Supplementary Material (ESI) for Journal of Materials Chemistry This journal is (c) The Royal Society of Chemistry 2011 data_global _journal_name_full J.Mater.Chem. _journal_coden_Cambridge 1145 _publ_contact_author_name 'Xilian Wei' _publ_contact_author_address ; Liaocheng Shandong China 252000 ; _publ_contact_author_email weixilian@126.com loop_ _publ_author_name 'Zengbin Wei' 'Xilian Wei' 'Xiuhong Wang' 'Zhongni Wang' 'Jie Liu' # Attachment 'jm-art-01-2011-010236-File008-v1-0.cif' data_090314a _database_code_depnum_ccdc_archive 'CCDC 808823' #TrackingRef 'jm-art-01-2011-010236-File008-v1-0.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H48 Br N O2' _chemical_formula_weight 438.52 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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 P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.9075(10) _cell_length_b 7.3979(13) _cell_length_c 28.899(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.5920(10) _cell_angle_gamma 90.00 _cell_volume 1262.9(3) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 1037 _cell_measurement_theta_min 2.82 _cell_measurement_theta_max 25.19 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_max 0.21 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.06 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.153 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 1.642 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7243 _exptl_absorpt_correction_T_max 0.9079 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 6617 _diffrn_reflns_av_R_equivalents 0.0654 _diffrn_reflns_av_sigmaI/netI 0.1371 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_limit_l_max 34 _diffrn_reflns_theta_min 1.41 _diffrn_reflns_theta_max 25.01 _reflns_number_total 4120 _reflns_number_gt 1613 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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. ; _chemical_absolute_configuration s _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^)+(0.0341P)^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 0.02(3) _refine_ls_number_reflns 4120 _refine_ls_number_parameters 240 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1723 _refine_ls_R_factor_gt 0.0692 _refine_ls_wR_factor_ref 0.1386 _refine_ls_wR_factor_gt 0.1202 _refine_ls_goodness_of_fit_ref 0.995 _refine_ls_restrained_S_all 0.995 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.68627(13) 0.3025(4) 0.93038(3) 0.0905(4) Uani 1 1 d . . . N1 N 0.9258(10) 0.289(2) 0.0709(2) 0.064(2) Uani 1 1 d . . . O1 O 0.9655(8) 0.299(2) 0.21668(18) 0.1043(19) Uani 1 1 d . . . O2 O 1.3472(10) 0.4322(9) 0.1249(2) 0.092(2) Uani 1 1 d . . . H2 H 1.3427 0.5269 0.1102 0.110 Uiso 1 1 calc R . . C20 C 1.0060(14) 0.260(3) 0.1193(3) 0.094(6) Uani 1 1 d . . . H20A H 0.8736 0.2311 0.1375 0.113 Uiso 1 1 calc R . . H20B H 1.0998 0.1521 0.1192 0.113 Uiso 1 1 calc R . . C21 C 1.1331(16) 0.3994(15) 0.1450(3) 0.085(3) Uani 1 1 d . . . H21A H 1.0452 0.5115 0.1465 0.102 Uiso 1 1 calc R . . C22 C 1.1737(14) 0.322(4) 0.1937(3) 0.109(4) Uani 1 1 d . . . H22A H 1.2506 0.2066 0.1915 0.131 Uiso 1 1 calc R . . H22B H 1.2699 0.4036 0.2114 0.131 Uiso 1 1 calc R . . C17 C 1.1172(10) 0.308(3) 0.0383(2) 0.073(2) Uani 1 1 d . . . H17A H 1.0606 0.3465 0.0087 0.109 Uiso 1 1 calc R . . H17B H 1.1924 0.1937 0.0351 0.109 Uiso 1 1 calc R . . H17C H 1.2223 0.3961 0.0501 0.109 Uiso 1 1 calc R . . C18 C 0.801(2) 0.454(3) 0.0636(4) 0.096(6) Uani 1 1 d . . . H18A H 0.8946 0.5557 0.0719 0.143 Uiso 1 1 calc R . . H18B H 0.6682 0.4538 0.0825 0.143 Uiso 1 1 calc R . . H18C H 0.7571 0.4636 0.0316 0.143 Uiso 1 1 calc R . . C19 C 0.770(2) 0.138(2) 0.0604(5) 0.096(6) Uani 1 1 d . . . H19A H 0.6728 0.1179 0.0863 0.144 Uiso 1 1 calc R . . H19B H 0.8556 0.0306 0.0543 0.144 Uiso 1 1 calc R . . H19C H 0.6793 0.1677 0.0336 0.144 Uiso 1 1 calc R . . C1 C 0.9807(14) 0.338(3) 0.2631(3) 0.109(6) Uani 1 1 d . . . H1A H 1.0208 0.4646 0.2666 0.130 Uiso 1 1 calc R . . H1B H 1.1024 0.2670 0.2766 0.130 Uiso 1 1 calc R . . C2 C 0.7734(13) 0.303(3) 0.2890(3) 0.097(3) Uani 1 1 d . . . H2A H 0.6507 0.3646 0.2728 0.116 Uiso 1 1 calc R . . H2B H 0.7429 0.1749 0.2869 0.116 Uiso 1 1 calc R . . C3 C 0.7603(15) 0.353(2) 0.3367(3) 0.110(7) Uani 1 1 d . . . H3A H 0.7747 0.4835 0.3382 0.132 Uiso 1 1 calc R . . H3B H 0.8930 0.3031 0.3521 0.132 Uiso 1 1 calc R . . C4 C 0.5637(12) 0.303(3) 0.3646(2) 0.089(3) Uani 1 1 d . . . H4A H 0.4306 0.3505 0.3488 0.107 Uiso 1 1 calc R . . H4B H 0.5519 0.1727 0.3639 0.107 Uiso 1 1 calc R . . C5 C 0.5487(15) 0.359(2) 0.4131(3) 0.105(6) Uani 1 1 d . . . H5A H 0.6816 0.3108 0.4289 0.126 Uiso 1 1 calc R . . H5B H 0.5625 0.4893 0.4138 0.126 Uiso 1 1 calc R . . C6 C 0.3547(12) 0.312(3) 0.4413(3) 0.086(3) Uani 1 1 d . . . H6A H 0.2224 0.3622 0.4257 0.103 Uiso 1 1 calc R . . H6B H 0.3393 0.1820 0.4400 0.103 Uiso 1 1 calc R . . C7 C 0.3384(13) 0.3623(17) 0.4889(3) 0.097(5) Uani 1 1 d . . . H7A H 0.3497 0.4930 0.4903 0.117 Uiso 1 1 calc R . . H7B H 0.4719 0.3147 0.5045 0.117 Uiso 1 1 calc R . . C8 C 0.1433(12) 0.311(3) 0.5169(3) 0.085(3) Uani 1 1 d . . . H8A H 0.0101 0.3581 0.5011 0.102 Uiso 1 1 calc R . . H8B H 0.1324 0.1802 0.5154 0.102 Uiso 1 1 calc R . . C9 C 0.1241(14) 0.360(2) 0.5649(3) 0.108(7) Uani 1 1 d . . . H9A H 0.1350 0.4911 0.5662 0.130 Uiso 1 1 calc R . . H9B H 0.2579 0.3135 0.5805 0.130 Uiso 1 1 calc R . . C10 C -0.0683(12) 0.310(3) 0.5932(2) 0.087(3) Uani 1 1 d . . . H10A H -0.2014 0.3572 0.5774 0.104 Uiso 1 1 calc R . . H10B H -0.0791 0.1794 0.5915 0.104 Uiso 1 1 calc R . . C11 C -0.0928(14) 0.356(2) 0.6405(3) 0.112(7) Uani 1 1 d . . . H11A H -0.0797 0.4861 0.6421 0.134 Uiso 1 1 calc R . . H11B H 0.0398 0.3073 0.6562 0.134 Uiso 1 1 calc R . . C12 C -0.2842(13) 0.308(3) 0.6690(2) 0.094(3) Uani 1 1 d . . . H12A H -0.4156 0.3584 0.6532 0.112 Uiso 1 1 calc R . . H12B H -0.2986 0.1780 0.6665 0.112 Uiso 1 1 calc R . . C13 C -0.3145(15) 0.348(3) 0.7166(3) 0.118(7) Uani 1 1 d . . . H13A H -0.1882 0.2916 0.7327 0.141 Uiso 1 1 calc R . . H13B H -0.2922 0.4774 0.7195 0.141 Uiso 1 1 calc R . . C14 C -0.5072(14) 0.308(3) 0.7429(3) 0.114(4) Uani 1 1 d . . . H14A H -0.6275 0.3801 0.7293 0.137 Uiso 1 1 calc R . . H14B H -0.5437 0.1832 0.7352 0.137 Uiso 1 1 calc R . . C15 C -0.5374(15) 