# Electronic Supplementary Material (ESI) for RSC Advances # 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_shelxl _database_code_depnum_ccdc_archive 'CCDC 897553' #TrackingRef 'AS3.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C23 H24 F2 N2 O3' _chemical_formula_sum 'C23 H24 F2 N2 O3' _chemical_formula_weight 414.44 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 5.8519(4) _cell_length_b 11.3138(8) _cell_length_c 15.5758(11) _cell_angle_alpha 76.561(4) _cell_angle_beta 84.861(3) _cell_angle_gamma 89.129(3) _cell_volume 998.95(12) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 7741 _cell_measurement_theta_min 5.062 _cell_measurement_theta_max 55.628 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.378 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 436 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9596 _exptl_absorpt_correction_T_max 0.9795 _exptl_absorpt_process_details 'SADABS (Bruker, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(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 axs kappa apex2 CCD Diffractometer' _diffrn_measurement_method '\w and \f scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17863 _diffrn_reflns_av_R_equivalents 0.0232 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 1.35 _diffrn_reflns_theta_max 28.26 _reflns_number_total 4894 _reflns_number_gt 3538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'APEX2/SAINT (Bruker, 2004)' _computing_data_reduction 'SAINT/XPREP (Bruker, 2004)' _computing_structure_solution 'SIR92 (Altornare et al., 1993)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1080P)^2^+0.2712P] 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 SHELXL _refine_ls_extinction_coef 0.020(6) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 4894 _refine_ls_number_parameters 272 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0784 _refine_ls_R_factor_gt 0.0558 _refine_ls_wR_factor_ref 0.2024 _refine_ls_wR_factor_gt 0.1642 _refine_ls_goodness_of_fit_ref 1.070 _refine_ls_restrained_S_all 1.070 _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 0.4601(4) 0.28567(18) 0.21268(14) 0.0548(5) Uani 1 1 d . . . H1 H 0.4947 0.3470 0.1621 0.066 Uiso 1 1 calc R . . C2 C 0.5969(4) 0.1849(2) 0.22925(17) 0.0647(6) Uani 1 1 d . . . H2 H 0.7246 0.1781 0.1907 0.078 Uiso 1 1 calc R . . C3 C 0.5437(4) 0.0950(2) 0.30268(17) 0.0661(6) Uani 1 1 d . . . C4 C 0.3595(5) 0.1011(2) 0.36043(17) 0.0727(7) Uani 1 1 d . . . H4 H 0.3283 0.0387 0.4107 0.087 Uiso 1 1 calc R . . C5 C 0.2175(4) 0.20189(19) 0.34361(15) 0.0621(5) Uani 1 1 d . . . H5 H 0.0867 0.2053 0.3815 0.075 Uiso 1 1 calc R . . C6 C 0.2693(3) 0.29769(16) 0.27073(12) 0.0450(4) Uani 1 1 d . . . C7 C -0.0406(4) 0.41872(18) 0.32367(13) 0.0529(5) Uani 1 1 d . . . H7A H -0.1729 0.3718 0.3174 