# 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_dipa
_database_code_depnum_ccdc_archive 'CCDC 2073361'
loop_
_audit_author_name
_audit_author_address
'Ewa Rozycka-Sokolowska'
;Jan Dlugosz University in Czestochowa
Poland
;
_audit_update_record             
;
2021-03-26 deposited with the CCDC.	2022-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'diisopropylammonium sulfate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C6 H16 N), S O4'
_chemical_formula_sum            'C12 H32 N2 O4 S'
_chemical_formula_weight         300.46

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   'P 21/n'
_symmetry_int_tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'

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

_cell_length_a                   8.7824(2)
_cell_length_b                   8.82350(10)
_cell_length_c                   22.0837(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.202(2)
_cell_angle_gamma                90.00
_cell_volume                     1704.25(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    10761
_cell_measurement_theta_min      5.0470
_cell_measurement_theta_max      67.3160

_exptl_crystal_description       tablet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.55
_exptl_crystal_size_mid          0.48
_exptl_crystal_size_min          0.36
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.171
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             664
_exptl_absorpt_coefficient_mu    1.791
_exptl_absorpt_correction_T_min  0.08087
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.24
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm
;
_exptl_special_details           
; 
 ? 
;
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance (Cu) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            25461
_diffrn_reflns_av_R_equivalents  0.0328
_diffrn_reflns_av_sigmaI/netI    0.0151
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         5.27
_diffrn_reflns_theta_max         67.23
_reflns_number_total             3063
_reflns_number_gt                2879
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.24'
_computing_cell_refinement       
'CrysAlisPro, Agilent Technologies, Version 1.171.36.24'
_computing_data_reduction        
'CrysAlisPro, Agilent Technologies, Version 1.171.36.24'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'PLATON (Spek,2003), DIAMOND (Brandenburg, 2006)'
_computing_publication_material  ?


