Supplementary Material (ESI) for Organic & Biomolecular Chemistry This journal is (c) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Mogens Brondsted Nielsen' _publ_contact_author_address ; Department of Chemistry University of Copenhagen Universitetsparken 5 Copenhagen DK-2100 DENMARK ; _publ_contact_author_email MBN@KIKU.DK _publ_section_title ; Novel Retylidene Iminium Salts for Defining Opsin Shifts: Synthesis and Intrinsic Chromophoric Properties ; _publ_section_references ; Mackay, S., Gilmore, C. J.,Edwards, C., Stewart, N. & Shankland, K. (1999). maXus Computer Program for the Solution and Refinement of Crystal Structures. Bruker Nonius, The Netherlands, MacScience, Japan & The University of Glasgow. Johnson, C. K. (1976). ORTEP-II. A Fortran Thermal-Ellipsoid Plot Program. Report ORNL-5138. Oak Ridge National Laboratory, Oak Ridge, Tennessee, USA. Otwinowski, Z. and Minor, W, (1997). In Methods in Enzymology, 276, edited by C.W. Carter, Jr. & R.M. Sweet pp. 307-326, New York:Academic Press. Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of Gottingen, Germany. Coppens, P. (1970). In Crystallographic Computing, edited by F.R. Ahmed, S.R.Hall & C.P.Huber, pp 255-270. Copenhagen: Munksgaard. Duisenberg, A. J. M., Kroon-Batenburg, L. M. J. & Schreurs, A. M. M. (2003) J. Appl. Cryst. 36, 220. ; loop_ _publ_author_name 'Mogens Brondsted Nielsen' 'Lars Henrik Andersen' 'Anders Kadziola' 'Michael B. Kristensen' 'Lutz Lammich' ; I.B.Nielsen ; 'Michael A. Petersen' # Attachment 'CCDC294256.cif' data_shelxl _database_code_depnum_ccdc_archive 'CCDC 294256' _audit_creation_method maXus/SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H29 N' _chemical_formula_weight 307.46 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.8070(8) _cell_length_b 11.7490(12) _cell_length_c 16.027(2) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1846.7(4) _cell_formula_units_Z 4 _cell_measurement_temperature 122(2) _cell_measurement_reflns_used 29983 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 35.01 _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 0.59 _exptl_crystal_size_mid 0.49 _exptl_crystal_size_min 0.37 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.106 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 122(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 52673 _diffrn_reflns_av_R_equivalents 0.0449 _diffrn_reflns_av_sigmaI/netI 0.0255 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 35.01 _reflns_number_total 8043 _reflns_number_gt 7116 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'COLLECT (Nonius, 1999)' _computing_data_reduction 'EvalCCD (Duisenberg, 2003)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material ? _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^)+(0.0485P)^2^+0.2961P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0(3) _refine_ls_number_reflns 8043 _refine_ls_number_parameters 209 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0428 _refine_ls_wR_factor_ref 0.1093 _refine_ls_wR_factor_gt 0.0998 _refine_ls_goodness_of_fit_ref 1.117 _refine_ls_restrained_S_all 1.117 _refine_ls_shift/su_max 0.001 _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 N1 N 0.27584(11) -0.27342(9) 0.92034(7) 0.0342(2) Uani 1 1 d . . . C2 C 0.63227(11) 0.30760(9) 1.00213(7) 0.0271(2) Uani 1 1 d . . . H2A H 0.7249 0.2746 0.9979 0.033 Uiso 1 1 calc R . . H2B H 0.6419 0.3881 1.0193 0.033 Uiso 1 1 calc R . . C3 C 0.55287(12) 0.24381(9) 1.06852(7) 0.02811(19) Uani 1 1 d . . . H3A H 0.4599 0.2760 1.0734 0.034 Uiso 1 1 calc R . . H3B H 0.5989 0.2520 1.1232 0.034 Uiso 1 1 calc R . . C4 C 0.56378(9) 0.30291(7) 0.91603(6) 0.02083(16) Uani 1 1 d . . . C5 C 0.67057(12) 0.33786(10) 0.85054(8) 0.0323(2) Uani 1 1 d . . . H5A H 0.7378 0.2768 0.8442 0.039 Uiso 1 1 calc R . . H5B H 0.7166 0.4076 0.8688 0.039 Uiso 1 1 calc R . . H5C H 0.6253 0.3515 0.7970 0.039 Uiso 1 1 calc R . . C6 C 0.44539(11) 0.38890(8) 0.91236(7) 0.02689(19) Uani 1 1 d . . . H6A H 0.3786 0.3706 0.9558 0.032 Uiso 1 1 calc R . . H6B H 0.4016 0.3849 0.8575 0.032 Uiso 1 1 calc R . . H6C H 0.4807 0.4659 0.9215 0.032 Uiso 1 1 calc R . . C7 C 0.54429(11) 0.11831(9) 1.04490(7) 0.02514(18) Uani 1 1 d . . . H7A H 0.6338 0.0821 1.0553 0.030 Uiso 1 1 calc R . . H7B H 0.4763 0.0805 1.0812 0.030 Uiso 1 1 calc R . . C8 C 0.50925(9) 0.18317(7) 0.89740(6) 0.01835(15) Uani 1 1 d . . . C9 C 0.50506(9) 0.09947(7) 0.95484(6) 0.01992(15) Uani 1 1 d . . . C10 C 0.46227(11) -0.02114(8) 0.93696(7) 0.02668(19) Uani 1 1 d . . . H10A H 0.4628 -0.0341 0.8766 0.032 Uiso 1 1 calc R . . H10B H 0.3702 -0.0340 0.9588 0.032 Uiso 1 1 calc R . . H10C H 0.5260 -0.0739 0.9639 0.032 Uiso 1 1 calc R . . C11 C 0.45527(10) 0.16862(8) 0.81191(6) 0.02066(16) Uani 1 1 d . . . H11 H 0.5137 0.1855 0.7663 0.025 Uiso 1 1 calc R . . C12 C 0.32756(9) 0.13264(7) 0.79528(5) 0.01829(15) Uani 1 1 d . . . H12 H 0.2744 0.1059 0.8408 0.022 Uiso 1 1 calc R . . C13 C 0.26490(10) 0.13165(7) 0.71278(5) 0.01948(16) Uani 1 1 d . . . C14 C 0.34408(13) 0.18311(9) 0.64172(6) 0.0284(2) Uani 1 1 d . . . H14A H 0.2910 0.1766 0.5901 0.034 Uiso 1 1 calc R . . H14B H 0.4308 0.1426 0.6352 0.034 Uiso 1 1 calc R . . H14C H 0.3620 0.2636 0.6536 0.034 Uiso 1 1 calc R . . C15 C 0.13700(10) 0.09211(7) 0.69859(6) 0.02079(16) Uani 1 1 d . . . H15 H 0.1026 0.1037 0.6438 0.025 Uiso 1 1 calc R . . C16 C 0.04505(10) 0.03405(7) 0.75645(5) 0.01910(15) Uani 1 1 d . . . C17 C 0.08822(9) -0.04533(7) 0.81216(5) 0.01853(15) Uani 1 1 d . . . H17 H 0.1808 -0.0690 0.8106 0.022 Uiso 1 1 calc R . . C18 C -0.10437(11) 0.06326(9) 0.74843(7) 0.02588(19) Uani 1 1 d . . . H18A H -0.1288 0.0660 0.6885 0.031 Uiso 1 1 calc R . . H18B H -0.1200 0.1400 0.7721 0.031 Uiso 1 1 calc R . . C19 C -0.00185(10) -0.09532(8) 0.87395(6) 0.02006(15) Uani 1 1 d . . . C20 C -0.19773(10) -0.02155(11) 0.79245(7) 0.0298(2) Uani 1 1 d . . . H20A H -0.2909 0.0104 0.7964 0.036 Uiso 1 1 calc R . . H20B H -0.2025 -0.0929 0.7597 0.036 Uiso 1 1 calc R . . C21 C -0.14347(10) -0.04693(10) 0.87981(7) 0.02722(19) Uani 1 1 d . . . H21A H -0.1419 0.0239 0.9132 0.033 Uiso 1 1 calc R . . H21B