# Electronic Supplementary Material (ESI) for ChemComm.
# 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_121011-zyl02-zz

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H22 Cl N O4 S2'
_chemical_formula_weight         524.03

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P2(1)/n  '

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

_cell_length_a                   12.3840(11)
_cell_length_b                   9.8375(8)
_cell_length_c                   23.1860(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.290(7)
_cell_angle_gamma                90.00
_cell_volume                     2816.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.236
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1088
_exptl_absorpt_coefficient_mu    0.315
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.948
_exptl_absorpt_correction_T_max  0.960
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10353
_diffrn_reflns_av_R_equivalents  0.0342
_diffrn_reflns_av_sigmaI/netI    0.0512
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.01
_diffrn_reflns_theta_max         25.01
_reflns_number_total             4960
_reflns_number_gt                3506
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1846P)²+1.7574P] 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         4960
_refine_ls_number_parameters     322
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1059
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2812
_refine_ls_wR_factor_gt          0.2511
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_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 0.74596(11) 0.17845(13) 0.20480(5) 0.0527(4) Uani 1 1 d . . .
S2 S 0.71131(11) 0.34062(14) 0.10002(6) 0.0601(5) Uani 1 1 d . . .
Cl1 Cl 0.07542(13) 0.56260(17) 0.18742(7) 0.0771(5) Uani 1 1 d . . .
C1 C 0.4688(4) -0.2124(4) 0.16713(18) 0.0428(11) Uani 1 1 d . . .
C2 C 0.3884(4) -0.2211(5) 0.2039(2) 0.0554(13) Uani 1 1 d . . .
H2 H 0.3453 -0.1460 0.2103 0.066 Uiso 1 1 calc R . .
C3 C 0.3716(5) -0.3426(7) 0.2317(2) 0.0660(16) Uani 1 1 d . . .
H3 H 0.3155 -0.3486 0.2561 0.079 Uiso 1 1 calc R . .
C4 C 0.4348(5) -0.4548(6) 0.2244(2) 0.0611(15) Uani 1 1 d . . .
C5 C 0.5178(5) -0.4422(5) 0.1882(2) 0.0621(14) Uani 1 1 d . . .
H5 H 0.5631 -0.5159 0.1831 0.075 Uiso 1 1 calc R . .
C6 C 0.5346(5) -0.3220(5) 0.1593(2) 0.0553(13) Uani 1 1 d . . .
H6 H 0.5904 -0.3155 0.1347 0.066 Uiso 1 1 calc R . .
N1 N 0.4831(3) -0.0869(4) 0.13494(15) 0.0427(9) Uani 1 1 d . . .
C8 C 0.5527(4) 0.0134(5) 0.16032(19) 0.0452(11) Uani 1 1 d . . .
C9 C 0.5692(4) 0.1361(4) 0.12604(18) 0.0399(10) Uani 1 1 d . . .
C10 C 0.4945(4) 0.1628(4) 0.07709(18) 0.0378(10) Uani 1 1 d . . .
C11 C 0.4253(4) 0.0618(4) 0.05464(18) 0.0409(10) Uani 1 1 d . . .
C12 C 0.4226(4) -0.0727(4) 0.08179(19) 0.0427(10) Uani 1 1 d . . .
C13 C 0.3537(4) 0.0815(4) 0.00389(18) 0.0415(10) Uani 1 1 d . . .
H13 H 0.3249 0.0061 -0.0159 0.050 Uiso 1 1 calc R . .
C14 C 0.3270(4) 0.2073(5) -0.01585(19) 0.0440(11) Uani 1 1 d . . .
C15 C 0.3719(4) 0.3296(4) 0.01647(19) 0.0415(10) Uani 1 1 d . . .
C16 C 0.4863(4) 0.2980(4) 0.04533(19) 0.0418(10) Uani 1 1 d . . .
H16A H 0.5377 0.2981 0.0157 0.050 Uiso 1 1 calc R . .
