# Supplementary Material (ESI) for Journal of Materials Chemistry # This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_coden_Cambridge 1145 _journal_volume ? _journal_page_first ? _journal_year ? loop_ _publ_author_name 'Sui, Yan' 'Liu, Dong-Sheng' 'Hu, Rong-Hua' 'Chen, Hong-Mei' _publ_contact_author_name 'Dr Yan Sui' _publ_contact_author_email ysui@163.com _publ_section_title ; Discovery of New Type of Organic Ferroelectric Materials in Natural Biomass Dehydroabietylamine Schiff Bases ; # Attachment '- BrDHA.cif' data_90622dm _database_code_depnum_ccdc_archive 'CCDC 806391' #TrackingRef '- BrDHA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H34 Br N O' _chemical_formula_sum 'C27 H34 Br N O' _chemical_formula_weight 468.46 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_space_group_name_Hall 'P 2yb ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.264(4) _cell_length_b 6.189(2) _cell_length_c 17.301(6) _cell_angle_alpha 90.00 _cell_angle_beta 102.785(7) _cell_angle_gamma 90.00 _cell_volume 1176.2(8) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 7118 _cell_measurement_theta_min 2.69 _cell_measurement_theta_max 20.72 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 492 _exptl_absorpt_coefficient_mu 1.766 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4604 _exptl_absorpt_correction_T_max 0.7417 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker Smart Apex CCD' _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 6409 _diffrn_reflns_av_R_equivalents 0.0886 _diffrn_reflns_av_sigmaI/netI 0.1022 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.98 _diffrn_reflns_theta_max 26.10 _reflns_number_total 4196 _reflns_number_gt 2315 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0300P)^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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.010(13) _chemical_absolute_configuration rm _refine_ls_number_reflns 4196 _refine_ls_number_parameters 275 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0875 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1191 _refine_ls_wR_factor_gt 0.1142 _refine_ls_goodness_of_fit_ref 1.019 _refine_ls_restrained_S_all 1.019 _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 Br1 Br 0.88674(5) -0.08203(14) 0.52161(4) 0.0994(3) Uani 1 1 d . . . C1 C 0.5308(5) -0.2468(10) 0.4180(3) 0.0541(14) Uani 1 1 d . . . C2 C 0.5427(5) -0.4593(9) 0.3947(3) 0.0557(14) Uani 1 1 d . . . C3 C 0.6553(5) -0.5530(12) 0.4074(3) 0.0699(16) Uani 1 1 d . . . H3 H 0.6632 -0.6932 0.3898 0.084 Uiso 1 1 calc R . . C4 C 0.7563(5) -0.4425(11) 0.4457(3) 0.0668(17) Uani 1 1 d . . . H4 H 0.8323 -0.5085 0.4552 0.080 Uiso 1 1 calc R . . C5 C 0.7454(5) -0.2359(11) 0.4698(3) 0.0620(15) Uani 1 1 d . . . C6 C 0.6344(4) -0.1366(9) 0.4569(3) 0.0565(15) Uani 1 1 d . . . H6 H 0.6281 0.0044 0.4741 0.068 Uiso 1 1 calc R . . C7 C 0.4135(4) -0.1348(9) 0.4005(3) 0.0567(15) Uani 1 1 d . . . H7 H 0.4094 0.0104 0.4136 0.068 Uiso 1 1 calc R . . C8 C 0.1999(4) -0.1266(10) 0.3471(3) 0.0623(16) Uani 1 1 d . . . H8A H 0.2113 0.0284 0.3531 0.075 Uiso 1 1 calc R . . H8B H 0.1497 -0.1735 0.3829 0.075 Uiso 1 1 calc R . . C9 C 0.1346(4) -0.1791(8) 0.2606(3) 0.0527(15) Uani 1 1 d . . . C10 C 0.2153(4) -0.0883(14) 0.2073(3) 0.0650(14) Uani 1 1 d . . . H10A H 0.2398 0.0574 0.2245 0.078 Uiso 1 1 calc R . . H10B H 0.2884 -0.1756 0.2142 0.078 Uiso 1 1 calc R . . C11 C 0.1536(4) -0.0834(14) 0.1203(3) 0.0734(15) Uani 1 1 d . . . H11A H 0.1346 -0.2298 0.1016 0.088 Uiso 1 1 calc R . . H11B H 0.2087 -0.0217 0.0904 0.088 Uiso 1 1 calc R . . C12 C 0.0362(4) 0.0506(10) 0.1060(3) 0.0605(15) Uani 1 1 d . . . H12A H -0.0016 0.0506 0.0498 0.073 Uiso 1 1 calc R . . H12B H 0.0556 0.1988 0.1222 0.073 Uiso 1 1 calc R . . C13 C -0.0537(4) -0.0421(10) 0.1527(3) 0.0504(14) Uani 1 1 d . . . C14 C 0.0116(3) -0.0564(10) 