# 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H20 Cl3 N O3'
_chemical_formula_sum            'C18 H20 Cl3 N O3'
_chemical_formula_weight         404.70
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   6.4986(13)
_cell_length_b                   7.2522(15)
_cell_length_c                   40.288(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1898.7(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    5223
_cell_measurement_theta_min      1.5164
_cell_measurement_theta_max      27.4739

_exptl_crystal_description       block
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.37
_exptl_crystal_size_min          0.29
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             840
_exptl_absorpt_coefficient_mu    0.499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11590
_diffrn_reflns_av_R_equivalents  0.0414
_diffrn_reflns_av_sigmaI/netI    0.0383
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       52
_diffrn_reflns_theta_min         2.99
_diffrn_reflns_theta_max         27.45
_reflns_number_total             4298
_reflns_number_gt                3813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_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)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_number_reflns         4298
_refine_ls_number_parameters     230
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0595
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1892
_refine_ls_wR_factor_gt          0.1730
_refine_ls_goodness_of_fit_ref   1.380
_refine_ls_restrained_S_all      1.380
_refine_ls_shift/su_max          0.027
_refine_ls_shift/su_mean         0.004

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.78424(15) 0.20003(13) 0.60118(2) 0.0514(3) Uani 1 1 d . . .
Cl2 Cl 0.72775(16) -0.12766(12) 0.64030(2) 0.0491(3) Uani 1 1 d . . .
Cl3 Cl 0.74331(15) 0.22713(15) 0.67175(2) 0.0559(3) Uani 1 1 d . . .
O1 O 0.2592(6) 0.5850(3) 0.61259(5) 0.0540(8) Uani 1 1 d . . .
O2 O 0.2542(4) 0.2355(3) 0.69138(5) 0.0407(6) Uani 1 1 d . . .
O3 O 0.2827(4) 0.5332(2) 0.67630(5) 0.0343(5) Uani 1 1 d . . .
N1 N 0.3433(4) 0.3084(3) 0.63783(6) 0.0304(5) Uani 1 1 d . . .
C1 C 0.2736(6) -0.1707(5) 0.44059(7) 0.0452(8) Uani 1 1 d . . .
H1A H 0.1448 -0.1301 0.4303 0.068 Uiso 1 1 calc R . .
H1C H 0.2743 -0.3055 0.4423 0.068 Uiso 1 1 calc R . .
H1B H 0.3902 -0.1304 0.4270 0.068 Uiso 1 1 calc R . .
C2 C 0.2915(5) -0.0875(4) 0.47494(7) 0.0346(6) Uani 1 1 d . . .
C3 C 0.3636(5) 0.0912(4) 0.47922(7) 0.0360(7) Uani 1 1 d . . .
H3 H 0.4052 0.1608 0.4604 0.043 Uiso 1 1 calc R . .
C4 C 0.3757(5) 0.1699(4) 0.51071(7) 0.0343(6) Uani 1 1 d . . .
H4 H 0.4240 0.2929 0.5131 0.041 Uiso 1 1 calc R . .
C5 C 0.3178(5) 0.0700(4) 0.53873(6) 0.0309(6) Uani 1 1 d . . .
C6 C 0.2525(5) -0.1121(4) 0.53442(7) 0.0343(6) Uani 1 1 d . . .
H6 H 0.2183 -0.1845 0.5533 0.041 Uiso 1 1 calc R . .
C7 C 0.2370(6) -0.1880(4) 0.50302(8) 0.0406(7) Uani 1 1 d . . .
H7 H 0.1883 -0.3108 0.5006 0.049 Uiso 1 1 calc R . .
C8 C 0.3236(5) 0.1527(4) 0.57241(7) 0.0297(6) Uani 1 1 d . . .
C9 C 0.3184(6) 0.3356(4) 0.57731(7) 0.0344(7) Uani 1 1 d . . .
H9 H 0.3218 0.4133 0.5583 0.041 Uiso 1 1 calc R . .
C10 C 0.3078(6) 0.4241(4) 0.61034(7) 0.0360(7) Uani 1 1 d . . .
C11 C 0.4173(5) 0.1182(4) 0.63341(7) 0.0313(6) Uani 1 1 d . . .
H11 H 0.3617 0.0460 0.6526 0.038 Uiso 1 1 calc R . .
C12 C 0.3317(6) 0.0269(4) 0.60201(7) 0.0338(7) Uani 1 1 d . . .
H12A H 0.4183 -0.0811 0.5965 0.041 Uiso 1 1 calc R . .
H12B H 0.1911 -0.0187 0.6067 0.041 Uiso 1 1 calc R . .
C13 C 0.6540(6) 0.1093(5) 0.63632(8) 0.0399(7) Uani 1 1 d . . .
C14 C 0.2858(5) 0.3543(4) 0.67136(7) 0.0305(6) Uani 1 1 d . . .
C15 C 0.2336(6) 0.6063(4) 0.70954(7) 0.0349(7) Uani 1 1 d . . .
C16 C 0.0119(6) 0.5567(5) 0.71875(9) 0.0455(8) Uani 1 1 d . . .
H16A H -0.0803 0.5919 0.7006 0.068 Uiso 1 1 calc R . .
H16C H -0.0276 0.6229 0.7390 0.068 Uiso 1 1 calc R . .
H16B H 0.0018 0.4236 0.7226 0.068 Uiso 1 1 calc R . .
C17 C 0.2537(7) 0.8136(4) 0.70407(7) 0.0401(7) Uani 1 1 d . . .
H17B H 0.3946 0.8426 0.6971 0.060 Uiso 1 1 calc R . .
H17C H 0.2225 0.8786 0.7248 0.060 Uiso 1 1 calc R . .
H17A H 0.1571 0.8527 0.6868 0.060 Uiso 1 1 calc R . .
