# Copyright The Royal Society of Chemistry, 1999 # CCDC Number :182/1110 data_global _audit_creation_method 'SHELXL and manual editing' # SUBMISSION DETAILS _publ_contact_author ; Dr J. D. Wallis ; _publ_contact_author_email jdw@ukc.ac.uk _publ_contact_author_fax 01227-827724 _publ_contact_author_phone 01277-764000 _publ_requested_journal 'Chemical Communications' _publ_section_title ; Addition of Nucleophiles to Electron Deficient Alkenes Structural Studies on the Incipient Reaction of the Zwitterionic Intermediate ; loop_ _publ_author_name _publ_author_address 'Paul C. Bell' ; Chemical Laboratory School of Physical Sciences University of Kent Canterbury UK CT2 7NH ; 'John D. Wallis' ; Chemical Laboratory School of Physical Sciences University of Kent Canterbury UK CT2 7NH ; # TEXT _publ_section_references ; Darr, J.A., Drake, S.R., Hursthouse, M.B. & Malik, K.M.A. (1993). Inorg. Chem., 32, 5704-5708. Karaoulov, A. I. (1992). ABSMAD. Program for FAST Data Processing. University of Wales, Cardiff, Wales. Nonius (1997a). Kappa-CCD Control Software. Nonius BV, Delft, The Netherlands. Nonius (1997b). Kappa-CCD DENZO Processing Software, Nonius BV, Delft, The Netherlands. Pflugrath, J.W. & Messerschmidt, A. (1989) MADNES version 11-09- 89, Program for Control of Data Collection with Enraf-Nonius FAST X-ray Diffractometer, Enraf-Nonius, Delft, The Netherlands. Sheldrick, G.M. (1990). Acta Cryst. A46, 467-473. Sheldrick, G.M. (1993). SHELXL-93 Program for the Refinement of Crystal Structures, University of G\"ottingen, Germany. ; _publ_section_exptl_refinement ; The structure was solved using direct methods and refined with the full-matrix least-squares technique. All non-hydrogen atoms were refined with anisotropic displacement parameters. ; # DATA data_(I) _chemical_name_systematic ; 5-(1,2-dihydro-1,1-dimethylbenzo(cd)indolium-2-yl)- 2,2-dimethyl-4,6-dioxo-1,3-dioxane-5-ide ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C19 H19 N O4' _chemical_formula_weight 325.35 _chemical_melting_point 460-463 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' '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/c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 9.918(3) _cell_length_b 12.7145(9) _cell_length_c 12.2801(8) _cell_angle_alpha 90.00 _cell_angle_beta 90.989(10) _cell_angle_gamma 90.00 _cell_volume 1548.3(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 250 _cell_measurement_theta_min 3 _cell_measurement_theta_max 20 _exptl_crystal_description block _exptl_crystal_colour white _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.396 _exptl_crystal_density_method ? _exptl_crystal_F_000 688 _exptl_absorpt_coefficient_mu 0.098 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Delft Instruments FAST-TV area-detector' _diffrn_measurement_method 'Darr et al. (1993)' _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 6308 _diffrn_reflns_av_R_equivalents 0.1133 _diffrn_reflns_av_sigmaI/netI 0.1074 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.05 _diffrn_reflns_theta_max 24.94 _reflns_number_total 2381 _reflns_number_observed 1724 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'MADNES (Pflugrath & esserschmidt,1989)' _computing_cell_refinement 'REFINE (incorporated in MADNES)' _computing_data_reduction 'ABSMAD (Karaulov, 1991)' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 169 with very egative F^2^ or flagged by the user for potential systematic errors. Weighted R- actors wR and all goodnesses of fit S are based on F^2^, conventional R- actors R are based on F, with F set to zero for negative F^2^. The observed riterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. nd is not relevant to the choice of reflections for refinement. R-factors ased on F^2^ are statistically about