H -0.2042 -0.1021 0.9081 0.033 Uiso 1 1 calc R . . C22 C 0.03781(11) -0.18023(8) 0.92592(6) 0.02390(17) Uani 1 1 d . . . H22 H -0.0250 -0.2073 0.9664 0.029 Uiso 1 1 calc R . . C23 C 0.17031(11) -0.23048(8) 0.92210(6) 0.02501(18) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0393(5) 0.0283(4) 0.0350(5) 0.0031(4) -0.0112(4) 0.0010(4) C2 0.0226(4) 0.0233(4) 0.0355(5) 0.0048(4) -0.0074(4) -0.0087(3) C3 0.0297(5) 0.0279(4) 0.0267(4) 0.0015(4) -0.0053(4) -0.0084(4) C4 0.0160(3) 0.0174(3) 0.0291(4) 0.0043(3) 0.0003(3) -0.0030(3) C5 0.0258(5) 0.0287(5) 0.0424(6) 0.0084(4) 0.0075(4) -0.0084(4) C6 0.0250(4) 0.0188(4) 0.0368(5) 0.0012(4) -0.0024(4) 0.0014(3) C7 0.0227(4) 0.0241(4) 0.0286(4) 0.0081(3) -0.0049(4) -0.0057(3) C8 0.0141(3) 0.0168(3) 0.0241(4) 0.0020(3) 0.0023(3) -0.0011(3) C9 0.0164(3) 0.0166(3) 0.0268(4) 0.0027(3) 0.0006(3) -0.0017(3) C10 0.0295(5) 0.0159(3) 0.0347(5) 0.0033(3) 0.0000(4) -0.0024(3) C11 0.0203(4) 0.0197(3) 0.0219(4) 0.0023(3) 0.0059(3) -0.0001(3) C12 0.0219(4) 0.0165(3) 0.0164(3) 0.0002(3) 0.0040(3) 0.0013(3) C13 0.0283(4) 0.0153(3) 0.0148(3) 0.0001(3) 0.0037(3) 0.0035(3) C14 0.0402(6) 0.0260(4) 0.0191(4) 0.0049(3) 0.0081(4) 0.0013(4) C15 0.0297(4) 0.0175(3) 0.0152(3) 0.0000(3) -0.0013(3) 0.0037(3) C16 0.0227(4) 0.0184(3) 0.0161(3) -0.0028(3) -0.0028(3) 0.0024(3) C17 0.0191(3) 0.0189(3) 0.0175(3) -0.0009(3) -0.0016(3) 0.0004(3) C18 0.0237(4) 0.0275(4) 0.0264(4) -0.0014(4) -0.0053(3) 0.0066(4) C19 0.0212(4) 0.0220(3) 0.0170(3) -0.0020(3) -0.0016(3) -0.0040(3) C20 0.0190(4) 0.0373(5) 0.0330(5) -0.0037(4) -0.0052(4) 0.0008(4) C21 0.0210(4) 0.0334(5) 0.0272(4) -0.0036(4) 0.0016(3) -0.0022(4) C22 0.0273(4) 0.0250(4) 0.0193(4) 0.0015(3) -0.0029(3) -0.0075(3) C23 0.0349(5) 0.0209(4) 0.0192(4) 0.0025(3) -0.0077(3) -0.0059(4) _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 N1 C23 1.1516(15) . ? C2 C3 1.5166(15) . ? C2 C4 1.5358(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C7 1.5246(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C5 1.5385(14) . ? C4 C8 1.5344(12) . ? C4 C6 1.5401(14) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C9 1.5101(15) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.3477(12) . ? C8 C11 1.4787(13) . ? C9 C10 1.5054(13) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3485(13) . ? C11 H11 0.9500 . ? C12 C13 1.4581(13) . ? C12 H12 0.9500 . ? C13 C15 1.3568(14) . ? C13 C14 1.5051(13) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.4623(13) . ? C15 H15 0.9500 . ? C16 C17 1.3588(12) . ? C16 C18 1.5105(14) . ? C17 C19 1.4511(13) . ? C17 H17 0.9500 . ? C18 C20 1.5261(17) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C22 1.3566(14) . ? C19 C21 1.5037(14) . ? C20 C21 1.5273(16) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.4286(15) . ? C22 H22 0.9500 . ? 