# Supplementary Material (ESI) for CrystEngComm # This journal is (c) The Royal Society of Chemistry 2009 data_global _journal_coden_Cambridge 1350 loop_ _publ_author_name 'Christer Aakeroy' 'John Desper' 'Antoin Douglawi' 'Silvia Giordani' 'Evan P Hurley' 'Manuel Natali' _publ_contact_author_name 'Christer Aakeroy' _publ_contact_author_email AAKEROY@KSU.EDU _publ_section_title ; The balance between closed and open forms of spiropyrans in the solid state ; # Attachment 'all.cif' data_2 _database_code_depnum_ccdc_archive 'CCDC 741054' _audit_creation_method SHELXL-97 _chemical_name_systematic ; EH-01-64-02 (ethylpropion-3-yl) nitro- spiropyran ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C24 H26 N2 O5' _chemical_formula_sum 'C24 H26 N2 O5' _chemical_formula_weight 422.47 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 23.033(3) _cell_length_b 14.036(2) _cell_length_c 27.135(4) _cell_angle_alpha 90.00 _cell_angle_beta 98.508(3) _cell_angle_gamma 90.00 _cell_volume 8676(2) _cell_formula_units_Z 16 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 7120 _cell_measurement_theta_min 2.90 _cell_measurement_theta_max 25.69 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.294 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 3584 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 87340 _diffrn_reflns_av_R_equivalents 0.1441 _diffrn_reflns_av_sigmaI/netI 0.1629 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -37 _diffrn_reflns_limit_l_max 36 _diffrn_reflns_theta_min 2.74 _diffrn_reflns_theta_max 29.52 _reflns_number_total 23631 _reflns_number_gt 9797 _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^)+(0.1000P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 23631 _refine_ls_number_parameters 1129 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.2143 _refine_ls_R_factor_gt 0.0849 _refine_ls_wR_factor_ref 0.2481 _refine_ls_wR_factor_gt 0.1995 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _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 N11_1 N 0.86537(13) 0.14177(19) 0.13019(12) 0.0270(7) Uani 1 1 d . . . C12_1 C 0.87553(15) 0.2100(2) 0.17088(15) 0.0274(8) Uani 1 1 d . . . C13_1 C 0.87794(15) 0.1470(2) 0.21922(15) 0.0281(8) Uani 1 1 d . . . C14_1 C 0.89747(15) 0.0529(2) 0.19994(16) 0.0296(9) Uani 1 1 d . . . C15_1 C 0.91872(17) -0.0279(3) 0.22568(19) 0.0419(11) Uani 1 1 d . . . H15_1 H 0.9243 -0.0290 0.2611 0.050 Uiso 1 1 calc R . . C16_1 C 0.93191(18) -0.1082(3) 0.1987(2) 0.0488(13) Uani 1 1 d . . . H16_1 H 0.9459 -0.1645 0.2160 0.059 Uiso 1 1 calc R . . C17_1 C 0.92480(18) -0.1064(3) 0.1480(2) 0.0470(13) Uani 1 1 d . . . H17_1 H 0.9348 -0.1611 0.1304 0.056 Uiso 1 1 calc R . . C18_1 C 0.90325(16) -0.0259(2) 0.12146(18) 0.0372(10) Uani 1 1 d . . . H18_1 H 0.8982 -0.0248 0.0861 0.045 Uiso 1 1 calc R . . C19_1 C 0.88925(15) 0.0532(2) 0.14849(16) 0.0295(9) Uani 1 1 d . . . C20_1 C 0.91857(19) 0.1881(3) 0.26382(17) 0.0429(11) Uani 1 1 d . . . H20A_1 H 0.9154 0.1499 0.2935 0.064 Uiso 1 1 calc R . . H20B_1 H 0.9072 0.2540 0.2695 0.064 Uiso 1 1 calc R . . H20C_1 H 0.9592 0.1867 0.2570 0.064 Uiso 1 1 calc R . . C21_1 C 0.81592(18) 0.1356(3) 0.23382(17) 0.0399(10) Uani 1 1 d . . . H21A_1 H 0.7882 0.1170 0.2044 0.060 Uiso 1 1 calc R . . H21B_1 H 0.8034 0.1963 0.2467 0.060 Uiso 1 1 calc R . . H21C_1 H 0.8168 0.0865 0.2596 0.060 Uiso 1 1 calc R . . C22_1 C 0.87111(16) 0.1739(2) 0.07987(15) 0.0307(9) Uani 1 1 d . . . H22A_1 H 0.9096 0.1529 0.0717 0.037 Uiso 1 1 calc R . . H22B_1 H 0.8704 0.2444 0.0791 0.037 Uiso 1 1 calc R . . C23_1 C 0.82208(17) 0.1356(3) 0.03983(16) 0.0369(10) Uani 1 1 d . . . H23A_1 H 0.8296 0.1575 0.0067 0.044 Uiso 1 1 calc R . . H23B_1 H 0.8236 0.0651 0.0400 0.044 Uiso 1 1 calc R . . C24_1 C 0.76021(17) 0.1676(2) 0.04764(17) 0.0361(10) Uani 1 1 d . . . H24A_1 H 0.7309 0.1261 0.0276 0.043 Uiso 1 1 calc R . . H24B_1 H 0.7560 0.1588 0.0831 0.043 Uiso 1 1 calc R . . C25_1 C 0.74683(17) 0.2697(3) 0.03342(16) 0.0349(9) Uani 1 1 d . . . O25_1 O 0.78140(13) 0.3297(2) 0.02423(14) 0.0588(10) Uani 1 1 d . . . O26_1 O 0.68953(12) 0.28839(16) 0.03244(11) 0.0369(7) Uani 1 1 d . . . C26_1 C 0.67053(18) 0.3862(2) 0.02214(17) 0.0400(10) Uani 1 1 d . . . H26A_1 H 0.6886 0.4121 -0.0059 0.048 Uiso 1 1 calc R . . H26B_1 H 0.6824 0.4266 0.0518 0.048 Uiso 1 1 calc R . . C27_1 C 0.6049(2) 0.3850(3) 0.0090(2) 0.0516(13) Uani 1 1 d . . . H27A_1 H 0.5907 0.4500 0.0016 0.077 Uiso 1 1 calc R . . H27B_1 H 0.5875 0.3598 0.0372 0.077 Uiso 1 1 calc R . . H27C_1 H 0.5937 0.3444 -0.0202 0.077 Uiso 1 1 calc R . . C28_1 C 0.83113(15) 0.2886(2) 0.16470(15) 0.0298(9) Uani 1 1 d . . . H28_1 H 0.7921 0.2740 0.1695 0.036 Uiso 1 1 calc R . . C29_1 C 0.84317(15) 0.3776(2) 0.15283(15) 0.0294(9) Uani 1 1 d . . . H29_1 H 0.8126 0.4236 0.1483 0.035 Uiso 1 1 calc R . . C31_1 C 0.94750(15) 0.3366(2) 0.15689(14) 0.0248(8) Uani 1 1 d . . . O31_1 O 0.93625(10) 0.24740(15) 0.17234(10) 0.0281(6) Uani 1 1 d . . . C32_1 C 1.00562(15) 0.3582(2) 0.15275(14) 0.0247(8) Uani 1 1 d . . . H32_1 H 1.0353 0.3112 0.1599 0.030 Uiso 1 1 calc R . . C33_1 C 1.01959(16) 0.4483(2) 0.13813(14) 0.0278(8) Uani 1 1 d . . . H33_1 H 1.0591 0.4641 0.1354 0.033 Uiso 1 1 calc R . . C34_1 C 0.97540(16) 0.5160(2) 0.12736(14) 0.0263(8) Uani 1 1 d . . . N34_1 N 0.98982(15) 0.61075(19) 0.11157(13) 0.0338(8) Uani 1 1 d . . . O33_1 O 1.04184(12) 0.63111(17) 0.11242(11) 0.0413(7) Uani 1 1 d . . . O34_1 O 0.94976(13) 0.66714(17) 0.09733(13) 0.0495(8) Uani 1 1 d . . . C35_1 C 0.91741(16) 0.4955(2) 0.13160(15) 0.0295(9) Uani 1 1 d . . . H35_1 H 0.8881 0.5430 0.1242 0.035 Uiso 1 1 calc R . . C36_1 C 0.90232(15) 0.4054(2) 0.14667(15) 0.0269(8) Uani 1 1 d . . . N11_2 N 0.61799(13) 0.12332(18) 0.15325(12) 0.0249(7) Uani 1 1 d . . . C12_2 C 0.62822(15) 0.0448(2) 0.18817(14) 0.0244(8) Uani 1 1 d . . . C13_2 C 0.63352(15) 0.0938(2) 0.24080(14) 0.0247(8) Uani 1 1 d . . . C14_2 C 0.65690(15) 0.1903(2) 0.22803(15) 0.0265(8) Uani 1 1 d . . . C15_2 C 0.68223(16) 0.2625(2) 0.25874(16) 0.0320(9) Uani 1 1 d . . . H15_2 H 0.6893 0.2537 0.2938 0.038 Uiso 1 1 calc R . . C16_2 C 0.69717(17) 0.3479(2) 0.23786(18) 0.0377(11) Uani 1 1 d . . . H16_2 H 0.7147 0.3976 0.2587 0.045 Uiso 1 1 calc R . . C17_2 C 0.68654(16) 0.3607(2) 0.18679(18) 0.0373(11) Uani 1 1 d . . . H17_2 H 0.6969 0.4194 0.1729 0.045 Uiso 1 1 calc R . . C18_2 C 0.66067(16) 0.2885(2) 0.15500(16) 0.0314(9) Uani 1 1 d . . . H18_2 H 0.6536 0.2970 0.1199 0.038 Uiso 1 1 calc R . . C19_2 C 0.64584(15) 0.2039(2) 0.17688(15) 0.0259(8) Uani 1 1 d . . . C20_2 C 0.67249(17) 0.0386(3) 0.28099(15) 0.0354(9) Uani 1 1 d . . . H20A_2 H 0.6725 0.0700 0.3132 0.053 Uiso 1 1 calc R . . H20B_2 H 0.7126 0.0367 0.2731 0.053 Uiso 1 1 calc R . . H20C_2 H 0.6575 -0.0265 0.2826 0.053 Uiso 1 1 calc R . . C21_2 C 0.57130(17) 0.1076(3) 0.25515(16) 0.0345(9) Uani 1 1 d . . . H21A_2 H 0.5739 0.1476 0.2850 0.052 Uiso 1 1 calc R . . H21B_2 H 0.5548 0.0454 0.2619 0.052 Uiso 1 1 calc R . . H21C_2 H 0.5459 0.1386 0.2276 0.052 Uiso 1 1 calc R . . C22_2 C 0.61599(16) 0.1053(2) 0.10044(14) 0.0284(9) Uani 1 1 d . . . H22A_2 H 0.6205 0.0360 0.0952 0.034 Uiso 1 1 calc R . . H22B_2 H 0.6495 0.1379 0.0887 0.034 Uiso 1 1 calc R . . C23_2 C 0.55963(16) 0.1386(2) 0.06954(14) 0.0289(8) Uani 1 1 d . . . H23A_2 H 0.5547 0.2078 0.0746 0.035 Uiso 1 1 calc R . . H23B_2 H 0.5259 0.1053 0.0807 0.035 Uiso 1 1 calc R . . C24_2 C 0.56004(17) 0.1187(2) 0.01445(15) 0.0322(9) Uani 1 1 d . . . H24A_2 H 0.5918 0.1569 0.0032 0.039 Uiso 1 1 calc R . . H24B_2 H 0.5698 0.0507 0.0106 0.039 Uiso 1 1 calc R . . C25_2 C 0.50423(18) 0.1398(3) -0.01888(15) 0.0323(9) Uani 1 1 d . . . O25_2 O 0.47994(14) 0.08847(19) -0.05116(11) 0.0477(8) Uani 1 1 d . . . O26_2 O 0.48282(11) 0.22617(17) -0.00865(10) 0.0342(6) Uani 1 1 d . . . C26_2 C 0.43015(17) 0.2558(3) -0.04132(16) 0.0374(10) Uani 1 1 d . . . H26A_2 H 0.3974 0.2117 -0.0382 0.045 Uiso 1 1 calc R . . H26B_2 H 0.4372 0.2559 -0.0765 0.045 Uiso 1 1 calc R . . C27_2 C 0.4156(2) 0.3546(3) -0.02564(19) 0.0540(13) Uani 1 1 d . . . H27A_2 H 0.3823 0.3794 -0.0487 0.081 Uiso 1 1 calc R . . H27B_2 H 0.4497 0.3962 -0.0261 0.081 Uiso 1 1 calc R . . H27C_2 H 0.4053 0.3526 0.0081 0.081 Uiso 1 1 calc R . . C28_2 C 0.58298(15) -0.0315(2) 0.17767(14) 0.0249(8) Uani 1 1 d . . . H28_2 H 0.5431 -0.0145 0.1779 0.030 Uiso 1 1 calc R . . C29_2 C 0.59483(15) -0.1217(2) 0.16804(14) 0.0252(8) Uani 1 1 d . . . H29_2 H 0.5639 -0.1670 0.1632 0.030 Uiso 1 1 calc R . . C31_2 C 0.69924(15) -0.0824(2) 0.17175(14) 0.0231(8) Uani 1 1 d . . . O31_2 O 0.68835(10) 0.00886(15) 0.18387(10) 0.0286(6) Uani 1 1 d . . . C32_2 C 0.75737(15) -0.1052(2) 0.16667(14) 0.0266(8) Uani 1 1 d . . . H32_2 H 0.7866 -0.0570 0.1703 0.032 Uiso 1 1 calc R . . C33_2 C 0.77203(16) -0.1976(2) 0.15646(14) 0.0273(8) Uani 1 1 d . . . H33_2 H 0.8114 -0.2141 0.1536 0.033 Uiso 1 1 calc R . . C34_2 C 0.72770(16) -0.2662(2) 0.15048(14) 0.0268(8) Uani 1 1 d . . . N34_2 N 0.74209(15) -0.3640(2) 0.13956(13) 0.0329(8) Uani 1 1 d . . . O33_2 O 0.79492(12) -0.38522(18) 0.14130(12) 0.0434(7) Uani 1 1 d . . . O34_2 O 0.70266(13) -0.42214(17) 0.12907(12) 0.0472(8) Uani 1 1 d . . . C35_2 C 0.67004(15) -0.2447(2) 0.15425(14) 0.0254(8) Uani 1 1 d . . . H35_2 H 0.6410 -0.2932 0.1496 0.030 Uiso 1 1 calc R . . C36_2 C 0.65466(15) -0.1520(2) 0.16483(13) 0.0219(7) Uani 1 1 d . . . N11_3 N 0.36689(12) 0.10265(18) 0.11053(11) 0.0243(7) Uani 1 1 d . . . C12_3 C 0.37381(14) 0.1902(2) 0.13924(14) 0.0239(8) Uani 1 1 d . . . C13_3 C 0.37281(15) 0.1567(2) 0.19432(14) 0.0258(8) Uani 1 1 d . . . C14_3 C 0.39776(15) 0.0575(2) 0.19170(14) 0.0237(8) Uani 1 1 d . . . C15_3 C 0.42075(16) -0.0036(2) 0.22958(16) 0.0307(9) Uani 1 1 d . . . H15_3 H 0.4239 0.0157 0.2634 0.037 Uiso 1 1 calc R . . C16_3 C 0.43937(16) -0.0944(2) 0.21734(17) 0.0332(9) Uani 1 1 d . . . H16_3 H 0.4552 -0.1374 0.2429 0.040 Uiso 1 1 calc R . . C17_3 C 0.43459(16) -0.1211(2) 0.16796(16) 0.0320(9) Uani 1 1 d . . . H17_3 H 0.4470 -0.1831 0.1600 0.038 Uiso 1 1 calc R . . C18_3 C 0.41198(15) -0.0597(2) 0.12921(15) 0.0273(8) Uani 1 1 d . . . H18_3 H 0.4096 -0.0781 0.0953 0.033 Uiso 1 1 calc R . . C19_3 C 0.39317(15) 0.0296(2) 0.14265(14) 0.0224(8) Uani 1 1 d . . . C20_3 C 0.40796(17) 0.2232(2) 0.23275(15) 0.0326(9) Uani 1 1 d . . . H20A_3 H 0.4059 0.1995 0.2664 0.049 Uiso 1 1 calc R . . H20B_3 H 0.3914 0.2875 0.2292 0.049 Uiso 1 1 calc R . . H20C_3 H 0.4490 0.2249 0.2272 0.049 Uiso 1 1 calc R . . C21_3 C 0.30890(16) 0.1501(2) 0.20523(16) 0.0340(9) Uani 1 1 d . . . H21A_3 H 0.3087 0.1230 0.2385 0.051 Uiso 1 1 calc R . . H21B_3 H 0.2860 0.1091 0.1803 0.051 Uiso 1 1 calc R . . H21C_3 H 0.2915 0.2139 0.2038 0.051 Uiso 1 1 calc R . . C22_3 C 0.37362(16) 0.1040(2) 0.05799(14) 