twice as large as those based on F, nd 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 w=1/[s^2^(Fo^2^)+( 0.0429P)^2^+0.0000P] where w=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2212 _refine_ls_number_parameters 293 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0573 _refine_ls_R_factor_obs 0.0400 _refine_ls_wR_factor_all 0.0950 _refine_ls_wR_factor_obs 0.0906 _refine_ls_goodness_of_fit_all 0.892 _refine_ls_goodness_of_fit_obs 0.999 _refine_ls_restrained_S_all 0.868 _refine_ls_restrained_S_obs 0.999 _refine_ls_shift/esd_max -0.051 _refine_ls_shift/esd_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.87750(14) 0.39645(12) -0.26321(10) 0.0217(4) Uani 1 d . . O2 O 0.67738(14) 0.27677(11) 0.05877(10) 0.0210(4) Uani 1 d . . O3 O 0.84635(14) 0.50073(11) -0.12178(10) 0.0200(4) Uani 1 d . . O4 O 0.74181(14) 0.44199(11) 0.03822(10) 0.0200(4) Uani 1 d . . N1 N 0.8398(2) 0.13697(13) -0.15689(11) 0.0163(4) Uani 1 d . . C1 C 0.7638(2) 0.0367(2) -0.16092(14) 0.0168(5) Uani 1 d . . C2 C 0.8123(2) -0.0630(2) -0.1695(2) 0.0218(5) Uani 1 d . . C3 C 0.7147(2) -0.1449(2) -0.1656(2) 0.0253(6) Uani 1 d . . C4 C 0.5793(3) -0.1263(2) -0.1517(2) 0.0243(6) Uani 1 d . . C5 C 0.3953(2) 0.0114(2) -0.12876(15) 0.0246(6) Uani 1 d . . C6 C 0.3664(2) 0.1169(2) -0.1230(2) 0.0239(6) Uani 1 d . . C7 C 0.4668(2) 0.1960(2) -0.13226(15) 0.0209(5) Uani 1 d . . C8 C 0.5978(2) 0.1656(2) -0.14641(14) 0.0164(5) Uani 1 d . . C9 C 0.5302(2) -0.0221(2) -0.14253(14) 0.0191(5) Uani 1 d . . C10 C 0.6267(2) 0.0583(2) -0.14940(14) 0.0169(5) Uani 1 d . . C11 C 0.7224(2) 0.2281(2) -0.1718(2) 0.0163(5) Uani 1 d . . C12 C 0.7521(2) 0.3282(2) -0.11639(14) 0.0153(5) Uani 1 d . . C13 C 0.8249(2) 0.4054(2) -0.17315(15) 0.0164(5) Uani 1 d . . C14 C 0.7570(2) 0.5289(2) -0.03545(15) 0.0184(5) Uani 1 d . . C15 C 0.7188(2) 0.3430(2) -0.0048(2) 0.0177(5) Uani 1 d . . C16 C 0.8283(3) 0.6134(2) 0.0287(2) 0.0258(6) Uani 1 d . . C17 C 0.6216(2) 0.5626(2) -0.0821(2) 0.0211(5) Uani 1 d . . C18 C 0.9120(3) 0.1468(2) -0.0495(2) 0.0215(5) Uani 1 d . . C19 C 0.9407(3) 0.1444(2) -0.2471(2) 0.0224(6) Uani 1 d . . H2 H 0.9168(24) -0.0806(18) -0.1757(15) 0.033(6) Uiso 1 d . . H3 H 0.7461(23) -0.2178(18) -0.1704(15) 0.026(6) Uiso 1 d . . H4 H 0.5191(24) -0.1816(18) -0.1446(16) 0.028(6) Uiso 1 d . . H5 H 0.3219(22) -0.0395(17) -0.1249(14) 0.024(6) Uiso 1 d . . H6 H 0.2721(24) 0.1373(17) -0.1134(15) 0.025(6) Uiso 1 d . . H7 H 0.4396(23) 0.2722(20) -0.1299(15) 0.030(6) Uiso 1 d . . H11 H 0.7211(21) 0.2401(17) -0.2503(16) 0.026(6) Uiso 1 d . . H16A H 0.9255(27) 0.5880(19) 0.0509(17) 0.039(7) Uiso 1 d . . H16B H 0.7687(25) 0.6330(18) 0.0879(17) 0.037(7) Uiso 1 d . . H16C H 0.8414(25) 0.6801(20) -0.0165(18) 0.042(7) Uiso 1 d . . H17A H 0.6363(22) 0.6208(19) -0.1336(16) 0.031(6) Uiso 1 d . . H17B H 0.5671(23) 0.5901(18) -0.0257(16) 0.030(6) Uiso 1 d . . H17C H 0.5761(22) 0.5034(18) -0.1213(15) 0.026(6) Uiso 1 d . . H18A H 0.8443(22) 0.1426(16) 0.0086(15) 0.021(5) Uiso 1 d . . H18B H 0.9566(21) 0.2155(17) -0.0474(14) 0.018(5) Uiso 1 d . . H18C H 0.9703(25) 0.0946(19) -0.0440(16) 0.030(7) Uiso 1 d . . H19A H 1.0088(24) 0.0917(19) -0.2366(14) 0.023(6) Uiso 1 d . . H19B H 0.9809(23) 0.2150(19) -0.2467(14) 0.026(6) Uiso 1 d . . H19C H 0.8924(22) 0.1307(16) -0.3184(17) 0.022(6) Uiso 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 0.0191(9) 0.0283(9) 0.0179(8) 0.0025(6) 0.0064(6) 0.0003(7) O2 0.0255(9) 0.0232(9) 0.0146(7) 0.0046(6) 0.0030(6) -0.0030(7) O3 0.0173(9) 0.0210(9) 0.0219(8) -0.0013(6) 0.0046(6) -0.0021(7) O4 0.0258(9) 0.0190(9) 0.0151(7) -0.0011(6) -0.0006(6) -0.0007(7) N1 0.0135(10) 0.0197(10) 0.0158(9) -0.0006(7) 0.0011(7) -0.0011(8) C1 0.0192(13) 0.0207(13) 0.0103(10) -0.0013(8) -0.0001(8) -0.0037(10) C2 0.0259(14) 0.0226(14) 0.0170(11) -0.0007(9) 0.0019(9) 