# Electronic Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is (c) The Royal Society of Chemistry and Owner Societies 2011 data_global _journal_name_full Photochem.Photobiol.Sci. _journal_coden_cambridge 0171 #TrackingRef 'PPS-Final-cif-File.cif' _audit_creation_method 'APEX2 v2010.5-0' _publ_contact_author_name 'Sivaguru Jayaraman' _publ_contact_author_address ; ; _publ_contact_author_email Sivaguru.Jayaraman@ndsu.edu _publ_contact_author_fax '701 231-8831' _publ_contact_author_phone '701 231-8923' loop_ _publ_author_name _publ_author_address 'Anoklase Ayitou' ; Dunbar Hall Department of Chemistry and Biochemistry North Dakota State University Fargo, ND 58108 USA ; 'Nandini Vallavoju' ; Dunbar Hall Department of Chemistry and Biochemistry North Dakota State University Fargo, ND 58108-6050 USA ; 'Sivaguru Jayaraman' ; Ladd Hall Department of Chemistry and Biochemistry North Dakota State University Fargo, ND 58108 USA ; 'Angel Ugrinov' ; Dunbar Hall Department of Chemistry and Biochemistry North Dakota State University Fargo, ND 58108 USA ; _publ_section_title ; Enantiospecific 6 -Photocyclization of Atropisomeric -substituted Acrylanilides In the Solid-State: Role of Crystalline Confinement on Enantiospecificity. ; _publ_section_abstract ; Direct irradiation of optically pure axially chiral -substituted acrylanilides in the crystalline state leads to dihydro-2-quinolin-2-one photoproduct with an enantiomeric ratio of 85:15 while, racemic mixture of photoproduct is observed in solution. ; _publ_section_references ; ; _publ_section_comment ; ; _publ_requested_category FO data_1c _database_code_depnum_ccdc_archive 'CCDC 810246' #TrackingRef 'PPS-Final-cif-File.cif' _audit_creation_date 2010-01-17T12:29:33-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.4 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_sum 'C17 H25 N O' _chemical_formula_weight 259.38 _chemical_absolute_configuration unk #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 8.7219(13) _cell_length_b 14.862(2) _cell_length_c 12.6513(18) _cell_angle_alpha 90 _cell_angle_beta 99.836(2) _cell_angle_gamma 90 _cell_volume 1615.8(4) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3931 _cell_measurement_theta_min 2.74 _cell_measurement_theta_max 26.04 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.4 _exptl_crystal_size_min 0.22 _exptl_crystal_density_diffrn 1.066 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 568 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.065 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.78531 _exptl_absorpt_correction_T_max 1 #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_reflns_av_R_equivalents 0.0197 _diffrn_reflns_av_unetI/netI 0.0255 _diffrn_reflns_number 6999 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 27.03 _diffrn_reflns_theta_full 27.03 _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _reflns_number_total 3366 _reflns_number_gt 2910 _reflns_threshold_expression >2\s(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' #----------------------------------------------------------------------------# # STRUCTURE SOLUTION #----------------------------------------------------------------------------# _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _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^ > 2\s(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^)+(0.0782P)^2^+0.1202P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 3366 _refine_ls_number_parameters 172 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0497 _refine_ls_R_factor_gt 0.0416 _refine_ls_wR_factor_ref 0.1215 _refine_ls_wR_factor_gt 0.1134 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -1.0(16) _refine_diff_density_max 0.141 _refine_diff_density_min -0.167 _refine_diff_density_rms 0.037 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 N001 N 0.59879(14) 0.32564(9) 0.80540(11) 0.0474(3) Uani 1 1 d . . . O002 O 0.37247(16) 0.39676(10) 0.74877(13) 0.0751(4) Uani 1 1 d . . . C003 C 0.87706(17) 0.32989(9) 0.77894(11) 0.0426(3) Uani 1 1 d . . . C004 C 0.7358(2) 0.18952(10) 0.78077(15) 0.0582(4) Uani 1 1 d . . . H004 H 0.6445 0.1598 0.7885 0.07 Uiso 1 1 calc R . . C005 C 0.49221(19) 0.36316(11) 0.72693(14) 0.0524(4) Uani 1 1 d . . . C006 C 0.74080(17) 0.28354(9) 0.78749(12) 0.0432(3) Uani 1 1 d . . . C007 C 0.90966(19) 0.43187(10) 0.78825(15) 0.0555(4) Uani 1 1 d . . . C008 C 1.00277(19) 0.27658(12) 0.75948(13) 0.0550(4) Uani 1 1 d . . . H008 H 1.0952 0.305 0.7517 0.066 Uiso 1 1 calc R . . C009 C 0.9947(2) 0.18434(13) 0.75145(15) 0.0646(5) Uani 1 1 d . . . H009 H 1.0806 0.152 0.7379 0.078 Uiso 1 1 calc R . . C010 C 0.5174(2) 0.36687(13) 0.61269(16) 0.0615(4) Uani 1 1 d . . . C011 C 0.7767(2) 0.49129(12) 0.8130(2) 0.0827(7) Uani 1 1 d . . . H01A H 0.6872 0.4837 0.7579 0.124 Uiso 1 1 calc R . . H01B H 0.8086 0.5532 0.8155 0.124 Uiso 1 1 calc R . . H01C H 0.7508 0.4743 0.881 0.124 Uiso 1 1 calc R . . C012 C 1.0496(2) 0.44766(15) 0.87911(19) 0.0715(5) Uani 