Electronic Supplementary Material for CrystEngComm This journal is © The Royal SOciety of Chemistry 2005 data_global _journal_coden_Cambridge 1350 _publ_contact_author_name 'John R. Scheffer' _publ_contact_author_address ; Department of Chemistry, 2036 Main Mall, Univeristy of British Columbia, Vancouver, BC, Canada, V6T 1Z1 ; _publ_contact_author_email scheffer@chem.ubc.ca _publ_contact_author_phone 1-604-8223496 _publ_contact_author_fax 1-604-8222847 loop_ _publ_author_name 'J. Scheffer' 'Brian O. Patrick' 'Wujiong Xia.' _publ_requested_journal 'Cryst Eng. Comm.' _publ_section_title ; Making Use of Crystallization-Induced Asymmetric Transformations in Solid State Organic Photochemistry: Application to the Enantioselective Yang Photocyclization of endo-Bicyclo[2.1.1]hexyl Aryl Ketones ; data_js198 _database_code_depnum_ccdc_archive 'CCDC 287133' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O3' _chemical_formula_weight 365.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 6.1272(8) _cell_length_b 7.2620(10) _cell_length_c 45.252(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2013.5(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 7038 _cell_measurement_theta_min 2.84 _cell_measurement_theta_max 20.91 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.206 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.079 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 24878 _diffrn_reflns_av_R_equivalents 0.0498 _diffrn_reflns_av_sigmaI/netI 0.0468 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 25.00 _reflns_number_total 3540 _reflns_number_gt 2818 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0672P)^2^+0.0228P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1.1(15) _refine_ls_number_reflns 3540 _refine_ls_number_parameters 258 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0601 _refine_ls_R_factor_gt 0.0444 _refine_ls_wR_factor_ref 0.1128 _refine_ls_wR_factor_gt 0.1085 _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_restrained_S_all 1.062 _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 C1 C 0.6702(3) 0.0092(3) 0.86180(4) 0.0272(5) Uani 1 1 d . . . C2 C 0.8840(3) 0.0753(3) 0.86367(4) 0.0271(5) Uani 1 1 d . . . H2 H 0.9648 0.0996 0.8462 0.033 Uiso 1 1 calc R . . C3 C 0.9779(3) 0.1055(3) 0.89120(4) 0.0253(5) Uani 1 1 d . . . H3 H 1.1237 0.1492 0.8924 0.030 Uiso 1 1 calc R . . C4 C 0.8613(3) 0.0725(3) 0.91704(4) 0.0233(5) Uani 1 1 d . . . C5 C 0.6488(3) 0.0060(3) 0.91510(4) 0.0263(5) Uani 1 1 d . . . H5 H 0.5673 -0.0159 0.9326 0.032 Uiso 1 1 calc R . . C6 C 0.5555(3) -0.0285(3) 0.88777(5) 0.0287(5) Uani 1 1 d . . . H6 H 0.4122 -0.0781 0.8867 0.034 Uiso 1 1 calc R . . C7 C 0.9635(3) 0.1138(3) 0.94653(5) 0.0250(5) Uani 1 1 d . . . C8 C 0.5542(4) -0.0171(3) 0.83296(5) 0.0361(6) Uani 1 1 d . . . C9 C 0.6678(4) 0.0040(3) 0.80342(5) 0.0391(6) Uani 1 1 d . . . C10 C 0.6657(6) 0.2118(4) 0.79662(7) 0.0706(9) Uani 1 1 d . . . H10A H 0.5144 0.2549 0.7953 0.106 Uiso 1 1 calc R . . H10B H 0.7403 0.2344 0.7778 0.106 Uiso 1 1 calc R . . H10C H 0.7409 0.2784 0.8125 0.106 Uiso 1 1 calc R . . C11 C 0.5767(4) -0.1196(4) 0.77848(5) 0.0450(7) Uani 1 1 d . . . H11 H 0.4425 -0.0807 0.7676 0.054 Uiso 1 1 calc R . . C12 C 0.8017(5) -0.1013(5) 0.76351(6) 0.0688(9) Uani 1 1 d . . . H12A H 0.8260 0.0160 0.7529 0.083 Uiso 1 1 calc R . . H12B H 0.8474 -0.2093 0.7517 0.083 Uiso 1 1 calc R . . C13 C 0.8807(4) -0.1027(4) 0.79654(5) 0.0555(8) Uani 1 1 d . . . H13 H 1.0259 -0.0500 0.8020 0.067 Uiso 1 1 calc R . . C14 C 0.8193(6) -0.2936(4) 0.80582(7) 0.0688(10) Uani 1 1 d . . . H14A H 0.8138 -0.3054 0.8276 0.083 Uiso 1 1 calc R . . H14B H 0.9214 -0.3864 0.7977 0.083 Uiso 1 1 calc R . . C15 C 0.5885(5) -0.3113(4) 0.79181(6) 0.0613(8) Uani 1 1 d . . . H15A H 0.5820 -0.4090 0.7766 0.074 Uiso 1 1 calc R . . H15B H 0.4736 -0.3322 0.8068 0.074 Uiso 1 1 calc R . . C16 C 0.3171(4) -0.4725(3) 0.93252(5) 0.0292(5) Uani 1 1 d . . . C17 C 0.4772(4) -0.5295(3) 0.91278(5) 0.0333(6) Uani 1 1 d . . . H17 H 0.6119 -0.5762 0.9200 0.040 Uiso 1 1 calc R . . C18 C 0.4407(4) -0.5185(3) 0.88238(5) 0.0398(6) Uani 1 1 d . . . H18 H 0.5498 -0.5584 0.8689 0.048 Uiso 1 1 calc R . . C19 C 0.2435(5) -0.4487(3) 0.87188(6) 0.0450(7) Uani 1 1 d . . . H19 H 0.2177 -0.4416 0.8512 0.054 Uiso 1 1 calc R . . C20 C 0.0879(4) -0.3906(3) 0.89121(6) 0.0427(6) Uani 1 1 d . . . H20 H -0.0452 -0.3410 0.8840 0.051 Uiso 1 1 calc R . . C21 C 0.1228(4) -0.4035(3) 0.92133(5) 0.0361(6) Uani 1 1 d . . . H21 H 0.0118 -0.3645 0.9346 0.043 Uiso 1 1 calc R . . C22 C 0.3518(4) -0.4833(3) 0.96553(4) 0.0298(5) Uani 1 1 d . . . H22 H 0.2076 -0.4596 0.9751 0.036 Uiso 1 1 calc R . . C23 C 0.5103(5) -0.3427(3) 0.97743(5) 0.0447(7) Uani 1 1 d . . . H23A H 0.6545 -0.3630 0.9686 0.067 Uiso 1 1 calc R . . H23B H 0.5204 -0.3550 0.9990 0.067 Uiso 1 1 calc R . . H23C H 0.4591 -0.2187 0.9724 0.067 Uiso 1 1 calc R . . N1 N 0.4234(3) -0.6721(3) 0.97463(4) 0.0240(4) Uani 1 1 d . . . O1 O 1.1585(2) 0.0691(2) 0.95048(3) 0.0319(4) Uani 1 1 d . . . O2 O 0.8459(2) 0.1930(2) 0.96586(3) 0.0354(4) Uani 1 1 d . . . O3 O 0.3577(3) -0.0478(3) 0.83324(4) 0.0709(7) Uani 1 1 d . . . H1A H 0.578(4) -0.700(3) 0.9692(5) 0.039(6) Uiso 1 1 d . . . H1B H 0.333(4) -0.762(3) 0.9682(5) 0.023(6) Uiso 1 1 d . . . H1C H 0.411(3) -0.681(3) 0.9953(6) 0.031(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0269(11) 0.0263(12) 0.0283(12) -0.0043(10) -0.0015(10) 0.0033(10) C2 0.0281(11) 0.0324(12) 0.0207(11) -0.0010(9) 0.0042(9) -0.0005(10) C3 0.0181(10) 0.0296(12) 0.0280(13) -0.0025(10) -0.0003(9) -0.0027(9) C4 0.0246(10) 0.0211(11) 0.0241(11) -0.0016(9) 0.0010(10) 0.0040(10) C5 0.0269(11) 0.0255(11) 0.0265(12) -0.0014(10) 