0.0004(11) C3 0.036(2) 0.0195(14) 0.0205(12) -0.0005(9) 0.0026(10) -0.0024(12) C4 0.033(2) 0.0251(15) 0.0148(12) -0.0011(9) 0.0012(9) -0.0115(12) C5 0.0246(15) 0.038(2) 0.0108(11) -0.0004(9) -0.0008(9) -0.0123(12) C6 0.0135(14) 0.045(2) 0.0135(11) -0.0002(10) -0.0003(9) -0.0022(12) C7 0.0183(14) 0.0316(15) 0.0127(11) -0.0009(9) -0.0005(8) 0.0014(11) C8 0.0174(13) 0.0239(13) 0.0078(10) -0.0008(8) -0.0011(8) -0.0012(10) C9 0.0212(13) 0.0296(14) 0.0064(10) -0.0003(8) -0.0012(8) -0.0075(11) C10 0.0180(13) 0.0254(13) 0.0074(10) -0.0009(8) -0.0001(8) -0.0011(10) C11 0.0140(12) 0.0223(12) 0.0124(11) 0.0029(9) -0.0004(8) 0.0038(10) C12 0.0142(12) 0.0190(12) 0.0127(11) 0.0006(8) 0.0009(8) 0.0013(9) C13 0.0116(12) 0.0203(12) 0.0171(11) 0.0007(9) -0.0025(9) 0.0030(9) C14 0.0187(13) 0.0191(13) 0.0176(11) 0.0018(9) 0.0040(8) -0.0006(10) C15 0.0138(12) 0.0191(13) 0.0200(12) -0.0008(9) -0.0021(9) 0.0022(10) C16 0.024(2) 0.0249(15) 0.0284(13) -0.0030(11) -0.0023(11) -0.0024(12) C17 0.0212(14) 0.0240(14) 0.0181(12) 0.0015(11) 0.0022(10) 0.0012(11) C18 0.0179(14) 0.024(2) 0.0223(13) -0.0003(10) -0.0078(10) 0.0014(12) C19 0.0167(13) 0.0263(15) 0.0245(14) -0.0005(10) 0.0090(10) 0.0003(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. lanes) are estimated using the full covariance matrix. The cell esds are aken into account individually in the estimation of esds in distances, ngles and torsion angles; correlations between esds in cell parameters are nly used when they are defined by crystal symmetry. An approximate isotropic) treatment of cell esds is used for estimating esds involving l.s. lanes. ; 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 C13 1.236(2) . ? O2 C15 1.224(2) . ? O3 C13 1.381(2) . ? O3 C14 1.439(2) . ? O4 C15 1.382(2) . ? O4 C14 1.438(2) . ? N1 C1 1.481(3) . ? N1 C18 1.495(3) . ? N1 C19 1.508(2) . ? N1 C11 1.651(3) . ? C1 C2 1.361(3) . ? C1 C10 1.397(3) . ? C2 C3 1.423(3) . ? C3 C4 1.377(3) . ? C4 C9 1.417(3) . ? C5 C6 1.374(3) . ? C5 C9 1.417(3) . ? C6 C7 1.422(3) . ? C7 C8 1.370(3) . ? C8 C10 1.395(3) . ? C8 C11 1.506(3) . ? C9 C10 1.404(3) . ? C11 C12 1.471(3) . ? C12 C13 1.409(3) . ? C12 C15 1.428(2) . ? C14 C16 1.501(3) . ? C14 C17 1.513(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 C13 O3 C14 117.59(15) . . ? C15 O4 C14 118.55(14) . . ? C1 N1 C18 109.7(2) . . ? C1 N1 C19 111.9(2) . . ? C18 N1 C19 109.2(2) . . ? C1 N1 C11 104.05(15) . . ? C18 N1 C11 111.4(2) . . ? C19 N1 C11 110.5(2) . . ? C2 C1 C10 122.5(2) . . ? C2 C1 N1 128.6(2) . . ? C10 C1 N1 108.8(2) . . ? C1 C2 C3 115.9(2) . . ? C4 C3 C2 123.0(2) . . ? C3 C4 C9 120.6(2) . . ? C6 C5 C9 119.8(2) . . ? C5 C6 C7 122.7(2) . . ? C8 C7 C6 118.5(2) . . ? C7 C8 C10 118.4(2) . . ? C7 C8 C11 131.4(2) . . ? C10 C8 C11 109.9(2) . . ? C10 C9 C4 116.1(2) . . ? C10 C9 C5 115.8(2) . . ? C4 C9 C5 128.1(2) . . ? C8 C10 C1 113.3(2) . . ? C8 C10 C9 124.7(2) . . ? C1 C10 C9 121.9(2) . . ? C12 C11 C8 121.2(2) . . ? C12 C11 N1 114.9(2) . . ? C8 C11 N1 100.7(2) . . ? C13 C12 C15 120.8(2) . . ? C13 C12 C11 118.3(2) . . ? C15 C12 C11 120.7(2) . . ? O1 C13 O3 115.1(2) . . ? O1 C13 C12 127.3(2) . . ? O3 C13 C12 117.5(2) . . ? O4 C14 O3 110.2(2) . . ? O4 C14 C16 105.9(2) . . ? O3 C14 C16 105.9(2) . . ? O4 C14 C17 110.7(2) . . ? O3 C14 C17 110.2(2) . . ? C16 C14 C17 113.8(2) . . ? O2 C15 O4 116.0(2) . . ? O2 C15 C12 127.4(2) . . ? O4 C15 C12 116.6(2) . . ? _refine_diff_density_max 0.283 _refine_diff_density_min -0.253 _refine_diff_density_rms 0.066 #=END data_dc10 _audit_creation_method SHELXL _chemical_name_systematic ; 2-(8-dimethylamino)naphth-1-yl)ethene-1,1-dinitrile ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C16 H13 N3' _chemical_formula_weight 247.29 _chemical_melting_point 429-431 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' '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 