data_a loop_ _journal_name_full 'European Journal of Chemistry' _journal_coden_ASTM EJCUA9 _journal_volume 8 _journal_issue 4 _journal_year 2017 _journal_page_first 422 _journal_page_last 429 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H9 Br N2 O4' _chemical_formula_sum 'C16 H9 Br N2 O4' _chemical_formula_weight 373.16 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 'P2(1)/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.5360(4) _cell_length_b 16.2361(11) _cell_length_c 13.6968(8) _cell_angle_alpha 90.00 _cell_angle_beta 96.2510(10) _cell_angle_gamma 90.00 _cell_volume 1444.85(16) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3606 _cell_measurement_theta_min 2.0 _cell_measurement_theta_max 28.3 _exptl_crystal_description Block _exptl_crystal_colour Colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.39 _exptl_crystal_size_min 0.28 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.715 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 2.868 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.221 _exptl_absorpt_correction_T_max 0.570 _exptl_absorpt_process_details 'SADABS(Bruker, 2000)' _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 ; Bruker SMART APEX CCD area-detector diffractometer ; _diffrn_measurement_method '\w scan' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10403 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0301 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.95 _diffrn_reflns_theta_max 28.34 _reflns_number_total 3606 _reflns_number_gt 2664 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART (Bruker, 2000)' _computing_cell_refinement 'SAINT (Bruker, 2000)' _computing_data_reduction 'SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)' _computing_publication_material ; SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2009) ; _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^)+(0.0712P)^2^+0.3071P] 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 3606 _refine_ls_number_parameters 208 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0622 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1237 _refine_ls_wR_factor_gt 0.1140 _refine_ls_goodness_of_fit_ref 1.060 _refine_ls_restrained_S_all 1.060 _refine_ls_shift/su_max 0.003 _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 1.20690(6) 0.06602(2) 1.48563(2) 0.07428(17) Uani 1 1 d . . . O3 O 1.1149(2) 0.12798(11) 1.10612(11) 0.0435(4) Uani 1 1 d . . . O4 O 1.3578(3) 0.21686(11) 1.06671(12) 0.0493(4) Uani 1 1 d . . . O1 O 0.5213(3) 0.19953(14) 0.72857(17) 0.0715(6) Uani 1 1 d . . . N2 N 1.2686(3) 0.05222(12) 0.95249(15) 0.0421(5) Uani 1 1 d . . . N1 N 0.6493(3) 0.14580(14) 0.73864(16) 0.0492(5) Uani 1 1 d . . . C11 C 1.3817(3) 0.16129(13) 1.22885(15) 0.0339(4) Uani 