# Supplementary Material (ESI) for Photochemical & Photobiological Sciences # This journal is (c) The Royal Society of Chemistry and Owner Societies 2009 data_global _journal_coden_Cambridge 171 loop_ _publ_author_name 'Jayaraman Sivaguru' 'Anoklase Jean-Luc Ayitou' 'Angel Ugrinov' _publ_contact_author_name 'Jayaraman Sivaguru' _publ_contact_author_email SIVAGURU.JAYARAMAN@NDSU.EDU _publ_section_title ; ?-Photocyclization O-tert-butylacrylanilides. N-substitution dictates the regiochemistry of cyclization ; # Attachment 'PPS_AA_Xray-Final.cif' data_Structure_4c _database_code_depnum_ccdc_archive 'CCDC 723727' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 N O' _chemical_formula_weight 231.33 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c 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 11.120(16) _cell_length_b 10.165(15) _cell_length_c 12.745(18) _cell_angle_alpha 90.00 _cell_angle_beta 108.04(3) _cell_angle_gamma 90.00 _cell_volume 1370(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 895 _cell_measurement_theta_min 3.54 _cell_measurement_theta_max 24.80 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.76 _exptl_crystal_size_mid 0.52 _exptl_crystal_size_min 0.44 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.122 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 504 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.692683 _exptl_absorpt_correction_T_max 1.000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6779 _diffrn_reflns_av_R_equivalents 0.0575 _diffrn_reflns_av_sigmaI/netI 0.0560 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2388 _reflns_number_gt 1905 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _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^)+(0.1325P)^2^+0.2400P] 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 SHELXL _refine_ls_extinction_coef 0.047(10) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 2388 _refine_ls_number_parameters 155 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0726 _refine_ls_R_factor_gt 0.0601 _refine_ls_wR_factor_ref 0.2029 _refine_ls_wR_factor_gt 0.1872 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _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 C1 C 1.0919(3) 0.0875(3) 0.1570(3) 0.0781(8) Uani 1 1 d . . . H1A H 1.1166 0.0496 0.2296 0.117 Uiso 0.50 1 calc PR . . H1B H 1.1496 0.1568 0.1544 0.117 Uiso 0.50 1 calc PR . . H1C H 1.0935 0.0210 0.1040 0.117 Uiso 0.50 1 calc PR . . H1D H 1.1232 0.1020 0.0958 0.117 Uiso 0.50 1 calc PR . . H1E H 1.0902 -0.0052 0.1709 0.117 Uiso 0.50 1 calc PR . . H1F H 1.1462 0.1306 0.2213 0.117 Uiso 0.50 1 calc PR . . C2 C 0.8993(3) 0.2000(3) 0.0375(2) 0.0682(7) Uani 1 1 d . . . H2A H 0.9361 0.2097 -0.0184 0.082 Uiso 1 1 calc R . . H2B H 0.8180 0.2315 0.0276 0.082 Uiso 1 1 calc R . . C3 C 0.96255(19) 0.1416(2) 0.13101(16) 0.0441(5) Uani 1 1 d . . . C4 C 0.90835(16) 0.13878(18) 0.22354(14) 0.0371(5) Uani 1 1 d . . . C5 C 0.7887(2) -0.0600(2) 0.13960(19) 0.0557(6) Uani 1 1 d . . . H5A H 0.7177 -0.1095 0.1457 0.084 Uiso 0.50 1 calc PR . . H5B H 0.8622 -0.1154 0.1577 0.084 Uiso 0.50 1 calc PR . . H5C H 0.7710 -0.0283 0.0654 0.084 Uiso 0.50 1 calc PR . . H5D H 0.8496 -0.0593 0.1002 0.084 Uiso 0.50 1 calc PR . . H5E H 0.7051 -0.0534 0.0882 0.084 Uiso 0.50 1 calc PR . . H5F H 0.7962 -0.1405 0.1805 0.084 Uiso 0.50 1 calc PR . . C6 C 0.77044(16) 0.03528(17) 0.31188(14) 0.0350(5) Uani 1 1 d . . . C7 C 0.65991(16) 0.09210(17) 0.32239(14) 0.0358(5) Uani 1 1 d . . . C8 C 0.63140(19) 0.0589(2) 0.41792(16) 0.0446(5) Uani 1 1 d . . . H8 H 0.5590 0.0941 0.4288 0.054 Uiso 1 1 calc R . . C9 C 0.7062(2) -0.0241(2) 0.49732(17) 0.0529(6) Uani 1 1 d . . . H9 H 0.6829 -0.0440 0.5596 0.063 Uiso 1 1 calc R . . C10 C 0.8136(2) -0.0772(2) 0.48555(17) 0.0529(6) Uani 1 1 d . . . H10 H 0.8644 -0.1323 0.5395 0.063 Uiso 1 1 calc R . . C11 C 0.84537(19) -0.0477(2) 0.39269(17) 0.0459(6) Uani 1 1 d . . . H11 H 0.9183 -0.0838 0.3835 0.055 Uiso 1 1 calc R . . C12 C 0.57480(18) 0.18848(19) 0.23877(17) 0.0430(5) Uani 1 1 d . . . C13 C 0.6472(2) 0.3166(2) 0.2386(2) 0.0669(7) Uani 1 1 d . . . H13A H 0.7230 0.2979 0.2204 0.100 Uiso 1 1 calc R . . H13B H 0.6690 0.3563 0.3104 0.100 Uiso 1 1 calc R . . H13C H 0.5951 0.3759 0.1849 0.100 Uiso 1 1 calc R . . C14 C 0.5310(3) 0.1313(3) 0.1222(2) 0.0742(8) Uani 1 1 d . . . H14A H 0.6035 0.1072 0.1006 0.111 Uiso 1 1 calc R . . H14B H 0.4823 0.1959 0.0719 0.111 Uiso 1 1 calc R . . H14C H 0.4799 0.0548 0.1209 0.111 Uiso 1 1 calc R . . C15 C 0.4556(2) 0.2242(3) 0.2676(3) 0.0727(8) Uani 1 1 d . . . H15A H 0.4053 0.2843 0.2135 0.109 Uiso 1 1 calc R . . H15B H 0.4787 0.2650 0.3391 0.109 Uiso 1 1 calc R . . H15C H 0.4075 0.1460 0.2685 0.109 Uiso 1 1 calc R . . N1 N 0.81224(14) 0.05327(15) 0.21690(12) 0.0380(5) Uani 1 1 d . . . O1 O 0.94893(14) 0.21355(15) 0.30153(11) 0.0527(5) Uani 