0.2419(2) 0.0470(12) Uani 1 1 d . . . H14 H 0.0329 0.0933 0.2575 0.056 Uiso 1 1 calc R . . C15 C -0.0793(4) -0.1216(11) 0.2905(3) 0.0632(16) Uani 1 1 d . . . H15A H -0.1204 -0.2534 0.2691 0.076 Uiso 1 1 calc R . . H15B H -0.0368 -0.1495 0.3448 0.076 Uiso 1 1 calc R . . C16 C -0.1715(5) 0.0548(11) 0.2892(3) 0.0774(19) Uani 1 1 d . . . H16A H -0.1346 0.1687 0.3252 0.093 Uiso 1 1 calc R . . H16B H -0.2394 -0.0030 0.3087 0.093 Uiso 1 1 calc R . . C17 C -0.2194(5) 0.1515(9) 0.2082(3) 0.0591(15) Uani 1 1 d . . . C18 C -0.1641(4) 0.1111(8) 0.1461(3) 0.0484(14) Uani 1 1 d . . . C19 C -0.2174(5) 0.2015(9) 0.0734(3) 0.0624(16) Uani 1 1 d . . . H19 H -0.1819 0.1769 0.0305 0.075 Uiso 1 1 calc R . . C20 C -0.3200(5) 0.3252(9) 0.0622(3) 0.0667(18) Uani 1 1 d . . . H20 H -0.3536 0.3795 0.0120 0.080 Uiso 1 1 calc R . . C21 C -0.3743(4) 0.3707(10) 0.1235(4) 0.0646(16) Uani 1 1 d . . . C22 C -0.3240(5) 0.2816(9) 0.1959(3) 0.0651(16) Uani 1 1 d . . . H22 H -0.3603 0.3084 0.2383 0.078 Uiso 1 1 calc R . . C23 C 0.1197(5) -0.4222(8) 0.2522(4) 0.0675(17) Uani 1 1 d . . . H23A H 0.0536 -0.4681 0.2750 0.101 Uiso 1 1 calc R . . H23B H 0.1934 -0.4918 0.2792 0.101 Uiso 1 1 calc R . . H23C H 0.1028 -0.4605 0.1971 0.101 Uiso 1 1 calc R . . C24 C -0.1049(5) -0.2564(9) 0.1159(4) 0.0694(17) Uani 1 1 d . . . H24A H -0.1599 -0.2294 0.0659 0.104 Uiso 1 1 calc R . . H24B H -0.1476 -0.3280 0.1508 0.104 Uiso 1 1 calc R . . H24C H -0.0393 -0.3464 0.1077 0.104 Uiso 1 1 calc R . . C25 C -0.4873(5) 0.5097(11) 0.1118(4) 0.084(2) Uani 1 1 d . . . H25 H -0.5059 0.5508 0.0558 0.100 Uiso 1 1 calc R . . C26 C -0.4671(6) 0.7148(11) 0.1564(5) 0.106(3) Uani 1 1 d . . . H26A H -0.4417 0.6846 0.2121 0.160 Uiso 1 1 calc R . . H26B H -0.5414 0.7966 0.1467 0.160 Uiso 1 1 calc R . . H26C H -0.4050 0.7967 0.1395 0.160 Uiso 1 1 calc R . . C27 C -0.5966(5) 0.3866(15) 0.1239(5) 0.113(3) Uani 1 1 d . . . H27A H -0.5853 0.3470 0.1787 0.169 Uiso 1 1 calc R . . H27B H -0.6066 0.2585 0.0919 0.169 Uiso 1 1 calc R . . H27C H -0.6678 0.4755 0.1090 0.169 Uiso 1 1 calc R . . N1 N 0.3178(4) -0.2345(7) 0.3678(3) 0.0598(12) Uani 1 1 d . . . O1 O 0.4440(3) -0.5755(8) 0.3581(2) 0.0767(10) Uani 1 1 d . . . H1 H 0.3786 -0.4531 0.3575 0.092 Uiso 1 1 d 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 Br1 0.0521(3) 0.1328(6) 0.1088(5) -0.0281(6) 0.0078(3) -0.0055(5) C1 0.048(3) 0.054(4) 0.059(4) 0.005(3) 0.009(3) 0.004(3) C2 0.063(4) 0.047(4) 0.057(4) -0.002(3) 0.015(3) 0.005(3) C3 0.076(4) 0.064(4) 0.069(4) -0.005(4) 0.015(3) 0.021(4) C4 0.061(4) 0.079(5) 0.062(4) 0.003(4) 0.016(3) 0.020(3) C5 0.052(3) 0.077(4) 0.058(4) 0.000(3) 0.012(3) -0.005(3) C6 0.058(3) 0.055(4) 0.057(3) -0.002(3) 0.012(2) 0.007(3) C7 0.059(3) 0.056(4) 0.054(3) -0.002(3) 0.009(3) -0.001(3) C8 0.052(3) 0.069(4) 0.063(3) -0.004(3) 0.009(2) 0.013(3) C9 0.052(3) 0.057(4) 0.049(3) -0.003(3) 0.012(3) 0.005(2) C10 0.045(2) 0.083(4) 0.070(4) -0.011(4) 0.019(2) 0.003(4) C11 0.059(3) 0.104(4) 0.063(3) -0.011(5) 0.027(3) -0.005(5) C12 0.054(3) 0.080(4) 0.051(3) 0.000(3) 0.018(3) 0.003(3) C13 0.050(3) 0.057(4) 0.046(3) -0.006(3) 0.013(2) 0.000(3) C14 0.045(2) 0.048(3) 0.050(3) 0.000(3) 0.016(2) 0.001(3) C15 0.057(3) 0.081(5) 0.055(3) 0.012(4) 0.018(2) 0.004(4) C16 0.061(4) 0.118(5) 0.057(4) 0.009(4) 0.021(3) 0.026(4) C17 0.053(3) 0.077(4) 0.048(3) 0.001(3) 0.013(3) 0.008(3) C18 0.042(3) 0.055(4) 0.047(4) -0.001(3) 0.006(3) -0.005(3) C19 0.059(4) 0.073(4) 0.055(4) -0.005(3) 0.012(3) -0.002(3) C20 0.053(3) 0.082(5) 0.060(4) 0.004(3) 0.000(3) 0.001(3) C21 0.044(3) 0.065(4) 0.082(4) 0.008(4) 0.006(3) 0.000(3) C22 0.055(4) 0.085(4) 0.057(4) -0.002(3) 0.016(3) 0.018(3) C23 0.056(4) 0.056(4) 0.083(4) -0.017(3) 0.001(3) 0.007(3) C24 0.067(4) 0.066(4) 0.073(4) -0.013(4) 0.010(3) 0.000(3) C25 0.058(4) 0.082(5) 0.106(5) 0.014(4) 0.007(3) 0.020(3) C26 0.071(5) 0.068(5) 