# Supplementary Material (ESI) for Perkin Transactions # This journal is © The Royal Society of Chemistry 2000 # CCDC Number: 188/180 data_j1412=3s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C14 H16 Cl N O2' _chemical_formula_weight 265.73 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 7.5589(8) _cell_length_b 9.3566(15) _cell_length_c 9.4213(9) _cell_angle_alpha 90.00 _cell_angle_beta 96.521(8) _cell_angle_gamma 90.00 _cell_volume 662.02(14) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 17.6 _cell_measurement_theta_max 20.4 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 280 _exptl_absorpt_coefficient_mu 0.282 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method '\w--2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0 _diffrn_reflns_number 1328 _diffrn_reflns_av_R_equivalents 0.0100 _diffrn_reflns_av_sigmaI/netI 0.0225 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 24.98 _reflns_number_total 1232 _reflns_number_gt 1100 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_cell_refinement ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_data_reduction ; TEXSAN for WINDOWS(Molecular Structure Corporation, 1997) ; _computing_structure_solution 'SIR-92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for WINDOWS (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0293P)^2^+0.0970P] 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 0.04(8) _refine_ls_number_reflns 1232 _refine_ls_number_parameters 189 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0270 _refine_ls_wR_factor_ref 0.0643 _refine_ls_wR_factor_gt 0.0611 _refine_ls_goodness_of_fit_ref 1.072 _refine_ls_restrained_S_all 1.072 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl 0.40535(10) 0.8402 0.71451(9) 0.0569(2) Uani 1 d . . . O1 O 1.1537(3) 0.1188(3) 0.6498(2) 0.0653(7) Uani 1 d . . . O4 O 0.8184(2) 0.2317(2) 0.9459(2) 0.0422(5) Uani 1 d . . . N8 N 0.9744(3) 0.2791(3) 0.7482(2) 0.0361(5) Uani 1 d . . . C1 C 1.0081(4) 0.1536(4) 0.6829(3) 0.0428(7) Uani 1 d . . . C2 C 0.8386(4) 0.0663(4) 0.6601(3) 0.0463(7) Uani 1 d . . . H2 H 0.851(4) -0.018(4) 0.733(3) 0.056 Uiso 1 d . . . C3 C 0.6981(4) 0.1676(4) 0.7071(4) 0.0456(7) Uani 1 d . . . H3A H 0.633(4) 0.209(4) 0.624(4) 0.055 Uiso 1 d . . . H3B H 0.615(4) 0.130(4) 0.753(3) 0.055 Uiso 1 d . . . C3A C 0.7999(3) 0.2805(3) 0.8009(3) 0.0354(6) Uani 1 d . . . C5 C 0.9476(4) 0.3130(4) 1.0367(3) 0.0493(8) Uani 1 d . . . H5A H 0.904(4) 0.413(4) 1.046(4) 0.059 Uiso 1 d . . . H5B H 0.943(4) 0.273(4) 1.133(4) 0.059 Uiso 1 d . . . C6 C 1.1293(4) 0.3097(4) 0.9843(4) 0.0524(9) Uani 1 d . . . H6A H 1.216(4) 0.370(4) 1.040(3) 0.063 Uiso 1 d . . . H6B H 1.179(4) 0.216(4) 0.993(4) 0.063 Uiso 1 d . . . C7 C 1.1175(4) 0.3591(4) 0.8303(3) 0.0451(7) Uani 1 d . . . H7A H 1.228(4) 0.338(4) 0.787(3) 0.054 Uiso 1 d . . . H7B H 1.093(4) 0.458(4) 0.819(3) 0.054 Uiso 1 d . . . C12 C 0.7105(3) 0.4265(3) 0.7849(3) 0.0342(6) Uani 1 d . . . C13 C 0.7367(4) 0.5150(4) 0.6719(3) 0.0418(7) Uani 1 d . . . H13 H 0.8177 0.4885 0.6095 0.050 Uiso 1 calc R . . C14 C 0.6447(4) 0.6422(4) 0.6498(3) 0.0452(7) Uani 1 d . . . H14 H 0.6636 0.7009 0.5733 0.054 Uiso 1 calc R . . C15 C 0.5246(3) 0.6810(3) 0.7427(3) 0.0402(7) Uani 1 d . . . C16 C 0.4952(4) 0.5948(3) 0.8563(3) 0.0401(6) Uani 1 d . . . H16 H 0.4138 0.6216 0.9184 0.048 Uiso 1 calc R . . C17 C 0.5884(3) 0.4675(3) 0.8768(3) 0.0375(6) Uani 1 d . . . H17 H 0.5689 0.4087 0.9531 0.045 Uiso 1 calc R . . C18 C 0.8021(5) 0.0062(4) 0.5121(3) 0.0615(9) Uani 1 d . . . H18A H 0.8074 0.0814 0.4435 0.092 Uiso 1 calc R . . H18B H 0.6857 -0.0364 0.5002 0.092 Uiso 1 calc R . . H18C H 0.8897 -0.0651 0.4979 0.092 Uiso 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 Cl 0.0607(5) 0.0414(4) 0.0691(5) 0.0007(4) 0.0097(4) 0.0132(4) O1 0.0525(13) 0.0734(18) 0.0732(15) -0.0140(13) 0.0216(11) 0.0135(13) O4 0.0473(11) 0.0410(11) 0.0395(11) 0.0056(9) 0.0104(8) -0.0015(10) N8 0.0277(11) 0.0395(13) 0.0416(12) 0.0000(10) 0.0067(9) 0.0016(10) C1 0.0466(16) 0.0467(17) 0.0362(15) 0.0012(13) 0.0099(12) 0.0088(14) C2 0.0558(18) 0.0406(18) 0.0430(16) -0.0025(15) 0.0083(14) 0.0006(14) C3 0.0372(16) 0.0466(18) 0.0539(19) -0.0088(16) 0.0088(14) -0.0048(14) C3A 0.0342(14) 0.0379(14) 0.0355(14) 0.0003(12) 0.0095(11) -0.0013(12) C5 0.0546(19) 0.059(2) 0.0335(15) 0.0022(14) 0.0016(13) 0.0069(16) C6 0.0431(17) 0.059(3) 0.0525(19) -0.0051(16) -0.0062(14) 0.0085(16) C7 0.0343(15) 0.046(2) 0.0545(17) -0.0023(16) 0.0047(12) -0.0017(15) C12 0.0289(13) 0.0386(15) 0.0348(14) -0.0027(12) 0.0021(11) 0.0005(12) C13 0.0392(16) 0.0472(18) 0.0409(16) 0.0027(14) 0.0123(12) 0.0062(14) C14 0.0471(17) 0.0454(17) 0.0439(16) 0.0070(14) 0.0082(13) 0.0042(14) C15 0.0347(14) 0.0353(16) 0.0496(17) -0.0052(13) 0.0006(12) 0.0019(12) C16 0.0346(14) 0.0431(16) 0.0436(15) -0.0069(14) 0.0093(11) 0.0006(13) C17 0.0343(14) 0.0408(16) 0.0386(14) 0.0003(12) 0.0096(11) -0.0038(12) C18 0.070(2) 0.055(2) 0.059(2) -0.0153(18) 0.0088(16) -0.0012(19) _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 C15 1.746(3) . y O1 C1 1.222(3) . y O4 C3A 1.432(3) . y O4 C5 1.440(4) . y N8 C1 1.363(4) . y N8 C3A 1.461(3) . y N8 C7 1.462(4) . y C1 C2 1.514(4) . ? C2 C18 1.499(4) . ? C2 C3 1.526(4) . ? C2 H2 1.04(3) . ? C3 C3A 1.528(4) . ? C3 H3A 0.96(3) . ? C3 H3B 0.88(3) . ? C3A C12 1.524(4) . ? C5 C6 1.512(4) . ? C5 H5A 1.00(4) . ? C5 H5B 0.98(3) . ? C6 C7 1.516(5) . ? C6 H6A 0.97(3) . ? C6 H6B 0.96(4) . ? C7 H7A 1.00(3) . ? C7 H7B 0.94(4) . ? C12 C13 1.381(4) . ? C12 C17 1.389(4) . ? C13 C14 1.382(4) . ? C13 H13 0.9300 . ? C14 C15 1.379(4) . ? C14 H14 0.9300 . ? C15 C16 1.378(4) . ? C16 C17 1.386(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C3A O4 C5 112.6(2) . . y C1 N8 C3A 112.5(2) . . y C1 N8 C7 121.0(2) . . y C3A N8 C7 117.3(2) . . y O1 C1 N8 124.4(3) . . y O1 C1 C2 126.3(3) . . y N8 C1 C2 109.3(2) . . y C18 C2 C1 113.5(3) . . ? C18 C2 C3 116.2(3) . . ? C1 C2 C3 103.2(2) . . ? C18 C2 H2 109.0(18) . . ? C1 C2 H2 107.4(17) . . ? C3 C2 H2 106.9(17) . . ? C2 C3 C3A 106.0(2) . . ? C2 C3 H3A 109(2) . . ? C3A C3 H3A 112(2) . . ? C2 C3 H3B 118(2) . . ? C3A C3 H3B 109(2) . . ? H3A C3 H3B 103(3) . . ? O4 C3A N8 109.1(2) . . ? O4 C3A C12 112.0(2) . . ? N8 C3A C12 112.4(2) . . ? O4 C3A C3 108.7(2) . . ? N8 C3A C3 102.2(2) . . ? C12 C3A C3 112.0(2) . . ? O4 C5 C6 112.0(3) . . ? O4 C5 H5A 110(2) . . ? C6 C5 H5A 112(2) . . ? O4 C5 H5B 105(2) . . ? C6 C5 H5B 115.1(19) . . ? H5A C5 H5B 103(3) . . ? C5 C6 C7 110.5(2) . . ? C5 C6 H6A 113.1(19) . . ? C7 C6 H6A 107.9(19) . . ? C5 C6 H6B 111(2) . . ? C7 C6 H6B 110(2) . . ? H6A C6 H6B 104(3) . . ? N8 C7 C6 108.0(3) . . ? N8 C7 H7A 106.6(19) . . ? C6 C7 H7A 111.8(17) . . ? N8 C7 H7B 108(2) . . ? C6 C7 H7B 113.5(19) . . ? H7A C7 H7B 108(3) . . ? C13 C12 C17 118.6(3) . . ? C13 C12 C3A 120.9(2) . . ? C17 C12 C3A 120.3(3) . . ? C12 C13 C14 121.3(3) . . ? C12 C13 H13 119.4 . . ? C14 C13 H13 119.4 . . ? C15 C14 C13 119.1(3) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C16 C15 C14 121.0(3) . . ? C16 C15 Cl 119.4(2) . . ? C14 C15 Cl 119.6(2) . . ? C15 C16 C17 119.1(2) . . ? C15 C16 H16 120.4 . . ? C17 C16 H16 120.4 . . ? C16 C17 C12 120.9(3) . . ? C16 C17 H17 119.5 . . ? C12 C17 H17 119.5 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C3A