# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # 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_c323 _database_code_depnum_ccdc_archive 'CCDC 903822' #TrackingRef 'web_deposit_cif_file_0_jianwang_1349079753.C323.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C17 H16 Br2 N2 O5' _chemical_formula_weight 488.14 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.6128(11) _cell_length_b 9.9153(12) _cell_length_c 12.1573(16) _cell_angle_alpha 104.434(2) _cell_angle_beta 100.523(3) _cell_angle_gamma 108.276(2) _cell_volume 915.5(2) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 941 _cell_measurement_theta_min 3.27 _cell_measurement_theta_max 27.22 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.13 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas 'Not Measured' _exptl_crystal_density_diffrn 1.771 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 484 _exptl_absorpt_coefficient_mu 4.458 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.2561 _exptl_absorpt_correction_T_max 0.7168 _exptl_absorpt_process_details 'Sadabs, (Sheldrick 2008)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 12044 _diffrn_reflns_av_R_equivalents 0.0314 _diffrn_reflns_av_sigmaI/netI 0.0356 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.80 _diffrn_reflns_theta_max 27.48 _reflns_number_total 4184 _reflns_number_gt 3663 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0476P)^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_number_reflns 4184 _refine_ls_number_parameters 245 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0345 _refine_ls_R_factor_gt 0.0278 _refine_ls_wR_factor_ref 0.0844 _refine_ls_wR_factor_gt 0.0711 _refine_ls_goodness_of_fit_ref 1.113 _refine_ls_restrained_S_all 1.113 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.76564(3) 0.73671(3) -0.11736(2) 0.02106(9) Uani 1 1 d . . . Br2 Br 1.37398(3) 0.99340(3) 0.25801(2) 0.02307(9) Uani 1 1 d . . . O1 O 0.6888(2) 0.49799(17) -0.00351(14) 0.0154(3) Uani 1 1 d . . . O2 O 0.6726(2) 0.6470(2) 0.24695(15) 0.0207(4) Uani 1 1 d . . . O3 O 0.5816(2) 0.51732(19) 0.36579(15) 0.0188(4) Uani 1 1 d . . . O4 O 1.1164(2) 0.60018(19) 0.44515(15) 0.0187(4) Uani 1 1 d . . . O5 O 0.9538(2) 0.73427(19) 0.48384(15) 0.0198(4) Uani 1 1 d . . . N1 N 0.5095(3) 0.2598(2) -0.07212(19) 0.0172(4) Uani 1 1 d . . . H1N H 0.463(4) 0.286(3) -0.127(3) 0.027(8) Uiso 1 1 d . . . H2N H 0.455(4) 0.155(4) -0.072(3) 0.041(10) Uiso 1 1 d . . . N2 N 0.6856(3) 0.0717(2) 0.11051(19) 0.0196(4) Uani 1 1 d . . . C1 C 0.9038(3) 0.7279(3) 0.0183(2) 0.0155(5) Uani 1 1 d . . . C2 C 1.0598(3) 0.8436(3) 0.0768(2) 0.0179(5) Uani 1 1 d . . . H2 H 1.0967 0.9276 0.0504 0.021 Uiso 1 1 calc R . . C3 C 1.1612(3) 0.8346(3) 0.1747(2) 0.0168(5) Uani 1 1 d . . . C4 C 1.1096(3) 0.7134(3) 0.2151(2) 0.0158(5) Uani 1 1 d . . . H4 H 1.1826 0.7087 0.2816 0.019 Uiso 1 1 calc R . . C5 C 0.9506(3) 0.5987(3) 0.1579(2) 0.0137(4) Uani 1 1 d . . . C6 C 0.8487(3) 0.6067(2) 0.0586(2) 0.0142(5) Uani 1 1 d . . . C7 C 0.6479(3) 0.3609(3) 0.0128(2) 0.0144(5) Uani 1 1 d . . . C8 C 0.7428(3) 0.3391(2) 0.1049(2) 0.0134(5) Uani 1 1 d . . . C9 C 0.8869(3) 0.4679(2) 0.20278(19) 0.0127(4) Uani 1 1 d . . . H9 H 0.9827 0.4331 0.2214 0.015 Uiso 1 1 calc R . . C10 C 0.7077(3) 0.1909(3) 0.1074(2) 0.0146(5) Uani 1 1 d . . . C11 C 0.8313(3) 0.5091(3) 0.3178(2) 0.0138(5) Uani 1 1 d . . . H11 H 0.7875 0.4142 0.3369 0.017 Uiso 1 1 calc R . . C12 C 0.6875(3) 0.5666(3) 0.3041(2) 0.0143(5) Uani 1 1 d . . . C13 C 0.4512(3) 0.5815(3) 0.3738(2) 0.0230(6) Uani 1 1 d . . . H13A H 0.3575 0.5155 0.3954 0.028 Uiso 1 1 calc R . . H13B H 0.4031 0.5888 0.2961 0.028 Uiso 1 1 calc R . . C14 C 0.5287(3) 0.7348(3) 0.4658(3) 0.0306(7) Uani 1 1 d . . . H14A H 0.5809 0.7276 0.5417 0.046 Uiso 1 1 calc R . . H14B H 0.4397 0.7753 0.4744 0.046 Uiso 1 1 calc R . . H14C H 0.6159 0.8016 0.4413 0.046 Uiso 1 1 calc R . . C15 C 0.9842(3) 0.6187(3) 0.4223(2) 0.0157(5) Uani 1 1 d . . . C16 C 1.0937(4) 0.8437(3) 0.5864(2) 0.0293(6) Uani 1 1 d . . . H16A H 1.1897 0.8982 0.5601 0.035 Uiso 1 1 calc R . . H16B H 1.1352 0.7919 0.6381 0.035 Uiso 1 1 calc R . . C17 C 1.0272(4) 0.9513(3) 0.6525(2) 0.0300(6) Uani 1 1 d . . . H17A H 0.9875 1.0025 0.6007 0.045 Uiso 1 1 calc R . . H17B H 1.1184 1.0258 0.7221 0.045 Uiso 1 1 calc R . . H17C H 0.9322 0.8961 0.6779 0.045 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 0.02931(15) 0.01442(14) 0.01615(14) 0.00765(10) 0.00243(10) 0.00419(11) Br2 0.01778(14) 0.01592(14) 0.02624(16) 0.00132(11) 0.00563(11) -0.00099(10) O1 0.0160(8) 0.0097(8) 0.0165(8) 0.0038(7) 0.0005(7) 0.0025(6) O2 0.0234(9) 0.0265(10) 0.0184(9) 0.0111(8) 0.0056(7) 0.0146(8) O3 0.0162(8) 0.0220(9) 0.0202(9) 0.0070(7) 0.0073(7) 0.0084(7) O4 0.0159(8) 0.0246(9) 0.0171(9) 0.0075(7) 0.0037(7) 0.0095(7) O5 0.0192(9) 0.0186(9) 0.0177(9) 0.0010(7) -0.0008(7) 0.0093(7) N1 0.0198(10) 0.0123(10) 0.0163(10) 0.0058(8) 0.0000(8) 0.0039(8) N2 0.0204(11) 0.0159(11) 0.0210(11) 0.0083(9) 0.0037(9) 0.0046(9) C1 0.0223(12) 0.0129(11) 0.0122(11) 0.0039(9) 0.0058(9) 0.0074(10) C2 0.0250(13) 0.0111(11) 0.0189(13) 0.0048(10) 0.0125(10) 0.0052(10) C3 0.0153(11) 0.0126(11) 0.0172(12) -0.0006(9) 0.0065(9) 0.0017(9) C4 0.0145(11) 0.0180(12) 0.0142(11) 0.0030(9) 0.0050(9) 0.0063(9) C5 0.0159(11) 0.0126(11) 0.0134(11) 0.0035(9) 0.0071(9) 0.0057(9) C6 0.0143(11) 0.0100(11) 0.0158(12) 0.0019(9) 0.0049(9) 0.0029(9) C7 0.0182(11) 