# 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_3h
_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C43 H38 Cl2 N4 O4 S2'
_chemical_formula_weight         809.79

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'
S S 0.1246 0.1234 '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   Pnna
_symmetry_space_group_name_Hall  '-P 2a 2bc'

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

_cell_length_a                   14.6631(3)
_cell_length_b                   22.9825(4)
_cell_length_c                   13.3003(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     4482.13(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9849
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      27.44

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1688
_exptl_absorpt_coefficient_mu    0.281
_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      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  'CCD area detector'
_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            37936
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_av_sigmaI/netI    0.0187
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.77
_diffrn_reflns_theta_max         27.51
_reflns_number_total             5155
_reflns_number_gt                4331
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_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)+(0.0930P)²+2.5975P] 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     SHELXL
_refine_ls_extinction_coef       0.0056(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         5155
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0618
_refine_ls_R_factor_gt           0.0528
_refine_ls_wR_factor_ref         0.1486
_refine_ls_wR_factor_gt          0.1425
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.003
_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 0.15425(4) 0.98211(2) 0.18965(5) 0.04098(17) Uani 1 1 d . . .
S1 S -0.14291(3) 1.26836(2) -0.03914(3) 0.02448(15) Uani 1 1 d . . .
O1 O -0.15210(8) 1.07337(6) 0.06254(11) 0.0293(3) Uani 1 1 d . . .
O2 O -0.07202(8) 1.15722(6) 0.06581(11) 0.0290(3) Uani 1 1 d . . .
N1 N -0.29868(10) 1.12701(7) -0.02934(11) 0.0246(3) Uani 1 1 d . . .
N2 N -0.30844(10) 1.21870(7) -0.08257(11) 0.0213(3) Uani 1 1 d . . .
C1 C -0.10752(19) 0.98412(10) 0.1385(3) 0.0599(8) Uani 1 1 d . . .
H1B H -0.0597 0.9641 0.1736 0.090 Uiso 1 1 calc R . .
H1C H -0.1209 0.9641 0.0770 0.090 Uiso 1 1 calc R . .
H1D H -0.1612 0.9853 0.1799 0.090 Uiso 1 1 calc R . .
C2 C -0.07762(15) 1.04473(9) 0.11548(19) 0.0398(5) Uani 1 1 d . . .
H2A H -0.0637 1.0654 0.1772 0.048 Uiso 1 1 calc R . .
H2B H -0.0233 1.0441 0.0738 0.048 Uiso 1 1 calc R . .
C3 C -0.13962(11) 1.12981(8) 0.04266(13) 0.0226(4) Uani 1 1 d . . .
C4 C -0.21763(11) 1.15572(8) -0.00912(13) 0.0215(4) Uani 1 1 d . . .
C5 C -0.22251(11) 1.21240(8) -0.04223(12) 0.0205(3) Uani 1 1 d . . .
C6 C -0.35071(12) 1.16542(8) -0.07277(14) 0.0248(4) Uani 1 1 d . . .
