# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'John Wallis' _publ_contact_author_email JOHN.WALLIS@NTU.AC.UK _publ_section_title ; Interactions and Reactions in 2,2'-Disubstituted Biphenyls - An Open or Shut Case. ; loop_ _publ_author_name 'John Wallis' "Jane O'Leary" # Attachment 'ALL_BIPHENYLS_WALLIS.cif' data_c:\xray\compound5 _database_code_depnum_ccdc_archive 'CCDC 658334' _audit_creation_method SHELXL-97 _chemical_name_systematic ; E-2-(2-(Dimethylamino)biphen-2-yl)-1-nitroethene ; _chemical_name_common E-2-(2-(Dimethylamino)biphen-2-yl)-1-nitroethene _chemical_melting_point 380-384 _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 N2 O2' _chemical_formula_weight 268.31 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' _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 8.8510(2) _cell_length_b 9.8816(3) _cell_length_c 18.2164(7) _cell_angle_alpha 92.1632(14) _cell_angle_beta 96.4141(15) _cell_angle_gamma 116.416(2) _cell_volume 1411.10(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 11811 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.14 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.952 _exptl_absorpt_correction_T_max 0.996 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 19677 _diffrn_reflns_av_R_equivalents 0.0714 _diffrn_reflns_av_sigmaI/netI 0.1009 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.48 _reflns_number_total 6274 _reflns_number_gt 3631 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _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^)+(0.1347P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 6274 _refine_ls_number_parameters 425 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1387 _refine_ls_R_factor_gt 0.0787 _refine_ls_wR_factor_ref 0.2342 _refine_ls_wR_factor_gt 0.2126 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.005 _refine_ls_shift/su_mean 0.001 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 O1A O 0.4288(3) 0.4400(3) 0.39322(12) 0.0411(6) Uani 1 1 d . . . O2A O 0.2755(3) 0.5217(3) 0.32539(12) 0.0421(6) Uani 1 1 d . . . N1A N 0.2998(3) 0.9346(3) 0.40848(13) 0.0282(6) Uani 1 1 d . . . N2A N 0.3384(3) 0.5061(3) 0.38632(14) 0.0293(6) Uani 1 1 d . . . C1A C 0.0078(3) 0.8002(3) 0.43395(15) 0.0232(6) Uani 1 1 d . . . C2A C 0.1216(3) 0.8762(3) 0.38426(15) 0.0246(6) Uani 1 1 d . . . C3A C 0.0550(4) 0.8937(3) 0.31343(16) 0.0321(7) Uani 1 1 d . . . C4A C -0.1182(4) 0.8412(4) 0.29387(18) 0.0387(8) Uani 1 1 d . . . C5A C -0.2297(4) 0.7708(3) 0.34289(18) 0.0360(8) Uani 1 1 d . . . C6A C -0.1670(4) 0.7505(3) 0.41257(17) 0.0293(7) Uani 1 1 d . . . C7A C 0.0670(3) 0.7703(3) 0.50878(15) 0.0230(6) Uani 1 1 d . . . C8A C 0.1612(3) 0.6859(3) 0.51709(15) 0.0229(6) Uani 1 1 d . . . C9A C 0.2084(4) 0.6574(3) 0.58921(16) 0.0282(7) Uani 1 1 d . . . C10A C 0.1653(4) 0.7108(3) 0.65054(17) 0.0324(7) Uani 1 1 d . . . C11A C 0.0728(4) 0.7922(3) 0.64223(17) 0.0316(7) Uani 1 1 d . . . C12A C 0.0248(4) 0.8220(3) 0.57152(16) 0.0277(6) Uani 1 1 d . . . C13A C 0.2022(4) 0.6263(3) 0.45223(17) 0.0264(6) Uani 1 1 d . . . C14A C 0.3117(4) 0.5674(3) 0.45329(16) 0.0260(6) Uani 1 1 d . . . C15A C 0.3672(4) 1.0748(4) 0.46002(18) 0.0378(8) Uani 1 1 d . . . H15A H 0.3655 1.1578 0.4327 0.057 Uiso 1 1 calc R . . H15B H 0.4846 1.1018 0.4818 0.057 Uiso 1 1 calc R . . H15C H 0.2962 1.0575 0.4996 0.057 Uiso 1 1 calc R . . C16A C 0.4064(4) 0.9550(4) 0.35037(19) 0.0454(9) Uani 1 1 d . . . H16A H 0.3560 0.8634 0.3153 0.068 Uiso 1 1 calc R . . H16B H 0.5207 0.9734 0.3726 0.068 Uiso 1 1 calc R . . H16C H 0.4141 1.0421 0.3241 0.068 Uiso 1 1 calc R . . O1B O 1.0074(3) 0.9869(2) 0.10912(12) 0.0365(5) Uani 1 1 d . . . O2B O 0.9015(3) 1.0997(3) 0.17603(11) 0.0387(6) Uani 1 1 d . . . N1B N 0.8679(3) 1.4749(3) 0.09673(13) 0.0285(6) Uani 1 1 d . . . N2B N 0.9210(3) 1.0564(3) 0.11505(14) 0.0288(6) Uani 1 1 d . . . C1B C 0.5583(3) 1.3274(3) 0.07101(16) 0.0261(6) Uani 1 1 d . . . C2B C 0.7052(4) 1.4231(3) 0.12107(15) 0.0260(6) Uani 1 1 d . . . C3B C 0.6876(4) 1.4651(3) 0.19239(17) 0.0308(7) Uani 1 1 d . . . C4B C 0.5264(4) 1.4142(4) 0.2140(2) 0.0400(8) Uani 1 1 d . . . C5B C 0.3826(4) 1.3275(4) 0.1641(2) 0.0406(8) Uani 1 1 d . . . C6B C 0.3987(4) 1.2838(3) 0.09332(18) 0.0323(7) Uani 1 1 d . . . C7B C 0.5679(3) 1.2702(3) -0.00389(15) 0.0253(6) Uani 1 1 d . . . C8B C 0.6515(3) 1.1800(3) -0.01387(15) 0.0237(6) Uani 1 1 d . . . C9B C 0.6457(4) 1.1190(3) -0.08584(16) 0.0284(7) Uani 1 1 d . . . C10B C 0.5630(4) 1.1508(4) -0.14684(18) 0.0345(7) Uani 1 1 d . . . C11B C 0.4856(4) 1.2428(4) -0.13727(17) 0.0365(8) Uani 1 1 d . . . C12B C 0.4860(4) 1.3007(3) -0.06709(17) 0.0320(7) Uani 1 1 d . . . C13B C 0.7385(3) 1.1458(3) 0.05064(16) 0.0249(6) Uani 1 1 d . . . C14B C 0.8453(4) 1.0863(3) 0.04822(16) 0.0248(6) Uani 1 1 d . . . C15B C 0.8987(4) 1.5921(4) 0.04451(18) 0.0373(8) Uani 1 1 d . . . H15D H 0.8038 1.5548 0.0036 0.056 Uiso 1 1 calc R . . H15E H 1.0050 1.6147 0.0247 0.056 Uiso 1 1 calc R . . H15F H 0.9079 1.6846 0.0706 0.056 Uiso 1 1 calc R . . C16B C 1.0138(4) 1.5199(4) 0.15428(19) 0.0428(8) Uani 1 1 d . . . H16D H 1.0357 1.6154 0.1819 0.064 Uiso 1 1 calc R . . H16E H 1.1143 1.5339 0.1314 0.064 Uiso 1 1 calc R . . H16F H 0.9898 1.4407 0.1883 0.064 Uiso 1 1 calc R . . H3A H 0.128(5) 0.937(5) 0.278(2) 0.064 Uiso 1 1 d . . . H4A H -0.158(5) 0.853(4) 0.242(2) 0.064 Uiso 1 1 d . . . H5A H -0.347(5) 