# Supplementary Material (ESI) for Organic and Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 177 loop_ _publ_author_name 'Jian-Hua Xu' 'Hong-wen Hu' 'Yun Liu' 'Yong-Miao Shen' 'Yan Zhang' _publ_contact_author_name 'Jian-Hua Xu' _publ_contact_author_email XUJH@NJU.EDU.CN _publ_section_title ; Regioselective Synthesis of 3-Acylindolizines and Benzo- Analogues via 1,3-Dipolar Cycloadditions of N-Ylides with Maleic Anhydride ; _publ_contact_author_address 'Institute of Chemistry and Chemical Engineering, Nanjing University, Nanjing 210093, PR China' _publ_contact_author_fax '+86 25 83317761' _publ_contact_author_phone '+86 25 83592709 ' #TrackingRef '6e.CIF' _publ_requested_journal Org.Biomol.Chem. # Attachment '6e.CIF' data_l _database_code_depnum_ccdc_archive 'CCDC 761435' _audit_creation_method SHELXL-97 _chemical_name_systematic 1-(4-Fluorobenzoyl)pyrrolo[1,2-a]quinoline _chemical_name_common ? _chemical_formula_moiety 'C19 H12 F N O' _chemical_formula_sum 'C38 H24 F2 N2 O2' _exptl_crystal_recrystallization_method 'petroleum ether-ethyl acetate' _chemical_melting_point 393K _exptl_crystal_description block _exptl_crystal_colour yellow _diffrn_ambient_temperature 293(2) _chemical_formula_weight 578.59 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' _symmetry_int_tables_number 2 _chemical_absolute_configuration ? _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.8880(16) _cell_length_b 13.530(3) _cell_length_c 14.876(3) _cell_angle_alpha 103.97(3) _cell_angle_beta 105.05(3) _cell_angle_gamma 102.57(3) _cell_volume 1419.7(5) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 9 _cell_measurement_theta_max 12 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.353 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 0.093 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_correction_T_min 0.9727 _exptl_absorpt_correction_T_max 0.9908 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_radiation_probe ? _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf--Nonius CAD-4' _diffrn_measurement_method \w/2\q _diffrn_detector_area_resol_mean ? _diffrn_standards_number 3 _diffrn_standards_interval_count 200 _diffrn_standards_interval_time 2h _diffrn_standards_decay_% 0 _diffrn_reflns_number 5569 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0906 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.49 _diffrn_reflns_theta_max 25.27 _reflns_number_total 5162 _reflns_number_gt 2829 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0600P)^2^+1.7500P] 