# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_coden_Cambridge 182 loop_ _publ_author_name 'Jun Harada' 'Yuta Kawazoe' 'Keiichiro Ogawa' _publ_contact_author_name 'Jun Harada' _publ_contact_author_email HARADA@RAMIE.C.U-TOKYO.AC.JP _publ_section_title ; Photochromism of spiropyrans and spirooxazines in the solid state: Low temperature enhances photocolorations ; data_SNP_rt _database_code_depnum_ccdc_archive 'CCDC 756906' #TrackingRef 'harada.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,3-Trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b]pyran] ; _chemical_name_common ? _chemical_melting_point 451.4 _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 N O' _chemical_formula_weight 327.41 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 P_1_21/n_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.6137(12) _cell_length_b 6.3473(5) _cell_length_c 19.4928(16) _cell_angle_alpha 90.00 _cell_angle_beta 103.501(2) _cell_angle_gamma 90.00 _cell_volume 1758.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 300 _cell_measurement_reflns_used 4378 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 25.6 _exptl_crystal_description block _exptl_crystal_colour pale_pink _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.237 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9852 _exptl_absorpt_correction_T_max 0.9925 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 20s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 300 _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 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 26272 _diffrn_reflns_av_R_equivalents 0.0382 _diffrn_reflns_av_sigmaI/netI 0.0315 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.58 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5123 _reflns_number_gt 2984 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0706P)^2^+0.3652P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5123 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1021 _refine_ls_R_factor_gt 0.0531 _refine_ls_wR_factor_ref 0.1588 _refine_ls_wR_factor_gt 0.1313 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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 0.55334(10) 0.3057(2) 0.13611(8) 0.0376(3) Uani 1 1 d . . . C2 C 0.58456(12) 0.4711(3) 0.09940(10) 0.0495(4) Uani 1 1 d . . . C3 C 0.67438(13) 0.4701(3) 0.09137(10) 0.0525(5) Uani 1 1 d . . . C4 C 0.73766(11) 0.3059(3) 0.11867(8) 0.0430(4) Uani 1 1 d . . . C5 C 0.83067(13) 0.3006(3) 0.10890(10) 0.0536(5) Uani 1 1 d . . . C6 C 0.88985(13) 0.1411(4) 0.13525(10) 0.0596(5) Uani 1 1 d . . . C7 C 0.85944(13) -0.0223(4) 0.17300(11) 0.0610(5) Uani 1 1 d . . . C8 C 0.77038(12) -0.0224(3) 0.18322(10) 0.0505(4) Uani 1 1 d . . . C9 C 0.70633(10) 0.1402(3) 0.15658(8) 0.0381(3) Uani 1 1 d . . . C10 C 0.61214(10) 0.1441(2) 0.16561(8) 0.0366(3) Uani 1 1 d . . . C11 C 0.57465(12) -0.0076(3) 0.20781(9) 0.0447(4) Uani 1 1 d . . . C12 C 0.48497(11) -0.0056(3) 0.20966(9) 0.0459(4) Uani 1 1 d . . . C13 C 0.41472(10) 0.1376(2) 0.16437(8) 0.0383(4) Uani 1 1 d . . . C14 C 0.26394(10) 0.2672(2) 0.15149(8) 0.0390(4) Uani 1 1 d . . . C15 C 0.18833(12) 0.3874(3) 0.16037(11) 0.0502(4) Uani 1 1 d . . . C16 C 0.11107(14) 0.4007(4) 0.10410(13) 0.0638(5) Uani 1 1 d . . . C17 C 0.10834(15) 0.2984(4) 0.04182(13) 0.0727(6) Uani 1 1 d . . . C18 C 0.18477(14) 0.1764(4) 0.03333(11) 0.0621(5) Uani 1 1 d . . . C19 C 0.26227(11) 0.1618(3) 0.08891(9) 0.0423(4) Uani 1 1 d . . . C20 C 0.35092(11) 0.0320(3) 0.09746(9) 0.0420(4) Uani 1 1 d . . . C21 C 0.38037(15) 0.3611(4) 0.26108(11) 0.0538(5) Uani 1 1 d . . . C22 C 0.32706(16) -0.1965(3) 0.11319(13) 0.0594(5) Uani 1 1 d . . . C23 C 0.39561(17) 0.0340(4) 0.03434(11) 0.0591(5) Uani 1 1 d . . . N1 N 0.34744(9) 0.2231(2) 0.20117(7) 0.0406(3) Uani 1 1 d . . . O1 O 0.46233(7) 0.31962(17) 0.14223(6) 0.0443(3) Uani 1 1 d . . . H2 H 0.5417(14) 0.585(3) 0.0827(10) 0.062(6) Uiso 1 1 d . . . H3 H 0.6965(15) 0.583(4) 0.0661(12) 0.075(6) Uiso 1 1 d . . . H5 H 0.8488(14) 0.415(3) 0.0818(11) 0.066(6) Uiso 1 1 d . . . H6 H 0.9536(15) 0.135(3) 0.1289(10) 0.065(6) Uiso 1 1 d . . . H7 H 0.9034(15) -0.140(3) 0.1909(11) 0.071(6) Uiso 1 1 d . . . H8 H 0.7503(13) -0.140(3) 0.2092(10) 0.058(5) Uiso 1 1 d . . . H11 H 0.6158(12) -0.104(3) 0.2352(9) 0.050(5) Uiso 1 1 d . . . H12 H 0.4614(12) -0.103(3) 0.2415(10) 0.054(5) Uiso 1 1 d . . . H15 H 0.1888(13) 0.470(3) 0.2065(10) 0.057(5) Uiso 1 1 d . . . H16 H 0.0552(16) 0.492(4) 0.1107(11) 0.079(7) Uiso 1 1 d . . . H17 H 0.0556(18) 0.290(4) 0.0047(14) 0.096(8) Uiso 1 1 d . . . H18 H 0.1850(12) 0.099(3) -0.0104(10) 0.050(5) Uiso 1 1 d . . . H211 H 0.4023(17) 0.494(4) 0.2443(13) 0.093(8) Uiso 1 1 d . . . H212 H 0.3305(16) 0.378(4) 0.2873(12) 0.083(7) Uiso 1 1 d . . . H213 H 0.4356(18) 0.291(4) 0.2942(13) 0.089(8) Uiso 1 1 d . . . H221 H 0.3014(14) -0.207(3) 0.1567(11) 0.067(6) Uiso 1 1 d . . . H222 H 0.2736(14) -0.263(3) 0.0677(11) 0.065(6) Uiso 1 1 d . . . H223 H 0.3825(15) -0.287(3) 0.1205(10) 0.064(6) Uiso 1 1 d . . . H231 H 0.4576(16) -0.050(4) 0.0464(12) 0.079(7) Uiso 1 1 d . . . H232 H 0.4085(15) 0.183(4) 0.0200(12) 0.075(7) Uiso 1 1 d . . . H233 H 0.3536(16) -0.038(4) -0.0040(13) 0.085(8) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0350(7) 0.0370(8) 0.0431(8) 0.0045(6) 0.0137(6) 0.0009(6) C2 0.0478(10) 0.0401(9) 0.0640(11) 0.0141(8) 0.0200(8) 0.0030(8) C3 0.0502(10) 0.0448(10) 0.0676(12) 0.0128(9) 0.0243(9) -0.0064(8) C4 0.0370(8) 0.0499(10) 0.0437(9) -0.0011(7) 0.0122(7) -0.0064(7) C5 0.0423(9) 0.0670(12) 0.0548(11) -0.0014(9) 0.0181(8) -0.0104(9) C6 0.0330(9) 0.0852(15) 0.0621(12) -0.0055(11) 0.0144(8) -0.0030(9) C7 0.0385(9) 0.0767(14) 0.0667(12) 0.0087(11) 0.0100(8) 0.0130(9) C8 0.0367(8) 0.0619(12) 0.0522(10) 0.0097(9) 0.0095(7) 0.0067(8) C9 0.0331(7) 0.0458(9) 0.0347(8) 0.0000(6) 0.0062(6) -0.0002(6) C10 0.0334(7) 0.0398(8) 0.0368(8) 0.0050(6) 0.0088(6) 0.0002(6) C11 0.0416(8) 0.0454(9) 0.0483(9) 0.0174(8) 0.0130(7) 0.0081(7) C12 0.0433(9) 0.0457(9) 0.0528(10) 0.0191(8) 0.0196(7) 0.0056(7) C13 0.0364(8) 0.0365(8) 0.0468(9) 0.0085(7) 0.0192(7) 0.0033(6) C14 0.0345(7) 0.0376(8) 0.0481(9) 0.0045(7) 0.0164(6) -0.0012(6) C15 0.0417(9) 0.0475(10) 0.0673(12) 0.0023(9) 0.0245(8) 0.0050(7) C16 0.0439(10) 0.0642(13) 0.0848(15) 0.0060(11) 0.0182(10) 0.0120(9) C17 0.0437(11) 0.0891(17) 0.0765(15) 0.0100(13) -0.0035(10) 0.0107(11) C18 0.0561(11) 0.0748(14) 0.0526(12) -0.0038(10) 0.0069(9) 0.0002(10) C19 0.0380(8) 0.0432(9) 0.0467(9) 0.0028(7) 0.0117(7) 0.0007(7) C20 0.0460(9) 0.0392(9) 0.0450(9) 