0.182(8) -0.008(5) 0.031(5) 0.011(4) C27 0.049(3) 0.115(6) 0.172(7) -0.003(7) 0.020(4) 0.007(5) N1 0.053(3) 0.064(3) 0.060(3) -0.008(3) 0.007(2) 0.010(2) O1 0.075(2) 0.058(2) 0.092(3) -0.016(3) 0.006(2) 0.006(3) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C5 1.901(6) . y C1 C6 1.390(7) . ? C1 C2 1.391(7) . ? C1 C7 1.463(7) . ? C2 O1 1.357(6) . y C2 C3 1.368(7) . ? C3 C4 1.367(8) . ? C3 H3 0.9300 . ? C4 C5 1.359(8) . ? C4 H4 0.9300 . ? C5 C6 1.367(7) . ? C6 H6 0.9300 . ? C7 N1 1.262(6) . y C7 H7 0.9300 . ? C8 N1 1.459(6) . y C8 C9 1.550(7) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C23 1.517(7) . ? C9 C10 1.537(7) . ? C9 C14 1.550(6) . ? C10 C11 1.513(6) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.534(7) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.540(7) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C24 1.528(8) . ? C13 C18 1.548(7) . ? C13 C14 1.557(6) . ? C14 C15 1.517(6) . ? C14 H14 0.9800 . ? C15 C16 1.503(8) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.509(7) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.380(7) . ? C17 C22 1.403(7) . ? C18 C19 1.386(7) . ? C19 C20 1.363(7) . ? C19 H19 0.9300 . ? C20 C21 1.366(8) . ? C20 H20 0.9300 . ? C21 C22 1.371(7) . ? C21 C25 1.512(7) . ? C22 H22 0.9300 . ? C23 H23A 0.9600 . ? C23 H23B 0.9600 . ? C23 H23C 0.9600 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 C26 1.477(9) . ? C25 C27 1.501(9) . ? C25 H25 0.9800 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? O1 H1 1.0549 . ? 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 C6 C1 C2 118.7(5) . . ? C6 C1 C7 119.4(5) . . ? C2 C1 C7 121.9(5) . . ? O1 C2 C3 119.0(6) . . ? O1 C2 C1 121.0(5) . . ? C3 C2 C1 120.0(6) . . ? C2 C3 C4 120.6(7) . . ? C2 C3 H3 119.7 . . ? C4 C3 H3 119.7 . . ? C5 C4 C3 119.8(6) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? C4 C5 C6 121.0(5) . . ? C4 C5 Br1 119.5(5) . . y C6 C5 Br1 119.5(5) . . y C5 C6 C1 119.9(6) . . ? C5 C6 H6 120.1 . . ? C1 C6 H6 120.1 . . ? N1 C7 C1 120.2(5) . . y N1 C7 H7 119.9 . . ? C1 C7 H7 119.9 . . ? N1 C8 C9 110.6(4) . . y N1 C8 H8A 109.5 . . ? C9 C8 H8A 109.5 . . ? N1 C8 H8B 109.5 . . ? C9 C8 H8B 109.5 . . ? H8A C8 H8B 108.1 . . ? C23 C9 C10 111.9(5) . . ? C23 C9 C14 113.0(4) . . ? C10 C9 C14 108.4(4) . . ? C23 C9 C8 108.6(5) . . ? C10 C9 C8 106.6(4) . . ? C14 C9 C8 108.1(4) . . ? C11 C10 C9 113.7(4) . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 111.2(5) . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11B 109.4 . . ? C12 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C13 110.9(5) . . ? C11 C12 H12A 109.4 . . ? C13 C12 H12A 109.4 . . ? C11 C12 H12B 109.4 . . ? C13 C12 H12B 109.4 . . ? H12A C12 H12B 108.0 . . ? C24 C13 C12 109.6(4) . . ? C24 C13 C18 106.1(4) . . ? C12 C13 C18 110.1(4) . . ? C24 C13 C14 114.6(5) . . ? C12 C13 C14 108.7(4) . . ? C18 C13 C14 107.7(4) . . ? C15 C14 C9 115.8(4) . . ? C15 C14 C13 109.6(4) . . ? C9 C14 C13 116.0(4) . . ? C15 C14 H14 104.6 . . ? C9 C14 H14 104.6 . . ? C13 C14 H14 104.6 . . ? C16 C15 C14 110.3(5) . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15B 109.6 . . ? C14 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 113.9(5) . . ? C15 C16 H16A 108.8 . . ? C17 C16 H16A 108.8 . . ? C15 C16 H16B 108.8 . . ? C17 C16 H16B 108.8 . . ? H16A C16 H16B 107.7 . . ? C18 C17 C22 119.6(5) . . ? C18 C17 C16 121.4(5) . . ? C22 C17 C16 119.0(5) . . ? C17 C18 C19 117.0(5) . . ? C17 C18 C13 123.1(5) . . ? C19 C18 C13 119.6(5) . . ? C20 C19 C18 122.6(5) . . ? C20 C19 H19 118.7 . . ? C18 C19 H19 118.7 . . ? C19 C20 C21 121.1(5) . . ? C19 C20 H20 119.4 . . ? C21 C20 H20 119.4 . . ? C20 C21 C22 117.4(5) . . ? C20 C21 C25 121.5(5) . . ? C22 C21 C25 121.1(5) . . ? C21 C22 C17 122.2(5) . . ? C21 C22 H22 118.9 . . ? C17 C22 H22 118.9 . . ? C9 C23 H23A 109.5 . . ? C9 C23 H23B 109.5 . . ? H23A C23 