0.320(4) 0.7897(3) 0.131(5) Uani 1 1 d . . . H15A H -0.4388 0.4187 0.7992 0.157 Uiso 1 1 calc R . . H15B H -0.4676 0.2115 0.8020 0.157 Uiso 1 1 calc R . . C16 C -0.7286(16) 0.343(3) 0.8161(3) 0.145(8) Uani 1 1 d . . . H16A H -0.8599 0.3088 0.7984 0.217 Uiso 1 1 calc R . . H16B H -0.7412 0.4674 0.8252 0.217 Uiso 1 1 calc R . . H16C H -0.7176 0.2685 0.8433 0.217 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 Br1 0.0827(6) 0.0885(6) 0.0998(7) 0.0009(15) -0.0218(4) -0.0008(14) N1 0.047(4) 0.086(7) 0.060(5) -0.009(9) -0.003(3) 0.014(9) O1 0.076(4) 0.181(6) 0.056(4) -0.005(11) 0.003(3) -0.006(11) O2 0.062(4) 0.125(5) 0.088(5) 0.009(4) 0.002(3) -0.007(4) C20 0.068(6) 0.154(19) 0.061(7) 0.004(9) 0.015(5) -0.017(8) C21 0.064(7) 0.125(9) 0.067(8) -0.016(7) 0.008(5) -0.005(6) C22 0.081(6) 0.186(12) 0.060(6) 0.001(14) -0.003(4) 0.000(14) C17 0.054(4) 0.099(6) 0.065(5) 0.024(12) 0.010(4) -0.020(11) C18 0.079(11) 0.123(17) 0.084(12) 0.001(11) -0.013(8) 0.001(10) C19 0.074(10) 0.084(13) 0.129(14) 0.008(10) 0.016(9) -0.055(9) C1 0.085(6) 0.174(18) 0.066(6) -0.017(10) -0.002(5) -0.015(10) C2 0.086(6) 0.145(8) 0.058(6) -0.003(15) -0.005(4) -0.015(17) C3 0.097(7) 0.17(2) 0.065(7) -0.006(8) -0.005(5) 0.003(8) C4 0.089(6) 0.114(7) 0.065(6) -0.012(16) 0.004(4) -0.011(16) C5 0.096(7) 0.155(19) 0.064(7) -0.001(8) -0.010(5) -0.010(8) C6 0.094(6) 0.111(8) 0.052(5) -0.002(14) -0.005(4) 0.000(15) C7 0.092(7) 0.143(17) 0.057(7) -0.012(7) -0.012(5) 0.003(7) C8 0.084(6) 0.109(8) 0.063(6) -0.022(13) 0.001(4) 0.004(13) C9 0.097(7) 0.16(2) 0.062(7) -0.019(8) -0.014(5) 0.002(8) C10 0.090(6) 0.122(8) 0.048(5) -0.024(13) -0.008(4) 0.011(16) C11 0.096(7) 0.17(2) 0.067(7) -0.015(9) -0.016(5) 0.002(8) C12 0.095(6) 0.132(8) 0.054(6) -0.011(14) -0.004(4) 0.024(16) C13 0.096(7) 0.19(2) 0.066(7) -0.004(10) -0.004(5) -0.014(10) C14 0.103(7) 0.181(11) 0.058(6) -0.018(18) 0.000(5) 0.03(2) C15 0.106(8) 0.209(14) 0.078(7) -0.027(17) -0.006(6) -0.009(18) C16 0.105(8) 0.22(2) 0.106(8) -0.059(13) 0.014(6) 0.054(13) _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 N1 C18 1.44(2) . ? N1 C19 1.478(19) . ? N1 C17 1.485(8) . ? N1 C20 1.490(10) . ? O1 C1 1.375(10) . ? O1 C22 1.414(9) . ? O2 C21 1.417(9) . ? O2 H2 0.8200 . ? C20 C21 1.472(16) . ? C20 H20A 0.9700 . ? C20 H20B 0.9700 . ? C21 C22 1.537(14) . ? C21 H21A 0.9800 . ? C22 H22A 0.9700 . ? C22 H22B 0.9700 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C1 C2 1.464(11) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.431(12) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.467(12) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.463(12) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.454(11) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.429(10) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.464(11) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.442(10) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.455(11) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.416(11) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.449(12) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.419(11) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.407(12) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.371(10) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.380(10) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 