1 1 d . . . H01D H 1.0715 0.5109 0.8857 0.107 Uiso 1 1 calc R . . H01E H 1.1391 0.4165 0.8626 0.107 Uiso 1 1 calc R . . H01F H 1.0252 0.4253 0.9455 0.107 Uiso 1 1 calc R . . C013 C 0.8617(3) 0.13984(11) 0.76316(15) 0.0661(5) Uani 1 1 d . . . H013 H 0.8566 0.0774 0.7593 0.079 Uiso 1 1 calc R . . C014 C 0.4400(3) 0.24812(18) 0.9249(2) 0.0909(7) Uani 1 1 d . . . H01G H 0.3507 0.256 0.8696 0.136 Uiso 1 1 calc R . . H01H H 0.4085 0.2515 0.9939 0.136 Uiso 1 1 calc R . . H01I H 0.486 0.1904 0.9168 0.136 Uiso 1 1 calc R . . C015 C 0.5580(2) 0.32161(14) 0.91581(14) 0.0619(5) Uani 1 1 d . . . H015 H 0.5089 0.3791 0.9282 0.074 Uiso 1 1 calc R . . C016 C 0.7002(3) 0.3121(2) 1.00146(17) 0.0883(7) Uani 1 1 d . . . H01J H 0.7722 0.3596 0.9941 0.132 Uiso 1 1 calc R . . H01K H 0.7486 0.255 0.9939 0.132 Uiso 1 1 calc R . . H01L H 0.6701 0.3156 1.0709 0.132 Uiso 1 1 calc R . . C017 C 0.9548(3) 0.46463(15) 0.6814(2) 0.0862(7) Uani 1 1 d . . . H012 H 0.8693 0.4549 0.6239 0.129 Uiso 1 1 calc R . . H023 H 1.0439 0.4316 0.6675 0.129 Uiso 1 1 calc R . . H024 H 0.9793 0.5276 0.6866 0.129 Uiso 1 1 calc R . . C018 C 0.5742(3) 0.3005(2) 0.56137(18) 0.0883(7) Uani 1 1 d . . . H025 H 0.5745 0.305 0.4881 0.106 Uiso 1 1 calc R . . H016 H 0.6139 0.2493 0.5986 0.106 Uiso 1 1 calc R . . C019 C 0.4527(4) 0.45013(19) 0.5550(2) 0.1061(10) Uani 1 1 d . . . H017 H 0.4168 0.4904 0.6048 0.159 Uiso 1 1 calc R . . H018 H 0.3673 0.4343 0.4996 0.159 Uiso 1 1 calc R . . H019 H 0.5324 0.4791 0.5235 0.159 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 N001 0.0383(6) 0.0492(7) 0.0567(7) -0.0068(6) 0.0139(5) 0.0001(5) O002 0.0475(7) 0.0860(9) 0.0952(10) 0.0102(7) 0.0215(6) 0.0175(7) C003 0.0394(7) 0.0436(7) 0.0455(7) 0.0004(6) 0.0091(6) 0.0058(6) C004 0.0657(11) 0.0421(8) 0.0692(10) -0.0030(7) 0.0183(8) -0.0020(8) C005 0.0396(8) 0.0489(8) 0.0690(10) -0.0036(7) 0.0101(7) -0.0027(6) C006 0.0426(7) 0.0398(7) 0.0485(7) -0.0049(6) 0.0118(6) 0.0028(6) C007 0.0433(9) 0.0460(8) 0.0756(11) 0.0022(8) 0.0052(7) -0.0044(6) C008 0.0449(9) 0.0681(10) 0.0545(9) 0.0076(8) 0.0160(7) 0.0142(8) C009 0.0727(13) 0.0630(11) 0.0623(10) 0.0057(8) 0.0236(9) 0.0330(10) C010 0.0507(9) 0.0667(11) 0.0642(10) -0.0047(8) 0.0012(7) -0.0061(8) C011 0.0520(11) 0.0420(8) 0.149(2) -0.0191(11) 0.0015(12) 0.0017(7) C012 0.0550(10) 0.0681(11) 0.0874(14) -0.0098(10) 0.0012(9) -0.0101(9) C013 0.0959(15) 0.0393(7) 0.0657(10) -0.0013(7) 0.0211(9) 0.0156(9) C014 0.0756(14) 0.1068(18) 0.0977(17) 0.0210(14) 0.0357(12) -0.0096(13) C015 0.0527(10) 0.0759(11) 0.0626(10) -0.0045(9) 0.0252(8) 0.0035(8) C016 0.0727(14) 0.136(2) 0.0583(11) -0.0095(12) 0.0178(10) 0.0025(13) C017 0.0921(16) 0.0704(12) 0.0929(15) 0.0258(12) 0.0068(12) -0.0206(12) C018 0.0831(15) 0.1170(19) 0.0597(11) -0.0164(11) -0.0027(10) 0.0230(14) C019 0.158(3) 0.0845(16) 0.0731(15) 0.0144(12) 0.0121(16) 0.0094(17) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All s.u.'s (except the s.u. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell s.u.'s are taken into account individually in the estimation of s.u.'s in distances, angles and torsion angles; correlations between s.u.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell s.u.'s is used for estimating s.u.'s 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 N001 C005 1.358(2) . ? N001 C006 1.4397(19) . ? N001 C015 1.500(2) . ? O002 C005 1.231(2) . ? C003 C006 1.394(2) . ? C003 C008 1.408(2) . ? C003 C007 1.543(2) . ? C004 C013 1.373(3) . ? C004 C006 1.400(2) . ? C004 H004 0.93 . ? C005 C010 1.499(3) . ? C007 C011 1.532(3) . ? C007 C012 1.545(3) . ? C007 C017 1.550(3) . ? C008 C009 1.375(3) . ? C008 H008 0.93 . ? C009 C013 1.365(3) . ? C009 H009 0.93 . ? C010 C018 1.324(3) . ? C010 C019 1.497(3) . ? C011 H01A 0.96 . ? C011 H01B 0.96 . ? C011 H01C 0.96 . ? C012 H01D 0.96 . ? C012 H01E 0.96 . ? C012 H01F 0.96 . ? C013 H013 0.93 . ? C014 C015 1.519(3) . ? C014 H01G 0.96 . ? C014 H01H 0.96 . ? C014 H01I 0.96 . ? C015 C016 1.508(3) . ? C015 H015 0.98 . ? C016 H01J 0.96 . ? C016 H01K 0.96 . ? C016 H01L 0.96 . ? C017 H012 0.96 . ? C017 H023 0.96 . ? C017 H024 0.96 . ? C018 H025 0.93 . ? C018 H016 0.93 . ? C019 H017 0.96 . ? C019 H018 0.96 . ? C019 H019 0.96 . ? 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 C005 N001 C006 124.27(13) . . ? C005 N001 C015 117.08(13) . . ? C006 N001 C015 118.45(13) . . ? C006 C003 C008 115.80(13) . . ? C006 C003 C007 128.91(13) . . ? C008 C003 C007 115.30(14) . . ? C013 C004 C006 121.94(16) . . ? C013 C004 H004 119 . . ? C006 C004 H004 119 . . ? O002 C005 N001 120.23(15) . . ? O002 C005 C010 118.09(15) . . ? N001 C005 C010 121.67(14) . . ? C003 C006 C004 120.44(14) . . ? C003 C006 N001 124.43(12) . . ? C004 C006 N001 115.11(14) . . ? C011 C007 C003 116.47(14) . . ? C011 C007 C012 106.87(16) . . ? C003 C007 C012 108.53(14) . . ? C011 C007 C017 108.12(18) . . ? C003 C007 C017 108.24(15) . . ? C012 C007 C017 108.36(16) . . ? C009 C008 C003 122.84(16) . . ? C009 C008 H008 118.6 . . ? C003 C008 H008 118.6 . . ? C013 