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

data_global

#===============================================================================

# 1. SUBMISSION DETAILS

_publ_contact_author             
;
	Dr. P.J. Stevenson
	School of Chemistry
	Queen's University of Belfast
	Belfast
	BT9 5AG
	UK
;
_publ_contact_author_phone       '00 44 2890 974426'
_publ_contact_author_email       p.stevenson@qub.ac.uk

_publ_requested_journal          'Organic and Biomolecular Chemistry'

#===============================================================================

# 2. TITLE AND AUTHOR LIST

_publ_section_title              
;Reactions of enantiopure cyclic diols with sulfuryl chloride.
;

loop_
_publ_author_name
_publ_author_address
'Boyd, Derek R.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Sharma, Narain D.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Kaik, Magdalena'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'McIntyre, Peter B.A.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Malone, John F.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Stevenson, Paul J.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;

#============================================================================

data_4c

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 Cl2 I O3 S'
_chemical_formula_sum            'C6 H7 Cl2 I O3 S'
_chemical_formula_weight         356.98
_chemical_absolute_configuration ad

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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           orthorhombic
_symmetry_space_group_name_H-M   P212121

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

_cell_length_a                   5.9357(12)
_cell_length_b                   8.960(3)
_cell_length_c                   20.683(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1100.0(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    39
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      12.50

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.35
_exptl_crystal_size_min          0.33
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.156
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    3.560
_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      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  'Bruker P4 diffractometer'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         3
_diffrn_standards_interval_count 97
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            2047
_diffrn_reflns_av_R_equivalents  0.0941
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       1
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_theta_min         2.48
_diffrn_reflns_theta_max         27.49
_reflns_number_total             1868
_reflns_number_gt                1525
_reflns_threshold_expression     >2sigma(I)

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

_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)+(0.1373P)²+1.0267P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.024(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.04(9)
_refine_ls_number_reflns         1868
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0715
_refine_ls_wR_factor_ref         0.1976
_refine_ls_wR_factor_gt          0.1840
_refine_ls_goodness_of_fit_ref   1.072
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.001
_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
C1 C 0.6069(16) 1.4472(12) 1.1324(4) 0.042(2) Uani 1 1 d . . .
H1 H 0.4895 1.3903 1.1548 0.050 Uiso 1 1 calc R . .
O1 O 0.8368(11) 1.3848(9) 1.1464(3) 0.0508(18) Uani 1 1 d . . .
S1 S 0.8817(5) 1.3040(3) 1.21077(11) 0.0477(6) Uani 1 1 d . . .
Cl1 Cl 0.7370(6) 1.1053(3) 1.19465(18) 0.0781(10) Uani 1 1 d . . .
O2 O 0.7659(18) 1.3672(9) 1.2617(3) 0.073(3) Uani 1 1 d . . .
O3 O 1.1134(14) 1.2795(12) 1.2139(4) 0.074(3) Uani 1 1 d . . .
C2 C 0.5886(16) 1.4290(11) 1.0606(4) 0.0390(19) Uani 1 1 d . . .
H2 H 0.6399 1.3288 1.0486 0.047 Uiso 1 1 calc R . .
Cl2 Cl 0.2932(4) 1.4484(4) 1.04040(16) 0.0640(8) Uani 1 1 d . . .
C3 C 0.7178(14) 1.5412(9) 1.0237(4) 0.0328(17) Uani 1 1 d . . .
I3 I 0.76066(13) 1.49845(8) 0.92466(3) 0.0604(4) Uani 1 1 d . . .
C4 C 0.8124(18) 1.6603(10) 1.0493(5) 0.044(2) Uani 1 1 d . . .
H4 H 0.8981 1.7228 1.0232 0.053 Uiso 1 1 calc R . .
C5 C 0.785(2) 1.6984(11) 1.1206(5) 0.053(3) Uani 1 1 d . . .
H5A H 0.9262 1.6786 1.1428 0.064 Uiso 1 1 calc R . .
H5B H 0.7531 1.8041 1.1248 0.064 Uiso 1 1 calc R . .
C6 C 0.6016(19) 1.6112(13) 1.1522(5) 0.053(3) Uani 1 1 d . . .
H6A H 0.4572 1.6539 1.1403 0.063 Uiso 1 1 calc R . .
H6B H 0.6169 1.6186 1.1987 0.063 Uiso 1 1 calc R . .

