data_in472 #?# MeasurementCode _publ_contact_author_name 'Thomas Lindel' _publ_contact_author_address ; Department of Chemistry and Biochemistry Ludwig Maximilian University Butenandtstrasse 5-13 (Haus F) D-81377 Munich Germany ; loop_ _publ_author_name _publ_author_address 'Michael Zoellinger' ; Department of Chemistry and Biochemistry Ludwig Maximilian University Butenandtstrasse 5-13 (Haus F) D-81377 Munich Germany ; 'Thomas Lindel' ; Department of Chemistry and Biochemistry Ludwig Maximilian University Butenandtstrasse 5-13 (Haus F) D-81377 Munich Germany ; 'Peter Mayer' ; Department of Chemistry and Biochemistry Ludwig Maximilian University Butenandtstrasse 5-13 (Haus D) D-81377 Munich Germany ; 'Kurt Polborn' ; Department of Chemistry and Biochemistry Ludwig Maximilian University Butenandtstrasse 5-13 (Haus D) D-81377 Munich Germany ; _publ_contact_author_email 'thomas.lindel@cup.uni-muenchen.de' _publ_contact_author_fax '+49 089-2180-77734' _publ_contact_author_phone ? _publ_requested_journal 'J. Am. Chem. Soc.' _publ_section_title ; Three-component imidazolidinone anellation as key to the total synthesis of phakellin-type pyrrole-imidazole alkaloids ; _publ_section_abstract ? _publ_section_comment ? _audit_update_record 06-Jul-06 _chemical_name_common ? _chemical_compound_source ? _exptl_crystal_description rod #?# e.g.: needle, platelet; pris _exptl_crystal_colour colourless _exptl_crystal_size_max 0.20 #?# in millimeters _exptl_crystal_size_mid 0.06 #?# in millimeters _exptl_crystal_size_min 0.02 #?# in millimeters _exptl_crystal_density_method 'not measured' _exptl_crystal_density_meas ? _exptl_special_details ? _audit_author_name 'Mayer, P.' #?# X-ray operator _audit_creation_date 14-Oct-04 #?# style: 18-Aug-1998 _diffrn_ambient_temperature 200(2) #?# in K _diffrn_source_type 'FR 591 generator' _diffrn_source_power 4.000 #?# in kW _diffrn_source_voltage 50.00 #?# in kV _diffrn_source_current 80.00 #?# in mA _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_radiation_collimation 0.35 _diffrn_measurement_device '95mm CCD camera on \k-goniostat' _diffrn_measurement_device_type 'KappaCCD' _diffrn_measurement_method 'omega-scan' _diffrn_detector_area_resol_mean 9 _diffrn_special_details ? _diffrn_orient_matrix_type 'by Nonius Collect from scalepack cell' _diffrn_orient_matrix_UB_11 -0.0048919 _diffrn_orient_matrix_UB_12 0.0398685 _diffrn_orient_matrix_UB_13 -0.0323194 _diffrn_orient_matrix_UB_21 -0.0465320 _diffrn_orient_matrix_UB_22 -0.0614986 _diffrn_orient_matrix_UB_23 -0.0136347 _diffrn_orient_matrix_UB_31 -0.0685303 _diffrn_orient_matrix_UB_32 0.0389115 _diffrn_orient_matrix_UB_33 0.0115650 loop_ _reflns_scale_group_code _reflns_scale_meas_F 1 1.0 _cell_length_a 12.0512(5) _cell_length_b 12.0512(5) _cell_length_c 27.0746(11) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3932.1(3) _cell_measurement_temperature 200(2) #?