0.0090(10) 0.0168(12) 0.0047(9) 0.0072(9) 0.0047(9) C8 0.0146(11) 0.0107(10) 0.0149(11) 0.0036(9) 0.0039(9) 0.0054(9) C9 0.0138(11) 0.0121(11) 0.0120(11) 0.0033(9) 0.0031(9) 0.0055(9) C10 0.0140(11) 0.0181(12) 0.0115(11) 0.0049(9) 0.0032(9) 0.0058(9) C11 0.0148(11) 0.0147(11) 0.0127(11) 0.0064(9) 0.0036(9) 0.0051(9) C12 0.0151(11) 0.0158(11) 0.0086(11) 0.0010(9) 0.0015(9) 0.0048(9) C13 0.0148(12) 0.0279(14) 0.0241(14) 0.0020(11) 0.0063(10) 0.0097(11) C14 0.0214(13) 0.0318(15) 0.0321(16) -0.0036(13) 0.0056(12) 0.0135(12) C15 0.0178(11) 0.0180(12) 0.0127(11) 0.0068(9) 0.0048(9) 0.0072(10) C16 0.0242(14) 0.0273(14) 0.0225(14) -0.0044(12) -0.0075(11) 0.0095(12) C17 0.0346(16) 0.0240(14) 0.0214(14) -0.0029(11) -0.0019(12) 0.0115(12) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C1 1.888(2) . ? Br2 C3 1.892(2) . ? O1 C7 1.368(3) . ? O1 C6 1.383(3) . ? O2 C12 1.201(3) . ? O3 C12 1.336(3) . ? O3 C13 1.461(3) . ? O4 C15 1.203(3) . ? O5 C15 1.332(3) . ? O5 C16 1.463(3) . ? N1 C7 1.333(3) . ? N2 C10 1.148(3) . ? C1 C2 1.380(3) . ? C1 C6 1.390(3) . ? C2 C3 1.382(3) . ? C3 C4 1.385(3) . ? C4 C5 1.391(3) . ? C5 C6 1.391(3) . ? C5 C9 1.516(3) . ? C7 C8 1.366(3) . ? C8 C10 1.414(3) . ? C8 C9 1.515(3) . ? C9 C11 1.560(3) . ? C11 C12 1.518(3) . ? C11 C15 1.528(3) . ? C13 C14 1.500(4) . ? C16 C17 1.495(4) . ? 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 C7 O1 C6 118.14(18) . . ? C12 O3 C13 116.12(19) . . ? C15 O5 C16 115.91(19) . . ? C2 C1 C6 120.6(2) . . ? C2 C1 Br1 119.05(18) . . ? C6 C1 Br1 120.34(18) . . ? C1 C2 C3 118.5(2) . . ? C2 C3 C4 121.7(2) . . ? C2 C3 Br2 119.31(18) . . ? C4 C3 Br2 119.00(18) . . ? C3 C4 C5 119.8(2) . . ? C4 C5 C6 118.8(2) . . ? C4 C5 C9 121.1(2) . . ? C6 C5 C9 120.1(2) . . ? O1 C6 C1 116.7(2) . . ? O1 C6 C5 122.7(2) . . ? C1 C6 C5 120.6(2) . . ? N1 C7 C8 127.8(2) . . ? N1 C7 O1 110.4(2) . . ? C8 C7 O1 121.8(2) . . ? C7 C8 C10 118.8(2) . . ? C7 C8 C9 122.2(2) . . ? C10 C8 C9 119.0(2) . . ? C8 C9 C5 109.23(18) . . ? C8 C9 C11 110.91(19) . . ? C5 C9 C11 113.83(19) . . ? N2 C10 C8 177.5(3) . . ? C12 C11 C15 111.37(19) . . ? C12 C11 C9 113.87(19) . . ? C15 C11 C9 110.93(19) . . ? O2 C12 O3 124.9(2) . . ? O2 C12 C11 124.5(2) . . ? O3 C12 C11 110.61(19) . . ? O3 C13 C14 109.5(2) . . ? O4 C15 O5 124.7(2) . . ? O4 C15 C11 122.7(2) . . ? O5 C15 C11 112.6(2) . . ? O5 C16 C17 107.7(2) . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A N1 H1N O2 0.85(3) 2.07(3) 2.916(3) 172(3) 2_665 N1 H2N N2 0.99(3) 2.08(3) 3.055(3) 167(3) 2_655 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.48 _diffrn_measured_fraction_theta_full 0.998 _refine_diff_density_max 0.722 _refine_diff_density_min -0.443 _refine_diff_density_rms 0.129