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
C1 0.033(4) 0.055(5) 0.038(4) 0.008(4) 0.006(4) 0.005(4)
O1 0.035(3) 0.068(5) 0.049(4) 0.024(4) 0.001(3) 0.003(4)
S1 0.0574(14) 0.0536(13) 0.0322(10) 0.0079(10) -0.0064(11) -0.0009(13)
Cl1 0.091(2) 0.0488(13) 0.094(2) -0.0033(14) 0.010(2) -0.0090(18)
O2 0.115(8) 0.068(5) 0.036(3) -0.004(3) 0.002(4) -0.001(7)
O3 0.052(4) 0.097(7) 0.072(5) 0.025(5) -0.016(4) 0.007(5)
C2 0.034(4) 0.038(5) 0.045(5) 0.006(4) -0.005(4) 0.002(4)
Cl2 0.0380(12) 0.0663(16) 0.088(2) 0.0195(16) -0.0141(13) -0.0086(13)
C3 0.033(4) 0.034(4) 0.031(4) 0.008(3) -0.004(3) 0.002(4)
I3 0.0761(6) 0.0729(6) 0.0323(4) -0.0009(3) -0.0001(3) 0.0139(5)
C4 0.049(5) 0.034(4) 0.049(5) 0.010(4) -0.003(5) -0.005(4)
C5 0.073(7) 0.042(4) 0.046(5) -0.008(4) -0.007(5) 0.004(6)
C6 0.053(6) 0.060(6) 0.045(5) -0.010(5) 0.007(5) -0.001(6)

_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
C1 C2 1.497(12) . ?
C1 O1 1.503(11) . ?
C1 C6 1.526(16) . ?
O1 S1 1.538(7) . ?
S1 O2 1.380(9) . ?
S1 O3 1.394(9) . ?
S1 Cl1 2.005(4) . ?
C2 C3 1.478(13) . ?
C2 Cl2 1.811(9) . ?
C3 C4 1.317(13) . ?
C3 I3 2.099(8) . ?
C4 C5 1.522(14) . ?
C5 C6 1.492(16) . ?

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 O1 102.5(7) . . ?
C2 C1 C6 111.7(8) . . ?
O1 C1 C6 109.0(9) . . ?
C1 O1 S1 120.0(5) . . ?
O2 S1 O3 121.4(6) . . ?
O2 S1 O1 112.4(5) . . ?
O3 S1 O1 106.6(5) . . ?
O2 S1 Cl1 106.1(5) . . ?
O3 S1 Cl1 106.9(5) . . ?
O1 S1 Cl1 101.5(4) . . ?
C3 C2 C1 113.6(8) . . ?
C3 C2 Cl2 108.5(6) . . ?
C1 C2 Cl2 106.8(7) . . ?
C4 C3 C2 124.4(8) . . ?
C4 C3 I3 119.3(7) . . ?
C2 C3 I3 116.3(6) . . ?
C3 C4 C5 121.8(9) . . ?
C6 C5 C4 112.5(9) . . ?
C5 C6 C1 111.9(9) . . ?

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 C1 O1 S1 -147.1(7) . . . . ?
C6 C1 O1 S1 94.4(8) . . . . ?
C1 O1 S1 O2 -36.0(10) . . . . ?
C1 O1 S1 O3 -171.2(8) . . . . ?
C1 O1 S1 Cl1 77.0(8) . . . . ?
O1 C1 C2 C3 -76.7(9) . . . . ?
C6 C1 C2 C3 39.8(12) . . . . ?
O1 C1 C2 Cl2 163.7(6) . . . . ?
C6 C1 C2 Cl2 -79.8(10) . . . . ?
C1 C2 C3 C4 -10.1(13) . . . . ?
Cl2 C2 C3 C4 108.5(9) . . . . ?
C1 C2 C3 I3 167.2(6) . . . . ?
Cl2 C2 C3 I3 -74.2(7) . . . . ?
C2 C3 C4 C5 -3.5(15) . . . . ?
I3 C3 C4 C5 179.3(7) . . . . ?
C3 C4 C5 C6 -14.0(14) . . . . ?
C4 C5 C6 C1 43.7(13) . . . . ?
C2 C1 C6 C5 -57.7(13) . . . . ?
O1 C1 C6 C5 54.8(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         2.976
_refine_diff_density_min         -1.226
_refine_diff_density_rms         0.246
_database_code_depnum_ccdc_archive 'CCDC 971376'
data_global