0.0007(7) 0.0191(7) 0.0027(7) C21 0.0547(11) 0.0594(12) 0.0507(11) -0.0079(9) 0.0191(9) -0.0058(9) C22 0.0659(13) 0.0408(10) 0.0771(14) 0.0001(9) 0.0282(11) -0.0004(9) C23 0.0652(13) 0.0692(15) 0.0501(11) -0.0045(10) 0.0281(10) 0.0033(11) N1 0.0370(7) 0.0460(8) 0.0424(7) 0.0012(6) 0.0165(5) 0.0030(6) O1 0.0366(6) 0.0387(6) 0.0620(7) 0.0149(5) 0.0207(5) 0.0053(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 C1 O1 1.3657(17) . ? C1 C10 1.375(2) . ? C1 C2 1.405(2) . ? C2 C3 1.358(2) . ? C2 H2 0.96(2) . ? C3 C4 1.412(2) . ? C3 H3 0.97(2) . ? C4 C5 1.416(2) . ? C4 C9 1.421(2) . ? C5 C6 1.352(3) . ? C5 H5 0.97(2) . ? C6 C7 1.403(3) . ? C6 H6 0.97(2) . ? C7 C8 1.362(2) . ? C7 H7 0.99(2) . ? C8 C9 1.408(2) . ? C8 H8 0.98(2) . ? C9 C10 1.428(2) . ? C10 C11 1.454(2) . ? C11 C12 1.320(2) . ? C11 H11 0.932(19) . ? C12 C13 1.495(2) . ? C12 H12 0.992(19) . ? C13 N1 1.4510(19) . ? C13 O1 1.4646(18) . ? C13 C20 1.566(2) . ? C14 C15 1.386(2) . ? C14 C19 1.387(2) . ? C14 N1 1.398(2) . ? C15 C16 1.381(3) . ? C15 H15 1.04(2) . ? C16 C17 1.369(3) . ? C16 H16 1.03(2) . ? C17 C18 1.400(3) . ? C17 H17 0.93(3) . ? C18 C19 1.376(3) . ? C18 H18 0.984(19) . ? C19 C20 1.511(2) . ? C20 C23 1.522(2) . ? C20 C22 1.539(3) . ? C21 N1 1.449(2) . ? C21 H211 0.98(3) . ? C21 H212 0.99(2) . ? C21 H213 1.01(3) . ? C22 H221 1.01(2) . ? C22 H222 1.12(2) . ? C22 H223 0.98(2) . ? C23 H231 1.03(2) . ? C23 H232 1.02(2) . ? C23 H233 0.97(3) . ? 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 O1 C1 C10 122.56(13) . . ? O1 C1 C2 115.76(14) . . ? C10 C1 C2 121.65(14) . . ? C3 C2 C1 119.53(17) . . ? C3 C2 H2 122.3(12) . . ? C1 C2 H2 118.1(12) . . ? C2 C3 C4 121.70(16) . . ? C2 C3 H3 120.1(13) . . ? C4 C3 H3 118.2(13) . . ? C3 C4 C5 122.10(16) . . ? C3 C4 C9 118.69(14) . . ? C5 C4 C9 119.21(17) . . ? C6 C5 C4 121.03(19) . . ? C6 C5 H5 122.3(12) . . ? C4 C5 H5 116.6(12) . . ? C5 C6 C7 119.99(17) . . ? C5 C6 H6 122.1(13) . . ? C7 C6 H6 117.9(12) . . ? C8 C7 C6 120.52(19) . . ? C8 C7 H7 120.6(12) . . ? C6 C7 H7 118.8(12) . . ? C7 C8 C9 121.41(19) . . ? C7 C8 H8 119.1(11) . . ? C9 C8 H8 119.5(11) . . ? C8 C9 C4 117.84(15) . . ? C8 C9 C10 122.95(15) . . ? C4 C9 C10 119.21(14) . . ? C1 C10 C9 119.19(14) . . ? C1 C10 C11 116.69(13) . . ? C9 C10 C11 124.03(14) . . ? C12 C11 C10 121.14(15) . . ? C12 C11 H11 120.1(11) . . ? C10 C11 H11 118.7(11) . . ? C11 C12 C13 122.60(14) . . ? C11 C12 H12 120.2(11) . . ? C13 C12 H12 117.2(11) . . ? N1 C13 O1 105.90(12) . . ? N1 C13 C12 112.73(13) . . ? O1 C13 C12 110.22(12) . . ? N1 C13 C20 103.38(12) . . ? O1 C13 C20 108.89(12) . . ? C12 C13 C20 115.13(14) . . ? C15 C14 C19 121.64(16) . . ? C15 C14 N1 128.04(16) . . ? C19 C14 N1 110.24(13) . . ? C16 C15 C14 117.52(18) . . ? C16 C15 H15 119.7(11) . . ? C14 C15 H15 122.7(11) . . ? C17 C16 C15 121.64(19) . . ? C17 C16 H16 121.1(12) . . ? C15 C16 H16 117.3(12) . . ? C16 C17 C18 120.5(2) . . ? C16 C17 H17 124.4(16) . . ? C18 C17 H17 114.7(16) . . ? C19 C18 C17 118.5(2) . . ? C19 C18 H18 118.7(11) . . ? C17 C18 H18 122.8(11) . . ? C18 C19 C14 120.17(16) . . ? C18 C19 C20 130.59(17) . . ? C14 C19 C20 109.12(14) . . ? C19 C20 C23 115.15(15) . . ? C19 C20 C22 107.90(14) . . ? C23 C20 C22 109.18(16) . . ? C19 C20 C13 100.78(12) . . ? C23 C20 C13 112.67(15) . . ? C22 C20 C13 110.86(15) . . ? N1 C21 H211 108.8(15) . . ? N1 C21 H212 109.7(14) . . ? H211 C21 H212 114(2) . . ? N1 C21 H213 108.4(14) . . ? H211 C21 H213 108(2) . . ? H212 C21 H213 107.1(19) . . ? C20 C22 H221 112.1(12) . . ? C20 C22 H222 110.4(11) . . ? H221 C22 H222 108.3(15) . . ? C20 C22 H223 111.4(12) . . ? H221 C22 H223 107.3(17) . . ? H222 C22 H223 107.1(16) . . ? C20 C23 H231 109.4(13) . . ? C20 C23 H232 111.8(12) . . ? H231 C23 H232 109.5(17) . . ? C20 C23 H233 107.8(14) . . ? H231 C23 H233 107.4(19) . . ? H232 C23 H233 110.8(19) . . ? C14 N1 C21 120.60(15) . . ? C14 N1 C13 108.37(12) . . ? C21 N1 C13 119.25(13) . . ? C1 O1 C13 120.92(11) . . ? 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 O1 C1 C2 C3 179.52(17) . . . . ? C10 C1 C2 C3 1.4(3) . . . . ? C1 C2 C3 C4 0.4(3) . . . . ? C2 C3 C4 C5 178.24(18) . . . . ? C2 C3 C4 C9 -1.2(3) . . . . ? C3 C4 C5 C6 -179.68(18) . . . . ? C9 C4 C5 C6 -0.2(3) . . . . ? C4 C5 C6 C7 -0.1(3) . . . . ? C5 C6 C7 C8 0.2(3) . . . . ? C6 C7 C8 C9 -0.1(3) . . . . ? C7 C8 C9 C4 -0.2(3) . . . . ? C7 C8 C9 C10 179.31(17) . . . . ? C3 C4 C9 C8 179.83(16) . . . . ? C5 C4 C9 C8 0.4(2) . . . . ? C3 C4 C9 C10 0.3(2) . . . . ? C5 C4 C9 C10 -179.16(15) . . . . ? O1 C1 C10 C9 179.73(14) . . . . ? C2 C1 C10 C9 -2.3(2) . . . . ? O1 C1 C10 C11 -3.5(2) . . . . ? C2 C1 C10 C11 174.48(16) . . . . ? C8 C9 C10 C1 -178.10(16) . . . . ? C4 C9 C10 C1 1.4(2) . . . . ? C8 C9 C10 C11 5.4(3) . . . . ? C4 C9 C10 C11 -175.11(15) . . . . ? C1 C10 C11 C12 8.8(3) . . . . ? C9 C10 C11 C12 -174.60(17) . . . . ? C10 C11 C12 C13 5.5(3) . . . . ? C11 C12 C13 N1 -140.65(18) . . . . ? C11 C12 C13 O1 -22.6(2) . . . . ? C11 C12 C13 C20 101.1(2) . . . . ? C19 C14 C15 C16 -0.7(3) . . . . ? N1 C14 C15 C16 -177.04(17) . . . . ? C14 C15 C16 C17 0.4(3) . . . . ? C15 C16 C17 C18 -0.1(4) . . . . ? C16 C17 C18 C19 0.1(4) . . . . ? C17 C18 C19 C14 -0.3(3) . . . . ? C17 C18 C19 C20 175.03(19) . . . . ? C15 C14 C19 C18 0.7(3) . . . . ? N1 C14 C19 C18 177.60(17) . . . . ? C15 C14 C19 C20 -175.59(15) . . . . ? N1 C14 C19 C20 1.32(18) . . . . ? C18 C19 C20 C23 45.2(3) . . . . ? C14 C19 C20 C23 -139.00(17) . . . . ? C18 C19 C20 C22 -77.0(2) . . . . ? C14 C19 C20 C22 98.78(17) . . . . ? C18 C19 C20 C13 166.76(19) . . . . ? C14 C19 C20 C13 -17.47(16) . . . . ? N1 C13 C20 C19 26.54(15) . . . . ? O1 C13 C20 C19 -85.74(13) . . . . ? C12 C13 C20 C19 149.93(13) . . . . ? N1 C13 C20 C23 149.80(15) . . . . ? O1 C13 C20 C23 37.52(18) . . . . ? C12 C13 C20 C23 -86.81(18) . . . . ? N1 C13 C20 C22 -87.50(16) . . . . ? O1 C13 C20 C22 160.22(13) . . . . ? C12 C13 C20 C22 35.89(18) . . . . ? C15 C14 N1 C21 -23.3(2) . . . . ? C19 C14 N1 C21 160.00(15) . . . . ? C15 C14 N1 C13 -165.95(16) . . . . ? C19 C14 N1 C13 17.38(17) . . . . ? O1 C13 N1 C14 86.81(14) . . . . ? C12 C13 N1 C14 -152.59(14) . . . . ? C20 C13 N1 C14 -27.63(15) . . . . ? O1 C13 N1 C21 -56.39(18) . . . . ? C12 C13 N1 C21 64.2(2) . . . . ? C20 C13 N1 C21 -170.83(15) . . . . ? C10 C1 O1 C13 -16.1(2) . . . . ? C2 C1 O1 C13 165.80(15) . . . . ? N1 C13 O1 C1 149.78(13) . . . . ? C12 C13 O1 C1 27.56(19) . . . . ? C20 C13 O1 C1 -99.63(15) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.270 _refine_diff_density_min -0.160 _refine_diff_density_rms 0.038 #===END data_SNP_90k _database_code_depnum_ccdc_archive 'CCDC 756907' #TrackingRef 'harada.