0.0021(10) -0.0026(10) C6 0.0228(11) 0.0278(12) 0.0356(13) -0.0044(10) -0.0002(11) -0.0027(9) C7 0.0241(12) 0.0249(12) 0.0259(12) 0.0008(10) 0.0005(10) -0.0024(10) C8 0.0326(14) 0.0376(14) 0.0380(15) -0.0082(11) -0.0074(11) 0.0021(11) C9 0.0490(14) 0.0400(14) 0.0283(13) -0.0007(11) -0.0123(12) 0.0029(13) C10 0.108(3) 0.0444(17) 0.0599(18) 0.0130(14) -0.027(2) -0.0120(19) C11 0.0507(15) 0.0517(16) 0.0326(13) -0.0041(12) -0.0139(12) 0.0022(12) C12 0.070(2) 0.103(3) 0.0331(15) -0.0160(17) -0.0012(15) -0.005(2) C13 0.0435(15) 0.086(2) 0.0375(15) -0.0168(15) -0.0042(13) 0.0030(16) C14 0.092(2) 0.063(2) 0.0514(18) -0.0122(15) -0.0231(17) 0.035(2) C15 0.088(2) 0.0449(17) 0.0511(17) -0.0134(14) -0.0184(16) -0.0040(16) C16 0.0343(13) 0.0226(12) 0.0307(13) -0.0011(9) -0.0002(11) -0.0005(10) C17 0.0382(13) 0.0290(13) 0.0327(14) 0.0015(10) 0.0003(11) 0.0047(10) C18 0.0583(16) 0.0332(14) 0.0278(13) 0.0000(11) 0.0095(12) -0.0052(12) C19 0.0689(19) 0.0355(16) 0.0306(14) 0.0079(12) -0.0133(14) -0.0125(14) C20 0.0445(15) 0.0390(14) 0.0446(16) 0.0092(12) -0.0141(13) -0.0068(12) C21 0.0330(13) 0.0342(13) 0.0412(15) 0.0030(11) -0.0026(11) 0.0028(12) C22 0.0350(12) 0.0255(12) 0.0287(12) 0.0007(10) 0.0036(11) 0.0062(11) C23 0.0639(17) 0.0363(15) 0.0340(14) -0.0047(11) -0.0025(12) -0.0112(13) N1 0.0243(11) 0.0266(11) 0.0210(11) -0.0002(8) -0.0012(9) -0.0011(9) O1 0.0264(8) 0.0361(9) 0.0331(9) -0.0078(7) -0.0065(7) 0.0016(7) O2 0.0351(8) 0.0481(10) 0.0229(8) -0.0065(8) -0.0012(7) 0.0108(8) O3 0.0333(10) 0.135(2) 0.0444(11) -0.0174(12) -0.0111(9) -0.0046(12) _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 C1 C6 1.397(3) . ? C1 C2 1.398(3) . ? C1 C8 1.498(3) . ? C2 C3 1.390(3) . ? C2 H2 0.9500 . ? C3 C4 1.391(3) . ? C3 H3 0.9500 . ? C4 C5 1.391(3) . ? C4 C7 1.504(3) . ? C5 C6 1.385(3) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.251(3) . ? C7 O2 1.271(2) . ? C8 O3 1.224(3) . ? C8 C9 1.515(3) . ? C9 C10 1.540(4) . ? C9 C11 1.546(3) . ? C9 C13 1.549(4) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C15 1.519(4) . ? C11 C12 1.542(4) . ? C11 C13 2.037(4) . ? C11 H11 1.0000 . ? C12 C13 1.571(4) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.497(4) . ? C13 H13 1.0000 . ? C14 C15 1.555(4) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C21 1.387(3) . ? C16 C17 1.390(3) . ? C16 C22 1.511(3) . ? C17 C18 1.396(3) . ? C17 H17 0.9500 . ? C18 C19 1.394(4) . ? C18 H18 0.9500 . ? C19 C20 1.361(3) . ? C19 H19 0.9500 . ? C20 C21 1.383(3) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 N1 1.497(3) . ? C22 C23 1.509(3) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N1 H1A 1.00(3) . ? N1 H1B 0.90(2) . ? N1 H1C 0.94(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 C6 C1 C2 119.21(19) . . ? C6 C1 C8 117.99(19) . . ? C2 C1 C8 122.77(19) . . ? C3 C2 C1 119.77(19) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C2 C3 C4 120.92(18) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C3 C4 C5 119.17(18) . . ? C3 C4 C7 119.83(18) . . ? C5 C4 C7 120.98(18) . . ? C6 C5 C4 120.35(19) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C1 120.54(19) . . ? C5 C6 H6 119.7 . . ? C1 C6 H6 119.7 . . ? O1 C7 O2 124.11(19) . . ? O1 C7 C4 118.21(18) . . ? O2 C7 C4 117.68(17) . . ? O3 C8 C1 118.7(2) . . ? O3 C8 C9 118.6(2) . . ? C1 C8 C9 122.5(2) . . ? C8 C9 C10 105.8(2) . . ? C8 C9 C11 114.8(2) . . ? C10 C9 C11 114.82(19) . . ? C8 C9 C13 120.9(2) . . ? C10 C9 C13 117.2(3) . . ? C11 C9 C13 82.35(18) . . ? 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 . . ? C15 C11 C12 102.2(2) . . ? C15 C11 C9 103.02(19) . . ? C12 C11 C9 87.02(19) . . ? C15 C11 C13 81.52(19) . . ? C12 C11 C13 49.74(14) . . ? C9 C11 C13 48.88(14) . . ? C15 C11 H11 119.6 . . ? C12 C11 H11 119.6 . . ? C9 C11 H11 119.6 . . ? C13 C11 H11 158.9 . . ? C11 C12 C13 81.76(19) . . ? C11 C12 H12A 115.0 . . ? C13 C12 H12A 115.0 . . ? C11 C12 H12B 115.0 . . ? C13 C12 H12B 115.0 . . ? H12A C12 H12B 112.0 . . ? C14 C13 C9 101.3(2) . . ? C14 C13 C12 101.3(2) . . ? C9 C13 C12 85.91(19) . . ? C14 C13 C11 80.05(19) . . ? C9 C13 C11 48.77(13) . . ? C12 C13 C11 48.50(14) . . ? C14 C13 H13 120.5 . . ? C9 C13 H13 120.5 . . ? C12 C13 H13 120.5 . . ? C11 C13 H13 159.4 . . ? C13 C14 C15 101.0(2) . . ? C13 C14 H14A 111.6 . . ? C15 C14 H14A 111.6 . . ? C13 C14 H14B 111.6 . . ? C15 C14 H14B 111.6 . . ? H14A C14 H14B 109.4 . . ? C11 C15 C14 97.4(2) . . ? C11 C15 H15A 112.3 . . ? C14 C15 H15A 112.3 . . ? C11 C15 H15B 112.3 . . ? C14 C15 H15B 112.3 . . ? H15A C15 H15B 109.9 . . ? C21 C16 C17 118.6(2) . . ? C21 C16 C22 120.0(2) . . ? C17 C16 C22 121.4(2) . . ? C16 C17 C18 120.2(2) . . ? C16 C17 H17 119.9 . . ? C18 C17 H17 119.9 . . ? C19 C18 C17 119.7(2) . . ? C19 C18 H18 120.1 . . ? C17 C18 H18 120.1 . . ? C20 C19 C18 120.1(2) . . ? C20 C19 H19 120.0 . . ? C18 C19 H19 120.0 . . ? C19 C20 C21 120.3(2) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? C20 C21 C16 121.1(2) . . ? C20 C21 H21 119.4 . . ? C16 C21 H21 119.4 . . ? N1 C22 C23 109.44(19) . . ? N1 C22 C16 111.15(17) . . ? C23 C22 C16 114.11(18) . . ? N1 C22 H22 107.3 . . ? C23 C22 H22 107.3 . . ? C16 C22 H22 107.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 N1 H1A 113.5(13) . . ? C22 N1 H1B 113.1(13) . . ? H1A N1 H1B 111(2) . . ? C22 N1 H1C 108.3(13) . . ? H1A N1 H1C 107.7(19) . . ? H1B N1 H1C 102.9(19) . . ? 