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

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#
#                 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
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# 
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  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.
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data_dj816_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H13 Br Cl2 N2 O2 S'
_chemical_formula_weight         460.16

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'
Br Br -0.2901 2.4595 '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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           ?
_symmetry_space_group_name_H-M   P-1

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

_cell_length_a                   8.9358(18)
_cell_length_b                   9.326(2)
_cell_length_c                   12.002(3)
_cell_angle_alpha                106.670(3)
_cell_angle_beta                 101.817(4)
_cell_angle_gamma                93.100(4)
_cell_volume                     931.0(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      1.82
_cell_measurement_theta_max      25.00

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.641
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             460
_exptl_absorpt_coefficient_mu    2.620
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6499
_exptl_absorpt_correction_T_max  0.7439
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4776
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_av_sigmaI/netI    0.0278
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.82
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3254
_reflns_number_gt                2472
_reflns_threshold_expression     >2sigma(I)

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

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.1414P)²+2.4968P] 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         3254
_refine_ls_number_parameters     226
_refine_ls_number_restraints     97
_refine_ls_R_factor_all          0.0941
_refine_ls_R_factor_gt           0.0770
_refine_ls_wR_factor_ref         0.2417
_refine_ls_wR_factor_gt          0.2260
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.025
_refine_ls_shift/su_mean         0.001