H6A H -0.4097 1.1578 -0.0947 0.030 Uiso 1 1 calc R . .
C7 C -0.34545(12) 1.27141(8) -0.11964(13) 0.0219(4) Uani 1 1 d . . .
C8 C -0.43987(12) 1.27802(8) -0.12636(14) 0.0263(4) Uani 1 1 d . . .
H8A H -0.4785 1.2479 -0.1074 0.032 Uiso 1 1 calc R . .
C9 C -0.47523(13) 1.32982(10) -0.16141(15) 0.0321(4) Uani 1 1 d . . .
H9A H -0.5380 1.3343 -0.1677 0.038 Uiso 1 1 calc R . .
C10 C -0.41769(14) 1.37535(10) -0.18729(16) 0.0350(5) Uani 1 1 d . . .
H10A H -0.4420 1.4104 -0.2094 0.042 Uiso 1 1 calc R . .
C11 C -0.32408(14) 1.36861(9) -0.18019(15) 0.0304(4) Uani 1 1 d . . .
H11A H -0.2860 1.3994 -0.1972 0.037 Uiso 1 1 calc R . .
C12 C -0.28608(12) 1.31613(8) -0.14786(13) 0.0236(4) Uani 1 1 d . . .
C13 C -0.18595(12) 1.30914(8) -0.14273(13) 0.0237(4) Uani 1 1 d . . .
C14 C -0.12931(13) 1.33344(9) -0.21017(14) 0.0277(4) Uani 1 1 d . . .
H14A H -0.1569 1.3525 -0.2638 0.033 Uiso 1 1 calc R . .
C15 C -0.02959(14) 1.33352(10) -0.20948(15) 0.0336(5) Uani 1 1 d . . .
C16 C 0.01763(15) 1.32558(11) -0.29971(16) 0.0427(6) Uani 1 1 d . . .
H16A H -0.0148 1.3212 -0.3593 0.051 Uiso 1 1 calc R . .
C17 C 0.11106(17) 1.32417(16) -0.3016(2) 0.0658(10) Uani 1 1 d . . .
H17A H 0.1411 1.3176 -0.3621 0.079 Uiso 1 1 calc R . .
C18 C 0.16168(17) 1.33238(19) -0.2143(2) 0.0828(13) Uani 1 1 d . . .
C19 C 0.11508(17) 1.34179(16) -0.1244(2) 0.0713(11) Uani 1 1 d . . .
H19A H 0.1477 1.3483 -0.0654 0.086 Uiso 1 1 calc R . .
C20 C 0.02089(16) 1.34158(13) -0.12200(18) 0.0498(7) Uani 1 1 d . . .
H20A H -0.0092 1.3469 -0.0611 0.060 Uiso 1 1 calc R . .
C21 C 0.26553(19) 1.3330(3) -0.2187(3) 0.141(3) Uani 1 1 d . . .
H21A H 0.2851 1.3256 -0.2864 0.212 Uiso 1 1 calc R . .
H21B H 0.2893 1.3034 -0.1750 0.212 Uiso 1 1 calc R . .
H21C H 0.2876 1.3703 -0.1974 0.212 Uiso 1 1 calc R . .
C22 C 0.2500 1.0000 0.1143(2) 0.0288(6) Uani 1 2 d S . .
H22A H 0.2350 1.0324 0.0719 0.035 Uiso 1 1 d 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 C22 1.7730(17) . ?
S1 C5 1.7373(18) . ?
S1 C13 1.7819(18) . ?
O1 C3 1.336(2) . ?
O1 C2 1.457(2) . ?
O2 C3 1.214(2) . ?
N1 C6 1.302(2) . ?
N1 C4 1.386(2) . ?
N2 C5 1.377(2) . ?
N2 C6 1.379(2) . ?
N2 C7 1.416(2) . ?
C1 C2 1.492(3) . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C1 H1D 0.9600 . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.462(2) . ?
C4 C5 1.377(3) . ?
C6 H6A 0.9300 . ?
C7 C8 1.396(2) . ?
C7 C12 1.398(2) . ?
C8 C9 1.380(3) . ?
C8 H8A 0.9300 . ?
C9 C10 1.388(3) . ?
C9 H9A 0.9300 . ?
C10 C11 1.385(3) . ?
C10 H10A 0.9300 . ?
C11 C12 1.397(3) . ?
C11 H11A 0.9300 . ?
C12 C13 1.479(2) . ?
C13 C14 1.344(3) . ?
C14 C15 1.462(3) . ?
C14 H14A 0.9300 . ?
C15 C20 1.391(3) . ?
C15 C16 1.398(3) . ?
C16 C17 1.371(3) . ?
C16 H16A 0.9300 . ?
C17 C18 1.391(4) . ?
C17 H17A 0.9300 . ?
C18 C19 1.394(5) . ?
C18 C21 1.524(4) . ?
C19 C20 1.382(3) . ?
C19 H19A 0.9300 . ?
C20 H20A 0.9300 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 Cl1 1.7730(17) 2_575 ?
C22 H22A 0.9601 . ?

