# 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 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_c:\nadeem

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
4-methyl-2-[({[(4-methylphenyl)sulfonyl]amino}acetyl)amino]pentanoic acid
hydrate
;
_chemical_name_common            
;
4-methyl-2-[({[(4-methylphenyl)sulfonyl]amino}acetyl)amino]pentanoic acid
hydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H22 N2 O5 S, H2 O'
_chemical_formula_sum            'C15 H24 N2 O6 S'
_chemical_formula_weight         360.42

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'
_chemical_absolute_configuration rm

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

_cell_length_a                   10.1962(11)
_cell_length_b                   5.9840(4)
_cell_length_c                   15.6595(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.232(10)
_cell_angle_gamma                90.00
_cell_volume                     949.80(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2085
_cell_measurement_theta_min      4.3584
_cell_measurement_theta_max      76.3007

_exptl_crystal_description       needles
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.260
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             384
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_min  0.45609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8328
_diffrn_reflns_av_R_equivalents  0.0547
_diffrn_reflns_av_sigmaI/netI    0.0439
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.36
_diffrn_reflns_theta_max         76.50
_reflns_number_total             2865
_reflns_number_gt                2132
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.0230P] 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_coef       0.0041(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.05(3)
_refine_ls_number_reflns         2865
_refine_ls_number_parameters     241
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0435
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.0977
_refine_ls_goodness_of_fit_ref   1.105
_refine_ls_restrained_S_all      1.104
_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
S1 S 0.13819(10) 0.35458(16) 0.82048(6) 0.0597(3) Uani 1 1 d . . .
O3 O 0.0354(3) 0.9124(4) 0.64930(18) 0.0597(7) Uani 1 1 d . . .
O5 O 0.2971(3) 1.2249(4) 0.56201(17) 0.0615(7) Uani 1 1 d . . .
O6W O 0.7820(3) 0.9828(4) 0.5652(2) 0.0677(8) Uani 1 1 d D . .
N2 N 0.2167(3) 0.6988(5) 0.64618(19) 0.0462(6) Uani 1 1 d . . .
N1 N 0.0984(3) 0.3467(5) 0.71743(18) 0.0507(7) Uani 1 1 d . . .
O1 O 0.2248(3) 0.1708(7) 0.8398(2) 0.0937(12) Uani 1 1 d . . .
O4 O 0.2113(3) 0.9310(4) 0.48972(16) 0.0677(8) Uani 1 1 d . . .
O2 O 0.1807(4) 0.5796(6) 0.8408(2) 0.0876(11) Uani 1 1 d . . .
C9 C 0.3078(3) 0.8809(5) 0.6358(2) 0.0457(7) Uani 1 1 d . . .
H9 H 0.3086 0.9810 0.6854 0.055 Uiso 1 1 calc R . .
C8 C 0.0913(4) 0.7290(5) 0.6573(2) 0.0452(7) Uani 1 1 d . . .
C11 C 0.4461(4) 0.7886(7) 0.6324(2) 0.0579(9) Uani 1 1 d . . .
H11A H 0.5053 0.9123 0.6250 0.070 Uiso 1 1 calc R . .
H11B H 0.4456 0.6932 0.5823 0.070 Uiso 1 1 calc R . .
C10 C 0.2648(4) 1.0125(5) 0.5552(2) 0.0485(8) Uani 1 1 d . . .
C12 C 0.5008(4) 0.6549(9) 0.7118(3) 0.0721(13) Uani 1 1 d . . .
H12 H 0.4433 0.5253 0.7164 0.087 Uiso 1 1 calc R . .
C5 C -0.1883(4) 0.0756(8) 0.8929(3) 0.0726(12) Uani 1 1 d . . .
H5 H -0.2318 -0.0606 0.8849 0.087 Uiso 1 1 calc R . .
C1 C -0.0078(4) 0.3094(6) 0.8689(2) 0.0520(8) Uani 1 1 d . . .
C7 C 0.0140(4) 0.5240(5) 0.6788(2) 0.0516(8) Uani 1 1 d . . .
H7A H -0.0490 0.5660 0.7182 0.062 Uiso 1 1 calc R . .
H7B H -0.0353 0.4681 0.6267 0.062 Uiso 1 1 calc R . .
C2 C -0.0574(4) 0.4756(7) 0.9175(2) 0.0649(10) Uani 1 1 d . . .
H2 H -0.0132 0.6110 0.9261 0.078 Uiso 1 1 calc R . .
C4 C -0.2418(4) 0.2412(9) 0.9411(3) 0.0697(11) Uani 1 1 d . . .
C6 C -0.0726(4) 0.1085(7) 0.8569(3) 0.0662(10) Uani 1 1 d . . .
H6 H -0.0385 -0.0040 0.8248 0.079 Uiso 1 1 calc R . .
C3 C -0.1736(5) 0.4384(8) 0.9533(3) 0.0719(12) Uani 1 1 d . . .
H3 H -0.2064 0.5499 0.9866 0.086 Uiso 1 1 calc R . .
C14 C 0.4998(6) 0.7903(13) 0.7934(3) 0.113(2) Uani 1 1 d . . .
H14A H 0.5439 0.7083 0.8408 0.169 Uiso 1 1 calc R . .
H14B H 0.4103 0.8189 0.8038 0.169 Uiso 1 1 calc R . .
H14C H 0.5446 0.9296 0.7872 0.169 Uiso 1 1 calc R . .