N1 C19 107.1(6) . . ? C18 N1 C17 102.7(14) . . ? C19 N1 C17 114.8(13) . . ? C18 N1 C20 114.7(12) . . ? C19 N1 C20 105.9(13) . . ? C17 N1 C20 111.9(5) . . ? C1 O1 C22 112.6(7) . . ? C21 O2 H2 109.5 . . ? C21 C20 N1 121.7(14) . . ? C21 C20 H20A 106.9 . . ? N1 C20 H20A 106.9 . . ? C21 C20 H20B 106.9 . . ? N1 C20 H20B 106.9 . . ? H20A C20 H20B 106.7 . . ? O2 C21 C20 111.6(8) . . ? O2 C21 C22 107.8(7) . . ? C20 C21 C22 105.9(12) . . ? O2 C21 H21A 110.5 . . ? C20 C21 H21A 110.5 . . ? C22 C21 H21A 110.5 . . ? O1 C22 C21 110.3(8) . . ? O1 C22 H22A 109.6 . . ? C21 C22 H22A 109.6 . . ? O1 C22 H22B 109.6 . . ? C21 C22 H22B 109.6 . . ? H22A C22 H22B 108.1 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? O1 C1 C2 114.5(9) . . ? O1 C1 H1A 108.6 . . ? C2 C1 H1A 108.6 . . ? O1 C1 H1B 108.6 . . ? C2 C1 H1B 108.6 . . ? H1A C1 H1B 107.6 . . ? C3 C2 C1 120.1(11) . . ? C3 C2 H2A 107.3 . . ? C1 C2 H2A 107.3 . . ? C3 C2 H2B 107.3 . . ? C1 C2 H2B 107.3 . . ? H2A C2 H2B 106.9 . . ? C2 C3 C4 121.1(11) . . ? C2 C3 H3A 107.0 . . ? C4 C3 H3A 107.0 . . ? C2 C3 H3B 107.0 . . ? C4 C3 H3B 107.0 . . ? H3A C3 H3B 106.8 . . ? C5 C4 C3 120.9(11) . . ? C5 C4 H4A 107.1 . . ? C3 C4 H4A 107.1 . . ? C5 C4 H4B 107.1 . . ? C3 C4 H4B 107.1 . . ? H4A C4 H4B 106.8 . . ? C6 C5 C4 121.8(10) . . ? C6 C5 H5A 106.9 . . ? C4 C5 H5A 106.9 . . ? C6 C5 H5B 106.9 . . ? C4 C5 H5B 106.9 . . ? H5A C5 H5B 106.7 . . ? C7 C6 C5 122.7(11) . . ? C7 C6 H6A 106.7 . . ? C5 C6 H6A 106.7 . . ? C7 C6 H6B 106.7 . . ? C5 C6 H6B 106.7 . . ? H6A C6 H6B 106.6 . . ? C6 C7 C8 121.7(9) . . ? C6 C7 H7A 106.9 . . ? C8 C7 H7A 106.9 . . ? C6 C7 H7B 106.9 . . ? C8 C7 H7B 106.9 . . ? H7A C7 H7B 106.7 . . ? C9 C8 C7 122.4(11) . . ? C9 C8 H8A 106.7 . . ? C7 C8 H8A 106.7 . . ? C9 C8 H8B 106.7 . . ? C7 C8 H8B 106.7 . . ? H8A C8 H8B 106.6 . . ? C8 C9 C10 123.1(10) . . ? C8 C9 H9A 106.6 . . ? C10 C9 H9A 106.6 . . ? C8 C9 H9B 106.6 . . ? C10 C9 H9B 106.6 . . ? H9A C9 H9B 106.5 . . ? C11 C10 C9 124.7(11) . . ? C11 C10 H10A 106.2 . . ? C9 C10 H10A 106.2 . . ? C11 C10 H10B 106.2 . . ? C9 C10 H10B 106.2 . . ? H10A C10 H10B 106.3 . . ? C10 C11 C12 125.4(11) . . ? C10 C11 H11A 106.0 . . ? C12 C11 H11A 106.0 . . ? C10 C11 H11B 106.0 . . ? C12 C11 H11B 106.0 . . ? H11A C11 H11B 106.3 . . ? C13 C12 C11 127.4(12) . . ? C13 C12 H12A 105.4 . . ? C11 C12 H12A 105.4 . . ? C13 C12 H12B 105.4 . . ? C11 C12 H12B 105.4 . . ? H12A C12 H12B 106.0 . . ? C14 C13 C12 126.2(12) . . ? C14 C13 H13A 105.8 . . ? C12 C13 H13A 105.8 . . ? C14 C13 H13B 105.8 . . ? C12 C13 H13B 105.8 . . ? H13A C13 H13B 106.2 . . ? C15 C14 C13 129.3(12) . . ? C15 C14 H14A 105.0 . . ? C13 C14 H14A 105.0 . . ? C15 C14 H14B 105.0 . . ? C13 C14 H14B 105.0 . . ? H14A C14 H14B 105.8 . . ? C14 C15 C16 132.1(9) . . ? C14 C15 H15A 104.2 . . ? C16 C15 H15A 104.2 . . ? C14 C15 H15B 104.2 . . ? C16 C15 H15B 104.2 . . ? H15A C15 H15B 105.