(14) . . ? C6 C5 C10 120.63(15) . . ? C5 C6 C7 120.64(14) . . ? C8 C7 C6 120.17(14) . . ? C7 C8 C9 120.54(14) . . ? C1 C9 C8 121.76(14) . . ? C1 C9 C10 119.06(13) . . ? C8 C9 C10 119.17(13) . . ? C4 C10 C5 122.15(14) . . ? C4 C10 C9 119.00(13) . . ? C5 C10 C9 118.85(14) . . ? O12 C11 O13 123.44(14) . . ? O12 C11 C2 123.69(14) . . ? O13 C11 C2 112.87(12) . . ? C22 C21 C29 120.90(14) . . ? C21 C22 C23 119.49(13) . . ? C21 C22 C31 120.71(13) . . ? C23 C22 C31 119.76(13) . . ? C24 C23 C22 120.76(14) . . ? C23 C24 C30 120.87(14) . . ? C26 C25 C30 120.62(16) . . ? C25 C26 C27 120.50(15) . . ? C28 C27 C26 120.35(16) . . ? C27 C28 C29 120.49(16) . . ? C28 C29 C21 121.55(14) . . ? C28 C29 C30 119.34(13) . . ? C21 C29 C30 119.11(14) . . ? C24 C30 C29 118.84(13) . . ? C24 C30 C25 122.45(15) . . ? C29 C30 C25 118.70(14) . . ? O33 C31 O32 122.34(12) . . ? O33 C31 C22 118.41(12) . . ? O32 C31 C22 119.25(12) . . ? C46 C41 C42 119.78(14) . . ? C46 C41 C47 119.93(14) . . ? C42 C41 C47 120.27(13) . . ? C43 C42 C41 118.24(15) . . ? F49 C43 C44 119.67(15) . . ? F49 C43 C42 117.20(16) . . ? C44 C43 C42 123.13(16) . . ? C43 C44 C45 118.01(15) . . ? C44 C45 C46 120.59(16) . . ? C41 C46 C45 120.24(16) . . ? N48 C47 C41 110.87(11) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 1.086 _refine_diff_density_min -0.503 _refine_diff_density_rms 0.055 data_imai###_4 _database_code_depnum_ccdc_archive 'CCDC 881758' #TrackingRef 'imai ver.2.cif' #data_im1670a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H16 F N O2' _chemical_formula_weight 297.32 _chemical_absolute_configuration rm 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 orthorhombic _symmetry_space_group_name_H-M P212121 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 6.3741(12) _cell_length_b 8.4170(15) _cell_length_c 27.401(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1470.1(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3707 _cell_measurement_theta_min 2.53 _cell_measurement_theta_max 30.71 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.27 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.343 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.9626 _exptl_absorpt_correction_T_max 0.9745 _exptl_absorpt_process_details multi-scan _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71075 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku Saturn' _diffrn_measurement_method \w-scans _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10787 _diffrn_reflns_av_R_equivalents 0.0300 _diffrn_reflns_av_sigmaI/netI 0.0272 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 2.53 _diffrn_reflns_theta_max 30.71 _reflns_number_total 4002 _reflns_number_gt 3707 _reflns_threshold_expression >2\s(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^ > 2\s(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^)+(0.0592P)^2^+0.3324P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(8) _refine_ls_number_reflns 