'P 21/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 13.606(10) _cell_length_b 9.042(5) _cell_length_c 11.073(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.38(2) _cell_angle_gamma 90.00 _cell_volume 1325.3(17) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6044 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.2 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.239 _exptl_crystal_density_method ? _exptl_crystal_F_000 520 _exptl_absorpt_coefficient_mu 0.076 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.928 _exptl_absorpt_correction_T_max 0.986 _exptl_special_details ; Absorption correction using SORTAV ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'Enraf Nonius FR591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'kappaCCD' _diffrn_measurement_method '\w' _diffrn_detector_area_resol_mean 9.09 _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 6044 _diffrn_reflns_av_R_equivalents 0.0423 _diffrn_reflns_av_sigmaI/netI 0.0681 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_h_max 16 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.73 _diffrn_reflns_theta_max 26.47 _reflns_number_total 2677 _reflns_number_observed 2082 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'KappaCCD (Nonius, 1997a)' _computing_cell_refinement 'DENZO (Nonius, 1997b)' _computing_data_reduction 'DENZO' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 170 with very egative F^2^ or flagged by the user for potential systematic errors. Weighted R- actors wR and all goodnesses of fit S are based on F^2^, conventional R- actors R are based on F, with F set to zero for negative F^2^. The observed riterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. nd is not relevant to the choice of reflections for refinement. R-factors ased on F^2^ are statistically about twice as large as those based on F, nd 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 w=1/[s^2^(Fo^2^)+( 0.0442P)^2^+0.3224P] where w=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2507 _refine_ls_number_parameters 224 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0679 _refine_ls_R_factor_obs 0.0502 _refine_ls_wR_factor_all 0.1280 _refine_ls_wR_factor_obs 0.1144 _refine_ls_goodness_of_fit_all 1.068 _refine_ls_goodness_of_fit_obs 1.124 _refine_ls_restrained_S_all 1.097 _refine_ls_restrained_S_obs 1.124 _refine_ls_shift/esd_max -0.040 _refine_ls_shift/esd_mean 0.006 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group N1 N 0.29086(10) 0.02318(14) 0.71672(12) 0.0242(3) Uani 1 d . . N2 N 0.4012(2) 0.5153(2) 0.6674(2) 0.0520(5) Uani 1 d . . N3 N 0.47361(14) 0.1659(2) 0.42449(15) 0.0453(5) Uani 1 d . . C1 C 0.30081(11) 0.0237(2) 0.84824(14) 0.0214(4) Uani 1 d . . C2 C 0.23580(13) -0.0460(2) 0.9070(2) 0.0289(4) Uani 1 d . . C3 C 0.24832(13) -0.0329(2) 1.0361(2) 0.0309(4) Uani 1 d . . C4 C 0.32313(13) 0.0519(2) 1.1051(2) 0.0263(4) Uani 1 d . . C5 C 0.46973(12) 0.2188(2) 1.11362(15) 0.0227(4) Uani 1 d . . C6 C 0.53255(12) 0.2902(2) 1.05389(15) 0.0245(4) Uani 1 d . . C7 C 0.52453(12) 0.2687(2) 0.92612(14) 0.0223(3) Uani 1 d . . C8 C 0.45217(11) 0.1770(2) 0.85876(13) 0.0179(3) Uani 1 d . . C9 C 0.39223(11) 0.1256(2) 1.04751(14) 0.0206(3) Uani 1 d . . C10 C 0.38211(11) 0.10720(15) 0.91816(13) 0.0178(3) Uani 1 d . . C11 C 0.45212(11) 0.1408(2) 0.72908(14) 0.0199(3) Uani 1 d . . C12 C 0.44847(12) 0.2438(2) 0.63936(14) 0.0232(4) Uani 1 d . . C13 C 0.42303(14) 0.3952(2) 0.65552(15) 0.0300(4) Uani 1 d . . C14 C 0.46291(13) 0.2020(2) 0.5195(2) 0.0292(4) Uani 1 d . . C18 C 0.2186(2) 0.1321(2) 0.6526(2) 0.0377(5) Uani 1 d . . C19 C 0.2758(2) -0.1222(2) 0.6572(2) 0.0413(5) Uani 1 d . . H2 H 0.1805(15) -0.1028(20) 0.8549(17) 0.039(5) Uiso 1 d . . H3 H 0.2030(16) -0.0846(22) 