#===============================================================================

# 1. SUBMISSION DETAILS

_publ_contact_author             
;
	Dr. P.J. Stevenson
	School of Chemistry
	Queen's University of Belfast
	Belfast
	BT9 5AG
	UK
;
_publ_contact_author_phone       '00 44 2890 974426'
_publ_contact_author_email       p.stevenson@qub.ac.uk

_publ_requested_journal          'Organic and Biomolecular Chemistry'

#===============================================================================

# 2. TITLE AND AUTHOR LIST

_publ_section_title              
;Reactions of enantiopure cyclic diols with sulfuryl chloride.
;

loop_
_publ_author_name
_publ_author_address
'Boyd, Derek R.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Sharma, Narain D.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Kaik, Magdalena'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'McIntyre, Peter B.A.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Malone, John F.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Stevenson, Paul J.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;

#============================================================================

data_12b

_audit_creation_date             
;
'Sun Feb 07 10:56:34 2010'
;
_audit_creation_method           
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H10 Cl2'
_chemical_formula_sum            'C10 H10 Cl2'
_chemical_formula_weight         201.08
_chemical_absolute_configuration ad

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'
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)

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

_cell_length_a                   7.4192(4)
_cell_length_b                   7.6708(4)
_cell_length_c                   8.1477(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.304(5)
_cell_angle_gamma                90.00
_cell_volume                     454.70(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1483
_cell_measurement_theta_min      2.7941
_cell_measurement_theta_max      30.8567

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             208
_exptl_absorpt_coefficient_mu    0.650
_exptl_absorpt_correction_T_min  0.93745
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3795
_diffrn_reflns_number            2509
_diffrn_reflns_av_R_equivalents  0.0214
_diffrn_reflns_av_sigmaI/netI    0.0549
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.7941
_diffrn_reflns_theta_max         30.8567
_reflns_number_total             1797
_reflns_number_gt                1578
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_cell_refinement       
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_data_reduction        
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET)
(compiled Jan  5 2010,16:28:46)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0238P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.05(6)
_refine_ls_number_reflns         1797
_refine_ls_number_parameters     109
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0368
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0593
_refine_ls_wR_factor_gt          0.0578
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
Cl1 Cl 0.24966(6) 1.28754(7) 0.89759(6) 0.02777(14) Uani 1 1 d . . .
C1 C 0.2937(3) 1.0615(3) 0.8436(3) 0.0198(5) Uani 1 1 d . . .
H1 H 0.4094 1.0203 0.9181 0.024 Uiso 1 1 calc R . .
Cl2 Cl 0.21122(7) 0.72926(7) 0.90109(7) 0.03221(16) Uani 1 1 d . . .
C2 C 0.1329(3) 0.9547(3) 0.8797(3) 0.0215(5) Uani 1 1 d . . .
H2 H 0.1016 0.9945 0.9876 0.026 Uiso 1 1 calc R . .
C3 C -0.0353(2) 0.9700(3) 0.7414(3) 0.0243(5) Uani 1 1 d . . .
H3A H -0.0787 1.0923 0.7342 0.029 Uiso 1 1 calc R . .
H3B H -0.1347 0.8962 0.7689 0.029 Uiso 1 1 calc R . .
C4 C 0.0045(3) 0.9147(3) 0.5732(3) 0.0242(5) Uani 1 1 d . . .
H4A H 0.0115 0.7859 0.5698 0.029 Uiso 1 1 calc R . .
H4B H -0.0987 0.9520 0.4838 0.029 Uiso 1 1 calc R . .
C4A C 0.1815(2) 0.9901(3) 0.5378(2) 0.0181(4) Uani 1 1 d . . .
C5 C 0.2124(3) 0.9913(4) 0.3747(2) 0.0236(5) Uani 1 1 d . . .
H5 H 0.1205 0.9470 0.2868 0.028 Uiso 1 1 calc R . .
C6 C 0.3735(3) 1.0556(3) 0.3381(3) 0.0279(6) Uani 1 1 d . . .
H6 H 0.3912 1.0567 0.2258 0.033 Uiso 1 1 calc R . .
C7 C 0.5093(3) 1.1184(3) 0.4656(3) 0.0274(5) Uani 1 1 d . . .
H7 H 0.6210 1.1620 0.4410 0.033 Uiso 1 1 calc R . .
C8 C 0.4824(3) 1.1178(3) 0.6286(3) 0.0228(5) Uani 1 1 d . . .
H8 H 0.5760 1.1604 0.7161 0.027 Uiso 1 1 calc R . .
C8A C 0.3179(2) 1.0548(3) 0.6654(3) 0.0183(5) Uani 1 1 d . . .

