 
data_7a 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C15 H14 Cl3 N3 O3' 
_chemical_formula_weight          390.64 
 
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                    10.730(2) 
_cell_length_b                    19.233(4) 
_cell_length_c                    8.9878(18) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  94.20(3) 
_cell_angle_gamma                 90.00 
_cell_volume                      1849.8(6) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     10938 
_cell_measurement_theta_min       2.12 
_cell_measurement_theta_max       27.47 
 
_exptl_crystal_description        'Block' 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.4 
_exptl_crystal_size_mid           0.3 
_exptl_crystal_size_min           0.3 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.403 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              800 
_exptl_absorpt_coefficient_mu     0.513 
_exptl_absorpt_correction_type    'Empirical' 
_exptl_absorpt_correction_T_min   0.602 
_exptl_absorpt_correction_T_max   0.857 
_exptl_special_details 
; 
ABSCOR by T.Higashi    8 March, 1995
  
; 
 
_diffrn_ambient_temperature       293(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   'Rigaku RAXIS RAPID IP' 
_diffrn_measurement_method        'Oscillation' 
_diffrn_detector_area_resol_mean  '100x100 microns' 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             10938 
_diffrn_reflns_av_R_equivalents   0.0471 
_diffrn_reflns_av_sigmaI/netI     0.0708 
_diffrn_reflns_limit_h_min        -13 
_diffrn_reflns_limit_h_max        13 
_diffrn_reflns_limit_k_min        -24 
_diffrn_reflns_limit_k_max        24 
_diffrn_reflns_limit_l_min        -11 
_diffrn_reflns_limit_l_max        11 
_diffrn_reflns_theta_min          2.12 
_diffrn_reflns_theta_max          27.47 
_reflns_number_total              3757 
_reflns_number_gt                 1659 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Molecular Structure Corporation (1994)
                                   MSC/AFC Diffractometer Control Software
                                   MSC, 3200 Research Forest Drive, The
                                   Woodlands, TX 77381, USA.'
_computing_cell_refinement        'Molecular Structure Corporation (1994)
                                   MSC/AFC Diffractometer Control Software
                                   MSC, 3200 Research Forest Drive, The
                                   Woodlands, TX 77381 USA.'
_computing_data_reduction         'Sheldrick, G. M. (1997) SHELXS97, Program
                                   for the Solution of Crystal Structure,
                                   University of Gottingen, Germany.'
_computing_structure_solution     'Sheldrick, G. M. (1997) SHELXS97, Program
                                   for the Solution of Crystal Structure,
                                   University of Gottingen, Germany.'
_computing_structure_refinement   'Sheldrick, G. M. (1997) SHELXL97, Program
                                   for the Refinement of Crystal Structure,
                                   University of Gottingen, Germany.'
_computing_molecular_graphics     'Interactive Molecular Graphics XP, Virsion
                                   4.2 for MSDOS (1990), Siemens Analytical
                                   X-ray Instruments Inc., Madison, Wisconsin,
                                   USA.'
_computing_publication_material   'Sheldrick, G. M. (1997) SHELXL97, Program
                                   for the refinement of Crystal Structure,
                                   University of Gottingen, Germany.'
 