H23B 109.5 . . ? C9 C23 H23C 109.5 . . ? H23A C23 H23C 109.5 . . ? H23B C23 H23C 109.5 . . ? C13 C24 H24A 109.5 . . ? C13 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C13 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C26 C25 C27 113.6(7) . . ? C26 C25 C21 113.0(5) . . ? C27 C25 C21 112.6(6) . . ? C26 C25 H25 105.6 . . ? C27 C25 H25 105.6 . . ? C21 C25 H25 105.6 . . ? C25 C26 H26A 109.5 . . ? C25 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C25 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C25 C27 H27A 109.5 . . ? C25 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C25 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C7 N1 C8 121.8(5) . . ? C2 O1 H1 97.0 . . ? 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 C6 C1 C2 O1 178.5(5) . . . . ? C7 C1 C2 O1 -3.5(8) . . . . ? C6 C1 C2 C3 -2.5(8) . . . . ? C7 C1 C2 C3 175.5(5) . . . . ? O1 C2 C3 C4 -178.4(5) . . . . ? C1 C2 C3 C4 2.6(8) . . . . ? C2 C3 C4 C5 -1.5(9) . . . . ? C3 C4 C5 C6 0.6(9) . . . . ? C3 C4 C5 Br1 -179.1(4) . . . . ? C4 C5 C6 C1 -0.6(8) . . . . ? Br1 C5 C6 C1 179.0(4) . . . . ? C2 C1 C6 C5 1.6(7) . . . . ? C7 C1 C6 C5 -176.5(5) . . . . ? C6 C1 C7 N1 -177.4(5) . . . . y C2 C1 C7 N1 4.5(8) . . . . ? N1 C8 C9 C23 58.1(6) . . . . ? N1 C8 C9 C10 -62.5(6) . . . . ? N1 C8 C9 C14 -178.9(4) . . . . ? C23 C9 C10 C11 73.5(8) . . . . ? C14 C9 C10 C11 -51.8(8) . . . . ? C8 C9 C10 C11 -167.9(6) . . . . ? C9 C10 C11 C12 57.9(9) . . . . y C10 C11 C12 C13 -58.9(8) . . . . ? C11 C12 C13 C24 -70.8(6) . . . . ? C11 C12 C13 C18 172.8(4) . . . . ? C11 C12 C13 C14 55.1(6) . . . . ? C23 C9 C14 C15 56.7(6) . . . . ? C10 C9 C14 C15 -178.7(5) . . . . ? C8 C9 C14 C15 -63.5(6) . . . . ? C23 C9 C14 C13 -74.0(6) . . . . ? C10 C9 C14 C13 50.6(6) . . . . ? C8 C9 C14 C13 165.8(5) . . . . ? C24 C13 C14 C15 -63.8(6) . . . . ? C12 C13 C14 C15 173.2(5) . . . . ? C18 C13 C14 C15 54.0(6) . . . . ? C24 C13 C14 C9 69.7(6) . . . . ? C12 C13 C14 C9 -53.2(6) . . . . ? C18 C13 C14 C9 -172.5(4) . . . . ? C9 C14 C15 C16 159.4(5) . . . . y C13 C14 C15 C16 -66.9(6) . . . . ? C14 C15 C16 C17 44.2(7) . . . . ? C15 C16 C17 C18 -12.7(8) . . . . ? C15 C16 C17 C22 166.0(5) . . . . ? C22 C17 C18 C19 -0.8(8) . . . . ? C16 C17 C18 C19 177.9(5) . . . . y C22 C17 C18 C13 -175.9(5) . . . . ? C16 C17 C18 C13 2.8(8) . . . . ? C24 C13 C18 C17 99.8(6) . . . . ? C12 C13 C18 C17 -141.7(5) . . . . ? C14 C13 C18 C17 -23.3(7) . . . . ? C24 C13 C18 C19 -75.2(6) . . . . ? C12 C13 C18 C19 43.3(6) . . . . ? C14 C13 C18 C19 161.7(5) . . . . ? C17 C18 C19 C20 -0.1(8) . . . . ? C13 C18 C19 C20 175.2(5) . . . . ? C18 C19 C20 C21 1.6(9) . . . . ? C19 C20 C21 C22 -2.0(8) . . . . ? C19 C20 C21 C25 179.3(5) . . . . ? C20 C21 C22 C17 1.1(9) . . . . ? C25 C21 C22 C17 179.8(5) . . . . ? C18 C17 C22 C21 0.3(9) . . . . ? C16 C17 C22 C21 -178.5(5) . . . . ? C20 C21 C25 C26 -115.2(7) . . . . ? C22 C21 C25 C26 66.2(8) . . . . ? C20 C21 C25 C27 114.4(7) . . . . ? C22 C21 C25 C27 -64.2(8) . . . . ? C1 C7 N1 C8 -178.0(4) . . . . ? C9 C8 N1 C7 131.4(5) . . . . ? 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 _geom_hbond_publ_flag O1 H1 N1 1.05 1.54 2.570(6) 162.6 . y _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.10 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.419 _refine_diff_density_min -0.199 _refine_diff_density_rms 0.048 # Attachment '- NODHA.cif' data_d _database_code_depnum_ccdc_archive 'CCDC 806392' #TrackingRef '- NODHA.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H34 N2 O3' _chemical_formula_sum 'C27 H34 N2 O3' _chemical_formula_weight 434.56 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21 ' _symmetry_space_group_name_Hall 'P 2yb ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 11.1580(17) _cell_length_b 6.2046(10) _cell_length_c 17.347(3) _cell_angle_alpha 90.00 _cell_angle_beta 101.490(3) _cell_angle_gamma 90.00 _cell_volume 1176.