data_Davies122007 _publ_contact_author_name 'Mateusz Pitak' _publ_contact_author_address ; Department of Chemistry State University of New York at Buffalo Buffalo, NY 14260-3000, USA ; _publ_contact_author_email mpitak@buffalo.edu _publ_contact_author_phone (716)645-6800x2233 loop_ _publ_author_name _publ_author_address 'Mateusz Pitak' ;Department of Chemistry State University of New York at Buffalo Buffalo, NY 14260-3000, USA ; 'Gembicky, Milan' ;Department of Chemistry State University of New York at Buffalo Buffalo, NY 14260-3000, USA ; 'Coppens, Philip' ;Department of Chemistry State University of New York at Buffalo Buffalo, NY 14260-3000, USA ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 Br N O3' _chemical_formula_sum 'C16 H14 Br N O3' _chemical_formula_weight 348.19 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/n' _symmetry_space_group_name_Hall '-P 2yn' 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 7.2150(8) _cell_length_b 10.9179(12) _cell_length_c 19.254(2) _cell_angle_alpha 90.00 _cell_angle_beta 94.616(2) _cell_angle_gamma 90.00 _cell_volume 1511.7(3) _cell_formula_units_Z 4 _cell_measurement_temperature 90(2) _cell_measurement_reflns_used 8763 _cell_measurement_theta_min 2.83 _cell_measurement_theta_max 28.27 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.40 _exptl_crystal_size_min 0.40 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.530 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.728 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.325 _exptl_absorpt_correction_T_max 0.341 _exptl_absorpt_process_details '(SADABS 2004/1 Bruker 2004)' _exptl_special_details ; Data collection was performed with four runs at \f = 0.00 \%, at \f = 72.00 \%, at \f = 144 \% and at \f = 216 \% (360 frames each). Frame width = 0.50 \% in \w. Data were merged, corrected for decay, and treated with multi-scan absorption corrections, Bruker (2004). ; _diffrn_ambient_temperature 90(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX2' _diffrn_source_type 'RIGAKU RU-2000BEH' _diffrn_detector_area_resol_mean 8.33 _diffrn_measurement_method '\f and \w scans' _diffrn_standards_number 0 _diffrn_standards_interval_count 0 _diffrn_standards_interval_time 0 _diffrn_standards_decay_% 0 _diffrn_reflns_number 21965 _diffrn_reflns_av_R_equivalents 0.0639 _diffrn_reflns_av_sigmaI/netI 0.0437 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _diffrn_reflns_theta_min 2.12 _diffrn_reflns_theta_max 28.36 _reflns_number_total 3792 _reflns_number_gt 3375 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'APEX2 (Bruker, 2004)' _computing_cell_refinement 'Bruker Saint v7.23A (Bruker, 