# Electronic Supplementary Material (ESI) for Polymer 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
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#  data retrieval see:
#                         www.ccdc.cam.ac.uk
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#  from this site to visualise CIF-encoded structures and 
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data_iwel54_benzol

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H30 Br2 N2 O2 S2'
_chemical_formula_sum            'C34 H30 Br2 N2 O2 S2'
_chemical_formula_weight         722.54

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'
Br Br -0.2901 2.4595 '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           monoclinic
_symmetry_space_group_name_H-M   P21/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                   6.8071(6)
_cell_length_b                   21.415(2)
_cell_length_c                   10.9248(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.159(3)
_cell_angle_gamma                90.00
_cell_volume                     1556.9(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7775
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      26.99
_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          .2
_exptl_crystal_size_mid          .03
_exptl_crystal_size_min          .03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             732
_exptl_absorpt_coefficient_mu    2.772
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(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  'Nonius KappaCCD'
_diffrn_measurement_method       Phi/Omega-Scans
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7775
_diffrn_reflns_av_R_equivalents  0.0768
_diffrn_reflns_av_sigmaI/netI    0.0789
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.90
_diffrn_reflns_theta_max         26.99
_reflns_number_total             3234
_reflns_number_gt                2355
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Nonius COLLECT'
_computing_cell_refinement       'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_data_reduction        'Nonius DENZO (Otwinowski, Minor 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SCHAKAL99 (E. Keller 1999)'
_computing_publication_material  'PLATON (A. L. Spek 1980-2004)'

_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)+(0.0661P)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_number_reflns         3234
_refine_ls_number_parameters     193
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0741
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1309
_refine_ls_wR_factor_gt          0.1102
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_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
Br1 Br 0.31354(6) 0.08266(2) 1.33909(4) 0.03163(18) Uani 1 1 d . . .
S1 S 0.52185(15) 0.07572(5) 1.14537(9) 0.0236(3) Uani 1 1 d . . .
O1 O 0.6069(4) 0.10553(13) 0.9312(2) 0.0239(6) Uani 1 1 d . . .
N1 N 0.8688(5) 0.05463(16) 0.8835(3) 0.0198(7) Uani 1 1 d . . .
C1 C 0.5316(6) 0.0561(2) 1.2911(4) 0.0245(9) Uani 1 1 d . . .
C2 C 0.7512(6) 0.03253(18) 1.1707(4) 0.0210(9) Uani 1 1 d . . .
C3 C 0.8351(6) 0.02782(18) 1.0721(4) 0.0193(8) Uani 1 1 d . . .
C4 C 0.7490(6) 0.06770(18) 0.9585(4) 0.0207(9) Uani 1 1 d . . .
C5 C 0.9890(6) -0.00821(18) 1.0586(3) 0.0197(8) Uani 1 1 d . . .
C11 C 0.7037(6) 0.01995(19) 1.3579(4) 0.0257(9) Uani 1 1 d . . .
H11 H 0.7209 0.0074 1.4429 0.031 Uiso 1 1 calc R . .
C12 C 0.8284(6) 0.00718(19) 1.2884(4) 0.0232(9) Uani 1 1 d . . .
H12 H 0.9506 -0.0154 1.3127 0.028 Uiso 1 1 calc R . .
C13 C 0.8819(6) 0.09790(17) 0.7930(4) 0.0206(9) Uani 1 1 d . . .
C14 C 0.7022(6) 0.11558(19) 0.6923(4) 0.0222(9) Uani 1 1 d . . .
H14 H 0.5762 0.0961 0.6901 0.027 Uiso 1 1 calc R . .
C15 C 0.7193(6) 0.15855(18) 0.6060(4) 0.0234(9) Uani 1 1 d . . .
H15 H 0.6092 0.1714 0.5423 0.028 Uiso 1 1 calc R . .
C16 C 0.9148(6) 0.18308(18) 0.6180(4) 0.0224(9) Uani 1 1 d . . .
C17 C 1.0949(6) 0.16411(18) 0.7217(4) 0.0233(9) Uani 1 1 d . . .
H17 H 1.2218 0.1829 0.7232 0.028 Uiso 1 1 calc R . .
