data_z:\s3027\work\s3027abs _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; #------------------------------------------------------------------------------ _publ_requested_journal ' ENTER JOURNAL NAME HERE' _publ_contact_author ; Madeleine Helliwell ; _publ_contact_letter ; ENTER TEXT OF LETTER ; _publ_requested_coeditor_name ? _publ_contact_author_phone ' ENTER PHONE NUMBER ' _publ_contact_author_fax ' ENTER FAX NUMBER ' _publ_contact_author_email ' ENTER EMAIL ADDRESS ' loop_ _publ_author_name _publ_author_address ' FIRST AUTHORS NAME ' ; FIRST AUTHORS ADDRESS ; _publ_section_title ; ENTER SECTION TITLE ; _publ_section_abstract ; ENTER ABSTRACT ; _publ_section_exptl_prep ; ENTER EXPERIMENTAL SECTION ; _publ_section_exptl_refinement ; The structure was solved by the direct methods. All non-H atoms were refined anisotropically. H atoms were included in calculated positions, except the one bonded to N1 which was found in a difference map and then allowed to ride on N1. The absolute configuration was determined by refining the Flack parameter. ; _publ_section_comment ; ENTER TEXT ; _publ_section_references ; Bruker (2001). SMART (Version 5.625), SADABS (Version 2.03a) and SHELXTL (Version 6.12). Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2002). SAINT. Version 6.36a. Bruker AXS Inc., Madison, Wisconsin, USA. M. C. Burla, R. Caliandro, M. Camalli, B. Carrozzini, G. L. Cascarano, L. De Caro,C. Giacovazzo, G. Polidori and R. Spagna SIR2004: an improved tool for crystal structure determination and refinement J. Appl. Cryst. (2005). 38, 381-388 Sheldrick, G. M. (1997). SHELXS-97 and SHELXL-97. University of G\"ottingen, Germany. Sheldrick, G, M. (2005). CELL_NOW. University of G\"ottingen, Germany. Sheldrick, G, M. (2007). TWINABS. University of G\"ottingen, Germany. Spek, A.L. (2003) J.Appl.Cryst. 36, 2003, 7-13. ; _publ_section_acknowledgements ; ENTER ACKNOWLEDGEMENTS ; _publ_section_table_legends ; ENTER TABLE LEGENDS ; _publ_section_figure_captions ; ENTER FIGURE CAPTIONS ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H25 Br N2 O' _chemical_formula_weight 389.33 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 Orthorhombic _symmetry_space_group_name_H-M P2(1)2(1)2(1) loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 8.010(2) _cell_length_b 10.902(2) _cell_length_c 20.373(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1779.0(7) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 840 _cell_measurement_theta_min 2.73 _cell_measurement_theta_max 20.93 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.454 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 808 _exptl_absorpt_coefficient_mu 2.320 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.704 