0.063 Uiso 1 1 calc R . . H7B H 0.0099 0.3864 0.3822 0.063 Uiso 1 1 calc R . . C8 C -0.1841(3) 0.59806(18) 0.22890(12) 0.0459(4) Uani 1 1 d . . . H8A H -0.2137 0.6837 0.2247 0.055 Uiso 1 1 calc R . . H8B H -0.3270 0.5596 0.2229 0.055 Uiso 1 1 calc R . . C9 C -0.0037(3) 0.58378(16) 0.15198(11) 0.0417(4) Uani 1 1 d . . . C10 C 0.0644(3) 0.44909(17) 0.16812(12) 0.0482(4) Uani 1 1 d . . . H10A H -0.0666 0.4008 0.1625 0.058 Uiso 1 1 calc R . . H10B H 0.1855 0.4388 0.1237 0.058 Uiso 1 1 calc R . . C11 C -0.1256(3) 0.61603(19) 0.06679(12) 0.0483(4) Uani 1 1 d . . . C12 C -0.1041(5) 0.7422(2) 0.01131(16) 0.0688(6) Uani 1 1 d . . . H12A H -0.2219 0.7914 0.0336 0.083 Uiso 1 1 calc R . . H12B H -0.1344 0.7408 -0.0487 0.083 Uiso 1 1 calc R . . C13 C 0.1236(5) 0.8028(2) 0.00784(15) 0.0722(6) Uani 1 1 d . . . H13A H 0.1132 0.8878 -0.0220 0.087 Uiso 1 1 calc R . . H13B H 0.2378 0.7652 -0.0262 0.087 Uiso 1 1 calc R . . C14 C 0.1984(3) 0.79300(18) 0.09960(13) 0.0519(5) Uani 1 1 d . . . C15 C 0.2129(3) 0.66122(17) 0.14677(12) 0.0444(4) Uani 1 1 d . . . H15A H 0.2511 0.6573 0.2067 0.053 Uiso 1 1 calc R . . H15B H 0.3385 0.6247 0.1172 0.053 Uiso 1 1 calc R . . C16 C 0.1864(5) 0.9340(3) 0.1831(2) 0.0849(8) Uani 1 1 d . . . H16A H 0.1984 0.8994 0.2456 0.102 Uiso 1 1 calc R . . H16B H 0.1201 1.0144 0.1764 0.102 Uiso 1 1 calc R . . C17 C 0.4114(6) 0.9408(3) 0.1341(3) 0.1088(12) Uani 1 1 d . . . H17A H 0.4314 1.0181 0.0913 0.131 Uiso 1 1 calc R . . H17B H 0.5315 0.9325 0.1741 0.131 Uiso 1 1 calc R . . C18 C 0.2175(3) 0.5775(2) 0.39807(13) 0.0558(5) Uani 1 1 d . . . H18 H 0.2864 0.5059 0.3899 0.067 Uiso 1 1 calc R . . C19 C 0.3189(4) 0.6458(2) 0.44688(15) 0.0660(6) Uani 1 1 d . . . H19 H 0.4544 0.6203 0.4723 0.079 Uiso 1 1 calc R . . C20 C 0.2179(4) 0.7515(2) 0.45739(14) 0.0648(6) Uani 1 1 d . . . C21 C 0.0190(4) 0.7919(2) 0.42104(14) 0.0614(5) Uani 1 1 d . . . H21 H -0.0459 0.8648 0.4286 0.074 Uiso 1 1 calc R . . C22 C -0.0836(3) 0.72317(18) 0.37312(12) 0.0518(5) Uani 1 1 d . . . H22 H -0.2196 0.7498 0.3485 0.062 Uiso 1 1 calc R . . C23 C 0.0120(3) 0.61456(17) 0.36062(11) 0.0438(4) Uani 1 1 d . . . N1 N 0.1438(3) 0.40649(14) 0.25643(10) 0.0483(4) Uani 1 1 d . . . N2 N -0.1052(3) 0.54364(14) 0.31537(10) 0.0473(4) Uani 1 1 d . . . O1 O -0.2522(3) 0.54436(17) 0.04832(10) 0.0717(5) Uani 1 1 d . . . O2 O 0.0503(3) 0.85975(14) 0.14773(12) 0.0671(4) Uani 1 1 d . . . O3 O 0.4190(3) 0.84693(15) 0.09204(12) 0.0716(5) Uani 1 1 d . . . F1 F 0.6817(3) -0.00434(15) 0.31884(13) 0.1035(6) Uani 1 1 d . . . F2 F 0.3167(4) 0.81837(15) 0.50643(11) 0.0983(6) 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 0.0594(11) 0.0454(10) 0.0558(11) -0.0056(8) -0.0013(9) 0.0026(8) C2 0.0664(13) 0.0586(13) 0.0700(14) -0.0175(11) -0.0058(10) 0.0119(10) C3 0.0830(15) 0.0457(11) 