Electronic Supplementary Material for CrystEngComm This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full CrystEngComm _journal_coden_Cambridge 1350 _publ_contact_author_name 'Angshuman Roychoudhury' _publ_contact_author_address ; Department of Chemistry The University of Liverpool Oxford Street Liverpool L697ZD UNITED KINGDOM ; _publ_contact_author_email ANGSHU@LIV.AC.UK _publ_section_title ; Solvent mediated centric/non-centric polymorph pairs of an indole derivative: Subtle variation of C-H***O hydrogen bonds and C-H***pi interactions ; loop_ _publ_author_name 'Angshuman Roychoudhury' 'Tayur N. Guru Row' 'Kuppuswamy Nagarajan' data_28p1lt_m _database_code_depnum_ccdc_archive 'CCDC 283793' _audit_creation_date 2003-09-18T11:49:57-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-(4-fluorophenyl)-6, 6-dimethyl-2-phenyl-1, 5, 6, 7-tetrahydro-4H-indol-4-one ; _chemical_formula_sum 'C22 H20 F N O' _chemical_formula_weight 333.39 #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# 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 12.874(8) _cell_length_b 6.713(4) _cell_length_c 20.311(13) _cell_angle_alpha 90 _cell_angle_beta 94.651(10) _cell_angle_gamma 90 _cell_volume 1749.5(19) _cell_formula_units_Z 4 _cell_measurement_temperature 90.0(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description 'Rectangular Block' _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.20 _exptl_crystal_density_diffrn 1.266 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9751 _exptl_absorpt_correction_T_max 0.9833 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 90.0(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0349 _diffrn_reflns_av_unetI/netI 0.0308 _diffrn_reflns_number 12157 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 1.81 _diffrn_reflns_theta_max 25.34 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.999 _reflns_number_total 3196 _reflns_number_gt 2762 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Farrugia, 1999)' _computing_publication_material 'WinGx (Farrugia, 1999) and PLATON (Spek, 1990)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3196 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0457 _refine_ls_R_factor_gt 0.0391 _refine_ls_wR_factor_ref 0.128 _refine_ls_wR_factor_gt 0.1214 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.26 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.043 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.51595(6) -0.10259(12) 0.08520(4) 0.0299(3) Uani 1 1 d . . . N1 N 0.20441(8) 0.45782(15) 0.03927(5) 0.0162(3) Uani 1 1 d . . . O1 O -0.06250(8) 0.87171(16) 0.08734(6) 0.0362(3) Uani 1 1 d . . . C14 C 0.26021(11) 0.11401(19) 0.05356(7) 0.0201(3) Uani 1 1 d . . . C20 C 0.28511(10) 0.4207(2) -0.09870(6) 0.0189(3) Uani 1 1 d . . . C8 C 0.07270(10) 0.65169(19) 0.06328(6) 0.0178(3) Uani 1 1 d . . . C16 C 0.24571(10) 0.7717(2) -0.10954(6) 0.0196(3) Uani 1 1 d . . . C19 C 0.32871(11) 0.4254(2) -0.15874(7) 0.0225(3) Uani 1 1 d . . . C11 C 0.46818(11) 0.2339(2) 0.06820(6) 0.0214(3) Uani 1 1 d . . . C9 C 0.28642(10) 0.31404(19) 0.04932(6) 0.0156(3) Uani 