data_oh163 _publ_section_title OH163 _publ_contact_author_name 'Olaf Hartmann' _publ_contact_author_address 'Dept. of Chemistry, Stanford Univeristy' _publ_contact_author_email olafh@stanford.edu _publ_contact_author_phone '650 723 8409' _publ_section_comment ; Discussion ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C12 H10 Cl N O' _chemical_formula_sum 'C12 H10 Cl N O' _chemical_formula_weight 219.66 _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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting orthorhmobic _symmetry_space_group_name_H-M P2(1)2(1)2(1) 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 7.9537(14) _cell_length_b 9.9845(17) _cell_length_c 12.839(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 1019.6(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used 6469 _cell_measurement_theta_min 2.59 _cell_measurement_theta_max 28.12 _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.431 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 0.343 _exptl_absorpt_correction_type numerical _exptl_absorpt_correction_T_min 0.9191 _exptl_absorpt_correction_T_max 0.9503 _exptl_absorpt_process_details 'Sheldrick, 2007' _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(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' _diffrn_measurement_method \w/2\q-scans _diffrn_detector_area_resol_mean 83.33 _diffrn_standards_number . _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% . _diffrn_reflns_number 11518 _diffrn_reflns_av_R_equivalents 0.0245 _diffrn_reflns_av_sigmaI/netI 0.0189 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.58 _diffrn_reflns_theta_max 28.27 _reflns_number_total 2528 _reflns_number_gt 2437 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX-II v2.1-4' _computing_cell_refinement 'Bruker SAINT v7.34' _computing_data_reduction 'Bruker SAINT v7.34' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _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^)+(0.0351P)^2^+0.2019P] 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' _refine_ls_abs_structure_Flack 0.01(5) _refine_ls_number_reflns 2528 _refine_ls_number_parameters 136 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0255 _refine_ls_R_factor_gt 0.0244 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0635 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _refine_ls_shift/su_max 0.002 _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 0.15386(4) 0.08210(4) 0.01777(2) 0.02876(9) Uani 1 1 d . . . O1 O 0.41013(12) 0.08520(11) -0.13873(7) 0.0280(2) Uani 1 1 d . . . N1 N 0.08243(16) 0.27760(14) -0.51492(10) 0.0319(3) Uani 1 1 d . . . C1 C 0.14122(17) 0.18310(12) -0.09864(9) 0.0189(2) Uani 1 1 d . . . C2 