# Copyright The Royal Society of Chemistry, 1999 # CCDC Number: 207/337 data_compound_1_and_2 #======================================================================= # 1. SUBMISSION DETAILS _publ_contact_author #Name and address of author for correspondence ; 'Ching-Fa Yao' Department of Chemistry National Taiwan Normal University 88, Sec. 4, Tingchow Road, Taipei 116, Taiwan Republic of China. ; _publ_contact_author_phone '886(2)29350749' _publ_contact_author_fax '886(2)29324249' _publ_contact_author_email Cheyaocf@scc.ntnu.edu.tw _publ_requested_journal ? _publ_requested_coeditor_name ? _publ_contact_letter ; Dear Managing Editor I would like to submit the paper " newcif977-971 " to PERKIN. ; #======================================================================= # 2. PROCESSING SUMMARY (IUCr Office Use Only) _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #======================================================================= # 3. TITLE AND AUTHOR LIST _publ_section_title ; Face selectivity in the reactions of Grignard reagents with 5- substituted -2-Dicyanomethyleneadamantanes ; # The loop structure below should contain the names and addresses of all # authors, in the required order of publication. Repeat as necessary. loop_ _publ_author_name _publ_author_address 'Ching-Fa Yao' ; Department of Chemistry National Taiwan Normal University 88, Sec. 4, Tingchow Road, Taipei 116, Taiwan Republic of China. ; #======================================================================= # 4. TEXT _publ_section_abstract ; Reactions of 5-substituted-2-dicyanomethyleneadamantane with benzylmagnesium bromide C~6~H~5~CH~2~MgBr or alkylmagnesium halides RMgX generated the 1,4-addition and/or the hydrogenation products. The substituent X varied from hydro, fluoro, chloro, bromo to phenyl group. The generation of the different isomeric products from the zu- face or en-face by the transfer of the benzyl, alkyl groups or the hydride from the Grignard reagents is discussed in terms of the electrostatic field influence and the steric hindrance between the Grignard reagents and the substrate 5-substituted-2-dicyanomethyleneadamantane. Reactions of 5-bromo-2-dicyanomethyleneadamantane or 5-phenyl-2- dicyanomethyleneadamantane with phenylmagnesium bromide generated 1,2-addition products 5-bromo-2-diiminomethyleneadamantane, 5-bromo-2-dibenzoylmethyleneadamantane or 2-dibenzoylmethylene-5-phenyladamantane when the intermediate A was added to dry methanol or was added to the dilute ice-cold hydrochloric acid solution. ; _publ_section_comment ; In summary, we have found that 5-substituted-2- dicyanomethyleneadamantanes reacted with various Grignard reagents to undergo Michael type and/or \b-hydride transfer reactions to generate 1,4-addition and/or hydrogenation products. The generation of the (E)-5-substituted-2-alkyl-2-dicyanomethylamantanes, (E)-5-substituted-2-benzyl-2-dicyanomethylamantanes and (E)-5-substituted-2-dicyanomethylamantanes as the major products by the transfer of the alkyl and benzyl groups or the hydride to the zu-face is governed by an electrostatic field influence. The formation of the (Z)-5-bromo-2-dicyanomethyl-2-ethyladamantane and (Z)-5-bromo-2-dicyanomethyl-2-isopropyladamantane as the major products by the addition of the ethyl or isopropyl group to the en-face and the generation of 1,2-addition products 5-bromo-2-diiminomethyleneadamantane, 5-bromo-2-dibenzoylmethyleneadamantane and 2-dibenzoylmethylene-5-phenyladamantane only can be mainly attributed to the steric hindrance between the Grignard reagents RMgX and substrates 5-substituted-2-dicyanomethyleneadamantanes. ; _publ_section_experimental ; ? #Insert appropriate text here if wanted. ; _publ_section_references ; Gabe, E.J., Le Page, Y., Charland,.J.