0.0287(9) Uani 1 1 d . . . H22A_3 H 0.4123 0.0768 0.0541 0.034 Uiso 1 1 calc R . . H22B_3 H 0.3728 0.1709 0.0463 0.034 Uiso 1 1 calc R . . C23_3 C 0.32582(16) 0.0481(2) 0.02581(15) 0.0304(9) Uani 1 1 d . . . H23A_3 H 0.3257 -0.0182 0.0384 0.036 Uiso 1 1 calc R . . H23B_3 H 0.3348 0.0457 -0.0087 0.036 Uiso 1 1 calc R . . C24_3 C 0.26462(16) 0.0918(2) 0.02548(16) 0.0305(9) Uani 1 1 d . . . H24A_3 H 0.2344 0.0448 0.0118 0.037 Uiso 1 1 calc R . . H24B_3 H 0.2588 0.1064 0.0601 0.037 Uiso 1 1 calc R . . C25_3 C 0.25688(17) 0.1816(3) -0.00531(15) 0.0325(9) Uani 1 1 d . . . O25_3 O 0.28760(12) 0.2074(2) -0.03508(11) 0.0436(7) Uani 1 1 d . . . O26_3 O 0.20882(11) 0.23069(17) 0.00393(10) 0.0343(6) Uani 1 1 d . . . C26_3 C 0.19350(17) 0.3152(3) -0.02624(17) 0.0377(10) Uani 1 1 d . . . H26A_3 H 0.1517 0.3308 -0.0258 0.045 Uiso 1 1 calc R . . H26B_3 H 0.1985 0.3016 -0.0612 0.045 Uiso 1 1 calc R . . C27_3 C 0.23070(19) 0.4000(3) -0.0078(2) 0.0488(12) Uani 1 1 d . . . H27A_3 H 0.2193 0.4549 -0.0294 0.073 Uiso 1 1 calc R . . H27B_3 H 0.2722 0.3851 -0.0085 0.073 Uiso 1 1 calc R . . H27C_3 H 0.2248 0.4152 0.0263 0.073 Uiso 1 1 calc R . . C28_3 C 0.32908(15) 0.2652(2) 0.12001(15) 0.0274(8) Uani 1 1 d . . . H28_3 H 0.2891 0.2470 0.1120 0.033 Uiso 1 1 calc R . . C29_3 C 0.34354(15) 0.3563(2) 0.11385(15) 0.0294(9) Uani 1 1 d . . . H29_3 H 0.3135 0.4018 0.1040 0.035 Uiso 1 1 calc R . . C31_3 C 0.44807(15) 0.3168(2) 0.13346(13) 0.0225(8) Uani 1 1 d . . . O31_3 O 0.43428(10) 0.22289(14) 0.13577(10) 0.0254(6) Uani 1 1 d . . . C32_3 C 0.50766(15) 0.3399(2) 0.14247(14) 0.0255(8) Uani 1 1 d . . . H32_3 H 0.5363 0.2913 0.1498 0.031 Uiso 1 1 calc R . . C33_3 C 0.52450(16) 0.4342(2) 0.14054(14) 0.0281(8) Uani 1 1 d . . . H33_3 H 0.5648 0.4515 0.1465 0.034 Uiso 1 1 calc R . . C34_3 C 0.48089(15) 0.5037(2) 0.12964(14) 0.0243(8) Uani 1 1 d . . . N34_3 N 0.49850(15) 0.6034(2) 0.12983(13) 0.0340(8) Uani 1 1 d . . . O33_3 O 0.55014(14) 0.62311(18) 0.14642(12) 0.0450(8) Uani 1 1 d . . . O34_3 O 0.46167(13) 0.66387(16) 0.11419(12) 0.0426(8) Uani 1 1 d . . . C35_3 C 0.42190(16) 0.4812(2) 0.12026(14) 0.0255(8) Uani 1 1 d . . . H35_3 H 0.3935 0.5301 0.1127 0.031 Uiso 1 1 calc R . . C36_3 C 0.40432(15) 0.3864(2) 0.12200(14) 0.0249(8) Uani 1 1 d . . . N11_4 N 0.10596(13) 0.11733(18) 0.10931(12) 0.0253(7) Uani 1 1 d . . . C12_4 C 0.11875(15) 0.0379(2) 0.14288(15) 0.0261(8) Uani 1 1 d . . . C13_4 C 0.12301(16) 0.0831(2) 0.19608(15) 0.0291(9) Uani 1 1 d . . . C14_4 C 0.14439(15) 0.1829(2) 0.18495(15) 0.0256(8) Uani 1 1 d . . . C15_4 C 0.16862(16) 0.2539(2) 0.21671(16) 0.0317(9) Uani 1 1 d . . . H15_4 H 0.1751 0.2438 0.2517 0.038 Uiso 1 1 calc R . . C16_4 C 0.18344(17) 0.3407(2) 0.19683(17) 0.0363(10) Uani 1 1 d . . . H16_4 H 0.1992 0.3904 0.2185 0.044 Uiso 1 1 calc R . . C17_4 C 0.17539(17) 0.3551(2) 0.14598(17) 0.0346(10) Uani 1 1 d . . . H17_4 H 0.1872 0.4137 0.1331 0.042 Uiso 1 1 calc R . . C18_4 C 0.14979(16) 0.2838(2) 0.11278(16) 0.0300(9) Uani 1 1 d . . . H18_4 H 0.1437 0.2937 0.0778 0.036 Uiso 1 1 calc R . . C19_4 C 0.13369(14) 0.1979(2) 0.13348(15) 0.0248(8) Uani 1 1 d . . . C20_4 C 0.16410(18) 0.0291(3) 0.23563(16) 0.0376(10) Uani 1 1 d . . . H20A_4 H 0.1631 0.0584 0.2683 0.056 Uiso 1 1 calc R . . H20B_4 H 0.2042 0.0318 0.2277 0.056 Uiso 1 1 calc R . . H20C_4 H 0.1515 -0.0375 0.2364 0.056 Uiso 1 1 calc R . . C21_4 C 0.06187(17) 0.0917(3) 0.21176(16) 0.0357(10) Uani 1 1 d . . . H21A_4 H 0.0347 0.1201 0.1845 0.053 Uiso 1 1 calc R . . H21B_4 H 0.0641 0.1322 0.2414 0.053 Uiso 1 1 calc R . . H21C_4 H 0.0478 0.0283 0.2194 0.053 Uiso 1 1 calc R . . C22_4 C 0.10164(17) 0.1014(2) 0.05587(15) 0.0332(9) Uani 1 1 d . . . H22A_4 H 0.1095 0.0334 0.0499 0.040 Uiso 1 1 calc R . . H22B_4 H 0.1323 0.1394 0.0429 0.040 Uiso 1 1 calc R . . C23_4 C 0.04169(17) 0.1280(2) 0.02704(16) 0.0342(9) Uani 1 1 d . . . H23A_4 H 0.0403 0.1093 -0.0083 0.041 Uiso 1 1 calc R . . H23B_4 H 0.0108 0.0920 0.0408 0.041 Uiso 1 1 calc R . . C24_4 C 0.02908(17) 0.2346(2) 0.02986(16) 0.0340(9) Uani 1 1 d . . . H24A_4 H 0.0338 0.2536 0.0654 0.041 Uiso 1 1 calc R . . H24B_4 H 0.0588 0.2698 0.0142 0.041 Uiso 1 1 calc R . . C25_4 C -0.03067(17) 0.2645(3) 0.00530(15) 0.0323(9) Uani 1 1 d . . . O25_4 O -0.06742(12) 0.21310(18) -0.01713(11) 0.0398(7) Uani 1 1 d . . . O26_4 O -0.03883(11) 0.35850(17) 0.01212(11) 0.0392(7) Uani 1 1 d . . . C26_4 C -0.09500(18) 0.3987(3) -0.00892(19) 0.0458(11) Uani 1 1 d . . . H26A_4 H -0.1244 0.3864 0.0135 0.055 Uiso 1 1 calc R . . H26B_4 H -0.1090 0.3692 -0.0417 0.055 Uiso 1 1 calc R . . C27_4 C -0.08721(19) 0.5029(3) -0.01486(18) 0.0428(11) Uani 1 1 d . . . H27A_4 H -0.1243 0.5311 -0.0307 0.064 Uiso 1 1 calc R . . H27B_4 H -0.0567 0.5144 -0.0358 0.064 Uiso 1 1 calc R . . H27C_4 H -0.0755 0.5320 0.0179 0.064 Uiso 1 1 calc R . . C28_4 C 0.07629(16) -0.0425(2) 0.13348(15) 0.0306(9) Uani 1 1 d . . . H28_4 H 0.0357 -0.0289 0.1325 0.037 Uiso 1 1 calc R . . C29_4 C 0.09187(16) -0.1323(2) 0.12632(15) 0.0303(9) Uani 1 1 d . . . H29_4 H 0.0629 -0.1810 0.1230 0.036 Uiso 1 1 calc R . . C31_4 C 0.19404(15) -0.0823(2) 0.12740(14) 0.0238(8) Uani 1 1 d . . . O31_4 O 0.17987(10) 0.00821(15) 0.13732(10) 0.0293(6) Uani 1 1 d . . . C32_4 C 0.25207(16) -0.0988(2) 0.12059(15) 0.0285(9) Uani 1 1 d . . . H32_4 H 0.2791 -0.0474 0.1227 0.034 Uiso 1 1 calc R . . C33_4 C 0.27018(16) -0.1894(2) 0.11078(14) 0.0283(8) Uani 1 1 d . . . H33_4 H 0.3095 -0.2010 0.1058 0.034 Uiso 1 1 calc R . . C34_4 C 0.22968(16) -0.2641(2) 0.10823(14) 0.0259(8) Uani 1 1 d . . . N34_4 N 0.24877(15) -0.36068(19) 0.09990(13) 0.0328(8) Uani 1 1 d . . . O33_4 O 0.30057(13) -0.37298(17) 0.09374(11) 0.0415(7) Uani 1 1 d . . . O34_4 O 0.21341(13) -0.42624(16) 0.09896(12) 0.0451(8) Uani 1 1 d . . . C35_4 C 0.17185(16) -0.2489(2) 0.11510(14) 0.0279(8) Uani 1 1 d . . . H35_4 H 0.1453 -0.3010 0.1141 0.033 Uiso 1 1 calc R . . C36_4 C 0.15281(15) -0.1565(2) 0.12352(15) 0.0258(8) 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 N11_1 0.0210(16) 0.0213(14) 0.039(2) -0.0015(13) 0.0061(14) -0.0005(12) C12_1 0.0144(18) 0.0206(16) 0.048(3) -0.0032(16) 0.0066(17) -0.0027(13) C13_1 0.0153(18) 0.0277(17) 0.043(2) 0.0014(16) 0.0076(17) -0.0047(15) C14_1 0.0169(19) 0.0195(16) 0.055(3) 0.0035(16) 0.0119(18) -0.0028(14) C15_1 0.025(2) 0.031(2) 0.070(3) 0.015(2) 0.010(2) -0.0030(17) C16_1 0.030(2) 0.0171(18) 0.100(4) 0.016(2) 0.012(3) 0.0033(16) C17_1 0.026(2) 0.0193(18) 0.099(4) -0.006(2) 0.019(3) 0.0000(16) C18_1 0.021(2) 0.0230(17) 0.070(3) -0.0113(18) 0.014(2) -0.0044(15) C19_1 0.0145(18) 0.0147(15) 0.061(3) -0.0017(16) 0.0103(18) -0.0034(13) C20_1 0.038(3) 0.047(2) 0.045(3) -0.003(2) 0.009(2) -0.007(2) C21_1 0.033(2) 0.033(2) 0.057(3) -0.0016(19) 0.018(2) -0.0036(18) C22_1 0.023(2) 0.0255(17) 0.045(3) -0.0023(16) 0.0088(18) -0.0014(15) C23_1 0.026(2) 0.037(2) 0.048(3) -0.0045(19) 0.0050(19) -0.0050(17) C24_1 0.028(2) 0.0306(19) 0.050(3) -0.0006(18) 0.0044(19) -0.0077(16) C25_1 0.023(2) 0.038(2) 0.044(3) 0.0041(18) 0.0040(18) -0.0072(17) O25_1 0.0286(17) 0.0465(17) 0.102(3) 0.0233(17) 0.0128(18) -0.0085(14) O26_1 0.0302(16) 0.0270(13) 0.055(2) 0.0052(12) 0.0128(14) -0.0025(11) C26_1 0.042(3) 0.0238(18) 0.057(3) 0.0070(18) 0.016(2) -0.0016(17) C27_1 0.043(3) 0.032(2) 0.080(4) 0.007(2) 0.008(3) 0.0042(19) C28_1 0.0158(18) 0.0229(16) 0.053(3) -0.0055(16) 0.0119(18) 0.0006(14) C29_1 0.0165(18) 0.0176(15) 0.055(3) -0.0029(16) 0.0100(18) 0.0020(14) C31_1 0.0179(18) 0.0173(15) 0.039(2) 0.0002(14) 0.0020(16) -0.0018(13) O31_1 0.0157(13) 0.0160(10) 0.0532(18) 0.0030(11) 0.0074(12) 0.0002(9) C32_1 0.0157(18) 0.0212(16) 0.037(2) 0.0020(15) 0.0045(16) -0.0002(14) C33_1 0.025(2) 0.0211(16) 0.038(2) -0.0033(15) 0.0075(17) -0.0057(15) C34_1 0.025(2) 0.0167(15) 0.038(2) 0.0004(15) 0.0078(17) -0.0050(14) N34_1 0.036(2) 0.0178(14) 0.049(2) -0.0032(14) 0.0090(17) -0.0029(14) O33_1 0.0342(17) 0.0283(13) 0.062(2) 0.0024(13) 0.0091(15) -0.0112(12) O34_1 0.0442(19) 0.0194(12) 0.084(3) 0.0074(14) 0.0078(17) 0.0016(12) C35_1 0.022(2) 0.0164(15) 0.050(3) -0.0023(15) 0.0054(18) 0.0026(14) C36_1 0.0196(19) 0.0190(15) 0.042(2) -0.0042(15) 0.0044(17) 0.0011(14) N11_2 0.0219(16) 0.0171(13) 0.037(2) 0.0033(12) 0.0085(14) -0.0012(11) C12_2 0.0141(17) 0.0183(15) 0.041(2) 0.0001(15) 0.0055(16) -0.0007(13) C13_2 0.0194(19) 0.0212(15) 0.034(2) 0.0006(15) 0.0067(16) -0.0011(14) C14_2 0.0147(18) 0.0201(16) 0.046(3) -0.0015(16) 0.0077(17) 0.0024(13) C15_2 0.024(2) 0.0278(18) 0.044(3) -0.0073(17) 0.0064(18) 0.0026(15) C16_2 0.024(2) 0.0189(17) 0.071(3) -0.0132(18) 0.009(2) -0.0039(15) C17_2 0.019(2) 0.0218(17) 0.073(3) 0.0006(19) 0.014(2) 0.0037(15) C18_2 0.023(2) 0.0258(17) 0.047(3) 0.0069(17) 0.0126(18) 0.0017(15) C19_2 0.0136(17) 0.0193(15) 0.046(3) -0.0041(15) 0.0098(17) 0.0044(13) C20_2 0.030(2) 0.035(2) 0.040(3) 0.0033(18) 0.0022(19) -0.0034(17) C21_2 0.028(2) 0.035(2) 0.043(3) -0.0006(18) 0.0124(19) 0.0009(17) C22_2 0.023(2) 0.0233(16) 0.040(2) 0.0005(16) 0.0081(17) 0.0000(15) C23_2 0.022(2) 0.0270(17) 0.038(2) -0.0029(16) 0.0061(17) 0.0004(15) C24_2 0.029(2) 0.0260(18) 0.042(3) -0.0019(16) 0.0085(19) 0.0025(16) C25_2 0.035(2) 0.0294(18) 0.034(2) -0.0036(17) 0.0088(19) -0.0041(17) O25_2 0.056(2) 0.0385(15) 0.044(2) -0.0069(14) -0.0058(16) -0.0035(14) O26_2 0.0284(15) 0.0345(14) 0.0387(17) -0.0006(12) 0.0019(13) 0.0037(11) C26_2 0.025(2) 0.045(2) 0.041(3) 0.0029(19) 0.0030(19) 0.0041(18) C27_2 0.050(3) 0.054(3) 0.058(3) 0.006(2) 0.006(2) 0.025(2) C28_2 0.0141(17) 0.0207(16) 0.041(2) 0.0003(15) 0.0068(16) -0.0014(13) C29_2 0.0197(19) 0.0206(16) 0.035(2) -0.0001(15) 0.0044(16) -0.0046(14) C31_2 0.0173(18) 0.0186(15) 0.035(2) 0.0005(14) 0.0095(16) 0.0008(13) O31_2 0.0136(12) 0.0194(11) 0.0539(18) -0.0067(11) 0.0082(12) -0.0010(10) C32_2 0.0168(18) 0.0235(16) 0.039(2) 0.0007(15) 0.0010(16) -0.0022(14) C33_2 0.0210(19) 0.0250(17) 0.037(2) 0.0028(15) 0.0071(17) 0.0035(15) C34_2 0.029(2) 0.0174(15) 0.035(2) 0.0023(15) 0.0097(17) 0.0021(14) N34_2 0.032(2) 0.0222(14) 0.045(2) 0.0046(14) 0.0099(16) 0.0028(14) O33_2 0.0344(17) 0.0334(14) 0.066(2) 0.0046(14) 0.0180(15) 0.0134(13) O34_2 0.0438(19) 0.0185(12) 0.080(2) -0.0037(13) 0.0127(16) -0.0049(12) C35_2 0.0212(19) 0.0175(15) 0.038(2) 0.0047(14) 0.0062(16) -0.0044(14) C36_2 0.0186(18) 0.0188(15) 0.029(2) 0.0018(14) 0.0052(15) -0.0019(13) N11_3 0.0206(16) 0.0166(13) 0.0358(19) -0.0024(12) 0.0045(14) 0.0006(11) C12_3 0.0127(17) 0.0184(15) 0.041(2) -0.0025(15) 0.0041(16) -0.0013(13) C13_3 0.0173(18) 0.0202(15) 0.041(2) -0.0088(15) 0.0079(17) -0.0017(13) C14_3 0.0184(18) 0.0150(14) 0.039(2) -0.0024(15) 0.0090(16) -0.0033(13) C15_3 0.022(2) 0.0262(17) 0.045(3) 0.0013(17) 0.0096(18) -0.0032(15) C16_3 0.024(2) 0.0211(16) 0.055(3) 0.0061(17) 0.0081(19) 