# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2020

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_abcm
_database_code_depnum_ccdc_archive 'CCDC 1504482'
loop_
_audit_author_name
_audit_author_address
'Dharmendra kumar gupta'
;Indian Institute of technology
India
;
_audit_update_record             
;
2019-12-08 deposited with the CCDC.	2020-01-23 downloaded from the CCDC.
;

_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H15 Cl3 N2 O4 S'
_chemical_formula_sum            'C13 H15 Cl3 N2 O4 S'
_chemical_formula_weight         401.68

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'
S S 0.1246 0.1234 '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                   8.1177(13)
_cell_length_b                   13.574(2)
_cell_length_c                   16.277(3)
_cell_angle_alpha                107.443(3)
_cell_angle_beta                 90.128(3)
_cell_angle_gamma                90.166(3)
_cell_volume                     1711.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    273(2)
_cell_measurement_reflns_used    4328
_cell_measurement_theta_min      2.33
_cell_measurement_theta_max      23.96

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_crystal_density_meas      1.559
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824.0
_exptl_absorpt_coefficient_mu    0.677
_exptl_absorpt_correction_T_min  0.827
_exptl_absorpt_correction_T_max  0.867
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      273(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16573
_diffrn_reflns_av_R_equivalents  0.0303
_diffrn_reflns_av_sigmaI/netI    0.0379
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.31
_diffrn_reflns_theta_max         25.00
_reflns_number_total             6043
_reflns_number_gt                5251
_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)+(0.0764P)²+4.5969P] 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     SHELXL
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         6029
_refine_ls_number_parameters     418
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0968
_refine_ls_R_factor_gt           0.0849
_refine_ls_wR_factor_ref         0.2071
_refine_ls_wR_factor_gt          0.2003
_refine_ls_goodness_of_fit_ref   1.191
_refine_ls_restrained_S_all      1.191
_refine_ls_shift/su_max          0.10
_refine_ls_shift/su_mean         0.10

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
S3 S 0.70090(16) 0.71787(9) 0.32998(8) 0.0343(3) Uani 1 1 d . . .
S2 S 0.19839(15) 0.78331(10) 0.16943(8) 0.0346(3) Uani 1 1 d . . .
Cl1 Cl 0.54162(18) 0.42825(13) 0.09045(9) 0.0538(4) Uani 1 1 d . . .
Cl5 Cl 0.0455(2) 1.07533(15) 0.40902(11) 0.0667(5) Uani 1 1 d . . .
Cl2 Cl 0.6489(2) 0.31288(12) 0.20366(12) 0.0667(5) Uani 1 1 d . . .
Cl3 Cl 1.1199(2) 0.44605(18) 0.08107(12) 0.0764(6) Uani 1 1 d . . .
Cl6 Cl 0.1540(3) 1.18906(12) 0.29655(13) 0.0748(6) Uani 1 1 d . . .
Cl4 Cl 0.6209(2) 1.0532(2) 0.41877(13) 0.0871(7) Uani 1 1 d . . .
N1 N 0.6747(5) 0.6132(3) 0.2479(3) 0.0318(9) Uani 1 1 d . . .
C5 C 0.5974(6) 0.5207(4) 0.2627(3) 0.0341(11) Uani 1 1 d . . .
H5 H 0.6437 0.5106 0.3153 0.041 Uiso 1 1 calc R . .
C6 C 0.1007(6) 0.9814(4) 0.2356(3) 0.0377(12) Uani 1 1 d . . .
H6 H 0.1463 0.9907 0.1827 0.045 Uiso 1 1 calc R . .
N3 N 0.1746(5) 0.8885(3) 0.2509(3) 0.0352(10) Uani 1 1 d . . .
C1 C 0.8597(6) 0.6934(4) 0.3949(3) 0.0301(10) Uani 1 1 d . . .
O5 O 0.2496(5) 0.7061(3) 0.2068(3) 0.0506(10) Uani 1 1 d . . .