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
Cl1 0.0341(3) 0.0222(3) 0.0269(3) -0.0064(3) 0.0057(2) 0.0019(2)
C1 0.0239(10) 0.0171(12) 0.0172(11) -0.0008(9) 0.0010(8) 0.0028(8)
Cl2 0.0352(3) 0.0236(3) 0.0373(3) 0.0108(3) 0.0059(2) 0.0013(2)
C2 0.0253(10) 0.0195(13) 0.0214(11) 0.0023(10) 0.0088(8) 0.0029(9)
C3 0.0161(9) 0.0312(16) 0.0268(11) 0.0032(11) 0.0071(8) -0.0014(9)
C4 0.0201(10) 0.0259(14) 0.0254(12) -0.0004(10) 0.0013(8) -0.0039(9)
C4A 0.0195(9) 0.0156(12) 0.0187(10) -0.0002(11) 0.0027(7) 0.0029(9)
C5 0.0258(11) 0.0247(14) 0.0188(11) -0.0024(12) 0.0010(8) 0.0008(10)
C6 0.0354(12) 0.0311(17) 0.0198(12) 0.0033(10) 0.0117(9) 0.0044(10)
C7 0.0253(11) 0.0284(15) 0.0316(13) 0.0037(12) 0.0131(9) -0.0028(9)
C8 0.0217(10) 0.0199(13) 0.0264(12) -0.0013(11) 0.0035(9) -0.0029(9)
C8A 0.0193(9) 0.0171(13) 0.0188(10) 0.0004(9) 0.0044(7) 0.0011(8)

_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 C1 1.834(2) . ?
C1 C8A 1.499(3) . ?
C1 C2 1.522(3) . ?
C1 H1 1.0000 . ?
Cl2 C2 1.821(2) . ?
C2 C3 1.513(3) . ?
C2 H2 1.0000 . ?
C3 C4 1.518(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C4A 1.513(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C4A C8A 1.392(3) . ?
C4A C5 1.392(3) . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.381(3) . ?
C7 H7 0.9500 . ?
C8 C8A 1.399(3) . ?
C8 H8 0.9500 . ?

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
C8A C1 C2 114.56(18) . . ?
C8A C1 Cl1 108.99(15) . . ?
C2 C1 Cl1 106.22(14) . . ?
C8A C1 H1 109.0 . . ?
C2 C1 H1 109.0 . . ?
Cl1 C1 H1 109.0 . . ?
C3 C2 C1 112.18(18) . . ?
C3 C2 Cl2 110.25(16) . . ?
C1 C2 Cl2 106.38(13) . . ?
C3 C2 H2 109.3 . . ?
C1 C2 H2 109.3 . . ?
Cl2 C2 H2 109.3 . . ?
C2 C3 C4 111.87(16) . . ?
C2 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
C2 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
C4A C4 C3 113.23(18) . . ?
C4A C4 H4A 108.9 . . ?
C3 C4 H4A 108.9 . . ?
C4A C4 H4B 108.9 . . ?
C3 C4 H4B 108.9 . . ?
H4A C4 H4B 107.7 . . ?
C8A C4A C5 118.57(18) . . ?
C8A C4A C4 121.68(17) . . ?
C5 C4A C4 119.72(19) . . ?
C6 C5 C4A 121.4(2) . . ?
C6 C5 H5 119.3 . . ?
C4A C5 H5 119.3 . . ?
C5 C6 C7 119.8(2) . . ?
C5 C6 H6 120.1 . . ?
C7 C6 H6 120.1 . . ?
C8 C7 C6 119.91(19) . . ?
C8 C7 H7 120.0 . . ?
C6 C7 H7 120.0 . . ?
C7 C8 C8A 120.3(2) . . ?
C7 C8 H8 119.9 . . ?
C8A C8 H8 119.9 . . ?
C4A C8A C8 120.03(19) . . ?
C4A C8A C1 121.87(16) . . ?
C8 C8A C1 118.10(19) . . ?

