####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_knih30 _database_code_depnum_ccdc_archive 'CCDC 656369' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H18 N2 O3' _chemical_formula_sum 'C15 H18 N2 O3' _chemical_formula_weight 274.31 _chemical_absolute_configuration . loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 7.4315(16) _cell_length_b 8.4430(18) _cell_length_c 21.576(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1353.7(5) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 9204 _cell_measurement_theta_min 2.60 _cell_measurement_theta_max 28.29 _exptl_crystal_description prism _exptl_crystal_colour yellow _exptl_crystal_size_max 0.64 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.346 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 584 _exptl_absorpt_coefficient_mu 0.095 ########################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # ########################################################## _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2000b)' _exptl_absorpt_correction_T_min 0.582 _exptl_absorpt_correction_T_max 0.974 _exptl_special_details ; Observed absorption in correction is likly due to glass rod and mounting materials in the beam path. Absolute configuration reported by PLATON: C1 = . R C4A = . R C9A = . R ; _diffrn_ambient_temperature 93(2) # SMART 1000 parameters _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 739 _diffrn_standards_interval_count ? _diffrn_standards_interval_time variable _diffrn_standards_decay_% 0.9 _diffrn_reflns_number 9044 _diffrn_reflns_av_R_equivalents 0.0409 _diffrn_reflns_av_sigmaI/netI 0.0418 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 28.05 _reflns_number_total 3138 _reflns_number_gt 2921 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 28.05 _diffrn_measured_fraction_theta_full 0.977 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.631 (Bruker, 2001b)' _computing_cell_refinement 'Bruker SMART v5.631 (Bruker, 2001b)' _computing_data_reduction ; Bruker SAINT v6.45 (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001a) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_molecular_graphics 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_publication_material 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _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^)+(0.0593P)^2^+0.2817P] 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 1.1(11) _refine_ls_number_reflns 3138 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0459 _refine_ls_R_factor_gt 0.0419 _refine_ls_wR_factor_ref 0.1085 _refine_ls_wR_factor_gt 0.1064 _refine_ls_goodness_of_fit_ref 1.094 _refine_ls_restrained_S_all 1.094 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.290 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.052 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 0.8771(2) 0.0901(2) 0.82728(7) 0.0158(3) Uani 1 1 d . . . H1A H 0.8153 0.0234 0.7954 0.019 Uiso 1 1 calc R . . N2 N 0.88950(19) -0.00323(16) 0.88569(6) 0.0149(3) Uani 1 1 d . . . C2 C 0.9981(2) -0.14758(19) 0.87730(8) 0.0191(4) Uani 1 1 d . . . H2A H 0.9609 -0.2015 0.8392 0.029 Uiso 1 1 calc R . . H2B H 0.9800 -0.2183 0.9128 0.029 Uiso 1 1 calc R . . H2C H 1.1256 -0.1189 0.8744 0.029 Uiso 1 1 calc R . . C3 C 0.9449(2) 0.08014(18) 0.94368(7) 0.0167(3) Uani 1 1 d . . . H3A H 1.0761 0.1001 0.9422 0.020 Uiso 1 1 calc R . . H3B H 0.9209 0.0101 0.9796 0.020 Uiso 1 1 calc R . . C4B C 0.7138(2) 0.47533(19) 0.88645(8) 0.0143(3) Uani 1 1 d . . . C4A C 0.8417(2) 0.33464(18) 0.89290(7) 0.0140(3) Uani 1 1 d . . . C4 C 0.8459(2) 0.23978(19) 0.95375(8) 0.0160(3) Uani 1 1 d . . . H4A H 0.7214 0.2195 0.9680 0.019 Uiso 1 1 calc R . . H4B H 0.9086 0.3019 0.9861 0.019 Uiso 1 1 calc R . . C5 C 0.6757(2) 0.60402(19) 0.92401(7) 0.0149(3) Uani 1 1 d . . . H5A H 0.7199 0.6105 0.9653 0.018 Uiso 1 1 calc R . . C6 C 0.5682(2) 0.72513(19) 0.89817(8) 0.0162(3) Uani 1 1 d . . . N6 N 0.5280(2) 0.86423(17) 0.93673(7) 0.0196(3) Uani 1 1 d . . . O6A O 0.43424(18) 0.97151(15) 0.91420(7) 0.0262(3) Uani 1 1 d . . . O6B O 0.5886(2) 0.86790(16) 0.99034(6) 0.0264(3) Uani 1 1 d . . . C7 C 0.5033(2) 0.7209(2) 0.83749(8) 0.0184(3) Uani 1 1 d . . . H7A H 0.4335 0.8063 0.8219 0.022 Uiso 1 1 calc R . . C8 C 0.5415(2) 0.59009(19) 0.79952(8) 0.0182(3) Uani 1 1 d . . . H8A H 0.4986 0.5844 0.7581 0.022 Uiso 1 1 calc R . . C9A C 0.7515(2) 0.2256(2) 0.84488(7) 0.0150(3) Uani 1 1 d . . . H9AA H 0.6409 0.1792 0.8641 0.018 Uiso 1 1 calc R . . O9 O 0.69495(17) 0.33275(14) 0.79409(5) 0.0181(3) Uani 1 1 d . . . C9 C 0.6450(2) 0.46896(19) 0.82519(8) 0.0157(3) Uani 1 1 d . . . C10 C 1.0323(2) 0.3929(2) 0.86987(8) 0.0178(3) Uani 1 1 d . . . H10A H 1.0135 0.4752 0.8378 0.021 Uiso 1 1 calc R . . H10B H 1.0945 0.4439 0.9052 0.021 Uiso 1 1 calc R . . C11 C 1.1594(2) 0.2640(2) 0.84257(9) 0.0226(4) Uani 1 1 d . . . H11A H 1.2583 0.3158 0.8195 0.027 Uiso 1 1 calc R . . H11B H 1.2131 0.2020 0.8768 0.027 Uiso 1 1 calc R . . C12 C 1.0567(3) 0.1521(2) 0.79890(8) 0.0218(4) Uani 1 1 d . . . H12A H 1.1346 0.0606 0.7888 0.026 Uiso 1 1 calc R . . H12B H 1.0300 0.2087 0.7598 0.026 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 0.0176(8) 0.0152(7) 0.0147(7) -0.0006(6) -0.0014(6) 0.0020(6) N2 0.0153(7) 0.0113(6) 0.0180(6) 0.0002(5) -0.0001(5) 0.0012(5) C2 0.0159(8) 0.0133(7) 0.0281(9) 0.0004(6) 0.0005(7) 0.0030(6) C3 0.0168(8) 0.0154(7) 0.0179(8) 0.0007(6) -0.0017(6) 0.0008(6) C4B 0.0112(7) 0.0130(7) 0.0187(7) 0.0012(6) -0.0001(6) 0.0003(6) C4A 0.0126(8) 0.0140(7) 0.0153(7) -0.0007(6) -0.0009(6) 0.0006(6) C4 0.0168(8) 0.0147(7) 0.0164(7) 0.0002(6) -0.0011(6) 0.0021(6) C5 0.0125(7) 0.0136(7) 0.0185(8) 0.0004(6) 0.0009(6) -0.0006(6) C6 0.0125(7) 0.0123(7) 0.0237(8) 0.0006(6) 0.0039(6) 0.0004(6) N6 0.0152(7) 0.0159(7) 0.0278(8) -0.0006(6) 0.0063(6) 0.0005(6) O6A 0.0184(6) 0.0167(6) 0.0436(8) -0.0023(6) -0.0003(6) 0.0060(5) O6B 0.0348(8) 0.0210(6) 0.0233(6) -0.0018(5) 0.0072(6) 0.0021(6) C7 0.0124(8) 0.0163(8) 0.0266(8) 0.0046(7) -0.0002(7) 0.0015(6) C8 0.0154(8) 0.0182(8) 0.0210(8) 0.0010(6) -0.0034(7) 0.0008(7) C9A 0.0154(8) 0.0138(7) 0.0159(8) 0.0010(6) -0.0023(6) 0.0003(6) O9 0.0228(6) 0.0153(6) 0.0163(5) -0.0001(5) -0.0047(5) 0.0041(5) C9 0.0133(8) 0.0141(7) 0.0196(7) -0.0007(6) 0.0004(6) -0.0017(6) C10 0.0139(8) 0.0157(7) 0.0240(8) 0.0005(6) -0.0009(6) 0.0005(7) C11 0.0157(8) 0.0196(8) 0.0327(10) 0.0023(7) 0.0066(7) 0.0010(7) C12 0.0240(9) 0.0175(8) 0.0240(8) 0.0005(7) 0.0088(7) 0.0036(7) _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 N2 1.489(2) . ? C1 C9A 1.525(2) . ? C1 C12 1.559(2) . ? C1 H1A 1.0000 . ? N2 C2 1.473(2) . ? N2 C3 1.493(2) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.551(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4B C5 1.385(2) . ? C4B C9 1.418(2) . ? C4B C4A 1.528(2) . ? C4A C4 1.538(2) . ? C4A C9A 1.540(2) . ? C4A C10 1.579(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 C6 1.412(2) . ? C5 H5A 0.9500 . ? C6 C7 1.396(2) . ? C6 N6 1.470(2) . ? N6 O6A 1.2420(19) . ? N6 O6B 1.242(2) . ? C7 C8 1.404(2) . ? C7 H7A 0.9500 . ? C8 C9 1.394(2) . ? C8 H8A 0.9500 . ? C9A O9 1.4821(19) . ? C9A H9AA 1.0000 . ? O9 C9 1.382(2) . ? C10 C11 1.557(2) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.537(3) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? 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 N2 C1 C9A 102.94(12) . . ? N2 C1 C12 117.20(14) . . ? C9A C1 C12 111.71(14) . . ? N2 C1 H1A 108.2 . . ? C9A C1 H1A 108.2 . . ? C12 C1 H1A 108.2 . . ? C2 N2 C1 111.55(13) . . ? C2 N2 C3 110.00(13) . . ? C1 N2 C3 118.48(13) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 113.35(13) . . ? N2 C3 H3A 108.9 . . ? C4 C3 H3A 108.9 . . ? N2 C3 H3B 108.9 . . ? C4 C3 H3B 108.9 . . ? H3A C3 H3B 107.7 . . ? C5 C4B C9 120.11(15) . . ? C5 C4B C4A 133.14(15) . . ? C9 C4B C4A 106.25(14) . . ? C4B C4A C4 119.69(14) . . ? C4B C4A C9A 97.63(13) . . ? C4 C4A C9A 105.77(13) . . ? C4B C4A C10 106.69(13) . . ? C4 C4A C10 114.35(14) . . ? C9A C4A C10 111.41(13) . . ? C4A C4 C3 110.04(13) . . ? C4A C4 H4A 109.7 . . ? C3 C4 H4A 109.7 . . ? C4A C4 H4B 109.7 . . ? C3 C4 H4B 109.7 . . ? H4A C4 H4B 108.2 . . ? C4B C5 C6 116.90(15) . . ? C4B C5 H5A 121.5 . . ? C6 C5 H5A 121.5 . . ? C7 C6 C5 123.18(15) . . ? C7 C6 N6 118.76(14) . . ? C5 C6 N6 118.03(15) . . ? O6A N6 O6B 123.35(15) . . ? O6A N6 C6 118.38(15) . . ? O6B N6 C6 118.27(15) . . ? C6 C7 C8 119.85(15) . . ? C6 C7 H7A 120.1 . . ? C8 C7 H7A 120.1 . . ? C9 C8 C7 117.17(15) . . ? C9 C8 H8A 121.4 . . ? C7 C8 H8A 121.4 . . ? O9 C9A C1 116.58(13) . . ? O9 C9A C4A 104.83(13) . . ? C1 C9A C4A 110.48(13) . . ? O9 C9A H9AA 108.2 . . ? C1 C9A H9AA 108.2 . . ? C4A C9A H9AA 108.2 . . ? C9 O9 C9A 103.01(12) . . ? O9 C9 C8 124.45(15) . . ? O9 C9 C4B 112.77(14) . . ? C8 C9 C4B 122.76(15) . . ? C11 C10 C4A 116.45(13) . . ? C11 C10 H10A 108.2 . . ? C4A C10 H10A 108.2 . . ? C11 C10 H10B 108.2 . . ? C4A C10 H10B 108.2 . . ? H10A C10 H10B 107.3 . . ? C12 C11 C10 111.13(15) . . ? C12 C11 H11A 109.4 . . ? C10 C11 H11A 109.4 . . ? C12 C11 H11B 109.4 . . ? C10 C11 H11B 109.4 . . ? H11A C11 H11B 108.0 . . ? C11 C12 C1 113.01(14) . . ? C11 C12 H12A 109.0 . . ? C1 C12 H12A 109.0 . . ? C11 C12 H12B 109.0 . . ? C1 C12 H12B 109.0 . . ? H12A C12 H12B 107.8 . . ? 