data_kw405sm _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C15 H14 Br N O4' _chemical_formula_sum 'C15 H14 Br N O4' _chemical_formula_weight 352.18 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 Monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 10.4432(14) _cell_length_b 10.3372(14) _cell_length_c 13.1172(17) _cell_angle_alpha 90.00 _cell_angle_beta 97.524(2) _cell_angle_gamma 90.00 _cell_volume 1403.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 298(2) _cell_measurement_reflns_used 3778 _cell_measurement_theta_min 2.52 _cell_measurement_theta_max 25.26 _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.60 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.10 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.666 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 712 _exptl_absorpt_coefficient_mu 2.944 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_correction_T_min 0.521 _exptl_absorpt_correction_T_max 0.745 _exptl_absorpt_process_details 'Sadabs (Bruker)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 298(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 11486 _diffrn_reflns_av_R_equivalents 0.0334 _diffrn_reflns_av_sigmaI/netI 0.0288 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.97 _diffrn_reflns_theta_max 26.45 _reflns_number_total 2888 _reflns_number_gt 2136 _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^)+(0.0357P)^2^+0.6209P] 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_number_reflns 2888 _refine_ls_number_parameters 191 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0515 _refine_ls_R_factor_gt 0.0301 _refine_ls_wR_factor_ref 0.0778 _refine_ls_wR_factor_gt 0.0697 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 Br Br 0.47798(3) -0.20607(3) -0.23508(2) 0.05776(12) Uani 1 1 d . . . O1 O 0.35913(16) -0.08102(15) -0.04770(12) 0.0406(4) Uani 1 1 d . . . O2 O 0.17814(15) -0.04913(15) 0.02477(12) 0.0391(4) Uani 1 1 d . . . O3 O -0.0166(2) 0.19107(19) 0.21258(16) 0.0611(5) Uani 1 1 d . . . O4 O 0.06196(16) 0.36447(16) 0.14579(13) 0.0458(4) Uani 1 1 d . . . N1 N 0.31393(18) -0.00654(18) 0.02894(14) 0.0356(4) Uani 1 1 d . . . C1 C 0.1441(3) 0.5566(3) 0.0840(2) 0.0479(6) Uani 1 1 d . . . H1 H 0.0872 0.6031 0.1189 0.058 Uiso 1 1 calc R . . C2 C 0.2280(3) 0.6194(2) 0.0285(2) 0.0545(7) Uani 1 1 d . . . H2 H 0.2281 0.7093 0.0257 0.065 Uiso 1 1 calc R . . C3 C 0.3124(3) 0.5499(3) -0.0231(2) 0.0524(7) Uani 1 1 d . . . H3 H 0.3695 0.5934 -0.0598 0.063 Uiso 1 1 calc R . . C4 C 0.3127(3) 0.4170(2) -0.02070(19) 0.0437(6) Uani 1 1 d . . . H4 H 0.3698 0.3716 -0.0562 0.052 Uiso 1 1 calc R . . C5 C 0.2285(2) 0.3490(2) 0.03420(17) 0.0350(5) Uani 1 1 d . . . C6 C 0.1459(2) 0.4229(2) 0.08693(18) 0.0382(6) Uani 1 1 d . . . C7 C 0.0563(2) 0.2330(2) 0.15672(19) 0.0417(6) Uani 1 1 d . . . C8 C 0.1386(2) 0.1543(2) 0.10000(17) 0.0345(5) Uani 1 1 d . . . C9 C 0.2209(2) 0.2095(2) 0.04182(17) 0.0330(5) Uani 1 1 d . . . C10 C 0.3062(2) 0.1252(2) -0.01481(17) 0.0335(5) Uani 1 1 d . . . H10 H 0.3932 0.1625 -0.0067 0.040 Uiso 1 1 calc R . . C11 C 0.2608(2) 0.1067(2) -0.13022(17) 0.0377(5) Uani 1 1 d . . . H11A H 0.1676 0.1125 -0.1453 0.045 Uiso 1 1 calc R . . H11B H 0.2999 0.1699 -0.1712 0.045 Uiso 1 1 calc R . . C12 C 0.3085(2) -0.0304(2) -0.14910(18) 