# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_shelx
_database_code_depnum_ccdc_archive 'CCDC 1542642'
_audit_update_record             
;
2017-12-22 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '2-chloro (methylsulfonyl) methanesulfonate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C4 H9 Cl O5 S2'
_chemical_formula_weight         236.68

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'
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'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   9.4479(7)
_cell_length_b                   5.5001(3)
_cell_length_c                   10.0650(7)
_cell_angle_alpha                90
_cell_angle_beta                 112.633(9)
_cell_angle_gamma                90
_cell_volume                     482.74(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    830
_cell_measurement_theta_min      5.0640
_cell_measurement_theta_max      71.6970
_exptl_crystal_description       fragment
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.628
_exptl_crystal_F_000             244
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.305
_exptl_crystal_size_mid          0.162
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    7.485
_shelx_estimated_absorpt_T_min   0.209
_shelx_estimated_absorpt_T_max   0.586
_exptl_absorpt_correction_T_min  0.83017
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Eos
_diffrn_detector_area_resol_mean 16.0604
_diffrn_reflns_number            1784
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_av_R_equivalents  0.0299
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.760
_diffrn_reflns_theta_max         70.824
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.679
_diffrn_reflns_point_group_measured_fraction_full 0.686
_reflns_number_total             1263
_reflns_number_gt                1186
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.227
_reflns_Friedel_fraction_max     0.283
_reflns_Friedel_fraction_full    0.292
_reflns_special_details          
;
Reflections were merged by SHELXL according to the crystal
class for the calculation of statistics and refinement.
_reflns_Friedel_fraction is defined as the number of unique
Friedel pairs measured divided by the number that would be
possible theoretically, ignoring centric projections and
systematic absences.
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXS (Sheldick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0566P)²+0.1322P] 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_abs_structure_details 
;
Flack x determined using 207 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
# start Validation Reply Form
_vrf_PLAT915_shelx               
;
PROBLEM: No Flack x Check Done: Low Friedel Pair Coverage         28 %     
RESPONSE: Because the data collection strategy followed by standard 
diffractometer softs does not check fon non-centrosymmetric crystal 
structures, unless overriding the default from the begining, it did 
not measure all Friedel pairs of the present chiral P2(1) group. 
Unfortunately, we lack of fresh crystals to re-collect a complete data 
set for this group. Though the somewhat small Friedel Pair coverage, 
still the Flack x parameter (calculated with the Parson's method) equal 
to 0.09(5) and R1=0.0427 for the correct absolute structure are in sharp 
contrast with the x=0.91(5) and R1=0.0484 values for the other molecule 
handeness.        
;
# end Validation Reply Form
_refine_ls_abs_structure_Flack   0.09(5)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1263
_refine_ls_number_parameters     110
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0427
_refine_ls_wR_factor_ref         0.1149
_refine_ls_wR_factor_gt          0.1081
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6736(10) 0.8152(16) 0.5522(8) 0.0694(18) Uani 1 1 d . . . . .
H1A H 0.5730 0.7529 0.4976 0.104 Uiso 1 1 calc R U . . .
H1B H 0.6878 0.9661 0.5110 0.104 Uiso 1 1 calc R U . . .
H1C H 0.6845 0.8418 0.6499 0.104 Uiso 1 1 calc R U . . .
C2 C 0.7937(6) 0.5995(12) 0.3642(5) 0.0423(10) Uani 1 1 d . . . . .
H2A H 0.7864 0.7652 0.3293 0.051 Uiso 1 1 calc R U . . .
H2B H 0.8862 0.5286 0.3605 0.051 Uiso 1 1 calc R U . . .
C3 C 0.7340(7) 0.3302(14) 0.0468(6) 0.0567(15) Uani 1 1 d . . . . .
H3A H 0.6861 0.1722 0.0189 0.068 Uiso 1 1 calc R U . . .
H3B H 0.8348 0.3077 0.1221 0.068 Uiso 1 1 calc R U . . .
C4 C 0.7466(7) 0.4540(15) -0.0783(6) 0.0575(16) Uani 1 1 d . . . . .
H4A H 0.6448 0.4961 -0.1462 0.069 Uiso 1 1 calc R U . . .
H4B H 0.7917 0.3433 -0.1260 0.069 Uiso 1 1 calc R U . . .
O3 O 0.6392(5) 0.4877(9) 0.0975(4) 0.0545(11) Uani 1 1 d . . . . .
O11 O 0.7742(7) 0.3732(9) 0.5872(5) 0.0695(14) Uani 1 1 d . . . . .
O12 O 0.9607(6) 0.7019(14) 0.6272(5) 0.0842(18) Uani 1 1 d . . . . .
O21 O 0.6532(6) 0.1816(9) 0.2768(5) 0.0637(12) Uani 1 1 d . . . . .
O22 O 0.4990(5) 0.5504(12) 0.2465(4) 0.0666(15) Uani 1 1 d . . . . .
S1 S 0.81108(16) 0.6057(3) 0.54873(13) 0.0485(3) Uani 1 1 d . . . . .
S2 S 0.63277(15) 0.4328(3) 0.24772(12) 0.0463(3) Uani 1 1 d . . . . .
Cl Cl 0.8599(2) 0.7216(5) -0.0285(3) 0.0842(6) 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
C1 0.097(5) 0.057(4) 0.072(4) -0.009(4) 0.053(4) -0.001(4)
C2 0.044(2) 0.045(3) 0.041(2) -0.004(2) 0.0195(18) -0.002(2)
C3 0.069(3) 0.059(4) 0.040(3) -0.006(3) 0.018(2) 0.004(3)
C4 0.053(3) 0.075(5) 0.045(2) -0.003(3) 0.019(2) 0.001(3)
O3 0.059(2) 0.068(3) 0.0356(16) 0.0033(18) 0.0166(15) 0.011(2)
O11 0.108(4) 0.052(3) 0.049(2) 0.0049(19) 0.031(2) -0.007(3)
O12 0.074(3) 0.117(5) 0.051(2) -0.015(3) 0.012(2) -0.034(3)
O21 0.085(3) 0.050(3) 0.052(2) -0.0012(19) 0.022(2) -0.016(2)
O22 0.045(2) 0.099(4) 0.054(2) 0.003(2) 0.0176(17) 0.001(2)
S1 0.0583(7) 0.0464(7) 0.0382(5) 0.0006(6) 0.0158(5) -0.0083(6)
S2 0.0473(6) 0.0549(7) 0.0348(5) 0.0020(6) 0.0138(4) -0.0049(6)
Cl 0.0748(11) 0.0786(13) 0.1049(15) -0.0010(12) 0.0407(11) -0.0100(10)