2005)' _computing_data_reduction 'Bruker Saint v7.23A (Bruker, 2005)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _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^)+(0.0530P)^2^+0.3528P] 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 SHELXL _refine_ls_extinction_coef 0.0376(19) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3792 _refine_ls_number_parameters 194 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0386 _refine_ls_R_factor_gt 0.0338 _refine_ls_wR_factor_ref 0.0937 _refine_ls_wR_factor_gt 0.0906 _refine_ls_goodness_of_fit_ref 1.046 _refine_ls_restrained_S_all 1.046 _refine_ls_shift/su_max 0.000 _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 -0.33061(3) -0.065965(18) 0.124509(11) 0.03324(10) Uani 1 1 d . . . N1 N 0.6299(2) 0.44184(13) 0.07960(8) 0.0237(3) Uani 1 1 d . . . O1 O 0.84604(18) 0.40330(12) -0.02276(7) 0.0270(3) Uani 1 1 d . . . O2 O 0.6643(2) 0.25230(13) -0.06879(7) 0.0343(3) Uani 1 1 d . . . O3 O 0.1946(2) 0.47925(14) 0.22670(8) 0.0359(3) Uani 1 1 d . . . C5 C 0.1797(3) 0.08334(16) 0.08700(10) 0.0259(4) Uani 1 1 d . . . H5 H 0.2932 0.0545 0.0711 0.031 Uiso 1 1 calc R . . C7 C 0.3215(2) 0.29079(15) 0.09664(9) 0.0223(3) Uani 1 1 d . . . C11 C 0.4238(2) 0.27945(16) 0.03855(9) 0.0238(3) Uani 1 1 d . . . H11 H 0.3888 0.2215 0.0031 0.029 Uiso 1 1 calc R . . C15 C 0.6980(2) 0.33087(16) -0.02560(9) 0.0248(3) Uani 1 1 d . . . C9 C 0.5308(3) 0.45582(16) 0.13501(9) 0.0238(3) Uani 1 1 d . . . C1 C -0.0062(2) 0.24811(16) 0.12686(9) 0.0245(3) Uani 1 1 d . . . H1 H -0.0204 0.3322 0.1380 0.029 Uiso 1 1 calc R . . C10 C 0.5774(2) 0.35415(16) 0.03347(9) 0.0227(3) Uani 1 1 d . . . C3 C -0.1305(3) 0.04509(17) 0.11640(9) 0.0255(4) Uani 1 1 d . . . C6 C 0.1618(2) 0.20678(16) 0.10405(9) 0.0223(3) Uani 1 1 d . . . C14 C 0.5978(3) 0.55450(17) 0.18539(10) 0.0309(4) Uani 1 1 d . . . H14A H 0.7315 0.5672 0.1827 0.046 Uiso 1 1 calc R . . H14C H 0.5742 0.5298 0.2328 0.046 Uiso 1 1 calc R . . H14B H 0.5312 0.6309 0.1735 0.046 Uiso 1 1 calc R . . C12 C 0.2879(3) 0.39117(17) 0.21459(9) 0.0258(4) Uani 1 1 d . . . C16 C 0.9753(3) 0.38015(18) -0.07508(10) 0.0300(4) Uani 1 1 d . . . H16B H 1.0167 0.2947 -0.0719 0.045 Uiso 1 1 calc R . . H16C H 1.0829 0.4346 -0.0672 0.045 Uiso 1 1 calc R . . H16A H 0.9135 0.3955 -0.1215 0.045 Uiso 1 1 calc R . . C8 C 0.3779(2) 0.38001(15) 0.14621(9) 0.0231(3) Uani 1 1 d . . . C2 C -0.1531(3) 0.16739(17) 0.13343(9) 0.0259(4) Uani 1 1 d . . . H2 H -0.2670 0.1955 0.1493 0.031 Uiso 1 1 calc R . . C13 C 0.3327(3) 0.29079(18) 0.26630(10) 0.0333(4) Uani 1 1 d . . . H13A H 0.4645 0.2952 0.2830 0.050 Uiso 1 1 calc R . . H13B H 0.3067 0.2113 0.2440 0.050 Uiso 1 1 calc