-P., Lee, F.L. and White, P.S. (1989) J. Appl. Cryst., 22, 384-387. Flack, H., (1983) Acta Cryst., A39, 876-881. International Tables for X-ray Crystallography, Vol. IV, (1974) Kynoch Press, Birmingham, England. Johnson, C.K., (1976) ORTEP - A Fortran Thermal Ellipsoid Plot Program, Tehnical Report ORNL-5138, Oak Ridge National Lab., U.S.A. Larson, A.C., (1970) p.293, Crystallographic Computing, Munksgaard, Copenhagen. Le Page, Y., (1988) J. Appl. Cryst., 21, 983-984. Le Page, Y. and Gabe, E.J., (1979) J. Appl. Cryst., 12, 464-466. Rogers, D., (1981) Acta Cryst., A37, 734-741. ? #Insert any other references here ; _publ_section_figure_captions ; ? #Insert figure captions here if wanted ; _publ_section_acknowledgements ; ? #Insert any acknowledgements here. ; #======================================================================= # If more than one structure is reported, sections 5-10 should be filled in # per structure. For each data set, replace the ? in the data_? line below # by a unique identifier. data_compound_1 #======================================================================= # 5. CHEMICAL DATA _chemical_name_systematic ; ? #Insert the chemical name here. ; _chemical_name_common ? _chemical_formula_moiety 'C14 H17 F N2 ' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C14 H17 F N2 ' _chemical_formula_weight 232.30 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 'International Tables Vol. IV Table 2.2B' H ? 0.000 0.000 'International Tables Vol. IV Table 2.2B' F ? 0.014 0.010 'International Tables Vol. IV Table 2.2B' N ? 0.004 0.003 'International Tables Vol. IV Table 2.2B' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/c' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,1/2+y,1/2-z x,1/2-y,1/2+z _cell_length_a 8.767(4) _cell_length_b 24.309(6) _cell_length_c 12.476(4) _cell_angle_alpha 90.0 _cell_angle_beta 110.44(3) _cell_angle_gamma 90.0 _cell_volume 2491.4(16) _cell_formula_units_Z 8 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 6.84 _cell_measurement_theta_max 11.78 _cell_special_details ; ? #Insert any comments here. ; _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.05 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method ? _exptl_crystal_F_000 992.40 _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 1.000 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? #Insert any special details here. ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_source 'xray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD-4 ' _diffrn_measurement_method 'Theta/2theta scan b/P/b ' _diffrn_standards_number 3 _diffrn_standards_interval_count 300 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 -6 -2 0 -14 0 -2 6 5 _diffrn_reflns_number 5956 _diffrn_reflns_av_R_equivalents 0.015 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 27.41 _diffrn_reflns_reduction_process ? _reflns_number_total 5704 _reflns_number_observed 1179 _reflns_observed_criterion 'Inet > 2.5\s(Inet)' _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'NRCVAX DATRD2' _computing_structure_solution 'NRCVAX SOLVER' _computing_structure_refinement 'NRCVAX LSTSQ' _computing_molecular_graphics 'NRCVAX' _computing_publication_material 'NRCVAX TABLES' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; ? #Insert any special details here. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type atomblock _refine_ls_weighting_scheme unit _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method Larson _refine_ls_extinction_coef 0.034 _refine_ls_number_reflns 1233 _refine_ls_number_parameters 208 _refine_ls_number_restraints ? _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.295 _refine_ls_R_factor_obs 0.067 _refine_ls_wR_factor_all 0.237 _refine_ls_wR_factor_obs 0.066 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 0.56 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/esd_max 0.002 _refine_ls_shift/esd_mean ? _refine_diff_density_max 0.25 _refine_diff_density_min -0.22 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol F 0.2832(7) 0.81707(22) 0.2264(6) 0.078(5) Uani ? . F N1 0.9445(12) 0.6908(6) 0.4299(9) 0.111(10) Uani ? . N N2 0.7687(11) 0.6652(5) 0.0695(8) 0.086(8) Uani ? . N C1 0.8356(15) 0.6941(6) 0.3480(11) 0.068(9) Uani ? . C C2 0.7353(11) 0.6794(5) 0.1462(10) 0.055(8) Uani ? . C C3 0.6929(11) 0.6988(4) 0.2430(9) 0.039(7) Uani ? . C C4 0.5858(11) 0.6052(4) 0.2659(9) 0.054(7) Uani ? . C C5 0.5420(11) 0.6672(4) 0.2525(8) 0.0378(24) Uiso ? . C C6 