C15 C -0.3704(5) 0.2021(13) 0.9794(3) 0.1020(19) Uani 1 1 d . . .
H15A H -0.3737 0.0504 0.9990 0.153 Uiso 1 1 calc R . .
H15B H -0.4433 0.2294 0.9365 0.153 Uiso 1 1 calc R . .
H15C H -0.3756 0.3019 1.0269 0.153 Uiso 1 1 calc R . .
C13 C 0.6368(5) 0.5689(15) 0.7008(4) 0.133(3) Uani 1 1 d . . .
H13A H 0.6944 0.6927 0.6934 0.200 Uiso 1 1 calc R . .
H13B H 0.6325 0.4739 0.6512 0.200 Uiso 1 1 calc R . .
H13C H 0.6701 0.4854 0.7508 0.200 Uiso 1 1 calc R . .
H2N H 0.248(4) 0.564(7) 0.653(2) 0.059(11) Uiso 1 1 d . . .
H1N H 0.082(4) 0.235(8) 0.698(3) 0.062(13) Uiso 1 1 d . . .
H5O H 0.269(5) 1.305(9) 0.502(3) 0.101(17) Uiso 1 1 d . . .
H1W H 0.859(3) 0.964(11) 0.595(3) 0.13(2) Uiso 1 1 d D . .
H2W H 0.788(6) 1.112(5) 0.539(3) 0.111(19) Uiso 1 1 d 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
S1 O1 1.422(3) . ?
S1 O2 1.439(3) . ?
S1 N1 1.621(3) . ?
S1 C1 1.764(4) . ?
O3 C8 1.237(4) . ?
O5 C10 1.314(4) . ?
O5 H5O 1.07(5) . ?
O6W H1W 0.881(10) . ?
O6W H2W 0.881(10) . ?
N2 C8 1.321(5) . ?
N2 C9 1.452(4) . ?
N2 H2N 0.87(4) . ?
N1 C7 1.456(4) . ?
N1 H1N 0.75(5) . ?
O4 C10 1.210(4) . ?
C9 C10 1.512(4) . ?
C9 C11 1.521(5) . ?
C9 H9 0.9800 . ?
C8 C7 1.516(4) . ?
C11 C12 1.532(5) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.506(7) . ?
C12 C14 1.513(7) . ?
C12 H12 0.9800 . ?
C5 C6 1.375(6) . ?
C5 C4 1.393(6) . ?
C5 H5 0.9300 . ?
C1 C6 1.375(5) . ?
C1 C2 1.381(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C2 C3 1.383(6) . ?
C2 H2 0.9300 . ?
C4 C3 1.373(7) . ?
C4 C15 1.517(6) . ?
C6 H6 0.9300 . ?
C3 H3 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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 S1 O2 120.8(2) . . ?
O1 S1 N1 105.8(2) . . ?
O2 S1 N1 106.51(17) . . ?
O1 S1 C1 108.89(19) . . ?
O2 S1 C1 107.22(19) . . ?
N1 S1 C1 106.95(16) . . ?
C10 O5 H5O 109(3) . . ?
H1W O6W H2W 105(5) . . ?
C8 N2 C9 123.5(3) . . ?
C8 N2 H2N 117(3) . . ?
C9 N2 H2N 118(3) . . ?
C7 N1 S1 117.7(2) . . ?
C7 N1 H1N 113(3) . . ?
S1 N1 H1N 117(3) . . ?
N2 C9 C10 110.7(3) . . ?
N2 C9 C11 109.8(3) . . ?
C10 C9 C11 110.2(3) . . ?
N2 C9 H9 108.7 . . ?
C10 C9 H9 108.7 . . ?
C11 C9 H9 108.7 . . ?
O3 C8 N2 123.3(3) . . ?
O3 C8 C7 119.7(3) . . ?
N2 C8 C7 116.9(3) . . ?
C9 C11 C12 114.7(3) . . ?
C9 C11 H11A 108.6 . . ?
C12 C11 H11A 108.6 . . ?
C9 C11 H11B 108.6 . . ?
C12 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
O4 C10 O5 123.0(3) . . ?
O4 C10 C9 124.1(3) . . ?
O5 C10 C9 112.8(3) . . ?
C13 C12 C14 111.8(5) . . ?
C13 C12 C11 110.1(4) . . ?
C14 C12 C11 111.7(4) . . ?
C13 C12 H12 107.7 . . ?
C14 C12 H12 107.7 . . ?
C11 C12 H12 107.7 . . ?
C6 C5 C4 121.6(4) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C6 C1 C2 120.4(4) . . ?
C6 C1 S1 119.4(3) . . ?
C2 C1 S1 120.2(3) . . ?
N1 C7 C8 112.5(3) . . ?
N1 C7 H7A 109.1 . . ?
C8 C7 H7A 109.1 . . ?
N1 C7 H7B 109.1 . . ?
C8 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?
C1 C2 C3 119.3(4) . . ?
C1 C2 H2 120.4 . . ?
C3 C2 H2 120.4 . . ?
C3 C4 C5 117.7(4) . . ?
C3 C4 C15 121.6(5) . . ?
C5 C4 C15 120.7(5) . . ?
C1 C6 C5 119.3(4) . . ?
C1 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C4 C3 C2 121.7(4) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
O1 S1 N1 C7 -177.3(3) . . . . ?
O2 S1 N1 C7 -47.6(3) . . . . ?
C1 S1 N1 C7 66.8(3) . . . . ?
C8 N2 C9 C10 -63.2(4) . . . . ?
C8 N2 C9 C11 175.0(3) . . . . ?
C9 N2 C8 O3 9.4(5) . . . . ?
C9 N2 C8 C7 -172.2(3) . . . . ?
N2 C9 C11 C12 -58.8(4) . . . . ?
C10 C9 C11 C12 179.1(3) . . . . ?
N2 C9 C10 O4 -34.2(5) . . . . ?
C11 C9 C10 O4 87.4(4) . . . . ?
N2 C9 C10 O5 148.8(3) . . . . ?
C11 C9 C10 O5 -89.7(4) . . . . ?
C9 C11 C12 C13 179.1(5) . . . . ?
C9 C11 C12 C14 -56.1(5) . . . . ?
O1 S1 C1 C6 -50.1(4) . . . . ?
O2 S1 C1 C6 177.6(3) . . . . ?
N1 S1 C1 C6 63.7(4) . . . . ?
O1 S1 C1 C2 130.7(4) . . . . ?
O2 S1 C1 C2 -1.6(4) . . . . ?
N1 S1 C1 C2 -115.5(3) . . . . ?
S1 N1 C7 C8 85.7(3) . . . . ?
O3 C8 C7 N1 -158.1(3) . . . . ?
N2 C8 C7 N1 23.5(4) . . . . ?
C6 C1 C2 C3 -0.6(6) . . . . ?
S1 C1 C2 C3 178.6(3) . . . . ?
C6 C5 C4 C3 -1.4(7) . . . . ?
C6 C5 C4 C15 179.3(5) . . . . ?
C2 C1 C6 C5 0.8(6) . . . . ?
S1 C1 C6 C5 -178.4(3) . . . . ?
C4 C5 C6 C1 0.2(7) . . . . ?
C5 C4 C3 C2 1.6(7) . . . . ?
C15 C4 C3 C2 -179.1(4) . . . . ?
C1 C2 C3 C4 -0.7(6) . . . . ?

