# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_7

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H13 Cl2 N3 O3 S'
_chemical_formula_sum            'C15 H13 Cl2 N3 O3 S'
_chemical_formula_weight         386.24

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'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.9294(12)
_cell_length_b                   12.763(2)
_cell_length_c                   16.761(3)
_cell_angle_alpha                96.664(17)
_cell_angle_beta                 99.981(17)
_cell_angle_gamma                97.378(14)
_cell_volume                     1640.1(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    7125
_cell_measurement_theta_min      2.6
_cell_measurement_theta_max      27.5

_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.62
_exptl_crystal_size_min          0.34
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.564
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             792
_exptl_absorpt_coefficient_mu    0.543
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2007)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15975
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         5.16
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5632
_reflns_number_gt                4964
_reflns_threshold_expression     >2sigma(I)


_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)+(0.0299P)²+1.0816P] where P=(Fo²+2Fc²)/3'

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5632
_refine_ls_number_parameters     445
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0735
_refine_ls_wR_factor_gt          0.0682
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_restrained_S_all      1.086
_refine_ls_shift/su_max          0.001
_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
N1 N 0.54097(19) -0.06927(12) 0.15880(9) 0.0245(3) Uani 1 1 d . . .
N2 N 0.62318(18) -0.03015(12) 0.23788(9) 0.0216(3) Uani 1 1 d . . .
C3 C 0.5027(2) -0.04490(13) 0.28295(10) 0.0175(3) Uani 1 1 d . . .
C4 C 0.1732(2) -0.12603(13) 0.25059(11) 0.0211(4) Uani 1 1 d . . .
C5 C 0.0427(2) -0.17038(15) 0.18499(12) 0.0283(4) Uani 1 1 d . . .
H5 H -0.0709 -0.1924 0.1938 0.034 Uiso 1 1 calc R . .
C6 C 0.0778(3) -0.18312(16) 0.10491(12) 0.0346(5) Uani 1 1 d . . .
H6 H -0.0143 -0.2143 0.0611 0.042 Uiso 1 1 calc R . .
C7 C 0.2378(3) -0.15281(16) 0.08705(12) 0.0320(4) Uani 1 1 d . . .
H7 H 0.2582 -0.1620 0.0326 0.038 Uiso 1 1 calc R . .
C8 C 0.3702(2) -0.10727(14) 0.15414(11) 0.0234(4) Uani 1 1 d . . .
C9 C 0.3399(2) -0.09350(13) 0.23459(10) 0.0197(3) Uani 1 1 d . . .
C10 C 0.6332(3) -0.05659(17) 0.09204(12) 0.0324(4) Uani 1 1 d . . .
H10A H 0.5807 -0.1115 0.0454 0.049 Uiso 1 1 calc R . .
H10B H 0.7549 -0.0640 0.1100 0.049 Uiso 1 1 calc R . .
H10C H 0.6261 0.0142 0.0757 0.049 Uiso 1 1 calc R . .
N11 N 0.53846(19) -0.01745(11) 0.36867(9) 0.0187(3) Uani 1 1 d . . .
H11 H 0.466(3) -0.0353(16) 0.3937(13) 0.023(5) Uiso 1 1 d . . .
S12 S 0.66845(5) 0.08859(3) 0.41748(2) 0.01719(10) Uani 1 1 d . . .
O13 O 0.65214(16) 0.09178(10) 0.50147(7) 0.0239(3) Uani 1 1 d . . .
O14 O 0.83530(15) 0.08802(10) 0.39646(8) 0.0263(3) Uani 1 1 d . . .
C15 C 0.5909(2) 0.20335(13) 0.38102(9) 0.0173(3) Uani 1 1 d . . .
C16 C 0.4259(2) 0.22825(13) 0.38694(10) 0.0195(3) Uani 1 1 d . . .
C17 C 0.3831(2) 0.32456(14) 0.36365(11) 0.0249(4) Uani 1 1 d . . .
C18 C 0.4992(3) 0.39360(15) 0.33372(12) 0.0301(4) Uani 1 1 d . . .
H18 H 0.4675 0.4584 0.3176 0.036 Uiso 1 1 calc R . .
C19 C 0.6605(3) 0.36783(15) 0.32742(11) 0.0299(4) Uani 1 1 d . . .
H19 H 0.7398 0.4147 0.3066 0.036 Uiso 1 1 calc R . .
C20 C 0.7071(2) 0.27330(14) 0.35158(10) 0.0232(4) Uani 1 1 d . . .
H20 H 0.8190 0.2563 0.3480 0.028 Uiso 1 1 calc R . .
Cl21 Cl 0.27674(5) 0.14353(3) 0.42242(3) 0.02677(11) Uani 1 1 d . . .
Cl22 Cl 0.18315(6) 0.36113(4) 0.37277(4) 0.04284(15) Uani 1 1 d . . .
O23 O 0.15945(15) -0.10902(10) 0.33047(7) 0.0244(3) Uani 1 1 d . . .
C24 C -0.0088(2) -0.13477(16) 0.35010(12) 0.0291(4) Uani 1 1 d . . .
H24A H -0.0896 -0.0937 0.3209 0.044 Uiso 1 1 calc R . .
H24B H -0.0014 -0.1169 0.4092 0.044 Uiso 1 1 calc R . .
H24C H -0.0503 -0.2112 0.3336 0.044 Uiso 1 1 calc R . .
N41 N 0.0961(2) 0.60548(12) 0.34952(9) 0.0244(3) Uani 1 1 d . . .
N42 N -0.01536(18) 0.56277(12) 0.27738(9) 0.0220(3) Uani 1 1 d . . .
C43 C 0.0814(2) 0.56651(13) 0.22034(10) 0.0174(3) Uani 1 1 d . . .
C44 C 0.4090(2) 0.63561(13) 0.22217(11) 0.0201(4) Uani 1 1 d . . .
C45 C 0.5609(2) 0.67758(15) 0.27646(12) 0.0279(4) Uani 1 1 d . . .
H45 H 0.6659 0.6918 0.2570 0.033 Uiso 1 1 calc R . .
C46 C 0.5599(3) 0.69936(16) 0.36104(12) 0.0334(5) Uani 1 1 d . . .
H46 H 0.6657 0.7290 0.3971 0.040 Uiso 1 1 calc R . .
C47 C 0.4138(3) 0.67988(15) 0.39363(12) 0.0310(4) Uani 1 1 d . . .
H47 H 0.4160 0.6958 0.4506 0.037 Uiso 1 1 calc R . .
C48 C 0.2603(2) 0.63501(13) 0.33798(11) 0.0220(4) Uani 1 1 d . . .
C49 C 0.2568(2) 0.61165(13) 0.25377(10) 0.0185(3) Uani 1 1 d . . .
C50 C 0.0358(3) 0.60949(18) 0.42676(12) 0.0360(5) Uani 1 1 d . . .
H50A H 0.0938 0.5621 0.4606 0.054 Uiso 1 1 calc R . .
H50B H -0.0897 0.5863 0.4162 0.054 Uiso 1 1 calc R . .
H50C H 0.0625 0.6828 0.4555 0.054 Uiso 1 1 calc R . .
N51 N 0.01271(19) 0.53124(11) 0.13673(9) 0.0187(3) Uani 1 1 d . . .
H51 H 0.075(3) 0.5462(17) 0.1070(13) 0.026(6) Uiso 1 1 d . . .
S52 S -0.11834(5) 0.41962(3) 0.10229(3) 0.01832(10) Uani 1 1 d . . .
O53 O -0.26933(15) 0.42053(10) 0.13798(8) 0.0281(3) Uani 1 1 d . . .
O54 O -0.13582(16) 0.40802(10) 0.01509(7) 0.0273(3) Uani 1 1 d . . .
C55 C -0.0168(2) 0.31200(13) 0.13858(10) 0.0168(3) Uani 1 1 d . . .
C56 C 0.1449(2) 0.29122(13) 0.12335(10) 0.0181(3) Uani 1 1 d . . .
C57 C 0.2096(2) 0.20331(14) 0.15180(11) 0.0228(4) Uani 1 1 d . . .
C58 C 0.1159(3) 0.13608(15) 0.19349(12) 0.0286(4) Uani 1 1 d . . .
H58 H 0.1619 0.0763 0.2123 0.034 Uiso 1 1 calc R . .
C59 C -0.0442(3) 0.15641(15) 0.20743(12) 0.0296(4) Uani 1 1 d . . .
H59 H -0.1088 0.1104 0.2357 0.036 Uiso 1 1 calc R . .
C60 C -0.1105(2) 0.24417(14) 0.18007(11) 0.0225(4) Uani 1 1 d . . .
H60 H -0.2207 0.2580 0.1897 0.027 Uiso 1 1 calc R . .
Cl61 Cl 0.26311(6) 0.37195(4) 0.07063(3) 0.02983(12) Uani 1 1 d . . .
Cl62 Cl 0.41118(6) 0.17551(4) 0.13624(3) 0.03614(13) Uani 1 1 d . . .
O63 O 0.38824(15) 0.61549(10) 0.13951(7) 0.0243(3) Uani 1 1 d . . .
C64 C 0.5362(2) 0.63910(16) 0.10293(13) 0.0311(4) Uani 1 1 d . . .
H64A H 0.5839 0.7149 0.1181 0.047 Uiso 1 1 calc R . .
H64B H 0.5019 0.6227 0.0433 0.047 Uiso 1 1 calc R . .
H64C H 0.6243 0.5958 0.1223 0.047 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
N1 C8 1.364(2) . yes
N1 N2 1.376(2) . yes
N1 C10 1.452(2) . yes
N2 C3 1.325(2) . yes
C3 N11 1.409(2) . yes
C3 C9 1.423(2) . yes
C4 O23 1.357(2) . yes
C4 C5 1.382(2) . yes
C4 C9 1.414(2) . yes
C5 C6 1.413(3) . yes
C5 H5 0.9500 . ?
C6 C7 1.372(3) . yes
C6 H6 0.9500 . ?
C7 C8 1.410(3) . yes
C7 H7 0.9500 . ?
C8 C9 1.406(2) . yes
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
N11 S12 1.6297(15) . yes
N11 H11 0.80(2) . ?
S12 O14 1.4276(13) . yes
S12 O13 1.4321(13) . yes
S12 C15 1.7905(17) . yes
C15 C20 1.392(2) . yes
C15 C16 1.402(2) . yes
C16 C17 1.397(2) . yes
C16 Cl21 1.7282(17) . yes
C17 C18 1.389(3) . yes
C17 Cl22 1.7355(19) . yes
C18 C19 1.379(3) . yes
C18 H18 0.9500 . ?
C19 C20 1.390(3) . yes
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
O23 C24 1.436(2) . yes
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
N41 C48 1.361(2) . yes
N41 N42 1.376(2) . yes
N41 C50 1.454(2) . yes
N42 C43 1.327(2) . yes
C43 N51 1.410(2) . yes
C43 C49 1.425(2) . yes
C44 O63 1.356(2) . yes
C44 C45 1.381(3) . yes
C44 C49 1.412(2) . yes
C45 C46 1.414(3) . yes
C45 H45 0.9500 . ?
C46 C47 1.370(3) . yes
C46 H46 0.9500 . ?
C47 C48 1.408(3) . yes
C47 H47 0.9500 . ?
C48 C49 1.403(2) . yes
C50 H50A 0.9800 . ?
C50 H50B 0.9800 . ?
C50 H50C 0.9800 . ?
N51 S52 1.6320(15) . yes
N51 H51 0.79(2) . ?
S52 O53 1.4289(13) . yes
S52 O54 1.4324(13) . yes
S52 C55 1.7924(17) . yes
C55 C60 1.392(2) . yes
C55 C56 1.402(2) . yes
C56 C57 1.392(2) . yes
C56 Cl61 1.7237(16) . yes
C57 C58 1.390(3) . yes
C57 Cl62 1.7369(18) . yes
C58 C59 1.381(3) . yes
C58 H58 0.9500 . ?
C59 C60 1.389(3) . yes
C59 H59 0.9500 . ?
C60 H60 0.9500 . ?
O63 C64 1.430(2) . yes
C64 H64A 0.9800 . ?
C64 H64B 0.9800 . ?
C64 H64C 0.9800 . ?