1 1 d . . . C1 C 0.18656(10) 0.59466(18) -0.01301(6) 0.0167(3) Uani 1 1 d . . . C15 C 0.24245(10) 0.59367(18) -0.07299(6) 0.0173(3) Uani 1 1 d . . . C10 C 0.38975(10) 0.3746(2) 0.05665(6) 0.0192(3) Uani 1 1 d . . . C7 C 0.13462(9) 0.49324(18) 0.08500(6) 0.0168(3) Uani 1 1 d . . . C5 C 0.07322(10) 0.5064(2) 0.19786(6) 0.0225(3) Uani 1 1 d . . . C13 C 0.33803(11) -0.0271(2) 0.06625(7) 0.0229(3) Uani 1 1 d . . . C3 C -0.00845(10) 0.7250(2) 0.10238(7) 0.0223(3) Uani 1 1 d . . . C6 C 0.12682(11) 0.3793(2) 0.14732(6) 0.0211(3) Uani 1 1 d . . . C12 C 0.43968(11) 0.0361(2) 0.07309(6) 0.0214(3) Uani 1 1 d . . . C2 C 0.10530(10) 0.71484(19) 0.00160(7) 0.0183(3) Uani 1 1 d . . . C17 C 0.28866(11) 0.7741(2) -0.16978(7) 0.0232(3) Uani 1 1 d . . . C4 C -0.02483(11) 0.6046(2) 0.16354(7) 0.0236(3) Uani 1 1 d . . . C18 C 0.33024(11) 0.6015(2) -0.19475(7) 0.0249(3) Uani 1 1 d . . . C21 C 0.04072(13) 0.3706(3) 0.25303(7) 0.0308(4) Uani 1 1 d . . . C22 C 0.14814(13) 0.6665(3) 0.22726(8) 0.0342(4) Uani 1 1 d . . . H11 H 0.5402(13) 0.277(2) 0.0730(7) 0.027(4) Uiso 1 1 d . . . H19 H 0.3584(13) 0.302(2) -0.1761(8) 0.031(4) Uiso 1 1 d . . . H2 H 0.0752(11) 0.821(2) -0.0267(7) 0.022(4) Uiso 1 1 d . . . H6B H 0.1955(13) 0.338(2) 0.1657(7) 0.025(4) Uiso 1 1 d . . . H20 H 0.2825(11) 0.293(2) -0.0760(7) 0.019(4) Uiso 1 1 d . . . H16 H 0.2145(13) 0.894(2) -0.0925(8) 0.032(4) Uiso 1 1 d . . . H6A H 0.0847(11) 0.256(2) 0.1380(7) 0.019(4) Uiso 1 1 d . . . H21B H -0.0101(14) 0.260(3) 0.2341(8) 0.037(5) Uiso 1 1 d . . . H14 H 0.1870(12) 0.072(2) 0.0479(7) 0.021(4) Uiso 1 1 d . . . H18 H 0.3588(12) 0.609(2) -0.2379(8) 0.028(4) Uiso 1 1 d . . . H4A H -0.0765(12) 0.501(2) 0.1498(7) 0.024(4) Uiso 1 1 d . . . H22A H 0.1702(14) 0.762(3) 0.1922(9) 0.046(5) Uiso 1 1 d . . . H17 H 0.2879(12) 0.901(2) -0.1951(8) 0.025(4) Uiso 1 1 d . . . H21C H 0.1015(14) 0.303(3) 0.2752(8) 0.036(4) Uiso 1 1 d . . . H10 H 0.4087(12) 0.519(3) 0.0524(8) 0.028(4) Uiso 1 1 d . . . H22B H 0.1117(15) 0.747(3) 0.2607(9) 0.049(5) Uiso 1 1 d . . . H4B H -0.0593(13) 0.690(3) 0.1944(8) 0.040(5) Uiso 1 1 d . . . H22C H 0.2093(17) 0.598(3) 0.2498(10) 0.049(5) Uiso 1 1 d . . . H13 H 0.3217(13) -0.167(3) 0.0704(8) 0.038(5) Uiso 1 1 d . . . H21A H 0.0041(14) 0.452(3) 0.2856(9) 0.043(5) Uiso 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 F1 0.0342(5) 0.0293(5) 0.0262(5) 0.0002(3) 0.0022(4) 0.0202(4) N1 0.0169(6) 0.0145(5) 0.0175(6) -0.0002(4) 0.0025(4) 0.0017(4) O1 0.0342(6) 0.0279(6) 0.0490(7) 0.0102(5) 0.0189(5) 0.0162(5) C14 0.0228(7) 0.0171(7) 0.0207(7) -0.0021(5) 0.0032(5) 0.0006(5) C20 0.0200(7) 0.0183(7) 0.0184(7) 0.0006(5) 0.0017(5) 0.0020(5) C8 0.0167(7) 0.0153(6) 0.0215(7) -0.0026(5) 0.0021(5) -0.0002(5) C16 0.0179(7) 0.0183(7) 0.0224(7) 0.0027(5) -0.0006(5) 0.0002(5) C19 0.0233(7) 0.0251(8) 0.0195(7) -0.0019(6) 0.0031(5) 0.0024(6) C11 0.0178(7) 0.0270(8) 0.0195(7) -0.0029(5) 0.0016(5) 0.0047(5) C9 0.0185(7) 0.0166(6) 0.0118(6) -0.0007(5) 0.0028(5) 0.0035(5) C1 0.0179(7) 0.0124(6) 0.0196(7) 0.0001(5) 0.0009(5) -0.0009(5) C15 0.0142(6) 0.0192(7) 0.0182(7) 0.0008(5) -0.0004(5) -0.0008(5) C10 0.0217(7) 0.0179(7) 