# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers # This journal is © The Partner Organisations 2014 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_110428_kwq_15_35 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N' _chemical_formula_sum 'C21 H27 N' _chemical_formula_weight 293.44 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 b c a' _symmetry_space_group_name_Hall '-P 2ac 2ab' 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' '-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 9.2391(3) _cell_length_b 17.1518(6) _cell_length_c 22.2035(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3518.53(19) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4531 _cell_measurement_theta_min 2.8625 _cell_measurement_theta_max 29.3164 _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1280 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9801 _exptl_absorpt_correction_T_max 0.9906 _exptl_absorpt_process_details ; CrysAlis PRO (Oxford Diffraction, 2010) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 21053 _diffrn_reflns_av_R_equivalents 0.0352 _diffrn_reflns_av_sigmaI/netI 0.0199 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -26 _diffrn_reflns_limit_l_max 26 _diffrn_reflns_theta_min 2.87 _diffrn_reflns_theta_max 25.34 _reflns_number_total 3218 _reflns_number_gt 2414 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Oxford Diffraction, 2010)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0577P)^2^+0.9709P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3218 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0676 _refine_ls_R_factor_gt 0.0479 _refine_ls_wR_factor_ref 0.1320 _refine_ls_wR_factor_gt 0.1184 _refine_ls_goodness_of_fit_ref 1.026 _refine_ls_restrained_S_all 1.026 _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 0.98833(15) 0.67571(8) -0.00153(6) 0.0536(4) Uani 1 1 d . . . C1 C 1.0723(2) 0.79335(12) 0.05511(10) 0.0692(6) Uani 1 1 d . . . H1 H 1.1307 0.8126 0.0244 0.083 Uiso 1 1 calc R . . C2 C 1.0602(2) 0.83186(12) 0.10913(11) 0.0743(6) Uani 1 1 d . . . H2 H 1.1121 0.8778 0.1145 0.089 Uiso 1 1 calc R . . C3 C 0.9739(2) 0.80521(11) 0.15600(9) 0.0653(5) Uani 1 1 d . . . C4 C 0.89596(19) 0.73715(10) 0.14791(8) 0.0548(4) Uani 1 1 d . . . H4 H 0.8373 0.7187 0.1788 0.066 Uiso 1 1 calc R . . C5 C 0.90451(16) 0.69589(9) 0.09377(7) 0.0453(4) Uani 1 1 d . . . C6 C 0.99417(18) 0.72458(10) 0.04788(8) 0.0521(4) Uani 1 1 d . . . C7 C 0.9655(3) 0.84880(14) 0.21523(11) 0.1011(8) Uani 1 1 d . . . H7B H 0.9302 0.9007 0.2082 0.152 Uiso 1 1 calc R . . H7C H 1.0601 0.8514 0.2330 0.152 Uiso 1 1 calc R . . H7A H 0.9009 0.8220 0.2420 0.152 Uiso 1 1 calc R . . C8 C 0.83904(16) 0.62566(9) 0.07042(7) 0.0421(4) Uani 1 1 d . . . C9 C 0.74071(17) 0.57196(9) 0.09495(7) 0.0450(4) Uani 1 1 d . . . C10 C 0.69844(17) 0.51111(10) 0.05845(8) 0.0519(4) Uani 1 1 d . . . H10 H 0.6332 