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,3-Trimethylspiro[indoline-2,3'-[3H]-naphtho[2,1-b]pyran] ; _chemical_name_common ? _chemical_melting_point 451.4 _chemical_formula_moiety ? _chemical_formula_sum 'C23 H21 N O' _chemical_formula_weight 327.41 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 P_1_21/n_1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 14.5329(7) _cell_length_b 6.2561(3) _cell_length_c 19.3262(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.547(1) _cell_angle_gamma 90.00 _cell_volume 1708.24(15) _cell_formula_units_Z 4 _cell_measurement_temperature 90 _cell_measurement_reflns_used 5071 _cell_measurement_theta_min 2.9 _cell_measurement_theta_max 29.8 _exptl_crystal_description block _exptl_crystal_colour pale_pink _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.273 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9847 _exptl_absorpt_correction_T_max 0.9923 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 10s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 90 _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 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 25364 _diffrn_reflns_av_R_equivalents 0.0388 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -20 _diffrn_reflns_limit_h_max 20 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 30.01 _reflns_number_total 4986 _reflns_number_gt 3768 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material 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^)+(0.0759P)^2^+0.6209P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4986 _refine_ls_number_parameters 310 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0761 _refine_ls_R_factor_gt 0.0541 _refine_ls_wR_factor_ref 0.1421 _refine_ls_wR_factor_gt 0.1294 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_restrained_S_all 1.040 _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 0.55449(9) 0.3057(2) 0.13667(7) 0.0144(3) Uani 1 1 d . . . C2 C 0.58585(10) 0.4744(2) 0.09959(8) 0.0188(3) Uani 1 1 d . . . C3 C 0.67657(10) 0.4735(2) 0.09106(8) 0.0202(3) Uani 1 1 d . . . C4 C 0.74000(9) 0.3051(2) 0.11875(7) 0.0163(3) Uani 1 1 d . . . C5 C 0.83358(10) 0.3007(2) 0.10871(7) 0.0192(3) Uani 1 1 d . . . C6 C 0.89401(9) 0.1368(3) 0.13562(8) 0.0208(3) Uani 1 1 d . . . C7 C 0.86284(10) -0.0294(3) 0.17354(8) 0.0216(3) Uani 1 1 d . . . C8 C 0.77253(9) -0.0306(2) 0.18378(7) 0.0185(3) Uani 1 1 d . . . C9 C 0.70839(9) 0.1361(2) 0.15682(7) 0.0143(2) Uani 1 1 d . . . C10 C 0.61342(9) 0.1397(2) 0.16602(7) 0.0139(2) Uani 1 1 d . . . C11 C 0.57614(9) -0.0141(2) 0.20880(7) 0.0166(3) Uani 1 1 d . . . C12 C 0.48522(9) -0.0116(2) 0.21101(7) 0.0166(3) Uani 1 1 d . . . C13 C 0.41497(9) 0.1352(2) 0.16519(7) 0.0143(2) Uani 1 1 d . . . C14 C 0.26279(9) 0.2677(2) 0.15163(7) 0.0149(3) Uani 1 1 d . . . C15 C 0.18660(9) 0.3892(2) 0.16037(8) 0.0181(3) Uani 1 1 d . . . C16 C 0.10846(10) 0.4027(3) 0.10276(8) 0.0231(3) Uani 1 1 d . . . C17 C 0.10627(10) 0.2984(3) 0.03927(8) 0.0261(3) Uani 1 1 d . . . C18 C 0.18393(10) 0.1759(3) 0.03144(8) 0.0228(3) Uani 1 1 d . . . C19 C 0.26182(9) 0.1619(2) 0.08799(7) 0.0163(3) Uani 1 1 d . . . C20 C 0.35092(9) 0.0296(2) 0.09705(7) 0.0158(3) Uani 1 1 d . . . C21 C 0.37979(10) 0.3617(2) 0.26279(8) 0.0195(3) Uani 1 1 d . . . C22 C 0.32708(11) -0.2026(2) 0.11297(9) 0.0222(3) Uani 1 1 d . . . C23 C 0.39653(11) 0.0319(3) 0.03380(8) 0.0223(3) Uani 1 1 d . . . N1 N 0.34693(7) 0.22146(18) 0.20229(6) 0.0147(2) Uani 1 1 d . . . O1 O 0.46327(6) 0.32097(15) 0.14356(5) 0.0164(2) Uani 1 1 d . . . H2 H 0.5430(13) 0.590(3) 0.0813(10) 0.027(5) Uiso 1 1 d . . . H3 H 0.7000(13) 0.590(3) 0.0655(10) 0.030(5) Uiso 1 1 d . . . H5 H 0.8534(12) 0.416(3) 0.0810(10) 0.024(4) Uiso 1 1 d . . . H6 H 0.9593(13) 0.136(3) 0.1288(9) 0.024(4) Uiso 1 1 d . . . H7 H 0.9062(12) -0.148(3) 0.1927(9) 0.023(4) Uiso 1 1 d . . . H8 H 0.7533(12) -0.146(3) 0.2090(9) 0.025(4) Uiso 1 1 d . . . H11 H 0.6180(12) -0.111(3) 0.2370(9) 0.021(4) Uiso 1 1 d . . . H12 H 0.4615(12) -0.110(3) 0.2419(9) 0.019(4) Uiso 1 1 d . . . H15 H 0.1884(12) 0.471(3) 0.2062(10) 0.024(4) Uiso 1 1 d . . . H16 H 0.0549(13) 0.489(3) 0.1088(9) 0.024(4) Uiso 1 1 d . . . H17 H 0.0513(14) 0.304(3) -0.0013(11) 0.037(5) Uiso 1 1 d . . . H18 H 0.1838(12) 0.101(3) -0.0125(9) 0.018(4) Uiso 1 1 d . . . H211 H 0.4004(12) 0.497(3) 0.2477(10) 0.028(5) Uiso 1 1 d . . . H212 H 0.3281(14) 0.376(3) 0.2878(10) 0.036(5) Uiso 1 1 d . . . H213 H 0.4317(14) 0.296(3) 0.2959(10) 0.030(5) Uiso 1 1 d . . . H221 H 0.3021(13) -0.211(3) 0.1568(10) 0.030(5) Uiso 1 1 d . . . H222 H 0.2754(12) -0.270(3) 0.0674(9) 0.020(4) Uiso 1 1 d . . . H223 H 0.3825(13) -0.295(3) 0.1205(9) 0.025(5) Uiso 1 1 d . . . H231 H 0.4581(13) -0.053(3) 0.0442(10) 0.028(5) Uiso 1 1 d . . . H232 H 0.4112(14) 0.179(3) 0.0209(10) 0.033(5) Uiso 1 1 d . . . H233 H 0.3554(14) -0.038(3) -0.0073(11) 0.037(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0111(5) 0.0157(6) 0.0168(6) 0.0010(5) 0.0041(4) 0.0004(4) C2 0.0176(6) 0.0150(6) 0.0243(7) 0.0054(5) 0.0060(5) 0.0017(5) C3 0.0184(6) 0.0176(7) 0.0257(7) 0.0052(5) 0.0072(5) -0.0011(5) C4 0.0135(6) 0.0188(6) 0.0161(6) -0.0003(5) 0.0029(5) -0.0029(5) C5 0.0160(6) 0.0242(7) 0.0181(6) -0.0004(5) 0.0052(5) -0.0039(5) C6 0.0116(6) 0.0305(8) 0.0206(7) -0.0016(6) 0.0043(5) -0.0023(5) C7 0.0145(6) 0.0264(7) 0.0230(7) 0.0022(6) 0.0026(5) 0.0041(5) C8 0.0131(6) 0.0221(7) 0.0194(6) 0.0040(5) 0.0022(5) 0.0023(5) C9 0.0111(5) 0.0177(6) 0.0131(6) -0.0004(5) 0.0009(4) -0.0007(5) C10 0.0125(6) 0.0156(6) 0.0136(6) 0.0017(5) 0.0029(4) -0.0007(5) C11 0.0154(6) 0.0166(6) 0.0176(6) 0.0057(5) 0.0035(5) 0.0030(5) C12 0.0159(6) 0.0167(6) 0.0176(6) 0.0052(5) 0.0048(5) 0.0013(5) C13 0.0127(6) 0.0142(6) 0.0171(6) 0.0032(5) 0.0056(5) 0.0005(4) C14 0.0121(6) 0.0151(6) 0.0179(6) 0.0019(5) 0.0041(5) -0.0006(4) C15 0.0152(6) 0.0181(6) 0.0226(7) 0.0007(5) 0.0074(5) 0.0010(5) C16 0.0143(6) 0.0242(7) 0.0310(8) 0.0034(6) 0.0056(5) 0.0042(5) C17 0.0163(6) 0.0329(8) 0.0256(8) 0.0037(6) -0.0024(6) 0.0039(6) C18 0.0206(7) 0.0274(8) 0.0192(7) -0.0012(6) 0.0018(5) 0.0004(6) C19 0.0149(6) 0.0156(6) 0.0187(6) 0.0016(5) 0.0043(5) 0.0002(5) C20 0.0147(6) 0.0170(6) 0.0164(6) -0.0002(5) 0.0047(5) 0.0011(5) C21 0.0179(6) 0.0217(7) 0.0194(7) -0.0019(5) 0.0052(5) -0.0018(5) C22 0.0231(7) 0.0163(7) 0.0286(8) 0.0002(5) 0.0089(6) -0.0009(5) C23 0.0239(7) 0.0271(8) 0.0178(7) -0.0011(6) 0.0090(5) 0.0012(6) N1 0.0115(5) 0.0184(5) 0.0148(5) 0.0000(4) 0.0043(4) 