0.0182(7) -0.0011(5) 0.0032(5) 0.0014(5) C7 0.0161(6) 0.0169(6) 0.0178(6) -0.0028(5) 0.0036(5) 0.0003(5) C5 0.0204(7) 0.0287(8) 0.0188(7) -0.0040(6) 0.0042(5) 0.0011(6) C13 0.0331(8) 0.0147(7) 0.0212(7) -0.0008(5) 0.0032(6) 0.0043(6) C3 0.0181(7) 0.0199(7) 0.0291(7) -0.0019(6) 0.0040(5) 0.0017(5) C6 0.0212(7) 0.0228(7) 0.0196(7) 0.0015(5) 0.0041(6) 0.0023(6) C12 0.0270(7) 0.0234(7) 0.0140(7) -0.0004(5) 0.0024(5) 0.0127(6) C2 0.0169(7) 0.0148(6) 0.0231(7) 0.0012(5) 0.0016(5) 0.0004(5) C17 0.0227(7) 0.0239(7) 0.0228(7) 0.0073(6) -0.0005(5) -0.0032(6) C4 0.0200(7) 0.0283(8) 0.0233(7) -0.0044(6) 0.0065(6) 0.0028(6) C18 0.0242(8) 0.0336(8) 0.0171(7) 0.0015(6) 0.0032(6) -0.0028(6) C21 0.0268(8) 0.0459(10) 0.0206(8) 0.0027(7) 0.0071(6) 0.0058(7) C22 0.0289(9) 0.0441(10) 0.0295(8) -0.0135(8) 0.0015(7) -0.0038(8) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C12 1.3611(16) . ? N1 C7 1.3644(17) . ? N1 C1 1.4087(17) . ? N1 C9 1.4328(17) . ? O1 C3 1.2303(17) . ? C14 C13 1.388(2) . ? C14 C9 1.389(2) . ? C14 H14 0.982(15) . ? C20 C19 1.384(2) . ? C20 C15 1.4030(19) . ? C20 H20 0.973(15) . ? C8 C7 1.3800(19) . ? C8 C2 1.418(2) . ? C8 C3 1.4486(19) . ? C16 C17 1.383(2) . ? C16 C15 1.4092(19) . ? C16 H16 0.988(17) . ? C19 C18 1.391(2) . ? C19 H19 0.991(17) . ? C11 C12 1.383(2) . ? C11 C10 1.3889(19) . ? C11 H11 0.968(16) . ? C9 C10 1.388(2) . ? C1 C2 1.3724(19) . ? C1 C15 1.4644(19) . ? C10 H10 1.004(17) . ? C7 C6 1.4892(19) . ? C5 C21 1.529(2) . ? C5 C22 1.533(2) . ? C5 C4 1.540(2) . ? C5 C6 1.5400(19) . ? C13 C12 1.372(2) . ? C13 H13 0.968(19) . ? C3 C4 1.511(2) . ? C6 H6B 0.973(16) . ? C6 H6A 0.999(15) . ? C2 H2 0.979(15) . ? C17 C18 1.389(2) . ? C17 H17 0.992(16) . ? C4 H4A 0.986(16) . ? C4 H4B 0.981(19) . ? C18 H18 0.979(16) . ? C21 H21B 1.041(18) . ? C21 H21C 0.981(18) . ? C21 H21A 1.003(19) . ? C22 H22A 1.014(19) . ? C22 H22B 1.01(2) . ? C22 H22C 0.99(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 C7 N1 C1 108.86(11) . . ? C7 N1 C9 122.60(11) . . ? C1 N1 C9 128.31(11) . . ? C13 C14 C9 119.73(13) . . ? C13 C14 H14 119.8(9) . . ? C9 C14 H14 120.5(9) . . ? C19 C20 C15 120.55(13) . . ? C19 C20 H20 118.0(8) . . ? C15 C20 H20 121.4(8) . . ? C7 C8 C2 107.95(11) . . ? C7 C8 C3 120.67(12) . . ? C2 C8 C3 131.38(12) . . ? C17 C16 C15 120.47(13) . . ? C17 C16 H16 120.2(10) . . ? C15 C16 H16 119.3(10) . . ? C20 C19 C18 120.46(13) . . ? C20 C19 H19 119.3(9) . . ? C18 C19 H19 120.2(9) . . ? C12 C11 C10 118.15(13) . . ? C12 C11 H11 122.3(9) . . ? C10 C11 H11 119.5(9) . . ? C10 C9 C14 120.83(12) . . ? C10 C9 N1 120.45(12) . . ? C14 C9 N1 118.69(12) . . ? C2 C1 N1 107.52(12) . . ? C2 C1 C15 128.11(12) . . ? N1 C1 C15 124.26(11) . . ? C20 C15 C16 118.44(13) . . ? C20 C15 C1 123.16(11) . . ? C16 C15 C1 118.17(12) . . ? C9 C10 C11 119.75(13) . . ? C9 C10 H10 120.7(9) . . ? C11 C10 H10 119.5(9) . . ? N1 C7 C8 108.18(11) . . ? N1 C7 C6 125.64(12) . . ? C8 C7 C6 126.18(12) . . ? C21 C5 C22 109.49(13) . . ? C21 C5 C4 108.90(12) . . ? C22 C5 C4 110.06(13) . . ? C21 C5 C6 108.81(13) . . ? C22 C5 C6 110.25(12) . . ? C4 C5 C6 109.30(11) . . ? C12 C13 C14 118.44(13) . . ? C12 