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 C3 C2 C4 112.84(8) . . ? C3 C2 H2A 109.0 . . ? C4 C2 H2A 109.0 . . ? C3 C2 H2B 109.0 . . ? C4 C2 H2B 109.0 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C7 109.39(10) . . ? C2 C3 H3A 109.8 . . ? C7 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C7 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C5 C4 C8 110.44(9) . . ? C5 C4 C6 108.18(8) . . ? C8 C4 C6 109.35(7) . . ? C5 C4 C2 107.80(8) . . ? C8 C4 C2 111.11(8) . . ? C6 C4 C2 109.91(9) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C9 C7 C3 113.15(8) . . ? C9 C7 H7A 108.9 . . ? C3 C7 H7A 108.9 . . ? C9 C7 H7B 108.9 . . ? C3 C7 H7B 108.9 . . ? H7A C7 H7B 107.8 . . ? C9 C8 C11 122.53(8) . . ? C9 C8 C4 123.14(9) . . ? C11 C8 C4 114.27(8) . . ? C8 C9 C10 124.42(9) . . ? C8 C9 C7 122.56(8) . . ? C10 C9 C7 113.02(8) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C8 123.50(8) . . ? C12 C11 H11 118.3 . . ? C8 C11 H11 118.3 . . ? C11 C12 C13 124.97(8) . . ? C11 C12 H12 117.5 . . ? C13 C12 H12 117.5 . . ? C15 C13 C12 122.98(8) . . ? C15 C13 C14 119.19(9) . . ? C12 C13 C14 117.74(9) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 C16 128.58(8) . . ? C13 C15 H15 115.7 . . ? C16 C15 H15 115.7 . . ? C17 C16 C15 123.01(9) . . ? C17 C16 C18 120.94(9) . . ? C15 C16 C18 115.99(8) . . ? C16 C17 C19 122.45(8) . . ? C16 C17 H17 118.8 . . ? C19 C17 H17 118.8 . . ? C16 C18 C20 113.23(8) . . ? C16 C18 H18A 108.9 . . ? C20 C18 H18A 108.9 . . ? C16 C18 H18B 108.9 . . ? C20 C18 H18B 108.9 . . ? H18A C18 H18B 107.7 . . ? C22 C19 C17 122.83(9) . . ? C22 C19 C21 120.30(9) . . ? C17 C19 C21 116.86(8) . . ? C21 C20 C18 110.01(8) . . ? C21 C20 H20A 109.7 . . ? C18 C20 H20A 109.7 . . ? C21 C20 H20B 109.7 . . ? C18 C20 H20B 109.7 . . ? H20A C20 H20B 108.2 . . ? C19 C21 C20 109.78(8) . . ? C19 C21 H21A 109.7 . . ? C20 C21 H21A 109.7 . . ? C19 C21 H21B 109.7 . . ? C20 C21 H21B 109.7 . . ? H21A C21 H21B 108.2 . . ? C19 C22 C23 122.57(9) . . ? C19 C22 H22 118.7 . . ? C23 C22 H22 118.7 . . ? N1 C23 C22 178.12(11) . . ? 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 C4 C2 C3 C7 61.80(12) . . . . ? C3 C2 C4 C5 -163.50(9) . . . . ? C3 C2 C4 C8 -42.36(12) . . . . ? C3 C2 C4 C6 78.80(11) . . . . ? C2 C3 C7 C9 -46.42(12) . . . . ? C5 C4 C8 C9 128.71(10) . . . . ? C6 C4 C8 C9 -112.36(10) . . . . ? C2 C4 C8 C9 9.13(12) . . . . ? C5 C4 C8 C11 -54.09(10) . . . . ? C6 C4 C8 C11 64.85(10) . . . . ? C2 C4 C8 C11 -173.66(8) . . . . ? C11 C8 C9 C10 7.89(14) . . . . ? C4 C8 C9 C10 -175.13(9) . . . . ? C11 C8 C9 C7 -172.40(9) . . . . ? C4 C8 C9 C7 4.57(14) . . . . ? C3 C7 C9 C8 14.77(14) . . . . ? C3 C7 C9 C10 -165.49(9) . . . . ? C9 C8 C11 C12 53.44(13) . . . . ? C4 C8 C11 C12 -123.79(9) . . . . ? C8 C11 C12 C13 171.41(8) . . . . ? C11 C12 C13 C15 178.38(9) . . . . ? C11 C12 C13 C14 -5.11(13) . . . . ? C12 C13 C15 C16 -7.07(14) . . . . ? C14 C13 C15 C16 176.48(9) . . . . ? C13 C15 C16 C17 -39.91(14) . . . . ? C13 C15 C16 C18 142.84(10) . . . . ? C15 C16 C17 C19 174.67(8) . . . . ? C18 C16 C17 C19 -8.21(13) . . . . ? C17 C16 C18 C20 -13.09(13) . . . . ? C15 C16 C18 C20 164.23(8) . . . . ? C16 C17 C19 C22 175.26(9) . . . . ? C16 C17 C19 C21 -6.01(13) . . . . ? C16 C18 C20 C21 46.42(12) . . . . ? C22 C19 C21 C20 -141.48(10) . . . . ? C17 C19 C21 C20 