4002 _refine_ls_number_parameters 210 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0438 _refine_ls_R_factor_gt 0.0407 _refine_ls_wR_factor_ref 0.1101 _refine_ls_wR_factor_gt 0.1081 _refine_ls_goodness_of_fit_ref 1.082 _refine_ls_restrained_S_all 1.082 _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 C1 C 0.12679(19) 0.46282(16) 0.16353(4) 0.0193(2) Uani 1 1 d . . . H1 H -0.0100 0.5061 0.1670 0.023 Uiso 1 1 calc R . . C2 C 0.23087(19) 0.47872(15) 0.11984(4) 0.0180(2) Uani 1 1 d . . . C3 C 0.4358(2) 0.41545(16) 0.11450(4) 0.0202(2) Uani 1 1 d . . . H3 H 0.5093 0.4289 0.0846 0.024 Uiso 1 1 calc R . . C4 C 0.5285(2) 0.33479(17) 0.15234(5) 0.0221(3) Uani 1 1 d . . . H4 H 0.6648 0.2913 0.1481 0.027 Uiso 1 1 calc R . . C5 C 0.5147(3) 0.23030(18) 0.23712(5) 0.0277(3) Uani 1 1 d . . . H5 H 0.6495 0.1836 0.2335 0.033 Uiso 1 1 calc R . . C6 C 0.4092(3) 0.21508(18) 0.28045(5) 0.0312(3) Uani 1 1 d . . . H6 H 0.4707 0.1571 0.3065 0.037 Uiso 1 1 calc R . . C7 C 0.2093(3) 0.28520(18) 0.28657(5) 0.0291(3) Uani 1 1 d . . . H7 H 0.1391 0.2760 0.3170 0.035 Uiso 1 1 calc R . . C8 C 0.1158(2) 0.36643(17) 0.24900(5) 0.0248(3) Uani 1 1 d . . . H8 H -0.0194 0.4119 0.2534 0.030 Uiso 1 1 calc R . . C9 C 0.2207(2) 0.38270(15) 0.20352(4) 0.0201(2) Uani 1 1 d . . . C10 C 0.4240(2) 0.31543(16) 0.19769(4) 0.0206(2) Uani 1 1 d . . . C11 C 0.1217(2) 0.55836(15) 0.07737(5) 0.0202(2) Uani 1 1 d . . . O12 O 0.23087(14) 0.58828(12) 0.03964(3) 0.0228(2) Uani 1 1 d . . . O13 O -0.06979(16) 0.58587(15) 0.08146(4) 0.0310(2) Uani 1 1 d . . . C21 C 0.3789(2) -0.04372(17) 0.08064(5) 0.0237(3) Uani 1 1 d . . . C22 C 0.3280(2) 0.03390(18) 0.03730(5) 0.0263(3) Uani 1 1 d . . . H22 H 0.4153 0.0229 0.0094 0.032 Uiso 1 1 calc R . . C23 C 0.1493(3) 0.12713(19) 0.03518(6) 0.0311(3) Uani 1 1 d . . . H23 H 0.1150 0.1788 0.0054 0.037 Uiso 0.428(3) 1 calc PR . . C24 C 0.0189(2) 0.14733(18) 0.07517(6) 0.0289(3) Uani 1 1 d . . . H24 H -0.1031 0.2119 0.0733 0.035 Uiso 1 1 calc R . . C25 C 0.0730(2) 0.06993(18) 0.11775(6) 0.0277(3) Uani 1 1 d . . . H25 H -0.0139 0.0824 0.1457 0.033 Uiso 0.572(3) 1 calc PR . . C26 C 0.2494(2) -0.02522(18) 0.12124(5) 0.0260(3) Uani 1 1 d . . . H26 H 0.2820 -0.0774 0.1510 0.031 Uiso 1 1 calc R . . C27 C 0.5756(2) -0.1422(2) 0.08487(5) 0.0275(3) Uani 1 1 d . . . H27A H 0.6980 -0.0702 0.0874 0.033 Uiso 1 1 calc R . . H27B H 0.5688 -0.2056 0.1152 0.033 Uiso 1 1 calc R . . N28 N 0.60767(16) -0.25127(14) 0.04281(4) 0.0202(2) Uani 1 1 d . . . H28A H 0.4928 -0.3144 0.0392 0.030 Uiso 1 1 calc R . . H28B H 0.7226 -0.3129 0.0483 0.030 Uiso 1 1 calc R . . H28C H 0.6273 -0.1933 0.0151 0.030 Uiso 1 1 calc R . . F29 F -0.0532(2) 0.0883(2) 0.15529(6) 0.0321(4) Uani 0.572(3) 1 d P . . F30 F 0.1122(4) 0.2015(3) -0.00295(8) 0.0367(6) Uani 0.428(3) 1 d P . . 