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
O6W H1W O3 0.881(10) 1.925(13) 2.802(4) 174(6) 1_655
N1 H1N O3 0.75(5) 2.11(5) 2.856(4) 176(4) 1_545
N2 H2N O5 0.87(4) 2.56(4) 3.269(4) 139(3) 1_545
N2 H2N N1 0.87(4) 2.32(4) 2.726(4) 109(3) .
O5 H5O O6W 1.07(5) 1.55(5) 2.579(4) 161(4) 2_656
C7 H7B O4 0.97 2.43 3.351(4) 159.6 2_546
O6W H2W O4 0.881(10) 1.960(19) 2.819(4) 165(5) 2_656

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        76.50
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.208
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.037
_database_code_depnum_ccdc_archive 'CCDC 989765'
#######################################################################
#
#                 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_c:\nadeem

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N'-[(1E)-1-(3-methoxyphenyl)ethylidene]benzenesulfonohydrazide
;
_chemical_name_common            
;
N'-[(1E)-1-(3-methoxyphenyl)ethylidene]benzenesulfonohydrazide
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H16 N2 O3 S'
_chemical_formula_sum            'C15 H16 N2 O3 S'
_chemical_formula_weight         304.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   8.0437(3)
_cell_length_b                   9.7182(2)
_cell_length_c                   19.7716(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1545.55(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7206
_cell_measurement_theta_min      4.4664
_cell_measurement_theta_max      76.0618