# in K _cell_measurement_reflns_used 8922 _cell_measurement_theta_min 3.134 _cell_measurement_theta_max 21.967 _cell_special_details ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 2 -5 17 0.09360 -5 2 -24 0.06845 -19 29 -13 0.03160 7 -23 0 0.02040 1 1 0 0.00832 -1 -1 0 0.01600 _exptl_absorpt_coefficient_mu 4.158 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.7259 _exptl_absorpt_correction_T_max 0.8940 _exptl_absorpt_process_details ; Crystal faces optimized with XShape, rev. 1.02, STOE (Darmstadt, Germany) Absorption correction with XRed, rev 1.09, STOE (Darmstadt, Germany) ; _diffrn_reflns_number 10222 #xl _diffrn_reflns_av_R_equivalents 0.0917 #xl _diffrn_reflns_av_sigmaI/netI 0.0757 #xl _diffrn_reflns_limit_h_min -7 #xl _diffrn_reflns_limit_h_max 12 #xl _diffrn_reflns_limit_k_min -12 #xl _diffrn_reflns_limit_k_max 12 #xl _diffrn_reflns_limit_l_min -27 #xl _diffrn_reflns_limit_l_max 28 #xl _diffrn_reflns_theta_min 3.29 #xl _diffrn_reflns_theta_max 21.96 #xl _diffrn_measured_fraction_theta_max 0.995 #xl _diffrn_reflns_theta_full 21.96 #xl _diffrn_measured_fraction_theta_full 0.995 #xl _symmetry_cell_setting tetragonal _symmetry_space_group_name_H-M 'P 41 21 2' _symmetry_Int_Tables_number 92 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' 'x+1/2, -y+1/2, -z+3/4' '-x+1/2, y+1/2, -z+1/4' '-y, -x, -z+1/2' 'y, x, -z' 'y+1/2, -x+1/2, z+3/4' '-y+1/2, x+1/2, z+1/4' 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' _reflns_number_total 2396 #xl _reflns_number_gt 1941 #xl _reflns_threshold_expression >2sigma(I) #xl _reflns_special_details ? _refine_ls_structure_factor_coef Fsqd #xl _refine_ls_matrix_type full #xl _refine_ls_weighting_scheme calc #xl _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0254P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' #xl _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed #?# mixed --> _refine_special_details _refine_ls_extinction_method none #xl _refine_ls_extinction_coef ? #xl _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' #xl _refine_ls_abs_structure_Flack -0.028(18) #xl _refine_ls_number_reflns 2396 #xl _refine_ls_number_parameters 244 #xl _refine_ls_number_restraints 0 #xl _refine_ls_R_factor_all 0.0589 #xl _refine_ls_R_factor_gt 0.0399 #xl _refine_ls_wR_factor_ref 0.0793 #xl _refine_ls_wR_factor_gt 0.0724 #xl _refine_ls_goodness_of_fit_ref 1.014 #xl _refine_ls_restrained_S_all 1.014 #xl _refine_ls_shift/su_max 0.001 #xl _refine_ls_shift/su_mean 