0.4749 0.0738 0.062 Uiso 1 1 calc R . . C11 C 0.74844(18) 0.50090(10) -0.00033(8) 0.0512(4) Uani 1 1 d . . . C12 C 0.84749(17) 0.55242(10) -0.02552(7) 0.0489(4) Uani 1 1 d . . . C13 C 0.89224(16) 0.61496(9) 0.01105(7) 0.0443(4) Uani 1 1 d . . . C14 C 0.9019(2) 0.53872(12) -0.08869(8) 0.0665(5) Uani 1 1 d . . . H14C H 0.8952 0.5862 -0.1114 0.100 Uiso 1 1 calc R . . H14A H 0.8442 0.4992 -0.1077 0.100 Uiso 1 1 calc R . . H14B H 1.0010 0.5220 -0.0872 0.100 Uiso 1 1 calc R . . C15 C 0.6918(2) 0.43174(12) -0.03566(9) 0.0719(6) Uani 1 1 d . . . H15B H 0.6373 0.4500 -0.0697 0.108 Uiso 1 1 calc R . . H15A H 0.6306 0.4007 -0.0103 0.108 Uiso 1 1 calc R . . H15C H 0.7718 0.4007 -0.0494 0.108 Uiso 1 1 calc R . . C16 C 1.0716(2) 0.69081(13) -0.05601(8) 0.0675(5) Uani 1 1 d . . . H16A H 1.0969 0.6415 -0.0746 0.081 Uiso 1 1 calc R . . H16B H 1.1608 0.7171 -0.0452 0.081 Uiso 1 1 calc R . . C17 C 0.9903(3) 0.74011(13) -0.10110(9) 0.0853(7) Uani 1 1 d . . . H17B H 1.0455 0.7438 -0.1376 0.128 Uiso 1 1 calc R . . H17C H 0.9756 0.7913 -0.0848 0.128 Uiso 1 1 calc R . . H17A H 0.8983 0.7165 -0.1095 0.128 Uiso 1 1 calc R . . C18 C 0.68886(17) 0.57684(10) 0.15908(7) 0.0510(4) Uani 1 1 d . . . H18A H 0.6006 0.5466 0.1631 0.061 Uiso 1 1 calc R . . H18B H 0.6660 0.6307 0.1684 0.061 Uiso 1 1 calc R . . C19 C 0.7997(2) 0.54703(11) 0.20431(7) 0.0585(5) Uani 1 1 d . . . H19A H 0.8215 0.4930 0.1951 0.070 Uiso 1 1 calc R . . H19B H 0.8884 0.5767 0.1996 0.070 Uiso 1 1 calc R . . C20 C 0.7510(2) 0.55240(12) 0.26964(8) 0.0714(6) Uani 1 1 d . . . H20A H 0.6581 0.5265 0.2736 0.086 Uiso 1 1 calc R . . H20B H 0.8198 0.5244 0.2946 0.086 Uiso 1 1 calc R . . C21 C 0.7371(3) 0.63431(14) 0.29323(9) 0.0931(8) Uani 1 1 d . . . H21A H 0.6693 0.6627 0.2689 0.140 Uiso 1 1 calc R . . H21C H 0.8297 0.6596 0.2918 0.140 Uiso 1 1 calc R . . H21B H 0.7033 0.6329 0.3341 0.140 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 N1 0.0506(8) 0.0599(9) 0.0502(8) 0.0127(7) 0.0076(6) -0.0018(7) C1 0.0591(11) 0.0652(12) 0.0835(14) 0.0167(11) 0.0034(10) -0.0119(10) C2 0.0717(13) 0.0541(11) 0.0970(17) 0.0050(11) -0.0110(12) -0.0145(10) C3 0.0726(12) 0.0483(11) 0.0750(13) -0.0021(9) -0.0120(10) -0.0009(9) C4 0.0586(10) 0.0496(10) 0.0562(10) 0.0033(8) -0.0029(8) 0.0026(8) C5 0.0422(8) 0.0434(9) 0.0504(9) 0.0078(7) -0.0025(7) 0.0047(7) C6 0.0456(9) 0.0510(10) 0.0597(10) 0.0119(8) -0.0015(8) -0.0010(8) C7 0.133(2) 0.0711(15) 0.0989(18) -0.0248(13) -0.0090(16) -0.0133(15) C8 0.0395(8) 0.0442(9) 0.0426(8) 0.0070(7) -0.0011(6) 0.0049(7) C9 0.0420(8) 0.0467(9) 0.0461(9) 0.0055(7) 0.0003(7) 0.0042(7) C10 0.0459(9) 0.0512(10) 0.0585(10) 0.0045(8) 0.0012(7) -0.0036(8) C11 0.0487(9) 0.0524(9) 0.0524(9) -0.0019(7) -0.0065(8) 0.0060(8) C12 0.0474(9) 0.0566(10) 0.0428(9) 0.0033(7) -0.0047(7) 0.0128(8) C13 0.0393(8) 0.0488(9) 0.0449(9) 0.0107(7) -0.0005(7) 0.0062(7) C14 0.0754(13) 0.0753(13) 