data_v72a _audit_creation_method SHELXTL _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H20 Cl N O2' _chemical_formula_weight 353.83 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 Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.5387(9) _cell_length_b 9.1358(14) _cell_length_c 34.448(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.723(2) _cell_angle_gamma 90.00 _cell_volume 1743.0(5) _cell_formula_units_Z 4 _cell_measurement_temperature 100(2) _cell_measurement_reflns_used 9966 _cell_measurement_theta_min 4.84 _cell_measurement_theta_max 67.47 _exptl_crystal_description 'Rectangular parallelepiped' _exptl_crystal_colour colourless _exptl_crystal_size_max 0.22 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.348 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 2.048 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.833 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 100(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'Bruker MicroStar microfocus rotating anode' _diffrn_radiation_monochromator 'Helios high-brilliance multilayer x-ray optics' _diffrn_measurement_device_type 'Bruker Platinum 135 CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 11082 _diffrn_reflns_av_R_equivalents 0.0230 _diffrn_reflns_av_sigmaI/netI 0.0213 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -41 _diffrn_reflns_limit_l_max 38 _diffrn_reflns_theta_min 5.01 _diffrn_reflns_theta_max 67.47 _reflns_number_total 3016 _reflns_number_gt 3004 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'Bruker SHELXTL' _computing_structure_refinement 'Bruker SHELXTL' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflectionsexcept those that were flagged by the user for being in the beamstop. 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^)+(0.0354P)^2^+1.3635P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment refall _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3016 _refine_ls_number_parameters 306 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0344 _refine_ls_R_factor_gt 0.0343 _refine_ls_wR_factor_ref 0.0845 _refine_ls_wR_factor_gt 0.0845 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_restrained_S_all 1.034 _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 Cl Cl 0.21559(7) 1.41272(4) 0.022858(10) 0.02244(13) Uani 1 1 d . . . O1 O 0.68720(18) 0.81721(11) 0.10024(3) 0.0195(2) Uani 1 1 d . . . O2 O 0.94025(19) 0.82677(12) 