_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)+(0.0919P)²+0.0000P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    'hydrogen atoms are generated by HFIX
                                  instructions'
_refine_ls_hydrogen_treatment     'hydrogen coordinates ride on the coordinates
                                  of the previous atom, the isotropic U values
                                  are 1.2 OR 1.5 time over the U values of the
                                  previous atom.'
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.0062(19) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          3757 
_refine_ls_number_parameters      222 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.1250 
_refine_ls_R_factor_gt            0.0595 
_refine_ls_wR_factor_ref          0.1799 
_refine_ls_wR_factor_gt           0.1599 
_refine_ls_goodness_of_fit_ref    0.921 
_refine_ls_restrained_S_all       0.921 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cl1 Cl 0.79905(12) 0.17119(6) 0.97556(11) 0.1017(5) Uani 1 1 d . . . 
Cl2 Cl 1.03062(12) 0.10942(9) 1.07957(14) 0.1264(6) Uani 1 1 d . . . 
Cl3 Cl 0.79949(18) 0.03353(7) 1.09360(16) 0.1490(8) Uani 1 1 d . . . 
O1 O 0.7697(3) 0.18623(15) 1.2840(3) 0.0933(9) Uani 1 1 d . . . 
O2 O 0.8699(3) -0.00967(14) 1.6023(4) 0.0939(9) Uani 1 1 d . . . 
O3 O 0.6731(3) 0.01399(13) 1.6695(3) 0.0851(8) Uani 1 1 d . . . 
N1 N 0.9253(3) 0.11720(18) 1.3794(3) 0.0655(8) Uani 1 1 d . . . 
N2 N 0.6998(3) 0.14452(16) 1.6162(3) 0.0641(8) Uani 1 1 d . . . 
N3 N 0.6195(4) 0.1794(2) 1.6382(4) 0.0933(11) Uani 1 1 d . . . 
C1 C 0.7852(4) 0.0317(2) 1.6217(4) 0.0685(10) Uani 1 1 d . . . 
C2 C 0.7965(3) 0.10522(19) 1.5942(4) 0.0617(9) Uani 1 1 d . . . 
C3 C 0.9093(3) 0.13998(18) 1.5336(4) 0.0633(9) Uani 1 1 d . . . 
H3 H 0.8924 0.1901 1.5300 0.076 Uiso 1 1 calc R . . 
C4 C 1.0304(3) 0.13003(19) 1.6259(4) 0.0645(9) Uani 1 1 d . . . 
H4 H 1.0659 0.0859 1.6307 0.077 Uiso 1 1 calc R . . 
C5 C 1.0891(3) 0.1812(2) 1.7009(4) 0.0706(10) Uani 1 1 d . . . 
H5 H 1.0499 0.2244 1.6952 0.085 Uiso 1 1 calc R . . 
C6 C 1.2103(3) 0.17807(19) 1.7931(4) 0.0656(9) Uani 1 1 d . . . 
C7 C 1.2423(4) 0.2337(2) 1.8927(5) 0.0942(14) Uani 1 1 d . . . 
H7 H 1.1880 0.2710 1.8996 0.113 Uiso 1 1 calc R . . 
C8 C 1.3556(4) 0.2322(3) 1.9805(6) 0.1073(17) Uani 1 1 d . . . 
H8 H 1.3753 0.2687 2.0458 0.129 Uiso 1 1 calc R . . 
C9 C 1.4373(5) 0.1789(3) 1.9727(5) 0.1027(15) Uani 1 1 d . . . 
H9 H 1.5109 0.1786 2.0340 0.123 Uiso 1 1 calc R . . 
C10 C 1.4117(4) 0.1255(3) 1.8746(6) 0.0955(14) Uani 1 1 d . . . 
H10 H 1.4690 0.0897 1.8658 0.115 Uiso 1 1 calc R . . 
C11 C 1.2973(4) 0.1254(2) 1.7872(5) 0.0753(10) Uani 1 1 d . . . 
H11 H 1.2796 0.0883 1.7227 0.090 Uiso 1 1 calc R . . 
C12 C 0.8505(3) 0.14387(18) 1.2689(4) 0.0595(9) Uani 1 1 d . . . 
C13 C 0.8697(3) 0.11578(16) 1.1096(4) 0.0611(9) Uani 1 1 d . . . 
C14 C 0.6493(5) -0.0591(3) 1.6946(8) 0.129(2) Uani 1 1 d . . . 
H14A H 0.6898 -0.0867 1.6217 0.155 Uiso 1 1 calc R . . 
H14B H 0.6847 -0.0722 1.7931 0.155 Uiso 1 1 calc R . . 
C15 C 0.5183(6) -0.0733(3) 1.6831(8) 0.156(3) Uani 1 1 d . . . 
H15A H 0.5048 -0.1218 1.7013 0.235 Uiso 1 1 calc R . . 
H15B H 0.4837 -0.0615 1.5849 0.235 Uiso 1 1 calc R . . 
H15C H 0.4783 -0.0462 1.7556 0.235 Uiso 1 1 calc R . . 
HN1 H 0.956(3) 0.0794(17) 1.360(3) 0.047(9) Uiso 1 1 d . . . 
 