_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 S1 1.746(8) . ?
C2 S2 1.777(5) . ?
C2 S1 1.801(5) . ?
C3 O3 1.472(8) . ?
C3 C4 1.475(8) . ?
C4 Cl 1.775(8) . ?
O3 S2 1.566(4) . ?
O11 S1 1.418(5) . ?
O12 S1 1.429(5) . ?
O21 S2 1.410(5) . ?
O22 S2 1.416(5) . ?

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
S2 C2 S1 113.9(3) . . ?
O3 C3 C4 106.5(5) . . ?
C3 C4 Cl 112.3(5) . . ?
C3 O3 S2 118.5(4) . . ?
O11 S1 O12 118.5(4) . . ?
O11 S1 C1 109.1(4) . . ?
O12 S1 C1 109.3(4) . . ?
O11 S1 C2 109.3(3) . . ?
O12 S1 C2 104.8(3) . . ?
C1 S1 C2 105.1(3) . . ?
O21 S2 O22 120.0(3) . . ?
O21 S2 O3 109.6(3) . . ?
O22 S2 O3 105.7(2) . . ?
O21 S2 C2 110.8(3) . . ?
O22 S2 C2 107.7(3) . . ?
O3 S2 C2 101.3(2) . . ?

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
O3 C3 C4 Cl 69.4(6) . . . . ?
C4 C3 O3 S2 -167.6(4) . . . . ?
S2 C2 S1 O11 40.4(4) . . . . ?
S2 C2 S1 O12 168.4(4) . . . . ?
S2 C2 S1 C1 -76.5(5) . . . . ?
C3 O3 S2 O21 -29.8(5) . . . . ?
C3 O3 S2 O22 -160.5(5) . . . . ?
C3 O3 S2 C2 87.2(5) . . . . ?
S1 C2 S2 O21 -70.2(4) . . . . ?
S1 C2 S2 O22 62.9(4) . . . . ?
S1 C2 S2 O3 173.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C1 H1A O22 0.96 2.60 3.225(9) 123.1 .
C1 H1B O11 0.96 2.41 3.192(10) 138.9 1_565
C1 H1B O21 0.96 2.54 3.372(9) 144.4 1_565
C1 H1C O22 0.96 2.61 3.314(8) 130.6 2_656
C2 H2A O21 0.97 2.57 3.448(8) 150.9 1_565
C2 H2B O12 0.97 2.28 3.165(9) 151.2 2_746
C3 H3A O22 0.97 2.66 3.305(7) 124.7 2_645
C3 H3B O12 0.97 2.59 3.507(8) 158.7 2_746