0.5028(11) 0.6888(4) 0.3576(7) 0.0390(23) Uiso ? . C C7 0.4637(11) 0.7511(4) 0.3453(8) 0.045(3) Uiso ? . C C8 0.3157(11) 0.7600(4) 0.2382(8) 0.046(3) Uiso ? . C C9 0.3515(12) 0.7412(4) 0.1340(8) 0.049(3) Uiso ? . C C10 0.3901(11) 0.6795(4) 0.1435(8) 0.0393(25) Uiso ? . C C11 0.2385(12) 0.6483(4) 0.1536(8) 0.048(3) Uiso ? . C C12 0.2068(13) 0.6691(4) 0.2601(9) 0.055(3) Uiso ? . C C13 0.1669(12) 0.7306(4) 0.2463(9) 0.054(3) Uiso ? . C C14 0.3524(12) 0.6586(4) 0.3671(8) 0.050(3) Uiso ? . C F' 0.2618(9) 0.31616(24) 0.3233(6) 0.095(6) Uani ? . F N1' -0.2554(11) 0.4765(5) 0.4022(8) 0.092(8) Uani ? . N N2' -0.4153(13) 0.4297(5) 0.0498(10) 0.104(9) Uani ? . N C1' -0.2196(12) 0.4577(5) 0.3329(10) 0.054(8) Uani ? . C C2' -0.3100(14) 0.4313(5) 0.1348(11) 0.064(9) Uani ? . C C3' -0.1694(11) 0.4316(4) 0.2427(9) 0.044(7) Uani ? . C C4' -0.0720(12) 0.5214(4) 0.1935(9) 0.054(7) Uani ? . C C5' -0.0189(10) 0.4621(3) 0.2296(8) 0.0329(22) Uiso ? . C C6' 0.1258(11) 0.4589(4) 0.3451(8) 0.0413(25) Uiso ? . C C7' 0.1739(12) 0.3993(4) 0.3802(9) 0.055(3) Uiso ? . C C8' 0.2192(12) 0.3713(4) 0.2877(9) 0.052(3) Uiso ? . C C9' 0.0816(12) 0.3704(4) 0.1751(8) 0.048(3) Uiso ? . C C10' 0.0311(11) 0.4308(4) 0.1367(8) 0.045(3) Uiso ? . C C11' 0.1834(12) 0.4588(4) 0.1261(9) 0.058(3) Uiso ? . C C12' 0.3216(13) 0.4587(4) 0.2381(9) 0.057(3) Uiso ? . C C13' 0.3704(13) 0.3987(4) 0.2759(9) 0.061(3) Uiso ? . C C14' 0.2755(12) 0.4881(4) 0.3304(9) 0.053(3) Uiso ? . C H3 0.658 0.743 0.233 0.0511 Uiso ? . H H4 0.614 0.592 0.193 0.0549 Uiso ? . H H4' 0.482 0.582 0.270 0.0549 Uiso ? . H H4" 0.689 0.602 0.345 0.0549 Uiso ? . H H6 0.610 0.682 0.437 0.0442 Uiso ? . H H7 0.568 0.774 0.337 0.0463 Uiso ? . H H7' 0.442 0.767 0.420 0.0463 Uiso ? . H H9 0.248 0.749 0.057 0.0566 Uiso ? . H H9' 0.456 0.764 0.128 0.0566 Uiso ? . H H10 0.416 0.665 0.068 0.0446 Uiso ? . H H11 0.258 0.604 0.155 0.0545 Uiso ? . H H11' 0.132 0.658 0.075 0.0545 Uiso ? . H H12 0.099 0.647 0.266 0.0608 Uiso ? . H H13 0.139 0.747 0.320 0.0499 Uiso ? . H H13' 0.061 0.740 0.170 0.0499 Uiso ? . H H14 0.327 0.672 0.442 0.0541 Uiso ? . H H14' 0.378 0.614 0.377 0.0541 Uiso ? . H H3' -0.130 0.389 0.269 0.0591 Uiso ? . H HA4 0.026 0.543 0.182 0.0624 Uiso ? . H HA4' -0.106 0.540 0.260 0.0624 Uiso ? . H HA4" -0.177 0.518 0.114 0.0624 Uiso ? . H H6' 0.094 0.480 0.411 0.0445 Uiso ? . H HA7 0.079 0.378 0.397 0.0559 Uiso ? . H HA7' 0.284 0.399 0.460 0.0559 Uiso ? . H HA9 0.115 0.349 0.110 0.0518 Uiso ? . H HA9' -0.023 0.349 0.184 0.0518 Uiso ? . H H10' -0.071 0.432 0.053 0.0511 Uiso ? . H HA11 0.155 0.502 0.097 0.0598 Uiso ? . H HA11' 0.219 0.438 0.061 0.0598 Uiso ? . H H12' 0.428 0.479 0.227 0.0660 Uiso ? . H HA13 0.469 0.398 0.363 0.0711 Uiso ? . H HA13' 0.417 0.376 0.221 0.0711 Uiso ? . H HA14 0.380 0.487 0.411 0.0669 Uiso ? . H HA14' 0.248 0.531 0.307 0.0669 Uiso ? . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol F 0.077(5) 0.035(3) 0.131(6) 0.031(7) 0.096(8) 0.006(8) F N1 0.044(7) 0.207(14) 0.076(8) -0.050(17) 0.027(12) 0.038(19) N N2 0.066(7) 0.130(10) 0.083(8) -0.026(13) 0.102(13) -0.031(15) N C1 0.050(8) 0.100(10) 0.066(9) -0.022(15) 0.074(15) -0.019(16) C C2 0.025(6) 0.074(8) 0.072(9) -0.002(11) 0.049(12) -0.006(14) C C3 0.029(6) 0.035(6) 0.060(7) -0.004(9) 0.046(11) -0.001(10) C C4 0.047(7) 0.046(6) 0.076(8) 0.002(10) 0.058(12) -0.014(12) C #======================================================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F C8 1.413(11) ? ? ? N1 C1 1.131(17) ? ? ? N2 C2 1.148(14) ? ? ? C1 C3 1.466(17) ? ? ? C2 C3 1.459(14) ? ? ? C3 C5 1.569(12) ? ? ? C3 H3 1.110(9) ? ? ? C4 C5 1.551(13) ? ? ? C4 H4 1.072(10) ? ? ? C4 H4' 1.083(9) ? ? ? C4 H4" 1.081(10) ? ? ? C5 C6 1.558(12) ? ? ? C5 C10 1.564(13) ? ? ? C6 C7 1.549(13) ? ? ? C6 C14 1.549(13) ? ? ? C6 H6 1.115(9) ? ? ? C7 C8 1.519(13) ? ? ? C7 H7 1.098(9) ? ? ? C7 H7' 1.085(9) ? ? ? C8 C9 1.511(14) ? ? ? C8 C13 1.521(14) ? ? ? C9 C10 1.532(13) ? ? ? C9 H9 1.084(10) ? ? ? C9 H9' 1.095(10) ? ? ? C10 C11 1.573(13) ? ? ? C10 H10 1.095(9) ? ? ? C11 C12 1.535(14) ? ? ? C11 H11 1.078(9) ? ? ? C11 H11' 1.119(10) ? ? ? C12 C13 1.532(14) ? ? ? C12 C14 1.512(15) ? ? ? C12 H12 