 
_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 C13 1.740(3) . ? 
Cl2 C13 1.771(4) . ? 
Cl3 C13 1.754(4) . ? 
O1 C12 1.204(4) . ? 
O2 C1 1.229(4) . ? 
O3 C1 1.350(4) . ? 
O3 C14 1.450(5) . ? 
N1 C12 1.333(4) . ? 
N1 C3 1.476(4) . ? 
N2 N3 1.121(4) . ? 
N2 C2 1.310(5) . ? 
C1 C2 1.443(5) . ? 
C2 C3 1.518(5) . ? 
C3 C4 1.502(5) . ? 
C4 C5 1.326(5) . ? 
C5 C6 1.492(5) . ? 
C6 C11 1.381(5) . ? 
C6 C7 1.420(5) . ? 
C7 C8 1.401(6) . ? 
C8 C9 1.353(6) . ? 
C9 C10 1.369(6) . ? 
C10 C11 1.408(6) . ? 
C12 C13 1.558(5) . ? 
C14 C15 1.429(7) . ? 
 
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 
C1 O3 C14 117.7(3) . . ? 
C12 N1 C3 118.7(3) . . ? 
N3 N2 C2 177.7(4) . . ? 
O2 C1 O3 124.6(4) . . ? 
O2 C1 C2 122.5(4) . . ? 
O3 C1 C2 112.9(3) . . ? 
N2 C2 C1 117.5(3) . . ? 
N2 C2 C3 117.4(3) . . ? 
C1 C2 C3 124.9(3) . . ? 
N1 C3 C4 109.0(3) . . ? 
N1 C3 C2 110.9(3) . . ? 
C4 C3 C2 115.2(3) . . ? 
C5 C4 C3 123.1(3) . . ? 
C4 C5 C6 127.9(4) . . ? 
C11 C6 C7 116.3(4) . . ? 
C11 C6 C5 124.9(3) . . ? 
C7 C6 C5 118.7(4) . . ? 
C8 C7 C6 120.0(4) . . ? 
C9 C8 C7 121.7(5) . . ? 
C8 C9 C10 120.1(5) . . ? 
C9 C10 C11 119.0(5) . . ? 
C6 C11 C10 122.8(4) . . ? 
O1 C12 N1 125.2(3) . . ? 
O1 C12 C13 118.9(3) . . ? 
N1 C12 C13 116.0(3) . . ? 
C12 C13 Cl1 110.1(2) . . ? 
C12 C13 Cl3 107.6(2) . . ? 
Cl1 C13 Cl3 109.4(2) . . ? 
C12 C13 Cl2 111.1(2) . . ? 
Cl1 C13 Cl2 108.50(19) . . ? 
Cl3 C13 Cl2 110.07(19) . . ? 
C15 C14 O3 111.0(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 
C14 O3 C1 O2 -2.3(6) . . . . ? 
C14 O3 C1 C2 177.4(4) . . . . ? 
N3 N2 C2 C1 123(10) . . . . ? 
N3 N2 C2 C3 -60(10) . . . . ? 
O2 C1 C2 N2 178.9(3) . . . . ? 
O3 C1 C2 N2 -0.8(4) . . . . ? 
O2 C1 C2 C3 2.4(5) . . . . ? 
O3 C1 C2 C3 -177.3(3) . . . . ? 
C12 N1 C3 C4 -155.4(3) . . . . ? 
C12 N1 C3 C2 76.8(4) . . . . ? 
N2 C2 C3 N1 -111.0(3) . . . . ? 
C1 C2 C3 N1 65.5(4) . . . . ? 
N2 C2 C3 C4 124.7(3) . . . . ? 
C1 C2 C3 C4 -58.9(4) . . . . ? 
N1 C3 C4 C5 123.4(4) . . . . ? 
C2 C3 C4 C5 -111.2(4) . . . . ? 
C3 C4 C5 C6 -178.6(3) . . . . ? 
C4 C5 C6 C11 16.9(6) . . . . ? 
C4 C5 C6 C7 -164.9(4) . . . . ? 
C11 C6 C7 C8 -1.4(6) . . . . ? 
C5 C6 C7 C8 -179.8(4) . . . . ? 
C6 C7 C8 C9 0.5(7) . . . . ? 
C7 C8 C9 C10 1.6(8) . . . . ? 
C8 C9 C10 C11 -2.7(7) . . . . ? 
C7 C6 C11 C10 0.4(6) . . . . ? 
C5 C6 C11 C10 178.7(4) . . . . ? 
C9 C10 C11 C6 1.7(6) . . . . ? 
C3 N1 C12 O1 0.6(6) . . . . ? 
C3 N1 C12 C13 -178.1(3) . . . . ? 
O1 C12 C13 Cl1 17.8(4) . . . . ? 
N1 C12 C13 Cl1 -163.4(3) . . . . ? 
O1 C12 C13 Cl3 -101.4(3) . . . . ? 
N1 C12 C13 Cl3 77.4(3) . . . . ? 
O1 C12 C13 Cl2 138.0(3) . . . . ? 
N1 C12 C13 Cl2 -43.2(4) . . . . ? 
C1 O3 C14 C15 -155.8(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 
N1 HN1 O2  0.82(3) 2.30(3) 3.013(4) 145(3) 3_758 
 