0.0489(10) 0.0006(9) 0.0005(9) 0.0086(10) C15 0.0733(13) 0.0687(13) 0.0738(13) -0.0140(10) -0.0101(10) -0.0005(10) C16 0.0565(11) 0.0835(14) 0.0625(12) 0.0166(10) 0.0167(9) -0.0057(10) C17 0.1022(17) 0.0869(16) 0.0668(13) 0.0301(11) 0.0122(12) -0.0060(13) C18 0.0475(9) 0.0539(10) 0.0515(9) 0.0058(8) 0.0090(7) 0.0008(8) C19 0.0629(11) 0.0610(11) 0.0517(10) 0.0115(8) 0.0080(8) 0.0100(9) C20 0.0806(13) 0.0832(14) 0.0504(11) 0.0119(10) 0.0084(10) 0.0108(11) C21 0.127(2) 0.0978(18) 0.0542(12) -0.0067(11) 0.0103(13) 0.0050(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 N1 C6 1.382(2) . ? N1 C13 1.397(2) . ? N1 C16 1.457(2) . ? C1 C2 1.374(3) . ? C1 C6 1.392(3) . ? C1 H1 0.9300 . ? C2 C3 1.389(3) . ? C2 H2 0.9300 . ? C3 C4 1.383(3) . ? C3 C7 1.515(3) . ? C4 C5 1.397(2) . ? C4 H4 0.9300 . ? C5 C6 1.402(2) . ? C5 C8 1.444(2) . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C7 H7A 0.9600 . ? C8 C9 1.404(2) . ? C8 C13 1.419(2) . ? C9 C10 1.378(2) . ? C9 C18 1.505(2) . ? C10 C11 1.396(2) . ? C10 H10 0.9300 . ? C11 C12 1.390(2) . ? C11 C15 1.515(3) . ? C12 C13 1.407(2) . ? C12 C14 1.508(2) . ? C14 H14C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C15 H15B 0.9600 . ? C15 H15A 0.9600 . ? C15 H15C 0.9600 . ? C16 C17 1.510(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C17 H17A 0.9600 . ? C18 C19 1.523(2) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.522(2) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.505(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21C 0.9600 . ? C21 H21B 0.9600 . ? 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 C6 N1 C13 108.57(13) . . ? C6 N1 C16 122.06(15) . . ? C13 N1 C16 129.36(15) . . ? C2 C1 C6 117.79(18) . . ? C2 C1 H1 121.1 . . ? C6 C1 H1 121.1 . . ? C1 C2 C3 122.86(19) . . ? C1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 118.66(18) . . ? C4 C3 C7 120.18(19) . . ? C2 C3 C7 121.16(19) . . ? C3 C4 C5 120.65(17) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C4 C5 C6 118.74(16) . . ? C4 C5 C8 135.05(15) . . ? C6 C5 C8 106.21(14) . . ? N1 C6 C1 128.75(16) . . ? N1 C6 C5 109.93(14) . . ? C1 C6 C5 121.31(17) . . ? C3 C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C3 C7 H7A 109.5 . . ? H7B C7 H7A 109.5 . . ? H7C C7 H7A 109.5 . . ? C9 C8 C13 119.99(14) . . ? C9 C8 C5 132.77(15) . . ? C13 C8 C5 107.24(13) . . ? C10 C9 C8 116.89(14) . . ? C10 C9 C18 120.56(15) . . ? C8 C9 C18 122.46(15) . . ? C9 C10 C11 123.46(16) . . ? C9 C10 H10 118.3 . . ? C11 C10 H10 118.3 . . ? C12 C11 C10 120.97(16) . . ? C12 C11 C15 121.11(16) . . ? C10 C11 C15 117.91(16) . . ? C11 C12 C13 116.48(15) . . ? C11 C12 C14 119.65(16) . . ? C13 C12 C14 123.87(16) . . ? N1 C13 C12 129.77(15) . . ? N1 C13 C8 108.02(14) . . ? C12 C13 C8 122.20(14) . . ? C12 C14 H14C 109.5 . . ? C12 C14 H14A 109.5 . . ? H14C C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C11 C15 H15B 109.5 . . ? C11 C15 H15A 109.5 . . ? H15B C15 H15A 109.5 . . ? C11 C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? N1 C16 C17 112.80(16) . . ? N1 C16 H16A 109.0 . . ? C17 C16 H16A 109.0 . . ? N1 C16 H16B 109.0 . . ? C17 C16 H16B 109.0 . . ? H16A C16 H16B 107.8 . . ? C16 C17 H17B 109.5 . . ? C16 C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C16 C17 H17A 109.5 . . ? H17B C17 H17A 109.5 . . ? H17C C17 H17A 109.5 . . ? C9 C18 C19 113.04(13) . . ? C9 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C9 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C18 114.18(15) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C21 C20 C19 114.42(17) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? H21C C21 H21B 109.5 . . ? 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 C6 C1 C2 C3 -0.2(3) . . . . ? C1 C2 C3 C4 -0.3(3) . . . . ? C1 C2 C3 C7 179.0(2) . . . . ? C2 C3 C4 C5 0.3(3) . . . . ? C7 C3 C4 C5 -179.08(19) . . . . ? C3 C4 C5 C6 0.3(2) . . . . ? C3 C4 C5 C8 -179.16(17) . . . . ? C13 N1 C6 C1 -178.20(17) . . . . ? C16 N1 C6 C1 1.1(3) . . . . ? C13 N1 C6 C5 1.12(18) . . . . ? C16 N1 C6 C5 -179.61(14) . . . . ? C2 C1 C6 N1 -179.91(18) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? C4 C5 C6 N1 179.73(14) . . . . ? C8 C5 C6 N1 -0.66(18) . . . . ? C4 C5 C6 C1 -0.9(2) . . . . ? C8 C5 C6 C1 178.72(15) . . . . ? C4 C5 C8 C9 -0.4(3) . . . . ? C6 C5 C8 C9 -179.93(16) . . . . ? C4 C5 C8 C13 179.48(17) . . . . ? C6 C5 C8 C13 -0.04(16) . . . . ? C13 C8 C9 C10 -1.2(2) . . . . ? C5 C8 C9 C10 178.67(15) . . . . ? C13 C8 C9 C18 175.42(14) . . . . ? C5 C8 C9 C18 -4.7(3) . . . . ? C8 C9 C10 C11 0.2(2) . . . . ? C18 C9 C10 C11 -176.55(15) . . . . ? C9 C10 C11 C12 0.8(3) . . . . ? C9 C10 C11 C15 -179.43(16) . . . . ? C10 C11 C12 C13 -0.7(2) . . . . ? C15 C11 C12 C13 179.58(15) . . . . ? C10 C11 C12 C14 178.63(15) . . . . ? C15 C11 C12 C14 -1.1(2) . . . . ? C6 N1 C13 C12 178.06(16) . . . . ? C16 N1 C13 C12 -1.1(3) . . . . ? C6 N1 C13 C8 -1.12(17) . . . . ? C16 N1 C13 C8 179.68(16) . . . . ? C11 C12 C13 N1 -179.46(15) . . . . ? C14 C12 C13 N1 1.2(3) . . . . ? C11 C12 C13 C8 -0.4(2) . . . . ? C14 C12 C13 C8 -179.67(15) . . . . ? C9 C8 C13 N1 -179.38(13) . . . . ? C5 C8 C13 N1 0.71(16) . . . . ? C9 C8 C13 C12 1.4(2) . . . . ? C5 C8 C13 C12 -178.55(14) . . . . ? C6 N1 C16 C17 -90.0(2) . . . . ? C13 N1 C16 C17 89.1(2) . . . . ? C10 C9 C18 C19 99.08(19) . . . . ? C8 C9 C18 C19 -77.4(2) . . . . ? C9 C18 C19 C20 179.14(16) . . . . ? C18 C19 C20 C21 -68.0(3) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.34 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.170 _refine_diff_density_min -0.143 _refine_diff_density_rms 0.032 _database_code_depnum_ccdc_archive 'CCDC 944138' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_120320_qya_4_096 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N' _chemical_formula_sum 