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 5162 _refine_ls_number_parameters 397 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1315 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.2004 _refine_ls_wR_factor_gt 0.1521 _refine_ls_goodness_of_fit_ref 1.004 _refine_ls_restrained_S_all 1.004 _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 F1 F 0.1644(4) -0.0461(2) 0.6364(2) 0.0954(9) Uani 1 1 d . . . O1 O 0.3313(4) -0.1821(3) 1.0177(2) 0.0784(10) Uani 1 1 d . . . N1 N 0.6438(4) -0.2734(3) 1.0351(3) 0.0617(9) Uani 1 1 d . . . C1 C 0.3838(8) -0.5050(4) 1.1407(3) 0.0836(16) Uani 1 1 d . . . H1A H 0.3266 -0.5583 1.1619 0.100 Uiso 1 1 calc R . . C2 C 0.5708(8) -0.4694(5) 1.1683(4) 0.0849(15) Uani 1 1 d . . . H2A H 0.6407 -0.4983 1.2093 0.102 Uiso 1 1 calc R . . C3 C 0.6621(7) -0.3888(4) 1.1357(3) 0.0734(13) Uani 1 1 d . . . C4 C 0.5515(6) -0.3496(4) 1.0730(3) 0.0619(11) Uani 1 1 d . . . C5 C 0.3613(6) -0.3834(4) 1.0461(3) 0.0694(12) Uani 1 1 d . . . H5A H 0.2886 -0.3551 1.0056 0.083 Uiso 1 1 calc R . . C6 C 0.2830(8) -0.4618(4) 1.0823(4) 0.0797(14) Uani 1 1 d . . . H6A H 0.1556 -0.4852 1.0653 0.096 Uiso 1 1 calc R . . C7 C 0.8543(8) -0.3611(5) 1.1555(4) 0.0900(16) Uani 1 1 d . . . H7A H 0.9251 -0.3874 1.1989 0.108 Uiso 1 1 calc R . . C8 C 0.9370(7) -0.2973(4) 1.1127(4) 0.0855(16) Uani 1 1 d . . . H8A H 1.0633 -0.2811 1.1253 0.103 Uiso 1 1 calc R . . C9 C 0.8323(6) -0.2559(4) 1.0497(4) 0.0696(13) Uani 1 1 d . . . C10 C 0.8793(6) -0.1959(4) 0.9903(4) 0.0770(14) Uani 1 1 d . . . H10A H 0.9957 -0.1727 0.9856 0.092 Uiso 1 1 calc R . . C11 C 0.7226(6) -0.1771(4) 0.9402(4) 0.0729(13) Uani 1 1 d . . . H11A H 0.7155 -0.1399 0.8950 0.088 Uiso 1 1 calc R . . C12 C 0.5763(5) -0.2229(3) 0.9679(3) 0.0580(11) Uani 1 1 d . . . C13 C 0.4118(6) -0.1892(4) 0.9565(3) 0.0655(12) Uani 1 1 d . . . C14 C 0.3468(5) -0.1540(3) 0.8689(3) 0.0562(11) Uani 1 1 d . . . C15 C 0.3557(6) -0.2006(3) 0.7782(3) 0.0611(11) Uani 1 1 d . . . H15A H 0.4070 -0.2565 0.7702 0.073 Uiso 1 1 calc R . . C16 C 0.2915(6) -0.1678(4) 0.6983(4) 0.0674(12) Uani 1 1 d . . . H16A H 0.2929 -0.2024 0.6364 0.081 Uiso 1 1 calc R . . C17 C 0.2257(6) -0.0819(4) 0.7144(4) 0.0700(13) Uani 1 1 d . . . C18 C 0.2130(6) -0.0318(4) 0.8014(4) 0.0753(14) Uani 1 1 d . . . H18A H 0.1643 0.0252 0.8084 0.090 Uiso 1 1 calc R . . C19 C 0.2751(6) -0.0678(4) 0.8803(4) 0.0735(14) Uani 1 1 d . . . H19A H 0.2686 -0.0342 0.9412 0.088 Uiso 1 1 calc R . . F2 F 0.7743(4) -0.0820(2) 0.7539(2) 0.0881(9) Uani 1 1 d . . . O2 O 0.6985(4) 0.2627(2) 0.5433(2) 0.0654(8) Uani 1 1 d . . . N2 