_diffrn_measured_fraction_theta_max    0.885 
_diffrn_reflns_theta_full              27.47 
_diffrn_measured_fraction_theta_full   0.885 
_refine_diff_density_max    0.328 
_refine_diff_density_min   -0.298 
_refine_diff_density_rms    0.052

#===END

 
data_7b 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C9 H12 Cl3 N3 O3' 
_chemical_formula_weight          316.57 
 
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                    9.6616(19) 
_cell_length_b                    10.436(2) 
_cell_length_c                    15.210(3) 
_cell_angle_alpha                 89.51(3) 
_cell_angle_beta                  71.86(3) 
_cell_angle_gamma                 78.36(3) 
_cell_volume                      1425.0(5) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     13008 
_cell_measurement_theta_min       2.27 
_cell_measurement_theta_max       27.48 
 
_exptl_crystal_description        'Block' 
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           0.35 
_exptl_crystal_size_mid           0.35 
_exptl_crystal_size_min           0.35 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.476 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              648 
_exptl_absorpt_coefficient_mu     0.646 
_exptl_absorpt_correction_type    'Empirical' 
_exptl_absorpt_correction_T_min   0.608 
_exptl_absorpt_correction_T_max   0.798 
_exptl_special_details 
; 
ABSCOR by T.Higashi    8 March, 1995
 
; 
 
_diffrn_ambient_temperature       293(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   'Rigaku RAXIS RAPID IP' 
_diffrn_measurement_method        'Oscillation' 
_diffrn_detector_area_resol_mean  '100x100 microns' 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6410 
_diffrn_reflns_av_R_equivalents   0.0298 
_diffrn_reflns_av_sigmaI/netI     0.0416 
_diffrn_reflns_limit_h_min        -12 
_diffrn_reflns_limit_h_max        12 
_diffrn_reflns_limit_k_min        -13 
_diffrn_reflns_limit_k_max        13 
_diffrn_reflns_limit_l_min        -19 
_diffrn_reflns_limit_l_max        19 
_diffrn_reflns_theta_min          2.27 
_diffrn_reflns_theta_max          27.48 
_reflns_number_total              6410 
_reflns_number_gt                 3811 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        'Molecular Structure Corporation (1994)
                                   MSC/AFC Diffractometer Control Software
                                   MSC, 3200 Research Forest Drive, The
                                   Woodlands, TX 77381, USA.'
_computing_cell_refinement        'Molecular Structure Corporation (1994)
                                   MSC/AFC Diffractometer Control Software
                                   MSC, 3200 Research Forest Drive, The
                                   Woodlands, TX 77381 USA.'
_computing_data_reduction         'Sheldrick, G. M. (1997) SHELXS97, Program
                                   for the Solution of Crystal Structure,
                                   University of Gottingen, Germany.'
_computing_structure_solution     'Sheldrick, G. M. (1997) SHELXS97, Program
                                   for the Solution of Crystal Structure,
                                   University of Gottingen, Germany.'
_computing_structure_refinement   'Sheldrick, G. M. (1997) SHELXL97, Program
                                   for the Refinement of Crystal Structure,
                                   University of Gottingen, Germany.'
_computing_molecular_graphics     'Interactive Molecular Graphics XP, Virsion
                                   4.2 for MSDOS (1990), Siemens Analytical
                                   X-ray Instruments Inc., Madison, Wisconsin,
                                   USA.'
_computing_publication_material   'Sheldrick, G. M. (1997) SHELXL97, Program
                                   for the refinement of Crystal Structure,
                                   University of Gottingen, Germany.'
 
