  
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 F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² 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/[σ²(Fo²)+(0.0490P)²+1.0893P] where P=(Fo²+2Fc²)/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 . . 
  
  
_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 