0.04916(3) 0.0210(2) Uani 1 1 d . . . N N 1.1138(2) 0.57475(14) 0.15129(4) 0.0190(3) Uani 1 1 d . . . C1 C 1.0725(3) 0.68508(17) 0.12046(4) 0.0181(3) Uani 1 1 d . . . H1A H 1.136(3) 0.780(2) 0.1297(5) 0.022(4) Uiso 1 1 d . . . H1B H 1.153(3) 0.655(2) 0.0958(5) 0.022(4) Uiso 1 1 d . . . C2 C 0.7970(3) 0.68786(16) 0.11756(4) 0.0164(3) Uani 1 1 d . . . C3 C 0.7131(3) 0.54913(17) 0.09698(4) 0.0181(3) Uani 1 1 d . . . H3A H 0.541(3) 0.5477(19) 0.0942(5) 0.018(4) Uiso 1 1 d . . . H3B H 0.780(3) 0.5472(19) 0.0710(5) 0.018(4) Uiso 1 1 d . . . C4 C 0.7971(3) 0.41396(17) 0.12004(5) 0.0203(3) Uani 1 1 d . . . H4A H 0.694(3) 0.4021(19) 0.1422(5) 0.018(4) Uiso 1 1 d . . . H4B H 0.776(3) 0.324(2) 0.1041(5) 0.025(5) Uiso 1 1 d . . . C5 C 1.0593(3) 0.42799(17) 0.13468(5) 0.0208(3) Uani 1 1 d . . . H5A H 1.177(3) 0.4128(19) 0.1135(5) 0.021(4) Uiso 1 1 d . . . H5B H 1.094(3) 0.357(2) 0.1541(5) 0.018(4) Uiso 1 1 d . . . C6 C 0.9351(3) 0.61162(16) 0.18030(4) 0.0185(3) Uani 1 1 d . . . C7 C 0.7296(3) 0.69338(17) 0.16075(4) 0.0178(3) Uani 1 1 d . . . H7A H 0.724(3) 0.797(2) 0.1689(5) 0.019(4) Uiso 1 1 d . . . H7B H 0.574(3) 0.648(2) 0.1662(5) 0.020(4) Uiso 1 1 d . . . C8 C 0.9647(3) 0.57043(17) 0.21724(5) 0.0219(3) Uani 1 1 d . . . H8 H 1.107(4) 0.513(2) 0.2231(5) 0.029(5) Uiso 1 1 d . . . C9 C 0.8001(3) 0.59218(17) 0.24989(4) 0.0224(3) Uani 1 1 d . . . C10 C 0.8280(4) 0.5039(2) 0.28258(5) 0.0383(5) Uani 1 1 d . . . H10 H 0.959(4) 0.433(3) 0.2826(7) 0.053(7) Uiso 1 1 d . . . C11 C 0.6749(5) 0.5169(2) 0.31403(6) 0.0481(6) Uani 1 1 d . . . H11 H 0.697(5) 0.449(3) 0.3357(8) 0.061(7) Uiso 1 1 d . . . C12 C 0.4969(4) 0.6207(2) 0.31451(5) 0.0362(4) Uani 1 1 d . . . H12 H 0.394(4) 0.629(3) 0.3363(7) 0.045(6) Uiso 1 1 d . . . C13 C 0.4656(4) 0.7096(2) 0.28273(5) 0.0352(4) Uani 1 1 d . . . H13 H 0.334(4) 0.786(3) 0.2828(7) 0.049(6) Uiso 1 1 d . . . C14 C 0.6153(3) 0.6962(2) 0.25082(5) 0.0318(4) Uani 1 1 d . . . H14 H 0.590(4) 0.763(2) 0.2288(6) 0.040(6) Uiso 1 1 d . . . C15 C 0.7723(3) 0.87467(16) 0.06706(4) 0.0156(3) Uani 1 1 d . . . C16 C 0.6311(3) 1.00787(16) 0.05610(4) 0.0154(3) Uani 1 1 d . . . C17 C 0.7161(3) 1.09888(16) 0.02683(4) 0.0173(3) Uani 1 1 d . . . H17 H 0.859(3) 1.0733(19) 0.0139(5) 0.022(4) Uiso 1 1 d . . . C18 C 0.5896(3) 1.22351(17) 0.01630(4) 0.0184(3) Uani 1 1 d . . . H18 H 0.647(3) 1.287(2) -0.0039(6) 0.024(5) Uiso 1 1 d . . . C19 C 0.3772(3) 1.25593(16) 0.03520(4) 0.0170(3) Uani 1 1 d . . . C20 C 0.2870(3) 1.16600(17) 0.06404(4) 0.0183(3) Uani 1 1 d . . . H20 H 0.139(3) 1.1883(19) 0.0760(5) 0.018(4) Uiso 1 1 d . . . C21 C 0.4156(3) 1.04216(17) 0.07449(4) 0.0173(3) Uani 1 1 d . . . H21 H 0.353(3) 0.977(2) 0.0937(5) 0.019(4) Uiso 1 1 d . . . 