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1122 _cell_measurement_theta_min 2.40 _cell_measurement_theta_max 19.22 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.58 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.17 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.226 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 468 _exptl_absorpt_coefficient_mu 0.080 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.9553 _exptl_absorpt_correction_T_max 0.9866 _exptl_absorpt_process_details 'SADABS; Bruker, 2000' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(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 'Bruker Smart Apex CCD' _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 7421 _diffrn_reflns_av_R_equivalents 0.0445 _diffrn_reflns_av_sigmaI/netI 0.1001 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min -7 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 1.86 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4172 _reflns_number_gt 1702 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement SMART _computing_data_reduction 'SAINT (Bruker, 2000)' _computing_structure_solution 'SHELXTL (Bruker, 2000)' _computing_structure_refinement SHELXTL _computing_molecular_graphics SHELXTL _computing_publication_material SHELXTL _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0270P)^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 SHELXL _refine_ls_extinction_coef 0.0191(16) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _chemical_absolute_configuration rm _refine_ls_abs_structure_Flack 0.1(1) _refine_ls_number_reflns 4172 _refine_ls_number_parameters 295 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1393 _refine_ls_R_factor_gt 0.0470 _refine_ls_wR_factor_ref 0.0986 _refine_ls_wR_factor_gt 0.0867 _refine_ls_goodness_of_fit_ref 0.989 _refine_ls_restrained_S_all 0.989 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C -0.1401(3) 0.2864(6) 0.04004(18) 0.0596(10) Uani 1 1 d . . . H1 H -0.1367 0.4284 0.0234 0.072 Uiso 1 1 calc R . . C2 C -0.0344(3) 0.1840(6) 0.0807(2) 0.0553(10) Uani 1 1 d . . . C3 C -0.0389(3) -0.0339(7) 0.1037(2) 0.0633(11) Uani 1 1 d . . . C4 C -0.1550(3) -0.1382(7) 0.08904(19) 0.0688(11) Uani 1 1 d . . . H4 H -0.1614 -0.2790 0.1062 0.083 Uiso 1 1 calc R . . C5 C -0.2570(3) -0.0343(7) 0.0501(2) 0.0680(11) Uani 1 1 d . . . H5 H -0.3322 -0.1044 0.0404 0.082 Uiso 1 1 calc R . . C6 C -0.2482(3) 0.1769(7) 0.0250(2) 0.0601(10) Uani 1 1 d . . . C7 C 0.0784(3) 0.3036(6) 0.09964(18) 0.0606(10) Uani 1 1 d . . . H7 H 0.0793 0.4500 0.0883 0.073 Uiso 1 1 calc R . . C8 C 0.2966(3) 0.3163(6) 0.15580(18) 0.0644(11) Uani 1 1 d . . . H8A H 0.2836 0.4709 0.1530 0.077 Uiso 1 1 calc R . . H8B H 0.3488 0.2788 0.1193 0.077 Uiso 1 1 calc R . . C9 C 0.3608(3) 0.2544(6) 0.2396(2) 0.0549(10) Uani 1 1 d . . . C10 C 0.2818(3) 0.3410(7) 0.29502(19) 0.0702(11) Uani 1 1 d . . . H10A H 0.2592 0.4887 0.2806 0.084 Uiso 1 1 calc R . . H10B H 0.2071 0.2568 0.2881 0.084 Uiso 1 1 calc R . . C11 C 0.3441(3) 0.3348(7) 0.3807(2) 0.0764(12) Uani 1 1 d . . . H11A H 0.3620 0.1866 0.3968 0.092 Uiso 1 1 calc R . . H11B H 0.2898 0.3938 0.4126 0.092 Uiso 1 1 calc R . . C12 C 0.4626(3) 0.4647(7) 0.39407(18) 0.0742(12) Uani 1 1 d . . . H12A H 0.5003 0.4608 0.4495 0.089 Uiso 1 1 calc R . . H12B H 0.4438 0.6138 0.3797 0.089 Uiso 1 1 calc R . . C13 C 0.5538(3) 0.3776(6) 0.34574(18) 0.0561(9) Uani 1 1 d . . . C14 C 0.4870(3) 0.3718(6) 0.25779(17) 0.0535(9) Uani 1 1 d . . . H14 H 0.4682 0.5229 0.2439 0.064 Uiso 1 1 calc R . . C15 C 0.5775(3) 0.3023(6) 0.20600(19) 0.0680(11) Uani 1 1 d . . . H15A H 0.6163 0.1675 0.2252 0.082 Uiso 1 1 calc R . . H15B H 0.5342 0.2808 0.1523 0.082 Uiso 1 1 calc R . . C16 C 0.6737(3) 0.4765(7) 0.20853(19) 0.0799(13) Uani 1 1 d . . . H16A H 0.7420 