39.76(12) . . . . ? C18 C20 C21 C19 -59.26(12) . . . . ? C17 C19 C22 C23 -2.36(14) . . . . ? C21 C19 C22 C23 178.96(9) . . . . ? C19 C22 C23 N1 -165(4) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 35.01 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.358 _refine_diff_density_min -0.144 _refine_diff_density_rms 0.043 data_shelxl2 _database_code_depnum_ccdc_archive 'CCDC 294257' _audit_creation_method maXus/SHELXL-97 _chemical_name_systematic ? _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H29 N' _chemical_formula_weight 307.46 _chemical_absolute_configuration unk 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 orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' _cell_length_a 9.8840(16) _cell_length_b 11.7110(11) _cell_length_c 16.091(2) _cell_angle_alpha 90.0 _cell_angle_beta 90.0 _cell_angle_gamma 90.0 _cell_volume 1862.6(4) _cell_formula_units_Z 4 _cell_measurement_temperature 122(2) _cell_measurement_reflns_used 27434 _cell_measurement_theta_min 2.15 _cell_measurement_theta_max 32.98 _exptl_crystal_description ? _exptl_crystal_colour yellow _exptl_crystal_size_max 0.72 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.096 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 122(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_method CCD _diffrn_detector_area_resol_mean 9 _diffrn_reflns_number 50833 _diffrn_reflns_av_R_equivalents 0.0674 _diffrn_reflns_av_sigmaI/netI 0.0339 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -24 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.15 _diffrn_reflns_theta_max 32.98 _reflns_number_total 6990 _reflns_number_gt 6132 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'COLLECT (Nonius, 1999)' _computing_data_reduction 'EvalCCD (Duisenberg, 2003)' _computing_structure_solution 'SIR97 (Altomare, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-II (Johnson, 1976)' _computing_publication_material ? _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^)+(0.0535P)^2^+0.2845P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1(3) _refine_ls_number_reflns 6990 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0553 _refine_ls_R_factor_gt 0.0431 _refine_ls_wR_factor_ref 0.1127 _refine_ls_wR_factor_gt 0.1036 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _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 N1 N -0.68506(13) 0.20313(11) -0.53260(8) 0.0406(3) Uani 1 1 d . . . C2 C 0.13433(11) -0.30182(9) -0.50686(7) 0.0262(2) Uani 1 1 d . . . H2A H 0.2253 -0.2674 -0.5010 0.031 Uiso 1 1 calc R . . H2B H 0.1462 -0.3817 -0.5257 0.031 Uiso 1 1 calc R . . C3 C 0.05507(12) -0.23594(10) -0.57239(7) 0.0275(2) Uani 1 1 d . . . H3A H -0.0361 -0.2699 -0.5789 0.033 Uiso 1 1 calc R . . H3B H 0.1023 -0.2406 -0.6265 0.033 Uiso 1 1 calc R . . C4 C 0.06394(10) -0.30184(8) -0.42179(6) 0.01989(17) Uani 1 1 d . . . C5 C 0.16955(12) -0.33819(10) -0.35642(8) 0.0310(2) Uani 1 1 d . . . H5A H 0.1236 -0.3572 -0.3043 0.037 Uiso 1 1 calc R . . H5B H 0.2331 -0.2753 -0.3469 0.037 Uiso 1 1 calc R . . H5C H 0.2191 -0.4052 -0.3766 