# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2005 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Prof Natia Frank' _publ_contact_author_address ; Department of Chemistry University of Washington Box 351700 Seattle Washington 98195-1700 USA ; _publ_contact_author_email frank@chem.washington.edu loop_ _publ_author_name _publ_author_address D.G.Patel ; Department of Chemistry, BOX 351700 University of Washington Seattle, WA 98195 USA ; J.B.Benedict ; Department of Chemistry University of Washington Seattle, WA 98195 USA ; N.L.Frank ; Department of Chemistry University of Washington Seattle, WA 98195 USA ; 'Roni A. Kopelman' ; ? ; _publ_section_title ; Photochromism of a Spirooxazine in the Single Crystalline Phase ; data_JA0362961 _database_code_depnum_ccdc_archive 'CCDC 256171' _audit_creation_method SHELXL-97 _chemical_name_systematic ; DP-1-137 ; _chemical_name_common DP-1-137 _chemical_melting_point ? _chemical_formula_moiety 'C21 H23 N3 O' _chemical_formula_sum 'C21 H23 N3 O' _chemical_formula_weight 333.42 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 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' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' 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 6.6340(2) _cell_length_b 15.3270(4) _cell_length_c 16.2050(6) _cell_angle_alpha 90.00 _cell_angle_beta 100.5580(12) _cell_angle_gamma 90.00 _cell_volume 1619.82(9) _cell_formula_units_Z 4 _cell_measurement_temperature 130(2) _cell_measurement_reflns_used 307 _exptl_crystal_description cut-block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.55 _exptl_crystal_size_mid 0.41 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 0.086 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9544 _exptl_absorpt_correction_T_max 0.9797 _exptl_absorpt_process_details 'Denzo2000, using redundancy' _exptl_special_details ; Data was collected with \w and \f scans in 2^o^ increments with 15 second exposures per degree. Crystal-to-detector distance was 30 mm. 11805 full and partial reflection were integrated. ; _diffrn_ambient_temperature 130(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 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans' _diffrn_reflns_number 4354 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0386 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.88 _diffrn_reflns_theta_max 23.54 _reflns_number_total 2381 _reflns_number_gt 2036 _reflns_threshold_expression >2sigma(I) _computing_data_collection KappaCCD _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction HKL2000 _computing_structure_solution SIR97 _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'maXus, Zortep' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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. Those H atoms that where placed were refined with a riding