data_gda1s _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C21 H19 Cl2 N O5' _chemical_formula_weight 436.27 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 8.1512(9) _cell_length_b 24.470(3) _cell_length_c 10.6260(12) _cell_angle_alpha 90.00 _cell_angle_beta 111.793(2) _cell_angle_gamma 90.00 _cell_volume 1968.0(4) _cell_formula_units_Z 4 _cell_measurement_temperature 98(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description Brick _exptl_crystal_colour clear _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_meas 0 _exptl_crystal_density_diffrn 1.472 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 904 _exptl_absorpt_coefficient_mu 0.364 _exptl_absorpt_correction_type NONE _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 98(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 17901 _diffrn_reflns_av_R_equivalents 0.0191 _diffrn_reflns_av_sigmaI/netI 0.0183 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -32 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_theta_min 2.23 _diffrn_reflns_theta_max 28.05 _reflns_number_total 4666 _reflns_number_gt 4278 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _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^)+(0.0490P)^2^+1.0893P] 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 4666 _refine_ls_number_parameters 264 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0406 _refine_ls_R_factor_gt 0.0373 _refine_ls_wR_factor_ref 0.0956 _refine_ls_wR_factor_gt 0.0933 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.041 _refine_ls_shift/su_max 0.002 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.50324(5) 0.573806(16) 1.12097(4) 0.03228(11) Uani 1 1 d . . . Cl2 Cl 1.18222(5) 0.632710(16) 1.27138(4) 0.03063(11) Uani 1 1 d . . . O1 O 0.95430(13) 0.70670(4) 0.86198(10) 0.0222(2) Uani 1 1 d . . . O3 O 0.87848(17) 0.63151(4) 0.47506(11) 0.0307(3) Uani 1 1 d . . . O2 O 0.89000(15) 0.54658(4) 0.53893(10) 0.0244(2) Uani 1 1 d . . . N1 N 0.53356(15) 0.56720(5) 0.81917(12) 0.0198(2) Uani 1 1 d . . . C15 C 0.82733(17) 0.58955(5) 0.91323(13) 0.0154(2) Uani 1 1 d . . . O4 O 0.49719(13) 0.55879(4) 0.59403(11) 0.0246(2) Uani 1 1 d . . . C14 C 0.67374(17) 0.58146(5) 0.94047(14) 0.0176(3) Uani 1 1 d . . . O5 O 0.28262(14) 0.61578(5) 0.82371(13) 0.0311(3) Uani 1 1 d . . . C11 C 0.88493(17) 0.52156(5) 0.76158(13) 0.0174(3) Uani 1 1 d . . . H11A H 1.0139 0.5263 0.8093 0.021 Uiso 1 1 calc R . . H11B H 0.8453 0.4927 0.8090 0.021 Uiso 1 1 calc R . . C16 C 0.98554(17) 0.60455(5) 1.01264(13) 0.0175(3) Uani 1 1 d . . . H16 H 1.0893 0.6095 0.9932 0.021 Uiso 1 1 calc R . . C8 C 0.84688(17) 0.61963(5) 0.68730(13) 0.0153(2) Uani 1 1 d . . . H8 H 0.9689 0.6304 0.7481 0.018 Uiso 1 1 calc R . . C9 C 0.86617(18) 0.59952(6) 0.55738(14) 0.0207(3) Uani 1 1 d . . . C17 C 0.98655(19) 0.61218(6) 1.14280(13) 0.0207(3) Uani 1 1 d . . . C2 C 0.79723(18) 0.71499(6) 0.75713(14) 0.0194(3) Uani 1 1 d . . . C19 C 0.68119(19) 