1.113(10) ? ? ? C13 H13 1.113(10) ? ? ? C13 H13' 1.098(10) ? ? ? C14 H14 1.088(10) ? ? ? C14 H14' 1.098(10) ? ? ? F' C8' 1.420(12) ? ? ? N1' C1' 1.116(15) ? ? ? N2' C2' 1.138(17) ? ? ? C1' C3' 1.487(15) ? ? ? C2' C3' 1.474(17) ? ? ? C3' C5' 1.571(12) ? ? ? C3' H3' 1.100(10) ? ? ? C4' C5' 1.533(12) ? ? ? C4' Ha4 1.069(10) ? ? ? C4' Ha4' 1.080(10) ? ? ? C4' Ha4" 1.099(10) ? ? ? C5' C6' 1.554(13) ? ? ? C5' C10' 1.570(13) ? ? ? C6' C7' 1.529(14) ? ? ? C6' C14' 1.558(13) ? ? ? C6' H6' 1.085(9) ? ? ? C7' C8' 1.508(14) ? ? ? C7' Ha7 1.060(10) ? ? ? C7' Ha7' 1.117(10) ? ? ? C8' C9' 1.499(15) ? ? ? C8' C13' 1.535(14) ? ? ? C9' C10' 1.560(13) ? ? ? C9' Ha9 1.084(9) ? ? ? C9' Ha9' 1.094(9) ? ? ? C10' C11' 1.544(14) ? ? ? C10' H10' 1.116(9) ? ? ? C11' C12' 1.496(15) ? ? ? C11' Ha11 1.103(11) ? ? ? C11' Ha11' 1.096(11) ? ? ? C12' C13' 1.548(15) ? ? ? C12' C14' 1.525(14) ? ? ? C12' H12' 1.105(10) ? ? ? C13' Ha13 1.132(11) ? ? ? C13' Ha13' 1.070(10) ? ? ? C14' Ha14 1.101(10) ? ? ? C14' Ha14' 1.085(10) ? ? ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C3 179.0(12) ? ? ? ? N2 C2 C3 178.7(12) ? ? ? ? C1 C3 C2 109.3(8) ? ? ? ? C1 C3 C5 112.0(8) ? ? ? ? C1 C3 H3 107.0(9) ? ? ? ? C2 C3 C5 111.7(8) ? ? ? ? C2 C3 H3 110.6(8) ? ? ? ? C5 C3 H3 106.2(7) ? ? ? ? C5 C4 H4 108.3(8) ? ? ? ? C5 C4 H4' 109.0(7) ? ? ? ? C5 C4 H4" 104.9(8) ? ? ? ? H4 C4 H4' 109.8(9) ? ? ? ? H4 C4 H4" 112.7(8) ? ? ? ? H4' C4 H4" 111.8(9) ? ? ? ? C3 C5 C4 107.4(7) ? ? ? ? C3 C5 C6 109.8(7) ? ? ? ? C3 C5 C10 109.0(7) ? ? ? ? C4 C5 C6 110.8(7) ? ? ? ? C4 C5 C10 112.5(7) ? ? ? ? C6 C5 C10 107.2(7) ? ? ? ? C5 C6 C7 110.6(7) ? ? ? ? C5 C6 C14 110.5(7) ? ? ? ? C5 C6 H6 109.9(7) ? ? ? ? C7 C6 C14 107.8(7) ? ? ? ? C7 C6 H6 108.5(7) ? ? ? ? C14 C6 H6 109.6(7) ? ? ? ? C6 C7 C8 108.6(7) ? ? ? ? C6 C7 H7 109.5(7) ? ? ? ? C6 C7 H7' 111.0(8) ? ? ? ? C8 C7 H7 109.3(8) ? ? ? ? C8 C7 H7' 110.6(8) ? ? ? ? H7 C7 H7' 107.8(8) ? ? ? ? F C8 C7 108.1(8) ? ? ? ? F C8 C9 107.6(8) ? ? ? ? F C8 C13 108.8(7) ? ? ? ? C7 C8 C9 110.1(8) ? ? ? ? C7 C8 C13 111.3(8) ? ? ? ? C9 C8 C13 110.8(8) ? ? ? ? C8 C9 C10 109.6(8) ? ? ? ? C8 C9 H9 110.0(8) ? ? ? ? C8 C9 H9' 109.4(8) ? ? ? ? C10 C9 H9 110.1(8) ? ? ? ? C10 C9 H9' 109.6(8) ? ? ? ? H9 C9 H9' 108.1(8) ? ? ? ? C5 C10 C9 110.6(7) ? ? ? ? C5 C10 C11 109.0(7) ? ? ? ? C5 C10 H10 108.4(7) ? ? ? ? C9 C10 C11 108.0(7) ? ? ? ? C9 C10 H10 110.5(8) ? ? ? ? C11 C10 H10 110.4(7) ? ? ? ? C10 C11 C12 108.9(8) ? ? ? ? C10 C11 H11 110.1(8) ? ? ? ? C10 C11 H11' 107.5(7) ? ? ? ? C12 C11 H11 112.9(8) ? ? ? ? C12 C11 H11' 110.5(8) ? ? ? ? H11 C11 H11' 106.8(8) ? ? ? ? C11 C12 C13 109.1(8) ? ? ? ? C11 C12 C14 110.9(8) ? ? ? ? C11 C12 H12 107.8(8) ? ? ? ? C13 C12 C14 110.7(8) ? ? ? ? C13 C12 H12 108.9(8) ? ? ? ? C14 C12 H12 109.5(8) ? ? ? ? C8 C13 C12 107.4(8) ? ? ? ? C8 C13 H13 109.0(8) ? ? ? ? C8 C13 H13' 109.2(8) ? ? ? ? C12 C13 H13 111.9(8) ? ? ? ? C12 C13 H13' 113.5(8) ? ? ? ? H13 C13 H13' 105.8(8) ? ? ? ? C6 C14 C12 109.4(8) ? ? ? ? C6 C14 H14 111.0(8) ? ? ? ? C6 C14 H14' 108.8(8) ? ? ? ? C12 C14 H14 110.0(8) ? ? ? ? C12 C14 H14' 110.0(8) ? ? ? ? H14 C14 H14' 107.6(8) ? ? ? ? N1' C1' C3' 178.5(12) ? ? ? ? N2' C2' C3' 177.4(12) ? ? ? ? C1' C3' C2' 108.6(8) ? ? ? ? C1' C3' C5' 111.0(8) ? ? ? ? C1' C3' H3' 108.4(9) ? ? ? ? C2' C3' C5' 111.9(8) ? ? ? ? C2' C3' H3' 110.1(9) ? ? ? ? C5' C3' H3' 106.8(7) ? ? ? ? C5' C4' Ha4 109.5(8) ? ? ? ? C5' C4' Ha4' 108.4(8) ? ? ? ? C5' C4' Ha4" 105.2(8) ? ? ? ? Ha4 C4' Ha4' 110.3(9) ? ? ? ? Ha4 C4' Ha4" 112.1(9) ? ? ? ? Ha4' C4' Ha4" 111.2(8) ? ? ? ? C3' C5' C4' 107.1(7) ? ? ? ? C3' C5' C6' 108.9(7) ? ? ? ? C3' C5' C10' 108.0(7) ? ? ? ? C4' C5' C6' 112.7(7) ? ? ? ? C4' C5' C10' 111.9(7) ? ? ? ? C6' C5' C10' 108.2(7) ? ? ? ? C5' C6' C7' 111.5(8) ? ? ? ? C5' C6' C14' 108.5(7) ? ? ? ? C5' C6' H6' 110.0(7) ? ? ? ? C7' C6' C14' 107.8(8) ? ? ? ? C7' C6' H6' 109.9(8) ? ? ? ? C14' C6' H6' 109.0(8) ? ? ? ? C6' C7' C8' 109.2(8) ? ? ? ? C6' C7' Ha7 111.3(8) ? ? ? ? C6' C7' Ha7' 108.7(8) ? ? ? ? C8' C7' Ha7 111.4(9) ? ? ? ? C8' C7' Ha7' 107.9(8) ? ? ? ? Ha7 C7' Ha7' 108.2(9) ? ? ? ? F' C8' C7' 107.3(8) ? ? ? ? F' C8' C9' 108.6(8) ? ? ? ? F' C8' C13' 107.3(8) ? ? ? ? C7' C8' C9' 