N8 C1 O1 -168.4(3) . . . . ? C7 N8 C1 O1 -22.6(4) . . . . ? C3A N8 C1 C2 11.1(3) . . . . ? C7 N8 C1 C2 156.9(2) . . . . ? O1 C1 C2 C18 -47.8(4) . . . . ? N8 C1 C2 C18 132.7(3) . . . . ? O1 C1 C2 C3 -174.4(3) . . . . ? N8 C1 C2 C3 6.0(3) . . . . ? C18 C2 C3 C3A -144.6(3) . . . . ? C1 C2 C3 C3A -19.7(3) . . . . ? C5 O4 C3A N8 55.3(3) . . . . ? C5 O4 C3A C12 -69.8(3) . . . . ? C5 O4 C3A C3 166.0(2) . . . . ? C1 N8 C3A O4 91.8(3) . . . . ? C7 N8 C3A O4 -55.4(3) . . . . ? C1 N8 C3A C12 -143.3(2) . . . . ? C7 N8 C3A C12 69.5(3) . . . . ? C1 N8 C3A C3 -23.1(3) . . . . ? C7 N8 C3A C3 -170.3(3) . . . . ? C2 C3 C3A O4 -89.7(3) . . . . ? C2 C3 C3A N8 25.6(3) . . . . ? C2 C3 C3A C12 146.1(2) . . . . ? C3A O4 C5 C6 -57.8(3) . . . . ? O4 C5 C6 C7 54.8(4) . . . . ? C1 N8 C7 C6 -91.2(3) . . . . ? C3A N8 C7 C6 53.1(3) . . . . ? C5 C6 C7 N8 -50.2(4) . . . . ? O4 C3A C12 C13 156.1(2) . . . . ? N8 C3A C12 C13 32.9(3) . . . . ? C3 C3A C12 C13 -81.6(3) . . . . ? O4 C3A C12 C17 -29.7(3) . . . . ? N8 C3A C12 C17 -153.0(2) . . . . ? C3 C3A C12 C17 92.6(3) . . . . ? C17 C12 C13 C14 0.2(4) . . . . ? C3A C12 C13 C14 174.5(2) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C13 C14 C15 C16 -0.1(4) . . . . ? C13 C14 C15 Cl -179.1(2) . . . . ? C14 C15 C16 C17 0.1(4) . . . . ? Cl C15 C16 C17 179.1(2) . . . . ? C15 C16 C17 C12 0.2(4) . . . . ? C13 C12 C17 C16 -0.3(4) . . . . ? C3A C12 C17 C16 -174.6(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13 N8 0.93 2.57 2.885(4) 100.4 . C17 H17 O4 0.93 2.52 2.839(3) 100.6 . _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 24.98 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.142 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.028 #===END data_j1403=5a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H22 Cl N O2' _chemical_formula_weight 319.82 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' 'x+1/2, -y+1/2, -z' '-x, y+1/2, -z+1/2' '-x+1/2, -y, z+1/2' '-x, -y, -z' '-x-1/2, y-1/2, z' 'x, -y-1/2, z-1/2' 'x-1/2, y, -z-1/2' _cell_length_a 26.623(2) _cell_length_b 11.443(3) _cell_length_c 10.698(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3259.2(12) _cell_formula_units_Z 8 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 20 _cell_measurement_theta_min 6.5 _cell_measurement_theta_max 9.1 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.304 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1360 _exptl_absorpt_coefficient_mu 0.241 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method '\w--2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_decay_% 0 _diffrn_reflns_number 2875 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0932 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 32 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 0 _diffrn_reflns_theta_min 1.53 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2875 _reflns_number_gt 1534 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_cell_refinement ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_data_reduction ; TEXSAN for WINDOWS(Molecular Structure Corporation, 1997) ; _computing_structure_solution 'SIR-92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for WINDOWS (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0356P)^2^+0.4890P] 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_number_reflns 2875 _refine_ls_number_parameters 244 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1465 _refine_ls_R_factor_gt 0.0526 _refine_ls_wR_factor_ref 0.1184 _refine_ls_wR_factor_gt 0.0968 _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_restrained_S_all 1.024 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl 0.94765(4) -0.20073(8) 1.04154(9) 0.0555(3) Uani 1 d . . . O1 O 0.84794(10) -0.0434(3) 0.3464(3) 0.0749(9) Uani 1 d . . . O4 O 0.87640(8) 0.22721(18) 0.6505(2) 0.0455(6) Uani 1 d . . . N10 N 0.85026(9) 0.0649(2) 0.5281(2) 0.0356(7) Uani 1 d . . . C1 C 0.87005(14) 0.0114(3) 0.4261(4) 0.0477(10) Uani 1 d . . . C2 C 0.92745(14) 0.0281(4) 0.4324(4) 0.0533(11) Uani 1 d . . . H2 H 0.9410(13) -0.056(3) 0.466(3) 0.064 Uiso 1 d . . . C3 C 0.93478(14) 0.1203(4) 0.5291(4) 0.0495(10) Uani 1 d . . . H3A H 0.9325(12) 0.199(3) 0.487(3) 0.059 Uiso 1 d . . . H3B H 0.9661(13) 0.119(3) 0.575(3) 0.059 Uiso 1 d . . . C3A C 0.88855(13) 0.1126(3) 0.6123(3) 0.0370(9) Uani 1 d . . . C5 C 0.82706(15) 0.2356(4) 0.7035(4) 0.0499(10) Uani 1 d . . . H5A H 0.8243(13) 0.319(3) 0.726(3) 0.060 Uiso 1 d . . . H5B H 0.8219(13) 0.184(3) 0.782(3) 0.060 Uiso 1 d . . . C5A C 0.78732(13) 0.1974(3) 0.6111(3) 0.0412(9) Uani 1 d . . . H5A1 H 0.7913(12) 0.243(3) 0.540(3) 0.049 Uiso 1 d . . . C6 C 0.73463(15) 0.2096(4) 0.6634(4) 0.0527(11) Uani 1 d . . . H6A H 0.7316(13) 0.162(3) 0.740(3) 0.063 Uiso 1 d . . . H6B H 0.7270(13) 0.292(3) 0.689(3) 0.063 Uiso 1 d . . . C7 C 0.69530(15) 0.1669(4) 0.5720(4) 0.0609(12) Uani 1 d . . . H7A H 0.6641(14) 0.173(3) 0.602(3) 0.073 Uiso 1 d . . . H7B H 0.6953(14) 0.218(3) 0.494(4) 0.073 Uiso 1 d . . . C8 C 0.70614(15) 0.0429(4) 0.5302(5) 0.0620(12) Uani 1 d . . . H8A H 0.6822(14) 0.016(3) 0.467(3) 0.074 Uiso 1 d . . . H8B H 0.7047(14) -0.014(3) 0.606(4) 0.074 Uiso 1 d . . . C9 C 0.75896(14) 0.0297(4) 0.4754(4) 0.0493(10) Uani 1 d . . . H9A H 0.7654(13) -0.052(3) 0.450(3) 0.059 Uiso 1 d . . . H9B H 0.7627(13) 0.076(3) 0.394(3) 0.059 Uiso 1 d . . . C9A C 0.79772(12) 0.0712(3) 0.5700(3) 0.0373(9) Uani 1 d . . . H9A1 H 0.7953(12) 0.024(3) 0.644(3) 0.045 Uiso 1 d . . . C12 C 0.89783(12) 0.0329(3) 0.7255(3) 0.0338(8) Uani 1 d . . . C13 C 0.88791(13) -0.0860(3) 0.7230(3) 0.0381(9) Uani 1 d . . . H13 H 0.8712 -0.1179 0.6547 0.046 Uiso 1 calc R . . C14 C 0.90237(12) -0.1581(3) 0.8204(3) 0.0404(9) Uani 1 d . . . H14 H 0.8954 -0.2377 0.8180 0.048 Uiso 1 calc R . . C15 C 0.92712(12) -0.1103(3) 0.9206(3) 0.0380(9) Uani 1 d . . . C16 C 0.93629(13) 0.0081(3) 0.9278(3) 0.0457(10) Uani 1 d . . . H16 H 0.9519 0.0401 0.9977 0.055 Uiso 1 calc R . . C17 C 0.92190(13) 0.0785(3) 0.8291(3) 0.0438(9) Uani 1 d . . . H17 H 0.9285 0.1582 0.8325 0.053 Uiso 1 calc R . . C18 C 0.95019(16) 0.0473(4) 0.3034(3) 0.0687(13) Uani 1 d . . . H18A H 0.9370 0.1181 0.2680 0.103 Uiso 1 calc R . . H18B H 0.9419 -0.0174 0.2502 0.103 Uiso 1 calc R . . H18C H 0.9860 0.0535 0.3105 0.103 Uiso 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 Cl 0.0611(6) 0.0545(6) 0.0510(6) 0.0163(5) -0.0062(5) 0.0048(5) O1 0.069(2) 0.096(2) 0.0601(19) -0.0401(18) 0.0007(16) -0.0087(18) O4 0.0495(15) 0.0324(14) 0.0545(15) -0.0005(12) -0.0102(13) -0.0001(12) N10 0.0337(17) 0.0418(16) 0.0312(16) -0.0045(14) -0.0026(14) 0.0017(13) C1 0.046(2) 0.048(2) 0.048(2) -0.001(2) 0.004(2) 0.0031(19) C2 0.048(2) 0.057(3) 0.055(3) 0.005(2) 0.011(2) 0.005(2) C3 0.041(2) 0.059(2) 0.049(3) 0.010(2) -0.003(2) -0.003(2) C3A 0.039(2) 0.036(2) 0.036(2) 0.0023(17) -0.0018(17) -0.0004(17) C5 0.051(2) 0.044(2) 0.055(3) -0.007(2) -0.006(2) 0.009(2) C5A 0.042(2) 0.038(2) 0.043(2) 0.0043(17) 0.0028(18) 0.0046(18) C6 0.048(2) 0.052(2) 0.058(3) -0.002(2) 0.004(2) 0.011(2) C7 0.036(2) 0.071(3) 0.076(3) 0.008(3) 0.005(2) 0.010(2) C8 0.041(3) 0.059(3) 0.085(3) -0.001(3) -0.007(2) -0.001(2) C9 0.042(3) 0.051(2) 0.055(2) -0.005(2) -0.009(2) 0.001(2) C9A 0.035(2) 