 
data_33 
 
_audit_creation_method            SHELXL-97 
_chemical_name_systematic 
; 
 ? 
; 
_chemical_name_common             ? 
_chemical_melting_point           ? 
_chemical_formula_moiety          ? 
_chemical_formula_sum 
 'C14 H16 Cl4 D6 N4 O4 Zn' 
_chemical_formula_weight          523.56 
 
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' 
 'Zn'  'Zn'   0.2839   1.4301 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 'D'  'D'   0.0000   0.0000 
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 
 
_symmetry_cell_setting           monoclinic 
_symmetry_space_group_name_H-M    C2/c 
 
loop_ 
 _symmetry_equiv_pos_as_xyz 
 'x, y, z' 
 '-x, y, -z+1/2' 
 'x+1/2, y+1/2, z' 
 '-x+1/2, y+1/2, -z+1/2' 
 '-x, -y, -z' 
 'x, -y, z-1/2' 
 '-x+1/2, -y+1/2, -z' 
 'x+1/2, -y+1/2, z-1/2' 
 
_cell_length_a                    19.0387(13) 
_cell_length_b                    15.0913(9) 
_cell_length_c                    7.2869(5) 
_cell_angle_alpha                 90.00 
_cell_angle_beta                  96.822(6) 
_cell_angle_gamma                 90.00 
_cell_volume                      2078.8(2) 
_cell_formula_units_Z             4 
_cell_measurement_temperature     293(2) 
_cell_measurement_reflns_used     2609
_cell_measurement_theta_min       2.7250 
_cell_measurement_theta_max       29.6380 
 
_exptl_crystal_description      cuboid
_exptl_crystal_colour             ? 
_exptl_crystal_size_max           ? 
_exptl_crystal_size_mid           ? 
_exptl_crystal_size_min           ? 
_exptl_crystal_density_meas       ? 
_exptl_crystal_density_diffrn     1.673 
_exptl_crystal_density_method     'not measured' 
_exptl_crystal_F_000              1056 
_exptl_absorpt_coefficient_mu     1.723 
_exptl_absorpt_correction_type    multi-scan 
_exptl_absorpt_correction_T_min   0.88144 
_exptl_absorpt_correction_T_max   1.00000 
_exptl_absorpt_process_details    ? 
 
_exptl_special_details 
; 
 ? 
; 
 
_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    'XtaLAB Synergy R, DW system, HyPix' 
_diffrn_measurement_method        'ω scans'
_diffrn_detector_area_resol_mean  ? 
_diffrn_standards_number          ? 
_diffrn_standards_interval_count  ? 
_diffrn_standards_interval_time   ? 
_diffrn_standards_decay_%         ? 
_diffrn_reflns_number             6276 
_diffrn_reflns_av_R_equivalents   0.0177 
_diffrn_reflns_av_sigmaI/netI     0.0204 
_diffrn_reflns_limit_h_min        -22 
_diffrn_reflns_limit_h_max        22 
_diffrn_reflns_limit_k_min        -17 
_diffrn_reflns_limit_k_max        17 
_diffrn_reflns_limit_l_min        -8 
_diffrn_reflns_limit_l_max        5 
_diffrn_reflns_theta_min          2.15 
_diffrn_reflns_theta_max          25.00 
_reflns_number_total              1839 
_reflns_number_gt                 1611 
_reflns_threshold_expression      >2sigma(I) 
 
_computing_data_collection        ? 
_computing_cell_refinement        ? 
_computing_data_reduction         ? 
_computing_structure_solution     'SHELXS-97 (Sheldrick, 1990)' 
_computing_structure_refinement   'SHELXL-97 (Sheldrick, 1997)' 
_computing_molecular_graphics     ? 
_computing_publication_material   ? 
 