1 1 d . . . C3 C 0.7833(3) 0.14046(14) 0.83196(16) 0.0374(5) Uani 1 1 d . . . C4 C 0.9737(3) 0.09690(13) 0.83869(15) 0.0329(4) Uani 1 1 d . . . O2 O 0.6670(4) 0.09372(19) 0.67589(17) 0.0864(8) Uani 1 1 d . . . C8 C 1.0870(3) 0.09317(13) 0.93361(15) 0.0322(4) Uani 1 1 d . . . C10 C 1.2908(3) 0.17310(14) 1.12551(15) 0.0353(4) Uani 1 1 d . . . C12 C 1.2742(4) 0.12103(14) 1.29648(15) 0.0383(5) Uani 1 1 d . . . H12A H 1.1427 0.0979 1.2769 0.046 Uiso 1 1 calc R . . C9 C 1.0086(3) 0.13439(14) 1.01266(15) 0.0369(5) Uani 1 1 d . . . C15 C 1.6607(4) 0.18518(18) 1.35436(18) 0.0514(6) Uani 1 1 d . . . H15A H 1.7946 0.2062 1.3737 0.062 Uiso 1 1 calc R . . C16 C 1.5744(4) 0.19440(15) 1.25786(17) 0.0439(5) Uani 1 1 d . . . H16A H 1.6468 0.2232 1.2120 0.053 Uiso 1 1 calc R . . C5 C 1.0668(4) 0.05961(14) 0.76150(17) 0.0427(5) Uani 1 1 d . . . H5A H 1.0020 0.0623 0.6960 0.051 Uiso 1 1 calc R . . C13 C 1.3610(4) 0.11511(15) 1.39256(16) 0.0431(5) Uani 1 1 d . . . C2 C 0.7126(4) 0.17750(16) 0.91000(19) 0.0462(6) Uani 1 1 d . . . H2B H 0.5837 0.2051 0.9022 0.055 Uiso 1 1 calc R . . C14 C 1.5553(4) 0.14614(16) 1.42211(17) 0.0476(6) Uani 1 1 d . . . H14A H 1.6145 0.1404 1.4882 0.057 Uiso 1 1 calc R . . C1 C 0.8280(4) 0.17555(17) 1.00235(18) 0.0470(6) Uani 1 1 d . . . H1A H 0.7800 0.2028 1.0569 0.056 Uiso 1 1 calc R . . C7 C 1.3435(4) 0.01640(16) 0.8780(2) 0.0501(6) Uani 1 1 d . . . H7A H 1.4685 -0.0135 0.8905 0.060 Uiso 1 1 calc R . . C6 C 1.2493(4) 0.01990(17) 0.7813(2) 0.0515(6) Uani 1 1 d . . . H6A H 1.3128 -0.0054 0.7298 0.062 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 0.0866(3) 0.1005(3) 0.03558(17) 0.01693(14) 0.00574(15) -0.02752(18) O3 0.0492(9) 0.0555(10) 0.0244(7) 0.0022(7) -0.0027(6) -0.0134(8) O4 0.0515(10) 0.0582(11) 0.0375(8) 0.0109(8) 0.0016(7) -0.0087(8) O1 0.0579(12) 0.0753(14) 0.0742(14) 0.0120(12) -0.0251(10) 0.0125(11) N2 0.0431(11) 0.0391(10) 0.0414(10) 0.0017(8) -0.0069(8) 0.0049(8) N1 0.0415(11) 0.0592(13) 0.0434(11) 0.0093(10) -0.0108(8) -0.0029(10) C11 0.0410(11) 0.0317(10) 0.0286(9) -0.0043(8) 0.0012(8) -0.0005(9) C3 0.0362(11) 0.0416(12) 0.0325(10) 0.0035(9) -0.0051(8) -0.0042(9) C4 0.0358(10) 0.0325(10) 0.0294(9) 0.0033(8) -0.0009(7) -0.0052(9) O2 0.0818(16) 0.120(2) 0.0501(12) -0.0233(14) -0.0270(11) 0.0214(15) C8 0.0359(10) 0.0304(10) 0.0292(9) 0.0019(8) -0.0015(8) -0.0032(8) C10 0.0395(11) 0.0380(11) 0.0285(9) -0.0007(8) 0.0035(8) 0.0003(9) C12 0.0439(12) 0.0399(12) 0.0298(10) 0.0002(9) -0.0011(8) -0.0040(10) C9 0.0411(11) 0.0425(12) 0.0260(9) 0.0015(8) -0.0013(8) -0.0069(9) C15 0.0461(14) 0.0627(16) 0.0432(13) -0.0099(12) -0.0050(10) -0.0119(12) C16 0.0442(13) 0.0504(14) 0.0371(12) -0.0061(10) 0.0048(9) -0.0089(11) C5 0.0486(13) 0.0473(13) 0.0316(11) -0.0062(9) 0.0014(9) -0.0016(10) C13 0.0569(14) 