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 S1 C13 97.65(8) . . ?
C3 O1 C2 115.56(14) . . ?
C6 N1 C4 105.42(15) . . ?
C5 N2 C6 106.32(15) . . ?
C5 N2 C7 125.19(15) . . ?
C6 N2 C7 128.36(15) . . ?
C2 C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C2 C1 H1D 109.5 . . ?
H1B C1 H1D 109.5 . . ?
H1C C1 H1D 109.5 . . ?
O1 C2 C1 107.51(17) . . ?
O1 C2 H2A 110.2 . . ?
C1 C2 H2A 110.2 . . ?
O1 C2 H2B 110.2 . . ?
C1 C2 H2B 110.2 . . ?
H2A C2 H2B 108.5 . . ?
O2 C3 O1 124.43(17) . . ?
O2 C3 C4 123.15(17) . . ?
O1 C3 C4 112.42(15) . . ?
C5 C4 N1 110.11(15) . . ?
C5 C4 C3 125.21(15) . . ?
N1 C4 C3 124.65(16) . . ?
C4 C5 N2 105.76(15) . . ?
C4 C5 S1 131.14(13) . . ?
N2 C5 S1 123.10(14) . . ?
N1 C6 N2 112.38(15) . . ?
N1 C6 H6A 123.8 . . ?
N2 C6 H6A 123.8 . . ?
C8 C7 C12 121.36(17) . . ?
C8 C7 N2 119.71(16) . . ?
C12 C7 N2 118.93(15) . . ?
C9 C8 C7 119.23(18) . . ?
C9 C8 H8A 120.4 . . ?
C7 C8 H8A 120.4 . . ?
C8 C9 C10 120.40(18) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C11 C10 C9 120.09(19) . . ?
C11 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C10 C11 C12 120.88(19) . . ?
C10 C11 H11A 119.6 . . ?
C12 C11 H11A 119.6 . . ?
C11 C12 C7 117.97(17) . . ?
C11 C12 C13 120.28(17) . . ?
C7 C12 C13 121.74(17) . . ?
C14 C13 C12 122.54(17) . . ?
C14 C13 S1 121.04(14) . . ?
C12 C13 S1 116.39(13) . . ?
C13 C14 C15 127.90(18) . . ?
C13 C14 H14A 116.0 . . ?
C15 C14 H14A 116.0 . . ?
C20 C15 C16 118.2(2) . . ?
C20 C15 C14 122.5(2) . . ?
C16 C15 C14 119.33(18) . . ?
C17 C16 C15 120.9(2) . . ?
C17 C16 H16A 119.5 . . ?
C15 C16 H16A 119.5 . . ?
C16 C17 C18 121.0(3) . . ?
C16 C17 H17A 119.5 . . ?
C18 C17 H17A 119.5 . . ?
C17 C18 C19 118.4(2) . . ?
C17 C18 C21 120.2(3) . . ?
C19 C18 C21 121.4(3) . . ?
C20 C19 C18 120.6(2) . . ?
C20 C19 H19A 119.7 . . ?
C18 C19 H19A 119.7 . . ?
C19 C20 C15 120.9(2) . . ?
C19 C20 H20A 119.6 . . ?
C15 C20 H20A 119.6 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
Cl1 C22 Cl1 111.20(16) . 2_575 ?
Cl1 C22 H22A 109.3 . . ?
Cl1 C22 H22A 109.5 2_575 . ?

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        27.51
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.542
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.146




# SQUEEZE RESULTS (APPEND TO CIF)
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 -0.005 0.500 0.000 381.0 21.8
2 0.734 1.000 0.500 381.0 21.8

_platon_squeeze_details          
; 
Some solvents were highly disordered, and attempts to locate and refine 
these solvent's peaks were unsuccessful. Thus, the SQUEEZE procedure in 
PLATON was performed to correct the intensities, corresponding to 
disordered part of the structure.
;

_database_code_depnum_ccdc_archive 'CCDC 1005205'