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0661(16) 0.093(2) 0.0875(19) -0.0036(16) 0.0426(15) 0.0121(15) C2 0.0829(17) 0.0774(18) 0.0496(13) 0.0100(12) 0.0279(12) -0.0050(13) C3 0.0491(11) 0.0449(11) 0.0428(11) -0.0040(8) 0.0206(9) -0.0049(9) C4 0.0346(9) 0.0394(10) 0.0358(9) 0.0015(8) 0.0090(7) 0.0029(7) C5 0.0660(14) 0.0501(13) 0.0575(13) -0.0158(10) 0.0283(11) -0.0098(10) C6 0.0350(10) 0.0350(10) 0.0361(9) -0.0008(7) 0.0126(7) -0.0033(7) C7 0.0333(9) 0.0337(10) 0.0405(10) -0.0014(8) 0.0115(8) -0.0031(7) C8 0.0422(11) 0.0492(12) 0.0473(11) -0.0024(9) 0.0208(9) -0.0021(8) C9 0.0596(13) 0.0607(14) 0.0412(11) 0.0075(9) 0.0200(9) -0.0060(10) C10 0.0532(12) 0.0561(13) 0.0448(12) 0.0151(10) 0.0086(9) 0.0018(10) C11 0.0387(10) 0.0478(12) 0.0495(12) 0.0067(9) 0.0112(8) 0.0052(8) C12 0.0367(10) 0.0405(11) 0.0501(11) 0.0048(9) 0.0109(8) 0.0046(8) C13 0.0564(14) 0.0452(13) 0.0979(19) 0.0202(12) 0.0222(13) 0.0076(10) C14 0.0693(16) 0.0843(19) 0.0525(13) 0.0025(13) -0.0050(12) 0.0196(14) C15 0.0514(14) 0.0765(17) 0.0959(19) 0.0267(15) 0.0309(13) 0.0243(12) N1 0.0388(9) 0.0405(9) 0.0368(8) -0.0034(6) 0.0146(7) -0.0018(6) O1 0.0538(9) 0.0608(10) 0.0443(8) -0.0139(7) 0.0164(7) -0.0126(7) _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 C3 1.478(4) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C1 H1D 0.9600 . ? C1 H1E 0.9600 . ? C1 H1F 0.9600 . ? C2 C3 1.323(3) . ? C2 H2A 0.9300 . ? C2 H2B 0.9300 . ? C3 C4 1.482(3) . ? C4 O1 1.221(2) . ? C4 N1 1.360(3) . ? C5 N1 1.485(3) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C5 H5D 0.9600 . ? C5 H5E 0.9600 . ? C5 H5F 0.9600 . ? C6 C11 1.391(3) . ? C6 C7 1.401(3) . ? C6 N1 1.436(3) . ? C7 C8 1.391(3) . ? C7 C12 1.538(3) . ? C8 C9 1.381(3) . ? C8 H8 0.9300 . ? C9 C10 1.361(4) . ? C9 H9 0.9300 . ? C10 C11 1.369(3) . ? C10 H10 0.9300 . ? C11 H11 0.9300 . ? C12 C15 1.526(3) . ? C12 C14 1.528(4) . ? C12 C13 1.531(4) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 H14A 0.9600 . ? C14 H14B 0.9600 . ? C14 H14C 0.9600 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 C1 H1A 109.5 . . ? C3 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C3 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C3 C1 H1D 109.5 . . ? H1A C1 H1D 141.1 . . ? H1B C1 H1D 56.3 . . ? H1C C1 H1D 56.3 . . ? C3 C1 H1E 109.5 . . ? H1A C1 H1E 56.3 . . ? H1B C1 H1E 141.1 . . ? H1C C1 H1E 56.3 . . ? H1D C1 H1E 109.5 . . ? C3 C1 H1F 109.5 . . ? H1A C1 H1F 56.3 . . ? H1B C1 H1F 56.3 . . ? H1C C1 H1F 141.1 . . ? H1D C1 H1F 109.5 . . ? H1E C1 H1F 109.5 . . ? C3 C2 H2A 120.0 . . ? C3 C2 H2B 120.0 . . ? H2A C2 H2B 120.0 . . ? C2 C3 C1 125.3(2) . . ? C2 C3 C4 119.5(2) . . ? C1 C3 C4 114.93(19) . . ? O1 C4 N1 122.25(17) . . ? O1 C4 C3 119.80(18) . . ? N1 C4 C3 117.94(16) . . ? N1 C5 H5A 109.5 . . ? N1 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? N1 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? N1 C5 H5D 109.5 . . ? H5A C5 H5D 141.1 . . ? H5B C5 H5D 56.3 . . ? H5C C5 H5D 56.3 . . ? N1 C5 H5E 109.5 . . ? H5A C5 H5E 56.3 . . ? H5B C5 H5E 141.1 . . ? H5C C5 H5E 56.3 . . ? H5D C5 H5E 109.5 . . ? N1 C5 H5F 109.5 . . ? H5A C5 H5F 56.3 . . ? H5B C5 H5F 56.3 . . ? H5C C5 H5F 141.1 . . ? H5D C5 H5F 109.5 . . ? H5E C5 H5F 109.5 . . ? C11 C6 C7 121.40(18) . . ? C11 C6 N1 115.16(18) . . ? C7 C6 N1 123.39(17) . . ? C8 C7 C6 115.34(17) . . ? C8 C7 C12 120.17(18) . . ? C6 C7 C12 124.46(17) . . ? C9 C8 C7 122.7(2) . . ? C9 C8 H8 118.6 . . ? C7 C8 H8 118.6 . . ? C10 C9 C8 120.8(2) . . ? C10 C9 H9 119.6 . . ? C8 C9 H9 119.6 . . ? C9 C10 C11 118.6(2) . . ? C9 C10 H10 120.7 . . ? C11 C10 H10 120.7 . . ? C10 C11 C6 121.1(2) . . ? C10 C11 H11 119.4 . . ? C6 C11 H11 119.4 . . ? C15 C12 C14 106.6(2) . . ? C15 C12 C13 107.1(2) . . ? C14 C12 C13 109.3(2) . . ? C15 C12 C7 112.26(19) . . ? C14 C12 C7 111.94(19) . . ? C13 C12 C7 109.37(19) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 H14A 109.5 . . ? C12 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? C12 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? H14B C14 H14C 109.5 . . ? C12 C15 H15A 109.5 . . ? C12 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C12 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 109.5 . . ? C4 N1 C6 118.83(15) . . ? C4 N1 C5 120.70(16) . . ? C6 N1 C5 115.07(17) . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.277 _refine_diff_density_min -0.244 _refine_diff_density_rms 0.066 #===END data_Structure_7a _database_code_depnum_ccdc_archive 'CCDC 723728' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C15 H21 N O' _chemical_formula_weight 231.33 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Tetragonal _symmetry_space_group_name_H-M I-4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z' 'y, -x, -z' '-y, x, -z' 'x+1/2, y+1/2, z+1/2' '-x+1/2, -y+1/2, z+1/2' 'y+1/2, -x+1/2, -z+1/2' '-y+1/2, x+1/2, -z+1/2' _cell_length_a 17.588(12) _cell_length_b 17.588(12) _cell_length_c 8.963(13) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2773(5) _cell_formula_units_Z 8 _cell_measurement_temperature 533(2) _cell_measurement_reflns_used 969 _cell_measurement_theta_min 2 _cell_measurement_theta_max 26 _exptl_crystal_description rod _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.108 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 0.069 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9600 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 533(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 7197 _diffrn_reflns_av_R_equivalents 0.0444 _diffrn_reflns_av_sigmaI/netI 0.0341 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 26.13 _reflns_number_total 1463 _reflns_number_gt 1101 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1486P)^2^+0.0000P] 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 0(10) _refine_ls_number_reflns 1463 _refine_ls_number_parameters 160 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0753 _refine_ls_R_factor_gt 0.0562 _refine_ls_wR_factor_ref 0.1964 _refine_ls_wR_factor_gt 0.1652 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.002 _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 0.75996(16) 0.30972(15) 1.0704(3) 0.0496(7) Uani 1 1 d . . . N1 N 0.71913(18) 0.2445(2) 0.8704(4) 0.0411(8) Uani 1 1 d . . . C1 C 0.5278(3) 0.1082(3) 1.0628(8) 0.0816(17) Uani 1 1 d . . . H1A H 0.5380 0.0569 1.0939 0.122 Uiso 1 1 calc R . . H1B H 0.4865 0.1083 0.9928 0.122 Uiso 1 1 calc R . . H1C H 0.5144 0.1383 1.1481 0.122 Uiso 1 1 calc R . . C2 C 0.6181(3) 0.0917(3) 0.8560(6) 0.0617(12) Uani 1 1 d . . . H2A H 0.6623 0.1119 0.8075 0.092 Uiso 1 1 calc R . . H2B H 0.5763 0.0911 0.7871 0.092 Uiso 1 1 calc R . . H2C H 0.6283 0.0408 0.8891 0.092 Uiso 1 1 calc R . . C3 C 0.6618(3) 0.1361(2) 1.1069(5) 0.0577(11) Uani 1 1 d . . . H3A H 0.7078 0.1569 1.0661 0.087 Uiso 1 1 calc R . . H3B H 0.6700 0.0839 1.1334 0.087 Uiso 1 1 calc R . . H3C H 0.6475 0.1644 1.1941 0.087 Uiso 1 1 calc R . . C4 C 0.5979(2) 0.1412(2) 0.9899(5) 0.0480(9) Uani 1 1 d . . . C5 C 0.5842(2) 0.2231(2) 0.9385(4) 0.0415(8) Uani 1 1 d . . . C6 C 0.5124(2) 0.2541(2) 0.9386(6) 0.0553(10) Uani 1 1 d . . . H6 H 0.4723 0.2241 0.9716 0.066 Uiso 1 1 calc R . . C7 C 0.4969(3) 0.3266(3) 0.8929(6) 0.0654(13) Uani 1 1 d . . . H7 H 0.4473 0.3450 0.8959 0.078 Uiso 1 1 calc R . . C8 C 0.5556(3) 0.3725(3) 0.8419(7) 0.0687(13) Uani 1 1 d . . . H8 H 0.5461 0.4221 0.8107 0.082 Uiso 1 1 calc R . . C9 C 0.6276(3) 0.3434(2) 0.8385(6) 0.0568(11) Uani 1 1 d . . . H9 H 0.6673 0.3738 0.8046 0.068 Uiso 1 1 calc R . . C10 C 0.6429(2) 0.2700(2) 0.8843(4) 0.0405(8) Uani 1 1 d . . . C11 C 0.7733(2) 0.2673(2) 0.9648(4) 0.0389(8) Uani 1 1 d . . . C12 C 0.8518(2) 0.2374(2) 0.9394(5) 0.0458(9) Uani 1 1 d . . . C13 C 0.9144(2) 0.2859(3) 0.9999(6) 0.0599(11) Uani 1 1 d . . . H13A H 0.9188 0.2778 1.1055 0.090 Uiso 1 1 calc R . . H13B H 0.9031 0.3384 0.9809 0.090 Uiso 1 1 calc R . . H13C H 0.9614 0.2726 0.9521 0.090 Uiso 1 1 calc R . . C14 C 0.8632(3) 0.1716(3) 0.8750(6) 0.0643(12) Uani 1 1 d . . . H14 H 0.8203 0.1451 0.8438 0.077 Uiso 1 1 calc R . . C15 C 0.9386(3) 0.1348(5) 0.8466(12) 0.104(2) Uani 1 1 d . . . H15A H 0.9462 0.1294 0.7411 0.156 Uiso 1 1 calc R . . H15B H 0.9397 0.0856 0.8929 0.156 Uiso 1 1 calc R . . H15C H 0.9783 0.1659 0.8877 0.156 Uiso 1 1 calc R . . H1 H 0.729(3) 0.223(3) 0.801(6) 0.044(13) 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 O1 0.0515(16) 0.0561(16) 0.0411(15) -0.0041(13) -0.0023(12) 0.0000(12) N1 0.0387(17) 0.0487(18) 0.0360(16) -0.0036(15) 0.0005(13) -0.0030(13) C1 0.069(3) 0.082(4) 0.094(4) 0.018(3) 0.009(3) -0.028(3) C2 0.081(3) 0.044(2) 0.060(3) -0.009(2) -0.013(2) 0.002(2) C3 0.076(3) 0.049(2) 0.048(2) 0.0088(18) -0.012(2) -0.008(2) C4 0.056(2) 0.0378(19) 0.050(2) 0.0011(17) -0.0010(18) -0.0084(15) C5 0.0402(19) 0.0413(19) 0.0431(17) -0.0037(16) 0.0017(16) -0.0037(15) C6 0.045(2) 0.058(3) 0.063(2) -0.005(2) 0.002(2) -0.0059(18) C7 0.051(3) 0.070(3) 0.076(3) -0.005(3) -0.004(2) 0.016(2) C8 0.071(3) 0.046(2) 0.089(3) 0.006(2) -0.009(3) 0.012(2) C9 0.056(3) 0.045(2) 0.069(3) 0.008(2) -0.008(2) -0.0029(17) C10 0.039(2) 0.045(2) 0.0376(17) -0.0005(15) 0.0002(14) -0.0019(14) C11 0.040(2) 0.0422(19) 0.0343(17) 0.0034(14) 0.0008(14) -0.0062(14) C12 0.039(2) 0.056(2) 0.0422(18) -0.0006(18) -0.0045(16) -0.0035(15) C13 0.044(2) 0.072(3) 0.064(2) -0.008(2) -0.007(2) -0.0124(19) C14 0.046(2) 0.069(3) 0.078(3) -0.019(3) -0.011(2) 0.0025(19) C15 0.053(3) 0.106(4) 0.153(6) -0.047(5) -0.015(4) 0.014(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 O1 C11 1.228(5) . ? N1 C11 1.336(5) . ? N1 C10 1.419(5) . ? N1 H1 0.75(5) . ? C1 C4 1.511(7) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C4 