0.0025(4) O1 0.0118(4) 0.0152(5) 0.0237(5) 0.0056(4) 0.0074(4) 0.0020(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 C1 O1 1.3664(15) . ? C1 C10 1.3806(18) . ? C1 C2 1.4100(18) . ? C2 C3 1.3665(19) . ? C2 H2 0.964(19) . ? C3 C4 1.4196(19) . ? C3 H3 0.99(2) . ? C4 C5 1.4183(18) . ? C4 C9 1.4242(18) . ? C5 C6 1.371(2) . ? C5 H5 0.980(19) . ? C6 C7 1.407(2) . ? C6 H6 0.988(18) . ? C7 C8 1.3725(19) . ? C7 H7 0.988(18) . ? C8 C9 1.4141(18) . ? C8 H8 0.952(19) . ? C9 C10 1.4325(17) . ? C10 C11 1.4534(18) . ? C11 C12 1.3320(18) . ? C11 H11 0.938(18) . ? C12 C13 1.4985(18) . ? C12 H12 0.976(17) . ? C13 N1 1.4546(16) . ? C13 O1 1.4684(15) . ? C13 C20 1.5694(18) . ? C14 C15 1.3856(18) . ? C14 C19 1.3939(19) . ? C14 N1 1.4059(16) . ? C15 C16 1.394(2) . ? C15 H15 1.016(18) . ? C16 C17 1.383(2) . ? C16 H16 0.977(18) . ? C17 C18 1.401(2) . ? C17 H17 0.98(2) . ? C18 C19 1.3799(19) . ? C18 H18 0.968(17) . ? C19 C20 1.5120(18) . ? C20 C23 1.5210(19) . ? C20 C22 1.541(2) . ? C21 N1 1.4503(18) . ? C21 H211 0.97(2) . ? C21 H212 0.99(2) . ? C21 H213 0.96(2) . ? C22 H221 0.998(19) . ? C22 H222 1.099(17) . ? C22 H223 0.973(19) . ? C23 H231 1.020(19) . ? C23 H232 0.99(2) . ? C23 H233 0.98(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag O1 C1 C10 122.35(11) . . ? O1 C1 C2 115.70(11) . . ? C10 C1 C2 121.91(12) . . ? C3 C2 C1 119.61(13) . . ? C3 C2 H2 121.2(11) . . ? C1 C2 H2 119.2(11) . . ? C2 C3 C4 121.14(13) . . ? C2 C3 H3 120.9(11) . . ? C4 C3 H3 118.0(11) . . ? C5 C4 C3 121.44(13) . . ? C5 C4 C9 119.47(12) . . ? C3 C4 C9 119.09(12) . . ? C6 C5 C4 120.82(13) . . ? C6 C5 H5 120.8(10) . . ? C4 C5 H5 118.3(10) . . ? C5 C6 C7 119.64(13) . . ? C5 C6 H6 120.4(11) . . ? C7 C6 H6 120.0(11) . . ? C8 C7 C6 120.97(13) . . ? C8 C7 H7 119.3(10) . . ? C6 C7 H7 119.8(10) . . ? C7 C8 C9 120.86(13) . . ? C7 C8 H8 118.9(11) . . ? C9 C8 H8 120.2(11) . . ? C8 C9 C4 118.23(12) . . ? C8 C9 C10 122.48(12) . . ? C4 C9 C10 119.29(12) . . ? C1 C10 C9 118.93(12) . . ? C1 C10 C11 116.98(11) . . ? C9 C10 C11 123.96(12) . . ? C12 C11 C10 121.01(12) . . ? C12 C11 H11 120.2(10) . . ? C10 C11 H11 118.7(10) . . ? C11 C12 C13 122.13(12) . . ? C11 C12 H12 120.5(10) . . ? C13 C12 H12 117.4(10) . . ? N1 C13 O1 105.78(10) . . ? N1 C13 C12 112.57(11) . . ? O1 C13 C12 110.38(10) . . ? N1 C13 C20 103.40(10) . . ? O1 C13 C20 108.87(10) . . ? C12 C13 C20 115.23(11) . . ? C15 C14 C19 121.66(12) . . ? C15 C14 N1 128.14(12) . . ? C19 C14 N1 110.13(11) . . ? C14 C15 C16 117.42(13) . . ? C14 C15 H15 121.5(10) . . ? C16 C15 H15 121.0(10) . . ? C17 C16 C15 121.66(13) . . ? C17 C16 H16 120.9(10) . . ? C15 C16 H16 117.5(10) . . ? C16 C17 C18 120.12(13) . . ? C16 C17 H17 122.4(12) . . ? C18 C17 H17 117.5(12) . . ? C19 C18 C17 118.77(14) . . ? C19 C18 H18 119.8(10) . . ? C17 C18 H18 121.5(10) . . ? C18 C19 C14 120.37(13) . . ? C18 C19 C20 130.38(13) . . ? C14 C19 C20 109.05(11) . . ? C19 C20 C23 115.11(12) . . ? C19 C20 C22 108.22(11) . . ? C23 C20 C22 109.30(12) . . ? C19 C20 C13 100.97(10) . . ? C23 C20 C13 112.69(11) . . ? C22 C20 C13 110.25(11) . . ? N1 C21 H211 110.7(11) . . ? N1 C21 H212 107.9(12) . . ? H211 C21 H212 113.0(17) . . ? N1 C21 H213 109.5(12) . . ? H211 C21 H213 109.2(15) . . ? H212 C21 H213 106.4(16) . . ? C20 C22 H221 111.4(11) . . ? C20 C22 H222 110.2(9) . . ? H221 C22 H222 110.1(14) . . ? C20 C22 H223 111.8(11) . . ? H221 C22 H223 107.1(15) . . ? H222 C22 H223 106.2(14) . . ? C20 C23 H231 111.3(11) . . ? C20 C23 H232 111.8(11) . . ? H231 C23 H232 107.8(15) . . ? C20 C23 H233 110.5(12) . . ? H231 C23 H233 105.5(16) . . ? H232 C23 H233 109.7(16) . . ? C14 N1 C21 120.36(11) . . ? C14 N1 C13 108.30(10) . . ? C21 N1 C13 119.24(11) . . ? C1 O1 C13 120.78(10) . . ? 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 O1 C1 C2 C3 179.11(13) . . . . ? C10 C1 C2 C3 1.1(2) . . . . ? C1 C2 C3 C4 0.2(2) . . . . ? C2 C3 C4 C5 178.56(14) . . . . ? C2 C3 C4 C9 -0.8(2) . . . . ? C3 C4 C5 C6 -179.88(14) . . . . ? C9 C4 C5 C6 -0.5(2) . . . . ? C4 C5 C6 C7 0.2(2) . . . . ? C5 C6 C7 C8 0.3(2) . . . . ? C6 C7 C8 C9 -0.4(2) . . . . ? C7 C8 C9 C4 0.0(2) . . . . ? C7 C8 C9 C10 179.58(13) . . . . ? C5 C4 C9 C8 0.38(19) . . . . ? C3 C4 C9 C8 179.80(13) . . . . ? C5 C4 C9 C10 -179.18(12) . . . . ? C3 C4 C9 C10 0.24(19) . . . . ? O1 C1 C10 C9 -179.56(11) . . . . ? C2 C1 C10 C9 -1.7(2) . . . . ? O1 C1 C10 C11 -3.59(19) . . . . ? C2 C1 C10 C11 174.25(13) . . . . ? C8 C9 C10 C1 -178.53(13) . . . . ? C4 C9 C10 C1 1.01(19) . . . . ? C8 C9 C10 C11 5.8(2) . . . . ? C4 C9 C10 C11 -174.66(12) . . . . ? C1 C10 C11 C12 9.3(2) . . . . ? C9 C10 C11 C12 -174.99(13) . . . . ? C10 C11 C12 C13 5.5(2) . . . . ? C11 C12 C13 N1 -141.28(14) . . . . ? C11 C12 C13 O1 -23.34(18) . . . . ? C11 C12 C13 C20 100.48(15) . . . . ? C19 C14 C15 C16 -0.2(2) . . . . ? N1 C14 C15 C16 -176.66(13) . . . . ? C14 C15 C16 C17 0.3(2) . . . . ? C15 C16 C17 C18 -0.2(2) . . . . ? C16 C17 C18 C19 0.0(2) . . . . ? C17 C18 C19 C14 0.1(2) . . . . ? C17 C18 C19 C20 174.41(14) . . . . ? C15 C14 C19 C18 0.0(2) . . . . ? N1 C14 C19 C18 177.04(13) . . . . ? C15 C14 C19 C20 -175.42(12) . . . . ? N1 C14 C19 C20 1.61(15) . . . . ? C18 C19 C20 C23 45.8(2) . . . . ? C14 C19 C20 C23 -139.38(13) . . . . ? C18 C19 C20 C22 -76.78(18) . . . . ? C14 C19 C20 C22 98.04(13) . . . . ? C18 C19 C20 C13 167.44(15) . . . . ? C14 C19 C20 C13 -17.74(14) . . . . ? N1 C13 C20 C19 26.74(12) . . . . ? O1 C13 C20 C19 -85.41(11) . . . . ? C12 C13 C20 C19 149.99(11) . . . . ? N1 C13 C20 C23 150.06(11) . . . . ? O1 C13 C20 C23 37.92(14) . . . . ? C12 C13 C20 C23 -86.68(14) . . . . ? N1 C13 C20 C22 -87.53(12) . . . . ? O1 C13 C20 C22 160.33(10) . . . . ? C12 C13 C20 C22 35.73(15) . . . . ? C15 C14 N1 C21 -23.9(2) . . . . ? C19 C14 N1 C21 159.34(12) . . . . ? C15 C14 N1 C13 -166.05(13) . . . . ? C19 C14 N1 C13 17.16(15) . . . . ? O1 C13 N1 C14 86.82(12) . . . . ? C12 C13 N1 C14 -152.56(11) . . . . ? C20 C13 N1 C14 -27.57(13) . . . . ? O1 C13 N1 C21 -55.84(14) . . . . ? C12 C13 N1 C21 64.78(15) . . . . ? C20 C13 N1 C21 -170.23(11) . . . . ? C10 C1 O1 C13 -16.89(18) . . . . ? C2 C1 O1 C13 165.14(12) . . . . ? N1 C13 O1 C1 150.84(11) . . . . ? C12 C13 O1 C1 28.81(15) . . . . ? C20 C13 O1 C1 -98.60(12) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.01 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.544 _refine_diff_density_min -0.225 _refine_diff_density_rms 0.059 #===END data_SNO_rt _database_code_depnum_ccdc_archive 'CCDC 756908' #TrackingRef 'harada.