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 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 C18 N1 C20 C21 -51.2(14) . . . . ? C19 N1 C20 C21 -169.1(11) . . . . ? C17 N1 C20 C21 65.2(18) . . . . ? N1 C20 C21 O2 -65.7(12) . . . . ? N1 C20 C21 C22 177.2(9) . . . . ? C1 O1 C22 C21 -142.9(16) . . . . ? O2 C21 C22 O1 175.7(14) . . . . ? C20 C21 C22 O1 -65(2) . . . . ? C22 O1 C1 C2 -176(2) . . . . ? O1 C1 C2 C3 -174.6(18) . . . . ? C1 C2 C3 C4 -173.8(19) . . . . ? C2 C3 C4 C5 -178.4(17) . . . . ? C3 C4 C5 C6 179.5(17) . . . . ? C4 C5 C6 C7 178.9(15) . . . . ? C5 C6 C7 C8 -178.7(17) . . . . ? C6 C7 C8 C9 -179.9(15) . . . . ? C7 C8 C9 C10 -179.9(16) . . . . ? C8 C9 C10 C11 179.8(17) . . . . ? C9 C10 C11 C12 179.3(18) . . . . ? C10 C11 C12 C13 179(2) . . . . ? C11 C12 C13 C14 177(2) . . . . ? C12 C13 C14 C15 171(3) . . . . ? C13 C14 C15 C16 155(3) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.01 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.595 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.058 # Attachment 'jm-art-01-2011-010236-File009-v1-0.cif' data_090428d _database_code_depnum_ccdc_archive 'CCDC 819472' #TrackingRef 'jm-art-01-2011-010236-File009-v1-0.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H42 Br N' _chemical_formula_weight 364.45 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 5.6382(6) _cell_length_b 7.2724(7) _cell_length_c 26.007(2) _cell_angle_alpha 90.00 _cell_angle_beta 93.778(2) _cell_angle_gamma 90.00 _cell_volume 1064.03(18) _cell_formula_units_Z 2 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 2776 _cell_measurement_theta_min 2.801 _cell_measurement_theta_max 26.706 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.49 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.138 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 1.929 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.4516 _exptl_absorpt_correction_T_max 0.6874 _exptl_absorpt_process_details sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5310 _diffrn_reflns_av_R_equivalents 0.0945 _diffrn_reflns_av_sigmaI/netI 0.0858 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 25.02 _reflns_number_total 3521 _reflns_number_gt 2758 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SHELXTL' _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^)+(0.1900P)^2^+0.9381P] 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 0.014(6) _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' _refine_ls_abs_structure_Flack ? _refine_ls_number_reflns 3521 _refine_ls_number_parameters 195 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.1109 _refine_ls_R_factor_gt 0.0903 _refine_ls_wR_factor_ref 0.2600 _refine_ls_wR_factor_gt 0.2336 _refine_ls_goodness_of_fit_ref 1.003 _refine_ls_restrained_S_all 1.003 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.86916(12) 0.6693(4) 0.42758(3) 0.0513(4) Uani 1 1 d . . . N1 N 0.4897(10) 0.171(3) 0.4211(2) 0.0332(14) Uani 1 1 d . . . C1 C 0.6774(11) 0.168(4) 0.3816(3) 0.0352(14) Uani 1 1 d . . . H1A H 0.7923 0.2639 0.3903 0.042 Uiso 1 1 calc R . . H1B H 0.7608 0.0512 0.3845 0.042 Uiso 1 1 calc R . . C2 C 0.5862(15) 0.193(3) 0.3261(3) 