N 0.4349(4) 0.3698(2) 0.6016(2) 0.0456(7) Uani 1 1 d . . . C20 C 0.8211(7) 0.6677(4) 0.6777(4) 0.0780(15) Uani 1 1 d . . . H20A H 0.9059 0.7345 0.6951 0.094 Uiso 1 1 calc R . . C21 C 0.6372(7) 0.6542(3) 0.6397(3) 0.0666(12) Uani 1 1 d . . . H21A H 0.5989 0.7125 0.6306 0.080 Uiso 1 1 calc R . . C22 C 0.5039(6) 0.5553(3) 0.6139(3) 0.0499(9) Uani 1 1 d . . . C23 C 0.5696(5) 0.4682(3) 0.6264(3) 0.0462(9) Uani 1 1 d . . . C24 C 0.7553(5) 0.4828(3) 0.6645(3) 0.0549(10) Uani 1 1 d . . . H24A H 0.7970 0.4254 0.6732 0.066 Uiso 1 1 calc R . . C25 C 0.8798(6) 0.5821(4) 0.6900(4) 0.0712(13) Uani 1 1 d . . . H25A H 1.0050 0.5911 0.7157 0.085 Uiso 1 1 calc R . . C26 C 0.3122(6) 0.5430(4) 0.5844(3) 0.0632(12) Uani 1 1 d . . . H26A H 0.2707 0.5993 0.5723 0.076 Uiso 1 1 calc R . . C27 C 0.1896(6) 0.4506(4) 0.5736(3) 0.0614(11) Uani 1 1 d . . . H27A H 0.0652 0.4452 0.5586 0.074 Uiso 1 1 calc R . . C28 C 0.2502(5) 0.3619(3) 0.5852(3) 0.0500(10) Uani 1 1 d . . . C29 C 0.1599(6) 0.2640(4) 0.5848(3) 0.0610(11) Uani 1 1 d . . . H29A H 0.0352 0.2387 0.5757 0.073 Uiso 1 1 calc R . . C30 C 0.2877(5) 0.2091(3) 0.6004(3) 0.0580(11) Uani 1 1 d . . . H30A H 0.2628 0.1402 0.6045 0.070 Uiso 1 1 calc R . . C31 C 0.4572(5) 0.2717(3) 0.6090(3) 0.0518(10) Uani 1 1 d . . . C32 C 0.6083(6) 0.2310(3) 0.5931(3) 0.0527(10) Uani 1 1 d . . . C33 C 0.6425(5) 0.1459(3) 0.6354(3) 0.0472(9) Uani 1 1 d . . . C34 C 0.6166(5) 0.1412(3) 0.7232(3) 0.0547(10) Uani 1 1 d . . . H34A H 0.5687 0.1904 0.7555 0.066 Uiso 1 1 calc R . . C35 C 0.6609(6) 0.0646(3) 0.7632(3) 0.0611(11) Uani 1 1 d . . . H35A H 0.6429 0.0611 0.8219 0.073 Uiso 1 1 calc R . . C36 C 0.7314(6) -0.0056(3) 0.7151(4) 0.0637(12) Uani 1 1 d . . . C37 C 0.7558(6) -0.0059(3) 0.6266(4) 0.0669(12) Uani 1 1 d . . . H37A H 0.7994 -0.0572 0.5939 0.080 Uiso 1 1 calc R . . C38 C 0.7137(6) 0.0720(3) 0.5879(3) 0.0595(11) Uani 1 1 d . . . H38A H 0.7332 0.0751 0.5295 0.071 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 F1 0.090(2) 0.093(2) 0.123(3) 0.055(2) 0.0415(19) 0.0365(17) O1 0.072(2) 0.098(2) 0.082(2) 0.0239(19) 0.0467(18) 0.0376(19) N1 0.045(2) 0.067(2) 0.064(2) 0.0081(19) 0.0200(17) 0.0138(17) C1 0.098(4) 0.095(4) 0.046(3) 0.012(3) 0.030(3) 0.009(3) C2 0.105(4) 0.103(4) 0.053(3) 0.033(3) 0.028(3) 0.034(3) C3 0.078(3) 0.092(4) 0.043(3) 0.014(2) 0.016(2) 0.025(3) C4 0.063(3) 0.076(3) 0.048(2) 0.013(2) 0.026(2) 0.020(2) C5 0.064(3) 0.082(3) 0.066(3) 0.021(3) 0.030(2) 0.024(3) C6 0.081(3) 0.100(4) 0.072(3) 0.033(3) 0.045(3) 0.025(3) C7 0.069(4) 0.099(4) 0.084(4) 0.021(3) 0.005(3) 0.022(3) C8 