1.0767(18) 0.046(6) Uiso 1 d . . H4 H 0.3296(14) 0.0628(20) 1.1942(18) 0.037(5) Uiso 1 d . . H5 H 0.4764(13) 0.2308(18) 1.2005(17) 0.029(4) Uiso 1 d . . H6 H 0.5827(13) 0.3526(18) 1.1005(15) 0.025(4) Uiso 1 d . . H7 H 0.5728(13) 0.3154(18) 0.8863(15) 0.026(4) Uiso 1 d . . H11 H 0.4709(12) 0.0405(18) 0.7137(15) 0.022(4) Uiso 1 d . . H18A H 0.2330(16) 0.2333(24) 0.6971(19) 0.048(6) Uiso 1 d . . H18B H 0.2236(17) 0.1446(23) 0.5628(23) 0.060(7) Uiso 1 d . . H18C H 0.1494(18) 0.1013(23) 0.6546(20) 0.054(6) Uiso 1 d . . H19A H 0.3272(18) -0.1907(23) 0.7076(20) 0.055(6) Uiso 1 d . . H19B H 0.2806(15) -0.1101(21) 0.5699(21) 0.048(6) Uiso 1 d . . H19C H 0.2089(18) -0.1563(22) 0.6586(19) 0.049(6) Uiso 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 N1 0.0250(7) 0.0229(7) 0.0227(7) -0.0033(5) 0.0016(6) -0.0011(5) N2 0.0883(14) 0.0274(9) 0.0345(10) -0.0007(7) 0.0025(9) 0.0086(9) N3 0.0679(12) 0.0486(10) 0.0238(8) 0.0028(7) 0.0193(8) 0.0100(8) C1 0.0225(8) 0.0178(8) 0.0243(8) 0.0004(6) 0.0064(6) 0.0031(6) C2 0.0250(9) 0.0234(9) 0.0399(10) 0.0001(7) 0.0109(8) -0.0026(7) C3 0.0316(10) 0.0272(9) 0.0404(11) 0.0070(8) 0.0216(8) 0.0014(7) C4 0.0311(9) 0.0258(8) 0.0262(9) 0.0057(7) 0.0155(7) 0.0078(7) C5 0.0268(8) 0.0260(8) 0.0153(8) 0.0001(6) 0.0049(6) 0.0068(6) C6 0.0248(8) 0.0263(8) 0.0209(8) -0.0034(7) 0.0023(6) -0.0024(7) C7 0.0213(8) 0.0240(8) 0.0226(8) 0.0004(6) 0.0072(6) -0.0017(6) C8 0.0202(8) 0.0177(7) 0.0166(8) 0.0012(5) 0.0056(6) 0.0033(6) C9 0.0238(8) 0.0193(8) 0.0208(8) 0.0030(6) 0.0090(6) 0.0073(6) C10 0.0183(7) 0.0160(7) 0.0196(8) 0.0008(6) 0.0055(6) 0.0042(6) C11 0.0185(8) 0.0213(8) 0.0209(8) -0.0025(6) 0.0065(6) 0.0007(6) C12 0.0287(9) 0.0233(8) 0.0184(8) -0.0010(6) 0.0070(6) 0.0002(6) C13 0.0446(11) 0.0254(10) 0.0191(8) 0.0018(6) 0.0055(7) -0.0013(8) C14 0.0386(10) 0.0291(9) 0.0210(9) 0.0036(7) 0.0093(7) 0.0021(7) C18 0.0351(11) 0.0398(11) 0.0347(11) 0.0053(8) 0.0009(8) 0.0083(9) C19 0.0528(14) 0.0318(11) 0.0344(12) -0.0111(8) 0.0002(10) -0.0072(9) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. lanes) are estimated using the full covariance matrix. The cell esds are aken into account individually in the estimation of esds in distances, ngles and torsion angles; correlations between esds in cell parameters are nly used when they are defined by crystal symmetry. An approximate isotropic) treatment of cell esds is used for estimating esds involving l.s. lanes. ; 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 N1 C1 1.431(2) . ? N1 C18 1.455(2) . ? N1 C19 1.464(2) . ? N1 C11 2.413(2) . ? N2 C13 1.142(2) . ? N3 C14 1.142(2) . ? C1 C2 1.367(2) . ? C1 C10 1.413(2) . ? C2 C3 1.405(3) . ? C3 C4 1.359(3) . ? C4 C9 1.419(2) . ? C5 C6 1.359(2) . ? C5 C9 1.414(2) . ? C6 C7 1.407(2) . ? C7 C8 1.369(2) . ? C8 C10 1.425(2) . ? C8 C11 1.473(2) . ? C9 C10 1.417(2) . ? C11 C12 1.354(2) . ? C12 C13 1.433(2) . ? C12 C14 1.437(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 C1 N1 C18 112.88(14) . . ? C1 N1 C19 115.58(14) . . ? C18 N1 C19 112.3(2) . . ? C1 N1 C11 94.03(9) . . ? C18 N1 C11 103.40(12) . . ? C19 N1 C11 116.87(13) . . ? C2 C1 C10 119.8(2) . . ? C2 C1 N1 124.29(15) . . ? C10 C1 N1 115.91(13) . . ? C1 C2 C3 120.4(2) . . ? C4 C3 C2 121.2(2) . . ? C3 C4 C9 120.0(2) . . ? C6 C5 C9 120.6(2) . . ? C5 C6 C7 120.8(2) . . ? C8 C7 C6 120.69(15) . . ? C7 C8 C10 119.38(14) . . ? C7 C8 C11 120.26(14) . . ? C10 C8 C11 120.16(13) . . ? C5 C9 C10 118.67(14) . . ? C5 C9 C4 122.6(2) . . ? C10 C9 C4 118.68(15) . . ? C1 C10 C9 119.83(14) . . ? C1 C10 C8 120.42(14) . . ? C9 C10 C8 119.72(14) . . ? C12 C11 C8 123.64(14) . . ? C12 C11 N1 112.51(11) . . ? C8 C11 N1 87.04(9) . . ? C11 C12 C13 122.30(15) . . ? C11 C12 C14 120.47(15) . . ? C13 C12 C14 117.08(14) . . ? N2 C13 C12 178.9(2) . . ? N3 C14 C12 178.6(2) . . ? _refine_diff_density_max 