C18 C 0.3861(7) 0.5386(5) 0.73514(8) 0.0480(9) Uani 1 1 d . . .
H18B H 0.3615 0.4076 0.7396 0.072 Uiso 1 1 calc R . .
H18C H 0.3693 0.6092 0.7557 0.072 Uiso 1 1 calc R . .
H18A H 0.5264 0.5550 0.7267 0.072 Uiso 1 1 calc R . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl1 C13 1.776(4) . ?
Cl2 C13 1.791(3) . ?
Cl3 C13 1.762(3) . ?
O1 C10 1.212(4) . ?
O2 C14 1.198(3) . ?
O3 C14 1.313(3) . ?
O3 C15 1.475(3) . ?
N1 C10 1.408(4) . ?
N1 C14 1.440(4) . ?
N1 C11 1.472(4) . ?
C1 C2 1.514(4) . ?
C1 H1A 0.9800 . ?
C1 H1C 0.9800 . ?
C1 H1B 0.9800 . ?
C2 C3 1.389(5) . ?
C2 C7 1.392(4) . ?
C3 C4 1.393(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(4) . ?
C5 C8 1.484(4) . ?
C6 C7 1.383(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.341(4) . ?
C8 C12 1.502(4) . ?
C9 C10 1.479(4) . ?
C9 H9 0.9500 . ?
C11 C12 1.533(4) . ?
C11 C13 1.544(5) . ?
C11 H11 1.0000 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C15 C18 1.512(5) . ?
C15 C17 1.525(4) . ?
C15 C16 1.530(5) . ?
C16 H16A 0.9800 . ?
C16 H16C 0.9800 . ?
C16 H16B 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C17 H17A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C18 H18A 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
C14 O3 C15 119.8(2) . . ?
C10 N1 C14 123.9(2) . . ?
C10 N1 C11 121.1(2) . . ?
C14 N1 C11 114.5(2) . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1C C1 H1B 109.5 . . ?
C3 C2 C7 118.3(3) . . ?
C3 C2 C1 120.8(3) . . ?
C7 C2 C1 121.0(3) . . ?
C2 C3 C4 121.0(3) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 120.6(3) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C4 C5 C6 118.2(3) . . ?
C4 C5 C8 121.6(3) . . ?
C6 C5 C8 120.2(3) . . ?
C7 C6 C5 120.8(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C9 C8 C5 122.3(3) . . ?
C9 C8 C12 119.0(3) . . ?
C5 C8 C12 118.8(2) . . ?
C8 C9 C10 124.3(3) . . ?
C8 C9 H9 117.9 . . ?
C10 C9 H9 117.9 . . ?
O1 C10 N1 123.9(3) . . ?
O1 C10 C9 119.8(3) . . ?
N1 C10 C9 116.2(2) . . ?
N1 C11 C12 112.7(2) . . ?
N1 C11 C13 110.8(3) . . ?
C12 C11 C13 114.0(3) . . ?
N1 C11 H11 106.2 . . ?
C12 C11 H11 106.2 . . ?
C13 C11 H11 106.2 . . ?
C8 C12 C11 113.9(2) . . ?
C8 C12 H12A 108.8 . . ?
C11 C12 H12A 108.8 . . ?
C8 C12 H12B 108.8 . . ?
C11 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C11 C13 Cl3 111.7(2) . . ?
C11 C13 Cl1 113.5(2) . . ?
Cl3 C13 Cl1 108.01(19) . . ?
C11 C13 Cl2 108.3(2) . . ?
Cl3 C13 Cl2 107.75(18) . . ?
Cl1 C13 Cl2 107.42(19) . . ?
O2 C14 O3 127.3(3) . . ?
O2 C14 N1 120.7(3) . . ?
O3 C14 N1 112.0(2) . . ?
O3 C15 C18 111.1(3) . . ?
O3 C15 C17 101.8(2) . . ?
C18 C15 C17 111.3(3) . . ?
O3 C15 C16 109.8(3) . . ?
C18 C15 C16 112.0(3) . . ?
C17 C15 C16 110.3(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
C15 C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
H17B C17 H17A 109.5 . . ?
H17C C17 H17A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
H18B C18 H18A 109.5 . . ?
H18C C18 H18A 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
C7 C2 C3 C4 -1.7(5) . . . . ?
C1 C2 C3 C4 178.5(3) . . . . ?
C2 C3 C4 C5 0.7(5) . . . . ?
C3 C4 C5 C6 1.6(5) . . . . ?
C3 C4 C5 C8 -178.2(3) . . . . ?
C4 C5 C6 C7 -2.9(5) . . . . ?
C8 C5 C6 C7 176.9(3) . . . . ?
C5 C6 C7 C2 1.9(5) . . . . ?
C3 C2 C7 C6 0.4(5) . . . . ?
C1 C2 C7 C6 -179.8(3) . . . . ?
C4 C5 C8 C9 22.1(5) . . . . ?
C6 C5 C8 C9 -157.7(3) . . . . ?
C4 C5 C8 C12 -159.0(3) . . . . ?
C6 C5 C8 C12 21.2(5) . . . . ?
C5 C8 C9 C10 175.1(3) . . . . ?
C12 C8 C9 C10 -3.8(6) . . . . ?
C14 N1 C10 O1 13.4(6) . . . . ?
C11 N1 C10 O1 -175.3(4) . . . . ?
C14 N1 C10 C9 -162.4(3) . . . . ?
C11 N1 C10 C9 9.0(5) . . . . ?
C8 C9 C10 O1 -164.0(4) . . . . ?
C8 C9 C10 N1 11.9(6) . . . . ?
C10 N1 C11 C12 -34.5(4) . . . . ?
C14 N1 C11 C12 137.6(3) . . . . ?
C10 N1 C11 C13 94.6(4) . . . . ?
C14 N1 C11 C13 -93.3(3) . . . . ?