0.4172 0.1886 0.096 Uiso 1 1 calc R . . H16B H 0.6392 0.5928 0.1737 0.096 Uiso 1 1 calc R . . C17 C 0.7213(3) 0.5687(7) 0.2898(2) 0.0667(11) Uani 1 1 d . . . C18 C 0.6645(3) 0.5301(6) 0.3527(2) 0.0564(10) Uani 1 1 d . . . C19 C 0.7173(3) 0.6156(6) 0.4254(2) 0.0682(11) Uani 1 1 d . . . H19 H 0.6820 0.5870 0.4685 0.082 Uiso 1 1 calc R . . C20 C 0.8213(4) 0.7425(7) 0.4353(2) 0.0811(13) Uani 1 1 d . . . H20 H 0.8545 0.7973 0.4849 0.097 Uiso 1 1 calc R . . C21 C 0.8761(3) 0.7885(7) 0.3735(3) 0.0739(12) Uani 1 1 d . . . C22 C 0.8271(3) 0.7010(7) 0.3016(2) 0.0761(13) Uani 1 1 d . . . H22 H 0.8643 0.7292 0.2593 0.091 Uiso 1 1 calc R . . C23 C 0.9896(4) 0.9289(8) 0.3842(3) 0.0978(15) Uani 1 1 d . . . H23 H 1.0059 0.9640 0.4404 0.117 Uiso 1 1 calc R . . C24 C 1.0997(3) 0.8127(9) 0.3741(3) 0.1341(19) Uani 1 1 d . . . H24A H 1.0907 0.7670 0.3204 0.201 Uiso 1 1 calc R . . H24B H 1.1112 0.6889 0.4080 0.201 Uiso 1 1 calc R . . H24C H 1.1694 0.9060 0.3873 0.201 Uiso 1 1 calc R . . C25 C 0.9682(4) 1.1385(9) 0.3461(3) 0.1246(18) Uani 1 1 d . . . H25A H 1.0414 1.2236 0.3586 0.187 Uiso 1 1 calc R . . H25B H 0.9032 1.2108 0.3644 0.187 Uiso 1 1 calc R . . H25C H 0.9461 1.1192 0.2902 0.187 Uiso 1 1 calc R . . C26 C 0.6039(3) 0.1593(6) 0.3812(2) 0.0766(12) Uani 1 1 d . . . H26A H 0.6462 0.0877 0.3455 0.115 Uiso 1 1 calc R . . H26B H 0.5372 0.0709 0.3899 0.115 Uiso 1 1 calc R . . H26C H 0.6593 0.1837 0.4304 0.115 Uiso 1 1 calc R . . C27 C 0.3745(3) 0.0059(6) 0.2422(2) 0.0823(13) Uani 1 1 d . . . H27A H 0.4143 -0.0379 0.2941 0.123 Uiso 1 1 calc R . . H27B H 0.4226 -0.0389 0.2049 0.123 Uiso 1 1 calc R . . H27C H 0.2951 -0.0596 0.2292 0.123 Uiso 1 1 calc R . . N1 N 0.1793(2) 0.2063(5) 0.13285(16) 0.0662(10) Uani 1 1 d . . . N2 N -0.3561(3) 0.2828(7) -0.0198(2) 0.0785(11) Uani 1 1 d . . . O1 O -0.3502(2) 0.4754(6) -0.0327(2) 0.1102(11) Uani 1 1 d . . . O2 O -0.4480(2) 0.1768(5) -0.04175(18) 0.1134(11) Uani 1 1 d . . . O3 O 0.0575(2) -0.1388(4) 0.13676(16) 0.0838(8) Uani 1 1 d . . . H3 H 0.1175 -0.0599 0.1412 0.126 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 C1 0.058(2) 0.054(3) 0.067(2) 0.002(2) 0.0139(19) -0.001(2) C2 0.063(3) 0.044(3) 0.061(2) 0.000(2) 0.015(2) -0.009(2) C3 0.055(3) 0.064(4) 0.068(3) 0.004(2) 0.006(2) -0.004(2) C4 0.076(3) 0.064(3) 0.068(3) 0.003(2) 0.017(2) -0.017(3) C5 0.060(3) 0.069(4) 0.077(3) -0.007(3) 0.021(2) -0.017(2) C6 0.051(3) 0.066(3) 0.062(2) -0.002(2) 0.0093(19) -0.006(2) C7 0.064(2) 0.055(3) 0.064(2) 0.001(2) 0.0152(19) -0.012(2) C8 0.056(2) 0.064(3) 0.072(3) 0.002(2) 0.0103(18) -0.006(2) C9 0.054(2) 0.054(3) 0.056(2) 0.003(2) 0.0097(18) -0.0079(19) C10 0.056(2) 0.084(3) 0.072(3) 0.011(3) 0.019(2) -0.009(2) C11 0.061(2) 0.098(4) 0.075(3) 0.005(3) 0.025(2) -0.007(2) C12 0.067(2) 0.091(3) 0.066(3) 0.002(3) 0.015(2) -0.008(2) C13 0.056(2) 0.058(3) 0.058(2) 0.003(2) 0.0188(19) 0.001(2) C14 0.053(2) 0.047(2) 0.061(2) -0.004(2) 0.0106(18) -0.0061(19) C15 0.056(2) 0.083(3) 0.067(2) -0.017(2) 0.0181(19) -0.008(2) C16 0.058(2) 0.122(4) 0.063(3) -0.010(3) 0.0184(19) -0.020(3) C17 0.054(2) 0.082(3) 0.063(3) 0.000(2) 0.009(2) -0.006(2) C18 0.051(2) 0.059(3) 0.059(3) 0.005(2) 0.011(2) -0.001(2) C19 0.063(3) 0.079(3) 0.059(3) -0.006(2) 0.004(2) -0.006(2) C20 0.074(3) 0.081(3) 0.084(3) -0.013(3) 0.004(3) -0.012(3) C21 0.050(2) 0.082(3) 0.085(3) -0.008(3) 0.002(2) -0.011(2) C22 0.056(2) 0.097(4) 0.077(3) 0.009(3) 0.017(2) -0.010(2) C23 0.070(3) 0.075(4) 0.143(4) -0.003(3) 0.008(3) -0.020(3) C24 0.053(3) 0.112(4) 0.240(6) -0.012(4) 0.035(3) -0.001(3) C25 0.074(3) 0.088(4) 0.217(5) 0.022(4) 0.042(3) -0.007(3) C26 0.075(3) 0.061(3) 0.090(3) 0.016(2) 0.007(2) -0.002(2) C27 0.074(3) 0.060(3) 0.109(3) 0.009(3) 0.008(2) -0.010(2) N1 0.0474(18) 0.075(3) 0.072(2) -0.0006(18) 0.0012(16) -0.0108(18) N2 0.065(3) 0.084(3) 0.085(3) 0.003(2) 0.013(2) -0.003(2) O1 0.077(2) 