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 Cl 0.0252(2) 0.0175(2) 0.0245(2) 0.00364(13) -0.00114(15) 0.00602(13) O1 0.0217(5) 0.0194(5) 0.0175(5) 0.0068(4) 0.0064(4) 0.0064(4) O2 0.0222(6) 0.0219(6) 0.0192(5) 0.0035(4) 0.0068(4) 0.0054(4) N 0.0175(6) 0.0208(7) 0.0186(6) 0.0028(5) 0.0010(5) 0.0012(5) C1 0.0175(7) 0.0173(8) 0.0196(8) 0.0029(6) 0.0023(6) -0.0013(6) C2 0.0173(7) 0.0161(7) 0.0159(7) 0.0045(6) 0.0031(6) 0.0036(6) C3 0.0148(8) 0.0221(8) 0.0173(7) -0.0006(6) 0.0013(6) 0.0008(6) C4 0.0223(8) 0.0170(8) 0.0218(8) 0.0000(6) 0.0032(6) -0.0007(6) C5 0.0213(8) 0.0182(8) 0.0229(8) 0.0032(6) 0.0029(6) 0.0039(6) C6 0.0185(7) 0.0178(7) 0.0192(7) 0.0001(6) 0.0004(6) -0.0015(6) C7 0.0191(8) 0.0188(8) 0.0154(7) 0.0015(6) 0.0029(6) 0.0019(6) C8 0.0227(8) 0.0217(8) 0.0211(8) 0.0019(6) -0.0030(6) 0.0002(6) C9 0.0293(9) 0.0211(8) 0.0167(8) -0.0001(6) -0.0026(6) -0.0038(6) C10 0.0541(12) 0.0377(10) 0.0233(9) 0.0081(8) 0.0031(8) 0.0161(9) C11 0.0775(16) 0.0442(12) 0.0228(9) 0.0136(9) 0.0115(10) 0.0169(11) C12 0.0572(12) 0.0305(10) 0.0214(9) 0.0000(7) 0.0139(8) 0.0003(9) C13 0.0449(11) 0.0391(11) 0.0218(9) -0.0013(8) 0.0048(8) 0.0074(9) C14 0.0414(10) 0.0368(10) 0.0171(8) 0.0048(7) 0.0024(7) 0.0082(8) C15 0.0172(7) 0.0161(7) 0.0136(7) 0.0005(6) 0.0010(5) -0.0013(6) C16 0.0176(7) 0.0153(7) 0.0135(7) -0.0015(5) -0.0004(5) -0.0004(6) C17 0.0171(8) 0.0195(8) 0.0153(7) -0.0007(6) 0.0026(6) -0.0004(6) C18 0.0225(8) 0.0177(7) 0.0150(7) 0.0031(6) 0.0006(6) -0.0019(6) C19 0.0201(7) 0.0131(7) 0.0177(7) -0.0004(6) -0.0045(6) 0.0018(6) C20 0.0168(7) 0.0194(7) 0.0188(7) -0.0013(6) 0.0029(6) 0.0014(6) C21 0.0196(7) 0.0171(7) 0.0151(7) 0.0013(6) 0.0026(6) -0.0019(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 Cl C19 1.7391(15) . ? O1 C15 1.3482(17) . ? O1 C2 1.4536(17) . ? O2 C15 1.2052(18) . ? N C6 1.4548(19) . ? N C1 1.4798(19) . ? N C5 1.487(2) . ? C1 C2 1.528(2) . ? C1 H1A 0.990(19) . ? C1 H1B 1.002(18) . ? C2 C3 1.522(2) . ? C2 C7 1.540(2) . ? C3 C4 1.537(2) . ? C3 H3A 0.958(18) . ? C3 H3B 0.972(18) . ? C4 C5 1.537(2) . ? C4 H4A 0.967(18) . ? C4 H4B 1.00(2) . ? C5 H5A 0.996(18) . ? C5 H5B 0.947(19) . ? C6 C8 1.335(2) . ? C6 C7 1.513(2) . ? C7 H7A 