0.000 #xl _refine_diff_density_max 0.374 #xl _refine_diff_density_min -0.313 #xl _refine_diff_density_rms 0.069 #xl _refine_special_details ; H with HFIX, riding with U(H)=1.2*U(C) for CH2 and C/NH, 1.5*U(C) for CH3 ; _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_structure_solution ; A. Altomare, M. C. Burla, M. Camalli, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Moliterni, G. Polidori, R. Spagna: SIR97: a new tool for crystal structure determination and refinement; J. Appl. Crystallogr. 1999, 32, 115-119. ; _computing_structure_refinement 'SHELXL-97 (G. M. Sheldrick. University of G\"ottingen, 97-2 version)' _computing_molecular_graphics ? _computing_publication_material ? 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 0.58457(7) -0.02994(7) 0.50320(3) 0.0423(2) Uani 1 1 d . . . Br2 Br 0.78583(7) -0.18507(7) 0.43446(3) 0.0494(3) Uani 1 1 d . . . O1 O 0.6643(4) 0.1392(4) 0.28205(15) 0.0368(14) Uani 1 1 d . . . O2 O 0.3692(4) 0.0103(4) 0.35824(17) 0.0403(14) Uani 1 1 d . . . O3 O 0.2434(4) -0.0036(4) 0.42042(17) 0.0420(15) Uani 1 1 d . . . O4 O 0.6694(4) 0.3031(4) 0.42350(17) 0.0434(14) Uani 1 1 d . . . O5 O 0.6267(4) 0.3359(4) 0.50380(18) 0.0473(14) Uani 1 1 d . . . N1 N 0.5814(5) 0.0728(5) 0.40752(19) 0.0297(16) Uani 1 1 d . . . N2 N 0.5337(5) 0.2165(5) 0.3308(2) 0.0300(16) Uani 1 1 d . . . N3 N 0.3914(4) 0.0976(5) 0.4329(2) 0.0307(15) Uani 1 1 d . . . H3 H 0.3649 0.1054 0.4630 0.037 Uiso 1 1 calc R . . N4 N 0.5243(5) 0.2183(5) 0.46194(19) 0.0318(16) Uani 1 1 d . . . H4 H 0.4866 0.2128 0.4897 0.038 Uiso 1 1 calc R . . C1 C 0.6250(6) -0.0081(6) 0.4375(2) 0.0300(18) Uani 1 1 d . . . C2 C 0.6986(6) -0.0674(6) 0.4107(2) 0.0314(19) Uani 1 1 d . . . C3 C 0.7046(6) -0.0240(6) 0.3625(3) 0.033(2) Uani 1 1 d . . . H3 H 0.7496 -0.0498 0.3361 0.040 Uiso 1 1 calc R . . C4 C 0.6323(6) 0.0628(6) 0.3616(2) 0.0243(18) Uani 1 1 d . . . C5 C 0.6112(6) 0.1414(6) 0.3222(3) 0.0293(19) Uani 1 1 d . . . C6 C 0.5026(6) 0.3060(6) 0.2965(3) 0.043(2) Uani 1 1 d . . . H6A H 0.4791 0.2753 0.2642 0.052 Uiso 1 1 calc R . . H6B H 0.5656 0.3574 0.2911 0.052 Uiso 1 1 calc R . . C7 C 0.4061(6) 0.3657(7) 0.3219(2) 0.043(2) Uani 1 1 d . . . H7A H 0.4208 0.4462 0.3250 0.052 Uiso 1 1 calc R . . H7B H 0.3358 0.3546 0.3036 0.052 Uiso 1 1 calc R . . C8 C 0.4014(6) 0.3108(7) 0.3722(3) 0.039(2) Uani 1 1 d . . . H8 H 0.3525 0.3323 0.3979 0.047 Uiso 1 1 calc R . . C9 C 0.4744(6) 0.2289(6) 0.3756(3) 0.0287(19) Uani 1 1 d . . . C10 C 0.4915(6) 0.1533(6) 0.4188(2) 0.030(2) Uani 1 1 d . . . C11 C 0.3369(6) 0.0314(6) 0.3991(3) 0.0307(18) Uani 1 1 d . . . C12 C 0.1687(7) -0.0695(7) 0.3900(3) 0.051(2) Uani 1 1 d . . . H12A H 0.2102 -0.1061 0.3630 0.061 Uiso 1 1 calc