C009 C008 120.55(16) . . ? C013 C009 H009 119.7 . . ? C008 C009 H009 119.7 . . ? C018 C010 C019 121.2(2) . . ? C018 C010 C005 125.0(2) . . ? C019 C010 C005 113.29(19) . . ? C007 C011 H01A 109.5 . . ? C007 C011 H01B 109.5 . . ? H01A C011 H01B 109.5 . . ? C007 C011 H01C 109.5 . . ? H01A C011 H01C 109.5 . . ? H01B C011 H01C 109.5 . . ? C007 C012 H01D 109.5 . . ? C007 C012 H01E 109.5 . . ? H01D C012 H01E 109.5 . . ? C007 C012 H01F 109.5 . . ? H01D C012 H01F 109.5 . . ? H01E C012 H01F 109.5 . . ? C009 C013 C004 118.38(14) . . ? C009 C013 H013 120.8 . . ? C004 C013 H013 120.8 . . ? C015 C014 H01G 109.5 . . ? C015 C014 H01H 109.5 . . ? H01G C014 H01H 109.5 . . ? C015 C014 H01I 109.5 . . ? H01G C014 H01I 109.5 . . ? H01H C014 H01I 109.5 . . ? N001 C015 C016 112.10(13) . . ? N001 C015 C014 111.75(17) . . ? C016 C015 C014 111.3(2) . . ? N001 C015 H015 107.1 . . ? C016 C015 H015 107.1 . . ? C014 C015 H015 107.1 . . ? C015 C016 H01J 109.5 . . ? C015 C016 H01K 109.5 . . ? H01J C016 H01K 109.5 . . ? C015 C016 H01L 109.5 . . ? H01J C016 H01L 109.5 . . ? H01K C016 H01L 109.5 . . ? C007 C017 H012 109.5 . . ? C007 C017 H023 109.5 . . ? H012 C017 H023 109.5 . . ? C007 C017 H024 109.5 . . ? H012 C017 H024 109.5 . . ? H023 C017 H024 109.5 . . ? C010 C018 H025 120 . . ? C010 C018 H016 120 . . ? H025 C018 H016 120 . . ? C010 C019 H017 109.5 . . ? C010 C019 H018 109.5 . . ? H017 C019 H018 109.5 . . ? C010 C019 H019 109.5 . . ? H017 C019 H019 109.5 . . ? H018 C019 H019 109.5 . . ? #===END data_1d _database_code_depnum_ccdc_archive 'CCDC 810247' #TrackingRef 'PPS-Final-cif-File.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H27 N O' _chemical_formula_sum 'C19 H27 N O' _chemical_formula_weight 285.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c _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 11.2894(3) _cell_length_b 8.7386(2) _cell_length_c 17.1678(4) _cell_angle_alpha 90.00 _cell_angle_beta 105.6230(10) _cell_angle_gamma 90.00 _cell_volume 1631.09(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9863 _cell_measurement_theta_min 4.07 _cell_measurement_theta_max 67.31 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max .108 _exptl_crystal_size_mid .089 _exptl_crystal_size_min .058 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.162 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 624 _exptl_absorpt_coefficient_mu 0.540 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6897 _exptl_absorpt_correction_T_max 0.7530 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 21695 _diffrn_reflns_av_R_equivalents 0.0262 _diffrn_reflns_av_sigmaI/netI 0.0166 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.07 _diffrn_reflns_theta_max 68.07 _reflns_number_total 2899 _reflns_number_gt 2788 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0437P)^2^+0.6553P] 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 2899 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0371 _refine_ls_R_factor_gt 0.0360 _refine_ls_wR_factor_ref 0.0920 _refine_ls_wR_factor_gt 0.0911 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _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 O1 O 0.59840(7) 0.67337(9) 0.22645(5) 0.0242(2) Uani 1 1 d . . . N1 N 0.69744(8) 0.89992(10) 0.23239(5) 0.0186(2) Uani 1 1 d . . . C1 C 0.45212(13) 0.94085(16) 0.09538(9) 0.0407(3) Uani 1 1 d . . . H1A H 0.3944 0.9503 0.0439 0.049 Uiso 1 1 calc R . . H1B H 0.4516 1.0125 0.1369 0.049 Uiso 1 1 calc R . . C2 C 0.53444(10) 0.82626(13) 0.10944(7) 0.0245(3) Uani 1 1 d . . . C3 C 0.61298(10) 0.79524(12) 0.19373(6) 0.0197(2) Uani 1 1 d . . . C4 C 0.72117(10) 1.04256(12) 0.19691(6) 0.0191(2) Uani 1 1 d . . . C5 C 0.80600(10) 1.05769(12) 0.15042(6) 0.0195(2) Uani 1 1 d . . . C6 C 0.88944(10) 0.93370(13) 0.12827(7) 0.0211(2) Uani 1 1 d . . . C7 C 0.85789(11) 0.91835(14) 0.03564(7) 0.0256(3) Uani 1 1 d . . . H7A H 0.9143 0.8453 0.0212 0.038 Uiso 1 1 calc R . . H7B H 0.8661 1.0183 0.0117 0.038 Uiso 1 1 calc R . . H7C H 0.7732 0.8817 0.0150 0.038 Uiso 1 1 calc R . . C8 C 1.02463(10) 0.98556(14) 0.15969(7) 0.0272(3) Uani 1 1 d . . . H8A H 1.0455 0.9978 0.2186 0.041 Uiso 1 1 calc R . . H8B H 1.0356 1.0834 0.1347 0.041 Uiso 1 1 calc R . . H8C H 1.0785 0.9084 0.1458 0.041 Uiso 1 1 calc R . . C9 C 0.88238(11) 0.77349(13) 0.16325(7) 0.0253(3) Uani 1 1 d . . . H9A H 0.7987 0.7334 0.1428 0.038 Uiso 1 1 calc R . . H9B H 0.9037 0.7794 0.2224 0.038 Uiso 1 1 calc R . . H9C H 0.9403 0.7053 0.1469 0.038 Uiso 1 1 calc R . . C10 C 0.81903(10) 1.20641(13) 0.12241(7) 0.0232(3) Uani 1 1 d . . . H10 H 0.8721 1.2208 0.0885 0.028 Uiso 1 1 calc R . . C11 C 0.75892(11) 1.33235(13) 0.14159(7) 0.0252(3) Uani 1 1 d . . . H11 H 0.7728 1.4307 0.1222 0.030 Uiso 1 1 calc R . . C12 C 0.67812(11) 1.31544(13) 0.18919(7) 0.0248(3) Uani 1 1 d . . . H12 H 0.6368 1.4014 0.2034 0.030 Uiso 1 1 calc R . . C13 C 0.65921(10) 1.17035(13) 0.21545(7) 0.0228(2) Uani 1 1 d . . . H13 H 0.6026 1.1570 0.2470 0.027 Uiso 1 1 calc R . . C14 C 0.75921(10) 0.86748(13) 0.31891(6) 