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.308
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             640
_exptl_absorpt_coefficient_mu    1.964
_exptl_absorpt_correction_T_min  0.71728
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15858
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_sigmaI/netI    0.0228
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.47
_diffrn_reflns_theta_max         76.33
_reflns_number_total             3224
_reflns_number_gt                3058
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0385P)²+0.1615P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.129(15)
_refine_ls_number_reflns         3224
_refine_ls_number_parameters     215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0763
_refine_ls_wR_factor_gt          0.0744
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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
S1 S 0.97385(5) 0.37499(4) 0.236584(18) 0.03722(10) Uani 1 1 d . . .
O1 O 0.9605(2) 0.28918(13) 0.17843(6) 0.0542(3) Uani 1 1 d . . .
O2 O 1.06737(15) 0.50040(11) 0.23291(7) 0.0468(3) Uani 1 1 d . . .
O3 O 1.0432(18) 0.6924(15) 0.5424(7) 0.080(2) Uani 0.50 1 d P A 1
O31 O 1.081(2) 0.6970(14) 0.5427(7) 0.120(6) Uani 0.50 1 d P A 2
N1 N 1.06398(19) 0.27820(14) 0.29417(7) 0.0401(3) Uani 1 1 d . . .
N2 N 1.07411(17) 0.34390(13) 0.35695(6) 0.0392(3) Uani 1 1 d . . .
C1 C 0.77431(19) 0.41548(15) 0.26674(9) 0.0379(3) Uani 1 1 d . . .
C2 C 0.7550(2) 0.52156(18) 0.31287(9) 0.0439(4) Uani 1 1 d . . .
H2 H 0.8459 0.5733 0.3269 0.053 Uiso 1 1 calc R . .
C3 C 0.5974(3) 0.5488(2) 0.33756(11) 0.0561(5) Uani 1 1 d . . .
H3 H 0.5823 0.6191 0.3689 0.067 Uiso 1 1 calc R . .
C4 C 0.4627(3) 0.4728(2) 0.31617(12) 0.0663(5) Uani 1 1 d . . .
H4 H 0.3571 0.4924 0.3327 0.080 Uiso 1 1 calc R . .
C5 C 0.4846(2) 0.3673(2) 0.27014(12) 0.0662(5) Uani 1 1 d . . .
H5 H 0.3935 0.3160 0.2559 0.079 Uiso 1 1 calc R . .
C6 C 0.6402(2) 0.3378(2) 0.24519(10) 0.0539(4) Uani 1 1 d . . .
H6 H 0.6551 0.2666 0.2143 0.065 Uiso 1 1 calc R . .
C7 C 1.1324(2) 0.27444(18) 0.40644(9) 0.0454(4) Uani 1 1 d . . .
C8 C 1.1415(2) 0.34940(19) 0.47195(9) 0.0478(4) Uani 1 1 d . . .
C9 C 1.0959(3) 0.4885(2) 0.47477(10) 0.0586(5) Uani 1 1 d . A .
H9 H 1.0611 0.5333 0.4357 0.070 Uiso 1 1 calc R . .
C10 C 1.1023(4) 0.5593(2) 0.53499(10) 0.0650(6) Uani 1 1 d . . .
C11 C 1.1564(3) 0.4934(3) 0.59388(10) 0.0711(6) Uani 1 1 d . A .
H11 H 1.1630 0.5414 0.6345 0.085 Uiso 1 1 calc R . .
C12 C 1.1994(4) 0.3574(3) 0.59097(11) 0.0769(7) Uani 1 1 d . . .
H12 H 1.2338 0.3128 0.6302 0.092 Uiso 1 1 calc R A .
C13 C 1.1926(3) 0.2846(2) 0.53058(11) 0.0661(6) Uani 1 1 d . A .
H13 H 1.2226 0.1921 0.5296 0.079 Uiso 1 1 calc R . .
C14 C 1.1905(4) 0.1280(2) 0.40091(12) 0.0797(8) Uani 1 1 d . . .
H14A H 1.0978 0.0670 0.4072 0.120 Uiso 1 1 calc R . .
H14B H 1.2727 0.1102 0.4350 0.120 Uiso 1 1 calc R . .
H14C H 1.2382 0.1130 0.3570 0.120 Uiso 1 1 calc R . .
C15A C 0.986(3) 0.7619(17) 0.4885(7) 0.113(6) Uani 0.50 1 d P A 1
H15A H 0.9526 0.8525 0.5023 0.169 Uiso 0.50 1 calc PR A 1
H15B H 0.8925 0.7141 0.4697 0.169 Uiso 0.50 1 calc PR A 1
H15F H 1.0723 0.7688 0.4551 0.169 Uiso 0.50 1 calc PR A 1
C15B C 1.043(3) 0.7717(19) 0.4786(9) 0.158(10) Uani 0.50 1 d P A 2
H15D H 1.0295 0.8680 0.4880 0.238 Uiso 0.50 1 calc PR A 2
H15E H 0.9423 0.7360 0.4594 0.238 Uiso 0.50 1 calc PR A 2
H20C H 1.1328 0.7593 0.4472 0.238 Uiso 0.50 1 calc PR A 2
H1 H 1.028(3) 0.199(2) 0.2921(9) 0.045(5) 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
S1 O1 1.4244(12) . ?
S1 O2 1.4341(12) . ?
S1 N1 1.6452(14) . ?
S1 C1 1.7568(17) . ?
O3 C15A 1.34(2) . ?
O3 C10 1.386(13) . ?
O31 C10 1.357(13) . ?
O31 C15B 1.49(2) . ?
N1 N2 1.3982(18) . ?
N1 H1 0.83(2) . ?
N2 C7 1.278(2) . ?
C1 C6 1.384(2) . ?
C1 C2 1.385(2) . ?
C2 C3 1.384(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.376(3) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C8 1.488(2) . ?
C7 C14 1.502(3) . ?
C8 C13 1.382(3) . ?
C8 C9 1.402(3) . ?
C9 C10 1.376(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.398(3) . ?
C11 C12 1.367(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.389(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15A H15A 0.9600 . ?
C15A H15B 0.9600 . ?
C15A H15F 0.9600 . ?
C15B H15D 0.9600 . ?
C15B H15E 0.9600 . ?
C15B H20C 0.9600 . ?