0.0003(15) C17_3 0.021(2) 0.0139(15) 0.062(3) -0.0009(17) 0.0094(19) -0.0005(14) C18_3 0.0191(19) 0.0216(16) 0.043(2) -0.0066(16) 0.0092(17) -0.0038(14) C19_3 0.0161(18) 0.0146(14) 0.037(2) -0.0021(14) 0.0042(16) -0.0028(13) C20_3 0.031(2) 0.0209(16) 0.046(3) -0.0084(16) 0.0043(19) 0.0022(15) C21_3 0.022(2) 0.0276(18) 0.055(3) -0.0076(18) 0.0128(19) 0.0004(15) C22_3 0.024(2) 0.0213(16) 0.042(3) -0.0056(15) 0.0095(18) -0.0018(14) C23_3 0.025(2) 0.0293(18) 0.037(2) -0.0079(16) 0.0043(17) -0.0021(16) C24_3 0.020(2) 0.0246(17) 0.047(3) -0.0033(16) 0.0063(18) -0.0040(15) C25_3 0.022(2) 0.041(2) 0.034(2) -0.0048(18) 0.0019(18) -0.0003(17) O25_3 0.0317(16) 0.0559(17) 0.046(2) 0.0101(14) 0.0154(15) 0.0060(14) O26_3 0.0226(14) 0.0322(13) 0.0504(19) 0.0068(12) 0.0126(13) 0.0043(11) C26_3 0.025(2) 0.035(2) 0.054(3) 0.0133(19) 0.009(2) 0.0054(17) C27_3 0.034(3) 0.034(2) 0.079(4) 0.010(2) 0.009(2) 0.0038(19) C28_3 0.0143(17) 0.0233(16) 0.044(2) -0.0046(16) 0.0028(16) -0.0016(14) C29_3 0.0148(18) 0.0206(16) 0.051(3) -0.0020(16) -0.0008(17) 0.0014(14) C31_3 0.0223(19) 0.0147(14) 0.031(2) -0.0031(14) 0.0058(16) 0.0016(13) O31_3 0.0129(12) 0.0162(10) 0.0471(17) -0.0019(10) 0.0039(11) 0.0009(9) C32_3 0.0137(17) 0.0223(16) 0.042(2) -0.0032(15) 0.0073(16) 0.0003(14) C33_3 0.0204(19) 0.0264(17) 0.039(2) -0.0052(16) 0.0094(17) -0.0060(15) C34_3 0.0232(19) 0.0169(15) 0.034(2) -0.0027(14) 0.0088(16) -0.0063(14) N34_3 0.038(2) 0.0204(14) 0.047(2) -0.0055(14) 0.0152(17) -0.0068(14) O33_3 0.0443(19) 0.0316(14) 0.059(2) -0.0013(13) 0.0075(15) -0.0231(13) O34_3 0.0427(18) 0.0165(12) 0.071(2) -0.0022(13) 0.0158(16) -0.0022(12) C35_3 0.0228(19) 0.0183(15) 0.037(2) -0.0017(15) 0.0083(17) 0.0013(14) C36_3 0.0195(19) 0.0185(15) 0.037(2) -0.0014(15) 0.0043(16) 0.0019(13) N11_4 0.0231(16) 0.0174(13) 0.036(2) -0.0016(12) 0.0047(14) -0.0032(12) C12_4 0.0168(18) 0.0194(15) 0.043(2) 0.0026(15) 0.0082(17) 0.0010(14) C13_4 0.0191(19) 0.0240(17) 0.044(3) 0.0047(16) 0.0056(17) 0.0002(14) C14_4 0.0152(18) 0.0195(15) 0.044(3) -0.0022(15) 0.0095(17) 0.0017(13) C15_4 0.022(2) 0.0272(18) 0.046(3) -0.0046(17) 0.0067(18) 0.0015(15) C16_4 0.028(2) 0.0175(16) 0.063(3) -0.0116(18) 0.004(2) 0.0019(15) C17_4 0.027(2) 0.0156(16) 0.062(3) 0.0014(17) 0.008(2) 0.0003(15) C18_4 0.022(2) 0.0183(16) 0.050(3) 0.0035(16) 0.0067(18) 0.0010(14) C19_4 0.0135(17) 0.0170(15) 0.044(3) -0.0020(15) 0.0047(16) 0.0016(13) C20_4 0.034(2) 0.0272(18) 0.051(3) 0.0114(18) 0.004(2) 0.0013(17) C21_4 0.027(2) 0.035(2) 0.046(3) -0.0004(18) 0.0091(19) -0.0001(17) C22_4 0.031(2) 0.0259(17) 0.045(3) -0.0026(17) 0.0128(19) 0.0020(16) C23_4 0.033(2) 0.0264(18) 0.043(3) -0.0064(17) 0.0036(19) 0.0010(16) C24_4 0.028(2) 0.0304(18) 0.043(3) 0.0023(17) 0.0036(19) -0.0020(16) C25_4 0.026(2) 0.0303(19) 0.041(3) 0.0015(17) 0.0092(19) -0.0037(17) O25_4 0.0330(16) 0.0354(14) 0.0501(19) -0.0015(13) 0.0029(14) -0.0053(13) O26_4 0.0237(15) 0.0340(14) 0.057(2) 0.0005(13) -0.0033(14) 0.0031(12) C26_4 0.022(2) 0.044(2) 0.070(3) 0.007(2) 0.002(2) 0.0036(18) C27_4 0.034(2) 0.038(2) 0.056(3) 0.002(2) 0.002(2) 0.0063(19) C28_4 0.022(2) 0.0193(16) 0.053(3) 0.0010(16) 0.0128(18) -0.0039(14) C29_4 0.023(2) 0.0204(16) 0.049(3) 0.0004(16) 0.0090(18) -0.0063(14) C31_4 0.0230(19) 0.0116(14) 0.037(2) -0.0009(14) 0.0064(16) 0.0005(13) O31_4 0.0167(13) 0.0149(10) 0.0583(19) -0.0031(11) 0.0120(12) -0.0018(9) C32_4 0.026(2) 0.0182(15) 0.043(2) -0.0008(15) 0.0098(18) -0.0037(14) C33_4 0.022(2) 0.0223(16) 0.041(2) -0.0002(16) 0.0041(17) 0.0021(14) C34_4 0.027(2) 0.0142(14) 0.036(2) 0.0007(14) 0.0022(17) 0.0029(14) N34_4 0.033(2) 0.0176(14) 0.046(2) 0.0005(13) 0.0005(16) 0.0066(14) O33_4 0.0345(17) 0.0280(13) 0.062(2) -0.0027(13) 0.0061(15) 0.0113(12) O34_4 0.0420(18) 0.0152(12) 0.077(2) -0.0016(13) 0.0047(16) -0.0022(12) C35_4 0.025(2) 0.0181(15) 0.039(2) -0.0015(15) 0.0005(17) -0.0045(14) C36_4 0.0194(19) 0.0173(15) 0.041(2) -0.0001(15) 0.0066(17) -0.0014(14) _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 N11_1 C19_1 1.419(4) . ? N11_1 C12_1 1.454(5) . ? N11_1 C22_1 1.462(5) . ? C12_1 O31_1 1.489(4) . ? C12_1 C28_1 1.496(5) . ? C12_1 C13_1 1.576(5) . ? C13_1 C14_1 1.513(5) . ? C13_1 C20_1 1.529(6) . ? C13_1 C21_1 1.546(5) . ? C14_1 C19_1 1.381(6) . ? C14_1 C15_1 1.382(5) . ? C15_1 C16_1 1.402(6) . ? C15_1 H15_1 0.9500 . ? C16_1 C17_1 1.362(7) . ? C16_1 H16_1 0.9500 . ? C17_1 C18_1 1.390(6) . ? C17_1 H17_1 0.9500 . ? C18_1 C19_1 1.394(5) . ? C18_1 H18_1 0.9500 . ? C20_1 H20A_1 0.9800 . ? C20_1 H20B_1 0.9800 . ? C20_1 H20C_1 0.9800 . ? C21_1 H21A_1 0.9800 . ? C21_1 H21B_1 0.9800 . ? C21_1 H21C_1 0.9800 . ? C22_1 C23_1 1.543(5) . ? C22_1 H22A_1 0.9900 . ? C22_1 H22B_1 0.9900 . ? C23_1 C24_1 1.538(5) . ? C23_1 H23A_1 0.9900 . ? C23_1 H23B_1 0.9900 . ? C24_1 C25_1 1.504(5) . ? C24_1 H24A_1 0.9900 . ? C24_1 H24B_1 0.9900 . ? C25_1 O25_1 1.210(4) . ? C25_1 O26_1 1.342(4) . ? O26_1 C26_1 1.455(4) . ? C26_1 C27_1 1.501(6) . ? C26_1 H26A_1 0.9900 . ? C26_1 H26B_1 0.9900 . ? C27_1 H27A_1 0.9800 . ? C27_1 H27B_1 0.9800 . ? C27_1 H27C_1 0.9800 . ? C28_1 C29_1 1.330(5) . ? C28_1 H28_1 0.9500 . ? C29_1 C36_1 1.450(5) . ? C29_1 H29_1 0.9500 . ? C31_1 O31_1 1.358(4) . ? C31_1 C32_1 1.393(5) . ? C31_1 C36_1 1.416(5) . ? C32_1 C33_1 1.377(4) . ? C32_1 H32_1 0.9500 . ? C33_1 C34_1 1.391(5) . ? C33_1 H33_1 0.9500 . ? C34_1 C35_1 1.387(5) . ? C34_1 N34_1 1.451(4) . ? N34_1 O33_1 1.229(4) . ? N34_1 O34_1 1.234(4) . ? C35_1 C36_1 1.389(5) . ? C35_1 H35_1 0.9500 . ? N11_2 C19_2 1.408(4) . ? N11_2 C22_2 1.449(5) . ? N11_2 C12_2 1.449(4) . ? C12_2 C28_2 1.492(4) . ? C12_2 O31_2 1.495(4) . ? C12_2 C13_2 1.573(5) . ? C13_2 C14_2 1.516(4) . ? C13_2 C20_2 1.518(5) . ? C13_2 C21_2 1.552(5) . ? C14_2 C15_2 1.385(5) . ? C14_2 C19_2 1.387(5) . ? C15_2 C16_2 1.391(5) . ? C15_2 H15_2 0.9500 . ? C16_2 C17_2 1.383(6) . ? C16_2 H16_2 0.9500 . ? C17_2 C18_2 1.405(5) . ? C17_2 H17_2 0.9500 . ? C18_2 C19_2 1.392(5) . ? C18_2 H18_2 0.9500 . ? C20_2 H20A_2 0.9800 . ? C20_2 H20B_2 0.9800 . ? C20_2 H20C_2 0.9800 . ? C21_2 H21A_2 0.9800 . ? C21_2 H21B_2 0.9800 . ? C21_2 H21C_2 0.9800 . ? C22_2 C23_2 1.511(5) . ? C22_2 H22A_2 0.9900 . ? C22_2 H22B_2 0.9900 . ? C23_2 C24_2 1.522(5) . ? C23_2 H23A_2 0.9900 . ? C23_2 H23B_2 0.9900 . ? C24_2 C25_2 1.488(6) . ? C24_2 H24A_2 0.9900 . ? C24_2 H24B_2 0.9900 . ? C25_2 O25_2 1.206(4) . ? C25_2 O26_2 1.352(4) . ? O26_2 C26_2 1.454(5) . ? C26_2 C27_2 1.502(6) . ? C26_2 H26A_2 0.9900 . ? C26_2 H26B_2 0.9900 . ? C27_2 H27A_2 0.9800 . ? C27_2 H27B_2 0.9800 . ? C27_2 H27C_2 0.9800 . ? C28_2 C29_2 1.330(4) . ? C28_2 H28_2 0.9500 . ? C29_2 C36_2 1.457(5) . ? C29_2 H29_2 0.9500 . ? C31_2 O31_2 1.356(4) . ? C31_2 C32_2 1.403(5) . ? C31_2 C36_2 1.409(4) . ? C32_2 C33_2 1.377(5) . ? C32_2 H32_2 0.9500 . ? C33_2 C34_2 1.395(5) . ? C33_2 H33_2 0.9500 . ? C34_2 C35_2 1.380(5) . ? C34_2 N34_2 1.454(4) . ? N34_2 O34_2 1.223(4) . ? N34_2 O33_2 1.247(4) . ? C35_2 C36_2 1.390(4) . ? C35_2 H35_2 0.9500 . ? N11_3 C19_3 1.421(4) . ? N11_3 C12_3 1.451(4) . ? N11_3 C22_3 1.457(5) . ? C12_3 O31_3 1.482(4) . ? C12_3 C28_3 1.511(5) . ? C12_3 C13_3 1.570(5) . ? C13_3 C14_3 1.512(4) . ? C13_3 C20_3 1.538(5) . ? C13_3 C21_3 1.547(5) . ? C14_3 C19_3 1.376(5) . ? C14_3 C15_3 1.383(5) . ? C15_3 C16_3 1.401(5) . ? C15_3 H15_3 0.9500 . ? C16_3 C17_3 1.380(6) . ? C16_3 H16_3 0.9500 . ? C17_3 C18_3 1.400(5) . ? C17_3 H17_3 0.9500 . ? C18_3 C19_3 1.393(4) . ? C18_3 H18_3 0.9500 . ? C20_3 H20A_3 0.9800 . ? C20_3 H20B_3 0.9800 . ? C20_3 H20C_3 0.9800 . ? C21_3 H21A_3 0.9800 . ? C21_3 H21B_3 0.9800 . ? C21_3 H21C_3 0.9800 . ? C22_3 C23_3 1.519(5) . ? C22_3 H22A_3 0.9900 . ? C22_3 H22B_3 0.9900 . ? C23_3 C24_3 1.536(5) . ? C23_3 H23A_3 0.9900 . ? C23_3 H23B_3 0.9900 . ? C24_3 C25_3 1.509(5) . ? C24_3 H24A_3 0.9900 . ? C24_3 H24B_3 0.9900 . ? C25_3 O25_3 1.205(4) . ? C25_3 O26_3 1.358(4) . ? O26_3 C26_3 1.455(4) . ? C26_3 C27_3 1.508(6) . ? C26_3 H26A_3 0.9900 . ? C26_3 H26B_3 0.9900 . ? C27_3 H27A_3 0.9800 . ? C27_3 H27B_3 0.9800 . ? C27_3 H27C_3 0.9800 . ? C28_3 C29_3 1.337(4) . ? C28_3 H28_3 0.9500 . ? C29_3 C36_3 1.448(5) . ? C29_3 H29_3 0.9500 . ? C31_3 O31_3 1.360(4) . ? C31_3 C32_3 1.396(5) . ? C31_3 C36_3 1.405(5) . ? C32_3 C33_3 1.382(4) . ? C32_3 H32_3 0.9500 . ? C33_3 C34_3 1.400(5) . ? C33_3 H33_3 0.9500 . ? C34_3 C35_3 1.382(5) . ? C34_3 N34_3 1.456(4) . ? N34_3 O34_3 1.230(4) . ? N34_3 O33_3 1.239(4) . ? C35_3 C36_3 1.393(4) . ? C35_3 H35_3 0.9500 . ? N11_4 C19_4 1.411(4) . ? N11_4 C12_4 1.443(4) . ? N11_4 C22_4 1.456(5) . ? C12_4 C28_4 1.490(5) . ? C12_4 O31_4 1.497(4) . ? C12_4 C13_4 1.566(5) . ? C13_4 C20_4 1.523(5) . ? C13_4 C14_4 1.530(5) . ? C13_4 C21_4 1.535(5) . ? C14_4 C15_4 1.380(5) . ? C14_4 C19_4 1.398(5) . ? C15_4 C16_4 1.395(5) . ? C15_4 H15_4 0.9500 . ? C16_4 C17_4 1.380(6) . ? C16_4 H16_4 0.9500 . ? C17_4 C18_4 1.415(5) . ? C17_4 H17_4 0.9500 . ? C18_4 C19_4 1.403(5) . ? C18_4 H18_4 0.9500 . ? C20_4 H20A_4 0.9800 . ? C20_4 H20B_4 0.9800 . ? C20_4 H20C_4 0.9800 . ? C21_4 H21A_4 0.9800 . ? C21_4 H21B_4 0.9800 . ? C21_4 H21C_4 0.9800 . ? C22_4 C23_4 1.529(5) . ? C22_4 H22A_4 0.9900 . ? C22_4 H22B_4 0.9900 . ? C23_4 C24_4 1.528(5) . ? C23_4 H23A_4 0.9900 . ? C23_4 H23B_4 0.9900 . ? C24_4 C25_4 1.498(5) . ? C24_4 H24A_4 0.9900 . ? C24_4 H24B_4 0.9900 . ? C25_4 O25_4 1.206(4) . ? C25_4 O26_4 1.349(4) . ? O26_4 C26_4 1.449(5) . ? C26_4 C27_4 1.485(5) . ? C26_4 H26A_4 0.9900 . ? C26_4 H26B_4 0.9900 . ? C27_4 H27A_4 0.9800 . ? C27_4 H27B_4 0.9800 . ? C27_4 H27C_4 0.9800 . ? C28_4 C29_4 1.332(5) . ? C28_4 H28_4 0.9500 . ? C29_4 C36_4 1.457(5) . ? C29_4 H29_4 0.9500 . ? C31_4 O31_4 1.349(4) . ? C31_4 C32_4 1.396(5) . ? C31_4 C36_4 1.402(4) . ? C32_4 C33_4 1.376(5) . ? C32_4 H32_4 0.9500 . ? C33_4 C34_4 1.399(5) . ? C33_4 H33_4 0.9500 . ? C34_4 C35_4 1.389(5) . ? C34_4 N34_4 1.453(4) . ? N34_4 O34_4 1.227(4) . ? N34_4 O33_4 1.241(4) . ? C35_4 C36_4 1.399(4) . ? C35_4 H35_4 0.9500 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C19_1 N11_1 C12_1 107.5(3) . . ? C19_1 N11_1 C22_1 120.9(3) . . ? C12_1 N11_1 C22_1 118.6(3) . . ? N11_1 C12_1 O31_1 107.3(3) . . ? N11_1 C12_1 C28_1 111.7(3) . . ? O31_1 C12_1 C28_1 111.5(3) . . ? N11_1 C12_1 C13_1 104.1(3) . . ? O31_1 C12_1 C13_1 105.0(3) . . ? C28_1 C12_1 C13_1 116.5(3) . . ? C14_1 C13_1 C20_1 115.1(3) . . ? C14_1 C13_1 C21_1 109.4(3) . . ? C20_1 C13_1 C21_1 108.4(3) . . ? C14_1 C13_1 C12_1 100.3(3) . . ? C20_1 C13_1 C12_1 112.9(3) . . ? C21_1 C13_1 C12_1 110.5(3) . . ? C19_1 C14_1 C15_1 119.9(4) . . ? C19_1 C14_1 C13_1 110.1(3) . . ? C15_1 C14_1 C13_1 130.0(4) . . ? C14_1 C15_1 C16_1 118.9(4) . . ? C14_1 C15_1 H15_1 120.5 . . ? C16_1 C15_1 H15_1 120.5 . . ? C17_1 C16_1 C15_1 120.6(4) . . ? C17_1 C16_1 H16_1 119.7 . . ? C15_1 C16_1 H16_1 119.7 . . ? C16_1 C17_1 C18_1 121.2(4) . . ? C16_1 C17_1 H17_1 119.4 . . ? C18_1 C17_1 H17_1 119.4 . . ? C17_1 C18_1 C19_1 117.8(4) . . ? C17_1 C18_1 H18_1 121.1 . . ? C19_1 C18_1 H18_1 121.1 . . ? C14_1 C19_1 C18_1 121.4(4) . . ? C14_1 C19_1 N11_1 110.2(3) . . ? C18_1 C19_1 N11_1 128.4(4) . . ? C13_1 C20_1 H20A_1 109.5 . . ? C13_1 C20_1 H20B_1 109.5 . . ? H20A_1 C20_1 H20B_1 109.5 . . ? C13_1 C20_1 H20C_1 109.5 . . ? H20A_1 C20_1 H20C_1 109.5 . . ? H20B_1 C20_1 H20C_1 109.5 . . ? C13_1 C21_1 H21A_1 109.5 . . ? C13_1 C21_1 H21B_1 109.5 . . ? H21A_1 C21_1 H21B_1 109.5 . . ? C13_1 C21_1 H21C_1 109.5 . . ? H21A_1 C21_1 H21C_1 109.5 . . ? H21B_1 C21_1 H21C_1 109.5 . . ? N11_1 C22_1 C23_1 113.1(3) . . ? N11_1 C22_1 H22A_1 109.0 . . ? C23_1 C22_1 H22A_1 109.0 . . ? N11_1 C22_1 H22B_1 109.0 . . ? C23_1 C22_1 H22B_1 109.0 . . ? H22A_1 C22_1 H22B_1 107.8 . . ? C24_1 C23_1 C22_1 113.4(3) . . ? C24_1 C23_1 H23A_1 108.9 . . ? C22_1 C23_1 H23A_1 108.9 . . ? C24_1 C23_1 H23B_1 108.9 . . ? C22_1 C23_1 H23B_1 108.9 . . ? H23A_1 C23_1 H23B_1 107.7 . . ? C25_1 C24_1 C23_1 113.7(3) . . ? C25_1 C24_1 H24A_1 108.8 . . ? C23_1 C24_1 H24A_1 108.8 . . ? C25_1 C24_1 H24B_1 108.8 . . ? C23_1 C24_1 H24B_1 108.8 . . ? H24A_1 C24_1 H24B_1 107.7 . . ? O25_1 C25_1 O26_1 122.3(4) . . ? O25_1 C25_1 C24_1 126.9(4) . . ? O26_1 C25_1 C24_1 110.8(3) . . ? C25_1 O26_1 C26_1 117.1(3) . . ? O26_1 C26_1 C27_1 107.4(3) . . ? O26_1 C26_1 H26A_1 110.2 . . ? C27_1 C26_1 H26A_1 110.2 . . ? O26_1 C26_1 H26B_1 110.2 . . ? C27_1 C26_1 H26B_1 110.2 . . ? H26A_1 C26_1 H26B_1 108.5 . . ? C26_1 C27_1 H27A_1 109.5 . . ? C26_1 C27_1 H27B_1 109.5 . . ? H27A_1 C27_1 H27B_1 109.5 . . ? C26_1 C27_1 H27C_1 109.5 . . ? H27A_1 C27_1 H27C_1 109.5 . . ? H27B_1 C27_1 H27C_1 109.5 . . ? C29_1 C28_1 C12_1 123.8(3) . . ? C29_1 C28_1 H28_1 118.1 . . ? C12_1 C28_1 H28_1 118.1 . . ? C28_1 C29_1 C36_1 120.9(3) . . ? C28_1 C29_1 H29_1 119.5 . . ? C36_1 C29_1 H29_1 119.5 . . ? O31_1 C31_1 C32_1 117.0(3) . . ? O31_1 C31_1 C36_1 121.4(3) . . ? C32_1 C31_1 C36_1 121.5(3) . . ? C31_1 O31_1 C12_1 122.6(3) . . ? C33_1 C32_1 C31_1 119.4(3) . . ? C33_1 C32_1 H32_1 120.3 . . ? C31_1 C32_1 H32_1 120.3 . . ? C32_1 C33_1 C34_1 119.5(3) . . ? C32_1 C33_1 H33_1 120.3 . . ? C34_1 C33_1 H33_1 120.3 . . ? C35_1 C34_1 C33_1 121.6(3) . . ? C35_1 C34_1 N34_1 118.6(3) . . ? C33_1 C34_1 N34_1 119.7(3) . . ? O33_1 N34_1 O34_1 122.6(3) . . ? O33_1 N34_1 C34_1 118.2(3) . . ? O34_1 N34_1 C34_1 119.2(3) . . ? C34_1 C35_1 C36_1 119.9(3) . . ? C34_1 C35_1 H35_1 120.0 . . ? C36_1 C35_1 H35_1 120.0 . . ? C35_1 C36_1 C31_1 118.0(3) . . ? C35_1 C36_1 C29_1 124.0(3) . . ? C31_1 C36_1 C29_1 118.0(3) . . ? C19_2 N11_2 C22_2 122.5(3) . . ? C19_2 N11_2 C12_2 107.1(3) . . ? C22_2 N11_2 C12_2 119.5(3) . . ? N11_2 C12_2 C28_2 112.3(3) . . ? N11_2 C12_2 O31_2 105.6(3) . . ? C28_2 C12_2 O31_2 111.8(2) . . ? N11_2 C12_2 C13_2 104.2(2) . . ? C28_2 C12_2 C13_2 116.4(3) . . ? O31_2 C12_2 C13_2 105.7(3) . . ? C14_2 C13_2 C20_2 115.3(3) . . ? C14_2 C13_2 C21_2 108.5(3) . . ? C20_2 C13_2 C21_2 110.7(3) . . ? C14_2 C13_2 C12_2 99.5(3) . . ? C20_2 C13_2 C12_2 112.8(3) . . ? C21_2 C13_2 C12_2 109.4(3) . . ? C15_2 C14_2 C19_2 120.0(3) . . ? C15_2 C14_2 C13_2 130.4(4) . . ? C19_2 C14_2 C13_2 109.5(3) . . ? C14_2 C15_2 C16_2 119.5(4) . . ? C14_2 C15_2 H15_2 120.2 . . ? C16_2 C15_2 H15_2 120.2 . . ? C17_2 C16_2 C15_2 120.2(4) . . ? C17_2 C16_2 H16_2 119.9 . . ? C15_2 C16_2 H16_2 119.9 . . ? C16_2 C17_2 C18_2 121.2(3) . . ? C16_2 C17_2 H17_2 119.4 . . ? C18_2 C17_2 H17_2 119.4 . . ? C19_2 C18_2 C17_2 117.5(4) . . ? C19_2 C18_2 H18_2 121.2 . . ? C17_2 C18_2 H18_2 121.2 . . ? C14_2 C19_2 C18_2 121.6(3) . . ? C14_2 C19_2 N11_2 110.4(3) . . ? C18_2 C19_2 N11_2 128.0(4) . . ? C13_2 C20_2 H20A_2 109.5 . . ? C13_2 C20_2 H20B_2 109.5 . . ? H20A_2 C20_2 H20B_2 109.5 . . ? C13_2 C20_2 H20C_2 109.5 . . ? H20A_2 C20_2 H20C_2 109.5 . . ? H20B_2 C20_2 H20C_2 109.5 . . ? C13_2 C21_2 H21A_2 109.5 . . ? C13_2 C21_2 H21B_2 109.5 . . ? H21A_2 C21_2 H21B_2 109.5 . . ? C13_2 C21_2 H21C_2 109.5 . . ? H21A_2 C21_2 H21C_2 109.5 . . ? H21B_2 C21_2 H21C_2 109.5 . . ? N11_2 C22_2 C23_2 113.2(3) . . ? N11_2 C22_2 H22A_2 108.9 . . ? C23_2 C22_2 H22A_2 108.9 . . ? N11_2 C22_2 H22B_2 108.9 . . ? C23_2 C22_2 H22B_2 108.9 . . ? H22A_2 C22_2 H22B_2 107.8 . . ? C22_2 C23_2 C24_2 111.0(3) . . ? C22_2 C23_2 H23A_2 109.4 . . ? C24_2 C23_2 H23A_2 109.4 . . ? C22_2 C23_2 H23B_2 109.4 . . ? C24_2 C23_2 H23B_2 109.4 . . ? H23A_2 C23_2 H23B_2 108.0 . . ? C25_2 C24_2 C23_2 115.5(3) . . ? C25_2 C24_2 H24A_2 108.4 . . ? C23_2 C24_2 H24A_2 108.4 . . ? C25_2 C24_2 H24B_2 108.4 . . ? C23_2 C24_2 H24B_2 108.4 . . ? H24A_2 C24_2 H24B_2 107.5 . . ? O25_2 C25_2 O26_2 122.7(4) . . ? O25_2 C25_2 C24_2 126.0(3) . . ? O26_2 C25_2 C24_2 111.2(3) . . ? C25_2 O26_2 C26_2 115.4(3) . . ? O26_2 C26_2 C27_2 107.0(3) . . ? O26_2 C26_2 H26A_2 110.3 . . ? C27_2 C26_2 H26A_2 110.3 . . ? O26_2 C26_2 H26B_2 110.3 . . ? C27_2 C26_2 H26B_2 110.3 . . ? H26A_2 C26_2 H26B_2 108.6 . . ? C26_2 C27_2 H27A_2 109.5 . . ? C26_2 C27_2 H27B_2 109.5 . . ? H27A_2 C27_2 H27B_2 109.5 . . ? C26_2 C27_2 H27C_2 109.5 . . ? H27A_2 C27_2 H27C_2 109.5 . . ? H27B_2 C27_2 H27C_2 109.5 . . ? C29_2 C28_2 C12_2 124.3(3) . . ? C29_2 C28_2 H28_2 117.9 . . ? C12_2 C28_2 H28_2 117.9 . . ? C28_2 C29_2 C36_2 120.9(3) . . ? C28_2 C29_2 H29_2 119.6 . . ? C36_2 C29_2 H29_2 119.6 . . ? O31_2 C31_2 C32_2 116.9(3) . . ? O31_2 C31_2 C36_2 122.0(3) . . ? C32_2 C31_2 C36_2 121.1(3) . . ? C31_2 O31_2 C12_2 123.0(2) . . ? C33_2 C32_2 C31_2 120.0(3) . . ? C33_2 C32_2 H32_2 120.0 . . ? C31_2 C32_2 H32_2 120.0 . . ? C32_2 C33_2 C34_2 118.4(3) . . ? C32_2 C33_2 H33_2 120.8 . . ? C34_2 C33_2 H33_2 120.8 . . ? C35_2 C34_2 C33_2 122.5(3) . . ? C35_2 C34_2 N34_2 118.2(3) . . ? C33_2 C34_2 N34_2 119.4(3) . . ? O34_2 N34_2 O33_2 122.5(3) . . ? O34_2 N34_2 C34_2 119.6(3) . . ? O33_2 N34_2 C34_2 117.9(3) . . ? C34_2 C35_2 C36_2 119.8(3) . . ? C34_2 C35_2 H35_2 120.1 . . ? C36_2 C35_2 H35_2 120.1 . . ? C35_2 C36_2 C31_2 118.3(3) . . ? C35_2 C36_2 C29_2 123.9(3) . . ? C31_2 C36_2 C29_2 117.8(3) . . ? C19_3 N11_3 C12_3 106.2(3) . . ? C19_3 N11_3 C22_3 120.8(3) . . ? C12_3 N11_3 C22_3 119.7(3) . . ? N11_3 C12_3 O31_3 104.9(2) . . ? N11_3 C12_3 C28_3 112.9(3) . . ? O31_3 C12_3 C28_3 111.2(3) . . ? N11_3 C12_3 C13_3 104.0(3) . . ? O31_3 C12_3 C13_3 107.4(3) . . ? C28_3 C12_3 C13_3 115.6(3) . . ? C14_3 C13_3 C20_3 115.2(3) . . ? C14_3 C13_3 C21_3 109.5(3) . . ? C20_3 C13_3 C21_3 109.1(3) . . ? C14_3 C13_3 C12_3 99.9(3) . . ? C20_3 C13_3 C12_3 112.5(3) . . ? C21_3 C13_3 C12_3 110.4(3) . . ? C19_3 C14_3 C15_3 120.6(3) . . ? C19_3 C14_3 C13_3 109.4(3) . . ? C15_3 C14_3 C13_3 130.0(3) . . ? C14_3 C15_3 C16_3 119.1(4) . . ? C14_3 C15_3 H15_3 120.5 . . ? C16_3 C15_3 H15_3 120.5 . . ? C17_3 C16_3 C15_3 119.6(4) . . ? C17_3 C16_3 H16_3 120.2 . . ? C15_3 C16_3 H16_3 120.2 . . ? C16_3 C17_3 C18_3 122.0(3) . . ? C16_3 C17_3 H17_3 119.0 . . ? C18_3 C17_3 H17_3 119.0 . . ? C19_3 C18_3 C17_3 117.0(4) . . ? C19_3 C18_3 H18_3 121.5 . . ? C17_3 C18_3 H18_3 121.5 . . ? C14_3 C19_3 C18_3 121.8(3) . . ? C14_3 C19_3 N11_3 110.7(3) . . ? C18_3 C19_3 N11_3 127.5(3) . . ? C13_3 C20_3 H20A_3 109.5 . . ? C13_3 C20_3 H20B_3 109.5 . . ? H20A_3 C20_3 H20B_3 109.5 . . ? C13_3 C20_3 H20C_3 109.5 . . ? H20A_3 C20_3 H20C_3 109.5 . . ? H20B_3 C20_3 H20C_3 109.5 . . ? C13_3 C21_3 H21A_3 109.5 . . ? C13_3 C21_3 H21B_3 109.5 . . ? H21A_3 C21_3 H21B_3 109.5 . . ? C13_3 C21_3 H21C_3 109.5 . . ? H21A_3 C21_3 H21C_3 109.5 . . ? H21B_3 C21_3 H21C_3 109.5 . . ? N11_3 C22_3 C23_3 112.5(3) . . ? N11_3 C22_3 H22A_3 109.1 . . ? C23_3 C22_3 H22A_3 109.1 . . ? N11_3 C22_3 H22B_3 109.1 . . ? C23_3 C22_3 H22B_3 109.1 . . ? H22A_3 C22_3 H22B_3 107.8 . . ? C22_3 C23_3 C24_3 112.5(3) . . ? C22_3 C23_3 H23A_3 109.1 . . ? C24_3 C23_3 H23A_3 109.1 . . ? C22_3 C23_3 H23B_3 109.1 . . ? C24_3 C23_3 H23B_3 109.1 . . ? H23A_3 C23_3 H23B_3 107.8 . . ? C25_3 C24_3 C23_3 111.7(3) . . ? C25_3 C24_3 H24A_3 109.3 . . ? C23_3 C24_3 H24A_3 109.3 . . ? C25_3 C24_3 H24B_3 109.3 . . ? C23_3 C24_3 H24B_3 109.3 . . ? H24A_3 C24_3 H24B_3 107.9 . . ? O25_3 C25_3 O26_3 123.1(4) . . ? O25_3 C25_3 C24_3 126.1(3) . . ? O26_3 C25_3 C24_3 110.8(3) . . ? C25_3 O26_3 C26_3 116.5(3) . . ? O26_3 C26_3 C27_3 112.3(3) . . ? O26_3 C26_3 H26A_3 109.2 . . ? C27_3 C26_3 H26A_3 109.2 . . ? O26_3 C26_3 H26B_3 109.1 . . ? C27_3 C26_3 H26B_3 109.2 . . ? H26A_3 C26_3 H26B_3 107.9 . . ? C26_3 C27_3 H27A_3 109.5 . . ? C26_3 C27_3 H27B_3 109.5 . . ? H27A_3 C27_3 H27B_3 109.5 . . ? C26_3 C27_3 H27C_3 109.5 . . ? H27A_3 C27_3 H27C_3 109.5 . . ? H27B_3 C27_3 H27C_3 109.5 . . ? C29_3 C28_3 C12_3 122.6(3) . . ? C29_3 C28_3 H28_3 118.7 . . ? C12_3 C28_3 H28_3 118.7 . . ? C28_3 C29_3 C36_3 120.9(3) . . ? C28_3 C29_3 H29_3 119.6 . . ? C36_3 C29_3 H29_3 119.6 . . ? O31_3 C31_3 C32_3 116.6(3) . . ? O31_3 C31_3 C36_3 121.3(3) . . ? C32_3 C31_3 C36_3 122.1(3) . . ? C31_3 O31_3 C12_3 122.1(2) . . ? C33_3 C32_3 C31_3 119.3(3) . . ? C33_3 C32_3 H32_3 120.3 . . ? C31_3 C32_3 H32_3 120.3 . . ? C32_3 C33_3 C34_3 118.6(3) . . ? C32_3 C33_3 H33_3 120.7 . . ? C34_3 C33_3 H33_3 120.7 . . ? C35_3 C34_3 C33_3 122.3(3) . . ? C35_3 C34_3 N34_3 119.1(3) . . ? C33_3 C34_3 N34_3 118.5(3) . . ? O34_3 N34_3 O33_3 123.1(3) . . ? O34_3 N34_3 C34_3 119.0(3) . . ? O33_3 N34_3 C34_3 117.9(3) . . ? C34_3 C35_3 C36_3 119.7(3) . . ? C34_3 C35_3 H35_3 120.2 . . ? C36_3 C35_3 H35_3 120.2 . . ? C35_3 C36_3 C31_3 118.0(3) . . ? C35_3 C36_3 C29_3 123.6(3) . . ? C31_3 C36_3 C29_3 118.4(3) . . ? C19_4 N11_4 C12_4 106.8(3) . . ? C19_4 N11_4 C22_4 123.0(3) . . ? C12_4 N11_4 C22_4 119.2(3) . . ? N11_4 C12_4 C28_4 114.2(3) . . ? N11_4 C12_4 O31_4 105.0(3) . . ? C28_4 C12_4 O31_4 112.1(3) . . ? N11_4 C12_4 C13_4 104.4(3) . . ? C28_4 C12_4 C13_4 114.5(3) . . ? O31_4 C12_4 C13_4 105.9(3) . . ? C20_4 C13_4 C14_4 114.2(3) . . ? C20_4 C13_4 C21_4 110.1(3) . . ? C14_4 C13_4 C21_4 108.5(3) . . ? C20_4 C13_4 C12_4 113.3(3) . . ? C14_4 C13_4 C12_4 99.6(3) . . ? C21_4 C13_4 C12_4 110.6(3) . . ? C15_4 C14_4 C19_4 120.7(3) . . ? C15_4 C14_4 C13_4 130.6(4) . . ? C19_4 C14_4 C13_4 108.7(3) . . ? C14_4 C15_4 C16_4 119.3(4) . . ? C14_4 C15_4 H15_4 120.4 . . ? C16_4 C15_4 H15_4 120.4 . . ? C17_4 C16_4 C15_4 120.7(4) . . ? C17_4 C16_4 H16_4 119.7 . . ? C15_4 C16_4 H16_4 119.7 . . ? C16_4 C17_4 C18_4 121.0(3) . . ? C16_4 C17_4 H17_4 119.5 . . ? C18_4 C17_4 H17_4 119.5 . . ? C19_4 C18_4 C17_4 117.5(4) . . ? C19_4 C18_4 H18_4 121.2 . . ? C17_4 C18_4 H18_4 121.2 . . ? C14_4 C19_4 C18_4 120.7(3) . . ? C14_4 C19_4 N11_4 110.2(3) . . ? C18_4 C19_4 N11_4 129.1(4) . . ? C13_4 C20_4 H20A_4 109.5 . . ? C13_4 C20_4 H20B_4 109.5 . . ? H20A_4 