0.742(5) 0.329(2) 0.064 Uiso 1 1 d . . . H6A H -0.248(5) 0.699(4) 0.453(2) 0.064 Uiso 1 1 d . . . H9A H 0.270(5) 0.588(5) 0.593(2) 0.064 Uiso 1 1 d . . . H10A H 0.208(5) 0.693(4) 0.703(2) 0.064 Uiso 1 1 d . . . H11A H 0.041(5) 0.837(5) 0.687(2) 0.064 Uiso 1 1 d . . . H12A H -0.040(5) 0.882(5) 0.567(2) 0.064 Uiso 1 1 d . . . H13A H 0.150(5) 0.626(4) 0.402(2) 0.064 Uiso 1 1 d . . . H14A H 0.381(5) 0.555(4) 0.498(2) 0.064 Uiso 1 1 d . . . H3B H 0.792(5) 1.532(5) 0.229(2) 0.064 Uiso 1 1 d . . . H4B H 0.522(5) 1.453(5) 0.263(2) 0.064 Uiso 1 1 d . . . H5B H 0.267(5) 1.274(5) 0.177(2) 0.064 Uiso 1 1 d . . . H6B H 0.290(5) 1.212(5) 0.056(2) 0.064 Uiso 1 1 d . . . H9B H 0.703(5) 1.054(5) -0.090(2) 0.064 Uiso 1 1 d . . . H10B H 0.558(5) 1.108(4) -0.200(2) 0.064 Uiso 1 1 d . . . H11B H 0.417(5) 1.266(5) -0.181(2) 0.064 Uiso 1 1 d . . . H12B H 0.433(5) 1.363(5) -0.057(2) 0.064 Uiso 1 1 d . . . H13B H 0.716(5) 1.166(4) 0.100(2) 0.064 Uiso 1 1 d . . . H14B H 0.883(5) 1.065(5) 0.006(2) 0.064 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 O1A 0.0467(13) 0.0501(14) 0.0438(13) 0.0045(11) 0.0135(11) 0.0356(12) O2A 0.0510(14) 0.0588(16) 0.0295(12) 0.0069(11) 0.0089(10) 0.0355(13) N1A 0.0268(13) 0.0309(14) 0.0297(13) 0.0059(11) 0.0090(10) 0.0142(11) N2A 0.0258(13) 0.0305(14) 0.0334(14) 0.0051(11) 0.0088(11) 0.0132(12) C1A 0.0275(15) 0.0195(14) 0.0230(14) 0.0005(11) 0.0040(11) 0.0110(12) C2A 0.0299(15) 0.0194(14) 0.0256(14) 0.0016(11) 0.0009(12) 0.0128(13) C3A 0.0426(19) 0.0242(16) 0.0264(16) 0.0029(12) 0.0020(13) 0.0131(15) C4A 0.043(2) 0.0310(18) 0.0323(18) 0.0030(14) -0.0069(15) 0.0111(16) C5A 0.0300(17) 0.0258(16) 0.0430(19) 0.0018(14) -0.0078(14) 0.0074(14) C6A 0.0286(16) 0.0223(15) 0.0354(17) 0.0019(13) 0.0031(13) 0.0106(13) C7A 0.0193(14) 0.0205(14) 0.0260(15) 0.0019(11) 0.0022(11) 0.0064(12) C8A 0.0219(14) 0.0185(14) 0.0260(15) 0.0008(11) 0.0026(11) 0.0073(12) C9A 0.0287(16) 0.0251(15) 0.0301(16) 0.0051(12) 0.0050(12) 0.0112(13) C10A 0.0346(17) 0.0303(17) 0.0294(16) 0.0052(13) 0.0035(13) 0.0120(15) C11A 0.0383(18) 0.0280(17) 0.0273(16) 0.0012(13) 0.0089(13) 0.0131(15) C12A 0.0297(16) 0.0271(16) 0.0282(16) 0.0026(12) 0.0064(12) 0.0140(14) C13A 0.0252(15) 0.0203(14) 0.0311(16) 0.0001(12) 0.0039(12) 0.0081(13) C14A 0.0260(15) 0.0235(15) 0.0282(16) 0.0037(12) 0.0051(12) 0.0105(13) C15A 0.0310(17) 0.0340(18) 0.0426(19) 0.0018(15) 0.0025(14) 0.0104(15) C16A 0.0375(19) 0.059(2) 0.040(2) 0.0099(17) 0.0153(15) 0.0193(18) O1B 0.0377(12) 0.0416(13) 0.0424(13) 0.0072(10) 0.0076(10) 0.0280(11) O2B 0.0507(14) 0.0491(14) 0.0259(11) 0.0008(10) 0.0045(10) 0.0317(12) N1B 0.0209(12) 0.0285(13) 0.0330(14) -0.0018(11) 0.0031(10) 0.0091(11) N2B 0.0278(13) 0.0271(13) 0.0319(14) 0.0044(11) 0.0067(10) 0.0120(11) C1B 0.0263(15) 0.0234(15) 0.0322(16) 0.0014(12) 0.0033(12) 0.0149(13) C2B 0.0282(15) 0.0209(15) 0.0318(16) 0.0039(12) 0.0096(12) 0.0124(13) C3B 0.0382(18) 0.0249(16) 0.0307(16) 0.0023(13) 0.0086(14) 0.0146(15) C4B 0.049(2) 0.040(2) 0.0413(19) 0.0041(16) 0.0205(16) 0.0255(18) C5B 0.0349(19) 0.0364(19) 0.053(2) 0.0000(16) 0.0205(16) 0.0156(16) C6B 0.0255(16) 0.0264(16) 0.0447(19) 0.0009(14) 0.0085(14) 0.0109(14) C7B 0.0198(14) 0.0203(14) 0.0315(16) 0.0018(12) 0.0028(12) 0.0055(12) C8B 0.0223(14) 0.0200(14) 0.0255(15) 0.0035(11) 0.0058(11) 0.0060(12) C9B 0.0249(15) 0.0272(16) 0.0287(16) 0.0031(12) 0.0064(12) 0.0071(13) C10B 0.0348(17) 0.0339(18) 0.0272(17) 0.0035(14) 0.0038(13) 0.0089(15) C11B 0.0329(17) 0.0352(18) 0.0334(18) 0.0062(14) -0.0036(14) 0.0100(15) C12B 0.0266(16) 0.0270(16) 0.0396(18) 0.0035(13) -0.0027(13) 0.0114(14) C13B 0.0251(15) 0.0202(15) 0.0269(15) 0.0025(12) 0.0082(12) 0.0070(12) C14B 0.0265(15) 0.0222(15) 0.0240(15) 0.0013(12) 0.0050(12) 0.0092(12) C15B 0.0334(18) 0.0359(18) 0.0419(19) 0.0071(15) 0.0089(14) 0.0141(15) C16B 0.0283(17) 0.047(2) 0.045(2) -0.0038(16) -0.0003(15) 0.0109(16) _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 O1A N2A 1.237(3) . ? O2A N2A 1.232(3) . ? N1A C2A 1.425(4) . ? N1A C16A 1.456(4) . ? N1A C15A 1.483(4) . ? N2A C14A 1.431(4) . ? C1A C6A 1.400(4) . ? C1A C2A 1.407(4) . ? C1A C7A 1.493(4) . ? C2A C3A 1.407(4) . ? C3A C4A 1.379(4) . ? C4A C5A 1.374(5) . ? C5A C6A 1.386(4) . ? C7A C12A 1.389(4) . ? C7A C8A 1.418(4) . ? C8A C9A 1.411(4) . ? C8A C13A 1.452(4) . ? C9A C10A 1.379(4) . ? C10A C11A 1.380(4) . ? C11A C12A 1.394(4) . ? C13A C14A 1.332(4) . ? O1B N2B 1.244(3) . ? O2B N2B 1.233(3) . ? N1B C2B 1.427(4) . ? N1B C16B 1.455(4) . ? N1B C15B 1.477(4) . ? N2B C14B 1.428(4) . ? C1B C6B 1.395(4) . ? C1B C2B 1.411(4) . ? C1B C7B 1.483(4) . ? C2B C3B 1.395(4) . ? C3B C4B 1.395(4) . ? C4B C5B 1.375(5) . ? C5B C6B 1.387(5) . ? C7B C12B 1.406(4) . ? C7B C8B 1.407(4) . ? C8B C9B 1.408(4) . ? C8B C13B 1.465(4) . ? C9B C10B 1.385(4) . ? C10B C11B 1.377(4) . ? C11B C12B 1.380(4) . ? C13B C14B 1.320(4) . ? 