# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_mei0113
_database_code_depnum_ccdc_archive 'CCDC 2173393'
loop_
_audit_author_name
_audit_author_address
'Haibo Mei'
;Nanjing Forestry University
China
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-07-19 downloaded from the CCDC.
;
_audit_creation_date             2022-01-13
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2021.12.09 svn.r5202d8cf for OlexSys, GUI svn.r6439)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H13 Br O4 S'
_chemical_formula_sum            'C10 H13 Br O4 S'
_chemical_formula_weight         309.17
_chemical_melting_point          ?
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'
Br Br -0.2901 2.4595 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.7194(6)
_cell_length_b                   7.7474(7)
_cell_length_c                   12.0130(11)
_cell_angle_alpha                88.533(7)
_cell_angle_beta                 79.948(8)
_cell_angle_gamma                87.813(7)
_cell_volume                     615.21(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1660
_cell_measurement_temperature    199.99(10)
_cell_measurement_theta_max      26.6600
_cell_measurement_theta_min      3.0710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    3.506
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.42029
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.669
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             312
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0343
_diffrn_reflns_av_unetI/netI     0.0582
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            3915
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         2.631
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      199.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  36.00   1.00    2.50    --   11.90 -57.00-150.00   89
  2  ω    -12.00  79.00   1.00    2.50    --   11.90  77.00 120.00   91
  3  ω    -14.00  85.00   1.00    2.50    --   11.90  57.00   0.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0771466000
_diffrn_orient_matrix_UB_12      0.0534913000
_diffrn_orient_matrix_UB_13      0.0309777000
_diffrn_orient_matrix_UB_21      0.0584853000
_diffrn_orient_matrix_UB_22      0.0062395000
_diffrn_orient_matrix_UB_23      0.0434177000
_diffrn_orient_matrix_UB_31      0.0462000000
_diffrn_orient_matrix_UB_32      0.0741417000
_diffrn_orient_matrix_UB_33      -0.0274301000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1673
_reflns_number_total             2155
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.459
_refine_diff_density_min         -0.429
_refine_diff_density_rms         0.075
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2155
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0418
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0872
_refine_ls_wR_factor_ref         0.0960
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C5(H5), C6(H6)
2.d Idealised Me refined as rotating group:
 C9(H9A,H9B,H9C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Br1 Br 0.94206(7) 0.23590(7) -0.13029(4) 0.0649(2) Uani 1 1 d . . . . .
S1 S 0.32683(12) 0.27749(11) 0.55688(7) 0.0266(2) Uani 1 1 d . . . . .
O1 O 0.1757(3) 0.1943(3) 0.3254(2) 0.0331(6) Uani 1 1 d . . . . .
O2 O 0.2467(3) 0.4510(3) 0.5600(2) 0.0339(6) Uani 1 1 d . . . . .
O3 O 0.4630(3) 0.2253(3) 0.6308(2) 0.0381(6) Uani 1 1 d . . . . .
O4 O 0.1496(3) 0.1497(3) 0.5846(2) 0.0307(6) Uani 1 1 d . . . . .
C1 C 0.4922(5) 0.2838(4) 0.2105(3) 0.0279(8) Uani 1 1 d . . . . .
C2 C 0.5782(5) 0.4304(5) 0.1570(3) 0.0355(9) Uani 1 1 d . . . . .
H2 H 0.545267 0.538265 0.188724 0.043 Uiso 1 1 calc R U . . .
C3 C 0.7144(5) 0.4158(5) 0.0553(3) 0.0405(10) Uani 1 1 d . . . . .
H3 H 0.773960 0.513551 0.019488 0.049 Uiso 1 1 calc R U . . .
C4 C 0.7593(5) 0.2573(5) 0.0091(3) 0.0384(10) Uani 1 1 d . . . . .
C5 C 0.6762(5) 0.1098(5) 0.0609(3) 0.0410(10) Uani 1 1 d . . . . .
H5 H 0.709411 0.002574 0.028377 0.049 Uiso 1 1 calc R U . . .
C6 C 0.5423(5) 0.1238(5) 0.1623(3) 0.0362(9) Uani 1 1 d . . . . .
H6 H 0.485584 0.025091 0.198248 0.043 Uiso 1 1 calc R U . . .
C7 C 0.3470(5) 0.2974(4) 0.3217(3) 0.0289(8) Uani 1 1 d . . . . .
H7 H 0.302554 0.418376 0.334461 0.035 Uiso 1 1 calc R U . . .
C8 C 0.4521(4) 0.2315(4) 0.4177(3) 0.0261(8) Uani 1 1 d . . . . .
H8A H 0.585080 0.280278 0.407009 0.031 Uiso 1 1 calc R U . . .
H8B H 0.471549 0.107215 0.411499 0.031 Uiso 1 1 calc R U . . .