O1 O 0.7563(5) 0.7951(3) 0.2937(3) 0.0517(10) Uani 1 1 d . . .
O2 O 0.5512(5) 0.7326(3) 0.3781(3) 0.0509(10) Uani 1 1 d . . .
O6 O 0.0498(5) 0.7703(3) 0.1203(3) 0.0504(10) Uani 1 1 d . . .
C7 C 0.3591(6) 0.8054(4) 0.1046(3) 0.0319(11) Uani 1 1 d . . .
C8 C 0.3269(7) 0.8531(4) 0.0423(3) 0.0382(12) Uani 1 1 d . . .
H8 H 0.2207 0.8744 0.0347 0.046 Uiso 1 1 calc R . .
C9 C 0.6610(7) 0.4349(4) 0.1843(3) 0.0381(12) Uani 1 1 d . . .
C10 C 0.8364(7) 0.4676(4) 0.1720(3) 0.0420(13) Uani 1 1 d . . .
H10 H 0.9047 0.4582 0.2188 0.050 Uiso 1 1 calc R . .
C11 C 0.8233(7) 0.6460(4) 0.4571(3) 0.0370(12) Uani 1 1 d . . .
H11 H 0.7161 0.6251 0.4634 0.044 Uiso 1 1 calc R . .
C2 C 1.0173(6) 0.7270(4) 0.3857(3) 0.0398(12) Uani 1 1 d . . .
H2 H 1.0402 0.7600 0.3445 0.048 Uiso 1 1 calc R . .
N4 N -0.1576(7) 1.0368(5) 0.1779(4) 0.0642(15) Uani 1 1 d . . .
C12 C 0.8148(7) 0.5824(4) 0.1864(4) 0.0419(13) Uani 1 1 d . . .
H12A H 0.9142 0.6199 0.2107 0.050 Uiso 1 1 calc R . .
H12B H 0.7895 0.5962 0.1327 0.050 Uiso 1 1 calc R . .
C13 C 0.5164(6) 0.7735(4) 0.1157(3) 0.0375(12) Uani 1 1 d . . .
H13 H 0.5373 0.7417 0.1579 0.045 Uiso 1 1 calc R . .
N2 N 0.3399(7) 0.4690(4) 0.3240(4) 0.0562(14) Uani 1 1 d . . .
C14 C 0.3122(7) 0.9186(4) 0.3144(4) 0.0450(13) Uani 1 1 d . . .
H14A H 0.4114 0.8805 0.2917 0.054 Uiso 1 1 calc R . .
H14B H 0.2834 0.9052 0.3679 0.054 Uiso 1 1 calc R . .
C15 C 0.1669(8) 1.0668(4) 0.3140(4) 0.0502(15) Uani 1 1 d . . .
C16 C 1.1074(7) 0.6631(4) 0.5017(4) 0.0470(14) Uani 1 1 d . . .
C17 C 0.4111(6) 0.5319(4) 0.2722(4) 0.0410(12) Uani 1 1 d . . .
H17A H 0.3847 0.6040 0.2995 0.049 Uiso 1 1 calc R . .
H17B H 0.3608 0.5113 0.2155 0.049 Uiso 1 1 calc R . .
C18 C 0.9475(8) 0.6302(4) 0.5095(4) 0.0482(14) Uani 1 1 d . . .
H18 H 0.9240 0.5972 0.5506 0.058 Uiso 1 1 calc R . .
C19 C 0.6124(8) 0.8367(4) 0.0020(4) 0.0490(15) Uani 1 1 d . . .
C20 C 0.4525(8) 0.8685(4) -0.0081(4) 0.0493(15) Uani 1 1 d . . .
H20 H 0.4311 0.9008 -0.0499 0.059 Uiso 1 1 calc R . .
C21 C 0.3375(8) 1.0331(5) 0.3286(4) 0.0540(15) Uani 1 1 d . . .
H21 H 0.4075 1.0410 0.2820 0.065 Uiso 1 1 calc R . .