0.049(3) 0.093(4) 0.092(4) 0.013(3) 0.002(3) 0.021(3) C9 0.047(3) 0.071(3) 0.078(3) 0.004(3) 0.019(2) 0.014(2) C10 0.048(3) 0.083(3) 0.093(4) 0.017(3) 0.029(3) 0.010(2) C11 0.062(3) 0.075(3) 0.094(4) 0.029(3) 0.044(3) 0.021(2) C12 0.048(2) 0.062(3) 0.064(3) 0.014(2) 0.023(2) 0.016(2) C13 0.058(3) 0.071(3) 0.075(3) 0.018(2) 0.039(2) 0.020(2) C14 0.046(2) 0.051(2) 0.074(3) 0.015(2) 0.029(2) 0.0120(19) C15 0.063(3) 0.056(3) 0.075(3) 0.020(2) 0.034(2) 0.024(2) C16 0.068(3) 0.067(3) 0.082(3) 0.026(3) 0.040(3) 0.028(2) C17 0.055(3) 0.068(3) 0.095(4) 0.035(3) 0.031(3) 0.016(2) C18 0.058(3) 0.060(3) 0.122(5) 0.033(3) 0.040(3) 0.028(2) C19 0.067(3) 0.060(3) 0.101(4) 0.014(3) 0.046(3) 0.023(2) F2 0.096(2) 0.0788(19) 0.120(2) 0.0586(18) 0.0471(18) 0.0435(16) O2 0.075(2) 0.0705(19) 0.083(2) 0.0410(17) 0.0524(18) 0.0358(16) N2 0.0427(18) 0.0475(18) 0.0564(19) 0.0197(15) 0.0237(15) 0.0204(15) C20 0.082(4) 0.048(3) 0.107(4) 0.016(3) 0.055(3) 0.007(2) C21 0.092(4) 0.047(2) 0.080(3) 0.026(2) 0.048(3) 0.027(2) C22 0.061(3) 0.048(2) 0.045(2) 0.0137(18) 0.0239(19) 0.018(2) C23 0.057(2) 0.048(2) 0.049(2) 0.0204(18) 0.0317(19) 0.0208(19) C24 0.053(2) 0.055(3) 0.066(3) 0.020(2) 0.033(2) 0.019(2) C25 0.062(3) 0.068(3) 0.092(4) 0.021(3) 0.046(3) 0.016(2) C26 0.080(3) 0.067(3) 0.067(3) 0.036(2) 0.032(2) 0.047(3) C27 0.053(3) 0.081(3) 0.063(3) 0.024(2) 0.024(2) 0.039(2) C28 0.044(2) 0.061(3) 0.048(2) 0.0156(19) 0.0165(18) 0.022(2) C29 0.050(2) 0.067(3) 0.075(3) 0.024(2) 0.031(2) 0.021(2) C30 0.052(2) 0.058(3) 0.071(3) 0.022(2) 0.027(2) 0.019(2) C31 0.051(2) 0.053(2) 0.069(3) 0.028(2) 0.033(2) 0.025(2) C32 0.058(2) 0.053(2) 0.065(3) 0.024(2) 0.034(2) 0.027(2) C33 0.043(2) 0.045(2) 0.065(3) 0.0218(19) 0.0294(19) 0.0178(17) C34 0.054(2) 0.053(2) 0.067(3) 0.019(2) 0.032(2) 0.022(2) C35 0.065(3) 0.057(3) 0.073(3) 0.030(2) 0.035(2) 0.017(2) C36 0.057(3) 0.056(3) 0.091(3) 0.033(3) 0.029(2) 0.026(2) C37 0.074(3) 0.056(3) 0.094(4) 0.026(2) 0.051(3) 0.036(2) C38 0.060(3) 0.055(3) 0.077(3) 0.021(2) 0.040(2) 0.022(2) _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 F1 C17 1.377(5) . ? O1 C13 1.235(5) . ? N1 C12 1.400(5) . ? N1 C9 1.403(5) . ? N1 C4 1.441(5) . ? C1 C6 1.348(7) . ? C1 C2 1.363(7) . ? C1 H1A 0.9300 . ? C2 C3 1.426(7) . ? C2 H2A 0.9300 . ? C3 C4 1.390(6) . ? C3 C7 1.412(7) . ? C4 C5 1.386(6) . ? C5 C6 1.401(6) . ? C5 H5A 0.9300 . ? C6 H6A 0.9300 . ? C7 C8 1.346(7) . ? C7 H7A 0.9300 . ? C8 C9 1.388(7) . ? C8 H8A 0.9300 . ? C9 C10 1.402(7) . ? C10 C11 1.377(6) . ? C10 H10A 0.9300 . ? C11 C12 1.395(6) . ? C11 H11A 