data_sand _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C22 H22 Cl N O6' _chemical_formula_weight 431.86 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 Triclinic _symmetry_space_group_name_H-M P-1 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 7.5319(15) _cell_length_b 11.179(2) _cell_length_c 12.639(3) _cell_angle_alpha 99.22(3) _cell_angle_beta 94.76(3) _cell_angle_gamma 93.14(3) _cell_volume 1044.3(4) _cell_formula_units_Z 2 _cell_measurement_temperature 296(2) _cell_measurement_reflns_used 2805 _cell_measurement_theta_min 2.67 _cell_measurement_theta_max 26.69 _exptl_crystal_description Parallelepiped _exptl_crystal_colour Colorless _exptl_crystal_size_max 0.32 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.21 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.373 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 452 _exptl_absorpt_coefficient_mu 0.222 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.9323 _exptl_absorpt_correction_T_max 0.9549 _exptl_absorpt_process_details 'SADABS (Sheldrick, 1999)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 296(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'normal-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% 1 _diffrn_reflns_number 7788 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_av_sigmaI/netI 0.0435 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_theta_min 1.64 _diffrn_reflns_theta_max 24.99 _reflns_number_total 3655 _reflns_number_gt 2619 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SAINT+' _computing_data_reduction 'Bruker SAINT+' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0700P)^2^+0.2000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 3655 _refine_ls_number_parameters 274 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0883 _refine_ls_R_factor_gt 0.0629 _refine_ls_wR_factor_ref 0.1554 _refine_ls_wR_factor_gt 0.1419 _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_restrained_S_all 1.071 _refine_ls_shift/su_max 0.016 _refine_ls_shift/su_mean 0.001 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 0.25571(13) 0.92468(8) 0.91603(7) 0.0735(3) Uani 1 1 d . . . O1 O 0.0823(4) 0.9434(3) 0.7055(2) 0.1087(11) Uani 1 1 d . . . O2 O 0.0755(3) 0.7834(2) 0.51571(17) 0.0598(6) Uani 1 1 d . . . O3 O -0.0388(4) 0.6625(3) 0.6208(2) 0.0910(9) Uani 1 1 d . . . O4 O 0.3222(3) 