1.524(6) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C4 1.541(6) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C4 C5 1.532(6) . ? C5 C6 1.374(6) . ? C5 C10 1.408(5) . ? C6 C7 1.367(7) . ? C6 H6 0.9300 . ? C7 C8 1.388(8) . ? C7 H7 0.9300 . ? C8 C9 1.367(7) . ? C8 H8 0.9300 . ? C9 C10 1.382(6) . ? C9 H9 0.9300 . ? C11 C12 1.495(5) . ? C12 C14 1.308(7) . ? C12 C13 1.494(6) . ? C13 H13A 0.9600 . ? C13 H13B 0.9600 . ? C13 H13C 0.9600 . ? C14 C15 1.497(7) . ? C14 H14 0.9300 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C11 N1 C10 121.6(3) . . ? C11 N1 H1 120(4) . . ? C10 N1 H1 117(4) . . ? C4 C1 H1A 109.5 . . ? C4 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C4 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C4 C2 H2A 109.5 . . ? C4 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C4 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C4 C3 H3A 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C4 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C1 C4 C2 108.1(4) . . ? C1 C4 C5 111.3(4) . . ? C2 C4 C5 109.7(4) . . ? C1 C4 C3 106.2(4) . . ? C2 C4 C3 109.4(4) . . ? C5 C4 C3 111.9(3) . . ? C6 C5 C10 116.3(4) . . ? C6 C5 C4 121.1(3) . . ? C10 C5 C4 122.6(3) . . ? C7 C6 C5 123.6(4) . . ? C7 C6 H6 118.2 . . ? C5 C6 H6 118.2 . . ? C6 C7 C8 119.5(4) . . ? C6 C7 H7 120.2 . . ? C8 C7 H7 120.2 . . ? C9 C8 C7 118.6(5) . . ? C9 C8 H8 120.7 . . ? C7 C8 H8 120.7 . . ? C8 C9 C10 121.6(5) . . ? C8 C9 H9 119.2 . . ? C10 C9 H9 119.2 . . ? C9 C10 C5 120.4(4) . . ? C9 C10 N1 116.9(3) . . ? C5 C10 N1 122.6(4) . . ? O1 C11 N1 122.3(3) . . ? O1 C11 C12 120.5(3) . . ? N1 C11 C12 117.2(3) . . ? C14 C12 C13 123.5(4) . . ? C14 C12 C11 121.4(4) . . ? C13 C12 C11 115.1(4) . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C12 C14 C15 126.4(5) . . ? C12 C14 H14 116.8 . . ? C15 C14 H14 116.8 . . ? 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 . . ? _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.13 _diffrn_measured_fraction_theta_full 0.990 _refine_diff_density_max 0.247 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.060 #===END data_Structure_4f _database_code_depnum_ccdc_archive 'CCDC 723729' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H29 N O' _chemical_formula_weight 287.43 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.073(10) _cell_length_b 14.119(13) _cell_length_c 14.351(13) _cell_angle_alpha 115.446(14) _cell_angle_beta 96.908(16) _cell_angle_gamma 107.764(15) _cell_volume 1845(3) _cell_formula_units_Z 4 _cell_measurement_temperature 273(2) _cell_measurement_reflns_used 900 _cell_measurement_theta_min 2.00 _cell_measurement_theta_max 26.00 _exptl_crystal_description parallelepiped _exptl_crystal_colour white _exptl_crystal_size_max .90 _exptl_crystal_size_mid .52 _exptl_crystal_size_min .50 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.035 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 0.063 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.755363 _exptl_absorpt_correction_T_max 1.0000000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 273(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type '1K CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13641 _diffrn_reflns_av_R_equivalents 0.0380 _diffrn_reflns_av_sigmaI/netI 0.0535 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 25.06 _reflns_number_total 6418 _reflns_number_gt 4199 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.1708P)^2^+0.4513P] 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 SHELXL _refine_ls_extinction_coef 0.009(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 6418 _refine_ls_number_parameters 393 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1161 _refine_ls_R_factor_gt 0.0854 _refine_ls_wR_factor_ref 0.2864 _refine_ls_wR_factor_gt 0.2523 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _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 0.1358(2) 0.3175(2) 0.0550(2) 0.0995(9) Uani 1 1 d . . . N1 N 0.3444(2) 0.4431(2) 0.1536(2) 0.0604(7) Uani 1 1 d . . . C1 C 0.4699(7) 0.7562(5) 0.4462(9) 0.196(6) Uani 0.796(8) 1 d P A 1 H1A H 0.5009 0.7751 0.3942 0.293 Uiso 0.796(8) 1 calc PR A 1 H1B H 0.5443 0.7814 0.5055 0.293 Uiso 0.796(8) 1 calc PR A 1 H1C H 0.4120 0.7934 0.4722 0.293 Uiso 0.796(8) 1 calc PR A 1 C2 C 0.3465(13) 0.5839(12) 0.4631(10) 0.202(7) Uani 0.796(8) 1 d P A 1 H2A H 0.3010 0.5022 0.4215 0.303 Uiso 0.796(8) 1 calc PR A 1 H2B H 0.2865 0.6166 0.4926 0.303 Uiso 0.796(8) 1 calc PR A 1 H2C H 0.4199 0.6038 0.5207 0.303 Uiso 0.796(8) 1 calc PR A 1 C3 C 0.2694(6) 0.6012(6) 0.3125(5) 0.118(3) Uani 0.796(8) 1 d P A 1 H3A H 0.2934 0.6308 0.2653 0.178 Uiso 0.796(8) 1 calc PR A 1 H3B H 0.2157 0.6362 0.3506 0.178 Uiso 0.796(8) 1 calc PR A 1 H3C H 0.2202 0.5200 0.2708 0.178 Uiso 0.796(8) 1 calc PR A 1 C1A C 0.420(3) 0.729(2) 0.390(2) 0.105(9) Uiso 0.204(8) 1 d P A 2 H1A1 H 