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 C9A C1 N2 C2 176.49(13) . . . . ? C12 C1 N2 C2 -60.51(18) . . . . ? C9A C1 N2 C3 -54.26(18) . . . . ? C12 C1 N2 C3 68.74(18) . . . . ? C2 N2 C3 C4 176.08(13) . . . . ? C1 N2 C3 C4 46.12(19) . . . . ? C5 C4B C4A C4 47.8(3) . . . . ? C9 C4B C4A C4 -140.61(15) . . . . ? C5 C4B C4A C9A 160.92(17) . . . . ? C9 C4B C4A C9A -27.52(16) . . . . ? C5 C4B C4A C10 -84.0(2) . . . . ? C9 C4B C4A C10 87.60(15) . . . . ? C4B C4A C4 C3 165.02(14) . . . . ? C9A C4A C4 C3 56.36(16) . . . . ? C10 C4A C4 C3 -66.60(17) . . . . ? N2 C3 C4 C4A -44.89(18) . . . . ? C9 C4B C5 C6 -0.3(2) . . . . ? C4A C4B C5 C6 170.31(16) . . . . ? C4B C5 C6 C7 -1.0(2) . . . . ? C4B C5 C6 N6 -179.11(14) . . . . ? C7 C6 N6 O6A 1.5(2) . . . . ? C5 C6 N6 O6A 179.69(14) . . . . ? C7 C6 N6 O6B -178.98(15) . . . . ? C5 C6 N6 O6B -0.8(2) . . . . ? C5 C6 C7 C8 1.3(2) . . . . ? N6 C6 C7 C8 179.35(15) . . . . ? C6 C7 C8 C9 -0.1(2) . . . . ? N2 C1 C9A O9 -173.62(12) . . . . ? C12 C1 C9A O9 59.77(18) . . . . ? N2 C1 C9A C4A 66.88(16) . . . . ? C12 C1 C9A C4A -59.72(17) . . . . ? C4B C4A C9A O9 38.25(14) . . . . ? C4 C4A C9A O9 162.11(12) . . . . ? C10 C4A C9A O9 -73.08(16) . . . . ? C4B C4A C9A C1 164.62(13) . . . . ? C4 C4A C9A C1 -71.52(16) . . . . ? C10 C4A C9A C1 53.29(17) . . . . ? C1 C9A O9 C9 -158.20(14) . . . . ? C4A C9A O9 C9 -35.71(15) . . . . ? C9A O9 C9 C8 -163.54(16) . . . . ? C9A O9 C9 C4B 17.79(17) . . . . ? C7 C8 C9 O9 -179.74(15) . . . . ? C7 C8 C9 C4B -1.2(2) . . . . ? C5 C4B C9 O9 -179.85(14) . . . . ? C4A C4B C9 O9 7.27(18) . . . . ? C5 C4B C9 C8 1.5(2) . . . . ? C4A C4B C9 C8 -171.43(15) . . . . ? C4B C4A C10 C11 -152.21(15) . . . . ? C4 C4A C10 C11 73.10(18) . . . . ? C9A C4A C10 C11 -46.76(19) . . . . ? C4A C10 C11 C12 43.6(2) . . . . ? C10 C11 C12 C1 -48.03(19) . . . . ? N2 C1 C12 C11 -60.52(19) . . . . ? C9A C1 C12 C11 57.87(18) . . . . ? data_knih33 _database_code_depnum_ccdc_archive 'CCDC 656370' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H17 O8, C15 H20 F N2 O3, 1.5(C2 H8 O2)' _chemical_formula_sum 'C36.50 H43 F N2 O12.50' _chemical_formula_weight 728.73 _chemical_absolute_configuration rm 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' F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' 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 8.7028(11) _cell_length_b 13.9149(15) _cell_length_c 30.493(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3692.7(7) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 3511 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 28.25 _exptl_crystal_description 'hexagonal plate' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.50 _exptl_crystal_size_mid 0.46 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.311 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1540 _exptl_absorpt_coefficient_mu 0.102 ########################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # ########################################################## _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2000b)' _exptl_absorpt_correction_T_min 0.821 _exptl_absorpt_correction_T_max 0.986 _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a # SMART 1000 parameters _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1976 _diffrn_standards_interval_count ? _diffrn_standards_interval_time variable _diffrn_standards_decay_% none _diffrn_reflns_number 29850 _diffrn_reflns_av_R_equivalents 0.0474 _diffrn_reflns_av_sigmaI/netI 0.0523 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 1.34 _diffrn_reflns_theta_max 28.34 _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.979 _reflns_number_total 8982 _reflns_number_gt 7731 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.631 (Bruker, 2001b)' _computing_cell_refinement 'Bruker SMART v5.631 (Bruker, 2001b)' _computing_data_reduction ; Bruker SAINT v6.45 (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001a) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_molecular_graphics 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_publication_material 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _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^)+(0.0526P)^2^+1.5491P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.5(8) _refine_ls_number_reflns 8982 _refine_ls_number_parameters 495 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0747 _refine_ls_R_factor_gt 0.0621 _refine_ls_wR_factor_ref 0.1312 _refine_ls_wR_factor_gt 0.1270 _refine_ls_goodness_of_fit_ref 1.122 _refine_ls_restrained_S_all 1.122 _refine_ls_shift/su_max 0.197 _refine_ls_shift/su_mean 0.003 _refine_diff_density_max 0.344 _refine_diff_density_min -0.359 _refine_diff_density_rms 0.055 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 0.1838(3) 0.21273(16) 0.11569(8) 0.0204(5) Uani 1 1 d . . . H1A H 0.0864 0.1969 0.1315 0.024 Uiso 1 1 calc R . . N2 N 0.3073(3) 0.22644(14) 0.14968(7) 0.0206(4) Uani 1 1 d . . . H2 H 0.271(4) 0.272(2) 0.1696(10) 0.031 Uiso 1 1 d . . . C2 C 0.3309(4) 0.13995(18) 0.17826(9) 0.0308(6) Uani 1 1 d . . . H2A H 0.2332 0.1220 0.1920 0.046 Uiso 1 1 calc R . . H2B H 0.4065 0.1550 0.2011 0.046 Uiso 1 1 calc R . . H2C H 0.3685 0.0863 0.1604 0.046 Uiso 1 1 calc R . . C3 C 0.4579(3) 0.25800(17) 0.13049(8) 0.0219(5) Uani 1 1 d . . . H3A H 0.5054 0.2035 0.1146 0.026 Uiso 1 1 calc R . . H3B H 0.5283 0.2772 0.1544 0.026 Uiso 1 1 calc R . . C4 C 0.4365(3) 0.34202(18) 0.09914(8) 0.0217(5) Uani 1 1 d . . . H4A H 0.5337 0.3510 0.0828 0.026 Uiso 1 1 calc R . . H4B H 0.4198 0.4007 0.1169 0.026 Uiso 1 1 calc R . . C4A C 0.3033(3) 0.33445(16) 0.06518(8) 0.0194(5) Uani 1 1 d . . . C4B C 0.2908(3) 0.43272(17) 0.04291(8) 0.0206(5) Uani 1 1 d . . . C5 C 0.1586(3) 0.48936(18) 0.04484(8) 0.0225(5) Uani 1 1 d . . . H5A H 0.0695 0.4658 0.0593 0.027 Uiso 1 1 calc R . . C6 C 0.1567(3) 0.57964(18) 0.02578(8) 0.0253(5) Uani 1 1 d . . . N6 N 0.0141(3) 0.63576(15) 0.02814(7) 0.0293(5) Uani 1 1 d . . . O6A O 0.0192(3) 0.72049(13) 0.01717(7) 0.0421(5) Uani 1 1 d . . . O6B O -0.1035(3) 0.59505(15) 0.03942(7) 0.0394(5) Uani 1 1 d . . . C7 C 0.2812(3) 0.61923(19) 0.00440(9) 0.0307(6) Uani 1 1 d . . . H7A H 0.2766 0.6820 -0.0077 0.037 Uiso 1 1 calc R . . C8 C 0.4123(3) 0.5642(2) 0.00129(9) 0.0301(6) Uani 1 1 d . . . H8A H 0.5003 0.5879 -0.0137 0.036 Uiso 1 1 calc R . . C9 C 0.4139(3) 0.47362(19) 0.02037(9) 0.0259(5) Uani 1 1 d . . . F9 F 0.54619(19) 0.42356(11) 0.01620(5) 0.0339(4) Uani 1 1 d . . . C9A C 0.1593(3) 0.31001(16) 0.09213(8) 0.0171(5) Uani 1 1 d . . . H9AA H 0.1406 0.3616 0.1143 0.021 Uiso 1 1 calc R . . O9 O 0.0292(2) 0.30100(13) 0.06464(6) 0.0249(4) Uani 1 1 d . . . H9 H -0.051(4) 0.309(2) 0.0821(11) 0.037 Uiso 1 1 d . . . C10 C 0.3241(3) 0.25648(18) 0.02930(8) 0.0251(5) Uani 1 1 d . . . H10A H 0.2366 0.2604 0.0086 0.030 Uiso 1 1 calc R . . H10B H 0.4190 0.2705 0.0126 0.030 Uiso 1 1 calc R . . C11 C 0.3338(3) 0.15407(18) 0.04727(9) 0.0283(6) Uani 1 1 d . . . H11A H 0.4372 0.1439 0.0600 0.034 Uiso 1 1 calc R . . H11B H 0.3211 0.1082 0.0227 0.034 Uiso 1 1 calc R . . C12 C 0.2127(3) 0.13249(17) 0.08234(9) 0.0259(6) Uani 1 1 d . . . H12A H 0.1145 0.1176 0.0674 0.031 Uiso 1 1 calc R . . H12B H 0.2447 0.0741 0.0985 0.031 Uiso 1 1 calc R . . O1' O 0.7819(2) 0.00313(11) 0.20381(5) 0.0213(4) Uani 1 1 d . . . C2' C 0.9035(3) 0.05158(15) 0.22606(8) 0.0182(5) Uani 1 1 