0.6135(2) 0.50420(17) 0.0708(7) Uani 1 1 d . . . O5 O 0.3415(3) 0.6015(2) 0.90348(17) 0.0627(6) Uani 1 1 d . . . H5 H 0.3781 0.5708 0.9551 0.094 Uiso 1 1 calc R . . O6 O 0.6966(3) 0.57928(18) 0.95700(15) 0.0555(6) Uani 1 1 d . . . N1 N 0.6449(3) 0.5587(2) 0.76992(19) 0.0468(6) Uani 1 1 d . . . C1 C 0.2893(4) 0.8359(3) 0.7945(2) 0.0509(8) Uani 1 1 d . . . C2 C 0.1897(5) 0.8668(3) 0.7003(3) 0.0624(9) Uani 1 1 d . . . C3 C 0.2333(4) 0.8022(3) 0.5893(2) 0.0524(8) Uani 1 1 d . . . C4 C 0.3245(4) 0.6833(3) 0.5894(2) 0.0485(7) Uani 1 1 d . . . C5 C 0.4202(4) 0.6674(2) 0.6889(2) 0.0455(7) Uani 1 1 d . . . C6 C 0.3919(4) 0.7405(2) 0.7887(2) 0.0461(7) Uani 1 1 d . . . C7 C 0.4688(4) 0.6932(3) 0.8870(2) 0.0506(8) Uani 1 1 d . . . H7 H 0.4793 0.7589 0.9492 0.061 Uiso 1 1 calc R . . C8 C 0.6523(4) 0.6444(3) 0.8719(2) 0.0478(7) Uani 1 1 d . . . C9 C 0.5406(4) 0.5784(3) 0.6866(2) 0.0466(7) Uani 1 1 d . . . H9 H 0.5486 0.5284 0.6211 0.056 Uiso 1 1 calc R . . C10 C 0.8486(5) 0.6403(3) 1.0244(3) 0.0680(10) Uani 1 1 d . . . H10A H 0.8230 0.6527 1.0992 0.082 Uiso 1 1 calc R . . H10B H 0.9510 0.5916 1.0174 0.082 Uiso 1 1 calc R . . C11 C 0.8860(7) 0.7546(4) 0.9912(4) 0.1073(16) Uani 1 1 d . . . H11A H 1.0138 0.7717 0.9924 0.129 Uiso 1 1 calc R . . H11B H 0.8385 0.8193 1.0391 0.129 Uiso 1 1 calc R . . C12 C 0.7993(4) 0.7460(3) 0.8799(2) 0.0604(9) Uani 1 1 d . . . H12A H 0.8838 0.7255 0.8271 0.073 Uiso 1 1 calc R . . H12B H 0.7494 0.8219 0.8694 0.073 Uiso 1 1 calc R . . C13 C 0.3586(5) 0.8891(3) 0.5447(3) 0.0730(10) Uani 1 1 d . . . H13A H 0.3858 0.8525 0.4745 0.110 Uiso 1 1 calc R . . H13B H 0.4669 0.9065 0.5917 0.110 Uiso 1 1 calc R . . H13C H 0.3021 0.9632 0.5399 0.110 Uiso 1 1 calc R . . C14 C -0.0530(5) 0.7069(4) 0.5404(3) 0.0728(10) Uani 1 1 d . . . C15 C -0.2080(5) 0.6864(5) 0.4565(4) 0.1118(17) Uani 1 1 d . . . H15A H -0.1904 0.6175 0.4033 0.168 Uiso 1 1 calc R . . H15B H -0.2177 0.7571 0.4227 0.168 Uiso 1 1 calc R . . H15C H -0.3156 0.6714 0.4894 0.168 Uiso 1 1 calc R . . C16 C 0.7777(4) 0.4680(3) 0.7556(2) 0.0519(8) Uani 1 1 d . . . H16A H 0.8809 0.4951 0.8067 0.062 Uiso 1 1 calc R . . H16B H 0.8165 0.4640 0.6839 0.062 Uiso 1 1 calc R . . C17 C 0.7134(4) 0.3422(3) 0.7701(2) 0.0486(7) Uani 1 1 d . . . C18 C 0.8301(5) 0.2519(3) 0.7592(3) 0.0659(9) Uani 1 1 d . . . H18 H 0.9465 0.2701 0.7444 0.079 Uiso 1 1 calc R . . C19 C 0.7774(6) 