data_14mrb1h _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C16 H16 Br N O' _chemical_formula_weight 318.21 _chemical_absolute_configuration ad 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.7753(3) _cell_length_b 9.7463(4) _cell_length_c 10.5571(5) _cell_angle_alpha 90.00 _cell_angle_beta 93.5333(6) _cell_angle_gamma 90.00 _cell_volume 695.80(5) _cell_formula_units_Z 2 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 8542 _cell_measurement_theta_min 2.85 _cell_measurement_theta_max 28.29 _exptl_crystal_description 'block' _exptl_crystal_colour 'colorless' _exptl_crystal_size_max 0.52 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.519 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 324 _exptl_absorpt_coefficient_mu 2.945 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.3096 _exptl_absorpt_correction_T_max 0.6192 _exptl_absorpt_process_details SADABS _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 APEX-II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 10824 _diffrn_reflns_av_R_equivalents 0.0209 _diffrn_reflns_av_sigmaI/netI 0.0196 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.93 _diffrn_reflns_theta_max 28.29 _reflns_number_total 3433 _reflns_number_gt 3383 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _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^)+(0.0364P)^2^+0.1290P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.007(5) _refine_ls_number_reflns 3433 _refine_ls_number_parameters 177 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0212 _refine_ls_R_factor_gt 0.0209 _refine_ls_wR_factor_ref 0.0529 _refine_ls_wR_factor_gt 0.0527 _refine_ls_goodness_of_fit_ref 1.067 _refine_ls_restrained_S_all 1.067 _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 0.885937(19) 0.688631(18) -0.307152(12) 0.01440(5) Uani 1 1 d . . . O1 O 0.04266(19) 0.51327(12) 0.01537(13) 0.0159(2) Uani 1 1 d . . . N1 N 0.1472(2) 0.73418(15) -0.00903(13) 0.0115(3) Uani 1 1 d D . . H1N H 0.110(3) 0.8179(12) 0.003(2) 0.014 Uiso 1 1 d D . . C1 C 0.0224(2) 0.63673(17) 0.03275(15) 0.0108(3) Uani 1 1 d . . . C2 C -0.1475(2) 0.6930(2) 0.10436(13) 0.0121(3) Uani 1 1 d . . . H2A H -0.2737 0.6741 0.0551 0.014 Uiso 1 1 calc R . . H2B H -0.1332 0.7937 0.1125 0.014 Uiso 1 1 calc R . . C3 C -0.1551(3) 0.62953(18) 0.23735(16) 0.0127(3) Uani 1 1 d . . . H3 H -0.1545 0.5274 0.2279 0.015 Uiso 1 1 calc R . . C4 C 0.0177(2) 0.66911(18) 0.32834(14) 0.0115(3) Uani 1 1 d . . . C5 C 0.0751(3) 0.80586(19) 0.34611(18) 0.0161(3) Uani 1 1 d . . . H5 H 0.0142 0.8754 0.2942 0.019 Uiso 1 1 calc R . . C6 C 0.2208(3) 0.8412(2) 0.43925(17) 0.0180(3) Uani 1 1 d . . . H6 H 0.2591 0.9344 0.4504 0.022 Uiso 1 1 calc R . . C7 C 0.3100(3) 0.7402(2) 0.51578(19) 0.0197(4) Uani 1 1 d . . . H7 H 0.4072 0.7645 0.5806 0.024 Uiso 1 1 calc R . . C8 C 0.2572(3) 0.6039(2) 0.49753(19) 0.0199(4) Uani 1 1 d . . . H8 H 0.3201 0.5344 0.5486 0.024 Uiso 1 1 calc R . . C9 C 0.1121(3) 0.56924(18) 0.40448(18) 0.0153(3) Uani 1 1 d . . . H9 H 0.0765 0.4756 0.3925 0.018 Uiso 1 1 calc R . . C10 C -0.3498(3) 0.6707(3) 0.29351(17) 0.0209(4) Uani 1 1 d . . . H10A H -0.3573 0.6286 0.3774 0.031 Uiso 1 1 calc R . . H10B H -0.4612 0.6392 0.2374 0.031 Uiso 1 1 calc R . . H10C H -0.3553 0.7708 0.3017 0.031 Uiso 1 1 calc R . . C11 C 0.3184(2) 0.71599(14) -0.07790(15) 0.0092(3) Uani 1 1 d . . . C12 C 0.3811(3) 0.58871(18) -0.12133(17) 0.0123(3) Uani 1 1 d . . . H12 H 0.3084 0.5079 -0.1051 0.015 Uiso 1 1 calc R . . C13 C 0.5518(3) 0.58143(19) -0.18889(18) 0.0127(3) Uani 1 1 d . . . H13 H 0.5958 0.4954 -0.2188 0.015 Uiso 1 1 calc R . . C14 C 0.6571(2) 0.7003(2) -0.21234(14) 0.0111(3) Uani 1 1 d . . . C15 C 0.5961(3) 0.8267(2) -0.16851(19) 0.0121(3) Uani 1 1 d . . . H15 H 0.6692 0.9074 -0.1844 0.015 Uiso 