C13 H13 120.2(10) . . ? C14 C13 H13 121.3(10) . . ? O1 C3 C8 123.66(13) . . ? O1 C3 C4 121.23(12) . . ? C8 C3 C4 115.09(12) . . ? C7 C6 C5 110.31(12) . . ? C7 C6 H6B 110.6(9) . . ? C5 C6 H6B 110.2(9) . . ? C7 C6 H6A 109.7(8) . . ? C5 C6 H6A 108.7(8) . . ? H6B C6 H6A 107.2(12) . . ? F1 C12 C13 118.36(13) . . ? F1 C12 C11 118.55(13) . . ? C13 C12 C11 123.09(12) . . ? C1 C2 C8 107.50(12) . . ? C1 C2 H2 125.1(9) . . ? C8 C2 H2 127.3(9) . . ? C16 C17 C18 120.46(13) . . ? C16 C17 H17 118.7(9) . . ? C18 C17 H17 120.9(9) . . ? C3 C4 C5 115.92(12) . . ? C3 C4 H4A 106.3(9) . . ? C5 C4 H4A 109.6(9) . . ? C3 C4 H4B 108.2(10) . . ? C5 C4 H4B 111.0(10) . . ? H4A C4 H4B 105.2(13) . . ? C17 C18 C19 119.62(14) . . ? C17 C18 H18 117.7(9) . . ? C19 C18 H18 122.6(9) . . ? C5 C21 H21B 110.8(9) . . ? C5 C21 H21C 110.9(10) . . ? H21B C21 H21C 107.2(14) . . ? C5 C21 H21A 109.4(10) . . ? H21B C21 H21A 108.3(14) . . ? H21C C21 H21A 110.3(14) . . ? C5 C22 H22A 111.8(10) . . ? C5 C22 H22B 109.0(11) . . ? H22A C22 H22B 107.7(15) . . ? C5 C22 H22C 107.9(11) . . ? H22A C22 H22C 111.0(16) . . ? H22B C22 H22C 109.4(16) . . ? 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 C15 C20 C19 C18 -0.5(2) . . . . ? C13 C14 C9 C10 0.95(19) . . . . ? C13 C14 C9 N1 -177.10(11) . . . . ? C7 N1 C9 C10 -112.79(14) . . . . ? C1 N1 C9 C10 60.99(17) . . . . ? C7 N1 C9 C14 65.27(16) . . . . ? C1 N1 C9 C14 -120.95(14) . . . . ? C7 N1 C1 C2 0.33(14) . . . . ? C9 N1 C1 C2 -174.13(11) . . . . ? C7 N1 C1 C15 -176.08(11) . . . . ? C9 N1 C1 C15 9.46(19) . . . . ? C19 C20 C15 C16 -0.37(19) . . . . ? C19 C20 C15 C1 174.05(12) . . . . ? C17 C16 C15 C20 0.95(19) . . . . ? C17 C16 C15 C1 -173.75(11) . . . . ? C2 C1 C15 C20 -147.82(14) . . . . ? N1 C1 C15 C20 27.83(19) . . . . ? C2 C1 C15 C16 26.62(19) . . . . ? N1 C1 C15 C16 -157.73(12) . . . . ? C14 C9 C10 C11 0.19(19) . . . . ? N1 C9 C10 C11 178.21(11) . . . . ? C12 C11 C10 C9 -1.06(19) . . . . ? C1 N1 C7 C8 -0.49(14) . . . . ? C9 N1 C7 C8 174.35(10) . . . . ? C1 N1 C7 C6 179.27(12) . . . . ? C9 N1 C7 C6 -5.88(19) . . . . ? C2 C8 C7 N1 0.46(14) . . . . ? C3 C8 C7 N1 -179.34(11) . . . . ? C2 C8 C7 C6 -179.30(12) . . . . ? C3 C8 C7 C6 0.9(2) . . . . ? C9 C14 C13 C12 -1.17(19) . . . . ? C7 C8 C3 O1 176.14(13) . . . . ? C2 C8 C3 O1 -3.6(2) . . . . ? C7 C8 C3 C4 -5.21(18) . . . . ? C2 C8 C3 C4 175.04(13) . . . . ? N1 C7 C6 C5 157.34(12) . . . . ? C8 C7 C6 C5 -22.94(18) . . . . ? C21 C5 C6 C7 165.25(11) . . . . ? C22 C5 C6 C7 -74.66(15) . . . . ? C4 C5 C6 C7 46.44(15) . . . . ? C14 C13 C12 F1 -179.68(11) . . . . ? C14 C13 C12 C11 0.3(2) . . . . ? C10 C11 C12 F1 -179.20(11) . . . . ? C10 C11 C12 C13 0.84(19) . . . . ? N1 C1 C2 C8 -0.04(14) . . . . ? C15 C1 C2 C8 176.19(12) . . . . ? C7 C8 C2 C1 -0.26(14) . . . . ? C3 C8 C2 C1 179.52(13) . . . . ? C15 C16 C17 C18 -0.7(2) . . . . ? O1 C3 C4 C5 -148.39(14) . . . . ? C8 C3 C4 C5 32.92(17) . . . . ? C21 C5 C4 C3 -172.98(12) . . . . ? C22 C5 C4 C3 66.99(15) . . . . ? C6 C5 C4 C3 -54.22(16) . . . . ? C16 C17 C18 C19 -0.1(2) . . . . ? C20 C19 C18 C17 0.7(2) . . . . ? _chemical_name_common ;1-(4-fluorophenyl)-6, 