0.1341(3) 0.7701(3) 0.0789(11) Uani 1 1 d . . . H19 H 0.8590 0.0745 0.7644 0.095 Uiso 1 1 calc R . . C20 C 0.6063(6) 0.1056(3) 0.7891(3) 0.0783(11) Uani 1 1 d . . . H20 H 0.5707 0.0266 0.7965 0.094 Uiso 1 1 calc R . . C21 C 0.4881(6) 0.1930(3) 0.7973(3) 0.0807(11) Uani 1 1 d . . . H21 H 0.3704 0.1735 0.8089 0.097 Uiso 1 1 calc R . . C22 C 0.5415(5) 0.3108(3) 0.7886(3) 0.0659(9) Uani 1 1 d . . . H22 H 0.4593 0.3701 0.7955 0.079 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.1007(7) 0.0561(5) 0.0634(6) -0.0059(4) 0.0322(5) 0.0123(5) O1 0.138(3) 0.109(2) 0.089(2) 0.0141(17) 0.0216(19) 0.082(2) O2 0.0545(13) 0.0709(15) 0.0613(14) 0.0271(11) 0.0099(11) 0.0139(11) O3 0.0813(18) 0.122(2) 0.0773(19) 0.0442(17) 0.0119(15) -0.0129(16) O4 0.0875(17) 0.0785(16) 0.0433(13) -0.0041(12) -0.0031(12) 0.0334(13) O5 0.0641(14) 0.0748(15) 0.0568(15) 0.0306(11) 0.0124(11) 0.0024(12) O6 0.0664(14) 0.0578(13) 0.0423(12) 0.0168(10) -0.0039(10) -0.0069(10) N1 0.0562(15) 0.0445(14) 0.0414(14) 0.0089(11) 0.0056(12) 0.0112(11) C1 0.064(2) 0.0387(16) 0.0514(19) 0.0052(13) 0.0189(16) 0.0032(14) C2 0.074(2) 0.051(2) 0.068(2) 0.0144(16) 0.0221(19) 0.0198(17) C3 0.0556(19) 0.0544(19) 0.0502(19) 0.0153(14) 0.0060(15) 0.0088(15) C4 0.0533(18) 0.0495(17) 0.0442(18) 0.0075(14) 0.0096(14) 0.0098(14) C5 0.0562(18) 0.0431(16) 0.0382(16) 0.0063(12) 0.0057(13) 0.0105(14) C6 0.0568(18) 0.0399(16) 0.0424(17) 0.0068(13) 0.0114(14) -0.0007(14) C7 0.0636(19) 0.0506(18) 0.0379(16) 0.0065(13) 0.0118(14) -0.0019(15) C8 0.0600(19) 0.0500(17) 0.0333(15) 0.0091(13) 0.0030(13) -0.0012(14) C9 0.0568(18) 0.0441(17) 0.0389(16) 0.0048(13) 0.0078(14) 0.0046(14) C10 0.069(2) 0.081(3) 0.050(2) 0.0107(18) -0.0069(17) -0.0032(19) C11 0.114(3) 0.101(3) 0.102(3) 0.045(3) -0.033(3) -0.049(3) C12 0.072(2) 0.059(2) 0.051(2) 0.0131(15) 0.0089(17) -0.0069(17) C13 0.085(3) 0.071(2) 0.069(2) 0.0268(18) 0.013(2) -0.0031(19) C14 0.053(2) 0.097(3) 0.073(3) 0.023(2) 0.0160(19) 0.006(2) C15 0.063(3) 0.174(5) 0.100(3) 0.042(3) -0.006(2) -0.012(3) C16 0.0500(17) 0.0595(19) 0.0472(18) 0.0101(14) 0.0050(14) 0.0097(15) C17 0.0567(19) 0.0530(18) 0.0346(16) 0.0037(13) -0.0009(14) 0.0097(15) C18 0.059(2) 0.063(2) 0.073(2) 0.0053(17) -0.0023(18) 0.0149(18) C19 0.099(3) 0.055(2) 0.080(3) 0.0036(19) -0.008(2) 0.027(2) C20 0.110(3) 0.048(2) 0.074(3) 0.0054(18) 0.008(2) 0.002(2) C21 0.092(3) 0.061(2) 