0.5137 0.7731 0.4135 0.158 Uiso 0.204(8) 1 calc PR A 2 H1A2 H 0.3782 0.7724 0.4355 0.158 Uiso 0.204(8) 1 calc PR A 2 H1A3 H 0.3843 0.7107 0.3167 0.158 Uiso 0.204(8) 1 calc PR A 2 C2A C 0.4395(16) 0.6820(14) 0.5289(12) 0.056(4) Uiso 0.204(8) 1 d P A 2 H2A1 H 0.5342 0.7218 0.5577 0.084 Uiso 0.204(8) 1 calc PR A 2 H2A2 H 0.4110 0.6208 0.5450 0.084 Uiso 0.204(8) 1 calc PR A 2 H2A3 H 0.3985 0.7341 0.5610 0.084 Uiso 0.204(8) 1 calc PR A 2 C3A C 0.258(3) 0.541(2) 0.379(2) 0.111(9) Uiso 0.204(8) 1 d P A 2 H3A1 H 0.2077 0.5825 0.4161 0.166 Uiso 0.204(8) 1 calc PR A 2 H3A2 H 0.2701 0.4948 0.4094 0.166 Uiso 0.204(8) 1 calc PR A 2 H3A3 H 0.2101 0.4936 0.3040 0.166 Uiso 0.204(8) 1 calc PR A 2 C4 C 0.9040(5) 0.4741(5) 0.3298(5) 0.151(3) Uani 1 1 d . . . H4A H 0.8724 0.4523 0.3800 0.226 Uiso 1 1 calc R . . H4B H 0.9511 0.5556 0.3656 0.226 Uiso 1 1 calc R . . H4C H 0.9624 0.4379 0.3028 0.226 Uiso 1 1 calc R . . C5 C 0.7232(5) 0.3067(4) 0.1862(5) 0.147(2) Uani 1 1 d . . . H5A H 0.6943 0.2880 0.2389 0.220 Uiso 1 1 calc R . . H5B H 0.7877 0.2760 0.1644 0.220 Uiso 1 1 calc R . . H5C H 0.6486 0.2745 0.1245 0.220 Uiso 1 1 calc R . . C6 C 0.8301(9) 0.4683(9) 0.1563(8) 0.230(5) Uani 1 1 d . . . H6A H 0.8937 0.4372 0.1327 0.344 Uiso 1 1 calc R . . H6B H 0.8705 0.5501 0.1893 0.344 Uiso 1 1 calc R . . H6C H 0.7556 0.4386 0.0954 0.344 Uiso 1 1 calc R . . C24 C 0.8644(6) 1.1801(4) 0.3765(4) 0.1096(16) Uani 1 1 d . . . H24A H 0.9538 1.2271 0.3870 0.164 Uiso 1 1 calc R . . H24B H 0.8242 1.2268 0.4205 0.164 Uiso 1 1 calc R . . H24C H 0.8148 1.1431 0.3020 0.164 Uiso 1 1 calc R . . C25 C 0.7238(4) 1.0125(4) 0.3922(4) 0.1079(16) Uani 1 1 d . . . H25A H 0.6807 1.0587 0.4326 0.162 Uiso 1 1 calc R . . H25B H 0.7267 0.9597 0.4168 0.162 Uiso 1 1 calc R . . H25C H 0.6754 0.9710 0.3170 0.162 Uiso 1 1 calc R . . C26 C 0.9326(4) 1.1534(3) 0.5305(3) 0.0799(10) Uani 1 1 d . . . H26A H 1.0223 1.2038 0.5461 0.120 Uiso 1 1 calc R . . H26B H 0.9325 1.0994 0.5543 0.120 Uiso 1 1 calc R . . H26C H 0.8852 1.1972 0.5675 0.120 Uiso 1 1 calc R . . C21 C 1.3501(4) 0.9230(5) 0.2802(4) 0.131(2) Uani 1 1 d . . . H21A H 1.3384 0.9098 0.3395 0.197 Uiso 1 1 calc R . . H21B H 1.3932 1.0036 0.3066 0.197 Uiso 1 1 calc R . . H21C H 1.4037 0.8853 0.2452 0.197 Uiso 1 1 calc R . . C22 C 1.2241(5) 0.8930(4) 0.1033(3) 0.1039(14) Uani 1 1 d . . . H22A H 1.1364 0.8614 0.0557 0.156 Uiso 1 1 calc R . . H22B H 1.2760 0.8552 0.0656 0.156 Uiso 1 1 calc R . . H22C H 1.2650 0.9733 0.1272 0.156 Uiso 1 1 calc R . . C23 C 1.1572(5) 0.7449(4) 0.1550(4) 0.1093(15) Uani 1 1 d . . . H23A H 1.0715 0.7112 0.1039 0.164 Uiso 1 1 calc R . . H23B H 1.1487 0.7290 0.2131 0.164 Uiso 1 1 calc R . . H23C H 1.2150 0.7132 0.1199 0.164 Uiso 1 1 calc R . . C101 C 0.6837(3) 0.4848(2) 0.2747(2) 0.0548(7) Uani 1 1 d . . . C102 C 0.7065(3) 0.5643(2) 0.3805(2) 0.0599(8) Uani 1 1 d . . . H102 H 0.7871 0.5908 0.4306 0.072 Uiso 1 1 calc R . . C103 C 0.4890(3) 0.5715(2) 0.3452(2) 0.0522(7) Uani 1 1 d . A . C104 C 0.4662(3) 0.4901(2) 0.2374(2) 0.0506(7) Uani 1 1 d . . . C105 C 0.5634(3) 0.4519(2) 0.2041(2) 0.0558(7) Uani 1 1 d . . . H105 H 0.5467 0.4021 0.1312 0.067 Uiso 1 1 calc R . . C106 C 0.6122(3) 0.6053(2) 0.4137(2) 0.0584(8) Uani 1 1 d . . . H106 H 0.6322 0.6587 0.4860 0.070 Uiso 1 1 calc R . . C107 C 0.7852(3) 0.4364(3) 0.2351(3) 0.0730(9) Uani 1 1 d . . . C108 C 0.3954(3) 0.6281(3) 0.3937(3) 0.0636(8) Uani 1 1 d . . . C109 C 0.2335(3) 0.3521(3) 0.1302(3) 0.0631(8) Uani 1 1 d . . . C110 C 0.2289(4) 0.2905(3) 0.1941(3) 0.0746(9) Uani 1 1 d . . . C111 C 0.3275(4) 0.2614(4) 0.2240(4) 0.1013(14) Uani 1 1 d . . . H11A H 0.3126 0.2144 0.2547 0.122 Uiso 1 1 calc R . . H11B H 0.4096 0.2886 0.2137 0.122 Uiso 1 1 calc R . . C112 C 0.3478(4) 0.4907(4) 0.0804(3) 0.0893(12) Uani 1 1 d . . . H11C H 0.4309 0.5546 0.1060 0.134 Uiso 0.50 1 calc PR . . H11D H 0.2764 0.5156 0.0779 0.134 Uiso 0.50 1 calc PR . . H11E H 0.3384 0.4331 0.0093 0.134 Uiso 0.50 1 calc PR . . H11F H 0.2663 0.4476 0.0228 0.134 Uiso 0.50 1 calc PR . . H11G H 0.4207 0.4866 0.0509 0.134 Uiso 0.50 1 calc PR . . H11H H 0.3587 0.5691 0.1195 0.134 Uiso 0.50 1 calc PR . . C113 C 0.1014(5) 0.2498(5) 0.2090(5) 0.134(2) Uani 1 1 d . . . H11I H 0.0446 0.2778 0.1824 0.202 Uiso 0.50 1 calc PR . . H11J H 0.1111 0.2766 0.2845 0.202 Uiso 0.50 1 calc PR . . H11K H 0.0631 0.1677 0.1703 0.202 Uiso 0.50 1 calc PR . . H11L H 0.1013 0.2036 0.2424 0.202 Uiso 0.50 1 calc PR . . H11M H 0.0348 0.2048 0.1403 0.202 Uiso 0.50 1 calc PR . . H11N H 0.0828 0.3136 0.2545 0.202 Uiso 0.50 1 calc PR . . O2 O 0.5622(2) 0.7625(2) 0.0877(2) 0.0949(9) Uani 1 1 d . . . N2 N 0.7615(2) 0.84054(18) 0.20921(18) 0.0493(6) Uani 1 1 d . . . C201 C 0.9002(2) 0.9161(2) 0.25888(19) 0.0415(6) Uani 1 1 d . . . C202 C 0.9875(3) 0.8694(2) 0.2158(2) 0.0461(6) Uani 1 1 d . . . H202 H 0.9523 0.7946 0.1590 0.055 Uiso 1 1 calc R . . C203 