0.039(2) 0.037(2) 0.0034(17) 0.0004(17) 0.0021(17) C12 0.0317(19) 0.0342(19) 0.0355(19) -0.0027(16) 0.0007(16) 0.0031(16) C13 0.042(2) 0.0323(19) 0.040(2) -0.0078(17) -0.0074(17) -0.0012(17) C14 0.044(2) 0.0283(17) 0.049(2) -0.0008(18) 0.0019(19) 0.0004(17) C15 0.035(2) 0.042(2) 0.038(2) 0.0051(17) 0.0029(17) 0.0063(17) C16 0.052(2) 0.046(2) 0.040(2) -0.0022(18) -0.0112(18) -0.0010(19) C17 0.052(2) 0.0324(19) 0.047(2) -0.0004(17) -0.0100(19) -0.0030(18) C18 0.068(3) 0.082(3) 0.056(3) 0.011(2) 0.017(2) 0.017(3) _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 C15 1.745(3) . y O1 C1 1.211(4) . y O4 C3A 1.412(4) . y O4 C5 1.434(4) . y N10 C1 1.358(4) . y N10 C3A 1.465(4) . y N10 C9A 1.470(4) . y C1 C2 1.541(5) . ? C2 C3 1.490(5) . ? C2 C18 1.524(5) . ? C2 H2 1.09(3) . ? C3 C3A 1.522(5) . ? C3 H3A 1.01(3) . ? C3 H3B 0.97(3) . ? C3A C12 1.536(4) . ? C5 C5A 1.513(5) . ? C5 H5A 0.99(3) . ? C5 H5B 1.04(3) . ? C5A C6 1.517(5) . ? C5A C9A 1.534(5) . ? C5A H5A1 0.93(3) . ? C6 C7 1.514(6) . ? C6 H6A 0.99(3) . ? C6 H6B 1.00(4) . ? C7 C8 1.515(6) . ? C7 H7A 0.89(4) . ? C7 H7B 1.02(4) . ? C8 C9 1.530(5) . ? C8 H8A 0.98(4) . ? C8 H8B 1.04(4) . ? C9 C9A 1.521(5) . ? C9 H9A 0.99(3) . ? C9 H9B 1.03(3) . ? C9A H9A1 0.97(3) . ? C12 C17 1.383(4) . ? C12 C13 1.387(4) . ? C13 C14 1.383(4) . ? C13 H13 0.9300 . ? C14 C15 1.372(4) . ? C14 H14 0.9300 . ? C15 C16 1.379(5) . ? C16 C17 1.382(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C3A O4 C5 112.8(3) . . Y C1 N10 C3A 113.1(3) . . y C1 N10 C9A 129.5(3) . . y C3A N10 C9A 117.1(3) . . y O1 C1 N10 127.6(3) . . y O1 C1 C2 125.2(4) . . y N10 C1 C2 107.1(3) . . y C3 C2 C18 118.3(3) . . ? C3 C2 C1 104.3(3) . . ? C18 C2 C1 111.8(3) . . ? C3 C2 H2 110.9(18) . . ? C18 C2 H2 107.1(18) . . ? C1 C2 H2 103.5(19) . . ? C2 C3 C3A 105.0(3) . . ? C2 C3 H3A 108.1(19) . . ? C3A C3 H3A 105.4(19) . . ? C2 C3 H3B 117(2) . . ? C3A C3 H3B 113(2) . . ? H3A C3 H3B 107(3) . . ? O4 C3A N10 111.4(3) . . ? O4 C3A C3 107.5(3) . . ? N10 C3A C3 103.0(3) . . ? O4 C3A C12 111.1(3) . . ? N10 C3A C12 112.1(3) . . ? C3 C3A C12 111.4(3) . . ? O4 C5 C5A 111.2(3) . . ? O4 C5 H5A 103(2) . . ? C5A C5 H5A 113(2) . . ? O4 C5 H5B 114(2) . . ? C5A C5 H5B 106(2) . . ? H5A C5 H5B 110(3) . . ? C5 C5A C6 112.2(3) . . ? C5 C5A C9A 109.5(3) . . ? C6 C5A C9A 111.1(3) . . ? C5 C5A H5A1 107(2) . . ? C6 C5A H5A1 111(2) . . ? C9A C5A H5A1 106(2) . . ? C7 C6 C5A 111.8(3) . . ? C7 C6 H6A 107(2) . . ? C5A C6 H6A 109(2) . . ? C7 C6 H6B 110(2) . . ? C5A C6 H6B 112(2) . . ? H6A C6 H6B 106(3) . . ? C6 C7 C8 111.2(4) . . ? C6 C7 H7A 113(3) . . ? C8 C7 H7A 111(3) . . ? C6 C7 H7B 110(2) . . ? C8 C7 H7B 107(2) . . ? H7A C7 H7B 105(3) . . ? C7 C8 C9 112.4(3) . . ? C7 C8 H8A 112(2) . . ? C9 C8 H8A 108(2) . . ? C7 C8 H8B 110(2) . . ? C9 C8 H8B 106(2) . . ? H8A C8 H8B 108(3) . . ? C9A C9 C8 109.8(3) . . ? C9A C9 H9A 111(2) . . ? C8 C9 H9A 111(2) . . ? C9A C9 H9B 110.0(19) . . ? C8 C9 H9B 111.4(19) . . ? H9A C9 H9B 104(3) . . ? N10 C9A C9 115.3(3) . . ? N10 C9A C5A 107.8(3) . . ? C9 C9A C5A 111.2(3) . . ? N10 C9A H9A1 106.6(19) . . ? C9 C9A H9A1 109.1(19) . . ? C5A C9A H9A1 106.4(19) . . ? C17 C12 C13 118.3(3) . . ? C17 C12 C3A 118.9(3) . . ? C13 C12 C3A 122.5(3) . . ? C14 C13 C12 121.2(3) . . ? C14 C13 H13 119.4 . . ? C12 C13 H13 119.4 . . ? C15 C14 C13 119.0(3) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C14 C15 C16 121.3(3) . . ? C14 C15 Cl 119.6(3) . . ? C16 C15 Cl 119.1(3) . . ? C15 C16 C17 118.8(3) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C16 C17 C12 121.4(3) . . ? C16 C17 H17 119.3 . . ? C12 C17 H17 119.3 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C3A N10 C1 O1 173.6(4) . . . . ? C9A N10 C1 O1 0.1(6) . . . . ? C3A N10 C1 C2 -3.7(4) . . . . ? C9A N10 C1 C2 -177.2(3) . . . . ? O1 C1 C2 C3 168.7(4) . . . . ? N10 C1 C2 C3 -13.9(4) . . . . ? O1 C1 C2 C18 39.7(6) . . . . ? N10 C1 C2 C18 -143.0(3) . . . . ? C18 C2 C3 C3A 150.1(3) . . . . ? C1 C2 C3 C3A 25.1(4) . . . . ? C5 O4 C3A N10 53.6(4) . . . . ? C5 O4 C3A C3 165.7(3) . . . . ? C5 O4 C3A C12 -72.1(3) . . . . ? C1 N10 C3A O4 134.2(3) . . . . ? C9A N10 C3A O4 -51.3(4) . . . . ? C1 N10 C3A C3 19.3(4) . . . . ? C9A N10 C3A C3 -166.3(3) . . . . ? C1 N10 C3A C12 -100.6(3) . . . . ? C9A N10 C3A C12 73.8(3) . . . . ? C2 C3 C3A O4 -144.6(3) . . . . ? C2 C3 C3A N10 -26.9(4) . . . . ? C2 C3 C3A C12 93.4(3) . . . . ? C3A O4 C5 C5A -59.4(4) . . . . ? O4 C5 C5A C6 -178.0(3) . . . . ? O4 C5 C5A C9A 58.2(4) . . . . ? C5 C5A C6 C7 -177.9(3) . . . . ? C9A C5A C6 C7 -55.0(4) . . . . ? C5A C6 C7 C8 54.2(5) . . . . ? C6 C7 C8 C9 -55.1(5) . . . . ? C7 C8 C9 C9A 55.9(5) . . . . ? C1 N10 C9A C9 -11.3(5) . . . . ? C3A N10 C9A C9 175.3(3) . . . . ? C1 N10 C9A C5A -136.2(3) . . . . ? C3A N10 C9A C5A 50.5(4) . . . . ? C8 C9 C9A N10 -179.0(3) . . . . ? C8 C9 C9A C5A -56.0(4) . . . . ? C5 C5A C9A N10 -52.0(4) . . . . ? C6 C5A C9A N10 -176.5(3) . . . . ? C5 C5A C9A C9 -179.2(3) . . . . ? C6 C5A C9A C9 56.3(4) . . . . ? O4 C3A C12 C17 -37.2(4) . . . . ? N10 C3A C12 C17 -162.5(3) . . . . ? C3 C3A C12 C17 82.6(4) . . . . ? O4 C3A C12 C13 149.9(3) . . . . ? N10 C3A C12 C13 24.6(4) . . . . ? C3 C3A C12 C13 -90.3(4) . . . . ? C17 C12 C13 C14 -1.1(5) . . . . ? C3A C12 C13 C14 171.9(3) . . . . ? C12 C13 C14 C15 -0.2(5) . . . . ? C13 C14 C15 C16 2.1(5) . . . . ? C13 C14 C15 Cl -177.7(3) . . . . ? C14 C15 C16 C17 -2.7(5) . . . . ? Cl C15 C16 C17 177.2(3) . . . . ? C15 C16 C17 C12 1.3(5) . . . . ? C13 C12 C17 C16 0.6(5) . . . . ? C3A C12 C17 C16 -172.6(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13 N10 0.93 2.55 2.887(4) 101.5 . C17 H17 O4 0.93 2.52 2.831(4) 99.9 . _diffrn_measured_fraction_theta_max 0.884 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.884 _refine_diff_density_max 0.194 _refine_diff_density_min -0.212 _refine_diff_density_rms 0.049 #===END data_j1404n=6a/6s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C18 H20 Cl N O2' _chemical_formula_weight 317.80 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 8.941(4) _cell_length_b 12.749(4) _cell_length_c 15.113(3) _cell_angle_alpha 90.00 _cell_angle_beta 105.06(2) _cell_angle_gamma 90.00 _cell_volume 1663.5(9) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 12.3 _cell_measurement_theta_max 16.6 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.32 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.269 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 672 _exptl_absorpt_coefficient_mu 0.236 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method '\w--2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3121 _diffrn_reflns_av_R_equivalents 0.0194 _diffrn_reflns_av_sigmaI/netI 0.0494 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 2.36 _diffrn_reflns_theta_max 24.99 _reflns_number_total 2925 _reflns_number_gt 1631 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_cell_refinement ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_data_reduction ; TEXSAN for WINDOWS(Molecular Structure Corporation, 1997) ; _computing_structure_solution 'SIR-92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for WINDOWS (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0518P)^2^+0.8440P] 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_number_reflns 