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 S1 O2 119.75(8) . . ?
O1 S1 N1 104.91(8) . . ?
O2 S1 N1 106.85(7) . . ?
O1 S1 C1 109.64(9) . . ?
O2 S1 C1 107.82(7) . . ?
N1 S1 C1 107.21(8) . . ?
C15A O3 C10 120.2(12) . . ?
C10 O31 C15B 114.1(12) . . ?
N2 N1 S1 112.27(10) . . ?
N2 N1 H1 119.4(13) . . ?
S1 N1 H1 110.4(14) . . ?
C7 N2 N1 117.38(14) . . ?
C6 C1 C2 121.42(16) . . ?
C6 C1 S1 119.03(13) . . ?
C2 C1 S1 119.53(12) . . ?
C3 C2 C1 118.53(17) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C4 C3 C2 120.61(19) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 120.0(2) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 120.47(19) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.99(18) . . ?
C5 C6 H6 120.5 . . ?
C1 C6 H6 120.5 . . ?
N2 C7 C8 115.21(15) . . ?
N2 C7 C14 123.99(17) . . ?
C8 C7 C14 120.80(16) . . ?
C13 C8 C9 118.97(19) . . ?
C13 C8 C7 121.43(18) . . ?
C9 C8 C7 119.60(15) . . ?
C10 C9 C8 120.44(18) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
O31 C10 C9 125.9(6) . . ?
O31 C10 O3 12.9(14) . . ?
C9 C10 O3 123.0(6) . . ?
O31 C10 C11 113.3(6) . . ?
C9 C10 C11 120.2(2) . . ?
O3 C10 C11 116.5(6) . . ?
C12 C11 C10 119.1(2) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 121.3(2) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C8 C13 C12 120.0(2) . . ?
C8 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C7 C14 H14A 109.5 . . ?
C7 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C7 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O3 C15A H15A 109.5 . . ?
O3 C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
O3 C15A H15F 109.5 . . ?
H15A C15A H15F 109.5 . . ?
H15B C15A H15F 109.5 . . ?
O31 C15B H15D 109.5 . . ?
O31 C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
O31 C15B H20C 109.5 . . ?
H15D C15B H20C 109.5 . . ?
H15E C15B H20C 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
O1 S1 N1 N2 -174.98(12) . . . . ?
O2 S1 N1 N2 56.92(13) . . . . ?
C1 S1 N1 N2 -58.46(13) . . . . ?
S1 N1 N2 C7 175.64(13) . . . . ?
O1 S1 C1 C6 16.42(17) . . . . ?
O2 S1 C1 C6 148.34(14) . . . . ?
N1 S1 C1 C6 -96.94(16) . . . . ?
O1 S1 C1 C2 -165.40(13) . . . . ?
O2 S1 C1 C2 -33.48(16) . . . . ?
N1 S1 C1 C2 81.24(14) . . . . ?
C6 C1 C2 C3 0.2(3) . . . . ?
S1 C1 C2 C3 -177.98(14) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C2 C3 C4 C5 0.6(3) . . . . ?
C3 C4 C5 C6 -0.2(3) . . . . ?
C4 C5 C6 C1 -0.2(3) . . . . ?
C2 C1 C6 C5 0.2(3) . . . . ?
S1 C1 C6 C5 178.39(15) . . . . ?
N1 N2 C7 C8 179.64(14) . . . . ?
N1 N2 C7 C14 0.2(3) . . . . ?
N2 C7 C8 C13 176.1(2) . . . . ?
C14 C7 C8 C13 -4.4(3) . . . . ?
N2 C7 C8 C9 -3.3(3) . . . . ?
C14 C7 C8 C9 176.1(2) . . . . ?
C13 C8 C9 C10 0.1(4) . . . . ?
C7 C8 C9 C10 179.5(2) . . . . ?
C15B O31 C10 C9 2(2) . . . . ?
C15B O31 C10 O3 -80(5) . . . . ?
C15B O31 C10 C11 173.2(14) . . . . ?
C8 C9 C10 O31 171.4(10) . . . . ?
C8 C9 C10 O3 -173.3(8) . . . . ?
C8 C9 C10 C11 0.8(4) . . . . ?
C15A O3 C10 O31 103(5) . . . . ?
C15A O3 C10 C9 -4.4(19) . . . . ?
C15A O3 C10 C11 -178.7(14) . . . . ?
O31 C10 C11 C12 -173.0(9) . . . . ?
C9 C10 C11 C12 -1.3(4) . . . . ?
O3 C10 C11 C12 173.2(7) . . . . ?
C10 C11 C12 C13 1.0(5) . . . . ?
C9 C8 C13 C12 -0.4(4) . . . . ?
C7 C8 C13 C12 -179.9(2) . . . . ?
C11 C12 C13 C8 -0.1(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.83(2) 2.13(2) 2.9481(18) 169.3(18) 4_745
C3 H3 O3 0.93 2.56 3.486(14) 178.4 3_466
C3 H3 O31 0.93 2.50 3.424(15) 172.3 3_466
C6 H6 O1 0.93 2.57 2.933(3) 103.9 .
C9 H9 N2 0.93 2.41 2.726(2) 99.6 .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        76.33
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.134
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.035
_database_code_depnum_ccdc_archive 'CCDC 989766'
#######################################################################
#
#                 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_c:\nadeem