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br -0.49015(11) -0.29166(11) 0.94239(10) 0.0845(4) Uani 1 1 d . . .
C1 C -0.3267(8) -0.0867(8) 0.8623(7) 0.0542(17) Uani 1 1 d . . .
H1 H -0.4159 -0.0397 0.8578 0.065 Uiso 1 1 calc R . .
C2 C -0.3195(9) -0.2138(8) 0.8966(7) 0.0551(17) Uani 1 1 d . . .
C3 C -0.1899(10) -0.2908(9) 0.9002(7) 0.0609(19) Uani 1 1 d . . .
H3 H -0.1898 -0.3794 0.9212 0.073 Uiso 1 1 calc R . .
C4 C -0.0606(9) -0.2329(8) 0.8719(7) 0.0552(17) Uani 1 1 d . . .
H4 H 0.0276 -0.2816 0.8738 0.066 Uiso 1 1 calc R . .
C5 C -0.0669(8) -0.1026(8) 0.8413(6) 0.0530(8) Uani 1 1 d U . .
C6 C -0.1985(8) -0.0297(8) 0.8345(6) 0.0522(8) Uani 1 1 d U . .
C7 C -0.1709(8) 0.1022(8) 0.7936(6) 0.0522(8) Uani 1 1 d U . .
C8 C 0.0026(8) 0.1075(8) 0.7916(6) 0.0531(8) Uani 1 1 d U . .
C9 C 0.1976(9) 0.3563(8) 0.6539(7) 0.0543(17) Uani 1 1 d . . .
C10 C 0.3528(11) 0.3481(11) 0.6888(9) 0.076(2) Uani 1 1 d . . .
H10 H 0.3960 0.3452 0.7654 0.091 Uiso 1 1 calc R . .
C11 C 0.1362(11) 0.3626(11) 0.5412(8) 0.075(2) Uani 1 1 d . . .
H11 H 0.0311 0.3667 0.5172 0.089 Uiso 1 1 calc R . .
C12 C 0.2300(14) 0.3629(12) 0.4636(9) 0.089(3) Uani 1 1 d . . .
H12 H 0.1894 0.3724 0.3886 0.107 Uiso 1 1 calc R . .
C13 C 0.3806(15) 0.3494(11) 0.4964(11) 0.092(3) Uani 1 1 d . . .
H13 H 0.4423 0.3436 0.4419 0.111 Uiso 1 1 calc R . .
C14 C 0.4432(12) 0.3442(13) 0.6071(12) 0.093(3) Uani 1 1 d . . .
H14 H 0.5481 0.3379 0.6289 0.111 Uiso 1 1 calc R . .
C15 C 0.2171(9) -0.1320(9) 0.6958(7) 0.0674(10) Uani 1 1 d DU . .
H15 H 0.1642 -0.0812 0.6467 0.081 Uiso 1 1 calc R . .
C16 C 0.2783(10) -0.2491(9) 0.6237(8) 0.0787(13) Uani 1 1 d DU . .
H16A H 0.3356 -0.3128 0.6575 0.094 Uiso 1 1 calc R . .
H16B H 0.2618 -0.2633 0.5420 0.094 Uiso 1 1 calc R . .
C17 C 0.2040(9) -0.0612(9) 0.8120(7) 0.0606(8) Uani 1 1 d U . .
H17A H 0.2781 0.0286 0.8470 0.073 Uiso 1 1 calc R . .
H17B H 0.2273 -0.1285 0.8600 0.073 Uiso 1 1 calc R . .
Cl1 Cl -0.2123(2) 0.2711(2) 0.88689(19) 0.0625(6) Uani 1 1 d . . .
Cl2 Cl -0.2792(3) 0.0643(3) 0.64213(19) 0.0725(6) Uani 1 1 d . . .
N1 N 0.0496(7) -0.0200(7) 0.8134(5) 0.0550(8) Uani 1 1 d U . .
N2 N 0.0990(7) 0.1999(7) 0.7747(6) 0.0570(15) Uani 1 1 d . . .
O1 O 0.1485(8) 0.4756(6) 0.8633(6) 0.0769(17) Uani 1 1 d . . .
O2 O -0.0748(7) 0.3767(7) 0.6965(6) 0.0765(16) Uani 1 1 d . . .
S1 S 0.0775(2) 0.3639(2) 0.75443(19) 0.0586(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
Br1 C2 1.899(7) . ?
C1 C2 1.362(10) . ?
C1 C6 1.378(10) . ?
C1 H1 0.9300 . ?
C2 C3 1.395(11) . ?
C3 C4 1.393(12) . ?
C3 H3 0.9300 . ?
C4 C5 1.367(10) . ?
C4 H4 0.9300 . ?
C5 C6 1.390(10) . ?
C5 N1 1.412(10) . ?
C6 C7 1.476(10) . ?
C7 C8 1.554(10) . ?
C7 Cl1 1.759(7) . ?
C7 Cl2 1.800(7) . ?
C8 N2 1.272(9) . ?
C8 N1 1.359(10) . ?
C9 C11 1.371(12) . ?
C9 C10 1.377(12) . ?
C9 S1 1.761(7) . ?
C10 C14 1.386(14) . ?
C10 H10 0.9300 . ?
C11 C12 1.375(14) . ?
C11 H11 0.9300 . ?
C12 C13 1.346(16) . ?
C12 H12 0.9300 . ?
C13 C14 1.348(16) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C17 1.394(11) . ?
C15 C16 1.3986(11) . ?
C15 H15 0.9300 . ?
C16 H16A 0.9300 . ?
C16 H16B 0.9300 . ?
C17 N1 1.454(10) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N2 S1 1.631(6) . ?
O1 S1 1.416(6) . ?
O2 S1 1.423(6) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 118.3(7) . . ?
C2 C1 H1 120.8 . . ?
C6 C1 H1 120.8 . . ?
C1 C2 C3 122.5(7) . . ?
C1 C2 Br1 119.8(6) . . ?
C3 C2 Br1 117.6(6) . . ?
C4 C3 C2 118.9(7) . . ?