2925 _refine_ls_number_parameters 238 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1232 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1483 _refine_ls_wR_factor_gt 0.1221 _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_restrained_S_all 1.015 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl 1.12195(13) 0.66047(13) 1.10606(10) 0.1455(7) Uani 1 d . . . O1A O 0.3126(5) 1.0360(4) 0.8258(3) 0.0530(12) Uiso 0.50 d P . . O1B O 0.3668(6) 1.0458(4) 0.8628(3) 0.0598(13) Uiso 0.50 d P . . O4 O 0.4950(2) 0.74716(15) 0.75945(14) 0.0584(6) Uani 1 d . . . N10 N 0.5083(3) 0.91030(17) 0.83662(16) 0.0460(6) Uani 1 d . . . C1 C 0.3824(4) 0.9497(3) 0.8572(3) 0.0735(11) Uani 1 d . . . C2B C 0.2739(10) 0.8593(7) 0.8719(6) 0.059(2) Uani 0.50 d P . . H2B H 0.1915 0.8487 0.8155 0.071 Uiso 0.50 calc PR . . C2A C 0.3392(9) 0.8696(7) 0.9227(6) 0.054(2) Uani 0.50 d P . . H2A H 0.3930 0.8819 0.9871 0.065 Uiso 0.50 calc PR . . C3 C 0.3845(4) 0.7679(3) 0.8861(3) 0.0650(10) Uani 1 d . . . H3A H 0.417(5) 0.728(3) 0.940(3) 0.113(15) Uiso 1 d . . . H3B H 0.312(5) 0.730(4) 0.840(3) 0.124(18) Uiso 1 d . . . C3A C 0.5215(3) 0.7958(2) 0.8469(2) 0.0474(7) Uani 1 d . . . C5 C 0.5836(5) 0.7914(3) 0.7015(2) 0.0609(9) Uani 1 d . . . H5A H 0.555(3) 0.754(3) 0.645(2) 0.073 Uiso 1 d . . . H5B H 0.698(4) 0.783(3) 0.730(2) 0.073 Uiso 1 d . . . C5A C 0.5456(4) 0.9070(3) 0.6840(2) 0.0542(8) Uani 1 d . . . H5A1 H 0.436(4) 0.915(2) 0.661(2) 0.065 Uiso 1 d . . . C6 C 0.6252(5) 0.9550(3) 0.6157(2) 0.0692(10) Uani 1 d . . . H6A H 0.630(4) 0.901(3) 0.567(2) 0.083 Uiso 1 d . . . H6B H 0.557(4) 1.009(3) 0.583(2) 0.083 Uiso 1 d . . . C7 C 0.7821(5) 0.9949(3) 0.6572(3) 0.0755(11) Uani 1 d . . . H7 H 0.8439 1.0114 0.6183 0.091 Uiso 1 calc R . . C8 C 0.8407(4) 1.0088(3) 0.7453(3) 0.0701(10) Uani 1 d . . . H8 H 0.9387 1.0386 0.7650 0.084 Uiso 1 calc R . . C9A C 0.5853(3) 0.9650(2) 0.7750(2) 0.0464(7) Uani 1 d . . . H9A H 0.546(3) 1.025(2) 0.766(2) 0.056 Uiso 1 d . . . C9 C 0.7583(4) 0.9792(3) 0.8156(2) 0.0595(9) Uani 1 d . . . H9B H 0.773(4) 1.028(3) 0.862(2) 0.071 Uiso 1 d . . . H9C H 0.803(3) 0.909(3) 0.844(2) 0.071 Uiso 1 d . . . C18A C 0.1580(9) 0.8789(6) 0.9029(6) 0.075(2) Uiso 0.50 d P . . H18A H 0.1119 0.8690 0.8386 0.090 Uiso 0.50 calc PR . . H18B H 0.1314 0.9471 0.9210 0.090 Uiso 0.50 calc PR . . H18C H 0.1203 0.8262 0.9370 0.090 Uiso 0.50 calc PR . . C18B C 0.2035(10) 0.8880(6) 0.9485(6) 0.075(2) Uiso 0.50 d P . . H18D H 0.1351 0.8331 0.9569 0.090 Uiso 0.50 calc PR . . H18E H 0.1462 0.9522 0.9337 0.090 Uiso 0.50 calc PR . . H18F H 0.2841 0.8972 1.0040 0.090 Uiso 0.50 calc PR . . C12 C 0.6746(3) 0.7614(2) 0.9104(2) 0.0480(7) Uani 1 d . . . C13 C 0.7340(4) 0.8140(3) 0.9929(2) 0.0598(9) Uani 1 d . . . H13 H 0.6812 0.8716 1.0075 0.072 Uiso 1 calc R . . C14 C 0.8697(5) 0.7817(3) 1.0530(2) 0.0793(11) Uani 1 d . . . H14 H 0.9082 0.8171 1.1080 0.095 Uiso 1 calc R . . C15 C 0.9473(4) 0.6973(4) 1.0314(3) 0.0811(12) Uani 1 d . . . C16 C 0.8903(4) 0.6429(3) 0.9522(3) 0.0783(11) Uani 1 d . . . H16 H 0.9433 0.5847 0.9388 0.094 Uiso 1 calc R . . C17 C 0.7535(4) 0.6744(2) 0.8918(2) 0.0592(8) Uani 1 d . . . H17 H 0.7142 0.6368 0.8381 0.071 Uiso 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 Cl 0.0702(7) 0.1934(15) 0.1513(12) 0.0752(11) -0.0098(7) 0.0164(8) O4 0.0665(13) 0.0443(12) 0.0622(13) -0.0086(11) 0.0126(11) -0.0114(11) N10 0.0477(14) 0.0375(13) 0.0583(15) 0.0020(11) 0.0238(12) 0.0027(11) C1 0.097(3) 0.0393(19) 0.106(3) 0.0103(18) 0.065(2) 0.0121(18) C2B 0.048(5) 0.066(5) 0.074(6) 0.004(5) 0.034(4) 0.008(4) C2A 0.044(5) 0.062(5) 0.060(5) 0.005(4) 0.018(4) 0.002(4) C3 0.059(2) 0.053(2) 0.091(3) 0.013(2) 0.033(2) -0.0011(18) C3A 0.0528(18) 0.0324(15) 0.0599(19) -0.0016(14) 0.0199(15) 0.0002(14) C5 0.087(3) 0.049(2) 0.0483(19) -0.0081(16) 0.0203(19) -0.0070(19) C5A 0.0567(19) 0.057(2) 0.0443(17) 0.0015(15) 0.0046(15) -0.0020(16) C6 0.094(3) 0.068(2) 0.048(2) 0.0059(18) 0.023(2) 0.005(2) C7 0.087(3) 0.080(3) 0.076(3) 0.010(2) 0.049(2) -0.001(2) C8 0.063(2) 0.076(3) 0.078(3) 0.004(2) 0.030(2) -0.0135(18) C9A 0.0516(19) 0.0369(16) 0.0557(18) 0.0030(15) 0.0226(15) 0.0022(14) C9 0.059(2) 0.067(2) 0.054(2) -0.0055(17) 0.0180(17) -0.0145(18) C12 0.0518(17) 0.0436(17) 0.0527(17) 0.0050(14) 0.0210(14) 0.0020(14) C13 0.068(2) 0.059(2) 0.0538(19) 0.0014(16) 0.0179(17) 0.0000(17) C14 0.078(3) 0.093(3) 0.058(2) 0.013(2) 0.003(2) -0.017(2) C15 0.051(2) 0.099(3) 0.090(3) 0.041(3) 0.012(2) 0.006(2) C16 0.063(2) 0.078(3) 0.101(3) 0.029(2) 0.034(2) 0.024(2) C17 0.061(2) 0.0497(19) 0.072(2) 0.0038(16) 0.0260(17) 0.0074(16) _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 C15 1.737(4) . y O1A C1 1.293(5) . y O1B C1 1.239(5) . y O4 C3A 1.423(3) . y O4 C5 1.440(4) . y N10 C1 1.341(4) . y N10 C3A 1.470(3) . y N10 C9A 1.471(3) . y C1 C2A 1.540(9) . ? C1 C2B 1.559(9) . ? C2B C18B 1.501(11) . ? C2B C3 1.508(9) . ? C2B H2B 0.9800 . ? C2A C3 1.507(9) . ? C2A C18A 1.573(10) . ? C2A H2A 0.9800 . ? C3 C3A 1.535(4) . ? C3 H3A 0.94(4) . ? C3 H3B 0.94(4) . ? C3A C12 1.518(4) . ? C5 C5A 1.520(4) . ? C5 H5A 0.95(3) . ? C5 H5B 1.01(3) . ? C5A C9A 1.519(4) . ? C5A C6 1.527(5) . ? C5A H5A1 0.96(3) . ? C6 C7 1.470(5) . ? C6 H6A 1.01(4) . ? C6 H6B 0.97(3) . ? C7 C8 1.310(5) . ? C7 H7 0.9300 . ? C8 C9 1.490(4) . ? C8 H8 0.9300 . ? C9A C9 1.519(4) . ? C9A H9A 0.84(3) . ? C9 H9B 0.93(3) . ? C9 H9C 1.03(3) . ? C18A H18A 0.9600 . ? C18A H18B 0.9600 . ? C18A H18C 0.9600 . ? C18B H18D 0.9600 . ? C18B H18E 0.9600 . ? C18B H18F 0.9600 . ? C12 C17 1.381(4) . ? C12 C13 1.394(4) . ? C13 C14 1.377(5) . ? C13 H13 0.9300 . ? C14 C15 1.366(5) . ? C14 H14 0.9300 . ? C15 C16 1.362(5) . ? C16 C17 1.383(5) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? 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 C3A O4 C5 114.1(2) . . y C1 N10 C3A 113.4(2) . . y C1 N10 C9A 121.9(2) . . y C3A N10 C9A 120.0(2) . . y O1B C1 O1A 29.6(3) . . y O1B C1 N10 120.2(4) . . y O1A C1 N10 126.0(3) . . y O1B C1 C2A 124.1(5) . . y O1A C1 C2A 128.5(4) . . y N10 C1 C2A 105.5(4) . . y O1B C1 C2B 129.5(4) . . y O1A C1 C2B 115.0(5) . . y N10 C1 C2B 110.3(4) . . y C2A C1 C2B 31.7(3) . . ? C18B C2B C3 118.0(7) . . ? C18B C2B C1 109.3(6) . . ? C3 C2B C1 100.5(5) . . ? C18B C2B H2B 109.5 . . ? C3 C2B H2B 109.5 . . ? C1 C2B H2B 109.5 . . ? C3 C2A C1 101.4(5) . . ? C3 C2A C18A 110.9(6) . . ? C1 C2A C18A 104.2(6) . . ? C3 C2A H2A 113.1 . . ? C1 C2A H2A 113.1 . . ? C18A C2A H2A 113.1 . . ? C2A C3 C2B 32.6(3) . . ? C2A C3 C3A 105.1(4) . . ? C2B C3 C3A 109.0(4) . . ? C2A C3 H3A 102(3) . . ? C2B C3 H3A 126(3) . . ? C3A C3 H3A 111(3) . . ? C2A C3 H3B 121(3) . . ? C2B C3 H3B 90(3) . . ? C3A C3 H3B 107(3) . . ? H3A C3 H3B 111(4) . . ? O4 C3A N10 110.2(2) . . ? O4 C3A C12 111.5(2) . . ? N10 C3A C12 112.9(2) . . ? O4 C3A C3 107.5(3) . . ? N10 C3A C3 102.8(2) . . ? C12 C3A C3 111.6(3) . . ? O4 C5 C5A 110.6(3) . . ? O4 C5 H5A 107(2) . . ? C5A C5 H5A 109.6(19) . . ? O4 C5 H5B 110.5(18) . . ? C5A C5 H5B 109.7(19) . . ? H5A C5 H5B 110(3) . . ? C9A C5A C5 109.0(3) . . ? C9A C5A C6 112.1(3) . . ? C5 C5A C6 112.6(3) . . ? C9A C5A H5A1 104.7(18) . . ? C5 C5A H5A1 109.2(19) . . ? C6 C5A H5A1 108.9(18) . . ? C7 C6 C5A 114.2(3) . . ? C7 C6 H6A 109.3(19) . . ? C5A C6 H6A 109.2(19) . . ? C7 