0.092(3) 0.011(2) 0.032(2) -0.002(2) C22 0.071(2) 0.051(2) 0.080(2) 0.0109(17) 0.0250(19) 0.0116(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 C1 1.735(3) . ? O1 C2 1.208(4) . ? O2 C14 1.345(4) . ? O2 C3 1.431(4) . ? O3 C14 1.199(4) . ? O4 C4 1.222(3) . ? O5 C7 1.417(3) . ? O6 C8 1.420(3) . ? O6 C10 1.438(4) . ? N1 C9 1.314(4) . ? N1 C16 1.464(4) . ? N1 C8 1.472(4) . ? C1 C6 1.347(4) . ? C1 C2 1.453(5) . ? C2 C3 1.541(4) . ? C3 C13 1.521(4) . ? C3 C4 1.530(4) . ? C4 C5 1.439(4) . ? C5 C9 1.381(4) . ? C5 C6 1.428(4) . ? C6 C7 1.511(4) . ? C7 C8 1.529(4) . ? C8 C12 1.528(4) . ? C10 C11 1.429(5) . ? C11 C12 1.487(5) . ? C14 C15 1.492(5) . ? C16 C17 1.506(4) . ? C17 C22 1.372(4) . ? C17 C18 1.372(4) . ? C18 C19 1.386(5) . ? C19 C20 1.360(5) . ? C20 C21 1.355(5) . ? C21 C22 1.380(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 C14 O2 C3 115.0(3) . . ? C8 O6 C10 109.8(2) . . ? C9 N1 C16 120.0(2) . . ? C9 N1 C8 119.2(2) . . ? C16 N1 C8 119.6(2) . . ? C6 C1 C2 122.3(3) . . ? C6 C1 Cl1 122.3(2) . . ? C2 C1 Cl1 115.2(2) . . ? O1 C2 C1 123.2(3) . . ? O1 C2 C3 119.6(3) . . ? C1 C2 C3 117.2(3) . . ? O2 C3 C13 105.6(2) . . ? O2 C3 C4 110.3(2) . . ? C13 C3 C4 107.5(3) . . ? O2 C3 C2 110.0(3) . . ? C13 C3 C2 107.3(3) . . ? C4 C3 C2 115.6(3) . . ? O4 C4 C5 124.8(3) . . ? O4 C4 C3 118.3(3) . . ? C5 C4 C3 116.7(3) . . ? C9 C5 C6 120.0(3) . . ? C9 C5 C4 118.6(3) . . ? C6 C5 C4 121.4(3) . . ? C1 C6 C5 122.5(3) . . ? C1 C6 C7 122.9(3) . . ? C5 C6 C7 114.2(3) . . ? O5 C7 C6 105.2(2) . . ? O5 C7 C8 111.9(2) . . ? C6 C7 C8 112.1(2) . . ? O6 C8 N1 107.8(2) . . ? O6 C8 C12 106.4(2) . . ? N1 C8 C12 112.2(2) . . ? O6 C8 C7 108.0(2) . . ? N1 C8 C7 109.9(2) . . ? C12 C8 C7 112.3(2) . . ? N1 C9 C5 125.1(3) . . ? C11 C10 O6 108.1(3) . . ? C10 C11 C12 107.1(3) . . ? C11 C12 C8 103.6(3) . . ? O3 C14 O2 122.2(4) . . ? O3 C14 C15 126.3(4) . . ? O2 C14 C15 111.6(3) . . ? N1 C16 C17 114.8(2) . . ? C22 C17 C18 117.6(3) . . ? C22 C17 C16 123.7(3) . . ? C18 C17 C16 118.6(3) . . ? C17 C18 C19 121.0(3) . . ? C20 C19 C18 120.1(4) . . ? C21 C20 C19 119.6(4) . . ? C20 C21 C22 120.3(4) . . ? C17 C22 C21 121.3(3) . . ? 