# Electronic Supplementary Material (ESI) for Catalysis Science & Technology.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_dengj-1
_database_code_depnum_ccdc_archive 'CCDC 1523385'
_audit_update_record             
;
2016-12-19 deposited with the CCDC.
2017-04-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C7 H12 N2 O3 S), C H4 O'
_chemical_formula_sum            'C15 H28 N4 O7 S2'
_chemical_formula_weight         440.53

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'
N N 0.0311 0.0180 '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           Monoclinic
_symmetry_space_group_name_H-M   P2(1)/c
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   7.8403(2)
_cell_length_b                   12.7512(3)
_cell_length_c                   10.5247(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.486(2)
_cell_angle_gamma                90.00
_cell_volume                     1051.83(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2585
_cell_measurement_theta_min      5.4
_cell_measurement_theta_max      73.9

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      none
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             468
_exptl_absorpt_coefficient_mu    2.686
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.658
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      295(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  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean 5.2137
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        0
_diffrn_reflns_number            3840
_diffrn_reflns_av_R_equivalents  0.0228
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         5.45
_diffrn_reflns_theta_max         74.07
_reflns_number_total             2084
_reflns_number_gt                1909
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.39.7e (Rigaku OD, 2015)'
_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)+(0.0010P)²+0.8000P] 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       0.0428(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2084
_refine_ls_number_parameters     138
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0801
_refine_ls_wR_factor_gt          0.0785
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.090
_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 0.37901(6) 0.73265(4) 0.02187(4) 0.03567(18) Uani 1 1 d . . .
O1 O 0.3353(2) 0.65694(12) -0.07693(13) 0.0485(4) Uani 1 1 d . . .
O2 O 0.5511(2) 0.77198(13) 0.00987(15) 0.0521(4) Uani 1 1 d . . .
O3 O 0.2528(2) 0.81532(13) 0.03154(15) 0.0569(5) Uani 1 1 d . . .
N1 N 0.3412(2) 0.45231(13) 0.29908(16) 0.0384(4) Uani 1 1 d . . .
N2 N 0.1572(2) 0.33258(15) 0.25064(19) 0.0481(5) Uani 1 1 d . . .
C1 C 0.3098(3) 0.37028(17) 0.2257(2) 0.0414(5) Uani 1 1 d . . .
H1 H 0.3833 0.3433 0.1659 0.050 Uiso 1 1 calc R . .
C2 C 0.2044(3) 0.4677(2) 0.3748(2) 0.0543(6) Uani 1 1 d . . .
H2 H 0.1931 0.5199 0.4358 0.065 Uiso 1 1 calc R . .
C3 C 0.0893(3) 0.3931(2) 0.3442(2) 0.0592(7) Uani 1 1 d . . .
H3 H -0.0169 0.3842 0.3800 0.071 Uiso 1 1 calc R . .
C4 C 0.4991(3) 0.51452(17) 0.2999(2) 0.0443(5) Uani 1 1 d . . .
H4A H 0.5965 0.4678 0.3064 0.053 Uiso 1 1 calc R . .
H4B H 0.5021 0.5599 0.3739 0.053 Uiso 1 1 calc R . .
C5 C 0.5123(3) 0.58096(17) 0.1805(2) 0.0409(5) Uani 1 1 d . . .
H5A H 0.6227 0.6152 0.1811 0.049 Uiso 1 1 calc R . .
H5B H 0.5056 0.5354 0.1067 0.049 Uiso 1 1 calc R . .
C6 C 0.3737(3) 0.66358(16) 0.16839(18) 0.0369(4) Uani 1 1 d . . .
H6A H 0.3870 0.7131 0.2379 0.044 Uiso 1 1 calc R . .
H6B H 0.2633 0.6301 0.1756 0.044 Uiso 1 1 calc R . .
C7 C 0.0765(4) 0.2428(2) 0.1883(3) 0.0781(9) Uani 1 1 d . . .
H7A H 0.1428 0.2217 0.1172 0.117 Uiso 1 1 calc R . .
H7B H -0.0364 0.2616 0.1590 0.117 Uiso 1 1 calc R . .
H7C H 0.0699 0.1857 0.2475 0.117 Uiso 1 1 calc R . .
C8 C 0.0323(13) 0.4742(13) 0.9732(11) 0.089(3) Uani 0.50 1 d PD . .
H8A H 0.0366 0.4040 1.0062 0.133 Uiso 0.50 1 d PR . .
H8B H 0.1448 0.5038 0.9733 0.133 Uiso 0.50 1 d PR . .
H8C H -0.0122 0.4736 0.8873 0.133 Uiso 0.50 1 d PR . .
O4 O -0.0894(13) 0.5098(9) 1.0527(12) 0.184(5) Uani 0.50 1 d PD . .
H4 H -0.1633 0.4604 1.0590 0.276 Uiso 0.50 1 d PR . .