_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)+(0.0776P)²+0.5844P] where P=(Fo²+2Fc²)/3' 
_atom_sites_solution_primary      direct 
_atom_sites_solution_secondary    difmap 
_atom_sites_solution_hydrogens    'hydrogen atoms are generated by HFIX
                                  instructions'
_refine_ls_hydrogen_treatment     'hydrogen coordinates ride on the coordinates
                                  of the previous atom, the isotropic U values
                                  are 1.2 OR 1.5 time over the U values of the
                                  previous atom.'
_refine_ls_extinction_method      SHELXL 
_refine_ls_extinction_coef        0.017(2) 
_refine_ls_extinction_expression 
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^' 
_refine_ls_number_reflns          6410 
_refine_ls_number_parameters      328 
_refine_ls_number_restraints      0 
_refine_ls_R_factor_all           0.0959 
_refine_ls_R_factor_gt            0.0591 
_refine_ls_wR_factor_ref          0.1786 
_refine_ls_wR_factor_gt           0.1663 
_refine_ls_goodness_of_fit_ref    1.084 
_refine_ls_restrained_S_all       1.084 
_refine_ls_shift/su_max           0.000 
_refine_ls_shift/su_mean          0.000 
 
loop_ 
 _atom_site_label 
 _atom_site_type_symbol 
 _atom_site_fract_x 
 _atom_site_fract_y 
 _atom_site_fract_z 
 _atom_site_U_iso_or_equiv 
 _atom_site_adp_type 
 _atom_site_occupancy 
 _atom_site_symmetry_multiplicity 
 _atom_site_calc_flag 
 _atom_site_refinement_flags 
 _atom_site_disorder_assembly 
 _atom_site_disorder_group 
Cl1 Cl -0.54106(12) 1.46533(12) 0.31875(8) 0.0844(4) Uani 1 1 d . . . 
Cl2 Cl -0.71170(14) 1.64671(10) 0.22842(8) 0.0826(3) Uani 1 1 d . . . 
Cl3 Cl -0.85899(13) 1.51226(14) 0.38204(8) 0.0914(4) Uani 1 1 d . . . 
Cl4 Cl 0.48509(13) 1.09219(14) 0.32619(11) 0.1026(5) Uani 1 1 d . . . 
Cl5 Cl 0.39364(13) 0.86073(15) 0.40866(8) 0.1049(5) Uani 1 1 d . . . 
Cl6 Cl 0.58234(11) 0.84645(12) 0.22065(8) 0.0805(3) Uani 1 1 d . . . 
O1 O -0.7827(3) 1.3120(3) 0.2407(2) 0.0828(8) Uani 1 1 d . . . 
O2 O -0.6297(3) 1.4678(3) -0.0555(2) 0.0904(9) Uani 1 1 d . . . 
O3 O -0.8146(3) 1.3769(2) -0.06904(17) 0.0643(6) Uani 1 1 d . . . 
O4 O 0.3081(3) 0.9631(3) 0.19179(17) 0.0719(7) Uani 1 1 d . . . 
O5 O -0.1036(3) 0.9181(3) 0.46226(17) 0.0670(7) Uani 1 1 d . . . 
O6 O -0.1598(3) 0.7943(2) 0.36372(15) 0.0548(6) Uani 1 1 d . . . 