0.091(3) 0.155(3) 0.030(3) 0.0055(17) 0.008(2) O2 0.0666(19) 0.113(3) 0.151(3) -0.002(2) -0.0032(17) -0.010(2) O3 0.0774(19) 0.067(2) 0.0993(19) 0.0119(18) -0.0005(17) -0.0134(17) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C6 1.363(4) . ? C1 C2 1.400(4) . ? C1 H1 0.9300 . ? C2 C3 1.414(5) . ? C2 C7 1.441(4) . ? C3 O3 1.290(4) . y C3 C4 1.425(4) . ? C4 C5 1.364(4) . ? C4 H4 0.9300 . ? C5 C6 1.390(5) . ? C5 H5 0.9300 . ? C6 N2 1.454(5) . y C7 N1 1.307(4) . y C7 H7 0.9300 . ? C8 N1 1.460(4) . y C8 C9 1.536(4) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.526(4) . ? C9 C27 1.550(5) . ? C9 C14 1.561(4) . ? C10 C11 1.511(4) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.526(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.540(4) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C18 1.541(4) . ? C13 C26 1.545(4) . ? C13 C14 1.559(4) . ? C14 C15 1.541(4) . ? C14 H14 0.9800 . ? C15 C16 1.518(4) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.517(4) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 C18 1.387(4) . ? C17 C22 1.419(4) . ? C18 C19 1.387(4) . ? C19 C20 1.385(4) . ? C19 H19 0.9300 . ? C20 C21 1.366(5) . ? C20 H20 0.9300 . ? C21 C22 1.369(5) . ? C21 C23 1.518(5) . ? C22 H22 0.9300 . ? C23 C25 1.457(6) . ? C23 C24 1.465(5) . ? C23 H23 0.9800 . ? C24 H24A 0.9600 . ? C24 H24B 0.9600 . ? C24 H24C 0.9600 . ? C25 H25A 0.9600 . ? C25 H25B 0.9600 . ? C25 H25C 0.9600 . ? C26 H26A 0.9600 . ? C26 H26B 0.9600 . ? C26 H26C 0.9600 . ? C27 H27A 0.9600 . ? C27 H27B 0.9600 . ? C27 H27C 0.9600 . ? N2 O2 1.214(4) . y N2 O1 1.220(4) . y O3 H3 0.8200 . ? 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 C6 C1 C2 119.6(4) . . ? C6 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? C1 C2 C3 120.2(3) . . ? C1 C2 C7 119.4(4) . . ? C3 C2 C7 120.4(3) . . ? O3 C3 C2 122.3(3) . . ? O3 C3 C4 119.9(4) . . ? C2 C3 C4 117.8(4) . . ? C5 C4 C3 120.9(4) . . ? C5 C4 H4 119.6 . . ? C3 C4 H4 119.6 . . ? C4 C5 C6 119.8(4) . . ? C4 C5 H5 120.1 . . ? C6 C5 H5 120.1 . . ? C1 C6 C5 121.7(4) . . ? C1 C6 N2 118.9(4) . . y C5 C6 N2 119.4(4) . . y N1 C7 C2 120.0(3) . . y N1 C7 H7 120.0 . . ? C2 C7 H7 120.0 . . ? N1 C8 C9 111.4(3) . . y N1 C8 H8A 109.3 . . ? C9 C8 H8A 109.3 . . ? N1 C8 H8B 109.3 . . ? C9 C8 H8B 109.3 . . ? H8A C8 H8B 108.0 . . ? C10 C9 C8 106.8(3) . . ? C10 C9 C27 113.4(3) . . ? C8 C9 C27 107.5(3) . . ? C10 C9 C14 108.6(3) . . ? C8 C9 C14 107.9(3) . . ? C27 C9 C14 112.3(3) . . ? C11 C10 C9 113.6(3) . . ? C11 C10 H10A 108.8 . . ? C9 C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C9 C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 110.5(3) . . ? C10 C11 H11A 109.5 . . ? C12 C11 H11A 109.5 . . ? C10 C11 H11B 109.5 . . ? C12 C11 H11B 109.5 . . ? H11A C11 H11B 108.1 . . ? C11 C12 C13 112.2(3) . . ? C11 C12 H12A 109.2 . . ? C13 C12 H12A 109.2 . . ? C11 C12 H12B 109.2 . . ? C13 C12 H12B 109.2 . . ? H12A C12 H12B 107.9 . . ? C12 C13 C18 110.4(3) . . ? C12 C13 C26 108.4(3) . . ? C18 C13 C26 106.7(3) . . ? C12 C13 C14 107.6(2) . . ? C18 C13 C14 108.1(3) . . ? C26 C13 C14 115.7(3) . . ? C15 C14 C13 109.6(2) . . ? C15 C14 C9 114.9(3) . . ? C13 C14 C9 116.4(3) . . ? C15 C14 H14 104.9 . . ? C13 C14 H14 104.9 . . ? C9 C14 H14 104.9 . . ? C16 C15 C14 109.0(3) . . ? C16 C15 H15A 109.9 . . ? C14 C15 H15A 109.9 . . ? C16 C15 H15B 109.9 . . ? C14 C15 H15B 109.9 . . ? H15A C15 H15B 108.3 . . ? C17 C16 C15 114.2(3) . . ? C17 C16 H16A 108.7 . . ? C15 C16 H16A 108.7 . . ? C17 C16 H16B 108.7 . . ? C15 C16 H16B 108.7 . . ? H16A C16 H16B 107.6 . . ? C18 C17 C22 119.0(3) . . ? C18 C17 C16 122.4(3) . . ? C22 C17 C16 118.6(3) . . ? C19 C18 C17 118.1(3) . . ? C19 C18 C13 119.7(3) . . ? C17 C18 C13 122.0(3) . . ? C20 C19 C18 121.7(3) . . ? C20 C19 H19 119.2 . . ? C18 C19 H19 119.2 . . ? C21 C20 C19 121.0(4) . . ? C21 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? C20 