0.0214(2) Uani 1 1 d . . . H14 H 0.7813 0.7564 0.3243 0.026 Uiso 1 1 calc R . . C15 C 0.67464(11) 0.90255(14) 0.37459(7) 0.0260(3) Uani 1 1 d . . . H15A H 0.6029 0.9643 0.3454 0.031 Uiso 1 1 calc R . . H15B H 0.6446 0.8064 0.3932 0.031 Uiso 1 1 calc R . . C16 C 0.75411(12) 0.99211(15) 0.44644(7) 0.0301(3) Uani 1 1 d . . . H16A H 0.7034 1.0637 0.4685 0.036 Uiso 1 1 calc R . . H16B H 0.7980 0.9220 0.4900 0.036 Uiso 1 1 calc R . . C17 C 0.84409(12) 1.07847(15) 0.41084(8) 0.0311(3) Uani 1 1 d . . . H17A H 0.9178 1.1102 0.4536 0.037 Uiso 1 1 calc R . . H17B H 0.8051 1.1703 0.3808 0.037 Uiso 1 1 calc R . . C18 C 0.87714(10) 0.96179(14) 0.35404(7) 0.0254(3) Uani 1 1 d . . . H18A H 0.9449 0.8948 0.3840 0.031 Uiso 1 1 calc R . . H18B H 0.9032 1.0141 0.3102 0.031 Uiso 1 1 calc R . . C19 C 0.54080(12) 0.71043(16) 0.04782(7) 0.0326(3) Uani 1 1 d . . . H19A H 0.4778 0.7325 -0.0026 0.049 Uiso 1 1 calc R . . H19B H 0.5265 0.6085 0.0673 0.049 Uiso 1 1 calc R . . H19C H 0.6223 0.7136 0.0379 0.049 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 O1 0.0280(4) 0.0186(4) 0.0281(4) 0.0010(3) 0.0110(3) -0.0022(3) N1 0.0196(5) 0.0176(5) 0.0194(5) 0.0011(3) 0.0069(4) -0.0002(3) C1 0.0369(7) 0.0365(7) 0.0393(7) -0.0022(6) -0.0061(6) 0.0043(6) C2 0.0224(6) 0.0252(6) 0.0254(6) 0.0010(5) 0.0057(5) -0.0049(4) C3 0.0192(5) 0.0188(5) 0.0235(6) -0.0018(4) 0.0099(4) 0.0011(4) C4 0.0197(5) 0.0177(5) 0.0192(5) 0.0007(4) 0.0042(4) -0.0008(4) C5 0.0189(5) 0.0202(5) 0.0186(5) -0.0004(4) 0.0037(4) -0.0010(4) C6 0.0203(5) 0.0222(6) 0.0222(6) -0.0004(4) 0.0083(4) 0.0000(4) C7 0.0275(6) 0.0271(6) 0.0239(6) -0.0025(5) 0.0096(5) 0.0000(5) C8 0.0213(6) 0.0317(6) 0.0294(6) -0.0039(5) 0.0080(5) -0.0009(5) C9 0.0269(6) 0.0222(6) 0.0303(6) 0.0013(5) 0.0136(5) 0.0054(5) C10 0.0251(6) 0.0237(6) 0.0216(5) 0.0011(4) 0.0077(4) -0.0039(4) C11 0.0309(6) 0.0177(5) 0.0246(6) 0.0029(4) 0.0033(5) -0.0026(5) C12 0.0270(6) 0.0199(6) 0.0261(6) -0.0011(4) 0.0047(5) 0.0037(4) C13 0.0226(6) 0.0226(6) 0.0242(6) -0.0005(4) 0.0078(5) 0.0014(4) C14 0.0227(5) 0.0215(5) 0.0203(5) 0.0019(4) 0.0063(4) 0.0008(4) C15 0.0268(6) 0.0313(6) 0.0222(6) 0.0006(5) 0.0105(5) -0.0031(5) C16 0.0337(7) 0.0328(7) 0.0255(6) -0.0033(5) 0.0109(5) -0.0004(5) C17 0.0337(7) 0.0308(7) 0.0280(6) -0.0037(5) 0.0068(5) -0.0054(5) C18 0.0221(6) 0.0309(6) 0.0233(6) 0.0003(5) 0.0060(5) -0.0020(5) C19 0.0284(6) 0.0434(8) 0.0262(6) -0.0067(5) 0.0075(5) -0.0060(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 O1 C3 1.2356(13) . ? N1 C3 1.3585(14) . ? N1 C4 1.4438(13) . ? N1 C14 1.4883(13) . ? C1 C2 1.3432(18) . ? C1 H1A 0.9500 . ? C1 H1B 0.9500 . ? C2 C19 1.4798(17) . ? C2 C3 1.5041(16) . ? C4 C13 1.3991(15) . ? C4 C5 1.4083(15) . ? C5 C10 1.4070(15) . ? C5 C6 1.5489(15) . ? C6 C9 1.5339(15) . ? C6 C7 1.5390(15) . ? C6 C8 1.5434(16) . ? C7 H7A 0.9800 . ? C7 H7B 0.9800 . ? C7 H7C 0.9800 . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.3787(17) . ? C10 H10 0.9500 . ? C11 C12 1.3867(17) . ? C11 H11 0.9500 . ? C12 C13 1.3813(16) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C18 1.5437(16) . ? C14 C15 1.5527(15) . ? C14 H14 1.0000 . ? C15 C16 1.5306(17) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.5196(17) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.5251(17) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9800 . ? C19 H19B 0.9800 . ? C19 H19C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 N1 C4 124.10(9) . . ? C3 N1 C14 115.98(9) . . ? C4 N1 C14 119.68(8) . . ? C2 C1 H1A 120.0 . . ? C2 C1 H1B 120.0 . . ? H1A C1 H1B 120.0 . . ? C1 C2 C19 123.08(12) . . ? C1 C2 C3 120.49(11) . . ? C19 C2 C3 115.79(10) . . ? O1 C3 N1 121.34(10) . . ? O1 C3 C2 118.46(10) . . ? N1 C3 C2 120.20(9) . . ? C13 C4 C5 120.79(10) . . ? C13 C4 N1 115.61(9) . . ? C5 C4 N1 123.50(9) . . ? C10 C5 C4 115.47(10) . . ? C10 C5 C6 115.83(9) . . ? C4 C5 C6 128.67(10) . . ? C9 C6 C7 107.64(9) . . ? C9 C6 C8 106.37(9) . . ? C7 C6 C8 108.58(9) . . ? C9 C6 C5 116.31(9) . . ? C7 C6 C5 109.13(9) . . ? C8 C6 C5 108.56(9) . . ? C6 C7 H7A 109.5 . . ? C6 C7 H7B 109.5 . . ? H7A C7 H7B 109.5 . . ? C6 C7 H7C 109.5 . . ? H7A C7 H7C 109.5 . . ? H7B C7 H7C 109.5 . . ? C6 C8 H8A 109.5 . . ? C6 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C6 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C6 C9 H9A 109.5 . . ? C6 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C6 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C5 123.52(10) . . ? C11 C10 H10 118.2 . . ? C5 C10 H10 118.2 . . ? C10 C11 C12 119.99(10) . . ? C10 C11 H11 120.0 . . ? C12 C11 H11 120.0 . . ? C13 C12 C11 118.31(10) . . ? C13 C12 H12 120.8 . . ? C11 C12 H12 120.8 . . ? C12 C13 C4 121.85(10) . . ? C12 C13 H13 119.1 . . ? C4 C13 H13 119.1 . . ? N1 C14 C18 114.28(9) . . ? N1 C14 C15 112.10(9) . . ? C18 C14 C15 105.23(9) . . ? N1 C14 H14 108.3 . . ? C18 C14 H14 108.3 . . ? C15 C14 H14 108.3 . . ? C16 C15 C14 105.83(9) . . ? C16 C15 H15A 110.6 . . ? C14 C15 H15A 110.6 . . ? C16 C15 H15B 110.6 . . ? C14 C15 H15B 110.6 . . ? H15A C15 H15B 