C9 C8 C12 C11 -23.0(5) . . . . ?
C5 C8 C12 C11 158.1(3) . . . . ?
N1 C11 C12 C8 40.5(4) . . . . ?
C13 C11 C12 C8 -87.0(3) . . . . ?
N1 C11 C13 Cl3 48.4(3) . . . . ?
C12 C11 C13 Cl3 176.84(19) . . . . ?
N1 C11 C13 Cl1 -74.0(3) . . . . ?
C12 C11 C13 Cl1 54.5(3) . . . . ?
N1 C11 C13 Cl2 166.89(19) . . . . ?
C12 C11 C13 Cl2 -64.7(3) . . . . ?
C15 O3 C14 O2 -0.8(6) . . . . ?
C15 O3 C14 N1 -178.0(3) . . . . ?
C10 N1 C14 O2 154.7(3) . . . . ?
C11 N1 C14 O2 -17.2(4) . . . . ?
C10 N1 C14 O3 -27.8(5) . . . . ?
C11 N1 C14 O3 160.3(3) . . . . ?
C14 O3 C15 C18 59.9(4) . . . . ?
C14 O3 C15 C17 178.4(3) . . . . ?
C14 O3 C15 C16 -64.7(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.988
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.475
_refine_diff_density_min         -0.374
_refine_diff_density_rms         0.064
_database_code_depnum_ccdc_archive 'CCDC 980927'
#######################################################################
#
#                 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_a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H23 N O6 S'
_chemical_formula_sum            'C22 H23 N O6 S'
_chemical_formula_weight         429.47
_chemical_absolute_configuration ad

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

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   5.8326(12)
_cell_length_b                   8.9210(18)
_cell_length_c                   40.497(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2107.2(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3917
_cell_measurement_theta_min      2.7368
_cell_measurement_theta_max      27.4770

_exptl_crystal_description       rod
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             904
_exptl_absorpt_coefficient_mu    0.192
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6309
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean 28.5714
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8536
_diffrn_reflns_av_R_equivalents  0.0497
_diffrn_reflns_av_sigmaI/netI    0.0755
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -52
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         3.04
_diffrn_reflns_theta_max         27.49
_reflns_number_total             4753
_reflns_number_gt                3911
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELX-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELX-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
 Mercury: visualization and analysis of crystal structures, C. F. Macrae,
 P. R. Edgington, P. McCabe, E. Pidcock, G. P. Shields, R. Taylor,
 M. Towler and J. van de Streek, J. Appl. Cryst., 39, 453-457, 2006.
;
_computing_publication_material  'SHELX-97 (Sheldrick, 2008)'

_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)+(0.0292P)²+1.6741P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.03(13)
_refine_ls_number_reflns         4753
_refine_ls_number_parameters     274
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0708
_refine_ls_wR_factor_ref         0.1377
_refine_ls_wR_factor_gt          0.1263
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.002
_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 0.42609(15) 0.49327(12) 0.92331(2) 0.0330(2) Uani 1 1 d . . .
O1 O -0.4505(5) 0.4094(3) 0.70682(6) 0.0447(7) Uani 1 1 d . . .
O2 O 0.5299(4) 0.3128(3) 0.86472(6) 0.0345(6) Uani 1 1 d . . .
O3 O 0.4489(4) 0.7753(3) 0.86584(8) 0.0424(7) Uani 1 1 d . . .
O4 O 0.0887(5) 0.8647(3) 0.86531(9) 0.0507(8) Uani 1 1 d . . .
O5 O 0.3147(5) 0.6106(3) 0.94100(7) 0.0411(7) Uani 1 1 d . . .
O6 O 0.6682(4) 0.4950(3) 0.91972(6) 0.0413(6) Uani 1 1 d . . .
N1 N 0.2984(4) 0.4958(4) 0.88577(7) 0.0302(6) Uani 1 1 d . . .
C1 C -0.6369(6) 0.5055(5) 0.69781(10) 0.0479(10) Uani 1 1 d . . .
H1A H -0.7003 0.4731 0.6766 0.072 Uiso 1 1 calc R . .
H1B H -0.5815 0.6089 0.6959 0.072 Uiso 1 1 calc R . .
H1C H -0.7564 0.5004 0.7148 0.072 Uiso 1 1 calc R . .
C2 C -0.3358(6) 0.4376(4) 0.73545(9) 0.0338(9) Uani 1 1 d . . .
C3 C -0.1529(6) 0.3430(5) 0.74223(10) 0.0387(9) Uani 1 1 d . . .
H3 H -0.1137 0.2665 0.7269 0.046 Uiso 1 1 calc R . .
C4 C -0.0281(6) 0.3584(4) 0.77069(10) 0.0370(9) Uani 1 1 d . . .
H4 H 0.0956 0.2917 0.7748 0.044 Uiso 1 1 calc R . .
C5 C -0.0791(6) 0.4705(4) 0.79384(8) 0.0286(7) Uani 1 1 d . . .
C6 C -0.2636(6) 0.5646(4) 0.78658(10) 0.0331(8) Uani 1 1 d . . .
H6 H -0.3042 0.6407 0.8019 0.040 Uiso 1 1 calc R . .
C7 C -0.3896(6) 0.5504(4) 0.75772(9) 0.0353(9) Uani 1 1 d . . .
H7 H -0.5121 0.6175 0.7532 0.042 Uiso 1 1 calc R . .
C8 C 0.3797(5) 0.4055(4) 0.86019(9) 0.0290(8) Uani 1 1 d . . .
C9 C 0.2633(6) 0.4222(4) 0.82834(9) 0.0300(8) Uani 1 1 d . . .
H9 H 0.3394 0.3865 0.8091 0.036 Uiso 1 1 calc R . .
C10 C 0.0555(6) 0.4849(4) 0.82463(8) 0.0275(7) Uani 1 1 d . . .