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
C8A C1 C2 C3 -40.8(2) . . . . ?
Cl1 C1 C2 C3 79.6(2) . . . . ?
C8A C1 C2 Cl2 79.86(19) . . . . ?
Cl1 C1 C2 Cl2 -159.77(10) . . . . ?
C1 C2 C3 C4 57.4(3) . . . . ?
Cl2 C2 C3 C4 -61.0(2) . . . . ?
C2 C3 C4 C4A -45.7(3) . . . . ?
C3 C4 C4A C8A 19.0(3) . . . . ?
C3 C4 C4A C5 -162.7(2) . . . . ?
C8A C4A C5 C6 -0.3(4) . . . . ?
C4 C4A C5 C6 -178.6(2) . . . . ?
C4A C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C6 C7 C8 C8A -0.3(4) . . . . ?
C5 C4A C8A C8 -0.5(3) . . . . ?
C4 C4A C8A C8 177.7(2) . . . . ?
C5 C4A C8A C1 178.7(2) . . . . ?
C4 C4A C8A C1 -3.0(3) . . . . ?
C7 C8 C8A C4A 0.9(3) . . . . ?
C7 C8 C8A C1 -178.4(2) . . . . ?
C2 C1 C8A C4A 13.9(3) . . . . ?
Cl1 C1 C8A C4A -104.9(2) . . . . ?
C2 C1 C8A C8 -166.82(19) . . . . ?
Cl1 C1 C8A C8 74.4(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_theta_full        30.93
_diffrn_measured_fraction_theta_full 0.972
_refine_diff_density_max         0.287
_refine_diff_density_min         -0.258
_refine_diff_density_rms         0.053
_database_code_depnum_ccdc_archive 'CCDC 971377'
data_global

#===============================================================================

# 1. SUBMISSION DETAILS

_publ_contact_author             
;
	Dr. P.J. Stevenson
	School of Chemistry
	Queen's University of Belfast
	Belfast
	BT9 5AG
	UK
;
_publ_contact_author_phone       '00 44 2890 974426'
_publ_contact_author_email       p.stevenson@qub.ac.uk

_publ_requested_journal          'Organic and Biomolecular Chemistry'

#===============================================================================

# 2. TITLE AND AUTHOR LIST

_publ_section_title              
;Reactions of enantiopure cyclic diols with sulfuryl chloride.
;

loop_
_publ_author_name
_publ_author_address
'Boyd, Derek R.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Sharma, Narain D.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Kaik, Magdalena'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'McIntyre, Peter B.A.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Malone, John F.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;
'Stevenson, Paul J.'
;     School of Chemistry and Chemical Engineering
      The Queen's University of Belfast
      Belfast
      UK
      BT9 5AG
;

#============================================================================

data_3a

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 Cl O4 S'
_chemical_formula_sum            'C6 H7 Cl O4 S'
_chemical_formula_weight         210.63
_chemical_absolute_configuration ad
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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   P212121

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

_cell_length_a                   6.6774(1)
_cell_length_b                   10.9657(2)
_cell_length_c                   11.0176(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     806.73(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6311
_cell_measurement_theta_min      4.009
_cell_measurement_theta_max      76.5176