d . . . H2'A H 1.0046 0.0255 0.2159 0.022 Uiso 1 1 calc R . . C2" C 0.8970(3) 0.16009(15) 0.21706(8) 0.0180(5) Uani 1 1 d . . . O2' O 1.0131(2) 0.20370(12) 0.23422(6) 0.0277(4) Uani 1 1 d . . . H2' H 1.007(4) 0.292(2) 0.2319(10) 0.042 Uiso 1 1 d . . . O2" O 0.7953(2) 0.19668(12) 0.19576(6) 0.0267(4) Uani 1 1 d . . . C3' C 0.8828(3) 0.03042(15) 0.27467(8) 0.0184(5) Uani 1 1 d . . . H3'A H 0.9693 0.0597 0.2916 0.022 Uiso 1 1 calc R . . C3" C 0.8784(3) -0.07873(16) 0.28297(8) 0.0207(5) Uani 1 1 d . . . O3' O 0.7647(2) -0.11596(12) 0.29981(6) 0.0242(4) Uani 1 1 d . . . O3" O 1.0010(2) -0.12055(12) 0.27072(7) 0.0348(5) Uani 1 1 d . . . O4' O 0.7416(2) 0.07477(11) 0.28703(5) 0.0204(4) Uani 1 1 d . . . C5' C 0.7170(3) 0.08459(15) 0.33090(8) 0.0198(5) Uani 1 1 d . . . O5' O 0.8125(2) 0.06552(13) 0.35807(6) 0.0282(4) Uani 1 1 d . . . C6' C 0.5603(3) 0.12237(16) 0.33960(8) 0.0218(5) Uani 1 1 d . . . C7' C 0.5189(3) 0.14041(17) 0.38304(8) 0.0235(5) Uani 1 1 d . . . H7'A H 0.5888 0.1269 0.4061 0.028 Uiso 1 1 calc R . . C8' C 0.3751(3) 0.17811(18) 0.39229(9) 0.0281(6) Uani 1 1 d . . . H8'A H 0.3472 0.1904 0.4219 0.034 Uiso 1 1 calc R . . C9' C 0.2714(3) 0.19817(18) 0.35898(10) 0.0288(6) Uani 1 1 d . . . C9A' C 0.1150(3) 0.2394(2) 0.36909(11) 0.0385(7) Uani 1 1 d . . . H9AB H 0.1219 0.2809 0.3950 0.058 Uiso 1 1 calc R . . H9AC H 0.0426 0.1869 0.3749 0.058 Uiso 1 1 calc R . . H9AD H 0.0789 0.2771 0.3440 0.058 Uiso 1 1 calc R . . C10' C 0.3126(3) 0.17863(19) 0.31588(9) 0.0307(6) Uani 1 1 d . . . H10C H 0.2417 0.1909 0.2928 0.037 Uiso 1 1 calc R . . C11' C 0.4570(3) 0.14110(19) 0.30621(9) 0.0274(6) Uani 1 1 d . . . H11C H 0.4846 0.1283 0.2766 0.033 Uiso 1 1 calc R . . C12' C 0.7923(3) -0.00064(17) 0.15955(8) 0.0232(5) Uani 1 1 d . . . O12' O 0.9027(2) 0.02618(15) 0.13945(6) 0.0339(5) Uani 1 1 d . . . C13' C 0.6503(3) -0.04123(16) 0.14062(9) 0.0250(6) Uani 1 1 d . . . C14' C 0.6213(4) -0.0298(2) 0.09626(10) 0.0335(6) Uani 1 1 d . . . H14A H 0.6943 0.0016 0.0781 0.040 Uiso 1 1 calc R . . C15' C 0.4854(4) -0.0643(2) 0.07841(10) 0.0386(7) Uani 1 1 d . . . H15A H 0.4655 -0.0551 0.0481 0.046 Uiso 1 1 calc R . . C16' C 0.3780(4) -0.11191(19) 0.10410(11) 0.0389(8) Uani 1 1 d . . . C16A C 0.2317(4) -0.1501(2) 0.08387(14) 0.0535(10) Uani 1 1 d . . . H16A H 0.2304 -0.1351 0.0525 0.080 Uiso 1 1 calc R . . H16B H 0.1429 -0.1201 0.0981 0.080 Uiso 1 1 calc R . . H16C H 0.2269 -0.2199 0.0879 0.080 Uiso 1 1 calc R . . C17' C 0.4079(4) -0.12348(19) 0.14801(11) 0.0365(7) Uani 1 1 d . . . H17A H 0.3354 -0.1561 0.1659 0.044 Uiso 1 1 calc R . . C18' C 0.5423(3) -0.08833(18) 0.16668(10) 0.0315(6) Uani 1 1 d . . . H18A H 0.5605 -0.0964 0.1972 0.038 Uiso 1 1 calc R . . C1S C 0.8061(4) 0.4405(2) 0.13268(14) 0.0546(10) Uani 1 1 d . . . H1SA H 0.7310 0.4577 0.1553 0.082 Uiso 1 1 calc R . . H1SB H 0.7761 0.4698 0.1047 0.082 Uiso 1 1 calc R . . H1SC H 0.9079 0.4641 0.1412 0.082 Uiso 1 1 calc R . . O1S O 0.8109(2) 0.33774(14) 0.12791(7) 0.0336(5) Uani 1 1 d . . . H1S H 0.813(4) 0.307(3) 0.1533(12) 0.050 Uiso 1 1 d . . . C2S C 0.4008(6) 0.9068(4) 0.26802(18) 0.0300(12) Uani 0.50 1 d P . . H2SA H 0.3848 0.9097 0.2998 0.045 Uiso 0.50 1 calc PR . . H2SB H 0.5000 0.9360 0.2607 0.045 Uiso 0.50 1 calc PR . . H2SC H 0.4000 0.8396 0.2584 0.045 Uiso 0.50 1 calc PR . . O2S O 0.2818(5) 0.9576(3) 0.24659(13) 0.0355(9) Uani 0.50 1 d P . . H2S H 0.1965 0.9404 0.2568 0.053 Uiso 0.50 1 calc PR . . 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 0.0168(12) 0.0189(10) 0.0255(12) -0.0006(9) 0.0016(10) -0.0004(10) N2 0.0225(11) 0.0174(9) 0.0219(10) -0.0006(8) 0.0011(9) 0.0049(8) C2 0.0360(16) 0.0257(12) 0.0308(14) 0.0092(11) 0.0029(13) 0.0069(12) C3 0.0155(12) 0.0250(11) 0.0251(13) 0.0002(10) -0.0035(10) 0.0031(10) C4 0.0137(12) 0.0266(11) 0.0247(12) -0.0004(10) -0.0022(10) -0.0003(10) C4A 0.0157(12) 0.0202(11) 0.0224(11) 0.0002(9) 0.0020(10) 0.0000(9) C4B 0.0211(13) 0.0246(11) 0.0162(10) -0.0001(9) -0.0002(10) -0.0020(10) C5 0.0190(13) 0.0266(12) 0.0218(12) 0.0006(10) -0.0017(10) -0.0020(10) C6 0.0286(14) 0.0244(11) 0.0229(12) 0.0015(10) -0.0061(11) 0.0027(11) N6 0.0341(14) 0.0273(11) 0.0266(11) 0.0030(9) -0.0057(10) 0.0085(10) O6A 0.0493(14) 0.0235(9) 0.0536(13) 0.0036(9) -0.0124(11) 0.0088(9) O6B 0.0310(12) 0.0395(11) 0.0478(12) 0.0092(10) 0.0061(10) 0.0109(10) C7 0.0367(17) 0.0274(12) 0.0280(13) 0.0081(11) -0.0024(12) -0.0058(12) C8 0.0265(15) 0.0354(14) 0.0283(13) 0.0043(11) 0.0043(12) -0.0074(12) C9 0.0212(14) 0.0295(12) 0.0270(13) -0.0010(11) 0.0016(11) -0.0004(11) F9 0.0225(8) 0.0389(8) 0.0404(9) 0.0066(7) 0.0101(7) 0.0022(7) C9A 0.0147(12) 0.0168(10) 0.0198(11) -0.0014(9) -0.0010(9) -0.0003(9) O9 0.0184(9) 0.0290(9) 0.0272(9) -0.0012(8) -0.0047(8) -0.0009(8) C10 0.0252(14) 0.0291(12) 0.0210(12) -0.0039(10) 0.0024(11) 0.0017(11) C11 0.0326(15) 0.0214(11) 0.0309(14) -0.0103(10) 0.0002(12) 0.0020(11) C12 0.0280(14) 0.0176(11) 0.0320(13) -0.0051(10) -0.0016(12) -0.0018(10) O1' 0.0205(9) 0.0166(7) 0.0267(9) -0.0035(7) 0.0014(7) -0.0051(7) C2' 0.0151(12) 0.0140(9) 0.0255(12) -0.0015(9) 0.0005(10) -0.0008(9) C2" 0.0189(12) 0.0137(9) 0.0215(11) -0.0002(9) 0.0055(10) 0.0001(9) O2' 0.0247(10) 0.0152(7) 0.0433(11) 0.0034(7) -0.0099(9) -0.0025(7) O2" 0.0271(10) 0.0174(8) 0.0357(10) 0.0046(7) -0.0073(8) -0.0012(7) C3' 0.0140(11) 0.0135(9) 0.0278(13) 0.0016(9) -0.0004(10) 0.0004(9) C3" 0.0237(13) 0.0140(10) 0.0242(12) 0.0014(9) -0.0038(10) 0.0012(10) O3' 0.0244(10) 0.0165(7) 0.0317(9) 0.0052(7) 0.0024(8) -0.0041(7) O3" 0.0238(10) 0.0136(8) 0.0671(14) 0.0051(9) 0.0067(10) 0.0040(8) O4' 0.0203(9) 0.0169(7) 0.0240(8) 0.0017(7) 0.0021(7) 0.0053(7) C5' 0.0200(13) 0.0148(10) 0.0245(12) 0.0014(9) -0.0019(10) -0.0032(9) O5' 0.0225(10) 0.0342(9) 0.0280(9) 0.0000(8) -0.0049(8) 0.0046(8) C6' 0.0223(13) 0.0162(10) 0.0268(13) -0.0020(9) -0.0010(11) -0.0016(10) C7' 0.0230(14) 0.0234(11) 0.0242(12) 0.0004(10) -0.0016(11) -0.0061(10) C8' 0.0290(15) 0.0266(12) 0.0287(13) -0.0042(10) 0.0103(12) -0.0061(11) C9' 0.0229(14) 0.0227(11) 0.0409(15) -0.0010(11) 0.0049(12) -0.0015(11) C9A' 0.0222(15) 0.0386(15) 0.055(2) -0.0010(14) 0.0087(14) 0.0030(13) C10' 0.0252(15) 0.0314(13) 0.0355(15) 0.0012(11) -0.0053(12) 0.0029(12) C11' 0.0253(14) 0.0318(13) 0.0249(13) -0.0011(10) -0.0035(11) 0.0032(11) C12' 0.0251(14) 0.0175(10) 0.0271(13) -0.0026(9) 0.0039(11) 0.0017(10) O12' 0.0301(11) 0.0407(10) 0.0308(10) -0.0059(9) 0.0063(9) -0.0057(9) C13' 0.0246(14) 0.0166(10) 0.0337(14) -0.0070(10) -0.0016(11) 0.0027(10) C14' 0.0337(16) 0.0291(13) 0.0376(15) -0.0097(12) 0.0013(13) 0.0050(12) C15' 0.0431(19) 0.0347(14) 0.0381(16) -0.0154(13) -0.0145(15) 0.0102(14) C16' 0.0308(16) 0.0220(12) 0.064(2) -0.0152(13) -0.0154(15) 0.0059(12) C16A 0.039(2) 0.0420(17) 0.080(3) -0.0159(17) -0.0280(19) 0.0060(15) C17' 0.0293(16) 0.0216(12) 0.0588(19) -0.0034(13) -0.0046(14) -0.0032(12) C18' 0.0270(15) 0.0216(12) 0.0458(17) -0.0030(11) -0.0075(13) -0.0019(11) C1S 0.0369(19) 0.0433(17) 0.084(3) -0.0124(18) -0.0161(19) 0.0068(16) O1S 0.0243(11) 0.0353(10) 0.0411(11) 0.0100(9) 0.0049(9) 0.0025(9) C2S 0.019(3) 0.046(3) 0.025(3) 0.000(2) 0.005(2) 0.009(2) O2S 0.022(2) 0.042(2) 0.043(2) 0.0151(18) 0.0038(18) -0.0031(18) _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 N2 1.506(3) . ? C1 C12 1.531(3) . ? C1 C9A 1.547(3) . ? C1 H1A 1.0000 . ? N2 C2 1.500(3) . ? N2 C3 1.501(3) . ? N2 H2 0.93(3) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.522(3) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C4A 1.558(3) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4A C4B 1.531(3) . ? C4A C9A 1.537(3) . ? C4A C10 1.551(3) . ? C4B C9 1.394(4) . ? C4B C5 1.396(4) . ? C5 C6 1.384(3) . ? C5 H5A 0.9500 . ? C6 C7 1.379(4) . ? C6 N6 1.468(4) . ? N6 O6B 1.220(3) . ? N6 O6A 1.226(3) . ? C7 C8 1.377(4) . ? C7 H7A 0.9500 . ? C8 C9 1.388(4) . ? C8 H8A 0.9500 . ? C9 F9 1.352(3) . ? C9A O9 1.414(3) . ? C9A H9AA 1.0000 . ? O9 H9 0.88(4) . ? C10 C11 1.529(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.531(4) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? O1' C12' 1.354(3) . ? O1' C2' 1.427(3) . ? C2' C3' 1.522(3) . ? C2' C2" 1.536(3) . ? C2' H2'A 1.0000 . ? C2" O2" 1.210(3) . ? C2" O2' 1.289(3) . ? O2' H2' 1.23(3) . ? C3' O4' 1.425(3) . ? C3' C3" 1.540(3) . ? C3' H3'A 1.0000 . ? C3" O3' 1.229(3) . ? C3" O3" 1.272(3) . ? O4' C5' 1.362(3) . ? C5' O5' 1.203(3) . ? C5' C6' 1.485(4) . ? C6' C11' 1.383(4) . ? C6' C7' 1.396(4) . ? C7' C8' 1.386(4) . ? C7' H7'A 0.9500 . ? C8' C9' 1.387(4) . ? C8' H8'A 0.9500 . ? C9' C10' 1.389(4) . ? C9' C9A' 1.509(4) . ? C9A' H9AB 0.9800 . ? C9A' H9AC 0.9800 . ? C9A' H9AD 0.9800 . ? C10' C11' 1.393(4) . ? C10' H10C 0.9500 . ? C11' H11C 0.9500 . ? C12' O12' 1.200(3) . ? C12' C13' 1.476(4) . ? C13' C14' 1.385(4) . ? C13' C18' 1.395(4) . ? C14' C15' 1.387(4) . ? C14' H14A 0.9500 . ? C15' C16' 1.388(5) . ? C15' H15A 0.9500 . ? C16' C17' 1.373(5) . ? C16' C16A 1.512(4) . ? C16A H16A 0.9800 . ? C16A H16B 0.9800 . ? C16A H16C 0.9800 . ? C17' C18' 1.390(4) . ? C17' H17A 0.9500 . ? C18' H18A 0.9500 . ? C1S O1S 1.438(4) . ? C1S H1SA 0.9800 . ? C1S H1SB 0.9800 . ? C1S H1SC 0.9800 . ? O1S H1S 0.88(4) . ? C2S O2S 1.413(7) . ? C2S H2SA 0.9800 . ? C2S H2SB 0.9800 . ? C2S H2SC 0.9800 . ? O2S H2S 0.8400 . ? 