112.5(8) ? ? ? ? C7' C8' C13' 110.2(8) ? ? ? ? C9' C8' C13' 110.8(8) ? ? ? ? C8' C9' C10' 108.9(8) ? ? ? ? C8' C9' Ha9 111.5(8) ? ? ? ? C8' C9' Ha9' 110.0(8) ? ? ? ? C10' C9' Ha9 109.6(8) ? ? ? ? C10' C9' Ha9' 108.6(8) ? ? ? ? Ha9 C9' Ha9' 108.1(8) ? ? ? ? C5' C10' C9' 110.5(7) ? ? ? ? C5' C10' C11' 108.9(7) ? ? ? ? C5' C10' H10' 109.3(7) ? ? ? ? C9' C10' C11' 106.2(8) ? ? ? ? C9' C10' H10' 111.8(8) ? ? ? ? C11' C10' H10' 110.0(8) ? ? ? ? C10' C11' C12' 111.2(9) ? ? ? ? C10' C11' Ha11 110.0(8) ? ? ? ? C10' C11' Ha11' 109.5(8) ? ? ? ? C12' C11' Ha11 109.0(9) ? ? ? ? C12' C11' Ha11' 110.4(9) ? ? ? ? Ha11 C11' Ha11' 106.6(9) ? ? ? ? C11' C12' C13' 109.5(8) ? ? ? ? C11' C12' C14' 111.3(9) ? ? ? ? C11' C12' H12' 109.1(9) ? ? ? ? C13' C12' C14' 109.2(8) ? ? ? ? C13' C12' H12' 107.8(8) ? ? ? ? C14' C12' H12' 109.9(8) ? ? ? ? C8' C13' C12' 106.4(8) ? ? ? ? C8' C13' Ha13 107.5(8) ? ? ? ? C8' C13' Ha13' 112.1(9) ? ? ? ? C12' C13' Ha13 109.8(9) ? ? ? ? C12' C13' Ha13' 114.5(9) ? ? ? ? Ha13 C13' Ha13' 106.3(9) ? ? ? ? C6' C14' C12' 109.4(8) ? ? ? ? C6' C14' Ha14 110.2(8) ? ? ? ? C6' C14' Ha14' 110.6(8) ? ? ? ? C12' C14' Ha14 109.2(8) ? ? ? ? C12' C14' Ha14' 109.9(8) ? ? ? ? Ha14 C14' Ha14' 107.5(9) ? ? ? ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N1 C1 C3 C2 -178.2( 14) N1 C1 C3 C5 -54.0( 9) N2 C2 C3 C1 -105.7( 11) N2 C2 C3 C5 129.8( 11) C1 C3 C5 C4 -64.2( 7) C1 C3 C5 C6 56.4( 7) C1 C3 C5 C10 173.6( 10) C2 C3 C5 C4 58.7( 7) C2 C3 C5 C6 179.3( 10) C2 C3 C5 C10 -63.5( 7) C3 C5 C6 C7 60.0( 6) C3 C5 C6 C14 179.2( 9) C4 C5 C6 C7 178.5( 9) C4 C5 C6 C14 -62.3( 6) C10 C5 C6 C7 -58.4( 6) C10 C5 C6 C14 60.8( 6) C3 C5 C10 C9 -61.0( 6) C3 C5 C10 C11 -179.5( 9) C4 C5 C10 C9 180.0( 10) C4 C5 C10 C11 61.4( 6) C6 C5 C10 C9 57.9( 6) C6 C5 C10 C11 -60.6( 6) C5 C6 C7 C8 60.8( 6) C14 C6 C7 C8 -60.0( 6) C5 C6 C14 C12 -60.4( 6) C7 C6 C14 C12 60.5( 6) C6 C7 C8 F -178.7( 10) C6 C7 C8 C9 -61.4( 6) C6 C7 C8 C13 61.9( 6) F C8 C9 C10 179.2( 10) C7 C8 C9 C10 61.5( 6) C13 C8 C9 C10 -62.0( 6) F C8 C13 C12 -179.5( 10) C7 C8 C13 C12 -60.5( 7) C9 C8 C13 C12 62.4( 7) C8 C9 C10 C5 -60.2( 6) C8 C9 C10 C11 59.0( 6) C5 C10 C11 C12 60.7( 6) C9 C10 C11 C12 -59.5( 6) C10 C11 C12 C13 62.0( 7) C10 C11 C12 C14 -60.2( 6) C11 C12 C13 C8 -62.3( 7) C14 C12 C13 C8 60.0( 7) C11 C12 C14 C6 59.7( 6) C13 C12 C14 C6 -61.5( 7) N1' C1' C3' C2' 139.4( 13) N1' C1' C3' C5' -97.1( 10) N2' C2' C3' C1' -171.4( 14) N2' C2' C3' C5' 65.7( 9) C1' C3' C5' C4' -61.5( 7) C1' C3' C5' C6' 60.5( 6) C1' C3' C5' C10' 177.8( 10) C2' C3' C5' C4' 60.0( 7) C2' C3' C5' C6' -178.0( 10) C2' C3' C5' C10' -60.7( 7) C3' C5' C6' C7' 60.2( 6) C3' C5' C6' C14' 178.8( 9) C4' C5' C6' C7' 178.8( 10) C4' C5' C6' C14' -62.6( 6) C10' C5' C6' C7' -57.0( 6) C10' C5' C6' C14' 61.6( 6) C3' C5' C10' C9' -61.4( 6) C3' C5' C10' C11' -177.7( 10) C4' C5' C10' C9' -179.0( 10) C4' C5' C10' C11' 64.7( 7) C6' C5' C10' C9' 56.3( 6) C6' C5' C10' C11' -60.0( 6) C5' C6' C7' C8' 58.4( 6) C14' C6' C7' C8' -60.5( 7) C5' C6' C14' C12' -60.8( 6) C7' C6' C14' C12' 60.1( 7) C6' C7' C8' F' -179.6( 11) C6' C7' C8' C9' -60.3( 7) C6' C7' C8' C13' 63.9( 7) F' C8' C9' C10' 178.6( 10) C7' C8' C9' C10' 60.0( 7) C13' C8' C9' C10' -63.7( 7) F' C8' C13' C12' -179.6( 11) C7' C8' C13' C12' -63.0( 7) C9' C8' C13' C12' 62.1( 7) C8' C9' C10' C5' -57.9( 6) C8' C9' C10' C11' 60.1( 7) C5' C10' C11' C12' 58.4( 6) C9' C10' C11' C12' -60.6( 7) C10' C11' C12' C13' 62.5( 7) C10' C11' C12' C14' -58.3( 7) C11' C12' C13' C8' -60.3( 7) C14' C12' C13' C8' 61.8( 7) C11' C12' C14' C6' 59.1( 7) C13' C12' C14' C6' -61.8( 7) #=END data_Compound_2 #======================================================================= # 5. CHEMICAL DATA _chemical_name_systematic ; ? #Insert the chemical name here. ; _chemical_name_common ? _chemical_formula_moiety 'C20 H21 N2 F ' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C20 H21 N2 F ' _chemical_formula_weight 308.39 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C ? 0.002 0.002 'International Tables Vol. IV Table 2.2B' H ? 0.000 0.000 'International Tables Vol. IV Table 2.2B' N ? 0.004 0.003 'International Tables Vol. IV Table 2.2B' F ? 