C20_4 H20B_4 109.5 . . ? C13_4 C20_4 H20C_4 109.5 . . ? H20A_4 C20_4 H20C_4 109.5 . . ? H20B_4 C20_4 H20C_4 109.5 . . ? C13_4 C21_4 H21A_4 109.5 . . ? C13_4 C21_4 H21B_4 109.5 . . ? H21A_4 C21_4 H21B_4 109.5 . . ? C13_4 C21_4 H21C_4 109.5 . . ? H21A_4 C21_4 H21C_4 109.5 . . ? H21B_4 C21_4 H21C_4 109.5 . . ? N11_4 C22_4 C23_4 113.3(3) . . ? N11_4 C22_4 H22A_4 108.9 . . ? C23_4 C22_4 H22A_4 108.9 . . ? N11_4 C22_4 H22B_4 108.9 . . ? C23_4 C22_4 H22B_4 108.9 . . ? H22A_4 C22_4 H22B_4 107.7 . . ? C24_4 C23_4 C22_4 112.2(3) . . ? C24_4 C23_4 H23A_4 109.2 . . ? C22_4 C23_4 H23A_4 109.2 . . ? C24_4 C23_4 H23B_4 109.2 . . ? C22_4 C23_4 H23B_4 109.2 . . ? H23A_4 C23_4 H23B_4 107.9 . . ? C25_4 C24_4 C23_4 114.9(3) . . ? C25_4 C24_4 H24A_4 108.5 . . ? C23_4 C24_4 H24A_4 108.5 . . ? C25_4 C24_4 H24B_4 108.5 . . ? C23_4 C24_4 H24B_4 108.5 . . ? H24A_4 C24_4 H24B_4 107.5 . . ? O25_4 C25_4 O26_4 123.5(4) . . ? O25_4 C25_4 C24_4 126.0(3) . . ? O26_4 C25_4 C24_4 110.5(3) . . ? C25_4 O26_4 C26_4 117.5(3) . . ? O26_4 C26_4 C27_4 108.1(3) . . ? O26_4 C26_4 H26A_4 110.1 . . ? C27_4 C26_4 H26A_4 110.1 . . ? O26_4 C26_4 H26B_4 110.1 . . ? C27_4 C26_4 H26B_4 110.1 . . ? H26A_4 C26_4 H26B_4 108.4 . . ? C26_4 C27_4 H27A_4 109.5 . . ? C26_4 C27_4 H27B_4 109.5 . . ? H27A_4 C27_4 H27B_4 109.5 . . ? C26_4 C27_4 H27C_4 109.5 . . ? H27A_4 C27_4 H27C_4 109.5 . . ? H27B_4 C27_4 H27C_4 109.5 . . ? C29_4 C28_4 C12_4 123.8(3) . . ? C29_4 C28_4 H28_4 118.1 . . ? C12_4 C28_4 H28_4 118.1 . . ? C28_4 C29_4 C36_4 120.7(3) . . ? C28_4 C29_4 H29_4 119.7 . . ? C36_4 C29_4 H29_4 119.7 . . ? O31_4 C31_4 C32_4 116.6(3) . . ? O31_4 C31_4 C36_4 122.2(3) . . ? C32_4 C31_4 C36_4 121.2(3) . . ? C31_4 O31_4 C12_4 122.8(2) . . ? C33_4 C32_4 C31_4 120.2(3) . . ? C33_4 C32_4 H32_4 119.9 . . ? C31_4 C32_4 H32_4 119.9 . . ? C32_4 C33_4 C34_4 118.9(3) . . ? C32_4 C33_4 H33_4 120.5 . . ? C34_4 C33_4 H33_4 120.5 . . ? C35_4 C34_4 C33_4 121.6(3) . . ? C35_4 C34_4 N34_4 118.9(3) . . ? C33_4 C34_4 N34_4 119.5(3) . . ? O34_4 N34_4 O33_4 122.8(3) . . ? O34_4 N34_4 C34_4 119.2(3) . . ? O33_4 N34_4 C34_4 118.0(3) . . ? C34_4 C35_4 C36_4 119.7(3) . . ? C34_4 C35_4 H35_4 120.2 . . ? C36_4 C35_4 H35_4 120.2 . . ? C35_4 C36_4 C31_4 118.4(3) . . ? C35_4 C36_4 C29_4 123.5(3) . . ? C31_4 C36_4 C29_4 118.0(3) . . ? 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 C19_1 N11_1 C12_1 O31_1 83.4(3) . . . . ? C22_1 N11_1 C12_1 O31_1 -58.3(4) . . . . ? C19_1 N11_1 C12_1 C28_1 -154.0(3) . . . . ? C22_1 N11_1 C12_1 C28_1 64.3(4) . . . . ? C19_1 N11_1 C12_1 C13_1 -27.5(3) . . . . ? C22_1 N11_1 C12_1 C13_1 -169.2(3) . . . . ? N11_1 C12_1 C13_1 C14_1 26.0(3) . . . . ? O31_1 C12_1 C13_1 C14_1 -86.7(3) . . . . ? C28_1 C12_1 C13_1 C14_1 149.4(3) . . . . ? N11_1 C12_1 C13_1 C20_1 149.0(3) . . . . ? O31_1 C12_1 C13_1 C20_1 36.3(4) . . . . ? C28_1 C12_1 C13_1 C20_1 -87.6(4) . . . . ? N11_1 C12_1 C13_1 C21_1 -89.4(3) . . . . ? O31_1 C12_1 C13_1 C21_1 158.0(3) . . . . ? C28_1 C12_1 C13_1 C21_1 34.0(4) . . . . ? C20_1 C13_1 C14_1 C19_1 -137.7(3) . . . . ? C21_1 C13_1 C14_1 C19_1 99.9(4) . . . . ? C12_1 C13_1 C14_1 C19_1 -16.4(4) . . . . ? C20_1 C13_1 C14_1 C15_1 44.8(5) . . . . ? C21_1 C13_1 C14_1 C15_1 -77.6(5) . . . . ? C12_1 C13_1 C14_1 C15_1 166.2(4) . . . . ? C19_1 C14_1 C15_1 C16_1 0.4(5) . . . . ? C13_1 C14_1 C15_1 C16_1 177.6(4) . . . . ? C14_1 C15_1 C16_1 C17_1 1.0(6) . . . . ? C15_1 C16_1 C17_1 C18_1 -1.3(6) . . . . ? C16_1 C17_1 C18_1 C19_1 0.2(6) . . . . ? C15_1 C14_1 C19_1 C18_1 -1.5(5) . . . . ? C13_1 C14_1 C19_1 C18_1 -179.3(3) . . . . ? C15_1 C14_1 C19_1 N11_1 178.0(3) . . . . ? C13_1 C14_1 C19_1 N11_1 0.3(4) . . . . ? C17_1 C18_1 C19_1 C14_1 1.3(5) . . . . ? C17_1 C18_1 C19_1 N11_1 -178.2(3) . . . . ? C12_1 N11_1 C19_1 C14_1 17.9(4) . . . . ? C22_1 N11_1 C19_1 C14_1 158.6(3) . . . . ? C12_1 N11_1 C19_1 C18_1 -162.6(3) . . . . ? C22_1 N11_1 C19_1 C18_1 -21.9(5) . . . . ? C19_1 N11_1 C22_1 C23_1 86.0(4) . . . . ? C12_1 N11_1 C22_1 C23_1 -137.5(3) . . . . ? N11_1 C22_1 C23_1 C24_1 61.1(4) . . . . ? C22_1 C23_1 C24_1 C25_1 75.5(5) . . . . ? C23_1 C24_1 C25_1 O25_1 -11.8(6) . . . . ? C23_1 C24_1 C25_1 O26_1 168.9(3) . . . . ? O25_1 C25_1 O26_1 C26_1 -3.0(6) . . . . ? C24_1 C25_1 O26_1 C26_1 176.4(3) . . . . ? C25_1 O26_1 C26_1 C27_1 164.7(4) . . . . ? N11_1 C12_1 C28_1 C29_1 -108.5(4) . . . . ? O31_1 C12_1 C28_1 C29_1 11.6(5) . . . . ? C13_1 C12_1 C28_1 C29_1 132.0(4) . . . . ? C12_1 C28_1 C29_1 C36_1 -2.2(6) . . . . ? C32_1 C31_1 O31_1 C12_1 -170.2(3) . . . . ? C36_1 C31_1 O31_1 C12_1 11.3(5) . . . . ? N11_1 C12_1 O31_1 C31_1 106.6(3) . . . . ? C28_1 C12_1 O31_1 C31_1 -16.1(5) . . . . ? C13_1 C12_1 O31_1 C31_1 -143.1(3) . . . . ? O31_1 C31_1 C32_1 C33_1 -178.8(3) . . . . ? C36_1 C31_1 C32_1 C33_1 -0.4(6) . . . . ? C31_1 C32_1 C33_1 C34_1 -0.5(6) . . . . ? C32_1 C33_1 C34_1 C35_1 0.9(6) . . . . ? C32_1 C33_1 C34_1 N34_1 -179.5(3) . . . . ? C35_1 C34_1 N34_1 O33_1 173.2(3) . . . . ? C33_1 C34_1 N34_1 O33_1 -6.4(5) . . . . ? C35_1 C34_1 N34_1 O34_1 -7.6(5) . . . . ? C33_1 C34_1 N34_1 O34_1 172.8(4) . . . . ? C33_1 C34_1 C35_1 C36_1 -0.3(6) . . . . ? N34_1 C34_1 C35_1 C36_1 -179.9(3) . . . . ? C34_1 C35_1 C36_1 C31_1 -0.5(6) . . . . ? C34_1 C35_1 C36_1 C29_1 179.1(4) . . . . ? O31_1 C31_1 C36_1 C35_1 179.2(3) . . . . ? C32_1 C31_1 C36_1 C35_1 0.9(6) . . . . ? O31_1 C31_1 C36_1 C29_1 -0.5(5) . . . . ? C32_1 C31_1 C36_1 C29_1 -178.8(4) . . . . ? C28_1 C29_1 C36_1 C35_1 176.2(4) . . . . ? C28_1 C29_1 C36_1 C31_1 -4.1(6) . . . . ? C19_2 N11_2 C12_2 C28_2 156.4(3) . . . . ? C22_2 N11_2 C12_2 C28_2 -58.6(4) . . . . ? C19_2 N11_2 C12_2 O31_2 -81.4(3) . . . . ? C22_2 N11_2 C12_2 O31_2 63.5(4) . . . . ? C19_2 N11_2 C12_2 C13_2 29.6(3) . . . . ? C22_2 N11_2 C12_2 C13_2 174.6(3) . . . . ? N11_2 C12_2 C13_2 C14_2 -28.6(3) . . . . ? C28_2 C12_2 C13_2 C14_2 -152.8(3) . . . . ? O31_2 C12_2 C13_2 C14_2 82.4(3) . . . . ? N11_2 C12_2 C13_2 C20_2 -151.3(3) . . . . ? C28_2 C12_2 C13_2 C20_2 84.5(4) . . . . ? O31_2 C12_2 C13_2 C20_2 -40.3(3) . . . . ? N11_2 C12_2 C13_2 C21_2 85.0(3) . . . . ? C28_2 C12_2 C13_2 C21_2 -39.2(4) . . . . ? O31_2 C12_2 C13_2 C21_2 -164.0(3) . . . . ? C20_2 C13_2 C14_2 C15_2 -44.9(5) . . . . ? C21_2 C13_2 C14_2 C15_2 79.9(5) . . . . ? C12_2 C13_2 C14_2 C15_2 -165.8(3) . . . . ? C20_2 C13_2 C14_2 C19_2 139.5(3) . . . . ? C21_2 C13_2 C14_2 C19_2 -95.7(3) . . . . ? C12_2 C13_2 C14_2 C19_2 18.6(3) . . . . ? C19_2 C14_2 C15_2 C16_2 -0.9(5) . . . . ? C13_2 C14_2 C15_2 C16_2 -176.1(3) . . . . ? C14_2 C15_2 C16_2 C17_2 0.3(5) . . . . ? C15_2 C16_2 C17_2 C18_2 0.0(5) . . . . ? C16_2 C17_2 C18_2 C19_2 0.4(5) . . . . ? C15_2 C14_2 C19_2 C18_2 1.3(5) . . . . ? C13_2 C14_2 C19_2 C18_2 177.4(3) . . . . ? C15_2 C14_2 C19_2 N11_2 -177.6(3) . . . . ? C13_2 C14_2 C19_2 N11_2 -1.5(4) . . . . ? C17_2 C18_2 C19_2 C14_2 -1.1(5) . . . . ? C17_2 C18_2 C19_2 N11_2 177.7(3) . . . . ? C22_2 N11_2 C19_2 C14_2 -162.1(3) . . . . ? C12_2 N11_2 C19_2 C14_2 -18.4(4) . . . . ? C22_2 N11_2 C19_2 C18_2 19.0(5) . . . . ? C12_2 N11_2 C19_2 C18_2 162.7(3) . . . . ? C19_2 N11_2 C22_2 C23_2 -96.6(4) . . . . ? C12_2 N11_2 C22_2 C23_2 124.0(3) . . . . ? N11_2 C22_2 C23_2 C24_2 179.5(3) . . . . ? C22_2 C23_2 C24_2 C25_2 174.1(3) . . . . ? C23_2 C24_2 C25_2 O25_2 -133.2(4) . . . . ? C23_2 C24_2 C25_2 O26_2 46.7(4) . . . . ? O25_2 C25_2 O26_2 C26_2 -3.6(5) . . . . ? C24_2 C25_2 O26_2 C26_2 176.4(3) . . . . ? C25_2 O26_2 C26_2 C27_2 -177.0(3) . . . . ? N11_2 C12_2 C28_2 C29_2 121.5(4) . . . . ? O31_2 C12_2 C28_2 C29_2 3.1(5) . . . . ? C13_2 C12_2 C28_2 C29_2 -118.5(4) . . . . ? C12_2 C28_2 C29_2 C36_2 -2.8(6) . . . . ? C32_2 C31_2 O31_2 C12_2 177.0(3) . . . . ? C36_2 C31_2 O31_2 C12_2 -3.5(5) . . . . ? N11_2 C12_2 O31_2 C31_2 -122.3(3) . . . . ? C28_2 C12_2 O31_2 C31_2 0.1(5) . . . . ? C13_2 C12_2 O31_2 C31_2 127.7(3) . . . . ? O31_2 C31_2 C32_2 C33_2 177.3(3) . . . . ? C36_2 C31_2 C32_2 C33_2 -2.3(6) . . . . ? C31_2 C32_2 C33_2 C34_2 1.2(6) . . . . ? C32_2 C33_2 C34_2 C35_2 0.2(6) . . . . ? C32_2 C33_2 C34_2 N34_2 179.8(3) . . . . ? C35_2 C34_2 N34_2 O34_2 7.4(5) . . . . ? C33_2 C34_2 N34_2 O34_2 -172.2(4) . . . . ? C35_2 C34_2 N34_2 O33_2 -172.7(3) . . . . ? C33_2 C34_2 N34_2 O33_2 7.7(5) . . . . ? C33_2 C34_2 C35_2 C36_2 -0.6(6) . . . . ? N34_2 C34_2 C35_2 C36_2 179.8(3) . . . . ? C34_2 C35_2 C36_2 C31_2 -0.4(5) . . . . ? C34_2 C35_2 C36_2 C29_2 178.0(3) . . . . ? O31_2 C31_2 C36_2 C35_2 -177.7(3) . . . . ? C32_2 C31_2 C36_2 C35_2 1.9(5) . . . . ? O31_2 C31_2 C36_2 C29_2 3.8(5) . . . . ? C32_2 C31_2 C36_2 C29_2 -176.7(3) . . . . ? C28_2 C29_2 C36_2 C35_2 -179.1(4) . . . . ? C28_2 C29_2 C36_2 C31_2 -0.6(5) . . . . ? C19_3 N11_3 C12_3 O31_3 82.0(3) . . . . ? C22_3 N11_3 C12_3 O31_3 -59.1(4) . . . . ? C19_3 N11_3 C12_3 C28_3 -156.7(3) . . . . ? C22_3 N11_3 C12_3 C28_3 62.1(4) . . . . ? C19_3 N11_3 C12_3 C13_3 -30.6(3) . . . . ? C22_3 N11_3 C12_3 C13_3 -171.8(3) . . . . ? N11_3 C12_3 C13_3 C14_3 29.2(3) . . . . ? O31_3 C12_3 C13_3 C14_3 -81.6(3) . . . . ? C28_3 C12_3 C13_3 C14_3 153.6(3) . . . . ? N11_3 C12_3 C13_3 C20_3 151.9(3) . . . . ? O31_3 C12_3 C13_3 C20_3 41.0(3) . . . . ? C28_3 C12_3 C13_3 C20_3 -83.8(4) . . . . ? N11_3 C12_3 C13_3 C21_3 -86.0(3) . . . . ? O31_3 C12_3 C13_3 C21_3 163.2(2) . . . . ? C28_3 C12_3 C13_3 C21_3 38.4(4) . . . . ? C20_3 C13_3 C14_3 C19_3 -139.0(3) . . . . ? C21_3 C13_3 C14_3 C19_3 97.6(4) . . . . ? C12_3 C13_3 C14_3 C19_3 -18.3(3) . . . . ? C20_3 C13_3 C14_3 C15_3 43.1(5) . . . . ? C21_3 C13_3 C14_3 C15_3 -80.2(5) . . . . ? C12_3 C13_3 C14_3 C15_3 163.9(3) . . . . ? C19_3 C14_3 C15_3 C16_3 0.0(5) . . . . ? C13_3 C14_3 C15_3 C16_3 177.7(3) . . . . ? C14_3 C15_3 C16_3 C17_3 0.1(5) . . . . ? C15_3 C16_3 C17_3 C18_3 0.5(5) . . . . ? C16_3 C17_3 C18_3 C19_3 -1.3(5) . . . . ? C15_3 C14_3 C19_3 C18_3 -0.9(5) . . . . ? C13_3 C14_3 C19_3 C18_3 -179.0(3) . . . . ? C15_3 C14_3 C19_3 N11_3 178.3(3) . . . . ? C13_3 C14_3 C19_3 N11_3 0.2(4) . . . . ? C17_3 C18_3 C19_3 C14_3 1.5(5) . . . . ? C17_3 C18_3 C19_3 N11_3 -177.6(3) . . . . ? C12_3 N11_3 C19_3 C14_3 19.9(4) . . . . ? C22_3 N11_3 C19_3 C14_3 160.6(3) . . . . ? C12_3 N11_3 C19_3 C18_3 -160.9(3) . . . . ? C22_3 N11_3 C19_3 C18_3 -20.3(5) . . . . ? C19_3 N11_3 C22_3 C23_3 89.3(4) . . . . ? C12_3 N11_3 C22_3 C23_3 -135.2(3) . . . . ? N11_3 C22_3 C23_3 C24_3 64.6(4) . . . . ? C22_3 C23_3 C24_3 C25_3 73.8(4) . . . . ? C23_3 C24_3 C25_3 O25_3 15.5(6) . . . . ? C23_3 C24_3 C25_3 O26_3 -165.9(3) . . . . ? O25_3 C25_3 O26_3 C26_3 3.3(6) . . . . ? C24_3 C25_3 O26_3 C26_3 -175.3(3) . . . . ? C25_3 O26_3 C26_3 C27_3 -79.8(4) . . . . ? N11_3 C12_3 C28_3 C29_3 -134.3(4) . . . . ? O31_3 C12_3 C28_3 C29_3 -16.7(5) . . . . ? C13_3 C12_3 C28_3 C29_3 106.1(4) . . . . ? C12_3 C28_3 