R . . H12B H 0.1105 -0.0218 0.3753 0.061 Uiso 1 1 calc R . . C13 C 0.1176(8) -0.1547(8) 0.4235(3) 0.076(3) Uani 1 1 d . . . H13A H 0.0656 -0.2007 0.4046 0.113 Uiso 1 1 calc R . . H13B H 0.0777 -0.1172 0.4503 0.113 Uiso 1 1 calc R . . H13C H 0.1760 -0.2017 0.4375 0.113 Uiso 1 1 calc R . . C14 C 0.6124(7) 0.2864(6) 0.4591(3) 0.034(2) Uani 1 1 d . . . C15 C 0.7157(7) 0.4158(7) 0.5072(3) 0.066(3) Uani 1 1 d . . . H15A H 0.7062 0.4741 0.4817 0.080 Uiso 1 1 calc R . . H15B H 0.7880 0.3788 0.5016 0.080 Uiso 1 1 calc R . . C16 C 0.7126(12) 0.4645(12) 0.5559(5) 0.189(9) Uani 1 1 d . . . H16A H 0.7711 0.5206 0.5587 0.284 Uiso 1 1 calc R . . H16B H 0.7244 0.4065 0.5807 0.284 Uiso 1 1 calc R . . H16C H 0.6402 0.4994 0.5613 0.284 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 0.0534(6) 0.0464(5) 0.0270(4) 0.0060(4) 0.0021(4) 0.0009(4) Br2 0.0543(6) 0.0461(6) 0.0479(5) 0.0092(4) -0.0055(4) 0.0115(5) O1 0.045(3) 0.044(4) 0.022(3) -0.002(3) 0.009(3) 0.005(3) O2 0.045(4) 0.052(4) 0.024(3) -0.011(3) 0.000(3) -0.001(3) O3 0.035(3) 0.056(4) 0.036(3) -0.009(3) 0.003(3) -0.018(3) O4 0.045(4) 0.049(4) 0.036(3) -0.008(3) 0.012(3) -0.015(3) O5 0.054(4) 0.053(4) 0.035(3) -0.010(3) 0.008(3) -0.032(3) N1 0.031(4) 0.035(4) 0.023(3) -0.003(3) 0.003(3) -0.004(3) N2 0.033(4) 0.033(4) 0.024(3) 0.009(3) 0.006(3) 0.007(4) N3 0.029(4) 0.042(4) 0.021(3) 0.001(3) 0.005(3) -0.008(3) N4 0.031(4) 0.039(4) 0.026(3) -0.011(3) 0.002(3) -0.012(4) C1 0.038(5) 0.026(5) 0.027(4) 0.004(4) 0.004(4) -0.007(4) C2 0.031(5) 0.030(5) 0.033(4) 0.013(4) -0.007(4) 0.003(4) C3 0.032(5) 0.031(5) 0.037(5) -0.006(4) -0.003(4) 0.001(4) C4 0.024(5) 0.028(5) 0.021(4) -0.004(3) -0.001(3) 0.001(4) C5 0.028(5) 0.031(5) 0.029(5) -0.009(4) 0.000(4) -0.004(4) C6 0.054(6) 0.040(5) 0.035(4) 0.001(4) 0.000(4) 0.007(5) C7 0.043(5) 0.049(6) 0.038(4) 0.009(4) 0.001(4) 0.009(5) C8 0.032(5) 0.052(6) 0.033(4) 0.002(4) 0.017(4) 0.005(5) C9 0.026(5) 0.029(5) 0.031(4) -0.005(4) 0.010(4) 0.001(4) C10 0.037(5) 0.029(5) 0.022(4) -0.003(4) 0.007(4) -0.001(4) C11 0.027(5) 0.029(5) 0.036(5) 0.004(4) -0.007(4) -0.003(4) C12 0.055(6) 0.051(6) 0.047(5) -0.009(5) -0.003(5) -0.022(5) C13 0.080(8) 0.079(8) 0.068(6) 0.002(6) -0.021(6) -0.033(6) C14 0.036(5) 0.027(5) 0.038(5) -0.014(4) -0.009(4) -0.007(4) C15 0.074(7) 0.076(7) 0.050(5) -0.020(5) 0.011(5) -0.052(6) C16 0.245(18) 0.192(15) 0.131(11) -0.079(11) 0.077(12) -0.188(15) 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 1.863(6) . ? Br2 C2 1.879(7) . ? O1 C5 1.262(8) . ? O2 C11 1.199(8) . ? O3 C11 1.335(8) . ? O3 C12 1.455(9) . ? O4 C14 1.200(8) . ? O5 C14 1.361(8) . ? O5 C15 1.443(8) . ? N1 C1 1.373(8) . ? N1 C4 1.391(8) . ? N1 C10 1.486(9) . ? N2 C5 