0.58703(6) 1.07275(15) 0.0213(3) Uani 1 1 d . . . C12 C 0.79051(16) 0.57553(5) 0.76708(13) 0.0147(2) Uani 1 1 d . . . C3 C 0.6979(2) 0.76296(6) 0.73948(16) 0.0254(3) Uani 1 1 d . . . H3 H 0.7351 0.7913 0.8050 0.030 Uiso 1 1 calc R . . C7 C 0.73969(17) 0.67213(5) 0.66297(13) 0.0179(3) Uani 1 1 d . . . C6 C 0.58587(19) 0.67951(6) 0.54908(15) 0.0239(3) Uani 1 1 d . . . H6 H 0.5466 0.6511 0.4836 0.029 Uiso 1 1 calc R . . C10 C 0.84704(19) 0.50391(5) 0.61707(14) 0.0214(3) Uani 1 1 d . . . H10A H 0.9170 0.4708 0.6174 0.026 Uiso 1 1 calc R . . H10B H 0.7204 0.4944 0.5732 0.026 Uiso 1 1 calc R . . C18 C 0.8389(2) 0.60318(6) 1.17420(14) 0.0232(3) Uani 1 1 d . . . H18 H 0.8449 0.6080 1.2645 0.028 Uiso 1 1 calc R . . C21 C 0.2965(2) 0.65867(7) 0.73891(19) 0.0327(4) Uani 1 1 d . . . H21A H 0.4210 0.6687 0.7640 0.049 Uiso 1 1 calc R . . H21B H 0.2297 0.6904 0.7498 0.049 Uiso 1 1 calc R . . H21C H 0.2485 0.6466 0.6443 0.049 Uiso 1 1 calc R . . C13 C 0.59043(17) 0.56630(5) 0.71128(14) 0.0181(3) Uani 1 1 d . . . C5 C 0.4890(2) 0.72762(6) 0.52955(17) 0.0299(3) Uani 1 1 d . . . H5 H 0.3852 0.7322 0.4508 0.036 Uiso 1 1 calc R . . C20 C 0.34649(19) 0.56531(6) 0.79665(18) 0.0277(3) Uani 1 1 d . . . H20A H 0.2790 0.5549 0.7013 0.033 Uiso 1 1 calc R . . H20B H 0.3265 0.5368 0.8556 0.033 Uiso 1 1 calc R . . C1 C 1.0014(2) 0.74399(7) 0.97363(16) 0.0323(4) Uani 1 1 d . . . H1A H 1.0227 0.7803 0.9437 0.048 Uiso 1 1 calc R . . H1B H 1.1088 0.7311 1.0462 0.048 Uiso 1 1 calc R . . H1C H 0.9049 0.7462 1.0074 0.048 Uiso 1 1 calc R . . C4 C 0.5446(2) 0.76882(6) 0.62557(18) 0.0307(3) Uani 1 1 d . . . H4 H 0.4771 0.8014 0.6133 0.037 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 0.0360(2) 0.0324(2) 0.0424(2) 0.00986(16) 0.03082(18) 0.00677(15) Cl2 0.0342(2) 0.0341(2) 0.01717(17) -0.00600(14) 0.00210(14) -0.00328(15) O1 0.0242(5) 0.0181(5) 0.0211(5) -0.0048(4) 0.0046(4) -0.0009(4) O3 0.0507(7) 0.0254(5) 0.0228(5) 0.0010(4) 0.0215(5) 0.0003(5) O2 0.0376(6) 0.0200(5) 0.0205(5) -0.0020(4) 0.0164(4) 0.0027(4) N1 0.0143(5) 0.0195(5) 0.0260(6) 0.0005(5) 0.0082(5) -0.0007(4) C15 0.0179(6) 0.0137(6) 0.0165(6) 0.0010(5) 0.0086(5) 0.0014(4) O4 0.0199(5) 0.0236(5) 0.0242(5) -0.0041(4) 0.0011(4) -0.0022(4) C14 0.0180(6) 0.0144(6) 0.0222(6) 0.0017(5) 0.0095(5) 0.0018(5) O5 0.0218(5) 0.0309(6) 0.0443(7) 0.0049(5) 0.0167(5) 0.0054(4) C11 0.0187(6) 0.0158(6) 0.0190(6) 0.0003(5) 0.0084(5) 0.0024(5) C16 0.0190(6) 0.0164(6) 0.0176(6) 0.0003(5) 0.0072(5) 0.0003(5) C8 0.0176(6) 0.0147(6) 0.0144(6) -0.0017(5) 0.0067(5) -0.0010(4) C9 0.0243(7) 0.0213(6) 0.0171(6) -0.0022(5) 0.0084(5) -0.0008(5) C17 0.0255(7) 0.0178(6) 0.0159(6) -0.0008(5) 0.0045(5) 0.0022(5) C2 0.0211(6) 0.0173(6) 0.0207(6) 0.0000(5) 0.0088(5) -0.0016(5) C19 0.0259(7) 0.0183(6) 0.0273(7) 0.0052(5) 0.0186(6) 0.0046(5) C12 0.0144(5) 0.0144(6) 0.0150(6) -0.0017(4) 0.0053(5) -0.0010(4) C3 0.0300(7) 0.0164(6) 0.0310(8) -0.0019(6) 0.0127(6) -0.0002(5) C7 0.0205(6) 0.0154(6) 0.0190(6) 