0.0410(12) 0.0307(10) 0.0018(9) 0.0010(9) -0.0050(11) C2 0.0343(11) 0.0558(14) 0.0478(13) 0.0017(11) 0.0021(9) 0.0065(10) C14 0.0552(14) 0.0538(14) 0.0306(11) -0.0032(10) -0.0093(9) -0.0020(12) C1 0.0446(13) 0.0582(15) 0.0389(12) -0.0053(11) 0.0078(10) 0.0023(11) C7 0.0439(13) 0.0448(14) 0.0601(16) -0.0050(12) -0.0012(11) 0.0107(11) C6 0.0554(15) 0.0519(15) 0.0482(14) -0.0130(12) 0.0103(11) 0.0029(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 C13 1.885(2) . ? O3 C10 1.365(3) . ? O3 C9 1.392(2) . ? O4 C10 1.193(3) . ? O1 N1 1.206(3) . ? N2 C7 1.314(3) . ? N2 C8 1.360(3) . ? N1 O2 1.220(3) . ? N1 C3 1.471(3) . ? C11 C12 1.386(3) . ? C11 C16 1.387(3) . ? C11 C10 1.486(3) . ? C3 C2 1.351(3) . ? C3 C4 1.426(3) . ? C4 C5 1.412(3) . ? C4 C8 1.426(3) . ? C8 C9 1.415(3) . ? C12 C13 1.378(3) . ? C12 H12A 0.9500 . ? C9 C1 1.350(3) . ? C15 C14 1.370(4) . ? C15 C16 1.388(3) . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C5 C6 1.357(4) . ? C5 H5A 0.9500 . ? C13 C14 1.385(4) . ? C2 C1 1.401(3) . ? C2 H2B 0.9500 . ? C14 H14A 0.9500 . ? C1 H1A 0.9500 . ? C7 C6 1.400(4) . ? C7 H7A 0.9500 . ? C6 H6A 0.9500 . ? 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 C10 O3 C9 117.66(17) . . ? C7 N2 C8 117.4(2) . . ? O1 N1 O2 122.6(2) . . ? O1 N1 C3 118.8(2) . . ? O2 N1 C3 118.5(2) . . ? C12 C11 C16 120.1(2) . . ? C12 C11 C10 121.23(19) . . ? C16 C11 C10 118.61(19) . . ? C2 C3 C4 122.7(2) . . ? C2 C3 N1 116.0(2) . . ? C4 C3 N1 121.2(2) . . ? C5 C4 C3 127.5(2) . . ? C5 C4 C8 116.2(2) . . ? C3 C4 C8 116.30(19) . . ? N2 C8 C9 117.81(19) . . ? N2 C8 C4 123.4(2) . . ? C9 C8 C4 118.83(19) . . ? O4 C10 O3 123.49(19) . . ? O4 C10 C11 125.6(2) . . ? O3 C10 C11 110.90(17) . . ? C13 C12 C11 119.0(2) . . ? C13 C12 H12A 120.5 . . ? C11 C12 H12A 120.5 . . ? C1 C9 O3 118.4(2) . . ? C1 C9 C8 122.6(2) . . ? O3 C9 C8 118.8(2) . . ? C14 C15 C16 120.9(2) . . ? C14 C15 H15A 119.6 . . ? C16 C15 H15A 119.6 . . ? C15 C16 C11 119.6(2) . . ? C15 C16 H16A 120.2 . . ? C11 C16 H16A 120.2 . . ? C6 C5 C4 119.7(2) . . ? C6 C5 H5A 120.2 . . ? C4 C5 H5A 120.2 . . ? C12 C13 C14 121.5(2) . . ? C12 C13 Br1 118.71(18) . . ? C14 C13 Br1 119.77(17) . . ? C3 C2 C1 120.5(2) . . ? C3 C2 H2B 119.7 . . ? C1 C2 H2B 119.7 . . ? C15 C14 C13 118.9(2) . . ? C15 C14 H14A 120.6 . . ? C13 C14 H14A 120.6 . . ? C9 C1 C2 119.0(2) . . ? C9 C1 H1A 120.5 . . ? C2 C1 H1A 120.5 . . ? N2 C7 C6 123.6(2) . . ? N2 C7 H7A 118.2 . . ? C6 C7 H7A 118.2 . . ? C5 C6 C7 119.6(2) . . ? C5 C6 H6A 120.2 . . ? C7 C6 H6A 120.2 . . ? 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 C7 H7A N2 0.95 2.68 3.432(3) 136.8 3_857 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.34 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.420 _refine_diff_density_min -1.131 _refine_diff_density_rms 0.134