N1 N -0.5857(3) 1.3723(3) 0.1370(2) 0.0638(8) Uani 1 1 d . . . 
N2 N -0.7719(5) 1.2013(4) 0.0440(3) 0.0825(11) Uani 1 1 d . . . 
N3 N -0.8524(7) 1.1348(5) 0.0604(4) 0.1259(19) Uani 1 1 d . . . 
N4 N 0.1693(3) 1.0329(3) 0.33768(18) 0.0500(6) Uani 1 1 d . . . 
N5 N -0.0403(4) 0.9271(3) 0.2251(2) 0.0635(8) Uani 1 1 d . . . 
N6 N -0.0375(5) 0.8953(4) 0.1544(3) 0.0991(13) Uani 1 1 d . . . 
C1 C -0.7026(4) 1.4975(3) 0.2838(2) 0.0543(8) Uani 1 1 d . . . 
C2 C -0.6944(4) 1.3833(3) 0.2172(3) 0.0543(8) Uani 1 1 d . . . 
C3 C -0.5597(6) 1.2620(6) 0.0710(4) 0.1088(19) Uani 1 1 d . . . 
H3 H -0.5877 1.1928 0.1127 0.131 Uiso 1 1 calc R . . 
C4 C -0.6771(5) 1.2809(4) 0.0236(3) 0.0712(11) Uani 1 1 d . . . 
C5 C -0.7017(4) 1.3834(4) -0.0366(3) 0.0641(9) Uani 1 1 d . . . 
C6 C -0.4169(7) 1.2083(7) 0.0233(5) 0.143(3) Uani 1 1 d . . . 
H6A H -0.3832 1.2671 -0.0247 0.172 Uiso 1 1 calc R . . 
H6B H -0.4173 1.1278 -0.0079 0.172 Uiso 1 1 calc R . . 
C7 C -0.3004(5) 1.1760(5) 0.0700(4) 0.0982(15) Uani 1 1 d . . . 
H7A H -0.2050 1.1448 0.0243 0.147 Uiso 1 1 calc R . . 
H7B H -0.3233 1.1092 0.1127 0.147 Uiso 1 1 calc R . . 
H7C H -0.2978 1.2531 0.1029 0.147 Uiso 1 1 calc R . . 
C8 C -0.8530(5) 1.4816(4) -0.1253(3) 0.0786(11) Uani 1 1 d . . . 
H8A H -0.7676 1.4862 -0.1788 0.094 Uiso 1 1 calc R . . 
H8B H -0.8848 1.5650 -0.0897 0.094 Uiso 1 1 calc R . . 
C9 C -0.9760(5) 1.4522(5) -0.1554(3) 0.0878(13) Uani 1 1 d . . . 
H9A H -1.0040 1.5193 -0.1938 0.132 Uiso 1 1 calc R . . 
H9B H -1.0602 1.4491 -0.1019 0.132 Uiso 1 1 calc R . . 
H9C H -0.9435 1.3690 -0.1898 0.132 Uiso 1 1 calc R . . 
C10 C 0.4333(4) 0.9457(4) 0.3057(2) 0.0612(9) Uani 1 1 d . . . 
C11 C 0.2951(4) 0.9812(3) 0.2730(2) 0.0507(8) Uani 1 1 d . . . 
C12 C 0.0329(3) 1.0790(3) 0.3128(2) 0.0511(8) Uani 1 1 d . . . 
H12 H 0.0620 1.1134 0.2510 0.061 Uiso 1 1 calc R . . 
C13 C -0.0393(4) 0.9642(3) 0.3066(2) 0.0502(8) Uani 1 1 d . . . 
C14 C -0.1021(3) 0.8930(3) 0.3842(2) 0.0489(7) Uani 1 1 d . . . 
C15 C -0.0685(4) 1.1901(3) 0.3797(3) 0.0647(10) Uani 1 1 d . . . 
H15A H -0.0149 1.2593 0.3799 0.078 Uiso 1 1 calc R . . 
H15B H -0.0966 1.1589 0.4417 0.078 Uiso 1 1 calc R . . 
C16 C -0.2083(5) 1.2456(4) 0.3545(4) 0.0971(16) Uani 1 1 d . . . 
H16A H -0.2701 1.3149 0.3991 0.146 Uiso 1 1 calc R . . 
H16B H -0.2620 1.1775 0.3546 0.146 Uiso 1 1 calc R . . 