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
N'-[(1E,2E)-1-(4-bromophenyl)-3-(3,4-dimethoxyphenyl)
prop-2-en-1-ylidene]benzenesulfonohydrazide
;
_chemical_name_common            
;
N'-[(1E,2E)-1-(4-bromophenyl)-3-(3,4-dimethoxyphenyl)
prop-2-en-1-ylidene]benzenesulfonohydrazide
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H21 Br N2 O4 S'
_chemical_formula_sum            'C23 H21 Br N2 O4 S'
_chemical_formula_weight         501.39

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 2 1/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   8.3535(2)
_cell_length_b                   15.3411(3)
_cell_length_c                   17.7711(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 98.086(2)
_cell_angle_gamma                90.00
_cell_volume                     2254.76(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9783
_cell_measurement_theta_min      2.8781
_cell_measurement_theta_max      76.3558

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1024
_exptl_absorpt_coefficient_mu    3.621
_exptl_absorpt_correction_T_min  0.45609
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies,
Version 1.171.36.20 (release 27-06-2012 CrysAlis171 .NET)
(compiled Jul 11 2012,15:38:31)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           ?

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas, CCD'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22055
_diffrn_reflns_av_R_equivalents  0.0256
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         76.55
_reflns_number_total             4720
_reflns_number_gt                4244
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlis PRO (Agilent, 2012)'
_computing_cell_refinement       'CrysAlis PRO (Agilent, 2012)'
_computing_data_reduction        'CrysAlis PRO (Agilent, 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0465P)²+1.5589P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4720
_refine_ls_number_parameters     286
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.1117
_refine_ls_wR_factor_gt          0.1085
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
Br1 Br 0.24689(5) 0.61949(3) 0.48020(2) 0.09077(16) Uani 1 1 d . . .
S1 S 0.18279(6) 0.16207(3) 0.79868(3) 0.04629(14) Uani 1 1 d . . .
O1 O 0.2455(2) 0.12146(12) 0.73690(12) 0.0635(5) Uani 1 1 d . . .
O2 O 0.1920(2) 0.11927(12) 0.87043(11) 0.0608(4) Uani 1 1 d . . .
O3 O 0.7735(3) 0.71193(11) 1.01579(10) 0.0662(5) Uani 1 1 d . . .
O4 O 0.9164(2) 0.60076(11) 1.10848(9) 0.0547(4) Uani 1 1 d . . .
N1 N 0.2828(2) 0.25435(13) 0.81712(12) 0.0497(4) Uani 1 1 d . . .
N2 N 0.2700(2) 0.30893(13) 0.75257(11) 0.0479(4) Uani 1 1 d . . .
C1 C 0.3294(3) 0.43914(15) 0.69366(13) 0.0462(5) Uani 1 1 d . . .
C2 C 0.4591(3) 0.47777(18) 0.66570(15) 0.0572(6) Uani 1 1 d . . .
H2A H 0.5633 0.4685 0.6906 0.069 Uiso 1 1 calc R . .
C3 C 0.4364(3) 0.52970(19) 0.60164(16) 0.0626(7) Uani 1 1 d . . .
H3 H 0.5245 0.5545 0.5830 0.075 Uiso 1 1 calc R . .
C4 C 0.2817(3) 0.54439(18) 0.56576(15) 0.0597(6) Uani 1 1 d . . .
C5 C 0.1496(3) 0.50728(18) 0.59220(15) 0.0576(6) Uani 1 1 d . . .
H5 H 0.0455 0.5179 0.5677 0.069 Uiso 1 1 calc R . .
C6 C 0.1740(3) 0.45464(17) 0.65505(14) 0.0517(5) Uani 1 1 d . . .
H6 H 0.0855 0.4286 0.6724 0.062 Uiso 1 1 calc R . .
C7 C 0.3502(3) 0.38130(14) 0.76111(13) 0.0454(5) Uani 1 1 d . . .
C8 C -0.0199(3) 0.19050(14) 0.76784(13) 0.0451(5) Uani 1 1 d . . .
C9 C -0.1217(3) 0.20453(18) 0.82166(17) 0.0621(6) Uani 1 1 d . . .
H9 H -0.0824 0.2017 0.8732 0.075 Uiso 1 1 calc R . .
C10 C -0.2838(4) 0.2229(2) 0.7974(2) 0.0785(9) Uani 1 1 d . . .
H10 H -0.3542 0.2313 0.8330 0.094 Uiso 1 1 calc R . .
C11 C -0.3396(4) 0.2287(2) 0.7220(2) 0.0801(9) Uani 1 1 d . . .
H11 H -0.4483 0.2407 0.7063 0.096 Uiso 1 1 calc R . .
C12 C -0.2374(4) 0.2171(2) 0.6685(2) 0.0783(9) Uani 1 1 d . . .
H12 H -0.2766 0.2227 0.6171 0.094 Uiso 1 1 calc R . .
C13 C -0.0753(3) 0.19686(18) 0.69112(16) 0.0611(6) Uani 1 1 d . . .
H13 H -0.0059 0.1878 0.6553 0.073 Uiso 1 1 calc R . .
C14 C 0.4567(3) 0.40569(16) 0.83051(14) 0.0484(5) Uani 1 1 d . . .
H14 H 0.4875 0.3618 0.8657 0.058 Uiso 1 1 calc R . .
C15 C 0.5129(3) 0.48513(16) 0.84739(13) 0.0483(5) Uani 1 1 d . . .
H15 H 0.4811 0.5290 0.8123 0.058 Uiso 1 1 calc R . .
C16 C 0.6210(3) 0.51011(15) 0.91649(12) 0.0445(5) Uani 1 1 d . . .
C17 C 0.7001(3) 0.45044(15) 0.96764(14) 0.0522(5) Uani 1 1 d . . .
H17 H 0.6852 0.3911 0.9587 0.063 Uiso 1 1 calc R . .
C18 C 0.8009(3) 0.47825(16) 1.03175(14) 0.0518(5) Uani 1 1 d . . .
H18 H 0.8536 0.4374 1.0651 0.062 Uiso 1 1 calc R . .
C19 C 0.8237(3) 0.56572(15) 1.04660(12) 0.0438(4) Uani 1 1 d . . .
C20 C 0.7458(3) 0.62680(14) 0.99547(13) 0.0458(5) Uani 1 1 d . . .
C21 C 0.6474(3) 0.59894(15) 0.93110(13) 0.0456(5) Uani 1 1 d . . .
H21 H 0.5977 0.6399 0.8969 0.055 Uiso 1 1 calc R . .
C22 C 1.0019(3) 0.5414(2) 1.16211(15) 0.0629(7) Uani 1 1 d . . .
H22A H 0.9257 0.5068 1.1848 0.094 Uiso 1 1 calc R . .
H22B H 1.0682 0.5737 1.2010 0.094 Uiso 1 1 calc R . .
H22C H 1.0689 0.5040 1.1365 0.094 Uiso 1 1 calc R . .
C23 C 0.7128(5) 0.77713(18) 0.96299(18) 0.0829(10) Uani 1 1 d . . .
H23A H 0.7455 0.7646 0.9145 0.124 Uiso 1 1 calc R . .
H23B H 0.7547 0.8329 0.9806 0.124 Uiso 1 1 calc R . .
H23C H 0.5969 0.7781 0.9582 0.124 Uiso 1 1 calc R . .
H1 H 0.256(4) 0.276(2) 0.8575(19) 0.070(9) Uiso 1 1 d . . .