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 N1 N2 111.95(14) . . yes
C8 N1 C10 128.08(15) . . yes
N2 N1 C10 119.62(15) . . yes
C3 N2 N1 105.30(14) . . yes
N2 C3 N11 122.41(15) . . yes
N2 C3 C9 111.87(15) . . yes
N11 C3 C9 125.69(15) . . yes
O23 C4 C5 126.92(16) . . yes
O23 C4 C9 115.09(14) . . yes
C5 C4 C9 117.99(17) . . yes
C4 C5 C6 120.20(18) . . yes
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 123.47(17) . . yes
C7 C6 H6 118.3 . . ?
C5 C6 H6 118.3 . . ?
C6 C7 C8 116.10(18) . . yes
C6 C7 H7 121.9 . . ?
C8 C7 H7 121.9 . . ?
N1 C8 C9 106.42(15) . . yes
N1 C8 C7 131.68(17) . . yes
C9 C8 C7 121.91(17) . . yes
C8 C9 C4 120.33(16) . . yes
C8 C9 C3 104.46(15) . . yes
C4 C9 C3 135.21(16) . . yes
N1 C10 H10A 109.5 . . ?
N1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C3 N11 S12 124.20(12) . . yes
C3 N11 H11 118.6(15) . . ?
S12 N11 H11 111.1(15) . . ?
O14 S12 O13 119.36(8) . . yes
O14 S12 N11 109.28(8) . . yes
O13 S12 N11 105.72(8) . . yes
O14 S12 C15 105.81(8) . . yes
O13 S12 C15 108.03(8) . . yes
N11 S12 C15 108.27(8) . . yes
C20 C15 C16 120.06(15) . . yes
C20 C15 S12 117.01(13) . . yes
C16 C15 S12 122.75(12) . . yes
C17 C16 C15 118.49(15) . . yes
C17 C16 Cl21 119.77(13) . . yes
C15 C16 Cl21 121.74(13) . . yes
C18 C17 C16 121.14(17) . . yes
C18 C17 Cl22 118.52(14) . . yes
C16 C17 Cl22 120.33(14) . . yes
C19 C18 C17 119.88(17) . . yes
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C18 C19 C20 119.97(17) . . yes
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C19 C20 C15 120.45(17) . . yes
C19 C20 H20 119.8 . . ?
C15 C20 H20 119.8 . . ?
C4 O23 C24 117.70(14) . . yes
O23 C24 H24A 109.5 . . ?
O23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C48 N41 N42 112.10(14) . . yes
C48 N41 C50 127.46(16) . . yes
N42 N41 C50 120.35(15) . . yes
C43 N42 N41 104.96(14) . . yes
N42 C43 N51 122.36(15) . . yes
N42 C43 C49 112.08(15) . . yes
N51 C43 C49 125.54(15) . . yes
O63 C44 C45 126.62(16) . . yes
O63 C44 C49 115.05(14) . . yes
C45 C44 C49 118.33(16) . . yes
C44 C45 C46 119.95(17) . . yes
C44 C45 H45 120.0 . . ?
C46 C45 H45 120.0 . . ?
C47 C46 C45 123.31(17) . . yes
C47 C46 H46 118.3 . . ?
C45 C46 H46 118.3 . . ?
C46 C47 C48 116.33(17) . . yes
C46 C47 H47 121.8 . . ?
C48 C47 H47 121.8 . . ?
N41 C48 C49 106.71(15) . . yes
N41 C48 C47 131.42(17) . . yes
C49 C48 C47 121.87(17) . . yes
C48 C49 C44 120.15(16) . . yes
C48 C49 C43 104.15(15) . . yes
C44 C49 C43 135.70(16) . . yes
N41 C50 H50A 109.5 . . ?
N41 C50 H50B 109.5 . . ?
H50A C50 H50B 109.5 . . ?
N41 C50 H50C 109.5 . . ?
H50A C50 H50C 109.5 . . ?
H50B C50 H50C 109.5 . . ?
C43 N51 S52 124.02(12) . . yes
C43 N51 H51 114.7(16) . . ?
S52 N51 H51 112.7(15) . . ?
O53 S52 O54 119.55(8) . . yes
O53 S52 N51 108.83(8) . . yes
O54 S52 N51 105.50(8) . . yes
O53 S52 C55 105.65(8) . . yes
O54 S52 C55 108.40(8) . . yes
N51 S52 C55 108.58(7) . . yes
C60 C55 C56 119.97(15) . . yes
C60 C55 S52 116.82(13) . . yes
C56 C55 S52 123.13(12) . . yes
C57 C56 C55 118.61(15) . . yes
C57 C56 Cl61 120.03(13) . . yes
C55 C56 Cl61 121.36(13) . . yes
C58 C57 C56 121.20(16) . . yes
C58 C57 Cl62 118.38(14) . . yes
C56 C57 Cl62 120.43(13) . . yes
C59 C58 C57 119.84(17) . . yes
C59 C58 H58 120.1 . . ?
C57 C58 H58 120.1 . . ?
C58 C59 C60 119.87(16) . . yes
C58 C59 H59 120.1 . . ?
C60 C59 H59 120.1 . . ?
C59 C60 C55 120.51(16) . . yes
C59 C60 H60 119.7 . . ?
C55 C60 H60 119.7 . . ?
C44 O63 C64 118.26(14) . . yes
O63 C64 H64A 109.5 . . ?
O63 C64 H64B 109.5 . . ?
H64A C64 H64B 109.5 . . ?
O63 C64 H64C 109.5 . . ?
H64A C64 H64C 109.5 . . ?
H64B C64 H64C 109.5 . . ?