C6 H6B 112(2) . . ? C5A C6 H6B 107(2) . . ? H6A C6 H6B 104(3) . . ? C8 C7 C6 124.5(3) . . ? C8 C7 H7 117.8 . . ? C6 C7 H7 117.8 . . ? C7 C8 C9 123.3(3) . . ? C7 C8 H8 118.4 . . ? C9 C8 H8 118.4 . . ? N10 C9A C9 113.3(2) . . ? N10 C9A C5A 107.7(2) . . ? C9 C9A C5A 113.4(3) . . ? N10 C9A H9A 107(2) . . ? C9 C9A H9A 107(2) . . ? C5A C9A H9A 108(2) . . ? C8 C9 C9A 112.5(3) . . ? C8 C9 H9B 112(2) . . ? C9A C9 H9B 108(2) . . ? C8 C9 H9C 107.9(18) . . ? C9A C9 H9C 107.8(18) . . ? H9B C9 H9C 108(3) . . ? C2A C18A H18A 109.5 . . ? C2A C18A H18B 109.5 . . ? H18A C18A H18B 109.5 . . ? C2A C18A H18C 109.5 . . ? H18A C18A H18C 109.5 . . ? H18B C18A H18C 109.5 . . ? C2B C18B H18D 109.5 . . ? C2B C18B H18E 109.5 . . ? H18D C18B H18E 109.5 . . ? C2B C18B H18F 109.5 . . ? H18D C18B H18F 109.5 . . ? H18E C18B H18F 109.5 . . ? C17 C12 C13 118.2(3) . . ? C17 C12 C3A 121.8(3) . . ? C13 C12 C3A 119.9(3) . . ? C14 C13 C12 120.8(3) . . ? C14 C13 H13 119.6 . . ? C12 C13 H13 119.6 . . ? C15 C14 C13 119.5(4) . . ? C15 C14 H14 120.2 . . ? C13 C14 H14 120.2 . . ? C16 C15 C14 121.0(4) . . ? C16 C15 Cl 120.1(4) . . ? C14 C15 Cl 119.0(4) . . ? C15 C16 C17 119.8(4) . . ? C15 C16 H16 120.1 . . ? C17 C16 H16 120.1 . . ? C12 C17 C16 120.7(3) . . ? C12 C17 H17 119.7 . . ? C16 C17 H17 119.7 . . ? 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 C3A N10 C1 O1B 170.9(4) . . . . ? C9A N10 C1 O1B -33.4(6) . . . . ? C3A N10 C1 O1A -154.3(4) . . . . ? C9A N10 C1 O1A 1.4(6) . . . . ? C3A N10 C1 C2A 24.4(5) . . . . ? C9A N10 C1 C2A -179.9(4) . . . . ? C3A N10 C1 C2B -8.6(5) . . . . ? C9A N10 C1 C2B 147.1(4) . . . . ? O1B C1 C2B C18B -37.0(10) . . . . ? O1A C1 C2B C18B -67.8(8) . . . . ? N10 C1 C2B C18B 142.4(6) . . . . ? C2A C1 C2B C18B 55.7(9) . . . . ? O1B C1 C2B C3 -161.8(5) . . . . ? O1A C1 C2B C3 167.4(5) . . . . ? N10 C1 C2B C3 17.6(7) . . . . ? C2A C1 C2B C3 -69.1(9) . . . . ? O1B C1 C2A C3 -178.9(5) . . . . ? O1A C1 C2A C3 144.6(5) . . . . ? N10 C1 C2A C3 -34.0(6) . . . . ? C2B C1 C2A C3 69.7(9) . . . . ? O1B C1 C2A C18A 65.9(8) . . . . ? O1A C1 C2A C18A 29.3(9) . . . . ? N10 C1 C2A C18A -149.3(5) . . . . ? C2B C1 C2A C18A -45.6(8) . . . . ? C1 C2A C3 C2B -70.9(9) . . . . ? C18A C2A C3 C2B 39.3(8) . . . . ? C1 C2A C3 C3A 30.9(6) . . . . ? C18A C2A C3 C3A 141.1(6) . . . . ? C18B C2B C3 C2A -50.1(9) . . . . ? C1 C2B C3 C2A 68.5(9) . . . . ? C18B C2B C3 C3A -138.6(7) . . . . ? C1 C2B C3 C3A -19.9(7) . . . . ? C5 O4 C3A N10 49.8(3) . . . . ? C5 O4 C3A C12 -76.3(3) . . . . ? C5 O4 C3A C3 161.1(3) . . . . ? C1 N10 C3A O4 110.0(3) . . . . ? C9A N10 C3A O4 -46.2(3) . . . . ? C1 N10 C3A C12 -124.6(3) . . . . ? C9A N10 C3A C12 79.1(3) . . . . ? C1 N10 C3A C3 -4.3(4) . . . . ? C9A N10 C3A C3 -160.5(3) . . . . ? C2A C3 C3A O4 -134.2(4) . . . . ? C2B C3 C3A O4 -100.3(5) . . . . ? C2A C3 C3A N10 -18.0(5) . . . . ? C2B C3 C3A N10 15.9(6) . . . . ? C2A C3 C3A C12 103.2(5) . . . . ? C2B C3 C3A C12 137.1(5) . . . . ? C3A O4 C5 C5A -59.8(3) . . . . ? O4 C5 C5A C9A 60.4(4) . . . . ? O4 C5 C5A C6 -174.6(3) . . . . ? C9A C5A C6 C7 36.2(4) . . . . ? C5 C5A C6 C7 -87.2(4) . . . . ? C5A C6 C7 C8 -13.1(6) . . . . ? C6 C7 C8 C9 4.0(6) . . . . ? C1 N10 C9A C9 128.1(3) . . . . ? C3A N10 C9A C9 -77.8(3) . . . . ? C1 N10 C9A C5A -105.7(3) . . . . ? C3A N10 C9A C5A 48.5(3) . . . . ? C5 C5A C9A N10 -52.4(3) . . . . ? C6 C5A C9A N10 -177.8(3) . . . . ? C5 C5A C9A C9 73.7(4) . . . . ? C6 C5A C9A C9 -51.6(4) . . . . ? C7 C8 C9 C9A -18.4(5) . . . . ? N10 C9A C9 C8 165.1(3) . . . . ? C5A C9A C9 C8 42.0(4) . . . . ? O4 C3A C12 C17 -15.6(4) . . . . ? N10 C3A C12 C17 -140.3(3) . . . . ? C3 C3A C12 C17 104.6(3) . . . . ? O4 C3A C12 C13 168.6(2) . . . . ? N10 C3A C12 C13 44.0(4) . . . . ? C3 C3A C12 C13 -71.1(4) . . . . ? C17 C12 C13 C14 1.7(5) . . . . ? C3A C12 C13 C14 177.6(3) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C13 C14 C15 C16 -1.7(6) . . . . ? C13 C14 C15 Cl 177.7(3) . . . . ? C14 C15 C16 C17 1.3(6) . . . . ? Cl C15 C16 C17 -178.1(3) . . . . ? C13 C12 C17 C16 -2.1(4) . . . . ? C3A C12 C17 C16 -178.0(3) . . . . ? C15 C16 C17 C12 0.7(5) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C17 H17 O4 0.93 2.45 2.792(4) 101.5 . C13 H13 N10 0.93 2.69 2.946(4) 96.8 . _diffrn_measured_fraction_theta_max 0.952 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.952 _refine_diff_density_max 0.292 _refine_diff_density_min -0.213 _refine_diff_density_rms 0.038 #===END data_j1407f=9a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 Cl N O2' _chemical_formula_weight 329.81 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/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 8.754(9) _cell_length_b 16.647(4) _cell_length_c 11.575(2) _cell_angle_alpha 90.00 _cell_angle_beta 103.47(3) _cell_angle_gamma 90.00 _cell_volume 1640.4(17) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.4 _cell_measurement_theta_max 16.3 _exptl_crystal_description bar _exptl_crystal_colour colourless _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.38 _exptl_crystal_size_min 0.36 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.335 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method '\w--2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3068 _diffrn_reflns_av_R_equivalents 0.0244 _diffrn_reflns_av_sigmaI/netI 0.0543 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 2.18 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2875 _reflns_number_gt 1758 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_cell_refinement ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_data_reduction ; TEXSAN for WINDOWS(Molecular Structure Corporation, 1997) ; _computing_structure_solution 'SIR-92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for WINDOWS (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0450P)^2^+0.6500P] 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_number_reflns 2875 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1049 _refine_ls_R_factor_gt 0.0455 _refine_ls_wR_factor_ref 0.1202 _refine_ls_wR_factor_gt 0.0995 _refine_ls_goodness_of_fit_ref 1.021 _refine_ls_restrained_S_all 1.021 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl -0.76402(12) 0.01245(6) 0.04415(7) 0.0758(3) Uani 1 d . . . O1 O -0.5505(3) -0.07636(13) -0.60653(17) 0.0576(6) Uani 1 d . . . O4 O -0.7912(2) -0.24558(11) -0.40655(16) 0.0440(5) Uani 1 d . . . N10 N -0.6214(3) -0.15021(13) -0.46059(19) 0.0395(6) Uani 1 d . . . C1 C -0.6455(4) -0.09386(17) -0.5481(2) 0.0444(7) Uani 1 d . . . C2 C -0.8080(4) -0.0582(2) -0.5601(2) 0.0499(8) Uani 1 d . . . H2 H -0.794(3) -0.0108(19) -0.513(3) 0.060 Uiso 1 d . . . C3 C -0.8904(4) -0.1237(2) -0.5054(3) 0.0480(8) Uani 1 d . . . H3A H -0.972(3) -0.1012(18) -0.471(3) 0.058 Uiso 1 d . . . H3B H -0.926(3) -0.1637(19) -0.566(3) 0.058 Uiso 1 d . . . C3A C -0.7599(3) -0.16253(16) -0.4113(2) 0.0383(6) Uani 1 d . . . C5 C -0.6612(4) -0.28809(19) -0.3327(3) 0.0470(7) Uani 1 d . . . H5A H -0.697(3) -0.3438(19) -0.329(2) 0.056 Uiso 1 d . . . H5B H -0.641(3) -0.2605(18) -0.252(3) 0.056 Uiso 1 d . . . C5A C -0.5151(3) -0.28590(18) -0.3826(3) 0.0437(7) Uani 1 d . . . H5A1 H -0.519(3) -0.3312(17) -0.434(2) 0.052 Uiso 1 d . . . C6 C -0.3630(4) -0.2919(2) -0.2812(3) 0.0524(8) Uani 