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 N2 C1 C12 115.6(2) . . ? N2 C1 C9A 107.89(18) . . ? C12 C1 C9A 110.6(2) . . ? N2 C1 H1A 107.5 . . ? C12 C1 H1A 107.5 . . ? C9A C1 H1A 107.5 . . ? C2 N2 C3 110.0(2) . . ? C2 N2 C1 113.3(2) . . ? C3 N2 C1 113.09(18) . . ? C2 N2 H2 102.3(18) . . ? C3 N2 H2 110.5(19) . . ? C1 N2 H2 107.1(19) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 111.3(2) . . ? N2 C3 H3A 109.4 . . ? C4 C3 H3A 109.4 . . ? N2 C3 H3B 109.4 . . ? C4 C3 H3B 109.4 . . ? H3A C3 H3B 108.0 . . ? C3 C4 C4A 117.2(2) . . ? C3 C4 H4A 108.0 . . ? C4A C4 H4A 108.0 . . ? C3 C4 H4B 108.0 . . ? C4A C4 H4B 108.0 . . ? H4A C4 H4B 107.2 . . ? C4B C4A C9A 112.1(2) . . ? C4B C4A C10 108.67(19) . . ? C9A C4A C10 108.48(19) . . ? C4B C4A C4 106.71(19) . . ? C9A C4A C4 105.46(19) . . ? C10 C4A C4 115.4(2) . . ? C9 C4B C5 115.1(2) . . ? C9 C4B C4A 121.9(2) . . ? C5 C4B C4A 123.0(2) . . ? C6 C5 C4B 120.3(2) . . ? C6 C5 H5A 119.9 . . ? C4B C5 H5A 119.9 . . ? C7 C6 C5 123.5(3) . . ? C7 C6 N6 118.3(2) . . ? C5 C6 N6 118.2(2) . . ? O6B N6 O6A 123.6(2) . . ? O6B N6 C6 118.5(2) . . ? O6A N6 C6 117.9(3) . . ? C8 C7 C6 117.5(2) . . ? C8 C7 H7A 121.3 . . ? C6 C7 H7A 121.3 . . ? C7 C8 C9 118.9(3) . . ? C7 C8 H8A 120.5 . . ? C9 C8 H8A 120.5 . . ? F9 C9 C8 115.9(2) . . ? F9 C9 C4B 119.4(2) . . ? C8 C9 C4B 124.7(3) . . ? O9 C9A C4A 110.83(19) . . ? O9 C9A C1 107.94(18) . . ? C4A C9A C1 109.23(19) . . ? O9 C9A H9AA 109.6 . . ? C4A C9A H9AA 109.6 . . ? C1 C9A H9AA 109.6 . . ? C9A O9 H9 105(2) . . ? C11 C10 C4A 113.9(2) . . ? C11 C10 H10A 108.8 . . ? C4A C10 H10A 108.8 . . ? C11 C10 H10B 108.8 . . ? C4A C10 H10B 108.8 . . ? H10A C10 H10B 107.7 . . ? C10 C11 C12 113.3(2) . . ? C10 C11 H11A 108.9 . . ? C12 C11 H11A 108.9 . . ? C10 C11 H11B 108.9 . . ? C12 C11 H11B 108.9 . . ? H11A C11 H11B 107.7 . . ? C1 C12 C11 115.7(2) . . ? C1 C12 H12A 108.3 . . ? C11 C12 H12A 108.3 . . ? C1 C12 H12B 108.3 . . ? C11 C12 H12B 108.3 . . ? H12A C12 H12B 107.4 . . ? C12' O1' C2' 116.27(19) . . ? O1' C2' C3' 106.47(18) . . ? O1' C2' C2" 110.61(19) . . ? C3' C2' C2" 111.09(18) . . ? O1' C2' H2'A 109.5 . . ? C3' C2' H2'A 109.5 . . ? C2" C2' H2'A 109.5 . . ? O2" C2" O2' 126.4(2) . . ? O2" C2" C2' 122.5(2) . . ? O2' C2" C2' 111.2(2) . . ? C2" O2' H2' 114.4(16) . . ? O4' C3' C2' 106.03(18) . . ? O4' C3' C3" 111.23(19) . . ? C2' C3' C3" 110.71(19) . . ? O4' C3' H3'A 109.6 . . ? C2' C3' H3'A 109.6 . . ? C3" C3' H3'A 109.6 . . ? O3' C3" O3" 127.3(2) . . ? O3' C3" C3' 120.3(2) . . ? O3" C3" C3' 112.5(2) . . ? C5' O4' C3' 116.05(18) . . ? O5' C5' O4' 123.1(2) . . ? O5' C5' C6' 126.1(2) . . ? O4' C5' C6' 110.8(2) . . ? C11' C6' C7' 119.8(2) . . ? C11' C6' C5' 122.1(2) . . ? C7' C6' C5' 118.1(2) . . ? C8' C7' C6' 119.7(2) . . ? C8' C7' H7'A 120.2 . . ? C6' C7' H7'A 120.2 . . ? C7' C8' C9' 121.0(2) . . ? C7' C8' H8'A 119.5 . . ? C9' C8' H8'A 119.5 . . ? C8' C9' C10' 119.1(3) . . ? C8' C9' C9A' 120.9(3) . . ? C10' C9' C9A' 120.0(3) . . ? C9' C9A' H9AB 109.5 . . ? C9' C9A' H9AC 109.5 . . ? H9AB C9A' H9AC 109.5 . . ? C9' C9A' H9AD 109.5 . . ? H9AB C9A' H9AD 109.5 . . ? H9AC C9A' H9AD 109.5 . . ? C9' C10' C11' 120.4(3) . . ? C9' C10' H10C 119.8 . . ? C11' C10' H10C 119.8 . . ? C6' C11' C10' 120.1(3) . . ? C6' C11' H11C 119.9 . . ? C10' C11' H11C 119.9 . . ? O12' C12' O1' 123.4(2) . . ? O12' C12' C13' 126.1(2) . . ? O1' C12' C13' 110.4(2) . . ? C14' C13' C18' 119.1(3) . . ? C14' C13' C12' 119.4(2) . . ? C18' C13' C12' 121.4(2) . . ? C13' C14' C15' 119.9(3) . . ? C13' C14' H14A 120.0 . . ? C15' C14' H14A 120.0 . . ? C14' C15' C16' 121.2(3) . . ? C14' C15' H15A 119.4 . . ? C16' C15' H15A 119.4 . . ? C17' C16' C15' 118.6(3) . . ? C17' C16' C16A 121.1(3) . . ? C15' C16' C16A 120.3(3) . . ? C16' C16A H16A 109.5 . . ? C16' C16A H16B 109.5 . . ? H16A C16A H16B 109.5 . . ? C16' C16A H16C 109.5 . . ? H16A C16A H16C 109.5 . . ? H16B C16A H16C 109.5 . . ? C16' C17' C18' 121.2(3) . . ? C16' C17' H17A 119.4 . . ? C18' C17' H17A 119.4 . . ? C17' C18' C13' 120.0(3) . . ? C17' C18' H18A 120.0 . . ? C13' C18' H18A 120.0 . . ? O1S C1S H1SA 109.5 . . ? O1S C1S H1SB 109.5 . . ? H1SA C1S H1SB 109.5 . . ? O1S C1S H1SC 109.5 . . ? H1SA C1S H1SC 109.5 . . ? H1SB C1S H1SC 109.5 . . ? C1S O1S H1S 113(2) . . ? O2S C2S H2SA 109.5 . . ? O2S C2S H2SB 109.5 . . ? H2SA C2S H2SB 109.5 . . ? O2S C2S H2SC 109.5 . . ? H2SA C2S H2SC 109.5 . . ? H2SB C2S H2SC 109.5 . . ? C2S O2S H2S 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 C12 C1 N2 C2 -61.7(3) . . . . ? C9A C1 N2 C2 173.9(2) . . . . ? C12 C1 N2 C3 64.4(3) . . . . ? C9A C1 N2 C3 -60.0(2) . . . . ? C2 N2 C3 C4 176.6(2) . . . . ? C1 N2 C3 C4 48.8(3) . . . . ? N2 C3 C4 C4A -46.0(3) . . . . ? C3 C4 C4A C4B 171.4(2) . . . . ? C3 C4 C4A C9A 52.0(3) . . . . ? C3 C4 C4A C10 -67.7(3) . . . . ? C9A C4A C4B C9 173.6(2) . . . . ? C10 C4A C4B C9 -66.5(3) . . . . ? C4 C4A C4B C9 58.6(3) . . . . ? C9A C4A C4B C5 -4.1(3) . . . . ? C10 C4A C4B C5 115.8(3) . . . . ? C4 C4A C4B C5 -119.1(3) . . . . ? C9 C4B C5 C6 -0.9(4) . . . . ? C4A C4B C5 C6 176.9(2) . . . . ? C4B C5 C6 C7 -0.3(4) . . . . ? C4B C5 C6 N6 179.1(2) . . . . ? C7 C6 N6 O6B 166.4(2) . . . . ? C5 C6 N6 O6B -13.1(4) . . . . ? C7 C6 N6 O6A -11.2(4) . . . . ? C5 C6 N6 O6A 169.4(2) . . . . ? C5 C6 C7 C8 1.5(4) . . . . ? N6 C6 C7 C8 -177.9(2) . . . . ? C6 C7 C8 C9 -1.3(4) . . . . ? C7 C8 C9 F9 -179.9(2) . . . . ? C7 C8 C9 C4B 0.1(4) . . . . ? C5 C4B C9 F9 -179.0(2) . . . . ? C4A C4B C9 F9 3.1(4) . . . . ? C5 C4B C9 C8 1.1(4) . . . . ? C4A C4B C9 C8 -176.8(2) . . . . ? C4B C4A C9A O9 64.4(2) . . . . ? C10 C4A C9A O9 -55.7(2) . . . . ? C4 C4A C9A O9 -179.89(18) . . . . ? C4B C4A C9A C1 -176.85(18) . . . . ? C10 C4A C9A C1 63.1(2) . . . . ? C4 C4A C9A C1 -61.1(2) . . . . ? N2 C1 C9A O9 -171.91(18) . . . . ? C12 C1 C9A O9 60.7(3) . . . . ? N2 C1 C9A C4A 67.5(2) . . . . ? C12 C1 C9A C4A -59.8(3) . . . . ? C4B C4A C10 C11 -178.5(2) . . . . ? C9A C4A C10 C11 -56.3(3) . . . . ? C4 C4A C10 C11 61.8(3) . . . . ? C4A C10 C11 C12 44.8(3) . . . . ? N2 C1 C12 C11 -74.1(3) . . . . ? C9A C1 C12 C11 48.9(3) . . . . ? C10 C11 C12 C1 -41.2(3) . . . . ? C12' O1' C2' C3' -169.65(18) . . . . ? C12' O1' C2' C2" 69.5(3) . . . . ? O1' C2' C2" O2" 3.7(3) . . . . ? C3' C2' C2" O2" -114.3(3) . . . . ? O1' C2' C2" O2' -175.07(19) . . . . ? C3' C2' C2" O2' 66.9(3) . . . . ? O1' C2' C3' O4' -65.1(2) . . . . ? C2" C2' C3' O4' 55.4(2) . . . . ? O1' C2' C3' C3" 55.6(2) . . . . ? C2" C2' C3' C3" 176.1(2) . . . . ? O4' C3' C3" O3' -2.5(3) . . . . ? C2' C3' C3" O3' -120.1(2) . . . . ? O4' C3' C3" O3" 177.6(2) . . . . ? C2' C3' C3" O3" 60.0(3) . . . . ? C2' C3' O4' C5' -165.19(18) . . . . ? C3" C3' O4' C5' 74.4(2) . . . . ? C3' O4' C5' O5' 6.5(3) . . . . ? C3' O4' C5' C6' -174.23(17) . . . . ? O5' C5' C6' C11' -179.1(2) . . . . ? O4' C5' C6' C11' 1.7(3) . . . . ? O5' C5' C6' C7' 1.8(4) . . . . ? O4' C5' C6' C7' -177.4(2) . . . . ? C11' C6' C7' C8' -0.8(4) . . . . ? C5' C6' C7' C8' 178.3(2) . . . . ? C6' C7' C8' C9' 0.1(4) . . . . ? C7' C8' C9' C10' 0.9(4) . . . . ? C7' C8' C9' C9A' -179.9(2) . . . . ? C8' C9' C10' C11' -1.2(4) . . . . ? C9A' C9' C10' C11' 179.6(3) . . . . ? C7' C6' C11' C10' 0.6(4) . . . . ? C5' C6' C11' C10' -178.5(2) . . . . ? C9' C10' C11' C6' 0.4(4) . . . . ? C2' O1' C12' O12' 7.0(3) . . . . ? C2' O1' C12' C13' -172.68(18) . . . . ? O12' C12' C13' C14' -15.5(4) . . . . ? O1' C12' C13' C14' 164.2(2) . . . . ? O12' C12' C13' C18' 