C3 C 1.1406(7) 0.7108(5) 0.4391(4) 0.0450(14) Uani 1 1 d . . .
H3 H 1.2475 0.7323 0.4330 0.054 Uiso 1 1 calc R . .
C22 C 0.6421(7) 0.7886(4) 0.0647(4) 0.0438(13) Uani 1 1 d . . .
H22 H 0.7479 0.7664 0.0721 0.053 Uiso 1 1 calc R . .
C23 C 0.9128(7) 0.4076(5) 0.0873(4) 0.0553(16) Uani 1 1 d . . .
H23A H 0.8499 0.4191 0.0402 0.066 Uiso 1 1 calc R . .
H23B H 0.9088 0.3344 0.0815 0.066 Uiso 1 1 calc R . .
C24 C 0.4163(9) 1.0944(6) 0.4137(5) 0.0660(19) Uani 1 1 d . . .
H24A H 0.3535 1.0845 0.4612 0.079 Uiso 1 1 calc R . .
H24B H 0.4154 1.1674 0.4185 0.079 Uiso 1 1 calc R . .
C25 C -0.0862(7) 0.9726(5) 0.2280(4) 0.0450(13) Uani 1 1 d . . .
H25A H -0.1161 0.9010 0.2006 0.054 Uiso 1 1 calc R . .
H25B H -0.1334 0.9933 0.2853 0.054 Uiso 1 1 calc R . .
O4 O 0.4133(7) 0.4603(6) 0.3854(4) 0.095(2) Uani 1 1 d . . .
O3 O 0.2038(8) 0.4336(6) 0.3025(5) 0.116(3) Uani 1 1 d . . .
O8 O -0.2923(9) 1.0728(6) 0.2004(6) 0.130(3) Uani 1 1 d . . .
O7 O -0.0866(8) 1.0464(6) 0.1169(4) 0.105(2) Uani 1 1 d . . .
C28 C 1.2414(10) 0.6505(6) 0.5619(6) 0.082(2) Uani 1 1 d . . .
H28A H 1.3269 0.6075 0.5294 0.123 Uiso 1 1 calc R . .
H28B H 1.1963 0.6189 0.6024 0.123 Uiso 1 1 calc R . .
H28C H 1.2863 0.7170 0.5923 0.123 Uiso 1 1 calc R . .
C4 C 0.7488(10) 0.8500(7) -0.0573(6) 0.083(2) Uani 1 1 d . . .
H4A H 0.8260 0.7943 -0.0659 0.125 Uiso 1 1 calc R . .
H4B H 0.8044 0.9145 -0.0318 0.125 Uiso 1 1 calc R . .
H4C H 0.7025 0.8495 -0.1117 0.125 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
S3 O1 1.421(4) . ?
S3 O2 1.429(4) . ?
S3 N1 1.645(4) . ?
S3 C1 1.759(5) . ?
S2 O5 1.423(4) . ?
S2 O6 1.427(4) . ?
S2 N3 1.644(4) . ?
S2 C7 1.760(5) . ?
Cl1 C9 1.785(5) . ?
Cl5 C15 1.810(7) . ?
Cl2 C9 1.780(5) . ?
Cl3 C23 1.771(6) . ?
Cl6 C15 1.768(6) . ?
Cl4 C24 1.765(7) . ?
N1 C5 1.486(6) . ?
N1 C12 1.492(7) . ?
C5 C17 1.524(7) . ?
C5 C9 1.538(7) . ?
C6 N3 1.485(6) . ?
C6 C25 1.524(7) . ?
C6 C15 1.539(8) . ?
N3 C14 1.490(7) . ?
C1 C2 1.380(7) . ?
C1 C11 1.384(7) . ?
C7 C13 1.379(7) . ?
C7 C8 1.382(7) . ?
C8 C20 1.364(8) . ?
C9 C10 1.521(8) . ?
C10 C23 1.511(8) . ?
C10 C12 1.515(8) . ?