C9 C -0.0557(5) 0.2041(5) 0.5714(3) 0.0356(9) Uani 1 1 d . . . . .
H9A H -0.072920 0.185871 0.494911 0.053 Uiso 1 1 calc R U . . .
H9B H -0.077769 0.324429 0.588277 0.053 Uiso 1 1 calc R U . . .
H9C H -0.151175 0.137626 0.622146 0.053 Uiso 1 1 calc R U . . .
C10 C 0.0448(5) 0.2552(6) 0.2502(3) 0.0456(11) Uani 1 1 d . . . . .
H10A H 0.117386 0.254400 0.173976 0.068 Uiso 1 1 calc R U . . .
H10B H -0.002906 0.370823 0.269513 0.068 Uiso 1 1 calc R U . . .
H10C H -0.068331 0.181293 0.256686 0.068 Uiso 1 1 calc R U . . .


_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
Br1 C4 1.903(4) . ?
S1 O2 1.427(2) . ?
S1 O3 1.423(2) . ?
S1 O4 1.563(2) . ?
S1 C8 1.774(3) . ?
O1 C7 1.420(4) . ?
O1 C10 1.426(4) . ?
O4 C9 1.461(4) . ?
C1 C2 1.386(5) . ?
C1 C6 1.386(5) . ?
C1 C7 1.514(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.397(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.362(5) . ?
C4 C5 1.377(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.386(5) . ?
C6 H6 0.9300 . ?
C7 H7 0.9800 . ?
C7 C8 1.521(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?

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
O2 S1 O4 109.55(13) . . ?
O2 S1 C8 109.34(16) . . ?
O3 S1 O2 119.32(14) . . ?
O3 S1 O4 104.74(14) . . ?
O3 S1 C8 106.66(15) . . ?
O4 S1 C8 106.47(14) . . ?
C7 O1 C10 113.2(3) . . ?
C9 O4 S1 120.7(2) . . ?
C2 C1 C7 120.4(3) . . ?
C6 C1 C2 119.5(3) . . ?
C6 C1 C7 120.1(3) . . ?
C1 C2 H2 120.1 . . ?
C1 C2 C3 119.8(4) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 Br1 119.9(3) . . ?
C3 C4 C5 121.7(4) . . ?
C5 C4 Br1 118.4(3) . . ?
C4 C5 H5 120.5 . . ?
C4 C5 C6 118.9(4) . . ?
C6 C5 H5 120.5 . . ?
C1 C6 C5 120.6(3) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
O1 C7 C1 112.4(3) . . ?
O1 C7 H7 109.5 . . ?
O1 C7 C8 106.2(3) . . ?
C1 C7 H7 109.5 . . ?
C1 C7 C8 109.6(3) . . ?
C8 C7 H7 109.5 . . ?
S1 C8 H8A 108.2 . . ?
S1 C8 H8B 108.2 . . ?
C7 C8 S1 116.5(2) . . ?
C7 C8 H8A 108.2 . . ?
C7 C8 H8B 108.2 . . ?
H8A C8 H8B 107.3 . . ?
O4 C9 H9A 109.5 . . ?
O4 C9 H9B 109.5 . . ?
O4 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O1 C10 H10A 109.5 . . ?
O1 C10 H10B 109.5 . . ?
O1 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
Br1 C4 C5 C6 -179.8(3) . . . . ?
O1 C7 C8 S1 -71.0(3) . . . . ?
O2 S1 O4 C9 20.8(3) . . . . ?
O2 S1 C8 C7 -42.1(3) . . . . ?
O3 S1 O4 C9 149.9(2) . . . . ?
O3 S1 C8 C7 -172.4(2) . . . . ?
O4 S1 C8 C7 76.2(3) . . . . ?
C1 C2 C3 C4 0.8(5) . . . . ?
C1 C7 C8 S1 167.4(2) . . . . ?
C2 C1 C6 C5 -0.5(5) . . . . ?
C2 C1 C7 O1 136.6(3) . . . . ?
C2 C1 C7 C8 -105.5(4) . . . . ?
C2 C3 C4 Br1 179.2(3) . . . . ?
C2 C3 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C4 C5 C6 C1 0.3(5) . . . . ?
C6 C1 C2 C3 -0.1(5) . . . . ?
C6 C1 C7 O1 -44.3(4) . . . . ?
C6 C1 C7 C8 73.6(4) . . . . ?
C7 C1 C2 C3 179.0(3) . . . . ?
C7 C1 C6 C5 -179.5(3) . . . . ?
C8 S1 O4 C9 -97.4(3) . . . . ?
C10 O1 C7 C1 -68.3(4) . . . . ?
C10 O1 C7 C8 171.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.893
_oxdiff_exptl_absorpt_empirical_full_min 0.637