C18 C 1.0799(6) 0.12267(18) 0.8089(4) 0.0211(9) Uani 1 1 d . . .
H18 H 1.1885 0.1108 0.8745 0.025 Uiso 1 1 calc R . .
C19 C 0.9375(7) 0.2281(2) 0.5214(4) 0.0304(10) Uani 1 1 d . . .
C20 C 1.0372(7) 0.2892(2) 0.5876(4) 0.0376(11) Uani 1 1 d . . .
H20A H 1.0641 0.3185 0.5242 0.056 Uiso 1 1 calc R . .
H20B H 1.1637 0.2785 0.6450 0.056 Uiso 1 1 calc R . .
H20C H 0.9458 0.3087 0.6347 0.056 Uiso 1 1 calc R . .
C21 C 0.7252(7) 0.2439(2) 0.4154(4) 0.0351(11) Uani 1 1 d . . .
H21A H 0.7537 0.2748 0.3554 0.053 Uiso 1 1 calc R . .
H21B H 0.6235 0.2604 0.4582 0.053 Uiso 1 1 calc R . .
H21C H 0.6749 0.2055 0.3707 0.053 Uiso 1 1 calc R . .
C22 C 1.0818(8) 0.1983(2) 0.4625(5) 0.0506(15) Uani 1 1 d . . .
H22A H 1.0276 0.1584 0.4265 0.076 Uiso 1 1 calc R . .
H22B H 1.2060 0.1908 0.5248 0.076 Uiso 1 1 calc R . .
H22C H 1.1105 0.2253 0.3959 0.076 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
Br1 C1 1.769(4) . ?
S1 C1 1.634(4) . ?
S1 C2 1.785(4) . ?
O1 C4 1.249(5) . ?
N1 C4 1.302(4) . ?
N1 C13 1.371(5) . ?
N1 C5 1.438(5) 3_757 ?
C1 C11 1.464(6) . ?
C2 C3 1.325(5) . ?
C2 C12 1.393(6) . ?
C3 C5 1.334(5) . ?
C3 C4 1.519(6) . ?
C5 C5 1.367(7) 3_757 ?
C5 N1 1.438(5) 3_757 ?
C11 C12 1.282(5) . ?
C11 H11 0.9500 . ?
C12 H12 0.9500 . ?
C13 C18 1.424(5) . ?
C13 C14 1.511(6) . ?
C14 C15 1.339(5) . ?
C14 H14 0.9500 . ?
C15 C16 1.411(5) . ?
C15 H15 0.9500 . ?
C16 C19 1.461(5) . ?
C16 C17 1.538(6) . ?
C17 C18 1.321(5) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C22 1.433(5) . ?
C19 C20 1.578(6) . ?
C19 C21 1.685(6) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
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
C1 S1 C2 82.01(19) . . ?
C4 N1 C13 116.9(3) . . ?
C4 N1 C5 109.0(3) . 3_757 ?
C13 N1 C5 130.1(3) . 3_757 ?
C11 C1 S1 119.0(3) . . ?
C11 C1 Br1 131.0(3) . . ?
S1 C1 Br1 110.0(2) . . ?
C3 C2 C12 125.3(4) . . ?
C3 C2 S1 115.2(3) . . ?
C12 C2 S1 119.5(3) . . ?
C2 C3 C5 128.1(4) . . ?
C2 C3 C4 117.6(3) . . ?
C5 C3 C4 114.3(3) . . ?
O1 C4 N1 123.0(4) . . ?
O1 C4 C3 135.0(3) . . ?
N1 C4 C3 102.0(3) . . ?
C3 C5 C5 101.4(4) . 3_757 ?
C3 C5 N1 145.4(3) . 3_757 ?
C5 C5 N1 113.2(4) 3_757 3_757 ?
C12 C11 C1 112.2(4) . . ?
C12 C11 H11 123.9 . . ?
C1 C11 H11 123.9 . . ?
C11 C12 C2 107.2(4) . . ?
C11 C12 H12 126.4 . . ?
C2 C12 H12 126.4 . . ?
N1 C13 C18 111.6(4) . . ?
N1 C13 C14 121.9(3) . . ?