0.9300 . ? C12 C13 1.450(6) . ? C13 C14 1.499(6) . ? C14 C15 1.372(6) . ? C14 C19 1.396(6) . ? C15 C16 1.381(6) . ? C15 H15A 0.9300 . ? C16 C17 1.367(6) . ? C16 H16A 0.9300 . ? C17 C18 1.347(7) . ? C18 C19 1.393(7) . ? C18 H18A 0.9300 . ? C19 H19A 0.9300 . ? F2 C36 1.362(5) . ? O2 C32 1.238(4) . ? N2 C28 1.389(4) . ? N2 C31 1.402(5) . ? N2 C23 1.408(5) . ? C20 C21 1.366(6) . ? C20 C25 1.372(6) . ? C20 H20A 0.9300 . ? C21 C22 1.405(6) . ? C21 H21A 0.9300 . ? C22 C23 1.418(5) . ? C22 C26 1.421(6) . ? C23 C24 1.377(5) . ? C24 C25 1.378(6) . ? C24 H24A 0.9300 . ? C25 H25A 0.9300 . ? C26 C27 1.349(6) . ? C26 H26A 0.9300 . ? C27 C28 1.417(5) . ? C27 H27A 0.9300 . ? C28 C29 1.358(5) . ? C29 C30 1.383(5) . ? C29 H29A 0.9300 . ? C30 C31 1.374(5) . ? C30 H30A 0.9300 . ? C31 C32 1.466(5) . ? C32 C33 1.481(5) . ? C33 C38 1.386(5) . ? C33 C34 1.388(5) . ? C34 C35 1.379(5) . ? C34 H34A 0.9300 . ? C35 C36 1.353(6) . ? C35 H35A 0.9300 . ? C36 C37 1.378(6) . ? C37 C38 1.377(6) . ? C37 H37A 0.9300 . ? C38 H38A 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C12 N1 C9 107.9(4) . . ? C12 N1 C4 131.8(4) . . ? C9 N1 C4 119.2(4) . . ? C6 C1 C2 118.9(5) . . ? C6 C1 H1A 120.5 . . ? C2 C1 H1A 120.5 . . ? C1 C2 C3 121.7(5) . . ? C1 C2 H2A 119.1 . . ? C3 C2 H2A 119.1 . . ? C4 C3 C7 121.3(5) . . ? C4 C3 C2 117.0(5) . . ? C7 C3 C2 121.2(5) . . ? C5 C4 C3 121.9(5) . . ? C5 C4 N1 121.2(4) . . ? C3 C4 N1 116.8(4) . . ? C4 C5 C6 117.3(5) . . ? C4 C5 H5A 121.3 . . ? C6 C5 H5A 121.3 . . ? C1 C6 C5 123.1(5) . . ? C1 C6 H6A 118.5 . . ? C5 C6 H6A 118.5 . . ? C8 C7 C3 121.2(5) . . ? C8 C7 H7A 119.4 . . ? C3 C7 H7A 119.4 . . ? C7 C8 C9 119.6(5) . . ? C7 C8 H8A 120.2 . . ? C9 C8 H8A 120.2 . . ? C8 C9 C10 131.2(5) . . ? C8 C9 N1 121.1(5) . . ? C10 C9 N1 107.7(4) . . ? C11 C10 C9 107.9(4) . . ? C11 C10 H10A 126.0 . . ? C9 C10 H10A 126.0 . . ? C10 C11 C12 109.2(5) . . ? C10 C11 H11A 125.4 . . ? C12 C11 H11A 125.4 . . ? C11 C12 N1 107.3(4) . . ? C11 C12 C13 123.0(4) . . ? N1 C12 C13 126.1(4) . . ? O1 C13 C12 123.4(4) . . ? O1 C13 C14 119.4(4) . . ? C12 C13 C14 117.1(4) . . ? C15 C14 C19 117.9(4) . . ? C15 C14 C13 123.9(4) . . ? C19 C14 C13 118.2(4) . . ? C14 C15 C16 122.6(4) . . ? C14 C15 H15A 118.7 . . ? C16 C15 H15A 118.7 . . ? C17 C16 C15 116.8(5) . . ? C17 C16 H16A 121.6 . . ? C15 C16 H16A 121.6 . . ? C18 C17 C16 124.0(5) . . ? C18 C17 F1 118.0(5) . . ? C16 C17 F1 118.0(5) . . ? C17 C18 C19 118.1(4) . . ? C17 C18 H18A 121.0 . . ? C19 C18 H18A 121.0 . . ? C18 C19 C14 120.6(5) . . ? C18 C19 H19A 119.7 . . ? C14 C19 H19A 119.7 . . ? C28 