6-dimethyl-2-phenyl-1, 5, 6, 7- tetrahydro-4H-indol-4-one ; # Attachment 'Form II.cif' data_28p2lt_m _database_code_depnum_ccdc_archive 'CCDC 283794' _audit_creation_date 2004-04-01T20:09:07-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; 1-(4-fluorophenyl)-6, 6-dimethyl-2-phenyl-1, 5, 6, 7-tetrahydro-4H-indol-4-one ; _chemical_formula_sum 'C22 H20 F N O' _chemical_formula_weight 333.39 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.892(5) _cell_length_b 10.861(6) _cell_length_c 10.786(6) _cell_angle_alpha 90 _cell_angle_beta 109.986(8) _cell_angle_gamma 90 _cell_volume 868.9(9) _cell_formula_units_Z 2 _cell_measurement_temperature 90(2) #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.35 _exptl_crystal_density_diffrn 1.274 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 352 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9668 _exptl_absorpt_correction_T_max 0.9709 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 90(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_reflns_av_R_equivalents 0.0167 _diffrn_reflns_av_unetI/netI 0.0245 _diffrn_reflns_number 6405 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 2.01 _diffrn_reflns_theta_max 25.35 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 1.000 _reflns_number_total 3154 _reflns_number_gt 3062 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SIR92 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997) and CAMERON (Farrugia, 1999)' _computing_publication_material 'WinGx (Farrugia, 1999) and PLATON (Spek, 1990)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^)+(0.0536P)^2^+0.0391P] 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 mixed _refine_ls_extinction_method none _refine_ls_number_reflns 3154 _refine_ls_number_parameters 306 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0283 _refine_ls_R_factor_gt 0.0274 _refine_ls_wR_factor_ref 0.0729 _refine_ls_wR_factor_gt 0.0723 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.033 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.3(6) _refine_diff_density_max 0.155 _refine_diff_density_min -0.174 _refine_diff_density_rms 0.034 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 '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' 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 0.69696(11) 0.74823(8) 1.36431(7) 0.0254(2) Uani 1 1 d . . . O1 O -0.03466(12) 1.03682(8) 0.45532(9) 0.0199(2) Uani 1 1 d . . . N1 N 0.26374(15) 0.94639(10) 0.89027(11) 0.0155(2) Uani 1 1 d . . . C20 C 0.11358(19) 1.05326(14) 1.10421(13) 0.0202(3) Uani 1 1 d . . . C12 C 0.59385(18) 0.79530(13) 1.24640(13) 0.0200(3) Uani 1 1 d . . . C7 C 0.24241(17) 0.90736(11) 0.76498(13) 0.0155(3) Uani 1 1 d . . . C13 C 0.4639(2) 0.72159(13) 1.16068(15) 0.0214(3) Uani 1 1 d . . . C1 C 0.15471(18) 1.05093(12) 0.88245(13) 0.0159(3) Uani 1 1 d . . . C15 C 0.14292(17) 1.11574(13) 0.99989(13) 0.0169(3) Uani 1 1 d . . . C11 C 0.62406(19) 0.91599(13) 1.21722(14) 0.0204(3) Uani 1 1 d . . . C9 C 0.38099(18) 0.89287(12) 1.01041(13) 0.0162(3) Uani 1 1 d . . . C16 C 0.15596(17) 1.24476(13) 1.00462(13) 0.0188(3) Uani 1 1 d . . . C18 C 0.11400(18) 1.24562(15) 1.21598(14) 0.0231(3) Uani 1 1 d . . . C2 C 0.06605(18) 1.07528(12) 0.75276(13) 0.0162(3) Uani 1 1 d . . . C3 C 0.06729(17) 0.96669(12) 0.53602(14) 0.0160(3) Uani 1 1 d . . . C10 C 0.51568(19) 0.96417(12) 1.09712(14) 0.0188(3) Uani 1 1 d . . . C14 C 0.35410(19) 0.77115(12) 1.04133(13) 0.0181(3) Uani 1 1 d . . . C8 C 0.12001(18) 0.98468(12) 0.67750(13) 0.0158(3) Uani 1 1 d . . . C17 C 0.14190(19) 1.30861(14) 1.11283(14) 0.0228(3) Uani 1 1 d . . . C5 C 0.33815(18) 0.82052(12) 0.58436(14) 0.0171(3) Uani 1 1 d . . . C19 C 0.0990(2) 1.11747(15) 1.21160(15) 0.0237(3) Uani 1 1 d . . . C6 C 0.33834(18) 0.80187(12) 0.72747(13) 0.0165(3) Uani 1 1 d . . . C4 C 0.14547(19) 0.85211(13) 0.49476(14) 0.0184(3) Uani 1 1 d . . . C22 C 0.3999(2) 0.70025(13) 0.53793(15) 0.0205(3) Uani 1 1 d . . . C21 C 0.4667(2) 0.92525(13) 0.57881(15) 0.0207(3) Uani 1 1 d . . . H19 H 0.075(2) 1.0740(17) 1.2810(18) 0.028(4) Uiso 1 1 d . . . H14 H 0.258(2) 0.7218(16) 0.9807(16) 0.019(4) Uiso 1 1 d . . . H21B H 0.465(2) 0.9352(17) 0.4870(19) 0.031(4) Uiso 1 1 d . . . H10 H 0.530(2) 1.0473(17) 1.0706(16) 0.024(4) Uiso 1 1 d . . . H4A H 0.138(2) 0.8641(14) 0.4042(16) 0.013(3) Uiso 1 1 d . . . H22A H 0.405(2) 0.7110(15) 0.4520(17) 0.021(4) Uiso 1 1 d . . . H20 H 0.109(2) 0.9669(17) 1.1044(17) 0.021(4) Uiso 1 1 d . . . H17 H 0.154(2) 1.4014(17) 1.1154(16) 0.025(4) Uiso 1 1 d . . . H13 H 0.449(2) 0.6402(17) 1.1843(17) 0.023(4) Uiso 1 1 d . . . H18 H 0.102(2) 1.2877(16) 1.2901(17) 0.027(4) Uiso 1 1 d . . . H6A H 0.459(2) 0.7917(13) 0.7891(14) 0.007(3) Uiso 1 1 d . . . H22C H 0.526(3) 0.6789(16) 0.5966(18) 0.025(4) Uiso 1 1 d . . . H4B H 0.063(2) 0.7852(16) 0.4982(16) 0.023(4) Uiso 1 1 d . . . H21A H 0.429(3) 1.0025(18) 0.6044(18) 0.034(5) Uiso 1 1 d . . . H16 H 0.179(2) 1.2912(16) 0.9326(17) 0.024(4) Uiso 1 1 d . . . H11 H 0.719(2) 0.9651(16) 1.2762(18) 0.023(4) Uiso 1 1 d . . . H6B H 0.273(2) 0.7236(17) 0.7290(17) 0.024(4) Uiso 1 1 d . . . H21C H 0.590(3) 0.9099(16) 0.6373(17) 0.024(4) Uiso 1 1 d . . . H2 H -0.023(3) 1.1416(17) 0.7152(18) 0.027(4) Uiso 1 1 d . . . H22B H 0.315(2) 0.6317(16) 0.5375(17) 0.023(4) Uiso 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 F1 0.0271(4) 0.0289(5) 0.0163(4) 0.0047(4) 0.0025(3) 0.0072(4) O1 0.0217(5) 0.0203(5) 0.0161(5) 0.0012(4) 0.0043(4) 0.0023(4) N1 0.0182(5) 0.0135(5) 0.0142(6) -0.0003(4) 0.0048(4) -0.0005(4) C20 0.0237(7) 0.0184(7) 0.0180(7) -0.0001(6) 0.0064(6) 0.0015(6) C12 0.0218(7) 0.0233(7) 0.0148(7) 0.0038(5) 0.0061(6) 0.0084(6) C7 0.0182(6) 0.0138(6) 0.0145(7) -0.0011(5) 0.0056(5) -0.0034(5) C13 0.0253(7) 0.0167(7) 0.0228(7) 0.0033(5) 0.0090(6) 0.0020(6) C1 0.0187(6) 0.0121(6) 0.0171(7) 0.0007(5) 0.0063(5) -0.0006(5) C15 0.0148(6) 0.0182(7) 0.0168(7) -0.0019(5) 0.0042(5) 0.0023(5) C11 0.0200(7) 0.0223(7) 0.0175(7) -0.0044(6) 0.0046(6) -0.0018(6) C9 0.0182(6) 0.0166(7) 0.0139(7) 0.0002(5) 0.0058(5) 0.0022(5) C16 0.0181(7) 0.0174(7) 0.0194(7) 0.0004(6) 0.0046(5) 0.0018(5) C18 0.0186(7) 0.0308(8) 0.0178(7) -0.0080(6) 0.0037(5) 0.0055(6) C2 0.0192(6) 0.0130(6) 0.0172(7) 0.0011(5) 0.0075(5) 0.0002(5) C3 