C11 C18 1.378(8) . ?
C2 C3 1.385(8) . ?
N4 O7 1.190(8) . ?
N4 O8 1.211(8) . ?
N4 C25 1.479(8) . ?
C13 C22 1.371(8) . ?
N2 O4 1.199(7) . ?
N2 O3 1.211(7) . ?
N2 C17 1.485(7) . ?
C14 C21 1.514(8) . ?
C15 C21 1.501(9) . ?
C16 C3 1.387(8) . ?
C16 C18 1.390(9) . ?
C16 C28 1.507(8) . ?
C19 C22 1.387(9) . ?
C19 C20 1.394(9) . ?
C19 C4 1.516(9) . ?
C21 C24 1.524(9) . ?

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
O1 S3 O2 119.8(3) . . ?
O1 S3 N1 105.5(2) . . ?
O2 S3 N1 106.5(2) . . ?
O1 S3 C1 108.3(2) . . ?
O2 S3 C1 108.4(2) . . ?
N1 S3 C1 107.8(2) . . ?
O5 S2 O6 120.3(3) . . ?
O5 S2 N3 105.3(2) . . ?
O6 S2 N3 106.3(2) . . ?
O5 S2 C7 108.6(2) . . ?
O6 S2 C7 107.7(2) . . ?
N3 S2 C7 108.1(2) . . ?
C5 N1 C12 110.5(4) . . ?
C5 N1 S3 119.2(3) . . ?
C12 N1 S3 116.7(3) . . ?
N1 C5 C17 111.7(4) . . ?
N1 C5 C9 100.9(4) . . ?
C17 C5 C9 116.7(4) . . ?
N3 C6 C25 111.6(4) . . ?
N3 C6 C15 100.8(4) . . ?
C25 C6 C15 115.6(5) . . ?
C6 N3 C14 110.5(4) . . ?
C6 N3 S2 119.3(3) . . ?
C14 N3 S2 117.4(3) . . ?
C2 C1 C11 121.2(5) . . ?
C2 C1 S3 119.0(4) . . ?
C11 C1 S3 119.7(4) . . ?
C13 C7 C8 120.4(5) . . ?
C13 C7 S2 119.5(4) . . ?
C8 C7 S2 120.1(4) . . ?
C20 C8 C7 119.4(5) . . ?
C10 C9 C5 104.4(4) . . ?
C10 C9 Cl2 113.4(4) . . ?
C5 C9 Cl2 110.3(4) . . ?
C10 C9 Cl1 109.6(4) . . ?
C5 C9 Cl1 111.0(4) . . ?
Cl2 C9 Cl1 108.2(3) . . ?
C23 C10 C12 116.0(5) . . ?
C23 C10 C9 114.1(5) . . ?
C12 C10 C9 101.3(4) . . ?
C18 C11 C1 119.3(5) . . ?
C1 C2 C3 118.8(5) . . ?
O7 N4 O8 123.9(7) . . ?
O7 N4 C25 119.9(6) . . ?
O8 N4 C25 116.1(6) . . ?
N1 C12 C10 105.2(4) . . ?
C22 C13 C7 120.1(5) . . ?
O4 N2 O3 124.2(6) . . ?
O4 N2 C17 119.8(6) . . ?
O3 N2 C17 115.8(5) . . ?
N3 C14 C21 105.1(4) . . ?
C21 C15 C6 105.1(5) . . ?
C21 C15 Cl6 115.3(4) . . ?
C6 C15 Cl6 110.9(4) . . ?
C21 C15 Cl5 108.3(5) . . ?
C6 C15 Cl5 111.0(4) . . ?
Cl6 C15 Cl5 106.3(3) . . ?
C3 C16 C18 118.9(5) . . ?
C3 C16 C28 120.4(6) . . ?
C18 C16 C28 120.7(6) . . ?
N2 C17 C5 112.7(5) . . ?
C11 C18 C16 120.7(5) . . ?
C22 C19 C20 118.6(5) . . ?