H16B H 0.5070 0.3701 0.0725 0.050 Uiso 1 1 calc R . .
C17 C 0.2491(4) 0.2329(5) -0.0660(2) 0.0482(11) Uani 1 1 d . . .
C18 C 0.6631(4) 0.2106(4) 0.14242(18) 0.0411(10) Uani 1 1 d . . .
C19 C 0.2943(4) 0.3846(5) 0.05941(19) 0.0422(10) Uani 1 1 d . . .
C20 C 0.2886(5) 0.5227(5) 0.0678(2) 0.0545(13) Uani 1 1 d . . .
H20 H 0.3309 0.5802 0.0470 0.065 Uiso 1 1 calc R . .
C21 C 0.2210(5) 0.5783(5) 0.1069(2) 0.0595(14) Uani 1 1 d . . .
H21 H 0.2179 0.6718 0.1123 0.071 Uiso 1 1 calc R . .
C22 C 0.1599(4) 0.4941(5) 0.1368(2) 0.0532(12) Uani 1 1 d . . .
C23 C 0.1615(5) 0.3574(6) 0.1292(2) 0.0619(14) Uani 1 1 d . . .
H23 H 0.1177 0.3012 0.1497 0.074 Uiso 1 1 calc R . .
C24 C 0.2297(4) 0.3030(5) 0.0902(2) 0.0543(13) Uani 1 1 d . . .
H24 H 0.2316 0.2093 0.0849 0.065 Uiso 1 1 calc R . .
C25 C 0.1420(7) 0.1409(8) -0.1456(3) 0.097(3) Uani 1 1 d . . .
H25A H 0.0736 0.1710 -0.1334 0.145 Uiso 1 1 calc R . .
H25B H 0.1323 0.0568 -0.1664 0.145 Uiso 1 1 calc R . .
H25C H 0.1705 0.2083 -0.1703 0.145 Uiso 1 1 calc R . .
C26 C 0.4115(6) -0.5901(7) 0.2522(3) 0.095(2) Uani 1 1 d . . .
H26A H 0.3587 -0.6390 0.2278 0.143 Uiso 1 1 calc R . .
H26B H 0.3840 -0.5747 0.2892 0.143 Uiso 1 1 calc R . .
H26C H 0.4770 -0.6424 0.2570 0.143 Uiso 1 1 calc R . .
C27 C 0.8595(5) 0.2795(6) 0.1857(2) 0.0614(14) Uani 1 1 d . . .
H27A H 0.9022 0.3081 0.2204 0.074 Uiso 1 1 calc R . .
H27B H 0.9054 0.2265 0.1622 0.074 Uiso 1 1 calc R . .
C7 C 0.8171(5) 0.3999(6) 0.1530(3) 0.0699(16) Uani 1 1 d . . .
H7A H 0.8746 0.4436 0.1337 0.084 Uiso 1 1 calc R . .
H7B H 0.7876 0.4651 0.1790 0.084 Uiso 1 1 calc R . .
O1 O 0.3689(3) -0.1670(3) 0.06165(15) 0.0598(10) Uani 1 1 d . . .
O2 O 0.5963(3) -0.0069(4) 0.20828(14) 0.0612(10) Uani 1 1 d . . .
O3 O 0.2180(4) 0.3445(4) -0.07993(18) 0.0734(12) Uani 1 1 d . . .
O4 O 0.2180(4) 0.1203(4) -0.09461(17) 0.0748(12) Uani 1 1 d . . .
H15 H 0.385(4) 0.407(5) -0.0092(19) 0.041(12) 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 C18 1.739(5) . ?
S1 C27 1.804(6) . ?
S2 C18 1.745(4) . ?
S2 C7 1.824(6) . ?
Cl1 C22 1.763(5) . ?
C1 C2 1.361(7) . ?
C1 C6 1.373(7) . ?
C1 N1 1.460(5) . ?
C2 C3 1.381(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.380(9) . ?
C4 C26 1.516(7) . ?
C5 C6 1.382(7) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
N1 C12 1.400(6) . ?
N1 C8 1.409(6) . ?
C8 O2 1.216(5) . ?
C8 C9 1.467(6) . ?
C9 C18 1.403(6) . ?
C9 C10 1.434(6) . ?
C10 C11 1.387(6) . ?
C10 C16 1.520(6) . ?
C11 C13 1.432(6) . ?
C11 C12 1.467(6) . ?
C12 O1 1.215(5) . ?
C13 C14 1.352(6) . ?
C13 H13 0.9300 . ?
C14 C17 1.476(7) . ?
C14 C15 1.502(6) . ?
C15 C19 1.533(7) . ?
C15 C16 1.553(7) . ?
C15 H15 0.99(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O3 1.199(6) . ?
C17 O4 1.334(6) . ?
C19 C24 1.371(7) . ?
C19 C20 1.375(6) . ?
C20 C21 1.390(8) . ?
C20 H20 0.9300 . ?
C21 C22 1.348(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.357(8) . ?
C23 C24 1.390(7) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C25 O4 1.469(7) . ?
C25 H25A 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25C 0.9600 . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
C27 C7 1.481(8) . ?
C27 H27A 0.9700 . ?
C27 H27B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?