_refine_diff_density_max         0.659
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.070

_shelx_res_file                  
;

    shelx.res created by SHELXL-2014/7


TITL shelxt_a.res in P2(1)
CELL  1.54184   9.4479   5.5001  10.0650   90.000  112.633   90.000
ZERR     2.00   0.0007   0.0003   0.0007    0.000    0.009    0.000
LATT  -1
SYMM  - X, 1/2 + Y, - Z
SFAC  C    H    O    S    CL
UNIT  8 18 10 4 2
OMIT -3 142
MERG   2
HTAB C1 O22
EQIV $1 x, y+1, z
HTAB C1 O11_$1
HTAB C1 O21_$1
EQIV $2 -x+1, y+1/2, -z+1
HTAB C1 O22_$2
HTAB C2 O21_$1
EQIV $3 -x+2, y-1/2, -z+1
HTAB C2 O12_$3
EQIV $4 -x+1, y-1/2, -z
HTAB C3 O22_$4
HTAB C3 O12_$3
CONF
SIZE  0.080 0.162 0.305
TEMP  23
REM   Crystal shape/color: fragment/colorless
ACTA
FMAP   2
PLAN  -3
L.S.  8
WGHT    0.056600    0.132200
FVAR      13.07810
C1    1    0.673630    0.815229    0.552186    11.00000    0.09713    0.05730 =
         0.07208   -0.00911    0.05297   -0.00053
AFIX 137
H1A   2    0.572982    0.752920    0.497555    11.00000   -1.50000
H1B   2    0.687810    0.966131    0.510977    11.00000   -1.50000
H1C   2    0.684542    0.841791    0.649921    11.00000   -1.50000
AFIX   0
C2    1    0.793748    0.599467    0.364243    11.00000    0.04402    0.04493 =
         0.04077   -0.00397    0.01950   -0.00215
AFIX  23
H2A   2    0.786393    0.765199    0.329258    11.00000   -1.20000
H2B   2    0.886158    0.528603    0.360503    11.00000   -1.20000
AFIX   0
C3    1    0.734037    0.330223    0.046754    11.00000    0.06859    0.05887 =
         0.03987   -0.00616    0.01772    0.00422
AFIX  23
H3A   2    0.686148    0.172211    0.018939    11.00000   -1.20000
H3B   2    0.834781    0.307669    0.122099    11.00000   -1.20000
AFIX   0
C4    1    0.746613    0.453974   -0.078258    11.00000    0.05273    0.07526 =
         0.04463   -0.00267    0.01870    0.00145
AFIX  23
H4A   2    0.644755    0.496088   -0.146200    11.00000   -1.20000
H4B   2    0.791749    0.343275   -0.125978    11.00000   -1.20000
AFIX   0
O3    3    0.639244    0.487721    0.097523    11.00000    0.05857    0.06798 =
         0.03560    0.00332    0.01658    0.01058
O11   3    0.774173    0.373180    0.587233    11.00000    0.10820    0.05208 =
         0.04873    0.00489    0.03065   -0.00719
O12   3    0.960726    0.701897    0.627218    11.00000    0.07371    0.11666 =
         0.05144   -0.01474    0.01219   -0.03416
O21   3    0.653208    0.181593    0.276771    11.00000    0.08521    0.04989 =
         0.05234   -0.00120    0.02236   -0.01562
O22   3    0.498954    0.550426    0.246522    11.00000    0.04526    0.09910 =
         0.05400    0.00299    0.01759    0.00110
S1    4    0.811080    0.605746    0.548735    11.00000    0.05833    0.04641 =
         0.03816    0.00057    0.01580   -0.00834
S2    4    0.632767    0.432792    0.247719    11.00000    0.04729    0.05495 =
         0.03479    0.00199    0.01376   -0.00488
CL    5    0.859905    0.721571   -0.028524    11.00000    0.07477    0.07861 =
         0.10488   -0.00098    0.04067   -0.01005
HKLF    4

REM  shelxt_a.res in P2(1)
REM R1 =  0.0427 for    1186 Fo > 4sig(Fo)  and  0.0459 for all    1263 data
REM    110 parameters refined using      1 restraints

END

WGHT      0.0556      0.1357

REM Highest difference peak  0.659,  deepest hole -0.296,  1-sigma level  0.070
Q1    1   0.8987  0.7139  0.0723  11.00000  0.05    0.66
Q2    1   0.7802  0.6088  0.4425  11.00000  0.05    0.43
Q3    1   0.6088  0.4543  0.1361  11.00000  0.05    0.31
;
_shelx_res_checksum              62625

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Dichloromethane'