108.7 . . ? C17 C16 C15 103.89(9) . . ? C17 C16 H16A 111.0 . . ? C15 C16 H16A 111.0 . . ? C17 C16 H16B 111.0 . . ? C15 C16 H16B 111.0 . . ? H16A C16 H16B 109.0 . . ? C16 C17 C18 103.31(10) . . ? C16 C17 H17A 111.1 . . ? C18 C17 H17A 111.1 . . ? C16 C17 H17B 111.1 . . ? C18 C17 H17B 111.1 . . ? H17A C17 H17B 109.1 . . ? C17 C18 C14 105.84(9) . . ? C17 C18 H18A 110.6 . . ? C14 C18 H18A 110.6 . . ? C17 C18 H18B 110.6 . . ? C14 C18 H18B 110.6 . . ? H18A C18 H18B 108.7 . . ? C2 C19 H19A 109.5 . . ? C2 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? C2 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? _diffrn_measured_fraction_theta_max 0.971 _diffrn_reflns_theta_full 68.07 _diffrn_measured_fraction_theta_full 0.971 _refine_diff_density_max 0.258 _refine_diff_density_min -0.183 _refine_diff_density_rms 0.033 #===END data_(-)-1e_or_M-1e _database_code_depnum_ccdc_archive 'CCDC 810248' #TrackingRef 'PPS-Final-cif-File.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H29 N O' _chemical_formula_sum 'C20 H29 N O' _chemical_formula_weight 299.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _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 8.7688(10) _cell_length_b 11.3647(14) _cell_length_c 17.512(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1745.2(4) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9963 _cell_measurement_theta_min 4.64 _cell_measurement_theta_max 66.24 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.140 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.526 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6992 _exptl_absorpt_correction_T_max 0.7528 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 13484 _diffrn_reflns_av_R_equivalents 0.0190 _diffrn_reflns_av_sigmaI/netI 0.0150 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.64 _diffrn_reflns_theta_max 66.63 _reflns_number_total 3004 _reflns_number_gt 2953 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0466P)^2^+0.2206P] 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 0.1(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 3004 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0266 _refine_ls_R_factor_gt 0.0261 _refine_ls_wR_factor_ref 0.0705 _refine_ls_wR_factor_gt 0.0701 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _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 O1 O 0.07429(9) 0.16582(7) 0.78598(5) 0.02534(19) Uani 1 1 d . . . N1 N 0.29747(10) 0.10673(8) 0.83753(5) 0.01766(19) Uani 1 1 d . . . C1 C 0.37542(13) 0.38861(10) 1.00042(6) 0.0234(2) Uani 1 1 d . . . H1A H 0.3498 0.4480 1.0398 0.028 Uiso 1 1 calc R . . H1B H 0.4860 0.3945 0.9896 0.028 Uiso 1 1 calc R . . C2 C 0.33902(13) 0.26580(10) 1.03080(6) 0.0218(2) Uani 1 1 d . . . H2A H 0.2307 0.2626 1.0466 0.026 Uiso 1 1 calc R . . H2B H 0.4027 0.2497 1.0763 0.026 Uiso 1 1 calc R . . C3 C 0.36877(13) 0.17113(10) 0.97030(6) 0.0205(2) Uani 1 1 d . . . H3A H 0.4789 0.1687 0.9580 0.025 Uiso 1 1 calc R . . H3B H 0.3389 0.0931 0.9906 0.025 Uiso 1 1 calc R . . C4 C 0.27772(12) 0.19767(9) 0.89812(6) 0.0180(2) Uani 1 1 d . . . H4 H 0.1674 0.1981 0.9126 0.022 Uiso 1 1 calc R . . C5 C 0.42876(12) 0.03014(10) 0.83990(6) 0.0186(2) Uani 1 1 d . . . C6 C 0.42295(12) -0.08780(9) 0.86371(6) 0.0194(2) Uani 1 1 d . . . C7 C 0.28386(13) -0.15768(10) 0.89381(6) 0.0220(2) Uani 1 1 d . . . C8 C 0.24798(15) -0.25739(11) 0.83700(8) 0.0302(3) Uani 1 1 d . . . H8A H 0.1596 -0.3021 0.8552 0.045 Uiso 1 1 calc R . . H8B H 0.3363 -0.3098 0.8329 0.045 Uiso 1 1 calc R . . H8C H 0.2252 -0.2236 0.7868 0.045 Uiso 1 1 calc R . . C9 C 0.13633(14) -0.08842(11) 0.90592(7) 0.0269(3) Uani 1 1 d . . . H9A H 0.0605 -0.1390 0.9307 0.040 Uiso 1 1 calc R . . H9B H 0.0970 -0.0619 0.8565 0.040 Uiso 1 1 calc R . . H9C H 0.1569 -0.0200 0.9384 0.040 Uiso 1 1 calc R . . C10 C 0.32543(16) -0.21176(12) 0.97175(7) 0.0343(3) Uani 1 1 d . . . H10A H 0.3497 -0.1488 1.0080 0.052 Uiso 1 1 calc R . . H10B H 0.4142 -0.2634 0.9659 0.052 Uiso 1 1 calc R . . H10C H 0.2389 -0.2575 0.9910 0.052 Uiso 1 1 calc R . . C11 C 0.28589(14) 0.41436(10) 0.92789(7) 0.0245(2) Uani 1 1 d . . . H11A H 0.3158 0.4924 0.9077 0.029 Uiso 1 1 calc R . . H11B H 0.1756 0.4167 0.9398 0.029 Uiso 1 1 calc R . . C12 C 0.31593(13) 0.32041(9) 0.86747(6) 0.0219(2) Uani 1 1 d . . . H12A H 0.4245 0.3230 0.8521 0.026 Uiso 1 1 calc R . . H12B H 0.2531 0.3368 0.8217 0.026 Uiso 1 1 calc R . . C13 C 0.18908(12) 0.10374(9) 0.78214(6) 0.0195(2) Uani 1 1 d . . . C14 C 0.20596(13) 0.02424(10) 0.71327(6) 0.0219(2) Uani 1 1 d . . . C15 C 0.05993(14) -0.03269(11) 0.68805(7) 0.0291(3) Uani 1 1 d . . . H15A H 0.0739 -0.0673 0.6373 0.044 Uiso 1 1 calc R . . H15B H -0.0211 0.0266 0.6860 0.044 Uiso 1 1 calc R . . H15C H 0.0317 -0.0945 0.7244 0.044 Uiso 1 1 calc R . . C16 C 0.33325(15) 0.01622(11) 0.67306(6) 0.0281(3) Uani 1 1 d . . . H16A H 0.3343 -0.0267 0.6265 0.034 Uiso 1 1 calc R . . H16B H 0.4236 0.0534 0.6907 0.034 Uiso 1 1 calc R . . C17 C 0.56722(13) 0.08153(10) 0.81890(6) 0.0217(2) Uani 1 1 d . . . H17 H 0.5688 0.1624 0.8051 0.026 Uiso 1 1 calc R . . C18 C 0.70162(13) 0.01867(11) 0.81754(6) 0.0247(3) Uani 1 1 d . . . H18 H 0.7948 0.0553 0.8034 0.030 Uiso 1 1 calc R . . C19 C 0.69712(13) -0.09948(11) 0.83733(6) 0.0260(3) Uani 1 1 d . . . H19 H 0.7875 -0.1455 0.8356 0.031 Uiso 1 1 calc R . . C20 C 0.56118(14) -0.14986(10) 0.85950(6) 0.0241(2) Uani 1 1 d . . . H20 H 0.5610 -0.2310 0.8726 0.029 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 O1 0.0227(4) 0.0250(4) 0.0284(4) -0.0051(3) -0.0054(3) 0.0047(3) N1 0.0173(4) 0.0172(4) 0.0184(4) -0.0018(3) 0.0002(4) 0.0013(4) C1 0.0248(6) 0.0234(6) 0.0222(5) -0.0049(4) -0.0006(4) -0.0016(5) C2 0.0213(5) 0.0253(5) 0.0188(5) -0.0015(4) -0.0017(4) 0.0002(5) C3 0.0215(5) 0.0211(5) 0.0189(5) 0.0010(4) -0.0011(4) 0.0007(4) C4 0.0171(5) 0.0192(5) 0.0178(5) -0.0023(4) 0.0008(4) 0.0009(4) C5 0.0173(5) 0.0228(5) 0.0158(5) -0.0026(4) -0.0010(4) 0.0017(4) C6 0.0190(5) 0.0230(5) 0.0161(5) -0.0023(4) -0.0014(4) 0.0007(5) C7 0.0236(6) 0.0193(5) 0.0231(5) 0.0013(4) 0.0024(5) 0.0004(4) C8 0.0299(6) 0.0225(6) 0.0382(7) -0.0038(5) 0.0016(5) -0.0012(5) C9 0.0238(6) 0.0226(6) 0.0344(6) 0.0013(5) 0.0077(5) -0.0027(5) C10 0.0348(7) 0.0382(7) 0.0301(6) 0.0098(5) 0.0037(6) 0.0021(6) C11 0.0300(6) 0.0191(5) 0.0244(5) -0.0012(4) -0.0008(5) 0.0001(5) C12 0.0262(6) 0.0202(5) 0.0195(5) 0.0003(4) -0.0016(4) -0.0014(5) C13 0.0193(5) 0.0176(5) 0.0215(5) 0.0002(4) -0.0016(4) -0.0003(4) C14 0.0248(6) 0.0200(5) 0.0209(5) -0.0015(4) -0.0045(5) 0.0033(4) C15 0.0257(6) 0.0317(6) 0.0300(6) -0.0098(5) -0.0055(5) 0.0023(5) C16 0.0284(6) 0.0346(6) 0.0212(5) -0.0051(5) -0.0016(5) 0.0008(5) C17 0.0222(5) 0.0245(5) 0.0183(5) -0.0018(4) 0.0006(4) -0.0017(5) C18 0.0179(5) 0.0353(6) 0.0208(5) -0.0050(5) 0.0016(4) -0.0019(5) C19 0.0188(5) 0.0356(6) 0.0235(5) -0.0067(5) -0.0030(5) 0.0084(5) C20 0.0259(6) 0.0246(6) 0.0217(6) -0.0012(4) -0.0017(4) 0.0045(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 O1 C13 1.2311(14) . ? N1 C13 1.3584(14) . ? N1 C5 1.4439(13) . ? N1 C4 1.4914(13) . ? C1 C11 1.5217(16) . ? C1 C2 1.5274(16) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5324(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5252(15) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C12 1.5317(15) . ? C4 H4 1.0000 . ? C5 C17 1.3965(16) . ? C5 C6 1.4046(15) . ? C6 C20 1.4043(16) . ? C6 C7 1.5479(15) . ? C7 C9 1.5291(16) . ? C7 C8 1.5404(16) . ? C7 C10 1.5407(16) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C12 1.5260(15) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.5142(14) . ? C14 C16 1.3229(17) . ? C14 C15 1.5011(16) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? C16 H16A 0.9500 . ? C16 H16B 0.9500 . ? C17 C18 1.3784(16) . ? C17 H17 0.9500 . ? C18 C19 1.3873(18) . ? C18 H18 0.9500 . ? C19 C20 1.3782(18) . ? C19 H19 0.9500 . ? C20 H20 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C13 N1 C5 124.29(8) . . ? C13 N1 C4 116.37(8) . . ? C5 N1 C4 119.34(8) . . ? C11 C1 C2 111.01(9) . . ? C11 C1 H1A 109.4 . . ? C2 C1 H1A 109.4 . . ? C11 C1 H1B 109.4 . . ? C2 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? C1 C2 C3 111.42(9) . . ? C1 C2 H2A 109.3 . . ? C3 C2 H2A 109.3 . . ? C1 C2 H2B 109.3 . . ? C3 C2 H2B 109.3 . . ? H2A C2 H2B 108.0 . . ? C4 C3 C2 110.19(9) . . ? C4 C3 H3A 109.6 . . ? C2 C3 H3A 109.6 . . ? C4 C3 H3B 109.6 . . ? C2 C3 H3B 109.6 . . ? H3A C3 H3B 108.1 . . ? N1 C4 C3 113.07(8) . . ? N1 C4 C12 110.88(8) . . ? C3 C4 C12 110.85(9) . . ? N1 C4 H4 107.2 . . ? C3 C4 H4 107.2 . . ? C12 C4 H4 107.2 . . ? C17 C5 C6 120.58(10) . . ? C17 C5 N1 115.69(9) . . ? C6 C5 N1 123.70(9) . . ? C20 C6 C5 115.62(10) . . ? C20 C6 C7 116.12(9) . . ? C5 C6 C7 128.26(10) . . ? C9 C7 C8 107.19(10) . . ? C9 C7 C10 106.42(10) . . ? C8 C7 C10 109.09(10) . . ? C9 C7 C6 116.73(9) . . ? C8 C7 C6 108.56(9) . . ? C10 C7 C6 108.66(10) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? H8A C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C7 C10 H10A 109.5 . . ? C7 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C7 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C1 C11 C12 110.81(9) . . ? C1 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C1 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C4 110.88(9) . . ? C11 C12 H12A 109.5 . . ? C4 C12 H12A 109.5 . . ? C11 C12 H12B 109.5 . . ? C4 C12 H12B 109.5 . . ? H12A C12 H12B 108.1 . . ? O1 C13 N1 121.25(9) . . ? O1 C13 C14 117.74(9) . . ? N1 C13 C14 121.02(9) . . ? C16 C14 C15 122.24(10) . . ? C16 C14 C13 123.20(10) . . ? C15 C14 C13 114.08(9) . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C14 C16 H16A 120.0 . . ? C14 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? C18 C17 C5 122.09(10) . . ? C18 C17 H17 119.0 . . ? C5 C17 H17 119.0 . . ? C17 C18 C19 118.22(11) . . ? C17 C18 H18 120.9 . . ? C19 C18 H18 120.9 . . ? C20 C19 C18 119.81(11) . . ? C20 C19 H19 120.1 . . ? C18 C19 H19 120.1 . . ? C19 C20 C6 123.55(10) . . ? C19 C20 H20 118.2 . . ? C6 C20 H20 118.2 . . ? _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 66.63 _diffrn_measured_fraction_theta_full 0.985 _refine_diff_density_max 0.147 _refine_diff_density_min -0.149 _refine_diff_density_rms 0.033 #===END data_(+)-1e_or_P-1e _database_code_depnum_ccdc_archive 'CCDC 810249' #TrackingRef 'PPS-Final-cif-File.