0.046(4) Uani 1 1 d . . . H2A H 0.5310 0.3185 0.3205 0.055 Uiso 1 1 calc R . . H2B H 0.4544 0.1105 0.3178 0.055 Uiso 1 1 calc R . . C3 C 0.7898(18) 0.152(5) 0.2922(4) 0.059(4) Uani 1 1 d . . . H3A H 0.9212 0.2335 0.3022 0.070 Uiso 1 1 calc R . . H3B H 0.8432 0.0272 0.2989 0.070 Uiso 1 1 calc R . . C4 C 0.7316(16) 0.173(5) 0.2354(3) 0.059(3) Uani 1 1 d . . . H4A H 0.6118 0.2682 0.2308 0.071 Uiso 1 1 calc R . . H4B H 0.6585 0.0590 0.2231 0.071 Uiso 1 1 calc R . . C5 C 0.9264(19) 0.218(2) 0.2008(4) 0.064(5) Uani 1 1 d . . . H5A H 0.9445 0.3506 0.2004 0.076 Uiso 1 1 calc R . . H5B H 1.0732 0.1673 0.2164 0.076 Uiso 1 1 calc R . . C6 C 0.9004(17) 0.154(5) 0.1460(4) 0.053(4) Uani 1 1 d . . . H6A H 0.7437 0.1880 0.1315 0.064 Uiso 1 1 calc R . . H6B H 0.9095 0.0204 0.1457 0.064 Uiso 1 1 calc R . . C7 C 1.085(2) 0.2295(17) 0.1114(4) 0.060(4) Uani 1 1 d . . . H7A H 1.0683 0.3622 0.1101 0.072 Uiso 1 1 calc R . . H7B H 1.2417 0.2028 0.1274 0.072 Uiso 1 1 calc R . . C8 C 1.0737(17) 0.159(6) 0.0581(3) 0.052(3) Uani 1 1 d . . . H8A H 0.9177 0.1869 0.0421 0.063 Uiso 1 1 calc R . . H8B H 1.0879 0.0259 0.0595 0.063 Uiso 1 1 calc R . . C9 C 1.257(2) 0.2306(18) 0.0236(4) 0.061(4) Uani 1 1 d . . . H9A H 1.2422 0.3634 0.0220 0.073 Uiso 1 1 calc R . . H9B H 1.4132 0.2033 0.0398 0.073 Uiso 1 1 calc R . . C10 C 1.2476(16) 0.159(5) -0.0296(3) 0.054(3) Uani 1 1 d . . . H10A H 1.0914 0.1862 -0.0457 0.064 Uiso 1 1 calc R . . H10B H 1.2634 0.0266 -0.0280 0.064 Uiso 1 1 calc R . . C11 C 1.430(2) 0.2321(19) -0.0638(4) 0.061(4) Uani 1 1 d . . . H11A H 1.4134 0.3647 -0.0657 0.073 Uiso 1 1 calc R . . H11B H 1.5865 0.2063 -0.0475 0.073 Uiso 1 1 calc R . . C12 C 1.4211(16) 0.158(5) -0.1174(4) 0.053(3) Uani 1 1 d . . . H12A H 1.2640 0.1820 -0.1335 0.064 Uiso 1 1 calc R . . H12B H 1.4408 0.0258 -0.1155 0.064 Uiso 1 1 calc R . . C13 C 1.603(2) 0.2337(18) -0.1521(4) 0.062(4) Uani 1 1 d . . . H13A H 1.5849 0.3663 -0.1538 0.074 Uiso 1 1 calc R . . H13B H 1.7600 0.2077 -0.1365 0.074 Uiso 1 1 calc R . . C14 C 1.5869(17) 0.160(6) -0.2055(4) 0.060(3) Uani 1 1 d . . . H14A H 1.4303 0.1880 -0.2213 0.072 Uiso 1 1 calc R . . H14B H 1.6017 0.0274 -0.2038 0.072 Uiso 1 1 calc R . . C15 C 1.771(2) 0.2334(19) -0.2403(4) 0.070(4) Uani 1 1 d . . . H15A H 1.7558 0.3661 -0.2422 0.084 Uiso 1 1 calc R . . H15B H 1.9281 0.2063 -0.2245 0.084 Uiso 1 1 calc R . . C16 C 1.756(3) 0.157(6) -0.2946(5) 0.093(5) Uani 1 1 d . . . H16A H 1.7944 0.0287 -0.2936 0.139 Uiso 1 1 calc R . . H16B H 1.8667 0.2212 -0.3147 0.139 Uiso 1 1 calc R . . H16C H 1.5978 0.1738 -0.3098 0.139 Uiso 1 1 calc R . . C17 C 0.338(3) 0.340(2) 0.4165(7) 0.043(5) Uani 1 1 d . . . H17A H 0.2482 0.3393 0.3839 0.064 Uiso 1 1 calc R . . H17B H 0.4378 0.4470 0.4189 0.064 Uiso 1 1 calc R . . H17C H 0.2316 0.3417 0.4438 0.064 Uiso 1 1 calc R . . C18 C 0.338(3) 0.003(3) 0.4157(6) 0.041(5) Uani 1 1 d . . . H18A H 0.2439 -0.0072 0.4451 0.061 Uiso 1 1 calc R . . H18B H 0.4368 -0.1035 0.4137 0.061 Uiso 1 1 calc R . . H18C H 0.2347 0.0126 0.3850 0.061 Uiso 1 1 calc R . . C19 C 0.6229(13) 0.172(4) 0.4727(3) 0.0476(18) Uani 1 1 d . . . H19A H 0.7009 0.2889 0.4779 0.071 