0.0727(14) -0.0156(10) -0.0213(12) 0.0187(10) C4 0.1051(19) 0.0461(11) 0.0604(13) 0.0010(10) -0.0087(13) 0.0096(12) C5 0.0798(14) 0.0472(11) 0.0533(12) -0.0023(9) 0.0015(10) 0.0044(10) C6 0.0548(9) 0.0380(9) 0.0429(9) -0.0093(7) -0.0084(7) -0.0008(7) C7 0.0648(11) 0.0487(10) 0.0405(9) -0.0040(8) 0.0026(8) 0.0036(8) C8 0.0381(8) 0.0567(10) 0.0414(9) -0.0092(8) -0.0026(7) 0.0056(7) C9 0.0381(8) 0.0498(9) 0.0363(8) -0.0076(7) -0.0049(6) 0.0038(7) C10 0.0540(10) 0.0498(10) 0.0405(9) -0.0109(8) -0.0022(7) 0.0028(8) C11 0.0405(8) 0.0647(12) 0.0407(9) -0.0138(8) -0.0057(7) 0.0074(8) C12 0.0859(16) 0.0692(14) 0.0529(12) -0.0090(10) -0.0303(11) 0.0159(12) C13 0.0922(17) 0.0659(14) 0.0503(12) 0.0021(10) -0.0036(11) 0.0016(12) C14 0.0477(9) 0.0540(11) 0.0517(11) -0.0092(9) 0.0004(8) -0.0002(8) C15 0.0352(7) 0.0543(10) 0.0422(9) -0.0080(8) -0.0037(6) 0.0053(7) C16 0.101(2) 0.0758(17) 0.0816(18) -0.0336(14) 0.0180(15) -0.0183(14) C17 0.0800(18) 0.108(2) 0.160(3) -0.079(2) 0.004(2) -0.0156(17) C18 0.0541(10) 0.0629(12) 0.0472(10) -0.0058(9) -0.0073(8) 0.0139(9) C19 0.0597(12) 0.0786(15) 0.0529(12) 0.0029(11) -0.0165(9) -0.0003(10) C20 0.0854(15) 0.0656(13) 0.0401(10) -0.0015(9) -0.0138(10) -0.0181(11) C21 0.0848(15) 0.0526(11) 0.0460(11) -0.0098(9) -0.0066(10) 0.0047(10) C22 0.0544(10) 0.0567(11) 0.0424(10) -0.0084(8) -0.0034(8) 0.0103(8) C23 0.0442(8) 0.0521(10) 0.0310(8) -0.0042(7) 0.0027(6) 0.0052(7) N1 0.0608(9) 0.0441(8) 0.0372(8) -0.0053(6) -0.0012(6) 0.0089(7) N2 0.0524(8) 0.0498(9) 0.0372(7) -0.0067(6) -0.0010(6) 0.0073(6) O1 0.0646(9) 0.0940(12) 0.0582(9) -0.0140(8) -0.0211(7) -0.0150(8) O2 0.0544(8) 0.0627(9) 0.0861(11) -0.0250(8) 0.0027(7) 0.0097(7) O3 0.0571(8) 0.0685(10) 0.0887(12) -0.0250(9) 0.0167(8) -0.0155(7) F1 0.1282(14) 0.0679(10) 0.1105(13) -0.0114(9) -0.0224(11) 0.0493(10) F2 0.1411(15) 0.0853(11) 0.0730(10) -0.0132(8) -0.0415(10) -0.0298(10) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.371(3) . ? C1 C6 1.398(3) . ? C1 H1 0.9300 . ? C2 C3 1.358(4) . ? C2 H2 0.9300 . ? C3 C4 1.353(4) . ? C3 F1 1.362(2) . ? C4 C5 1.389(3) . ? C4 H4 0.9300 . ? C5 C6 1.390(3) . ? C5 H5 0.9300 . ? C6 N1 1.407(2) . ? C7 N2 1.437(2) . ? C7 N1 1.463(2) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 N2 1.457(2) . ? C8 C9 1.560(2) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C11 1.529(2) . ? C9 C15 1.537(2) . ? C9 C10 1.538(2) . ? C10 N1 1.463(2) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 O1 1.206(2) . ? C11 C12 1.487(3) . ? C12 C13 1.498(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.511(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 O2 1.418(2) . ? C14 O3 1.420(2) . ? C14 C15 1.506(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 O2 1.399(3) . ? C16 C17 1.455(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 O3 1.370(3) . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? C18 C19 1.377(3) . ? C18 C23 1.400(3) . ? C18 H18 0.9300 . ? C19 C20 1.363(4) . ? C19 H19 0.9300 . ? C20 F2 1.361(3) . ? C20 C21 1.366(3) . ? C21 C22 1.374(3) . ? C21 H21 0.9300 . ? C22 C23 1.390(3) . ? C22 H22 0.9300 . ? C23 N2 1.406(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 C6 120.98(19) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 119.2(2) . . ? C3 C2 H2 120.4 . . ? C1 C2 H2 120.4 . . ? C4 C3 C2 122.3(2) . . ? C4 C3 F1 119.0(2) . . ? C2 C3 F1 118.8(2) . . ? C3 C4 C5 119.0(2) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? C4 C5 C6 120.6(2) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C5 C6 C1 117.77(18) . . ? C5 C6 N1 122.35(18) . . ? C1 C6 N1 119.82(16) . . ? N2 C7 N1 111.23(15) . . ? N2 C7 H7A 109.4 . . ? N1 C7 H7A 109.4 . . ? N2 C7 H7B 109.4 . . ? N1 C7 H7B 109.4 . . ? H7A C7 H7B 108.0 . . ? N2 C8 C9 111.66(13) . . ? N2 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N2 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 107.9 . . ? C11 C9 C15 112.56(15) . . ? C11 C9 C10 108.01(15) . . ? C15 C9 C10 108.96(14) . . ? C11 C9 C8 106.67(13) . . ? C15 C9 C8 112.56(14) . . ? C10 C9 C8 107.87(14) . . ? N1 C10 C9 110.72(14) . . ? N1 C10 H10A 109.5 . . ? C9 C10 H10A 109.5 . . ? N1 C10 H10B 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 108.1 . . ? O1 C11 C12 120.05(18) . . ? O1 C11 C9 121.05(18) . . ? C12 C11 C9 118.61(17) . . ? C11 C12 C13 115.63(18) . . ? C11 C12 H12A 108.4 . . ? C13 C12 H12A 108.4 . . ? C11 C12 H12B 108.4 . . ? C13 C12 H12B 108.4 . . ? H12A C12 H12B 107.4 . . ? C12 C13 C14 111.50(19) . . ? C12 C13 H13A 109.3 . . ? C14 C13 H13A 109.3 . . ? C12 C13 H13B 109.3 . . ? C14 C13 H13B 109.3 . . ? H13A C13 H13B 108.0 . . ? O2 C14 O3 106.09(16) . . ? O2 C14 C15 112.30(16) . . ? O3 C14 C15 108.70(16) . . ? O2 C14 C13 110.94(18) . . ? O3 C14 C13 108.97(18) . . ? C15 C14 C13 109.70(17) . . ? C14 C15 C9 116.29(14) . . ? C14 C15 H15A 108.2 . . ? C9 C15 H15A 108.2 . . ? C14 C15 H15B 108.2 . . ? C9 C15 H15B 108.2 . . ? H15A C15 H15B 107.4 . . ? O2 C16 C17 106.6(2) . . ? O2 C16 H16A 110.4 . . ? C17 C16 H16A 110.4 . . ? O2 C16 H16B 110.4 . . ? C17 C16 H16B 110.4 . . ? H16A C16 H16B 108.6 . . ? O3 C17 C16 106.1(2) . . ? O3 C17 H17A 110.5 . . ? C16 C17 H17A 110.5 . . ? O3 C17 H17B 110.5 . . ? C16 C17 H17B 110.5 . . ? H17A C17 H17B 108.7 . . ? C19 C18 C23 120.8(2) . . ? C19 C18 H18 119.6 . . ? C23 C18 H18 119.6 . . ? C20 C19 C18 119.0(2) . . ? C20 C19 H19 120.5 . . ? C18 C19 H19 120.5 . . ? F2 C20 C19 119.0(2) . . ? F2 C20 C21 118.8(2) . . ? C19 C20 C21 122.1(2) . . ? C20 C21 C22 118.9(2) . . ? C20 C21 H21 120.6 . . ? C22 C21 H21 120.6 . . ? C21 C22 C23 121.31(19) . . ? C21 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? C22 