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
C8 N1 N2 C3 0.58(18) . . . . yes
C10 N1 N2 C3 174.43(15) . . . . yes
N1 N2 C3 N11 178.14(14) . . . . yes
N1 N2 C3 C9 -0.13(18) . . . . yes
O23 C4 C5 C6 -179.85(17) . . . . yes
C9 C4 C5 C6 0.6(3) . . . . yes
C4 C5 C6 C7 -0.4(3) . . . . yes
C5 C6 C7 C8 0.2(3) . . . . yes
N2 N1 C8 C9 -0.79(19) . . . . yes
C10 N1 C8 C9 -173.99(17) . . . . yes
N2 N1 C8 C7 179.24(18) . . . . yes
C10 N1 C8 C7 6.0(3) . . . . yes
C6 C7 C8 N1 179.82(19) . . . . yes
C6 C7 C8 C9 -0.2(3) . . . . yes
N1 C8 C9 C4 -179.64(15) . . . . yes
C7 C8 C9 C4 0.3(3) . . . . yes
N1 C8 C9 C3 0.65(18) . . . . yes
C7 C8 C9 C3 -179.37(16) . . . . yes
O23 C4 C9 C8 179.84(14) . . . . yes
C5 C4 C9 C8 -0.6(2) . . . . yes
O23 C4 C9 C3 -0.6(3) . . . . yes
C5 C4 C9 C3 179.05(18) . . . . yes
N2 C3 C9 C8 -0.33(18) . . . . yes
N11 C3 C9 C8 -178.53(15) . . . . yes
N2 C3 C9 C4 -179.97(18) . . . . yes
N11 C3 C9 C4 1.8(3) . . . . yes
N2 C3 N11 S12 38.4(2) . . . . yes
C9 C3 N11 S12 -143.55(14) . . . . yes
C3 N11 S12 O14 -56.65(15) . . . . yes
C3 N11 S12 O13 173.71(13) . . . . yes
C3 N11 S12 C15 58.15(15) . . . . yes
O14 S12 C15 C20 -8.04(15) . . . . yes
O13 S12 C15 C20 120.87(13) . . . . yes
N11 S12 C15 C20 -125.09(13) . . . . yes
O14 S12 C15 C16 176.88(13) . . . . yes
O13 S12 C15 C16 -54.21(15) . . . . yes
N11 S12 C15 C16 59.83(15) . . . . yes
C20 C15 C16 C17 -0.7(2) . . . . yes
S12 C15 C16 C17 174.21(13) . . . . yes
C20 C15 C16 Cl21 179.54(13) . . . . yes
S12 C15 C16 Cl21 -5.5(2) . . . . yes
C15 C16 C17 C18 1.2(3) . . . . yes
Cl21 C16 C17 C18 -179.01(14) . . . . yes
C15 C16 C17 Cl22 -178.00(13) . . . . yes
Cl21 C16 C17 Cl22 1.7(2) . . . . yes
C16 C17 C18 C19 -0.7(3) . . . . yes
Cl22 C17 C18 C19 178.60(14) . . . . yes
C17 C18 C19 C20 -0.5(3) . . . . yes
C18 C19 C20 C15 1.0(3) . . . . yes
C16 C15 C20 C19 -0.4(3) . . . . yes
S12 C15 C20 C19 -175.59(14) . . . . yes
C5 C4 O23 C24 -3.0(2) . . . . yes
C9 C4 O23 C24 176.53(15) . . . . yes
C48 N41 N42 C43 -0.30(18) . . . . yes
C50 N41 N42 C43 -177.02(15) . . . . yes
N41 N42 C43 N51 -178.83(14) . . . . yes
N41 N42 C43 C49 -0.13(18) . . . . yes
O63 C44 C45 C46 176.61(16) . . . . yes
C49 C44 C45 C46 -2.5(3) . . . . yes
C44 C45 C46 C47 0.7(3) . . . . yes
C45 C46 C47 C48 0.6(3) . . . . yes
N42 N41 C48 C49 0.62(19) . . . . yes
C50 N41 C48 C49 177.04(16) . . . . yes
N42 N41 C48 C47 -178.94(18) . . . . yes
C50 N41 C48 C47 -2.5(3) . . . . yes
C46 C47 C48 N41 179.42(18) . . . . yes
C46 C47 C48 C49 -0.1(3) . . . . yes
N41 C48 C49 C44 178.70(14) . . . . yes
C47 C48 C49 C44 -1.7(2) . . . . yes
N41 C48 C49 C43 -0.64(17) . . . . yes
C47 C48 C49 C43 178.96(16) . . . . yes
O63 C44 C49 C48 -176.24(14) . . . . yes
C45 C44 C49 C48 2.9(2) . . . . yes
O63 C44 C49 C43 2.9(3) . . . . yes
C45 C44 C49 C43 -177.97(18) . . . . yes
N42 C43 C49 C48 0.49(18) . . . . yes
N51 C43 C49 C48 179.14(15) . . . . yes
N42 C43 C49 C44 -178.70(18) . . . . yes
N51 C43 C49 C44 0.0(3) . . . . yes
N42 C43 N51 S52 -45.3(2) . . . . yes
C49 C43 N51 S52 136.14(15) . . . . yes
C43 N51 S52 O53 58.57(15) . . . . yes
C43 N51 S52 O54 -172.00(13) . . . . yes
C43 N51 S52 C55 -55.97(15) . . . . yes
O53 S52 C55 C60 9.55(15) . . . . yes
O54 S52 C55 C60 -119.72(13) . . . . yes
N51 S52 C55 C60 126.14(13) . . . . yes
O53 S52 C55 C56 -173.78(13) . . . . yes
O54 S52 C55 C56 56.95(15) . . . . yes
N51 S52 C55 C56 -57.19(16) . . . . yes
C60 C55 C56 C57 -1.2(2) . . . . yes
S52 C55 C56 C57 -177.74(13) . . . . yes
C60 C55 C56 Cl61 178.85(13) . . . . yes
S52 C55 C56 Cl61 2.3(2) . . . . yes
C55 C56 C57 C58 0.9(3) . . . . yes
Cl61 C56 C57 C58 -179.10(14) . . . . yes
C55 C56 C57 Cl62 -178.78(12) . . . . yes
Cl61 C56 C57 Cl62 1.2(2) . . . . yes
C56 C57 C58 C59 -0.2(3) . . . . yes
Cl62 C57 C58 C59 179.50(15) . . . . yes
C57 C58 C59 C60 -0.3(3) . . . . yes
C58 C59 C60 C55 0.0(3) . . . . yes
C56 C55 C60 C59 0.7(3) . . . . yes
S52 C55 C60 C59 177.50(14) . . . . yes
C45 C44 O63 C64 0.1(2) . . . . yes
C49 C44 O63 C64 179.19(15) . . . . yes

_diffrn_measured_fraction_theta_max 0.971
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.971
_refine_diff_density_max         0.395
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.044
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.625
_exptl_absorpt_correction_T_max  0.822

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0.00 1.00 1.00 0.239
0.00 -1.00 2.00 0.451
0.00 -2.00 -1.00 0.216
0.00 0.00 -1.00 0.201
1.00 0.00 -1.00 0.574
-1.00 0.00 1.00 0.383

_exptl_crystal_description       wedge
_exptl_crystal_colour            colourless

_chemical_name_systematic        
;
2,3-Dichloro-N-[1-methyl-4-(methyloxy)-1H-indazol-3-yl]benzenesulfonamide
;

_computing_data_merging          'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.12 (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.12 (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.12 (Bruker, 2001)'
_computing_publication_material  'SHELXTL V6.12 (Bruker, 2001)'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed

_chemical_absolute_configuration .

_computing_data_collection       'COLLECT (Nonius, 1997-2000)'
_computing_cell_refinement       'DIRAX/LSQ (Duisenberg & Schreurs, 1989-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs, 1990-2000)'

_diffrn_measurement_device_type  'Nonius KappaCCD diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    '0.6 mm double-pinhole'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'normal focus sealed tube'
_database_code_depnum_ccdc_archive 'CCDC 975458'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_8

_audit_creation_method           SHELXL-97
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H14 Cl3 N3 O4 S'
_chemical_formula_sum            'C18 H14 Cl3 N3 O4 S'
_chemical_formula_weight         474.73

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'
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'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'


loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.0361(16)
_cell_length_b                   20.725(2)
_cell_length_c                   21.381(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.612(16)
_cell_angle_gamma                90.00
_cell_volume                     3977.5(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)

_exptl_crystal_size_max          0.64
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.586
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1936
_exptl_absorpt_coefficient_mu    0.597
_exptl_absorpt_process_details   'SADABS (Bruker, 2000)'

_exptl_special_details           
;
 Corrections were applied to the diffraction data for the presence of 
 non-merohedral twinning with the twin law 1 0 0 / 0 -1 0 / -0.47 0 -1.
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            21167
_diffrn_reflns_av_R_equivalents  0.067
_diffrn_reflns_av_sigmaI/netI    0.0726
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         1.92
_diffrn_reflns_theta_max         25.49
_reflns_number_total             7066
_reflns_number_gt                4994
_reflns_threshold_expression     >2sigma(I)


_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)+(0.0526P)²+11.0588P] where P=(Fo²+2Fc²)/3'