C 0.28960(16) 0.14711(13) -0.16905(10) 0.0194(2) Uani 1 1 d . . . C3 C 0.28101(15) 0.19814(13) -0.28066(10) 0.0194(2) Uani 1 1 d . . . H3A H 0.3650 0.1460 -0.3221 0.023 Uiso 1 1 calc R . . C4 C 0.10448(15) 0.17094(13) -0.32948(9) 0.0194(2) Uani 1 1 d . . . H4A H 0.0937 0.0718 -0.3383 0.023 Uiso 1 1 calc R . . C5 C -0.03685(15) 0.21540(13) -0.25801(10) 0.0195(2) Uani 1 1 d . . . C6 C -0.02714(16) 0.15010(14) -0.15285(10) 0.0213(3) Uani 1 1 d . . . H6A H -0.0379 0.0518 -0.1608 0.026 Uiso 1 1 calc R . . H6B H -0.1215 0.1818 -0.1090 0.026 Uiso 1 1 calc R . . C7 C 0.14641(17) 0.32760(13) -0.06496(9) 0.0211(2) Uani 1 1 d . . . H7A H 0.0906 0.3478 -0.0015 0.025 Uiso 1 1 calc R . . C8 C 0.21947(15) 0.43075(13) -0.11308(10) 0.0219(3) Uani 1 1 d . . . H8A H 0.2108 0.5137 -0.0772 0.026 Uiso 1 1 calc R . . C9 C 0.31073(15) 0.43735(13) -0.21197(10) 0.0227(3) Uani 1 1 d . . . H9A H 0.3612 0.5215 -0.2267 0.027 Uiso 1 1 calc R . . C10 C 0.33407(16) 0.34408(13) -0.28439(10) 0.0222(2) Uani 1 1 d . . . H10A H 0.3907 0.3721 -0.3458 0.027 Uiso 1 1 calc R . . C11 C 0.09315(17) 0.23082(14) -0.43394(10) 0.0233(3) Uani 1 1 d . . . C12 C -0.15893(18) 0.29871(13) -0.28578(10) 0.0247(3) Uani 1 1 d . . . H12C H -0.2462 0.3198 -0.2380 0.030 Uiso 1 1 calc R . . H12A H -0.1590 0.3373 -0.3534 0.030 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 0.03254(16) 0.03292(17) 0.02083(14) 0.00881(13) -0.00258(13) -0.00190(15) O1 0.0263(4) 0.0321(5) 0.0256(5) -0.0043(4) -0.0054(4) 0.0106(4) N1 0.0338(6) 0.0392(7) 0.0227(6) 0.0001(5) -0.0010(5) 0.0019(5) C1 0.0202(5) 0.0218(6) 0.0148(5) 0.0025(4) -0.0005(5) 0.0000(5) C2 0.0198(5) 0.0182(6) 0.0202(6) -0.0042(5) -0.0027(5) 0.0001(5) C3 0.0169(5) 0.0238(6) 0.0174(5) -0.0029(5) 0.0012(5) 0.0019(5) C4 0.0209(6) 0.0199(6) 0.0175(5) -0.0026(5) -0.0022(4) 0.0001(4) C5 0.0179(5) 0.0215(6) 0.0190(6) -0.0025(5) -0.0018(4) -0.0047(5) C6 0.0189(5) 0.0261(6) 0.0191(6) 0.0011(5) -0.0014(5) -0.0033(5) C7 0.0195(5) 0.0271(6) 0.0168(5) -0.0046(5) -0.0004(5) 0.0036(5) C8 0.0209(5) 0.0217(6) 0.0233(6) -0.0057(5) -0.0030(5) 0.0017(5) C9 0.0190(5) 0.0229(6) 0.0262(6) 0.0029(5) -0.0023(5) -0.0037(5) C10 0.0175(5) 0.0288(6) 0.0203(5) 0.0031(5) 0.0003(5) -0.0032(5) C11 0.0223(6) 0.0269(6) 0.0207(6) -0.0044(5) -0.0011(5) 0.0006(5) C12 0.0228(5) 0.0286(6) 0.0228(6) -0.0015(5) -0.0029(5) 0.0014(5) _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 1.8058(12) . ? O1 C2 1.2053(16) . ? N1 C11 1.1430(19) . ? C1 C7 1.5067(17) . ? C1 C2 1.5295(18) . ? C1 C6 1.5447(17) . ? C2 C3 1.5223(17) . ? C3 C10 1.5178(18) . ? C3 C4 1.5614(17) . ? C3 H3A 1.0000 . ? C4 C11 1.4711(18) . ? C4 C5 1.5175(17) . ? C4 H4A 1.0000 . ? C5 C12 1.3273(19) . ? C5 C6 1.5014(18) . ? C6 