1.321(9) . ? N2 C9 1.417(9) . ? N2 C6 1.473(9) . ? N3 C11 1.382(9) . ? N3 C10 1.433(8) . ? N3 H3 0.8800 . ? N4 C14 1.345(9) . ? N4 C10 1.461(8) . ? N4 H4 0.8800 . ? C1 C2 1.351(9) . ? C2 C3 1.407(9) . ? C3 C4 1.362(9) . ? C3 H3 0.9500 . ? C4 C5 1.448(10) . ? C6 C7 1.531(10) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.514(9) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C8 C9 1.325(9) . ? C8 H8 0.9500 . ? C9 C10 1.495(10) . ? C12 C13 1.503(10) . ? C12 H12A 0.9900 . ? C12 H12B 0.9900 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C15 C16 1.444(13) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 H16A 0.9800 . ? C16 H16B 0.9800 . ? C16 H16C 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 C11 O3 C12 116.7(6) . . ? C14 O5 C15 116.3(6) . . ? C1 N1 C4 107.4(6) . . ? C1 N1 C10 128.4(5) . . ? C4 N1 C10 124.1(6) . . ? C5 N2 C9 125.4(6) . . ? C5 N2 C6 124.8(6) . . ? C9 N2 C6 109.6(6) . . ? C11 N3 C10 119.6(6) . . ? C11 N3 H3 120.2 . . ? C10 N3 H3 120.2 . . ? C14 N4 C10 119.6(6) . . ? C14 N4 H4 120.2 . . ? C10 N4 H4 120.2 . . ? C2 C1 N1 108.0(6) . . ? C2 C1 Br1 127.6(6) . . ? N1 C1 Br1 124.4(5) . . ? C1 C2 C3 109.6(6) . . ? C1 C2 Br2 125.6(5) . . ? C3 C2 Br2 124.7(6) . . ? C4 C3 C2 105.6(6) . . ? C4 C3 H3 127.2 . . ? C2 C3 H3 127.2 . . ? C3 C4 N1 109.4(6) . . ? C3 C4 C5 128.9(6) . . ? N1 C4 C5 121.6(6) . . ? O1 C5 N2 121.7(7) . . ? O1 C5 C4 122.1(7) . . ? N2 C5 C4 116.3(6) . . ? N2 C6 C7 104.6(6) . . ? N2 C6 H6A 110.8 . . ? C7 C6 H6A 110.8 . . ? N2 C6 H6B 110.8 . . ? C7 C6 H6B 110.8 . . ? H6A C6 H6B 108.9 . . ? C8 C7 C6 103.1(6) . . ? C8 C7 H7A 111.1 . . ? C6 C7 H7A 111.1 . . ? C8 C7 H7B 111.1 . . ? C6 C7 H7B 111.1 . . ? H7A C7 H7B 109.1 . . ? C9 C8 C7 111.4(7) . . ? C9 C8 H8 124.3 . . ? C7 C8 H8 124.3 . . ? C8 C9 N2 110.6(7) . . ? C8 C9 C10 126.9(6) . . ? N2 C9 C10 122.4(6) . . ? N3 C10 N4 105.4(5) . . ? N3 C10 N1 111.2(6) . . ? N4 C10 N1 108.5(6) . . ? N3 C10 C9 112.2(6) . . ? N4 C10 C9 109.6(6) . . ? N1 C10 C9 109.7(5) . . ? O2 C11 O3 127.3(7) . . ? O2 C11 N3 125.4(7) . . ? O3 C11 N3 107.3(6) . . ? O3 C12 C13 106.6(6) . . ? O3 C12 H12A 110.4 . . ? C13 C12 H12A 110.4 . . ? O3 C12 H12B 110.4 . . ? C13 C12 H12B 110.4 . . ? H12A C12 H12B 108.6 . . ? C12 C13 H13A 109.5 . . ? C12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? C12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? O4 C14 N4 127.0(7) . . ? O4 C14 O5 124.6(7) . . ? N4 C14 O5 108.4(7) . . ? O5 C15 C16 108.0(7) . . ? O5 C15 H15A 110.1 . . ? C16 C15 H15A 110.1 . . ? O5 C15 H15B 110.1 . . ? C16 C15 H15B 110.1 . . ? H15A C15 H15B 108.4 . . ? C15 C16 H16A 109.5 . . ? C15 C16 H16B 109.5 . . ? H16A C16 H16B 109.5 . . ? C15 C16 H16C 109.5 . . ? H16A