_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C4 1.897(3) . ?
S1 O1 1.4247(19) . ?
S1 O2 1.4267(19) . ?
S1 N1 1.653(2) . ?
S1 C8 1.760(2) . ?
O3 C20 1.366(3) . ?
O3 C23 1.416(3) . ?
O4 C19 1.363(3) . ?
O4 C22 1.434(3) . ?
N1 N2 1.412(3) . ?
N1 H1 0.85(3) . ?
N2 C7 1.295(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.400(3) . ?
C1 C7 1.482(3) . ?
C2 C3 1.381(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.382(4) . ?
C5 C6 1.370(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 C14 1.464(3) . ?
C8 C13 1.380(3) . ?
C8 C9 1.383(4) . ?
C9 C10 1.391(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.359(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.376(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.391(4) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.325(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.469(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.390(3) . ?
C16 C21 1.399(3) . ?
C17 C18 1.385(3) . ?
C17 H17 0.9300 . ?
C18 C19 1.376(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.401(3) . ?
C20 C21 1.379(3) . ?
C21 H21 0.9300 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?

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 S1 O2 120.54(12) . . ?
O1 S1 N1 107.27(12) . . ?
O2 S1 N1 104.76(11) . . ?
O1 S1 C8 108.09(11) . . ?
O2 S1 C8 108.70(11) . . ?
N1 S1 C8 106.68(10) . . ?
C20 O3 C23 117.9(2) . . ?
C19 O4 C22 117.33(19) . . ?
N2 N1 S1 111.60(15) . . ?
N2 N1 H1 117(2) . . ?
S1 N1 H1 109(2) . . ?
C7 N2 N1 115.74(19) . . ?
C2 C1 C6 118.0(2) . . ?
C2 C1 C7 122.5(2) . . ?
C6 C1 C7 119.6(2) . . ?
C3 C2 C1 121.2(2) . . ?
C3 C2 H2A 119.4 . . ?
C1 C2 H2A 119.4 . . ?
C4 C3 C2 119.2(2) . . ?
C4 C3 H3 120.4 . . ?
C2 C3 H3 120.4 . . ?
C3 C4 C5 121.2(3) . . ?
C3 C4 Br1 119.9(2) . . ?
C5 C4 Br1 118.9(2) . . ?
C6 C5 C4 119.0(2) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.4(2) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
N2 C7 C14 124.1(2) . . ?
N2 C7 C1 114.8(2) . . ?
C14 C7 C1 121.09(19) . . ?
C13 C8 C9 121.2(2) . . ?
C13 C8 S1 119.96(19) . . ?
C9 C8 S1 118.79(19) . . ?
C8 C9 C10 119.0(3) . . ?
C8 C9 H9 120.5 . . ?
C10 C9 H9 120.5 . . ?
C11 C10 C9 120.2(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 120.8(3) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C11 C12 C13 120.2(3) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 118.6(3) . . ?
C8 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C7 125.4(2) . . ?
C15 C14 H14 117.3 . . ?
C7 C14 H14 117.3 . . ?
C14 C15 C16 125.8(2) . . ?
C14 C15 H15 117.1 . . ?
C16 C15 H15 117.1 . . ?
C17 C16 C21 118.2(2) . . ?
C17 C16 C15 123.7(2) . . ?
C21 C16 C15 118.1(2) . . ?
C18 C17 C16 120.9(2) . . ?
C18 C17 H17 119.6 . . ?
C16 C17 H17 119.6 . . ?