H6A 0.9900 . ? C6 H6B 0.9900 . ? C7 C8 1.3341(19) . ? C7 H7A 0.9500 . ? C8 C9 1.4640(18) . ? C8 H8A 0.9500 . ? C9 C10 1.3290(18) . ? C9 H9A 0.9500 . ? C10 H10A 0.9500 . ? C12 H12C 0.9500 . ? C12 H12A 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 C7 C1 C2 111.93(11) . . ? C7 C1 C6 110.94(11) . . ? C2 C1 C6 110.64(10) . . ? C7 C1 Cl1 107.20(8) . . ? C2 C1 Cl1 108.36(9) . . ? C6 C1 Cl1 107.58(8) . . ? O1 C2 C3 120.75(11) . . ? O1 C2 C1 122.91(11) . . ? C3 C2 C1 116.30(10) . . ? C10 C3 C2 109.79(10) . . ? C10 C3 C4 113.85(10) . . ? C2 C3 C4 111.10(10) . . ? C10 C3 H3A 107.3 . . ? C2 C3 H3A 107.3 . . ? C4 C3 H3A 107.3 . . ? C11 C4 C5 112.76(11) . . ? C11 C4 C3 110.51(10) . . ? C5 C4 C3 111.87(10) . . ? C11 C4 H4A 107.1 . . ? C5 C4 H4A 107.1 . . ? C3 C4 H4A 107.1 . . ? C12 C5 C6 123.46(12) . . ? C12 C5 C4 124.25(12) . . ? C6 C5 C4 112.25(10) . . ? C5 C6 C1 110.92(10) . . ? C5 C6 H6A 109.5 . . ? C1 C6 H6A 109.5 . . ? C5 C6 H6B 109.5 . . ? C1 C6 H6B 109.5 . . ? H6A C6 H6B 108.0 . . ? C8 C7 C1 128.19(11) . . ? C8 C7 H7A 115.9 . . ? C1 C7 H7A 115.9 . . ? C7 C8 C9 130.71(12) . . ? C7 C8 H8A 114.6 . . ? C9 C8 H8A 114.6 . . ? C10 C9 C8 130.12(12) . . ? C10 C9 H9A 114.9 . . ? C8 C9 H9A 114.9 . . ? C9 C10 C3 127.72(12) . . ? C9 C10 H10A 116.1 . . ? C3 C10 H10A 116.1 . . ? N1 C11 C4 179.22(15) . . ? C5 C12 H12C 120.0 . . ? C5 C12 H12A 120.0 . . ? H12C C12 H12A 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 C7 C1 C2 O1 102.89(14) . . . . ? C6 C1 C2 O1 -132.83(13) . . . . ? Cl1 C1 C2 O1 -15.12(16) . . . . ? C7 C1 C2 C3 -75.05(13) . . . . ? C6 C1 C2 C3 49.24(14) . . . . ? Cl1 C1 C2 C3 166.95(9) . . . . ? O1 C2 C3 C10 -97.70(14) . . . . ? C1 C2 C3 C10 80.28(13) . . . . ? O1 C2 C3 C4 135.47(12) . . . . ? C1 C2 C3 C4 -46.54(14) . . . . ? C10 C3 C4 C11 50.62(14) . . . . ? C2 C3 C4 C11 175.18(10) . . . . ? C10 C3 C4 C5 -75.92(13) . . . . ? C2 C3 C4 C5 48.64(14) . . . . ? C11 C4 C5 C12 0.33(18) . . . . ? C3 C4 C5 C12 125.64(13) . . . . ? C11 C4 C5 C6 178.09(11) . . . . ? C3 C4 C5 C6 -56.60(14) . . . . ? C12 C5 C6 C1 -123.01(13) . . . . ? C4 C5 C6 C1 59.21(14) . . . . ? C7 C1 C6 C5 71.00(13) . . . . ? C2 C1 C6 C5 -53.85(14) . . . . ? Cl1 C1 C6 C5 -172.04(9) . . . . ? C2 C1 C7 C8 25.28(18) . . . . ? C6 C1 C7 C8 -98.84(16) . . . . ? Cl1 C1 C7 C8 143.97(12) . . . . ? C1 C7 C8 C9 1.9(2) . . . . ? C7 C8 C9 C10 5.9(2) . . . . ? C8 C9 C10 C3 -4.8(2) . . . . ? C2 C3 C10 C9 -32.91(17) . . . . ? C4 C3 C10 C9 92.35(15) . . . . ? C5 C4 C11 N1 -22(11) . . . . ? C3 C4 C11 N1 -148(11) . . . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 28.27 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.250 _refine_diff_density_min -0.129 _refine_diff_density_rms 0.037