C 0.9468(2) 1.0269(2) 0.3480(2) 0.0445(6) Uani 1 1 d . . . C204 C 1.0844(3) 1.0858(2) 0.3828(2) 0.0567(7) Uani 1 1 d . . . H204 H 1.1203 1.1607 0.4396 0.068 Uiso 1 1 calc R . . C205 C 1.1241(3) 0.9283(2) 0.2529(2) 0.0482(6) Uani 1 1 d . . . C206 C 1.1699(3) 1.0403(2) 0.3384(2) 0.0572(7) Uani 1 1 d . . . H206 H 1.2605 1.0849 0.3658 0.069 Uiso 1 1 calc R . . C207 C 1.2159(3) 0.8758(3) 0.2002(2) 0.0610(8) Uani 1 1 d . . . C208 C 0.6775(3) 0.8358(2) 0.1295(2) 0.0586(8) Uani 1 1 d . . . C209 C 0.8650(3) 1.0893(2) 0.4084(2) 0.0558(7) Uani 1 1 d . . . C210 C 0.7191(3) 0.9216(3) 0.0922(2) 0.0629(8) Uani 1 1 d . . . C211 C 0.7155(3) 0.7497(3) 0.2374(3) 0.0773(10) Uani 1 1 d . . . H41A H 0.7833 0.7636 0.2957 0.116 Uiso 0.50 1 calc PR . . H41B H 0.6964 0.6771 0.1758 0.116 Uiso 0.50 1 calc PR . . H41C H 0.6367 0.7492 0.2590 0.116 Uiso 0.50 1 calc PR . . H41D H 0.6276 0.6963 0.1913 0.116 Uiso 0.50 1 calc PR . . H41E H 0.7145 0.7828 0.3112 0.116 Uiso 0.50 1 calc PR . . H41F H 0.7743 0.7107 0.2280 0.116 Uiso 0.50 1 calc PR . . C212 C 0.8319(4) 0.9485(3) 0.0667(3) 0.0808(10) Uani 1 1 d . . . H21D H 0.8485 0.9954 0.0360 0.097 Uiso 1 1 calc R . . H21E H 0.8939 0.9202 0.0797 0.097 Uiso 1 1 calc R . . C218 C 0.6176(4) 0.9656(4) 0.0724(4) 0.1007(13) Uani 1 1 d . . . H21G H 0.5428 0.9361 0.0942 0.151 Uiso 0.50 1 calc PR . . H21H H 0.5894 0.9413 -0.0030 0.151 Uiso 0.50 1 calc PR . . H21I H 0.6554 1.0476 0.1133 0.151 Uiso 0.50 1 calc PR . . H21J H 0.6489 1.0139 0.0421 0.151 Uiso 0.50 1 calc PR . . H21K H 0.6023 1.0087 0.1394 0.151 Uiso 0.50 1 calc PR . . H21L H 0.5363 0.9024 0.0230 0.151 Uiso 0.50 1 calc PR . . 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 0.0699(16) 0.0854(17) 0.0971(19) 0.0297(15) -0.0210(14) 0.0139(13) N1 0.0506(14) 0.0643(15) 0.0600(15) 0.0312(12) 0.0049(11) 0.0186(12) C1 0.075(4) 0.066(4) 0.300(13) -0.031(5) 0.023(6) 0.039(3) C2 0.284(15) 0.335(17) 0.251(13) 0.234(14) 0.229(13) 0.259(15) C3 0.088(4) 0.134(5) 0.114(4) 0.021(4) 0.017(3) 0.085(4) C4 0.080(3) 0.162(5) 0.159(5) 0.018(4) 0.011(3) 0.084(3) C5 0.108(4) 0.084(3) 0.203(6) 0.019(3) 0.032(4) 0.063(3) C6 0.292(9) 0.368(12) 0.353(11) 0.297(11) 0.286(10) 0.284(10) C24 0.182(5) 0.131(4) 0.094(3) 0.070(3) 0.071(3) 0.126(4) C25 0.064(2) 0.109(3) 0.101(3) 0.008(2) 0.039(2) 0.032(2) C26 0.097(3) 0.082(2) 0.0551(19) 0.0240(17) 0.0274(18) 0.042(2) C21 0.071(3) 0.188(5) 0.104(3) 0.028(3) 0.010(2) 0.084(3) C22 0.137(4) 0.137(4) 0.096(3) 0.075(3) 0.074(3) 0.085(3) C23 0.123(4) 0.109(3) 0.148(4) 0.071(3) 0.070(3) 0.085(3) C101 0.0466(15) 0.0494(15) 0.0666(18) 0.0237(14) 0.0179(13) 0.0236(12) C102 0.0418(15) 0.0576(16) 0.0673(19) 0.0228(15) 0.0061(13) 0.0194(13) C103 0.0479(15) 0.0488(14) 0.0580(16) 0.0233(13) 0.0151(13) 0.0217(12) C104 0.0435(14) 0.0483(14) 0.0553(16) 0.0252(13) 0.0098(12) 0.0146(12) C105 0.0520(16) 0.0499(15) 0.0554(16) 0.0195(13) 0.0139(13) 0.0181(13) C106 0.0513(16) 0.0569(16) 0.0514(16) 0.0142(13) 0.0099(13) 0.0226(13) C107 0.0598(19) 0.073(2) 0.088(2) 0.0312(18) 0.0273(18) 0.0393(16) C108 0.0523(17) 0.0675(18) 0.0709(19) 0.0273(16) 0.0238(15) 0.0316(14) C109 0.0516(17) 0.0538(16) 0.0620(18) 0.0185(14) 0.0016(14) 0.0147(14) C110 0.068(2) 0.0589(18) 0.077(2) 0.0235(17) 0.0140(17) 0.0178(16) C111 0.094(3) 0.087(3) 0.131(4) 0.074(3) 0.016(3) 0.024(2) C112 0.085(3) 0.106(3) 0.084(2) 0.063(2) 0.008(2) 0.029(2) C113 0.100(4) 0.128(4) 0.193(6) 0.094(4) 0.062(4) 0.038(3) O2 0.0500(13) 0.0800(16) 0.114(2) 0.0386(15) -0.0151(13) 0.0039(12) N2 0.0410(12) 0.0463(12) 0.0555(13) 0.0250(10) 0.0091(10) 0.0130(9) C201 0.0399(13) 0.0446(13) 0.0412(13) 0.0233(11) 0.0097(10) 0.0159(11) C202 0.0484(15) 0.0473(14) 0.0401(13) 0.0187(11) 0.0095(11) 0.0215(12) C203 0.0439(14) 0.0454(13) 0.0437(13) 0.0217(11) 0.0113(11) 0.0181(11) C204 0.0499(16) 0.0432(14) 0.0570(17) 0.0128(12) 0.0058(13) 0.0152(12) C205 0.0458(15) 0.0658(17) 0.0478(14) 0.0346(13) 0.0178(12) 0.0291(13) C206 0.0358(14) 0.0599(17) 0.0654(18) 0.0277(14) 0.0069(13) 0.0137(12) C207 0.0555(17) 0.086(2) 0.0597(17) 0.0391(16) 0.0259(14) 0.0420(16) C208 0.0443(16) 0.0551(16) 0.0636(17) 0.0217(14) 0.0055(13) 0.0190(13) C209 0.0612(17) 0.0602(16) 0.0497(16) 0.0231(13) 0.0194(13) 0.0335(14) C210 0.0611(19) 0.0690(19) 0.0543(17) 0.0262(15) 0.0048(14) 0.0313(15) C211 0.072(2) 0.0629(19) 0.096(3) 0.0478(19) 0.0198(19) 0.0151(16) C212 0.088(3) 0.103(3) 0.076(2) 0.060(2) 0.022(2) 0.045(2) C218 0.087(3) 0.113(3) 0.117(3) 0.065(3) 0.011(2) 0.054(2) _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 C109 1.231(4) . ? N1 C109 1.357(4) . ? N1 C104 1.443(4) . ? N1 C112 1.469(4) . ? C1 C108 1.513(8) . ? C1 H1A 0.9600 . ? C1 H1B 0.9600 . ? C1 H1C 0.9600 . ? C2 C108 1.459(8) . ? C2 H2A 0.9600 . ? C2 H2B 0.9600 . ? C2 H2C 0.9600 . ? C3 C108 1.535(6) . ? C3 H3A 0.9600 . ? C3 H3B 0.9600 . ? C3 H3C 0.9600 . ? C1A C108 1.40(3) . ? C1A H1A1 0.9600 . ? C1A H1A2 0.9600 . ? C1A H1A3 0.9600 . ? C2A C108 1.691(16) . ? C2A H2A1 0.9600 . ? C2A H2A2 0.9600 . ? C2A H2A3 0.9600 . ? C3A C108 1.56(3) . ? C3A H3A1 0.9600 . ? C3A H3A2 0.9600 . ? C3A H3A3 0.9600 . ? C4 C107 1.543(6) . ? C4 H4A 0.9600 . ? C4 H4B 0.9600 . ? C4 H4C 0.9600 . ? C5 C107 1.527(6) . ? C5 H5A 0.9600 . ? C5 H5B 0.9600 . ? C5 H5C 0.9600 . ? C6 C107 1.472(7) . ? C6 H6A 0.9600 . ? C6 H6B 0.9600 . ? C6 H6C 0.9600 . ? C24 C209 1.538(5) . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C209 1.528(5) . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 C209 1.535(5) . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C21 C207 1.517(5) . ? C21 H21A 0.9600 . ? C21 H21B 0.9600 . ? C21 H21C 0.9600 . ? C22 C207 1.519(5) . ? C22 H22A 0.9600 . ? C22 H22B 0.9600 . ? C22 H22C 0.9600 . ? C23 C207 1.548(6) . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C101 C102 1.379(4) . ? C101 C105 1.383(4) . ? C101 C107 1.530(4) . ? C102 C106 1.380(4) . ? C102 H102 0.9300 . ? C103 C106 1.390(4) . ? C103 C104 1.407(4) . ? C103 C108 1.548(4) . ? C104 C105 1.392(4) . ? C105 H105 0.9300 . ? C106 H106 0.9300 . ? C109 C110 1.506(5) . ? C110 C111 1.362(5) . ? C110 C113 1.433(6) . ? C111 H11A 0.9300 . ? C111 H11B 0.9300 . ? C112 H11C 0.9600 . ? C112 H11D 0.9600 . ? C112 H11E 0.9600 . ? C112 H11F 0.9600 . ? C112 H11G 0.9600 . ? C112 H11H 0.9600 . ? C113 H11I 0.9600 . ? C113 H11J 0.9600 . ? C113 H11K 0.9600 . ? C113 H11L 0.9600 . ? C113 H11M 0.9600 . ? C113 H11N 0.9600 . ? O2 C208 1.240(4) . ? N2 C208 1.348(4) . ? N2 C201 1.445(3) . ? N2 C211 1.471(4) . ? C201 C202 1.391(4) . ? C201 C203 1.407(4) . ? C202 C205 1.386(4) . ? C202 H202 0.9300 . ? C203 C204 1.396(4) . ? C203 C209 1.539(4) . ? C204 C206 1.372(4) . ? C204 H204 0.9300 . ? C205 C206 1.399(4) . ? C205 C207 1.522(4) . ? C206 H206 0.9300 . ? C208 C210 1.497(5) . ? C210 C212 1.333(5) . ? C210 C218 1.493(5) . ? C211 H41A 0.9600 . ? C211 H41B 0.9600 . ? C211 H41C 0.9600 . ? C211 H41D 0.9600 . ? C211 H41E 0.9600 . ? C211 H41F 0.9600 . ? C212 H21D 0.9300 . ? C212 H21E 0.9300 . ? C218 H21G 0.9600 . ? C218 H21H 0.9600 . ? C218 H21I 0.9600 . ? C218 H21J 0.9600 . ? C218 H21K 0.9600 . ? C218 H21L 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C109 N1 C104 125.7(3) . . ? C109 N1 C112 117.8(3) . . ? C104 N1 C112 116.1(3) . . ? C108 C1 H1A 109.5 . . ? C108 C1 H1B 109.5 . . ? H1A C1 H1B 109.5 . . ? C108 C1 H1C 109.5 . . ? H1A C1 H1C 109.5 . . ? H1B C1 H1C 109.5 . . ? C108 C2 H2A 109.5 . . ? C108 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? C108 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? C108 C3 H3A 109.5 . . ? C108 C3 H3B 109.5 . . ? H3A C3 H3B 109.5 . . ? C108 C3 H3C 109.5 . . ? H3A C3 H3C 109.5 . . ? H3B C3 H3C 109.5 . . ? C108 C1A H1A1 109.5 . . ? C108 C1A H1A2 109.5 . . ? H1A1 C1A H1A2 109.5 . . ? C108 C1A H1A3 109.5 . . ? H1A1 C1A H1A3 109.5 . . ? H1A2 C1A H1A3 109.5 . . ? C108 C2A H2A1 109.5 . . ? C108 C2A H2A2 109.5 . . ? H2A1 C2A H2A2 109.5 . . ? C108 C2A H2A3 109.5 . . ? H2A1 C2A H2A3 109.5 . . ? H2A2 C2A H2A3 109.5 . . ? C108 C3A H3A1 109.5 . . ? C108 C3A H3A2 109.5 . . ? H3A1 C3A H3A2 109.5 . . ? C108 C3A H3A3 109.5 . . ? H3A1 C3A H3A3 109.5 . . ? H3A2 C3A H3A3 109.5 . . ? C107 C4 H4A 109.5 . . ? C107 C4 H4B 109.5 . . ? H4A C4 H4B 109.5 . . ? C107 C4 H4C 109.5 . . ? H4A C4 H4C 109.5 . . ? H4B C4 H4C 109.5 . . ? C107 C5 H5A 109.5 . . ? C107 C5 H5B 109.5 . . ? H5A C5 H5B 109.5 . . ? C107 C5 H5C 109.5 . . ? H5A C5 H5C 109.5 . . ? H5B C5 H5C 109.5 . . ? C107 C6 H6A 109.5 . . ? C107 C6 H6B 109.5 . . ? H6A C6 H6B 109.5 . . ? C107 C6 H6C 109.5 . . ? H6A C6 H6C 109.5 . . ? H6B C6 H6C 109.5 . . ? C209 C24 H24A 109.5 . . ? C209 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C209 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C209 C25 H25A 109.5 . . ? C209 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C209 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C209 C26 H26A 109.5 . . ? C209 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C209 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C207 C21 H21A 109.5 . . ? C207 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C207 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C207 C22 H22A 109.5 . . ? C207 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? C207 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? C207 C23 H23A 109.5 . . ? C207 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C207 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C102 C101 C105 116.1(3) . . ? C102 C101 C107 122.9(3) . . ? C105 C101 C107 121.0(3) . . ? C101 C102 C106 121.4(3) . . ? C101 C102 H102 119.3 . . ? C106 C102 H102 119.3 . . ? C106 C103 C104 114.5(2) . . ? C106 C103 C108 117.7(3) . . ? C104 C103 C108 127.7(3) . . ? C105 C104 C103 121.3(3) . . ? C105 C104 N1 115.3(2) . . ? C103 C104 