data_sr06 _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H22 Cl N O2' _chemical_formula_weight 343.84 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 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 19.495(4) _cell_length_b 6.6031(13) _cell_length_c 13.671(3) _cell_angle_alpha 90.00 _cell_angle_beta 100.01(3) _cell_angle_gamma 90.00 _cell_volume 1733.1(6) _cell_formula_units_Z 4 _cell_measurement_temperature 173(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description colorless _exptl_crystal_colour plate _exptl_crystal_size_max 0.15 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.318 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 728 _exptl_absorpt_coefficient_mu 0.232 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9660 _exptl_absorpt_correction_T_max 0.9817 _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 173(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 'Nonius KappaCCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 5651 _diffrn_reflns_av_R_equivalents 0.0772 _diffrn_reflns_av_sigmaI/netI 0.1274 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 26.99 _reflns_number_total 3581 _reflns_number_gt 1897 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Nonius Collect' _computing_cell_refinement Denzo _computing_data_reduction Denzo _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics XP _computing_publication_material XCIF _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^)+(0.1000P)^2^+0.0000P] 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 SHELXL _refine_ls_extinction_coef 0.015(4) _refine_ls_extinction_expression 'Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^' _refine_ls_number_reflns 3581 _refine_ls_number_parameters 222 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1590 _refine_ls_R_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.2199 _refine_ls_wR_factor_gt 0.1809 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _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 0.56417(6) 0.6527(2) 0.76813(9) 0.0661(5) Uani 1 1 d . . . O1 O 0.71476(14) 0.3330(5) 1.0759(2) 0.0475(8) Uani 1 1 d . . . O2 O 0.91308(13) 0.5533(4) 0.9251(2) 0.0387(7) Uani 1 1 d . . . N1 N 0.94952(16) 0.2784(5) 1.0223(2) 0.0341(8) Uani 1 1 d . . . H1 H 0.997(2) 0.313(6) 1.041(3) 0.048(12) Uiso 1 1 d . . . C1 C 0.70919(18) 0.4013(6) 0.9930(3) 0.0319(9) Uani 1 1 d . . . C2 C 0.63670(18) 0.4627(6) 0.9341(3) 0.0357(10) Uani 1 1 d . . . C3 C 0.64710(19) 0.5796(6) 0.8400(3) 0.0418(10) Uani 1 1 d . . . H3A H 0.6738 0.7059 0.8616 0.050 Uiso 1 1 calc R . . C4 C 0.6880(2) 0.4600(6) 0.7743(3) 0.0400(10) Uani 1 1 d . . . H4A H 0.6884 0.5334 0.7112 0.048 Uiso 1 1 calc R . . H4B H 0.6663 0.3258 0.7585 0.048 Uiso 1 1 calc R . . C5 C 0.76273(18) 0.4344(5) 0.8311(3) 0.0302(9) Uani 1 1 d . . . H5A H 0.7932 0.5388 0.8074 0.036 Uiso 1 1 calc R . . C6 C 0.77235(18) 0.4439(5) 0.9456(3) 0.0311(9) Uani 1 1 d . . . H6A H 0.7928 0.5777 0.9692 0.037 Uiso 1 1 calc R . . C7 C 0.5933(2) 0.2743(6) 0.9084(3) 0.0460(11) Uani 1 1 d . . . H7A H 0.5769 0.2506 0.8398 0.055 Uiso 1 1 calc R . . C8 C 0.5760(3) 0.1416(8) 0.9694(4) 0.0650(14) Uani 1 1 d . . . H8A H 0.5910 0.1576 1.0389 0.078 Uiso 1 1 calc R . . H8B H 0.5484 0.0282 0.9447 0.078 Uiso 1 1 calc R . . C9 C 0.6032(2) 0.5995(7) 1.0043(4) 0.0529(12) Uani 1 1 d . . . H9A H 0.5969 0.5221 1.0632 0.079 Uiso 1 1 calc R . . H9B H 0.5578 0.6473 0.9697 0.079 Uiso 1 1 calc R . . H9C H 0.6335 0.7158 1.0244 0.079 Uiso 1 1 calc R . . C10 C 0.83107(18) 0.2832(5) 0.9533(3) 0.0296(9) Uani 1 1 d . . . C11 C 0.80112(19) 0.2278(6) 0.8399(3) 0.0306(9) Uani 1 1 d . . . C12 C 0.75226(19) 0.0467(6) 0.8322(3) 0.0348(9) Uani 1 1 d . . . H12A H 0.7349 0.0167 0.7620 0.052 Uiso 1 1 calc R . . H12B H 0.7130 0.0779 0.8656 0.052 Uiso 1 1 calc R . . H12C H 0.7775 -0.0711 0.8639 0.052 Uiso 1 1 calc R . . C13 C 0.85483(19) 0.1907(6) 0.7735(3) 0.0360(10) Uani 1 1 d . . . H13A H 0.8310 0.1585 0.7061 0.054 Uiso 1 1 calc R . . H13B H 0.8848 0.0770 0.7997 0.054 Uiso 1 1 calc R . . H13C H 0.8833 0.3125 0.7718 0.054 Uiso 1 1 calc R . . C14 C 0.84720(19) 0.1137(5) 1.0280(3) 0.0292(9) Uani 1 1 d . . . C15 C 0.8068(2) -0.0327(6) 1.0625(3) 0.0340(9) Uani 1 1 d . . . H15A H 0.7578 -0.0340 1.0409 0.041 Uiso 1 1 calc R . . C16 C 0.8386(2) -0.1788(6) 1.1292(3) 0.0385(10) Uani 1 1 d . . . H16A H 0.8110 -0.2791 1.1537 0.046 Uiso 1 1 calc R . . C17 C 0.9097(2) -0.1780(6) 1.1595(3) 0.0416(10) Uani 1 1 d . . . H17A H 0.9307 -0.2802 1.2037 0.050 Uiso 1 1 calc R . . C18 C 0.9509(2) -0.0318(6) 1.1270(3) 0.0404(10) Uani 1 1 d . . . H18A H 0.9999 -0.0306 1.1489 0.049 Uiso 1 1 calc R . . C19 C 0.91892(19) 0.1125(6) 1.0619(3) 0.0312(9) Uani 1 1 d . . . C20 C 0.90160(18) 0.3913(6) 0.9631(3) 0.0312(9) Uani 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 Cl1 0.0426(7) 0.0840(10) 0.0678(9) 0.0182(7) -0.0013(6) 0.0183(6) O1 0.0427(17) 0.073(2) 0.0283(17) 0.0074(15) 0.0092(12) 0.0085(15) O2 0.0365(15) 0.0390(17) 0.0393(17) 0.0033(13) 0.0027(12) -0.0085(13) N1 0.0250(18) 0.040(2) 0.036(2) 0.0015(15) 0.0026(14) 0.0009(15) C1 0.033(2) 0.032(2) 0.030(2) -0.0051(18) 0.0051(16) 0.0003(16) C2 0.028(2) 0.034(2) 0.045(3) 0.0034(19) 0.0068(17) 0.0017(17) C3 0.031(2) 0.043(3) 0.050(3) 0.003(2) 0.0023(18) 0.0006(18) C4 0.042(2) 0.046(3) 0.032(2) 0.0039(19) 0.0042(18) 0.0009(19) C5 0.0306(19) 0.028(2) 0.031(2) 0.0023(17) 0.0039(16) -0.0019(16) C6 0.0303(19) 0.025(2) 0.037(2) -0.0037(17) 0.0041(16) 0.0006(16) C7 0.038(2) 0.049(3) 0.051(3) -0.001(2) 0.009(2) -0.008(2) C8 0.064(3) 0.059(3) 0.072(4) 0.008(3) 0.010(3) -0.013(3) C9 0.044(3) 0.049(3) 0.068(3) -0.003(2) 0.017(2) 