model. U~iso~ values were fixed such that they were 1.2U~eq7~ of their parent atom U~eq~ for CH's and 1.5U~eq~ of their parent atom U~eq~ in case of methyl groups. ; _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^)+(0.0655P)^2^+0.3377P] 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 'H atoms riding' _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2381 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0445 _refine_ls_R_factor_gt 0.0365 _refine_ls_wR_factor_ref 0.1038 _refine_ls_wR_factor_gt 0.0972 _refine_ls_goodness_of_fit_ref 1.000 _refine_ls_restrained_S_all 1.000 _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 0.47008(16) 0.17802(6) 0.97471(6) 0.0225(3) Uani 1 1 d . . . N1 N 0.20095(19) 0.03438(8) 0.94122(8) 0.0227(3) Uani 1 1 d . . . N2 N 0.2669(2) -0.13429(8) 0.74478(8) 0.0274(3) Uani 1 1 d . . . N4 N 0.13603(19) 0.24617(8) 0.93735(7) 0.0209(3) Uani 1 1 d . . . C1 C 0.0314(2) 0.33773(10) 1.10116(10) 0.0266(4) Uani 1 1 d . . . H1 H -0.0819 0.3510 1.1323 0.032 Uiso 1 1 calc R . . C2 C -0.0441(2) 0.35689(10) 1.00827(10) 0.0267(4) Uani 1 1 d . . . H2A H -0.0887 0.4185 1.0017 0.032 Uiso 1 1 calc R . . H2B H -0.1645 0.3197 0.9872 0.032 Uiso 1 1 calc R . . C3 C 0.1216(2) 0.34042(10) 0.95543(10) 0.0244(4) Uani 1 1 d . . . H3 H 0.0717 0.3692 0.9001 0.029 Uiso 1 1 calc R . . C5 C 0.2601(2) 0.18766(9) 0.99404(9) 0.0203(4) Uani 1 1 d . . . C6 C 0.2935(2) 0.21493(10) 1.08712(9) 0.0231(4) Uani 1 1 d . . . H6 H 0.3426 0.1613 1.1198 0.028 Uiso 1 1 calc R . . C7 C 0.4624(3) 0.28359(10) 1.11255(10) 0.0259(4) Uani 1 1 d . . . H7A H 0.5109 0.2807 1.1740 0.031 Uiso 1 1 calc R . . H7B H 0.5799 0.2696 1.0850 0.031 Uiso 1 1 calc R . . C8 C 0.3896(2) 0.37615(10) 1.08864(10) 0.0255(4) Uani 1 1 d . . . H8 H 0.5051 0.4174 1.1086 0.031 Uiso 1 1 calc R . . C9 C 0.2125(3) 0.39800(10) 1.13384(10) 0.0280(4) Uani 1 1 d . . . H9A H 0.1710 0.4596 1.1233 0.034 Uiso 1 1 calc R . . H9B H 0.2566 0.3899 1.1951 0.034 Uiso 1 1 calc R . . C10 C 0.0940(3) 0.24170(10) 1.11658(10) 0.0259(4) Uani 1 1 d . . . H10A H -0.0190 0.2044 1.0875 0.031 Uiso 1 1 calc R . . H10B H 0.1101 0.2297 1.1775 0.031 Uiso 1 1 calc R . . C11 C 0.3232(3) 0.38714(10) 0.99360(10) 0.0259(4) Uani 1 1 d . . . H11A H 0.4339 0.3648 0.9658 0.031 Uiso 1 1 calc R . . H11B H 0.3074 0.4502 0.9808 0.031 Uiso 1 1 calc R . . C12 C 0.1581(2) 0.09842(10) 0.98558(9) 0.0220(4) Uani 1 1 d . . . H12 H 0.0514 0.0893 1.0165 0.026 Uiso 1 1 calc R . . C13 C 0.3645(2) 0.04745(9) 0.89837(9) 0.0207(4) Uani 1 1 d . . . C14 C 0.3936(2) -0.01217(9) 0.83408(9) 0.0216(4) Uani 1 1 d . . . C15 C 0.2507(3) -0.07936(10) 0.80581(10) 0.0251(4) Uani 1 1 d . . . H15 H 0.1355 -0.0852 0.8327 0.030 Uiso 1 1 calc R . . C16 C 0.4337(3) -0.12540(10) 0.70755(10) 0.0267(4) Uani 1 1 d . . . H16 H 0.4487 -0.1650 0.6640 0.032 Uiso 1 1 calc R . . C17 C 0.5811(2) -0.06277(10) 0.72909(9) 0.0251(4) Uani 