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H29 N O' _chemical_formula_sum 'C20 H29 N O' _chemical_formula_weight 299.44 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) _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 8.7698(5) _cell_length_b 11.3683(7) _cell_length_c 17.5191(10) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1746.61(18) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9165 _cell_measurement_theta_min 4.64 _cell_measurement_theta_max 67.21 _exptl_crystal_description chunk _exptl_crystal_colour colourless _exptl_crystal_size_max 0.18 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.13 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.139 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 656 _exptl_absorpt_coefficient_mu 0.525 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.6848 _exptl_absorpt_correction_T_max 0.7530 _exptl_absorpt_process_details 'Acta Cryst (1995). A51, 33-38' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11331 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0240 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_theta_min 4.64 _diffrn_reflns_theta_max 67.69 _reflns_number_total 3080 _reflns_number_gt 3033 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0323P)^2^+0.2778P] 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 -0.1(2) _chemical_absolute_configuration ad _refine_ls_number_reflns 3080 _refine_ls_number_parameters 203 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0259 _refine_ls_R_factor_gt 0.0253 _refine_ls_wR_factor_ref 0.0656 _refine_ls_wR_factor_gt 0.0651 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_restrained_S_all 1.064 _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 O1 O 0.07423(9) 0.33411(7) 0.28598(5) 0.02408(18) Uani 1 1 d . . . N1 N 0.29750(9) 0.39322(7) 0.33758(5) 0.01638(18) Uani 1 1 d . . . C1 C 0.37539(13) 0.11144(10) 0.50043(6) 0.0220(2) Uani 1 1 d . . . H1A H 0.4860 0.1055 0.4897 0.026 Uiso 1 1 calc R . . H1B H 0.3496 0.0521 0.5397 0.026 Uiso 1 1 calc R . . C2 C 0.28596(13) 0.08575(9) 0.42788(6) 0.0231(2) Uani 1 1 d . . . H2A H 0.1756 0.0833 0.4398 0.028 Uiso 1 1 calc R . . H2B H 0.3160 0.0078 0.4077 0.028 Uiso 1 1 calc R . . C3 C 0.31580(13) 0.17970(9) 0.36742(6) 0.0203(2) Uani 1 1 d . . . H3A H 0.2529 0.1633 0.3217 0.024 Uiso 1 1 calc R . . H3B H 0.4244 0.1771 0.3520 0.024 Uiso 1 1 calc R . . C4 C 0.27754(11) 0.30226(9) 0.39810(6) 0.0165(2) Uani 1 1 d . . . H4 H 0.1673 0.3019 0.4126 0.020 Uiso 1 1 calc R . . C5 C 0.42874(11) 0.47002(9) 0.33986(6) 0.0173(2) Uani 1 1 d . . . C6 C 0.42296(12) 0.58766(9) 0.36367(6) 0.0183(2) Uani 1 1 d . . . C7 C 0.56141(13) 0.64985(10) 0.35955(6) 0.0228(2) Uani 1 1 d . . . H7 H 0.5612 0.7309 0.3728 0.027 Uiso 1 1 calc R . . C8 C 0.69730(13) 0.59948(11) 0.33735(6) 0.0249(2) Uani 1 1 d . . . H8 H 0.7876 0.6455 0.3356 0.030 Uiso 1 1 calc R . . C9 C 0.32551(15) 0.71172(12) 0.47174(7) 0.0331(3) Uani 1 1 d . . . H9A H 0.2393 0.7580 0.4908 0.050 Uiso 1 1 calc R . . H9B H 0.4147 0.7628 0.4660 0.050 Uiso 1 1 calc R . . H9C H 0.3490 0.6486 0.5080 0.050 Uiso 1 1 calc R . . C10 C 0.28387(12) 0.65776(9) 0.39372(6) 0.0207(2) Uani 1 1 d . . . C11 C 0.24779(14) 0.75731(10) 0.33704(8) 0.0289(3) Uani 1 1 d . . . H11A H 0.2242 0.7235 0.2869 0.043 Uiso 1 1 calc R . . H11B H 0.3363 0.8095 0.3326 0.043 Uiso 1 1 calc R . . H11C H 0.1599 0.8023 0.3555 0.043 Uiso 1 1 calc R . . C12 C 0.70186(12) 0.48129(10) 0.31752(6) 0.0233(2) Uani 1 1 d . . . H12 H 0.7951 0.4447 0.3034 0.028 Uiso 1 1 calc R . . C13 C 0.56730(12) 0.41839(10) 0.31895(6) 0.0202(2) Uani 1 1 d . . . H13 H 0.5689 0.3375 0.3053 0.024 Uiso 1 1 calc R . . C14 C 0.18901(12) 0.39623(9) 0.28208(6) 0.0182(2) Uani 1 1 d . . . C15 C 0.20596(12) 0.47575(9) 0.21332(6) 0.0207(2) Uani 1 1 d . . . C16 C 0.33328(14) 0.48371(11) 0.17295(6) 0.0268(3) Uani 1 1 d . . . H16A H 0.3341 0.5265 0.1264 0.032 Uiso 1 1 calc R . . H16B H 0.4237 0.4466 0.1906 0.032 Uiso 1 1 calc R . . C17 C 0.05999(13) 0.53273(11) 0.18798(7) 0.0278(3) Uani 1 1 d . . . H17A H 0.0745 0.5681 0.1375 0.042 Uiso 1 1 calc R . . H17B H 0.0310 0.5939 0.2246 0.042 Uiso 1 1 calc R . . H17C H -0.0208 0.4733 0.1853 0.042 Uiso 1 1 calc R . . C18 C 0.33911(12) 0.23425(9) 0.53079(6) 0.0205(2) Uani 1 1 d . . . H18A H 0.4029 0.2503 0.5762 0.025 Uiso 1 1 calc R . . H18B H 0.2309 0.2375 0.5467 0.025 Uiso 1 1 calc R . . C19 C 0.36869(12) 0.32883(9) 0.47028(6) 0.0192(2) Uani 1 1 d . . . H19A H 0.3388 0.4068 0.4905 0.023 Uiso 1 1 calc R . . H19B H 0.4788 0.3312 0.4580 0.023 Uiso 1 1 calc R . . C20 C 0.13610(13) 0.58836(10) 0.40591(7) 0.0253(3) Uani 1 1 d . . . H20A H 0.1566 0.5201 0.4385 0.038 Uiso 1 1 calc R . . H20B H 0.0970 0.5615 0.3565 0.038 Uiso 1 1 