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 C2A N1A C16A 116.1(2) . . ? C2A N1A C15A 112.0(2) . . ? C16A N1A C15A 110.8(3) . . ? O2A N2A O1A 122.7(2) . . ? O2A N2A C14A 120.6(2) . . ? O1A N2A C14A 116.7(2) . . ? C6A C1A C2A 119.1(2) . . ? C6A C1A C7A 118.8(2) . . ? C2A C1A C7A 122.2(2) . . ? C3A C2A C1A 118.7(3) . . ? C3A C2A N1A 122.8(3) . . ? C1A C2A N1A 118.4(2) . . ? C4A C3A C2A 120.6(3) . . ? C5A C4A C3A 121.0(3) . . ? C4A C5A C6A 119.4(3) . . ? C5A C6A C1A 121.2(3) . . ? C12A C7A C8A 119.1(2) . . ? C12A C7A C1A 119.4(2) . . ? C8A C7A C1A 121.4(2) . . ? C9A C8A C7A 118.5(2) . . ? C9A C8A C13A 121.2(2) . . ? C7A C8A C13A 120.3(2) . . ? C10A C9A C8A 121.1(3) . . ? C9A C10A C11A 120.3(3) . . ? C10A C11A C12A 119.7(3) . . ? C7A C12A C11A 121.3(3) . . ? C14A C13A C8A 125.4(3) . . ? C13A C14A N2A 121.1(3) . . ? C2B N1B C16B 116.5(2) . . ? C2B N1B C15B 112.5(2) . . ? C16B N1B C15B 111.1(3) . . ? O2B N2B O1B 121.9(2) . . ? O2B N2B C14B 120.5(2) . . ? O1B N2B C14B 117.6(2) . . ? C6B C1B C2B 118.7(3) . . ? C6B C1B C7B 119.0(3) . . ? C2B C1B C7B 122.3(2) . . ? C3B C2B C1B 119.4(3) . . ? C3B C2B N1B 121.9(3) . . ? C1B C2B N1B 118.7(2) . . ? C2B C3B C4B 120.4(3) . . ? C5B C4B C3B 120.2(3) . . ? C4B C5B C6B 119.7(3) . . ? C5B C6B C1B 121.4(3) . . ? C12B C7B C8B 118.4(3) . . ? C12B C7B C1B 119.8(2) . . ? C8B C7B C1B 121.8(2) . . ? C7B C8B C9B 119.5(2) . . ? C7B C8B C13B 119.9(2) . . ? C9B C8B C13B 120.6(2) . . ? C10B C9B C8B 120.6(3) . . ? C11B C10B C9B 119.9(3) . . ? C10B C11B C12B 120.5(3) . . ? C11B C12B C7B 121.1(3) . . ? C14B C13B C8B 125.5(3) . . ? C13B C14B N2B 120.4(3) . . ? _diffrn_measured_fraction_theta_max 0.970 _diffrn_reflns_theta_full 27.45 _diffrn_measured_fraction_theta_full 0.970 _refine_diff_density_max 0.454 _refine_diff_density_min -0.381 _refine_diff_density_rms 0.077 data_compound4 _database_code_depnum_ccdc_archive 'CCDC 658335' _audit_creation_method SHELXL-97 _chemical_name_systematic ; Methyl E-2-cyano-3-(2-(Dimethylamino)biphen-2-yl)propenoate ; _chemical_name_common 'Methyl E-2-cyano-3-(2-(Dimethylamino)biphen-2-yl)propenoate' _chemical_melting_point 377-379 _chemical_formula_moiety ? _chemical_formula_sum 'C19 H18 N2 O2' _chemical_formula_weight 306.35 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z' '-x, -y, -z' 'x-1/2, -y-1/2, z' _cell_length_a 8.2446(2) _cell_length_b 17.2928(4) _cell_length_c 11.6833(2) _cell_angle_alpha 90.00 _cell_angle_beta 107.1770(17) _cell_angle_gamma 90.00 _cell_volume 1591.42(6) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7231 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.279 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 648 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.96 _exptl_absorpt_correction_T_max 0.99 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15927 _diffrn_reflns_av_R_equivalents 0.0493 _diffrn_reflns_av_sigmaI/netI 0.0408 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 22 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.46 _reflns_number_total 3568 _reflns_number_gt 2837 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _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^)+(0.0620P)^2^+0.3097P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3568 _refine_ls_number_parameters 280 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0603 _refine_ls_R_factor_gt 0.0434 _refine_ls_wR_factor_ref 0.1142 _refine_ls_wR_factor_gt 0.1070 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.009 _refine_ls_shift/su_mean 0.002 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 O1 O 0.67732(12) 0.12629(5) 0.83276(8) 0.0273(2) Uani 1 1 d . . . O2 O 0.42734(11) 0.18895(5) 0.77137(8) 0.0246(2) Uani 1 1 d . . . N1 N 0.65233(14) -0.11098(6) 0.87964(10) 0.0243(3) Uani 1 1 d . . . N2 N 0.10908(15) 0.07448(8) 0.63347(12) 0.0355(3) Uani 1 1 d . . . C1 C 0.77507(16) -0.12249(7) 0.71378(11) 0.0223(3) Uani 1 1 d . . . C2 C 0.79832(16) -0.11332(7) 0.83800(11) 0.0223(3) Uani 1 1 d . . . C3 C 0.96329(17) -0.10522(8) 0.91539(12) 0.0256(3) Uani 1 1 d . . . C4 C 1.10222(18) -0.10819(8) 0.87107(13) 0.0288(3) Uani 1 1 d . . . C5 C 1.08084(18) -0.11905(8) 0.75048(13) 0.0294(3) Uani 1 1 d . . . C6 C 0.91720(17) -0.12603(8) 0.67271(13) 0.0265(3) Uani 1 1 d . . . C7 C 0.60277(16) -0.12757(8) 0.62529(11) 0.0220(3) Uani 1 1 d . . . C8 C 0.47967(15) -0.06831(7) 0.61292(11) 0.0201(3) Uani 1 1 d . . . C9 C 0.32143(16) -0.07723(8) 0.52689(11) 0.0220(3) Uani 1 1 d . . . C10 C 0.28415(17) -0.14304(8) 0.45569(12) 0.0246(3) Uani 1 1 d . . . C11 C 0.40428(18) -0.20067(8) 0.46824(12) 0.0265(3) Uani 1 1 d . . . C12 C 0.56206(17) -0.19275(8) 0.55184(12) 0.0251(3) Uani 1 1 d . . . C13 C 0.52873(16) 0.00173(7) 0.68474(11) 0.0201(3) Uani 1 1 d . . . C14 C 0.43528(15) 0.06135(8) 0.70507(11) 0.0205(3) Uani 1 1 d . . . C15 C 0.25389(17) 0.06764(8) 0.66349(11) 0.0239(3) Uani 1 1 d . . . C16 C 0.52881(16) 0.12764(7) 0.77695(11) 0.0205(3) Uani 1 1 d . . . C17 C 0.51018(19) 0.25699(8) 0.83484(13) 0.0287(3) Uani 1 1 d . . . C18 C 0.56292(19) -0.18493(9) 0.87054(14) 0.0304(3) Uani 1 1 d . . . C19 C 0.6769(2) -0.07575(10) 0.99650(13) 0.0335(4) Uani 1 1 d . . . H3 H 0.9764(19) -0.0961(10) 1.0013(15) 0.030(4) Uiso 1 1 d . . . H4 H 1.218(2) -0.1036(10) 0.9307(15) 0.035(4) Uiso 1 1 d . . . H5 H 1.182(2) -0.1234(9) 0.7195(14) 0.031(4) Uiso 1 1 d . . . H6 H 0.899(2) -0.1314(9) 0.5853(15) 0.032(4) Uiso 1 1 d . . . H9 H 0.2384(19) -0.0378(9) 0.5167(13) 0.027(4) Uiso 1 1 d . . . H10 H 0.171(2) -0.1470(9) 0.3982(14) 0.029(4) Uiso 1 1 d . . . H11 H 0.379(2) -0.2471(11) 0.4197(15) 0.039(4) Uiso 1 1 d . . . H12 H 0.647(2) -0.2349(10) 0.5612(13) 0.031(4) Uiso 1 1 d . . . H13 H 0.6513(17) 0.0081(8) 0.7207(12) 0.016(3) Uiso 1 1 d . . . H17A H 0.595(2) 0.2756(10) 0.7972(14) 0.031(4) Uiso 1 1 d . . . H17B H 0.569(2) 0.2427(11) 0.9193(16) 0.043(5) Uiso 1 1 d . . . H17C H 0.421(2) 0.2936(10) 0.8300(14) 