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 -1.0(3) . . . . ? C8 C1 C2 C3 176.7(2) . . . . ? C1 C2 C3 C4 -0.7(3) . . . . ? C2 C3 C4 C5 0.9(3) . . . . ? C2 C3 C4 C7 -177.43(19) . . . . ? C3 C4 C5 C6 0.6(3) . . . . ? C7 C4 C5 C6 178.90(19) . . . . ? C4 C5 C6 C1 -2.3(3) . . . . ? C2 C1 C6 C5 2.5(3) . . . . ? C8 C1 C6 C5 -175.30(19) . . . . ? C3 C4 C7 O1 -42.8(3) . . . . ? C5 C4 C7 O1 138.9(2) . . . . ? C3 C4 C7 O2 136.9(2) . . . . ? C5 C4 C7 O2 -41.4(3) . . . . ? C6 C1 C8 O3 9.0(3) . . . . ? C2 C1 C8 O3 -168.8(2) . . . . ? C6 C1 C8 C9 -174.7(2) . . . . ? C2 C1 C8 C9 7.5(3) . . . . ? O3 C8 C9 C10 92.9(3) . . . . ? C1 C8 C9 C10 -83.4(3) . . . . ? O3 C8 C9 C11 -34.8(3) . . . . ? C1 C8 C9 C11 148.9(2) . . . . ? O3 C8 C9 C13 -130.8(3) . . . . ? C1 C8 C9 C13 52.9(3) . . . . ? C8 C9 C11 C15 -54.3(3) . . . . ? C10 C9 C11 C15 -177.2(3) . . . . ? C13 C9 C11 C15 66.2(2) . . . . ? C8 C9 C11 C12 -156.2(2) . . . . ? C10 C9 C11 C12 81.0(3) . . . . ? C13 C9 C11 C12 -35.6(2) . . . . ? C8 C9 C11 C13 -120.6(2) . . . . ? C10 C9 C11 C13 116.5(3) . . . . ? C15 C11 C12 C13 -67.6(2) . . . . ? C9 C11 C12 C13 35.0(2) . . . . ? C8 C9 C13 C14 48.5(3) . . . . ? C10 C9 C13 C14 -179.9(2) . . . . ? C11 C9 C13 C14 -65.9(2) . . . . ? C8 C9 C13 C12 149.2(3) . . . . ? C10 C9 C13 C12 -79.2(3) . . . . ? C11 C9 C13 C12 34.9(2) . . . . ? C8 C9 C13 C11 114.4(3) . . . . ? C10 C9 C13 C11 -114.0(2) . . . . ? C11 C12 C13 C14 65.7(2) . . . . ? C11 C12 C13 C9 -35.0(2) . . . . ? C15 C11 C13 C14 -0.93(19) . . . . ? C12 C11 C13 C14 -114.9(3) . . . . ? C9 C11 C13 C14 114.7(2) . . . . ? C15 C11 C13 C9 -115.6(2) . . . . ? C12 C11 C13 C9 130.4(3) . . . . ? C15 C11 C13 C12 113.9(3) . . . . ? C9 C11 C13 C12 -130.4(3) . . . . ? C9 C13 C14 C15 45.1(2) . . . . ? C12 C13 C14 C15 -42.9(3) . . . . ? C11 C13 C14 C15 0.92(19) . . . . ? C12 C11 C15 C14 46.4(2) . . . . ? C9 C11 C15 C14 -43.3(2) . . . . ? C13 C11 C15 C14 0.89(18) . . . . ? C13 C14 C15 C11 -1.2(3) . . . . ? C21 C16 C17 C18 -0.6(3) . . . . ? C22 C16 C17 C18 179.8(2) . . . . ? C16 C17 C18 C19 0.5(3) . . . . ? C17 C18 C19 C20 0.4(4) . . . . ? C18 C19 C20 C21 -1.2(4) . . . . ? C19 C20 C21 C16 1.1(4) . . . . ? C17 C16 C21 C20 -0.2(3) . . . . ? C22 C16 C21 C20 179.4(2) . . . . ? C21 C16 C22 N1 128.4(2) . . . . ? C17 C16 C22 N1 -52.0(3) . . . . ? C21 C16 C22 C23 -107.2(3) . . . . ? C17 C16 C22 C23 72.4(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.218 _refine_diff_density_min -0.197 _refine_diff_density_rms 0.040 # Attachment 'js199Feb22.cif' data_js199 _database_code_depnum_ccdc_archive 'CCDC 287134' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O3' _chemical_formula_weight 365.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 6.2120(10) _cell_length_b 7.213(2) _cell_length_c 44.481(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1993.1(8) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 4178 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 20.49 _exptl_crystal_description needle _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.855 _exptl_absorpt_correction_T_max 0.997 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22894 _diffrn_reflns_av_R_equivalents 0.0592 _diffrn_reflns_av_sigmaI/netI 0.0630 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -53 _diffrn_reflns_limit_l_max 48 _diffrn_reflns_theta_min 1.83 _diffrn_reflns_theta_max 25.04 _reflns_number_total 3527 _reflns_number_gt 2492 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.1139P)^2^+1.8015P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 1(4) _refine_ls_number_reflns 3527 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1165 _refine_ls_R_factor_gt 0.0843 _refine_ls_wR_factor_ref 0.2437 _refine_ls_wR_factor_gt 0.2254 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.035 _refine_ls_shift/su_mean 0.005 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 C1 C 0.6693(7) 0.0341(7) 0.85613(12) 0.0522(13) Uani 1 1 d . . . C2 C 0.8789(8) 0.0970(8) 0.86200(11) 0.0532(13) Uani 1 1 d . . . H2 H 0.9700 0.1289 0.8457 0.064 Uiso 1 1 calc R . . C3 C 0.9559(7) 0.1134(7) 0.89114(11) 0.0477(12) Uani 1 1 d . . . H3 H 1.1002 0.1516 0.8946 0.057 Uiso 1 1 calc R . . C4 C 0.8215(7) 0.0740(6) 0.91533(10) 0.0399(10) Uani 1 1 d . . . C5 C 0.6136(7) 0.0154(6) 0.90967(11) 0.0450(11) Uani 1 1 d . . . H5 H 0.5183 -0.0076 0.9259 0.054 Uiso 1 1 calc R . . C6 C 0.5427(7) -0.0103(7) 0.88011(12) 0.0496(12) Uani 1 1 d . . . H6 H 0.4031 -0.0598 0.8767 0.060 Uiso 1 1 calc R . . C7 C 0.9023(7) 0.1059(6) 0.94696(11) 0.0432(11) Uani 1 1 d . . . C16 C 0.2965(8) -0.4602(7) 0.92990(11) 0.0487(12) Uani 1 1 d . . . C17 C 0.4568(9) -0.5169(7) 0.91021(12) 0.0557(13) Uani 1 1 d . . . H17 H 0.5889 -0.5624 0.9180 0.067 Uiso 1 1 calc R . . C18 C 0.4279(10) -0.5086(7) 0.87932(13) 0.0615(15) Uani 1 1 d . . . H18 H 0.5388 -0.5492 0.8662 0.074 Uiso 1 1 calc R . . C19 C 0.2355(11) -0.4404(8) 0.86770(14) 0.0675(16) Uani 1 1 d . . . H19 H 0.2155 -0.4325 0.8466 0.081 Uiso 1 1 calc R . . C20 C 0.0743(10) -0.3844(9) 0.88693(15) 0.0705(17) Uani 1 1 d . . . H20 H -0.0578 -0.3399 0.8789 0.085 Uiso 1 1 calc R . . C21 C 0.1024(8) -0.3922(8) 0.91742(14) 0.0623(15) Uani 1 1 d . . . H21 H -0.0096 -0.3514 0.9304 0.075 Uiso 1 1 calc R . . C22 C 0.3253(8) -0.4671(6) 0.96364(11) 0.0517(12) Uani 1 1 d . . . H22 H 0.1854 -0.4294 0.9729 0.062 Uiso 1 1 calc R . . C23 C 0.4957(13) -0.3394(9) 0.97561(14) 0.086(2) Uani 1 1 d . . . H23A H 0.6337 -0.3678 0.9660 0.129 Uiso 1 1 calc R . . H23B H 0.5088 -0.3563 0.9974 0.129 Uiso 1 1 calc R . . H23C H 0.4558 -0.2107 0.9713 0.129 Uiso 1 1 calc R . . N1 N 0.3737(8) -0.6640(6) 0.97409(12) 0.0445(11) Uani 1 1 d . . . O1 O 1.0961(5) 0.0759(5) 0.95223(7) 0.0516(9) Uani 1 1 d . . . O2 O 0.7683(6) 0.1630(6) 0.96621(7) 0.0606(10) Uani 1 1 d . . . C8A C 0.5778(9) 0.0329(10) 0.82393(14) 0.0715(17) Uani 1 1 d . . . C9A C 0.6951(13) 0.1233(12) 0.79755(15) 0.098(2) Uani 1 1 d . . . C10A C 0.7247(18) 0.3311(12) 0.79455(19) 0.119(3) Uani 1 1 d . . . H10A H 0.8052 0.3583 0.7761 0.179 Uiso 1 1 calc R . . H10B H 0.8045 0.3780 0.8120 0.179 Uiso 1 1 