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
C18 S1 C27 96.8(2) . . ?
C18 S2 C7 96.5(2) . . ?
C2 C1 C6 120.2(4) . . ?
C2 C1 N1 119.8(4) . . ?
C6 C1 N1 120.1(4) . . ?
C1 C2 C3 119.3(5) . . ?
C1 C2 H2 120.3 . . ?
C3 C2 H2 120.3 . . ?
C4 C3 C2 122.1(5) . . ?
C4 C3 H3 118.9 . . ?
C2 C3 H3 118.9 . . ?
C3 C4 C5 117.4(5) . . ?
C3 C4 C26 121.7(6) . . ?
C5 C4 C26 120.8(6) . . ?
C4 C5 C6 121.2(5) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C5 119.7(5) . . ?
C1 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
C12 N1 C8 124.6(4) . . ?
C12 N1 C1 117.2(4) . . ?
C8 N1 C1 118.2(4) . . ?
O2 C8 N1 118.9(4) . . ?
O2 C8 C9 124.1(4) . . ?
N1 C8 C9 117.1(4) . . ?
C18 C9 C10 126.2(4) . . ?
C18 C9 C8 115.4(4) . . ?
C10 C9 C8 118.1(4) . . ?
C11 C10 C9 120.7(4) . . ?
C11 C10 C16 115.3(4) . . ?
C9 C10 C16 124.0(4) . . ?
C10 C11 C13 122.6(4) . . ?
C10 C11 C12 121.2(4) . . ?
C13 C11 C12 116.3(4) . . ?
O1 C12 N1 120.3(4) . . ?
O1 C12 C11 123.6(4) . . ?
N1 C12 C11 116.1(4) . . ?
C14 C13 C11 121.5(4) . . ?
C14 C13 H13 119.2 . . ?
C11 C13 H13 119.2 . . ?
C13 C14 C17 123.5(4) . . ?
C13 C14 C15 119.5(4) . . ?
C17 C14 C15 116.9(4) . . ?
C14 C15 C19 112.4(4) . . ?
C14 C15 C16 110.2(4) . . ?
C19 C15 C16 112.8(4) . . ?
C14 C15 H15 113(3) . . ?
C19 C15 H15 105(3) . . ?
C16 C15 H15 103(3) . . ?
C10 C16 C15 114.2(4) . . ?
C10 C16 H16A 108.7 . . ?
C15 C16 H16A 108.7 . . ?
C10 C16 H16B 108.7 . . ?
C15 C16 H16B 108.7 . . ?
H16A C16 H16B 107.6 . . ?
O3 C17 O4 123.4(5) . . ?
O3 C17 C14 123.1(5) . . ?
O4 C17 C14 113.4(4) . . ?
C9 C18 S1 123.8(3) . . ?
C9 C18 S2 122.8(3) . . ?
S1 C18 S2 113.3(3) . . ?
C24 C19 C20 117.8(5) . . ?
C24 C19 C15 123.3(4) . . ?
C20 C19 C15 118.8(4) . . ?
C19 C20 C21 121.4(5) . . ?
C19 C20 H20 119.3 . . ?
C21 C20 H20 119.3 . . ?
C22 C21 C20 118.9(5) . . ?
C22 C21 H21 120.6 . . ?
C20 C21 H21 120.6 . . ?
C21 C22 C23 121.8(5) . . ?
C21 C22 Cl1 119.5(4) . . ?
C23 C22 Cl1 118.7(4) . . ?
C22 C23 C24 118.8(5) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C19 C24 C23 121.3(5) . . ?
C19 C24 H24 119.4 . . ?
C23 C24 H24 119.4 . . ?
O4 C25 H25A 109.5 . . ?
O4 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
O4 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C4 C26 H26A 109.5 . . ?
C4 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C4 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C7 C27 S1 108.3(4) . . ?
C7 C27 H27A 110.0 . . ?
S1 C27 H27A 110.0 . . ?
C7 C27 H27B 110.0 . . ?
S1 C27 H27B 110.0 . . ?
H27A C27 H27B 108.4 . . ?
C27 C7 S2 107.3(4) . . ?
C27 C7 H7A 110.2 . . ?
S2 C7 H7A 110.2 . . ?
C27 C7 H7B 110.2 . . ?
S2 C7 H7B 110.2 . . ?
H7A C7 H7B 108.5 . . ?
C17 O4 C25 115.4(5) . . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.903
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.096
_database_code_depnum_ccdc_archive 'CCDC 957105'
