# Supplementary Material (ESI) for Dalton Transactions
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               'Dalton Trans.'

_journal_coden_Cambridge         0222

_publ_contact_author_name        'Don Darensbourg'
_publ_contact_author_email       DJDARENS@MAIL.CHEM.TAMU.EDU

_publ_section_title              
;
Investigations into the Coupling of Cyclohexene Oxide and
Carbon Disulfide Catalyzed by (Salen)CrCl. Selectivity for the Production
of Copolymers vs Cyclic Thiocarbonates.
;
loop_
_publ_author_name
'Don Darensbourg'
'Jeremy R. Andreatta'
'Matthew J. Jungman'
'Joseph H Reibenspies'

# Attachment 's3.cif'

data_s3
_database_code_depnum_ccdc_archive 'CCDC 734841'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ddj1
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H40 S12'
_chemical_formula_weight         761.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   12.6954(14)
_cell_length_b                   10.0870(11)
_cell_length_c                   6.6497(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     851.55(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    110(2)
_cell_measurement_reflns_used    1250
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.485
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             400
_exptl_absorpt_coefficient_mu    7.302
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3229
_exptl_absorpt_correction_T_max  0.5288
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      110(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'MWPC area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6223
_diffrn_reflns_av_R_equivalents  0.1165
_diffrn_reflns_av_sigmaI/netI    0.0463
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         6.98
_diffrn_reflns_theta_max         62.98
_reflns_number_total             718
_reflns_number_gt                629
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker FRAMBO'
_computing_cell_refinement       'Bruker FRAMBO'
_computing_data_reduction        'Bruker Saint'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    XSEED
_computing_publication_material  ?

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger. Similarity restraints were used.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[\s^2^(Fo^2^)+(0.0464P)^2^+0.5200P] where P=(Fo^2^+2Fc^2^)/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         718
_refine_ls_number_parameters     85
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0829
_refine_ls_wR_factor_gt          0.0811
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.038
_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 0.17568(6) 0.2500 0.10293(11) 0.0190(3) Uani 1 2 d S . .
C1 C 0.2551(2) 0.2500 0.2969(4) 0.0149(7) Uani 1 2 d SD . .
S2A S 0.2896(5) 0.1046(5) 0.4214(11) 0.0195(11) Uani 0.50 1 d PD . -1
C2A C 0.3595(5) 0.1760(7) 0.6226(10) 0.0176(15) Uani 0.50 1 d PD . -1
H2AA H 0.3029 0.1806 0.7180 0.021 Uiso 0.50 1 d PR . -1
C3A C 0.4505(7) 0.0972(10) 0.7141(12) 0.019(2) Uani 0.50 1 d PD . -1
H3AA H 0.5073 0.0911 0.6193 0.022 Uiso 0.50 1 d PR . -1
H3AB H 0.4277 0.0090 0.7468 0.022 Uiso 0.50 1 d PR . -1
C4A C 0.4867(8) 0.1672(12) 0.9057(13) 0.024(2) Uani 0.50 1 d PD . -1
H4AA H 0.5571 0.1382 0.9347 0.029 Uiso 0.50 1 d PR . -1
H4AB H 0.4429 0.1382 1.0149 0.029 Uiso 0.50 1 d PR . -1
S2B S 0.3111(5) 0.1071(4) 0.3970(11) 0.0204(12) Uani 0.50 1 d PD . -2
C2B C 0.3956(5) 0.1830(7) 0.5732(10) 0.0140(14) Uani 0.50 1 d PD . -2
H2BA H 0.4565 0.1896 0.4883 0.017 Uiso 0.50 1 d PR . -2
C3B C 0.4274(7) 0.1110(11) 0.7661(11) 0.022(2) Uani 0.50 1 d PD . -2
H3BA H 0.4492 0.0227 0.7318 0.026 Uiso 0.50 1 d PR . -2
H3BB H 0.3683 0.1052 0.8555 0.026 Uiso 0.50 1 d PR . -2
C4B C 0.5158(7) 0.1876(11) 0.8695(14) 0.0185(18) Uani 0.50 1 d PD . -2
H4BA H 0.5801 0.1591 0.8071 0.022 Uiso 0.50 1 d PR . -2
H4BB H 0.5185 0.1591 1.0071 0.022 Uiso 0.50 1 d PR . -2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0178(4) 0.0240(5) 0.0150(4) 0.000 -0.0052(3) 0.000
C1 0.0139(15) 0.0165(16) 0.0144(15) 0.000 0.0026(12) 0.000
S2A 0.013(2) 0.0168(10) 0.0285(16) 0.0055(8) -0.0093(15) -0.0069(9)
C2A 0.017(4) 0.021(3) 0.015(3) -0.003(2) 0.003(2) 0.004(3)
C3A 0.026(4) 0.016(3) 0.014(4) 0.004(3) -0.004(3) -0.004(3)
C4A 0.025(6) 0.032(5) 0.017(4) 0.003(3) -0.001(3) -0.004(4)
S2B 0.017(2) 0.0142(11) 0.0299(18) 0.0046(8) -0.0124(17) -0.0057(10)
C2B 0.010(4) 0.017(2) 0.015(3) -0.004(3) -0.002(2) 0.002(3)
C3B 0.025(4) 0.026(4) 0.014(4) 0.004(3) -0.002(3) -0.001(3)
C4B 0.018(5) 0.024(4) 0.013(4) 0.005(3) -0.009(3) 0.002(3)