calc R . . H10C H 0.5834 0.3913 0.7936 0.179 Uiso 1 1 calc R . . C11A C 0.5701(11) 0.0056(11) 0.77436(15) 0.084(2) Uani 1 1 d . . . H11A H 0.4346 0.0529 0.7649 0.101 Uiso 1 1 calc R . . C12A C 0.7749(13) -0.0185(18) 0.75587(18) 0.134(4) Uani 1 1 d . . . H12A H 0.8103 0.0868 0.7425 0.161 Uiso 1 1 calc R . . H12B H 0.7885 -0.1393 0.7455 0.161 Uiso 1 1 calc R . . C13A C 0.8810(13) -0.0098(13) 0.78794(18) 0.102(3) Uani 1 1 d . . . H13A H 1.0333 0.0335 0.7898 0.122 Uiso 1 1 calc R . . C14A C 0.8202(14) -0.1850(13) 0.80134(19) 0.105(3) Uani 1 1 d . . . H14A H 0.8894 -0.2062 0.8211 0.126 Uiso 1 1 calc R . . H14B H 0.8466 -0.2919 0.7879 0.126 Uiso 1 1 calc R . . C15A C 0.5624(17) -0.1327(14) 0.8043(3) 0.143(4) Uani 1 1 d . . . H15A H 0.4487 -0.2294 0.8070 0.172 Uiso 1 1 calc R . . O3A O 0.3633(7) 0.1102(11) 0.82450(12) 0.121(2) Uani 1 1 d . . . H3A H 0.3257 0.1382 0.8069 0.182 Uiso 1 1 calc R . . H1B H 0.509(12) -0.713(9) 0.9666(15) 0.09(2) Uiso 1 1 d . . . H1A H 0.302(7) -0.722(6) 0.9690(9) 0.013(13) Uiso 1 1 d . . . H1C H 0.378(9) -0.670(8) 0.9959(15) 0.074(18) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.037(2) 0.056(3) 0.063(3) -0.009(3) -0.005(2) -0.010(2) C2 0.039(2) 0.071(4) 0.050(3) 0.002(2) 0.008(2) -0.006(3) C3 0.024(2) 0.052(3) 0.067(3) 0.001(2) 0.001(2) -0.002(2) C4 0.036(2) 0.030(2) 0.054(3) 0.000(2) 0.000(2) 0.0091(19) C5 0.035(2) 0.040(2) 0.061(3) 0.003(2) 0.010(2) -0.008(2) C6 0.033(2) 0.047(3) 0.069(3) 0.006(2) -0.001(2) -0.009(2) C7 0.039(2) 0.034(2) 0.057(3) 0.007(2) -0.002(2) 0.0000(19) C16 0.048(3) 0.041(3) 0.057(3) 0.000(2) -0.001(2) 0.007(2) C17 0.054(3) 0.044(3) 0.069(4) 0.007(2) -0.001(3) 0.010(2) C18 0.079(4) 0.042(3) 0.064(3) -0.005(3) 0.005(3) -0.002(3) C19 0.091(5) 0.045(3) 0.067(3) 0.009(3) -0.014(3) -0.008(3) C20 0.062(4) 0.067(4) 0.082(4) 0.022(3) -0.022(3) -0.008(3) C21 0.045(3) 0.061(3) 0.082(4) 0.016(3) -0.002(3) 0.008(3) C22 0.058(3) 0.039(3) 0.058(3) 0.004(2) 0.001(3) 0.008(2) C23 0.138(6) 0.052(3) 0.067(4) 0.001(3) -0.013(4) -0.026(4) N1 0.036(2) 0.039(2) 0.058(3) 0.004(2) -0.001(2) -0.005(2) O1 0.0348(17) 0.055(2) 0.065(2) -0.0017(17) -0.0109(15) -0.0024(15) O2 0.051(2) 0.083(3) 0.0481(19) -0.0065(19) -0.0015(18) 0.0213(19) C8A 0.046(3) 0.099(5) 0.070(4) -0.016(3) 0.002(3) -0.016(3) C9A 0.103(5) 0.127(7) 0.065(4) -0.029(4) -0.020(4) 0.004(5) C10A 0.153(8) 0.090(6) 0.116(6) 0.009(5) -0.038(6) -0.003(6) C11A 0.072(4) 0.112(6) 0.069(4) -0.016(4) -0.010(3) 0.005(4) C12A 0.084(5) 0.212(11) 0.108(6) -0.042(7) 0.015(5) -0.032(7) C13A 0.079(5) 0.127(7) 0.100(5) -0.026(5) -0.022(4) -0.004(5) C14A 0.114(7) 0.110(6) 0.090(5) -0.025(5) -0.013(5) -0.005(5) C15A 0.122(7) 0.113(7) 0.194(11) -0.049(7) -0.071(7) 0.006(6) O3A 0.055(3) 0.207(7) 0.102(4) -0.039(4) -0.025(3) 0.017(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 C1 C6 1.364(7) . ? C1 C2 1.403(7) . ? C1 C8A 1.541(8) . ? C2 C3 1.387(7) . ? C2 H2 0.9500 . ? C3 C4 1.391(6) . ? C3 H3 0.9500 . ? C4 C5 1.382(6) . ? C4 C7 1.511(7) . ? C5 C6 1.399(7) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.246(5) . ? C7 O2 1.263(6) . ? C16 C17 1.388(7) . ? C16 C21 1.415(7) . ? C16 C22 1.512(7) . ? C17 C18 1.387(8) . ? C17 H17 0.9500 . ? C18 C19 1.392(8) . ? C18 H18 0.9500 . ? C19 C20 1.378(9) . ? C19 H19 0.9500 . ? C20 C21 1.368(8) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.501(8) . ? C22 N1 1.524(6) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N1 H1B 0.97(8) . ? N1 H1A 0.65(4) . ? N1 H1C 0.97(6) . ? C8A O3A 1.444(8) . ? C8A C15A 1.484(11) . ? C8A C9A 1.527(10) . ? C9A C10A 1.516(12) . ? C9A C11A 1.545(10) . ? C9A C13A 1.561(11) . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C11A C12A 1.525(10) . ? C11A C15A 1.664(14) . ? C11A C13A 2.026(10) . ? C11A H11A 1.0000 . ? C12A C13A 1.572(10) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C14A 1.448(12) . ? C13A H13A 1.0000 . ? C14A C15A 1.650(13) . ? C14A H14A 0.9900 . ? C14A H14B 0.9900 . ? C15A H15A 1.0000 . ? O3A H3A 0.8400 . ? 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 C1 C2 117.8(5) . . ? C6 C1 C8A 120.8(4) . . ? C2 C1 C8A 121.1(5) . . ? C3 C2 C1 121.5(5) . . ? C3 C2 H2 119.3 . . ? C1 C2 H2 119.3 . . ? C2 C3 C4 119.9(4) . . ? C2 C3 H3 120.1 . . ? C4 C3 H3 120.1 . . ? C5 C4 C3 118.8(4) . . ? C5 C4 C7 121.8(4) . . ? C3 C4 C7 119.3(4) . . ? C4 C5 C6 120.4(4) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 121.5(4) . . ? C1 C6 H6 119.3 . . ? C5 C6 H6 119.3 . . ? O1 C7 O2 124.5(4) . . ? O1 C7 C4 118.0(4) . . ? O2 C7 C4 117.5(4) . . ? C17 C16 C21 117.8(5) . . ? C17 C16 C22 122.1(4) . . ? C21 C16 C22 120.1(5) . . ? C18 C17 C16 121.3(5) . . ? C18 C17 H17 119.3 . . ? C16 C17 H17 119.3 . . ? C17 C18 C19 119.6(5) . . ? C17 C18 H18 120.2 . . ? C19 C18 H18 120.2 . . ? C20 C19 C18 119.8(5) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C21 C20 C19 120.7(6) . . ? C21 C20 H20 119.6 . . ? C19 C20 H20 119.6 . . ? C20 C21 C16 120.8(6) . . ? C20 C21 H21 119.6 . . ? C16 C21 H21 119.6 . . ? C23 C22 C16 114.6(4) . . ? C23 C22 N1 108.9(5) . . ? C16 C22 N1 110.9(4) . . ? C23 C22 H22 107.4 . . ? C16 C22 H22 107.4 . . ? N1 C22 H22 107.4 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 N1 H1B 114(4) . . ? C22 N1 H1A 111(4) . . ? H1B N1 H1A 104(5) . . ? C22 N1 H1C 111(3) . . ? H1B N1 H1C 108(5) . . ? H1A N1 H1C 110(5) . . ? O3A C8A C15A 105.1(6) . . ? O3A C8A C9A 106.8(6) . . ? C15A C8A C9A 85.5(7) . . ? O3A C8A C1 108.8(5) . . ? C15A C8A C1 125.2(7) . . ? C9A C8A C1 122.4(5) . . ? C10A C9A C8A 123.2(7) . . ? C10A C9A C11A 123.0(7) . . ? C8A C9A C11A 92.2(6) . . ? C10A C9A C13A 119.6(8) . . ? C8A C9A C13A 107.5(7) . . ? C11A C9A C13A 81.4(5) . . ? C9A C10A H10A 109.5 . . ? C9A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C9A