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 C1 C2 O1 171.6(3) . . . . ? Cl1 C1 C2 O1 -4.5(5) . . . . ? C6 C1 C2 C3 -11.8(4) . . . . ? Cl1 C1 C2 C3 172.1(2) . . . . ? C14 O2 C3 C13 179.2(3) . . . . ? C14 O2 C3 C4 63.4(3) . . . . ? C14 O2 C3 C2 -65.3(3) . . . . ? O1 C2 C3 O2 -36.7(4) . . . . ? C1 C2 C3 O2 146.6(3) . . . . ? O1 C2 C3 C13 77.7(4) . . . . ? C1 C2 C3 C13 -99.0(3) . . . . ? O1 C2 C3 C4 -162.4(3) . . . . ? C1 C2 C3 C4 20.9(4) . . . . ? O2 C3 C4 O4 36.4(4) . . . . ? C13 C3 C4 O4 -78.2(4) . . . . ? C2 C3 C4 O4 162.0(3) . . . . ? O2 C3 C4 C5 -148.8(2) . . . . ? C13 C3 C4 C5 96.5(3) . . . . ? C2 C3 C4 C5 -23.2(4) . . . . ? O4 C4 C5 C9 10.7(5) . . . . ? C3 C4 C5 C9 -163.7(3) . . . . ? O4 C4 C5 C6 -168.8(3) . . . . ? C3 C4 C5 C6 16.8(4) . . . . ? C2 C1 C6 C5 4.3(5) . . . . ? Cl1 C1 C6 C5 -179.9(2) . . . . ? C2 C1 C6 C7 -168.4(3) . . . . ? Cl1 C1 C6 C7 7.4(4) . . . . ? C9 C5 C6 C1 173.5(3) . . . . ? C4 C5 C6 C1 -7.0(4) . . . . ? C9 C5 C6 C7 -13.2(4) . . . . ? C4 C5 C6 C7 166.3(3) . . . . ? C1 C6 C7 O5 92.1(3) . . . . ? C5 C6 C7 O5 -81.2(3) . . . . ? C1 C6 C7 C8 -146.0(3) . . . . ? C5 C6 C7 C8 40.7(3) . . . . ? C10 O6 C8 N1 126.8(3) . . . . ? C10 O6 C8 C12 6.3(3) . . . . ? C10 O6 C8 C7 -114.5(3) . . . . ? C9 N1 C8 O6 152.2(2) . . . . ? C16 N1 C8 O6 -40.0(3) . . . . ? C9 N1 C8 C12 -91.0(3) . . . . ? C16 N1 C8 C12 76.8(3) . . . . ? C9 N1 C8 C7 34.7(3) . . . . ? C16 N1 C8 C7 -157.5(2) . . . . ? O5 C7 C8 O6 -49.9(3) . . . . ? C6 C7 C8 O6 -167.8(2) . . . . ? O5 C7 C8 N1 67.4(3) . . . . ? C6 C7 C8 N1 -50.4(3) . . . . ? O5 C7 C8 C12 -166.9(2) . . . . ? C6 C7 C8 C12 75.3(3) . . . . ? C16 N1 C9 C5 -175.0(3) . . . . ? C8 N1 C9 C5 -7.2(4) . . . . ? C6 C5 C9 N1 -4.9(4) . . . . ? C4 C5 C9 N1 175.6(3) . . . . ? C8 O6 C10 C11 8.3(4) . . . . ? O6 C10 C11 C12 -19.8(5) . . . . ? C10 C11 C12 C8 22.8(5) . . . . ? O6 C8 C12 C11 -17.7(4) . . . . ? N1 C8 C12 C11 -135.3(3) . . . . ? C7 C8 C12 C11 100.3(3) . . . . ? C3 O2 C14 O3 3.3(5) . . . . ? C3 O2 C14 C15 -176.6(3) . . . . ? C9 N1 C16 C17 -91.3(3) . . . . ? C8 N1 C16 C17 101.1(3) . . . . ? N1 C16 C17 C22 3.9(4) . . . . ? N1 C16 C17 C18 -179.3(3) . . . . ? C22 C17 C18 C19 -2.0(5) . . . . ? C16 C17 C18 C19 -179.0(3) . . . . ? C17 C18 C19 C20 1.7(6) . . . . ? C18 C19 C20 C21 0.0(6) . . . . ? C19 C20 C21 C22 -1.3(6) . . . . ? C18 C17 C22 C21 0.7(5) . . . . ? C16 C17 C22 C21 177.6(3) . . . . ? C20 C21 C22 C17 1.0(6) . . . . ? _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 24.99 _diffrn_measured_fraction_theta_full 0.997 _refine_diff_density_max 0.266 _refine_diff_density_min -0.216 _refine_diff_density_rms 0.044