N2 C31 107.4(3) . . ? C28 N2 C23 122.1(3) . . ? C31 N2 C23 129.2(3) . . ? C21 C20 C25 119.6(4) . . ? C21 C20 H20A 120.2 . . ? C25 C20 H20A 120.2 . . ? C20 C21 C22 122.2(4) . . ? C20 C21 H21A 118.9 . . ? C22 C21 H21A 118.9 . . ? C21 C22 C23 116.7(4) . . ? C21 C22 C26 122.6(4) . . ? C23 C22 C26 120.5(4) . . ? C24 C23 N2 123.2(3) . . ? C24 C23 C22 120.5(4) . . ? N2 C23 C22 116.3(3) . . ? C23 C24 C25 120.3(4) . . ? C23 C24 H24A 119.9 . . ? C25 C24 H24A 119.9 . . ? C20 C25 C24 120.7(4) . . ? C20 C25 H25A 119.6 . . ? C24 C25 H25A 119.6 . . ? C27 C26 C22 120.8(4) . . ? C27 C26 H26A 119.6 . . ? C22 C26 H26A 119.6 . . ? C26 C27 C28 120.0(4) . . ? C26 C27 H27A 120.0 . . ? C28 C27 H27A 120.0 . . ? C29 C28 N2 109.1(3) . . ? C29 C28 C27 131.9(4) . . ? N2 C28 C27 118.9(4) . . ? C28 C29 C30 107.3(4) . . ? C28 C29 H29A 126.4 . . ? C30 C29 H29A 126.4 . . ? C31 C30 C29 109.7(4) . . ? C31 C30 H30A 125.2 . . ? C29 C30 H30A 125.2 . . ? C30 C31 N2 106.5(3) . . ? C30 C31 C32 124.6(4) . . ? N2 C31 C32 125.6(3) . . ? O2 C32 C31 121.9(3) . . ? O2 C32 C33 121.2(3) . . ? C31 C32 C33 116.8(3) . . ? C38 C33 C34 119.1(4) . . ? C38 C33 C32 118.2(4) . . ? C34 C33 C32 122.6(3) . . ? C35 C34 C33 120.8(4) . . ? C35 C34 H34A 119.6 . . ? C33 C34 H34A 119.6 . . ? C36 C35 C34 118.4(4) . . ? C36 C35 H35A 120.8 . . ? C34 C35 H35A 120.8 . . ? C35 C36 F2 118.7(4) . . ? C35 C36 C37 123.0(4) . . ? F2 C36 C37 118.3(4) . . ? C38 C37 C36 118.1(4) . . ? C38 C37 H37A 120.9 . . ? C36 C37 H37A 120.9 . . ? C37 C38 C33 120.6(4) . . ? C37 C38 H38A 119.7 . . ? C33 C38 H38A 119.7 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 -0.9(8) . . . . ? C1 C2 C3 C4 -1.2(7) . . . . ? C1 C2 C3 C7 -172.8(5) . . . . ? C7 C3 C4 C5 174.2(5) . . . . ? C2 C3 C4 C5 2.7(7) . . . . ? C7 C3 C4 N1 -4.5(7) . . . . ? C2 C3 C4 N1 -176.1(4) . . . . ? C12 N1 C4 C5 -2.3(7) . . . . ? C9 N1 C4 C5 -168.6(4) . . . . ? C12 N1 C4 C3 176.4(4) . . . . ? C9 N1 C4 C3 10.1(6) . . . . ? C3 C4 C5 C6 -2.0(7) . . . . ? N1 C4 C5 C6 176.7(4) . . . . ? C2 C1 C6 C5 1.7(8) . . . . ? C4 C5 C6 C1 -0.3(7) . . . . ? C4 C3 C7 C8 -1.3(8) . . . . ? C2 C3 C7 C8 169.9(5) . . . . ? C3 C7 C8 C9 1.5(8) . . . . ? C7 C8 C9 C10 -174.1(5) . . . . ? C7 C8 C9 N1 4.5(8) . . . . ? C12 N1 C9 C8 -179.7(4) . . . . ? C4 N1 C9 C8 -10.4(6) . . . . ? C12 N1 C9 C10 -0.8(5) . . . . ? C4 N1 C9 C10 168.5(4) . . . . ? C8 C9 C10 C11 178.6(5) . . . . ? N1 C9 C10 C11 -0.1(5) . . . . ? C9 C10 C11 C12 1.0(6) . . . . ? C10 C11 C12 N1 -1.5(5) . . . . ? C10 C11 C12 C13 158.4(4) . . . . ? C9 N1 C12 C11 1.4(5) . . . . ? C4 N1 C12 C11 -166.0(4) . . . . ? C9 N1 C12 C13 -157.7(4) . . . . ? C4 N1 C12 C13 34.9(7) . . . . ? C11 C12 C13 O1 -141.1(5) . . . . ? N1 C12 C13 O1 14.9(7) . . . . ? C11 C12 C13 C14 34.4(6) . . . . ? N1 C12 C13 C14 -169.7(4) . . . . ? O1 C13 C14 C15 -147.0(4) . . . . ? C12 C13 C14 C15 37.3(6) . . . . ? O1 C13 C14 C19 33.8(6) . . . . ? C12 C13 C14 C19 -141.8(4) . . . . ? C19 C14 C15 C16 -2.1(6) . . . . ? C13 C14 C15 C16 178.7(4) . . . . ? C14 C15 C16 C17 3.2(7) . . . . ? C15 C16 C17 C18 -3.0(7) . . . . ? C15 C16 C17 F1 178.7(4) . . . . ? C16 C17 C18 C19 1.7(7) . . . . ? F1 C17 C18 C19 -180.0(4) . . . . ? C17 C18 C19 C14 -0.5(7) . . . . ? C15 C14 C19 C18 0.7(6) . . . . ? C13 C14 C19 C18 179.9(4) . . . . ? C25 C20 C21 C22 1.1(7) . . . . ? C20 C21 C22 C23 -1.9(6) . . . . ? C20 C21 C22 C26 173.1(4) . . . . ? C28 N2 C23 C24 164.7(4) . . . . ? C31 N2 C23 C24 -0.4(6) . . . . ? C28 N2 C23 C22 -12.6(5) . . . . ? C31 N2 C23 C22 -177.8(4) . . . . ? C21 C22 C23 C24 1.8(5) . . . . ? C26 C22 C23 C24 -173.4(4) . . . . ? C21 C22 C23 N2 179.2(3) . . . . ? C26 C22 C23 N2 4.1(5) . . . . ? N2 C23 C24 C25 -178.0(4) . . . . ? C22 C23 C24 C25 -0.8(6) . . . . ? C21 C20 C25 C24 -0.1(7) . . . . ? C23 C24 C25 C20 0.0(7) . . . . ? C21 C22 C26 C27 -170.5(4) . . . . ? C23 C22 C26 C27 4.3(6) . . . . ? C22 C26 C27 C28 -4.4(6) . . . . ? C31 N2 C28 C29 1.6(4) . . . . ? C23 N2 C28 C29 -166.4(3) . . . . ? C31 N2 C28 C27 -179.2(3) . . . . ? C23 N2 C28 C27 12.9(5) . . . . ? C26 C27 C28 C29 175.1(5) . . . . ? C26 C27 C28 N2 -4.0(6) . . . . ? N2 C28 C29 C30 -0.4(5) . . . . ? C27 C28 C29 C30 -179.5(4) . . . . ? C28 C29 C30 C31 -1.0(5) . . . . ? C29 C30 C31 N2 1.9(5) . . . . ? C29 C30 C31 C32 -158.5(4) . . . . ? C28 N2 C31 C30 -2.1(4) . . . . ? C23 N2 C31 C30 164.7(4) . . . . ? C28 N2 C31 C32 158.1(4) . . . . ? C23 N2 C31 C32 -35.1(6) . . . . ? C30 C31 C32 O2 134.0(5) . . . . ? N2 C31 C32 O2 -22.8(7) . . . . ? C30 C31 C32 C33 -43.0(6) . . . . ? N2 C31 C32 C33 160.2(4) . . . . ? O2 C32 C33 C38 -27.2(6) . . . . ? C31 C32 C33 C38 149.8(4) . . . . ? O2 C32 C33 C34 148.8(4) . . . . ? C31 C32 C33 C34 -34.2(6) . . . . ? C38 C33 C34 C35 0.1(6) . . . . ? C32 C33 C34 C35 -175.9(4) . . . . ? C33 C34 C35 C36 0.4(6) . . . . ? C34 C35 C36 F2 -179.6(4) . . . . ? C34 C35 C36 C37 -2.0(7) . . . . ? C35 C36 C37 C38 2.9(7) . . . . ? F2 C36 C37 C38 -179.5(4) . . . . ? C36 C37 C38 C33 -2.3(7) . . . . ? C34 C33 C38 C37 0.9(6) . . . . ? C32 C33 C38 C37 177.1(4) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.276 _refine_diff_density_min -0.283 _refine_diff_density_rms 0.074