C29_3 C36_3 4.6(6) . . . . ? C32_3 C31_3 O31_3 C12_3 164.9(3) . . . . ? C36_3 C31_3 O31_3 C12_3 -15.8(5) . . . . ? N11_3 C12_3 O31_3 C31_3 144.6(3) . . . . ? C28_3 C12_3 O31_3 C31_3 22.2(4) . . . . ? C13_3 C12_3 O31_3 C31_3 -105.2(3) . . . . ? O31_3 C31_3 C32_3 C33_3 179.8(3) . . . . ? C36_3 C31_3 C32_3 C33_3 0.6(6) . . . . ? C31_3 C32_3 C33_3 C34_3 0.1(5) . . . . ? C32_3 C33_3 C34_3 C35_3 -0.7(6) . . . . ? C32_3 C33_3 C34_3 N34_3 177.3(3) . . . . ? C35_3 C34_3 N34_3 O34_3 -11.1(5) . . . . ? C33_3 C34_3 N34_3 O34_3 170.8(3) . . . . ? C35_3 C34_3 N34_3 O33_3 168.1(3) . . . . ? C33_3 C34_3 N34_3 O33_3 -10.0(5) . . . . ? C33_3 C34_3 C35_3 C36_3 0.6(6) . . . . ? N34_3 C34_3 C35_3 C36_3 -177.4(3) . . . . ? C34_3 C35_3 C36_3 C31_3 0.1(5) . . . . ? C34_3 C35_3 C36_3 C29_3 178.5(4) . . . . ? O31_3 C31_3 C36_3 C35_3 -179.9(3) . . . . ? C32_3 C31_3 C36_3 C35_3 -0.7(5) . . . . ? O31_3 C31_3 C36_3 C29_3 1.6(5) . . . . ? C32_3 C31_3 C36_3 C29_3 -179.2(3) . . . . ? C28_3 C29_3 C36_3 C35_3 -174.5(4) . . . . ? C28_3 C29_3 C36_3 C31_3 4.0(6) . . . . ? C19_4 N11_4 C12_4 C28_4 157.7(3) . . . . ? C22_4 N11_4 C12_4 C28_4 -57.1(4) . . . . ? C19_4 N11_4 C12_4 O31_4 -79.2(3) . . . . ? C22_4 N11_4 C12_4 O31_4 66.0(4) . . . . ? C19_4 N11_4 C12_4 C13_4 31.9(3) . . . . ? C22_4 N11_4 C12_4 C13_4 177.2(3) . . . . ? N11_4 C12_4 C13_4 C20_4 -151.1(3) . . . . ? C28_4 C12_4 C13_4 C20_4 83.4(4) . . . . ? O31_4 C12_4 C13_4 C20_4 -40.5(4) . . . . ? N11_4 C12_4 C13_4 C14_4 -29.4(3) . . . . ? C28_4 C12_4 C13_4 C14_4 -154.9(3) . . . . ? O31_4 C12_4 C13_4 C14_4 81.2(3) . . . . ? N11_4 C12_4 C13_4 C21_4 84.7(3) . . . . ? C28_4 C12_4 C13_4 C21_4 -40.8(4) . . . . ? O31_4 C12_4 C13_4 C21_4 -164.8(3) . . . . ? C20_4 C13_4 C14_4 C15_4 -43.9(5) . . . . ? C21_4 C13_4 C14_4 C15_4 79.3(5) . . . . ? C12_4 C13_4 C14_4 C15_4 -165.0(3) . . . . ? C20_4 C13_4 C14_4 C19_4 138.4(3) . . . . ? C21_4 C13_4 C14_4 C19_4 -98.3(4) . . . . ? C12_4 C13_4 C14_4 C19_4 17.4(3) . . . . ? C19_4 C14_4 C15_4 C16_4 -1.2(5) . . . . ? C13_4 C14_4 C15_4 C16_4 -178.6(3) . . . . ? C14_4 C15_4 C16_4 C17_4 -1.5(5) . . . . ? C15_4 C16_4 C17_4 C18_4 2.5(6) . . . . ? C16_4 C17_4 C18_4 C19_4 -0.8(5) . . . . ? C15_4 C14_4 C19_4 C18_4 2.9(5) . . . . ? C13_4 C14_4 C19_4 C18_4 -179.2(3) . . . . ? C15_4 C14_4 C19_4 N11_4 -176.8(3) . . . . ? C13_4 C14_4 C19_4 N11_4 1.1(4) . . . . ? C17_4 C18_4 C19_4 C14_4 -1.9(5) . . . . ? C17_4 C18_4 C19_4 N11_4 177.7(3) . . . . ? C12_4 N11_4 C19_4 C14_4 -21.4(4) . . . . ? C22_4 N11_4 C19_4 C14_4 -165.0(3) . . . . ? C12_4 N11_4 C19_4 C18_4 158.9(3) . . . . ? C22_4 N11_4 C19_4 C18_4 15.3(5) . . . . ? C19_4 N11_4 C22_4 C23_4 -100.4(4) . . . . ? C12_4 N11_4 C22_4 C23_4 120.2(3) . . . . ? N11_4 C22_4 C23_4 C24_4 64.7(4) . . . . ? C22_4 C23_4 C24_4 C25_4 -176.0(3) . . . . ? C23_4 C24_4 C25_4 O25_4 -2.6(6) . . . . ? C23_4 C24_4 C25_4 O26_4 176.6(3) . . . . ? O25_4 C25_4 O26_4 C26_4 -0.1(6) . . . . ? C24_4 C25_4 O26_4 C26_4 -179.3(3) . . . . ? C25_4 O26_4 C26_4 C27_4 -158.2(4) . . . . ? N11_4 C12_4 C28_4 C29_4 126.0(4) . . . . ? O31_4 C12_4 C28_4 C29_4 6.8(5) . . . . ? C13_4 C12_4 C28_4 C29_4 -113.8(4) . . . . ? C12_4 C28_4 C29_4 C36_4 -4.7(6) . . . . ? C32_4 C31_4 O31_4 C12_4 176.7(3) . . . . ? C36_4 C31_4 O31_4 C12_4 -2.6(5) . . . . ? N11_4 C12_4 O31_4 C31_4 -127.6(3) . . . . ? C28_4 C12_4 O31_4 C31_4 -3.1(5) . . . . ? C13_4 C12_4 O31_4 C31_4 122.4(3) . . . . ? O31_4 C31_4 C32_4 C33_4 179.4(3) . . . . ? C36_4 C31_4 C32_4 C33_4 -1.2(6) . . . . ? C31_4 C32_4 C33_4 C34_4 -0.6(6) . . . . ? C32_4 C33_4 C34_4 C35_4 0.3(6) . . . . ? C32_4 C33_4 C34_4 N34_4 -177.5(4) . . . . ? C35_4 C34_4 N34_4 O34_4 0.2(5) . . . . ? C33_4 C34_4 N34_4 O34_4 178.2(4) . . . . ? C35_4 C34_4 N34_4 O33_4 179.9(3) . . . . ? C33_4 C34_4 N34_4 O33_4 -2.2(5) . . . . ? C33_4 C34_4 C35_4 C36_4 1.7(6) . . . . ? N34_4 C34_4 C35_4 C36_4 179.6(3) . . . . ? C34_4 C35_4 C36_4 C31_4 -3.4(6) . . . . ? C34_4 C35_4 C36_4 C29_4 173.9(4) . . . . ? O31_4 C31_4 C36_4 C35_4 -177.5(3) . . . . ? C32_4 C31_4 C36_4 C35_4 3.2(6) . . . . ? O31_4 C31_4 C36_4 C29_4 5.1(6) . . . . ? C32_4 C31_4 C36_4 C29_4 -174.2(4) . . . . ? C28_4 C29_4 C36_4 C35_4 -178.7(4) . . . . ? C28_4 C29_4 C36_4 C31_4 -1.5(6) . . . . ? _diffrn_measured_fraction_theta_max 0.976 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 0.326 _refine_diff_density_min -0.331 _refine_diff_density_rms 0.080 # data_3 _database_code_depnum_ccdc_archive 'CCDC 741055' _audit_creation_method SHELXL-97 _chemical_name_systematic ; EH-01-65-10 (ethylpropion-3-yl) methoxy nitro- spiropyran ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C25 H28 N2 O6' _chemical_formula_sum 'C25 H28 N2 O6' _chemical_formula_weight 452.49 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 Cc loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x, -y, z+1/2' 'x+1/2, y+1/2, z' 'x+1/2, -y+1/2, z+1/2' _cell_length_a 15.1881(13) _cell_length_b 12.6063(10) _cell_length_c 12.1356(10) _cell_angle_alpha 90.00 _cell_angle_beta 103.863(3) _cell_angle_gamma 90.00 _cell_volume 2255.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 4488 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 31.30 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 960 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 11726 _diffrn_reflns_av_R_equivalents 0.0283 _diffrn_reflns_av_sigmaI/netI 0.0324 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.13 _diffrn_reflns_theta_max 31.50 _reflns_number_total 3756 _reflns_number_gt 3361 _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^)+(0.0750P)^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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3756 _refine_ls_number_parameters 302 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0474 _refine_ls_R_factor_gt 0.0406 _refine_ls_wR_factor_ref 0.1082 _refine_ls_wR_factor_gt 0.1022 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.016 _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 N11 N 0.74189(10) 0.62159(12) 0.92194(12) 0.0200(3) Uani 1 1 d . . . C12 C 0.65874(11) 0.63521(14) 0.83462(13) 0.0174(3) Uani 1 1 d . . . C13 C 0.63105(11) 0.75301(14) 0.84965(14) 0.0187(3) Uani 1 1 d . . . C14 C 0.67462(12) 0.76950(14) 0.97478(14) 0.0192(3) Uani 1 1 d . . . C15 C 0.66144(14) 0.84903(16) 1.04805(16) 0.0260(4) Uani 1 1 d . . . H15 H 0.6172 0.9026 1.0231 0.031 Uiso 1 1 calc R . . C16 C 0.71467(16) 0.84883(19) 1.15982(17) 0.0319(4) Uani 1 1 d . . . H16 H 0.7064 0.9027 1.2112 0.038 Uiso 1 1 calc R . . C17 C 0.77899(15) 0.7707(2) 1.19560(17) 0.0329(5) Uani 1 1 d . . . H17 H 0.8145 0.7721 1.2715 0.040 Uiso 1 1 calc R . . C18 C 0.79323(13) 0.68931(18) 1.12264(16) 0.0264(4) Uani 1 1 d . . . H18 H 0.8374 0.6357 1.1477 0.032 Uiso 1 1 calc R . . C19 C 0.73975(12) 0.69057(15) 1.01189(14) 0.0198(3) Uani 1 1 d . . . C20 C 0.52841(13) 0.77032(17) 0.81515(16) 0.0263(4) Uani 1 1 d . . . H20A H 0.5152 0.8461 0.8191 0.039 Uiso 1 1 calc R . . H20B H 0.4997 0.7310 0.8668 0.039 Uiso 1 1 calc R . . H20C H 0.5046 0.7449 0.7374 0.039 Uiso 1 1 calc R . . C21 C 0.67576(14) 0.82892(15) 0.77932(15) 0.0232(3) Uani 1 1 d . . . H21A H 0.6651 0.9025 0.7988 0.035 Uiso 1 1 calc R . . H21B H 0.6494 0.8172 0.6983 0.035 Uiso 1 1 calc R . . H21C H 0.7411 0.8153 0.7962 0.035 Uiso 1 1 calc R . . C22 C 0.78615(13) 0.51755(15) 0.93692(16) 0.0235(3) Uani 1 1 d . . . H22A H 0.7435 0.4635 0.8955 0.028 Uiso 1 1 calc R . . H22B H 0.8011 0.4986 1.0185 0.028 Uiso 1 1 calc R . . C23 C 0.87307(13) 0.51577(16) 0.89372(16) 0.0240(3) Uani 1 1 d . . . H23A H 0.8950 0.4418 0.8937 0.029 Uiso 1 1 calc R . . H23B H 0.8596 0.5422 0.8146 0.029 Uiso 1 1 calc R . . C24 C 0.94680(14) 0.58390(16) 0.96735(17) 0.0262(4) Uani 1 1 d . . . H24A H 0.9199 0.6527 0.9814 0.031 Uiso 1 1 calc R . . H24B H 0.9688 0.5484 1.0416 0.031 Uiso 1 1 calc R . . C25 C 1.02704(13) 0.60508(17) 0.91675(16) 0.0254(4) Uani 1 1 d . . . O25 O 1.04016(10) 0.56509(13) 0.83241(13) 0.0325(3) Uani 1 1 d . . . O26 O 1.08277(10) 0.67742(12) 0.98030(12) 0.0291(3) Uani 1 1 d . . . C26 C 1.16252(15) 0.70785(19) 0.94134(18) 0.0316(4) Uani 1 1 d . . . H26A H 1.1833 0.7788 0.9719 0.038 Uiso 1 1 calc R . . H26B H 1.1465 0.7125 0.8575 0.038 Uiso 1 1 calc R . . C27 C 1.23842(15) 0.6284(2) 0.97914(19) 0.0358(5) Uani 1 1 d . . . H27A H 1.2922 0.6526 0.9550 0.054 Uiso 1 1 calc R . . H27B H 1.2193 0.5592 0.9449 0.054 Uiso 1 1 calc R . . H27C H 1.2530 0.6221 1.0620 0.054 Uiso 1 1 calc R . . C28 C 0.67127(12) 0.60497(15) 0.71987(14) 0.0198(3) Uani 1 1 d . . . H28 H 0.7087 0.6485 0.6863 0.024 Uiso 1 1 calc R . . C29 C 0.63268(12) 0.52035(14) 0.66272(14) 0.0195(3) Uani 1 1 d . . . H29 H 0.6458 0.5031 0.5922 0.023 Uiso 1 1 calc R . . C31 C 0.55015(11) 0.48465(14) 0.80794(13) 0.0173(3) Uani 1 1 d . . . O31 O 0.58822(9) 0.56992(11) 0.86821(10) 0.0221(3) Uani 1 1 d . . . C32 C 0.48575(11) 0.42832(15) 0.85210(14) 0.0189(3) Uani 1 1 d . . . O32 O 0.46931(9) 0.46828(11) 0.94930(11) 0.0242(3) Uani 1 1 d . . . C33 C 0.44415(12) 0.33994(14) 0.79440(14) 0.0195(3) Uani 1 1 d . . . H33 H 0.4009 0.3005 0.8225 0.023 Uiso 1 1 calc R . . C34 C 0.46709(12) 0.31007(15) 0.69389(15) 0.0201(3) Uani 1 1 d . . . N34 N 0.42070(12) 0.21900(13) 0.63192(14) 0.0258(3) Uani 1 1 d . . . O33 O 0.35900(10) 0.17689(12) 0.66568(13) 0.0302(3) Uani 1 1 d . . . O34 O 0.44423(15) 0.18877(17) 0.54760(17) 0.0502(5) Uani 1 1 d . . . C35 C 0.52912(12) 0.36428(14) 0.64901(14) 0.0199(3) Uani 1 1 d . . . H35 H 0.5433 0.3413 0.5807 0.024 Uiso 1 1 calc R . . C36 C 0.57068(11) 0.45394(14) 0.70659(14) 0.0182(3) Uani 1 1 d . . . C37 C 0.41229(15) 0.40743(19) 1.00356(17) 0.0302(4) Uani 1 1 d . . . H37A H 0.4068 0.4436 1.0731 0.045 Uiso 1 1 calc R . . H37B H 0.4389 0.3370 1.0226 0.045 Uiso 1 1 calc R . . H37C H 0.3521 0.4000 0.9521 0.045 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 N11 0.0184(6) 0.0216(7) 0.0203(6) 0.0013(5) 0.0053(5) 0.0009(5) C12 0.0163(7) 0.0194(7) 0.0182(7) -0.0010(5) 0.0073(6) -0.0041(6) C13 0.0167(7) 0.0214(8) 0.0186(7) -0.0003(6) 0.0056(6) -0.0006(6) C14 0.0197(7) 0.0205(8) 0.0182(7) -0.0006(6) 0.0066(6) -0.0045(6) C15 0.0307(9) 0.0254(9) 0.0246(8) -0.0024(7) 0.0118(7) -0.0015(7) C16 0.0370(11) 0.0386(11) 0.0221(8) -0.0086(7) 0.0107(8) -0.0059(9) C17 0.0307(10) 0.0497(14) 0.0180(8) -0.0036(8) 0.0052(7) -0.0047(9) C18 0.0218(8) 0.0363(10) 0.0208(7) 0.0018(7) 0.0045(6) 0.0004(7) C19 0.0181(7) 0.0241(8) 0.0180(7) 0.0005(6) 0.0059(6) -0.0035(6) C20 0.0192(8) 0.0321(10) 0.0276(9) 0.0001(7) 0.0059(7) 0.0033(7) C21 0.0278(9) 0.0223(8) 0.0204(7) 0.0026(6) 0.0077(6) -0.0010(7) C22 0.0227(8) 0.0220(9) 0.0273(8) 0.0059(6) 0.0088(7) 0.0035(7) C23 0.0236(8) 0.0224(9) 0.0279(8) 0.0034(6) 0.0100(7) 0.0036(7) C24 0.0235(8) 0.0300(10) 0.0268(8) 0.0010(7) 0.0094(7) 