_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         7066
_refine_ls_number_parameters     541
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1002
_refine_ls_R_factor_gt           0.0615
_refine_ls_wR_factor_ref         0.1716
_refine_ls_wR_factor_gt          0.1476
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_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
N1 N 0.3860(6) 0.6298(3) -0.0597(2) 0.0219(12) Uani 1 1 d . . .
C2 C 0.3609(8) 0.6354(3) -0.1230(3) 0.0260(15) Uani 1 1 d . . .
H2 H 0.4396 0.6471 -0.1466 0.031 Uiso 1 1 calc R . .
C3 C 0.2225(8) 0.6240(3) -0.1525(3) 0.0192(14) Uani 1 1 d . . .
N4 N 0.1073(6) 0.6075(2) -0.1225(2) 0.0207(12) Uani 1 1 d . . .
C5 C 0.1302(7) 0.6026(3) -0.0606(3) 0.0133(12) Uani 1 1 d . . .
C6 C 0.2723(7) 0.6143(3) -0.0294(3) 0.0163(13) Uani 1 1 d . . .
Cl7 Cl 0.1903(2) 0.63377(9) -0.23318(7) 0.0344(4) Uani 1 1 d . . .
N8 N 0.0103(6) 0.5864(2) -0.0274(2) 0.0159(11) Uani 1 1 d . . .
H8 H 0.018(8) 0.594(3) 0.008(3) 0.02(2) Uiso 1 1 d . . .
S9 S -0.15496(17) 0.56593(7) -0.05949(7) 0.0150(3) Uani 1 1 d . . .
O10 O -0.2415(5) 0.55344(19) -0.00879(19) 0.0200(10) Uani 1 1 d . . .
O11 O -0.1379(5) 0.51639(19) -0.10436(19) 0.0211(10) Uani 1 1 d . . .
C12 C -0.2223(7) 0.6339(3) -0.1027(3) 0.0151(13) Uani 1 1 d . . .
C13 C -0.2532(7) 0.6919(3) -0.0744(3) 0.0174(13) Uani 1 1 d . . .
C14 C -0.2974(8) 0.7445(3) -0.1112(3) 0.0285(16) Uani 1 1 d . . .
C15 C -0.3151(8) 0.7394(3) -0.1762(3) 0.0290(17) Uani 1 1 d . . .
H15 H -0.3486 0.7754 -0.2015 0.035 Uiso 1 1 calc R . .
C16 C -0.2843(8) 0.6827(3) -0.2037(3) 0.0285(16) Uani 1 1 d . . .
H16 H -0.2950 0.6796 -0.2484 0.034 Uiso 1 1 calc R . .
C17 C -0.2375(7) 0.6291(3) -0.1680(3) 0.0228(15) Uani 1 1 d . . .
H17 H -0.2161 0.5897 -0.1878 0.027 Uiso 1 1 calc R . .
Cl18 Cl -0.2335(2) 0.70062(8) 0.00628(7) 0.0288(4) Uani 1 1 d . . .
Cl19 Cl -0.3276(3) 0.81787(10) -0.07734(10) 0.0641(8) Uani 1 1 d . . .
O20 O 0.2861(5) 0.6079(2) 0.03382(18) 0.0189(10) Uani 1 1 d . . .
C21 C 0.4386(7) 0.6139(3) 0.0643(3) 0.0222(15) Uani 1 1 d . . .
H21A H 0.4727 0.6592 0.0631 0.027 Uiso 1 1 calc R . .
H21B H 0.5068 0.5864 0.0428 0.027 Uiso 1 1 calc R . .
C22 C 0.4360(7) 0.5923(3) 0.1306(3) 0.0175(13) Uani 1 1 d . . .
C23 C 0.4910(8) 0.5306(3) 0.1461(3) 0.0269(16) Uani 1 1 d . . .
H23 H 0.5318 0.5052 0.1152 0.032 Uiso 1 1 calc R . .
C24 C 0.4863(8) 0.5064(3) 0.2059(3) 0.0324(18) Uani 1 1 d . . .
H24 H 0.5230 0.4643 0.2159 0.039 Uiso 1 1 calc R . .
C25 C 0.4285(9) 0.5432(3) 0.2515(3) 0.0319(18) Uani 1 1 d . . .
H25 H 0.4244 0.5262 0.2926 0.038 Uiso 1 1 calc R . .
C26 C 0.3770(8) 0.6046(3) 0.2370(3) 0.0289(17) Uani 1 1 d . . .
H26 H 0.3377 0.6298 0.2683 0.035 Uiso 1 1 calc R . .
C27 C 0.3817(7) 0.6301(3) 0.1774(3) 0.0206(14) Uani 1 1 d . . .
C28 C 0.3278(8) 0.6985(3) 0.1657(3) 0.0226(15) Uani 1 1 d . . .
H28A H 0.3909 0.7279 0.1939 0.027 Uiso 1 1 calc R . .
H28B H 0.3397 0.7106 0.1218 0.027 Uiso 1 1 calc R . .
O29 O 0.1752(5) 0.7073(2) 0.1760(2) 0.0201(10) Uani 1 1 d . . .
H29 H 0.130(8) 0.680(3) 0.166(3) 0.024 Uiso 1 1 d . . .
N31 N -0.3566(6) 0.7725(3) 0.1303(3) 0.0259(13) Uani 1 1 d . . .
C32 C -0.4191(8) 0.8204(4) 0.0931(3) 0.0308(17) Uani 1 1 d . . .
H32 H -0.5235 0.8208 0.0807 0.037 Uiso 1 1 calc R . .
C33 C -0.3296(8) 0.8685(3) 0.0734(3) 0.0283(16) Uani 1 1 d . . .
N34 N -0.1832(6) 0.8710(3) 0.0862(2) 0.0242(13) Uani 1 1 d . . .
C35 C -0.1229(7) 0.8238(3) 0.1209(3) 0.0159(13) Uani 1 1 d . . .
C36 C -0.2123(7) 0.7741(3) 0.1441(3) 0.0200(14) Uani 1 1 d . . .
Cl37 Cl -0.4145(2) 0.93039(9) 0.02808(10) 0.0437(5) Uani 1 1 d . . .
N38 N 0.0288(6) 0.8219(3) 0.1359(2) 0.0191(12) Uani 1 1 d . . .
H38 H 0.065(8) 0.789(3) 0.148(3) 0.023 Uiso 1 1 d . . .
S39 S 0.14580(19) 0.87648(7) 0.11656(7) 0.0200(4) Uani 1 1 d . . .
O40 O 0.2877(5) 0.8513(2) 0.1397(2) 0.0266(11) Uani 1 1 d . . .
O41 O 0.1005(6) 0.9383(2) 0.1370(2) 0.0296(12) Uani 1 1 d . . .
C42 C 0.1336(8) 0.8809(3) 0.0336(3) 0.0211(14) Uani 1 1 d . . .
C43 C 0.1278(7) 0.8272(3) -0.0066(3) 0.0174(13) Uani 1 1 d . . .
C44 C 0.1116(8) 0.8360(3) -0.0707(3) 0.0234(15) Uani 1 1 d . . .
C45 C 0.1079(9) 0.8968(3) -0.0963(3) 0.0300(17) Uani 1 1 d . . .
H45 H 0.0957 0.9024 -0.1407 0.036 Uiso 1 1 calc R . .
C46 C 0.1219(10) 0.9497(3) -0.0572(3) 0.0361(19) Uani 1 1 d . . .
H46 H 0.1238 0.9919 -0.0746 0.043 Uiso 1 1 calc R . .
C47 C 0.1333(8) 0.9418(3) 0.0071(3) 0.0265(16) Uani 1 1 d . . .
H47 H 0.1411 0.9787 0.0336 0.032 Uiso 1 1 calc R . .
Cl48 Cl 0.1448(2) 0.74993(7) 0.02361(7) 0.0300(4) Uani 1 1 d . . .
Cl49 Cl 0.0942(2) 0.77043(8) -0.12084(8) 0.0373(5) Uani 1 1 d . . .
O50 O -0.1398(5) 0.7286(2) 0.18019(19) 0.0187(10) Uani 1 1 d . . .
C51 C -0.2351(8) 0.6859(3) 0.2119(3) 0.0251(15) Uani 1 1 d . . .
H51A H -0.3174 0.6696 0.1814 0.030 Uiso 1 1 calc R . .
H51B H -0.2787 0.7097 0.2455 0.030 Uiso 1 1 calc R . .
C52 C -0.1427(7) 0.6302(3) 0.2400(3) 0.0195(14) Uani 1 1 d . . .
C53 C -0.1146(8) 0.6255(3) 0.3052(3) 0.0264(16) Uani 1 1 d . . .
H53 H -0.1447 0.6594 0.3308 0.032 Uiso 1 1 calc R . .
C54 C -0.0438(9) 0.5724(3) 0.3330(3) 0.0311(17) Uani 1 1 d . . .
H54 H -0.0248 0.5702 0.3776 0.037 Uiso 1 1 calc R . .
C55 C -0.0006(9) 0.5228(3) 0.2975(3) 0.0306(17) Uani 1 1 d . . .
H55 H 0.0466 0.4859 0.3170 0.037 Uiso 1 1 calc R . .
C56 C -0.0266(9) 0.5271(3) 0.2324(3) 0.0273(16) Uani 1 1 d . . .
H56 H 0.0035 0.4926 0.2075 0.033 Uiso 1 1 calc R . .
C57 C -0.0949(7) 0.5803(3) 0.2030(3) 0.0186(14) Uani 1 1 d . . .
C58 C -0.1164(7) 0.5825(3) 0.1325(3) 0.0189(14) Uani 1 1 d . . .
H58A H -0.1406 0.5387 0.1158 0.023 Uiso 1 1 calc R . .
H58B H -0.2015 0.6111 0.1183 0.023 Uiso 1 1 calc R . .
O59 O 0.0174(5) 0.6061(2) 0.10709(19) 0.0172(9) Uani 1 1 d . . .
H59 H 0.080(7) 0.579(3) 0.112(3) 0.010(18) 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
N1 C6 1.316(8) . yes
N1 C2 1.351(8) . yes
C2 C3 1.354(9) . yes
C2 H2 0.9500 . ?
C3 N4 1.329(8) . yes
C3 Cl7 1.729(6) . yes
N4 C5 1.320(7) . yes
C5 C6 1.398(8) . yes
C5 N8 1.402(8) . yes
C6 O20 1.350(7) . yes
N8 S9 1.626(5) . yes
N8 H8 0.76(7) . ?
S9 O11 1.426(4) . yes
S9 O10 1.431(4) . yes
S9 C12 1.754(6) . yes
C12 C13 1.389(8) . yes
C12 C17 1.390(8) . yes
C13 C14 1.376(9) . yes
C13 Cl18 1.724(6) . yes
C14 C15 1.385(9) . yes
C14 Cl19 1.719(7) . yes
C15 C16 1.358(10) . yes
C15 H15 0.9500 . ?
C16 C17 1.387(9) . yes
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O20 C21 1.460(7) . yes
C21 C22 1.489(9) . yes
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 C23 1.398(9) . yes
C22 C27 1.402(9) . yes
C23 C24 1.379(10) . yes
C23 H23 0.9500 . ?
C24 C25 1.387(10) . yes
C24 H24 0.9500 . ?
C25 C26 1.377(9) . yes
C25 H25 0.9500 . ?
C26 C27 1.385(9) . yes
C26 H26 0.9500 . ?
C27 C28 1.511(9) . yes
C28 O29 1.433(8) . yes
C28 H28A 0.9900 . ?
C28 H28B 0.9900 . ?
O29 H29 0.71(7) . ?
N31 C36 1.304(9) . yes
N31 C32 1.353(9) . yes
C32 C33 1.381(10) . yes
C32 H32 0.9500 . ?
C33 N34 1.321(9) . yes
C33 Cl37 1.732(7) . yes
N34 C35 1.308(8) . yes
C35 N38 1.372(8) . yes
C35 C36 1.432(9) . yes
C36 O50 1.341(7) . yes
N38 S39 1.635(6) . yes
N38 H38 0.79(7) . ?
S39 O40 1.420(5) . yes
S39 O41 1.429(5) . yes
S39 C42 1.767(6) . yes
C42 C47 1.383(9) . yes
C42 C43 1.405(8) . yes
C43 C44 1.373(9) . yes
C43 Cl48 1.727(6) . yes
C44 C45 1.372(9) . yes
C44 Cl49 1.727(6) . yes
C45 C46 1.375(10) . yes
C45 H45 0.9500 . ?
C46 C47 1.376(9) . yes
C46 H46 0.9500 . ?
C47 H47 0.9500 . ?
O50 C51 1.455(8) . yes
C51 C52 1.507(9) . yes
C51 H51A 0.9900 . ?
C51 H51B 0.9900 . ?
C52 C53 1.392(9) . yes
C52 C57 1.400(9) . yes
C53 C54 1.373(10) . yes
C53 H53 0.9500 . ?
C54 C55 1.360(10) . yes
C54 H54 0.9500 . ?
C55 C56 1.388(9) . yes
C55 H55 0.9500 . ?
C56 C57 1.378(9) . yes
C56 H56 0.9500 . ?
C57 C58 1.500(8) . yes
C58 O59 1.466(7) . yes
C58 H58A 0.9900 . ?
C58 H58B 0.9900 . ?
O59 H59 0.79(6) . ?