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,3-Trimethylspiro[indoline-2,3'-[3H]naphth[2,1-b][1,4]oxazine] ; _chemical_name_common ? _chemical_melting_point 416.9 _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 N2 O' _chemical_formula_weight 328.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P_b_c_a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.1642(8) _cell_length_b 16.8250(8) _cell_length_c 12.4068(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3582.9(3) _cell_formula_units_Z 8 _cell_measurement_temperature 300 _cell_measurement_reflns_used 7059 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 29.8 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.218 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.075 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9633 _exptl_absorpt_correction_T_max 0.9705 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 300 _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 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 53515 _diffrn_reflns_av_R_equivalents 0.0258 _diffrn_reflns_av_sigmaI/netI 0.0131 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5238 _reflns_number_gt 3612 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2008)' _computing_publication_material 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^)+(0.0577P)^2^+1.5292P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5238 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0852 _refine_ls_R_factor_gt 0.0554 _refine_ls_wR_factor_ref 0.1645 _refine_ls_wR_factor_gt 0.1347 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 C2 C 0.40063(9) 0.13193(10) 0.45689(12) 0.0446(3) Uani 1 1 d . . . C3 C 0.38771(10) 0.17027(11) 0.55613(13) 0.0527(4) Uani 1 1 d . . . C4 C 0.43361(11) 0.23244(11) 0.58511(13) 0.0529(4) Uani 1 1 d . . . C5 C 0.49481(9) 0.26001(10) 0.51779(12) 0.0456(3) Uani 1 1 d . . . C6 C 0.54228(12) 0.32519(12) 0.54628(15) 0.0586(4) Uani 1 1 d . . . C7 C 0.60116(14) 0.34982(13) 0.48027(17) 0.0702(6) Uani 1 1 d . . . C8 C 0.61497(13) 0.31050(14) 0.38259(17) 0.0686(5) Uani 1 1 d . . . C9 C 0.57018(10) 0.24738(12) 0.35223(15) 0.0547(4) Uani 1 1 d . . . C10 C 0.50860(9) 0.22034(9) 0.41873(12) 0.0418(3) Uani 1 1 d . . . C11 C 0.46044(9) 0.15513(9) 0.39016(12) 0.0411(3) Uani 1 1 d . . . C13 C 0.43020(11) 0.05724(12) 0.26819(15) 0.0570(4) Uani 1 1 d . . . C14 C 0.35534(9) 0.03571(10) 0.32401(13) 0.0461(4) Uani 1 1 d . . . C16 C 0.26918(10) -0.06817(9) 0.33871(13) 0.0480(4) Uani 1 1 d . . . C17 C 0.23445(15) -0.13872(12) 0.37121(17) 0.0673(5) Uani 1 1 d . . . C18 C 0.15463(17) -0.14383(16) 0.3646(2) 0.0813(7) Uani 1 1 d . . . C19 C 0.11050(15) -0.08208(18) 0.3274(2) 0.0852(8) Uani 1 1 d . . . C20 C 0.14518(12) -0.01183(15) 0.29343(18) 0.0686(5) Uani 1 1 d . . . C21 C 0.22534(10) -0.00565(10) 0.29915(13) 0.0479(4) Uani 1 1 d . . . C22 C 0.27982(10) 0.05916(9) 0.26192(14) 0.0498(4) Uani 1 1 d . . . C23 C 0.40391(18) -0.09257(19) 0.4010(3) 0.0882(8) Uani 1 1 d . . . C24 C 0.29210(18) 0.04955(19) 0.13935(18) 0.0793(7) Uani 1 1 d . . . C25 C 0.25395(17) 0.14381(13) 0.2873(3) 0.0804(7) Uani 1 1 d . . . N12 N 0.47745(8) 0.11172(9) 0.29559(11) 0.0538(4) Uani 1 1 d . . . N15 N 0.34831(8) -0.04904(8) 0.33537(13) 0.0533(4) Uani 1 1 d . . . O1 O 0.35318(7) 0.06941(8) 0.43201(10) 0.0582(3) Uani 1 1 d . . . H3 H 0.3462(13) 0.1505(12) 0.6008(18) 0.071(6) Uiso 1 1 d . . . H4 H 0.4263(10) 0.2597(11) 0.6538(16) 0.058(5) Uiso 1 1 d . . . H6 H 0.5327(12) 0.3519(12) 0.6152(19) 0.070(6) Uiso 1 1 d . . . H7 H 0.6332(14) 0.3940(14) 0.5004(19) 0.080(7) Uiso 1 1 d . . . H8 H 0.6583(15) 0.3277(15) 0.336(2) 0.093(8) Uiso 1 1 d . . . H9 H 0.5800(11) 0.2210(11) 0.2844(17) 0.059(5) Uiso 1 1 d . . . H13 H 0.4422(12) 0.0233(12) 0.2016(18) 0.070(6) Uiso 1 1 d . . . H17 H 0.2684(14) -0.1797(15) 0.402(2) 0.090(8) Uiso 1 1 d . . . H18 H 0.1301(17) -0.1918(18) 0.386(3) 0.118(10) Uiso 1 1 d . . . H19 H 0.0517(18) -0.0869(16) 0.324(2) 0.111(9) Uiso 1 1 d . . . H20 H 0.1139(15) 0.0343(15) 0.264(2) 0.096(8) Uiso 1 1 d . . . H231 H 0.456(2) -0.0692(18) 0.385(3) 0.117(11) Uiso 1 1 d . . . H232 H 0.3965(19) -0.0734(18) 0.482(3) 0.130(12) Uiso 1 1 d . . . H233 H 0.403(2) -0.150(3) 0.383(3) 0.170(16) Uiso 1 1 d . . . H241 H 0.3307(18) 0.0921(17) 0.110(3) 0.111(9) Uiso 1 1 d . . . H242 H 0.3113(17) -0.0046(17) 0.119(2) 0.102(9) Uiso 1 1 d . . . H243 H 0.2413(19) 0.0601(19) 0.100(3) 0.125(11) Uiso 1 1 d . . . H251 H 0.2935(16) 0.1823(16) 0.264(2) 0.101(9) Uiso 1 1 d . . . H252 H 0.2077(17) 0.1513(15) 0.246(2) 0.093(8) Uiso 1 1 d . . . H253 H 0.2403(15) 0.1516(15) 0.368(2) 0.092(8) 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 C2 0.0420(8) 0.0520(8) 0.0397(7) 0.0015(6) 0.0033(6) 0.0031(6) C3 0.0508(9) 0.0673(11) 0.0401(8) 0.0002(7) 0.0100(7) 0.0007(8) C4 0.0573(10) 0.0639(10) 0.0374(8) -0.0042(7) 0.0042(7) 0.0064(8) C5 0.0501(8) 0.0489(8) 0.0379(7) 0.0034(6) -0.0031(6) 0.0066(7) C6 0.0721(12) 0.0584(10) 0.0453(9) -0.0013(8) -0.0032(8) -0.0012(9) C7 0.0843(15) 0.0674(12) 0.0589(11) 0.0019(10) -0.0039(10) -0.0222(11) C8 0.0704(13) 0.0775(13) 0.0579(11) 0.0048(10) 0.0084(10) -0.0200(11) C9 0.0542(10) 0.0636(10) 0.0463(9) 0.0010(8) 0.0060(7) -0.0055(8) C10 0.0408(7) 0.0472(8) 0.0372(7) 0.0059(6) 0.0002(6) 0.0073(6) C11 0.0385(7) 0.0481(8) 0.0366(7) 0.0019(6) 0.0042(6) 0.0065(6) C13 0.0532(10) 0.0645(11) 0.0534(10) -0.0136(8) 0.0166(8) -0.0044(8) C14 0.0459(8) 0.0479(8) 0.0446(8) -0.0006(6) 0.0060(6) 0.0014(6) C16 0.0582(10) 0.0420(8) 0.0438(8) -0.0014(6) 0.0060(7) -0.0006(7) C17 0.0950(16) 0.0478(10) 0.0591(11) 0.0017(8) 0.0123(11) -0.0089(10) C18 0.0933(18) 0.0760(15) 0.0747(14) -0.0145(12) 0.0258(13) -0.0377(14) C19 0.0611(13) 0.107(2) 0.0876(16) -0.0281(15) 0.0114(12) -0.0295(14) C20 0.0519(11) 0.0843(14) 0.0697(12) -0.0117(11) -0.0039(9) -0.0006(10) C21 0.0489(8) 0.0505(8) 0.0444(8) -0.0036(7) 0.0001(6) 0.0004(7) C22 0.0518(9) 0.0437(8) 0.0540(9) 0.0080(7) 0.0009(7) 0.0064(7) C23 0.0796(17) 0.0838(17) 0.101(2) 0.0203(15) -0.0169(15) 0.0301(14) C24 0.0904(17) 0.0960(18) 0.0517(11) 0.0205(12) -0.0006(11) 0.0021(15) C25 0.0754(15) 0.0471(11) 0.119(2) 0.0126(12) 0.0045(15) 0.0164(10) N12 0.0486(8) 0.0638(9) 0.0490(7) -0.0100(6) 0.0150(6) -0.0040(7) N15 0.0527(8) 0.0460(7) 0.0611(9) 0.0072(6) 0.0007(7) 0.0117(6) O1 0.0558(7) 0.0704(8) 0.0484(6) -0.0091(6) 0.0154(5) -0.0136(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 C2 O1 1.366(2) . ? C2 C11 1.375(2) . ? C2 C3 1.408(2) . ? C3 C4 1.358(3) . ? C3 H3 0.96(2) . ? C4 C5 1.420(2) . ? C4 H4 0.98(2) . ? C5 C6 1.411(3) . ? C5 C10 1.418(2) . ? C6 C7 1.365(3) . ? C6 H6 0.98(2) . ? C7 C8 1.401(3) . ? C7 H7 0.96(2) . ? C8 C9 1.364(3) . ? C8 H8 0.98(3) . ? C9 C10 1.416(2) . ? C9 H9 0.97(2) . ? C10 C11 1.419(2) . ? C11 N12 1.4127(19) . ? C13 N12 1.270(2) . ? C13 C14 1.504(2) . ? C13 H13 1.02(2) . ? C14 N15 1.438(2) . ? C14 O1 1.455(2) . ? C14 C22 1.559(2) . ? C16 C21 1.383(2) . ? C16 C17 1.388(2) . ? C16 N15 1.396(2) . ? C17 C18 1.375(4) . ? C17 H17 0.98(3) . ? C18 C19 1.366(4) . ? C18 H18 0.95(3) . ? C19 C20 1.389(3) . ? C19 H19 1.01(3) . ? C20 C21 1.382(3) . ? C20 H20 1.01(3) . ? C21 C22 1.509(2) . ? C22 C25 1.525(3) . ? C22 C24 1.544(3) . ? C23 N15 1.453(3) . ? C23 H231 0.99(3) . ? C23 H232 1.07(4) . ? C23 H233 0.99(4) . ? C24 H241 1.04(3) . ? C24 H242 1.00(3) . ? C24 H243 1.01(3) . ? C25 H251 0.98(3) . ? C25 H252 0.95(3) . ? C25 H253 1.04(3) . ? 