C4 C3 H3 120.5 . . ?
C2 C3 H3 120.5 . . ?
C5 C4 C3 118.2(7) . . ?
C5 C4 H4 120.9 . . ?
C3 C4 H4 120.9 . . ?
C4 C5 C6 122.2(7) . . ?
C4 C5 N1 128.7(7) . . ?
C6 C5 N1 109.1(6) . . ?
C1 C6 C5 119.7(7) . . ?
C1 C6 C7 131.3(7) . . ?
C5 C6 C7 108.9(6) . . ?
C6 C7 C8 103.2(6) . . ?
C6 C7 Cl1 113.4(5) . . ?
C8 C7 Cl1 111.8(5) . . ?
C6 C7 Cl2 109.2(5) . . ?
C8 C7 Cl2 107.6(5) . . ?
Cl1 C7 Cl2 111.1(4) . . ?
N2 C8 N1 119.2(7) . . ?
N2 C8 C7 134.5(7) . . ?
N1 C8 C7 106.3(6) . . ?
C11 C9 C10 120.0(8) . . ?
C11 C9 S1 119.4(7) . . ?
C10 C9 S1 120.5(6) . . ?
C9 C10 C14 118.5(9) . . ?
C9 C10 H10 120.8 . . ?
C14 C10 H10 120.8 . . ?
C9 C11 C12 119.9(9) . . ?
C9 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C12 C11 119.9(10) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C14 120.8(9) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
C13 C14 C10 120.7(10) . . ?
C13 C14 H14 119.6 . . ?
C10 C14 H14 119.6 . . ?
C17 C15 C16 144.8(9) . . ?
C17 C15 H15 107.6 . . ?
C16 C15 H15 107.6 . . ?
C15 C16 H16A 120.0 . . ?
C15 C16 H16B 120.0 . . ?
H16A C16 H16B 120.0 . . ?
C15 C17 N1 111.1(7) . . ?
C15 C17 H17A 109.4 . . ?
N1 C17 H17A 109.4 . . ?
C15 C17 H17B 109.4 . . ?
N1 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C8 N1 C5 111.9(6) . . ?
C8 N1 C17 123.1(6) . . ?
C5 N1 C17 124.9(6) . . ?
C8 N2 S1 129.6(5) . . ?
O1 S1 O2 118.3(4) . . ?
O1 S1 N2 107.5(4) . . ?
O2 S1 N2 114.1(4) . . ?
O1 S1 C9 108.0(4) . . ?
O2 S1 C9 108.6(4) . . ?
N2 S1 C9 98.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -2.5(12) . . . . ?
C6 C1 C2 Br1 177.3(5) . . . . ?
C1 C2 C3 C4 2.4(12) . . . . ?
Br1 C2 C3 C4 -177.4(6) . . . . ?
C2 C3 C4 C5 -0.2(11) . . . . ?
C3 C4 C5 C6 -1.8(11) . . . . ?
C3 C4 C5 N1 177.5(7) . . . . ?
C2 C1 C6 C5 0.4(11) . . . . ?
C2 C1 C6 C7 179.0(7) . . . . ?
C4 C5 C6 C1 1.8(11) . . . . ?
N1 C5 C6 C1 -177.7(6) . . . . ?
C4 C5 C6 C7 -177.2(7) . . . . ?
N1 C5 C6 C7 3.4(8) . . . . ?
C1 C6 C7 C8 174.8(8) . . . . ?
C5 C6 C7 C8 -6.5(8) . . . . ?
C1 C6 C7 Cl1 53.6(10) . . . . ?
C5 C6 C7 Cl1 -127.6(6) . . . . ?
C1 C6 C7 Cl2 -70.9(9) . . . . ?
C5 C6 C7 Cl2 107.8(6) . . . . ?
C6 C7 C8 N2 -172.8(8) . . . . ?
Cl1 C7 C8 N2 -50.5(11) . . . . ?
Cl2 C7 C8 N2 71.8(10) . . . . ?
C6 C7 C8 N1 7.3(7) . . . . ?
Cl1 C7 C8 N1 129.6(5) . . . . ?
Cl2 C7 C8 N1 -108.1(6) . . . . ?
C11 C9 C10 C14 -0.9(13) . . . . ?
S1 C9 C10 C14 -179.2(8) . . . . ?
C10 C9 C11 C12 -1.0(13) . . . . ?
S1 C9 C11 C12 177.4(7) . . . . ?
C9 C11 C12 C13 3.3(15) . . . . ?
C11 C12 C13 C14 -3.8(16) . . . . ?
C12 C13 C14 C10 1.9(17) . . . . ?
C9 C10 C14 C13 0.5(16) . . . . ?
C16 C15 C17 N1 -139.4(13) . . . . ?
N2 C8 N1 C5 174.4(7) . . . . ?
C7 C8 N1 C5 -5.8(8) . . . . ?
N2 C8 N1 C17 -3.6(11) . . . . ?
C7 C8 N1 C17 176.3(6) . . . . ?
C4 C5 N1 C8 -177.7(8) . . . . ?
C6 C5 N1 C8 1.7(8) . . . . ?
C4 C5 N1 C17 0.2(12) . . . . ?
C6 C5 N1 C17 179.6(6) . . . . ?
C15 C17 N1 C8 -82.5(9) . . . . ?
C15 C17 N1 C5 99.9(9) . . . . ?
N1 C8 N2 S1 -176.2(6) . . . . ?
C7 C8 N2 S1 4.0(14) . . . . ?
C8 N2 S1 O1 102.7(8) . . . . ?
C8 N2 S1 O2 -30.6(9) . . . . ?
C8 N2 S1 C9 -145.4(7) . . . . ?
C11 C9 S1 O1 -129.7(7) . . . . ?
C10 C9 S1 O1 48.7(7) . . . . ?
C11 C9 S1 O2 -0.2(8) . . . . ?
C10 C9 S1 O2 178.1(7) . . . . ?
C11 C9 S1 N2 118.7(7) . . . . ?
C10 C9 S1 N2 -62.9(7) . . . . ?

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.620
_refine_diff_density_min         -2.251
_refine_diff_density_rms         0.113
_database_code_depnum_ccdc_archive 'CCDC 1006093'