N1 123.4(3) . . ? C101 C105 C104 122.8(3) . . ? C101 C105 H105 118.6 . . ? C104 C105 H105 118.6 . . ? C102 C106 C103 123.8(3) . . ? C102 C106 H106 118.1 . . ? C103 C106 H106 118.1 . . ? C6 C107 C5 111.0(6) . . ? C6 C107 C101 111.0(3) . . ? C5 C107 C101 108.9(3) . . ? C6 C107 C4 111.0(5) . . ? C5 C107 C4 103.1(4) . . ? C101 C107 C4 111.6(3) . . ? C1A C108 C2 136.2(13) . . ? C1A C108 C1 30.8(12) . . ? C2 C108 C1 116.7(7) . . ? C1A C108 C3 75.9(12) . . ? C2 C108 C3 104.4(6) . . ? C1 C108 C3 104.4(5) . . ? C1A C108 C103 110.7(12) . . ? C2 C108 C103 108.2(4) . . ? C1 C108 C103 107.6(3) . . ? C3 C108 C103 115.9(3) . . ? C1A C108 C3A 126.3(16) . . ? C2 C108 C3A 47.8(10) . . ? C1 C108 C3A 138.3(11) . . ? C3 C108 C3A 58.8(11) . . ? C103 C108 C3A 114.1(11) . . ? C1A C108 C2A 99.8(12) . . ? C2 C108 C2A 47.3(7) . . ? C1 C108 C2A 72.0(7) . . ? C3 C108 C2A 132.7(6) . . ? C103 C108 C2A 109.7(6) . . ? C3A C108 C2A 91.8(12) . . ? O1 C109 N1 120.3(3) . . ? O1 C109 C110 119.1(3) . . ? N1 C109 C110 120.6(3) . . ? C111 C110 C113 121.1(4) . . ? C111 C110 C109 125.2(3) . . ? C113 C110 C109 113.1(4) . . ? C110 C111 H11A 120.0 . . ? C110 C111 H11B 120.0 . . ? H11A C111 H11B 120.0 . . ? N1 C112 H11C 109.5 . . ? N1 C112 H11D 109.5 . . ? H11C C112 H11D 109.5 . . ? N1 C112 H11E 109.5 . . ? H11C C112 H11E 109.5 . . ? H11D C112 H11E 109.5 . . ? N1 C112 H11F 109.5 . . ? H11C C112 H11F 141.1 . . ? H11D C112 H11F 56.3 . . ? H11E C112 H11F 56.3 . . ? N1 C112 H11G 109.5 . . ? H11C C112 H11G 56.3 . . ? H11D C112 H11G 141.1 . . ? H11E C112 H11G 56.3 . . ? H11F C112 H11G 109.5 . . ? N1 C112 H11H 109.5 . . ? H11C C112 H11H 56.3 . . ? H11D C112 H11H 56.3 . . ? H11E C112 H11H 141.1 . . ? H11F C112 H11H 109.5 . . ? H11G C112 H11H 109.5 . . ? C110 C113 H11I 109.5 . . ? C110 C113 H11J 109.5 . . ? H11I C113 H11J 109.5 . . ? C110 C113 H11K 109.5 . . ? H11I C113 H11K 109.5 . . ? H11J C113 H11K 109.5 . . ? C110 C113 H11L 109.5 . . ? H11I C113 H11L 141.1 . . ? H11J C113 H11L 56.3 . . ? H11K C113 H11L 56.3 . . ? C110 C113 H11M 109.5 . . ? H11I C113 H11M 56.3 . . ? H11J C113 H11M 141.1 . . ? H11K C113 H11M 56.3 . . ? H11L C113 H11M 109.5 . . ? C110 C113 H11N 109.5 . . ? H11I C113 H11N 56.3 . . ? H11J C113 H11N 56.3 . . ? H11K C113 H11N 141.1 . . ? H11L C113 H11N 109.5 . . ? H11M C113 H11N 109.5 . . ? C208 N2 C201 126.0(2) . . ? C208 N2 C211 117.7(2) . . ? C201 N2 C211 115.6(2) . . ? C202 C201 C203 121.2(2) . . ? C202 C201 N2 115.0(2) . . ? C203 C201 N2 123.7(2) . . ? C205 C202 C201 123.6(2) . . ? C205 C202 H202 118.2 . . ? C201 C202 H202 118.2 . . ? C204 C203 C201 114.4(2) . . ? C204 C203 C209 117.7(2) . . ? C201 C203 C209 128.0(2) . . ? C206 C204 C203 124.1(3) . . ? C206 C204 H204 118.0 . . ? C203 C204 H204 118.0 . . ? C202 C205 C206 115.0(2) . . ? C202 C205 C207 121.9(3) . . ? C206 C205 C207 123.0(2) . . ? C204 C206 C205 121.6(2) . . ? C204 C206 H206 119.2 . . ? C205 C206 H206 119.2 . . ? C21 C207 C22 113.4(4) . . ? C21 C207 C205 111.7(3) . . ? C22 C207 C205 108.3(3) . . ? C21 C207 C23 106.5(3) . . ? C22 C207 C23 105.9(3) . . ? C205 C207 C23 110.8(3) . . ? O2 C208 N2 120.8(3) . . ? O2 C208 C210 118.2(3) . . ? N2 C208 C210 121.0(2) . . ? C25 C209 C26 105.4(3) . . ? C25 C209 C24 110.8(3) . . ? C26 C209 C24 106.8(3) . . ? C25 C209 C203 115.4(3) . . ? C26 C209 C203 109.8(2) . . ? C24 C209 C203 108.2(3) . . ? C212 C210 C218 121.3(3) . . ? C212 C210 C208 123.2(3) . . ? C218 C210 C208 115.1(3) . . ? N2 C211 H41A 109.5 . . ? N2 C211 H41B 109.5 . . ? H41A C211 H41B 109.5 . . ? N2 C211 H41C 109.5 . . ? H41A C211 H41C 109.5 . . ? H41B C211 H41C 109.5 . . ? N2 C211 H41D 109.5 . . ? H41A C211 H41D 141.1 . . ? H41B C211 H41D 56.3 . . ? H41C C211 H41D 56.3 . . ? N2 C211 H41E 109.5 . . ? H41A C211 H41E 56.3 . . ? H41B C211 H41E 141.1 . . ? H41C C211 H41E 56.3 . . ? H41D C211 H41E 109.5 . . ? N2 C211 H41F 109.5 . . ? H41A C211 H41F 56.3 . . ? H41B C211 H41F 56.3 . . ? H41C C211 H41F 141.1 . . ? H41D C211 H41F 109.5 . . ? H41E C211 H41F 109.5 . . ? C210 C212 H21D 120.0 . . ? C210 C212 H21E 120.0 . . ? H21D C212 H21E 120.0 . . ? C210 C218 H21G 109.5 . . ? C210 C218 H21H 109.5 . . ? H21G C218 H21H 109.5 . . ? C210 C218 H21I 109.5 . . ? H21G C218 H21I 109.5 . . ? H21H C218 H21I 109.5 . . ? C210 C218 H21J 109.5 . . ? H21G C218 H21J 141.1 . . ? H21H C218 H21J 56.3 . . ? H21I C218 H21J 56.3 . . ? C210 C218 H21K 109.5 . . ? H21G C218 H21K 56.3 . . ? H21H C218 H21K 141.1 . . ? H21I C218 H21K 56.3 . . ? H21J C218 H21K 109.5 . . ? C210 C218 H21L 109.5 . . ? H21G C218 H21L 56.3 . . ? H21H C218 H21L 56.3 . . ? H21I C218 H21L 141.1 . . ? H21J C218 H21L 109.5 . . ? H21K C218 H21L 109.5 . . ? _diffrn_measured_fraction_theta_max 0.982 _diffrn_reflns_theta_full 25.06 _diffrn_measured_fraction_theta_full 0.982 _refine_diff_density_max 0.431 _refine_diff_density_min -0.223 _refine_diff_density_rms 0.068 #===END