0.0164(6) 0.0158(6) 0.0164(7) 0.0007(5) 0.0063(5) -0.0023(5) C10 0.0229(7) 0.0153(7) 0.0190(7) 0.0005(5) 0.0080(6) 0.0003(5) C14 0.0204(6) 0.0154(7) 0.0173(7) -0.0010(6) 0.0049(5) -0.0001(5) C8 0.0179(6) 0.0129(6) 0.0165(7) -0.0004(5) 0.0057(5) -0.0013(5) C17 0.0208(7) 0.0188(7) 0.0259(8) -0.0040(6) 0.0044(6) 0.0037(6) C5 0.0209(6) 0.0139(6) 0.0179(7) -0.0010(5) 0.0085(5) 0.0004(5) C19 0.0222(7) 0.0316(8) 0.0179(7) 0.0021(6) 0.0076(6) 0.0023(6) C6 0.0183(7) 0.0139(6) 0.0165(7) 0.0001(5) 0.0051(6) 0.0005(6) C4 0.0243(7) 0.0172(7) 0.0143(7) -0.0022(5) 0.0075(6) -0.0028(6) C22 0.0234(8) 0.0176(7) 0.0217(8) -0.0033(6) 0.0094(6) -0.0007(6) C21 0.0232(7) 0.0172(7) 0.0235(8) -0.0012(6) 0.0101(6) -0.0013(6) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _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 C12 1.3541(16) . ? O1 C3 1.2274(16) . ? N1 C7 1.3706(18) . ? N1 C1 1.4096(19) . ? N1 C9 1.4331(18) . ? C20 C19 1.390(2) . ? C20 C15 1.399(2) . ? C20 H20 0.938(18) . ? C12 C13 1.378(2) . ? C12 C11 1.388(2) . ? C7 C8 1.380(2) . ? C7 C6 1.5030(19) . ? C13 C14 1.391(2) . ? C13 H13 0.938(19) . ? C1 C2 1.359(2) . ? C1 C15 1.4797(19) . ? C15 C16 1.405(2) . ? C11 C10 1.388(2) . ? C11 H11 0.963(19) . ? C9 C10 1.387(2) . ? C9 C14 1.397(2) . ? C16 C17 1.394(2) . ? C16 H16 0.994(18) . ? C18 C17 1.386(2) . ? C18 C19 1.396(2) . ? C18 H18 0.955(18) . ? C2 C8 1.4299(19) . ? C2 H2 0.989(19) . ? C3 C8 1.451(2) . ? C3 C4 1.522(2) . ? C10 H10 0.964(19) . ? C14 H14 0.976(18) . ? C17 H17 1.012(18) . ? C5 C4 1.536(2) . ? C5 C22 1.5367(19) . ? C5 C21 1.539(2) . ? C5 C6 1.556(2) . ? C19 H19 0.958(19) . ? C6 H6A 0.963(15) . ? C6 H6B 0.999(19) . ? C4 H4A 0.968(16) . ? C4 H4B 0.982(18) . ? C22 H22A 0.950(17) . ? C22 H22C 1.007(19) . ? C22 H22B 1.003(18) . ? C21 H21B 0.99(2) . ? C21 H21A 0.96(2) . ? C21 H21C 0.979(19) . ? 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 C7 N1 C1 108.86(10) . . ? C7 N1 C9 126.14(11) . . ? C1 N1 C9 124.97(11) . . ? C19 C20 C15 120.68(14) . . ? C19 C20 H20 119.0(10) . . ? C15 C20 H20 120.3(10) . . ? F1 C12 C13 118.78(13) . . ? F1 C12 C11 118.35(13) . . ? C13 C12 C11 122.87(13) . . ? N1 C7 C8 107.89(12) . . ? N1 C7 C6 126.71(12) . . ? C8 C7 C6 125.37(13) . . ? C12 C13 C14 118.77(13) . . ? C12 C13 H13 119.9(11) . . ? C14 C13 H13 121.3(11) . . ? C2 C1 N1 107.90(11) . . ? C2 C1 C15 128.88(13) . . ? N1 C1 C15 123.21(11) . . ? C20 C15 C16 119.00(12) . . ? C20 C15 C1 122.26(13) . . ? C16 C15 C1 118.71(12) . . ? C12 C11 C10 117.97(13) . . ? C12 C11 H11 121.9(10) . . ? C10 C11 H11 120.1(10) . . ? C10 C9 C14 120.73(13) . . ? C10 C9 N1 119.50(12) . . ? C14 C9 N1 119.73(12) . . ? C17 C16 C15 120.05(13) . . ? C17 C16 H16 119.4(10) . . ? C15 C16 H16 120.6(10) . . ? C17 C18 C19 119.97(14) . . ? C17 C18 H18 121.7(11) . . ? C19 C18 H18 118.3(11) . . ? C1 C2 C8 107.57(12) . . ? C1 C2 H2 127.3(11) . . ? C8 C2 H2 125.1(11) . . ? O1 C3 C8 123.03(12) . . ? O1 C3 C4 122.22(12) . . ? C8 C3 C4 114.74(11) . . ? C9 C10 C11 120.31(13) . . ? C9 C10 H10 117.4(10) . . ? C11 C10 H10 122.3(10) . . ? C13 C14 C9 119.32(13) . . ? C13 C14 H14 120.2(10) . . ? C9 C14 H14 120.5(10) . . ? C7 