0.030(4) Uiso 1 1 d . . . H18A H 0.631(2) -0.2234(10) 0.9312(15) 0.038(4) Uiso 1 1 d . . . H18B H 0.543(2) -0.2092(11) 0.7897(16) 0.043(5) Uiso 1 1 d . . . H18C H 0.449(2) -0.1760(10) 0.8855(14) 0.036(4) Uiso 1 1 d . . . H19A H 0.559(2) -0.0670(10) 1.0073(14) 0.035(4) Uiso 1 1 d . . . H19B H 0.734(2) -0.0266(11) 0.9985(14) 0.037(4) Uiso 1 1 d . . . H19C H 0.751(2) -0.1091(9) 1.0660(14) 0.030(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 O1 0.0243(5) 0.0264(5) 0.0277(5) -0.0023(4) 0.0024(4) 0.0005(4) O2 0.0254(5) 0.0206(5) 0.0276(5) -0.0043(4) 0.0072(4) 0.0004(4) N1 0.0287(6) 0.0222(6) 0.0231(6) 0.0017(4) 0.0094(4) 0.0020(5) N2 0.0246(6) 0.0372(8) 0.0428(8) -0.0059(6) 0.0071(5) 0.0027(5) C1 0.0250(7) 0.0178(7) 0.0238(7) 0.0028(5) 0.0069(5) 0.0015(5) C2 0.0289(7) 0.0140(6) 0.0242(7) 0.0024(5) 0.0081(5) 0.0030(5) C3 0.0299(7) 0.0190(7) 0.0257(7) 0.0011(5) 0.0049(5) 0.0024(5) C4 0.0243(7) 0.0233(7) 0.0348(8) 0.0023(6) 0.0026(6) 0.0011(6) C5 0.0270(7) 0.0262(8) 0.0368(8) 0.0034(6) 0.0124(6) 0.0011(6) C6 0.0271(7) 0.0251(7) 0.0283(8) 0.0017(5) 0.0099(6) 0.0032(6) C7 0.0237(7) 0.0216(7) 0.0219(6) 0.0029(5) 0.0087(5) -0.0004(5) C8 0.0215(6) 0.0201(6) 0.0202(6) 0.0022(5) 0.0083(5) -0.0011(5) C9 0.0207(6) 0.0237(7) 0.0224(6) 0.0019(5) 0.0078(5) 0.0001(5) C10 0.0242(7) 0.0285(7) 0.0218(7) 0.0000(5) 0.0077(5) -0.0049(6) C11 0.0313(7) 0.0237(7) 0.0266(7) -0.0028(5) 0.0121(6) -0.0051(6) C12 0.0281(7) 0.0222(7) 0.0269(7) 0.0008(5) 0.0111(5) 0.0012(6) C13 0.0204(6) 0.0216(7) 0.0182(6) 0.0042(5) 0.0055(5) -0.0008(5) C14 0.0205(6) 0.0223(7) 0.0180(6) 0.0017(5) 0.0048(5) -0.0009(5) C15 0.0257(7) 0.0217(7) 0.0241(7) -0.0029(5) 0.0071(5) 0.0008(5) C16 0.0230(6) 0.0212(7) 0.0182(6) 0.0022(5) 0.0077(5) 0.0018(5) C17 0.0308(7) 0.0228(7) 0.0316(8) -0.0070(6) 0.0077(6) -0.0009(6) C18 0.0320(8) 0.0290(8) 0.0329(8) 0.0024(6) 0.0137(6) -0.0024(6) C19 0.0431(9) 0.0324(9) 0.0283(8) -0.0044(6) 0.0154(7) 0.0020(7) _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 O1 C16 1.2055(15) . ? O2 C16 1.3401(16) . ? O2 C17 1.4497(16) . ? N1 C2 1.4259(17) . ? N1 C19 1.4535(18) . ? N1 C18 1.4642(19) . ? N2 C15 1.1467(17) . ? C1 C6 1.3926(19) . ? C1 C2 1.4155(19) . ? C1 C7 1.4924(18) . ? C2 C3 1.4003(18) . ? C3 C4 1.390(2) . ? C4 C5 1.380(2) . ? C5 C6 1.392(2) . ? C7 C12 1.3962(19) . ? C7 C8 1.4193(18) . ? C8 C9 1.4006(17) . ? C8 C13 1.4608(18) . ? C9 C10 1.3895(19) . ? C10 C11 1.382(2) . ? C11 C12 1.3837(19) . ? C13 C14 1.3495(18) . ? C14 C15 1.4336(17) . ? C14 C16 1.4938(18) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C16 O2 C17 115.10(10) . . ? C2 N1 C19 115.77(11) . . ? C2 N1 C18 114.08(11) . . ? C19 N1 C18 111.22(12) . . ? C6 C1 C2 119.03(12) . . ? C6 C1 C7 118.97(12) . . ? C2 C1 C7 121.99(12) . . ? C3 C2 C1 119.01(12) . . ? C3 C2 N1 122.25(12) . . ? C1 C2 N1 118.73(11) . . ? C4 C3 C2 120.38(13) . . ? C5 C4 C3 120.95(13) . . ? C4 C5 C6 119.03(13) . . ? C5 C6 C1 121.56(13) . . ? C12 C7 C8 119.05(12) . . ? C12 C7 C1 118.69(12) . . ? C8 C7 C1 122.26(11) . . ? C9 C8 C7 118.69(12) . . ? C9 C8 C13 123.01(11) . . ? C7 C8 C13 118.15(11) . . ? C10 C9 C8 120.95(12) . . ? C11 C10 C9 120.15(12) . . ? C10 C11 C12 119.90(13) . . ? C11 C12 C7 121.26(13) . . ? C14 C13 C8 131.21(12) . . ? C13 C14 C15 126.23(12) . . ? C13 C14 C16 117.29(11) . . ? C15 C14 C16 116.48(11) . . ? N2 C15 C14 177.58(14) . . ? O1 C16 O2 124.15(12) . . ? O1 C16 C14 124.22(11) . . ? O2 C16 C14 111.63(10) . . ? _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 27.49 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 0.283 _refine_diff_density_min -0.221 _refine_diff_density_rms 0.045 data_d:\biphen_compound8 _database_code_depnum_ccdc_archive 'CCDC 658336' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 5-(1,2-Dihydro-1,1-dimethylbenzo(c)quinolinium-2-yl) -dicyanomethide ; _chemical_name_common ;5-(1,2-Dihydro-1,1-dimethylbenzo(c)quinolinium-2-yl) - dicyanomethide ; _chemical_melting_point 92-94 _chemical_formula_moiety 'C18 H15 N3' _chemical_formula_sum 'C18 H15 N3' _chemical_formula_weight 273.33 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.4599(4) _cell_length_b 8.2053(3) _cell_length_c 14.7752(7) _cell_angle_alpha 90.00 _cell_angle_beta 92.1420(10) _cell_angle_gamma 90.00 _cell_volume 1388.37(10) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 8822 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.308 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 576 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.964 _exptl_absorpt_correction_T_max 0.998 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10933 _diffrn_reflns_av_R_equivalents 0.0516 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_theta_min 3.32 _diffrn_reflns_theta_max 27.46 _reflns_number_total 5657 _reflns_number_gt 4750 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _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^)+(0.0602P)^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_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration unk _refine_ls_abs_structure_Flack 0.2(19) _refine_ls_number_reflns 5657 _refine_ls_number_parameters 387 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0465 _refine_ls_wR_factor_ref 0.1120 _refine_ls_wR_factor_gt 0.1059 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.988 _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 N1A N 