H16C H -0.1811 1.2793 0.2940 0.146 Uiso 1 1 calc R . . 
C17 C -0.2344(4) 0.7257(3) 0.4422(2) 0.0603(9) Uani 1 1 d . . . 
H17A H -0.3250 0.7829 0.4807 0.072 Uiso 1 1 calc R . . 
H17B H -0.1700 0.6981 0.4797 0.072 Uiso 1 1 calc R . . 
C18 C -0.2703(5) 0.6095(4) 0.4049(3) 0.0714(11) Uani 1 1 d . . . 
H18A H -0.3191 0.5618 0.4554 0.107 Uiso 1 1 calc R . . 
H18B H -0.1800 0.5538 0.3668 0.107 Uiso 1 1 calc R . . 
H18C H -0.3349 0.6380 0.3686 0.107 Uiso 1 1 calc R . . 
HN1 H -0.5227 1.4409 0.1186 0.084(13) Uiso 1 1 d R . . 
HN4 H 0.1620 1.0466 0.4010 0.058(10) Uiso 1 1 d 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 C1 1.770(3) . ? 
Cl2 C1 1.764(4) . ? 
Cl3 C1 1.744(4) . ? 
Cl4 C10 1.761(4) . ? 
Cl5 C10 1.768(4) . ? 
Cl6 C10 1.755(4) . ? 
O1 C2 1.214(4) . ? 
O2 C5 1.209(5) . ? 
O3 C5 1.342(4) . ? 
O3 C8 1.443(5) . ? 
O4 C11 1.215(4) . ? 
O5 C14 1.213(4) . ? 
O6 C14 1.347(4) . ? 
O6 C17 1.455(4) . ? 
N1 C2 1.326(5) . ? 
N1 C3 1.464(5) . ? 
N2 N3 1.115(6) . ? 
N2 C4 1.322(6) . ? 
N4 C11 1.318(4) . ? 
N4 C12 1.471(4) . ? 
N5 N6 1.119(4) . ? 
N5 C13 1.305(4) . ? 
C1 C2 1.544(5) . ? 
C3 C6 1.348(7) . ? 
C3 C4 1.504(6) . ? 
C4 C5 1.435(6) . ? 
C6 C7 1.491(7) . ? 
C8 C9 1.485(6) . ? 
C10 C11 1.542(5) . ? 
C12 C15 1.511(5) . ? 
C12 C13 1.520(4) . ? 
C13 C14 1.425(5) . ? 
C15 C16 1.520(5) . ? 
C17 C18 1.489(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 
C5 O3 C8 116.4(3) . . ? 
C14 O6 C17 115.8(3) . . ? 
C2 N1 C3 119.7(4) . . ? 
N3 N2 C4 179.3(5) . . ? 
C11 N4 C12 120.0(3) . . ? 
N6 N5 C13 178.3(4) . . ? 
C2 C1 Cl3 110.8(2) . . ? 
C2 C1 Cl2 110.7(2) . . ? 
Cl3 C1 Cl2 108.75(19) . . ? 
C2 C1 Cl1 108.7(2) . . ? 
Cl3 C1 Cl1 108.75(19) . . ? 
Cl2 C1 Cl1 109.18(19) . . ? 
O1 C2 N1 125.5(4) . . ? 
O1 C2 C1 119.8(3) . . ? 
N1 C2 C1 114.7(3) . . ? 
C6 C3 N1 117.0(5) . . ? 
C6 C3 C4 120.3(5) . . ? 
N1 C3 C4 111.0(4) . . ? 
N2 C4 C5 117.1(4) . . ? 
N2 C4 C3 117.2(5) . . ? 
C5 C4 C3 125.6(4) . . ? 
O2 C5 O3 123.4(4) . . ? 
O2 C5 C4 123.7(4) . . ? 
O3 C5 C4 113.0(4) . . ? 
C3 C6 C7 121.7(6) . . ? 
O3 C8 C9 106.9(4) . . ? 
C11 C10 Cl6 110.8(2) . . ? 
C11 C10 Cl4 108.1(3) . . ? 
Cl6 C10 Cl4 109.0(2) . . ? 
C11 C10 Cl5 110.8(2) . . ? 
Cl6 C10 Cl5 108.5(2) . . ? 
Cl4 C10 Cl5 109.5(2) . . ? 
O4 C11 N4 124.7(3) . . ? 
O4 C11 C10 119.7(3) . . ? 
N4 C11 C10 115.6(3) . . ? 
N4 C12 C15 110.0(3) . . ? 
N4 C12 C13 109.7(3) . . ? 