C23 C18 117.84(18) . . ? C22 C23 N2 119.42(16) . . ? C18 C23 N2 122.66(17) . . ? C6 N1 C10 116.18(14) . . ? C6 N1 C7 117.58(15) . . ? C10 N1 C7 109.63(15) . . ? C23 N2 C7 118.66(15) . . ? C23 N2 C8 120.29(15) . . ? C7 N2 C8 112.33(15) . . ? C16 O2 C14 107.90(18) . . ? C17 O3 C14 110.26(19) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.8(3) . . . . ? C1 C2 C3 C4 0.1(4) . . . . ? C1 C2 C3 F1 -179.5(2) . . . . ? C2 C3 C4 C5 0.9(4) . . . . ? F1 C3 C4 C5 -179.5(2) . . . . ? C3 C4 C5 C6 -2.9(4) . . . . ? C4 C5 C6 C1 3.7(3) . . . . ? C4 C5 C6 N1 -173.3(2) . . . . ? C2 C1 C6 C5 -2.7(3) . . . . ? C2 C1 C6 N1 174.36(18) . . . . ? N2 C8 C9 C11 166.90(16) . . . . ? N2 C8 C9 C15 -69.18(19) . . . . ? N2 C8 C9 C10 51.07(19) . . . . ? C11 C9 C10 N1 -169.66(14) . . . . ? C15 C9 C10 N1 67.77(18) . . . . ? C8 C9 C10 N1 -54.71(18) . . . . ? C15 C9 C11 O1 157.54(18) . . . . ? C10 C9 C11 O1 37.2(2) . . . . ? C8 C9 C11 O1 -78.5(2) . . . . ? C15 C9 C11 C12 -28.6(2) . . . . ? C10 C9 C11 C12 -148.93(18) . . . . ? C8 C9 C11 C12 95.3(2) . . . . ? O1 C11 C12 C13 -150.4(2) . . . . ? C9 C11 C12 C13 35.6(3) . . . . ? C11 C12 C13 C14 -50.2(3) . . . . ? C12 C13 C14 O2 -66.2(3) . . . . ? C12 C13 C14 O3 177.38(19) . . . . ? C12 C13 C14 C15 58.5(2) . . . . ? O2 C14 C15 C9 69.6(2) . . . . ? O3 C14 C15 C9 -173.35(15) . . . . ? C13 C14 C15 C9 -54.3(2) . . . . ? C11 C9 C15 C14 38.7(2) . . . . ? C10 C9 C15 C14 158.46(15) . . . . ? C8 C9 C15 C14 -81.92(19) . . . . ? O2 C16 C17 O3 -16.7(4) . . . . ? C23 C18 C19 C20 -0.9(3) . . . . ? C18 C19 C20 F2 179.3(2) . . . . ? C18 C19 C20 C21 0.0(3) . . . . ? F2 C20 C21 C22 -178.62(18) . . . . ? C19 C20 C21 C22 0.7(3) . . . . ? C20 C21 C22 C23 -0.5(3) . . . . ? C21 C22 C23 C18 -0.4(3) . . . . ? C21 C22 C23 N2 176.45(17) . . . . ? C19 C18 C23 C22 1.0(3) . . . . ? C19 C18 C23 N2 -175.65(17) . . . . ? C5 C6 N1 C10 -130.2(2) . . . . ? C1 C6 N1 C10 52.9(2) . . . . ? C5 C6 N1 C7 2.6(3) . . . . ? C1 C6 N1 C7 -174.29(18) . . . . ? C9 C10 N1 C6 -162.95(15) . . . . ? C9 C10 N1 C7 60.7(2) . . . . ? N2 C7 N1 C6 162.26(15) . . . . ? N2 C7 N1 C10 -62.1(2) . . . . ? C22 C23 N2 C7 -163.10(16) . . . . ? C18 C23 N2 C7 13.5(3) . . . . ? C22 C23 N2 C8 51.8(2) . . . . ? C18 C23 N2 C8 -131.59(18) . . . . ? N1 C7 N2 C23 -88.44(19) . . . . ? N1 C7 N2 C8 59.3(2) . . . . ? C9 C8 N2 C23 92.84(19) . . . . ? C9 C8 N2 C7 -54.3(2) . . . . ? C17 C16 O2 C14 17.5(3) . . . . ? O3 C14 O2 C16 -11.6(2) . . . . ? C15 C14 O2 C16 107.0(2) . . . . ? C13 C14 O2 C16 -129.8(2) . . . . ? C16 C17 O3 C14 9.7(4) . . . . ? O2 C14 O3 C17 0.9(3) . . . . ? C15 C14 O3 C17 -120.1(3) . . . . ? C13 C14 O3 C17 120.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 28.26 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.460 _refine_diff_density_min -0.449 _refine_diff_density_rms 0.070