1 1 d . . . H17 H 0.6951 -0.0600 0.7012 0.030 Uiso 1 1 calc R . . C18 C 0.5625(2) -0.00243(9) 0.79293(9) 0.0221(4) Uani 1 1 d . . . C19 C 0.7005(2) 0.06754(10) 0.81717(10) 0.0248(4) Uani 1 1 d . . . H19 H 0.8176 0.0737 0.7916 0.030 Uiso 1 1 calc R . . C20 C 0.6675(2) 0.12619(10) 0.87674(10) 0.0243(4) Uani 1 1 d . . . H20 H 0.7597 0.1735 0.8914 0.029 Uiso 1 1 calc R . . C21 C 0.4974(2) 0.11675(9) 0.91641(9) 0.0211(4) Uani 1 1 d . . . C22 C 0.1249(2) 0.22791(10) 0.84800(9) 0.0226(4) Uani 1 1 d . . . H22A H 0.2537 0.2454 0.8313 0.034 Uiso 1 1 calc R . . H22B H 0.0110 0.2608 0.8151 0.034 Uiso 1 1 calc R . . H22C H 0.1026 0.1653 0.8378 0.034 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 0.0219(6) 0.0209(6) 0.0253(6) -0.0040(4) 0.0059(5) -0.0005(4) N1 0.0250(7) 0.0210(7) 0.0225(7) 0.0006(5) 0.0055(6) -0.0003(5) N2 0.0329(8) 0.0238(7) 0.0254(7) -0.0015(6) 0.0051(6) -0.0012(6) N4 0.0259(7) 0.0194(7) 0.0174(7) -0.0010(5) 0.0035(5) 0.0005(5) C1 0.0262(9) 0.0275(9) 0.0288(9) -0.0053(7) 0.0120(7) -0.0007(7) C2 0.0261(9) 0.0228(8) 0.0314(9) -0.0031(7) 0.0053(7) 0.0026(7) C3 0.0303(9) 0.0195(8) 0.0235(8) 0.0022(6) 0.0053(7) 0.0035(7) C5 0.0190(8) 0.0217(8) 0.0210(8) 0.0018(6) 0.0058(7) -0.0002(6) C6 0.0281(9) 0.0212(8) 0.0196(8) 0.0020(6) 0.0034(7) 0.0003(6) C7 0.0264(9) 0.0278(9) 0.0224(8) -0.0035(7) 0.0015(7) -0.0005(7) C8 0.0267(9) 0.0239(8) 0.0264(9) -0.0050(7) 0.0061(7) -0.0054(7) C9 0.0341(10) 0.0242(8) 0.0265(9) -0.0046(7) 0.0079(7) -0.0019(7) C10 0.0327(9) 0.0257(8) 0.0208(8) -0.0022(6) 0.0088(7) -0.0039(7) C11 0.0313(9) 0.0182(8) 0.0294(9) -0.0009(6) 0.0084(7) -0.0018(6) C12 0.0242(9) 0.0210(8) 0.0209(8) 0.0026(6) 0.0046(7) 0.0002(6) C13 0.0209(8) 0.0193(8) 0.0219(8) 0.0027(6) 0.0036(6) 0.0023(6) C14 0.0246(9) 0.0175(7) 0.0217(8) 0.0029(6) 0.0016(7) 0.0029(6) C15 0.0273(9) 0.0217(8) 0.0262(8) 0.0010(7) 0.0049(7) -0.0005(7) C16 0.0336(10) 0.0226(8) 0.0238(9) -0.0022(7) 0.0049(7) 0.0023(7) C17 0.0269(9) 0.0260(8) 0.0230(8) 0.0012(7) 0.0062(7) 0.0040(7) C18 0.0241(8) 0.0208(8) 0.0213(8) 0.0027(6) 0.0037(7) 0.0044(6) C19 0.0203(9) 0.0268(8) 0.0276(9) 0.0002(7) 0.0053(7) 0.0003(6) C20 0.0223(9) 0.0227(8) 0.0274(9) -0.0012(7) 0.0031(7) -0.0010(6) C21 0.0224(8) 0.0200(8) 0.0198(8) 0.0004(6) 0.0012(6) 0.0034(6) C22 0.0247(9) 0.0245(8) 0.0187(8) -0.0002(6) 0.0041(7) -0.0001(6) _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 C21 1.3675(18) . ? O1 C5 1.4901(18) . ? N1 C12 1.279(2) . ? N1 C13 1.406(2) . ? N2 C15 1.318(2) . ? N2 C16 1.361(2) . ? N4 C5 1.4313(19) . ? N4 C22 1.4632(18) . ? N4 C3 1.4807(19) . ? C1 C2 1.525(2) . ? C1 C9 1.531(2) . ? C1 C10 1.537(2) . ? C1 H1 1.0000 . ? C2 C3 1.533(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C11 1.543(2) . ? C3 H3 1.0000 . ? C5 C12 1.521(2) . ? C5 C6 1.542(2) . ? C6 C7 1.538(2) . ? C6 C10 1.543(2) . ? C6 H6 1.0000 . ? C7 C8 