166.5(3) . . . . ? O1' C12' C13' C18' -13.8(3) . . . . ? C18' C13' C14' C15' 0.6(4) . . . . ? C12' C13' C14' C15' -177.4(2) . . . . ? C13' C14' C15' C16' -1.2(4) . . . . ? C14' C15' C16' C17' 0.8(4) . . . . ? C14' C15' C16' C16A -179.1(3) . . . . ? C15' C16' C17' C18' 0.1(4) . . . . ? C16A C16' C17' C18' -179.9(3) . . . . ? C16' C17' C18' C13' -0.7(4) . . . . ? C14' C13' C18' C17' 0.3(4) . . . . ? C12' C13' C18' C17' 178.3(2) . . . . ? data_knih34 _database_code_depnum_ccdc_archive 'CCDC 656371' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H19 N2 O3, C10 H14 Br O4 S' _chemical_formula_sum 'C25 H33 Br N2 O7 S' _chemical_formula_weight 585.50 _chemical_absolute_configuration ad 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' S S 0.1246 0.1234 '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 'P 21 21 21' 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 7.719(3) _cell_length_b 13.922(5) _cell_length_c 24.899(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2675.7(18) _cell_formula_units_Z 4 _cell_measurement_temperature 93(2) _cell_measurement_reflns_used 2099 _cell_measurement_theta_min 2.76 _cell_measurement_theta_max 28.21 _exptl_crystal_description prism _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.65 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1216 _exptl_absorpt_coefficient_mu 1.660 ########################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # ########################################################## _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2000b)' _exptl_absorpt_correction_T_min 0.430 _exptl_absorpt_correction_T_max 0.793 _exptl_special_details ; ? ; _diffrn_ambient_temperature 93(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a # SMART 1000 parameters _diffrn_radiation_source 'sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART 1000 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number 1476 _diffrn_standards_interval_count ? _diffrn_standards_interval_time variable _diffrn_standards_decay_% none _diffrn_reflns_number 18485 _diffrn_reflns_av_R_equivalents 0.0508 _diffrn_reflns_av_sigmaI/netI 0.0607 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_theta_min 1.68 _diffrn_reflns_theta_max 28.51 _diffrn_measured_fraction_theta_max 0.918 _diffrn_reflns_theta_full 28.51 _diffrn_measured_fraction_theta_full 0.918 _reflns_number_total 6212 _reflns_number_gt 5322 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.631 (Bruker, 2001b)' _computing_cell_refinement 'Bruker SMART v5.631 (Bruker, 2001b)' _computing_data_reduction ; Bruker SAINT v6.45 (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001a) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_molecular_graphics 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _computing_publication_material 'Bruker SHELXTL v6.14 (Bruker, 2000a)' _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^)+(0.0793P)^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 mixed _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 0.090(8) _refine_ls_number_reflns 6212 _refine_ls_number_parameters 331 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0508 _refine_ls_R_factor_gt 0.0394 _refine_ls_wR_factor_ref 0.1159 _refine_ls_wR_factor_gt 0.1069 _refine_ls_goodness_of_fit_ref 0.939 _refine_ls_restrained_S_all 0.939 _refine_ls_shift/su_max 0.122 _refine_ls_shift/su_mean 0.024 _refine_diff_density_max 0.551 _refine_diff_density_min -0.348 _refine_diff_density_rms 0.074 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 1.0294(4) -0.0268(2) 0.09278(13) 0.0234(7) Uani 1 1 d . . . H1A H 1.1267 0.0011 0.1142 0.028 Uiso 1 1 calc R . . N2 N 1.1027(4) -0.10131(19) 0.05393(11) 0.0207(5) Uani 1 1 d . . . H2 H 1.170(6) -0.065(3) 0.0291(16) 0.031 Uiso 1 1 d . . . C2 C 1.2220(4) -0.1705(2) 0.08144(14) 0.0244(7) Uani 1 1 d . . . H2A H 1.2895 -0.2056 0.0545 0.037 Uiso 1 1 calc R . . H2B H 1.1538 -0.2161 0.1027 0.037 Uiso 1 1 calc R . . H2C H 1.3008 -0.1351 0.1051 0.037 Uiso 1 1 calc R . . C3 C 0.9614(4) -0.1505(2) 0.02275(12) 0.0200(6) Uani 1 1 d . . . H3A H 0.8870 -0.1875 0.0477 0.024 Uiso 1 1 calc R . . H3B H 1.0135 -0.1961 -0.0032 0.024 Uiso 1 1 calc R . . C4 C 0.8509(4) -0.0769(2) -0.00758(13) 0.0204(6) Uani 1 1 d . . . H4A H 0.7460 -0.1098 -0.0212 0.024 Uiso 1 1 calc R . . H4B H 0.9174 -0.0542 -0.0391 0.024 Uiso 1 1 calc R . . C4A C 0.7920(4) 0.0136(2) 0.02615(13) 0.0190(6) Uani 1 1 d . . . C4B C 0.7796(4) 0.0975(2) -0.01335(13) 0.0206(6) Uani 1 1 d . . . C5 C 0.6505(4) 0.1279(2) -0.04847(13) 0.0211(6) Uani 1 1 d . . . H5A H 0.5379 0.1004 -0.0480 0.025 Uiso 1 1 calc R . . C6 C 0.6955(5) 0.2020(2) -0.08486(13) 0.0217(6) Uani 1 1 d . . . N6 N 0.5598(4) 0.24046(19) -0.12056(12) 0.0242(6) Uani 1 1 d . . . O6A O 0.4061(3) 0.21624(17) -0.11149(11) 0.0313(6) Uani 1 1 d . . . O6B O 0.6013(4) 0.29632(19) -0.15725(11) 0.0382(7) Uani 1 1 d . . . C7 C 0.8614(5) 0.2421(2) -0.08840(14) 0.0259(7) Uani 1 1 d . . . H7A H 0.8860 0.2900 -0.1145 0.031 Uiso 1 1 calc R . . C8 C 0.9919(5) 0.2106(2) -0.05284(15) 0.0271(7) Uani 1 1 d . . . H8A H 1.1059 0.2362 -0.0542 0.032 Uiso 1 1 calc R . . C9 C 0.9463(4) 0.1405(2) -0.01572(14) 0.0232(7) Uani 1 1 d . . . O9 O 1.0578(3) 0.10446(16) 0.02338(10) 0.0270(5) Uani 1 1 d . . . C9A C 0.9432(5) 0.0530(2) 0.06083(14) 0.0241(7) Uani 1 1 d . . . H9AA H 0.8946 0.1007 0.0868 0.029 Uiso 1 1 calc R . . C10 C 0.6427(4) -0.0070(2) 0.06558(14) 0.0241(7) Uani 1 1 d . . . H10A H 0.5423 -0.0332 0.0457 0.029 Uiso 1 1 calc R . . H10B H 0.6060 0.0536 0.0830 0.029 Uiso 1 1 calc R . . C11 C 0.7014(5) -0.0805(2) 0.10943(14) 0.0267(7) Uani 1 1 d . . . H11A H 0.6186 -0.0773 0.1397 0.032 Uiso 1 1 calc R . . H11B H 0.6941 -0.1459 0.0940 0.032 Uiso 1 1 calc R . . C12 C 0.8883(5) -0.0653(3) 0.13201(14) 0.0295(8) Uani 1 1 d . . . H12A H 0.8805 -0.0201 0.1626 0.035 Uiso 1 1 calc R . . H12B H 0.9291 -0.1276 0.1465 0.035 Uiso 1 1 calc R . . C1' C 0.3035(5) -0.0230(2) 0.26940(13) 0.0235(6) Uani 1 1 d . . . C1A' C 0.1605(5) -0.0943(3) 0.25566(14) 0.0314(8) Uani 1 1 d . . . H1AA H 0.2001 -0.1371 0.2269 0.047 Uiso 1 1 calc R . . H1AB H 0.0573 -0.0593 0.2437 0.047 Uiso 1 1 calc R . . H1AC H 0.1319 -0.1324 0.2876 0.047 Uiso 1 1 calc R . . C2' C 0.3680(4) 0.0377(2) 0.22191(13) 0.0220(7) Uani 1 1 d . . . O2' O 0.3582(3) 0.01878(19) 0.17391(10) 0.0300(6) Uani 1 1 d . . . C3' C 0.4539(4) 0.1279(2) 0.24628(13) 0.0241(7) Uani 1 1 d . . . H3'A H 0.3764 0.1842 0.2396 0.029 Uiso 1 1 calc R . . C4' C 0.4527(4) 0.1057(2) 0.30760(13) 0.0191(6) Uani 1 1 d . . . H4'A H 0.4722 0.1626 0.3313 0.023 Uiso 1 1 calc R . . C5' C 0.5748(5) 0.0196(3) 0.31826(14) 0.0287(7) Uani 1 1 d . . . H5'A H 0.5907 0.0091 0.3573 0.034 Uiso 1 1 calc R . . H5'B H 0.6894 0.0300 0.3014 0.034 Uiso 1 1 calc R . . C6' C 0.4781(4) -0.0674(2) 0.29166(15) 0.0268(7) Uani 1 1 d . . . H6'A H 0.4541 -0.1182 0.3185 0.032 Uiso 1 1 calc R . . H6'B H 0.5479 -0.0951 0.2621 0.032 Uiso 1 1 calc R . . C7' C 0.2656(4) 0.0588(2) 0.31212(12) 0.0179(6) Uani 1 1 d . . . C7A' C 0.1152(4) 0.1253(3) 0.29399(15) 0.0261(7) Uani 1 1 d . . . H7AA H 0.0041 0.0940 0.3015 0.039 Uiso 1 1 calc R . . H7AB H 0.1250 0.1378 0.2554 0.039 Uiso 1 1 calc R . . H7AC H 0.1216 0.1862 0.3137 0.039 Uiso 1 1 calc R . . C8' C 0.2263(4) 0.0150(2) 0.36854(13) 0.0216(6) Uani 1 1 d . . . H8'A H 0.3295 -0.0216 0.3803 0.026 Uiso 1 1 calc R . . H8'B H 0.1301 -0.0315 0.3646 0.026 Uiso 1 1 calc R . . S8' S 0.16943(11) 0.09884(5) 0.42118(3) 0.02122(16) Uani 1 1 d . . . O8A' O 0.1828(4) 0.04063(16) 0.47112(9) 0.0280(5) Uani 1 1 d . . . O8B' O 0.2990(3) 0.17679(15) 0.41943(9) 0.0258(5) Uani 1 1 d . . . O8C' O -0.0080(3) 0.13159(19) 0.41137(11) 0.0313(6) Uani 1 1 d . . . Br3' Br 0.68005(5) 0.15403(3) 0.212686(14) 0.03096(11) 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 C1 0.0247(16) 0.0200(15) 0.0254(17) -0.0075(13) -0.0093(14) 0.0031(12) N2 0.0223(13) 0.0185(12) 0.0214(14) -0.0023(11) -0.0029(11) 0.0018(11) C2 0.0232(16) 0.0229(15) 0.0271(17) 0.0020(13) -0.0044(13) 0.0037(12) C3 0.0210(14) 0.0174(13) 0.0217(15) -0.0024(13) -0.0039(12) 0.0000(12) C4 0.0216(16) 0.0197(14) 0.0198(15) -0.0032(12) -0.0029(12) -0.0007(11) C4A 0.0169(15) 0.0181(13) 0.0219(15) 0.0007(12) -0.0037(12) 0.0012(11) C4B 0.0230(16) 0.0172(13) 0.0217(15) -0.0024(12) 0.0034(12) -0.0027(11) C5 0.0250(16) 