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 O1 C2 C11 121.85(14) . . ? O1 C2 C3 117.18(14) . . ? C11 C2 C3 120.93(16) . . ? C4 C3 C2 119.55(16) . . ? C4 C3 H3 123.0(13) . . ? C2 C3 H3 117.5(13) . . ? C3 C4 C5 121.68(15) . . ? C3 C4 H4 121.2(11) . . ? C5 C4 H4 117.1(11) . . ? C6 C5 C10 119.10(15) . . ? C6 C5 C4 122.25(15) . . ? C10 C5 C4 118.65(15) . . ? C7 C6 C5 120.86(18) . . ? C7 C6 H6 120.5(13) . . ? C5 C6 H6 118.6(12) . . ? C6 C7 C8 120.1(2) . . ? C6 C7 H7 120.3(15) . . ? C8 C7 H7 119.7(15) . . ? C9 C8 C7 120.74(19) . . ? C9 C8 H8 119.5(15) . . ? C7 C8 H8 119.7(15) . . ? C8 C9 C10 120.66(18) . . ? C8 C9 H9 120.0(12) . . ? C10 C9 H9 119.4(12) . . ? C9 C10 C5 118.58(15) . . ? C9 C10 C11 122.54(14) . . ? C5 C10 C11 118.88(14) . . ? C2 C11 N12 120.50(14) . . ? C2 C11 C10 120.27(14) . . ? N12 C11 C10 119.13(13) . . ? N12 C13 C14 126.59(15) . . ? N12 C13 H13 119.3(12) . . ? C14 C13 H13 114.1(12) . . ? N15 C14 O1 107.10(13) . . ? N15 C14 C13 110.84(14) . . ? O1 C14 C13 110.60(13) . . ? N15 C14 C22 103.28(13) . . ? O1 C14 C22 109.59(13) . . ? C13 C14 C22 114.95(14) . . ? C21 C16 C17 121.32(18) . . ? C21 C16 N15 110.08(14) . . ? C17 C16 N15 128.56(17) . . ? C18 C17 C16 117.6(2) . . ? C18 C17 H17 124.9(15) . . ? C16 C17 H17 117.3(15) . . ? C19 C18 C17 121.7(2) . . ? C19 C18 H18 119.7(18) . . ? C17 C18 H18 118.6(18) . . ? C18 C19 C20 120.8(2) . . ? C18 C19 H19 120.4(16) . . ? C20 C19 H19 118.8(16) . . ? C21 C20 C19 118.4(2) . . ? C21 C20 H20 119.2(15) . . ? C19 C20 H20 122.4(14) . . ? C20 C21 C16 120.18(18) . . ? C20 C21 C22 130.98(17) . . ? C16 C21 C22 108.73(14) . . ? C21 C22 C25 115.56(17) . . ? C21 C22 C24 108.09(17) . . ? C25 C22 C24 109.9(2) . . ? C21 C22 C14 100.43(12) . . ? C25 C22 C14 112.14(18) . . ? C24 C22 C14 110.29(16) . . ? N15 C23 H231 105.8(18) . . ? N15 C23 H232 107.4(17) . . ? H231 C23 H232 100(3) . . ? N15 C23 H233 111(2) . . ? H231 C23 H233 110(3) . . ? H232 C23 H233 120(3) . . ? C22 C24 H241 111.1(17) . . ? C22 C24 H242 113.0(17) . . ? H241 C24 H242 109(2) . . ? C22 C24 H243 109.8(19) . . ? H241 C24 H243 105(2) . . ? H242 C24 H243 109(3) . . ? C22 C25 H251 110.8(16) . . ? C22 C25 H252 104.9(16) . . ? H251 C25 H252 110(2) . . ? C22 C25 H253 112.5(14) . . ? H251 C25 H253 111(2) . . ? H252 C25 H253 108(2) . . ? C13 N12 C11 117.60(14) . . ? C16 N15 C14 108.24(13) . . ? C16 N15 C23 120.40(19) . . ? C14 N15 C23 119.98(19) . . ? C2 O1 C14 119.54(12) . . ? 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 O1 C2 C3 C4 179.55(16) . . . . ? C11 C2 C3 C4 1.8(3) . . . . ? C2 C3 C4 C5 -0.1(3) . . . . ? C3 C4 C5 C6 179.15(17) . . . . ? C3 C4 C5 C10 -1.0(3) . . . . ? C10 C5 C6 C7 -0.5(3) . . . . ? C4 C5 C6 C7 179.38(19) . . . . ? C5 C6 C7 C8 0.3(3) . . . . ? C6 C7 C8 C9 -0.1(4) . . . . ? C7 C8 C9 C10 0.1(3) . . . . ? C8 C9 C10 C5 -0.4(3) . . . . ? C8 C9 C10 C11 179.80(17) . . . . ? C6 C5 C10 C9 0.5(2) . . . . ? C4 C5 C10 C9 -179.34(15) . . . . ? C6 C5 C10 C11 -179.64(15) . . . . ? C4 C5 C10 C11 0.5(2) . . . . ? O1 C2 C11 N12 -3.5(2) . . . . ? C3 C2 C11 N12 174.13(15) . . . . ? O1 C2 C11 C10 -179.94(14) . . . . ? C3 C2 C11 C10 -2.3(2) . . . . ? C9 C10 C11 C2 -179.05(15) . . . . ? C5 C10 C11 C2 1.1(2) . . . . ? C9 C10 C11 N12 4.5(2) . . . . ? C5 C10 C11 N12 -175.35(14) . . . . ? N12 C13 C14 N15 -135.0(2) . . . . ? N12 C13 C14 O1 -16.4(3) . . . . ? N12 C13 C14 C22 108.3(2) . . . . ? C21 C16 C17 C18 -1.2(3) . . . . ? N15 C16 C17 C18 -178.39(19) . . . . ? C16 C17 C18 C19 0.0(3) . . . . ? C17 C18 C19 C20 0.9(4) . . . . ? C18 C19 C20 C21 -0.6(3) . . . . ? C19 C20 C21 C16 -0.5(3) . . . . ? C19 C20 C21 C22 175.12(19) . . . . ? C17 C16 C21 C20 1.4(3) . . . . ? N15 C16 C21 C20 179.11(17) . . . . ? C17 C16 C21 C22 -175.09(16) . . . . ? N15 C16 C21 C22 2.60(19) . . . . ? C20 C21 C22 C25 43.7(3) . . . . ? C16 C21 C22 C25 -140.3(2) . . . . ? C20 C21 C22 C24 -79.9(2) . . . . ? C16 C21 C22 C24 96.12(18) . . . . ? C20 C21 C22 C14 164.57(19) . . . . ? C16 C21 C22 C14 -19.42(17) . . . . ? N15 C14 C22 C21 28.62(15) . . . . ? O1 C14 C22 C21 -85.25(15) . . . . ? C13 C14 C22 C21 149.48(14) . . . . ? N15 C14 C22 C25 151.88(17) . . . . ? O1 C14 C22 C25 38.0(2) . . . . ? C13 C14 C22 C25 -87.3(2) . . . . ? N15 C14 C22 C24 -85.25(19) . . . . ? O1 C14 C22 C24 160.88(17) . . . . ? C13 C14 C22 C24 35.6(2) . . . . ? C14 C13 N12 C11 2.6(3) . . . . ? C2 C11 N12 C13 8.3(2) . . . . ? C10 C11 N12 C13 -175.21(16) . . . . ? C21 C16 N15 C14 17.52(19) . . . . ? C17 C16 N15 C14 -165.00(17) . . . . ? C21 C16 N15 C23 161.0(2) . . . . ? C17 C16 N15 C23 -21.5(3) . . . . ? O1 C14 N15 C16 86.57(16) . . . . ? C13 C14 N15 C16 -152.71(15) . . . . ? C22 C14 N15 C16 -29.09(17) . . . . ? O1 C14 N15 C23 -57.1(2) . . . . ? C13 C14 N15 C23 63.7(2) . . . . ? C22 C14 N15 C23 -172.7(2) . . . . ? C11 C2 O1 C14 -12.1(2) . . . . ? C3 C2 O1 C14 170.20(15) . . . . ? N15 C14 O1 C2 141.05(14) . . . . ? C13 C14 O1 C2 20.2(2) . . . . ? C22 C14 O1 C2 -107.57(16) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.292 _refine_diff_density_min -0.171 _refine_diff_density_rms 0.037 #===END data_SNO_90k _database_code_depnum_ccdc_archive 'CCDC 756909' #TrackingRef 'harada.