'C21 H27 N' _chemical_formula_weight 293.44 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/c' _symmetry_space_group_name_Hall '-P 2ybc' 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 13.1716(7) _cell_length_b 8.3809(5) _cell_length_c 20.3900(12) _cell_angle_alpha 90.00 _cell_angle_beta 127.363(4) _cell_angle_gamma 90.00 _cell_volume 1789.0(2) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1649 _cell_measurement_theta_min 2.8759 _cell_measurement_theta_max 29.3792 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.089 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 640 _exptl_absorpt_coefficient_mu 0.062 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9780 _exptl_absorpt_correction_T_max 0.9840 _exptl_absorpt_process_details ; CrysAlis PRO (Agilent Technologies, 2011) ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Xcalibur, Atlas, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 10.3592 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7221 _diffrn_reflns_av_R_equivalents 0.0252 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 25.35 _reflns_number_total 3258 _reflns_number_gt 2138 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement 'CrysAlis PRO (Agilent Technologies, 2011)' _computing_data_collection 'CrysAlis PRO' _computing_data_reduction 'CrysAlis PRO' _computing_molecular_graphics 'OLEX2 (Dolomanov et al., 2009)' _computing_publication_material OLEX2 _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0715P)^2^+0.2742P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3258 _refine_ls_number_parameters 204 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0533 _refine_ls_wR_factor_ref 0.1538 _refine_ls_wR_factor_gt 0.1332 _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_restrained_S_all 1.022 _refine_ls_shift/su_max 0.012 _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 0.04810(16) 0.42881(19) 0.72158(10) 0.0587(4) Uani 1 1 d . . . C1 C 0.2298(2) 0.4104(3) 0.87240(14) 0.0724(6) Uani 1 1 d . . . H1 H 0.1892 0.4667 0.8899 0.087 Uiso 1 1 calc R . . C2 C 0.3515(2) 0.3533(3) 0.92831(14) 0.0819(7) Uani 1 1 d . . . H2 H 0.3933 0.3722 0.9842 0.098 Uiso 1 1 calc R . . C3 C 0.4150(2) 0.2679(3) 0.90427(14) 0.0735(6) Uani 1 1 d . . . C4 C 0.35338(19) 0.2405(2) 0.82162(13) 0.0607(5) Uani 1 1 d . . . H4 H 0.3952 0.1845 0.8050 0.073 Uiso 1 1 calc R . . C5 C 0.22861(18) 0.2952(2) 0.76196(12) 0.0519(5) Uani 1 1 d . . . C6 C 0.16839(19) 0.3820(2) 0.78894(12) 0.0556(5) Uani 1 1 d . . . C7 C 0.5501(2) 0.2086(4) 0.96788(15) 0.1061(10) Uani 1 1 d . . . H7A H 0.5636 0.1134 0.9479 0.159 Uiso 1 1 calc R . . H7B H 0.5628 0.1855 1.0185 0.159 Uiso 1 1 calc R . . H7C H 0.6096 0.2892 0.9776 0.159 Uiso 1 1 calc R . . C8 C -0.0497(2) 0.5028(3) 0.72400(15) 0.0693(6) Uani 1 1 d . . . H8A H -0.1000 0.5749 0.6775 0.083 Uiso 1 1 calc R . . H8B H -0.0086 0.5655 0.7741 0.083 