0.0183(13) 0.0200(15) -0.0034(12) 0.0013(13) 0.0009(11) C6 0.0269(16) 0.0173(13) 0.0210(15) -0.0005(12) 0.0004(14) 0.0025(13) N6 0.0293(15) 0.0190(12) 0.0244(15) 0.0004(11) -0.0027(12) 0.0020(11) O6A 0.0308(13) 0.0258(12) 0.0373(14) 0.0066(11) -0.0082(11) -0.0001(10) O6B 0.0485(16) 0.0367(14) 0.0293(14) 0.0159(12) 0.0014(13) -0.0044(13) C7 0.0306(18) 0.0213(15) 0.0259(17) 0.0021(13) 0.0062(14) -0.0036(13) C8 0.0265(17) 0.0213(16) 0.0334(19) -0.0006(14) 0.0040(15) -0.0062(13) C9 0.0188(14) 0.0192(15) 0.0317(18) -0.0046(13) -0.0023(13) -0.0010(12) O9 0.0233(11) 0.0221(11) 0.0357(14) -0.0028(10) -0.0080(10) -0.0025(10) C9A 0.0248(16) 0.0175(14) 0.0302(18) -0.0038(13) -0.0058(14) 0.0010(13) C10 0.0259(18) 0.0237(15) 0.0228(16) 0.0028(13) -0.0021(13) 0.0031(12) C11 0.0297(18) 0.0311(16) 0.0193(15) 0.0019(13) 0.0053(14) 0.0096(14) C12 0.0376(19) 0.0334(18) 0.0175(16) -0.0020(14) -0.0077(15) 0.0096(15) C1' 0.0256(16) 0.0278(15) 0.0170(14) -0.0044(12) -0.0035(13) 0.0013(14) C1A' 0.039(2) 0.0312(17) 0.0244(17) -0.0049(14) -0.0052(16) -0.0073(16) C2' 0.0191(14) 0.0284(15) 0.0186(16) -0.0015(12) 0.0003(12) 0.0055(12) O2' 0.0254(13) 0.0465(14) 0.0182(11) -0.0054(11) -0.0028(10) 0.0024(11) C3' 0.0218(15) 0.0281(16) 0.0224(17) 0.0012(13) 0.0070(13) 0.0007(12) C4' 0.0186(14) 0.0217(14) 0.0170(14) -0.0021(12) 0.0024(12) -0.0013(12) C5' 0.0215(17) 0.045(2) 0.0201(17) 0.0007(15) -0.0045(14) 0.0033(15) C6' 0.0283(16) 0.0261(15) 0.0261(17) -0.0047(14) 0.0000(15) 0.0103(13) C7' 0.0161(14) 0.0226(14) 0.0150(15) -0.0006(12) 0.0015(11) 0.0008(11) C7A' 0.0194(14) 0.0335(17) 0.0252(17) 0.0025(14) 0.0015(14) 0.0055(12) C8' 0.0292(17) 0.0174(13) 0.0182(15) -0.0004(12) 0.0011(13) 0.0009(12) S8' 0.0235(4) 0.0213(3) 0.0188(4) -0.0016(3) 0.0033(3) 0.0005(3) O8A' 0.0366(13) 0.0301(11) 0.0174(11) 0.0000(9) 0.0026(11) -0.0061(11) O8B' 0.0323(13) 0.0214(11) 0.0236(11) -0.0018(9) 0.0028(10) -0.0036(9) O8C' 0.0206(11) 0.0408(14) 0.0324(14) -0.0026(11) 0.0028(10) 0.0069(10) Br3' 0.02809(17) 0.03677(18) 0.02803(18) -0.00170(14) 0.00858(15) -0.00543(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 C1 C9A 1.520(5) . ? C1 N2 1.527(4) . ? C1 C12 1.558(5) . ? C1 H1A 1.0000 . ? N2 C2 1.498(4) . ? N2 C3 1.504(4) . ? N2 H2 0.95(4) . ? C2 H2A 0.9800 . ? C2 H2B 0.9800 . ? C2 H2C 0.9800 . ? C3 C4 1.532(4) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C4 C4A 1.581(4) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C4A C4B 1.529(4) . ? C4A C10 1.541(5) . ? C4A C9A 1.552(4) . ? C4B C5 1.392(5) . ? C4B C9 1.420(4) . ? C5 C6 1.416(4) . ? C5 H5A 0.9500 . ? C6 C7 1.400(5) . ? C6 N6 1.475(4) . ? N6 O6B 1.242(4) . ? N6 O6A 1.253(4) . ? C7 C8 1.411(5) . ? C7 H7A 0.9500 . ? C8 C9 1.390(5) . ? C8 H8A 0.9500 . ? C9 O9 1.393(4) . ? O9 C9A 1.471(4) . ? C9A H9AA 1.0000 . ? C10 C11 1.564(4) . ? C10 H10A 0.9900 . ? C10 H10B 0.9900 . ? C11 C12 1.563(5) . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C1' C1A' 1.523(5) . ? C1' C2' 1.536(5) . ? C1' C7' 1.586(4) . ? C1' C6' 1.583(5) . ? C1A' H1AA 0.9800 . ? C1A' H1AB 0.9800 . ? C1A' H1AC 0.9800 . ? C2' O2' 1.226(4) . ? C2' C3' 1.545(5) . ? C3' C4' 1.558(5) . ? C3' Br3' 1.970(3) . ? C3' H3'A 1.0000 . ? C4' C5' 1.547(5) . ? C4' C7' 1.589(4) . ? C4' H4'A 1.0000 . ? C5' C6' 1.569(5) . ? C5' H5'A 0.9900 . ? C5' H5'B 0.9900 . ? C6' H6'A 0.9900 . ? C6' H6'B 0.9900 . ? C7' C8' 1.561(4) . ? C7' C7A' 1.552(4) . ? C7A' H7AA 0.9800 . ? C7A' H7AB 0.9800 . ? C7A' H7AC 0.9800 . ? C8' S8' 1.809(3) . ? C8' H8'A 0.9900 . ? C8' H8'B 0.9900 . ? S8' O8C' 1.464(3) . ? S8' O8B' 1.476(2) . ? S8' O8A' 1.488(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9A C1 N2 109.1(3) . . ? C9A C1 C12 105.9(3) . . ? N2 C1 C12 115.0(3) . . ? C9A C1 H1A 108.9 . . ? N2 C1 H1A 108.9 . . ? C12 C1 H1A 108.9 . . ? C2 N2 C3 112.9(2) . . ? C2 N2 C1 112.0(3) . . ? C3 N2 C1 111.6(2) . . ? C2 N2 H2 108(3) . . ? C3 N2 H2 107(2) . . ? C1 N2 H2 105(2) . . ? N2 C2 H2A 109.5 . . ? N2 C2 H2B 109.5 . . ? H2A C2 H2B 109.5 . . ? N2 C2 H2C 109.5 . . ? H2A C2 H2C 109.5 . . ? H2B C2 H2C 109.5 . . ? N2 C3 C4 110.7(2) . . ? N2 C3 H3A 109.5 . . ? C4 C3 H3A 109.5 . . ? N2 C3 H3B 109.5 . . ? C4 C3 H3B 109.5 . . ? H3A C3 H3B 108.1 . . ? C3 C4 C4A 115.5(3) . . ? C3 C4 H4A 108.4 . . ? C4A C4 H4A 108.4 . . ? C3 C4 H4B 108.4 . . ? C4A C4 H4B 108.4 . . ? H4A C4 H4B 107.5 . . ? C4B C4A C10 120.3(3) . . ? C4B C4A C9A 97.8(2) . . ? C10 C4A C9A 105.9(3) . . ? C4B C4A C4 106.5(2) . . ? C10 C4A C4 113.9(2) . . ? C9A C4A C4 111.2(2) . . ? C5 C4B C9 119.6(3) . . ? C5 C4B C4A 132.9(3) . . ? C9 C4B C4A 106.9(3) . . ? C4B C5 C6 116.6(3) . . ? C4B C5 H5A 121.7 . . ? C6 C5 H5A 121.7 . . ? C7 C6 C5 123.7(3) . . ? C7 C6 N6 117.9(3) . . ? C5 C6 N6 118.4(3) . . ? O6B N6 O6A 123.0(3) . . ? O6B N6 C6 119.2(3) . . ? O6A N6 C6 117.8(3) . . ? C6 C7 C8 119.3(3) . . ? C6 C7 H7A 120.3 . . ? C8 C7 H7A 120.3 . . ? C9 C8 C7 117.1(3) . . ? C9 C8 H8A 121.5 . . ? C7 C8 H8A 121.5 . . ? C8 C9 O9 124.1(3) . . ? C8 C9 C4B 123.6(3) . . ? O9 C9 C4B 112.3(3) . . ? C9 O9 C9A 104.3(2) . . ? O9 C9A C1 115.1(3) . . ? O9 C9A C4A 105.7(3) . . ? C1 C9A C4A 111.2(3) . . ? O9 C9A H9AA 108.2 . . ? C1 C9A H9AA 108.2 . . ? C4A C9A H9AA 108.2 . . ? C4A C10 C11 110.5(3) . . ? C4A C10 H10A 109.6 . . ? C11 C10 H10A 109.6 . . ? C4A C10 H10B 109.6 . . ? C11 C10 H10B 109.6 . . ? H10A C10 H10B 108.1 . . ? C12 C11 C10 115.5(3) . . ? C12 C11 H11A 108.4 . . ? C10 C11 H11A 108.4 . . ? C12 C11 H11B 108.4 . . ? C10 C11 H11B 108.4 . . ? H11A C11 H11B 107.5 . . ? C1 C12 C11 117.8(3) . . ? C1 C12 H12A 107.9 . . ? C11 C12 H12A 107.9 . . ? C1 C12 H12B 107.8 . . ? C11 C12 H12B 107.9 . . ? H12A C12 H12B 107.2 . . ? C1A' C1' C2' 114.8(3) . . ? C1A' C1' C7' 119.0(3) . . ? C2' C1' C7' 100.4(2) . . ? C1A' C1' C6' 116.2(3) . . ? C2' C1' C6' 102.0(3) . . ? C7' C1' C6' 101.7(2) . . ? C1' C1A' H1AA 109.5 . . ? C1' C1A' H1AB 109.5 . . ? H1AA C1A' H1AB 109.5 . . ? C1' C1A' H1AC 109.5 . . ? H1AA C1A' H1AC 109.5 . . ? H1AB C1A' H1AC 109.5 . . ? O2' C2' C1' 127.8(3) . . ? O2' C2' C3' 125.7(3) . . ? C1' C2' C3' 106.5(3) . . ? C4' C3' C2' 102.8(3) . . ? C4' C3' Br3' 117.3(2) . . ? C2' C3' Br3' 111.4(2) . . ? C4' C3' H3'A 108.4 . . ? C2' C3' H3'A 108.4 . . ? Br3' C3' H3'A 108.4 . . ? C3' C4' C5' 108.5(3) . . ? C3' C4' C7' 99.0(2) . . ? C5' C4' C7' 102.9(2) . . ? C3' C4' H4'A 114.9 . . ? C5' C4' H4'A 114.9 . . ? C7' C4' H4'A 114.9 . . ? C4' C5' C6' 103.6(3) . . ? C4' C5' H5'A 111.0 . . ? C6' C5' H5'A 111.0 . . ? C4' C5' H5'B 111.0 . . ? C6' C5' H5'B 111.0 . . ? H5'A C5' H5'B 109.0 . . ? C5' C6' C1' 104.6(2) . . ? C5' C6' H6'A 110.8 . . ? C1' C6' H6'A 110.8 . . ? C5' C6' H6'B 110.8 . . ? C1' C6' H6'B 110.8 . . ? H6'A C6' H6'B 108.9 . . ? C8' C7' C7A' 110.5(3) . . ? C8' C7' C1' 111.0(2) . . ? C7A' C7' C1' 111.8(3) . . ? C8' C7' C4' 113.6(3) . . ? C7A' C7' C4' 114.5(3) . . ? C1' C7' C4' 94.6(2) . . ? C7' C7A' H7AA 109.5 . . ? C7' C7A' H7AB 109.5 . . ? H7AA C7A' H7AB 109.5 . . ? C7' C7A' H7AC 109.5 . . ? H7AA C7A' H7AC 109.5 . . ? H7AB C7A' H7AC 109.5 . . ? C7' C8' S8' 116.5(2) . . ? C7' C8' H8'A 108.2 . . ? S8' C8' H8'A 108.1 . . ? C7' C8' H8'B 108.2 . . ? S8' C8' H8'B 108.2 . . ? H8'A C8' H8'B 107.3 . . ? O8C' S8' O8B' 113.58(15) . . ? O8C' S8' O8A' 111.95(16) . . ? O8B' S8' O8A' 112.20(14) . . ? O8C' S8' C8' 107.89(16) . . ? O8B' S8' C8' 106.77(14) . . ? O8A' S8' C8' 103.72(14) . . ? 