1.526(2) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.531(2) . ? C8 C11 1.532(2) . ? C8 H8 1.0000 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12 0.9500 . ? C13 C21 1.377(2) . ? C13 C14 1.425(2) . ? C14 C18 1.413(2) . ? C14 C15 1.418(2) . ? C15 H15 0.9500 . ? C16 C17 1.369(2) . ? C16 H16 0.9500 . ? C17 C18 1.410(2) . ? C17 H17 0.9500 . ? C18 C19 1.418(2) . ? C19 C20 1.366(2) . ? C19 H19 0.9500 . ? C20 C21 1.405(2) . ? C20 H20 0.9500 . ? C22 H22A 0.9800 . ? C22 H22B 0.9800 . ? C22 H22C 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 C21 O1 C5 117.41(11) . . ? C12 N1 C13 116.06(13) . . ? C15 N2 C16 116.97(14) . . ? C5 N4 C22 115.73(12) . . ? C5 N4 C3 122.33(12) . . ? C22 N4 C3 112.90(12) . . ? C2 C1 C9 108.66(13) . . ? C2 C1 C10 112.02(13) . . ? C9 C1 C10 110.48(13) . . ? C2 C1 H1 108.5 . . ? C9 C1 H1 108.5 . . ? C10 C1 H1 108.5 . . ? C1 C2 C3 112.35(13) . . ? C1 C2 H2A 109.1 . . ? C3 C2 H2A 109.1 . . ? C1 C2 H2B 109.1 . . ? C3 C2 H2B 109.1 . . ? H2A C2 H2B 107.9 . . ? N4 C3 C2 110.51(12) . . ? N4 C3 C11 116.70(13) . . ? C2 C3 C11 110.93(13) . . ? N4 C3 H3 106.0 . . ? C2 C3 H3 106.0 . . ? C11 C3 H3 106.0 . . ? N4 C5 O1 112.15(11) . . ? N4 C5 C12 108.16(12) . . ? O1 C5 C12 108.02(11) . . ? N4 C5 C6 114.88(12) . . ? O1 C5 C6 105.09(11) . . ? C12 C5 C6 108.29(12) . . ? C7 C6 C5 114.50(12) . . ? C7 C6 C10 111.07(12) . . ? C5 C6 C10 113.41(13) . . ? C7 C6 H6 105.7 . . ? C5 C6 H6 105.7 . . ? C10 C6 H6 105.7 . . ? C8 C7 C6 112.78(13) . . ? C8 C7 H7A 109.0 . . ? C6 C7 H7A 109.0 . . ? C8 C7 H7B 109.0 . . ? C6 C7 H7B 109.0 . . ? H7A C7 H7B 107.8 . . ? C7 C8 C9 108.47(13) . . ? C7 C8 C11 112.15(12) . . ? C9 C8 C11 110.64(13) . . ? C7 C8 H8 108.5 . . ? C9 C8 H8 108.5 . . ? C11 C8 H8 108.5 . . ? C8 C9 C1 108.96(12) . . ? C8 C9 H9A 109.9 . . ? C1 C9 H9A 109.9 . . ? C8 C9 H9B 109.9 . . ? C1 C9 H9B 109.9 . . ? H9A C9 H9B 108.3 . . ? C1 C10 C6 115.21(13) . . ? C1 C10 H10A 108.5 . . ? C6 C10 H10A 108.5 . . ? C1 C10 H10B 108.5 . . ? C6 C10 H10B 108.5 . . ? H10A C10 H10B 107.5 . . ? C8 C11 C3 114.86(13) . . ? C8 C11 H11A 108.6 . . ? C3 C11 H11A 108.6 . . ? C8 C11 H11B 108.6 . . ? C3 C11 H11B 108.6 . . ? H11A C11 H11B 107.5 . . ? N1 C12 C5 126.87(14) . . ? N1 C12 H12 116.6 . . ? C5 C12 H12 116.6 . . ? C21 C13 N1 121.80(13) . . ? C21 C13 C14 118.87(14) . . ? N1 C13 C14 119.33(13) . . ? C18 C14 C15 117.74(14) . . ? C18 C14 C13 120.17(14) . . ? C15 C14 C13 122.00(14) . . ? N2 C15 C14 124.38(15) . . ? N2 C15 H15 117.8 . . ? C14 C15 H15 117.8 . . ? N2 C16 C17 123.92(14) . . ? N2 C16 H16 118.0 . . ? C17 C16 H16 118.0 . . ? C16 C17 C18 119.50(15) . . ? C16 C17 H17 120.3 . . ? C18 C17 H17 120.3 . . ? C17 C18 C14 117.44(14) . . ? C17 C18 C19 124.09(14) . . ? C14 C18 C19 118.47(14) . . ? C20 C19 C18 120.97(14) . . ? C20 C19 H19 119.5 . . ? C18 C19 H19 119.5 . . ? C19 C20 C21 120.12(14) . . ? C19 C20 H20 119.9 . . ? C21 C20 H20 119.9 . . ? O1 