0.014 0.010 'International Tables Vol. IV Table 2.2B' #======================================================================= # 6. CRYSTAL DATA _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z 1/2-x,1/2+y,1/2-z 1/2+x,1/2-y,1/2+z _cell_length_a 7.5393(9) _cell_length_b 9.1199(10) _cell_length_c 23.597(5) _cell_angle_alpha 90.0 _cell_angle_beta 95.474(13) _cell_angle_gamma 90.0 _cell_volume 1615.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 11.99 _cell_measurement_theta_max 14.35 _cell_special_details ; ? #Insert any comments here. ; _exptl_crystal_description ? _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.35 _exptl_crystal_size_rad ? _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.268 _exptl_crystal_density_method ? _exptl_crystal_F_000 656.25 _exptl_absorpt_coefficient_mu 0.08 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.878 _exptl_absorpt_correction_T_max 1.000 #======================================================================= # 7. EXPERIMENTAL DATA _exptl_special_details ; ? #Insert any special details here. ; _diffrn_ambient_temperature 293 _diffrn_radiation_wavelength 0.70930 _diffrn_radiation_type 'Molybdenum K\a' _diffrn_radiation_source 'xray tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius CAD-4 ' _diffrn_measurement_method 'Theta/2theta scan b/P/b ' _diffrn_standards_number 3 _diffrn_standards_interval_count 300 _diffrn_standards_interval_time 7200 _diffrn_standards_decay_% 0 loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 5 1 -2 1 6 0 4 0 -8 _diffrn_reflns_number 4802 _diffrn_reflns_av_R_equivalents 0.010 _diffrn_reflns_av_sigmaI/netI ? _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 1.5 _diffrn_reflns_theta_max 29.90 _diffrn_reflns_reduction_process ? _reflns_number_total 4702 _reflns_number_observed 3145 _reflns_observed_criterion 'Inet > 2.5\s(Inet)' _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction 'NRCVAX DATRD2' _computing_structure_solution 'NRCVAX SOLVER' _computing_structure_refinement 'NRCVAX LSTSQ' _computing_molecular_graphics 'NRCVAX' _computing_publication_material 'NRCVAX TABLES' #======================================================================= # 8. REFINEMENT DATA _refine_special_details ; ? #Insert any special details here. ; _refine_ls_structure_factor_coef F _refine_ls_matrix_type atomblock _refine_ls_weighting_scheme unit _refine_ls_hydrogen_treatment ? _refine_ls_extinction_method Larson _refine_ls_extinction_coef 0.211 _refine_ls_number_reflns 3145 _refine_ls_number_parameters 209 _refine_ls_number_restraints ? _refine_ls_number_constraints ? _refine_ls_R_factor_all 0.079 _refine_ls_R_factor_obs 0.052 _refine_ls_wR_factor_all 0.067 _refine_ls_wR_factor_obs 0.056 _refine_ls_goodness_of_fit_all ? _refine_ls_goodness_of_fit_obs 1.83 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean ? _refine_diff_density_max 3.10 _refine_diff_density_min -2.40 #======================================================================= # 9. ATOMIC COORDINATES AND THERMAL PARAMETERS loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_type_symbol F 0.18586(18) 0.05585(17) 0.14598(8) 0.0639(10) Uani ? . F N1 -0.1801(4) 0.6313(3) 0.02542(12) 0.0776(18) Uani ? . N N2 -0.2125(3) 0.6085(3) 0.20504(11) 0.0668(15) Uani ? . N C1 -0.1712(4) 0.5578(3) 0.06412(12) 0.0497(14) Uani ? . C C2 -0.1960(3) 0.5431(3) 0.16538(11) 0.0432(12) Uani ? . C C3 -0.1583(3) 0.45892(24) 0.11423(9) 0.0360(10) Uani ? . C C4 -0.2746(3) 0.31657(23) 0.10270(9) 0.0325(9) Uani ? . C C5 -0.2629(3) 0.22032(24) 0.15719(10) 0.0355(11) Uani ? . C C6 -0.3689(3) 0.0775(3) 0.14525(12) 0.0496(14) Uani ? . C C7 -0.2914(3) -0.0082(3) 0.09705(15) 0.0599(17) Uani ? . C C8 -0.2983(3) 0.0852(3) 0.04293(13) 0.0567(15) Uani ? . C C9 -0.1909(3) 0.2270(3) 0.05529(10) 0.0421(12) Uani ? . C C10 0.0037(3) 0.1826(3) 0.07454(11) 0.0444(12) Uani ? . C C11 0.0053(3) 0.0918(3) 0.12820(12) 0.0467(13) Uani ? . C C12 -0.0964(4) -0.0497(3) 0.11663(15) 0.0617(18) Uani ? . C C13 -0.0672(3) 0.1776(3) 0.17599(10) 0.0411(11) Uani ? . C C14 -0.4684(3) 0.3610(3) 0.08093(10) 0.0412(11) Uani ? . C C1A -0.5641(3) 0.4649(3) 0.11745(10) 0.0400(11) Uani ? . C C2A -0.5892(3) 0.6105(3) 0.10116(12) 0.0541(15) Uani ? . C C3A -0.6784(4) 0.7074(3) 0.13350(16) 0.0673(19) Uani ? . C C4A -0.7446(4) 0.6605(3) 0.18260(15) 0.0655(17) Uani ? . C C5A -0.7233(3) 0.5154(3) 0.19939(12) 0.0562(15) Uani ? . C C6A -0.6345(3) 0.4182(3) 0.16679(11) 0.0457(13) Uani ? . C H3 -0.021 0.421 0.121 0.0434 Uiso ? . H H5 -0.318 0.281 0.192 0.0426 Uiso ? . H H6 -0.359 0.010 0.184 0.0548 Uiso ? . H H6' -0.508 0.104 0.134 0.0548 Uiso ? . H H7 -0.370 -0.108 0.087 0.0639 Uiso ? . H H8 -0.243 0.024 0.008 0.0611 Uiso ? . H H8' -0.436 0.112 0.028 0.0611 Uiso ? . H H9 -0.195 0.294 0.016 0.0484 Uiso ? . H H10 0.085 0.280 0.082 0.0508 Uiso ? . H H10' 0.058 0.119 0.041 0.0508 Uiso ? . H H12 -0.036 -0.113 0.084 0.0641 Uiso ? . H H12' -0.090 -0.115 0.155 0.0641 Uiso ? . H H13 -0.059 0.112 0.214 0.0474 Uiso ? . H H13' 0.012 0.277 0.185 0.0474 Uiso ? . H H14 -0.547 0.261 0.075 0.0478 Uiso ? . H H14' -0.464 0.413 0.039 0.0478 Uiso ? . H H2A -0.542 0.645 0.065 0.0595 Uiso ? . H H3A -0.694 0.812 0.122 0.0694 Uiso ? . H H4A -0.805 0.730 0.206 0.0664 Uiso ? . H H5A -0.771 0.481 0.236 0.0613 Uiso ? . H H6A -0.622 0.314 0.179 0.0510 Uiso ? . H loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 _atom_site_aniso_type_symbol F 0.0339(7) 0.0510(9) 0.1070(14) 0.0261(13) 0.0148(16) 0.0158(18) F N1 0.1038(22) 0.0664(17) 0.0631(17) -0.015(3) 0.022(3) 0.045(3) N N2 0.0717(16) 0.0692(17) 0.0606(15) -0.015(3) 0.0248(25) -0.051(3) N C1 0.0599(15) 0.0405(13) 0.0499(15) -0.0040(23) 0.0209(24) -0.0006(23) C C2 0.0446(12) 0.0377(12) 0.0472(14) -0.0052(20) 0.0086(20) -0.0076(22) C C3 0.0394(11) 0.0311(11) 0.0378(11) 0.0039(17) 0.0104(18) -0.0020(18) C C4 0.0304(9) 0.0301(10) 0.0370(11) 0.0040(16) 0.0048(16) -0.0086(17) C C5 0.0296(10) 0.0345(11) 0.0429(12) 0.0032(16) 0.0132(17) 0.0071(18) C C6 0.0336(11) 0.0382(13) 0.0783(19) -0.0080(20) 0.0230(23) 0.0091(25) C C7 0.0419(13) 0.0318(12) 0.1066(25) -0.0122(21) 0.021(3) -0.031(3) C C8 0.0497(14) 0.0495(15) 0.0707(19) 0.0002(24) 0.008(3) -0.058(3) C C9 0.0421(12) 0.0416(13) 0.0435(13) 0.0053(20) 0.0158(20) -0.0211(21) C C10 0.0386(11) 0.0397(12) 0.0574(15) 0.0078(19) 0.0339(21) -0.0185(22) C C11 0.0281(10) 0.0355(12) 0.0769(18) 0.0119(18) 0.0157(21) 0.0032(24) C C12 0.0464(14) 0.0307(12) 0.109(3) 0.0081(22) 0.029(3) -0.004(3) C C13 0.0317(10) 0.0405(12) 0.0509(14) 0.0085(18) 0.0062(19) 0.0226(21) C C14 0.0341(10) 0.0439(13) 0.0440(13) 0.0176(19) -0.0083(18) -0.0127(21) C C1A 0.0297(10) 0.0391(12) 0.0497(14) 0.0130(18) -0.0072(18) -0.0110(21) C C2A 0.0485(14) 0.0460(15) 0.0673(18) 0.0280(23) 0.0066(25) 0.010(3) C C3A 0.0560(16) 0.0413(15) 0.104(3) 0.033(3) 0.011(3) -0.009(3) C C4A 0.0461(14) 0.0592(18) 0.0908(24) 0.023(3) 0.011(3) -0.063(3) C C5A 0.0407(13) 0.0665(18) 0.0621(17) 0.005(3) 0.0164(23) -0.029(3) C C6A 0.0339(11) 0.0437(13) 0.0595(16) 0.0047(20) 0.0086(21) -0.0093(23) C #======================================================================= # 10. MOLECULAR GEOMETRY loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag F C11 1.424(3) ? ? ? N1 C1 1.129(4) ? ? ? N2 C2 1.127(3) ? ? ? C1 C3 1.483(4) ? ? ? C2 C3 1.481(3) ? ? ? C3 C4 1.576(3) ? ? ? C3 H3 1.0924(21) ? ? ? C4 C5 1.552(3) ? ? ? C4 C9 1.566(3) ? ? ? C4 C14 1.555(3) ? ? ? C5 C6 1.540(3) ? ? ? C5 C13 1.549(3) ? ? ? C5 H5 1.0953(22) ? ? ? C6 C7 1.540(4) ? ? ? C6 H6 1.092(3) ? ? ? C6 H6' 1.0857(23) ? ? ? C7 C8 1.532(5) ? ? ? C7 C12 1.545(4) ? ? ? C7 H7 1.1005(24) ? ? ? C8 C9 1.539(4) ? ? ? C8 H8 1.100(3) ? ? ? C8 H8' 1.096(3) ? ? ? C9 C10 1.548(3) ? ? ? C9 H9 1.101(3) ? ? ? C10 C11 1.512(4) ? ? ? C10 H10 1.0824(24) ? ? ? C10 H10' 1.0924(23) ? ? ? C11 C12 1.512(4) ? ? ? C11 C13 1.517(4) ? ? ? C12 H12 1.092(3) ? ? ? C12 H12' 1.087(3) ? ? ? C13 H13 1.0832(23) ? ? ? C13 H13' 1.0941(24) ? ? ? C14 C1a 1.510(3) ? ? ? C14 H14 1.0889(24) ? ? ? C14 H14' 1.0988(25) ? ? ? C1a C2a 1.391(4) ? ? ? C1a C6a 1.392(4) ? ? ? C2a C3a 1.383(4) ? ? ? C2a H2a 1.014(3) ? ? ? C3a C4a 1.373(5) ? ? ? C3a H3a 0.993(3) ? ? ? C4a C5a 1.386(5) ? ? ? C4a H4a 0.989(3) ? ? ? C5a C6a 1.387(4) ? ? ? C5a H5a 1.013(3) ? ? ? C6a H6a 0.996(3) ? ? ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? 