Uiso 1 1 calc R . . C9 C -0.1372(2) 0.3837(3) 0.72131(16) 0.0824(7) Uani 1 1 d . . . H9A H -0.1799 0.3229 0.6712 0.124 Uiso 1 1 calc R . . H9B H -0.1994 0.4387 0.7231 0.124 Uiso 1 1 calc R . . H9C H -0.0883 0.3133 0.7678 0.124 Uiso 1 1 calc R . . C10 C 0.02826(18) 0.3710(2) 0.65073(12) 0.0533(5) Uani 1 1 d U . . C11 C 0.13739(17) 0.2872(2) 0.67267(12) 0.0495(5) Uani 1 1 d . . . C12 C 0.13904(19) 0.2188(2) 0.60998(12) 0.0536(5) Uani 1 1 d . . . C13 C 0.0340(2) 0.2427(2) 0.52786(12) 0.0598(6) Uani 1 1 d . . . C14 C -0.0746(2) 0.3273(2) 0.50752(13) 0.0631(6) Uani 1 1 d . . . C15 C -0.07759(19) 0.3894(2) 0.56914(13) 0.0613(5) Uani 1 1 d U . . H15 H -0.1497 0.4428 0.5560 0.074 Uiso 1 1 calc R . . C16 C -0.1884(2) 0.3526(3) 0.41881(14) 0.0861(8) Uani 1 1 d . . . H16A H -0.1627 0.4127 0.3910 0.129 Uiso 1 1 calc R . . H16B H -0.2533 0.4101 0.4167 0.129 Uiso 1 1 calc R . . H16C H -0.2215 0.2510 0.3922 0.129 Uiso 1 1 calc R . . C17 C 0.0351(3) 0.1814(3) 0.45833(15) 0.0864(8) Uani 1 1 d . . . H17A H 0.1217 0.1732 0.4771 0.130 Uiso 1 1 calc R . . H17B H -0.0112 0.2540 0.4126 0.130 Uiso 1 1 calc R . . H17C H -0.0046 0.0782 0.4412 0.130 Uiso 1 1 calc R . . C18 C 0.25347(19) 0.1227(2) 0.63371(13) 0.0605(5) Uani 1 1 d . . . H18A H 0.2258 0.0441 0.5910 0.073 Uiso 1 1 calc R . . H18B H 0.2861 0.0654 0.6843 0.073 Uiso 1 1 calc R . . C19 C 0.36175(19) 0.2193(2) 0.64647(13) 0.0621(6) Uani 1 1 d . . . H19A H 0.3312 0.2711 0.5950 0.075 Uiso 1 1 calc R . . H19B H 0.3865 0.3021 0.6869 0.075 Uiso 1 1 calc R . . C20 C 0.4781(2) 0.1199(3) 0.67535(15) 0.0786(7) Uani 1 1 d . . . H20A H 0.5094 0.0700 0.7274 0.094 Uiso 1 1 calc R . . H20B H 0.4526 0.0355 0.6356 0.094 Uiso 1 1 calc R . . C21 C 0.5850(2) 0.2128(4) 0.68646(16) 0.0925(8) Uani 1 1 d . . . H21A H 0.5547 0.2643 0.6355 0.139 Uiso 1 1 calc R . . H21B H 0.6536 0.1416 0.7023 0.139 Uiso 1 1 calc R . . H21C H 0.6153 0.2918 0.7287 0.139 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 N1 0.0586(11) 0.0548(10) 0.0816(11) -0.0048(8) 0.0524(10) -0.0021(8) C1 0.0806(16) 0.0804(15) 0.0812(15) -0.0133(13) 0.0620(14) -0.0159(13) C2 0.0762(17) 0.1040(19) 0.0668(14) -0.0065(13) 0.0441(13) -0.0158(15) C3 0.0630(14) 0.0865(16) 0.0704(14) 0.0059(12) 0.0402(12) -0.0069(12) C4 0.0547(12) 0.0632(12) 0.0745(14) 0.0038(11) 0.0446(11) -0.0029(10) C5 0.0547(12) 0.0473(10) 0.0683(12) -0.0011(9) 0.0449(10) -0.0101(9) C6 0.0566(12) 0.0521(11) 0.0748(13) -0.0040(10) 0.0485(11) -0.0096(10) C7 0.0785(18) 0.136(3) 0.0793(17) 0.0111(17) 0.0349(14) 0.0083(18) C8 0.0709(14) 0.0565(12) 0.1046(17) -0.0060(12) 0.0659(13) 0.0009(11) C9 0.0759(15) 0.0775(16) 0.126(2) -0.0049(14) 0.0784(16) -0.0001(13) C10 0.0542(10) 0.0441(10) 0.0738(10) 0.0024(9) 0.0452(8) -0.0045(9) C11 0.0516(11) 0.0419(10) 0.0692(12) 0.0015(9) 0.0441(10) -0.0052(9) C12 0.0617(12) 0.0426(10) 0.0717(13) -0.0023(9) 0.0484(11) -0.0092(9) C13 0.0733(15) 