C22 C19 C4 120.9(6) . . ?
C20 C19 C4 120.4(6) . . ?
C8 C20 C19 121.1(5) . . ?
C15 C21 C14 101.7(5) . . ?
C15 C21 C24 114.7(5) . . ?
C14 C21 C24 116.8(6) . . ?
C2 C3 C16 121.1(5) . . ?
C13 C22 C19 120.4(5) . . ?
C10 C23 Cl3 110.9(4) . . ?
C21 C24 Cl4 109.9(5) . . ?
N4 C25 C6 113.0(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.958
_refine_diff_density_min         -0.693
_refine_diff_density_rms         0.091
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_dkg1m
_database_code_depnum_ccdc_archive 'CCDC 1504483'
loop_
_audit_author_name
_audit_author_address
'Dharmendra kumar gupta'
;Indian Institute of technology
India
;
_audit_update_record             
;
2019-12-08 deposited with the CCDC.	2020-01-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H12 Cl3 N O2'
_chemical_formula_sum            'C13 H12 Cl3 N O2'
_chemical_formula_weight         320.59

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   P21/c
_symmetry_space_group_name_Hall  -P2ybc

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                   12.302(3)
_cell_length_b                   13.884(3)
_cell_length_c                   8.368(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.188(4)
_cell_angle_gamma                90.00
_cell_volume                     1402.1(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    2237
_cell_measurement_theta_min      0.895
_cell_measurement_theta_max      0.923

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.171
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.124
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.519
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.649
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.895
_exptl_absorpt_correction_T_max  0.923
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13072
_diffrn_reflns_av_R_equivalents  0.0478
_diffrn_reflns_av_sigmaI/netI    0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.69
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2462
_reflns_number_gt                2237
_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)+(0.0507P)²+3.0422P] where P=(Fo²+2Fc²)/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         2462
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0976
_refine_ls_R_factor_gt           0.0861
_refine_ls_wR_factor_ref         0.1723
_refine_ls_wR_factor_gt          0.1667
_refine_ls_goodness_of_fit_ref   1.275
_refine_ls_restrained_S_all      1.275
_refine_ls_shift/su_max          0.005
_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 0.24480(13) 1.04951(9) 0.16765(17) 0.0496(4) Uani 1 1 d . . .
Cl2 Cl 0.10849(11) 0.90142(11) -0.01181(16) 0.0503(4) Uani 1 1 d . . .
Cl3 Cl 0.55101(11) 0.86562(12) 0.06411(18) 0.0560(4) Uani 1 1 d . . .
O1 O 0.3783(4) 0.9282(4) 0.6463(5) 0.0724(14) Uani 1 1 d . . .
O2 O 0.1375(3) 0.8529(3) 0.5221(4) 0.0449(9) Uani 1 1 d . . .
N1 N 0.3489(3) 0.8655(3) 0.3816(5) 0.0389(10) Uani 1 1 d . . .
C1 C 0.3228(4) 0.9064(4) 0.5169(6) 0.0438(13) Uani 1 1 d . . .
C2 C 0.1994(4) 0.9119(4) 0.4366(6) 0.0383(12) Uani 1 1 d . . .
H2 H 0.1709 0.9778 0.4192 0.046 Uiso 1 1 calc R . .
C3 C 0.2370(4) 0.8669(4) 0.2848(6) 0.0322(11) Uani 1 1 d . . .
H3 H 0.2077 0.8016 0.2627 0.039 Uiso 1 1 calc R . .
C4 C 0.2357(4) 0.9226(4) 0.1279(6) 0.0360(12) Uani 1 1 d . . .
C5 C 0.3311(4) 0.8916(4) 0.0497(6) 0.0370(12) Uani 1 1 d . . .
H5A H 0.3303 0.9292 -0.0482 0.044 Uiso 1 1 calc R . .
H5B H 0.3217 0.8244 0.0182 0.044 Uiso 1 1 calc R . .