0.21299(14) 0.70104(19) 0.76413(11) 0.0182(4) Uani 1 1 d . . . N2A N 0.34773(17) 0.4594(2) 0.52226(13) 0.0299(5) Uani 1 1 d . . . N3A N 0.07572(16) 0.2411(2) 0.68856(14) 0.0337(5) Uani 1 1 d . . . C1A C 0.37818(17) 0.7836(2) 0.67242(13) 0.0187(4) Uani 1 1 d . . . C2A C 0.34106(17) 0.7059(2) 0.75103(13) 0.0179(4) Uani 1 1 d . . . C3A C 0.41847(18) 0.6346(3) 0.81255(14) 0.0237(5) Uani 1 1 d . . . H3A H 0.3912 0.5859 0.8661 0.028 Uiso 1 1 calc R . . C4A C 0.53689(19) 0.6347(3) 0.79540(16) 0.0274(5) Uani 1 1 d . . . H4A H 0.5913 0.5858 0.8372 0.033 Uiso 1 1 calc R . . C5A C 0.57517(19) 0.7066(3) 0.71682(16) 0.0281(5) Uani 1 1 d . . . H5A H 0.6559 0.7048 0.7045 0.034 Uiso 1 1 calc R . . C6A C 0.49763(18) 0.7804(2) 0.65657(15) 0.0230(5) Uani 1 1 d . . . H6A H 0.5256 0.8299 0.6034 0.028 Uiso 1 1 calc R . . C7A C 0.29123(17) 0.8577(2) 0.60862(13) 0.0186(4) Uani 1 1 d . . . C8A C 0.17675(18) 0.7988(2) 0.60733(13) 0.0187(4) Uani 1 1 d . . . C9A C 0.09019(18) 0.8705(2) 0.55213(13) 0.0220(5) Uani 1 1 d . . . H9A H 0.0126 0.8296 0.5516 0.026 Uiso 1 1 calc R . . C10A C 0.1175(2) 1.0020(3) 0.49790(14) 0.0265(5) Uani 1 1 d . . . H10A H 0.0587 1.0516 0.4602 0.032 Uiso 1 1 calc R . . C11A C 0.2313(2) 1.0612(3) 0.49875(14) 0.0276(5) Uani 1 1 d . . . H11A H 0.2496 1.1513 0.4615 0.033 Uiso 1 1 calc R . . C12A C 0.31758(19) 0.9907(3) 0.55290(13) 0.0244(5) Uani 1 1 d . . . H12A H 0.3950 1.0319 0.5527 0.029 Uiso 1 1 calc R . . C13A C 0.14912(18) 0.6587(2) 0.66852(13) 0.0179(4) Uani 1 1 d . . . H13A H 0.0656(18) 0.658(2) 0.6868(13) 0.018(5) Uiso 1 1 d . . . C14A C 0.18259(17) 0.4952(2) 0.63354(13) 0.0180(4) Uani 1 1 d . . . C15A C 0.27324(18) 0.4760(2) 0.57296(13) 0.0203(4) Uani 1 1 d . . . C16A C 0.12416(18) 0.3555(2) 0.66228(14) 0.0231(5) Uani 1 1 d . . . C17A C 0.16652(18) 0.8617(2) 0.79687(14) 0.0241(5) Uani 1 1 d . . . H17U H 0.0822 0.8528 0.8045 0.036 Uiso 1 1 calc R . . H17V H 0.1820 0.9468 0.7524 0.036 Uiso 1 1 calc R . . H17W H 0.2052 0.8898 0.8551 0.036 Uiso 1 1 calc R . . C18A C 0.17956(18) 0.5748(2) 0.83224(14) 0.0239(5) Uani 1 1 d . . . H18U H 0.0947 0.5760 0.8384 0.036 Uiso 1 1 calc R . . H18V H 0.2182 0.5992 0.8910 0.036 Uiso 1 1 calc R . . H18W H 0.2040 0.4668 0.8118 0.036 Uiso 1 1 calc R . . N1B N 0.24624(14) 0.66512(19) 0.27248(11) 0.0181(4) Uani 1 1 d . . . N2B N 0.11270(16) 1.1354(2) 0.22915(13) 0.0277(4) Uani 1 1 d . . . N3B N 0.29921(17) 0.9087(2) 0.00574(13) 0.0307(5) Uani 1 1 d . . . C1B C 0.37880(17) 0.5715(2) 0.15599(13) 0.0186(4) Uani 1 1 d . . . C2B C 0.36703(17) 0.6515(2) 0.23905(13) 0.0183(4) Uani 1 1 d . . . C3B C 0.46198(18) 0.7156(2) 0.28743(15) 0.0226(4) Uani 1 1 d . . . H3B H 0.4520 0.7676 0.3441 0.027 Uiso 1 1 calc R . . C4B C 0.57201(19) 0.7029(3) 0.25208(15) 0.0270(5) Uani 1 1 d . . . H4B H 0.6379 0.7470 0.2844 0.032 Uiso 1 1 calc R . . C5B C 0.58585(18) 0.6260(3) 0.16988(15) 0.0260(5) Uani 1 1 d . . . H5B H 0.6613 0.6184 0.1458 0.031 Uiso 1 1 calc R . . C6B C 0.49128(17) 0.5604(2) 0.12272(14) 0.0221(5) Uani 1 1 d . . . H6B H 0.5025 0.5069 0.0667 0.027 Uiso 1 1 calc R . . C7B C 0.27487(17) 0.5064(2) 0.10625(12) 0.0178(4) Uani 1 1 d . . . C8B C 0.16594(17) 0.5771(2) 0.12242(13) 0.0170(4) Uani 1 1 d . . . C9B C 0.06608(18) 0.5194(2) 0.07788(13) 0.0200(4) Uani 1 1 d . . . H9B H -0.0070 0.5691 0.0886 0.024 Uiso 1 1 calc R . . C10B C 0.07100(18) 0.3897(2) 0.01774(14) 0.0224(5) Uani 1 1 d . . . H10B H 0.0021 0.3512 -0.0130 0.027 Uiso 1 1 calc R . . C11B C 0.17838(19) 0.3171(2) 0.00312(14) 0.0225(5) Uani 1 1 d . . . H11B H 0.1825 0.2269 -0.0369 0.027 Uiso 1 1 calc R . . C12B C 0.27896(18) 0.3751(2) 0.04630(13) 0.0206(4) Uani 1 1 d . . . H12B H 0.3518 0.3251 0.0351 0.025 Uiso 1 1 calc R . . C13B C 0.16056(17) 0.7146(2) 0.19025(14) 0.0171(4) Uani 1 1 d . . . H13B H 0.0860(17) 0.714(2) 0.2201(13) 0.014(5) Uiso 1 1 d . . . C14B C 0.18668(17) 0.8772(2) 0.15151(13) 0.0183(4) Uani 1 1 d . . . C15B C 0.14629(17) 1.0191(2) 0.19285(14) 0.0206(4) Uani 1 1 d . . . C16B C 0.24903(18) 0.8939(2) 0.07204(14) 0.0202(4) Uani 1 1 d . . . C17B C 0.20460(19) 0.5065(2) 0.31231(13) 0.0237(5) Uani 1 1 d . . . H17X H 0.1253 0.5207 0.3337 0.035 Uiso 1 1 calc R . . H17Y H 0.2570 0.4749 0.3632 0.035 Uiso 1 1 calc R . . H17Z H 0.2045 0.4213 0.2658 0.035 Uiso 1 1 calc R . . C18B C 0.2368(2) 0.7918(3) 0.34504(14) 0.0249(5) Uani 1 1 d . . . H18X H 0.1563 0.7960 0.3650 0.037 Uiso 1 1 calc R . . H18Y H 0.2587 0.8984 0.3210 0.037 Uiso 1 1 calc R . . H18Z H 0.2894 0.7636 0.3965 0.037 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 N1A 0.0193(9) 0.0188(9) 0.0165(9) 0.0014(7) 0.0036(7) -0.0008(7) N2A 0.0360(11) 0.0254(10) 0.0290(10) -0.0053(8) 0.0121(9) -0.0029(9) N3A 0.0335(11) 0.0237(10) 0.0455(13) -0.0048(9) 0.0206(10) -0.0057(8) C1A 0.0217(11) 0.0178(10) 0.0167(10) -0.0043(8) 0.0021(8) -0.0041(8) C2A 0.0166(10) 0.0182(10) 0.0189(10) -0.0034(8) 0.0016(8) -0.0001(8) C3A 0.0267(12) 0.0220(10) 0.0221(11) 0.0008(9) -0.0018(9) -0.0014(9) C4A 0.0243(12) 0.0212(10) 0.0361(13) -0.0004(10) -0.0054(10) -0.0005(9) C5A 0.0198(11) 0.0248(11) 0.0399(14) -0.0071(10) 0.0039(10) -0.0026(9) C6A 0.0230(11) 0.0203(11) 0.0262(12) -0.0054(9) 0.0065(9) -0.0058(9) C7A 0.0258(11) 0.0166(10) 0.0137(10) -0.0025(8) 0.0042(8) -0.0012(9) C8A 0.0240(11) 0.0166(10) 0.0158(10) -0.0030(8) 0.0043(8) -0.0001(8) C9A 0.0265(11) 0.0193(10) 0.0202(10) -0.0037(8) 0.0017(9) 0.0039(9) C10A 0.0414(14) 