0.989(18) . ? C7 H7B 0.974(19) . ? C8 C9 1.470(2) . ? C8 H8 0.96(2) . ? C9 C10 1.392(2) . ? C9 C14 1.398(2) . ? C10 C11 1.389(3) . ? C10 H10 0.97(3) . ? C11 C12 1.368(3) . ? C11 H11 0.98(3) . ? C12 C13 1.372(3) . ? C12 H12 0.95(2) . ? C13 C14 1.391(2) . ? C13 H13 1.01(2) . ? C14 H14 0.98(2) . ? C15 C16 1.492(2) . ? C16 C17 1.393(2) . ? C16 C21 1.394(2) . ? C17 C18 1.383(2) . ? C17 H17 0.944(19) . ? C18 C19 1.384(2) . ? C18 H18 0.961(19) . ? C19 C20 1.387(2) . ? C20 C21 1.382(2) . ? C20 H20 0.942(18) . ? C21 H21 0.954(19) . ? 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 C15 O1 C2 121.03(11) . . ? C6 N C1 103.60(11) . . ? C6 N C5 109.68(12) . . ? C1 N C5 108.02(12) . . ? N C1 C2 101.73(11) . . ? N C1 H1A 108.5(10) . . ? C2 C1 H1A 111.0(10) . . ? N C1 H1B 110.6(10) . . ? C2 C1 H1B 113.8(10) . . ? H1A C1 H1B 110.7(15) . . ? O1 C2 C3 111.23(12) . . ? O1 C2 C1 116.91(12) . . ? C3 C2 C1 108.39(12) . . ? O1 C2 C7 105.34(11) . . ? C3 C2 C7 113.65(12) . . ? C1 C2 C7 101.04(12) . . ? C2 C3 C4 109.84(12) . . ? C2 C3 H3A 110.9(10) . . ? C4 C3 H3A 109.7(10) . . ? C2 C3 H3B 109.0(10) . . ? C4 C3 H3B 110.1(10) . . ? H3A C3 H3B 107.3(14) . . ? C5 C4 C3 112.41(12) . . ? C5 C4 H4A 108.5(10) . . ? C3 C4 H4A 108.6(10) . . ? C5 C4 H4B 110.8(10) . . ? C3 C4 H4B 110.3(11) . . ? H4A C4 H4B 105.9(14) . . ? N C5 C4 112.81(12) . . ? N C5 H5A 106.1(10) . . ? C4 C5 H5A 111.9(10) . . ? N C5 H5B 107.8(11) . . ? C4 C5 H5B 110.9(10) . . ? H5A C5 H5B 107.0(14) . . ? C8 C6 N 120.88(14) . . ? C8 C6 C7 130.25(14) . . ? N C6 C7 108.84(12) . . ? C6 C7 C2 102.94(12) . . ? C6 C7 H7A 112.1(10) . . ? C2 C7 H7A 108.3(10) . . ? C6 C7 H7B 111.6(10) . . ? C2 C7 H7B 113.5(10) . . ? H7A C7 H7B 108.4(14) . . ? C6 C8 C9 128.41(15) . . ? C6 C8 H8 116.3(11) . . ? C9 C8 H8 115.2(11) . . ? C10 C9 C14 116.69(16) . . ? C10 C9 C8 118.50(16) . . ? C14 C9 C8 124.81(15) . . ? C11 C10 C9 121.28(18) . . ? C11 C10 H10 121.2(14) . . ? C9 C10 H10 117.6(14) . . ? C12 C11 C10 121.03(18) . . ? C12 C11 H11 120.9(15) . . ? C10 C11 H11 118.1(15) . . ? C11 C12 C13 118.96(17) . . ? C11 C12 H12 120.1(14) . . ? C13 C12 H12 120.9(14) . . ? C12 C13 C14 120.54(18) . . ? C12 C13 H13 119.3(13) . . ? C14 C13 H13 120.1(14) . . ? C13 C14 C9 121.47(16) . . ? C13 C14 H14 118.3(12) . . ? C9 C14 H14 120.2(12) . . ? O2 C15 O1 124.95(13) . . ? O2 C15 C16 124.89(13) . . ? O1 C15 C16 110.16(12) . . ? C17 C16 C21 119.59(13) . . ? C17 C16 C15 119.27(13) . . ? C21 C16 C15 