R . . H13C H 0.2561 0.3002 0.3058 0.050 Uiso 1 1 calc R . . C4 C 0.0335(3) 0.00195(16) 0.09296(10) 0.0269(4) Uani 1 1 d . . . H4 H 0.0461 -0.0819 0.0811 0.032 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 0.02773(14) 0.03377(14) 0.03862(15) -0.00128(7) 0.00514(9) -0.00968(7) N1 0.0262(8) 0.0233(7) 0.0215(7) -0.0003(5) 0.0022(6) -0.0021(5) O1 0.0284(7) 0.0295(6) 0.0239(6) -0.0046(5) 0.0076(5) -0.0086(5) O2 0.0363(7) 0.0382(7) 0.0299(7) -0.0127(6) 0.0108(6) -0.0142(6) O3 0.0431(8) 0.0332(7) 0.0328(7) -0.0044(6) 0.0121(6) 0.0033(6) C5 0.0249(9) 0.0262(8) 0.0270(9) -0.0012(7) 0.0039(7) -0.0007(7) C7 0.0224(8) 0.0219(8) 0.0224(8) 0.0012(6) 0.0010(6) -0.0013(6) C11 0.0263(8) 0.0245(8) 0.0207(8) -0.0014(6) 0.0017(6) -0.0032(6) C15 0.0260(9) 0.0265(8) 0.0222(8) 0.0001(6) 0.0035(6) -0.0046(6) C9 0.0266(9) 0.0238(8) 0.0212(8) 0.0006(6) 0.0026(7) -0.0007(6) C1 0.0245(8) 0.0242(8) 0.0249(8) 0.0005(6) 0.0028(7) -0.0004(6) C10 0.0251(8) 0.0235(8) 0.0196(8) 0.0012(6) 0.0013(6) -0.0018(6) C3 0.0244(9) 0.0292(8) 0.0224(8) 0.0014(7) -0.0005(7) -0.0063(7) C6 0.0238(8) 0.0246(8) 0.0185(7) 0.0007(6) 0.0019(6) -0.0016(6) C14 0.0384(11) 0.0287(9) 0.0264(9) -0.0064(7) 0.0074(8) -0.0088(7) C12 0.0292(9) 0.0262(8) 0.0223(8) -0.0024(7) 0.0037(7) -0.0053(7) C16 0.0309(10) 0.0327(9) 0.0278(9) -0.0068(7) 0.0119(7) -0.0089(7) C8 0.0263(8) 0.0221(8) 0.0208(8) 0.0007(6) 0.0020(6) 0.0007(6) C2 0.0234(8) 0.0299(9) 0.0246(8) 0.0011(7) 0.0031(6) -0.0011(7) C13 0.0438(11) 0.0332(10) 0.0234(9) 0.0032(7) 0.0062(8) -0.0024(8) C4 0.0295(9) 0.0238(8) 0.0275(9) -0.0019(7) 0.0030(7) -0.0026(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 Br1 C3 1.9016(18) . ? N1 C10 1.340(2) . ? N1 C9 1.340(2) . ? O1 C15 1.326(2) . ? O1 C16 1.449(2) . ? O2 C15 1.206(2) . ? O3 C12 1.207(2) . ? C5 C4 1.391(2) . ? C5 C6 1.396(2) . ? C5 H5 0.9500 . ? C7 C11 1.394(2) . ? C7 C8 1.401(2) . ? C7 C6 1.489(2) . ? C11 C10 1.386(2) . ? C11 H11 0.9500 . ? C15 C10 1.508(2) . ? C9 C8 1.410(2) . ? C9 C14 1.503(2) . ? C1 C2 1.392(2) . ? C1 C6 1.397(2) . ? C1 H1 0.9500 . ? C3 C4 1.382(3) . ? C3 C2 1.388(2) . ? C14 H14A 0.9800 . ? C14 H14C 0.9800 . ? C14 H14B 0.9800 . ? C12 C13 1.498(3) . ? C12 C8 1.519(2) . ? C16 H16B 0.9800 . ? C16 H16C 0.9800 . ? C16 H16A 0.9800 . ? C2 H2 0.9500 . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? C4 H4 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 N1 C9 117.95(16) . . ? C15 O1 C16 115.36(14) . . ? C4 C5 C6 120.80(17) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C11 C7 C8 117.68(15) . . ? C11 C7 C6 119.08(15) . . ? C8 C7 C6 123.22(15) . . ? C10 C11 C7 118.84(16) . . ? C10 C11 H11 120.6 . . ? C7 C11 H11 120.6 . . ? O2 C15 