# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full Chem.Commun. _journal_coden_cambridge 0182 _journal_year ? _journal_volume ? _journal_page_first ? loop_ _publ_author_address ; School of Pharmacy Tokyo University of Pharmacy and Life Science 1432-1 Horinouchi Hachioji Tokyo 192-0392 Japan ; _publ_contact_author_address ; School of Pharmacy, Tokyo University of Pharmacy and Life Sciences, 1432-1 Horinouchi Hachioji, Tokyo, 192-0392, Japan ; _publ_contact_author_email aoyagis@toyaku.ac.jp _publ_contact_author_fax ? _publ_contact_author_phone ? # SUBMISSION DETAILS _publ_contact_author_name 'Sakae Aoyagi ' _publ_contact_letter ; ? ; _publ_requested_category ? _publ_section_title ; ; _publ_author_name 'Sakae Aoyagi' data_m-hs187 _database_code_depnum_ccdc_archive 'CCDC 823962' #TrackingRef '- M-HS187.cif' #============================================================================== _audit_creation_date '10 DECEMBER 08' _audit_creation_method SHELXL-97 _publ_section_abstract ; ; _publ_section_comment ; ; #============================================================================== # TEXT #============================================================================== _publ_section_acknowledgements ; ; _publ_section_references ; Sheldrick, G. M. (1997). SHELXL97. Program for the Refinement of Crystal Structures. University of G\"ottingen, Germany. A.L.Spek (2004) PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. or A.L.Spek, J.Appl.Cryst. 2003, 36, 7-13. ; #============================================================================== # CHEMICAL DATA #============================================================================== _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H34 N2' _chemical_formula_sum 'C24 H34 N2' _chemical_formula_weight 350.53 _chemical_formula_structural ? _chemical_formula_analytical ? _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 ' _symmetry_space_group_name_Hall 'P 2ac 2ab ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' _cell_length_a 8.0477(18) _cell_length_b 9.343(2) _cell_length_c 27.225(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2047.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 9891 _cell_measurement_theta_min 2.30 _cell_measurement_theta_max 27.50 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.37 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.137 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 768 _exptl_absorpt_coefficient_mu 0.066 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9761 _exptl_absorpt_correction_T_max 0.9941 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; #============================================================================== # EXPERIMENTAL DATA #============================================================================== _diffrn_ambient_temperature 90 _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus rotating anode' _diffrn_radiation_monochromator 'multilayer confocal mirror' _diffrn_measurement_device_type 'Bruker APEXII CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 8.333 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 23092 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0340 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.50 _diffrn_reflns_theta_max 27.59 _reflns_number_total 4657 _reflns_number_gt 4400 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker AXS, 2006)' _computing_cell_refinement 'APEX2 (Bruker AXS, 2006)' _computing_data_reduction 'SAINT (Bruker AXS, 2004)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'XSHEL (Bruker AXS,2002)' _computing_publication_material 'XCIF (Bruker AXS, 2001)' _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^)+(0.0621P)^2^+0.4732P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(2) _refine_ls_number_reflns 4657 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0425 _refine_ls_R_factor_gt 0.0393 _refine_ls_wR_factor_ref 0.1062 _refine_ls_wR_factor_gt 0.1037 _refine_ls_goodness_of_fit_ref 1.025 _refine_ls_restrained_S_all 1.025 _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 N2 N 0.73359(16) 0.28070(13) 0.72172(5) 0.0244(3) Uani 1 1 d . . . N1 N 0.31216(14) 0.30479(12) 0.76654(4) 0.0151(2) Uani 1 1 d . . . C12 C 0.2801(2) 0.3053(2) 0.94075(6) 0.0350(4) Uani 1 1 d . . . H12 H 0.2035 0.3109 0.9672 0.042 Uiso 1 1 calc R . . C1 C 0.4364(2) 0.24844(18) 0.94825(5) 0.0295(4) Uani 1 1 d . . . H1 H 0.4672 0.2140 0.9798 0.035 Uiso 1 1 calc R . . C18 C 0.1078(2) 0.10240(17) 0.55853(5) 0.0278(3) Uani 1 1 d . . . H18A H 0.1912 0.1407 0.5352 0.033 Uiso 1 1 calc R . . H18B H 0.0752 0.0057 0.5472 0.033 Uiso 1 1 calc R . . C20 C -0.18115(19) 0.42360(18) 0.58597(6) 0.0269(3) Uani 1 1 d . . . H20A H -0.2389 0.3756 0.6131 0.040 Uiso 1 1 calc R . . H20B H -0.2478 0.4157 0.5560 0.040 Uiso 1 1 calc R . . H20C H -0.1651 0.5248 0.5941 0.040 Uiso 1 1 calc R . . C2 C 0.5480(2) 0.24182(17) 0.90972(6) 0.0267(3) Uani 1 1 d . . . H2 H 0.6557 0.2031 0.9149 0.032 Uiso 1 1 calc R . . C13 C 0.2351(2) 0.35423(18) 0.89439(5) 0.0267(3) Uani 1 1 d . . . H13 H 0.1268 0.3919 0.8893 0.032 Uiso 1 1 calc R . . C19 C -0.0443(2) 0.19958(17) 0.55892(5) 0.0257(3) Uani 1 1 d . . . H19A H -0.1309 0.1553 0.5798 0.031 Uiso 1 1 calc R . . H19B H -0.0890 0.2057 0.5251 0.031 Uiso 1 1 calc R . . C11 C 0.0825(2) 0.44082(17) 0.53879(5) 0.0252(3) Uani 1 1 d . . . H11A H 0.0143 0.4481 0.5091 0.038 Uiso 1 1 calc R . . H11B H 0.1880 0.3939 0.5308 0.038 Uiso 1 1 calc R . . H11C H 0.1044 0.5369 0.5517 0.038 Uiso 1 1 calc R . . C3 C 0.50356(19) 0.29154(16) 0.86338(5) 0.0230(3) Uani 1 1 d . . . H3 H 0.5809 0.2863 0.8371 0.028 Uiso 1 1 calc R . . C17 C 0.18470(19) 0.09213(15) 0.60992(5) 0.0209(3) Uani 1 1 d . . . H17A H 0.2848 0.0307 0.6084 0.025 Uiso 1 1 calc R . . H17B H 0.1042 0.0462 0.6324 0.025 Uiso 1 1 calc R . . C10 C -0.01067(18) 0.35216(17) 0.57774(5) 0.0208(3) Uani 1 1 d . . . C21 C 0.38667(18) 0.29205(17) 0.60109(5) 0.0207(3) Uani 1 1 d . . . H21A H 0.3727 0.2665 0.5664 0.031 Uiso 1 1 calc R . . H21B H 0.4871 0.2461 0.6140 0.031 Uiso 1 1 calc R . . H21C H 0.3972 0.3962 0.6041 0.031 Uiso 1 1 calc R . . C5 C 0.2992(2) 0.41117(14) 0.80592(5) 0.0196(3) Uani 1 1 d . . . H5A H 0.1838 0.4475 0.8074 0.023 Uiso 1 1 calc R . . H5B H 0.3732 0.4930 0.7984 0.023 Uiso 1 1 calc R . . C4 C 0.34640(18) 0.34890(14) 0.85537(5) 0.0180(3) Uani 1 1 d . . . C15 C 0.61833(17) 0.35064(15) 0.71511(5) 0.0176(3) Uani 1 1 d . . . C14 C 0.47271(17) 0.44135(14) 0.70634(5) 0.0166(3) Uani 1 1 d . . . H14A H 0.4749 0.4755 0.6719 0.020 Uiso 1 1 calc R . . H14B H 0.4788 0.5262 0.7280 0.020 Uiso 1 1 calc R . . C24 C 0.18091(17) 0.19549(14) 0.77006(5) 0.0167(3) Uani 1 1 d . . . H24A H 0.0749 0.2389 0.7809 0.020 Uiso 1 1 calc R . . H24B H 0.2127 0.1197 0.7937 0.020 Uiso 1 1 calc R . . C23 C 0.16409(17) 0.13381(14) 0.71797(5) 0.0165(3) Uani 1 1 d . . . H23A H 0.0486 0.1439 0.7059 0.020 Uiso 1 1 calc R . . H23B H 0.1947 0.0312 0.7175 0.020 Uiso 1 1 calc R . . C8 C 0.12108(17) 0.48585(14) 0.65200(5) 0.0164(3) Uani 1 1 d . . . H8A H 0.0253 0.5515 0.6484 0.020 Uiso 1 1 calc R . . H8B H 0.2177 0.5294 0.6352 0.020 Uiso 1 1 calc R . . C9 C 0.08016(17) 0.34173(15) 0.62824(5) 0.0159(3) Uani 1 1 d . . . H9 H -0.0032 0.2971 0.6508 0.019 Uiso 1 1 calc R . . C16 C 0.23339(16) 0.24045(14) 0.63071(5) 0.0157(3) Uani 1 1 d . . . C7 C 0.16097(17) 0.46593(14) 0.70670(5) 0.0158(3) Uani 1 1 d . . . H7A H 0.0610 0.4290 0.7237 0.019 Uiso 1 1 calc R . . H7B H 0.1884 0.5602 0.7212 0.019 Uiso 1 1 calc R . . C22 C 0.28540(16) 0.22228(13) 0.68569(5) 0.0140(3) Uani 1 1 d . . . H22 H 0.3948 0.1716 0.6860 0.017 Uiso 1 1 calc R . . C6 C 0.30684(16) 0.36227(14) 0.71574(4) 0.0138(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 N2 0.0192(6) 0.0181(6) 0.0359(7) 0.0025(5) -0.0013(5) -0.0017(5) N1 0.0187(5) 0.0101(5) 0.0165(5) 0.0000(4) -0.0011(4) -0.0020(4) C12 0.0366(9) 0.0469(10) 0.0215(7) 0.0013(7) 0.0037(7) 0.0030(8) C1 0.0446(10) 0.0239(7) 0.0198(7) -0.0005(6) -0.0095(6) 0.0021(7) C18 0.0386(9) 0.0240(7) 0.0207(7) -0.0062(6) -0.0024(6) -0.0064(7) C20 0.0195(7) 0.0362(9) 0.0251(7) 0.0051(6) -0.0061(6) 0.0003(7) C2 0.0299(8) 0.0204(7) 0.0299(7) -0.0063(6) -0.0107(6) 0.0076(6) C13 0.0247(8) 0.0321(8) 0.0234(7) -0.0014(6) -0.0002(6) 0.0063(7) C19 0.0308(8) 0.0257(7) 0.0204(6) 0.0002(6) -0.0066(6) -0.0081(7) C11 0.0289(8) 0.0282(8) 0.0185(6) 0.0053(6) -0.0013(6) -0.0044(6) C3 0.0239(7) 0.0213(7) 0.0237(7) -0.0047(6) -0.0013(6) 0.0026(6) C17 0.0264(7) 0.0161(7) 0.0203(6) -0.0041(5) -0.0004(6) -0.0021(6) C10 0.0202(7) 0.0242(7) 0.0179(6) 0.0034(5) -0.0027(5) -0.0029(6) C21 0.0202(7) 0.0218(7) 0.0202(6) -0.0013(5) 0.0038(5) -0.0012(6) C5 0.0269(7) 0.0121(6) 0.0197(6) -0.0015(5) -0.0030(6) 0.0030(5) C4 0.0238(7) 0.0101(6) 0.0202(6) -0.0033(5) -0.0030(5) 0.0005(5) C15 0.0179(6) 0.0145(6) 0.0205(6) 0.0008(5) -0.0010(5) -0.0062(5) C14 0.0171(6) 0.0108(6) 0.0219(6) 0.0009(5) -0.0018(5) -0.0015(5) C24 0.0162(6) 0.0140(6) 0.0201(6) 0.0015(5) 0.0014(5) -0.0002(5) C23 0.0180(6) 0.0120(6) 0.0197(6) 0.0026(5) -0.0013(5) -0.0025(5) C8 0.0164(6) 0.0139(6) 0.0190(6) 0.0022(5) 0.0000(5) 0.0026(5) C9 0.0164(6) 0.0168(6) 0.0144(5) 0.0015(5) -0.0001(5) -0.0020(5) C16 0.0166(6) 0.0128(6) 0.0177(6) -0.0011(5) 0.0003(5) -0.0030(5) C7 0.0165(6) 0.0123(6) 0.0187(6) -0.0009(5) -0.0012(5) 0.0012(5) C22 0.0132(6) 0.0100(6) 0.0189(6) -0.0009(5) 0.0003(5) -0.0002(5) C6 0.0144(6) 0.0103(6) 0.0167(6) -0.0004(5) -0.0014(5) 0.0001(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N2 C15 1.1488(19) . ? N1 C5 1.4655(17) . ? N1 C24 1.4724(17) . ? N1 C6 1.4843(16) . ? C12 C1 1.380(3) . ? C12 C13 1.391(2) . ? C12 H12 0.9500 . ? C1 C2 1.382(2) . ? C1 H1 0.9500 . ? C18 C19 1.524(2) . ? C18 C17 1.533(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C20 C10 1.542(2) . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C2 C3 1.391(2) . ? C2 H2 0.9500 . ? C13 C4 1.390(2) . ? C13 H13 0.9500 . ? C19 C10 1.539(2) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C11 C10 1.540(2) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C3 C4 1.391(2) . ? C3 H3 0.9500 . ? C17 C16 1.5472(19) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C10 C9 1.5602(18) . ? C21 C16 1.5506(19) . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C5 C4 1.5150(19) . ? C5 H5A 0.9900 . ? C5 H5B 0.9900 . ? C15 C14 1.4659(19) . ? C14 C6 1.5470(18) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C24 C23 1.5368(18) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C23 C22 1.5519(18) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C8 C9 1.5298(19) . ? C8 C7 1.5348(18) . ? C8 H8A 0.9900 . ? C8 H8B 0.9900 . ? C9 C16 1.5558(19) . ? C9 H9 1.0000 . ? C16 C22 1.5637(18) . ? C7 C6 1.5416(18) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C22 C6 1.5524(17) . ? C22 H22 1.0000 . ? 