C11 C -0.0498(6) 0.5586(4) 0.85412(8) 0.0297(7) Uani 1 1 d . . .
H11B H -0.1533 0.4864 0.8652 0.036 Uiso 1 1 calc R . .
H11A H -0.1436 0.6447 0.8467 0.036 Uiso 1 1 calc R . .
C12 C 0.1285(6) 0.6139(4) 0.87905(9) 0.0294(8) Uani 1 1 d . . .
H12 H 0.0457 0.6339 0.9002 0.035 Uiso 1 1 calc R . .
C13 C 0.2478(6) 0.7579(4) 0.86922(9) 0.0308(8) Uani 1 1 d . . .
C14 C 0.1615(6) 1.0193(4) 0.86093(11) 0.0419(10) Uani 1 1 d . . .
H14A H 0.1613 1.0467 0.8372 0.050 Uiso 1 1 calc R . .
H14B H 0.3178 1.0343 0.8699 0.050 Uiso 1 1 calc R . .
C15 C -0.0072(7) 1.1115(5) 0.87942(11) 0.0440(10) Uani 1 1 d . . .
H15A H -0.1615 1.0927 0.8708 0.066 Uiso 1 1 calc R . .
H15B H 0.0305 1.2179 0.8768 0.066 Uiso 1 1 calc R . .
H15C H -0.0019 1.0848 0.9029 0.066 Uiso 1 1 calc R . .
C16 C 0.3427(6) 0.3208(5) 0.94056(9) 0.0328(8) Uani 1 1 d . . .
C17 C 0.1369(6) 0.3131(5) 0.95780(9) 0.0345(9) Uani 1 1 d . . .
H17 H 0.0397 0.3983 0.9594 0.041 Uiso 1 1 calc R . .
C18 C 0.0765(7) 0.1784(5) 0.97257(9) 0.0404(9) Uani 1 1 d . . .
H18 H -0.0631 0.1719 0.9846 0.048 Uiso 1 1 calc R . .
C19 C 0.2161(8) 0.0532(5) 0.97016(10) 0.0433(10) Uani 1 1 d . . .
C20 C 0.4194(8) 0.0651(5) 0.95288(10) 0.0488(11) Uani 1 1 d . . .
H20 H 0.5164 -0.0201 0.9511 0.059 Uiso 1 1 calc R . .
C21 C 0.4850(6) 0.1983(5) 0.93811(10) 0.0392(9) Uani 1 1 d . . .
H21 H 0.6260 0.2050 0.9265 0.047 Uiso 1 1 calc R . .
C22 C 0.1444(10) -0.0912(5) 0.98633(13) 0.0690(16) Uani 1 1 d . . .
H22A H 0.1835 -0.1756 0.9719 0.104 Uiso 1 1 calc R . .
H22B H -0.0214 -0.0899 0.9902 0.104 Uiso 1 1 calc R . .
H22C H 0.2246 -0.1022 1.0075 0.104 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
S1 O6 1.420(2) . ?
S1 O5 1.425(3) . ?
S1 N1 1.693(3) . ?
S1 C16 1.758(4) . ?
O1 C2 1.362(4) . ?
O1 C1 1.432(5) . ?
O2 C8 1.219(4) . ?
O3 C13 1.191(4) . ?
O4 C13 1.339(4) . ?
O4 C14 1.454(5) . ?
N1 C8 1.396(4) . ?
N1 C12 1.471(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C2 C7 1.387(5) . ?
C2 C3 1.388(5) . ?
C3 C4 1.370(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.403(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.396(5) . ?
C5 C10 1.479(4) . ?
C6 C7 1.386(5) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.465(5) . ?
C9 C10 1.343(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.495(5) . ?
C11 C12 1.531(5) . ?
C11 H11B 0.9900 . ?
C11 H11A 0.9900 . ?
C12 C13 1.515(5) . ?
C12 H12 1.0000 . ?
C14 C15 1.485(5) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C21 1.376(5) . ?
C16 C17 1.390(5) . ?
C17 C18 1.388(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.386(6) . ?
C18 H18 0.9500 . ?
C19 C20 1.381(6) . ?
C19 C22 1.505(6) . ?
C20 C21 1.384(6) . ?
C20 H20 0.9500 . ?
C21 H21 0.9500 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 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
O6 S1 O5 119.81(19) . . ?
O6 S1 N1 110.21(15) . . ?
O5 S1 N1 103.94(16) . . ?
O6 S1 C16 108.97(18) . . ?
O5 S1 C16 108.49(18) . . ?
N1 S1 C16 104.29(17) . . ?
C2 O1 C1 118.6(3) . . ?
C13 O4 C14 119.1(3) . . ?
C8 N1 C12 120.3(3) . . ?
C8 N1 S1 120.6(2) . . ?
C12 N1 S1 118.2(2) . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
O1 C2 C7 125.2(4) . . ?
O1 C2 C3 115.7(3) . . ?
C7 C2 C3 119.1(3) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C3 C4 C5 121.4(4) . . ?
C3 C4 H4 119.3 . . ?
C5 C4 H4 119.3 . . ?
C6 C5 C4 116.8(3) . . ?
C6 C5 C10 122.3(3) . . ?
C4 C5 C10 120.8(3) . . ?
C7 C6 C5 122.1(4) . . ?
C7 C6 H6 119.0 . . ?
C5 C6 H6 119.0 . . ?
C6 C7 C2 119.6(3) . . ?
C6 C7 H7 120.2 . . ?
C2 C7 H7 120.2 . . ?
O2 C8 N1 121.6(3) . . ?
O2 C8 C9 122.3(3) . . ?
N1 C8 C9 115.9(3) . . ?
C10 C9 C8 124.0(3) . . ?
C10 C9 H9 118.0 . . ?