C8 C2 107.77(12) . . ? C7 C8 C3 121.27(12) . . ? C2 C8 C3 130.96(12) . . ? C18 C17 C16 120.42(14) . . ? C18 C17 H17 120.6(9) . . ? C16 C17 H17 119.0(9) . . ? C4 C5 C22 109.92(11) . . ? C4 C5 C21 109.54(12) . . ? C22 C5 C21 109.22(11) . . ? C4 C5 C6 108.55(11) . . ? C22 C5 C6 108.64(11) . . ? C21 C5 C6 110.95(11) . . ? C20 C19 C18 119.88(14) . . ? C20 C19 H19 120.0(11) . . ? C18 C19 H19 120.1(11) . . ? C7 C6 C5 109.76(11) . . ? C7 C6 H6A 111.8(8) . . ? C5 C6 H6A 111.4(8) . . ? C7 C6 H6B 109.4(10) . . ? C5 C6 H6B 107.6(10) . . ? H6A C6 H6B 106.6(13) . . ? C3 C4 C5 114.32(11) . . ? C3 C4 H4A 107.1(9) . . ? C5 C4 H4A 111.8(9) . . ? C3 C4 H4B 104.8(9) . . ? C5 C4 H4B 109.5(10) . . ? H4A C4 H4B 108.9(13) . . ? C5 C22 H22A 109.8(10) . . ? C5 C22 H22C 110.3(10) . . ? H22A C22 H22C 106.0(14) . . ? C5 C22 H22B 110.2(10) . . ? H22A C22 H22B 109.9(14) . . ? H22C C22 H22B 110.5(13) . . ? C5 C21 H21B 109.6(11) . . ? C5 C21 H21A 111.0(12) . . ? H21B C21 H21A 107.0(16) . . ? C5 C21 H21C 112.0(10) . . ? H21B C21 H21C 109.4(15) . . ? H21A C21 H21C 107.7(15) . . ? 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 C1 N1 C7 C8 -0.62(14) . . . . ? C9 N1 C7 C8 -178.97(11) . . . . ? C1 N1 C7 C6 177.61(12) . . . . ? C9 N1 C7 C6 -0.7(2) . . . . ? F1 C12 C13 C14 177.98(11) . . . . ? C11 C12 C13 C14 -2.1(2) . . . . ? C7 N1 C1 C2 0.39(14) . . . . ? C9 N1 C1 C2 178.77(11) . . . . ? C7 N1 C1 C15 179.00(12) . . . . ? C9 N1 C1 C15 -2.62(19) . . . . ? C19 C20 C15 C16 -0.5(2) . . . . ? C19 C20 C15 C1 -178.48(13) . . . . ? C2 C1 C15 C20 129.47(16) . . . . ? N1 C1 C15 C20 -48.84(19) . . . . ? C2 C1 C15 C16 -48.47(19) . . . . ? N1 C1 C15 C16 133.22(14) . . . . ? F1 C12 C11 C10 -178.90(11) . . . . ? C13 C12 C11 C10 1.1(2) . . . . ? C7 N1 C9 C10 120.29(15) . . . . ? C1 N1 C9 C10 -57.81(17) . . . . ? C7 N1 C9 C14 -62.19(17) . . . . ? C1 N1 C9 C14 119.71(15) . . . . ? C20 C15 C16 C17 0.8(2) . . . . ? C1 C15 C16 C17 178.78(12) . . . . ? N1 C1 C2 C8 -0.01(14) . . . . ? C15 C1 C2 C8 -178.53(13) . . . . ? C14 C9 C10 C11 -1.06(19) . . . . ? N1 C9 C10 C11 176.43(12) . . . . ? C12 C11 C10 C9 0.4(2) . . . . ? C12 C13 C14 C9 1.4(2) . . . . ? C10 C9 C14 C13 0.13(19) . . . . ? N1 C9 C14 C13 -177.36(12) . . . . ? N1 C7 C8 C2 0.60(14) . . . . ? C6 C7 C8 C2 -177.66(12) . . . . ? N1 C7 C8 C3 -179.47(11) . . . . ? C6 C7 C8 C3 2.28(19) . . . . ? C1 C2 C8 C7 -0.36(14) . . . . ? C1 C2 C8 C3 179.72(13) . . . . ? O1 C3 C8 C7 -176.55(12) . . . . ? C4 C3 C8 C7 4.60(17) . . . . ? O1 C3 C8 C2 3.4(2) . . . . ? C4 C3 C8 C2 -175.49(13) . . . . ? C19 C18 C17 C16 -0.3(2) . . . . ? C15 C16 C17 C18 -0.4(2) . . . . ? C15 C20 C19 C18 -0.1(2) . . . . ? C17 C18 C19 C20 0.5(2) . . . . ? N1 C7 C6 C5 -156.84(12) . . . . ? C8 C7 C6 C5 21.09(17) . . . . ? C4 C5 C6 C7 -48.62(14) . . . . ? C22 C5 C6 C7 -168.13(11) . . . . ? C21 C5 C6 C7 71.80(14) . . . . ? O1 C3 C4 C5 145.22(12) . . . . ? C8 C3 C4 C5 -35.91(16) . . . . ? C22 C5 C4 C3 177.18(11) . . . . ? C21 C5 C4 C3 -62.81(15) . . . . ? C6 C5 C4 C3 58.47(14) . . . . ? _chemical_name_common ;1-(4-fluorophenyl)-6, 6-dimethyl-2-phenyl-1, 5, 6, 7- tetrahydro-4H-indol-4-one ;