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 C9A C1 N2 C2 167.6(3) . . . . ? C12 C1 N2 C2 -73.6(3) . . . . ? C9A C1 N2 C3 -64.7(3) . . . . ? C12 C1 N2 C3 54.0(4) . . . . ? C2 N2 C3 C4 -176.2(3) . . . . ? C1 N2 C3 C4 56.6(3) . . . . ? N2 C3 C4 C4A -46.4(4) . . . . ? C3 C4 C4A C4B 148.7(3) . . . . ? C3 C4 C4A C10 -76.2(3) . . . . ? C3 C4 C4A C9A 43.3(4) . . . . ? C10 C4A C4B C5 -48.0(5) . . . . ? C9A C4A C4B C5 -161.6(3) . . . . ? C4 C4A C4B C5 83.5(4) . . . . ? C10 C4A C4B C9 140.3(3) . . . . ? C9A C4A C4B C9 26.7(3) . . . . ? C4 C4A C4B C9 -88.2(3) . . . . ? C9 C4B C5 C6 -0.4(4) . . . . ? C4A C4B C5 C6 -171.2(3) . . . . ? C4B C5 C6 C7 2.6(5) . . . . ? C4B C5 C6 N6 -176.4(3) . . . . ? C7 C6 N6 O6B 10.1(4) . . . . ? C5 C6 N6 O6B -170.8(3) . . . . ? C7 C6 N6 O6A -168.5(3) . . . . ? C5 C6 N6 O6A 10.6(4) . . . . ? C5 C6 C7 C8 -2.4(5) . . . . ? N6 C6 C7 C8 176.6(3) . . . . ? C6 C7 C8 C9 -0.1(5) . . . . ? C7 C8 C9 O9 -177.5(3) . . . . ? C7 C8 C9 C4B 2.4(5) . . . . ? C5 C4B C9 C8 -2.2(5) . . . . ? C4A C4B C9 C8 170.8(3) . . . . ? C5 C4B C9 O9 177.7(3) . . . . ? C4A C4B C9 O9 -9.3(4) . . . . ? C8 C9 O9 C9A 165.7(3) . . . . ? C4B C9 O9 C9A -14.1(3) . . . . ? C9 O9 C9A C1 154.9(3) . . . . ? C9 O9 C9A C4A 31.7(3) . . . . ? N2 C1 C9A O9 -59.6(3) . . . . ? C12 C1 C9A O9 176.1(3) . . . . ? N2 C1 C9A C4A 60.6(4) . . . . ? C12 C1 C9A C4A -63.7(3) . . . . ? C4B C4A C9A O9 -35.3(3) . . . . ? C10 C4A C9A O9 -160.0(2) . . . . ? C4 C4A C9A O9 75.9(3) . . . . ? C4B C4A C9A C1 -160.9(3) . . . . ? C10 C4A C9A C1 74.4(3) . . . . ? C4 C4A C9A C1 -49.8(4) . . . . ? C4B C4A C10 C11 -167.7(3) . . . . ? C9A C4A C10 C11 -58.5(3) . . . . ? C4 C4A C10 C11 64.0(3) . . . . ? C4A C10 C11 C12 41.1(4) . . . . ? C9A C1 C12 C11 43.1(4) . . . . ? N2 C1 C12 C11 -77.4(4) . . . . ? C10 C11 C12 C1 -34.2(4) . . . . ? C1A' C1' C2' O2' -22.9(5) . . . . ? C7' C1' C2' O2' -151.9(3) . . . . ? C6' C1' C2' O2' 103.7(4) . . . . ? C1A' C1' C2' C3' 158.6(3) . . . . ? C7' C1' C2' C3' 29.6(3) . . . . ? C6' C1' C2' C3' -74.8(3) . . . . ? O2' C2' C3' C4' -171.6(3) . . . . ? C1' C2' C3' C4' 6.9(3) . . . . ? O2' C2' C3' Br3' -45.3(4) . . . . ? C1' C2' C3' Br3' 133.3(2) . . . . ? C2' C3' C4' C5' 66.4(3) . . . . ? Br3' C3' C4' C5' -56.1(3) . . . . ? C2' C3' C4' C7' -40.6(3) . . . . ? Br3' C3' C4' C7' -163.1(2) . . . . ? C3' C4' C5' C6' -68.9(3) . . . . ? C7' C4' C5' C6' 35.4(3) . . . . ? C4' C5' C6' C1' -1.8(3) . . . . ? C1A' C1' C6' C5' -163.2(3) . . . . ? C2' C1' C6' C5' 71.1(3) . . . . ? C7' C1' C6' C5' -32.3(3) . . . . ? C1A' C1' C7' C8' 63.3(4) . . . . ? C2' C1' C7' C8' -170.5(3) . . . . ? C6' C1' C7' C8' -65.8(3) . . . . ? C1A' C1' C7' C7A' -60.6(4) . . . . ? C2' C1' C7' C7A' 65.6(3) . . . . ? C6' C1' C7' C7A' 170.3(3) . . . . ? C1A' C1' C7' C4' -179.2(3) . . . . ? C2' C1' C7' C4' -53.0(3) . . . . ? C6' C1' C7' C4' 51.7(3) . . . . ? C3' C4' C7' C8' 172.9(3) . . . . ? C5' C4' C7' C8' 61.3(3) . . . . ? C3' C4' C7' C7A' -58.9(3) . . . . ? C5' C4' C7' C7A' -170.5(3) . . . . ? C3' C4' C7' C1' 57.5(3) . . . . ? C5' C4' C7' C1' -54.0(3) . . . . ? C7A' C7' C8' S8' -52.3(3) . . . . ? C1' C7' C8' S8' -177.0(2) . . . . ? C4' C7' C8' S8' 77.9(3) . . . . ? C7' C8' S8' O8C' 74.5(3) . . . . ? C7' C8' S8' O8B' -47.9(3) . . . . ? C7' C8' S8' O8A' -166.6(2) . . . . ? data_knih40 _database_code_depnum_ccdc_archive 'CCDC 656372' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C22 H26 N O2, Br' _chemical_formula_sum 'C22 H26 Br N O2' _chemical_formula_weight 416.35 _chemical_absolute_configuration ad 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 'P 21 21 21' 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 7.5366(2) _cell_length_b 11.9922(4) _cell_length_c 21.9804(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1986.60(13) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 8107 _cell_measurement_theta_min 2.51 _cell_measurement_theta_max 26.06 _exptl_crystal_description prisim _exptl_crystal_colour colorless _exptl_crystal_size_min 0.30 _exptl_crystal_size_mid 0.54 _exptl_crystal_size_max 0.84 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 864 _exptl_absorpt_coefficient_mu 2.085 ########################################################## # # # NOTE on absorbtion correction with SADABS: # # # # (Semi)empirical correction methods for absorption correction are more of # # a problem in that they often specify only a relative correction range # # [ Tmin(emp) & Tmax(emp)]. # # # # Acta Cryst. procedures call in such cases for the multiplication of both # # empirical values with Tmax(expected). # # # # THIS RECOMMENDATION IS CURRENTLY UNDER REVIEW! (George # # and Ton are agruing this point!) # ########################################################## _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS v2.10 (Bruker, 2000c)' _exptl_absorpt_correction_T_min 0.348 _exptl_absorpt_correction_T_max 0.535 _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) # SMART APEX II parameters _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 II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 22724 _diffrn_reflns_av_R_equivalents 0.0247 _diffrn_reflns_av_sigmaI/netI 0.0436 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.85 _diffrn_reflns_theta_max 30.32 _diffrn_measured_fraction_theta_max 0.973 _diffrn_reflns_theta_full 30.32 _diffrn_measured_fraction_theta_full 0.973 _reflns_number_total 5648 _reflns_number_gt 4773 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker SMART v5.631 (Bruker, 2001)' _computing_cell_refinement 'Bruker SMART v5.631 (Bruker, 2001)' _computing_data_reduction ; Bruker SAINT v6.45A (Bruker, 2002), Bruker XPREP v6.14 (Bruker, 2001) ; _computing_structure_solution 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_structure_refinement 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_molecular_graphics 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _computing_publication_material 'Bruker SHELXTL v6.14 (Bruker, 2000b)' _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^)+(0.0333P)^2^+0.2137P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.019(7) _refine_ls_number_reflns 5648 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0436 _refine_ls_R_factor_gt 0.0329 _refine_ls_wR_factor_ref 0.0787 _refine_ls_wR_factor_gt 0.0750 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_diff_density_max 0.833 _refine_diff_density_min -0.327 _refine_diff_density_rms 0.049 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 0.51862(3) 0.76573(2) 0.079652(9) 0.04777(8) Uani 1 1 d . . . C1 C 0.9174(3) 0.85021(15) 0.17427(8) 0.0313(4) Uani 1 1 d . . . H1A H 0.8529 0.7904 0.1951 0.038 Uiso 1 1 calc R . . N2 N 0.9325(2) 0.82020(13) 0.10690(7) 0.0313(4) Uani 1 1 d . . . H2 H 0.823(4) 0.808(2) 0.0989(10) 0.041 Uiso 1 1 d . . . C3 C 0.9997(4) 0.91161(15) 0.06560(8) 0.0421(5) Uani 1 1 d . . . H3A H 0.9775 0.8902 0.0237 0.051 Uiso 1 1 calc R . . H3B H 1.1271 0.9182 0.0708 0.051 Uiso 1 1 calc R . . C4 C 0.9145(4) 1.02613(16) 0.07714(10) 0.0431(5) Uani 1 1 d . . . H4A H 0.9861 1.0834 0.0579 0.052 Uiso 1 1 calc R . . H4B H 0.7977 1.0279 0.0586 0.052 Uiso 1 1 calc R . . C4A C 0.8974(3) 1.05183(15) 0.14524(9) 0.0312(4) Uani 1 1 d . . . C4B C 0.7667(3) 1.14082(16) 0.16538(9) 0.0343(4) Uani 1 1 d . . . C5 C 0.7305(3) 1.24809(17) 0.14621(10) 0.0459(5) Uani 1 1 d . . . H5A H 0.7858 1.2782 0.1121 0.055 Uiso 1 1 calc R . . C6 C 0.6082(4) 1.3094(2) 0.17979(13) 0.0551(7) Uani 1 1 d . . . H6A H 0.5801 1.3815 0.1675 0.066 Uiso 1 1 calc R . . C7 C 0.5279(3) 1.2662(2) 0.23052(13) 0.0574(6) Uani 1 1 d . . . H7A H 0.4463 1.3096 0.2516 0.069 Uiso 1 1 calc R . . C8 C 0.5649(3) 1.15971(19) 0.25124(12) 0.0481(6) Uani 1 1 d . . . O8 O 0.4883(4) 1.11082(17) 0.30063(10) 0.0783(7) Uani 1 1 d . . . H8 H 0.489(7) 1.146(4) 0.323(2) 0.118 Uiso 1 1 d . . . C9 C 0.6848(3) 1.09846(16) 0.21696(9) 0.0360(4) Uani 1 1 d . . . O9 O 0.7342(2) 0.98965(11) 0.23058(7) 0.0394(3) Uani 1 1 d . . . C9A C 0.8008(3) 0.95218(15) 0.17252(8) 0.0300(4) Uani 1 1 d . . . H9AA H 0.6986 0.9354 0.1465 0.036 Uiso 1 1 calc R . . C10 C 1.0748(3) 1.07328(18) 0.17796(11) 0.0419(5) Uani 1 1 d . . . H10A H 1.0496 1.1039 0.2179 0.050 Uiso 1 1 calc R . . H10B H 1.1399 1.1294 0.1553 0.050 Uiso 1 1 calc R . . C11 C 1.1958(4) 0.9699(2) 0.18597(14) 0.0563(7) Uani 1 1 d . . . H11A H 1.2539 0.9534 0.1476 0.068 Uiso 1 1 calc R . . H11B H 1.2870 0.9864 0.2158 0.068 Uiso 1 1 calc R . . C12 C 1.0904(4) 0.8685(2) 0.20663(12) 0.0503(6) Uani 1 1 d . . . H12A H 1.1636 0.8027 0.2011 0.060 Uiso 1 1 calc R . . H12B H 1.0666 0.8758 0.2498 0.060 Uiso 1 1 calc R . . C13 C 1.0326(3) 0.71423(15) 0.09374(10) 0.0392(5) Uani 1 1 d . . . H13A H 1.1558 0.7247 0.1052 0.047 Uiso 1 1 calc R . . H13B H 1.0292 0.7004 0.0503 0.047 Uiso 1 1 calc R . . C14 C 0.9612(4) 0.61238(17) 0.12653(10) 0.0462(5) Uani 1 1 d . . . H14A H 1.0101 0.6088 0.1673 0.055 Uiso 1 1 calc R . . H14B H 0.8330 0.6172 0.1298 0.055 Uiso 1 1 calc R . . C15 C 1.0123(3) 0.50879(15) 0.09127(9) 0.0382(4) Uani 1 1 d . . . C16 C 0.9246(4) 0.4831(2) 0.03773(12) 0.0548(6) Uani 1 1 d . . . H16A H 0.8320 0.5281 0.0243 0.066 Uiso 1 1 calc R . . C17 C 0.9746(5) 0.3907(2) 0.00411(12) 0.0666(8) Uani 1 1 d . . . H17A H 0.9157 0.3743 -0.0320 0.080 Uiso 1 1 calc R . . C18 C 1.1084(5) 0.3239(2) 0.02327(13) 0.0625(8) Uani 1 1 d . . . H18A H 1.1401 