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
C6 N1 C2 117.6(6) . . yes
N1 C2 C3 119.4(6) . . yes
N1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
N4 C3 C2 123.6(6) . . yes
N4 C3 Cl7 117.4(5) . . yes
C2 C3 Cl7 119.0(5) . . yes
C5 N4 C3 117.5(5) . . yes
N4 C5 C6 119.6(6) . . yes
N4 C5 N8 119.0(5) . . yes
C6 C5 N8 121.4(5) . . yes
N1 C6 O20 121.9(5) . . yes
N1 C6 C5 122.3(5) . . yes
O20 C6 C5 115.7(5) . . yes
C5 N8 S9 125.0(4) . . yes
C5 N8 H8 117(6) . . ?
S9 N8 H8 116(6) . . ?
O11 S9 O10 119.3(3) . . yes
O11 S9 N8 107.8(3) . . yes
O10 S9 N8 106.4(3) . . yes
O11 S9 C12 106.3(3) . . yes
O10 S9 C12 110.9(3) . . yes
N8 S9 C12 105.0(3) . . yes
C13 C12 C17 119.8(6) . . yes
C13 C12 S9 122.8(4) . . yes
C17 C12 S9 117.3(5) . . yes
C14 C13 C12 119.8(6) . . yes
C14 C13 Cl18 118.6(5) . . yes
C12 C13 Cl18 121.5(4) . . yes
C13 C14 C15 120.3(6) . . yes
C13 C14 Cl19 120.6(5) . . yes
C15 C14 Cl19 119.0(5) . . yes
C16 C15 C14 119.7(6) . . yes
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 121.3(6) . . yes
C15 C16 H16 119.4 . . ?
C17 C16 H16 119.4 . . ?
C16 C17 C12 119.0(6) . . yes
C16 C17 H17 120.5 . . ?
C12 C17 H17 120.5 . . ?
C6 O20 C21 114.4(5) . . yes
O20 C21 C22 106.4(5) . . yes
O20 C21 H21A 110.4 . . ?
C22 C21 H21A 110.4 . . ?
O20 C21 H21B 110.4 . . ?
C22 C21 H21B 110.4 . . ?
H21A C21 H21B 108.6 . . ?
C23 C22 C27 119.2(6) . . yes
C23 C22 C21 117.1(6) . . yes
C27 C22 C21 123.7(6) . . yes
C24 C23 C22 120.2(7) . . yes
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C23 C24 C25 120.5(7) . . yes
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C26 C25 C24 119.5(7) . . yes
C26 C25 H25 120.2 . . ?
C24 C25 H25 120.2 . . ?
C25 C26 C27 121.0(7) . . yes
C25 C26 H26 119.5 . . ?
C27 C26 H26 119.5 . . ?
C26 C27 C22 119.5(6) . . yes
C26 C27 C28 117.8(6) . . yes
C22 C27 C28 122.7(6) . . yes
O29 C28 C27 113.1(5) . . yes
O29 C28 H28A 109.0 . . ?
C27 C28 H28A 109.0 . . ?
O29 C28 H28B 109.0 . . ?
C27 C28 H28B 109.0 . . ?
H28A C28 H28B 107.8 . . ?
C28 O29 H29 112(6) . . ?
C36 N31 C32 116.9(6) . . yes
N31 C32 C33 119.3(6) . . yes
N31 C32 H32 120.3 . . ?
C33 C32 H32 120.3 . . ?
N34 C33 C32 124.9(6) . . yes
N34 C33 Cl37 117.1(6) . . yes
C32 C33 Cl37 117.9(6) . . yes
C35 N34 C33 115.5(6) . . yes
N34 C35 N38 119.6(6) . . yes
N34 C35 C36 121.3(6) . . yes
N38 C35 C36 119.0(5) . . yes
N31 C36 O50 121.4(6) . . yes
N31 C36 C35 122.0(6) . . yes
O50 C36 C35 116.6(6) . . yes
C35 N38 S39 125.3(4) . . yes
C35 N38 H38 117(5) . . ?
S39 N38 H38 116(5) . . ?
O40 S39 O41 120.1(3) . . yes
O40 S39 N38 104.0(3) . . yes
O41 S39 N38 109.1(3) . . yes
O40 S39 C42 108.6(3) . . yes
O41 S39 C42 105.9(3) . . yes
N38 S39 C42 108.9(3) . . yes
C47 C42 C43 118.3(6) . . yes
C47 C42 S39 117.1(5) . . yes
C43 C42 S39 124.5(5) . . yes
C44 C43 C42 119.8(5) . . yes
C44 C43 Cl48 119.5(5) . . yes
C42 C43 Cl48 120.7(5) . . yes
C45 C44 C43 121.0(6) . . yes
C45 C44 Cl49 118.7(5) . . yes
C43 C44 Cl49 120.4(5) . . yes
C44 C45 C46 119.6(6) . . yes
C44 C45 H45 120.2 . . ?
C46 C45 H45 120.2 . . ?
C45 C46 C47 120.2(6) . . yes
C45 C46 H46 119.9 . . ?
C47 C46 H46 119.9 . . ?
C46 C47 C42 121.0(6) . . yes
C46 C47 H47 119.5 . . ?
C42 C47 H47 119.5 . . ?
C36 O50 C51 114.9(5) . . yes
O50 C51 C52 108.7(5) . . yes
O50 C51 H51A 109.9 . . ?
C52 C51 H51A 109.9 . . ?
O50 C51 H51B 109.9 . . ?
C52 C51 H51B 109.9 . . ?
H51A C51 H51B 108.3 . . ?
C53 C52 C57 118.7(6) . . yes
C53 C52 C51 118.8(6) . . yes
C57 C52 C51 122.3(6) . . yes
C54 C53 C52 120.8(6) . . yes
C54 C53 H53 119.6 . . ?
C52 C53 H53 119.6 . . ?
C55 C54 C53 120.9(6) . . yes
C55 C54 H54 119.6 . . ?
C53 C54 H54 119.6 . . ?
C54 C55 C56 119.0(6) . . yes
C54 C55 H55 120.5 . . ?
C56 C55 H55 120.5 . . ?
C57 C56 C55 121.6(6) . . yes
C57 C56 H56 119.2 . . ?
C55 C56 H56 119.2 . . ?
C56 C57 C52 119.0(6) . . yes
C56 C57 C58 118.8(6) . . yes
C52 C57 C58 122.1(6) . . yes
O59 C58 C57 111.5(5) . . yes
O59 C58 H58A 109.3 . . ?
C57 C58 H58A 109.3 . . ?
O59 C58 H58B 109.3 . . ?
C57 C58 H58B 109.3 . . ?
H58A C58 H58B 108.0 . . ?
C58 O59 H59 109(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
C6 N1 C2 C3 -0.9(9) . . . . yes
N1 C2 C3 N4 0.0(10) . . . . yes
N1 C2 C3 Cl7 177.9(5) . . . . yes
C2 C3 N4 C5 0.7(9) . . . . yes
Cl7 C3 N4 C5 -177.3(4) . . . . yes
C3 N4 C5 C6 -0.5(8) . . . . yes
C3 N4 C5 N8 178.8(5) . . . . yes
C2 N1 C6 O20 -179.7(5) . . . . yes
C2 N1 C6 C5 1.1(9) . . . . yes
N4 C5 C6 N1 -0.4(9) . . . . yes
N8 C5 C6 N1 -179.7(5) . . . . yes
N4 C5 C6 O20 -179.7(5) . . . . yes
N8 C5 C6 O20 1.1(8) . . . . yes
N4 C5 N8 S9 6.2(8) . . . . yes
C6 C5 N8 S9 -174.5(4) . . . . yes
C5 N8 S9 O11 50.7(5) . . . . yes
C5 N8 S9 O10 179.9(5) . . . . yes
C5 N8 S9 C12 -62.4(5) . . . . yes
O11 S9 C12 C13 179.7(5) . . . . yes
O10 S9 C12 C13 48.5(6) . . . . yes
N8 S9 C12 C13 -66.1(6) . . . . yes
O11 S9 C12 C17 -3.5(6) . . . . yes
O10 S9 C12 C17 -134.7(5) . . . . yes
N8 S9 C12 C17 110.7(5) . . . . yes
C17 C12 C13 C14 -0.5(10) . . . . yes
S9 C12 C13 C14 176.2(5) . . . . yes
C17 C12 C13 Cl18 -179.1(5) . . . . yes
S9 C12 C13 Cl18 -2.4(8) . . . . yes
C12 C13 C14 C15 1.7(11) . . . . yes
Cl18 C13 C14 C15 -179.7(6) . . . . yes
C12 C13 C14 Cl19 -176.9(5) . . . . yes
Cl18 C13 C14 Cl19 1.7(9) . . . . yes
C13 C14 C15 C16 -1.9(11) . . . . yes
Cl19 C14 C15 C16 176.6(6) . . . . yes
C14 C15 C16 C17 1.0(11) . . . . yes
C15 C16 C17 C12 0.1(11) . . . . yes
C13 C12 C17 C16 -0.4(10) . . . . yes
S9 C12 C17 C16 -177.3(5) . . . . yes
N1 C6 O20 C21 -5.3(8) . . . . yes
C5 C6 O20 C21 174.0(5) . . . . yes
C6 O20 C21 C22 -168.6(5) . . . . yes
O20 C21 C22 C23 102.9(6) . . . . yes
O20 C21 C22 C27 -76.9(7) . . . . yes
C27 C22 C23 C24 2.5(10) . . . . yes
C21 C22 C23 C24 -177.3(6) . . . . yes
C22 C23 C24 C25 -0.6(11) . . . . yes
C23 C24 C25 C26 -0.7(11) . . . . yes
C24 C25 C26 C27 0.2(11) . . . . yes
C25 C26 C27 C22 1.8(10) . . . . yes
C25 C26 C27 C28 -178.0(7) . . . . yes
C23 C22 C27 C26 -3.1(9) . . . . yes
C21 C22 C27 C26 176.8(6) . . . . yes
C23 C22 C27 C28 176.7(6) . . . . yes
C21 C22 C27 C28 -3.5(10) . . . . yes
C26 C27 C28 O29 -60.0(8) . . . . yes
C22 C27 C28 O29 120.3(6) . . . . yes
C36 N31 C32 C33 -1.6(10) . . . . yes
N31 C32 C33 N34 2.5(11) . . . . yes
N31 C32 C33 Cl37 -177.9(5) . . . . yes
C32 C33 N34 C35 -0.9(10) . . . . yes
Cl37 C33 N34 C35 179.5(5) . . . . yes
C33 N34 C35 N38 179.1(6) . . . . yes
C33 N34 C35 C36 -1.3(9) . . . . yes
C32 N31 C36 O50 -179.5(6) . . . . yes
C32 N31 C36 C35 -0.5(9) . . . . yes
N34 C35 C36 N31 2.1(9) . . . . yes
N38 C35 C36 N31 -178.3(6) . . . . yes
N34 C35 C36 O50 -178.9(5) . . . . yes
N38 C35 C36 O50 0.7(8) . . . . yes
N34 C35 N38 S39 3.0(8) . . . . yes
C36 C35 N38 S39 -176.6(4) . . . . yes
C35 N38 S39 O40 -177.1(5) . . . . yes
C35 N38 S39 O41 53.6(6) . . . . yes
C35 N38 S39 C42 -61.5(6) . . . . yes
O40 S39 C42 C47 -110.2(6) . . . . yes
O41 S39 C42 C47 20.0(7) . . . . yes
N38 S39 C42 C47 137.1(6) . . . . yes
O40 S39 C42 C43 68.2(7) . . . . yes
O41 S39 C42 C43 -161.6(6) . . . . yes
N38 S39 C42 C43 -44.4(7) . . . . yes
C47 C42 C43 C44 -4.6(10) . . . . yes
S39 C42 C43 C44 177.0(5) . . . . yes
C47 C42 C43 Cl48 174.1(6) . . . . yes
S39 C42 C43 Cl48 -4.3(9) . . . . yes
C42 C43 C44 C45 3.1(11) . . . . yes
Cl48 C43 C44 C45 -175.6(6) . . . . yes
C42 C43 C44 Cl49 -176.5(5) . . . . yes
Cl48 C43 C44 Cl49 4.8(8) . . . . yes
C43 C44 C45 C46 0.6(12) . . . . yes
Cl49 C44 C45 C46 -179.8(6) . . . . yes
C44 C45 C46 C47 -2.7(12) . . . . yes
C45 C46 C47 C42 1.2(13) . . . . yes
C43 C42 C47 C46 2.4(11) . . . . yes
S39 C42 C47 C46 -179.0(6) . . . . yes
N31 C36 O50 C51 -11.5(8) . . . . yes
C35 C36 O50 C51 169.5(5) . . . . yes
C36 O50 C51 C52 169.2(5) . . . . yes
O50 C51 C52 C53 111.6(6) . . . . yes
O50 C51 C52 C57 -73.9(7) . . . . yes
C57 C52 C53 C54 -1.2(10) . . . . yes
C51 C52 C53 C54 173.5(6) . . . . yes
C52 C53 C54 C55 -0.6(11) . . . . yes
C53 C54 C55 C56 1.2(12) . . . . yes
C54 C55 C56 C57 0.0(12) . . . . yes
C55 C56 C57 C52 -1.7(11) . . . . yes
C55 C56 C57 C58 178.6(7) . . . . yes
C53 C52 C57 C56 2.3(10) . . . . yes
C51 C52 C57 C56 -172.2(6) . . . . yes
C53 C52 C57 C58 -178.0(6) . . . . yes
C51 C52 C57 C58 7.5(9) . . . . yes
C56 C57 C58 O59 -83.9(7) . . . . yes
C52 C57 C58 O59 96.4(7) . . . . yes