C18 C13 C14 126.5(3) . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 114.2(4) . . ?
C14 C15 H15 122.9 . . ?
C16 C15 H15 122.9 . . ?
C15 C16 C19 114.8(4) . . ?
C15 C16 C17 124.0(3) . . ?
C19 C16 C17 121.1(4) . . ?
C18 C17 C16 122.5(4) . . ?
C18 C17 H17 118.7 . . ?
C16 C17 H17 118.7 . . ?
C17 C18 C13 112.2(4) . . ?
C17 C18 H18 123.9 . . ?
C13 C18 H18 123.9 . . ?
C22 C19 C16 102.5(4) . . ?
C22 C19 C20 107.8(4) . . ?
C16 C19 C20 108.5(4) . . ?
C22 C19 C21 110.5(4) . . ?
C16 C19 C21 115.0(3) . . ?
C20 C19 C21 111.9(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
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
C2 S1 C1 C11 1.7(3) . . . . ?
C2 S1 C1 Br1 -176.5(2) . . . . ?
C1 S1 C2 C3 178.1(3) . . . . ?
C1 S1 C2 C12 -2.2(3) . . . . ?
C12 C2 C3 C5 10.4(7) . . . . ?
S1 C2 C3 C5 -170.0(4) . . . . ?
C12 C2 C3 C4 -169.6(4) . . . . ?
S1 C2 C3 C4 10.0(5) . . . . ?
C13 N1 C4 O1 22.1(6) . . . . ?
C5 N1 C4 O1 -178.2(4) 3_757 . . . ?
C13 N1 C4 C3 -156.9(3) . . . . ?
C5 N1 C4 C3 2.8(4) 3_757 . . . ?
C2 C3 C4 O1 -1.9(7) . . . . ?
C5 C3 C4 O1 178.0(4) . . . . ?
C2 C3 C4 N1 176.9(4) . . . . ?
C5 C3 C4 N1 -3.1(4) . . . . ?
C2 C3 C5 C5 -178.2(4) . . . 3_757 ?
C4 C3 C5 C5 1.9(5) . . . 3_757 ?
C2 C3 C5 N1 1.8(9) . . . 3_757 ?
C4 C3 C5 N1 -178.2(5) . . . 3_757 ?
S1 C1 C11 C12 -1.0(5) . . . . ?
Br1 C1 C11 C12 176.8(3) . . . . ?
C1 C11 C12 C2 -0.7(5) . . . . ?
C3 C2 C12 C11 -178.3(4) . . . . ?
S1 C2 C12 C11 2.1(5) . . . . ?
C4 N1 C13 C18 117.2(4) . . . . ?
C5 N1 C13 C18 -37.4(5) 3_757 . . . ?
C4 N1 C13 C14 -62.2(5) . . . . ?
C5 N1 C13 C14 143.2(4) 3_757 . . . ?
N1 C13 C14 C15 179.2(3) . . . . ?
C18 C13 C14 C15 -0.1(6) . . . . ?
C13 C14 C15 C16 1.2(5) . . . . ?
C14 C15 C16 C19 177.6(3) . . . . ?
C14 C15 C16 C17 -1.3(5) . . . . ?
C15 C16 C17 C18 0.1(6) . . . . ?
C19 C16 C17 C18 -178.7(4) . . . . ?
C16 C17 C18 C13 1.0(5) . . . . ?
N1 C13 C18 C17 179.5(3) . . . . ?
C14 C13 C18 C17 -1.1(5) . . . . ?
C15 C16 C19 C22 -118.6(4) . . . . ?
C17 C16 C19 C22 60.3(5) . . . . ?
C15 C16 C19 C20 127.5(4) . . . . ?
C17 C16 C19 C20 -53.6(5) . . . . ?
C15 C16 C19 C21 1.4(5) . . . . ?
C17 C16 C19 C21 -179.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.952
_diffrn_reflns_theta_full        26.99
_diffrn_measured_fraction_theta_full 0.952
_refine_diff_density_max         0.891
_refine_diff_density_min         -0.551
_refine_diff_density_rms         0.173
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Benzene'
_database_code_depnum_ccdc_archive 'CCDC 1019442'