0.188 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.052 #=END data_benzo _audit_creation_method SHELXL _chemical_name_systematic ; 1,1-dibenzoyl-2-(8-dimethylamino)naphth-1-yl)ethene ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C28 H23 N O2' _chemical_formula_weight 405.47 _chemical_melting_point 415-416 _chemical_compound_source ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' '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/n' 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 11.2537(4) _cell_length_b 11.4933(5) _cell_length_c 16.7819(6) _cell_angle_alpha 90.00 _cell_angle_beta 93.884(2) _cell_angle_gamma 90.00 _cell_volume 2165.62(14) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 10407 _cell_measurement_theta_min 1.5 _cell_measurement_theta_max 27.5 _exptl_crystal_description block _exptl_crystal_colour orange _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.244 _exptl_crystal_density_method ? _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 150 _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoKa _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device 'Nonius KappaCCD' _diffrn_measurement_method '\w' _diffn_detector_area_resol_mean 9.09 _diffrn_standards_number 'not measured' _diffrn_standards_interval_count 'not measured' _diffrn_standards_interval_time 'not measured' _diffrn_standards_decay_% 'not measured' _diffrn_reflns_number 10407 _diffrn_reflns_av_R_equivalents 0.0644 _diffrn_reflns_av_sigmaI/netI 0.0745 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 3.01 _diffrn_reflns_theta_max 28.28 _reflns_number_total 5350 _reflns_number_observed 3759 _reflns_observed_criterion >2sigma(I) _computing_data_collection 'KappaCCD (Nonius, 1997a)' _computing_cell_refinement 'DENZO (Nonius, 1997b)' _computing_data_reduction 'DENZO' _computing_structure_solution 'SHELXS-86 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-93 (Sheldrick, 1993)' _computing_molecular_graphics ? _computing_publication_material 'SHELXL-93 (Sheldrick, 1993)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 422 with very egative F^2^ or flagged by the user for potential systematic errors. Weighted R- actors wR and all goodnesses of fit S are based on F^2^, conventional R- actors R are based on F, with F set to zero for negative F^2^. The observed riterion of F^2^ > 2sigma(F^2^) is used only for calculating _R_factor_obs etc. nd is not relevant to the choice of reflections for refinement. R-factors ased on F^2^ are statistically about twice as large as those based on F, nd 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 w=1/[s^2^(Fo^2^)+( 0.0890P)^2^+0.5475P] where w=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.1050(61) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^l^3^/sin(2q)]^-1/4^' _refine_ls_number_reflns 4928 _refine_ls_number_parameters 373 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0902 _refine_ls_R_factor_obs 0.0566 _refine_ls_wR_factor_all 0.1635 _refine_ls_wR_factor_obs 0.1385 _refine_ls_goodness_of_fit_all 0.976 _refine_ls_goodness_of_fit_obs 1.030 _refine_ls_restrained_S_all 1.008 _refine_ls_restrained_S_obs 1.030 _refine_ls_shift/esd_max -0.050 _refine_ls_shift/esd_mean 0.007 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_thermal_displace_type _atom_site_occupancy _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_group O1 O 0.11798(12) 0.84014(12) 1.00519(8) 0.0346(3) Uani 1 d . . O2 O 0.22289(11) 0.98203(11) 0.84022(7) 0.0304(3) Uani 1 d . . N1 N 0.49071(13) 0.76866(13) 1.02101(9) 0.0283(4) Uani 1 d . . C1 C 0.4776(2) 0.66214(15) 1.06249(10) 0.0252(4) Uani 1 d . . C2 C 0.5632(2) 0.6215(2) 1.11845(12) 0.0348(5) Uani 1 d . . C3 C 0.5440(2) 0.5208(2) 1.16327(12) 0.0387(5) Uani 1 d . . C4 C 0.4399(2) 