0.0373(5) Uani 1 1 d . . . H12 H 0.2371 -0.0842 -0.1810 0.045 Uiso 1 1 calc R . . C13 C 0.4183(2) -0.0314(2) -0.21337(19) 0.0403(6) Uani 1 1 d . . . H13A H 0.4894 0.0195 -0.1792 0.048 Uiso 1 1 calc R . . H13B H 0.3899 0.0085 -0.2794 0.048 Uiso 1 1 calc R . . C14 C 0.1273(2) 0.0099(2) 0.11012(18) 0.0393(6) Uani 1 1 d . . . H14 H 0.0351 -0.0109 0.1035 0.047 Uiso 1 1 calc R . . C15 C 0.1884(3) -0.0413(3) 0.2128(2) 0.0525(7) Uani 1 1 d . . . H15A H 0.2779 -0.0171 0.2239 0.079 Uiso 1 1 calc R . . H15B H 0.1813 -0.1339 0.2135 0.079 Uiso 1 1 calc R . . H15C H 0.1448 -0.0055 0.2664 0.079 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 Br 0.0647(2) 0.04478(16) 0.0680(2) -0.01151(13) 0.02440(15) 0.00800(13) O1 0.0506(10) 0.0333(9) 0.0407(10) 0.0031(7) 0.0172(8) 0.0086(7) O2 0.0423(10) 0.0326(8) 0.0452(10) -0.0008(7) 0.0156(7) -0.0072(7) O3 0.0631(12) 0.0605(13) 0.0685(13) 0.0032(10) 0.0418(10) 0.0008(10) O4 0.0520(11) 0.0420(10) 0.0475(10) -0.0017(8) 0.0220(8) 0.0068(8) N1 0.0371(11) 0.0325(10) 0.0395(11) 0.0013(9) 0.0137(9) 0.0020(8) C1 0.0560(17) 0.0407(14) 0.0463(15) -0.0066(12) 0.0039(13) 0.0097(12) C2 0.081(2) 0.0269(12) 0.0541(17) 0.0009(12) 0.0028(15) -0.0002(13) C3 0.0703(19) 0.0383(14) 0.0501(16) 0.0038(12) 0.0132(14) -0.0124(13) C4 0.0534(16) 0.0350(13) 0.0456(15) 0.0010(11) 0.0170(12) -0.0028(11) C5 0.0406(13) 0.0320(11) 0.0327(12) 0.0013(10) 0.0061(10) -0.0009(10) C6 0.0414(14) 0.0364(13) 0.0365(13) -0.0011(10) 0.0043(11) 0.0034(10) C7 0.0430(15) 0.0443(15) 0.0399(14) 0.0001(11) 0.0128(11) 0.0007(11) C8 0.0342(13) 0.0355(12) 0.0348(13) 0.0016(10) 0.0088(10) 0.0006(10) C9 0.0346(12) 0.0333(11) 0.0320(12) -0.0011(10) 0.0076(9) -0.0010(10) C10 0.0340(13) 0.0282(12) 0.0400(13) 0.0039(10) 0.0116(10) -0.0001(9) C11 0.0452(14) 0.0366(12) 0.0339(13) 0.0036(10) 0.0148(10) 0.0030(11) C12 0.0387(14) 0.0365(13) 0.0380(13) -0.0005(10) 0.0102(10) -0.0006(10) C13 0.0429(14) 0.0368(13) 0.0438(14) -0.0024(11) 0.0150(11) 0.0003(11) C14 0.0377(14) 0.0397(13) 0.0439(14) 0.0018(11) 0.0175(11) -0.0039(11) C15 0.0604(17) 0.0526(16) 0.0479(16) 0.0146(13) 0.0197(13) 0.0015(13) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br C13 1.943(2) . ? O1 N1 1.397(2) . ? O1 C12 1.462(3) . ? O2 C14 1.436(3) . ? O2 N1 1.479(2) . ? O3 C7 1.204(3) . ? O4 C7 1.369(3) . ? O4 C6 1.381(3) . ? N1 C10 1.476(3) . ? C1 C2 1.374(4) . ? C1 C6 1.383(3) . ? C1 H1 0.9300 . ? C2 C3 1.381(4) . ? C2 H2 0.9300 . ? C3 C4 1.375(3) . ? C3 H3 0.9300 . ? C4 C5 1.397(3) . ? C4 H4 0.9300 . ? C5 C6 1.400(3) . ? C5 C9 1.449(3) . ? C7 C8 1.456(3) . ? C8 C9 1.348(3) . ? C8 C14 1.505(3) . ? C9 C10 1.510(3) . ? C10 C11 1.538(3) . ? C10 H10 0.9800 . ? C11 C12 1.532(3) . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C13 1.509(3) . ? C12 H12 0.9800 . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.509(4) . ? C14 H14 0.9800 . ? C15 H15A 0.9600 . ? C15 H15B 0.9600 . ? C15 H15C 0.9600 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag N1 O1 C12 109.96(16) . . ? C14 O2 N1 107.16(16) . . ? C7 O4 C6 122.14(18) . . ? O1 N1 C10 103.60(16) . . ? O1 N1 O2 102.83(15) . . ? C10 N1 O2 104.90(16) . . ? C2 C1 C6 118.7(3) . . ? C2 C1 H1 120.7 . . ? C6 C1 H1 120.7 . . ? C1 C2 C3 120.4(2) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C4 C3 C2 120.6(3) . . ? C4 C3 H3 119.7 . . ? C2 C3 H3 119.7 . . ? C3 C4 C5 121.0(2) . . ? C3 C4 H4 119.5 . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 116.8(2) . . ? C4 C5 C9 125.5(2) . . ? C6 C5 C9 117.8(2) . . ? O4 C6 C1 116.4(2) . . ? O4 C6 C5 121.0(2) . . ? C1 C6 C5 122.6(2) . . ? O3 C7 O4 117.4(2) . . ? O3 C7 C8 124.9(2) . . ? O4 C7 C8 117.7(2) . . ? C9 C8 C7 121.0(2) . . ? C9 C8 C14 122.2(2) . . ? C7 C8 C14 116.8(2) . . ? C8 C9 C5 120.3(2) . . ? C8 C9 C10 119.7(2) . . ? C5 C9 C10 119.97(19) . . ? N1 C10 C9 110.31(17) . . ? N1 C10 C11 105.19(18) . . ? C9 C10 C11 115.51(19) . . ? N1 C10 H10 108.5 . . ? C9 C10 H10 108.5 . . ? C11 C10 H10 108.5 . . ? C12 C11 C10 102.09(18) . . ? C12 C11 H11A 111.4 . . ? C10 C11 H11A 111.4 . . ? C12 C11 H11B 111.4 . . ? C10 C11 H11B 111.4 . . ? H11A C11 H11B 109.2 . . ? O1 C12 C13 107.16(19) . . ? O1 C12 C11 105.69(17) . . ? C13 C12 C11 112.55(19) . . ? O1 C12 H12 110.4 . . ? C13 C12 H12 110.4 . . ? C11 C12 H12 110.4 . . ? C12 C13 Br 111.71(16) . . ? C12 C13 H13A 109.3 . . ? Br C13 H13A 109.3 . . ? C12 C13 H13B 109.3 . . ? Br C13 H13B 109.3 . . ? H13A C13 H13B 107.9 . . ? O2 C14 C8 108.15(18) . . ? O2 C14 C15 113.0(2) . . ? C8 C14 C15 113.5(2) . . ? O2 C14 H14 107.3 . . ? C8 C14 H14 107.3 . . ? C15 C14 H14 107.3 . . ? C14 C15 H15A 109.5 . . ? C14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? C14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 O1 N1 C10 -33.8(2) . . . . ? C12 O1 N1 O2 75.25(19) . . . . ? C14 O2 N1 O1 172.64(16) . . . . ? C14 O2 N1 C10 -79.29(19) . . . . ? C6 C1 C2 C3 -0.1(4) . . . . ? C1 C2 C3 C4 0.7(4) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C3 C4 C5 C6 -0.7(4) . . . . ? C3 C4 C5 C9 -180.0(2) . . . . ? C7 O4 C6 C1 -178.6(2) . . . . ? C7 O4 C6 C5 0.9(3) . . . . ? C2 C1 C6 O4 178.5(2) . . . . ? C2 C1 C6 C5 -1.0(4) . . . . ? C4 C5 C6 O4 -178.1(2) . . . . ? C9 C5 C6 O4 1.3(3) . . . . ? C4 C5 C6 C1 1.4(4) . . . . ? C9 C5 C6 C1 -179.3(2) . . . . ? C6 O4 C7 O3 177.4(2) . . . . ? C6 O4 C7 C8 -2.7(3) . . . . ? O3 C7 C8 C9 -177.7(3) . . . . ? O4 C7 C8 C9 2.4(4) . . . . ? O3 C7 C8 C14 2.1(4) . . . . ? O4 C7 C8 C14 -177.8(2) . . . . ? C7 C8 C9 C5 -0.3(4) . . . . ? C14 C8 C9 C5 180.0(2) . . . . ? C7 C8 C9 C10 179.1(2) . . . . ? C14 C8 C9 C10 -0.6(3) . . . . ? C4 C5 C9 C8 177.8(2) . . . . ? C6 C5 C9 C8 -1.5(3) . . . . ? C4 C5 C9 C10 -1.7(4) . . . . ? C6 C5 C9 C10 179.0(2) . . . . ? O1 N1 C10 C9 162.18(17) . . . . ? O2 N1 C10 C9 54.7(2) . . . . ? O1 N1 C10 C11 37.0(2) . . . . ? O2 N1 C10 C11 -70.51(19) . . . . ? C8 C9 C10 N1 -17.7(3) . . . . ? C5 C9 C10 N1 161.7(2) . . . . ? C8 C9 C10 C11 101.3(3) . . . . ? C5 C9 C10 C11 -79.2(3) . . . . ? N1 C10 C11 C12 -26.1(2) . . . . ? C9 C10 C11 C12 -147.99(19) . . . . ? N1 O1 C12 C13 137.13(18) . . . . ? N1 O1 C12 C11 16.9(2) . . . . ? C10 C11 C12 O1 6.5(2) . . . . ? C10 C11 C12 C13 -110.2(2) . . . . ? O1 C12 C13 Br 63.7(2) . . . . ? C11 C12 C13 Br 179.47(16) . . . . ? N1 O2 C14 C8 58.8(2) . . . . ? N1 O2 C14 C15 -67.6(2) . . . . ? C9 C8 C14 O2 -20.1(3) . . . . ? C7 C8 C14 O2 160.2(2) . . . . ? C9 C8 C14 C15 106.1(3) . . . . ? C7 C8 C14 C15 -73.6(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 26.45 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.322 _refine_diff_density_min -0.299 _refine_diff_density_rms 0.051