C19 C18 C17 120.7(2) . . ?
C19 C18 H18 119.7 . . ?
C17 C18 H18 119.7 . . ?
O4 C19 C18 126.0(2) . . ?
O4 C19 C20 114.78(19) . . ?
C18 C19 C20 119.3(2) . . ?
O3 C20 C21 125.1(2) . . ?
O3 C20 C19 114.96(19) . . ?
C21 C20 C19 119.9(2) . . ?
C20 C21 C16 121.0(2) . . ?
C20 C21 H21 119.5 . . ?
C16 C21 H21 119.5 . . ?
O4 C22 H22A 109.5 . . ?
O4 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
O4 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
O3 C23 H23A 109.5 . . ?
O3 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
O3 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 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
O1 S1 N1 N2 57.14(19) . . . . ?
O2 S1 N1 N2 -173.65(16) . . . . ?
C8 S1 N1 N2 -58.49(18) . . . . ?
S1 N1 N2 C7 -177.37(16) . . . . ?
C6 C1 C2 C3 -0.2(4) . . . . ?
C7 C1 C2 C3 178.4(2) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C2 C3 C4 C5 -0.8(4) . . . . ?
C2 C3 C4 Br1 177.3(2) . . . . ?
C3 C4 C5 C6 -0.3(4) . . . . ?
Br1 C4 C5 C6 -178.5(2) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C2 C1 C6 C5 -0.9(4) . . . . ?
C7 C1 C6 C5 -179.6(2) . . . . ?
N1 N2 C7 C14 3.6(3) . . . . ?
N1 N2 C7 C1 -177.56(19) . . . . ?
C2 C1 C7 N2 -132.5(2) . . . . ?
C6 C1 C7 N2 46.2(3) . . . . ?
C2 C1 C7 C14 46.4(3) . . . . ?
C6 C1 C7 C14 -134.9(2) . . . . ?
O1 S1 C8 C13 -19.4(2) . . . . ?
O2 S1 C8 C13 -151.9(2) . . . . ?
N1 S1 C8 C13 95.7(2) . . . . ?
O1 S1 C8 C9 159.4(2) . . . . ?
O2 S1 C8 C9 27.0(2) . . . . ?
N1 S1 C8 C9 -85.5(2) . . . . ?
C13 C8 C9 C10 1.8(4) . . . . ?
S1 C8 C9 C10 -177.0(2) . . . . ?
C8 C9 C10 C11 -1.3(5) . . . . ?
C9 C10 C11 C12 -0.4(5) . . . . ?
C10 C11 C12 C13 1.6(5) . . . . ?
C9 C8 C13 C12 -0.6(4) . . . . ?
S1 C8 C13 C12 178.2(2) . . . . ?
C11 C12 C13 C8 -1.2(5) . . . . ?
N2 C7 C14 C15 -164.8(2) . . . . ?
C1 C7 C14 C15 16.4(4) . . . . ?
C7 C14 C15 C16 -179.4(2) . . . . ?
C14 C15 C16 C17 11.2(4) . . . . ?
C14 C15 C16 C21 -169.7(2) . . . . ?
C21 C16 C17 C18 0.7(4) . . . . ?
C15 C16 C17 C18 179.8(2) . . . . ?
C16 C17 C18 C19 0.6(4) . . . . ?
C22 O4 C19 C18 1.9(3) . . . . ?
C22 O4 C19 C20 -178.8(2) . . . . ?
C17 C18 C19 O4 178.3(2) . . . . ?
C17 C18 C19 C20 -1.0(4) . . . . ?
C23 O3 C20 C21 -7.8(4) . . . . ?
C23 O3 C20 C19 173.4(3) . . . . ?
O4 C19 C20 O3 -0.5(3) . . . . ?
C18 C19 C20 O3 178.9(2) . . . . ?
O4 C19 C20 C21 -179.3(2) . . . . ?
C18 C19 C20 C21 0.0(3) . . . . ?
O3 C20 C21 C16 -177.4(2) . . . . ?
C19 C20 C21 C16 1.3(4) . . . . ?
C17 C16 C21 C20 -1.7(3) . . . . ?
C15 C16 C21 C20 179.2(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        76.55
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.485
_refine_diff_density_min         -0.535
_refine_diff_density_rms         0.047
_database_code_depnum_ccdc_archive 'CCDC 989767'