C8 C9 H9 118.0 . . ?
C9 C10 C5 122.5(3) . . ?
C9 C10 C11 117.7(3) . . ?
C5 C10 C11 119.6(3) . . ?
C10 C11 C12 112.9(3) . . ?
C10 C11 H11B 109.0 . . ?
C12 C11 H11B 109.0 . . ?
C10 C11 H11A 109.0 . . ?
C12 C11 H11A 109.0 . . ?
H11B C11 H11A 107.8 . . ?
N1 C12 C13 110.3(3) . . ?
N1 C12 C11 110.4(3) . . ?
C13 C12 C11 114.3(3) . . ?
N1 C12 H12 107.2 . . ?
C13 C12 H12 107.2 . . ?
C11 C12 H12 107.2 . . ?
O3 C13 O4 125.2(4) . . ?
O3 C13 C12 126.4(3) . . ?
O4 C13 C12 108.4(3) . . ?
O4 C14 C15 105.7(3) . . ?
O4 C14 H14A 110.6 . . ?
C15 C14 H14A 110.6 . . ?
O4 C14 H14B 110.6 . . ?
C15 C14 H14B 110.6 . . ?
H14A C14 H14B 108.7 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C21 C16 C17 121.2(4) . . ?
C21 C16 S1 120.0(3) . . ?
C17 C16 S1 118.8(3) . . ?
C18 C17 C16 118.6(4) . . ?
C18 C17 H17 120.7 . . ?
C16 C17 H17 120.7 . . ?
C19 C18 C17 121.2(4) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C20 C19 C18 118.6(4) . . ?
C20 C19 C22 121.6(4) . . ?
C18 C19 C22 119.8(4) . . ?
C19 C20 C21 121.5(4) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C16 C21 C20 118.9(4) . . ?
C16 C21 H21 120.5 . . ?
C20 C21 H21 120.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 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
O6 S1 N1 C8 43.7(3) . . . . ?
O5 S1 N1 C8 173.3(3) . . . . ?
C16 S1 N1 C8 -73.1(3) . . . . ?
O6 S1 N1 C12 -125.5(3) . . . . ?
O5 S1 N1 C12 4.1(3) . . . . ?
C16 S1 N1 C12 117.7(3) . . . . ?
C1 O1 C2 C7 2.5(5) . . . . ?
C1 O1 C2 C3 -178.2(3) . . . . ?
O1 C2 C3 C4 -178.5(4) . . . . ?
C7 C2 C3 C4 0.9(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C3 C4 C5 C10 179.3(3) . . . . ?
C4 C5 C6 C7 -1.0(6) . . . . ?
C10 C5 C6 C7 -179.8(3) . . . . ?
C5 C6 C7 C2 1.5(6) . . . . ?
O1 C2 C7 C6 177.9(3) . . . . ?
C3 C2 C7 C6 -1.4(6) . . . . ?
C12 N1 C8 O2 175.7(3) . . . . ?
S1 N1 C8 O2 6.8(4) . . . . ?
C12 N1 C8 C9 -8.1(4) . . . . ?
S1 N1 C8 C9 -177.1(2) . . . . ?
O2 C8 C9 C10 157.9(4) . . . . ?
N1 C8 C9 C10 -18.2(5) . . . . ?
C8 C9 C10 C5 -166.2(3) . . . . ?
C8 C9 C10 C11 7.8(5) . . . . ?
C6 C5 C10 C9 -163.2(4) . . . . ?
C4 C5 C10 C9 18.0(5) . . . . ?
C6 C5 C10 C11 23.0(5) . . . . ?
C4 C5 C10 C11 -155.8(3) . . . . ?
C9 C10 C11 C12 26.0(5) . . . . ?
C5 C10 C11 C12 -159.9(3) . . . . ?
C8 N1 C12 C13 -87.5(4) . . . . ?
S1 N1 C12 C13 81.8(3) . . . . ?
C8 N1 C12 C11 39.9(4) . . . . ?
S1 N1 C12 C11 -150.9(2) . . . . ?
C10 C11 C12 N1 -47.8(4) . . . . ?
C10 C11 C12 C13 77.2(4) . . . . ?
C14 O4 C13 O3 -8.8(6) . . . . ?
C14 O4 C13 C12 170.4(3) . . . . ?
N1 C12 C13 O3 2.9(5) . . . . ?
C11 C12 C13 O3 -122.2(4) . . . . ?
N1 C12 C13 O4 -176.2(3) . . . . ?
C11 C12 C13 O4 58.6(4) . . . . ?
C13 O4 C14 C15 -141.9(4) . . . . ?
O6 S1 C16 C21 -21.7(4) . . . . ?
O5 S1 C16 C21 -153.7(3) . . . . ?
N1 S1 C16 C21 96.0(3) . . . . ?
O6 S1 C16 C17 155.5(3) . . . . ?
O5 S1 C16 C17 23.5(3) . . . . ?
N1 S1 C16 C17 -86.8(3) . . . . ?
C21 C16 C17 C18 -0.1(6) . . . . ?
S1 C16 C17 C18 -177.3(3) . . . . ?
C16 C17 C18 C19 -0.5(6) . . . . ?
C17 C18 C19 C20 0.5(6) . . . . ?
C17 C18 C19 C22 -179.6(4) . . . . ?
C18 C19 C20 C21 0.0(7) . . . . ?
C22 C19 C20 C21 -179.8(4) . . . . ?
C17 C16 C21 C20 0.6(6) . . . . ?
S1 C16 C21 C20 177.8(3) . . . . ?