0.037 Uiso 1 1 calc R . . C6 C -0.05104(12) -0.39045(9) -0.42142(8) 0.0269(2) Uani 1 1 d . . . H6A H -0.0151 -0.4652 -0.4376 0.032 Uiso 1 1 calc R . . H6B H -0.1213 -0.3672 -0.4609 0.032 Uiso 1 1 calc R . . H6C H -0.0899 -0.3954 -0.3655 0.032 Uiso 1 1 calc R . . C7 C 0.04236(11) -0.11164(9) -0.54589(7) 0.0248(2) Uani 1 1 d . . . H7A H 0.1305 -0.0732 -0.5542 0.030 Uiso 1 1 calc R . . H7B H -0.0248 -0.0733 -0.5820 0.030 Uiso 1 1 calc R . . C8 C 0.00577(9) -0.18356(8) -0.40095(6) 0.01793(16) Uani 1 1 d . . . C9 C -0.00009(10) -0.09741(8) -0.45639(6) 0.01964(17) Uani 1 1 d . . . C10 C -0.04653(13) 0.02211(9) -0.43632(8) 0.0273(2) Uani 1 1 d . . . H10A H 0.0184 0.0773 -0.4589 0.033 Uiso 1 1 calc R . . H10B H -0.0524 0.0314 -0.3759 0.033 Uiso 1 1 calc R . . H10C H -0.1357 0.0354 -0.4612 0.033 Uiso 1 1 calc R . . C11 C -0.04652(10) -0.17253(8) -0.31521(6) 0.02025(17) Uani 1 1 d . . . H11 H 0.0129 -0.1913 -0.2709 0.024 Uiso 1 1 calc R . . C12 C -0.17236(10) -0.13775(9) -0.29554(6) 0.01968(17) Uani 1 1 d . . . H12 H -0.2294 -0.1121 -0.3392 0.024 Uiso 1 1 calc R . . C13 C -0.22646(11) -0.13703(9) -0.21113(6) 0.02163(19) Uani 1 1 d . . . C14 C -0.13657(13) -0.18161(11) -0.14300(7) 0.0298(2) Uani 1 1 d . . . H14A H -0.1865 -0.1819 -0.0904 0.036 Uiso 1 1 calc R . . H14B H -0.0568 -0.1324 -0.1378 0.036 Uiso 1 1 calc R . . H14C H -0.1079 -0.2596 -0.1564 0.036 Uiso 1 1 calc R . . C15 C -0.35418(12) -0.10286(9) -0.19230(6) 0.0242(2) Uani 1 1 d . . . H15 H -0.3795 -0.1119 -0.1357 0.029 Uiso 1 1 calc R . . C16 C -0.45843(11) -0.05429(9) -0.24610(6) 0.02263(19) Uani 1 1 d . . . C17 C -0.43361(11) 0.02360(9) -0.30687(7) 0.02330(19) Uani 1 1 d . . . H17 H -0.3446 0.0534 -0.3122 0.028 Uiso 1 1 calc R . . C18 C -0.60131(12) -0.09362(11) -0.22845(7) 0.0290(2) Uani 1 1 d . . . H18A H -0.6140 -0.1003 -0.1676 0.035 Uiso 1 1 calc R . . H18B H -0.6149 -0.1703 -0.2530 0.035 Uiso 1 1 calc R . . C19 C -0.53705(11) 0.06324(9) -0.36404(7) 0.0242(2) Uani 1 1 d . . . C20 C -0.70703(12) -0.01217(12) -0.26335(9) 0.0333(3) Uani 1 1 d . . . H20A H -0.7064 0.0598 -0.2310 0.040 Uiso 1 1 calc R . . H20B H -0.7980 -0.0469 -0.2583 0.040 Uiso 1 1 calc R . . C21 C -0.67727(11) 0.01359(11) -0.35461(8) 0.0293(2) Uani 1 1 d . . . H21A H -0.6843 -0.0576 -0.3876 0.035 Uiso 1 1 calc R . . H21B H -0.7449 0.0684 -0.3762 0.035 Uiso 1 1 calc R . . C22 C -0.50646(12) 0.13919(10) -0.42489(7) 0.0276(2) Uani 1 1 d . . . H22 H -0.4173 0.1692 -0.4282 0.033 Uiso 1 1 calc R . . C23 C -0.60553(13) 0.17513(11) -0.48428(8) 0.0317(2) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 N1 0.0377(6) 0.0405(6) 0.0437(6) 0.0045(5) 0.0041(5) 0.0098(5) C2 0.0207(4) 0.0244(5) 0.0334(5) 0.0029(4) 0.0078(4) 0.0063(4) C3 0.0290(5) 0.0292(5) 0.0244(5) 0.0002(4) 0.0054(4) 0.0056(4) C4 0.0156(4) 0.0170(4) 0.0270(5) 0.0029(3) 0.0009(3) 0.0016(3) C5 0.0246(5) 0.0290(5) 0.0394(6) 0.0080(5) -0.0058(4) 0.0074(4) C6 0.0250(5) 0.0192(4) 0.0367(5) -0.0008(4) 0.0050(4) -0.0036(4) C7 0.0223(4) 0.0250(5) 0.0270(5) 0.0061(4) 0.0031(4) 0.0028(4) C8 0.0133(3) 0.0176(4) 0.0229(4) 