1 d . . . H6 H -0.369(3) -0.3327(19) -0.221(3) 0.063 Uiso 1 d . . . C7 C -0.2288(4) -0.3009(2) -0.3424(3) 0.0642(10) Uani 1 d . . . H7 H -0.1703 -0.3473 -0.3446 0.077 Uiso 1 calc R . . C8 C -0.2098(4) -0.2320(2) -0.3917(3) 0.0698(10) Uani 1 d . . . H8 H -0.1352 -0.2205 -0.4349 0.084 Uiso 1 calc R . . C9 C -0.3314(4) -0.1746(2) -0.3656(3) 0.0580(9) Uani 1 d . . . H9 H -0.318(4) -0.120(2) -0.374(3) 0.070 Uiso 1 d . . . C9A C -0.4889(3) -0.20539(18) -0.4444(3) 0.0418(7) Uani 1 d . . . H9A H -0.475(3) -0.2159(17) -0.525(3) 0.050 Uiso 1 d . . . C11 C -0.3413(4) -0.2041(2) -0.2424(3) 0.0590(9) Uani 1 d . . . H11A H -0.238(4) -0.1991(19) -0.181(3) 0.071 Uiso 1 d . . . H11B H -0.425(4) -0.184(2) -0.216(3) 0.071 Uiso 1 d . . . C12 C -0.7466(3) -0.12215(17) -0.2906(2) 0.0379(6) Uani 1 d . . . C13 C -0.6538(3) -0.05506(17) -0.2573(2) 0.0438(7) Uani 1 d . . . H13 H -0.5882 -0.0374 -0.3047 0.053 Uiso 1 calc R . . C14 C -0.6574(3) -0.01369(18) -0.1536(2) 0.0485(7) Uani 1 d . . . H14 H -0.5948 0.0314 -0.1315 0.058 Uiso 1 calc R . . C15 C -0.7553(4) -0.04056(19) -0.0839(2) 0.0480(8) Uani 1 d . . . C16 C -0.8474(3) -0.10751(19) -0.1143(2) 0.0483(8) Uani 1 d . . . H16 H -0.9120 -0.1251 -0.0661 0.058 Uiso 1 calc R . . C17 C -0.8431(3) -0.14854(18) -0.2175(2) 0.0445(7) Uani 1 d . . . H17 H -0.9049 -0.1941 -0.2384 0.053 Uiso 1 calc R . . C18 C -0.8877(4) -0.0354(2) -0.6869(3) 0.0688(10) Uani 1 d . . . H18A H -0.8182 -0.0025 -0.7197 0.103 Uiso 1 calc R . . H18B H -0.9824 -0.0062 -0.6874 0.103 Uiso 1 calc R . . H18C H -0.9128 -0.0833 -0.7338 0.103 Uiso 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 Cl 0.0946(7) 0.0908(8) 0.0470(5) -0.0177(5) 0.0263(5) 0.0083(6) O1 0.0736(15) 0.0601(14) 0.0487(12) 0.0076(10) 0.0335(12) -0.0096(11) O4 0.0438(11) 0.0426(12) 0.0476(11) -0.0009(9) 0.0146(9) -0.0085(10) N10 0.0484(14) 0.0363(14) 0.0385(12) 0.0017(11) 0.0198(11) -0.0032(11) C1 0.0617(19) 0.0406(17) 0.0336(14) -0.0031(13) 0.0169(14) -0.0079(15) C2 0.067(2) 0.0480(19) 0.0365(16) 0.0022(14) 0.0158(15) 0.0044(17) C3 0.0499(19) 0.055(2) 0.0409(16) 0.0033(15) 0.0134(15) 0.0030(16) C3A 0.0422(16) 0.0359(16) 0.0401(15) -0.0007(13) 0.0164(13) -0.0055(13) C5 0.0527(19) 0.0372(18) 0.0542(19) 0.0058(15) 0.0185(15) -0.0023(15) C5A 0.0459(17) 0.0408(17) 0.0468(17) -0.0059(14) 0.0160(14) -0.0032(14) C6 0.0520(19) 0.050(2) 0.0537(19) 0.0039(16) 0.0094(16) 0.0047(16) C7 0.0446(19) 0.068(3) 0.076(2) -0.008(2) 0.0072(17) 0.0028(18) C8 0.042(2) 0.089(3) 0.078(2) -0.004(2) 0.0143(17) -0.0106(19) C9 0.0515(19) 0.050(2) 0.071(2) -0.0032(18) 0.0118(17) -0.0178(17) C9A 0.0423(17) 0.0485(18) 0.0374(15) 0.0004(14) 0.0147(13) -0.0053(14) C11 0.055(2) 0.062(2) 0.055(2) -0.0106(17) 0.0016(17) 0.0003(18) C12 0.0411(16) 0.0392(16) 0.0359(14) 0.0042(12) 0.0141(12) 0.0008(13) C13 0.0515(17) 0.0427(18) 0.0422(16) 0.0017(14) 0.0211(13) -0.0038(14) C14 0.0516(19) 0.0454(18) 0.0495(17) -0.0025(15) 0.0140(15) -0.0037(15) C15 0.0548(19) 0.056(2) 0.0345(14) 0.0017(14) 0.0124(14) 0.0127(16) C16 0.0509(18) 0.062(2) 0.0364(16) 0.0115(15) 0.0183(14) 0.0013(16) C17 0.0473(17) 0.0478(18) 0.0413(16) 0.0069(14) 0.0165(14) -0.0040(14) C18 0.087(3) 0.074(3) 0.0443(18) 0.0133(17) 0.0138(17) 0.009(2) _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 C15 1.742(3) . y O1 C1 1.223(3) . y O4 C3A 1.413(3) . y O4 C5 1.440(4) . y N10 C1 1.361(3) . y N10 C9A 1.457(4) . y N10 C3A 1.470(3) . y C1 C2 1.519(4) . ? C2 C18 1.519(4) . ? C2 C3 1.525(4) . ? C2 H2 0.95(3) . ? C3 C3A 1.527(4) . ? C3 H3A 0.97(3) . ? C3 H3B 0.97(3) . ? C3A C12 1.530(4) . ? C5 C5A 1.520(4) . ? C5 H5A 0.98(3) . ? C5 H5B 1.02(3) . ? C5A C6 1.560(4) . ? C5A C9A 1.561(4) . ? C5A H5A1 0.96(3) . ? C6 C7 1.514(5) . ? C6 C11 1.528(5) . ? C6 H6 0.98(3) . ? C7 C8 1.310(5) . ? C7 H7 0.9300 . ? C8 C9 1.513(5) . ? C8 H8 0.9300 . ? C9 C11 1.529(5) . ? C9 C9A 1.552(4) . ? C9 H9 0.92(3) . ? C9A H9A 0.98(3) . ? C11 H11A 1.01(3) . ? C11 H11B 0.92(3) . ? C12 C13 1.382(4) . ? C12 C17 1.398(4) . ? C13 C14 1.391(4) . ? C13 H13 0.9300 . ? C14 C15 1.380(4) . ? C14 H14 0.9300 . ? C15 C16 1.373(4) . ? C16 C17 1.384(4) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C3A O4 C5 111.7(2) . . y C1 N10 C9A 120.7(2) . . y C1 N10 C3A 112.8(2) . . y C9A N10 C3A 124.5(2) . . y O1 C1 N10 124.7(3) . . y O1 C1 C2 126.9(3) . . y N10 C1 C2 108.5(2) . . y C1 C2 C18 113.3(3) . . ? C1 C2 C3 101.9(3) . . ? C18 C2 C3 115.1(3) . . ? C1 C2 H2 106.1(19) . . ? C18 C2 H2 108.3(19) . . ? C3 C2 H2 111.8(18) . . ? C2 C3 C3A 104.6(2) . . ? C2 C3 H3A 111.0(18) . . ? C3A C3 H3A 111.6(17) . . ? C2 C3 H3B 107.2(18) . . ? C3A C3 H3B 106.8(18) . . ? H3A C3 H3B 115(2) . . ? O4 C3A N10 109.7(2) . . ? O4 C3A C3 108.8(2) . . ? N10 C3A C3 102.2(2) . . ? O4 C3A C12 111.6(2) . . ? N10 C3A C12 113.5(2) . . ? C3 C3A C12 110.5(2) . . ? O4 C5 C5A 112.4(2) . . ? O4 C5 H5A 105.8(16) . . ? C5A C5 H5A 110.3(17) . . ? O4 C5 H5B 105.6(16) . . ? C5A C5 H5B 110.9(16) . . ? H5A C5 H5B 112(2) . . ? C5 C5A C6 111.0(3) . . ? C5 C5A C9A 114.9(2) . . ? C6 C5A C9A 102.0(2) . . ? C5 C5A H5A1 107.8(17) . . ? C6 C5A H5A1 108.6(17) . . ? C9A C5A H5A1 112.3(17) . . ? C7 C6 C11 100.1(3) . . ? C7 C6 C5A 105.9(3) . . ? C11 C6 C5A 100.7(3) . . ? C7 C6 H6 115.9(18) . . ? C11 C6 H6 118.4(18) . . ? C5A C6 H6 113.7(18) . . ? C8 C7 C6 108.0(3) . . ? C8 C7 H7 126.0 . . ? C6 C7 H7 126.0 . . ? C7 C8 C9 107.4(3) . . ? C7 C8 H8 126.3 . . ? C9 C8 H8 126.3 . . ? C8 C9 C11 100.3(3) . . ? C8 C9 C9A 104.2(3) . . ? C11 C9 C9A 101.9(3) . . ? C8 C9 H9 119(2) . . ? C11 C9 H9 117(2) . . ? C9A C9 H9 112(2) . . ? N10 C9A C9 116.1(3) . . ? N10 C9A C5A 113.7(2) . . ? C9 C9A C5A 102.7(2) . . ? N10 C9A H9A 105.1(16) . . ? C9 C9A H9A 109.1(16) . . ? C5A C9A H9A 110.2(17) . . ? C6 C11 C9 93.6(3) . . ? C6 C11 H11A 108.2(19) . . ? C9 C11 H11A 113.0(18) . . ? C6 C11 H11B 113(2) . . ? C9 C11 H11B 114(2) . . ? H11A C11 H11B 113(3) . . ? C13 C12 C17 119.0(3) . . ? C13 C12 C3A 121.6(2) . . ? C17 C12 C3A 119.1(2) . . ? C12 C13 C14 120.7(3) . . ? C12 C13 H13 119.7 . . ? C14 C13 H13 119.7 . . ? C15 C14 C13 119.1(3) . . ? C15 C14 H14 120.5 . . ? C13 C14 H14 120.5 . . ? C16 C15 C14 121.4(3) . . ? C16 C15 Cl 119.3(2) . . ? C14 C15 Cl 119.3(3) . . ? C15 C16 C17 119.3(3) . . ? C15 C16 H16 120.3 . . ? C17 C16 H16 120.3 . . ? C16 C17 C12 120.6(3) . . ? C16 C17 H17 119.7 . . ? C12 C17 H17 119.7 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C9A N10 C1 O1 -11.6(4) . . . . ? C3A N10 C1 O1 -176.0(3) . . . . ? C9A N10 C1 C2 168.1(2) . . . . ? C3A N10 C1 C2 3.6(3) . . . . ? O1 C1 C2 C18 33.6(4) . . . . ? N10 C1 C2 C18 -146.0(3) . . . . ? O1 C1 C2 C3 157.8(3) . . . . ? N10 C1 C2 C3 -21.8(3) . . . . ? C1 C2 C3 C3A 30.9(3) . . . . ? C18 C2 C3 C3A 153.9(3) . . . . ? C5 O4 C3A N10 60.2(3) . . . . ? C5 O4 C3A C3 171.2(2) . . . . ? C5 O4 C3A C12 -66.5(3) . . . . ? C1 N10 C3A O4 131.5(2) . . . . ? C9A N10 C3A O4 -32.3(3) . . . . ? C1 N10 C3A C3 16.2(3) . . . . ? C9A N10 C3A C3 -147.6(3) . . . . ? C1 N10 C3A C12 -102.9(3) . . . . ? C9A N10 C3A C12 93.4(3) . . . . ? C2 C3 C3A O4 -144.9(2) . . . . ? C2 C3 C3A N10 -29.0(3) . . . . ? C2 C3 C3A C12 92.2(3) . . . . ? C3A O4 C5 C5A -64.7(3) . . . . ? O4 C5 C5A C6 151.7(3) . . . . ? O4 C5 C5A C9A 36.5(4) . . . . ? C5 C5A C6 C7 172.2(3) . . . . ? C9A C5A C6 C7 -64.9(3) . . . . ? C5 C5A C6 C11 -83.9(3) . . . . ? C9A C5A C6 C11 39.0(3) . . . . ? C11 C6 C7 C8 -33.1(4) . . . . ? C5A C6 C7 C8 71.2(3) . . . . ? C6 C7 C8 C9 -0.3(4) . . . . ? C7 C8 C9 C11 33.6(4) . . . . ? C7 C8 C9 C9A -71.6(4) . . . . ? C1 N10 C9A C9 86.1(3) . . . . ? C3A N10 C9A C9 -111.3(3) . . . . ? C1 N10 C9A C5A -155.1(2) . . . . ? C3A N10 C9A C5A 7.5(4) . . . . ? C8 C9 C9A N10 -165.0(3) . . . . ? C11 C9 C9A N10 91.0(3) . . . . ? C8 C9 C9A C5A 70.3(3) . . . . ? C11 C9 C9A C5A -33.7(3) . . . . ? C5 C5A C9A N10 -9.1(4) . . . . ? C6 C5A C9A N10 -129.4(2) . . . . ? C5 C5A C9A C9 117.1(3) . . . . ? C6 C5A C9A C9 -3.2(3) . . . . ? C7 C6 C11 C9 49.8(3) . . . . ? C5A C6 C11 C9 -58.7(3) . . . . ? C8 C9 C11 C6 -50.1(3) . . . . ? C9A C9 C11 C6 56.9(3) . . . . ? O4 C3A C12 C13 151.1(2) . . . . ? N10 C3A C12 C13 26.6(4) . . . . ? C3 C3A C12 C13 -87.6(3) . . . . ? O4 C3A C12 C17 -35.6(3) . . . . ? N10 C3A C12 C17 -160.2(2) . . . . ? C3 C3A C12 C17 85.6(3) . . . . ? C17 C12 C13 C14 -0.8(4) . . . . ? C3A C12 C13 C14 172.4(3) . . . . ? C12 C13 C14 C15 0.0(4) . . . . ? C13 C14 C15 C16 0.7(4) . . . . ? C13 C14 C15 Cl -178.4(2) . . . . ? C14 C15 C16 C17 -0.6(4) . . . . ? Cl C15 C16 C17 178.5(2) . . . . ? C15 C16 C17 C12 -0.3(4) . . . . ? C13 C12 C17 C16 0.9(4) . . . . ? C3A C12 C17 C16 -172.4(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C13 H13 N10 0.93 2.57 2.905(3) 101.5 . C17 H17 O4 0.93 2.53 2.840(3) 99.6 . _diffrn_measured_fraction_theta_max 0.958 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.958 _refine_diff_density_max 0.182 _refine_diff_density_min -0.193 _refine_diff_density_rms 0.044 #===END data_j1406=10a _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_formula_moiety ? _chemical_formula_sum 'C19 H20 Cl N O2' _chemical_formula_weight 329.81 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' 'Cl' 'Cl' 0.1484 0.1585 '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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M P21/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.640(4) _cell_length_b 10.747(2) _cell_length_c 17.6570(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.853(17) _cell_angle_gamma 90.00 _cell_volume 1639.4(9) _cell_formula_units_Z 4 _cell_measurement_temperature 294(2) _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15.3 _cell_measurement_theta_max 18.8 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.26 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.336 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 696 _exptl_absorpt_coefficient_mu 0.242 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 294(2) _diffrn_radiation_wavelength 0.71069 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Rigaku AFC5S' _diffrn_measurement_method '\w--2\q' _diffrn_standards_number 3 _diffrn_standards_interval_count 150 _diffrn_standards_interval_time ? _diffrn_standards_decay_% 0 _diffrn_reflns_number 3085 _diffrn_reflns_av_R_equivalents 0.0169 _diffrn_reflns_av_sigmaI/netI 0.0397 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_limit_l_max 21 _diffrn_reflns_theta_min 2.22 _diffrn_reflns_theta_max 25.00 _reflns_number_total 2883 _reflns_number_gt 1861 _reflns_threshold_expression I>2\s(I) _computing_data_collection ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_cell_refinement ; MSC/AFC5S Control Program (Molecular Structure Corporation, 1995) ; _computing_data_reduction ; TEXSAN for WINDOWS(Molecular Structure Corporation, 1997) ; _computing_structure_solution 'SIR-92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP-3 for WINDOWS (Farrugia, 1997)' _computing_publication_material 'SHELXL-97 (Sheldrick, 1997)' _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 w=1/[\s^2^(Fo^2^)+(0.0333P)^2^+0.4430P] 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_number_reflns 2883 _refine_ls_number_parameters 241 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0850 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_ref 0.0964 _refine_ls_wR_factor_gt 0.0827 _refine_ls_goodness_of_fit_ref 1.020 _refine_ls_restrained_S_all 1.020 _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_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl Cl 0.21338(11) 0.90620(7) 0.62180(4) 0.0815(3) Uani 1 d . . . O1 O -0.13422(19) 0.89969(15) 1.06187(9) 0.0581(5) Uani 1 d . . . O4 O -0.13925(17) 0.58540(13) 0.89810(8) 0.0464(4) Uani 1 d . . . N10 N -0.14990(19) 0.78596(15) 0.95259(9) 0.0379(4) Uani 1 d . . . C1 C -0.0748(3) 0.8323(2) 1.01458(12) 0.0423(5) Uani 1 d . . . C2 C 0.0910(3) 0.7879(2) 1.01356(12) 0.0451(6) Uani 1 d . . . H2 H 0.149(3) 0.852(2) 0.9880(12) 0.054 Uiso 1 d . . . C3 C 0.0809(3) 0.6724(2) 0.96310(13) 0.0452(6) Uani 1 d . . . H3A H 0.054(3) 0.603(2) 0.9917(13) 0.054 Uiso 1 d . . . H3B H 0.175(3) 0.655(2) 0.9381(12) 0.054 Uiso 1 d . . . C3A C -0.0568(2) 0.69794(19) 0.90896(11) 0.0383(5) Uani 1 d . . . C5 C -0.2835(3) 0.6050(2) 0.85834(15) 0.0531(6) Uani 1 d . . . H5A H -0.322(3) 0.523(2) 0.8484(13) 0.064 Uiso 1 d . . . H5B H -0.265(3) 0.646(2) 0.8094(14) 0.064 Uiso 1 d . . . C5A C -0.3960(3) 0.6839(2) 0.90313(14) 0.0513(6) Uani 1 d . . . H5A1 H -0.449(3) 0.632(2) 0.9381(13) 0.062 Uiso 1 d . . . C6 C -0.5192(3) 0.7554(3) 0.85445(16) 0.0634(8) Uani 1 d . . . H6 H -0.602(3) 0.704(2) 0.8363(14) 0.076 Uiso 1 d . . . C7 C -0.4311(3) 0.8281(3) 0.79607(15) 0.0725(8) Uani 1 d . . . H7 H -0.4302 0.8122 0.7443 0.087 Uiso 1 calc R . . C8 C -0.3557(3) 0.9181(3) 0.83142(16) 0.0650(7) Uani 1 d . . . H8 H -0.2905 0.9760 0.8092 0.078 Uiso 1 calc R . . C9A C -0.3185(3) 0.7929(2) 0.94815(12) 0.0438(6) Uani 1 d . . . H9A H -0.355(2) 0.787(2) 1.0014(12) 0.053 Uiso 1 d . . . C9 C -0.3940(3) 0.9103(2) 0.91383(14) 0.0532(6) Uani 1 d . . . H9 H -0.375(3) 0.987(2) 0.9428(13) 0.064 Uiso 1 d . . . C11 C -0.5611(3) 0.8622(3) 0.90789(18) 0.0652(8) Uani 1 d . . . H11A H -0.632(3) 0.924(3) 0.8832(15) 0.078 Uiso 1 d . . . H11B H -0.597(3) 0.833(3) 0.9591(15) 0.078 Uiso 1 d . . . C12 C 0.0010(2) 0.75160(19) 0.83416(11) 0.0366(5) Uani 1 d . . . C13 C 0.0297(3) 0.8780(2) 0.82666(12) 0.0419(5) Uani 1 d . . . H13 H 0.0040 0.9317 0.8658 0.050 Uiso 1 calc R . . C14 C 0.0956(3) 0.9254(2) 0.76201(12) 0.0470(6) Uani 1 d . . . H14 H 0.1153 1.0102 0.7578 0.056 Uiso 1 calc R . . C15 C 0.1320(3) 0.8458(2) 0.70385(12) 0.0483(6) Uani 1 d . . . C16 C 0.1076(3) 0.7194(2) 0.71004(12) 0.0520(6) Uani 1 d . . . H16 H 0.1342 0.6661 0.6709 0.062 Uiso 1 calc R . . C17 C 0.0429(3) 0.6734(2) 0.77543(12) 0.0459(6) Uani 1 d . . . H17 H 0.0271 0.5882 0.7802 0.055 Uiso 1 calc R . . C18 C 0.1592(3) 0.7645(3) 1.09205(14) 0.0705(8) Uani 1 d . . . H18A H 0.1441 0.8367 1.1231 0.085 Uiso 1 calc R . . H18B H 0.2680 0.7479 1.0882 0.085 Uiso 1 calc R . . H18C H 0.1088 0.6943 1.1144 0.085 Uiso 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 Cl 0.1267(7) 0.0631(5) 0.0557(4) 0.0072(3) 0.0349(4) -0.0049(5) O1 0.0653(11) 0.0563(10) 0.0529(10) -0.0214(9) 0.0082(8) -0.0081(9) O4 0.0523(10) 0.0311(8) 0.0557(9) -0.0039(7) -0.0005(8) -0.0078(7) N10 0.0399(10) 0.0346(10) 0.0392(10) -0.0058(8) 0.0037(8) -0.0040(8) C1 0.0508(14) 0.0360(12) 0.0402(12) -0.0029(10) 0.0062(11) -0.0117(11) C2 0.0502(14) 0.0417(13) 0.0434(13) 0.0016(11) -0.0023(11) -0.0073(11) C3 