0.0192(11) 0.0183(10) -0.0021(9) -0.0056(9) 0.0080(10) C11A 0.0490(14) 0.0162(10) 0.0177(11) 0.0009(8) 0.0027(10) 0.0006(10) C12A 0.0339(13) 0.0226(11) 0.0170(10) -0.0041(9) 0.0065(9) -0.0064(10) C13A 0.0167(10) 0.0208(10) 0.0164(10) -0.0010(8) 0.0019(8) 0.0004(8) C14A 0.0188(10) 0.0158(10) 0.0197(10) -0.0005(8) 0.0049(8) -0.0001(8) C15A 0.0262(11) 0.0152(10) 0.0196(10) -0.0013(8) 0.0016(9) -0.0024(8) C16A 0.0231(11) 0.0207(11) 0.0258(12) -0.0051(9) 0.0065(9) 0.0036(9) C17A 0.0268(11) 0.0245(11) 0.0212(11) -0.0075(9) 0.0059(9) 0.0014(9) C18A 0.0267(11) 0.0251(11) 0.0204(11) 0.0064(9) 0.0065(9) -0.0047(9) N1B 0.0219(9) 0.0185(9) 0.0141(8) 0.0006(7) 0.0041(7) -0.0004(7) N2B 0.0250(10) 0.0209(9) 0.0378(11) -0.0012(8) 0.0103(9) -0.0011(8) N3B 0.0388(12) 0.0306(11) 0.0233(10) 0.0020(8) 0.0088(9) -0.0036(9) C1B 0.0208(10) 0.0187(10) 0.0164(10) 0.0039(8) 0.0014(8) 0.0018(8) C2B 0.0194(10) 0.0171(9) 0.0185(10) 0.0037(8) 0.0025(8) 0.0016(8) C3B 0.0274(11) 0.0186(10) 0.0215(11) 0.0008(8) -0.0021(9) 0.0022(9) C4B 0.0231(11) 0.0224(11) 0.0349(13) 0.0042(9) -0.0079(10) -0.0035(9) C5B 0.0201(11) 0.0255(11) 0.0327(13) 0.0074(10) 0.0031(10) 0.0014(9) C6B 0.0215(11) 0.0222(11) 0.0229(11) 0.0022(8) 0.0042(9) 0.0027(9) C7B 0.0215(11) 0.0185(10) 0.0137(9) 0.0017(8) 0.0041(8) -0.0005(8) C8B 0.0203(10) 0.0143(9) 0.0169(10) 0.0023(8) 0.0057(8) -0.0017(8) C9B 0.0205(10) 0.0182(10) 0.0217(10) 0.0039(8) 0.0036(8) -0.0003(8) C10B 0.0264(11) 0.0203(10) 0.0204(11) 0.0021(9) -0.0016(9) -0.0041(9) C11B 0.0355(13) 0.0172(10) 0.0148(10) -0.0009(8) 0.0015(9) 0.0000(9) C12B 0.0255(11) 0.0198(10) 0.0167(10) -0.0020(8) 0.0045(8) 0.0030(9) C13B 0.0171(10) 0.0174(10) 0.0172(10) 0.0000(8) 0.0036(8) 0.0017(8) C14B 0.0205(10) 0.0177(10) 0.0170(10) 0.0016(8) 0.0039(8) 0.0011(8) C15B 0.0176(10) 0.0198(10) 0.0244(11) 0.0026(9) 0.0030(8) -0.0005(8) C16B 0.0238(11) 0.0156(10) 0.0212(11) 0.0008(8) -0.0012(9) -0.0012(8) C17B 0.0313(12) 0.0193(10) 0.0208(10) 0.0048(9) 0.0072(9) -0.0014(9) C18B 0.0312(12) 0.0273(11) 0.0165(11) -0.0038(9) 0.0045(9) 0.0033(9) _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 N1A C2A 1.488(2) . ? N1A C18A 1.504(2) . ? N1A C17A 1.508(2) . ? N1A C13A 1.604(3) . ? N2A C15A 1.164(3) . ? N3A C16A 1.164(3) . ? C1A C6A 1.398(3) . ? C1A C2A 1.405(3) . ? C1A C7A 1.477(3) . ? C2A C3A 1.377(3) . ? C3A C4A 1.390(3) . ? C4A C5A 1.388(3) . ? C5A C6A 1.375(3) . ? C7A C8A 1.398(3) . ? C7A C12A 1.406(3) . ? C8A C9A 1.391(3) . ? C8A C13A 1.503(3) . ? C9A C10A 1.387(3) . ? C10A C11A 1.390(3) . ? C11A C12A 1.376(3) . ? C13A C14A 1.493(3) . ? C14A C16A 1.402(3) . ? C14A C15A 1.405(3) . ? N1B C2B 1.491(2) . ? N1B C18B 1.500(2) . ? N1B C17B 1.513(2) . ? N1B C13B 1.586(3) . ? N2B C15B 1.167(3) . ? N3B C16B 1.161(3) . ? C1B C6B 1.400(3) . ? C1B C2B 1.403(3) . ? C1B C7B 1.476(3) . ? C2B C3B 1.383(3) . ? C3B C4B 1.387(3) . ? C4B C5B 1.383(3) . ? C5B C6B 1.376(3) . ? C7B C12B 1.396(3) . ? C7B C8B 1.405(3) . ? C8B C9B 1.382(3) . ? C8B C13B 1.512(3) . ? C9B C10B 1.389(3) . ? C10B C11B 1.391(3) . ? C11B C12B 1.381(3) . ? C13B C14B 1.487(3) . ? C14B C15B 1.402(3) . ? C14B C16B 1.404(3) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A N1A C18A 112.50(15) . . ? C2A N1A C17A 112.33(15) . . ? C18A N1A C17A 106.59(14) . . ? C2A N1A C13A 108.12(14) . . ? C18A N1A C13A 108.72(15) . . ? C17A N1A C13A 108.46(15) . . ? C6A C1A C2A 117.31(18) . . ? C6A C1A C7A 122.85(18) . . ? C2A C1A C7A 119.78(17) . . ? C3A C2A C1A 122.09(18) . . ? C3A C2A N1A 121.13(17) . . ? C1A C2A N1A 116.77(17) . . ? C2A C3A C4A 119.3(2) . . ? C5A C4A C3A 119.6(2) . . ? C6A C5A C4A 120.81(19) . . ? C5A C6A C1A 120.88(19) . . ? C8A C7A C12A 118.85(19) . . ? C8A C7A C1A 118.47(17) . . ? C12A C7A C1A 122.59(18) . . ? C9A C8A C7A 120.66(18) . . ? C9A C8A C13A 120.96(18) . . ? C7A C8A C13A 118.37(18) . . ? C10A C9A C8A 119.75(19) . . ? C9A C10A C11A 119.9(2) . . ? C12A C11A C10A 120.80(19) . . ? C11A C12A C7A 120.1(2) . . ? C14A C13A C8A 114.59(16) . . ? C14A C13A N1A 112.61(16) . . ? C8A C13A N1A 105.35(15) . . ? C16A C14A C15A 118.27(17) . . ? C16A C14A C13A 119.90(16) . . ? C15A C14A C13A 121.82(17) . . ? N2A C15A C14A 179.5(2) . . ? N3A C16A C14A 178.1(2) . . ? C2B N1B C18B 112.40(16) . . ? C2B N1B C17B 112.01(14) . . ? C18B N1B C17B 106.61(14) . . ? C2B N1B C13B 108.73(14) . . ? C18B N1B C13B 108.13(14) . . ? C17B N1B C13B 108.84(15) . . ? C6B C1B C2B 117.22(18) . . ? C6B C1B C7B 122.58(17) . . ? C2B C1B C7B 120.19(17) . . ? C3B C2B C1B 122.05(18) . . ? C3B C2B N1B 121.49(18) . . ? C1B C2B N1B 116.46(17) . . ? C2B C3B C4B 119.0(2) . . ? C5B C4B C3B 120.1(2) . . ? C6B C5B C4B 120.6(2) . . ? C5B C6B C1B 121.02(19) . . ? C12B C7B C8B 118.52(18) . . ? C12B C7B C1B 123.32(17) . . ? C8B C7B C1B 118.13(17) . . ? C9B C8B C7B 120.18(18) . . ? C9B C8B C13B 121.18(17) . . ? C7B C8B C13B 118.64(17) . . ? C8B C9B C10B 120.96(18) . . ? C9B C10B C11B 119.00(19) . . ? C12B C11B C10B 120.56(19) . . ? C11B C12B C7B 120.77(18) . . ? C14B C13B C8B 113.63(16) . . ? C14B C13B N1B 113.39(16) . . ? C8B C13B N1B 106.09(15) . . ? C15B C14B C16B 118.03(18) . . ? C15B C14B C13B 120.22(16) . . ? C16B C14B C13B 121.73(17) . . ? N2B C15B C14B 178.4(2) . . ? N3B C16B C14B 179.0(2) . . ? _diffrn_measured_fraction_theta_max 0.994 _diffrn_reflns_theta_full 27.46 _diffrn_measured_fraction_theta_full 0.994 _refine_diff_density_max 0.197 _refine_diff_density_min -0.251 _refine_diff_density_rms 0.051 data_c:\xray\compound9 _database_code_depnum_ccdc_archive 'CCDC 658337' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 2-(1',2'-Dihydo-1',1'-dimethylbenzo(c)-quinolinium-2'-yl)- 5,5-dimethyl-1,3-dioxocyclohexan-2-ide ; _chemical_name_common ; 2-(1',2'-Dihydo-1',1'-dimethylbenzo(c)-quinolinium-2'-yl)-5,5- dimethyl-1,3-dioxocyclohexan-2-ide ; _chemical_melting_point 395-401 _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O3' _chemical_formula_weight 365.46 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' _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 9.3343(2) _cell_length_b 10.2514(2) _cell_length_c 11.3449(2) _cell_angle_alpha 114.4419(8) _cell_angle_beta 91.7559(8) _cell_angle_gamma 105.0489(8) _cell_volume 942.56(3) _cell_formula_units_Z 2 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6297 _cell_measurement_theta_min 2.91 _cell_measurement_theta_max 27.48 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.075 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.288 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 392 _exptl_absorpt_coefficient_mu 0.085 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_T_max 1.00 _exptl_absorpt_process_details ; using multiple and symmetry-related data measurements via the program SORTAV (Blessing, 1995) See R.H. Blessing, Acta Cryst., (1995), A51, 33-38 ; _exptl_special_details ; PLEASE NOTE cell_measurement_ fields are not relecvant to area detector data, the entire data set is used to refine the cell, which is indexed from all observed reflections in a 10 degree phi range. ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Enraf Nonius KappaCCD area detector' _diffrn_measurement_method 'Phi and Omega scans to fill Ewald sphere' _diffrn_detector_area_resol_mean 9.091 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14933 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0438 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.91 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4243 _reflns_number_gt 3328 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_cell_refinement ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_data_reduction ; DENZO (Otwinowski and Minor, 1997) and COLLECT (Hooft, 1998) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEPIII (Johnson and Burnett, 1996)' _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^)+(0.0645P)^2^+0.0475P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4243 _refine_ls_number_parameters 352 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0590 _refine_ls_R_factor_gt 0.0421 _refine_ls_wR_factor_ref 0.1107 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.047 _refine_ls_restrained_S_all 1.047 _refine_ls_shift/su_max 0.010 _refine_ls_shift/su_mean 0.002 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 O1 O 0.49907(9) 0.89933(9) 0.16960(8) 0.0204(2) Uani 1 1 d . . . O2 O 0.00383(9) 0.92056(9) 0.20375(8) 0.0216(2) Uani 1 1 d . . . N1 N 0.17973(11) 0.76631(10) -0.07248(9) 0.0175(2) Uani 1 1 d . . . C1 C 0.10862(13) 0.49052(13) -0.19166(11) 0.0166(2) Uani 1 1 d . . . C2 C 0.08703(13) 0.62313(13) -0.18388(11) 0.0169(3) Uani 1 1 d . . . C3 C -0.01044(14) 0.62418(15) -0.27844(12) 0.0217(3) Uani 1 1 d . . . C4 C -0.08890(15) 0.48876(15) -0.38327(12) 0.0249(3) Uani 1 1 d . . . C5 C -0.06860(14) 0.35509(15) -0.39539(12) 0.0231(3) Uani 1 1 d . . . C6 C 0.02939(14) 0.35664(14) -0.29980(11) 0.0200(3) Uani 1 1 d . . . C7 C 0.20481(13) 0.49178(12) -0.08510(11) 0.0152(2) Uani 1 1 d . . . C8 C 0.23389(12) 0.61377(12) 0.03933(11) 0.0150(2) Uani 1 1 d . . . C9 C 0.30536(13) 0.60545(13) 0.14456(12) 0.0177(3) Uani 1 1 d . . . C10 C 0.35392(14) 0.48226(13) 0.12533(12) 0.0206(3) Uani 1 1 d . . . C11 C 0.33496(14) 0.36637(13) 0.00067(12) 0.0204(3) Uani 1 1 d . . . C12 C 0.26010(13) 0.37147(13) -0.10404(12) 0.0182(3) Uani 1 1 d . . . C13 C 0.17592(13) 0.74513(12) 0.05827(11) 0.0148(2) Uani 1 1 d . . . C14 C 0.24384(13) 0.88864(12) 0.18042(11) 0.0152(2) Uani 1 1 d . . . C15 C 0.39994(13) 0.94737(12) 0.23077(11) 0.0159(2) Uani 1 1 d . . . C16 C 0.45038(14) 1.07358(13) 0.36908(12) 0.0197(3) Uani 1 1 d . . . C17 C 0.35748(13) 1.18288(13) 0.41064(11) 0.0184(3) Uani 1 1 d . . . C18 C 0.19361(13) 1.08942(13) 0.38638(11) 0.0188(3) Uani 1 1 d . . . C19 C 0.14058(13) 0.96101(12) 0.25015(11) 0.0158(3) Uani 1 1 d . . . C20 C 0.40726(16) 1.28999(16) 0.55622(13) 0.0270(3) Uani 1 1 d . . . C21 C 0.37919(16) 1.27378(14) 0.33069(13) 0.0248(3) Uani 1 1 d . . . C22 C 0.33646(15) 0.80348(15) -0.10332(13) 0.0239(3) Uani 1 1 d . . . C23 C 0.11995(18) 0.89474(15) -0.05408(13) 0.0269(3) Uani 1 1 d . . . O3 O 0.78359(12) 1.02828(12) 0.33154(10) 0.0348(3) Uani 1 1 d . . . H3 H -0.0237(15) 0.7148(16) -0.2721(13) 0.024(3) Uiso 1 1 d . . . H4 H -0.1600(17) 0.4893(16) -0.4498(14) 0.029(4) Uiso 1 1 d . . . H5 H -0.1212(15) 0.2610(16) -0.4684(14) 0.022(3) Uiso 1 1 d . . . H6 H 0.0400(15) 0.2643(16) -0.3070(13) 0.022(3) Uiso 1 1 d . . . H9 H 0.3164(16) 0.6865(16) 0.2343(14) 0.026(4) Uiso 1 1 d . . . H10 H 0.4050(16) 0.4777(15) 0.2027(14) 0.025(3) Uiso 1 1 d . . . H11 H 0.3759(16) 0.2809(17) -0.0140(14) 0.032(4) Uiso 1 1 d . . . H12 H 0.2450(15) 0.2895(15) -0.1929(13) 0.021(3) Uiso 1 1 d . . . H13 H 0.0651(14) 0.7131(13) 0.0568(11) 0.011(3) Uiso 1 1 d . . . H16A H 0.5563(18) 1.1259(16) 