C21 C13 121.06(14) . . ? O1 C21 C20 117.68(13) . . ? C13 C21 C20 121.25(14) . . ? N4 C22 H22A 109.5 . . ? N4 C22 H22B 109.5 . . ? H22A C22 H22B 109.5 . . ? N4 C22 H22C 109.5 . . ? H22A C22 H22C 109.5 . . ? H22B C22 H22C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9 C1 C2 C3 60.86(16) . . . . ? C10 C1 C2 C3 -61.48(17) . . . . ? C5 N4 C3 C2 -85.96(17) . . . . ? C22 N4 C3 C2 128.46(13) . . . . ? C5 N4 C3 C11 42.00(19) . . . . ? C22 N4 C3 C11 -103.58(15) . . . . ? C1 C2 C3 N4 80.22(16) . . . . ? C1 C2 C3 C11 -50.83(17) . . . . ? C22 N4 C5 O1 52.23(16) . . . . ? C3 N4 C5 O1 -92.46(15) . . . . ? C22 N4 C5 C12 -66.79(15) . . . . ? C3 N4 C5 C12 148.52(13) . . . . ? C22 N4 C5 C6 172.14(12) . . . . ? C3 N4 C5 C6 27.45(19) . . . . ? C21 O1 C5 N4 -86.27(15) . . . . ? C21 O1 C5 C12 32.82(15) . . . . ? C21 O1 C5 C6 148.26(12) . . . . ? N4 C5 C6 C7 -81.21(16) . . . . ? O1 C5 C6 C7 42.54(16) . . . . ? C12 C5 C6 C7 157.79(12) . . . . ? N4 C5 C6 C10 47.69(17) . . . . ? O1 C5 C6 C10 171.43(11) . . . . ? C12 C5 C6 C10 -73.32(15) . . . . ? C5 C6 C7 C8 80.46(16) . . . . ? C10 C6 C7 C8 -49.60(17) . . . . ? C6 C7 C8 C9 60.53(16) . . . . ? C6 C7 C8 C11 -61.96(17) . . . . ? C7 C8 C9 C1 -64.63(16) . . . . ? C11 C8 C9 C1 58.77(16) . . . . ? C2 C1 C9 C8 -64.05(16) . . . . ? C10 C1 C9 C8 59.21(16) . . . . ? C2 C1 C10 C6 71.31(17) . . . . ? C9 C1 C10 C6 -49.98(17) . . . . ? C7 C6 C10 C1 44.42(18) . . . . ? C5 C6 C10 C1 -86.21(16) . . . . ? C7 C8 C11 C3 70.72(17) . . . . ? C9 C8 C11 C3 -50.53(17) . . . . ? N4 C3 C11 C8 -81.90(16) . . . . ? C2 C3 C11 C8 45.85(17) . . . . ? C13 N1 C12 C5 2.4(2) . . . . ? N4 C5 C12 N1 97.10(17) . . . . ? O1 C5 C12 N1 -24.5(2) . . . . ? C6 C5 C12 N1 -137.82(15) . . . . ? C12 N1 C13 C21 13.1(2) . . . . ? C12 N1 C13 C14 -166.48(13) . . . . ? C21 C13 C14 C18 3.3(2) . . . . ? N1 C13 C14 C18 -177.13(12) . . . . ? C21 C13 C14 C15 -173.03(13) . . . . ? N1 C13 C14 C15 6.6(2) . . . . ? C16 N2 C15 C14 0.5(2) . . . . ? C18 C14 C15 N2 1.3(2) . . . . ? C13 C14 C15 N2 177.67(14) . . . . ? C15 N2 C16 C17 -0.9(2) . . . . ? N2 C16 C17 C18 -0.6(2) . . . . ? C16 C17 C18 C14 2.4(2) . . . . ? C16 C17 C18 C19 -176.70(14) . . . . ? C15 C14 C18 C17 -2.7(2) . . . . ? C13 C14 C18 C17 -179.13(13) . . . . ? C15 C14 C18 C19 176.45(13) . . . . ? C13 C14 C18 C19 0.0(2) . . . . ? C17 C18 C19 C20 176.71(14) . . . . ? C14 C18 C19 C20 -2.4(2) . . . . ? C18 C19 C20 C21 1.4(2) . . . . ? C5 O1 C21 C13 -22.40(19) . . . . ? C5 O1 C21 C20 158.70(13) . . . . ? N1 C13 C21 O1 -2.8(2) . . . . ? C14 C13 C21 O1 176.84(13) . . . . ? N1 C13 C21 C20 176.11(13) . . . . ? C14 C13 C21 C20 -4.3(2) . . . . ? C19 C20 C21 O1 -179.10(13) . . . . ? C19 C20 C21 C13 2.0(2) . . . . ? _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 23.54 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.159 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.039