_exptl_crystal_description       blocks
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.2358
_exptl_crystal_size_mid          0.1663
_exptl_crystal_size_min          0.1450
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             432
_exptl_absorpt_coefficient_mu    6.431
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_correction_T_min  0.370
_exptl_absorpt_correction_T_max  0.540
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54180
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.3196
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5964
_diffrn_reflns_av_R_equivalents  0.0254
_diffrn_reflns_av_sigmaI/netI    0.0141
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         5.69
_diffrn_reflns_theta_max         76.72
_reflns_number_total             1674
_reflns_number_gt                1670
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
;
_computing_data_reduction        
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.33.55 (release 05-01-2010 CrysAlis171 .NET) 
(compiled Jan  5 2010,16:28:46) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'

_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)+(0.0375P)²+0.3139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.006(14)
_refine_ls_number_reflns         1675
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0226
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0603
_refine_ls_wR_factor_gt          0.0603
_refine_ls_goodness_of_fit_ref   1.081
_refine_ls_restrained_S_all      1.081
_refine_ls_shift/su_max          0.001
_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
C1 C -0.5276(2) -0.54326(15) -0.88071(15) 0.0155(3) Uani 1 1 d . . .
H1 H -0.5874 -0.6266 -0.8742 0.019 Uiso 1 1 calc R . .
O1 O -0.31136(18) -0.54734(11) -0.85475(10) 0.0170(2) Uani 1 1 d . . .
C2 C -0.5351(2) -0.49820(15) -1.01258(14) 0.0150(3) Uani 1 1 d . . .
H2 H -0.6566 -0.5314 -1.0541 0.018 Uiso 1 1 calc R . .
O2 O -0.35238(19) -0.54858(12) -1.06873(10) 0.0205(3) Uani 1 1 d . . .
S1 S -0.19665(6) -0.59250(3) -0.97045(3) 0.01546(11) Uani 1 1 d . . .
O3 O -0.01578(19) -0.52473(12) -0.98178(13) 0.0249(3) Uani 1 1 d . . .
O4 O -0.1856(2) -0.72186(11) -0.97278(12) 0.0231(3) Uani 1 1 d . . .
C3 C -0.5322(2) -0.36175(15) -1.02178(15) 0.0162(3) Uani 1 1 d . . .
Cl3 Cl -0.53020(6) -0.30755(4) -1.17104(4) 0.02222(11) Uani 1 1 d . . .
C4 C -0.5323(3) -0.28578(16) -0.92835(16) 0.0195(3) Uani 1 1 d . . .
H4 H -0.5285 -0.2005 -0.9435 0.023 Uiso 1 1 calc R . .
C5 C -0.5381(3) -0.32963(16) -0.79914(15) 0.0194(3) Uani 1 1 d . . .
H5A H -0.6214 -0.2734 -0.7502 0.023 Uiso 1 1 calc R . .
H5B H -0.4008 -0.3287 -0.7652 0.023 Uiso 1 1 calc R . .
C6 C -0.6231(3) -0.45807(16) -0.79015(14) 0.0174(3) Uani 1 1 d . . .
H6A H -0.6009 -0.4898 -0.7071 0.021 Uiso 1 1 calc R . .
H6B H -0.7694 -0.4553 -0.8046 0.021 Uiso 1 1 calc R . .

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
C1 0.0151(7) 0.0172(7) 0.0143(7) -0.0006(6) -0.0014(6) -0.0026(6)
O1 0.0167(6) 0.0219(6) 0.0123(5) -0.0015(4) -0.0009(4) 0.0053(5)
C2 0.0146(7) 0.0163(7) 0.0140(7) -0.0017(6) 0.0005(6) 0.0002(6)
O2 0.0225(6) 0.0264(6) 0.0127(5) -0.0016(5) 0.0007(4) 0.0093(5)
S1 0.01616(19) 0.01512(19) 0.01509(19) -0.00034(14) 0.00100(15) 0.00233(14)
O3 0.0203(6) 0.0276(6) 0.0267(6) -0.0002(5) 0.0024(5) -0.0045(5)
O4 0.0282(6) 0.0149(6) 0.0262(6) -0.0010(5) 0.0022(6) 0.0047(5)
C3 0.0131(7) 0.0176(7) 0.0179(7) 0.0037(6) 0.0000(7) 0.0003(6)
Cl3 0.0225(2) 0.0247(2) 0.0194(2) 0.00762(16) 0.00024(15) 0.00124(16)
C4 0.0162(8) 0.0159(7) 0.0263(9) 0.0002(6) -0.0005(7) 0.0015(7)
C5 0.0181(8) 0.0194(8) 0.0206(8) -0.0060(6) -0.0005(6) 0.0011(7)
C6 0.0155(7) 0.0221(8) 0.0146(7) -0.0012(6) 0.0011(6) -0.0001(7)