_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 O2 1.4481(15) . ?
S1 O3 1.4511(16) . ?
S1 O1 1.4534(15) . ?
S1 C6 1.7773(19) . ?
N1 C1 1.320(3) . ?
N1 C2 1.367(3) . ?
N1 C4 1.470(3) . ?
N2 C1 1.322(3) . ?
N2 C3 1.369(3) . ?
N2 C7 1.457(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.345(4) . ?
C2 H2 0.9300 . ?
C3 H3 0.9300 . ?
C4 C5 1.522(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.516(3) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 O4 1.363(7) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
O4 H4 0.8601 . ?

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 O3 113.14(10) . . ?
O2 S1 O1 111.76(10) . . ?
O3 S1 O1 112.59(10) . . ?
O2 S1 C6 106.86(10) . . ?
O3 S1 C6 105.54(9) . . ?
O1 S1 C6 106.33(9) . . ?
C1 N1 C2 108.53(19) . . ?
C1 N1 C4 125.16(18) . . ?
C2 N1 C4 126.30(19) . . ?
C1 N2 C3 108.0(2) . . ?
C1 N2 C7 125.5(2) . . ?
C3 N2 C7 126.5(2) . . ?
N1 C1 N2 109.16(19) . . ?
N1 C1 H1 125.4 . . ?
N2 C1 H1 125.4 . . ?
C3 C2 N1 106.9(2) . . ?
C3 C2 H2 126.6 . . ?
N1 C2 H2 126.6 . . ?
C2 C3 N2 107.5(2) . . ?
C2 C3 H3 126.3 . . ?
N2 C3 H3 126.3 . . ?
N1 C4 C5 111.75(16) . . ?
N1 C4 H4A 109.3 . . ?
C5 C4 H4A 109.3 . . ?
N1 C4 H4B 109.3 . . ?
C5 C4 H4B 109.3 . . ?
H4A C4 H4B 107.9 . . ?
C6 C5 C4 113.09(17) . . ?
C6 C5 H5A 109.0 . . ?
C4 C5 H5A 109.0 . . ?
C6 C5 H5B 109.0 . . ?
C4 C5 H5B 109.0 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 S1 112.61(13) . . ?
C5 C6 H6A 109.1 . . ?
S1 C6 H6A 109.1 . . ?
C5 C6 H6B 109.1 . . ?
S1 C6 H6B 109.1 . . ?
H6A C6 H6B 107.8 . . ?
N2 C7 H7A 109.5 . . ?
N2 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N2 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 H8A 96.1 . . ?
O4 C8 H8B 121.8 . . ?
H8A C8 H8B 110.0 . . ?
O4 C8 H8C 109.8 . . ?
H8A C8 H8C 110.0 . . ?
H8B C8 H8C 108.4 . . ?
C8 O4 H4 106.7 . . ?

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
O4 H4 O1 0.86 2.03 2.886(8) 178.9 3_566

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        70.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.233
_refine_diff_density_min         -0.301
_refine_diff_density_rms         0.050