1 1 calc R . . C16 C 0.4274(3) 0.83363(17) -0.10132(16) 0.0120(3) Uani 1 1 d . . . H16 H 0.3852 0.9198 -0.0707 0.014 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 0.01347(8) 0.01475(8) 0.01551(8) 0.00089(8) 0.00512(5) 0.00018(8) O1 0.0174(6) 0.0105(6) 0.0205(6) 0.0004(5) 0.0053(5) 0.0008(4) N1 0.0121(7) 0.0086(5) 0.0139(6) -0.0024(5) 0.0024(5) 0.0013(5) C1 0.0113(7) 0.0123(6) 0.0087(7) 0.0006(6) -0.0007(6) 0.0011(6) C2 0.0107(6) 0.0125(6) 0.0130(6) 0.0007(9) 0.0011(5) 0.0017(9) C3 0.0124(7) 0.0124(7) 0.0137(7) -0.0003(6) 0.0029(6) -0.0026(6) C4 0.0126(6) 0.0132(9) 0.0090(6) -0.0005(6) 0.0031(5) -0.0001(6) C5 0.0172(8) 0.0165(9) 0.0144(8) 0.0007(7) -0.0001(7) 0.0013(6) C6 0.0173(9) 0.0210(9) 0.0156(8) -0.0024(7) 0.0003(7) -0.0012(7) C7 0.0164(9) 0.0295(10) 0.0131(8) -0.0006(8) -0.0003(7) 0.0026(8) C8 0.0200(10) 0.0254(10) 0.0144(9) 0.0044(7) 0.0021(8) 0.0076(8) C9 0.0170(8) 0.0152(8) 0.0144(8) 0.0016(7) 0.0057(7) 0.0021(7) C10 0.0138(7) 0.0295(13) 0.0201(8) -0.0011(8) 0.0063(6) -0.0008(8) C11 0.0109(7) 0.0065(10) 0.0098(6) -0.0003(5) -0.0011(5) 0.0012(5) C12 0.0130(8) 0.0081(7) 0.0159(8) -0.0007(6) 0.0022(6) -0.0009(6) C13 0.0150(9) 0.0098(8) 0.0135(8) -0.0009(6) 0.0012(6) 0.0020(7) C14 0.0103(6) 0.0133(9) 0.0096(6) 0.0009(7) 0.0001(5) 0.0002(8) C15 0.0132(9) 0.0099(8) 0.0132(7) 0.0007(6) -0.0001(6) -0.0018(6) C16 0.0140(8) 0.0081(8) 0.0136(8) -0.0002(6) -0.0014(6) 0.0006(6) _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 C14 1.8999(15) . ? O1 C1 1.226(2) . ? N1 C1 1.363(2) . ? N1 C11 1.418(2) . ? N1 H1N 0.864(9) . ? C1 C2 1.518(2) . ? C2 C3 1.538(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C3 C4 1.518(2) . ? C3 C10 1.532(2) . ? C3 H3 1.0000 . ? C4 C9 1.393(2) . ? C4 C5 1.398(2) . ? C5 C6 1.393(2) . ? C5 H5 0.9500 . ? C6 C7 1.388(3) . ? C6 H6 0.9500 . ? C7 C8 1.387(3) . ? C7 H7 0.9500 . ? C8 C9 1.388(3) . ? C8 H8 0.9500 . ? C9 H9 0.9500 . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 C16 1.394(2) . ? C11 C12 1.398(2) . ? C12 C13 1.397(3) . ? C12 H12 0.9500 . ? C13 C14 1.391(3) . ? C13 H13 0.9500 . ? C14 C15 1.388(3) . ? C15 C16 1.384(3) . ? C15 H15 0.9500 . ? C16 H16 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 C1 N1 C11 128.49(14) . . ? C1 N1 H1N 115.0(16) . . ? C11 N1 H1N 116.3(16) . . ? O1 C1 N1 123.92(16) . . ? O1 C1 C2 121.62(16) . . ? N1 C1 C2 114.46(15) . . ? C1 C2 C3 112.25(15) . . ? C1 C2 H2A 109.2 . . ? C3 C2 H2A 109.2 . . ? C1 C2 H2B 109.2 . . ? C3 C2 H2B 109.2 . . ? H2A C2 H2B 107.9 . . ? C4 C3 C10 109.72(14) . . ? C4 C3 C2 114.05(14) . . ? C10 C3 C2 109.02(14) . . ? C4 C3 H3 108.0 . . ? C10 C3 H3 108.0 . . ? C2 C3 H3 108.0 . . ? C9 C4 C5 118.36(16) . . ? C9 C4 C3 119.77(16) . . ? C5 C4 C3 121.64(15) . . ? C6 C5 C4 120.63(17) . . ? C6 C5 H5 119.7 . . ? C4 C5 H5 119.7 . . ? C7 C6 C5 120.00(18) . . ? C7 C6 H6 120.0 . . ? C5 C6 H6 120.0 . . ? C8 C7 C6 119.9(2) . . ? C8 C7 H7 120.0 . . ? C6 C7 H7 120.0 . . ? C7 C8 C9 119.79(19) . . ? C7 C8 H8 120.1 . . ? C9 C8 H8 120.1 . . ? C8 C9 C4 121.25(18) . . ? C8 C9 H9 119.4 . . ? C4 C9 H9 119.4 . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C16 C11 C12 119.78(15) . . ? C16 C11 N1 116.56(14) . . ? C12 C11 N1 123.66(15) . . ? C13 C12 C11 119.37(16) . . ? C13 C12 H12 120.3 . . ? C11 C12 H12 120.3 . . ? C14 C13 C12 119.89(17) . . ? C14 C13 H13 120.1 . . ? C12 C13 H13 120.1 . . ? C15 C14 C13 120.89(15) . . ? C15 C14 Br1 119.90(15) . . ? C13 C14 Br1 119.21(16) . . ? C16 C15 C14 119.11(17) . . ? C16 C15 H15 120.4 . . ? C14 C15 H15 120.4 . . ? C15 C16 C11 120.95(16) . . ? C15 C16 H16 119.5 . . ? C11 C16 H16 119.5 . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 28.29 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.200 _refine_diff_density_min -0.474 _refine_diff_density_rms 0.097