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(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 10334 _diffrn_reflns_av_R_equivalents 0.0520 _diffrn_reflns_av_sigmaI/netI 0.0776 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 2.00 _diffrn_reflns_theta_max 26.38 _reflns_number_total 3620 _reflns_number_gt 3042 _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^)+(0.0205P)^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 0.017(9) _chemical_absolute_configuration ad _refine_ls_number_reflns 3620 _refine_ls_number_parameters 219 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0535 _refine_ls_R_factor_gt 0.0399 _refine_ls_wR_factor_ref 0.0733 _refine_ls_wR_factor_gt 0.0699 _refine_ls_goodness_of_fit_ref 0.969 _refine_ls_restrained_S_all 0.969 _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 -0.19644(5) 0.62275(4) -0.043656(19) 0.02409(11) Uani 1 1 d . . . O1 O 0.5765(3) 0.4115(2) 0.30044(12) 0.0194(6) Uani 1 1 d . . . N1 N -0.1125(3) 0.4696(2) 0.23751(15) 0.0150(7) Uani 1 1 d . . . N2 N 0.3223(3) 0.5077(2) 0.29378(13) 0.0136(6) Uani 1 1 d . . . C1 C -0.1761(4) 0.5723(3) 0.04561(18) 0.0179(8) Uani 1 1 d . . . C2 C -0.3120(5) 0.5131(3) 0.07496(17) 0.0183(8) Uani 1 1 d . . . H2 H -0.4111 0.4991 0.0505 0.022 Uiso 1 1 calc R . . C3 C -0.3022(5) 0.4748(3) 0.13939(18) 0.0178(8) Uani 1 1 d . . . H3 H -0.3932 0.4337 0.1597 0.021 Uiso 1 1 calc R . . C4 C -0.1559(4) 0.4980(3) 0.17382(18) 0.0136(8) Uani 1 1 d . . . C5 C -0.0176(4) 0.5579(3) 0.14389(18) 0.0137(8) Uani 1 1 d . . . C6 C -0.0290(4) 0.5941(3) 0.07833(17) 0.0136(8) Uani 1 1 d . . . H6 H 0.0623 0.6328 0.0569 0.016 Uiso 1 1 calc R . . C7 C 0.0494(4) 0.5107(3) 0.24867(18) 0.0134(8) Uani 1 1 d . . . C8 C 0.1100(4) 0.5647(3) 0.19318(18) 0.0130(8) Uani 1 1 d . . . C9 C 0.2847(4) 0.6134(3) 0.18780(16) 0.0150(7) Uani 1 1 d . . . H9A H 0.2818 0.6978 0.1700 0.018 Uiso 1 1 calc R . . H9B H 0.3495 0.5617 0.1570 0.018 Uiso 1 1 calc R . . C10 C 0.3708(4) 0.6141(3) 0.25501(16) 0.0152(7) Uani 1 1 d . . . H10A H 0.4934 0.6140 0.2488 0.018 Uiso 1 1 calc R . . H10B H 0.3402 0.6899 0.2789 0.018 Uiso 1 1 calc R . . C11 C 0.1447(4) 0.4884(3) 0.31087(18) 0.0147(8) Uani 1 1 d . . . C12 C 0.1423(4) 0.3518(3) 0.33218(18) 0.0141(8) Uani 1 1 d . . . H12A H 0.0709 0.3404 0.3714 0.017 Uiso 1 1 calc R . . H12B H 0.0993 0.2992 0.2963 0.017 Uiso 1 1 calc R . . C13 C 0.3234(4) 0.3200(3) 0.34774(17) 0.0168(8) Uani 1 1 d . . . H13A H 0.3442 0.3240 0.3956 0.020 Uiso 1 1 calc R . . H13B H 0.3512 0.2366 0.3319 0.020 Uiso 1 1 calc R . . C14 C 0.4257(4) 0.4159(3) 0.31172(17) 0.0145(8) Uani 1 1 d . . . C15 C 0.0906(4) 0.5771(3) 0.36549(17) 0.0165(8) Uani 1 1 d . . . H15A H 0.1055 0.6620 0.3493 0.020 Uiso 1 1 calc R . . H15B H -0.0302 0.5649 0.3737 0.020 Uiso 1 1 calc R . . C16 C 0.1827(5) 0.5649(3) 