121.13(13) . . ? C18 C17 C16 120.44(14) . . ? C18 C17 H17 120.4(11) . . ? C16 C17 H17 119.2(11) . . ? C17 C18 C19 118.92(14) . . ? C17 C18 H18 120.8(11) . . ? C19 C18 H18 120.3(11) . . ? C18 C19 C20 121.75(14) . . ? C18 C19 Cl 119.95(12) . . ? C20 C19 Cl 118.30(11) . . ? C21 C20 C19 118.84(14) . . ? C21 C20 H20 120.7(11) . . ? C19 C20 H20 120.4(11) . . ? C20 C21 C16 120.45(14) . . ? C20 C21 H21 119.9(11) . . ? C16 C21 H21 119.6(11) . . ? 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 C6 N C1 C2 -43.18(14) . . . . ? C5 N C1 C2 73.11(14) . . . . ? C15 O1 C2 C3 -79.22(16) . . . . ? C15 O1 C2 C1 46.00(18) . . . . ? C15 O1 C2 C7 157.22(12) . . . . ? N C1 C2 O1 159.20(12) . . . . ? N C1 C2 C3 -74.16(14) . . . . ? N C1 C2 C7 45.54(14) . . . . ? O1 C2 C3 C4 -170.40(11) . . . . ? C1 C2 C3 C4 59.75(15) . . . . ? C7 C2 C3 C4 -51.71(16) . . . . ? C2 C3 C4 C5 -43.24(17) . . . . ? C6 N C5 C4 52.04(16) . . . . ? C1 N C5 C4 -60.23(16) . . . . ? C3 C4 C5 N 43.85(18) . . . . ? C1 N C6 C8 -157.61(14) . . . . ? C5 N C6 C8 87.27(17) . . . . ? C1 N C6 C7 24.00(15) . . . . ? C5 N C6 C7 -91.12(14) . . . . ? C8 C6 C7 C2 -173.48(16) . . . . ? N C6 C7 C2 4.71(15) . . . . ? O1 C2 C7 C6 -152.48(11) . . . . ? C3 C2 C7 C6 85.51(15) . . . . ? C1 C2 C7 C6 -30.36(14) . . . . ? N C6 C8 C9 -177.19(14) . . . . ? C7 C6 C8 C9 0.8(3) . . . . ? C6 C8 C9 C10 160.45(18) . . . . ? C6 C8 C9 C14 -19.7(3) . . . . ? C14 C9 C10 C11 1.6(3) . . . . ? C8 C9 C10 C11 -178.56(19) . . . . ? C9 C10 C11 C12 -2.4(4) . . . . ? C10 C11 C12 C13 2.2(4) . . . . ? C11 C12 C13 C14 -1.2(3) . . . . ? C12 C13 C14 C9 0.4(3) . . . . ? C10 C9 C14 C13 -0.6(3) . . . . ? C8 C9 C14 C13 179.55(17) . . . . ? C2 O1 C15 O2 0.1(2) . . . . ? C2 O1 C15 C16 -178.89(12) . . . . ? O2 C15 C16 C17 -10.5(2) . . . . ? O1 C15 C16 C17 168.42(13) . . . . ? O2 C15 C16 C21 169.16(14) . . . . ? O1 C15 C16 C21 -11.87(19) . . . . ? C21 C16 C17 C18 0.8(2) . . . . ? C15 C16 C17 C18 -179.54(13) . . . . ? C16 C17 C18 C19 -0.2(2) . . . . ? C17 C18 C19 C20 -0.7(2) . . . . ? C17 C18 C19 Cl 179.47(11) . . . . ? C18 C19 C20 C21 1.1(2) . . . . ? Cl C19 C20 C21 -179.09(11) . . . . ? C19 C20 C21 C16 -0.5(2) . . . . ? C17 C16 C21 C20 -0.4(2) . . . . ? C15 C16 C21 C20 179.93(13) . . . . ? _diffrn_measured_fraction_theta_max 0.959 _diffrn_reflns_theta_full 66.00 _diffrn_measured_fraction_theta_full 0.976 _refine_diff_density_max 0.480 _refine_diff_density_min -0.322 _refine_diff_density_rms 0.043