Uiso 1 1 calc R . . H19B H 0.7394 0.0760 0.4742 0.071 Uiso 1 1 calc R . . H19C H 0.5142 0.1535 0.4991 0.071 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 Br1 0.0450(5) 0.0382(5) 0.0724(7) -0.0017(11) 0.0167(4) -0.0013(11) N1 0.037(3) 0.042(3) 0.021(3) 0.006(8) 0.012(2) -0.019(8) C1 0.036(3) 0.043(4) 0.028(3) -0.002(10) 0.013(3) 0.002(12) C2 0.044(4) 0.071(12) 0.023(4) 0.003(6) 0.012(3) -0.001(7) C3 0.060(5) 0.081(11) 0.037(5) -0.004(9) 0.019(4) -0.005(11) C4 0.056(5) 0.099(8) 0.025(4) 0.001(15) 0.015(3) -0.012(17) C5 0.058(5) 0.105(16) 0.030(5) -0.003(5) 0.014(4) -0.008(6) C6 0.053(4) 0.076(11) 0.032(4) -0.004(8) 0.016(3) -0.019(11) C7 0.058(6) 0.093(12) 0.029(5) -0.001(5) 0.014(4) -0.009(5) C8 0.056(4) 0.073(9) 0.029(4) -0.009(10) 0.014(3) -0.011(12) C9 0.058(6) 0.092(11) 0.033(6) 0.000(5) 0.011(4) -0.006(5) C10 0.054(5) 0.074(9) 0.034(5) -0.007(10) 0.017(4) -0.017(13) C11 0.063(6) 0.086(11) 0.034(6) 0.006(4) 0.018(5) -0.008(6) C12 0.053(4) 0.071(8) 0.038(5) -0.004(10) 0.016(4) -0.012(12) C13 0.065(6) 0.086(10) 0.036(6) 0.004(5) 0.020(5) 0.007(6) C14 0.063(5) 0.080(9) 0.037(5) -0.012(13) 0.015(4) 0.010(15) C15 0.077(7) 0.100(12) 0.035(6) 0.005(5) 0.024(5) 0.012(7) C16 0.125(10) 0.112(14) 0.044(7) -0.024(15) 0.033(6) 0.01(2) C17 0.043(10) 0.031(11) 0.057(11) -0.002(8) 0.022(8) 0.013(7) C18 0.049(11) 0.049(13) 0.023(8) 0.002(7) 0.002(7) -0.003(8) C19 0.046(4) 0.076(5) 0.021(4) 0.003(11) 0.006(3) 0.000(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 Br1 Br1 0.0000(14) 1 ? N1 C18 1.49(2) . ? N1 C19 1.492(9) . ? N1 C17 1.50(3) . ? N1 C1 1.523(8) . ? C1 C2 1.512(12) . ? C1 H1A 0.9700 . ? C1 H1B 0.9700 . ? C2 C3 1.523(14) . ? C2 H2A 0.9700 . ? C2 H2B 0.9700 . ? C3 C4 1.497(14) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C5 1.502(14) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C5 C6 1.498(18) . ? C5 H5A 0.9700 . ? C5 H5B 0.9700 . ? C6 C7 1.524(18) . ? C6 H6A 0.9700 . ? C6 H6B 0.9700 . ? C7 C8 1.478(19) . ? C7 H7A 0.9700 . ? C7 H7B 0.9700 . ? C8 C9 1.506(19) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C9 C10 1.48(2) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.501(17) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.492(19) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.512(18) . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.49(2) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.52(2) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.51(2) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 H16A 0.9600 . ? C16 H16B 0.9600 . ? C16 H16C 0.9600 . ? C17 H17A 0.9600 . ? C17 H17B 0.9600 . ? C17 H17C 0.9600 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C18 N1 C19 110.1(14) . . ? C18 N1 C17 110.0(5) . . ? C19 N1 C17 108.4(16) . . ? C18 N1 C1 110.2(14) . . ? C19 N1 C1 106.0(5) . . ? C17 N1 C1 112.0(13) . . ? C2 C1 N1 115.8(6) . . ? C2 C1 H1A 108.3 . . ? N1 C1 H1A 108.3 . . ? C2 C1 H1B 108.3 . . ? N1 C1 H1B 108.3 . . ? H1A C1 H1B 107.4 . . ? C1 C2 C3 107.9(9) . . ? C1 C2 H2A 110.1 . . ? C3 C2 H2A 110.1 . . ? C1 C2 H2B 110.1 . . ? C3 C2 H2B 110.1 . . ? H2A C2 H2B 108.4 . . ? C4 C3 C2 115.3(11) . . ? C4 