0.4616(2) 1.15315(11) 0.0348(5) Uani 1 d . . C5 C 0.2433(2) 0.4331(2) 1.08096(11) 0.0303(4) Uani 1 d . . C6 C 0.1614(2) 0.4620(2) 1.02092(12) 0.0304(4) Uani 1 d . . C7 C 0.1833(2) 0.5558(2) 0.97023(11) 0.0251(4) Uani 1 d . . C8 C 0.28532(14) 0.62206(14) 0.98074(9) 0.0201(3) Uani 1 d . . C9 C 0.3506(2) 0.49677(15) 1.09393(10) 0.0260(4) Uani 1 d . . C10 C 0.37143(15) 0.59567(14) 1.04527(9) 0.0216(4) Uani 1 d . . C11 C 0.30698(15) 0.71014(14) 0.91907(9) 0.0206(3) Uani 1 d . . C12 C 0.23077(15) 0.79417(14) 0.89388(9) 0.0213(4) Uani 1 d . . C13 C 0.11731(15) 0.82182(14) 0.93373(10) 0.0235(4) Uani 1 d . . C15 C 0.26320(15) 0.88365(14) 0.83523(10) 0.0215(4) Uani 1 d . . C18 C 0.4175(2) 0.8634(2) 1.04897(12) 0.0313(4) Uani 1 d . . C19 C 0.6124(2) 0.8077(2) 1.0122(2) 0.0503(6) Uani 1 d . . C21 C 0.0047(2) 0.82806(15) 0.88128(10) 0.0257(4) Uani 1 d . . C22 C -0.0088(2) 0.7639(2) 0.81122(11) 0.0317(4) Uani 1 d . . C23 C -0.1152(2) 0.7677(2) 0.76415(13) 0.0439(5) Uani 1 d . . C24 C -0.2059(2) 0.8393(2) 0.7859(2) 0.0494(6) Uani 1 d . . C25 C -0.1920(2) 0.9050(2) 0.8545(2) 0.0508(6) Uani 1 d . . C26 C -0.0881(2) 0.8984(2) 0.90370(14) 0.0400(5) Uani 1 d . . C31 C 0.34792(14) 0.85579(14) 0.77282(9) 0.0207(4) Uani 1 d . . C32 C 0.4241(2) 0.9438(2) 0.75078(10) 0.0258(4) Uani 1 d . . C33 C 0.5020(2) 0.9241(2) 0.69117(11) 0.0326(4) Uani 1 d . . C34 C 0.5020(2) 0.8174(2) 0.65240(11) 0.0326(4) Uani 1 d . . C35 C 0.4248(2) 0.7304(2) 0.67277(10) 0.0293(4) Uani 1 d . . C36 C 0.3480(2) 0.74870(15) 0.73345(10) 0.0236(4) Uani 1 d . . H2 H 0.6344(21) 0.6646(20) 1.1267(13) 0.040(6) Uiso 1 d . . H3 H 0.6066(21) 0.4946(20) 1.2042(15) 0.046(6) Uiso 1 d . . H4 H 0.4250(19) 0.3926(21) 1.1841(13) 0.041(6) Uiso 1 d . . H5 H 0.2326(19) 0.3678(19) 1.1137(12) 0.036(6) Uiso 1 d . . H6 H 0.0904(19) 0.4135(19) 1.0102(12) 0.033(5) Uiso 1 d . . H7 H 0.1302(17) 0.5719(16) 0.9239(11) 0.023(5) Uiso 1 d . . H11 H 0.3810(17) 0.7027(16) 0.8946(11) 0.022(5) Uiso 1 d . . H18A H 0.3374(19) 0.8335(18) 1.0600(12) 0.033(5) Uiso 1 d . . H18B H 0.4071(18) 0.9278(19) 1.0064(13) 0.035(6) Uiso 1 d . . H18C H 0.4538(19) 0.8982(20) 1.1010(13) 0.041(6) Uiso 1 d . . H19A H 0.6654(24) 0.7408(24) 0.9956(15) 0.061(8) Uiso 1 d . . H19B H 0.6543(25) 0.8464(24) 1.0663(18) 0.070(8) Uiso 1 d . . H19C H 0.6062(24) 0.8688(25) 0.9723(16) 0.061(8) Uiso 1 d . . H22 H 0.0585(18) 0.7152(18) 0.7962(12) 0.032(5) Uiso 1 d . . H23 H -0.1216(22) 0.7181(22) 0.7162(16) 0.054(7) Uiso 1 d . . H24 H -0.2763(26) 0.8433(24) 0.7519(17) 0.068(8) Uiso 1 d . . H25 H -0.2507(24) 0.9578(23) 0.8664(16) 0.058(7) Uiso 1 d . . H26 H -0.0778(22) 0.9411(23) 0.9537(16) 0.056(7) Uiso 1 d . . H33 H 0.5564(20) 0.9869(20) 0.6765(13) 0.041(6) Uiso 1 d . . H32 H 0.4249(17) 1.0200(18) 0.7767(12) 0.028(5) Uiso 1 d . . H34 H 0.5565(18) 0.8052(18) 0.6107(12) 0.034(6) Uiso 1 d . . H35 H 0.4232(18) 0.6549(19) 0.6457(12) 0.035(6) Uiso 1 d . . H36 H 0.2914(17) 0.6860(17) 0.7464(11) 0.025(5) Uiso 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 0.0377(7) 0.0417(8) 0.0253(7) -0.0039(6) 0.0077(5) 0.0076(6) O2 0.0358(7) 0.0226(6) 0.0334(7) 0.0035(5) 0.0064(6) 0.0067(6) N1 0.0294(8) 0.0211(7) 0.0349(8) -0.0036(6) 0.0044(7) 0.0003(6) C1 0.0311(9) 0.0220(8) 0.0225(8) -0.0065(7) 0.0005(7) 0.0062(7) C2 0.0360(11) 0.0321(10) 0.0349(10) -0.0127(8) -0.0082(8) 0.0098(9) C3 0.0518(13) 0.0337(10) 0.0284(10) -0.0071(8) -0.0129(9) 0.0190(10) C4 0.0561(13) 0.0256(10) 0.0224(9) 0.0028(7) -0.0001(8) 0.0151(9) C5 0.0422(11) 0.0216(8) 0.0288(9) 0.0062(7) 0.0155(8) 0.0052(8) C6 0.0298(9) 0.0252(9) 0.0376(10) 0.0010(8) 0.0116(8) -0.0004(8) C7 0.0260(9) 0.0242(8) 0.0253(8) 0.0014(7) 0.0027(7) 0.0030(7) C8 0.0240(8) 0.0185(8) 0.0181(7) -0.0018(6) 0.0040(6) 0.0051(6) C9 0.0376(10) 0.0207(8) 0.0202(8) 0.0006(6) 0.0061(7) 0.0092(7) C10 0.0274(8) 0.0197(8) 