0.3815(14) 0.027(4) Uiso 1 1 d . . . H16B H 0.4457(16) 1.0246(16) 0.4307(15) 0.032(4) Uiso 1 1 d . . . H18A H 0.1238(15) 1.1519(15) 0.4019(13) 0.021(3) Uiso 1 1 d . . . H18B H 0.1823(18) 1.0453(18) 0.4521(16) 0.044(4) Uiso 1 1 d . . . H20A H 0.5140(18) 1.3460(16) 0.5724(14) 0.029(4) Uiso 1 1 d . . . H20B H 0.3468(18) 1.3608(17) 0.5848(15) 0.037(4) Uiso 1 1 d . . . H20C H 0.4001(18) 1.2357(18) 0.6104(16) 0.041(4) Uiso 1 1 d . . . H21A H 0.4878(17) 1.3362(16) 0.3472(13) 0.026(4) Uiso 1 1 d . . . H21B H 0.3212(18) 1.3477(18) 0.3579(15) 0.039(4) Uiso 1 1 d . . . H21C H 0.3449(17) 1.2082(17) 0.2327(16) 0.036(4) Uiso 1 1 d . . . H22A H 0.3310(16) 0.8197(16) -0.1836(15) 0.030(4) Uiso 1 1 d . . . H22B H 0.3778(16) 0.7178(16) -0.1187(13) 0.029(4) Uiso 1 1 d . . . H22C H 0.3993(19) 0.8934(19) -0.0298(16) 0.041(4) Uiso 1 1 d . . . H23A H 0.1284(17) 0.9121(16) -0.1317(15) 0.032(4) Uiso 1 1 d . . . H23B H 0.0139(18) 0.8698(16) -0.0385(14) 0.028(4) Uiso 1 1 d . . . H23C H 0.1863(17) 0.9826(17) 0.0243(15) 0.028(4) Uiso 1 1 d . . . HO3A H 0.695(2) 0.975(2) 0.2765(18) 0.051(5) Uiso 1 1 d . . . HO3B H 0.857(2) 0.993(2) 0.2958(18) 0.050(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 O1 0.0174(4) 0.0195(4) 0.0232(5) 0.0067(4) 0.0044(3) 0.0080(4) O2 0.0159(4) 0.0213(4) 0.0249(5) 0.0065(4) 0.0031(3) 0.0074(4) N1 0.0233(6) 0.0141(5) 0.0151(5) 0.0062(4) 0.0018(4) 0.0064(4) C1 0.0152(6) 0.0185(6) 0.0162(6) 0.0078(5) 0.0050(4) 0.0044(5) C2 0.0172(6) 0.0178(6) 0.0138(6) 0.0056(5) 0.0029(4) 0.0043(5) C3 0.0243(7) 0.0244(6) 0.0194(6) 0.0103(5) 0.0036(5) 0.0109(5) C4 0.0228(7) 0.0338(7) 0.0180(6) 0.0105(6) 0.0013(5) 0.0098(6) C5 0.0215(7) 0.0247(7) 0.0162(6) 0.0049(5) 0.0020(5) 0.0028(5) C6 0.0213(6) 0.0183(6) 0.0182(6) 0.0064(5) 0.0043(5) 0.0049(5) C7 0.0143(6) 0.0144(5) 0.0165(6) 0.0072(5) 0.0040(4) 0.0028(5) C8 0.0135(6) 0.0137(5) 0.0182(6) 0.0076(5) 0.0049(4) 0.0032(5) C9 0.0200(6) 0.0160(6) 0.0159(6) 0.0061(5) 0.0025(5) 0.0049(5) C10 0.0227(6) 0.0194(6) 0.0220(7) 0.0107(5) 0.0016(5) 0.0075(5) C11 0.0210(6) 0.0164(6) 0.0257(7) 0.0095(5) 0.0045(5) 0.0081(5) C12 0.0180(6) 0.0145(6) 0.0199(6) 0.0055(5) 0.0044(5) 0.0044(5) C13 0.0160(6) 0.0148(6) 0.0145(6) 0.0069(5) 0.0035(4) 0.0053(5) C14 0.0174(6) 0.0132(5) 0.0147(6) 0.0054(4) 0.0024(4) 0.0050(5) C15 0.0191(6) 0.0134(5) 0.0184(6) 0.0087(5) 0.0029(5) 0.0071(5) C16 0.0179(6) 0.0196(6) 0.0190(6) 0.0052(5) -0.0006(5) 0.0071(5) C17 0.0205(6) 0.0167(6) 0.0156(6) 0.0037(5) 0.0023(5) 0.0074(5) C18 0.0205(6) 0.0183(6) 0.0169(6) 0.0051(5) 0.0052(5) 0.0086(5) C19 0.0173(6) 0.0136(5) 0.0180(6) 0.0084(5) 0.0029(5) 0.0042(5) C20 0.0255(8) 0.0250(7) 0.0199(7) 0.0007(6) 0.0015(5) 0.0062(6) C21 0.0280(7) 0.0181(6) 0.0287(8) 0.0101(6) 0.0052(6) 0.0076(6) C22 0.0249(7) 0.0233(7) 0.0203(7) 0.0110(6) 0.0038(5) -0.0001(6) C23 0.0445(9) 0.0194(6) 0.0209(7) 0.0087(6) 0.0013(6) 0.0164(6) O3 0.0204(5) 0.0379(6) 0.0295(5) -0.0030(4) 0.0012(4) 0.0128(5) _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 O1 C15 1.2544(14) . ? O2 C19 1.2577(14) . ? N1 C2 1.4962(14) . ? N1 C23 1.4999(15) . ? N1 C22 1.5034(17) . ? N1 C13 1.5857(14) . ? C1 C2 1.3931(16) . ? C1 C6 1.3998(17) . ? C1 C7 1.4773(15) . ? C2 C3 1.3905(16) . ? C3 C4 1.3894(18) . ? C4 C5 1.3831(19) . ? C5 C6 1.3894(18) . ? C7 C12 1.3971(16) . ? C7 C8 1.4034(16) . ? C8 C9 1.3938(16) . ? C8 C13 1.5161(15) . ? C9 C10 1.3868(17) . ? C10 C11 1.3885(17) . ? C11 C12 1.3862(17) . ? C13 H13 0.998(12) . ? C13 C14 1.5038(15) . ? C14 C15 1.4215(16) . ? C14 C19 1.4274(15) . ? C15 C16 1.5219(16) . ? C16 C17 1.5239(16) . ? C17 C18 1.5259(17) . ? C17 C20 1.5286(17) . ? C17 C21 1.5313(18) . ? C18 C19 1.5159(16) . ? 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 N1 C23 111.74(9) . . ? C2 N1 C22 108.28(9) . . ? C23 N1 C22 107.83(10) . . ? C2 N1 C13 108.74(8) . . ? C23 N1 C13 108.11(9) . . ? C22 N1 C13 112.18(9) . . ? C2 C1 C6 117.52(10) . . ? C2 C1 C7 120.63(10) . . ? C6 C1 C7 121.75(10) . . ? C3 C2 C1 121.91(11) . . ? C3 C2 N1 121.06(10) . . ? C1 C2 N1 116.96(9) . . ? C4 C3 C2 118.88(12) . . ? C5 C4 C3 120.85(11) . . ? C4 C5 C6 119.30(12) . . ? C5 C6 C1 121.52(12) . . ? C12 C7 C8 119.82(10) . . ? C12 C7 C1 121.50(10) . . ? C8 C7 C1 118.59(10) . . ? C9 C8 C7 118.80(10) . . ? C9 C8 C13 121.59(10) . . ? C7 C8 C13 119.42(10) . . ? C10 C9 C8 120.55(11) . . ? C9 C10 C11 120.68(11) . . ? C12 C11 C10 119.18(11) . . ? C11 C12 C7 120.67(11) . . ? H13 C13 C14 108.2(7) . . ? H13 C13 C8 108.3(7) . . ? C14 C13 C8 117.05(9) . . ? H13 C13 N1 99.8(7) . . ? C14 C13 N1 113.67(9) . . ? C8 C13 N1 108.30(9) . . ? C15 C14 C19 120.40(10) . . ? C15 C14 C13 123.49(10) . . ? C19 C14 C13 116.01(10) . . ? O1 C15 C14 124.15(10) . . ? O1 C15 C16 117.59(10) . . ? C14 C15 C16 118.23(10) . . ? C15 C16 C17 115.28(9) . . ? C16 C17 C18 107.05(9) . . ? C16 C17 C20 109.44(10) . . ? C18 C17 C20 110.18(10) . . ? C16 C17 C21 110.14(10) . . ? C18 C17 C21 110.73(10) . . ? C20 C17 C21 109.28(10) . . ? C19 C18 C17 114.48(10) . . ? O2 C19 C14 122.37(10) . . ? O2 C19 C18 117.54(10) . . ? C14 C19 C18 120.08(10) . . ? 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 C23 N1 C2 C3 17.82(15) . . . . ? C22 N1 C2 C1 76.12(12) . . . . ? C14 C13 C8 C9 21.36(16) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 27.50 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.213 _refine_diff_density_min -0.255 _refine_diff_density_rms 0.052