data_su030 _publ_section_title SU030 _publ_contact_author_name 'Dustin Bringley' _publ_contact_author_address 'Dept. of Chemistry, Stanford University' _publ_contact_author_email dbringle@stanford.edu _publ_contact_author_phone '650 723 1100' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C16 H14 Cl N O2' _chemical_formula_sum 'C16 H14 Cl N O2' _chemical_formula_weight 287.73 _chemical_absolute_configuration rmad loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0181 0.0091 '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' 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M P212121 _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.93800(10) _cell_length_b 7.9686(2) _cell_length_c 27.9472(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1322.39(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 3933 _cell_measurement_theta_min 5.78 _cell_measurement_theta_max 69.34 _exptl_crystal_description plate _exptl_crystal_colour colorless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.445 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 600 _exptl_absorpt_coefficient_mu 2.562 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.5917 _exptl_absorpt_correction_T_max 0.8873 _exptl_absorpt_process_details 'SADABS, Sheldrick, 2008' _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX' _diffrn_measurement_method 'combination of \w and \f-scans ' _diffrn_detector_area_resol_mean 8.33 _diffrn_reflns_number 12932 _diffrn_reflns_av_R_equivalents 0.0392 _diffrn_reflns_av_sigmaI/netI 0.0302 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 69.67 _reflns_number_total 2472 _reflns_number_gt 2309 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX-II v2009-9' _computing_cell_refinement 'Bruker SAINT v7.66A' _computing_data_reduction 'Bruker SAINT v7.66A' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics ? _computing_publication_material ? _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^)+(0.0415P)^2^+0.4903P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881, 992 Friedel Pairs measured' _refine_ls_abs_structure_Flack 0.016(16) _refine_ls_number_reflns 2472 _refine_ls_number_parameters 181 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0356 _refine_ls_R_factor_gt 0.0318 _refine_ls_wR_factor_ref 0.0808 _refine_ls_wR_factor_gt 0.0785 _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_restrained_S_all 1.049 _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 Cl1 Cl 0.52869(9) 0.89340(7) 0.265670(18) 0.02388(14) Uani 1 1 d . . . O1 O 0.6182(3) 1.1558(2) 0.33909(6) 0.0330(4) Uani 1 1 d . . . O2 O 0.2619(3) 1.2073(2) 0.33262(7) 0.0345(4) Uani 1 1 d . . . N1 N 0.4237(3) 1.1147(3) 0.33176(6) 0.0238(4) Uani 1 1 d . . . C1 C 0.3815(4) 0.9293(3) 0.32086(8) 0.0196(5) Uani 1 1 d . . . C2 C 0.1351(4) 0.8831(3) 0.31511(8) 0.0210(4) Uani 1 1 d . . . H2A H 0.0771 0.9166 0.2833 0.025 Uiso 1 1 calc R . . H2B H 0.0413 0.9355 0.3403 0.025 Uiso 1 1 calc R . . C3 C 0.1419(4) 0.6932(3) 0.32041(8) 0.0197(4) Uani 1 1 d . . . C4 C 0.3599(4) 0.6441(3) 0.34589(7) 0.0190(5) Uani 1 1 d . . . H4A H 0.4590 0.5794 0.3242 0.023 Uiso 1 1 calc R . . H4B H 0.3271 0.5750 0.3745 0.023 Uiso 1 1 calc R . . C5 C 0.4733(4) 0.8111(3) 0.36051(7) 0.0172(4) Uani 1 1 d . . . H5A H 0.6405 0.8007 0.3574 0.021 Uiso 1 1 calc R . . C6 C 0.4131(3) 0.8716(3) 0.41068(7) 0.0169(4) Uani 1 1 d . . . C7 C 0.5658(4) 0.9644(3) 0.43651(7) 0.0171(4) Uani 1 1 d . . . H7A H 0.7057 0.9935 0.4223 0.021 Uiso 1 1 calc R . . C8 C 0.5192(4) 1.0182(2) 0.48427(7) 0.0154(4) Uani 1 1 d . . . C9 C 0.6770(4) 1.1120(3) 0.51136(7) 0.0182(4) Uani 1 1 d . . . H9A H 0.8175 1.1421 0.4976 0.022 Uiso 1 1 calc R . . C10 C 0.6278(4) 1.1594(3) 0.55735(8) 0.0212(5) Uani 1 1 d . . . H10A H 0.7342 1.2229 0.5752 0.025 Uiso 1 1 calc R . . C11 C 0.4207(4) 1.1148(3) 0.57841(7) 0.0221(5) Uani 1 1 d . . . H11A H 0.3888 1.1480 0.6103 0.027 Uiso 1 1 calc R . . C12 C 0.2653(4) 1.0240(3) 0.55328(8) 0.0200(5) Uani 1 1 d . . . H12A H 0.1263 0.9945 0.5679 0.024 Uiso 1 1 calc R . . C13 C 0.3101(4) 0.9732(3) 0.50541(8) 0.0169(4) Uani 1 1 d . . . C14 C 0.1541(3) 0.8785(3) 0.47811(8) 0.0186(4) Uani 1 1 d . . . H14A H 0.0128 0.8494 0.4917 0.022 Uiso 1 1 calc R . . C15 C 0.2037(4) 0.8284(3) 0.43247(8) 0.0181(4) Uani 1 1 d . . . H15A H 0.0971 0.7639 0.4150 0.022 Uiso 1 1 calc R . . C16 C -0.0119(4) 0.5887(3) 0.30385(7) 0.0235(5) Uani 1 1 d . . . H16A H -0.1391 0.6308 0.2871 0.028 Uiso 1 1 calc R . . H16B H 0.0047 0.4713 0.3087 0.028 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 Cl1 0.0269(3) 0.0273(3) 0.0175(2) 0.0010(2) 0.0017(2) 0.0008(2) O1 0.0387(10) 0.0276(9) 0.0327(9) 0.0041(7) -0.0088(8) -0.0115(8) O2 0.0436(11) 0.0205(9) 0.0395(10) -0.0014(8) 0.0028(9) 0.0049(8) N1 0.0330(11) 0.0219(10) 0.0166(9) 0.0026(8) -0.0017(8) -0.0042(9) C1 0.0222(11) 0.0176(11) 0.0190(10) -0.0015(8) 0.0035(9) 0.0016(9) C2 0.0218(11) 0.0218(11) 0.0195(10) 0.0003(9) -0.0017(8) 0.0017(10) C3 0.0222(11) 0.0208(11) 0.0161(10) -0.0011(8) 0.0013(9) 0.0021(10) C4 0.0205(11) 0.0185(11) 0.0181(10) -0.0012(8) -0.0007(9) 0.0020(9) C5 0.0174(10) 0.0178(10) 0.0166(10) 0.0001(8) -0.0021(9) 0.0010(9) C6 0.0203(10) 0.0132(10) 0.0172(10) 0.0019(8) -0.0010(8) 0.0025(8) C7 0.0160(10) 0.0153(10) 0.0200(10) 0.0028(8) 0.0020(8) -0.0002(8) C8 0.0162(10) 0.0113(9) 0.0188(9) 0.0021(7) -0.0007(8) 0.0025(8) C9 0.0186(10) 0.0143(10) 0.0216(11) 0.0039(9) 0.0003(8) 0.0006(9) C10 0.0246(11) 0.0172(11) 0.0217(11) -0.0002(8) -0.0056(9) 0.0016(9) C11 0.0294(12) 0.0202(11) 0.0167(10) -0.0009(9) 0.0010(8) 0.0059(10) C12 0.0197(11) 0.0196(11) 0.0208(11) 0.0046(9) 0.0035(9) 0.0039(9) C13 0.0188(11) 0.0116(9) 0.0204(11) 0.0036(8) -0.0009(8) 0.0028(9) C14 0.0139(10) 0.0169(10) 0.0250(11) 0.0042(9) 0.0023(8) 0.0021(9) C15 0.0175(11) 0.0149(10) 0.0219(11) 0.0015(8) -0.0041(9) -0.0004(8) C16 0.0257(12) 0.0244(11) 0.0206(10) -0.0020(8) -0.0026(9) 0.0028(10) _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 Cl1 C1 1.796(2) . ? O1 N1 1.218(3) . ? O2 N1 1.212(3) . ? N1 C1 1.529(3) . ? C1 C2 1.517(3) . ? C1 C5 1.553(3) . ? C2 C3 1.521(3) . ? C3 C16 1.320(3) . ? C3 C4 1.528(3) . ? C4 C5 1.546(3) . ? C5 C6 1.525(3) . ? C6 C7 1.375(3) . ? C6 C15 1.426(3) . ? C7 C8 1.429(3) . ? C8 C9 1.417(3) . ? C8 C13 1.421(3) . ? C9 C10 1.371(3) . ? C10 C11 1.409(3) . ? C11 C12 1.367(3) . ? C12 C13 1.423(3) . ? C13 C14 1.417(3) . ? C14 C15 1.369(3) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C5 H5A 1.0000 . ? C7 H7A 0.9500 . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C11 H11A 0.9500 . ? C12 H12A 0.9500 . ? C14 H14A 0.9500 . ? C15 H15A 0.9500 . ? C16 H16A 0.9500 . ? C16 H16B 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 O2 N1 O1 125.8(2) . . ? O2 N1 C1 117.54(19) . . ? O1 N1 C1 116.69(19) . . ? C2 C1 N1 114.43(18) . . ? C2 C1 C5 105.49(18) . . ? N1 C1 C5 112.70(17) . . ? C2 C1 Cl1 109.87(15) . . ? N1 C1 Cl1 104.19(14) . . ? C5 C1 Cl1 110.21(14) . . ? C1 C2 C3 101.84(18) . . ? C16 C3 C2 125.1(2) . . ? C16 C3 C4 126.0(2) . . ? C2 C3 C4 108.81(18) . . ? C3 C4 C5 105.76(17) . . ? C6 C5 C4 114.38(17) . . ? C6 C5 C1 112.48(17) . . ? C4 C5 C1 100.39(16) . . ? C7 C6 C15 118.71(19) . . ? C7 C6 C5 119.86(19) . . ? C15 C6 C5 121.38(19) . . ? C6 C7 C8 121.6(2) . . ? C9 C8 C13 119.25(18) . . ? C9 C8 C7 121.94(19) . . ? C13 C8 C7 118.79(19) . . ? C10 C9 C8 120.3(2) . . ? C9 C10 C11 120.5(2) . . ? C12 C11 C10 120.5(2) . . ? C11 C12 C13 120.5(2) . . ? C14 C13 C8 118.79(19) . . ? C14 C13 C12 122.4(2) . . ? C8 C13 C12 118.8(2) . . ? C15 C14 C13 121.1(2) . . ? C14 C15 C6 121.0(2) . . ? C1 C2 H2A 111.4 . . ? C3 C2 H2A 111.4 . . ? C1 C2 H2B 111.4 . . ? C3 C2 H2B 111.4 . . ? H2A C2 H2B 109.3 . . ? C3 C4 H4A 110.6 . . ? C5 C4 H4A 110.6 . . ? C3 C4 H4B 110.6 . . ? C5 C4 H4B 110.6 . . ? H4A C4 H4B 108.7 . . ? C6 C5 H5A 109.7 . . ? C4 C5 H5A 109.7 . . ? C1 C5 H5A 109.7 . . ? C6 C7 H7A 119.2 . . ? C8 C7 H7A 119.2 . . ? C10 C9 H9A 119.8 . . ? C8 C9 H9A 119.8 . . ? C9 C10 H10A 119.7 . . ? C11 C10 H10A 119.7 . . ? C12 C11 H11A 119.7 . . ? C10 C11 H11A 119.7 . . ? C11 C12 H12A 119.7 . . ? C13 C12 H12A 119.7 . . ? C15 C14 H14A 119.5 . . ? C13 C14 H14A 119.5 . . ? C14 C15 H15A 119.5 . . ? C6 C15 H15A 119.5 . . ? C3 C16 H16A 120.0 . . ? C3 C16 H16B 120.0 . . ? H16A C16 H16B 120.0 . . ? 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 O2 N1 C1 C2 -3.3(3) . . . . ? O1 N1 C1 C2 176.35(18) . . . . ? O2 N1 C1 C5 -123.8(2) . . . . ? O1 N1 C1 C5 55.8(2) . . . . ? O2 N1 C1 Cl1 116.72(18) . . . . ? O1 N1 C1 Cl1 -63.7(2) . . . . ? N1 C1 C2 C3 -163.08(17) . . . . ? C5 C1 C2 C3 -38.6(2) . . . . ? Cl1 C1 C2 C3 80.15(18) . . . . ? C1 C2 C3 C16 -157.4(2) . . . . ? C1 C2 C3 C4 20.0(2) . . . . ? C16 C3 C4 C5 -176.9(2) . . . . ? C2 C3 C4 C5 5.7(2) . . . . ? C3 C4 C5 C6 92.4(2) . . . . ? C3 C4 C5 C1 -28.2(2) . . . . ? C2 C1 C5 C6 -80.0(2) . . . . ? N1 C1 C5 C6 45.5(2) . . . . ? Cl1 C1 C5 C6 161.43(15) . . . . ? C2 C1 C5 C4 42.0(2) . . . . ? N1 C1 C5 C4 167.51(17) . . . . ? Cl1 C1 C5 C4 -76.57(18) . . . . ? C4 C5 C6 C7 149.90(19) . . . . ? C1 C5 C6 C7 -96.4(2) . . . . ? C4 C5 C6 C15 -27.6(3) . . . . ? C1 C5 C6 C15 86.1(2) . . . . ? C15 C6 C7 C8 -0.1(3) . . . . ? C5 C6 C7 C8 -177.69(18) . . . . ? C6 C7 C8 C9 179.11(19) . . . . ? C6 C7 C8 C13 0.4(3) . . . . ? C13 C8 C9 C10 -0.3(3) . . . . ? C7 C8 C9 C10 -179.1(2) . . . . ? C8 C9 C10 C11 0.4(3) . . . . ? C9 C10 C11 C12 -0.2(3) . . . . ? C10 C11 C12 C13 -0.1(3) . . . . ? C9 C8 C13 C14 -179.61(18) . . . . ? C7 C8 C13 C14 -0.9(3) . . . . ? C9 C8 C13 C12 0.1(3) . . . . ? C7 C8 C13 C12 178.82(19) . . . . ? C11 C12 C13 C14 179.8(2) . . . . ? C11 C12 C13 C8 0.1(3) . . . . ? C8 C13 C14 C15 1.1(3) . . . . ? C12 C13 C14 C15 -178.6(2) . . . . ? C13 C14 C15 C6 -0.8(3) . . . . ? C7 C6 C15 C14 0.3(3) . . . . ? C5 C6 C15 C14 177.83(19) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 69.67 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.268 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.045