0.0482(11) 0.0686(13) -0.0046(10) 0.0486(12) -0.0153(11) C14 0.0641(13) 0.0518(12) 0.0702(13) 0.0048(10) 0.0392(11) -0.0128(10) C15 0.0534(11) 0.0518(11) 0.0817(11) 0.0090(10) 0.0425(8) -0.0016(10) C16 0.0831(17) 0.0772(16) 0.0767(15) 0.0099(12) 0.0375(13) -0.0125(14) C17 0.106(2) 0.0831(17) 0.0823(16) -0.0140(13) 0.0635(15) -0.0208(15) C18 0.0717(14) 0.0489(11) 0.0787(13) -0.0054(10) 0.0549(12) -0.0027(10) C19 0.0672(13) 0.0583(12) 0.0789(13) -0.0012(10) 0.0537(12) -0.0010(11) C20 0.0749(15) 0.0760(15) 0.1025(17) -0.0001(13) 0.0630(14) 0.0060(13) C21 0.0674(15) 0.117(2) 0.1057(19) -0.0076(16) 0.0588(15) -0.0024(15) _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 C6 1.382(2) . ? N1 C10 1.390(2) . ? N1 C8 1.457(2) . ? C1 C2 1.372(3) . ? C1 C6 1.392(3) . ? C1 H1 0.9300 . ? C2 C3 1.396(3) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 C7 1.516(3) . ? C4 C5 1.402(3) . ? C4 H4 0.9300 . ? C5 C6 1.411(3) . ? C5 C11 1.452(3) . ? C7 H7A 0.9600 . ? C7 H7B 0.9600 . ? C7 H7C 0.9600 . ? C8 C9 1.500(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 C15 1.386(3) . ? C10 C11 1.407(3) . ? C11 C12 1.413(3) . ? C12 C13 1.395(3) . ? C12 C18 1.507(3) . ? C13 C14 1.415(3) . ? C13 C17 1.516(3) . ? C14 C15 1.382(3) . ? C14 C16 1.507(3) . ? C15 H15 0.9300 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 C19 1.519(3) . ? C18 H18A 0.9700 . ? C18 H18B 0.9700 . ? C19 C20 1.514(3) . ? C19 H19A 0.9700 . ? C19 H19B 0.9700 . ? C20 C21 1.502(3) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? 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 C6 N1 C10 108.25(16) . . ? C6 N1 C8 126.24(17) . . ? C10 N1 C8 124.81(17) . . ? C2 C1 C6 118.4(2) . . ? C2 C1 H1 120.8 . . ? C6 C1 H1 120.8 . . ? C1 C2 C3 122.3(2) . . ? C1 C2 H2 118.8 . . ? C3 C2 H2 118.8 . . ? C4 C3 C2 118.8(2) . . ? C4 C3 C7 120.5(2) . . ? C2 C3 C7 120.7(2) . . ? C3 C4 C5 121.2(2) . . ? C3 C4 H4 119.4 . . ? C5 C4 H4 119.4 . . ? C4 C5 C6 118.10(18) . . ? C4 C5 C11 135.67(18) . . ? C6 C5 C11 106.23(17) . . ? N1 C6 C1 129.16(19) . . ? N1 C6 C5 109.62(17) . . ? C1 C6 C5 121.2(2) . . ? C3 C7 H7A 109.5 . . ? C3 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C3 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? N1 C8 C9 113.03(17) . . ? N1 C8 H8A 109.0 . . ? C9 C8 H8A 109.0 . . ? N1 C8 H8B 109.0 . . ? C9 C8 H8B 109.0 . . ? H8A C8 H8B 107.8 . . ? C8 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C8 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C15 C10 N1 128.82(18) . . ? C15 C10 C11 121.78(18) . . ? N1 C10 C11 109.40(16) . . ? C10 C11 C12 119.25(17) . . ? C10 C11 C5 106.50(16) . . ? C12 C11 C5 134.24(18) . . ? C13 C12 C11 118.63(18) . . ? C13 C12 C18 122.16(17) . . ? C11 C12 C18 119.21(17) . . ? C12 C13 C14 120.88(18) . . ? C12 C13 C17 120.6(2) . . ? C14 C13 C17 118.5(2) . . ? C15 C14 C13 120.25(19) . . ? C15 C14 C16 118.8(2) . . ? C13 C14 C16 