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 0.0166(5) 0.0205(6) 0.0208(5) 0.0008(4) -0.0017(4) 0.0002(5) C2 0.0172(5) 0.0175(5) 0.0192(5) 0.0012(4) -0.0036(4) 0.0002(4) C3 0.0190(5) 0.0219(6) 0.0197(5) 0.0011(4) -0.0004(4) 0.0021(5) C4 0.0201(6) 0.0228(6) 0.0235(6) 0.0005(5) -0.0025(5) 0.0055(5) C5 0.0357(7) 0.0235(7) 0.0240(6) 0.0021(5) -0.0068(5) 0.0071(6) C6 0.0484(9) 0.0232(7) 0.0221(6) 0.0035(5) -0.0072(6) 0.0034(6) C7 0.0421(8) 0.0262(7) 0.0190(6) 0.0027(5) 0.0011(5) -0.0046(6) C8 0.0277(6) 0.0258(7) 0.0210(5) 0.0000(5) 0.0015(5) -0.0024(5) C9 0.0228(6) 0.0186(6) 0.0189(5) 0.0009(4) -0.0015(4) -0.0020(5) C10 0.0238(6) 0.0175(6) 0.0204(5) 0.0004(4) -0.0048(5) 0.0021(5) C11 0.0192(5) 0.0208(6) 0.0204(5) 0.0030(4) -0.0047(4) -0.0011(5) O12 0.0202(4) 0.0275(5) 0.0207(4) 0.0057(4) -0.0035(3) -0.0035(4) O13 0.0189(4) 0.0450(6) 0.0291(5) 0.0084(5) -0.0028(4) 0.0071(4) C21 0.0210(6) 0.0258(6) 0.0243(6) -0.0051(5) -0.0010(5) -0.0029(5) C22 0.0302(6) 0.0248(6) 0.0239(6) -0.0049(5) 0.0024(5) 0.0002(5) C23 0.0380(8) 0.0252(7) 0.0302(7) -0.0026(6) 0.0018(6) 0.0021(6) C24 0.0282(7) 0.0215(6) 0.0371(7) -0.0043(5) 0.0028(6) 0.0028(5) C25 0.0245(6) 0.0247(7) 0.0339(7) -0.0044(5) 0.0069(5) -0.0034(5) C26 0.0252(6) 0.0275(6) 0.0254(6) -0.0026(5) 0.0012(5) -0.0037(5) C27 0.0207(6) 0.0384(8) 0.0235(6) -0.0061(5) -0.0044(5) 0.0008(6) N28 0.0150(4) 0.0254(5) 0.0201(4) 0.0033(4) -0.0001(4) 0.0012(4) F29 0.0297(8) 0.0352(9) 0.0315(8) 0.0032(6) 0.0129(6) 0.0053(7) F30 0.0448(13) 0.0347(12) 0.0307(10) 0.0065(9) -0.0007(9) 0.0152(10) _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 1.3754(17) . ? C1 C9 1.4190(17) . ? C2 C3 1.4182(17) . ? C2 C11 1.5125(16) . ? C3 C4 1.3732(17) . ? C4 C10 1.4194(18) . ? C5 C6 1.371(2) . ? C5 C10 1.4198(17) . ? C6 C7 1.414(2) . ? C7 C8 1.372(2) . ? C8 C9 1.4208(17) . ? C9 C10 1.4231(18) . ? C11 O13 1.2476(16) . ? C11 O12 1.2712(16) . ? C21 C22 1.394(2) . ? C21 C26 1.3939(18) . ? C21 C27 1.508(2) . ? C22 C23 1.385(2) . ? C23 C24 1.386(2) . ? C24 C25 1.380(2) . ? C25 C26 1.384(2) . ? C27 N28 1.4874(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 C2 C1 C9 121.01(11) . . ? C1 C2 C3 119.84(11) . . ? C1 C2 C11 119.41(11) . . ? C3 C2 C11 120.71(11) . . ? C4 C3 C2 120.28(11) . . ? C3 C4 C10 121.04(12) . . ? C6 C5 C10 120.43(14) . . ? C5 C6 C7 120.39(13) . . ? C8 C7 C6 120.71(13) . . ? C7 C8 C9 120.10(13) . . ? C1 C9 C8 121.65(12) . . ? C1 C9 C10 119.10(11) . . ? C8 C9 C10 119.25(12) . . ? C4 C10 C5 122.19(12) . . ? C4 C10 C9 118.70(11) . . ? C5 C10 C9 119.10(12) . . ? O13 C11 O12 124.88(12) . . ? O13 C11 C2 117.60(11) . . ? O12 C11 C2 117.50(11) . . ? C22 C21 C26 119.34(13) . . ? C22 C21 C27 121.12(12) . . ? C26 C21 C27 119.50(12) . . ? C23 C22 C21 119.53(13) . . ? C22 C23 C24 122.01(14) . . ? C25 C24 C23 117.41(14) . . ? C24 C25 C26 122.33(13) . . ? C25 C26 C21 119.37(13) . . ? N28 C27 C21 113.20(11) . . ? _diffrn_measured_fraction_theta_max 0.912 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.282 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.046 #===END