C6 C 0.4426(4) 0.9044(4) 0.1644(6) 0.0386(12) Uani 1 1 d . . .
H6 H 0.4532 0.9729 0.1915 0.046 Uiso 1 1 calc R . .
C7 C 0.4494(4) 0.8470(4) 0.3223(6) 0.0463(14) Uani 1 1 d . . .
H7A H 0.4562 0.7787 0.3016 0.056 Uiso 1 1 calc R . .
H7B H 0.5134 0.8671 0.4023 0.056 Uiso 1 1 calc R . .
C8 C 0.0232(4) 0.8563(3) 0.4783(6) 0.0347(11) Uani 1 1 d . . .
C9 C -0.0335(4) 0.9057(4) 0.3452(6) 0.0412(12) Uani 1 1 d . . .
H9 H 0.0043 0.9413 0.2792 0.049 Uiso 1 1 calc R . .
C10 C -0.1488(5) 0.9013(4) 0.3115(7) 0.0481(14) Uani 1 1 d . . .
H10 H -0.1886 0.9338 0.2217 0.058 Uiso 1 1 calc R . .
C11 C -0.2041(5) 0.8492(4) 0.4105(7) 0.0494(14) Uani 1 1 d . . .
H11 H -0.2810 0.8461 0.3866 0.059 Uiso 1 1 calc R . .
C12 C -0.1468(4) 0.8019(4) 0.5434(7) 0.0473(14) Uani 1 1 d . . .
H12 H -0.1846 0.7672 0.6105 0.057 Uiso 1 1 calc R . .
C13 C -0.0338(4) 0.8057(4) 0.5775(6) 0.0405(13) Uani 1 1 d . . .
H13 H 0.0051 0.7739 0.6686 0.049 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 C4 1.792(5) . ?
Cl2 C4 1.787(5) . ?
Cl3 C6 1.791(5) . ?
O1 C1 1.202(6) . ?
O2 C8 1.382(6) . ?
O2 C2 1.405(6) . ?
N1 C1 1.359(7) . ?
N1 C7 1.442(6) . ?
N1 C3 1.456(6) . ?
C1 C2 1.538(7) . ?
C2 C3 1.564(7) . ?
C2 H2 0.9800 . ?
C3 C4 1.521(7) . ?
C3 H3 0.9800 . ?
C4 C5 1.513(7) . ?
C5 C6 1.525(7) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.532(7) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C13 1.378(7) . ?
C8 C9 1.378(7) . ?
C9 C10 1.392(7) . ?
C9 H9 0.9300 . ?
C10 C11 1.375(8) . ?
C10 H10 0.9300 . ?
C11 C12 1.364(8) . ?
C11 H11 0.9300 . ?
C12 C13 1.365(7) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?

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
C8 O2 C2 118.0(4) . . ?
C1 N1 C7 135.9(4) . . ?
C1 N1 C3 96.2(4) . . ?
C7 N1 C3 126.3(4) . . ?
O1 C1 N1 132.2(5) . . ?
O1 C1 C2 136.1(5) . . ?
N1 C1 C2 91.7(4) . . ?
O2 C2 C1 109.6(4) . . ?
O2 C2 C3 117.1(4) . . ?
C1 C2 C3 85.0(4) . . ?
O2 C2 H2 113.9 . . ?
C1 C2 H2 113.9 . . ?
C3 C2 H2 113.9 . . ?
N1 C3 C4 109.7(4) . . ?
N1 C3 C2 87.1(3) . . ?
C4 C3 C2 122.9(4) . . ?
N1 C3 H3 111.5 . . ?
C4 C3 H3 111.5 . . ?
C2 C3 H3 111.5 . . ?
C5 C4 C3 110.4(4) . . ?
C5 C4 Cl2 108.9(3) . . ?
C3 C4 Cl2 110.0(3) . . ?
C5 C4 Cl1 109.6(3) . . ?
C3 C4 Cl1 110.5(3) . . ?
Cl2 C4 Cl1 107.4(3) . . ?
