# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_MSMA
_database_code_depnum_ccdc_archive 'CCDC 2093843'
loop_
_audit_author_name
_audit_author_address
'Sachio Horiuchi'
;National Institute of Advanced Science and Technology 
Japan
;
_audit_update_record             
;
2021-07-01 deposited with the CCDC.	2021-09-20 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C4 H8 N2 O4 S'
_chemical_formula_moiety         'C4 H8 N2 O4 S'
_chemical_formula_weight         180.18
_chemical_melting_point          ?
_chemical_absolute_configuration 'CHOOSE rm ad rmad syn or unk'

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
_space_group_IT_number           33
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,1/2+Z
3 1/2-X,1/2+Y,1/2+Z
4 1/2+X,1/2-Y,+Z
#------------------------------------------------------------------------------
_cell_length_a                   9.2973(4)
_cell_length_b                   6.9862(3)
_cell_length_c                   11.4143(4)
_cell_angle_alpha                90.0000
_cell_angle_beta                 90.0000
_cell_angle_gamma                90.0000
_cell_volume                     741.39(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2349
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      29.92
_cell_measurement_temperature    296
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.140
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             376.00
_exptl_absorpt_coefficient_mu    0.406
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_correction_T_min  0.934
_exptl_absorpt_correction_T_max  0.945

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      296
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_reflns_number            2463
_diffrn_reflns_av_unetI/netI     0.0077
_diffrn_reflns_av_R_equivalents  0.0059
_diffrn_reflns_theta_max         27.447
_diffrn_reflns_theta_min         3.419
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.750
_diffrn_reflns_point_group_measured_fraction_full 0.792
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             1266
_reflns_number_gt                1240
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.454
_reflns_Friedel_fraction_max     0.493
_reflns_Friedel_fraction_full    0.570

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0238
_refine_ls_wR_factor_ref         0.0629
_refine_ls_wR_factor_gt          0.0626
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_reflns         1266
_refine_ls_number_parameters     118
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0361P)²+0.2253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.32
_refine_diff_density_min         -0.27
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.015(3)
_refine_ls_abs_structure_details 
;
 Flack x determined using 385 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.347(18)

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
S S 0.1246 0.1234
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
S1 S 0.45253(5) -0.01455(7) 0.11824(8) 0.02727(18) Uani 1 1 d . . . . .
O2 O 0.4089(3) -0.0725(3) 0.2332(2) 0.0548(6) Uani 1 1 d . . . . .
O3 O 0.6022(2) -0.0274(2) 0.0901(2) 0.0414(6) Uani 1 1 d . . . . .
O4 O 0.5716(2) 0.3468(4) 0.2306(2) 0.0515(7) Uani 1 1 d . . . . .
O5 O 0.5639(2) 0.3492(3) -0.03559(17) 0.0351(5) Uani 1 1 d . . . . .
N6 N 0.3466(3) 0.4529(5) 0.2532(3) 0.0516(8) Uani 1 1 d . . . . .
N7 N 0.3328(2) 0.3604(4) -0.0898(2) 0.0331(5) Uani 1 1 d . . . . .
C8 C 0.3557(4) -0.1421(5) 0.0121(3) 0.0545(10) Uani 1 1 d . . . . .
H12A H 0.254648 -0.119190 0.022334 0.065 Uiso 1 1 calc R U . . .
H13B H 0.374912 -0.276438 0.020316 0.065 Uiso 1 1 calc R U . . .
H14C H 0.384426 -0.100534 -0.064605 0.065 Uiso 1 1 calc R U . . .
C9 C 0.38860(19) 0.2271(3) 0.09940(19) 0.0197(4) Uani 1 1 d . . . . .
H19 H 0.283240 0.225772 0.101820 0.024 Uiso 1 1 calc R U . . .
C10 C 0.4437(3) 0.3480(4) 0.2021(2) 0.0240(5) Uani 1 1 d . . . . .
C11 C 0.4363(3) 0.3164(3) -0.0167(2) 0.0214(5) Uani 1 1 d . . . . .
H15 H 0.381(5) 0.539(6) 0.309(4) 0.072(13) Uiso 1 1 d . . . . .
H16 H 0.271(5) 0.454(5) 0.236(4) 0.062(12) Uiso 1 1 d . . . . .
H17 H 0.354(4) 0.424(5) -0.150(3) 0.041(9) Uiso 1 1 d . . . . .
H18 H 0.245(4) 0.340(5) -0.068(3) 0.044(9) Uiso 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL Version 2018/3 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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 O3 1.431(2) . ?
S1 O2 1.431(2) . ?
S1 C8 1.753(3) . ?
S1 C9 1.802(2) . ?
O4 C10 1.232(3) . ?
O5 C11 1.227(3) . ?
N6 C10 1.301(3) . ?
N6 H15 0.93(4) . ?
N6 H16 0.73(4) . ?
N7 C11 1.310(3) . ?
N7 H17 0.84(4) . ?
N7 H18 0.86(4) . ?
C8 H12A 0.9600 . ?
C8 H13B 0.9600 . ?
C8 H14C 0.9600 . ?
C9 C11 1.531(3) . ?
C9 C10 1.533(3) . ?
C9 H19 0.9800 . ?