calc R . . H20C H 0.0602 0.6390 0.4305 0.038 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 O1 0.0189(4) 0.0243(4) 0.0291(4) 0.0052(3) -0.0055(3) -0.0050(3) N1 0.0140(4) 0.0165(4) 0.0186(4) 0.0015(3) -0.0001(4) -0.0010(4) C1 0.0214(5) 0.0224(5) 0.0222(5) 0.0050(4) -0.0008(4) 0.0016(4) C2 0.0264(6) 0.0183(5) 0.0247(5) 0.0010(4) -0.0014(5) -0.0001(4) C3 0.0221(5) 0.0194(5) 0.0195(5) -0.0006(4) -0.0012(4) 0.0011(5) C4 0.0133(5) 0.0183(5) 0.0181(5) 0.0022(4) 0.0009(4) -0.0005(4) C5 0.0142(5) 0.0217(5) 0.0159(5) 0.0028(4) -0.0010(4) -0.0020(4) C6 0.0168(5) 0.0221(5) 0.0161(5) 0.0025(4) -0.0013(4) -0.0006(4) C7 0.0224(6) 0.0239(5) 0.0221(5) 0.0009(4) -0.0013(4) -0.0046(5) C8 0.0161(5) 0.0353(6) 0.0233(5) 0.0066(5) -0.0028(5) -0.0084(5) C9 0.0321(7) 0.0375(7) 0.0299(6) -0.0102(5) 0.0038(5) -0.0020(6) C10 0.0201(6) 0.0183(5) 0.0238(5) -0.0016(4) 0.0023(5) -0.0004(4) C11 0.0269(6) 0.0214(5) 0.0384(7) 0.0039(5) 0.0016(5) 0.0006(5) C12 0.0147(5) 0.0345(6) 0.0208(5) 0.0048(5) 0.0006(4) 0.0017(5) C13 0.0190(5) 0.0237(5) 0.0181(5) 0.0023(4) 0.0005(4) 0.0015(4) C14 0.0164(5) 0.0169(5) 0.0213(5) -0.0005(4) -0.0016(4) 0.0008(4) C15 0.0217(5) 0.0187(5) 0.0218(5) 0.0014(4) -0.0044(5) -0.0032(4) C16 0.0248(6) 0.0339(6) 0.0217(5) 0.0054(5) -0.0017(5) -0.0011(5) C17 0.0226(6) 0.0299(6) 0.0310(6) 0.0100(5) -0.0059(5) -0.0022(5) C18 0.0182(5) 0.0247(5) 0.0186(5) 0.0011(4) -0.0012(4) 0.0001(4) C19 0.0183(5) 0.0199(5) 0.0194(5) -0.0011(4) -0.0010(4) -0.0009(4) C20 0.0204(5) 0.0216(5) 0.0340(6) -0.0011(5) 0.0071(5) 0.0022(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 O1 C14 1.2315(13) . ? N1 C14 1.3606(13) . ? N1 C5 1.4452(13) . ? N1 C4 1.4914(13) . ? C1 C2 1.5219(16) . ? C1 C18 1.5275(15) . ? C1 H1A 0.9900 . ? C1 H1B 0.9900 . ? C2 C3 1.5268(15) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.5306(14) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C19 1.5263(15) . ? C4 H4 1.0000 . ? C5 C13 1.3983(15) . ? C5 C6 1.4018(15) . ? C6 C7 1.4069(15) . ? C6 C10 1.5492(15) . ? C7 C8 1.3782(17) . ? C7 H7 0.9500 . ? C8 C12 1.3884(17) . ? C8 H8 0.9500 . ? C9 C10 1.5419(16) . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C20 1.5322(15) . ? C10 C11 1.5385(16) . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? C12 C13 1.3800(16) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 C15 1.5136(14) . ? C15 C16 1.3248(17) . ? C15 C17 1.5018(15) . ? C16 H16A 0.9500 . ? C16 H16B 0.9500 . ? C17 H17A 0.9800 . ? C17 H17B 0.9800 . ? C17 H17C 0.9800 . ? C18 C19 1.5321(15) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? 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 C14 N1 C5 124.16(8) . . ? C14 N1 C4 116.31(8) . . ? C5 N1 C4 119.52(8) . . ? C2 C1 C18 111.03(9) . . ? C2 C1 H1A 109.4 . . ? C18 C1 H1A 109.4 . . ? C2 C1 H1B 109.4 . . ? C18 C1 H1B 109.4 . . ? H1A C1 H1B 108.0 . . ? C1 C2 C3 110.90(9) . . ? C1 C2 H2A 109.5 . . ? C3 C2 H2A 109.5 . . ? C1 C2 H2B 109.5 . . ? C3 C2 H2B 109.5 . . ? H2A C2 H2B 108.0 . . ? C2 C3 C4 110.83(9) . . ? C2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? C2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? N1 C4 C19 112.98(8) . . ? N1 C4 C3 110.85(8) . . ? C19 C4 C3 110.87(8) . . ? N1 C4 H4 107.3 . . ? C19 C4 H4 107.3 . . ? C3 C4 H4 107.3 . . ? C13 C5 C6 120.65(10) . . ? C13 C5 N1 115.55(9) . . ? C6 C5 N1 123.77(9) . . ? C5 C6 C7 115.65(10) . . ? C5 C6 C10 128.34(9) . . ? C7 C6 C10 116.01(9) . . ? C8 C7 C6 123.50(10) . . ? C8 C7 H7 118.2 . . ? C6 C7 H7 118.2 . . ? C7 C8 C12 119.84(10) . . ? C7 C8 H8 120.1 . . ? C12 C8 H8 120.1 . . ? C10 C9 H9A 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 109.5 . . ? C10 C9 H9C 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C20 C10 C11 107.15(9) . . ? C20 C10 C9 106.35(10) . . ? C11 C10 C9 109.16(10) . . ? C20 C10 C6 116.64(9) . . ? C11 C10 C6 108.72(9) . . ? C9 C10 C6 108.62(9) . . ? 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 . . ? C13 C12 C8 118.18(10) . . ? C13 C12 H12 120.9 . . ? C8 C12 H12 120.9 . . ? C12 C13 C5 122.03(10) . . ? C12 C13 H13 119.0 . . ? C5 C13 H13 119.0 . . ? O1 C14 N1 121.17(9) . . ? O1 C14 C15 117.84(9) . . ? N1 C14 C15 121.00(9) . . ? C16 C15 C17 122.09(10) . . ? C16 C15 C14 123.26(10) . . ? C17 C15 C14 114.15(9) . . ? C15 C16 H16A 120.0 . . ? C15 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? C15 C17 H17A 109.5 . . ? C15 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? C15 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? C1 C18 C19 111.42(9) . . ? C1 C18 H18A 109.3 . . ? C19 C18 H18A 109.3 . . ? C1 C18 H18B 109.3 . . ? C19 C18 H18B 109.3 . . ? H18A C18 H18B 108.0 . . ? C4 C19 C18 110.23(9) . . ? C4 C19 H19A 109.6 . . ? C18 C19 H19A 109.6 . . ? C4 C19 H19B 109.6 . . ? C18 C19 H19B 109.6 . . ? H19A C19 H19B 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 . . ? _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 67.69 _diffrn_measured_fraction_theta_full 0.989 _refine_diff_density_max 0.125 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.030