C21 C22 118.2(4) . . ? C20 C21 C23 121.0(4) . . ? C22 C21 C23 120.8(4) . . ? C21 C22 C17 122.0(4) . . ? C21 C22 H22 119.0 . . ? C17 C22 H22 119.0 . . ? C25 C23 C24 116.7(4) . . ? C25 C23 C21 113.5(4) . . ? C24 C23 C21 113.7(4) . . ? C25 C23 H23 103.6 . . ? C24 C23 H23 103.6 . . ? C21 C23 H23 103.6 . . ? C23 C24 H24A 109.5 . . ? C23 C24 H24B 109.5 . . ? H24A C24 H24B 109.5 . . ? C23 C24 H24C 109.5 . . ? H24A C24 H24C 109.5 . . ? H24B C24 H24C 109.5 . . ? C23 C25 H25A 109.5 . . ? C23 C25 H25B 109.5 . . ? H25A C25 H25B 109.5 . . ? C23 C25 H25C 109.5 . . ? H25A C25 H25C 109.5 . . ? H25B C25 H25C 109.5 . . ? C13 C26 H26A 109.5 . . ? C13 C26 H26B 109.5 . . ? H26A C26 H26B 109.5 . . ? C13 C26 H26C 109.5 . . ? H26A C26 H26C 109.5 . . ? H26B C26 H26C 109.5 . . ? C9 C27 H27A 109.5 . . ? C9 C27 H27B 109.5 . . ? H27A C27 H27B 109.5 . . ? C9 C27 H27C 109.5 . . ? H27A C27 H27C 109.5 . . ? H27B C27 H27C 109.5 . . ? C7 N1 C8 123.5(3) . . y O2 N2 O1 123.1(4) . . y O2 N2 C6 118.8(4) . . y O1 N2 C6 118.1(4) . . y C3 O3 H3 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 C6 C1 C2 C3 2.0(5) . . . . ? C6 C1 C2 C7 -177.1(3) . . . . ? C1 C2 C3 O3 175.5(3) . . . . ? C7 C2 C3 O3 -5.4(5) . . . . ? C1 C2 C3 C4 -4.2(5) . . . . ? C7 C2 C3 C4 174.9(3) . . . . ? O3 C3 C4 C5 -176.2(3) . . . . ? C2 C3 C4 C5 3.6(5) . . . . ? C3 C4 C5 C6 -0.7(5) . . . . ? C2 C1 C6 C5 1.0(5) . . . . ? C2 C1 C6 N2 -177.7(3) . . . . ? C4 C5 C6 C1 -1.7(5) . . . . ? C4 C5 C6 N2 177.0(3) . . . . ? C1 C2 C7 N1 -175.5(3) . . . . y C3 C2 C7 N1 5.4(5) . . . . ? N1 C8 C9 C10 -65.6(4) . . . . ? N1 C8 C9 C27 56.5(4) . . . . ? N1 C8 C9 C14 177.8(3) . . . . ? C8 C9 C10 C11 -168.1(3) . . . . ? C27 C9 C10 C11 73.6(4) . . . . ? C14 C9 C10 C11 -52.0(4) . . . . ? C9 C10 C11 C12 58.3(5) . . . . y C10 C11 C12 C13 -59.9(4) . . . . ? C11 C12 C13 C18 172.7(3) . . . . ? C11 C12 C13 C26 -70.8(4) . . . . ? C11 C12 C13 C14 55.1(4) . . . . ? C12 C13 C14 C15 175.6(3) . . . . ? C18 C13 C14 C15 56.5(4) . . . . ? C26 C13 C14 C15 -63.0(4) . . . . ? C12 C13 C14 C9 -51.8(4) . . . . ? C18 C13 C14 C9 -171.0(3) . . . . ? C26 C13 C14 C9 69.6(4) . . . . ? C10 C9 C14 C15 -179.7(3) . . . . ? C8 C9 C14 C15 -64.3(4) . . . . ? C27 C9 C14 C15 54.0(4) . . . . ? C10 C9 C14 C13 50.2(4) . . . . ? C8 C9 C14 C13 165.7(3) . . . . ? C27 C9 C14 C13 -76.1(4) . . . . ? C13 C14 C15 C16 -66.8(4) . . . . ? C9 C14 C15 C16 159.9(3) . . . . y C14 C15 C16 C17 42.8(4) . . . . ? C15 C16 C17 C18 -12.6(5) . . . . ? C15 C16 C17 C22 168.0(3) . . . . ? C22 C17 C18 C19 -2.8(5) . . . . ? C16 C17 C18 C19 177.9(3) . . . . y C22 C17 C18 C13 -176.4(3) . . . . ? C16 C17 C18 C13 4.3(6) . . . . ? C12 C13 C18 C19 43.2(4) . . . . ? C26 C13 C18 C19 -74.4(4) . . . . ? C14 C13 C18 C19 160.5(3) . . . . ? C12 C13 C18 C17 -143.4(3) . . . . ? C26 C13 C18 C17 99.0(4) . . . . ? C14 C13 C18 C17 -26.0(4) . . . . ? C17 C18 C19 C20 2.2(5) . . . . ? C13 C18 C19 C20 176.0(3) . . . . ? C18 C19 C20 C21 0.0(6) . . . . ? C19 C20 C21 C22 -1.7(6) . . . . ? C19 C20 C21 C23 179.6(4) . . . . ? C20 C21 C22 C17 1.1(6) . . . . ? C23 C21 C22 C17 179.8(4) . . . . ? C18 C17 C22 C21 1.2(6) . . . . ? C16 C17 C22 C21 -179.4(4) . . . . ? C20 C21 C23 C25 -110.8(5) . . . . ? C22 C21 C23 C25 70.5(6) . . . . ? C20 C21 C23 C24 112.5(5) . . . . ? C22 C21 C23 C24 -66.2(5) . . . . ? C2 C7 N1 C8 -178.4(3) . . . . ? C9 C8 N1 C7 133.0(3) . . . . ? C1 C6 N2 O2 170.6(3) . . . . y C5 C6 N2 O2 -8.1(5) . . . . y C1 C6 N2 O1 -10.2(5) . . . . y C5 C6 N2 O1 171.1(4) . . . . y 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 _geom_hbond_publ_flag C8 H8B O1 0.97 2.41 3.146(5) 132.4 2_545 y O3 H3 N1 0.82 1.81 2.544(4) 148.8 . y _diffrn_measured_fraction_theta_max 0.988 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 0.988 _refine_diff_density_max 0.161 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.032