120.9(2) . . ? C14 C15 C10 119.1(2) . . ? C14 C15 H15 120.4 . . ? C10 C15 H15 120.4 . . ? C14 C16 H16A 109.5 . . ? C14 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C14 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? C13 C17 H17A 109.5 . . ? C13 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C13 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C12 C18 C19 114.98(16) . . ? C12 C18 H18A 108.5 . . ? C19 C18 H18A 108.5 . . ? C12 C18 H18B 108.5 . . ? C19 C18 H18B 108.5 . . ? H18A C18 H18B 107.5 . . ? C20 C19 C18 113.35(18) . . ? C20 C19 H19A 108.9 . . ? C18 C19 H19A 108.9 . . ? C20 C19 H19B 108.9 . . ? C18 C19 H19B 108.9 . . ? H19A C19 H19B 107.7 . . ? C21 C20 C19 114.1(2) . . ? C21 C20 H20A 108.7 . . ? C19 C20 H20A 108.7 . . ? C21 C20 H20B 108.7 . . ? C19 C20 H20B 108.7 . . ? H20A C20 H20B 107.6 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? 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 C6 C1 C2 C3 -0.2(4) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C1 C2 C3 C7 179.3(2) . . . . ? C2 C3 C4 C5 -0.6(3) . . . . ? C7 C3 C4 C5 -179.7(2) . . . . ? C3 C4 C5 C6 1.0(3) . . . . ? C3 C4 C5 C11 -179.5(2) . . . . ? C10 N1 C6 C1 -179.43(19) . . . . ? C8 N1 C6 C1 -8.7(3) . . . . ? C10 N1 C6 C5 1.0(2) . . . . ? C8 N1 C6 C5 171.72(17) . . . . ? C2 C1 C6 N1 -178.9(2) . . . . ? C2 C1 C6 C5 0.7(3) . . . . ? C4 C5 C6 N1 178.54(16) . . . . ? C11 C5 C6 N1 -1.1(2) . . . . ? C4 C5 C6 C1 -1.1(3) . . . . ? C11 C5 C6 C1 179.32(18) . . . . ? C6 N1 C8 C9 -90.6(2) . . . . ? C10 N1 C8 C9 78.6(3) . . . . ? C6 N1 C10 C15 -179.38(18) . . . . ? C8 N1 C10 C15 9.7(3) . . . . ? C6 N1 C10 C11 -0.5(2) . . . . ? C8 N1 C10 C11 -171.40(16) . . . . ? C15 C10 C11 C12 -0.5(3) . . . . ? N1 C10 C11 C12 -179.46(15) . . . . ? C15 C10 C11 C5 178.82(17) . . . . ? N1 C10 C11 C5 -0.16(19) . . . . ? C4 C5 C11 C10 -178.8(2) . . . . ? C6 C5 C11 C10 0.73(19) . . . . ? C4 C5 C11 C12 0.4(4) . . . . ? C6 C5 C11 C12 179.89(19) . . . . ? C10 C11 C12 C13 2.8(3) . . . . ? C5 C11 C12 C13 -176.28(18) . . . . ? C10 C11 C12 C18 -177.21(16) . . . . ? C5 C11 C12 C18 3.7(3) . . . . ? C11 C12 C13 C14 -3.0(3) . . . . ? C18 C12 C13 C14 177.02(17) . . . . ? C11 C12 C13 C17 175.80(17) . . . . ? C18 C12 C13 C17 -4.2(3) . . . . ? C12 C13 C14 C15 0.8(3) . . . . ? C17 C13 C14 C15 -177.98(18) . . . . ? C12 C13 C14 C16 -179.72(18) . . . . ? C17 C13 C14 C16 1.5(3) . . . . ? C13 C14 C15 C10 1.5(3) . . . . ? C16 C14 C15 C10 -177.95(18) . . . . ? N1 C10 C15 C14 177.07(17) . . . . ? C11 C10 C15 C14 -1.7(3) . . . . ? C13 C12 C18 C19 93.6(2) . . . . ? C11 C12 C18 C19 -86.4(2) . . . . ? C12 C18 C19 C20 176.44(18) . . . . ? C18 C19 C20 C21 178.68(19) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.35 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.215 _refine_diff_density_min -0.179 _refine_diff_density_rms 0.031 _database_code_depnum_ccdc_archive 'CCDC 944139'