0.43094(16) 0.0194(8) Uani 1 1 d . . . H16A H 0.1543 0.4851 0.4513 0.023 Uiso 1 1 calc R . . H16B H 0.3046 0.5661 0.4229 0.023 Uiso 1 1 calc R . . C17 C 0.1374(4) 0.6678(3) 0.47796(18) 0.0200(9) Uani 1 1 d . . . H17A H 0.0144 0.6713 0.4822 0.024 Uiso 1 1 calc R . . H17B H 0.1750 0.7466 0.4589 0.024 Uiso 1 1 calc R . . C18 C 0.2130(4) 0.6540(3) 0.54595(18) 0.0179(8) Uani 1 1 d . . . H18A H 0.3360 0.6499 0.5418 0.021 Uiso 1 1 calc R . . H18B H 0.1746 0.5756 0.5652 0.021 Uiso 1 1 calc R . . C19 C 0.1679(4) 0.7583(3) 0.59273(17) 0.0200(8) Uani 1 1 d . . . H19A H 0.2155 0.8358 0.5756 0.024 Uiso 1 1 calc R . . H19B H 0.0450 0.7674 0.5939 0.024 Uiso 1 1 calc R . . C20 C 0.2316(4) 0.7375(3) 0.66235(18) 0.0214(9) Uani 1 1 d . . . H20A H 0.1673 0.6716 0.6831 0.032 Uiso 1 1 calc R . . H20B H 0.2188 0.8131 0.6879 0.032 Uiso 1 1 calc R . . H20C H 0.3498 0.7145 0.6609 0.032 Uiso 1 1 calc R . . H1N H -0.1788 0.4528 0.2757 0.050(13) 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 0.02247(18) 0.03179(19) 0.01801(18) 0.0034(2) -0.00419(19) -0.00199(19) O1 0.0118(13) 0.0262(15) 0.0203(14) 0.0024(12) 0.0018(11) 0.0018(10) N1 0.0096(15) 0.0194(16) 0.0158(17) 0.0018(14) 0.0033(13) -0.0009(12) N2 0.0112(14) 0.0112(14) 0.0182(17) 0.0031(13) 0.0002(15) -0.0020(13) C1 0.0206(18) 0.0171(16) 0.0160(18) -0.0009(17) -0.006(2) 0.0029(14) C2 0.0123(17) 0.0214(18) 0.021(2) -0.0045(16) -0.0080(18) 0.0005(17) C3 0.0102(16) 0.0139(17) 0.029(2) 0.0011(16) 0.003(2) -0.0027(16) C4 0.0107(19) 0.0135(18) 0.016(2) -0.0017(16) 0.0030(14) 0.0052(13) C5 0.0124(17) 0.0107(18) 0.018(2) 0.0000(16) 0.0044(16) 0.0043(14) C6 0.0148(17) 0.0103(18) 0.0157(19) -0.0009(15) 0.0058(15) 0.0002(13) C7 0.0108(18) 0.0122(17) 0.017(2) -0.0014(16) 0.0011(15) -0.0012(14) C8 0.0091(17) 0.0079(16) 0.022(2) 0.0000(16) -0.0004(16) 0.0019(13) C9 0.0144(17) 0.0125(16) 0.0181(18) 0.0032(17) 0.0013(15) -0.0007(17) C10 0.0116(16) 0.0149(17) 0.0192(19) 0.0029(19) 0.0018(14) -0.0041(16) C11 0.0102(18) 0.0174(19) 0.017(2) 0.0030(17) 0.0020(15) -0.0005(14) C12 0.0129(18) 0.014(2) 0.0150(19) 0.0023(16) 0.0019(14) -0.0032(13) C13 0.018(2) 0.0158(17) 0.017(2) 0.0039(16) 0.0000(18) 0.0025(15) C14 0.0151(18) 0.019(2) 0.0098(19) -0.0011(15) 0.0016(15) -0.0002(14) C15 0.0142(18) 0.0170(18) 0.018(2) 0.0031(16) 0.0033(16) 0.0002(14) C16 0.0197(19) 0.0198(17) 0.0188(19) 0.0026(16) 0.0002(18) 0.0019(16) C17 0.019(2) 0.0198(19) 0.021(2) 0.0027(17) 0.0016(16) 0.0013(14) C18 0.0172(18) 0.0133(18) 0.0233(19) -0.0002(18) 0.001(2) -0.0001(14) C19 0.018(2) 0.0186(18) 0.023(2) -0.0014(17) 0.0029(17) -0.0011(15) C20 0.019(2) 0.023(2) 0.022(2) -0.0065(18) 0.0052(17) -0.0027(15) _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 C1 1.907(4) . ? O1 C14 1.231(4) . ? N1 C4 1.378(5) . ? N1 C7 1.391(4) . ? N1 H1N 0.9598 . ? N2 C14 1.349(4) . ? N2 C10 1.456(4) . ? N2 C11 1.480(4) . ? C1 C6 1.374(5) . ? C1 C2 1.400(5) . ? C2 C3 1.380(5) . ? C2 H2 0.9500 . ? C3 C4 1.389(5) . ? C3 H3 0.9500 . ? C4 C5 1.423(4) . ? C5 C6 1.396(5) . ? C5 C8 1.435(5) . ? C6 H6 0.9500 . ? C7 C8 1.364(5) . ? C7 C11 1.499(5) . ? C8 C9 1.500(4) . ? C9 C10 1.533(4) . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C15 1.536(5) . ? C11 C12 1.552(5) . ? C12 C13 1.525(5) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 C14 1.518(4) . ? C13 H13A 0.9900 . ? C13 H13B 0.9900 . ? C15 C16 1.530(5) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.519(5) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.519(5) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.527(4) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.524(5) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 H20A 0.9800 . ? C20 H20B 0.9800 . ? C20 H20C 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 C4 N1 C7 108.5(3) . . ? C4 N1 H1N 131.8 . . ? C7 N1 H1N 116.4 . . ? C14 N2 C10 125.0(3) . . ? C14 N2 C11 114.9(3) . . ? C10 N2 C11 119.8(3) . . ? C6 C1 C2 122.6(3) . . ? C6 C1 Br1 119.1(3) . . ? C2 C1 Br1 118.3(3) . . ? C3 C2 C1 120.1(3) . . ? C3 C2 H2 119.9 . . ? C1 C2 H2 119.9 . . ? C2 C3 C4 118.3(3) . . ? C2 C3 H3 120.9 . . ? C4 C3 H3 120.9 . . ? N1 C4 C3 130.3(3) . . ? N1 C4 C5 108.1(3) . . ? C3 C4 C5 121.6(3) . . ? C6 C5 C4 119.3(3) . . ? C6 C5 C8 134.6(3) . . ? C4 C5 C8 106.2(3) . . ? C1 C6 C5 118.1(3) . . ? C1 C6 H6 120.9 . . ? C5 C6 H6 120.9 . . ? C8 C7 N1 109.6(3) . . ? C8 C7 C11 126.1(3) . . ? N1 C7 C11 124.1(3) . . ? C7 C8 C5 107.7(3) . . ? C7 C8 C9 123.0(3) . . ? C5 C8 C9 129.2(3) . . ? C8 C9 C10 110.8(3) . . ? C8 C9 H9A 109.5 . . ? C10 C9 H9A 109.5 . . ? C8 C9 H9B 109.5 . . ? C10 C9 H9B 109.5 . . ? H9A C9 H9B 108.1 . . ? N2 C10 C9 111.1(3) . . ? N2 C10 H10A 109.4 . . ? C9 C10 H10A 109.4 . . ? N2 C10 H10B 109.4 . . ? C9 C10 H10B 109.4 . . ? H10A C10 H10B 108.0 . . ? N2 C11 C7 105.5(3) . . ? N2 C11 C15 110.6(3) . . ? C7 C11 C15 111.5(3) . . ? N2 C11 C12 102.3(2) . . ? C7 C11 C12 112.7(3) . . ? C15 C11 C12 113.4(3) . . ? C13 C12 C11 105.3(3) . . ? C13 C12 H12A 110.7 . . ? C11 C12 H12A 110.7 . . ? C13 C12 H12B 110.7 . . ? C11 C12 H12B 110.7 . . ? H12A C12 H12B 108.8 . . ? C14 C13 C12 104.9(3) . . ? C14 C13 H13A 110.8 . . ? C12 C13 H13A 110.8 . . ? C14 C13 H13B 110.8 . . ? C12 C13 H13B 110.8 . . ? H13A C13 H13B 108.9 . . ? O1 C14 N2 125.6(3) . . ? O1 C14 C13 126.3(3) . . ? N2 C14 C13 108.1(3) . . ? C16 C15 C11 116.1(3) . . ? C16 C15 H15A 108.3 . . ? C11 C15 H15A 108.3 . . ? C16 C15 H15B 108.3 . . ? C11 C15 H15B 108.3 . . ? H15A C15 H15B 107.4 . . ? C17 C16 C15 111.7(3) . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C16 C17 C18 114.0(3) . . ? C16 C17 H17A 108.8 . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17B 108.8 . . ? C18 C17 H17B 108.8 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 113.7(3) . . ? C17 C18 H18A 108.8 . . ? C19 C18 H18A 108.8 . . ? C17 C18 H18B 108.8 . . ? C19 C18 H18B 108.8 . . ? H18A C18 H18B 107.7 . . ? C20 C19 C18 113.0(3) . . ? C20 C19 H19A 109.0 . . ? C18 C19 H19A 109.0 . . ? C20 C19 H19B 109.0 . . ? C18 C19 H19B 109.0 . . ? H19A C19 H19B 107.8 . . ? C19 C20 H20A 109.5 . . ? C19 C20 H20B 109.5 . . ? H20A C20 H20B 109.5 . . ? C19 C20 H20C 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 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 0.6(5) . . . . ? Br1 C1 C2 C3 179.8(2) . . . . ? C1 C2 C3 C4 0.7(5) . . . . ? C7 N1 C4 C3 179.1(3) . . . . ? C7 N1 C4 C5 0.4(4) . . . . ? C2 C3 C4 N1 -179.5(3) . . . . ? C2 C3 C4 C5 -0.9(5) . . . . ? N1 C4 C5 C6 178.8(3) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? N1 C4 C5 C8 -0.5(3) . . . . ? C3 C4 C5 C8 -179.3(3) . . . . ? C2 C1 C6 C5 -1.5(5) . . . . ? Br1 C1 C6 C5 179.2(2) . . . . ? C4 C5 C6 C1 1.3(5) . . . . ? C8 C5 C6 C1 -179.7(3) . . . . ? C4 N1 C7 C8 -0.1(4) . . . . ? C4 N1 C7 C11 -175.4(3) . . . . ? N1 C7 C8 C5 -0.3(4) . . . . ? C11 C7 C8 C5 175.0(3) . . . . ? N1 C7 C8 C9 -177.0(3) . . . . ? C11 C7 C8 C9 -1.7(5) . . . . ? C6 C5 C8 C7 -178.7(4) . . . . ? C4 C5 C8 C7 0.5(4) . . . . ? C6 C5 C8 C9 -2.2(6) . . . . ? C4 C5 C8 C9 176.9(3) . . . . ? C7 C8 C9 C10 -9.8(4) . . . . ? C5 C8 C9 C10 174.3(3) . . . . ? C14 N2 C10 C9 113.7(3) . . . . ? C11 N2 C10 C9 -60.2(4) . . . . ? C8 C9 C10 N2 36.8(4) . . . . ? C14 N2 C11 C7 -128.9(3) . . . . ? C10 N2 C11 C7 45.6(4) . . . . ? C14 N2 C11 C15 110.3(3) . . . . ? C10 N2 C11 C15 -75.1(4) . . . . ? C14 N2 C11 C12 -10.8(4) . . . . ? C10 N2 C11 C12 163.7(3) . . . . ? C8 C7 C11 N2 -13.7(5) . . . . ? N1 C7 C11 N2 160.9(3) . . . . ? C8 C7 C11 C15 106.5(4) . . . . ? N1 C7 C11 C15 -79.0(4) . . . . ? C8 C7 C11 C12 -124.6(4) . . . . ? N1 C7 C11 C12 50.0(4) . . . . ? N2 C11 C12 C13 19.1(4) . . . . ? C7 C11 C12 C13 132.0(3) . . . . ? C15 C11 C12 C13 -100.1(3) . . . . ? C11 C12 C13 C14 -20.8(4) . . . . ? C10 N2 C14 O1 3.3(5) . . . . ? C11 N2 C14 O1 177.5(3) . . . . ? C10 N2 C14 C13 -176.5(3) . . . . ? C11 N2 C14 C13 -2.3(4) . . . . ? C12 C13 C14 O1 -165.1(3) . . . . ? C12 C13 C14 N2 14.8(4) . . . . ? N2 C11 C15 C16 -61.4(4) . . . . ? C7 C11 C15 C16 -178.5(3) . . . . ? C12 C11 C15 C16 52.9(4) . . . . ? C11 C15 C16 C17 171.9(3) . . . . ? C15 C16 C17 C18 174.7(3) . . . . ? C16 C17 C18 C19 179.5(3) . . . . ? C17 C18 C19 C20 174.9(3) . . . . ? 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 N1 H1N O1 0.96 2.07 2.872(4) 139.6 1_455 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.568 _refine_diff_density_min -0.364 _refine_diff_density_rms 0.074