O1 124.72(16) . . ? O2 C15 C10 122.91(16) . . ? O1 C15 C10 112.33(15) . . ? N1 C9 C8 121.96(16) . . ? N1 C9 C14 115.54(16) . . ? C8 C9 C14 122.48(16) . . ? C2 C1 C6 120.69(16) . . ? C2 C1 H1 119.7 . . ? C6 C1 H1 119.7 . . ? N1 C10 C11 123.99(16) . . ? N1 C10 C15 118.08(15) . . ? C11 C10 C15 117.86(15) . . ? C4 C3 C2 121.68(17) . . ? C4 C3 Br1 119.02(13) . . ? C2 C3 Br1 119.30(14) . . ? C5 C6 C1 119.02(16) . . ? C5 C6 C7 119.03(15) . . ? C1 C6 C7 121.94(15) . . ? C9 C14 H14A 109.5 . . ? C9 C14 H14C 109.5 . . ? H14A C14 H14C 109.5 . . ? C9 C14 H14B 109.5 . . ? H14A C14 H14B 109.5 . . ? H14C C14 H14B 109.5 . . ? O3 C12 C13 123.24(17) . . ? O3 C12 C8 121.01(17) . . ? C13 C12 C8 115.64(16) . . ? O1 C16 H16B 109.5 . . ? O1 C16 H16C 109.5 . . ? H16B C16 H16C 109.5 . . ? O1 C16 H16A 109.5 . . ? H16B C16 H16A 109.5 . . ? H16C C16 H16A 109.5 . . ? C7 C8 C9 119.48(16) . . ? C7 C8 C12 121.67(15) . . ? C9 C8 C12 118.69(15) . . ? C3 C2 C1 118.86(17) . . ? C3 C2 H2 120.6 . . ? C1 C2 H2 120.6 . . ? 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 . . ? C3 C4 C5 118.95(16) . . ? C3 C4 H4 120.5 . . ? C5 C4 H4 120.5 . . ? 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 C8 C7 C11 C10 1.5(2) . . . . ? C6 C7 C11 C10 -177.12(16) . . . . ? C16 O1 C15 O2 -2.0(3) . . . . ? C16 O1 C15 C10 175.81(15) . . . . ? C10 N1 C9 C8 1.3(3) . . . . ? C10 N1 C9 C14 179.25(16) . . . . ? C9 N1 C10 C11 1.9(3) . . . . ? C9 N1 C10 C15 -174.83(16) . . . . ? C7 C11 C10 N1 -3.4(3) . . . . ? C7 C11 C10 C15 173.40(16) . . . . ? O2 C15 C10 N1 178.42(18) . . . . ? O1 C15 C10 N1 0.5(2) . . . . ? O2 C15 C10 C11 1.5(3) . . . . ? O1 C15 C10 C11 -176.42(16) . . . . ? C4 C5 C6 C1 -0.4(3) . . . . ? C4 C5 C6 C7 -179.76(16) . . . . ? C2 C1 C6 C5 0.8(3) . . . . ? C2 C1 C6 C7 -179.87(16) . . . . ? C11 C7 C6 C5 41.1(2) . . . . ? C8 C7 C6 C5 -137.39(18) . . . . ? C11 C7 C6 C1 -138.16(18) . . . . ? C8 C7 C6 C1 43.3(3) . . . . ? C11 C7 C8 C9 1.5(2) . . . . ? C6 C7 C8 C9 -179.97(16) . . . . ? C11 C7 C8 C12 -173.85(16) . . . . ? C6 C7 C8 C12 4.7(3) . . . . ? N1 C9 C8 C7 -3.0(3) . . . . ? C14 C9 C8 C7 179.20(17) . . . . ? N1 C9 C8 C12 172.46(17) . . . . ? C14 C9 C8 C12 -5.3(3) . . . . ? O3 C12 C8 C7 -112.5(2) . . . . ? C13 C12 C8 C7 71.2(2) . . . . ? O3 C12 C8 C9 72.2(2) . . . . ? C13 C12 C8 C9 -104.19(19) . . . . ? C4 C3 C2 C1 -0.2(3) . . . . ? Br1 C3 C2 C1 -179.56(13) . . . . ? C6 C1 C2 C3 -0.5(3) . . . . ? C2 C3 C4 C5 0.6(3) . . . . ? Br1 C3 C4 C5 179.94(14) . . . . ? C6 C5 C4 C3 -0.3(3) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 28.36 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.402 _refine_diff_density_min -0.827 _refine_diff_density_rms 0.083