_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)+(0.0563P)²+0.5384P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0217(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3063
_refine_ls_number_parameters     226
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0366
_refine_ls_R_factor_gt           0.0349
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0960
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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
N1 N 0.21373(15) 0.07331(15) 0.20077(6) 0.0336(3) Uani 1 1 d . . .
H1A H 0.227(2) 0.073(2) 0.2395(11) 0.054(6) Uiso 1 1 d . . .
H1B H 0.236(2) 0.167(2) 0.1854(9) 0.047(5) Uiso 1 1 d . . .
C2 C 0.04739(19) 0.04006(18) 0.18446(7) 0.0398(4) Uani 1 1 d . . .
H2A H 0.031(2) 0.044(2) 0.1410(9) 0.046(5) Uiso 1 1 d . . .
C3 C 0.0068(2) -0.1169(2) 0.20590(9) 0.0506(4) Uani 1 1 d . . .
H3A H 0.0585 -0.1917 0.1837 0.076 Uiso 1 1 calc R . .
H3B H -0.1017 -0.1318 0.1990 0.076 Uiso 1 1 calc R . .
H3C H 0.0378 -0.1265 0.2485 0.076 Uiso 1 1 calc R . .
C4 C -0.0431(2) 0.1631(2) 0.21274(9) 0.0534(4) Uani 1 1 d . . .
H4A H -0.0199 0.1623 0.2561 0.080 Uiso 1 1 calc R . .
H4B H -0.1504 0.1452 0.2032 0.080 Uiso 1 1 calc R . .
H4C H -0.0165 0.2599 0.1969 0.080 Uiso 1 1 calc R . .
C5 C 0.3280(2) -0.03598(18) 0.17959(8) 0.0421(4) Uani 1 1 d . . .
H5A H 0.307(2) -0.129(2) 0.1978(8) 0.045(5) Uiso 1 1 d . . .
C6 C 0.3097(3) -0.0520(3) 0.11118(10) 0.0689(6) Uani 1 1 d . . .
H6A H 0.2092 -0.0894 0.0986 0.103 Uiso 1 1 calc R . .
H6B H 0.3847 -0.1218 0.0987 0.103 Uiso 1 1 calc R . .
H6C H 0.3236 0.0450 0.0928 0.103 Uiso 1 1 calc R . .
C7 C 0.4852(2) 0.0201(2) 0.20319(11) 0.0600(5) Uani 1 1 d . . .
H7A H 0.5034 0.1173 0.1857 0.090 Uiso 1 1 calc R . .
H7B H 0.5611 -0.0506 0.1922 0.090 Uiso 1 1 calc R . .
H7C H 0.4908 0.0291 0.2467 0.090 Uiso 1 1 calc R . .
N11 N 0.80017(16) 0.54142(16) 0.04731(6) 0.0365(3) Uani 1 1 d D . .
H11A H 0.881(3) 0.514(2) 0.0618(10) 0.049(6) Uiso 1 1 d . . .
H11B H 0.789(2) 0.517(2) 0.0090(7) 0.046(5) Uiso 1 1 d D . .
C12 C 0.68243(18) 0.4464(2) 0.07547(8) 0.0477(4) Uani 1 1 d . . .
H12A H 0.587(3) 0.475(2) 0.0521(10) 0.059(6) Uiso 1 1 d . . .
C13 C 0.7199(2) 0.2818(2) 0.06468(10) 0.0615(5) Uani 1 1 d . . .
H13A H 0.8191 0.2587 0.0844 0.092 Uiso 1 1 calc R . .
H13B H 0.7198 0.2638 0.0218 0.092 Uiso 1 1 calc R . .
H13C H 0.6447 0.2184 0.0810 0.092 Uiso 1 1 calc R . .
C14 C 0.6774(3) 0.4834(3) 0.14192(10) 0.0720(7) Uani 1 1 d . . .
H14A H 0.7774 0.4707 0.1627 0.108 Uiso 1 1 calc R . .
H14B H 0.6068 0.4167 0.1593 0.108 Uiso 1 1 calc R . .
H14C H 0.6448 0.5864 0.1461 0.108 Uiso 1 1 calc R . .
C15 C 0.7899(2) 0.7096(2) 0.05318(8) 0.0483(4) Uani 1 1 d . . .
H15A H 0.800(2) 0.729(2) 0.0936(10) 0.054(5) Uiso 1 1 d . . .
C16 C 0.9228(2) 0.7778(3) 0.02351(10) 0.0659(6) Uani 1 1 d . . .
H16A H 1.0168 0.7351 0.0414 0.099 Uiso 1 1 calc R . .
H16B H 0.9240 0.8856 0.0295 0.099 Uiso 1 1 calc R . .
H16C H 0.9118 0.7560 -0.0193 0.099 Uiso 1 1 calc R . .
C17 C 0.6366(2) 0.7658(2) 0.02530(11) 0.0664(6) Uani 1 1 d . . .
H17A H 0.6234 0.7372 -0.0168 0.100 Uiso 1 1 calc R . .
H17B H 0.6326 0.8742 0.0286 0.100 Uiso 1 1 calc R . .
H17C H 0.5566 0.7217 0.0464 0.100 Uiso 1 1 calc R . .
S1 S 0.22167(4) 0.47868(4) 0.126328(14) 0.02870(16) Uani 1 1 d . . .
O1 O 0.2769(3) 0.5349(3) 0.06919(11) 0.0472(5) Uani 0.854(8) 1 d P A 1
O2 O 0.2981(4) 0.3337(2) 0.14375(12) 0.0505(5) Uani 0.854(8) 1 d P A 1
O3 O 0.0550(3) 0.4612(4) 0.11993(16) 0.0798(9) Uani 0.854(8) 1 d P A 1
O4 O 0.2669(4) 0.5878(2) 0.17515(7) 0.0531(7) Uani 0.854(8) 1 d P A 1
O1A O 0.305(2) 0.549(2) 0.0843(7) 0.0472(5) Uani 0.146(8) 1 d P A 2
O2A O 0.2461(18) 0.3278(17) 0.1332(8) 0.0505(5) Uani 0.146(8) 1 d P A 2
O3A O 0.075(2) 0.439(3) 0.0982(9) 0.0798(9) Uani 0.146(8) 1 d P A 2
O4A O 0.193(2) 0.5721(14) 0.1720(5) 0.0531(7) Uani 0.146(8) 1 d P A 2