0.006(2) C10 0.030(2) 0.034(2) 0.025(2) 0.0008(17) 0.0045(15) -0.0016(16) C11 0.033(2) 0.037(2) 0.022(2) 0.0018(17) 0.0061(15) -0.0027(17) C12 0.039(2) 0.033(2) 0.031(2) -0.0039(18) 0.0058(17) -0.0027(17) C13 0.037(2) 0.038(2) 0.033(2) 0.0007(19) 0.0082(17) 0.0013(18) C14 0.036(2) 0.028(2) 0.024(2) -0.0025(16) 0.0047(16) 0.0025(16) C15 0.042(2) 0.033(2) 0.027(2) -0.0016(18) 0.0056(17) -0.0050(18) C16 0.054(3) 0.036(2) 0.028(2) 0.0021(18) 0.0108(18) -0.001(2) C17 0.060(3) 0.032(2) 0.031(2) 0.0067(19) 0.0035(19) 0.008(2) C18 0.043(2) 0.046(3) 0.031(2) -0.003(2) 0.0025(18) 0.005(2) C19 0.037(2) 0.030(2) 0.027(2) -0.0018(17) 0.0060(16) 0.0011(17) C20 0.031(2) 0.038(2) 0.026(2) -0.0042(18) 0.0068(16) 0.0005(17) _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 C3 1.806(4) . ? O1 C1 1.207(4) . ? O2 C20 1.227(4) . ? N1 H1 0.94(4) . ? N1 C20 1.349(5) . ? N1 C19 1.401(5) . ? C1 C6 1.514(5) . ? C1 C2 1.553(5) . ? C2 C7 1.511(6) . ? C2 C9 1.543(5) . ? C2 C3 1.544(5) . ? C3 C4 1.522(5) . ? C4 C5 1.536(5) . ? C5 C6 1.546(5) . ? C5 C11 1.551(5) . ? C6 C10 1.551(5) . ? C7 C8 1.294(6) . ? C10 C14 1.511(5) . ? C10 C20 1.534(5) . ? C10 C11 1.601(5) . ? C11 C12 1.521(5) . ? C11 C13 1.521(5) . ? C14 C15 1.380(5) . ? C14 C19 1.395(5) . ? C15 C16 1.396(5) . ? C16 C17 1.376(5) . ? C17 C18 1.379(5) . ? C18 C19 1.377(5) . ? 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 H1 N1 C20 125(3) . . ? H1 N1 C19 123(2) . . ? C20 N1 C19 111.5(3) . . ? O1 C1 C6 121.6(3) . . ? O1 C1 C2 120.6(3) . . ? C6 C1 C2 117.7(3) . . ? C7 C2 C9 110.2(3) . . ? C7 C2 C3 111.5(4) . . ? C9 C2 C3 110.9(3) . . ? C7 C2 C1 109.1(3) . . ? C9 C2 C1 106.1(3) . . ? C3 C2 C1 108.8(3) . . ? C4 C3 C2 113.0(3) . . ? C4 C3 Cl1 109.2(3) . . ? C2 C3 Cl1 110.6(3) . . ? C3 C4 C5 107.9(3) . . ? C4 C5 C6 116.4(3) . . ? C4 C5 C11 122.6(3) . . ? C6 C5 C11 89.1(3) . . ? C1 C6 C5 117.5(3) . . ? C1 C6 C10 119.3(3) . . ? C5 C6 C10 90.0(3) . . ? C8 C7 C2 127.2(5) . . ? C14 C10 C20 102.0(3) . . ? C14 C10 C6 128.1(3) . . ? C20 C10 C6 109.1(3) . . ? C14 C10 C11 118.9(3) . . ? C20 C10 C11 111.2(3) . . ? C6 C10 C11 87.1(3) . . ? C12 C11 C13 108.6(3) . . ? C12 C11 C5 113.5(3) . . ? C13 C11 C5 117.9(3) . . ? C12 C11 C10 111.4(3) . . ? C13 C11 C10 116.2(3) . . ? C5 C11 C10 88.0(3) . . ? C15 C14 C19 118.8(3) . . ? C15 C14 C10 133.3(3) . . ? C19 C14 C10 107.9(3) . . ? C14 C15 C16 119.5(4) . . ? C17 C16 C15 120.2(4) . . ? C16 C17 C18 121.3(4) . . ? C19 C18 C17 117.9(4) . . ? C18 C19 C14 122.3(4) . . ? C18 C19 N1 128.0(4) . . ? C14 C19 N1 109.7(3) . . ? O2 C20 N1 125.3(3) . . ? O2 C20 C10 126.6(3) . . ? N1 C20 C10 108.2(3) . . ? _diffrn_measured_fraction_theta_max 0.947 _diffrn_reflns_theta_full 26.99 _diffrn_measured_fraction_theta_full 0.947 _refine_diff_density_max 0.311 _refine_diff_density_min -0.284 _refine_diff_density_rms 0.066