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 C5 N1 C24 111.84(11) . . ? C5 N1 C6 115.73(11) . . ? C24 N1 C6 106.91(10) . . ? C1 C12 C13 119.88(15) . . ? C1 C12 H12 120.1 . . ? C13 C12 H12 120.1 . . ? C12 C1 C2 119.78(14) . . ? C12 C1 H1 120.1 . . ? C2 C1 H1 120.1 . . ? C19 C18 C17 110.81(12) . . ? C19 C18 H18A 109.5 . . ? C17 C18 H18A 109.5 . . ? C19 C18 H18B 109.5 . . ? C17 C18 H18B 109.5 . . ? H18A C18 H18B 108.1 . . ? C10 C20 H20A 109.5 . . ? C10 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C10 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C1 C2 C3 120.43(15) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C13 C12 120.93(15) . . ? C4 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C18 C19 C10 114.40(12) . . ? C18 C19 H19A 108.7 . . ? C10 C19 H19A 108.7 . . ? C18 C19 H19B 108.7 . . ? C10 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C10 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C10 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C4 C3 C2 120.30(14) . . ? C4 C3 H3 119.8 . . ? C2 C3 H3 119.8 . . ? C18 C17 C16 112.33(12) . . ? C18 C17 H17A 109.1 . . ? C16 C17 H17A 109.1 . . ? C18 C17 H17B 109.1 . . ? C16 C17 H17B 109.1 . . ? H17A C17 H17B 107.9 . . ? C19 C10 C11 110.77(12) . . ? C19 C10 C20 107.04(13) . . ? C11 C10 C20 107.47(12) . . ? C19 C10 C9 108.54(12) . . ? C11 C10 C9 114.34(12) . . ? C20 C10 C9 108.41(11) . . ? C16 C21 H21A 109.5 . . ? C16 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C16 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N1 C5 C4 111.83(11) . . ? N1 C5 H5A 109.3 . . ? C4 C5 H5A 109.3 . . ? N1 C5 H5B 109.3 . . ? C4 C5 H5B 109.3 . . ? H5A C5 H5B 107.9 . . ? C13 C4 C3 118.66(13) . . ? C13 C4 C5 120.26(13) . . ? C3 C4 C5 121.01(13) . . ? N2 C15 C14 179.21(16) . . ? C15 C14 C6 112.75(11) . . ? C15 C14 H14A 109.0 . . ? C6 C14 H14A 109.0 . . ? C15 C14 H14B 109.0 . . ? C6 C14 H14B 109.0 . . ? H14A C14 H14B 107.8 . . ? N1 C24 C23 105.26(10) . . ? N1 C24 H24A 110.7 . . ? C23 C24 H24A 110.7 . . ? N1 C24 H24B 110.7 . . ? C23 C24 H24B 110.7 . . ? H24A C24 H24B 108.8 . . ? C24 C23 C22 105.51(10) . . ? C24 C23 H23A 110.6 . . ? C22 C23 H23A 110.6 . . ? C24 C23 H23B 110.6 . . ? C22 C23 H23B 110.6 . . ? H23A C23 H23B 108.8 . . ? C9 C8 C7 110.40(11) . . ? C9 C8 H8A 109.6 . . ? C7 C8 H8A 109.6 . . ? C9 C8 H8B 109.6 . . ? C7 C8 H8B 109.6 . . ? H8A C8 H8B 108.1 . . ? C8 C9 C16 110.27(11) . . ? C8 C9 C10 114.74(11) . . ? C16 C9 C10 116.57(11) . . ? C8 C9 H9 104.6 . . ? C16 C9 H9 104.6 . . ? C10 C9 H9 104.6 . . ? C17 C16 C21 106.84(11) . . ? C17 C16 C9 109.16(11) . . ? C21 C16 C9 114.77(11) . . ? C17 C16 C22 108.70(10) . . ? C21 C16 C22 108.58(11) . . ? C9 C16 C22 108.63(10) . . ? C8 C7 C6 112.98(11) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C23 C22 C6 102.72(10) . . ? C23 C22 C16 115.56(11) . . ? C6 C22 C16 116.29(10) . . ? C23 C22 H22 107.2 . . ? C6 C22 H22 107.2 . . ? C16 C22 H22 107.2 . . ? N1 C6 C7 113.46(10) . . ? N1 C6 C14 107.58(10) . . ? C7 C6 C14 109.30(10) . . ? N1 C6 C22 100.92(10) . . ? C7 C6 C22 111.13(11) . . ? C14 C6 C22 114.27(11) . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 27.59 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.320 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.043