C10A H10C 109.5 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C12A C11A C9A 90.2(6) . . ? C12A C11A C15A 112.8(8) . . ? C9A C11A C15A 79.1(5) . . ? C12A C11A C13A 50.2(4) . . ? C9A C11A C13A 49.6(4) . . ? C15A C11A C13A 75.9(5) . . ? C12A C11A H11A 121.0 . . ? C9A C11A H11A 121.0 . . ? C15A C11A H11A 121.0 . . ? C13A C11A H11A 161.0 . . ? C11A C12A C13A 81.7(5) . . ? C11A C12A H12A 115.0 . . ? C13A C12A H12A 115.0 . . ? C11A C12A H12B 115.0 . . ? C13A C12A H12B 115.0 . . ? H12A C12A H12B 112.1 . . ? C14A C13A C9A 103.4(7) . . ? C14A C13A C12A 103.3(7) . . ? C9A C13A C12A 87.9(6) . . ? C14A C13A C11A 85.5(6) . . ? C9A C13A C11A 48.9(4) . . ? C12A C13A C11A 48.1(4) . . ? C14A C13A H13A 119.0 . . ? C9A C13A H13A 119.0 . . ? C12A C13A H13A 119.0 . . ? C11A C13A H13A 155.5 . . ? C13A C14A C15A 94.9(8) . . ? C13A C14A H14A 112.7 . . ? C15A C14A H14A 112.7 . . ? C13A C14A H14B 112.8 . . ? C15A C14A H14B 112.8 . . ? H14A C14A H14B 110.2 . . ? C8A C15A C14A 99.7(7) . . ? C8A C15A C11A 89.2(7) . . ? C14A C15A C11A 92.6(8) . . ? C8A C15A H15A 122.4 . . ? C14A C15A H15A 122.4 . . ? C11A C15A H15A 122.4 . . ? C8A O3A H3A 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 0.1(8) . . . . ? C8A C1 C2 C3 174.4(5) . . . . ? C1 C2 C3 C4 -2.5(8) . . . . ? C2 C3 C4 C5 1.2(7) . . . . ? C2 C3 C4 C7 -175.6(4) . . . . ? C3 C4 C5 C6 2.4(7) . . . . ? C7 C4 C5 C6 179.1(4) . . . . ? C2 C1 C6 C5 3.6(7) . . . . ? C8A C1 C6 C5 -170.8(5) . . . . ? C4 C5 C6 C1 -4.9(7) . . . . ? C5 C4 C7 O1 148.1(4) . . . . ? C3 C4 C7 O1 -35.2(6) . . . . ? C5 C4 C7 O2 -32.5(6) . . . . ? C3 C4 C7 O2 144.2(4) . . . . ? C21 C16 C17 C18 -0.4(8) . . . . ? C22 C16 C17 C18 -179.6(5) . . . . ? C16 C17 C18 C19 0.7(8) . . . . ? C17 C18 C19 C20 -1.0(8) . . . . ? C18 C19 C20 C21 1.1(9) . . . . ? C19 C20 C21 C16 -0.9(9) . . . . ? C17 C16 C21 C20 0.5(8) . . . . ? C22 C16 C21 C20 179.7(5) . . . . ? C17 C16 C22 C23 65.3(7) . . . . ? C21 C16 C22 C23 -113.9(6) . . . . ? C17 C16 C22 N1 -58.5(7) . . . . ? C21 C16 C22 N1 122.3(5) . . . . ? C6 C1 C8A O3A 40.2(8) . . . . ? C2 C1 C8A O3A -133.9(6) . . . . ? C6 C1 C8A C15A -85.0(9) . . . . ? C2 C1 C8A C15A 100.9(9) . . . . ? C6 C1 C8A C9A 165.5(6) . . . . ? C2 C1 C8A C9A -8.6(9) . . . . ? O3A C8A C9A C10A 57.9(9) . . . . ? C15A C8A C9A C10A 162.4(9) . . . . ? C1 C8A C9A C10A -68.3(10) . . . . ? O3A C8A C9A C11A -74.8(6) . . . . ? C15A C8A C9A C11A 29.7(6) . . . . ? C1 C8A C9A C11A 159.1(6) . . . . ? O3A C8A C9A C13A -156.5(5) . . . . ? C15A C8A C9A C13A -52.0(6) . . . . ? C1 C8A C9A C13A 77.4(8) . . . . ? C10A C9A C11A C12A 87.4(10) . . . . ? C8A C9A C11A C12A -139.9(7) . . . . ? C13A C9A C11A C12A -32.5(7) . . . . ? C10A C9A C11A C15A -159.4(9) . . . . ? C8A C9A C11A C15A -26.7(6) . . . . ? C13A C9A C11A C15A 80.7(6) . . . . ? C10A C9A C11A C13A 119.9(10) . . . . ? C8A C9A C11A C13A -107.4(7) . . . . ? C9A C11A C12A C13A 32.2(7) . . . . ? C15A C11A C12A C13A -46.0(8) . . . . ? C10A C9A C13A C14A 165.0(7) . . . . ? C8A C9A C13A C14A 17.9(7) . . . . ? C11A C9A C13A C14A -71.7(7) . . . . ? C10A C9A C13A C12A -91.9(8) . . . . ? C8A C9A C13A C12A 121.0(7) . . . . ? C11A C9A C13A C12A 31.4(6) . . . . ? C10A C9A C13A C11A -123.3(8) . . . . ? C8A C9A C13A C11A 89.6(6) . . . . ? C11A C12A C13A C14A 71.4(7) . . . . ? C11A C12A C13A C9A -31.8(7) . . . . ? C12A C11A C13A C14A -112.3(8) . . . . ? C9A C11A C13A C14A 112.1(7) . . . . ? C15A C11A C13A C14A 24.5(6) . . . . ? C12A C11A C13A C9A 135.6(10) . . . . ? C15A C11A C13A C9A -87.5(7) . . . . ? C9A C11A C13A C12A -135.6(10) . . . . ? C15A C11A C13A C12A 136.8(8) . . . . ? C9A C13A C14A C15A 21.9(7) . . . . ? C12A C13A C14A C15A -69.1(7) . . . . ? C11A C13A C14A C15A -24.1(5) . . . . ? O3A C8A C15A C14A 171.4(7) . . . . ? C9A C8A C15A C14A 65.2(8) . . . . ? C1 C8A C15A C14A -61.8(11) . . . . ? O3A C8A C15A C11A 78.8(7) . . . . ? C9A C8A C15A C11A -27.4(6) . . . . ? C1 C8A C15A C11A -154.4(6) . . . . ? C13A C14A C15A C8A -60.0(9) . . . . ? C13A C14A C15A C11A 29.7(6) . . . . ? C12A C11A C15A C8A 113.0(7) . . . . ? C9A C11A C15A C8A 27.5(6) . . . . ? C13A C11A C15A C8A 78.3(5) . . . . ? C12A C11A C15A C14A 13.4(8) . . . . ? C9A C11A C15A C14A -72.1(6) . . . . ? C13A C11A C15A C14A -21.3(5) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 25.04 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.362 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.057 # Attachment 'js200Feb22.cif' data_js200 _database_code_depnum_ccdc_archive 'CCDC 287135' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C23 H27 N O3' _chemical_formula_weight 365.46 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting 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 6.1739(8) _cell_length_b 7.1907(9) _cell_length_c 44.763(7) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1987.2(5) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used 3592 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 21.14 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.222 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.613 _exptl_absorpt_correction_T_max 0.994 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker X8 APEX' _diffrn_measurement_method 'area detector' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 9447 _diffrn_reflns_av_R_equivalents 0.0485 _diffrn_reflns_av_sigmaI/netI 0.0571 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_l_min -46 _diffrn_reflns_limit_l_max 47 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 22.43 _reflns_number_total 2570 _reflns_number_gt 2280 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution ? _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _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^)+(0.0292P)^2^+10.4972P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -3(6) _refine_ls_number_reflns 2570 _refine_ls_number_parameters 205 _refine_ls_number_restraints 29 _refine_ls_R_factor_all 0.1260 _refine_ls_R_factor_gt 0.1161 _refine_ls_wR_factor_ref 0.2515 _refine_ls_wR_factor_gt 0.2475 _refine_ls_goodness_of_fit_ref 1.165 _refine_ls_restrained_S_all 1.158 _refine_ls_shift/su_max 0.026 _refine_ls_shift/su_mean 0.003 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 C1A C 0.6762(17) 0.0294(18) 0.8561(2) 0.024(5) Uiso 0.57(2) 1 d PGD A 1 C2A C 0.8800(16) 0.1057(18) 0.86106(17) 0.024(4) Uiso 0.57(2) 1 d PGD A 1 H2A H 0.9676 0.1415 0.8446 0.029 Uiso 0.57(2) 1 calc PR A 1 C3A C 0.9554(13) 0.1296(17) 0.89006(19) 0.026(4) Uiso 0.57(2) 1 d PGD A 1 H3A H 1.0947 0.1818 0.8934 0.032 Uiso 0.57(2) 1 calc PR A 1 C4A C 0.8272(15) 0.0772(18) 0.91415(17) 0.022(5) Uiso 0.57(2) 1 d PGD A 1 C5A C 0.6234(14) 0.0008(19) 0.9092(2) 0.027(5) Uiso 0.57(2) 1 d PGD A 1 H5A H 0.5358 -0.0350 0.9257 0.032 Uiso 0.57(2) 1 calc PR A 1 C6A C 0.5479(14) -0.0230(18) 0.8802(3) 0.028(5) Uiso 0.57(2) 1 d PGD A 1 H6A H 0.4087 -0.0752 0.8769 0.033 Uiso 0.57(2) 1 calc PR A 1 C7A C 0.9119(18) 0.105(3) 0.9451(2) 0.0246(18) Uiso 0.57(2) 1 d PD A 1 O1A O 1.1123(14) 0.0858(19) 0.9493(3) 0.031(4) Uiso 0.57(2) 1 d PD A 1 O2A O 0.7768(15) 0.1510(19) 0.96538(19) 0.027(4) Uiso 0.57(2) 1 d PD A 1 C16 C 0.2964(14) -0.4639(12) 0.93093(19) 0.040(2) Uani 1 1 d . . . C17 C 0.4573(14) -0.5210(12) 0.91168(18) 0.044(2) Uani 1 1 d . . . H17 H 0.5906 -0.5640 0.9197 0.053 Uiso 1 1 calc R . . C18 C 0.4299(16) -0.5173(12) 0.8808(2) 0.051(2) Uani 1 1 d . . . H18 H 0.5399 -0.5623 0.8678 0.061 Uiso 1 1 calc R . . C19 C 0.2372(18) -0.4461(14) 0.8694(2) 0.062(3) Uani 1 1 d . . . H19 H 0.2166 -0.4371 0.8484 0.074 Uiso 1 1 calc R . . C20 C 0.0766(19) -0.3887(15) 0.8886(2) 0.068(3) Uani 1 1 d . . . H20 H -0.0569 -0.3444 0.8808 0.082 Uiso 1 1 calc R . . C21 C 0.1079(14) -0.3950(12) 0.9190(2) 0.048(2) Uani 1 1 d . . . H21 H -0.0026 -0.3509 0.9320 0.058 Uiso 1 1 calc R . . C22 C 0.3240(13) -0.4693(11) 0.96456(17) 0.038(2) Uani 1 1 d . . . H22 H 0.1827 -0.4349 0.9740 0.046 Uiso 1 1 calc R . . C23 C 0.4969(17) -0.3375(13) 0.9762(2) 0.064(3) Uani 1 1 d . . . H23A H 0.6371 -0.3702 0.9673 0.096 Uiso 1 1 calc R . . H23B H 0.5058 -0.3477 0.9980 0.096 Uiso 1 1 calc R . . H23C H 0.4593 -0.2096 0.9707 0.096 Uiso 1 1 calc R . . N1 N 0.3830(9) -0.6661(8) 0.97446(13) 0.0317(16) Uani 1 1 d . . . H1A H 0.2880 -0.7485 0.9663 0.048 Uiso 1 1 calc R . . H1B H 0.3767 -0.6735 0.9947 0.048 Uiso 1 1 calc R . . H1C H 0.5196 -0.6936 0.9682 0.048 Uiso 1 1 calc R . . C8A C 0.566(4) 0.039(4) 0.8246(4) 0.066(10) Uiso 0.57(2) 1 d PD A 1 C9A C 0.683(3) 0.095(3) 0.8012(4) 0.046(5) Uiso 0.57(2) 1 d PD A 1 C10A C 0.732(5) 0.303(3) 0.7943(6) 0.101(9) Uiso 0.57(2) 1 d PD A 1 H10A H 0.8183 0.3120 0.7760 0.151 Uiso 0.57(2) 1 calc PR A 1 H10B H 0.8121 0.3581 0.8110 0.151 Uiso 0.57(2) 1 calc PR A 1 H10C H 0.5950 0.3706 0.7915 0.151 Uiso 0.57(2) 1 calc PR A 1 C11A C 0.573(3) -0.013(3) 0.7752(4) 0.055(6) Uiso 0.57(2) 1 d PD A 1 H11A H 0.4323 0.0351 0.7672 0.066 Uiso 0.57(2) 1 calc PR A 1 C12A C 0.777(4) 0.009(6) 0.7562(4) 0.145(13) Uiso 0.57(2) 1 d PD A 1 H12A H 0.7942 0.1315 0.7463 0.174 Uiso 0.57(2) 1 calc PR A 1 H12B H 0.8099 -0.0960 0.7427 0.174 Uiso 0.57(2) 1 calc PR A 1 C13A C 0.877(3) -0.006(3) 0.7896(4) 0.064(6) Uiso 0.57(2) 1 d PD A 1 H13A H 1.0226 0.0517 0.7932 0.076 Uiso 0.57(2) 1 calc PR A 1 C14A C 0.843(4) -0.200(3) 0.8003(6) 0.070(7) Uiso 0.57(2) 1 d PD A 1 H14A H 0.9269 -0.2306 0.8185 0.084 Uiso 0.57(2) 1 calc PR A 1 H14B H 0.8660 -0.2951 0.7846 0.084 Uiso 0.57(2) 1 calc PR A 1 C15A C 0.568(4) -0.154(3) 0.8074(5) 0.083(7) Uiso 0.57(2) 1 d P A 1 H15C H 0.4578 -0.2535 0.8108 0.100 Uiso 0.57(2) 1 calc PR A 1 O3A O 0.3651(19) 0.088(2) 0.8255(3) 0.061(5) Uiso 0.57(2) 1 d P A 1 H3O H 0.3562 0.2041 0.8232 0.091 Uiso 0.57(2) 1 calc PR A 1 O3 O 0.359(4) -0.052(4) 0.8312(5) 0.104(9) Uiso 0.43(2) 1 d P A 2 C8 C 0.582(4) -0.006(3) 0.8288(4) 0.021(6) Uiso 0.43(2) 1 d PD A 2 C9 C 0.711(6) 0.036(6) 0.7977(10) 0.110(17) Uiso 0.43(2) 1 d PD A 2 C10 C 0.648(7) 0.246(5) 0.7970(9) 0.117(15) Uiso 0.43(2) 1 d PD A 2 H10D H 0.7377 0.3145 0.8113 0.176 Uiso 0.43(2) 1 calc PR A 2 H10E H 0.4950 0.2594 0.8024 0.176 Uiso 0.43(2) 1 calc PR A 2 H10F H 0.6716 0.2955 0.7769 0.176 Uiso 0.43(2) 1 calc PR A 2 C11 C 0.575(4) -0.094(5) 0.7770(7) 0.073(9) Uiso 0.43(2) 1 d PD A 2 H11 H 0.4378 -0.0522 0.7673 0.088 Uiso 0.43(2) 1 calc PR A 2 C12 C 0.793(4) -0.084(5) 0.7612(5) 0.074(9) Uiso 0.43(2) 1 d PD A 2 H12C H 0.8164 0.0320 0.7497 0.088 Uiso 0.43(2) 1 calc PR A 2 H12D H 0.8272 -0.1949 0.7489 0.088 Uiso 0.43(2) 1 calc PR A 2 C13 C 0.907(4) -0.085(5) 0.7939(5) 0.077(10) Uiso 0.43(2) 1 d PD A 2 H13 H 1.0590 -0.0448 0.7979 0.093 Uiso 0.43(2) 1 calc PR A 2 C14 C 0.801(6) -0.250(5) 0.8079(9) 0.092(13) Uiso 0.43(2) 1 d PD A 2 H14C H 0.8927 -0.3615 0.8053 0.110 Uiso 0.43(2) 1 calc PR A 2 H14D H 0.7808 -0.2281 0.8296 0.110 Uiso 0.43(2) 1 calc PR A 2 C1 C 0.663(2) 0.018(3) 0.8618(3) 0.035(8) Uiso 0.43(2) 1 d PGD A 2 C2 C 0.881(2) 0.062(3) 0.8652(2) 0.045(7) Uiso 0.43(2) 1 d PGD A 2 H2 H 0.9709 0.0759 0.8481 0.054 Uiso 0.43(2) 1 calc PR A 2 C3 C 0.9672(17) 0.087(3) 0.8936(3) 0.030(6) Uiso 0.43(2) 1 d PGD A 2 H3 H 1.1160 0.1170 0.8959 0.036 Uiso 0.43(2) 1 calc PR A 2 C4 C 0.836(2) 0.067(3) 0.9186(2) 0.040(9) Uiso 0.43(2) 1 d PGD A 2 C5 C 0.6180(19) 0.022(2) 0.9152(3) 0.027(6) Uiso 0.43(2) 1 d PGD A 2 H5 H 0.5281 0.0088 0.9323 0.033 Uiso 0.43(2) 1 calc PR A 2 C6 C 0.5317(18) -0.002(2) 0.8868(3) 0.027(6) Uiso 0.43(2) 1 d PGD A 2 H6 H 0.3829 -0.0323 0.8844 