_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)+(0.0849P)²+5.0209P] 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          1839 
_refine_ls_number_parameters      201 
_refine_ls_number_restraints      192 
_refine_ls_R_factor_all           0.0472 
_refine_ls_R_factor_gt            0.0413 
_refine_ls_wR_factor_ref          0.1331 
_refine_ls_wR_factor_gt           0.1294 
_refine_ls_goodness_of_fit_ref    1.081 
_refine_ls_restrained_S_all       1.028 
_refine_ls_shift/su_max           0.008 
_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 
Zn1 Zn 0.5000 0.255051(15) 0.2500 0.03227(6) Uani 1 2 d SU . . 
Cl2 Cl 0.49110(2) 0.16809(3) -0.00474(5) 0.04538(10) Uani 1 1 d U . . 
Cl3 Cl 0.40236(2) 0.34072(3) 0.24052(7) 0.05717(13) Uani 1 1 d U . . 
O1 O 0.82198(5) 0.60610(6) 0.71537(17) 0.0470(3) Uani 1 1 d U . . 
N1 N 0.63001(6) 0.27131(8) 0.8399(2) 0.0408(4) Uani 1 1 d DU . . 
C1 C 0.78582(7) 0.45693(8) 0.72848(18) 0.0280(3) Uani 1 1 d U . . 
N2 N 0.89884(6) 0.50440(8) 0.63830(19) 0.0420(3) Uani 1 1 d DU . . 
C4 C 0.68478(7) 0.33503(9) 0.8000(2) 0.0316(3) Uani 1 1 d U . . 
C7 C 0.83791(7) 0.52754(9) 0.69325(18) 0.0316(3) Uani 1 1 d U . . 
C5 C 0.67319(7) 0.42369(9) 0.8289(2) 0.0376(4) Uani 1 1 d U . . 
C3 C 0.74583(8) 0.30505(9) 0.7375(2) 0.0363(4) Uani 1 1 d U . . 
C6 C 0.72400(7) 0.48412(9) 0.7936(2) 0.0341(4) Uani 1 1 d U . . 
C2 C 0.79674(7) 0.36651(9) 0.7020(2) 0.0355(4) Uani 1 1 d U . . 
O2 O 0.5000 0.62570(16) 0.2500 0.1989(18) Uani 1 2 d SD . . 
D2 D 0.51660(10) 0.6105(2) 0.15763(16) 0.298 Uiso 1 1 d D . . 
O3 O 0.5000 0.5000 1.0000 0.1989(18) Uani 1 2 d SD . . 
D3 D 0.46267(5) 0.47704(14) 0.9613(6) 0.298 Uiso 1 1 d D . . 
H2 H 0.8350(7) 0.3451(9) 0.6585(18) 0.0281(6) Uani 1 1 d U . . 
H5 H 0.6330(7) 0.4372(10) 0.878(2) 0.038(3) Uani 1 1 d U . . 
H6 H 0.7170(7) 0.5445(10) 0.814(2) 0.044(4) Uani 1 1 d U . . 
H3 H 0.7555(9) 0.2426(9) 0.720(3) 0.043(4) Uani 1 1 d U . . 
H1 H 0.9051(7) 0.4501(5) 0.6052(18) 0.0364(6) Uani 1 1 d DU . . 
H4 H 0.9263(5) 0.5477(6) 0.6092(18) 0.0373(6) Uani 1 1 d DU . . 
D1 D 0.6435(8) 0.2146(11) 0.821(2) 0.042(4) Uiso 1 1 d . . . 
H8 H 0.5952(5) 0.2780(11) 0.7524(16) 0.059(3) Uani 1 1 d DU . . 
H7 H 0.6192(7) 0.2838(13) 0.9523(12) 0.073(4) Uani 1 1 d DU . . 
 
 
_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 
Zn1 Cl3 2.2587(4) . ? 
Zn1 Cl3 2.2587(4) 2_655 ? 
Zn1 Cl2 2.2632(4) . ? 
Zn1 Cl2 2.2632(4) 2_655 ? 
O1 C7 1.2389(17) . ? 
N1 H8 0.869(10) . ? 
N1 H7 0.888(10) . ? 
N1 C4 1.4724(18) . ? 
C1 C6 1.383(2) . ? 
C1 C2 1.3972(19) . ? 
C1 C7 1.4984(19) . ? 
N2 H1 0.867(8) . ? 
N2 H4 0.878(9) . ? 
N2 C7 1.3185(19) . ? 
C4 C3 1.375(2) . ? 
C4 C5 1.3762(19) . ? 
C5 H5 0.906(15) . ? 
C5 C6 1.376(2) . ? 
C3 H3 0.972(14) . ? 
C3 C2 1.388(2) . ? 
C6 H6 0.934(15) . ? 
C2 H2 0.889(14) . ? 
O3 D3 0.8106(13) . ? 
 
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 
Cl3 Zn1 Cl3 110.16(2) . 2_655 ? 
Cl3 Zn1 Cl2 109.009(17) . . ? 
Cl3 Zn1 Cl2 109.764(17) 2_655 . ? 
Cl3 Zn1 Cl2 109.764(17) . 2_655 ? 
Cl3 Zn1 Cl2 109.009(17) 2_655 2_655 ? 
Cl2 Zn1 Cl2 109.11(2) . 2_655 ? 
H8 N1 H7 114.4(12) . . ? 
H8 N1 C4 106.0(10) . . ? 
H7 N1 C4 106.9(12) . . ? 
C6 C1 C2 118.94(12) . . ? 
C6 C1 C7 117.10(11) . . ? 
C2 C1 C7 123.96(12) . . ? 
H1 N2 H4 122.1(12) . . ? 
H1 N2 C7 119.3(9) . . ? 
H4 N2 C7 116.5(7) . . ? 
C3 C4 C5 121.86(13) . . ? 
C3 C4 N1 119.79(12) . . ? 
C5 C4 N1 118.35(12) . . ? 
O1 C7 N2 122.05(13) . . ? 
O1 C7 C1 118.75(12) . . ? 
N2 C7 C1 119.19(12) . . ? 
H5 C5 C6 124.7(9) . . ? 
H5 C5 C4 116.0(10) . . ? 
C6 C5 C4 119.15(13) . . ? 
H3 C3 C4 122.9(11) . . ? 
H3 C3 C2 118.5(10) . . ? 
C4 C3 C2 118.60(12) . . ? 
H6 C6 C5 120.0(9) . . ? 
H6 C6 C1 119.1(9) . . ? 
C5 C6 C1 120.90(13) . . ? 
H2 C2 C3 116.3(9) . . ? 
H2 C2 C1 123.1(9) . . ? 
C3 C2 C1 120.56(13) . . ? 
 
_diffrn_measured_fraction_theta_max    0.999 
_diffrn_reflns_theta_full              25.00 
_diffrn_measured_fraction_theta_full   0.999 
_refine_diff_density_max    1.084 
_refine_diff_density_min   -1.151 
_refine_diff_density_rms    0.107 