_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
N1 C5 1.497(2) . ?
N1 C2 1.502(2) . ?
N1 H1A 0.85(2) . ?
N1 H1B 0.92(2) . ?
C2 C4 1.514(2) . ?
C2 C3 1.516(2) . ?
C2 H2A 0.96(2) . ?
C3 H3A 0.9600 . ?
C3 H3B 0.9600 . ?
C3 H3C 0.9600 . ?
C4 H4A 0.9600 . ?
C4 H4B 0.9600 . ?
C4 H4C 0.9600 . ?
C5 C6 1.511(3) . ?
C5 C7 1.514(3) . ?
C5 H5A 0.94(2) . ?
C6 H6A 0.9600 . ?
C6 H6B 0.9600 . ?
C6 H6C 0.9600 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
N11 C15 1.493(2) . ?
N11 C12 1.509(2) . ?
N11 H11A 0.79(2) . ?
N11 H11B 0.870(15) . ?
C12 C14 1.508(3) . ?
C12 C13 1.513(3) . ?
C12 H12A 0.98(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C17 1.512(3) . ?
C15 C16 1.514(3) . ?
C15 H15A 0.91(2) . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
S1 O4A 1.344(11) . ?
S1 O2A 1.354(15) . ?
S1 O1A 1.377(17) . ?
S1 O3A 1.424(19) . ?
S1 O3 1.466(2) . ?
S1 O4 1.473(2) . ?
S1 O1 1.478(2) . ?
S1 O2 1.479(2) . ?

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
C5 N1 C2 117.67(13) . . ?
C5 N1 H1A 106.1(14) . . ?
C2 N1 H1A 106.5(14) . . ?
C5 N1 H1B 107.0(12) . . ?
C2 N1 H1B 108.7(11) . . ?
H1A N1 H1B 110.9(18) . . ?
N1 C2 C4 107.27(13) . . ?
N1 C2 C3 110.78(13) . . ?
C4 C2 C3 112.28(14) . . ?
N1 C2 H2A 106.9(11) . . ?
C4 C2 H2A 110.6(11) . . ?
C3 C2 H2A 108.9(11) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
N1 C5 C6 111.04(15) . . ?
N1 C5 C7 107.36(14) . . ?
C6 C5 C7 112.69(17) . . ?
N1 C5 H5A 105.6(11) . . ?
C6 C5 H5A 109.7(11) . . ?
C7 C5 H5A 110.2(11) . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C15 N11 C12 117.87(14) . . ?
C15 N11 H11A 109.2(14) . . ?
C12 N11 H11A 106.6(15) . . ?
C15 N11 H11B 109.3(12) . . ?
C12 N11 H11B 103.8(12) . . ?
H11A N11 H11B 109.7(19) . . ?
C14 C12 N11 111.25(16) . . ?
C14 C12 C13 112.79(17) . . ?
N11 C12 C13 107.55(14) . . ?
C14 C12 H12A 111.0(13) . . ?
N11 C12 H12A 103.1(12) . . ?
C13 C12 H12A 110.7(12) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N11 C15 C17 110.43(15) . . ?
N11 C15 C16 107.61(15) . . ?
C17 C15 C16 112.70(18) . . ?
N11 C15 H15A 106.0(13) . . ?
C17 C15 H15A 110.2(12) . . ?
C16 C15 H15A 109.7(12) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4A S1 O2A 123.8(9) . . ?
O4A S1 O1A 112.1(9) . . ?
O2A S1 O1A 115.3(11) . . ?
O4A S1 O3A 105.0(10) . . ?
O2A S1 O3A 86.2(13) . . ?
O1A S1 O3A 109.3(9) . . ?
O3 S1 O4 109.88(14) . . ?
O3 S1 O1 110.80(12) . . ?
O4 S1 O1 108.56(10) . . ?
O3 S1 O2 111.08(19) . . ?
O4 S1 O2 106.79(18) . . ?
O1 S1 O2 109.62(14) . . ?

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
C5 N1 C2 C4 178.09(14) . . . . ?
C5 N1 C2 C3 55.23(18) . . . . ?
C2 N1 C5 C6 58.01(19) . . . . ?
C2 N1 C5 C7 -178.39(14) . . . . ?
C15 N11 C12 C14 -54.6(2) . . . . ?
C15 N11 C12 C13 -178.62(15) . . . . ?
C12 N11 C15 C17 -58.6(2) . . . . ?
C12 N11 C15 C16 177.97(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.23
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.441
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.038