_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
C1 O1 1.4727(19) . ?
C1 C6 1.508(2) . ?
C1 C2 1.535(2) . ?
C1 H1 1.0000 . ?
O1 S1 1.5674(11) . ?
C2 O2 1.475(2) . ?
C2 C3 1.500(2) . ?
C2 H2 1.0000 . ?
O2 S1 1.5766(12) . ?
S1 O4 1.4207(12) . ?
S1 O3 1.4235(13) . ?
C3 C4 1.324(2) . ?
C3 Cl3 1.7487(17) . ?
C4 C5 1.503(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.522(2) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?

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
O1 C1 C6 107.76(13) . . ?
O1 C1 C2 103.03(12) . . ?
C6 C1 C2 114.38(14) . . ?
O1 C1 H1 110.5 . . ?
C6 C1 H1 110.5 . . ?
C2 C1 H1 110.5 . . ?
C1 O1 S1 109.32(9) . . ?
O2 C2 C3 109.55(13) . . ?
O2 C2 C1 104.44(12) . . ?
C3 C2 C1 112.61(13) . . ?
O2 C2 H2 110.0 . . ?
C3 C2 H2 110.0 . . ?
C1 C2 H2 110.0 . . ?
C2 O2 S1 111.83(10) . . ?
O4 S1 O3 118.39(8) . . ?
O4 S1 O1 110.83(7) . . ?
O3 S1 O1 108.72(8) . . ?
O4 S1 O2 109.09(8) . . ?
O3 S1 O2 109.87(8) . . ?
O1 S1 O2 98.03(6) . . ?
C4 C3 C2 125.11(15) . . ?
C4 C3 Cl3 121.14(13) . . ?
C2 C3 Cl3 113.75(12) . . ?
C3 C4 C5 122.34(15) . . ?
C3 C4 H4 118.8 . . ?
C5 C4 H4 118.8 . . ?
C4 C5 C6 111.54(14) . . ?
C4 C5 H5A 109.3 . . ?
C6 C5 H5A 109.3 . . ?
C4 C5 H5B 109.3 . . ?
C6 C5 H5B 109.3 . . ?
H5A C5 H5B 108.0 . . ?
C1 C6 C5 111.85(14) . . ?
C1 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
C1 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?

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 O1 S1 -159.06(11) . . . . ?
C2 C1 O1 S1 -37.79(14) . . . . ?
O1 C1 C2 O2 32.35(15) . . . . ?
C6 C1 C2 O2 149.01(14) . . . . ?
O1 C1 C2 C3 -86.44(15) . . . . ?
C6 C1 C2 C3 30.23(19) . . . . ?
C3 C2 O2 S1 104.44(13) . . . . ?
C1 C2 O2 S1 -16.40(15) . . . . ?
C1 O1 S1 O4 -87.42(11) . . . . ?
C1 O1 S1 O3 140.82(11) . . . . ?
C1 O1 S1 O2 26.59(11) . . . . ?
C2 O2 S1 O4 110.20(12) . . . . ?
C2 O2 S1 O3 -118.49(11) . . . . ?
C2 O2 S1 O1 -5.19(12) . . . . ?
O2 C2 C3 C4 -118.64(18) . . . . ?
C1 C2 C3 C4 -2.9(2) . . . . ?
O2 C2 C3 Cl3 61.77(15) . . . . ?
C1 C2 C3 Cl3 177.52(11) . . . . ?
C2 C3 C4 C5 -0.8(3) . . . . ?
Cl3 C3 C4 C5 178.76(13) . . . . ?
C3 C4 C5 C6 -22.1(2) . . . . ?
O1 C1 C6 C5 60.24(17) . . . . ?
C2 C1 C6 C5 -53.67(19) . . . . ?
C4 C5 C6 C1 48.1(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        76.71
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.058
_database_code_depnum_ccdc_archive 'CCDC 971378'