C19 C20 C21 C16 -0.6(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.286
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.056
_database_code_depnum_ccdc_archive 'CCDC 980928'
#######################################################################
#
#                 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_sa2772

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H12 Cl3 N O'
_chemical_formula_sum            'C12 H12 Cl3 N O'
_chemical_formula_weight         292.58
_chemical_absolute_configuration ad

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   P2(1)2(1)2(1)

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

_cell_length_a                   9.4908(18)
_cell_length_b                   11.747(2)
_cell_length_c                   23.965(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2671.9(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    7753
_cell_measurement_theta_min      1.70
_cell_measurement_theta_max      27.49

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.72
_exptl_crystal_size_mid          0.70
_exptl_crystal_size_min          0.60
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1200
_exptl_absorpt_coefficient_mu    0.668
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5523
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2007)'


_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            16984
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_sigmaI/netI    0.0365
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.31
_diffrn_reflns_theta_max         27.48
_reflns_number_total             6075
_reflns_number_gt                5932
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2007)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2007)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2007)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'Olex2 ver 1.1'
_computing_molecular_graphics    'Olex2 ver 1.1'
_computing_publication_material  'SHELX97 (Sheldrick, 2008)'


_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)+(0.0415P)²+0.5879P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.00(5)
_refine_ls_number_reflns         6075
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0374
_refine_ls_wR_factor_ref         0.0953
_refine_ls_wR_factor_gt          0.0947
_refine_ls_goodness_of_fit_ref   1.109
_refine_ls_restrained_S_all      1.109
_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
Cl1 Cl 0.19166(9) 0.42586(6) 0.64610(3) 0.05114(18) Uani 1 1 d . . .
Cl2 Cl 0.24860(8) 0.19555(6) 0.61376(3) 0.04838(16) Uani 1 1 d . . .
Cl3 Cl 0.40535(8) 0.37645(7) 0.56318(3) 0.05317(18) Uani 1 1 d . . .
Cl4 Cl 0.01401(7) 0.42245(6) 0.23595(3) 0.04644(16) Uani 1 1 d . . .
Cl5 Cl 0.08565(7) 0.24958(5) 0.31546(3) 0.04415(15) Uani 1 1 d . . .
Cl6 Cl 0.30262(7) 0.34881(6) 0.24767(3) 0.04322(15) Uani 1 1 d . . .
O1 O -0.2397(2) 0.28378(14) 0.56707(7) 0.0380(4) Uani 1 1 d . . .
O2 O 0.4722(2) 0.44998(16) 0.41835(8) 0.0504(5) Uani 1 1 d . . .
N1 N -0.0045(2) 0.29523(17) 0.55977(8) 0.0351(4) Uani 1 1 d . . .
H1 H 0.0013 0.2313 0.5787 0.042 Uiso 1 1 calc R . .
N2 N 0.2728(2) 0.43273(17) 0.36849(8) 0.0349(4) Uani 1 1 d . . .
H2 H 0.2620 0.3641 0.3826 0.042 Uiso 1 1 calc R . .
C1 C 0.1279(3) 0.3447(2) 0.54131(10) 0.0352(5) Uani 1 1 d . . .
H1A H 0.1637 0.2979 0.5095 0.042 Uiso 1 1 calc R . .
C2 C 0.1110(3) 0.4671(2) 0.52067(11) 0.0422(6) Uani 1 1 d . . .
H2A H 0.1042 0.5191 0.5530 0.051 Uiso 1 1 calc R . .
H2B H 0.1948 0.4891 0.4986 0.051 Uiso 1 1 calc R . .
C3 C -0.0207(3) 0.4786(2) 0.48474(10) 0.0360(5) Uani 1 1 d . . .
H3 H -0.0142 0.4227 0.4534 0.043 Uiso 1 1 calc R . .
C4 C -0.1485(3) 0.4479(2) 0.52058(10) 0.0405(6) Uani 1 1 d . . .
H4A H -0.1638 0.5092 0.5483 0.049 Uiso 1 1 calc R . .
H4B H -0.2328 0.4445 0.4964 0.049 Uiso 1 1 calc R . .
C5 C -0.1343(3) 0.3364(2) 0.55103(9) 0.0330(5) Uani 1 1 d . . .
C6 C -0.0425(3) 0.5971(2) 0.46006(11) 0.0424(6) Uani 1 1 d . . .
C7 C -0.1209(4) 0.6073(3) 0.41169(13) 0.0524(7) Uani 1 1 d . . .
H7 H -0.1563 0.5409 0.3939 0.063 Uiso 1 1 calc R . .
C8 C -0.1484(4) 0.7131(3) 0.38887(16) 0.0656(9) Uani 1 1 d . . .
H8 H -0.2018 0.7188 0.3555 0.079 Uiso 1 1 calc R . .
C9 C -0.0989(5) 0.8103(3) 0.41423(16) 0.0671(10) Uani 1 1 d . . .
H9 H -0.1177 0.8829 0.3983 0.081 Uiso 1 1 calc R . .
C10 C -0.0221(5) 0.8019(3) 0.46277(16) 0.0682(10) Uani 1 1 d . . .
H10 H 0.0103 0.8689 0.4809 0.082 Uiso 1 1 calc R . .
C11 C 0.0082(4) 0.6958(2) 0.48544(13) 0.0581(8) Uani 1 1 d . . .
H11 H 0.0637 0.6905 0.5183 0.070 Uiso 1 1 calc R . .
C12 C 0.2372(3) 0.3376(2) 0.58896(10) 0.0396(5) Uani 1 1 d . . .
C13 C 0.1661(3) 0.47046(19) 0.32877(10) 0.0327(5) Uani 1 1 d . . .
H13 H 0.0753 0.4796 0.3495 0.039 Uiso 1 1 calc R . .
C14 C 0.2022(3) 0.5845(2) 0.30239(10) 0.0411(6) Uani 1 1 d . . .
H14A H 0.1156 0.6190 0.2868 0.049 Uiso 1 1 calc R . .
H14B H 0.2692 0.5723 0.2713 0.049 Uiso 1 1 calc R . .