0.0015(7) C25 0.0217(8) 0.0285(9) 0.0264(8) 0.0037(7) 0.0067(7) 0.0044(7) O25 0.0283(7) 0.0381(8) 0.0345(7) -0.0053(6) 0.0141(6) -0.0011(6) O26 0.0261(7) 0.0364(8) 0.0270(7) -0.0014(6) 0.0104(6) -0.0030(6) C26 0.0295(10) 0.0368(11) 0.0304(9) 0.0015(8) 0.0108(8) -0.0087(8) C27 0.0256(9) 0.0515(14) 0.0306(10) -0.0007(9) 0.0076(8) -0.0040(9) C28 0.0185(7) 0.0240(8) 0.0195(7) 0.0002(6) 0.0100(6) -0.0022(6) C29 0.0197(7) 0.0231(8) 0.0181(7) -0.0001(6) 0.0091(6) -0.0009(6) C31 0.0166(7) 0.0187(7) 0.0168(7) -0.0001(5) 0.0046(5) -0.0017(6) O31 0.0235(6) 0.0257(7) 0.0207(5) -0.0047(5) 0.0124(5) -0.0098(5) C32 0.0174(7) 0.0231(8) 0.0173(7) 0.0003(6) 0.0062(6) -0.0023(6) O32 0.0273(7) 0.0276(7) 0.0214(6) -0.0057(5) 0.0134(5) -0.0109(5) C33 0.0177(7) 0.0215(8) 0.0206(7) 0.0000(6) 0.0070(6) -0.0034(6) C34 0.0193(7) 0.0199(8) 0.0219(7) -0.0039(6) 0.0062(6) -0.0048(6) N34 0.0276(8) 0.0256(8) 0.0260(7) -0.0076(6) 0.0101(6) -0.0095(6) O33 0.0289(7) 0.0312(8) 0.0332(7) -0.0047(6) 0.0129(6) -0.0137(6) O34 0.0603(11) 0.0549(11) 0.0475(10) -0.0323(9) 0.0366(9) -0.0351(10) C35 0.0204(7) 0.0214(8) 0.0196(7) -0.0025(6) 0.0081(6) -0.0030(6) C36 0.0171(7) 0.0208(8) 0.0182(7) -0.0002(6) 0.0072(6) -0.0015(6) C37 0.0324(10) 0.0389(11) 0.0251(8) -0.0079(8) 0.0183(8) -0.0161(8) _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 N11 C19 1.402(2) . ? N11 C12 1.451(2) . ? N11 C22 1.465(2) . ? C12 O31 1.4833(19) . ? C12 C28 1.499(2) . ? C12 C13 1.566(3) . ? C13 C14 1.518(2) . ? C13 C20 1.530(3) . ? C13 C21 1.544(2) . ? C14 C15 1.386(3) . ? C14 C19 1.399(3) . ? C15 C16 1.403(3) . ? C15 H15 0.9500 . ? C16 C17 1.382(4) . ? C16 H16 0.9500 . ? C17 C18 1.406(3) . ? C17 H17 0.9500 . ? C18 C19 1.394(3) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.533(3) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 C24 1.520(3) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? C24 C25 1.514(3) . ? C24 H24A 0.9900 . ? C24 H24B 0.9900 . ? C25 O25 1.200(2) . ? C25 O26 1.353(3) . ? O26 C26 1.453(2) . ? C26 C27 1.513(3) . ? C26 H26A 0.9900 . ? C26 H26B 0.9900 . ? C27 H27A 0.9800 . ? C27 H27B 0.9800 . ? C27 H27C 0.9800 . ? C28 C29 1.330(3) . ? C28 H28 0.9500 . ? C29 C36 1.453(2) . ? C29 H29 0.9500 . ? C31 O31 1.350(2) . ? C31 C36 1.394(2) . ? C31 C32 1.414(2) . ? C32 O32 1.360(2) . ? C32 C33 1.385(2) . ? O32 C37 1.430(2) . ? C33 C34 1.398(2) . ? C33 H33 0.9500 . ? C34 C35 1.377(2) . ? C34 N34 1.458(2) . ? N34 O34 1.223(2) . ? N34 O33 1.230(2) . ? C35 C36 1.397(2) . ? C35 H35 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 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 C19 N11 C12 108.47(14) . . ? C19 N11 C22 123.65(15) . . ? C12 N11 C22 119.32(15) . . ? N11 C12 O31 107.04(13) . . ? N11 C12 C28 111.49(14) . . ? O31 C12 C28 112.02(13) . . ? N11 C12 C13 103.78(13) . . ? O31 C12 C13 105.21(13) . . ? C28 C12 C13 116.53(14) . . ? C14 C13 C20 115.19(14) . . ? C14 C13 C21 108.91(14) . . ? C20 C13 C21 108.34(15) . . ? C14 C13 C12 100.45(13) . . ? C20 C13 C12 112.82(15) . . ? C21 C13 C12 110.94(14) . . ? C15 C14 C19 120.50(17) . . ? C15 C14 C13 130.18(17) . . ? C19 C14 C13 109.25(15) . . ? C14 C15 C16 118.73(19) . . ? C14 C15 H15 120.6 . . ? C16 C15 H15 120.6 . . ? C17 C16 C15 120.36(19) . . ? C17 C16 H16 119.8 . . ? C15 C16 H16 119.8 . . ? C16 C17 C18 121.75(18) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C19 C18 C17 117.20(19) . . ? C19 C18 H18 121.4 . . ? C17 C18 H18 121.4 . . ? C18 C19 C14 121.47(17) . . ? C18 C19 N11 128.82(17) . . ? C14 C19 N11 109.69(14) . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 C21 H21A 109.5 . . ? C13 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C13 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N11 C22 C23 112.20(15) . . ? N11 C22 H22A 109.2 . . ? C23 C22 H22A 109.2 . . ? N11 C22 H22B 109.2 . . ? C23 C22 H22B 109.2 . . ? H22A C22 H22B 107.9 . . ? C24 C23 C22 111.36(16) . . ? C24 C23 H23A 109.4 . . ? C22 C23 H23A 109.4 . . ? C24 C23 H23B 109.4 . . ? C22 C23 H23B 109.4 . . ? H23A C23 H23B 108.0 . . ? C25 C24 C23 114.35(16) . . ? C25 C24 H24A 108.7 . . ? C23 C24 H24A 108.7 . . ? C25 C24 H24B 108.7 . . ? C23 C24 H24B 108.7 . . ? H24A C24 H24B 107.6 . . ? O25 C25 O26 124.09(18) . . ? O25 C25 C24 125.90(19) . . ? O26 C25 C24 110.01(16) . . ? C25 O26 C26 116.67(15) . . ? O26 C26 C27 111.14(18) . . ? O26 C26 H26A 109.4 . . ? C27 C26 H26A 109.4 . . ? O26 C26 H26B 109.4 . . ? C27 C26 H26B 109.4 . . ? H26A C26 H26B 108.0 . . ? C26 C27 H27A 109.5 . . ? C26 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C26 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C29 C28 C12 123.39(15) . . ? C29 C28 H28 118.3 . . ? C12 C28 H28 118.3 . . ? C28 C29 C36 120.97(15) . . ? C28 C29 H29 119.5 . . ? C36 C29 H29 119.5 . . ? O31 C31 C36 122.81(15) . . ? O31 C31 C32 116.10(14) . . ? C36 C31 C32 121.07(15) . . ? C31 O31 C12 122.46(12) . . ? O32 C32 C33 125.46(15) . . ? O32 C32 C31 115.48(15) . . ? C33 C32 C31 119.05(15) . . ? C32 O32 C37 117.27(14) . . ? C32 C33 C34 118.60(15) . . ? C32 C33 H33 120.7 . . ? C34 C33 H33 120.7 . . ? C35 C34 C33 123.26(16) . . ? C35 C34 N34 118.59(15) . . ? C33 C34 N34 118.12(15) . . ? O34 N34 O33 122.90(17) . . ? O34 N34 C34 118.35(16) . . ? O33 N34 C34 118.74(15) . . ? C34 C35 C36 118.25(15) . . ? C34 C35 H35 120.9 . . ? C36 C35 H35 120.9 . . ? C31 C36 C35 119.74(15) . . ? C31 C36 C29 117.70(15) . . ? C35 C36 C29 122.51(15) . . ? O32 C37 H37A 109.5 . . ? O32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 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 C19 N11 C12 O31 -82.67(16) . . . . ? C22 N11 C12 O31 66.37(18) . . . . ? C19 N11 C12 C28 154.50(14) . . . . ? C22 N11 C12 C28 -56.46(19) . . . . ? C19 N11 C12 C13 28.29(17) . . . . ? C22 N11 C12 C13 177.33(14) . . . . ? N11 C12 C13 C14 -26.90(15) . . . . ? O31 C12 C13 C14 85.40(14) . . . . ? C28 C12 C13 C14 -149.85(14) . . . . ? N11 C12 C13 C20 -150.07(14) . . . . ? O31 C12 C13 C20 -37.77(17) . . . . ? C28 C12 C13 C20 86.98(17) . . . . ? N11 C12 C13 C21 88.16(16) . . . . ? O31 C12 C13 C21 -159.55(13) . . . . ? C28 C12 C13 C21 -34.8(2) . . . . ? C20 C13 C14 C15 -44.1(3) . . . . ? C21 C13 C14 C15 77.8(2) . . . . ? C12 C13 C14 C15 -165.61(18) . . . . ? C20 C13 C14 C19 138.99(16) . . . . ? C21 C13 C14 C19 -99.10(17) . . . . ? C12 C13 C14 C19 17.48(17) . . . . ? C19 C14 C15 C16 0.1(3) . . . . ? C13 C14 C15 C16 -176.55(18) . . . . ? C14 C15 C16 C17 0.1(3) . . . . ? C15 C16 C17 C18 -0.2(3) . . . . ? C16 C17 C18 C19 0.2(3) . . . . ? C17 C18 C19 C14 0.0(3) . . . . ? C17 C18 C19 N11 177.86(19) . . . . ? C15 C14 C19 C18 -0.1(3) . . . . ? C13 C14 C19 C18 177.13(16) . . . . ? C15 C14 C19 N11 -178.35(16) . . . . ? C13 C14 C19 N11 -1.09(19) . . . . ? C12 N11 C19 C18 164.14(18) . . . . ? C22 N11 C19 C18 16.7(3) . . . . ? C12 N11 C19 C14 -17.81(19) . . . . ? C22 N11 C19 C14 -165.21(16) . . . . ? C19 N11 C22 C23 -108.80(19) . . . . ? C12 N11 C22 C23 107.08(18) . . . . ? N11 C22 C23 C24 68.3(2) . . . . ? C22 C23 C24 C25 -167.65(16) . . . . ? C23 C24 C25 O25 -7.8(3) . . . . ? C23 C24 C25 O26 171.73(17) . . . . ? O25 C25 O26 C26 0.6(3) . . . . ? C24 C25 O26 C26 -178.87(17) . . . . ? C25 O26 C26 C27 -82.6(2) . . . . ? N11 C12 C28 C29 111.30(19) . . . . ? O31 C12 C28 C29 -8.6(2) . . . . ? C13 C12 C28 C29 -129.85(19) . . . . ? C12 C28 C29 C36 3.5(3) . . . . ? C36 C31 O31 C12 -3.1(2) . . . . ? C32 C31 O31 C12 178.22(15) . . . . ? N11 C12 O31 C31 -114.07(16) . . . . ? C28 C12 O31 C31 8.4(2) . . . . ? C13 C12 O31 C31 135.96(15) . . . . ? O31 C31 C32 O32 0.9(2) . . . . ? C36 C31 C32 O32 -177.75(16) . . . . ? O31 C31 C32 C33 -179.96(16) . . . . ? C36 C31 C32 C33 1.4(3) . . . . ? C33 C32 O32 C37 7.6(3) . . . . ? C31 C32 O32 C37 -173.33(17) . . . . ? O32 C32 C33 C34 178.64(17) . . . . ? C31 C32 C33 C34 -0.4(3) . . . . ? C32 C33 C34 C35 -0.1(3) . . . . ? C32 C33 C34 N34 -178.02(17) . . . . ? C35 C34 N34 O34 6.1(3) . . . . ? C33 C34 N34 O34 -175.8(2) . . . . ? C35 C34 N34 O33 -172.90(18) . . . . ? C33 C34 N34 O33 5.1(3) . . . . ? C33 C34 C35 C36 -0.4(3) . . . . ? N34 C34 C35 C36 177.54(17) . . . . ? O31 C31 C36 C35 179.56(16) . . . . ? C32 C31 C36 C35 -1.9(3) . . . . ? O31 C31 C36 C29 -2.9(3) . . . . ? C32 C31 C36 C29 175.67(16) . . . . ? C34 C35 C36 C31 1.4(3) . . . . ? C34 C35 C36 C29 -176.07(17) . . . . ? C28 C29 C36 C31 2.7(3) . . . . ? C28 C29 C36 C35 -179.81(18) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 31.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.354 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.051 # data_5 _database_code_depnum_ccdc_archive 'CCDC 741056' _audit_creation_method SHELXL-97 _chemical_name_systematic ; EH-01-64-04 nitro- methoxy- hydroxyethyl spiropyran ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H22 N2 O5' _chemical_formula_sum 'C21 H22 N2 O5' _chemical_formula_weight 382.41 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 P2(1)/n 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 6.7336(3) _cell_length_b 30.1846(12) _cell_length_c 9.5144(4) _cell_angle_alpha 90.00 _cell_angle_beta 96.314(2) _cell_angle_gamma 90.00 _cell_volume 1922.08(14) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 9949 _cell_measurement_theta_min 2.26 _cell_measurement_theta_max 32.41 _exptl_crystal_description prism _exptl_crystal_colour green _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.321 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 0.095 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 19947 _diffrn_reflns_av_R_equivalents 0.0242 _diffrn_reflns_av_sigmaI/netI 0.0236 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -43 _diffrn_reflns_limit_k_max 32 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.54 _diffrn_reflns_theta_max 32.36 _reflns_number_total 5830 _reflns_number_gt 4870 _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^)+(0.0700P)^2^+0.3500P] 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_number_reflns 5830 _refine_ls_number_parameters 259 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0498 _refine_ls_R_factor_gt 0.0408 _refine_ls_wR_factor_ref 0.1205 _refine_ls_wR_factor_gt 0.1139 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.037 _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 N11 N 0.19002(12) 0.14656(3) 0.26963(8) 0.01922(16) Uani 1 1 d . . . C12 C 0.33014(13) 0.11589(3) 0.30358(10) 0.01789(17) Uani 1 1 d . . . C13 C 0.29041(14) 0.07556(3) 0.20776(9) 0.01818(17) Uani 1 1 d . . . C14 C 0.10918(14) 0.09084(3) 0.11240(10) 0.02027(18) Uani 1 1 d . . . C15 C 0.00231(15) 0.07036(4) -0.00243(10) 0.0256(2) Uani 1 1 d . . . H15 H 0.0349 0.0412 -0.0296 0.031 Uiso 1 1 calc R . . C16 C -0.15421(15) 0.09361(4) -0.07722(11) 0.0295(2) Uani 1 1 d . . . H16 H -0.2299 0.0800 -0.1557 0.035 Uiso 1 1 calc R . . C17 C -0.20087(16) 0.13630(4) -0.03869(12) 0.0310(2) Uani 1 1 d . . . H17 H -0.3062 0.1516 -0.0929 0.037 Uiso 1 1 calc R . . C18 C -0.09718(15) 0.15739(4) 0.07758(12) 0.0281(2) Uani 1 1 d . . . H18 H -0.1296 0.1866 0.1049 0.034 Uiso 1 1 calc R . . C19 C 0.05635(14) 0.13321(3) 0.15107(10) 0.02113(19) Uani 1 1 d . . . C20 C 0.46498(15) 0.06675(4) 0.11990(11) 0.0270(2) Uani 1 1 d . . . H20A H 0.4954 0.0939 0.0698 0.041 Uiso 1 1 calc R . . H20B H 0.4278 0.0432 0.0512 0.041 Uiso 1 1 calc R . . H20C H 0.5829 0.0576 0.1828 0.041 Uiso 1 1 calc R . . C21 C 0.24237(15) 0.03404(3) 0.29202(10) 0.02207(19) Uani 1 1 d . . . H21A H 0.1290 0.0403 0.3453 0.033 Uiso 1 1 calc R . . H21B H 0.3592 0.0260 0.3578 0.033 Uiso 1 1 calc R . . H21C H 0.2084 0.0094 0.2266 0.033 Uiso 1 1 calc R . . C22 C 0.17279(16) 0.18913(3) 0.34245(11) 0.0239(2) Uani 1 1 d . . . H22A H 0.2174 0.1852 0.4444 0.029 Uiso 1 1 calc R . . H22B H 0.0307 0.1982 0.3333 0.029 Uiso 1 1 calc R . . C23 C 0.29526(19) 0.22561(3) 0.28424(12) 0.0305(2) Uani 1 1 d . . . H23A H 0.2852 0.2531 0.3397 0.037 Uiso 1 1 calc R . . H23B H 0.4375 0.2167 0.2908 0.037 Uiso 1 1 calc R . . O23 O 0.22115(18) 0.23295(3) 0.14242(9) 0.0475(3) Uani 1 1 d . . . H23 H 0.255(3) 0.2605(6) 0.1229(19) 0.057 Uiso 1 1 d . . . C24 C 0.49195(14) 0.12484(3) 0.40743(10) 0.01950(18) Uani 1 1 d . . . H24 H 0.4955 0.1531 0.4518 0.023 Uiso 1 1 calc R . . C25 C 0.64405(14) 0.09592(3) 0.44898(9) 0.01834(17) Uani 1 1 d . . . H25 H 0.6298 0.0664 0.4151 0.022 Uiso 1 1 calc R . . C31 C 0.86967(14) 0.15102(3) 0.58907(10) 0.02109(19) Uani 1 1 d . . . O31 O 0.75567(12) 0.18368(2) 0.56137(10) 0.0343(2) Uani 1 1 d . . . C32 C 1.06280(14) 0.15721(3) 0.67314(10) 0.01967(18) Uani 1 1 d . . . O32 O 1.09536(11) 0.20009(2) 0.71422(8) 0.02714(17) Uani 1 1 d . . . C33 C 1.19403(14) 0.12322(3) 0.70284(10) 0.01890(18) Uani 1 1 d . . . H33 H 1.3199 0.1283 0.7560 0.023 Uiso 1 1 calc R . . C34 C 1.13905(13) 0.08025(3) 0.65289(9) 0.01729(17) Uani 1 1 d . . . N34 N 1.27650(12) 0.04458(3) 0.68603(9) 0.02068(17) Uani 1 1 d . . . O33 O 1.43877(12) 0.05268(3) 0.75490(10) 0.0351(2) Uani 1 1 d . . . O34 O 1.22923(11) 0.00653(2) 0.64504(8) 0.02867(18) Uani 1 1 d . . . C35 C 0.95955(13) 0.07186(3) 0.57391(9) 0.01699(17) Uani 1 1 d . . . H35 H 0.9277 0.0426 0.5427 0.020 Uiso 1 1 calc R . . C36 C 0.82282(13) 0.10638(3) 0.53905(9) 0.01757(17) Uani 1 1 d . . . C37 C 1.27557(18) 0.20895(4) 0.80324(14) 0.0342(3) Uani 1 1 d . . . H37A H 1.2785 0.2402 0.8315 0.051 Uiso 1 1 calc R . . H37B H 1.3905 0.2026 0.7517 0.051 Uiso 1 1 calc R . . H37C H 1.2815 0.1902 0.8876 0.051 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 N11 0.0175(4) 0.0161(3) 0.0230(4) 0.0033(3) -0.0028(3) -0.0006(3) C12 0.0173(4) 0.0153(4) 0.0206(4) 0.0029(3) -0.0004(3) -0.0015(3) C13 0.0179(4) 0.0174(4) 0.0187(4) 0.0004(3) -0.0006(3) -0.0024(3) C14 0.0166(4) 0.0235(4) 0.0201(4) 0.0033(3) -0.0006(3) -0.0048(3) C15 0.0221(5) 0.0326(5) 0.0215(4) 0.0001(4) 0.0003(4) -0.0096(4) C16 0.0205(5) 0.0453(6) 0.0215(4) 0.0051(4) -0.0027(4) -0.0116(4) C17 0.0184(4) 0.0428(6) 0.0298(5) 0.0132(5) -0.0058(4) -0.0059(4) C18 0.0204(5) 0.0292(5) 0.0330(5) 0.0101(4) -0.0042(4) -0.0012(4) C19 0.0167(4) 0.0229(4) 0.0226(4) 0.0059(3) -0.0028(3) -0.0038(3) C20 0.0220(5) 0.0358(5) 0.0235(5) -0.0016(4) 0.0033(4) -0.0017(4) C21 0.0259(5) 0.0166(4) 0.0233(4) 0.0006(3) 0.0012(4) -0.0028(3) C22 0.0263(5) 0.0180(4) 0.0267(5) 0.0013(3) -0.0006(4) 0.0045(4) C23 0.0417(6) 0.0177(4) 0.0301(5) 0.0039(4) -0.0059(4) -0.0038(4) O23 0.0807(8) 0.0240(4) 0.0327(4) 0.0112(3) -0.0159(5) -0.0203(4) C24 0.0191(4) 0.0170(4) 0.0213(4) -0.0004(3) -0.0030(3) 0.0004(3) C25 0.0188(4) 0.0160(4) 0.0193(4) -0.0009(3) -0.0020(3) -0.0004(3) C31 0.0209(4) 0.0162(4) 0.0249(4) -0.0035(3) -0.0036(3) 0.0007(3) O31 0.0308(4) 0.0165(3) 0.0510(5) -0.0092(3) -0.0170(4) 0.0060(3) C32 0.0208(4) 0.0157(4) 0.0216(4) -0.0035(3) -0.0017(3) -0.0024(3) O32 0.0270(4) 0.0163(3) 0.0354(4) -0.0070(3) -0.0086(3) -0.0019(3) C33 0.0178(4) 0.0184(4) 0.0197(4) -0.0028(3) -0.0015(3) -0.0019(3) C34 0.0164(4) 0.0166(4) 0.0184(4) -0.0011(3) -0.0005(3) 0.0014(3) N34 0.0184(4) 0.0198(4) 0.0225(4) -0.0029(3) -0.0040(3) 0.0020(3) O33 0.0223(4) 0.0296(4) 0.0488(5) -0.0096(4) -0.0170(3) 0.0040(3) O34 0.0277(4) 0.0171(3) 0.0382(4) -0.0056(3) -0.0098(3) 0.0031(3) C35 0.0179(4) 0.0147(4) 0.0178(4) -0.0015(3) -0.0005(3) -0.0002(3) C36 0.0181(4) 0.0150(4) 0.0188(4) -0.0015(3) -0.0018(3) 0.0002(3) C37 0.0308(5) 0.0242(5) 0.0439(6) -0.0105(4) -0.0123(5) -0.0053(4) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag N11 C12 1.3358(11) . ? N11 C19 1.4218(11) . ? N11 C22 1.4705(13) . ? C12 C24 1.4141(12) . ? C12 C13 1.5269(13) . ? C13 C14 1.5105(13) . ? C13 C20 1.5386(14) . ? C13 C21 1.5411(13) . ? C14 C15 1.3858(13) . ? C14 C19 1.3881(14) . ? C15 C16 1.3945(15) . ? C15 H15 0.9500 . ? C16 C17 1.3852(18) . ? C16 H16 0.9500 . ? C17 C18 1.3952(15) . ? C17 H17 0.9500 . ? C18 C19 1.3897(13) . ? C18 H18 0.9500 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 0.9800 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? C22 C23 1.5164(15) . ? C22 H22A 0.9900 . ? C22 H22B 0.9900 . ? C23 O23 1.4038(13) . ? C23 H23A 0.9900 . ? C23 H23B 0.9900 . ? O23 H23 0.89(2) . ? C24 C25 1.3704(12) . ? C24 H24 0.9500 . ? C25 C36 1.4340(12) . ? C25 H25 0.9500 . ? C31 O31 1.2593(12) . ? C31 C36 1.4521(12) . ? C31 C32 1.4619(13) . ? C32 O32 1.3627(11) . ? C32 C33 1.3633(13) . ? O32 C37 1.4266(12) . ? C33 C34 1.4165(12) . ? C33 H33 0.9500 . ? C34 C35 1.3748(12) . ? C34 N34 1.4323(11) . ? N34 O33 1.2351(10) . ? N34 O34 1.2431(10) . ? C35 C36 1.4058(12) . ? C35 H35 0.9500 . ? C37 H37A 0.9800 . ? C37 H37B 0.9800 . ? C37 H37C 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 C12 N11 C19 111.36(8) . . ? C12 N11 C22 125.58(8) . . ? C19 N11 C22 123.06(8) . . ? N11 C12 C24 120.41(8) . . ? N11 C12 C13 109.60(8) . . ? C24 C12 C13 129.82(8) . . ? C14 C13 C12 101.08(7) . . ? C14 C13 C20 109.97(8) . . ? C12 C13 C20 111.59(8) . . ? C14 C13 C21 111.03(7) . . ? C12 C13 C21 111.77(7) . . ? C20 C13 C21 111.02(8) . . ? C15 C14 C19 119.60(9) . . ? C15 C14 C13 130.74(10) . . ? C19 C14 C13 109.62(8) . . ? C14 C15 C16 118.40(10) . . ? C14 C15 H15 120.8 . . ? C16 C15 H15 120.8 . . ? C17 C16 C15 120.92(10) . . ? C17 C16 H16 119.5 . . ? C15 C16 H16 119.5 . . ? C16 C17 C18 121.73(10) . . ? C16 C17 H17 119.1 . . ? C18 C17 H17 119.1 . . ? C19 C18 C17 116.04(11) . . ? C19 C18 H18 122.0 . . ? C17 C18 H18 122.0 . . ? C14 C19 C18 123.28(9) . . ? C14 C19 N11 108.24(8) . . ? C18 C19 N11 128.41(10) . . ? C13 C20 H20A 109.5 . . ? C13 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C13 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 C21 H21A 109.5 . . ? C13 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C13 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? N11 C22 C23 112.84(9) . . ? N11 C22 H22A 109.0 . . ? C23 C22 H22A 109.0 . . ? N11 C22 H22B 109.0 . . ? C23 C22 H22B 109.0 . . ? H22A C22 H22B 107.8 . . ? O23 C23 C22 108.39(9) . . ? O23 C23 H23A 110.0 . . ? C22 C23 H23A 110.0 . . ? O23 C23 H23B 110.0 . . ? C22 C23 H23B 110.0 . . ? H23A C23 H23B 108.4 . . ? C23 O23 H23 106.1(12) . . ? C25 C24 C12 125.03(9) . . ? C25 C24 H24 117.5 . . ? C12 C24 H24 117.5 . . ? C24 C25 C36 125.71(8) . . ? C24 C25 H25 117.1 . . ? C36 C25 H25 117.1 . . ? O31 C31 C36 123.52(8) . . ? O31 C31 C32 119.97(8) . . ? C36 C31 C32 116.50(8) . . ? O32 C32 C33 125.11(8) . . ? O32 C32 C31 112.57(8) . . ? C33 C32 C31 122.31(8) . . ? C32 O32 C37 116.61(8) . . ? C32 C33 C34 118.69(8) . . ? C32 C33 H33 120.7 . . ? C34 C33 H33 120.7 . . ? C35 C34 C33 122.26(8) . . ? C35 C34 N34 119.32(8) . . ? C33 C34 N34 118.42(8) . . ? O33 N34 O34 122.03(8) . . ? O33 N34 C34 118.71(8) . . ? O34 N34 C34 119.25(8) . . ? C34 C35 C36 120.39(8) . . ? C34 C35 H35 119.8 . . ? C36 C35 H35 119.8 . . ? C35 C36 C25 117.56(8) . . ? C35 C36 C31 119.83(8) . . ? C25 C36 C31 122.55(8) . . ? O32 C37 H37A 109.5 . . ? O32 C37 H37B 109.5 . . ? H37A C37 H37B 109.5 . . ? O32 C37 H37C 109.5 . . ? H37A C37 H37C 109.5 . . ? H37B C37 H37C 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 C19 N11 C12 C24 172.34(8) . . . . ? C22 N11 C12 C24 -7.20(14) . . . . ? C19 N11 C12 C13 -3.36(11) . . . . ? C22 N11 C12 C13 177.10(8) . . . . ? N11 C12 C13 C14 2.29(10) . . . . ? C24 C12 C13 C14 -172.88(9) . . . . ? N11 C12 C13 C20 119.14(9) . . . . ? C24 C12 C13 C20 -56.03(13) . . . . ? N11 C12 C13 C21 -115.87(9) . . . . ? C24 C12 C13 C21 68.96(13) . . . . ? C12 C13 C14 C15 177.05(10) . . . . ? C20 C13 C14 C15 59.01(13) . . . . ? C21 C13 C14 C15 -64.26(13) . . . . ? C12 C13 C14 C19 -0.43(10) . . . . ? C20 C13 C14 C19 -118.46(9) . . . . ? C21 C13 C14 C19 118.27(9) . . . . ? C19 C14 C15 C16 1.02(14) . . . . ? C13 C14 C15 C16 -176.24(9) . . . . ? C14 C15 C16 C17 0.59(15) . . . . ? C15 C16 C17 C18 -1.46(16) . . . . ? C16 C17 C18 C19 0.64(16) . . . . ? C15 C14 C19 C18 -1.89(15) . . . . ? C13 C14 C19 C18 175.91(9) . . . . ? C15 C14 C19 N11 -179.24(8) . . . . ? C13 C14 C19 N11 -1.44(10) . . . . ? C17 C18 C19 C14 1.03(15) . . . . ? C17 C18 C19 N11 177.82(10) . . . . ? C12 N11 C19 C14 3.07(11) . . . . ? C22 N11 C19 C14 -177.39(8) . . . . ? C12 N11 C19 C18 -174.11(10) . . . . ? C22 N11 C19 C18 5.44(16) . . . . ? C12 N11 C22 C23 87.52(11) . . . . ? C19 N11 C22 C23 -91.96(11) . . . . ? N11 C22 C23 O23 62.83(12) . . . . ? N11 C12 C24 C25 -179.38(9) . . . . ? C13 C12 C24 C25 -4.65(16) . . . . ? C12 C24 C25 C36 170.76(9) . . . . ? O31 C31 C32 O32 0.63(14) . . . . ? C36 C31 C32 O32 179.30(8) . . . . ? O31 C31 C32 C33 -178.17(10) . . . . ? C36 C31 C32 C33 0.50(14) . . . . ? C33 C32 O32 C37 -4.50(15) . . . . ? C31 C32 O32 C37 176.74(9) . . . . ? O32 C32 C33 C34 179.97(9) . . . . ? C31 C32 C33 C34 -1.38(15) . . . . ? C32 C33 C34 C35 0.99(14) . . . . ? C32 C33 C34 N34 -179.19(8) . . . . ? C35 C34 N34 O33 178.72(9) . . . . ? C33 C34 N34 O33 -1.10(14) . . . . ? C35 C34 N34 O34 -1.38(14) . . . . ? C33 C34 N34 O34 178.80(9) . . . . ? C33 C34 C35 C36 0.32(14) . . . . ? N34 C34 C35 C36 -179.49(8) . . . . ? C34 C35 C36 C25 176.14(8) . . . . ? C34 C35 C36 C31 -1.22(14) . . . . ? C24 C25 C36 C35 177.97(9) . . . . ? C24 C25 C36 C31 -4.75(15) . . . . ? O31 C31 C36 C35 179.43(10) . . . . ? C32 C31 C36 C35 0.82(14) . . . . ? O31 C31 C36 C25 2.21(16) . . . . ? C32 C31 C36 C25 -176.40(9) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O23 H23 O31 0.89(2) 1.78(2) 2.6499(11) 164.8(17) 4_565 _diffrn_measured_fraction_theta_max 0.847 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.984 _refine_diff_density_max 0.410 _refine_diff_density_min -0.200 _refine_diff_density_rms 0.046 #END