0.0008(3) -0.0012(3) 0.0004(3) C9 0.0159(4) 0.0174(4) 0.0256(4) 0.0012(3) -0.0003(3) 0.0003(3) C10 0.0301(5) 0.0168(4) 0.0351(5) 0.0014(4) -0.0003(4) 0.0016(4) C11 0.0186(4) 0.0205(4) 0.0216(4) 0.0005(3) -0.0032(3) -0.0016(3) C12 0.0203(4) 0.0205(4) 0.0183(4) -0.0019(3) -0.0018(3) -0.0022(3) C13 0.0268(5) 0.0203(4) 0.0177(4) -0.0032(3) -0.0013(3) -0.0053(4) C14 0.0355(6) 0.0332(6) 0.0209(5) 0.0025(4) -0.0052(4) -0.0037(5) C15 0.0290(5) 0.0246(5) 0.0190(4) -0.0055(4) 0.0038(4) -0.0060(4) C16 0.0220(4) 0.0239(4) 0.0220(4) -0.0083(4) 0.0054(4) -0.0037(4) C17 0.0193(4) 0.0235(4) 0.0271(5) -0.0058(4) 0.0046(4) -0.0015(3) C18 0.0254(5) 0.0346(6) 0.0271(5) -0.0045(4) 0.0077(4) -0.0085(4) C19 0.0213(4) 0.0224(4) 0.0290(5) -0.0066(4) 0.0054(4) 0.0013(4) C20 0.0210(5) 0.0391(6) 0.0398(6) -0.0074(5) 0.0112(5) -0.0040(4) C21 0.0195(4) 0.0312(5) 0.0372(6) -0.0023(5) 0.0020(4) -0.0003(4) C22 0.0244(5) 0.0263(5) 0.0322(5) -0.0022(4) 0.0053(4) 0.0028(4) C23 0.0301(5) 0.0280(5) 0.0371(6) -0.0018(5) 0.0088(5) 0.0051(4) _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 N1 C23 1.1532(18) . ? C2 C3 1.5234(16) . ? C2 C4 1.5356(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C7 1.5220(16) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C6 1.5390(14) . ? C4 C8 1.5368(13) . ? C4 C5 1.5418(15) . ? C5 H5A 0.9800 . ? C5 H5B 0.9800 . ? C5 H5C 0.9800 . ? C6 H6A 0.9800 . ? C6 H6B 0.9800 . ? C6 H6C 0.9800 . ? C7 C9 1.5092(15) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.3480(13) . ? C8 C11 1.4789(14) . ? C9 C10 1.5080(14) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.3465(15) . ? C11 H11 0.9500 . ? C12 C13 1.4598(14) . ? C12 H12 0.9500 . ? C13 C15 1.3585(16) . ? C13 C14 1.5046(16) . ? C14 H14A 0.9800 . ? C14 H14B 0.9800 . ? C14 H14C 0.9800 . ? C15 C16 1.4610(16) . ? C15 H15 0.9500 . ? C16 C17 1.3596(15) . ? C16 C18 1.5124(16) . ? C17 C19 1.4516(16) . ? C17 H17 0.9500 . ? C18 C20 1.5222(19) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C22 1.3570(16) . ? C19 C21 1.5106(16) . ? C20 C21 1.5278(19) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9900 . ? C21 H21B 0.9900 . ? C22 C23 1.4315(18) . ? C22 H22 0.9500 . ? 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 C3 C2 C4 112.58(8) . . ? C3 C2 H2A 109.1 . . ? C4 C2 H2A 109.1 . . ? C3 C2 H2B 109.1 . . ? C4 C2 H2B 109.1 . . ? H2A C2 H2B 107.8 . . ? C2 C3 C7 109.45(10) . . ? C2 C3 H3A 109.8 . . ? C7 C3 H3A 109.8 . . ? C2 C3 H3B 109.8 . . ? C7 C3 H3B 109.8 . . ? H3A C3 H3B 108.2 . . ? C6 C4 C2 109.76(9) . . ? C6 C4 C8 109.31(8) . . ? C2 C4 C8 111.34(8) . . ? C6 C4 C5 108.13(9) . . ? C2 C4 C5 107.54(9) . . ? C8 C4 C5 110.69(9) . . ? C4 C5 H5A 109.5 . . ? C4 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C4 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C4 C6 H6A 109.5 . . ? C4 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C4 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C9 C7 C3 113.32(9) . . ? C9 C7 H7A 108.9 . . ? C3 C7 H7A 108.9 . . ? C9 C7 H7B 108.9 . . ? C3 C7 H7B 108.9 . . ? H7A C7 H7B 107.7 . . ? C9 C8 C11 