C15 C 0.2673(3) 0.66609(19) 0.34454(10) 0.0336(5) Uani 1 1 d . . .
H15 H 0.2013 0.6726 0.3769 0.040 Uiso 1 1 calc R . .
C16 C 0.4038(3) 0.6129(2) 0.36550(11) 0.0409(6) Uani 1 1 d . . .
H16A H 0.4741 0.6139 0.3350 0.049 Uiso 1 1 calc R . .
H16B H 0.4413 0.6599 0.3964 0.049 Uiso 1 1 calc R . .
C17 C 0.3859(3) 0.4919(2) 0.38573(10) 0.0364(5) Uani 1 1 d . . .
C18 C 0.2907(2) 0.78434(19) 0.32122(10) 0.0327(5) Uani 1 1 d . . .
C19 C 0.3441(3) 0.8030(2) 0.26771(11) 0.0388(5) Uani 1 1 d . . .
H19 H 0.3669 0.7397 0.2448 0.047 Uiso 1 1 calc R . .
C20 C 0.3645(3) 0.9126(2) 0.24742(12) 0.0417(5) Uani 1 1 d . . .
H20 H 0.4012 0.9237 0.2110 0.050 Uiso 1 1 calc R . .
C21 C 0.3313(3) 1.0053(2) 0.28024(12) 0.0443(6) Uani 1 1 d . . .
H21 H 0.3449 1.0803 0.2664 0.053 Uiso 1 1 calc R . .
C22 C 0.2782(3) 0.9886(2) 0.33327(11) 0.0459(7) Uani 1 1 d . . .
H22 H 0.2556 1.0521 0.3561 0.055 Uiso 1 1 calc R . .
C23 C 0.2580(3) 0.8789(2) 0.35317(11) 0.0416(6) Uani 1 1 d . . .
H23 H 0.2208 0.8684 0.3896 0.050 Uiso 1 1 calc R . .
C24 C 0.1440(2) 0.3777(2) 0.28382(10) 0.0318(5) 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
Cl1 C12 1.771(3) . ?
Cl2 C12 1.775(3) . ?
Cl3 C12 1.771(3) . ?
Cl4 C24 1.765(2) . ?
Cl5 C24 1.774(2) . ?
Cl6 C24 1.769(2) . ?
O1 C5 1.237(3) . ?
O2 C17 1.235(3) . ?
N1 C5 1.340(3) . ?
N1 C1 1.453(3) . ?
N1 H1 0.8800 . ?
N2 C17 1.344(3) . ?
N2 C13 1.459(3) . ?
N2 H2 0.8800 . ?
C1 C2 1.528(3) . ?
C1 C12 1.545(4) . ?
C1 H1A 1.0000 . ?
C2 C3 1.524(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C6 1.526(3) . ?
C3 C4 1.529(3) . ?
C3 H3 1.0000 . ?
C4 C5 1.506(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C6 C7 1.383(4) . ?
C6 C11 1.395(4) . ?
C7 C8 1.383(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.376(5) . ?
C8 H8 0.9500 . ?
C9 C10 1.376(6) . ?
C9 H9 0.9500 . ?
C10 C11 1.389(4) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C13 C14 1.521(3) . ?
C13 C24 1.546(3) . ?
C13 H13 1.0000 . ?
C14 C15 1.523(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C15 C18 1.514(3) . ?
C15 C16 1.524(3) . ?
C15 H15 1.0000 . ?
C16 C17 1.511(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C18 C23 1.384(3) . ?
C18 C19 1.396(4) . ?
C19 C20 1.390(4) . ?
C19 H19 0.9500 . ?
C20 C21 1.379(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.381(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.387(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 C1 127.09(19) . . ?
C5 N1 H1 116.5 . . ?
C1 N1 H1 116.5 . . ?
C17 N2 C13 126.7(2) . . ?
C17 N2 H2 116.6 . . ?
C13 N2 H2 116.6 . . ?
N1 C1 C2 112.6(2) . . ?
N1 C1 C12 109.49(19) . . ?
C2 C1 C12 111.2(2) . . ?
N1 C1 H1A 107.8 . . ?
C2 C1 H1A 107.8 . . ?
C12 C1 H1A 107.8 . . ?
C3 C2 C1 110.7(2) . . ?
C3 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.1 . . ?
C2 C3 C6 114.3(2) . . ?
C2 C3 C4 108.2(2) . . ?
C6 C3 C4 109.0(2) . . ?
C2 C3 H3 108.4 . . ?
C6 C3 H3 108.4 . . ?
C4 C3 H3 108.4 . . ?
C5 C4 C3 114.0(2) . . ?
C5 C4 H4A 108.8 . . ?
C3 C4 H4A 108.8 . . ?
C5 C4 H4B 108.8 . . ?
C3 C4 H4B 108.8 . . ?
H4A C4 H4B 107.7 . . ?
O1 C5 N1 121.0(2) . . ?
O1 C5 C4 120.8(2) . . ?
N1 C5 C4 118.2(2) . . ?
C7 C6 C11 118.6(3) . . ?
C7 C6 C3 118.5(2) . . ?
C11 C6 C3 122.9(2) . . ?
C6 C7 C8 120.8(3) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.6(3) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C9 C10 C11 120.3(3) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C6 120.2(3) . . ?
C10 C11 H11 119.9 . . ?
C6 C11 H11 119.9 . . ?
C1 C12 Cl3 109.45(17) . . ?
C1 C12 Cl1 112.07(19) . . ?
Cl3 C12 Cl1 109.80(14) . . ?
C1 C12 Cl2 109.85(18) . . ?
Cl3 C12 Cl2 107.72(15) . . ?
Cl1 C12 Cl2 107.85(13) . . ?
N2 C13 C14 112.5(2) . . ?
N2 C13 C24 109.53(18) . . ?