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
N8 H8 O59 0.76(7) 2.14(7) 2.898(7) 173(8) .
O29 H29 O59 0.71(7) 2.17(7) 2.849(6) 161(8) .
N38 H38 O29 0.79(7) 2.01(7) 2.804(7) 174(7) .
O59 H59 O11 0.79(6) 2.07(6) 2.766(6) 148(6) 3_565

_diffrn_measured_fraction_theta_max 0.949
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.123
_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/n
_symmetry_space_group_name_Hall  '-P 2yn'

_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_correction_T_min  0.567

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless

_chemical_name_systematic        
;
 2,3-Dichloro-N-[6-chloro-3-({[2-(hydroxymethyl)phenyl]methyl}oxy)-2-
 pyrazinyl]benzenesulfonamide
;

_computing_data_merging          'SHELXTL V6.10 [NT] (Bruker, 2001)'
_computing_structure_solution    'SHELXTL V6.10 [NT] (Bruker, 2001)'
_computing_structure_refinement  'SHELXTL V6.10 [NT] (Bruker, 2001)'
_computing_molecular_graphics    'SHELXTL V6.10 [NT] (Bruker, 2001)'
_computing_publication_material  'SHELXTL V6.10 [NT] (Bruker, 2001)'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed

_computing_data_collection       'SMART V5.054 [NT] (Bruker, 2000)'
_computing_cell_refinement       'SMART V5.054 [NT] (Bruker, 2000)'
_computing_data_reduction        'SAINT+ V6.22 [NT] (Bruker, 2001)'

_diffrn_measurement_device_type  'Bruker AXS SMART 1K'
_diffrn_measurement_method       ω
_diffrn_radiation_collimation    '0.8 mm double-pinhole'
_diffrn_radiation_monochromator  'graphite - parallel geometry'
_diffrn_radiation_source         'normal focus sealed tube'
_database_code_depnum_ccdc_archive 'CCDC 975459'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_14

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 Cl2 N3 O2 S'
_chemical_formula_sum            'C15 H11 Cl2 N3 O2 S'
_chemical_formula_weight         368.23

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'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.5758(9)
_cell_length_b                   8.7573(9)
_cell_length_c                   23.065(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.905(8)
_cell_angle_gamma                90.00
_cell_volume                     1529.4(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)

_exptl_crystal_size_max          0.44
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.599
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             752
_exptl_absorpt_coefficient_mu    0.573

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_number            4880
_diffrn_reflns_av_R_equivalents  0.0282
_diffrn_reflns_av_sigmaI/netI    0.0497
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.80
_diffrn_reflns_theta_max         26.76
_reflns_number_total             2872
_reflns_number_gt                2434
_reflns_threshold_expression     >2sigma(I)

_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)+(0.0370P)²+0.1512P] where P=(Fo²+2Fc²)/3'

_refine_ls_extinction_coef       0.0023(5)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         2872
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0456
_refine_ls_R_factor_gt           0.0367
_refine_ls_wR_factor_ref         0.0949
_refine_ls_wR_factor_gt          0.0858
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_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
C1 C 1.0091(3) 0.8897(3) 0.58755(10) 0.0216(5) Uani 1 1 d . . .
C2 C 0.9604(3) 0.7984(3) 0.53994(10) 0.0226(5) Uani 1 1 d . . .
C3 C 1.0892(3) 0.7599(3) 0.50059(10) 0.0255(5) Uani 1 1 d . . .
C4 C 1.2615(3) 0.8104(3) 0.50858(10) 0.0283(6) Uani 1 1 d . . .
H4 H 1.3480 0.7833 0.4815 0.034 Uiso 1 1 calc R . .
C5 C 1.3071(3) 0.8992(3) 0.55547(10) 0.0300(6) Uani 1 1 d . . .
H5 H 1.4253 0.9341 0.5608 0.036 Uiso 1 1 calc R . .
C6 C 1.1822(3) 0.9387(3) 0.59524(10) 0.0259(5) Uani 1 1 d . . .
H6 H 1.2152 0.9995 0.6279 0.031 Uiso 1 1 calc R . .
Cl7 Cl 0.74805(7) 0.73128(7) 0.52931(3) 0.02893(18) Uani 1 1 d . . .
Cl8 Cl 1.03505(8) 0.65106(8) 0.44018(3) 0.0358(2) Uani 1 1 d . . .
N9 N 0.7735(3) 0.7941(2) 0.66625(8) 0.0224(4) Uani 1 1 d . . .
C10 C 0.8686(3) 0.6729(3) 0.69258(9) 0.0216(5) Uani 1 1 d . . .
C11 C 0.8001(3) 0.5243(3) 0.68950(9) 0.0217(5) Uani 1 1 d . . .
C12 C 0.8943(3) 0.4058(3) 0.71529(10) 0.0293(6) Uani 1 1 d . . .
H12 H 0.8480 0.3051 0.7135 0.035 Uiso 1 1 calc R . .
C13 C 1.0547(3) 0.4318(3) 0.74361(11) 0.0353(6) Uani 1 1 d . . .
H13 H 1.1191 0.3490 0.7605 0.042 Uiso 1 1 calc R . .
C14 C 1.1213(3) 0.5776(3) 0.74747(11) 0.0364(7) Uani 1 1 d . . .
H14 H 1.2312 0.5958 0.7673 0.044 Uiso 1 1 calc R . .
C15 C 1.0282(3) 0.6975(3) 0.72256(10) 0.0295(6) Uani 1 1 d . . .
H15 H 1.0738 0.7982 0.7260 0.035 Uiso 1 1 calc R . .
N16 N 0.6343(2) 0.4910(2) 0.66082(8) 0.0221(4) Uani 1 1 d . . .
N17 N 0.5090(2) 0.6006(2) 0.65132(9) 0.0285(5) Uani 1 1 d . . .
C18 C 0.3741(3) 0.5275(3) 0.62622(11) 0.0314(6) Uani 1 1 d . . .
H18 H 0.2661 0.5749 0.6142 0.038 Uiso 1 1 calc R . .
C19 C 0.4097(3) 0.3731(3) 0.61957(11) 0.0334(6) Uani 1 1 d . . .
H19 H 0.3341 0.2972 0.6029 0.040 Uiso 1 1 calc R . .
C20 C 0.5761(3) 0.3543(3) 0.64204(11) 0.0307(6) Uani 1 1 d . . .
H20 H 0.6400 0.2610 0.6441 0.037 Uiso 1 1 calc R . .
S21 S 0.85383(7) 0.94706(7) 0.63964(2) 0.02290(17) Uani 1 1 d . . .
O22 O 0.70788(19) 1.02100(18) 0.61052(7) 0.0271(4) Uani 1 1 d . . .
O23 O 0.9535(2) 1.02902(19) 0.68323(7) 0.0315(4) Uani 1 1 d . . .
H9 H 0.675(3) 0.770(3) 0.6549(10) 0.020(7) 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
C1 C6 1.385(3) . Y
C1 C2 1.398(3) . Y
C1 S21 1.782(2) . Y
C2 C3 1.396(3) . Y
C2 Cl7 1.723(2) . Y
C3 C4 1.384(3) . Y
C3 Cl8 1.726(2) . Y
C4 C5 1.367(3) . Y
C4 H4 0.9500 . ?
C5 C6 1.383(3) . Y
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N9 C10 1.409(3) . Y
N9 S21 1.602(2) . Y
N9 H9 0.81(2) . ?
C10 C15 1.389(3) . Y
C10 C11 1.402(3) . Y
C11 C12 1.383(3) . Y
C11 N16 1.430(3) . Y
C12 C13 1.379(3) . Y
C12 H12 0.9500 . ?
C13 C14 1.375(4) . Y
C13 H13 0.9500 . ?
C14 C15 1.379(3) . Y
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N16 C20 1.343(3) . Y
N16 N17 1.363(3) . Y
N17 C18 1.323(3) . Y
C18 C19 1.389(4) . Y
C18 H18 0.9500 . ?
C19 C20 1.357(3) . Y
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
S21 O22 1.4296(16) . Y
S21 O23 1.4304(16) . Y