0.033 Uiso 0.43(2) 1 calc PR A 2 C7 C 0.926(2) 0.115(4) 0.9486(3) 0.0246(18) Uiso 0.43(2) 1 d PD A 2 O1 O 1.1118(17) 0.056(2) 0.9550(3) 0.025(6) Uiso 0.43(2) 1 d PD A 2 O2 O 0.804(2) 0.206(3) 0.9663(3) 0.034(5) Uiso 0.43(2) 1 d PD A 2 C15 C 0.592(10) -0.278(8) 0.7935(12) 0.23(3) Uiso 0.43(2) 1 d PD A 2 H15A H 0.4734 -0.2936 0.8083 0.278 Uiso 0.43(2) 1 calc PR A 2 H15B H 0.5933 -0.3854 0.7797 0.278 Uiso 0.43(2) 1 calc PR A 2 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 C16 0.041(5) 0.032(5) 0.047(5) -0.004(4) -0.007(4) -0.004(4) C17 0.047(5) 0.041(5) 0.044(6) 0.003(4) 0.003(4) 0.010(4) C18 0.060(7) 0.042(6) 0.052(6) -0.007(5) 0.012(5) 0.001(5) C19 0.086(8) 0.049(6) 0.050(6) 0.009(5) -0.006(6) -0.014(6) C20 0.068(8) 0.064(7) 0.072(8) 0.030(6) -0.016(6) -0.011(6) C21 0.033(5) 0.048(6) 0.063(7) 0.013(5) 0.000(5) 0.014(4) C22 0.044(5) 0.032(5) 0.038(5) -0.007(4) 0.004(4) 0.014(4) C23 0.086(8) 0.050(6) 0.056(6) -0.010(5) 0.000(6) -0.036(6) N1 0.022(3) 0.041(4) 0.032(4) 0.004(3) 0.004(3) -0.002(3) _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 C1A C2A 1.3900 . ? C1A C6A 1.3900 . ? C1A C8A 1.571(14) . ? C2A C3A 1.3900 . ? C2A H2A 0.9500 . ? C3A C4A 1.3900 . ? C3A H3A 0.9500 . ? C4A C5A 1.3900 . ? C4A C7A 1.494(9) . ? C5A C6A 1.3900 . ? C5A H5A 0.9500 . ? C6A H6A 0.9500 . ? C7A O1A 1.259(9) . ? C7A O2A 1.277(9) . ? C16 C21 1.372(12) . ? C16 C17 1.377(11) . ? C16 C22 1.516(11) . ? C17 C18 1.394(12) . ? C17 H17 0.9500 . ? C18 C19 1.392(14) . ? C18 H18 0.9500 . ? C19 C20 1.375(14) . ? C19 H19 0.9500 . ? C20 C21 1.378(13) . ? C20 H20 0.9500 . ? C21 H21 0.9500 . ? C22 C23 1.519(12) . ? C22 N1 1.527(10) . ? C22 H22 1.0000 . ? C23 H23A 0.9800 . ? C23 H23B 0.9800 . ? C23 H23C 0.9800 . ? N1 H1A 0.9100 . ? N1 H1B 0.9100 . ? N1 H1C 0.9100 . ? C8A O3A 1.29(3) . ? C8A C9A 1.34(3) . ? C8A C15A 1.58(3) . ? C9A C13A 1.50(2) . ? C9A C11A 1.55(3) . ? C9A C10A 1.56(3) . ? C10A H10A 0.9800 . ? C10A H10B 0.9800 . ? C10A H10C 0.9800 . ? C11A C12A 1.529(19) . ? C11A C15A 1.76(3) . ? C11A H11A 1.0000 . ? C12A C13A 1.62(2) . ? C12A H12A 0.9900 . ? C12A H12B 0.9900 . ? C13A C14A 1.49(3) . ? C13A H13A 1.0000 . ? C14A C15A 1.76(3) . ? C14A H14A 0.9900 . ? C14A H14B 0.9900 . ? C15A H15C 1.0000 . ? O3A H3O 0.8400 . ? O3 C8 1.42(3) . ? C8 C1 1.569(13) . ? C8 C9 1.63(5) . ? C9 C13 1.50(3) . ? C9 C10 1.56(3) . ? C9 C11 1.56(5) . ? C10 H10D 0.9800 . ? C10 H10E 0.9800 . ? C10 H10F 0.9800 . ? C11 C15 1.52(5) . ? C11 C12 1.525(19) . ? C11 H11 1.0000 . ? C12 C13 1.62(2) . ? C12 H12C 0.9900 . ? C12 H12D 0.9900 . ? C13 C14 1.49(3) . ? C13 H13 1.0000 . ? C14 C15 1.46(6) . ? C14 H14C 0.9900 . ? C14 H14D 0.9900 . ? C1 C2 1.3900 . ? C1 C6 1.3900 . ? C2 C3 1.3900 . ? C2 H2 0.9500 . ? C3 C4 1.3900 . ? C3 H3 0.9500 . ? C4 C5 1.3900 . ? C4 C7 1.495(9) . ? C5 C6 1.3900 . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 O1 1.258(10) . ? C7 O2 1.275(10) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2A C1A C6A 120.0 . . ? C2A C1A C8A 121.2(12) . . ? C6A C1A C8A 117.5(13) . . ? C3A C2A C1A 120.0 . . ? C3A C2A H2A 120.0 . . ? C1A C2A H2A 120.0 . . ? C4A C3A C2A 120.0 . . ? C4A C3A H3A 120.0 . . ? C2A C3A H3A 120.0 . . ? C3A C4A C5A 120.0 . . ? C3A C4A C7A 118.9(5) . . ? C5A C4A C7A 121.1(5) . . ? C6A C5A C4A 120.0 . . ? C6A C5A H5A 120.0 . . ? C4A C5A H5A 120.0 . . ? C5A C6A C1A 120.0 . . ? C5A C6A H6A 120.0 . . ? C1A C6A H6A 120.0 . . ? O1A C7A O2A 124.3(8) . . ? O1A C7A C4A 117.9(8) . . ? O2A C7A C4A 117.7(7) . . ? C21 C16 C17 118.5(8) . . ? C21 C16 C22 119.3(8) . . ? C17 C16 C22 122.2(8) . . ? C16 C17 C18 121.8(9) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C19 C18 C17 118.3(9) . . ? C19 C18 H18 120.9 . . ? C17 C18 H18 120.9 . . ? C20 C19 C18 119.9(9) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C21 120.5(10) . . ? C19 C20 H20 119.8 . . ? C21 C20 H20 119.8 . . ? C16 C21 C20 121.0(10) . . ? C16 C21 H21 119.5 . . ? C20 C21 H21 119.5 . . ? C16 C22 C23 113.8(7) . . ? C16 C22 N1 109.8(6) . . ? C23 C22 N1 108.1(7) . . ? C16 C22 H22 108.3 . . ? C23 C22 H22 108.3 . . ? N1 C22 H22 108.3 . . ? C22 C23 H23A 109.5 . . ? C22 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C22 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C22 N1 H1A 109.5 . . ? C22 N1 H1B 109.5 . . ? H1A N1 H1B 109.5 . . ? C22 N1 H1C 109.5 . . ? H1A N1 H1C 109.5 . . ? H1B N1 H1C 109.5 . . ? O3A C8A C9A 117(2) . . ? O3A C8A C1A 113.6(18) . . ? C9A C8A C1A 118.9(19) . . ? O3A C8A C15A 105.4(18) . . ? C9A C8A C15A 83.2(17) . . ? C1A C8A C15A 113(2) . . ? C8A C9A C13A 124(2) . . ? C8A C9A C11A 101.4(16) . . ? C13A C9A C11A 81.3(12) . . ? C8A C9A C10A 124(2) . . ? C13A C9A C10A 104.0(18) . . ? C11A C9A C10A 114.6(17) . . ? C9A C10A H10A 109.5 . . ? C9A C10A H10B 109.5 . . ? H10A C10A H10B 109.5 . . ? C9A C10A H10C 109.4 . . ? H10A C10A H10C 109.5 . . ? H10B C10A H10C 109.5 . . ? C12A C11A C9A 90.3(13) . . ? C12A C11A C15A 122.0(19) . . ? C9A C11A C15A 71.5(13) . . ? C12A C11A H11A 118.5 . . ? C9A C11A H11A 118.5 . . ? C15A C11A H11A 118.5 . . ? C11A C12A C13A 78.1(14) . . ? C11A C12A H12A 115.5 . . ? C13A C12A H12A 115.6 . . ? C11A C12A H12B 115.5 . . ? C13A C12A H12B 115.5 . . ? H12A C12A H12B 112.5 . . ? C14A C13A C9A 103.2(17) . . ? C14A C13A C12A 108(2) . . ? C9A C13A C12A 88.8(13) . . ? C14A C13A H13A 117.6 . . ? C9A C13A H13A 117.6 . . ? C12A C13A H13A 117.6 . . ? C13A C14A C15A 91.1(16) . . ? C13A C14A H14A 113.4 . . ? C15A C14A H14A 113.5 . . ? C13A C14A H14B 113.4 . . ? C15A C14A H14B 113.5 . . ? H14A C14A H14B 110.8 . . ? C8A C15A C14A 105.2(19) . . ? C8A C15A C11A 83.9(15) . . ? C14A C15A C11A 86.8(15) . . ? C8A C15A H15C 123.3 . . ? C14A C15A H15C 123.2 . . ? C11A C15A H15C 123.2 . . ? O3 C8 C1 