C3 H3A 108.5 . . ? C2 C3 H3A 108.5 . . ? C4 C3 H3B 108.5 . . ? C2 C3 H3B 108.5 . . ? H3A C3 H3B 107.5 . . ? C3 C4 C5 119.4(9) . . ? C3 C4 H4A 107.5 . . ? C5 C4 H4A 107.5 . . ? C3 C4 H4B 107.5 . . ? C5 C4 H4B 107.5 . . ? H4A C4 H4B 107.0 . . ? C6 C5 C4 118.2(12) . . ? C6 C5 H5A 107.8 . . ? C4 C5 H5A 107.8 . . ? C6 C5 H5B 107.8 . . ? C4 C5 H5B 107.8 . . ? H5A C5 H5B 107.1 . . ? C5 C6 C7 114.9(17) . . ? C5 C6 H6A 108.6 . . ? C7 C6 H6A 108.6 . . ? C5 C6 H6B 108.6 . . ? C7 C6 H6B 108.6 . . ? H6A C6 H6B 107.5 . . ? C8 C7 C6 116.0(13) . . ? C8 C7 H7A 108.3 . . ? C6 C7 H7A 108.3 . . ? C8 C7 H7B 108.3 . . ? C6 C7 H7B 108.3 . . ? H7A C7 H7B 107.4 . . ? C7 C8 C9 116.6(19) . . ? C7 C8 H8A 108.1 . . ? C9 C8 H8A 108.1 . . ? C7 C8 H8B 108.1 . . ? C9 C8 H8B 108.1 . . ? H8A C8 H8B 107.3 . . ? C10 C9 C8 116.8(13) . . ? C10 C9 H9A 108.1 . . ? C8 C9 H9A 108.1 . . ? C10 C9 H9B 108.1 . . ? C8 C9 H9B 108.1 . . ? H9A C9 H9B 107.3 . . ? C9 C10 C11 116.6(18) . . ? C9 C10 H10A 108.1 . . ? C11 C10 H10A 108.1 . . ? C9 C10 H10B 108.1 . . ? C11 C10 H10B 108.1 . . ? H10A C10 H10B 107.3 . . ? C12 C11 C10 116.4(14) . . ? C12 C11 H11A 108.2 . . ? C10 C11 H11A 108.2 . . ? C12 C11 H11B 108.2 . . ? C10 C11 H11B 108.2 . . ? H11A C11 H11B 107.4 . . ? C11 C12 C13 116.4(18) . . ? C11 C12 H12A 108.2 . . ? C13 C12 H12A 108.2 . . ? C11 C12 H12B 108.2 . . ? C13 C12 H12B 108.2 . . ? H12A C12 H12B 107.3 . . ? C14 C13 C12 115.3(14) . . ? C14 C13 H13A 108.5 . . ? C12 C13 H13A 108.5 . . ? C14 C13 H13B 108.5 . . ? C12 C13 H13B 108.5 . . ? H13A C13 H13B 107.5 . . ? C13 C14 C15 115(2) . . ? C13 C14 H14A 108.4 . . ? C15 C14 H14A 108.4 . . ? C13 C14 H14B 108.4 . . ? C15 C14 H14B 108.4 . . ? H14A C14 H14B 107.5 . . ? C16 C15 C14 115.4(16) . . ? C16 C15 H15A 108.4 . . ? C14 C15 H15A 108.4 . . ? C16 C15 H15B 108.4 . . ? C14 C15 H15B 108.4 . . ? H15A C15 H15B 107.5 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? N1 C17 H17A 109.5 . . ? N1 C17 H17B 109.5 . . ? H17A C17 H17B 109.5 . . ? N1 C17 H17C 109.5 . . ? H17A C17 H17C 109.5 . . ? H17B C17 H17C 109.5 . . ? N1 C18 H18A 109.5 . . ? N1 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? N1 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? N1 C19 H19A 109.5 . . ? N1 C19 H19B 109.5 . . ? H19A C19 H19B 109.5 . . ? N1 C19 H19C 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 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 C18 N1 C1 C2 69(2) . . . . ? C19 N1 C1 C2 -171(2) . . . . ? C17 N1 C1 C2 -53(2) . . . . ? N1 C1 C2 C3 -170(2) . . . . ? C1 C2 C3 C4 -179(3) . . . . ? C2 C3 C4 C5 153(3) . . . . ? C3 C4 C5 C6 152(3) . . . . ? C4 C5 C6 C7 171(2) . . . . ? C5 C6 C7 C8 176(2) . . . . ? C6 C7 C8 C9 -179(2) . . . . ? C7 C8 C9 C10 180(2) . . . . ? C8 C9 C10 C11 180(2) . . . . ? C9 C10 C11 C12 179(2) . . . . ? C10 C11 C12 C13 179.0(19) . . . . ? C11 C12 C13 C14 -179(2) . . . . ? C12 C13 C14 C15 -179(2) . . . . ? C13 C14 C15 C16 180(2) . . . . ? _diffrn_measured_fraction_theta_max 0.991 _diffrn_reflns_theta_full 25.02 _diffrn_measured_fraction_theta_full 0.991 _refine_diff_density_max 1.118 _refine_diff_density_min -1.099 _refine_diff_density_rms 0.128