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
C6 C1 C2 120.1(2) . . Y
C6 C1 S21 118.00(17) . . Y
C2 C1 S21 121.90(17) . . Y
C3 C2 C1 118.5(2) . . Y
C3 C2 Cl7 119.66(18) . . Y
C1 C2 Cl7 121.85(17) . . Y
C4 C3 C2 120.8(2) . . Y
C4 C3 Cl8 118.79(18) . . Y
C2 C3 Cl8 120.36(18) . . Y
C5 C4 C3 120.0(2) . . Y
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.4(2) . . Y
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.2(2) . . Y
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C10 N9 S21 126.84(16) . . Y
C10 N9 H9 113.5(17) . . ?
S21 N9 H9 116.6(17) . . ?
C15 C10 C11 118.9(2) . . Y
C15 C10 N9 121.5(2) . . Y
C11 C10 N9 119.6(2) . . Y
C12 C11 C10 119.3(2) . . Y
C12 C11 N16 118.6(2) . . Y
C10 C11 N16 122.1(2) . . Y
C13 C12 C11 120.9(2) . . Y
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C14 C13 C12 120.0(2) . . Y
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 119.9(2) . . Y
C13 C14 H14 120.1 . . ?
C15 C14 H14 120.1 . . ?
C14 C15 C10 120.9(2) . . Y
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
C20 N16 N17 110.88(19) . . Y
C20 N16 C11 127.2(2) . . Y
N17 N16 C11 121.84(18) . . Y
C18 N17 N16 104.7(2) . . Y
N17 C18 C19 111.7(2) . . Y
N17 C18 H18 124.2 . . ?
C19 C18 H18 124.2 . . ?
C20 C19 C18 104.9(2) . . Y
C20 C19 H19 127.5 . . ?
C18 C19 H19 127.5 . . ?
N16 C20 C19 107.8(2) . . Y
N16 C20 H20 126.1 . . ?
C19 C20 H20 126.1 . . ?
O22 S21 O23 119.02(10) . . Y
O22 S21 N9 105.14(10) . . Y
O23 S21 N9 110.41(10) . . Y
O22 S21 C1 109.18(10) . . Y
O23 S21 C1 105.70(10) . . Y
N9 S21 C1 106.87(10) . . Y

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
C6 C1 C2 C3 -0.6(3) . . . . Y
S21 C1 C2 C3 179.15(17) . . . . Y
C6 C1 C2 Cl7 178.61(17) . . . . Y
S21 C1 C2 Cl7 -1.6(3) . . . . Y
C1 C2 C3 C4 0.3(3) . . . . Y
Cl7 C2 C3 C4 -179.00(18) . . . . Y
C1 C2 C3 Cl8 -178.55(17) . . . . Y
Cl7 C2 C3 Cl8 2.2(3) . . . . Y
C2 C3 C4 C5 -0.1(4) . . . . Y
Cl8 C3 C4 C5 178.74(19) . . . . Y
C3 C4 C5 C6 0.3(4) . . . . Y
C4 C5 C6 C1 -0.7(4) . . . . Y
C2 C1 C6 C5 0.8(4) . . . . Y
S21 C1 C6 C5 -178.94(18) . . . . Y
S21 N9 C10 C15 30.7(3) . . . . Y
S21 N9 C10 C11 -150.44(18) . . . . Y
C15 C10 C11 C12 -1.3(3) . . . . Y
N9 C10 C11 C12 179.8(2) . . . . Y
C15 C10 C11 N16 178.2(2) . . . . Y
N9 C10 C11 N16 -0.7(3) . . . . Y
C10 C11 C12 C13 -0.4(3) . . . . Y
N16 C11 C12 C13 -179.8(2) . . . . Y
C11 C12 C13 C14 1.3(4) . . . . Y
C12 C13 C14 C15 -0.5(4) . . . . Y
C13 C14 C15 C10 -1.1(4) . . . . Y
C11 C10 C15 C14 2.0(3) . . . . Y
N9 C10 C15 C14 -179.1(2) . . . . Y
C12 C11 N16 C20 -19.0(3) . . . . Y
C10 C11 N16 C20 161.5(2) . . . . Y
C12 C11 N16 N17 158.1(2) . . . . Y
C10 C11 N16 N17 -21.4(3) . . . . Y
C20 N16 N17 C18 -0.2(2) . . . . Y
C11 N16 N17 C18 -177.8(2) . . . . Y
N16 N17 C18 C19 0.2(3) . . . . Y
N17 C18 C19 C20 -0.1(3) . . . . Y
N17 N16 C20 C19 0.2(3) . . . . Y
C11 N16 C20 C19 177.5(2) . . . . Y
C18 C19 C20 N16 0.0(3) . . . . Y
C10 N9 S21 O22 171.30(18) . . . . Y
C10 N9 S21 O23 -59.2(2) . . . . Y
C10 N9 S21 C1 55.3(2) . . . . Y
C6 C1 S21 O22 125.10(18) . . . . Y
C2 C1 S21 O22 -54.7(2) . . . . Y
C6 C1 S21 O23 -4.0(2) . . . . Y
C2 C1 S21 O23 176.17(18) . . . . Y
C6 C1 S21 N9 -121.68(19) . . . . Y
C2 C1 S21 N9 58.5(2) . . . . Y

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
N9 H9 N17 0.81(2) 1.95(2) 2.638(3) 143(2) .

_diffrn_measured_fraction_theta_max 0.879
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.385
_refine_diff_density_min         -0.354
_refine_diff_density_rms         0.061

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 0 0 0.09232
-1 0 0 0.09232
0 1 0 0.21719
0 -1 0 0.21719
0 0 1 0.05541
0 0 -1 0.05541

_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;

_cell_measurement_reflns_used    2450
_cell_measurement_theta_min      2.65
_cell_measurement_theta_max      26.71
_exptl_absorpt_correction_T_min  0.796
_exptl_absorpt_correction_T_max  0.940
_exptl_absorpt_correction_type   gaussian

_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.3968
_diffrn_orient_matrix_UB_11      0.0007825000
_diffrn_orient_matrix_UB_12      -0.0788439000
_diffrn_orient_matrix_UB_13      0.0067273000
_diffrn_orient_matrix_UB_21      -0.0044468000
_diffrn_orient_matrix_UB_22      -0.0179527000
_diffrn_orient_matrix_UB_23      -0.0300392000
_diffrn_orient_matrix_UB_31      0.0936712000
_diffrn_orient_matrix_UB_32      -0.0005923000
_diffrn_orient_matrix_UB_33      -0.0004382000

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -85.00   59.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292   38.0000   90.0000 144

#__ type_ start__ end____ width___ exp.time_
  2 omega   -8.00   34.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292  -54.0000 -153.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega  -81.00  -56.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -23.7292  179.0000    0.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   -5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       25.1354  133.0000  136.0000 36
;

_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_cell_setting           monoclinic

_exptl_crystal_description       block
_exptl_crystal_colour            colourless

_chemical_name_systematic        
;
2,3-Dichloro-N-[2-(1H-pyrazol-1-yl)phenyl]benzenesulfonamide
;

_computing_data_merging          'SHELXTL V2008/4 (Bruker, 2008)'
_computing_structure_solution    'SHELXTL V2008/4 (Bruker, 2008)'
_computing_structure_refinement  'SHELXTL V2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL V2008/4 (Bruker, 2008)'
_computing_publication_material  'SHELXTL V2008/4 (Bruker, 2008)'
_refine_ls_extinction_method     'SHELXTL V2008/4 (Bruker, 2008)'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_chemical_absolute_configuration .
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_collimation    '0.8 mm double-pinhole'
_database_code_depnum_ccdc_archive 'CCDC 975460'
#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_16

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H9 Cl2 N5 O2 S'
_chemical_formula_sum            'C13 H9 Cl2 N5 O2 S'
_chemical_formula_weight         370.21

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'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.4390(9)
_cell_length_b                   8.4770(12)
_cell_length_c                   13.0579(15)
_cell_angle_alpha                88.763(11)
_cell_angle_beta                 84.177(10)
_cell_angle_gamma                64.880(13)
_cell_volume                     741.50(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)

_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.658
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376
_exptl_absorpt_coefficient_mu    0.595

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_reflns_number            8747
_diffrn_reflns_av_R_equivalents  0.0377
_diffrn_reflns_av_sigmaI/netI    0.0426
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         28.50
_reflns_number_total             3152
_reflns_number_gt                2634
_reflns_threshold_expression     >2sigma(I)

_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)+(0.0356P)²+0.3323P] where P=(Fo²+2Fc²)/3'

_refine_ls_extinction_coef       0.0025(14)

_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^

_refine_ls_number_reflns         3152
_refine_ls_number_parameters     213
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0461
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0872
_refine_ls_wR_factor_gt          0.0802
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_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
C1 C 0.7750(3) 0.1870(2) 0.12060(15) 0.0177(4) Uani 1 1 d . . .
C2 C 0.9496(3) 0.2048(3) 0.08668(15) 0.0189(4) Uani 1 1 d . . .
C3 C 0.9698(3) 0.2627(3) -0.01229(16) 0.0210(4) Uani 1 1 d . . .
C4 C 0.8215(3) 0.3020(3) -0.07670(17) 0.0258(5) Uani 1 1 d . . .
H4 H 0.8379 0.3401 -0.1445 0.031 Uiso 1 1 calc R . .
C5 C 0.6496(3) 0.2855(3) -0.04210(17) 0.0294(5) Uani 1 1 d . . .
H5 H 0.5465 0.3139 -0.0861 0.035 Uiso 1 1 calc R . .
C6 C 0.6252(3) 0.2281(3) 0.05608(16) 0.0237(5) Uani 1 1 d . . .
H6 H 0.5060 0.2168 0.0792 0.028 Uiso 1 1 calc R . .
N7 N 0.7299(3) 0.2397(2) 0.33336(13) 0.0176(4) Uani 1 1 d . . .
H7 H 0.839(4) 0.222(3) 0.3475(18) 0.024(6) Uiso 1 1 d . . .
C8 C 0.5949(3) 0.4198(2) 0.33299(15) 0.0167(4) Uani 1 1 d . . .
C9 C 0.3931(3) 0.4796(2) 0.36852(14) 0.0168(4) Uani 1 1 d . . .
C10 C 0.2653(3) 0.6555(3) 0.36736(16) 0.0221(4) Uani 1 1 d . . .
H10 H 0.1277 0.6947 0.3907 0.026 Uiso 1 1 calc R . .
C11 C 0.3392(3) 0.7735(3) 0.33205(17) 0.0248(5) Uani 1 1 d . . .
H11 H 0.2518 0.8938 0.3303 0.030 Uiso 1 1 calc R . .
C12 C 0.5398(3) 0.7172(3) 0.29926(16) 0.0241(5) Uani 1 1 d . . .
H12 H 0.5907 0.7991 0.2768 0.029 Uiso 1 1 calc R . .
C13 C 0.6664(3) 0.5412(3) 0.29916(15) 0.0200(4) Uani 1 1 d . . .
H13 H 0.8037 0.5030 0.2757 0.024 Uiso 1 1 calc R . .
N15 N 0.3096(2) 0.3614(2) 0.40506(12) 0.0176(4) Uani 1 1 d . . .
N16 N 0.1300(2) 0.3840(2) 0.37813(14) 0.0243(4) Uani 1 1 d . . .
N17 N 0.0961(3) 0.2572(2) 0.41884(14) 0.0273(4) Uani 1 1 d . . .
N18 N 0.2499(3) 0.1506(2) 0.47176(14) 0.0263(4) Uani 1 1 d . . .
C19 C 0.3796(3) 0.2184(3) 0.46162(15) 0.0217(4) Uani 1 1 d . . .
H19 H 0.5039 0.1729 0.4900 0.026 Uiso 1 1 calc R . .
S20 S 0.73559(7) 0.10480(6) 0.24386(4) 0.01772(14) Uani 1 1 d . . .
O21 O 0.5402(2) 0.11065(18) 0.24788(11) 0.0210(3) Uani 1 1 d . . .
O22 O 0.9020(2) -0.05591(17) 0.25892(11) 0.0249(3) Uani 1 1 d . . .
Cl23 Cl 1.13793(7) 0.15990(7) 0.16508(4) 0.02681(15) Uani 1 1 d . . .
Cl24 Cl 1.18321(8) 0.28540(8) -0.05794(4) 0.03176(16) Uani 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
C1 C6 1.386(3) . Y
C1 C2 1.398(3) . Y
C1 S20 1.786(2) . Y
C2 C3 1.389(3) . Y
C2 Cl23 1.725(2) . Y
C3 C4 1.378(3) . Y
C3 Cl24 1.725(2) . Y
C4 C5 1.374(3) . Y
C4 H4 0.9500 . ?
C5 C6 1.384(3) . Y
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
N7 C8 1.427(2) . Y
N7 S20 1.6377(18) . Y
N7 H7 0.80(2) . ?
C8 C13 1.391(3) . Y
C8 C9 1.396(3) . Y
C9 C10 1.388(3) . Y
C9 N15 1.437(2) . Y
C10 C11 1.382(3) . Y
C10 H10 0.9500 . ?
C11 C12 1.383(3) . Y
C11 H11 0.9500 . ?
C12 C13 1.385(3) . Y
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
N15 C19 1.338(3) . Y
N15 N16 1.350(2) . Y
N16 N17 1.296(3) . Y
N17 N18 1.363(3) . Y
N18 C19 1.311(3) . Y
C19 H19 0.9500 . ?
S20 O22 1.4257(15) . Y
S20 O21 1.4290(14) . Y