0.0179(7) -0.0022(6) 0.0037(6) 0.0067(7) C11 0.0227(8) 0.0219(8) 0.0175(7) -0.0012(6) 0.0037(6) 0.0005(7) C12 0.0251(8) 0.0220(8) 0.0168(7) 0.0002(6) 0.0034(6) 0.0026(7) C13 0.0284(9) 0.0202(8) 0.0227(8) 0.0012(6) 0.0068(7) 0.0038(7) C15 0.0223(8) 0.0209(8) 0.0211(8) 0.0007(6) -0.0009(6) 0.0016(7) C18 0.0347(10) 0.0219(9) 0.0371(11) -0.0053(8) 0.0000(8) 0.0037(8) C19 0.0388(12) 0.0315(12) 0.083(2) -0.0074(12) 0.0213(13) -0.0027(10) C21 0.0247(8) 0.0227(8) 0.0303(9) 0.0075(7) 0.0058(7) 0.0026(7) C22 0.0287(9) 0.0384(11) 0.0285(9) 0.0060(8) 0.0053(7) 0.0005(8) C23 0.0382(11) 0.0604(14) 0.0325(11) 0.0122(11) -0.0021(9) -0.0126(11) C24 0.0279(11) 0.065(2) 0.0538(14) 0.0281(13) -0.0043(10) -0.0055(11) C25 0.0275(11) 0.0499(14) 0.076(2) 0.0181(13) 0.0100(11) 0.0137(10) C26 0.0304(10) 0.0374(11) 0.0531(13) -0.0011(10) 0.0084(9) 0.0082(9) C31 0.0222(8) 0.0227(8) 0.0171(7) 0.0052(6) -0.0009(6) 0.0035(7) C32 0.0271(9) 0.0250(9) 0.0253(8) 0.0031(7) 0.0010(7) -0.0005(7) C33 0.0300(10) 0.0383(11) 0.0301(9) 0.0104(8) 0.0061(8) -0.0032(8) C34 0.0300(9) 0.0448(11) 0.0236(9) 0.0045(8) 0.0070(8) 0.0074(9) C35 0.0335(10) 0.0313(10) 0.0232(8) -0.0026(8) 0.0025(7) 0.0036(8) C36 0.0258(8) 0.0229(8) 0.0220(8) 0.0016(6) -0.0003(7) 0.0012(7) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. lanes) are estimated using the full covariance matrix. The cell esds are aken into account individually in the estimation of esds in distances, ngles and torsion angles; correlations between esds in cell parameters are nly used when they are defined by crystal symmetry. An approximate isotropic) treatment of cell esds is used for estimating esds involving l.s. lanes. ; 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 C13 1.217(2) . ? O2 C15 1.223(2) . ? N1 C1 1.421(2) . ? N1 C19 1.458(3) . ? N1 C18 1.462(2) . ? C1 C2 1.381(3) . ? C1 C10 1.431(3) . ? C2 C3 1.405(3) . ? C3 C4 1.356(3) . ? C4 C9 1.423(3) . ? C5 C6 1.360(3) . ? C5 C9 1.416(3) . ? C6 C7 1.406(2) . ? C7 C8 1.379(2) . ? C8 C10 1.436(2) . ? C8 C11 1.480(2) . ? C9 C10 1.428(2) . ? C11 C12 1.341(2) . ? C12 C15 1.486(2) . ? C12 C13 1.515(2) . ? C13 C21 1.494(2) . ? C15 C31 1.498(2) . ? C21 C22 1.387(3) . ? C21 C26 1.393(3) . ? C22 C23 1.390(3) . ? C23 C24 1.379(4) . ? C24 C25 1.376(4) . ? C25 C26 1.388(3) . ? C31 C32 1.392(2) . ? C31 C36 1.397(2) . ? C32 C33 1.393(3) . ? C33 C34 1.388(3) . ? C34 C35 1.383(3) . ? C35 C36 1.396(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 C1 N1 C19 116.4(2) . . ? C1 N1 C18 113.89(15) . . ? C19 N1 C18 110.9(2) . . ? C2 C1 N1 122.3(2) . . ? C2 C1 C10 119.4(2) . . ? N1 C1 C10 118.28(15) . . ? C1 C2 C3 121.1(2) . . ? C4 C3 C2 120.6(2) . . ? C3 C4 C9 120.6(2) . . ? C6 C5 C9 121.1(2) . . ? C5 C6 C7 119.8(2) . . ? C8 C7 C6 121.7(2) . . ? C7 C8 C10 119.6(2) . . ? C7 C8 C11 117.62(15) . . ? C10 C8 C11 122.49(15) . . ? C5 C9 C4 121.0(2) . . ? C5 C9 C10 119.6(2) . . ? C4 C9 C10 119.3(2) . . ? C9 C10 C1 118.4(2) . . ? C9 C10 C8 118.1(2) . . ? C1 C10 C8 123.5(2) . . ? C12 C11 C8 125.53(15) . . ? C11 C12 C15 121.79(15) . . ? C11 C12 C13 123.52(15) . . ? C15 C12 C13 113.54(14) . . ? O1 C13 C21 121.4(2) . . ? O1 C13 C12 121.5(2) . . ? C21 C13 C12 117.15(14) . . ? O2 C15 C12 119.05(15) . . ? O2 C15 C31 120.14(15) . . ? C12 C15 C31 120.77(14) . . ? C22 C21 C26 119.7(2) . . ? C22 C21 C13 120.9(2) . . ? C26 C21 C13 119.4(2) . . ? C21 C22 C23 120.4(2) . . ? C24 C23 C22 119.5(2) . . ? C25 C24 C23 120.3(2) . . ? C24 C25 C26 120.7(2) . . ? C25 C26 C21 119.2(2) . . ? C32 C31 C36 119.6(2) . . ? C32 C31 C15 117.6(2) . . ? C36 C31 C15 122.67(15) . . ? C31 C32 C33 120.1(2) . . ? C34 C33 C32 120.1(2) . . ? C35 C34 C33 120.2(2) . . ? C34 C35 C36 120.2(2) . . ? C35 C36 C31 119.9(2) . . ? _refine_diff_density_max 0.294 _refine_diff_density_min -0.254 _refine_diff_density_rms 0.055