122.48(9) . . ? C9 C8 C4 123.12(9) . . ? C11 C8 C4 114.39(8) . . ? C8 C9 C10 124.48(9) . . ? C8 C9 C7 122.47(9) . . ? C10 C9 C7 113.05(9) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C12 C11 C8 124.65(9) . . ? C12 C11 H11 117.7 . . ? C8 C11 H11 117.7 . . ? C11 C12 C13 123.98(9) . . ? C11 C12 H12 118.0 . . ? C13 C12 H12 118.0 . . ? C15 C13 C12 123.34(10) . . ? C15 C13 C14 119.24(10) . . ? C12 C13 C14 117.37(10) . . ? C13 C14 H14A 109.5 . . ? C13 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C13 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C13 C15 C16 129.64(9) . . ? C13 C15 H15 115.2 . . ? C16 C15 H15 115.2 . . ? C17 C16 C15 124.06(10) . . ? C17 C16 C18 120.53(10) . . ? C15 C16 C18 115.38(9) . . ? C16 C17 C19 122.91(10) . . ? C16 C17 H17 118.5 . . ? C19 C17 H17 118.5 . . ? C16 C18 C20 112.39(10) . . ? C16 C18 H18A 109.1 . . ? C20 C18 H18A 109.1 . . ? C16 C18 H18B 109.1 . . ? C20 C18 H18B 109.1 . . ? H18A C18 H18B 107.9 . . ? C22 C19 C17 120.66(10) . . ? C22 C19 C21 121.95(11) . . ? C17 C19 C21 117.35(10) . . ? C18 C20 C21 110.25(10) . . ? C18 C20 H20A 109.6 . . ? C21 C20 H20A 109.6 . . ? C18 C20 H20B 109.6 . . ? C21 C20 H20B 109.6 . . ? H20A C20 H20B 108.1 . . ? C19 C21 C20 110.44(10) . . ? C19 C21 H21A 109.6 . . ? C20 C21 H21A 109.6 . . ? C19 C21 H21B 109.6 . . ? C20 C21 H21B 109.6 . . ? H21A C21 H21B 108.1 . . ? C19 C22 C23 121.47(11) . . ? C19 C22 H22 119.3 . . ? C23 C22 H22 119.3 . . ? N1 C23 C22 179.31(14) . . ? 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 C4 C2 C3 C7 61.55(12) . . . . ? C3 C2 C4 C6 79.02(11) . . . . ? C3 C2 C4 C8 -42.15(12) . . . . ? C3 C2 C4 C5 -163.57(10) . . . . ? C2 C3 C7 C9 -46.75(13) . . . . ? C6 C4 C8 C9 -111.90(11) . . . . ? C2 C4 C8 C9 9.54(13) . . . . ? C5 C4 C8 C9 129.10(10) . . . . ? C6 C4 C8 C11 66.74(11) . . . . ? C2 C4 C8 C11 -171.82(8) . . . . ? C5 C4 C8 C11 -52.25(11) . . . . ? C11 C8 C9 C10 6.36(15) . . . . ? C4 C8 C9 C10 -175.11(9) . . . . ? C11 C8 C9 C7 -174.69(9) . . . . ? C4 C8 C9 C7 3.84(15) . . . . ? C3 C7 C9 C8 15.51(15) . . . . ? C3 C7 C9 C10 -165.43(10) . . . . ? C9 C8 C11 C12 53.19(15) . . . . ? C4 C8 C11 C12 -125.46(11) . . . . ? C8 C11 C12 C13 174.28(9) . . . . ? C11 C12 C13 C15 -179.26(10) . . . . ? C11 C12 C13 C14 -2.03(15) . . . . ? C12 C13 C15 C16 -4.60(17) . . . . ? C14 C13 C15 C16 178.22(10) . . . . ? C13 C15 C16 C17 -40.14(17) . . . . ? C13 C15 C16 C18 141.76(11) . . . . ? C15 C16 C17 C19 174.63(10) . . . . ? C18 C16 C17 C19 -7.36(15) . . . . ? C17 C16 C18 C20 -18.49(14) . . . . ? C15 C16 C18 C20 159.68(9) . . . . ? C16 C17 C19 C22 -178.48(10) . . . . ? C16 C17 C19 C21 -0.52(15) . . . . ? C16 C18 C20 C21 50.45(13) . . . . ? C22 C19 C21 C20 -148.95(11) . . . . ? C17 C19 C21 C20 33.12(14) . . . . ? C18 C20 C21 C19 -57.49(13) . . . . ? C17 C19 C22 C23 176.99(10) . . . . ? C21 C19 C22 C23 -0.88(17) . . . . ? C19 C22 C23 N1 -85(14) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 32.98 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.308 _refine_diff_density_min -0.194 _refine_diff_density_rms 0.043