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
C6 C1 C2 119.99(18) . . Y
C6 C1 S20 116.85(15) . . Y
C2 C1 S20 123.12(15) . . Y
C3 C2 C1 118.82(18) . . Y
C3 C2 Cl23 119.44(15) . . Y
C1 C2 Cl23 121.73(15) . . Y
C4 C3 C2 121.10(18) . . Y
C4 C3 Cl24 118.35(16) . . Y
C2 C3 Cl24 120.54(16) . . Y
C5 C4 C3 119.5(2) . . Y
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 120.7(2) . . Y
C4 C5 H5 119.6 . . ?
C6 C5 H5 119.6 . . ?
C5 C6 C1 119.85(19) . . Y
C5 C6 H6 120.1 . . ?
C1 C6 H6 120.1 . . ?
C8 N7 S20 120.51(14) . . Y
C8 N7 H7 114.2(17) . . ?
S20 N7 H7 112.5(17) . . ?
C13 C8 C9 118.43(18) . . Y
C13 C8 N7 119.41(18) . . Y
C9 C8 N7 122.14(17) . . Y
C10 C9 C8 120.89(18) . . Y
C10 C9 N15 117.78(17) . . Y
C8 C9 N15 121.32(17) . . Y
C11 C10 C9 119.61(19) . . Y
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.34(19) . . Y
C10 C11 H11 119.8 . . ?
C12 C11 H11 119.8 . . ?
C11 C12 C13 119.87(19) . . Y
C11 C12 H12 120.1 . . ?
C13 C12 H12 120.1 . . ?
C12 C13 C8 120.83(19) . . Y
C12 C13 H13 119.6 . . ?
C8 C13 H13 119.6 . . ?
C19 N15 N16 108.18(16) . . Y
C19 N15 C9 132.27(17) . . Y
N16 N15 C9 119.49(16) . . Y
N17 N16 N15 105.95(17) . . Y
N16 N17 N18 111.30(16) . . Y
C19 N18 N17 105.12(17) . . Y
N18 C19 N15 109.45(18) . . Y
N18 C19 H19 125.3 . . ?
N15 C19 H19 125.3 . . ?
O22 S20 O21 119.82(9) . . Y
O22 S20 N7 105.89(9) . . Y
O21 S20 N7 107.33(9) . . Y
O22 S20 C1 109.55(9) . . Y
O21 S20 C1 105.02(9) . . Y
N7 S20 C1 108.90(9) . . Y

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
C6 C1 C2 C3 -0.4(3) . . . . Y
S20 C1 C2 C3 177.19(15) . . . . Y
C6 C1 C2 Cl23 178.54(15) . . . . Y
S20 C1 C2 Cl23 -3.8(2) . . . . Y
C1 C2 C3 C4 -0.2(3) . . . . Y
Cl23 C2 C3 C4 -179.17(16) . . . . Y
C1 C2 C3 Cl24 -179.57(15) . . . . Y
Cl23 C2 C3 Cl24 1.4(2) . . . . Y
C2 C3 C4 C5 0.8(3) . . . . Y
Cl24 C3 C4 C5 -179.81(17) . . . . Y
C3 C4 C5 C6 -0.8(3) . . . . Y
C4 C5 C6 C1 0.2(3) . . . . Y
C2 C1 C6 C5 0.4(3) . . . . Y
S20 C1 C6 C5 -177.33(17) . . . . Y
S20 N7 C8 C13 -103.20(19) . . . . Y
S20 N7 C8 C9 78.8(2) . . . . Y
C13 C8 C9 C10 1.9(3) . . . . Y
N7 C8 C9 C10 179.92(18) . . . . Y
C13 C8 C9 N15 -179.67(17) . . . . Y
N7 C8 C9 N15 -1.6(3) . . . . Y
C8 C9 C10 C11 -1.0(3) . . . . Y
N15 C9 C10 C11 -179.52(18) . . . . Y
C9 C10 C11 C12 -0.8(3) . . . . Y
C10 C11 C12 C13 1.7(3) . . . . Y
C11 C12 C13 C8 -0.8(3) . . . . Y
C9 C8 C13 C12 -1.0(3) . . . . Y
N7 C8 C13 C12 -179.05(18) . . . . Y
C10 C9 N15 C19 -142.2(2) . . . . Y
C8 C9 N15 C19 39.3(3) . . . . Y
C10 C9 N15 N16 40.7(2) . . . . Y
C8 C9 N15 N16 -137.76(19) . . . . Y
C19 N15 N16 N17 0.4(2) . . . . Y
C9 N15 N16 N17 178.06(16) . . . . Y
N15 N16 N17 N18 -0.3(2) . . . . Y
N16 N17 N18 C19 0.1(2) . . . . Y
N17 N18 C19 N15 0.2(2) . . . . Y
N16 N15 C19 N18 -0.4(2) . . . . Y
C9 N15 C19 N18 -177.62(19) . . . . Y
C8 N7 S20 O22 172.47(15) . . . . Y
C8 N7 S20 O21 -58.44(17) . . . . Y
C8 N7 S20 C1 54.75(17) . . . . Y
C6 C1 S20 O22 126.79(16) . . . . Y
C2 C1 S20 O22 -50.91(19) . . . . Y
C6 C1 S20 O21 -3.13(17) . . . . Y
C2 C1 S20 O21 179.17(16) . . . . Y
C6 C1 S20 N7 -117.83(16) . . . . Y
C2 C1 S20 N7 64.47(18) . . . . Y

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
N7 H7 N17 0.80(2) 2.34(2) 3.107(2) 161(2) 1_655
N7 H7 Cl23 0.80(2) 2.98(2) 3.3863(18) 114.0(19) .

_diffrn_measured_fraction_theta_max 0.839
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.461
_refine_diff_density_min         -0.447
_refine_diff_density_rms         0.064

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.03846
0 0 -1 0.03846
-1 -1 0 0.15052
1 1 0 0.15052
0 2 1 0.02923
0 -2 -1 0.02923

_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
;

_cell_measurement_reflns_used    4566
_cell_measurement_theta_min      3.03
_cell_measurement_theta_max      28.44
_exptl_absorpt_correction_T_min  0.882
_exptl_absorpt_correction_T_max  0.970
_exptl_absorpt_correction_type   gaussian

_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.34.44 (release 25-10-2010 CrysAlis171 .NET)
(compiled Oct 25 2010,18:11:34)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
;

_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.3968
_diffrn_orient_matrix_UB_11      0.0723637000
_diffrn_orient_matrix_UB_12      -0.0045749000
_diffrn_orient_matrix_UB_13      0.0328030000
_diffrn_orient_matrix_UB_21      -0.0504190000
_diffrn_orient_matrix_UB_22      0.0913560000
_diffrn_orient_matrix_UB_23      0.0092011000
_diffrn_orient_matrix_UB_31      -0.0585496000
_diffrn_orient_matrix_UB_32      -0.0133538000
_diffrn_orient_matrix_UB_33      0.0426883000

_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -42.00   54.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -7.9507   77.0000 -150.0000 96

#__ type_ start__ end____ width___ exp.time_
  2 omega  -34.00   -8.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -7.9507   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   -1.00   88.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   77.0000  -30.0000 89

#__ type_ start__ end____ width___ exp.time_
  4 omega    5.00   31.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   77.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -17.00   84.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257   77.0000  120.0000 101

#__ type_ start__ end____ width___ exp.time_
  6 omega  -84.00  -59.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -       -7.9507  -38.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  7 omega  -66.00   28.00   1.0000   30.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8257  -38.0000    0.0000 94
;

_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_cell_setting           triclinic

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless

_chemical_name_systematic        
;
2,3-Dichloro-N-[2-(1H-tetrazol-1-yl)phenyl]benzenesulfonamide
;

_computing_data_merging          'SHELXTL V2008/4 (Bruker, 2008)'
_computing_structure_solution    'SHELXTL V2008/4 (Bruker, 2008)'
_computing_structure_refinement  'SHELXTL V2008/4 (Bruker, 2008)'
_computing_molecular_graphics    'SHELXTL V2008/4 (Bruker, 2008)'
_computing_publication_material  'SHELXTL V2008/4 (Bruker, 2008)'
_refine_ls_extinction_method     'SHELXTL V2008/4 (Bruker, 2008)'

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_chemical_absolute_configuration .
_diffrn_measurement_device_type  'Oxford Diffraction Gemini A Ultra'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_collimation    '0.8 mm double-pinhole'
_database_code_depnum_ccdc_archive 'CCDC 975461'