0.0008(5) 0.0086(5) -0.0004(5) C6 0.0253(7) 0.0201(7) 0.0226(7) 0.0011(5) 0.0045(6) -0.0006(5) C10 0.0284(7) 0.0164(6) 0.0211(6) -0.0025(5) 0.0111(6) 0.0000(5) C18 0.0355(8) 0.0199(6) 0.0181(6) 0.0019(5) 0.0145(6) 0.0066(6) C21 0.0235(7) 0.0296(8) 0.0456(10) 0.0042(7) 0.0135(7) 0.0048(6) C13 0.0161(6) 0.0135(6) 0.0235(7) -0.0008(5) 0.0061(5) -0.0007(4) C5 0.0255(7) 0.0250(7) 0.0319(8) 0.0063(6) 0.0022(6) 0.0029(6) C20 0.0163(6) 0.0247(7) 0.0437(9) 0.0016(6) 0.0131(6) -0.0010(5) C1 0.0370(9) 0.0259(8) 0.0270(8) -0.0116(6) 0.0038(7) -0.0019(6) C4 0.0300(8) 0.0178(7) 0.0428(9) 0.0049(6) 0.0119(7) 0.0057(6) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C19 1.7387(14) . ? Cl2 C17 1.7449(14) . ? O1 C2 1.3648(17) . ? O1 C1 1.4316(17) . ? O3 C9 1.2055(18) . ? O2 C9 1.3352(17) . ? O2 C10 1.4553(17) . ? N1 C13 1.3872(18) . ? N1 C14 1.4125(18) . ? N1 C20 1.4538(17) . ? C15 C16 1.3792(18) . ? C15 C14 1.3998(18) . ? C15 C12 1.5078(17) . ? O4 C13 1.2086(17) . ? C14 C19 1.3909(19) . ? O5 C20 1.4108(18) . ? O5 C21 1.415(2) . ? C11 C10 1.5125(18) . ? C11 C12 1.5406(17) . ? C16 C17 1.3926(18) . ? C8 C7 1.5208(18) . ? C8 C9 1.5278(18) . ? C8 C12 1.5438(17) . ? C17 C18 1.381(2) . ? C2 C3 1.3985(19) . ? C2 C7 1.4043(18) . ? C19 C18 1.394(2) . ? C12 C13 1.5311(17) . ? C3 C4 1.387(2) . ? C7 C6 1.3938(19) . ? C6 C5 1.389(2) . ? C5 C4 1.385(2) . ? 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 C2 O1 C1 117.61(11) . . ? C9 O2 C10 122.23(11) . . ? C13 N1 C14 110.65(11) . . ? C13 N1 C20 121.02(12) . . ? C14 N1 C20 127.00(12) . . ? C16 C15 C14 122.21(12) . . ? C16 C15 C12 128.42(12) . . ? C14 C15 C12 109.24(11) . . ? C19 C14 C15 119.23(12) . . ? C19 C14 N1 131.56(12) . . ? C15 C14 N1 109.20(11) . . ? C20 O5 C21 113.37(13) . . ? C10 C11 C12 111.51(11) . . ? C15 C16 C17 117.10(12) . . ? C7 C8 C9 111.34(11) . . ? C7 C8 C12 114.49(10) . . ? C9 C8 C12 114.99(11) . . ? O3 C9 O2 117.88(13) . . ? O3 C9 C8 120.72(13) . . ? O2 C9 C8 120.98(12) . . ? C18 C17 C16 122.30(13) . . ? C18 C17 Cl2 118.82(11) . . ? C16 C17 Cl2 118.88(11) . . ? O1 C2 C3 123.72(13) . . ? O1 C2 C7 115.76(12) . . ? C3 C2 C7 120.51(13) . . ? C14 C19 C18 119.41(12) . . ? C14 C19 Cl1 123.46(11) . . ? C18 C19 Cl1 117.12(11) . . ? C15 C12 C13 102.03(10) . . ? C15 C12 C11 108.83(10) . . ? C13 C12 C11 109.52(10) . . ? C15 C12 C8 114.87(10) . . ? C13 C12 C8 112.45(10) . . ? C11 C12 C8 108.89(10) . . ? C4 C3 C2 119.52(14) . . ? C6 C7 C2 118.47(12) . . ? C6 C7 C8 122.13(12) . . ? C2 C7 C8 119.40(12) . . ? C5 C6 C7 121.17(14) . . ? O2 C10 C11 111.88(11) . . ? C17 C18 C19 119.66(13) . . ? O4 C13 N1 125.39(13) . . ? O4 C13 C12 126.40(13) . . ? N1 C13 C12 108.20(11) . . ? C4 C5 C6 119.59(14) . . ? O5 C20 N1 112.48(12) . . ? C5 C4 C3 120.68(14) . . ? _diffrn_measured_fraction_theta_max 0.980 _diffrn_reflns_theta_full 28.05 _diffrn_measured_fraction_theta_full 0.980 _refine_diff_density_max 0.505 _refine_diff_density_min -0.238 _refine_diff_density_rms 0.057