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_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 C1 C3 178.8(3) ? ? ? ? N2 C2 C3 175.2(3) ? ? ? ? C1 C3 C2 109.35(19) ? ? ? ? C1 C3 C4 111.74(19) ? ? ? ? C1 C3 H3 107.55(19) ? ? ? ? C2 C3 C4 114.89(18) ? ? ? ? C2 C3 H3 107.31(19) ? ? ? ? C4 C3 H3 105.59(17) ? ? ? ? C3 C4 C5 109.63(17) ? ? ? ? C3 C4 C9 107.29(17) ? ? ? ? C3 C4 C14 109.39(17) ? ? ? ? C5 C4 C9 107.57(17) ? ? ? ? C5 C4 C14 113.49(17) ? ? ? ? C9 C4 C14 109.27(17) ? ? ? ? C4 C5 C6 109.83(19) ? ? ? ? C4 C5 C13 110.92(17) ? ? ? ? C4 C5 H5 109.51(17) ? ? ? ? C6 C5 C13 107.65(18) ? ? ? ? C6 C5 H5 109.55(18) ? ? ? ? C13 C5 H5 109.36(19) ? ? ? ? C5 C6 C7 109.70(19) ? ? ? ? C5 C6 H6 109.36(22) ? ? ? ? C5 C6 H6' 109.45(20) ? ? ? ? C7 C6 H6 109.18(22) ? ? ? ? C7 C6 H6' 110.97(24) ? ? ? ? H6 C6 H6' 108.16(20) ? ? ? ? C6 C7 C8 110.41(21) ? ? ? ? C6 C7 C12 108.70(25) ? ? ? ? C6 C7 H7 110.12(23) ? ? ? ? C8 C7 C12 109.92(23) ? ? ? ? C8 C7 H7 108.1(3) ? ? ? ? C12 C7 H7 109.58(22) ? ? ? ? C7 C8 C9 109.52(21) ? ? ? ? C7 C8 H8 110.61(24) ? ? ? ? C7 C8 H8' 110.55(24) ? ? ? ? C9 C8 H8 109.53(23) ? ? ? ? C9 C8 H8' 109.73(23) ? ? ? ? H8 C8 H8' 106.86(23) ? ? ? ? C4 C9 C8 109.45(19) ? ? ? ? C4 C9 C10 111.26(18) ? ? ? ? C4 C9 H9 109.00(19) ? ? ? ? C8 C9 C10 107.58(20) ? ? ? ? C8 C9 H9 109.74(21) ? ? ? ? C10 C9 H9 109.80(20) ? ? ? ? C9 C10 C11 108.70(18) ? ? ? ? C9 C10 H10 109.89(20) ? ? ? ? C9 C10 H10' 109.71(21) ? ? ? ? C11 C10 H10 110.32(22) ? ? ? ? C11 C10 H10' 109.84(21) ? ? ? ? H10 C10 H10' 108.37(19) ? ? ? ? F C11 C10 107.68(18) ? ? ? ? F C11 C12 108.14(19) ? ? ? ? F C11 C13 107.58(20) ? ? ? ? C10 C11 C12 110.65(23) ? ? ? ? C10 C11 C13 111.41(19) ? ? ? ? C12 C11 C13 111.21(21) ? ? ? ? C7 C12 C11 107.27(20) ? ? ? ? C7 C12 H12 111.8(3) ? ? ? ? C7 C12 H12' 110.36(24) ? ? ? ? C11 C12 H12 109.63(22) ? ? ? ? C11 C12 H12' 109.7(3) ? ? ? ? H12 C12 H12' 108.10(21) ? ? ? ? C5 C13 C11 108.53(19) ? ? ? ? C5 C13 H13 110.70(18) ? ? ? ? C5 C13 H13' 109.68(18) ? ? ? ? C11 C13 H13 110.12(20) ? ? ? ? C11 C13 H13' 109.62(19) ? ? ? ? H13 C13 H13' 108.19(21) ? ? ? ? C4 C14 C1a 117.39(18) ? ? ? ? C4 C14 H14 108.18(19) ? ? ? ? C4 C14 H14' 107.40(18) ? ? ? ? C1a C14 H14 108.43(19) ? ? ? ? C1a C14 H14' 107.60(19) ? ? ? ? H14 C14 H14' 107.44(19) ? ? ? ? C14 C1a C2a 120.09(23) ? ? ? ? C14 C1a C6a 121.78(21) ? ? ? ? C2a C1a C6a 118.09(22) ? ? ? ? C1a C2a C3a 121.2(3) ? ? ? ? C1a C2a H2a 118.94(25) ? ? ? ? C3a C2a H2a 119.9(3) ? ? ? ? C2a C3a C4a 120.1(3) ? ? ? ? C2a C3a H3a 120.9(3) ? ? ? ? C4a C3a H3a 119.0(3) ? ? ? ? C3a C4a C5a 119.8(3) ? ? ? ? C3a C4a H4a 120.1(3) ? ? ? ? C5a C4a H4a 120.1(3) ? ? ? ? C4a C5a C6a 120.0(3) ? ? ? ? C4a C5a H5a 120.0(3) ? ? ? ? C6a C5a H5a 120.0(3) ? ? ? ? C1a C6a C5a 120.74(24) ? ? ? ? C1a C6a H6a 119.54(23) ? ? ? ? C5a C6a H6a 119.7(3) ? ? ? ? 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 N1 C1 C3 C2 174.8(3) N1 C1 C3 C4 -56.9(2) N2 C2 C3 C1 -94.3(3) N2 C2 C3 C4 139.1(3) C1 C3 C4 C5 -177.6(3) C1 C3 C4 C9 65.9(2) C1 C3 C4 C14 -52.5(2) C2 C3 C4 C5 -52.2(2) C2 C3 C4 C9 -168.8(2) C2 C3 C4 C14 72.8(2) C3 C4 C5 C6 -177.2(2) C3 C4 C5 C13 -58.4(2) C9 C4 C5 C6 -60.9(2) C9 C4 C5 C13 58.0(2) C14 C4 C5 C6 60.1(2) C14 C4 C5 C13 179.0(2) C3 C4 C9 C8 179.2(3) C3 C4 C9 C10 60.4(2) C5 C4 C9 C8 61.3(2) C5 C4 C9 C10 -57.4(2) C14 C4 C9 C8 -62.3(2) C14 C4 C9 C10 178.9(3) C3 C4 C14 C1A -55.1(2) C5 C4 C14 C1A 67.7(2) C9 C4 C14 C1A -172.2(3) C4 C5 C6 C7 60.0(2) C13 C5 C6 C7 -60.9(2) C4 C5 C13 C11 -60.1(2) C6 C5 C13 C11 60.1(2) C5 C6 C7 C8 -58.6(2) C5 C6 C7 C12 62.0(2) C6 C7 C8 C9 59.1(2) C12 C7 C8 C9 -60.8(2) C6 C7 C12 C11 -60.9(2) C8 C7 C12 C11 60.0(2) C7 C8 C9 C4 -60.8(2) C7 C8 C9 C10 60.2(2) C4 C9 C10 C11 58.8(2) C8 C9 C10 C11 -61.1(2) C9 C10 C11 F -178.3(3) C9 C10 C11 C12 63.7(2) C9 C10 C11 C13 -60.6(2) F C11 C12 C7 -179.6(3) C10 C11 C12 C7 -61.9(2) C13 C11 C12 C7 62.4(2) F C11 C13 C5 179.0(3) C10 C11 C13 C5 61.2(2) C12 C11 C13 C5 -62.7(2) C4 C14 C1A C2A 105.7(2) C4 C14 C1A C6A -76.4(2) C14 C1A C2A C3A 179.2(3) C6A C1A C2A C3A 1.3(2) C14 C1A C6A C5A -179.4(3) C2A C1A C6A C5A -1.5(2) C1A C2A C3A C4A -0.2(2) C2A C3A C4A C5A -0.6(2) C3A C4A C5A C6A 0.3(2) C4A C5A C6A C1A 0.8(2)