C15 C12 C13 113.9(3) . . ? 
N5 C13 C14 118.4(3) . . ? 
N5 C13 C12 117.8(3) . . ? 
C14 C13 C12 123.8(3) . . ? 
O5 C14 O6 122.3(3) . . ? 
O5 C14 C13 123.3(3) . . ? 
O6 C14 C13 114.4(3) . . ? 
C12 C15 C16 112.1(3) . . ? 
O6 C17 C18 107.6(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 
C3 N1 C2 O1 -4.0(6) . . . . ? 
C3 N1 C2 C1 175.4(3) . . . . ? 
Cl3 C1 C2 O1 -6.1(4) . . . . ? 
Cl2 C1 C2 O1 -126.8(3) . . . . ? 
Cl1 C1 C2 O1 113.3(3) . . . . ? 
Cl3 C1 C2 N1 174.5(2) . . . . ? 
Cl2 C1 C2 N1 53.8(4) . . . . ? 
Cl1 C1 C2 N1 -66.1(3) . . . . ? 
C2 N1 C3 C6 -142.0(6) . . . . ? 
C2 N1 C3 C4 74.8(6) . . . . ? 
N3 N2 C4 C5 15(53) . . . . ? 
N3 N2 C4 C3 -170(100) . . . . ? 
C6 C3 C4 N2 106.9(7) . . . . ? 
N1 C3 C4 N2 -111.3(5) . . . . ? 
C6 C3 C4 C5 -77.8(7) . . . . ? 
N1 C3 C4 C5 64.1(6) . . . . ? 
C8 O3 C5 O2 -3.1(5) . . . . ? 
C8 O3 C5 C4 176.0(3) . . . . ? 
N2 C4 C5 O2 174.7(4) . . . . ? 
C3 C4 C5 O2 -0.6(6) . . . . ? 
N2 C4 C5 O3 -4.4(5) . . . . ? 
C3 C4 C5 O3 -179.8(4) . . . . ? 
N1 C3 C6 C7 46.4(10) . . . . ? 
C4 C3 C6 C7 -173.9(6) . . . . ? 
C5 O3 C8 C9 178.3(3) . . . . ? 
C12 N4 C11 O4 -2.8(5) . . . . ? 
C12 N4 C11 C10 175.7(3) . . . . ? 
Cl6 C10 C11 O4 -14.4(4) . . . . ? 
Cl4 C10 C11 O4 105.1(3) . . . . ? 
Cl5 C10 C11 O4 -134.9(3) . . . . ? 
Cl6 C10 C11 N4 167.1(2) . . . . ? 
Cl4 C10 C11 N4 -73.5(3) . . . . ? 
Cl5 C10 C11 N4 46.6(4) . . . . ? 
C11 N4 C12 C15 -151.0(3) . . . . ? 
C11 N4 C12 C13 83.0(4) . . . . ? 
N6 N5 C13 C14 -128(14) . . . . ? 
N6 N5 C13 C12 50(15) . . . . ? 
N4 C12 C13 N5 -112.1(3) . . . . ? 
C15 C12 C13 N5 124.1(4) . . . . ? 
N4 C12 C13 C14 66.1(4) . . . . ? 
C15 C12 C13 C14 -57.6(4) . . . . ? 
C17 O6 C14 O5 4.5(5) . . . . ? 
C17 O6 C14 C13 -175.7(3) . . . . ? 
N5 C13 C14 O5 178.4(3) . . . . ? 
C12 C13 C14 O5 0.1(5) . . . . ? 
N5 C13 C14 O6 -1.4(4) . . . . ? 
C12 C13 C14 O6 -179.6(3) . . . . ? 
N4 C12 C15 C16 177.5(3) . . . . ? 
C13 C12 C15 C16 -58.9(4) . . . . ? 
C14 O6 C17 C18 -171.9(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 
N1 HN1 O2  1.01 1.91 2.900(5) 163.2 2_485 
N4 HN4 O5  0.95 1.99 2.935(4) 168.7 2_576 
 
_diffrn_measured_fraction_theta_max    0.979 
_diffrn_reflns_theta_full              27.48 
_diffrn_measured_fraction_theta_full   0.979 
_refine_diff_density_max    0.485 
_refine_diff_density_min   -0.441 
_refine_diff_density_rms    0.069 

#===END