C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 C2 -1.1(8) . . . . ? C10 N1 C1 C2 175.1(7) . . . . ? C4 N1 C1 Br1 179.8(5) . . . . ? C10 N1 C1 Br1 -4.0(10) . . . . ? N1 C1 C2 C3 0.7(8) . . . . ? Br1 C1 C2 C3 179.7(5) . . . . ? N1 C1 C2 Br2 177.7(5) . . . . ? Br1 C1 C2 Br2 -3.3(10) . . . . ? C1 C2 C3 C4 0.0(9) . . . . ? Br2 C2 C3 C4 -177.0(5) . . . . ? C2 C3 C4 N1 -0.7(8) . . . . ? C2 C3 C4 C5 175.3(7) . . . . ? C1 N1 C4 C3 1.2(8) . . . . ? C10 N1 C4 C3 -175.2(6) . . . . ? C1 N1 C4 C5 -175.2(6) . . . . ? C10 N1 C4 C5 8.4(10) . . . . ? C9 N2 C5 O1 -176.4(6) . . . . ? C6 N2 C5 O1 -1.8(11) . . . . ? C9 N2 C5 C4 3.0(10) . . . . ? C6 N2 C5 C4 177.7(6) . . . . ? C3 C4 C5 O1 -2.3(12) . . . . ? N1 C4 C5 O1 173.4(6) . . . . ? C3 C4 C5 N2 178.3(7) . . . . ? N1 C4 C5 N2 -6.1(10) . . . . ? C5 N2 C6 C7 177.0(7) . . . . ? C9 N2 C6 C7 -7.6(8) . . . . ? N2 C6 C7 C8 6.7(8) . . . . ? C6 C7 C8 C9 -3.9(9) . . . . ? C7 C8 C9 N2 -0.8(9) . . . . ? C7 C8 C9 C10 -177.8(7) . . . . ? C5 N2 C9 C8 -179.1(7) . . . . ? C6 N2 C9 C8 5.5(8) . . . . ? C5 N2 C9 C10 -2.0(11) . . . . ? C6 N2 C9 C10 -177.3(6) . . . . ? C11 N3 C10 N4 177.9(6) . . . . ? C11 N3 C10 N1 -64.8(8) . . . . ? C11 N3 C10 C9 58.6(8) . . . . ? C14 N4 C10 N3 -175.6(6) . . . . ? C14 N4 C10 N1 65.2(8) . . . . ? C14 N4 C10 C9 -54.6(8) . . . . ? C1 N1 C10 N3 -57.3(9) . . . . ? C4 N1 C10 N3 118.3(7) . . . . ? C1 N1 C10 N4 58.1(9) . . . . ? C4 N1 C10 N4 -126.3(6) . . . . ? C1 N1 C10 C9 177.9(6) . . . . ? C4 N1 C10 C9 -6.5(9) . . . . ? C8 C9 C10 N3 55.7(10) . . . . ? N2 C9 C10 N3 -120.9(7) . . . . ? C8 C9 C10 N4 -61.1(10) . . . . ? N2 C9 C10 N4 122.3(7) . . . . ? C8 C9 C10 N1 179.9(7) . . . . ? N2 C9 C10 N1 3.3(9) . . . . ? C12 O3 C11 O2 -3.9(11) . . . . ? C12 O3 C11 N3 176.2(6) . . . . ? C10 N3 C11 O2 4.4(10) . . . . ? C10 N3 C11 O3 -175.7(6) . . . . ? C11 O3 C12 C13 144.3(7) . . . . ? C10 N4 C14 O4 1.4(11) . . . . ? C10 N4 C14 O5 -179.1(6) . . . . ? C15 O5 C14 O4 1.8(11) . . . . ? C15 O5 C14 N4 -177.7(7) . . . . ? C14 O5 C15 C16 175.9(10) . . . . ? loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 _geom_contact_publ_flag ? ? ? ? ? ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N3 H3 O1 0.88 2.00 2.826(7) 155.8 8_545 ? N4 H4 O1 0.88 1.99 2.812(7) 155.2 8_545 ? _geom_special_details ? _audit_block_code C16H18Br2N4O5_in472_lindel _audit_creation_method 'form98_non/compatible with shelxl97-2' _chemical_name_systematic ? _chemical_formula_moiety 'C16 H18 Br2 N4 O5' _chemical_formula_sum 'C16 H18 Br2 N4 O5' _chemical_formula_weight 506.146 _chemical_melting_point ? #?# in K! _cell_formula_units_Z 8 #?# adjust to _chemical_formula_[] _exptl_crystal_density_diffrn 1.71000(13) _exptl_crystal_F_000 2016 #===END