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; 1,3,3-Trimethylspiro[indoline-2,3'-[3H]naphth[2,1-b][1,4]oxazine] ; _chemical_name_common ? _chemical_melting_point 416.9 _chemical_formula_moiety ? _chemical_formula_sum 'C22 H20 N2 O' _chemical_formula_weight 328.40 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P_b_c_a loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 17.275(2) _cell_length_b 16.559(2) _cell_length_c 12.2061(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3491.6(8) _cell_formula_units_Z 8 _cell_measurement_temperature 90 _cell_measurement_reflns_used 6422 _cell_measurement_theta_min 2.4 _cell_measurement_theta_max 30.0 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.50 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.249 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1392 _exptl_absorpt_coefficient_mu 0.077 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9624 _exptl_absorpt_correction_T_max 0.9698 _exptl_absorpt_process_details 'SADABS (Sheldrick, 2002)' _exptl_special_details ; The data collection covered over a full sphere of reciprocal space by a combination of four sets of exposures; each set had a different \f angle (0, 90, 180 and 270\%) for the crystal and each exposure of 5s covered 0.3\% in \w. The crystal-to-detector distance was 4 cm and the detector swing angle was -32\%. Crystal decay was monitored by repeating the measurement of the initial 50 frames at the end of data collection and analyzing the duplicate reflections. ; _diffrn_ambient_temperature 90 _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 'Bruker SMART 1000 CCD diffractometer' _diffrn_measurement_method \w_scan _diffrn_detector_area_resol_mean 8.192 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 52107 _diffrn_reflns_av_R_equivalents 0.0174 _diffrn_reflns_av_sigmaI/netI 0.0085 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 23 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 30.05 _reflns_number_total 5101 _reflns_number_gt 4606 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 1998)' _computing_cell_refinement 'SAINT (Bruker, 1998)' _computing_data_reduction SAINT _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Bruker, 2008)' _computing_publication_material 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^)+(0.0739P)^2^+1.2302P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary ? _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5101 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0492 _refine_ls_R_factor_gt 0.0448 _refine_ls_wR_factor_ref 0.1284 _refine_ls_wR_factor_gt 0.1226 _refine_ls_goodness_of_fit_ref 1.056 _refine_ls_restrained_S_all 1.056 _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 C2 C 0.40075(5) 0.13039(6) 0.45985(7) 0.01710(18) Uani 1 1 d . . . C3 C 0.38780(6) 0.17017(6) 0.56058(8) 0.01977(19) Uani 1 1 d . . . C4 C 0.43410(6) 0.23417(6) 0.58939(7) 0.01962(19) Uani 1 1 d . . . C5 C 0.49502(5) 0.26141(6) 0.51990(7) 0.01719(18) Uani 1 1 d . . . C6 C 0.54262(6) 0.32801(6) 0.54824(8) 0.02093(19) Uani 1 1 d . . . C7 C 0.60184(6) 0.35199(6) 0.48058(9) 0.0248(2) Uani 1 1 d . . . C8 C 0.61586(6) 0.31074(7) 0.38142(9) 0.0249(2) Uani 1 1 d . . . C9 C 0.57032(5) 0.24634(6) 0.35122(8) 0.02033(19) Uani 1 1 d . . . C10 C 0.50888(5) 0.22010(5) 0.41978(7) 0.01572(17) Uani 1 1 d . . . C11 C 0.46050(5) 0.15341(5) 0.39140(7) 0.01582(17) Uani 1 1 d . . . C13 C 0.42950(6) 0.05368(6) 0.26798(8) 0.02125(19) Uani 1 1 d . . . C14 C 0.35448(5) 0.03353(6) 0.32514(7) 0.01710(18) Uani 1 1 d . . . C16 C 0.26667(5) -0.07036(5) 0.33839(7) 0.01744(18) Uani 1 1 d . . . C17 C 0.23125(6) -0.14176(6) 0.37100(8) 0.0233(2) Uani 1 1 d . . . C18 C 0.15075(7) -0.14566(7) 0.36467(9) 0.0278(2) Uani 1 1 d . . . C19 C 0.10738(6) -0.08085(8) 0.32739(10) 0.0288(2) Uani 1 1 d . . . C20 C 0.14386(6) -0.00949(7) 0.29361(9) 0.0237(2) Uani 1 1 d . . . C21 C 0.22375(5) -0.00488(5) 0.29944(7) 0.01694(18) Uani 1 1 d . . . C22 C 0.27954(5) 0.06015(5) 0.26273(8) 0.01769(18) Uani 1 1 d . . . C23 C 0.39996(7) -0.09812(7) 0.40160(10) 0.0293(2) Uani 1 1 d . . . C24 C 0.29113(7) 0.05225(7) 0.13784(9) 0.0287(2) Uani 1 1 d . . . C25 C 0.25544(7) 0.14656(6) 0.29040(10) 0.0277(2) Uani 1 1 d . . . N12 N 0.47744(5) 0.10858(5) 0.29615(7) 0.02006(17) Uani 1 1 d . . . N15 N 0.34577(5) -0.05283(5) 0.33443(7) 0.01929(17) Uani 1 1 d . . . O1 O 0.35372(4) 0.06658(4) 0.43572(6) 0.02063(16) Uani 1 1 d . . . H3 H 0.3456(9) 0.1527(9) 0.6071(13) 0.033(4) Uiso 1 1 d . . . H4 H 0.4269(8) 0.2620(9) 0.6561(12) 0.024(3) Uiso 1 1 d . . . H6 H 0.5324(9) 0.3576(9) 0.6168(12) 0.026(3) Uiso 1 1 d . . . H7 H 0.6341(10) 0.3970(10) 0.5018(14) 0.036(4) Uiso 1 1 d . . . H8 H 0.6591(10) 0.3285(10) 0.3329(15) 0.041(4) Uiso 1 1 d . . . H9 H 0.5798(9) 0.2192(9) 0.2833(12) 0.028(4) Uiso 1 1 d . . . H13 H 0.4408(8) 0.0200(9) 0.2006(12) 0.026(3) Uiso 1 1 d . . . H17 H 0.2620(10) -0.1882(10) 0.4012(14) 0.037(4) Uiso 1 1 d . . . H18 H 0.1238(10) -0.1942(10) 0.3873(14) 0.040(4) Uiso 1 1 d . . . H19 H 0.0492(10) -0.0843(10) 0.3226(14) 0.041(4) Uiso 1 1 d . . . H20 H 0.1120(9) 0.0376(9) 0.2662(13) 0.031(4) Uiso 1 1 d . . . H231 H 0.4541(11) -0.0776(11) 0.3860(14) 0.043(4) Uiso 1 1 d . . . H232 H 0.3898(11) -0.0885(11) 0.4835(16) 0.050(5) Uiso 1 1 d . . . H233 H 0.3957(11) -0.1549(12) 0.3829(15) 0.048(5) Uiso 1 1 d . . . H241 H 0.3300(11) 0.0926(11) 0.1105(15) 0.046(5) Uiso 1 1 d . . . H242 H 0.3094(10) -0.0025(10) 0.1170(13) 0.034(4) Uiso 1 1 d . . . H243 H 0.2405(11) 0.0643(11) 0.0991(15) 0.044(5) Uiso 1 1 d . . . H251 H 0.2949(10) 0.1864(10) 0.2698(14) 0.035(4) Uiso 1 1 d . . . H252 H 0.2100(11) 0.1590(11) 0.2492(16) 0.044(4) Uiso 1 1 d . . . H253 H 0.2442(9) 0.1542(9) 0.3707(13) 0.032(4) 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 C2 0.0155(4) 0.0194(4) 0.0164(4) 0.0005(3) 0.0009(3) 0.0002(3) C3 0.0182(4) 0.0253(5) 0.0158(4) 0.0001(3) 0.0033(3) 0.0000(3) C4 0.0197(4) 0.0240(4) 0.0152(4) -0.0011(3) 0.0016(3) 0.0016(3) C5 0.0177(4) 0.0184(4) 0.0155(4) 0.0018(3) -0.0008(3) 0.0021(3) C6 0.0248(5) 0.0203(4) 0.0177(4) -0.0004(3) -0.0007(3) -0.0009(3) C7 0.0293(5) 0.0233(5) 0.0218(5) 0.0004(4) -0.0008(4) -0.0071(4) C8 0.0259(5) 0.0276(5) 0.0212(4) 0.0017(4) 0.0035(4) -0.0076(4) C9 0.0199(4) 0.0231(4) 0.0179(4) 0.0005(3) 0.0031(3) -0.0019(3) C10 0.0145(4) 0.0174(4) 0.0152(4) 0.0020(3) 0.0006(3) 0.0021(3) C11 0.0145(4) 0.0183(4) 0.0147(4) 0.0006(3) 0.0012(3) 0.0014(3) C13 0.0199(4) 0.0232(4) 0.0206(4) -0.0039(3) 0.0057(3) -0.0013(3) C14 0.0167(4) 0.0173(4) 0.0173(4) -0.0008(3) 0.0018(3) -0.0002(3) C16 0.0195(4) 0.0156(4) 0.0172(4) -0.0006(3) 0.0018(3) -0.0004(3) C17 0.0306(5) 0.0172(4) 0.0219(4) 0.0006(3) 0.0030(4) -0.0038(4) C18 0.0322(5) 0.0262(5) 0.0250(5) -0.0049(4) 0.0078(4) -0.0128(4) C19 0.0204(5) 0.0361(6) 0.0299(5) -0.0093(4) 0.0034(4) -0.0085(4) C20 0.0184(4) 0.0279(5) 0.0247(5) -0.0050(4) -0.0015(3) 0.0005(4) C21 0.0176(4) 0.0167(4) 0.0166(4) -0.0020(3) 0.0001(3) 0.0000(3) C22 0.0181(4) 0.0153(4) 0.0196(4) 0.0020(3) 0.0001(3) 0.0021(3) C23 0.0260(5) 0.0266(5) 0.0352(6) 0.0057(4) -0.0057(4) 0.0076(4) C24 0.0333(5) 0.0330(6) 0.0198(5) 0.0061(4) 0.0008(4) 0.0007(4) C25 