C4 C5 C6 111.9(4) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C5 C6 C7 111.9(4) . . ?
C5 C6 Cl3 109.3(3) . . ?
C7 C6 Cl3 109.1(4) . . ?
C5 C6 H6 108.8 . . ?
C7 C6 H6 108.8 . . ?
Cl3 C6 H6 108.8 . . ?
N1 C7 C6 107.3(4) . . ?
N1 C7 H7A 110.3 . . ?
C6 C7 H7A 110.3 . . ?
N1 C7 H7B 110.3 . . ?
C6 C7 H7B 110.3 . . ?
H7A C7 H7B 108.5 . . ?
C13 C8 C9 120.2(5) . . ?
C13 C8 O2 115.7(4) . . ?
C9 C8 O2 124.1(4) . . ?
C8 C9 C10 118.6(5) . . ?
C8 C9 H9 120.7 . . ?
C10 C9 H9 120.7 . . ?
C11 C10 C9 120.3(5) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C12 C11 C10 120.5(5) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.7(5) . . ?
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.7(5) . . ?
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?

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
C7 N1 C1 O1 -13.4(11) . . . . ?
C3 N1 C1 O1 -178.7(7) . . . . ?
C7 N1 C1 C2 166.6(6) . . . . ?
C3 N1 C1 C2 1.3(4) . . . . ?
C8 O2 C2 C1 173.4(4) . . . . ?
C8 O2 C2 C3 -92.2(5) . . . . ?
O1 C1 C2 O2 -64.2(9) . . . . ?
N1 C1 C2 O2 115.8(4) . . . . ?
O1 C1 C2 C3 178.8(7) . . . . ?
N1 C1 C2 C3 -1.2(4) . . . . ?
C1 N1 C3 C4 122.7(4) . . . . ?
C7 N1 C3 C4 -44.6(7) . . . . ?
C1 N1 C3 C2 -1.3(4) . . . . ?
C7 N1 C3 C2 -168.7(5) . . . . ?
O2 C2 C3 N1 -108.3(4) . . . . ?
C1 C2 C3 N1 1.1(4) . . . . ?
O2 C2 C3 C4 140.0(5) . . . . ?
C1 C2 C3 C4 -110.6(5) . . . . ?
N1 C3 C4 C5 46.3(5) . . . . ?
C2 C3 C4 C5 146.0(4) . . . . ?
N1 C3 C4 Cl2 166.5(3) . . . . ?
C2 C3 C4 Cl2 -93.8(5) . . . . ?
N1 C3 C4 Cl1 -75.1(4) . . . . ?
C2 C3 C4 Cl1 24.6(6) . . . . ?
C3 C4 C5 C6 -57.2(5) . . . . ?
Cl2 C4 C5 C6 -178.1(3) . . . . ?
Cl1 C4 C5 C6 64.8(5) . . . . ?
C4 C5 C6 C7 58.7(6) . . . . ?
C4 C5 C6 Cl3 179.6(3) . . . . ?
C1 N1 C7 C6 -117.4(6) . . . . ?
C3 N1 C7 C6 44.4(7) . . . . ?
C5 C6 C7 N1 -47.3(6) . . . . ?
Cl3 C6 C7 N1 -168.4(4) . . . . ?
C2 O2 C8 C13 -172.9(4) . . . . ?
C2 O2 C8 C9 7.3(7) . . . . ?
C13 C8 C9 C10 -1.6(8) . . . . ?
O2 C8 C9 C10 178.3(5) . . . . ?
C8 C9 C10 C11 0.5(8) . . . . ?
C9 C10 C11 C12 0.6(9) . . . . ?
C10 C11 C12 C13 -0.6(9) . . . . ?
C11 C12 C13 C8 -0.5(8) . . . . ?
C9 C8 C13 C12 1.6(8) . . . . ?
O2 C8 C13 C12 -178.3(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.407
_refine_diff_density_min         -0.268
_refine_diff_density_rms         0.074