_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 C1 1.637(3) . ?
C1 S2B 1.739(3) 8_565 ?
C1 S2B 1.739(3) . ?
C1 S2A 1.740(3) 8_565 ?
C1 S2A 1.740(3) . ?
S2A C2A 1.760(4) . ?
C2A C3A 1.528(4) . ?
C2A C2B 1.529(3) 8_565 ?
C3A C4A 1.528(4) . ?
C4A C4B 1.529(4) 8_565 ?
S2B C2B 1.764(3) . ?
C2B C3B 1.528(4) . ?
C2B C2A 1.529(3) 8_565 ?
C3B C4B 1.527(4) . ?
C4B C4A 1.529(4) 8_565 ?

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
S1 C1 S2B 123.6(2) . 8_565 ?
S1 C1 S2B 123.6(2) . . ?
S2B C1 S2B 111.9(5) 8_565 . ?
S1 C1 S2A 122.0(2) . 8_565 ?
S2B C1 S2A 10.5(5) 8_565 8_565 ?
S2B C1 S2A 114.44(16) . 8_565 ?
S1 C1 S2A 122.0(2) . . ?
S2B C1 S2A 114.44(16) 8_565 . ?
S2B C1 S2A 10.5(5) . . ?
S2A C1 S2A 114.9(5) 8_565 . ?
C1 S2A C2A 98.3(4) . . ?
C3A C2A C2B 110.1(7) . 8_565 ?
C3A C2A S2A 118.1(6) . . ?
C2B C2A S2A 111.6(6) 8_565 . ?
C4A C3A C2A 108.6(8) . . ?
C3A C4A C4B 112.6(11) . 8_565 ?
C1 S2B C2B 98.2(4) . . ?
C3B C2B C2A 109.9(7) . 8_565 ?
C3B C2B S2B 120.8(6) . . ?
C2A C2B S2B 111.4(6) 8_565 . ?
C4B C3B C2B 109.4(8) . . ?
C3B C4B C4A 112.2(12) . 8_565 ?

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
S1 C1 S2A C2A -173.3(3) . . . . ?
S2B C1 S2A C2A 6.3(3) 8_565 . . . ?
S2B C1 S2A C2A 85(2) . . . . ?
S2A C1 S2A C2A -5.2(7) 8_565 . . . ?
C1 S2A C2A C3A -149.3(6) . . . . ?
C1 S2A C2A C2B -20.3(5) . . . 8_565 ?
C2B C2A C3A C4A 59.6(8) 8_565 . . . ?
S2A C2A C3A C4A -170.6(6) . . . . ?
C2A C3A C4A C4B -55.1(10) . . . 8_565 ?
S1 C1 S2B C2B 173.3(3) . . . . ?
S2B C1 S2B C2B 4.0(7) 8_565 . . . ?
S2A C1 S2B C2B -7.1(3) 8_565 . . . ?
S2A C1 S2B C2B -102(3) . . . . ?
C1 S2B C2B C3B 151.9(6) . . . . ?
C1 S2B C2B C2A 20.6(5) . . . 8_565 ?
C2A C2B C3B C4B -58.7(8) 8_565 . . . ?
S2B C2B C3B C4B 169.4(6) . . . . ?
C2B C3B C4B C4A 54.1(10) . . . 8_565 ?

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        62.98
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.387
_refine_diff_density_min         -0.326
_refine_diff_density_rms         0.072