C14 C13 C24 111.20(19) . . ?
N2 C13 H13 107.8 . . ?
C14 C13 H13 107.8 . . ?
C24 C13 H13 107.8 . . ?
C13 C14 C15 111.71(19) . . ?
C13 C14 H14A 109.3 . . ?
C15 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
C15 C14 H14B 109.3 . . ?
H14A C14 H14B 107.9 . . ?
C18 C15 C14 113.06(19) . . ?
C18 C15 C16 111.9(2) . . ?
C14 C15 C16 107.8(2) . . ?
C18 C15 H15 108.0 . . ?
C14 C15 H15 108.0 . . ?
C16 C15 H15 108.0 . . ?
C17 C16 C15 113.3(2) . . ?
C17 C16 H16A 108.9 . . ?
C15 C16 H16A 108.9 . . ?
C17 C16 H16B 108.9 . . ?
C15 C16 H16B 108.9 . . ?
H16A C16 H16B 107.7 . . ?
O2 C17 N2 121.2(2) . . ?
O2 C17 C16 120.3(2) . . ?
N2 C17 C16 118.6(2) . . ?
C23 C18 C19 117.6(2) . . ?
C23 C18 C15 119.9(2) . . ?
C19 C18 C15 122.4(2) . . ?
C20 C19 C18 121.1(2) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C21 C20 C19 120.0(3) . . ?
C21 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C20 C21 C22 119.7(2) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C21 C22 C23 119.9(2) . . ?
C21 C22 H22 120.0 . . ?
C23 C22 H22 120.0 . . ?
C18 C23 C22 121.6(3) . . ?
C18 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C13 C24 Cl4 109.72(16) . . ?
C13 C24 Cl6 111.18(16) . . ?
Cl4 C24 Cl6 109.49(13) . . ?
C13 C24 Cl5 110.01(16) . . ?
Cl4 C24 Cl5 108.18(12) . . ?
Cl6 C24 Cl5 108.19(12) . . ?

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
C5 N1 C1 C2 13.0(3) . . . . ?
C5 N1 C1 C12 137.1(2) . . . . ?
N1 C1 C2 C3 -42.5(3) . . . . ?
C12 C1 C2 C3 -165.8(2) . . . . ?
C1 C2 C3 C6 -177.4(2) . . . . ?
C1 C2 C3 C4 61.0(3) . . . . ?
C2 C3 C4 C5 -50.6(3) . . . . ?
C6 C3 C4 C5 -175.4(2) . . . . ?
C1 N1 C5 O1 177.1(2) . . . . ?
C1 N1 C5 C4 -2.2(3) . . . . ?
C3 C4 C5 O1 -157.6(2) . . . . ?
C3 C4 C5 N1 21.8(3) . . . . ?
C2 C3 C6 C7 155.1(3) . . . . ?
C4 C3 C6 C7 -83.7(3) . . . . ?
C2 C3 C6 C11 -27.7(4) . . . . ?
C4 C3 C6 C11 93.5(3) . . . . ?
C11 C6 C7 C8 0.1(5) . . . . ?
C3 C6 C7 C8 177.4(3) . . . . ?
C6 C7 C8 C9 -0.5(5) . . . . ?
C7 C8 C9 C10 -0.3(6) . . . . ?
C8 C9 C10 C11 1.5(6) . . . . ?
C9 C10 C11 C6 -1.9(6) . . . . ?
C7 C6 C11 C10 1.1(5) . . . . ?
C3 C6 C11 C10 -176.1(3) . . . . ?
N1 C1 C12 Cl3 170.65(16) . . . . ?
C2 C1 C12 Cl3 -64.3(2) . . . . ?
N1 C1 C12 Cl1 -67.3(2) . . . . ?
C2 C1 C12 Cl1 57.7(2) . . . . ?
N1 C1 C12 Cl2 52.6(2) . . . . ?
C2 C1 C12 Cl2 177.59(18) . . . . ?
C17 N2 C13 C14 5.9(3) . . . . ?
C17 N2 C13 C24 130.1(2) . . . . ?
N2 C13 C14 C15 -39.3(3) . . . . ?
C24 C13 C14 C15 -162.5(2) . . . . ?
C13 C14 C15 C18 -174.1(2) . . . . ?
C13 C14 C15 C16 61.7(3) . . . . ?
C18 C15 C16 C17 -176.4(2) . . . . ?
C14 C15 C16 C17 -51.4(3) . . . . ?
C13 N2 C17 O2 -177.7(2) . . . . ?
C13 N2 C17 C16 3.9(4) . . . . ?
C15 C16 C17 O2 -158.3(3) . . . . ?
C15 C16 C17 N2 20.2(3) . . . . ?
C14 C15 C18 C23 137.2(3) . . . . ?
C16 C15 C18 C23 -100.8(3) . . . . ?
C14 C15 C18 C19 -42.4(3) . . . . ?
C16 C15 C18 C19 79.6(3) . . . . ?
C23 C18 C19 C20 0.4(4) . . . . ?
C15 C18 C19 C20 -180.0(2) . . . . ?
C18 C19 C20 C21 -0.2(4) . . . . ?
C19 C20 C21 C22 0.2(4) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C19 C18 C23 C22 -0.5(4) . . . . ?
C15 C18 C23 C22 179.9(2) . . . . ?
C21 C22 C23 C18 0.4(4) . . . . ?
N2 C13 C24 Cl4 179.56(16) . . . . ?
C14 C13 C24 Cl4 -55.5(2) . . . . ?
N2 C13 C24 Cl6 -59.2(2) . . . . ?
C14 C13 C24 Cl6 65.7(2) . . . . ?
N2 C13 C24 Cl5 60.7(2) . . . . ?
C14 C13 C24 Cl5 -174.42(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         0.318
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.054
_database_code_depnum_ccdc_archive 'CCDC 980929'