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
O3 S1 O2 117.63(15) . . ?
O3 S1 C8 108.18(16) . . ?
O2 S1 C8 110.13(19) . . ?
O3 S1 C9 110.66(10) . . ?
O2 S1 C9 106.30(12) . . ?
C8 S1 C9 102.95(13) . . ?
C10 N6 H15 116(3) . . ?
C10 N6 H16 124(3) . . ?
H15 N6 H16 120(4) . . ?
C11 N7 H17 118(2) . . ?
C11 N7 H18 118(2) . . ?
H17 N7 H18 123(3) . . ?
S1 C8 H12A 109.5 . . ?
S1 C8 H13B 109.5 . . ?
H12A C8 H13B 109.5 . . ?
S1 C8 H14C 109.5 . . ?
H12A C8 H14C 109.5 . . ?
H13B C8 H14C 109.5 . . ?
C11 C9 C10 109.88(17) . . ?
C11 C9 S1 112.94(15) . . ?
C10 C9 S1 108.35(16) . . ?
C11 C9 H19 108.5 . . ?
C10 C9 H19 108.5 . . ?
S1 C9 H19 108.5 . . ?
O4 C10 N6 123.7(3) . . ?
O4 C10 C9 121.4(2) . . ?
N6 C10 C9 114.9(2) . . ?
O5 C11 N7 123.7(2) . . ?
O5 C11 C9 120.5(2) . . ?
N7 C11 C9 115.7(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 S1 C9 C11 47.0(2) . . . . ?
O2 S1 C9 C11 175.76(17) . . . . ?
C8 S1 C9 C11 -68.4(2) . . . . ?
O3 S1 C9 C10 -75.01(19) . . . . ?
O2 S1 C9 C10 53.79(18) . . . . ?
C8 S1 C9 C10 169.59(19) . . . . ?
C11 C9 C10 O4 -73.7(3) . . . . ?
S1 C9 C10 O4 50.1(3) . . . . ?
C11 C9 C10 N6 104.7(3) . . . . ?
S1 C9 C10 N6 -131.5(3) . . . . ?
C10 C9 C11 O5 55.0(3) . . . . ?
S1 C9 C11 O5 -66.1(3) . . . . ?
C10 C9 C11 N7 -122.5(2) . . . . ?
S1 C9 C11 N7 116.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N6 H15 O5 . . 2_665 2.901(4) 0.93(4) 2.01(4) 161(4) no
N6 H16 O3 . . 4_455 2.984(4) 0.73(4) 2.34(4) 147(4) no
N7 H17 O4 . . 2_664 3.030(4) 0.84(4) 2.22(4) 163(3) no
N7 H18 O5 . . 4_455 2.963(3) 0.86(4) 2.17(4) 152(3) no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.



#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        2-(methylsulfonyl)malonamide
_chemical_name_common            MSMA
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: methanol'
_exptl_crystal_preparation       ferroelectric