0.0273(5) 0.0159(4) 0.0399(6) 0.0029(4) 0.0015(4) 0.0045(4) N12 0.0185(4) 0.0228(4) 0.0189(4) -0.0028(3) 0.0050(3) -0.0009(3) N15 0.0177(4) 0.0159(4) 0.0243(4) 0.0022(3) -0.0003(3) 0.0025(3) O1 0.0210(3) 0.0230(3) 0.0180(3) -0.0029(3) 0.0046(2) -0.0055(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 C2 O1 1.3650(11) . ? C2 C11 1.3816(12) . ? C2 C3 1.4127(13) . ? C3 C4 1.3735(14) . ? C3 H3 0.968(16) . ? C4 C5 1.4249(13) . ? C4 H4 0.944(14) . ? C5 C6 1.4185(13) . ? C5 C10 1.4207(12) . ? C6 C7 1.3734(14) . ? C6 H6 0.985(15) . ? C7 C8 1.4107(15) . ? C7 H7 0.965(16) . ? C8 C9 1.3754(14) . ? C8 H8 0.998(18) . ? C9 C10 1.4198(12) . ? C9 H9 0.957(15) . ? C10 C11 1.4275(13) . ? C11 N12 1.4100(12) . ? C13 N12 1.2768(13) . ? C13 C14 1.5092(13) . ? C13 H13 1.012(15) . ? C14 N15 1.4423(12) . ? C14 O1 1.4566(11) . ? C14 C22 1.5654(13) . ? C16 C17 1.3894(13) . ? C16 C21 1.3968(13) . ? C16 N15 1.3979(12) . ? C17 C18 1.3944(16) . ? C17 H17 1.005(17) . ? C18 C19 1.3856(18) . ? C18 H18 0.969(17) . ? C19 C20 1.4012(16) . ? C19 H19 1.008(18) . ? C20 C21 1.3841(13) . ? C20 H20 1.013(15) . ? C21 C22 1.5130(13) . ? C22 C25 1.5281(14) . ? C22 C24 1.5431(14) . ? C23 N15 1.4529(13) . ? C23 H231 1.014(18) . ? C23 H232 1.027(19) . ? C23 H233 0.971(19) . ? C24 H241 1.004(19) . ? C24 H242 0.994(16) . ? C24 H243 1.014(18) . ? C25 H251 0.981(17) . ? C25 H252 0.954(19) . ? C25 H253 1.007(16) . ? 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 O1 C2 C11 121.86(8) . . ? O1 C2 C3 117.03(8) . . ? C11 C2 C3 121.06(9) . . ? C4 C3 C2 119.37(8) . . ? C4 C3 H3 121.2(9) . . ? C2 C3 H3 119.4(10) . . ? C3 C4 C5 121.45(9) . . ? C3 C4 H4 121.4(9) . . ? C5 C4 H4 117.1(9) . . ? C6 C5 C10 119.10(8) . . ? C6 C5 C4 121.94(8) . . ? C10 C5 C4 118.96(8) . . ? C7 C6 C5 120.66(9) . . ? C7 C6 H6 120.0(9) . . ? C5 C6 H6 119.3(9) . . ? C6 C7 C8 120.25(9) . . ? C6 C7 H7 119.5(10) . . ? C8 C7 H7 120.3(10) . . ? C9 C8 C7 120.48(9) . . ? C9 C8 H8 119.9(10) . . ? C7 C8 H8 119.7(10) . . ? C8 C9 C10 120.46(9) . . ? C8 C9 H9 119.9(9) . . ? C10 C9 H9 119.6(9) . . ? C9 C10 C5 119.05(8) . . ? C9 C10 C11 122.10(8) . . ? C5 C10 C11 118.85(8) . . ? C2 C11 N12 120.55(8) . . ? C2 C11 C10 120.27(8) . . ? N12 C11 C10 119.07(8) . . ? N12 C13 C14 126.15(9) . . ? N12 C13 H13 119.1(8) . . ? C14 C13 H13 114.8(8) . . ? N15 C14 O1 107.38(7) . . ? N15 C14 C13 110.19(8) . . ? O1 C14 C13 110.67(7) . . ? N15 C14 C22 103.37(7) . . ? O1 C14 C22 109.74(7) . . ? C13 C14 C22 115.02(8) . . ? C17 C16 C21 121.62(9) . . ? C17 C16 N15 128.10(9) . . ? C21 C16 N15 110.24(8) . . ? C16 C17 C18 117.56(10) . . ? C16 C17 H17 121.5(10) . . ? C18 C17 H17 120.8(9) . . ? C19 C18 C17 121.44(10) . . ? C19 C18 H18 118.4(10) . . ? C17 C18 H18 120.2(10) . . ? C18 C19 C20 120.43(10) . . ? C18 C19 H19 120.9(10) . . ? C20 C19 H19 118.6(10) . . ? C21 C20 C19 118.68(10) . . ? C21 C20 H20 121.1(9) . . ? C19 C20 H20 120.2(9) . . ? C20 C21 C16 120.25(9) . . ? C20 C21 C22 131.24(9) . . ? C16 C21 C22 108.37(8) . . ? C21 C22 C25 115.30(8) . . ? C21 C22 C24 108.36(8) . . ? C25 C22 C24 109.45(9) . . ? C21 C22 C14 100.50(7) . . ? C25 C22 C14 112.43(8) . . ? C24 C22 C14 110.47(8) . . ? N15 C23 H231 108.4(10) . . ? N15 C23 H232 111.1(10) . . ? H231 C23 H232 106.7(14) . . ? N15 C23 H233 108.6(11) . . ? H231 C23 H233 110.5(15) . . ? H232 C23 H233 111.5(15) . . ? C22 C24 H241 111.0(11) . . ? C22 C24 H242 111.8(9) . . ? H241 C24 H242 108.0(14) . . ? C22 C24 H243 109.4(10) . . ? H241 C24 H243 106.9(15) . . ? H242 C24 H243 109.6(14) . . ? C22 C25 H251 112.6(10) . . ? C22 C25 H252 108.1(11) . . ? H251 C25 H252 106.9(14) . . ? C22 C25 H253 112.6(9) . . ? H251 C25 H253 107.4(13) . . ? H252 C25 H253 109.1(15) . . ? C13 N12 C11 117.54(8) . . ? C16 N15 C14 108.09(7) . . ? C16 N15 C23 120.21(9) . . ? C14 N15 C23 119.27(9) . . ? C2 O1 C14 119.04(7) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C2 C3 C4 179.26(9) . . . . ? C11 C2 C3 C4 1.81(14) . . . . ? C2 C3 C4 C5 -0.03(15) . . . . ? C3 C4 C5 C6 179.28(9) . . . . ? C3 C4 C5 C10 -1.33(14) . . . . ? C10 C5 C6 C7 -0.61(14) . . . . ? C4 C5 C6 C7 178.79(10) . . . . ? C5 C6 C7 C8 0.31(16) . . . . ? C6 C7 C8 C9 0.22(17) . . . . ? C7 C8 C9 C10 -0.43(16) . . . . ? C8 C9 C10 C5 0.12(14) . . . . ? C8 C9 C10 C11 -179.84(9) . . . . ? C6 C5 C10 C9 0.39(13) . . . . ? C4 C5 C10 C9 -179.02(8) . . . . ? C6 C5 C10 C11 -179.65(8) . . . . ? C4 C5 C10 C11 0.94(13) . . . . ? O1 C2 C11 N12 -3.31(14) . . . . ? C3 C2 C11 N12 174.00(8) . . . . ? O1 C2 C11 C10 -179.51(8) . . . . ? C3 C2 C11 C10 -2.19(14) . . . . ? C9 C10 C11 C2 -179.25(9) . . . . ? C5 C10 C11 C2 0.79(13) . . . . ? C9 C10 C11 N12 4.50(13) . . . . ? C5 C10 C11 N12 -175.46(8) . . . . ? N12 C13 C14 N15 -136.38(11) . . . . ? N12 C13 C14 O1 -17.77(14) . . . . ? N12 C13 C14 C22 107.29(12) . . . . ? C21 C16 C17 C18 -0.69(14) . . . . ? N15 C16 C17 C18 -178.09(10) . . . . ? C16 C17 C18 C19 -0.06(16) . . . . ? C17 C18 C19 C20 0.77(17) . . . . ? C18 C19 C20 C21 -0.71(16) . . . . ? C19 C20 C21 C16 -0.03(14) . . . . ? C19 C20 C21 C22 175.27(10) . . . . ? C17 C16 C21 C20 0.74(14) . . . . ? N15 C16 C21 C20 178.56(9) . . . . ? C17 C16 C21 C22 -175.53(9) . . . . ? N15 C16 C21 C22 2.29(10) . . . . ? C20 C21 C22 C25 43.82(14) . . . . ? C16 C21 C22 C25 -140.45(9) . . . . ? C20 C21 C22 C24 -79.20(13) . . . . ? C16 C21 C22 C24 96.52(9) . . . . ? C20 C21 C22 C14 164.94(10) . . . . ? C16 C21 C22 C14 -19.33(9) . . . . ? N15 C14 C22 C21 28.90(9) . . . . ? O1 C14 C22 C21 -85.39(8) . . . . ? C13 C14 C22 C21 149.06(8) . . . . ? N15 C14 C22 C25 152.05(8) . . . . ? O1 C14 C22 C25 37.75(10) . . . . ? C13 C14 C22 C25 -87.79(10) . . . . ? N15 C14 C22 C24 -85.37(9) . . . . ? O1 C14 C22 C24 160.34(8) . . . . ? C13 C14 C22 C24 34.79(11) . . . . ? C14 C13 N12 C11 2.05(15) . . . . ? C2 C11 N12 C13 9.50(14) . . . . ? C10 C11 N12 C13 -174.25(9) . . . . ? C17 C16 N15 C14 -164.39(9) . . . . ? C21 C16 N15 C14 17.97(10) . . . . ? C17 C16 N15 C23 -22.64(15) . . . . ? C21 C16 N15 C23 159.72(9) . . . . ? O1 C14 N15 C16 86.49(9) . . . . ? C13 C14 N15 C16 -152.90(8) . . . . ? C22 C14 N15 C16 -29.49(9) . . . . ? O1 C14 N15 C23 -55.69(11) . . . . ? C13 C14 N15 C23 64.92(12) . . . . ? C22 C14 N15 C23 -171.68(9) . . . . ? C11 C2 O1 C14 -14.29(13) . . . . ? C3 C2 O1 C14 168.29(8) . . . . ? N15 C14 O1 C2 143.14(8) . . . . ? C13 C14 O1 C2 22.83(11) . . . . ? C22 C14 O1 C2 -105.16(9) . . . . ? _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 30.05 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.509 _refine_diff_density_min -0.172 _refine_diff_density_rms 0.052