0.0517(15) 0.0372(13) 0.0467(13) 0.0039(11) 0.0005(11) 0.0006(12) C3A 0.0445(12) 0.0287(11) 0.0417(12) -0.0039(9) 0.0023(10) -0.0029(10) C5 0.0549(16) 0.0413(14) 0.0630(16) -0.0126(13) -0.0018(13) -0.0121(13) C5A 0.0498(15) 0.0510(15) 0.0533(14) -0.0060(12) 0.0048(12) -0.0142(12) C6 0.0503(16) 0.0728(19) 0.0666(17) -0.0157(15) -0.0103(13) -0.0025(14) C7 0.077(2) 0.092(2) 0.0482(15) 0.0001(16) -0.0089(14) 0.0200(19) C8 0.0614(17) 0.0658(19) 0.0679(18) 0.0161(16) 0.0005(14) 0.0076(15) C9A 0.0443(14) 0.0467(14) 0.0405(12) -0.0036(11) 0.0074(10) -0.0064(11) C9 0.0490(15) 0.0484(15) 0.0623(16) -0.0088(13) 0.0006(12) 0.0042(13) C11 0.0444(16) 0.074(2) 0.078(2) -0.0083(16) -0.0003(14) 0.0070(14) C12 0.0372(12) 0.0334(12) 0.0392(12) -0.0040(9) -0.0027(9) 0.0002(9) C13 0.0495(14) 0.0349(12) 0.0412(12) -0.0044(10) 0.0043(10) -0.0001(11) C14 0.0579(15) 0.0341(12) 0.0490(13) -0.0004(10) 0.0003(11) -0.0025(11) C15 0.0576(15) 0.0468(14) 0.0408(13) 0.0053(11) 0.0070(11) -0.0010(12) C16 0.0683(17) 0.0471(15) 0.0410(13) -0.0079(11) 0.0092(12) 0.0031(13) C17 0.0597(15) 0.0308(12) 0.0473(13) -0.0063(10) 0.0046(11) -0.0024(11) C18 0.090(2) 0.0702(19) 0.0505(15) -0.0001(14) -0.0168(14) -0.0071(16) _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 C15 1.745(2) . y O1 C1 1.224(2) . y O4 C3A 1.415(2) . y O4 C5 1.437(3) . y N10 C1 1.359(3) . y N10 C9A 1.460(3) . y N10 C3A 1.468(3) . y C1 C2 1.510(3) . ? C2 C18 1.519(3) . ? C2 C3 1.530(3) . ? C2 H2 0.96(2) . ? C3 C3A 1.540(3) . ? C3 H3A 0.93(2) . ? C3 H3B 0.95(2) . ? C3A C12 1.532(3) . ? C5 C5A 1.520(3) . ? C5 H5A 0.96(3) . ? C5 H5B 0.99(2) . ? C5A C6 1.561(4) . ? C5A C9A 1.561(3) . ? C5A H5A1 0.96(2) . ? C6 C7 1.508(4) . ? C6 C11 1.533(4) . ? C6 H6 0.96(3) . ? C7 C8 1.318(4) . ? C7 H7 0.9300 . ? C8 C9 1.499(4) . ? C8 H8 0.9300 . ? C9A C9 1.540(3) . ? C9A H9A 1.00(2) . ? C9 C11 1.535(4) . ? C9 H9 0.98(2) . ? C11 H11A 0.99(3) . ? C11 H11B 1.01(3) . ? C12 C17 1.387(3) . ? C12 C13 1.388(3) . ? C13 C14 1.381(3) . ? C13 H13 0.9300 . ? C14 C15 1.377(3) . ? C14 H14 0.9300 . ? C15 C16 1.379(3) . ? C16 C17 1.382(3) . ? C16 H16 0.9300 . ? C17 H17 0.9300 . ? C18 H18A 0.9600 . ? C18 H18B 0.9600 . ? C18 H18C 0.9600 . ? 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 C3A O4 C5 111.82(17) . . y C1 N10 C9A 119.28(17) . . y C1 N10 C3A 113.58(18) . . y C9A N10 C3A 123.99(17) . . y O1 C1 N10 124.5(2) . . y O1 C1 C2 127.1(2) . . ?y N10 C1 C2 108.47(18) . . y C1 C2 C18 113.4(2) . . ? C1 C2 C3 102.53(19) . . ? C18 C2 C3 114.5(2) . . ? C1 C2 H2 106.0(14) . . ? C18 C2 H2 110.5(14) . . ? C3 C2 H2 109.3(13) . . ? C2 C3 C3A 104.72(18) . . ? C2 C3 H3A 110.1(14) . . ? C3A C3 H3A 106.4(15) . . ? C2 C3 H3B 113.0(14) . . ? C3A C3 H3B 114.1(14) . . ? H3A C3 H3B 108(2) . . ? O4 C3A N10 110.09(17) . . ? O4 C3A C12 112.02(16) . . ? N10 C3A C12 113.47(17) . . ? O4 C3A C3 108.33(17) . . ? N10 C3A C3 102.32(17) . . ? C12 C3A C3 110.09(18) . . ? O4 C5 C5A 112.6(2) . . ? O4 C5 H5A 104.4(14) . . ? C5A C5 H5A 112.8(14) . . ? O4 C5 H5B 110.0(14) . . ? C5A C5 H5B 108.5(14) . . ? H5A C5 H5B 108(2) . . ? C5 C5A C6 115.1(2) . . ? C5 C5A C9A 114.3(2) . . ? C6 C5A C9A 101.2(2) . . ? C5 C5A H5A1 109.2(14) . . ? C6 C5A H5A1 108.3(15) . . ? C9A C5A H5A1 108.4(14) . . ? C7 C6 C11 99.2(2) . . ? C7 C6 C5A 106.6(2) . . ? C11 C6 C5A 101.3(2) . . ? C7 C6 H6 117.1(16) . . ? C11 C6 H6 117.2(15) . . ? C5A C6 H6 113.5(16) . . ? C8 C7 C6 107.9(2) . . ? C8 C7 H7 126.1 . . ? C6 C7 H7 126.1 . . ? C7 C8 C9 107.7(3) . . ? C7 C8 H8 126.2 . . ? C9 C8 H8 126.2 . . ? N10 C9A C9 118.65(19) . . ? N10 C9A C5A 114.12(19) . . ? C9 C9A C5A 103.83(19) . . ? N10 C9A H9A 106.1(12) . . ? C9 C9A H9A 106.3(13) . . ? C5A C9A H9A 107.1(13) . . ? C8 C9 C11 100.0(2) . . ? C8 C9 C9A 109.2(2) . . ? C11 C9 C9A 98.2(2) . . ? C8 C9 H9 114.9(14) . . ? C11 C9 H9 117.6(14) . . ? C9A C9 H9 114.7(14) . . ? C6 C11 C9 93.6(2) . . ? C6 C11 H11A 112.1(16) . . ? C9 C11 H11A 112.1(16) . . ? C6 C11 H11B 113.1(16) . . ? C9 C11 H11B 110.2(15) . . ? H11A C11 H11B 114(2) . . ? C17 C12 C13 118.2(2) . . ? C17 C12 C3A 120.58(18) . . ? C13 C12 C3A 120.79(18) . . ? C14 C13 C12 121.1(2) . . ? C14 C13 H13 119.5 . . ? C12 C13 H13 119.5 . . ? C15 C14 C13 119.3(2) . . ? C15 C14 H14 120.4 . . ? C13 C14 H14 120.4 . . ? C14 C15 C16 121.1(2) . . ? C14 C15 Cl 119.16(18) . . ? C16 C15 Cl 119.75(18) . . ? C15 C16 C17 118.9(2) . . ? C15 C16 H16 120.6 . . ? C17 C16 H16 120.6 . . ? C16 C17 C12 121.4(2) . . ? C16 C17 H17 119.3 . . ? C12 C17 H17 119.3 . . ? C2 C18 H18A 109.5 . . ? C2 C18 H18B 109.5 . . ? H18A C18 H18B 109.5 . . ? C2 C18 H18C 109.5 . . ? H18A C18 H18C 109.5 . . ? H18B C18 H18C 109.5 . . ? 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 C9A N10 C1 O1 -13.6(3) . . . . ? C3A N10 C1 O1 -174.4(2) . . . . ? C9A N10 C1 C2 167.21(18) . . . . ? C3A N10 C1 C2 6.5(2) . . . . ? O1 C1 C2 C18 34.7(3) . . . . ? N10 C1 C2 C18 -146.2(2) . . . . ? O1 C1 C2 C3 158.7(2) . . . . ? N10 C1 C2 C3 -22.1(2) . . . . ? C1 C2 C3 C3A 28.7(2) . . . . ? C18 C2 C3 C3A 151.9(2) . . . . ? C5 O4 C3A N10 59.4(2) . . . . ? C5 O4 C3A C12 -67.9(2) . . . . ? C5 O4 C3A C3 170.50(18) . . . . ? C1 N10 C3A O4 127.01(18) . . . . ? C9A N10 C3A O4 -32.7(3) . . . . ? C1 N10 C3A C12 -106.5(2) . . . . ? C9A N10 C3A C12 93.8(2) . . . . ? C1 N10 C3A C3 12.0(2) . . . . ? C9A N10 C3A C3 -147.69(19) . . . . ? C2 C3 C3A O4 -141.33(18) . . . . ? C2 C3 C3A N10 -25.1(2) . . . . ? C2 C3 C3A C12 95.9(2) . . . . ? C3A O4 C5 C5A -64.8(3) . . . . ? O4 C5 C5A C6 155.0(2) . . . . ? O4 C5 C5A C9A 38.5(3) . . . . ? C5 C5A C6 C7 -53.2(3) . . . . ? C9A C5A C6 C7 70.6(2) . . . . ? C5 C5A C6 C11 -156.4(2) . . . . ? C9A C5A C6 C11 -32.6(2) . . . . ? C11 C6 C7 C8 34.9(3) . . . . ? C5A C6 C7 C8 -69.8(3) . . . . ? C6 C7 C8 C9 -1.4(3) . . . . ? C1 N10 C9A C9 88.3(2) . . . . ? C3A N10 C9A C9 -113.1(2) . . . . ? C1 N10 C9A C5A -148.84(19) . . . . ? C3A N10 C9A C5A 9.8(3) . . . . ? C5 C5A C9A N10 -12.0(3) . . . . ? C6 C5A C9A N10 -136.3(2) . . . . ? C5 C5A C9A C9 118.6(2) . . . . ? C6 C5A C9A C9 -5.7(2) . . . . ? C7 C8 C9 C11 -32.7(3) . . . . ? C7 C8 C9 C9A 69.8(3) . . . . ? N10 C9A C9 C8 66.0(3) . . . . ? C5A C9A C9 C8 -61.9(2) . . . . ? N10 C9A C9 C11 169.6(2) . . . . ? C5A C9A C9 C11 41.7(2) . . . . ? C7 C6 C11 C9 -50.9(2) . . . . ? C5A C6 C11 C9 58.1(2) . . . . ? C8 C9 C11 C6 50.6(2) . . . . ? C9A C9 C11 C6 -60.7(2) . . . . ? O4 C3A C12 C17 -32.5(3) . . . . ? N10 C3A C12 C17 -157.89(19) . . . . ? C3 C3A C12 C17 88.1(2) . . . . ? O4 C3A C12 C13 155.0(2) . . . . ? N10 C3A C12 C13 29.6(3) . . . . ? C3 C3A C12 C13 -84.3(2) . . . . ? C17 C12 C13 C14 1.1(3) . . . . ? C3A C12 C13 C14 173.8(2) . . . . ? C12 C13 C14 C15 0.7(4) . . . . ? C13 C14 C15 C16 -1.8(4) . . . . ? C13 C14 C15 Cl 179.30(18) . . . . ? C14 C15 C16 C17 1.2(4) . . . . ? Cl C15 C16 C17 -179.95(18) . . . . ? C15 C16 C17 C12 0.6(4) . . . . ? C13 C12 C17 C16 -1.8(3) . . . . ? C3A C12 C17 C16 -174.4(2) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C17 H17 O4 0.93 2.55 2.857(3) 99.8 . C13 H13 N10 0.93 2.58 2.904(3) 101.3 . _diffrn_measured_fraction_theta_max 0.942 _diffrn_reflns_theta_full 25.00 _diffrn_measured_fraction_theta_full 0.942 _refine_diff_density_max 0.128 _refine_diff_density_min -0.208 _refine_diff_density_rms 0.034 #===END