0.2616 0.0006 0.075 Uiso 1 1 calc R . . C19 C 1.1969(4) 0.34807(19) 0.07593(13) 0.0592(7) Uani 1 1 d . . . H19A H 1.2890 0.3022 0.0889 0.071 Uiso 1 1 calc R . . C20 C 1.1497(4) 0.4409(2) 0.11005(11) 0.0491(6) Uani 1 1 d . . . H20A H 1.2108 0.4574 0.1457 0.059 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 0.03735(11) 0.06548(14) 0.04048(10) -0.00292(9) -0.00319(9) -0.00916(10) C1 0.0375(11) 0.0271(9) 0.0294(8) -0.0019(7) 0.0028(8) 0.0007(8) N2 0.0316(9) 0.0286(8) 0.0338(8) -0.0050(6) 0.0033(7) 0.0013(6) C3 0.0573(14) 0.0336(9) 0.0356(9) -0.0014(7) 0.0160(10) -0.0006(10) C4 0.0649(15) 0.0315(9) 0.0329(10) 0.0031(8) 0.0079(11) 0.0052(9) C4A 0.0353(11) 0.0266(9) 0.0319(9) -0.0008(7) 0.0048(8) 0.0028(8) C4B 0.0351(11) 0.0293(9) 0.0386(10) -0.0082(8) -0.0034(8) 0.0029(8) C5 0.0586(14) 0.0340(11) 0.0450(11) -0.0036(9) -0.0109(9) 0.0065(10) C6 0.0590(17) 0.0346(11) 0.0718(16) -0.0142(11) -0.0235(14) 0.0137(11) C7 0.0329(11) 0.0502(12) 0.0890(18) -0.0351(13) 0.0007(12) 0.0041(11) C8 0.0355(13) 0.0448(12) 0.0639(14) -0.0252(11) 0.0106(11) -0.0070(9) O8 0.0845(17) 0.0617(11) 0.0888(14) -0.0344(9) 0.0540(14) -0.0228(12) C9 0.0319(11) 0.0322(10) 0.0440(11) -0.0123(8) 0.0037(8) -0.0042(8) O9 0.0496(10) 0.0308(7) 0.0378(7) -0.0059(6) 0.0157(7) -0.0029(6) C9A 0.0318(10) 0.0293(9) 0.0289(9) -0.0036(7) 0.0028(7) -0.0001(8) C10 0.0350(12) 0.0366(11) 0.0542(12) -0.0030(9) 0.0033(10) -0.0062(9) C11 0.0357(13) 0.0521(14) 0.0811(19) -0.0151(13) -0.0173(12) 0.0031(11) C12 0.0542(15) 0.0409(12) 0.0557(13) -0.0037(10) -0.0213(12) 0.0098(10) C13 0.0380(12) 0.0305(9) 0.0490(10) -0.0057(7) 0.0107(8) 0.0051(8) C14 0.0548(15) 0.0344(10) 0.0496(11) -0.0017(8) 0.0128(11) 0.0093(10) C15 0.0442(12) 0.0293(9) 0.0413(10) -0.0003(7) 0.0042(10) 0.0006(9) C16 0.0596(17) 0.0446(13) 0.0602(14) 0.0026(11) -0.0130(12) -0.0016(11) C17 0.092(2) 0.0547(15) 0.0533(13) -0.0108(11) -0.0072(15) -0.0272(17) C18 0.087(2) 0.0375(13) 0.0629(16) -0.0110(11) 0.0223(15) -0.0073(14) C19 0.0640(17) 0.0410(12) 0.0726(17) 0.0011(13) 0.0121(16) 0.0155(11) C20 0.0540(16) 0.0441(13) 0.0491(13) -0.0032(10) -0.0050(11) 0.0078(11) _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 C12 1.501(3) . ? C1 C9A 1.506(3) . ? C1 N2 1.528(2) . ? C1 H1A 0.9800 . ? N2 C13 1.506(3) . ? N2 C3 1.511(3) . ? N2 H2 0.86(3) . ? C3 C4 1.537(3) . ? C3 H3A 0.9700 . ? C3 H3B 0.9700 . ? C4 C4A 1.534(3) . ? C4 H4A 0.9700 . ? C4 H4B 0.9700 . ? C4A C4B 1.518(3) . ? C4A C9A 1.523(3) . ? C4A C10 1.540(3) . ? C4B C5 1.381(3) . ? C4B C9 1.388(3) . ? C5 C6 1.391(4) . ? C5 H5A 0.9300 . ? C6 C7 1.370(4) . ? C6 H6A 0.9300 . ? C7 C8 1.384(4) . ? C7 H7A 0.9300 . ? C8 O8 1.362(3) . ? C8 C9 1.387(3) . ? O8 H8 0.65(4) . ? C9 O9 1.390(3) . ? O9 C9A 1.443(2) . ? C9A H9AA 0.9800 . ? C10 C11 1.549(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 C12 1.522(4) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 H12A 0.9700 . ? C12 H12B 0.9700 . ? C13 C14 1.517(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.514(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C20 1.380(3) . ? C15 C16 1.384(3) . ? C16 C17 1.385(4) . ? C16 H16A 0.9300 . ? C17 C18 1.355(5) . ? C17 H17A 0.9300 . ? C18 C19 1.367(4) . ? C18 H18A 0.9300 . ? C19 C20 1.389(3) . ? C19 H19A 0.9300 . ? C20 H20A 0.9300 . ? 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 C1 C9A 113.61(16) . . ? C12 C1 N2 115.40(18) . . ? C9A C1 N2 102.10(15) . . ? C12 C1 H1A 108.5 . . ? C9A C1 H1A 108.5 . . ? N2 C1 H1A 108.5 . . ? C13 N2 C3 109.19(15) . . ? C13 N2 C1 114.97(15) . . ? C3 N2 C1 115.87(14) . . ? C13 N2 H2 107.3(16) . . ? C3 N2 H2 109.0(16) . . ? C1 N2 H2 99.6(16) . . ? N2 C3 C4 114.15(17) . . ? N2 C3 H3A 108.7 . . ? C4 C3 H3A 108.7 . . ? N2 C3 H3B 108.7 . . ? C4 C3 H3B 108.7 . . ? H3A C3 H3B 107.6 . . ? C4A C4 C3 112.07(16) . . ? C4A C4 H4A 109.2 . . ? C3 C4 H4A 109.2 . . ? C4A C4 H4B 109.2 . . ? C3 C4 H4B 109.2 . . ? H4A C4 H4B 107.9 . . ? C4B C4A C9A 97.27(16) . . ? C4B C4A C4 118.70(17) . . ? C9A C4A C4 105.47(16) . . ? C4B C4A C10 108.05(16) . . ? C9A C4A C10 111.26(17) . . ? C4 C4A C10 114.62(19) . . ? C5 C4B C9 120.2(2) . . ? C5 C4B C4A 134.0(2) . . ? C9 C4B C4A 105.65(17) . . ? C4B C5 C6 117.5(2) . . ? C4B C5 H5A 121.3 . . ? C6 C5 H5A 121.3 . . ? C7 C6 C5 121.6(2) . . ? C7 C6 H6A 119.2 . . ? C5 C6 H6A 119.2 . . ? C6 C7 C8 121.9(2) . . ? C6 C7 H7A 119.1 . . ? C8 C7 H7A 119.1 . . ? O8 C8 C7 125.0(2) . . ? O8 C8 C9 118.8(2) . . ? C7 C8 C9 116.2(2) . . ? C8 O8 H8 109(4) . . ? C4B C9 C8 122.7(2) . . ? C4B C9 O9 113.61(17) . . ? C8 C9 O9 123.7(2) . . ? C9 O9 C9A 101.25(14) . . ? O9 C9A C1 115.66(15) . . ? O9 C9A C4A 105.67(14) . . ? C1 C9A C4A 111.59(17) . . ? O9 C9A H9AA 107.9 . . ? C1 C9A H9AA 107.9 . . ? C4A C9A H9AA 107.9 . . ? C4A C10 C11 115.51(18) . . ? C4A C10 H10A 108.4 . . ? C11 C10 H10A 108.4 . . ? C4A C10 H10B 108.4 . . ? C11 C10 H10B 108.4 . . ? H10A C10 H10B 107.5 . . ? C12 C11 C10 111.5(2) . . ? C12 C11 H11A 109.3 . . ? C10 C11 H11A 109.3 . . ? C12 C11 H11B 109.3 . . ? C10 C11 H11B 109.3 . . ? H11A C11 H11B 108.0 . . ? C1 C12 C11 115.36(19) . . ? C1 C12 H12A 108.4 . . ? C11 C12 H12A 108.4 . . ? C1 C12 H12B 108.4 . . ? C11 C12 H12B 108.4 . . ? H12A C12 H12B 107.5 . . ? N2 C13 C14 114.22(17) . . ? N2 C13 H13A 108.7 . . ? C14 C13 H13A 108.7 . . ? N2 C13 H13B 108.7 . . ? C14 C13 H13B 108.7 . . ? H13A C13 H13B 107.6 . . ? C15 C14 C13 109.09(17) . . ? C15 C14 H14A 109.9 . . ? C13 C14 H14A 109.9 . . ? C15 C14 H14B 109.9 . . ? C13 C14 H14B 109.9 . . ? H14A C14 H14B 108.3 . . ? C20 C15 C16 118.8(2) . . ? C20 C15 C14 121.5(2) . . ? C16 C15 C14 119.7(2) . . ? C15 C16 C17 120.1(3) . . ? C15 C16 H16A 119.9 . . ? C17 C16 H16A 119.9 . . ? C18 C17 C16 120.7(3) . . ? C18 C17 H17A 119.7 . . ? C16 C17 H17A 119.7 . . ? C17 C18 C19 120.1(2) . . ? C17 C18 H18A 120.0 . . ? C19 C18 H18A 120.0 . . ? C18 C19 C20 120.1(3) . . ? C18 C19 H19A 119.9 . . ? C20 C19 H19A 119.9 . . ? C15 C20 C19 120.2(2) . . ? C15 C20 H20A 119.9 . . ? C19 C20 H20A 119.9 . . ? 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 C12 C1 N2 C13 60.6(2) . . . . ? C9A C1 N2 C13 -175.68(17) . . . . ? C12 C1 N2 C3 -68.4(2) . . . . ? C9A C1 N2 C3 55.4(2) . . . . ? C13 N2 C3 C4 -176.79(19) . . . . ? C1 N2 C3 C4 -45.1(3) . . . . ? N2 C3 C4 C4A 42.6(3) . . . . ? C3 C4 C4A C4B -160.6(2) . . . . ? C3 C4 C4A C9A -53.1(2) . . . . ? C3 C4 C4A C10 69.7(2) . . . . ? C9A C4A C4B C5 -159.5(2) . . . . ? C4 C4A C4B C5 -47.4(3) . . . . ? C10 C4A C4B C5 85.3(3) . . . . ? C9A C4A C4B C9 26.3(2) . . . . ? C4 C4A C4B C9 138.42(19) . . . . ? C10 C4A C4B C9 -88.9(2) . . . . ? C9 C4B C5 C6 -1.1(3) . . . . ? C4A C4B C5 C6 -174.6(2) . . . . ? C4B C5 C6 C7 0.9(4) . . . . ? C5 C6 C7 C8 0.4(4) . . . . ? C6 C7 C8 O8 -178.9(3) . . . . ? C6 C7 C8 C9 -1.4(4) . . . . ? C5 C4B C9 C8 0.1(3) . . . . ? C4A C4B C9 C8 175.2(2) . . . . ? C5 C4B C9 O9 179.99(19) . . . . ? C4A C4B C9 O9 -4.9(2) . . . . ? O8 C8 C9 C4B 178.9(2) . . . . ? C7 C8 C9 C4B 1.2(3) . . . . ? O8 C8 C9 O9 -1.1(4) . . . . ? C7 C8 C9 O9 -178.7(2) . . . . ? C4B C9 O9 C9A -20.5(2) . . . . ? C8 C9 O9 C9A 159.4(2) . . . . ? C9 O9 C9A C1 161.77(17) . . . . ? C9 O9 C9A C4A 37.8(2) . . . . ? C12 C1 C9A O9 -66.0(2) . . . . ? N2 C1 C9A O9 169.07(16) . . . . ? C12 C1 C9A C4A 54.8(2) . . . . ? N2 C1 C9A C4A -70.11(19) . . . . ? C4B C4A C9A O9 -39.55(19) . . . . ? C4 C4A C9A O9 -162.07(17) . . . . ? C10 C4A C9A O9 73.1(2) . . . . ? C4B C4A C9A C1 -166.04(15) . . . . ? C4 C4A C9A C1 71.4(2) . . . . ? C10 C4A C9A C1 -53.4(2) . . . . ? C4B C4A C10 C11 155.0(2) . . . . ? C9A C4A C10 C11 49.4(3) . . . . ? C4 C4A C10 C11 -70.1(3) . . . . ? C4A C10 C11 C12 -43.9(3) . . . . ? C9A C1 C12 C11 -50.8(3) . . . . ? N2 C1 C12 C11 66.7(3) . . . . ? C10 C11 C12 C1 43.9(3) . . . . ? C3 N2 C13 C14 -172.48(19) . . . . ? C1 N2 C13 C14 55.3(3) . . . . ? N2 C13 C14 C15 155.47(19) . . . . ? C13 C14 C15 C20 102.9(3) . . . . ? C13 C14 C15 C16 -74.6(3) . . . . ? C20 C15 C16 C17 0.2(4) . . . . ? C14 C15 C16 C17 177.8(2) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C16 C17 C18 C19 -0.7(5) . . . . ? C17 C18 C19 C20 0.2(4) . . . . ? C16 C15 C20 C19 -0.7(4) . . . . ? C14 C15 C20 C19 -178.2(2) . . . . ? C18 C19 C20 C15 0.5(4) . . . . ? 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 N2 H2 Br1 0.86(3) 2.38(3) 3.2424(19) 177(2) . O8 H8 Br1 0.65(4) 2.57(4) 3.2216(18) 174(5) 3_655