105.4(17) . . ? O3 C8 C9 126(2) . . ? C1 C8 C9 129(2) . . ? C13 C9 C10 140(4) . . ? C13 C9 C11 91(3) . . ? C10 C9 C11 116(3) . . ? C13 C9 C8 113(3) . . ? C10 C9 C8 94(3) . . ? C11 C9 C8 97(2) . . ? C9 C10 H10D 109.5 . . ? C9 C10 H10E 109.5 . . ? H10D C10 H10E 109.5 . . ? C9 C10 H10F 109.4 . . ? H10D C10 H10F 109.5 . . ? H10E C10 H10F 109.5 . . ? C15 C11 C12 102(3) . . ? C15 C11 C9 101(4) . . ? C12 C11 C9 77(2) . . ? C15 C11 H11 122.2 . . ? C12 C11 H11 122.2 . . ? C9 C11 H11 122.2 . . ? C11 C12 C13 87.8(19) . . ? C11 C12 H12C 114.0 . . ? C13 C12 H12C 114.0 . . ? C11 C12 H12D 114.0 . . ? C13 C12 H12D 114.0 . . ? H12C C12 H12D 111.2 . . ? C14 C13 C9 93(2) . . ? C14 C13 C12 101(2) . . ? C9 C13 C12 76(2) . . ? C14 C13 H13 124.6 . . ? C9 C13 H13 124.5 . . ? C12 C13 H13 124.5 . . ? C15 C14 C13 108(3) . . ? C15 C14 H14C 110.0 . . ? C13 C14 H14C 110.0 . . ? C15 C14 H14D 110.1 . . ? C13 C14 H14D 110.1 . . ? H14C C14 H14D 108.4 . . ? C2 C1 C6 120.0 . . ? C2 C1 C8 116.0(12) . . ? C6 C1 C8 124.0(12) . . ? C1 C2 C3 120.0 . . ? C1 C2 H2 120.0 . . ? C3 C2 H2 120.0 . . ? C4 C3 C2 120.0 . . ? C4 C3 H3 120.0 . . ? C2 C3 H3 120.0 . . ? C5 C4 C3 120.0 . . ? C5 C4 C7 120.7(5) . . ? C3 C4 C7 118.9(6) . . ? C4 C5 C6 120.0 . . ? C4 C5 H5 120.0 . . ? C6 C5 H5 120.0 . . ? C5 C6 C1 120.0 . . ? C5 C6 H6 120.0 . . ? C1 C6 H6 120.0 . . ? O1 C7 O2 124.8(9) . . ? O1 C7 C4 117.7(9) . . ? O2 C7 C4 117.4(8) . . ? C14 C15 C11 99(3) . . ? C14 C15 H15A 112.0 . . ? C11 C15 H15A 112.0 . . ? C14 C15 H15B 112.0 . . ? C11 C15 H15B 112.0 . . ? H15A C15 H15B 109.7 . . ? 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 C6A C1A C2A C3A 0.0 . . . . ? C8A C1A C2A C3A 167.0(17) . . . . ? C1A C2A C3A C4A 0.0 . . . . ? C2A C3A C4A C5A 0.0 . . . . ? C2A C3A C4A C7A -179.8(12) . . . . ? C3A C4A C5A C6A 0.0 . . . . ? C7A C4A C5A C6A 179.8(12) . . . . ? C4A C5A C6A C1A 0.0 . . . . ? C2A C1A C6A C5A 0.0 . . . . ? C8A C1A C6A C5A -167.5(16) . . . . ? C3A C4A C7A O1A -34(2) . . . . ? C5A C4A C7A O1A 146.1(14) . . . . ? C3A C4A C7A O2A 144.2(14) . . . . ? C5A C4A C7A O2A -36(2) . . . . ? C21 C16 C17 C18 -2.6(14) . . . . ? C22 C16 C17 C18 179.4(8) . . . . ? C16 C17 C18 C19 2.8(14) . . . . ? C17 C18 C19 C20 -2.6(15) . . . . ? C18 C19 C20 C21 2.3(16) . . . . ? C17 C16 C21 C20 2.2(14) . . . . ? C22 C16 C21 C20 -179.7(9) . . . . ? C19 C20 C21 C16 -2.1(16) . . . . ? C21 C16 C22 C23 -112.5(10) . . . . ? C17 C16 C22 C23 65.4(11) . . . . ? C21 C16 C22 N1 126.2(8) . . . . ? C17 C16 C22 N1 -55.9(11) . . . . ? C2A C1A C8A O3A -134.3(17) . . . . ? C6A C1A C8A O3A 33(3) . . . . ? C2A C1A C8A C9A 10(3) . . . . ? C6A C1A C8A C9A 177.5(19) . . . . ? C2A C1A C8A C15A 105(2) . . . . ? C6A C1A C8A C15A -87(2) . . . . ? O3A C8A C9A C13A -153.5(19) . . . . ? C1A C8A C9A C13A 63(3) . . . . ? C15A C8A C9A C13A -50(2) . . . . ? O3A C8A C9A C11A -66(3) . . . . ? C1A C8A C9A C11A 150(2) . . . . ? C15A C8A C9A C11A 37.5(18) . . . . ? O3A C8A C9A C10A 64(3) . . . . ? C1A C8A C9A C10A -80(3) . . . . ? C15A C8A C9A C10A 168(2) . . . . ? C8A C9A C11A C12A -159(2) . . . . ? C13A C9A C11A C12A -35.6(18) . . . . ? C10A C9A C11A C12A 66(3) . . . . ? C8A C9A C11A C15A -34.9(18) . . . . ? C13A C9A C11A C15A 88.2(14) . . . . ? C10A C9A C11A C15A -170(2) . . . . ? C9A C11A C12A C13A 32.9(18) . . . . ? C15A C11A C12A C13A -35(2) . . . . ? C8A C9A C13A C14A 23(2) . . . . ? C11A C9A C13A C14A -74.7(16) . . . . ? C10A C9A C13A C14A 172.0(18) . . . . ? C8A C9A C13A C12A 131(2) . . . . ? C11A C9A C13A C12A 33.3(17) . . . . ? C10A C9A C13A C12A -80(2) . . . . ? C11A C12A C13A C14A 69(2) . . . . ? C11A C12A C13A C9A -34.3(18) . . . . ? C9A C13A C14A C15A 16.5(17) . . . . ? C12A C13A C14A C15A -76.6(17) . . . . ? O3A C8A C15A C14A 169.6(18) . . . . ? C9A C8A C15A C14A 53.1(19) . . . . ? C1A C8A C15A C14A -66(2) . . . . ? O3A C8A C15A C11A 84.6(18) . . . . ? C9A C8A C15A C11A -31.9(15) . . . . ? C1A C8A C15A C11A -150.5(19) . . . . ? C13A C14A C15A C8A -46.3(19) . . . . ? C13A C14A C15A C11A 36.4(16) . . . . ? C12A C11A C15A C8A 107(2) . . . . ? C9A C11A C15A C8A 28.4(14) . . . . ? C12A C11A C15A C14A 1(2) . . . . ? C9A C11A C15A C14A -77.2(14) . . . . ? O3 C8 C9 C13 -125(3) . . . . ? C1 C8 C9 C13 63(4) . . . . ? O3 C8 C9 C10 86(4) . . . . ? C1 C8 C9 C10 -86(3) . . . . ? O3 C8 C9 C11 -31(4) . . . . ? C1 C8 C9 C11 157(2) . . . . ? C13 C9 C11 C15 59(3) . . . . ? C10 C9 C11 C15 -152(4) . . . . ? C8 C9 C11 C15 -54(3) . . . . ? C13 C9 C11 C12 -41(2) . . . . ? C10 C9 C11 C12 108(4) . . . . ? C8 C9 C11 C12 -154(2) . . . . ? C15 C11 C12 C13 -62(3) . . . . ? C9 C11 C12 C13 37(2) . . . . ? C10 C9 C13 C14 164(6) . . . . ? C11 C9 C13 C14 -62(3) . . . . ? C8 C9 C13 C14 36(3) . . . . ? C10 C9 C13 C12 -95(6) . . . . ? C11 C9 C13 C12 38(2) . . . . ? C8 C9 C13 C12 137(3) . . . . ? C11 C12 C13 C14 51(3) . . . . ? C11 C12 C13 C9 -40(3) . . . . ? C9 C13 C14 C15 51(4) . . . . ? C12 C13 C14 C15 -26(4) . . . . ? O3 C8 C1 C2 179.4(17) . . . . ? C9 C8 C1 C2 -7(3) . . . . ? O3 C8 C1 C6 -1(3) . . . . ? C9 C8 C1 C6 172(2) . . . . ? C6 C1 C2 C3 0.0 . . . . ? C8 C1 C2 C3 179.8(18) . . . . ? C1 C2 C3 C4 0.0 . . . . ? C2 C3 C4 C5 0.0 . . . . ? C2 C3 C4 C7 -173.0(16) . . . . ? C3 C4 C5 C6 0.0 . . . . ? C7 C4 C5 C6 172.9(16) . . . . ? C4 C5 C6 C1 0.0 . . . . ? C2 C1 C6 C5 0.0 . . . . ? C8 C1 C6 C5 -179.8(19) . . . . ? C5 C4 C7 O1 141.3(18) . . . . ? C3 C4 C7 O1 -46(3) . . . . ? C5 C4 C7 O2 -36(3) . . . . ? C3 C4 C7 O2 137.2(19) . . . . ? C13 C14 C15 C11 -13(5) . . . . ? C12 C11 C15 C14 50(4) . . . . ? C9 C11 C15 C14 -28(4) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 22.43 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.368 _refine_diff_density_min -0.352 _refine_diff_density_rms 0.073